[ CAS No. 623-53-0 ] {[proInfo.proName]}

Name: 623-53-0|Ethyl methyl carbonate|97%
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SKU: A146927
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Quality Control of [ 623-53-0 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 623-53-0 ]

SDS Specification

Alternatived Products of [ 623-53-0 ]

Product Details of [ 623-53-0 ]

CAS No. :	623-53-0	MDL No. :	MFCD00191398
Formula :	C₄H₈O₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	JBTWLSYIZRCDFO-UHFFFAOYSA-N
M.W :	104.10	Pubchem ID :	522046
Synonyms :

Calculated chemistry of [ 623-53-0 ]

Physicochemical Properties

Num. heavy atoms :	7
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.75
Num. rotatable bonds :	3
Num. H-bond acceptors :	3.0
Num. H-bond donors :	0.0
Molar Refractivity :	24.1
TPSA :	35.53 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.3 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.9
Log Po/w (XLOGP3) :	0.89
Log Po/w (WLOGP) :	0.79
Log Po/w (MLOGP) :	0.01
Log Po/w (SILICOS-IT) :	-0.03
Consensus Log Po/w :	0.71

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	2.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-0.85
Solubility :	14.8 mg/ml ; 0.142 mol/l
Class :	Very soluble
Log S (Ali) :	-1.22
Solubility :	6.26 mg/ml ; 0.0601 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-0.42
Solubility :	39.9 mg/ml ; 0.383 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.65

Safety of [ 623-53-0 ]

Signal Word:	Danger	Class:	3
Precautionary Statements:	P261-P305+P351+P338	UN#:	3272
Hazard Statements:	H225-H315-H319-H335	Packing Group:	Ⅲ
GHS Pictogram:

Application In Synthesis of [ 623-53-0 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 623-53-0 ]
Downstream synthetic route of [ 623-53-0 ]

[ 623-53-0 ] Synthesis Path-Upstream 1~2

1
[ 623-53-0 ]
[ 99-90-1 ]
[ 26510-95-2 ]

Reference： [1] Chemical Communications, 2011, vol. 47, # 39, p. 11143 - 11145

2
[ 623-53-0 ]
[ 100-06-1 ]
[ 2881-83-6 ]

Reference： [1] Chemical Communications, 2011, vol. 47, # 39, p. 11143 - 11145

[ 623-53-0 ] Synthesis Path-Downstream 1~61

1
[ 67-56-1 ]
[ 87463-09-0 ]
[ 74-87-3 ]
[ 623-53-0 ]

Reference： [1]Journal of the American Chemical Society,1955,vol. 77,p. 1899

2
[ 67-56-1 ]
[ 541-41-3 ]
[ 623-53-0 ]

Reference： [1]Justus Liebigs Annalen der Chemie,1880,vol. 205,p. 231

3
[ 124-41-4 ]
[ 541-41-3 ]
[ 623-53-0 ]

Reference： [1]Justus Liebigs Annalen der Chemie,1880,vol. 205,p. 231

4
[ 64-17-5 ]
[ 79-22-1 ]
[ 623-53-0 ]

Yield	Reaction Conditions	Operation in experiment
98.1%	With 1,2-dimethyl-1H-imidazole; at 0 - 20℃; for 1.0h;Product distribution / selectivity;	20.0 g (0.434 moles) of ethanol was dissolved in 53.5 g (0.651 moles) of 1- methylimidazole, and slowly added dropwise with 49.2 g (0.521 mole) of methyl chloroformate at 0 0C, followed by stirring for 1 hour. The temperature of the reactants was elevated up to the room temperature. Upper layer was separated and subject to the conversion analysis using a gas-liquid chromatography equipped with a capillary column. The conversion of ethanol was 98.6%. The upper layer was distilled at reduced pressure and colorless transparent liquid ethyl methyl carbonate was obtained in the yield of 97.4%. Ionic liquid imidazolium salt of Formula 5 was instantaneously produced as an intermediate product in the form of white solid when 1-methylimidazole was mixed with methyl chloroformate in the absence of alcohol compound (yield 97%).1H NMR (300 MHz, DMSOd6, 25 0C): delta (ppm) = 10.10 (s, IH, CH-Im), 8.15, 7.96 (d, 2H, CH-Im), 4.08 (s, 3H, CH3-Im), 3.96 (s, 3H, CH3-O); Dialkylcarbonates were synthesized under the same conditions as in Example 1 except by changing imidazoles as shown in Table 1. The results are presented in Table 1. Table 3.
97.4%	With 1-methyl-1H-imidazole; at 0 - 20℃; for 1.0h;	20.0 g (0.434 moles) of ethanol was dissolved in 53.5 g (0.651 moles) of 1- methylimidazole, and slowly added dropwise with 49.2 g (0.521 mole) of methyl chloroformate at 0 0C, followed by stirring for 1 hour. The temperature of the reactants was elevated up to the room temperature. Upper layer was separated and subject to the conversion analysis using a gas-liquid chromatography equipped with a capillary column. The conversion of ethanol was 98.6%. The upper layer was distilled at reduced pressure and colorless transparent liquid ethyl methyl carbonate was obtained in the yield of 97.4%. Ionic liquid imidazolium salt of Formula 5 was instantaneously produced as an intermediate product in the form of white solid when 1-methylimidazole was mixed with methyl chloroformate in the absence of alcohol compound (yield 97%).1H NMR (300 MHz, DMSOd6, 25 0C): delta (ppm) = 10.10 (s, IH, CH-Im), 8.15, 7.96 (d, 2H, CH-Im), 4.08 (s, 3H, CH3-Im), 3.96 (s, 3H, CH3-O).
97.6%	With 1-methyl-1H-imidazole; In bis-2-propyl carbonate; at 0 - 20℃; for 1.0h;	20.0 g (0.434 moles) of ethanol was dissolved in 53.5 g (0.651 moles) of 1- methylimidazole, and slowly added dropwise with 49.2 g (0.521 mole) of methyl chloroformate at 0 0C, followed by stirring for 1 hour. The temperature of the reactants was elevated up to the room temperature. Upper layer was separated and subject to the conversion analysis using a gas-liquid chromatography equipped with a capillary column. The conversion of ethanol was 98.6%. The upper layer was distilled at reduced pressure and colorless transparent liquid ethyl methyl carbonate was obtained in the yield of 97.4%.Ionic liquid imidazolium salt of Formula 5 was instantaneously produced as an intermediate product in the form of white solid when 1-methylimidazole was mixed with methyl chloroformate in the absence of alcohol compound (yield 97%).1H NMR (300 MHz, DMSOd6, 25 0C): delta (ppm) = 10.10 (s, IH, CH-Im), 8.15, 7.96 (d, 2H, CH-Im), 4.08 (s, 3H, CH3-Im), 3.96 (s, 3H, CH3-O); Dialkylcarbonates are synthesized under the same conditions as in Examples 1, 2 and 13 except by adding 200 mL of the same kind of the produced dialkylcarbonates as a solvent. The results are presented in Table 5.

94.8%	With 1-vinylimidazole; at 0 - 20℃; for 1.0h;Product distribution / selectivity;	20.0 g (0.434 moles) of ethanol was dissolved in 53.5 g (0.651 moles) of 1- methylimidazole, and slowly added dropwise with 49.2 g (0.521 mole) of methyl chloroformate at 0 0C, followed by stirring for 1 hour. The temperature of the reactants was elevated up to the room temperature. Upper layer was separated and subject to the conversion analysis using a gas-liquid chromatography equipped with a capillary column. The conversion of ethanol was 98.6%. The upper layer was distilled at reduced pressure and colorless transparent liquid ethyl methyl carbonate was obtained in the yield of 97.4%. Ionic liquid imidazolium salt of Formula 5 was instantaneously produced as an intermediate product in the form of white solid when 1-methylimidazole was mixed with methyl chloroformate in the absence of alcohol compound (yield 97%).1H NMR (300 MHz, DMSOd6, 25 0C): delta (ppm) = 10.10 (s, IH, CH-Im), 8.15, 7.96 (d, 2H, CH-Im), 4.08 (s, 3H, CH3-Im), 3.96 (s, 3H, CH3-O); Dialkylcarbonates were synthesized under the same conditions as in Example 1 except by changing imidazoles as shown in Table 1. The results are presented in Table 1. Table 3.
94.8%	With 1-Butylimidazole; at 0 - 20℃; for 1.0h;Product distribution / selectivity;	20.0 g (0.434 moles) of ethanol was dissolved in 53.5 g (0.651 moles) of 1- methylimidazole, and slowly added dropwise with 49.2 g (0.521 mole) of methyl chloroformate at 0 0C, followed by stirring for 1 hour. The temperature of the reactants was elevated up to the room temperature. Upper layer was separated and subject to the conversion analysis using a gas-liquid chromatography equipped with a capillary column. The conversion of ethanol was 98.6%. The upper layer was distilled at reduced pressure and colorless transparent liquid ethyl methyl carbonate was obtained in the yield of 97.4%. Ionic liquid imidazolium salt of Formula 5 was instantaneously produced as an intermediate product in the form of white solid when 1-methylimidazole was mixed with methyl chloroformate in the absence of alcohol compound (yield 97%).1H NMR (300 MHz, DMSOd6, 25 0C): delta (ppm) = 10.10 (s, IH, CH-Im), 8.15, 7.96 (d, 2H, CH-Im), 4.08 (s, 3H, CH3-Im), 3.96 (s, 3H, CH3-O); Dialkylcarbonates were synthesized under the same conditions as in Example 1 except by changing imidazoles as shown in Table 1. The results are presented in Table 1. Table 3.
92.9%	With 1-allylimidazole; at 0 - 20℃; for 1.0h;Product distribution / selectivity;	20.0 g (0.434 moles) of ethanol was dissolved in 53.5 g (0.651 moles) of 1- methylimidazole, and slowly added dropwise with 49.2 g (0.521 mole) of methyl chloroformate at 0 0C, followed by stirring for 1 hour. The temperature of the reactants was elevated up to the room temperature. Upper layer was separated and subject to the conversion analysis using a gas-liquid chromatography equipped with a capillary column. The conversion of ethanol was 98.6%. The upper layer was distilled at reduced pressure and colorless transparent liquid ethyl methyl carbonate was obtained in the yield of 97.4%. Ionic liquid imidazolium salt of Formula 5 was instantaneously produced as an intermediate product in the form of white solid when 1-methylimidazole was mixed with methyl chloroformate in the absence of alcohol compound (yield 97%).1H NMR (300 MHz, DMSOd6, 25 0C): delta (ppm) = 10.10 (s, IH, CH-Im), 8.15, 7.96 (d, 2H, CH-Im), 4.08 (s, 3H, CH3-Im), 3.96 (s, 3H, CH3-O); Dialkylcarbonates were synthesized under the same conditions as in Example 1 except by changing imidazoles as shown in Table 1. The results are presented in Table 1. Table 3.
63.5 - 98.0%	With 1-methyl-1H-imidazole; at 0 - 20℃; for 1.0h;Product distribution / selectivity;	20.0 g (0.434 moles) of ethanol was dissolved in 53.5 g (0.651 moles) of 1- methylimidazole, and slowly added dropwise with 49.2 g (0.521 mole) of methyl chloroformate at 0 0C, followed by stirring for 1 hour. The temperature of the reactants was elevated up to the room temperature. Upper layer was separated and subject to the conversion analysis using a gas-liquid chromatography equipped with a capillary column. The conversion of ethanol was 98.6%. The upper layer was distilled at reduced pressure and colorless transparent liquid ethyl methyl carbonate was obtained in the yield of 97.4%. Ionic liquid imidazolium salt of Formula 5 was instantaneously produced as an intermediate product in the form of white solid when 1-methylimidazole was mixed with methyl chloroformate in the absence of alcohol compound (yield 97%).1H NMR (300 MHz, DMSOd6, 25 0C): delta (ppm) = 10.10 (s, IH, CH-Im), 8.15, 7.96 (d, 2H, CH-Im), 4.08 (s, 3H, CH3-Im), 3.96 (s, 3H, CH3-O); Dialkylcarbonates are synthesized under the same conditions as in Example 1 except by changing each of the molar ratios of methyl chloroformate and 1- methylimidazole to alcohols as shown in Table 6. The results are presented in Table 6.
62.4 - 97.4%	With 1-methyl-1H-imidazole; at -20 - 50℃; for 1.0h;Product distribution / selectivity;	20.0 g (0.434 moles) of ethanol was dissolved in 53.5 g (0.651 moles) of 1- methylimidazole, and slowly added dropwise with 49.2 g (0.521 mole) of methyl chloroformate at 0 0C, followed by stirring for 1 hour. The temperature of the reactants was elevated up to the room temperature. Upper layer was separated and subject to the conversion analysis using a gas-liquid chromatography equipped with a capillary column. The conversion of ethanol was 98.6%. The upper layer was distilled at reduced pressure and colorless transparent liquid ethyl methyl carbonate was obtained in the yield of 97.4%. Ionic liquid imidazolium salt of Formula 5 was instantaneously produced as an intermediate product in the form of white solid when 1-methylimidazole was mixed with methyl chloroformate in the absence of alcohol compound (yield 97%).1H NMR (300 MHz, DMSOd6, 25 0C): delta (ppm) = 10.10 (s, IH, CH-Im), 8.15, 7.96 (d, 2H, CH-Im), 4.08 (s, 3H, CH3-Im), 3.96 (s, 3H, CH3-O); Dialkylcarbonates are synthesized under the same conditions as in Example 1 except by changing the reaction temperature as shown in Table 7. The results are presented in Table 7.
	With calcium hydroxide; In dichloromethane; at 0 - 20℃; for 16.0h;	General procedure: Stirring of 2,2,2-trifluoroethanol (1 g, 10 mmol), calcium oxide (560 mg, 10 mmol), and dichloromethane (2.84 g, 30 mmol) was performed at 0 C. to 5 C. To the resulting mixture was carefully dropwise added methyl chloroformate (0.992 g, 10.5 mmol) while preventing heat generation. After the completion of the dropping, the mixture was stirred for about 16 hours while gradually raising the temperature to room temperature, and then filtrated and distillated, thereby producing a composition containing CF3CH2OCOOCH3 and CH3OCOOCH3 with a conversion rate of 99.0%. The conversion rate means the conversion rate of the alcohol (2,2,2-trifluoroethanol in Example 1) determined by gas chromatography (GC). Table 1 shows the result. With regard to the water content of the system, the composition produced by the reaction was pulled out with a dry syringe and subjected to measurement using a Karl Fischer moisture meter to confirm that the composition contained water in an amount of 22 ppm (average of three measures).

Reference： [1]Patent: WO2008/1985,2008,A1 .Location in patent: Page/Page column 8; 11
[2]Patent: WO2008/1985,2008,A1 .Location in patent: Page/Page column 8
[3]Patent: WO2008/1985,2008,A1 .Location in patent: Page/Page column 8; 10; 12
[4]Patent: WO2008/1985,2008,A1 .Location in patent: Page/Page column 8; 11
[5]Patent: WO2008/1985,2008,A1 .Location in patent: Page/Page column 8; 11
[6]Patent: WO2008/1985,2008,A1 .Location in patent: Page/Page column 8; 11
[7]Organic Process Research and Development,2019,vol. 23,p. 667 - 673
[8]Patent: WO2008/1985,2008,A1 .Location in patent: Page/Page column 8; 13
[9]Patent: WO2008/1985,2008,A1 .Location in patent: Page/Page column 8; 14
[10]Journal of the Chemical Society. Perkin transactions II,1983,p. 291 - 296
[11]Journal of Physical Organic Chemistry,2003,vol. 16,p. 839 - 848
[12]Journal of Organic Chemistry USSR (English Translation),1983,p. 1981 - 1987
Zhurnal Organicheskoi Khimii,1983,vol. 19,p. 2271 - 2277
[13]Justus Liebigs Annalen der Chemie,1880,vol. 205,p. 231
[14]Journal of Chemical Research - Part S,1999,p. 150 - 151
[15]Patent: US2018/346404,2018,A1 .Location in patent: Paragraph 0125; 0130; 0137

5
[ 141-52-6 ]
[ 79-22-1 ]
[ 623-53-0 ]

Reference： [1]Justus Liebigs Annalen der Chemie,1880,vol. 205,p. 231
[2]Bulletin of the Chemical Society of Japan,1971,vol. 44,p. 3419 - 3423

6
[ 67-56-1 ]
[ 100314-09-8 ]
[ 623-53-0 ]

Reference： [1]Justus Liebigs Annalen der Chemie,1960,vol. 634,p. 49 - 64

7
[ 63755-37-3 ]
[ 623-53-0 ]
[ 3475-21-6 ]

Reference： [1]Heterocycles,1990,vol. 31,p. 2025 - 2028

8
[ 64-17-5 ]
[ 107820-42-8 ]
[ 623-53-0 ]
[ 36316-70-8 ]

Reference： [1]Doklady Chemistry,1991,vol. 317,p. 88 - 91
Dokl. Akad. Nauk SSSR Ser. Khim.,1991,vol. 317,p. 893 - 896

9
[ 64-17-5 ]
3-Cyano-1-methoxycarbonyl-pyridinium; chloride [ No CAS ]
[ 623-53-0 ]
[ 65520-09-4 ]

Reference： [1]Doklady Chemistry,1991,vol. 317,p. 88 - 91
Dokl. Akad. Nauk SSSR Ser. Khim.,1991,vol. 317,p. 893 - 896

10
[ 623-53-0 ]
[ 124-38-9 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions II,1983,p. 291 - 296

11
[ 623-53-0 ]
[ 97070-91-2 ]

Reference： [1]Canadian Journal of Chemistry,1985,vol. 63,p. 958 - 962

12
[ 132819-57-9 ]
[ 6304-31-0 ]
[ 623-53-0 ]

Reference： [1]Heterocycles,1990,vol. 31,p. 2025 - 2028

13
[ 82126-20-3 ]
[ 939-23-1 ]
[ 623-53-0 ]

Reference： [1]Heterocycles,1990,vol. 31,p. 2025 - 2028

14
[ 132819-55-7 ]
[ 15032-21-0 ]
[ 623-53-0 ]

Reference： [1]Heterocycles,1990,vol. 31,p. 2025 - 2028

15
[ 132819-56-8 ]
[ 2052-92-8 ]
[ 623-53-0 ]

Reference： [1]Heterocycles,1990,vol. 31,p. 2025 - 2028

16
[ 67-56-1 ]
[ 589-41-3 ]
[ 623-53-0 ]
[ 105-58-8 ]

Reference： [1]Collection of Czechoslovak Chemical Communications,1996,vol. 61,p. 1053 - 1063

17
[ 64-17-5 ]
[ 584-07-6 ]
[ 623-53-0 ]
[ 616-38-6 ]

Reference： [1]Collection of Czechoslovak Chemical Communications,1996,vol. 61,p. 1053 - 1063
[2]Collection of Czechoslovak Chemical Communications,1996,vol. 61,p. 1053 - 1063

18
[ 1609-47-8 ]
[ 4525-33-1 ]
[ 623-53-0 ]
[ 124-38-9 ]

Reference： [1]Journal of the Chemical Society, Dalton Transactions,1997,p. 3733 - 3740

19
[ 160663-37-6 ]
[ 124-41-4 ]
[ 619-33-0 ]
[ 623-53-0 ]

Reference： [1]Russian Chemical Bulletin,1998,vol. 47,p. 663 - 665

20
[ 631-22-1 ]
[ 110-83-8 ]
[ 623-53-0 ]
[ 2415-79-4 ]

Reference： [1]Tetrahedron Letters,1999,vol. 40,p. 1459 - 1462
[2]Tetrahedron Letters,1999,vol. 40,p. 1459 - 1462

21
[ 623-53-0 ]
[ 108-95-2 ]
[ 100-66-3 ]
[ 103-73-1 ]

Reference： [1]Synlett,2000,p. 272 - 274

Yield	Reaction Conditions	Operation in experiment
		EXAMPLE 13 To a one-liter, reactor were added 250 grams of MNPC obtained from example 2 and 250 grams of ENPC obtained from Example 3 and 1 gram of Zr(NO3)4. The mixture was heated to 180 C. and subjected to reaction for 5 hours under stirring. After the reaction was completed, the mixture was cooled to a temperature below 20 C. and sampled for the analysis of HPLC and GC. A conversion of 80.4% for (MNPC+ENPC) and selectivities of 26.1%, 8.8%and 36.5% for DMC, DEC and the resulting product ethyl methyl carbonate (abbreviated as EMC; chemical formula: H5 C2 --O--CO--O--CH3), respectively, were found.
		Example 13 To a one-litre reactor were added 250 grams of MNPC obtained from example 2 and 250 grams of ENPC obtained from Example 3 and 1 gram of Zr(NO3)4. The mixture was heated to 180C and subjected to reaction for 5 hours under stirring. After the reaction was completed, the mixture was cooled to a temperature below 20C and sampled for the analysis of HPLC and GC. A conversion of 80.4% for (MNPC + ENPC) and selectivities of 26.1%, 8.8% and 36.5% for DMC, DEC and the resulting product ethyl methyl carbonate (abbreviated as EMC; chemical formula: H5C2-O-CO-O-CH3), respectively, were found.

24
[ 681-84-5 ]
[ 105-58-8 ]
magnesium aluminium-ethylate [ No CAS ]
[ 623-53-0 ]

Reference： [1]Journal of the American Chemical Society,1946,vol. 68,p. 78

25
[ 563-17-7 ]
methylcarbonate potassium [ No CAS ]
[ 623-53-0 ]

Reference： [1]Justus Liebigs Annalen der Chemie,1851,vol. 79,p. 91

26
[ 623-53-0 ]
[ 67-56-1 ]
[ 74-85-1 ]

Reference： [1]Journal of Physical Organic Chemistry,2003,vol. 16,p. 839 - 848

27
[ 67-56-1 ]
[ 745829-72-5 ]
[ 623-53-0 ]
[ 3871-28-1 ]
ethyl N,N-dimethoxycarbamate [ No CAS ]

Reference： [1]Russian Chemical Bulletin,2003,vol. 52,p. 2251 - 2260

28
[ 67-56-1 ]
ethyl N-acetoxy-N-isopropoxycarbamate [ No CAS ]
[ 623-53-0 ]
ethyl N-isopropoxy-N-isopropoxycarbamate [ No CAS ]

Reference： [1]Russian Chemical Bulletin,2003,vol. 52,p. 2251 - 2260

29
[ 64-17-5 ]
[ 124-38-9 ]
[ 6257-10-9 ]
[ 623-53-0 ]
[ 105-58-8 ]

Reference： [1]Journal of Organic Chemistry,2005,vol. 70,p. 6177 - 6186

30
[ 67-56-1 ]
[ 64-17-5 ]
[ 124-38-9 ]
[ 623-53-0 ]
[ 616-38-6 ]
[ 105-58-8 ]

Yield	Reaction Conditions	Operation in experiment
23%; 2%; 3%	titanium tetramethoxide; at -168 - 150℃; for 15.0h;Cooling with ethanol-dry ice;	Into a 10-ml high pressure reactor (manufactured and sold by Thar Designs Inc., U.S.A.) equipped with a valve were charged 0.9 g (5 mmol) of titanium tetramethoxide (manufactured and sold by AZmax. co., Japan), about 0.9 g (30 mmol) of methanol (manufactured and sold by Wako Pure Chemical Industries, Ltd., Japan; a dehydrated grade), about 1.4 g (30 mmol) of ethanol (manufactured and sold by Wako Pure Chemical Industries, Ltd., Japan; a dehydrated grade) and a SUS ball (which was for use in stirring the contents of the reactor). The inside of the reactor was cooled to about -68 C with a dry ice/ethanol mixture. Then, from a carbon dioxide gas bomb, 2.0 g of a high purity carbon dioxide gas, the pressure of which was lowered to about 2 MPa by means of a pressure regulator connected to the carbon dioxide gas bomb, was gently introduced into the autoclave. The reactor was placed in an oil bath which was maintained at 150 C, and shaken for 15 hours. After that period, the inside of the reactor was cooled to about 20 C, and the internal pressure of the reactor was returned to atmospheric pressure by gently purging an excess amount of the carbon dioxide gas, thereby obtaining a white slurry as a reaction mixture. In the reaction mixture, methylethyl carbonate, dimethyl carbonate and diethyl carbonate were obtained in yields of 25 %, 3 % and 4 %, respectively. Step (2): Isolation of carbonic esters The above-obtained slurry was transferred into a 50-ml eggplant-shaped flask, and subjected to a reduced pressure distillation at 30 C. By the distillation, carbonic esters were recovered. With respect to the yields of the recovered carbonic esters, methylethyl carbonate, dimethyl carbonate and diethyl carbonate were obtained in yields of 23 %, 2 % and 3 %, respectively.

Reference： [1]Patent: EP1460056,2004,A1 .Location in patent: Page 33

31
[ 141-78-6 ]
[ 616-38-6 ]
[ 79-20-9 ]
[ 623-53-0 ]
[ 105-58-8 ]

Yield	Reaction Conditions	Operation in experiment
50%	lithium methanolate; at 77℃; for 3.0h;Product distribution / selectivity;	[25] [Example 1]; [26] 1.1 mole (99g) of dimethyl carbonate(DMC), 1.3 mole ( 114.4g) of ethyl acetate(EA), 0.21g (0.1 weight%) of LiOCH as a catalyst were added to a 500ml reaction flask equipped with a fractional distillation apparatus having the number of theoretical plates of 50 and containing a magnetic stirring bar. The mixtures were stirred while being heated to 77C for carrying out the transesterification reaction. During the initial stage of the reaction, all of the liquid condensed at the top plate of the fractional distillation apparatus was refluxed. After 30 minutes of reaction, the temperature of the top plate reached to 58C, which is the boiling point of methyl acetate, and the condensed liquid was refluxed with the reflux ratio of 3, and the unrefluxed condensed water was removed. After 3 hours of reaction, it was confirmed by a gas chromatography that the acetate compound did not exist in the reaction product, and then the reaction was completed. After completion of the reaction, the reaction product was analyzed with a gas chromatography. The gas chromatography analysis indicated that the molar ratio of dimethyl carbonate: ethyl methyl carbonate: diethyl carbonate was determined to be 1 : 2 : 1, and the reaction yield of ethyl methyl carbonate was 50% with respect to dimethyl carbonate(DMC). Next, the temperature of the reaction product was elevated to 1100C, and the reaction product was fractional distillated with the reflux ratio of equal or more than 5 to obtain ethyl methyl carbonate having the purity of 99.9%(Distillation yield: 85%). The moisture content of the obtained ethyl methyl carbonate was 50 ppm, which was measured by Karl Fisher titration.
50%	lithium amide; at 78℃; for 4.0h;Product distribution / selectivity;	[25] [Example 2]; [26] Except for using 0.5 weight% (1.73g) of LiNH instead of 0. lweight% of LiNH as the catalyst, and carrying out the reaction for 4 hours, the asymmetric linear carbonate was prepared in the same manner as described in Example 1. After completion of the reaction, the reaction product was analyzed with a gas chromatography. The gas chro¬ matography analysis indicated that the molar ratio of methyl acetate: ethyl acetate was determined to be 1 : 1, and the molar ratio of dimethyl carbonate: ethyl methyl carbonate: diethyl carbonate was determined to be 1 : 2 : 1, and the reaction yield of ethyl methyl carbonate was 50% with respect to dimethyl carbonate. Next, the reaction product was distilled at atmospheric pressure in a distillation tower having the number of theoretical plates of 50 and reflux ratio of more than 5 to produce ethyl methyl carbonate having the purity of 99% (Distillation yield: 78%).
50%	lithium methanolate; at 78℃; for 3.0h;Product distribution / selectivity;	[22] [Example 1]; [23] 1.3 mole ( 117g) of dimethyl carbonate(DMC), 2.6 mole (229g) of ethyl acetate(EA), and 1.35g (0.1 weight%) of LiOCH as a catalyst were added to a 500 ml reaction flask equipped with a condenser and containing a magnetic stirring bar. The mixtures were stirred while being heated to 78C for carrying out the transesterification EPO <DP n="6"/>reaction. The vapor generated during the reaction was sent to the condenser, condensed in the condenser, and was refluxed to the reactor. The reaction product was sampled periodically, and the composition of the reaction product was analyzed with a gas chro¬ matography. After 3 hours, from the moment at which the temperature of the reactor reached to 780C, the composition of the reaction product was not changed any more, and the reaction was completed. After completion of the reaction, the reaction product was analyzed with a gas chromatography. The gas chromatography analysis indicated that methyl acetate(MA) and ethyl methyl carbonate(EMC) were newly generated, and the molar ratio of methyl acetate(MA): ethyl acetate(EA) was determined to be 1 : 1, and the molar ratio of dimethyl carbonate(DMC): ethyl methyl carbonate(EMC): diethyl carbonate(DEC) was determined to be 1 : 2 : 1, and the reaction yield of ethyl methyl carbonate(EMC) was 50% with respect to dimethyl carbonate(DMC). Next, the reaction product was distilled at atmospheric pressure in a distillation tower having the number of theoretical plates of 50 and reflux ratio of more than 5 to produce ethyl methyl carbonate having the purity of 99% (Distillation yield: 80%).

47%

lithium amide; at 77℃; for 4.0h;Product distribution / selectivity;

[28] [Example 2]; [29] Except for using 0.5weight% (1.07g) of LiNH instead of 0.1weight% of LiOCH , and carrying out the reaction for 4 hours, the asymmetric linear carbonate was prepared in the same manner as described in Example 1. After completion of the reaction, the reaction product was analyzed by a gas chromatography. The gas chromatography analysis indicated that the molar ratio of dimethyl carbonate: ethyl methyl carbonate: diethyl carbonate in the reaction product was determined to be 1: 1.8: 1, and the reaction yield of ethyl methyl carbonate was 47% with respect to dimethyl carbonate. Next, the reaction product was fractional distillated with the reflux ratio of equal or more than 5 to obtain ethyl methyl carbonate having the purity of 99.9%(Distillation yield: 78%). The moisture content of the obtained ethyl methyl carbonate was 50 ppm, which was measured by Karl Fisher titration.

Reference： [1]Patent: WO2006/54832,2006,A1 .Location in patent: Page/Page column 5
[2]Patent: WO2006/54833,2006,A1 .Location in patent: Page/Page column 5
[3]Patent: WO2006/54833,2006,A1 .Location in patent: Page/Page column 4-5
[4]Patent: WO2006/54832,2006,A1 .Location in patent: Page/Page column 5

32
[ 79-20-9 ]
[ 105-58-8 ]
[ 623-53-0 ]
[ 616-38-6 ]

Yield	Reaction Conditions	Operation in experiment
50%	lithium methanolate; at 78℃; for 3.0h;Product distribution / selectivity;	[28] [Example 3]; [29] Except for using 1.3 mole (153g) of diethyl carbonate(DEC) and 2.6 mole (192.4g) of methyl acetate(MA) instead of 1.3 mole of dimethyl carbonate and 2.6 mole of ethyl acetate, the asymmetric linear carbonate was prepared in the same manner as described in Example 1. After completion of the reaction, the reaction product was analyzed with a gas chromatography. The gas chromatography analysis indicated that the molar ratio of ethyl acetate: methyl acetate was determined to be 1:1, and the molar ratio of diethyl carbonate: ethyl methyl carbonate: dimethyl carbonate was determined to be 1 : 2 : 1, and the reaction yield of ethyl methyl carbonate was 50% with respect to diethyl EPO <DP n="7"/>carbonate. Next, the reaction product was distilled at atmospheric pressure in a dis¬ tillation tower having the number of theoretical plates of 50 and reflux ratio of more than 5 to produce ethyl methyl carbonate having the purity of 99% (Distillation yield: 81%).

Reference： [1]Patent: WO2006/54833,2006,A1 .Location in patent: Page/Page column 5-6

33
[ 64-17-5 ]
[ 616-38-6 ]
[ 67-56-1 ]
[ 623-53-0 ]
[ 105-58-8 ]

Yield	Reaction Conditions	Operation in experiment
44%	lithium methanolate; at 78℃; for 4.0h;Product distribution / selectivity;	[31] [Comparative Example 1]; [32] Except for using 2.5mole (115g) of ethanol instead of 2.6 mole of ethyl acetate, and carrying out the reaction for 4 hours, the asymmetric linear carbonate was prepared in the same manner as described in Example 1. After completion of the reaction, the reaction product was analyzed with a gas chromatography. The gas chromatography analysis indicated that the reaction product included 4.6 weight% of unreacted ethanol, 9.4 weight% of methanol (byproduct), and the molar ratio of dimethyl carbonate: ethyl methyl carbonate: diethyl carbonate was determined to be 1: 1.6: 1, and the reaction yield of ethyl methyl carbonate was 44% with respect to dimethyl carbonate.

Reference： [1]Patent: WO2006/54833,2006,A1 .Location in patent: Page/Page column 6

34
[ 67-56-1 ]
[ 623-49-4 ]
[ 623-53-0 ]

Reference： [1]Chemistry - A European Journal,2009,vol. 15,p. 11642 - 11659

35
[ 616-38-6 ]
[ 105-58-8 ]
[ 623-53-0 ]

Yield	Reaction Conditions	Operation in experiment
83.39%	With Zeolitic imidazole framework (ZIF)-67; at 100℃; for 24.0h;	A mixture of DMC (9.000g, 0.1mol), DEC (11.800g, 0.1mol) and catalyst (0.200g, 2wt.%), was charged into a 50mL flask equipped with a magnetic stirring and a reflux condenser. The reaction mixture was then heated to 100C with continuous stirring. After 24h, the mixture was cooled to room temperature. And the product was filtered and analyzed by a gas chromatograph (GC, Agilent-7890A) equipped with a flame-ionized detector. In the reusability experiment, catalysts were separated by filtration and washed using methanol (10mL×3), then dried in air at 150C for the next reaction.
65.7%	With Zn(2-methylimidazolate)2; at 100℃; for 3.0h;	Typical procedure for the synthesis of EMC: 9.000 g (0.1 mol) DMC, 11.800 g (0.1 mol) DEC and 0.208 g (1 wt%) catalyst were charged into a 50 mL flask equipped with a magnetic stirring and a reflux condenser. The reaction mixture was then heated to 100 C with continuous stirring. After 3 h, the mixture was cooled to room temperature. And the product analyzed by GC (Shandong Lunan Ruihong Co. SP-6890). The structure of the product was defined by GC-MS (HP 6890/5973). In the experiment to test the reusability of catalyst, ZIF-8 was separated by filtration, washed using ethanol. After drying in oven, ZIF-8 was reused for the next time.
	at 92.84℃;	The liquid-phase transesterification of DEC with DMC was carried out as follows: 5.9 g (0.05 mol) of DEC, 4.5 g (0.05 mol) of DMC and 0.5 g of the catalyst were charged to a 50-mL two-neck flask. Then the mixture was heated up to 366 K with stirring to start the reaction. The reaction products were analyzed by gas chromatography (GC-8A)equipped with an HP-5 capillary column and FID.

83.39%Chromat.	With zeolitic imidazole framework-67; at 100℃; for 24.0h;Catalytic behavior; Mechanism;	A mixture of DMC (9.000 g, 0.1 mol), DEC (11.800 g, 0.1 mol) and catalyst (0.200 g, 2 wt.%), was charged into a 50 mL flask equipped with a magnetic stirring and a reflux condenser. The reaction mixture was then heated to 100 C with continuous stirring. After 24 h, the mixture was cooled to room temperature. And the product was filtered and analyzed by a gas chromatograph (GC, Agilent-7890A) equipped with a flame-ionized detector. In the reusability experiment, catalysts were separated by filtration and washed using methanol (10 mL × 3), then dried in air at 150 C for the next reaction.
	With titanium citrate; at 100℃; for 3.0h;	9.0 g of dimethyl carbonate (0.1 mol), 11.8 g of diethyl carbonate (0.1 mol),0.03 g of titanium citrate (0.15% of the total mass of dimethyl carbonate and diethyl carbonate)Add 100 ml of a two-neck round bottom flask equipped with a condenser tube.Stir well, heat to 100 C for 3 hours, after the reaction mixture by gas chromatography - mass spectrometry for qualitative and quantitative analysis,The conversion of dimethyl carbonate is 85%, and the selectivity of ethyl methyl carbonate is more than 99%.

Reference： [1]Catalysis Communications,2014,vol. 54,p. 86 - 90
[2]RSC Advances,2015,vol. 5,p. 25849 - 25856
[3]Journal of Molecular Catalysis A: Chemical,2013,vol. 366,p. 43 - 47
[4]Journal of Molecular Catalysis A: Chemical,2010,vol. 327,p. 32 - 37
[5]Catalysis Communications,2011,vol. 12,p. 721 - 725
[6]Catalysis Letters,2014,vol. 144,p. 1602 - 1608,7
[7]Catalysis Communications,2014,vol. 54,p. 86 - 90
[8]Patent: CN108976126,2018,A .Location in patent: Paragraph 0016-0026

36
[ 624-91-9 ]
[ 64-17-5 ]
[ 201230-82-2 ]
[ 623-53-0 ]

Yield	Reaction Conditions	Operation in experiment
	palladium and copper on lithium aluminate; at 120℃; for 3.0h;Product distribution / selectivity;	A porous lithium aluminate support having a spinel structure (Li/Al = 0.8/5, specific surface area: 95 m2/g) was placed in an aqueous ammonia solution containing palladium chloride and cupric chloride so that 1 wt.% of palladium and 1.2 wt.% of copper were deposited on the support. The support is then dried at 110C and fired to 200C in an airy atmosphere, to obtain a solid catalyst on which palladium and copper were deposited. To a gaseous mixture of methyl nitrite and carbon monoxide charged into a gas passing reaction vessel having a fixed bed and the above solid catalyst was added ethanol. The resulting gaseous mixture was subjected to gaseous catalytic reaction, to give methyl ethyl carbonate. The reaction conditions are given below: Gaseous starting mixture: methyl nitrite 15 vol.% and carbon monoxide 15 vol.%,Methanol content/added ethanol (molar ratio) = 0.8,Hydrogen chloride: 60 ppm,Amount of ethanol/methyl nitrite (molar ratio) = 0.25,Gas supply: supply rate (space velocity in terms of STP) 3,000 hr-1, at 3 kg/cm2G,Reaction temperature under pressure: 120C,Reaction period: 3 hours,Amount of catalyst: 5 g (7 mL) The results of the reaction are set forth in Table 1.

Reference： [1]Patent: EP2330096,2011,A1 .Location in patent: Page/Page column 5-6

37
[ 623-53-0 ]
[ 99-90-1 ]
[ 26510-95-2 ]

Reference： [1]Chemical Communications,2011,vol. 47,p. 11143 - 11145

38
[ 623-53-0 ]
[ 98-86-2 ]
[ 94-02-0 ]

Reference： [1]Chemical Communications,2011,vol. 47,p. 11143 - 11145

39
[ 623-53-0 ]
[ 122-00-9 ]
[ 27835-00-3 ]

Reference： [1]Chemical Communications,2011,vol. 47,p. 11143 - 11145

40
[ 623-53-0 ]
[ 100-06-1 ]
[ 2881-83-6 ]

Reference： [1]Chemical Communications,2011,vol. 47,p. 11143 - 11145

41
[ 96-49-1 ]
[ 67-56-1 ]
[ 64-17-5 ]
[ 623-53-0 ]
[ 35466-85-4 ]
[ 106729-72-0 ]
[ 616-38-6 ]

Yield	Reaction Conditions	Operation in experiment
	strongly basic ionexchange resin SA-11A; at 60℃; under 759.826 Torr; for 2.0h;	<Transesterification Reaction> The transesterification reactor after adjustment of catalyst above was kept at a temperature of 60C externally by the jacket, and a mixed raw material of ethylene carbonate, methanol and ethanol (compositional ratio: 1/1/1 (by mol)) was introduced. The reaction was performed at a pressure of 101.3 kPa for a residence time of 2 hours (SV=0.5 hr-1) to obtain a reaction product solution having the following composition. (Composition of Reaction Product Solution) Dimethyl carbonate : 7.5 wt% Ethyl methyl carbonate : 8.5 wt% Diethyl carbonate : 2.1 wt% Methyl glycol ether : 0.007 wt% Ethyl glycol ether : 0.002 wt% Ethylene glycol : 11.4 wt% Hydroxyethyl methyl carbonate : 5.8 wt% Hydroxyethyl ethyl carbonate : 7.2 wt% Ethylene carbonate : 27.9 wt% Methanol : 9.7 wt% Ethanol : 19.9 wt%

Reference： [1]Patent: EP2380868,2011,A1 .Location in patent: Page/Page column 14

42
[ 67-56-1 ]
[ 64-17-5 ]
[ 201230-82-2 ]
[ 623-53-0 ]

Reference： [1]Journal of the American Chemical Society,2011,vol. 133,p. 20378 - 20383

43
[ 623-53-0 ]
[ 108-98-5 ]
[ 100-68-5 ]
[ 622-38-8 ]
[ 139-66-2 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogen; at 400℃; under 760.051 Torr; for 3.0h;Gas phase;	General procedure: The general procedure for the catalytic reaction is described for the benzenethiol/methanol/1 system. A conventional vertical glass fixed-bed microreactor with a continuous gas-flow system was operated at atmospheric pressure [20]. In each experiment, a weighed supported sample of 1/SiO2 (10.0 mg) was packed in a borosilicate glass tube (3 mm i.d.) with the aid of quartz glass and placed in the center of an electric furnace. The supported cluster sample was initially heated from room temperature to a fixed temperature between 150 and 500 C in 15 min in a hydrogen stream (300 mL/h), and then it was held at that temperature for 45 min for activation. Then, the reaction was initiated by feeding a mixture of benzenethiol (22 muL/h, 0.2 mmol/h) and methanol (64 muL/h, 2.0 mmol/h) into the hydrogen stream without changing the temperature. The reaction was monitored every 30 min by sampling the reaction gas (1 mL) with a six-way valve kept at 150 C followed by analysis using an online gas-liquid chromatograph (GLC) with a methyl silicone column. The reactor effluent was collected in an ice trap containing tetrahydrofuran for subsequent analyses by GLC with a poly(ethylene glycol) capillary column or a dimethylpolysiloxane capillary column and gas chromatography-mass spectrometry (GC-MS) with a dimethylpolysiloxane capillary column. Catalytic reactions using the other alkylating reagents and catalysts were performed in the same way. In this paper, conversion and selectivity are defined as follows: conversion = products/(products + recovered benzenethiol) × 100 (%), and selectivity = product/(total amount of products) × 100 (%) based on benzenethiol.

Reference： [1]Applied Catalysis A: General,2013,vol. 450,p. 50 - 56

44
[ 64-17-5 ]
[ 616-38-6 ]
[ 623-53-0 ]

Yield	Reaction Conditions	Operation in experiment
51.47%	With lanthanum(III) chloride; calcium chloride; sodium hydroxide; at 90℃; for 12.0h;Molecular sieve; Glovebox;	In the fixed bed reactor, are respectively put into the self-made, the use of urea hydrolysis MgCl2, CaCl2And LaCl3(27), MgCl2, CaCl2And La2(SO4)3(28), MgCl2, CaCl2And La (NO3)3(29), MgCl2, CaSO4And LaCl3(30), MgCl2, Ca (NO3)2And LaCl3(31), MgSO4, CaCl2And LaCl3(32), Mg (NO3)2, CaCl2And LaCl3(22) Of 7.5% Mg - 7.5% Ca - 5% La/Al2O3- SiO2Catalyst each 50 g, wherein the carrier is made of SiO purchase2Sol [...] concentration is 0.5 mol/L of sodium hydroxide for 90 C heat treatment 12 h, after washing in 120 C drying 7 h made, carrier in from Al Al (NO3)3Urea hydrolysis, the active components in the load process SiO2Carrier, the active component of the salt solution, urea weight ratio of 1: 0.2: 5, the amount of the deionized water in the process of preparing raw materials quality of 15 times; the temperature of the oil bath by the room heating to 90 C, holding time is 6 h, catalyst aging time is 3 h; catalyst of the catalyst washing solvent consumption is 10 times, the drying temperature is 120 C, drying time is 6 h; catalyst the roasting temperature is 500 C, the roasting time is 3 h; the use of a constant flow pump will be dimethyl carbonate and ethanol in accordance with the molar ratio of the 1:1 ratio in the pumping into the reactor, atmospheric conditions, the reaction temperature is 100 C, raw material quality of the airspeed is 30 h-1The reaction is stable under the conditions of reaction 500 h after, sampling for chromatographic analysis and calculation, the results as shown in table 2 is shown.Table 2. The activity of the catalyst component sources to the conversion rate of raw materials, product selectivity and the yield impactFrom table 2 it can be seen that, in the same carrier, equivalent amount of active component of 7.5% Mg - 7.5% Ca - 5% La/Al2O3- SiO2In, the use of LaCl3And La (NO3)3As La component when the source of similar effect, but La2(SO4)3The catalyst prepared by the least effective, only yield coefficient a and b carbonate 35.44%; the same in order to CaSO4As the active component of the Ca sources for preparing a catalyst for the most active difference (methyl ethyl carbonate to yield coefficient 32.70%); the Mg (NO3)2, MgSO4And MgCl2As Mg component source prepared in the catalytic activity of the catalyst does not have the obvious difference on; in sum, active component from Mg (NO3)2, CaCl2And LaCl3Of 7.5% Mg - 7.5% Ca - 5% La/Al2O3- SiO2Catalyst (22) has the best catalytic activity, selectivity of the methyl ethyl carbonate 51.47%.
	With K-ZSM-5; at 130 - 180℃;Molecular sieve; Inert atmosphere;	6.0 g of the molecular sieve catalyst of Example 1 was packed in a fixed bed reactor, the temperature was raised to 180 C and nitrogen purged for 2 hours, and then the temperature was lowered to 130 C, dimethyl carbonate was mixed with ethanol at a molar ratio of 1:1 pumped into the reactor space velocity 4H-1, the reaction at atmospheric pressure, respectively, in the feed 30min, 1h, 2h, 4h, 8hsamples were collected, analyzed by chromatography, the conversion of dimethyl carbonate was 46.9%, The selectivity of methyl ethyl carbonate was 96.2%.
	With titanium glycinate; at 80℃; for 3.0h;	9.0 g of dimethyl carbonate(Dimethyl carbonate, Referred to as DMC, 0.1 mol), 18.4 g of ethanol (0.4 mol),0.02 g of glycine titanium(0.2% of the mass of dimethyl carbonate) was added to a 100 ml round-bottomed flask equipped with a condenser tube, stirred uniformly, and heated to 80 C for 3 hours. After the reaction, the mixture was qualitatively and quantitatively analyzed by gas chromatography-mass spectrometry. The conversion of dimethyl carbonate is 90%, and the selectivity of Ethyl methyl carbonate (EMC) is 91%.

Reference： [1]Russian Journal of Organic Chemistry,2014,vol. 50,p. 790 - 795
Zh. Org. Khim.,2014,vol. 50,p. 808 - 813,6
[2]RSC Advances,2014,vol. 4,p. 7013 - 7018
[3]Patent: CN109503377,2019,A .Location in patent: Paragraph 0023-0033
[4]Patent: CN103483200,2016,B .Location in patent: Paragraph 0024; 0025
[5]New Journal of Chemistry,2018,vol. 42,p. 13054 - 13064
[6]Patent: CN108976125,2018,A .Location in patent: Paragraph 0011; 0020; 0021; 0022; 0024; 0026; 0028

45
[ 64-17-5 ]
[ 616-38-6 ]
[ 623-53-0 ]
[ 105-58-8 ]

Yield	Reaction Conditions	Operation in experiment
73%	With sodium methylate; In methanol; at 69 - 120℃; for 6.0h;Reflux;	Example 5 Production of Diethyl Carbonate [Production Apparatus] (0142) The reactive distillation column the same as in Example 1 was used. [Reaction Method] (0143) A raw material for production composed of dimethyl carbonate (DMC) and ethanol (EtOH) (mass ratio: EtOH (% by weight)/DMC (% by weight)=49.86/50.14) was continuously fed at a rate of 88.7 g/hr from the raw material introduction port (M in FIG. 1) between the 32th and 33th trays from the column top of the reactive distillation column. (0144) Simultaneously, a sodium methoxide (MeONa) solution (mass ratio: MeONa (% by weight)/MeOH (% by weight)/EtOH (% by weight)=0.22/0.57/99.21) as a transesterification catalyst was also continuously fed at a rate of 25.1 g/hr from the catalyst introduction port (C in FIG. 1) between the 2nd and 3rd trays from the column top of the reactive distillation column. (0145) At the above described feed rates, under reaction conditions of the reactive distillation column including under normal pressure, column top temperature of 69 C. to 73 C., column temperature of 73 C. to 78 C. (25th tray), column bottom temperature of 105 C. to 120 C., and reflux ratio: r of 2.8, reactive distillation was continuously carried out. (0146) After the above described reaction was carried out continuously for 6 hours, a solution that was continuously distilled out at a rate of 68.7 g/hr from the column top distillation port (T in FIG. 1) of the reactive distillation column was recovered and an analysis of the contents showed that methanol was 36.1% by weight, ethanol was 48.1% by weight, dimethyl carbonate was 10.4% by weight (16% by weight for the raw material feed amount), ethyl methyl carbonate was 5.2% by weight, and the others were 0.2% by weight (the reaction conversion rate of dimethyl carbonate: 84%). A solution that was continuously extracted out at a rate of 45.1 g/hr from the column bottom part (B in FIG. 1) of the reactive distillation column was recovered and an analysis of the contents showed that ethanol was 1.4% by weight, ethyl methyl carbonate was 5.1% by weight, diethyl carbonate was 93.2% by weight, and the others were 0.3% by weight (the reaction yield of diethyl carbonate: 73%).
63.90%	With silica-alumina; at 78℃; under 760.051 Torr; for 2.0h;pH 11;	In a three-necked flask, 67.5 g of dimethyl carbonate, 58.5 g of ethanol, and 0.2 g of different kinds of catalysts of Example 9 were placed, and placed in a heating mantle, and heated to reflux at 78 C. for 2 h. The reaction equilibrium was determined by sampling and chromatographic analysis. The conversion of the raw materials, the selectivity of the products, and the yield of the products are shown in Table 14.
57.37%	With 15percentMgO-5percentMgCl-2percentLa2CO3 supported on Al2O3-SiO2; at 200℃; under 760.051 Torr;	In a fixed-bed reactor, 50 g each of the above-prepared catalysts were respectively charged, and dimethyl carbonate and ethanol were fed into the reactor in a molar ratio of 1:1 using a constant flow pump, and the space velocity was 30 1T1. Under normal pressure, the reaction temperature was 200C, and the stability was 500 hours. After stabilizing, the sample was taken for chromatographic analysis. The conversion of raw materials, product selectivity, and product yield are shown in Table 1. As can be seen from Table 1, different catalyst carriers have a great influence on the reaction. When Al203-Si02 is used as the catalyst carrier, the reaction effect is the best, the conversion rate of ethanol is 76.69%, and the conversion rate of dimethyl carbonate is 69.96%. This shows that the pore structure of the catalyst support Al203-Si02 is more suitable for the transesterification reaction. When using the small pore Si02 as the carrier, the ethanol conversion rate was only 7.99%, because the reaction is a mass transfer controlled reaction, and the small pore carrier is not conducive to reaction mass transfer, so the reaction efficiency The result is poor. When macroporous Si02 was used as the carrier, the ethanol conversion rate was only 12.20%, because the active component MgO could not achieve high dispersion on the surface of the macroporous catalyst. Therefore, in the preparation of a supported catalyst having a composite pore structure, the catalyst carrier is preferably Al203-SiO2

	at 80℃; for 4.0h;Autoclave;Catalytic behavior;	General procedure: EC (10 mmol), alcohol (100 mmol), and catalyst (5 wt% of EC) were taken in a Teflon-lined stainless-steel autoclave placed in a rotating hydrothermal reactor (Hiro Co., Japan; rotation speed = 50 rpm). Reactions were conducted at 40-100C for 0.5-6 h. After completion of the reaction, the autoclave was cooled to 25C, and the catalyst was separated by centrifugation/filtration. The liquid product was analyzed and quantified by gas chromatography (GC, Varian 3800; CP-SIL 5 column; 50 m × 0.25 mm × 0.25 m). The influence of reaction parameters (reaction time, reaction temperature, catalyst amount, and type of alcohol) on product yield was investigated. For comparison, experiments were also conducted with PC instead of EC. Those runs were carried out at 80-170C. In a different set of reactions, dialkyl carbonates were syn-thesized from DMC by reaction with alcohols. In a typicalreaction, DMC (10 mmol), ethanol/n-propanol/n-butanol/benzyl alcohol (100 mmol), and catalyst (10 wt% of DMC) were loaded on a Teflon-lined stainless-steel autoclave placed in a rotating hydrothermal reactor. Reactions were conducted at 80-150C for 6 h. After the reaction, the autoclave was cooled to 25C, and the catalyst was separated by centrifugation/filtration. Liquid product was analyzed and quantified by GC. The dialkyl carbonates formed from ethanol, n-propanol, n-butanol, and n-benzyl alcohol were designated as DEC, DPC, DBC, and DBzC, respectively.
	With calcium methylate; at 80℃;Large scale;	The use of the raw material is dimethyl carbonate (1.0mol), ethanol (2.0mol) and catalyst calcium methoxide (2% wt). The mass of the raw materials are dimethyl carbonate 90.8 kg, ethanol 92.14 kg, calcium methoxide 3.64 kg; The dimethyl carbonate, ethanol, calcium methoxide in accordance with the mass ratio are continuously inputted into the reaction kettle. At atmospheric pressure reflux reaction for 1 hour. The reaction temperature is 80 C. After reaching the balance, the reaction generated methanol was evaporated out by reduced pressure distillation. After condensation, enter into a methanol storage tank. Reaction generated diethyl carbonate, methyl ethyl carbonate and unreacted ethanol, dimethyl carbonate enter the rectifying column to be separated. The separated ethanol and dimethyl carbonate returns to the reactor to continue to participate in the reaction. The separated methyl ethyl carbonate and diethyl carbonate respectively enter into methyl ethyl carbonate storage tank and diethyl carbonate storage tank.

Reference： [1]Patent: US2015/291504,2015,A1 .Location in patent: Paragraph 0142-0146
[2]Patent: CN107501095,2017,A .Location in patent: Paragraph 0022; 0023; 0024; 0025; 0026; 0027-0075
[3]Patent: CN107473968,2017,A .Location in patent: Paragraph 0026; 0027; 0030; 0032; 0034; 0041; 0044; 0048
[4]Journal of Molecular Catalysis A: Chemical,2015,vol. 398,p. 42 - 49
[5]Patent: CN105541630,2016,A .Location in patent: Paragraph 0007
[6]Green Chemistry,2017,vol. 19,p. 1519 - 1528

46
[ 79-20-9 ]
[ 623-53-0 ]
[ 108-59-8 ]

Reference： [1]Advanced Synthesis and Catalysis,2015,vol. 357,p. 3076 - 3080

47
[ 67-56-1 ]
[ 745829-70-3 ]
[ 623-53-0 ]
[ 3871-28-1 ]
[ 90222-29-0 ]

Yield	Reaction Conditions	Operation in experiment
30%; 11%; 14%	With sodium acetate; at 30 - 31℃; for 96.0h;	A mixture of MeOH (5 mL) and AcONa (1.85 g) was added to ethyl N-chloro-N-methoxycarbamate 20 (1.23 g, 7.312 mmol). The reaction mixture was allowed to stand at 30-31 C for 4 days, then MeOH was distilled off in vacuo (20 Torr) and condensed in a cooled trap, the residue was extracted with Et2O (40 mL). The extract was concentrated in vacuo (20 Torr), the residue was subjected to chromatography on a column (Al2O3, Et2O-hexane). to obtain ethyl N-methoxycarbamate (26) (0.092 g, 11%) and N,N'-bis(ethoxycarbonyl)-N,N'-dimethoxyhydrazine (27) (0.124 g, 14%), which were identified based on the 1H NMR spectra (see Refs 18 and 36). GLC analysis showed that the methanol condensate contained methyl ethyl carbonate 28 (0.230 g, 30%).

Reference： [1]Russian Chemical Bulletin,2015,vol. 64,p. 62 - 75
Izv. Akad. Nauk, Ser. Khim.,2015,p. 62 - 75,14

48
[ 149-73-5 ]
[ 745829-70-3 ]
[ 623-53-0 ]
[ 3871-28-1 ]

Yield	Reaction Conditions	Operation in experiment
22%; 35%	In methanol; at -8 - 5℃; for 21.0h;	A solution of CH(OMe)3 (0.630 g, 5.969 mmol) in MeOH (5 mL) was added to ethyl N-chloro-N-methoxycarbamate 20 (0.611 g, 3.979 mmol) at -8 C, the mixture was allowed to stand at -8 C for 1 h and at 5 C for 20 h. MeOH was distilled off in vacuo (20 Torr) and condensed in a cooled trap, the residue was allowed to stand at 20 C and 8 Torr for 20 min to obtain ethyl N-methoxycarbamate (26) (0.165 g, 35%), which was identified based on the 1H NMR spectrum by the comparison with an authentic sample.36 1H NMR (300 MHz, CDCl3), delta: 1.30 (t, 3 H, CO2CH2Me, J = 6.9 Hz); 3.73 (s, 3 H, NOMe); 4.23 (q, 2 H, CO2CH2Me, J = 6.9 Hz); 7.87 (br.s, 1 H, NH). GLC analysis showed that the methanol condensate contained methyl ethyl carbonate 28 (0.093 g, 22%).

Reference： [1]Russian Chemical Bulletin,2015,vol. 64,p. 62 - 75
Izv. Akad. Nauk, Ser. Khim.,2015,p. 62 - 75,14

49
[ 75-89-8 ]
[ 623-53-0 ]
2,2,2-trifluoroethyl methyl carbonate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
91%	With tributylmethylammonium bis(trifluoromethanesulfonyl)imide salt; In triethylamine; at 50 - 80℃; for 15.0h;Autoclave; Large scale;	A process for the preparation of methyl trifluoroethylcarbonate, characterized by comprising the steps of:(1) In the 500L reactor were added strong alkaline quaternary ammonium I type anion exchange resin 100Kg, tributyl methylAmmonium bis (trifluoromethanesulfonyl) imide salt ion liquid 5Kg, triethylamine 50Kg, at 50 for 5h, the composite catalyst, spare;(2) 100 kg of trifluoroethanol was added to a 500 L autoclave, 50 kg of the composite catalyst obtained in step (1)Methyl methacrylate (45Kg), mixed and reacted at 80 C for 10 hours. After the completion of the reaction, the composite catalyst was recovered by filtration,The filtrate was distilled to give methyl trifluoroethyl carbonate product. Yield and selectivity are shown in Table 1.

Reference： [1]Patent: CN105061207,2017,B .Location in patent: Paragraph 0026; 0027; 0028; 0029; 0030; 0031; 0032-0054

50
[ 96-49-1 ]
[ 67-56-1 ]
[ 64-17-5 ]
[ 623-53-0 ]
[ 616-38-6 ]

Yield	Reaction Conditions	Operation in experiment
	With Zn-Y zeolite catalyst; at 100℃; under 15001.5 Torr; for 10.0h;Green chemistry;	In the slurry bed reactor 50L kettle 2MPa reaction pressure, the reaction raw material ethylene carbonate: methanol: ethanol = 1: 3: 2, divided respectively into the above-described method for preparing the basic catalyst obtained each 1.2 kg, the total volume of the reaction solution is 40 L. The reaction was mechanically stirred, and the reaction temperature was 100 C. After 10 hours of reaction, a sample was taken for chromatographic analysis, and the conversion of the raw materials and the product yield are shown in Table 1.

Reference： [1]Patent: CN108191660,2018,A .Location in patent: Paragraph 0052; 0053; 0061

51
[ 96-49-1 ]
[ 67-56-1 ]
[ 64-17-5 ]
[ 623-53-0 ]
[ 616-38-6 ]
[ 105-58-8 ]

Yield	Reaction Conditions	Operation in experiment
	With CsO/Al2O3 catalyst; at 100℃; under 15001.5 Torr; for 10.0h;Green chemistry;	In the slurry bed reactor 50L kettle 2MPa reaction pressure, the reaction raw material ethylene carbonate: methanol: ethanol = 1: 3: 2, divided respectively into the above-described method for preparing the basic catalyst obtained each 1.2 kg, the total volume of the reaction solution is 40 L. The reaction was mechanically stirred, and the reaction temperature was 100 C. After 10 hours of reaction, a sample was taken for chromatographic analysis, and the conversion of the raw materials and the product yield are shown in Table 1.
	With 15%BaO-5%MgO-3%La2O3/Cs-meso-EMT; at 100℃; under 82508.3 Torr; for 10.0h;Green chemistry;	In a 50L slurry bed reactor, The reaction pressure is 2 MPa, Reaction raw material ethylene carbonate: methanol: various alcohols = 1:3:2, Inject 15% BaO-5% MgO-3% La2O3/Cs-meso-EMT catalyst 1.2kg, The total volume of the reaction solution was 40 L. Mechanical stirring reaction, Reaction temperature 100 C, After 10 hours of reaction, samples were taken for chromatographic analysis. Raw material conversion rate, The product selectivity is not as shown in Table 2.

Reference： [1]Patent: CN108191660,2018,A .Location in patent: Paragraph 0052; 0053; 0059; 0061
[2]Patent: CN108191660,2018,A .Location in patent: Paragraph 0053; 0054; 0055; 0057; 0059; 0061; 0063; 0065

52
[ 623-53-0 ]
[ 38861-78-8 ]
[ 51407-46-6 ]

Reference： [1]Patent: US2018/170847,2018,A1 .Location in patent: Paragraph 0106

53
[ 284462-37-9 ]
[ 623-53-0 ]
[ 320-51-4 ]
[ 284461-73-0 ]

Yield	Reaction Conditions	Operation in experiment
	With 1-methyl-pyrrolidin-2-one; N-benzyl-trimethylammonium hydroxide; at 50℃; for 1.33333h;Green chemistry;	47 mmol of the above intermediate I, 3-trifluoromethyl-4-chloroaniline 47 mmol and 0.4 mmol of benzyltrimethylammonium hydroxide weredissolved in 100 mL of N-methylpyrrolidone, and ethyl methyl carbonate 50 mmol was added dropwise in portions. The temperature was raised to 50 C for 80 min, cooled to room temperature, and the reaction solution was added to a mixed solvent of 60 mL of water and 40 mL of ethyl acetate, stirred, layered, and the aqueous phase was extracted with ethyl acetate. The sodium chloride was washed, dried, and dried under vacuum at 40 C to obtain 20.99 g of crude sorafenib in a yield of 96.1%.

Reference： [1]Patent: CN108276327,2018,A .Location in patent: Paragraph 0028; 0048-0081

54
[ 64-17-5 ]
[ 79-22-1 ]
[ 623-53-0 ]
[ 616-38-6 ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine; In dichloromethane; at 0 - 20℃; for 16.0h;	General procedure: Stirring of 2,2,2-trifluoroethanol (1 g, 10 mmol), calcium oxide (560 mg, 10 mmol), and dichloromethane (2.84 g, 30 mmol) was performed at 0 C. to 5 C. To the resulting mixture was carefully dropwise added methyl chloroformate (0.992 g, 10.5 mmol) while preventing heat generation. After the completion of the dropping, the mixture was stirred for about 16 hours while gradually raising the temperature to room temperature, and then filtrated and distillated, thereby producing a composition containing CF3CH2OCOOCH3 and CH3OCOOCH3 with a conversion rate of 99.0%. The conversion rate means the conversion rate of the alcohol (2,2,2-trifluoroethanol in Example 1) determined by gas chromatography (GC). Table 1 shows the result. With regard to the water content of the system, the composition produced by the reaction was pulled out with a dry syringe and subjected to measurement using a Karl Fischer moisture meter to confirm that the composition contained water in an amount of 22 ppm (average of three measures).

Reference： [1]Patent: US2018/346404,2018,A1 .Location in patent: Paragraph 0125; 0130; 0135; 0137

55
[ 623-53-0 ]
[ 25015-63-8 ]
[ 1126-93-8 ]
[ 1195-66-0 ]

Yield	Reaction Conditions	Operation in experiment
	With C42H50Mg2N4; for 6.0h;	The beta-diimine monovalent magnesium compound catalyzes the reaction of <strong>[623-53-0]ethyl methyl carbonate</strong> with pinacol borane as follows:In the glove box, 1 mol% of beta-diimine monovalent magnesium compound, 0.4 mmol of <strong>[623-53-0]methyl ethyl carbonate</strong>, and 1.6 mmol of pinacol borane were sequentially added to the reaction flask.It was then removed from the glove box and stirred for 6 h. The yield was 98% by NMR

Reference： [1]Patent: CN110003261,2019,A .Location in patent: Paragraph 0076-0081
[2]Dalton Transactions,2020,vol. 49,p. 2776 - 2780

56
[ 67-56-1 ]
C₁₄H₉Cl₂F₃N₄O₂ [ No CAS ]
[ 623-53-0 ]
[ 120068-79-3 ]

Yield	Reaction Conditions	Operation in experiment
37.6 g; 5.8 g	With hydrogenchloride; In water; at 80℃;pH Ca. 7;	Add acid methanol dropwise to the cyclization liquid until the pH value is around 7 to obtain a neutralization liquid.The neutralized liquid was distilled under reduced pressure to -0.1 MPa. When no fraction was distilled out at 80 C, the distillation was completed, the vacuum was broken by passing nitrogen, and the temperature was lowered to normal temperature.Add 142g of chlorobenzene to the distillate and raise the temperature to about 70 C. Filter while hot. The filter cake is washed with 20g of hot chlorobenzene (the filter cake is washed as solid waste). The filtrate is combined and heated with 20g of water. After stirring for 10 minutes, The water phase was separated by standing, the organic phase was stirred and the temperature was lowered to 0 C, and the temperature was maintained for 4 hours. After the temperature was maintained, the filter was filtered.After pressure filtration, the filter cake was dried to obtain 119.6g of off-white crystalline powder with arylpyrazolenitrile content of 98.46% (HPLC external standard method); after the filtrate was distilled, the distillate was recrystallized to obtain 5.8g of light yellow powder. The content of pyrazolonitrile is 97.06% (HPLC external standard method), and the total yield is 89.51% (calculated by 2,6-dichloro-4-trifluoromethylaniline);The distillate of the cyclic liquid distillation is rectified at atmospheric pressure, methanol is recovered at the top of the tower, and secondary rectification is carried out at the bottom of the tower; low-boiling substances are separated at the top of the secondary rectification tower, and third-level rectification is produced at the bottom of the tower Distillation; 37.60g of ethyl methyl carbonate was recovered from the top of the three-stage rectification tower, with a content of 99.93% (GC, area normalization method), water content of 0.006%, and a yield of 84.03% (with 2,6-dichloro-4- Calculation of trifluoromethylaniline).

Reference： [1]Patent: CN110981806,2020,A .Location in patent: Paragraph 0008; 0029; 0032-0033

57
[ 623-53-0 ]
[ 7637-07-2 ]
[ 220991-85-5 ]

Yield	Reaction Conditions	Operation in experiment
>97%	for 48.0h;Schlenk technique; Inert atmosphere; Glovebox;	General procedure: BF3 (typical sizes 2.36 g, 34.84 mmol, 1.1equivalents) were condensed into an evacuated flask and weighed.Then the carbonate donor (D = dimethyl carbonate (DMC), ethylenecarbonate (EC), <strong>[623-53-0]ethyl methyl carbonate</strong> (<strong>[623-53-0]EMC</strong>), propylene carbonate(PC) and fluoroethylene carbonate (FEC)) were weighed (typicalsizes 5 g, 31.67 mmol, 1.0 equivalent) into a second flask in aglovebox. After condensing the preweighed BF3 into the flask with the donor, the mixtures were stirred until a white precipitate had formed. Next, the excess of BF3 was removed in vacuo. The solidswere transferred to a glovebox and mortared. These powders werefilled into a flask and gaseous BF3 (0.2 equivalents) were introducedagain. After two days the excess of BF3 was removed in vacuo andthe BF3 adducts (except BF3·FEC) were obtained as colorlesspowders (typical yields > 97%, see supporting information (SI) isavailable online at stacks.iop.org/JES/167/060514/mmedia).

Reference： [1]Journal of the Electrochemical Society,2020,vol. 167

58
[ 623-53-0 ]
[ 67-56-1 ]

Reference： [1]RSC Advances,2020,vol. 10,p. 13083 - 13094

59
[ 67-56-1 ]
[ 74-96-4 ]
[ 124-38-9 ]
[ 623-53-0 ]

Yield	Reaction Conditions	Operation in experiment
96%Chromat.	With 1,8-diazabicyclo[5.4.0]undec-7-ene; In acetonitrile; at 70℃; under 1875.19 Torr; for 2.0h;Autoclave;	Acetonitrile (0.3mL), DBU (1.5mmol), bromoethane (1.0mmol) and methanol (2.0mmol) were added to the 25mL autoclave, and then carbon dioxide was introduced to make the system pressure reach 0.25MPa at 70 C The reaction was magnetically stirred for 2 hours. After the reaction was completed, it was quantitatively analyzed by gas chromatography internal standard method, and the yield of ethyl methyl carbonate was 96%.

Reference： [1]Patent: CN111138285,2020,A .Location in patent: Paragraph 0016-0017; 0021

60
[ 623-53-0 ]
[ 135285-90-4 ]
2C₆H₆N₁₂O₁₂*3C₄H₈O₃ [ No CAS ]

Reference： [1]CrystEngComm,2020,vol. 22,p. 3451 - 3462

61
[ 497-06-3 ]
[ 623-53-0 ]
[ 4427-96-7 ]

Yield	Reaction Conditions	Operation in experiment
720 g	With 2,6-di-tert-butyl-4-methyl-phenol; potassium bromide at 80 - 92℃; for 6h;	6 Example 6 Take Example 3 after distillation of 3,4-DHB 600g in a 2L three-mouth flask, add 0.5g potassium bromide, 0.5g BHT, 1200g methyl ethyl carbonate stirred to heat up to 80 °C, start the transesterification dehygarization, ethanol reaction, temperature control 80-92 °C reaction for 6 hours, sampling 3,4- DhB chromatographic content of 0.34%, cooled to 40 °C filtering, filtrate and then heated up distillation to produce excess methyl ethyl carbonate, high vacuum distillation out of VEC crude 762g, content 99.16%, yield 98.83%. The resulting VEC crude product was added to 0.8gBHT, high vacuum vacuum distillation, and 77-88 °C/5mmHg fraction was collected to give VEC720g, purity 99.96%, moisture 53ppm

Reference： [1]Current Patent Assignee: SUZHOU HUA NEW ENERGY SCIENCE AND TECH - CN114149401, 2022, A Location in patent: Paragraph 0043-0045

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[ CAS No. 623-53-0 ] {[proInfo.proName]}

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Water Solubility

Medicinal Chemistry

Safety of [ 623-53-0 ]

Application In Synthesis of [ 623-53-0 ]

[ 623-53-0 ] Synthesis Path-Upstream 1~2

[ 623-53-0 ] Synthesis Path-Downstream 1~61

Related Functional Groups of [ 623-53-0 ]

Aliphatic Chain Hydrocarbons

Esters

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 623-53-0 ]