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[ CAS No. 111-27-3 ] {[proInfo.proName]}

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Chemical Structure| 111-27-3
Chemical Structure| 111-27-3
Structure of 111-27-3 * Storage: {[proInfo.prStorage]}
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Quality Control of [ 111-27-3 ]

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Product Details of [ 111-27-3 ]

CAS No. :111-27-3 MDL No. :MFCD00002982
Formula : C6H14O Boiling Point : -
Linear Structure Formula :- InChI Key :ZSIAUFGUXNUGDI-UHFFFAOYSA-N
M.W :102.17 Pubchem ID :8103
Synonyms :
1-Hexanol

Calculated chemistry of [ 111-27-3 ]

Physicochemical Properties

Num. heavy atoms : 7
Num. arom. heavy atoms : 0
Fraction Csp3 : 1.0
Num. rotatable bonds : 4
Num. H-bond acceptors : 1.0
Num. H-bond donors : 1.0
Molar Refractivity : 32.12
TPSA : 20.23 Ų

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) : -5.48 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.03
Log Po/w (XLOGP3) : 2.03
Log Po/w (WLOGP) : 1.56
Log Po/w (MLOGP) : 1.53
Log Po/w (SILICOS-IT) : 1.28
Consensus Log Po/w : 1.69

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.49
Solubility : 3.32 mg/ml ; 0.0325 mol/l
Class : Very soluble
Log S (Ali) : -2.08
Solubility : 0.845 mg/ml ; 0.00827 mol/l
Class : Soluble
Log S (SILICOS-IT) : -1.64
Solubility : 2.34 mg/ml ; 0.0229 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.07

Safety of [ 111-27-3 ]

Signal Word:Danger Class:3
Precautionary Statements:P210-P233-P240-P241-P242-P243-P264-P270-P273-P280-P301+P312+P330-P303+P361+P353-P305+P351+P338-P337+P313-P363-P370+P378-P403+P235-P501 UN#:2282
Hazard Statements:H225-H302+H312-H319-H412 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 111-27-3 ]

* 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 [ 111-27-3 ]
  • Downstream synthetic route of [ 111-27-3 ]

[ 111-27-3 ] Synthesis Path-Upstream   1~40

  • 1
  • [ 95-54-5 ]
  • [ 111-27-3 ]
  • [ 5851-46-7 ]
Reference: [1] ACS Catalysis, 2017, vol. 7, # 11, p. 7456 - 7460
[2] ChemCatChem, 2018, vol. 10, # 7, p. 1607 - 1613
[3] Chemistry - A European Journal, 2014, vol. 20, # 19, p. 5569 - 5572
[4] Dalton Transactions, 2017, vol. 46, # 43, p. 15012 - 15022
[5] Organic Preparations and Procedures International, 2008, vol. 40, # 1, p. 101 - 105
[6] Chemische Berichte, 1936, vol. 69, p. 2263,2270
  • 2
  • [ 95-54-5 ]
  • [ 111-27-3 ]
  • [ 5851-46-7 ]
  • [ 144991-21-9 ]
Reference: [1] ACS Catalysis, 2017, vol. 7, # 11, p. 7456 - 7460
  • 3
  • [ 637-88-7 ]
  • [ 111-27-3 ]
  • [ 67399-93-3 ]
  • [ 18979-55-0 ]
Reference: [1] European Journal of Organic Chemistry, 2013, # 26, p. 5902 - 5916
[2] European Journal of Organic Chemistry, 2013, # 26, p. 5902 - 5916
  • 4
  • [ 123-31-9 ]
  • [ 111-27-3 ]
  • [ 18979-55-0 ]
Reference: [1] Chemical and Pharmaceutical Bulletin, 1994, vol. 42, # 3, p. 570 - 575
[2] Chemical and Pharmaceutical Bulletin, 1994, vol. 42, # 3, p. 576 - 579
[3] Journal of Organic Chemistry USSR (English Translation), 1991, vol. 27, # 9.1, p. 1609 - 1611[4] Zhurnal Organicheskoi Khimii, 1991, vol. 27, # 9, p. 1828 - 1831
  • 5
  • [ 111-25-1 ]
  • [ 123-31-9 ]
  • [ 67399-93-3 ]
  • [ 18979-55-0 ]
  • [ 111-27-3 ]
Reference: [1] Bulletin de la Societe Chimique de France, 1993, vol. 130, p. 475 - 480
  • 6
  • [ 33332-25-1 ]
  • [ 111-27-3 ]
  • [ 668972-67-6 ]
  • [ 668972-68-7 ]
  • [ 36070-80-1 ]
Reference: [1] Patent: WO2004/18428, 2004, A1, . Location in patent: Page 350-351
  • 7
  • [ 928-89-2 ]
  • [ 2009-83-8 ]
  • [ 111-27-3 ]
Reference: [1] Bulletin of the Chemical Society of Japan, 1992, vol. 65, # 2, p. 530 - 534
  • 8
  • [ 57392-44-6 ]
  • [ 111-27-3 ]
  • [ 115-20-8 ]
  • [ 2639-63-6 ]
Reference: [1] Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1992, vol. 31, # 12, p. 883 - 885
  • 9
  • [ 111-27-3 ]
  • [ 115-20-8 ]
Reference: [1] Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1992, vol. 31, # 12, p. 883 - 885
  • 10
  • [ 111-27-3 ]
  • [ 115-20-8 ]
Reference: [1] Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1992, vol. 31, # 12, p. 883 - 885
  • 11
  • [ 111-27-3 ]
  • [ 115-20-8 ]
  • [ 13141-13-4 ]
Reference: [1] Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1992, vol. 31, # 12, p. 883 - 885
  • 12
  • [ 57978-00-4 ]
  • [ 110-53-2 ]
  • [ 66-25-1 ]
  • [ 108-93-0 ]
  • [ 111-27-3 ]
Reference: [1] Journal of the American Chemical Society, 1989, vol. 111, # 7, p. 2674 - 2681
  • 13
  • [ 1068-55-9 ]
  • [ 111-27-3 ]
  • [ 6485-79-6 ]
Reference: [1] Journal of Organometallic Chemistry, 2006, vol. 691, # 1-2, p. 182 - 192
  • 14
  • [ 32315-10-9 ]
  • [ 111-27-3 ]
  • [ 6092-54-2 ]
Reference: [1] Pharmaceutical Research, 2004, vol. 21, # 6, p. 940 - 946
[2] Synthetic Communications, 2006, vol. 36, # 23, p. 3537 - 3548
[3] Patent: EP1202959, 2004, B1, . Location in patent: Page 13-14; 15-16
[4] Patent: CN103848762, 2016, B, . Location in patent: Paragraph 0109; 0112-0114
  • 15
  • [ 75-44-5 ]
  • [ 111-27-3 ]
  • [ 6092-54-2 ]
Reference: [1] Bulletin de la Societe Chimique de France, 1936, vol. <5>3, p. 1065
[2] Journal of the Chemical Society [Section] C: Organic, 1966, p. 346 - 350
[3] Patent: US2006/84822, 2006, A1, . Location in patent: Page/Page column 7-8
[4] Patent: US2006/84822, 2006, A1, . Location in patent: Page/Page column 7-8
  • 16
  • [ 111-27-3 ]
  • [ 503-38-8 ]
  • [ 6092-54-2 ]
Reference: [1] Journal of the Chinese Chemical Society, 2000, vol. 47, # 1, p. 271 - 274
[2] Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 8, p. 1716 - 1727
  • 17
  • [ 127-19-5 ]
  • [ 111-27-3 ]
  • [ 1118-92-9 ]
Reference: [1] Journal of the American Chemical Society, 2016, vol. 138, # 34, p. 10786 - 10789
[2] RSC Advances, 2013, vol. 3, # 33, p. 13702 - 13704
[3] Organic and Biomolecular Chemistry, 2016, vol. 14, # 39, p. 9215 - 9220
  • 18
  • [ 124-63-0 ]
  • [ 111-27-3 ]
  • [ 16156-50-6 ]
YieldReaction ConditionsOperation in experiment
99% With triethylamine In dichloromethane at 0 - 20℃; General procedure: Alcohols (50 mmol, 1 equiv.) and 11.08 mL Et3N (80 mmol, 1.6 equiv.) was dissolved in 60 mL CH2Cl2, and the solution was cooleddown to 0 °C, then 4.33 mL methanesulfonyl chloride (56 mmol, 1.12 equiv.) was introduced by syringe successively. The mixture is stirredfor 30 min at 0 °C, and then stirred overnight at room temperature. The organic layer is washed successively with 1M hydrochloric acid solution, saturated aqueous sodium bicarbonate solution, and brine. The organic layer is dried over Na2SO4, filtered, and concentrated under reduced pressure. The product was purified by column chromatography with silica gel (EtOAc: petroleum=1: 2).
Reference: [1] Organic and Biomolecular Chemistry, 2018, vol. 16, # 41, p. 7753 - 7759
[2] Journal of the American Chemical Society, 1985, vol. 107, # 18, p. 5210 - 5219
[3] Journal of Fluorine Chemistry, 2018, vol. 214, p. 35 - 41
[4] Journal of the Electrochemical Society, 2010, vol. 157, # 9, p. F124-F129
[5] European Journal of Organic Chemistry, 2018, vol. 2018, # 35, p. 4850 - 4856
[6] Canadian Journal of Chemistry, 1956, vol. 34, p. 757,760
[7] Journal of the American Chemical Society, 1954, vol. 76, p. 2984,2986
[8] Journal of Medicinal Chemistry, 1990, vol. 33, # 10, p. 2807 - 2813
[9] Tetrahedron Letters, 1990, vol. 31, # 17, p. 2457 - 2460
[10] Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999), 1991, # 8, p. 1201 - 1208
[11] Synthetic Communications, 1984, vol. 14, # 5, p. 469 - 476
[12] Green Chemistry, 2009, vol. 11, # 12, p. 1955 - 1960
[13] Physical Chemistry Chemical Physics, 2009, vol. 11, # 39, p. 8939 - 8948
[14] Catalysis Communications, 2010, vol. 11, # 5, p. 470 - 475
[15] Tetrahedron Letters, 2017, vol. 58, # 1, p. 59 - 62
  • 19
  • [ 112-30-1 ]
  • [ 111-27-3 ]
  • [ 3913-02-8 ]
  • [ 2425-77-6 ]
  • [ 21078-85-3 ]
  • [ 5333-42-6 ]
YieldReaction ConditionsOperation in experiment
8.4% at 255℃; for 6 h; Dean-Stark; Inert atmosphere General procedure: A 100 mL five-neck flask equipped with; a magnetic stirring-bar, a temperature probe, a nitrogen inlet, a condenser and a Dean-Stark system for separating the water formed by the reaction, was charged with 40 g of 1 -octanol, 0.6 g of granular potassium hydroxide (1 .5 wtpercent) and 0.4 g of copper-nickel catalyst comprised in a hydrotalcite (the Cu/Ni molar ratio was 2.5/7.5; and the total content of copper and nickel metals in the whole catalyst was 13percent by weight). The temperature was elevated under N2 flow (rate of 50 to 60 mL/min) up to the boiling point of the alcohol (195 9C). The time when the reaction mixture reached 190 to 200 QC (reflux) was designed as the point of initiation of the reaction. The highest temperature allowed for the reaction to be conducted was 225 QC. The reaction was terminated after 8 hours. Then, the liquid reaction mixture was cooled and centrifuged to remove the copper- nickel catalyst and the precipitated soap-type products (potassium carboxylates). The composition of the final reaction mixture was analysed by GC, as follow: 83.4percent 2-hexyl-1 - decanol; 5.3percent C16-non-Guerbet; 5.3percent C24-products; 2.1 percent 1 -octanol. (0223) The 1 -octanol conversion, 2-hexyl-1 -decanol (C16-Guerbet alcohol) product selectivity, C16- Guerbet (alcohol) product yield after 6 hours reaction and the C16-non-Guerbet (alcohol) (such as 2-hexyl-2-decenal, 2-hexyldecanal and 2-hexyl-2-decen-1 -ol) product yield after 6 hours reaction are shown in Table 1 . A purity of the final target product (2-hexyl-1 -decanol (C16-Guerbet alcohol)) was calculated considering the losses in the mass balance during the reaction (due to the formation of carboxylic salts and 1 -octanol evaporation) and subtracting the un reacted 1 -octanol. This value is a good agreement with the purity of the Cl 6-Guerbet estimated after distillation of the final reaction mixture.
Reference: [1] Patent: WO2017/93473, 2017, A1, . Location in patent: Page/Page column 17-18; 30
  • 20
  • [ 124-38-9 ]
  • [ 111-27-3 ]
  • [ 7523-15-1 ]
YieldReaction ConditionsOperation in experiment
85% at 109.84℃; for 48 h; Autoclave General procedure: All the reactions were carried out in an autoclave reactor withan inner volume of 190 ml. A typical procedure of the reaction of CO2 + methanol with 2-cyanopyridine was as follows: 0.34 g of CeO2 catalyst, 0.64 g of methanol (20 mmol, Wako Pure Chemical Industries, 99.8percent min.), and 10.4 g of 2-cyanopyridine (100 mmol,Tokyo Chemical Industry Co., Ltd., 99.0percent min.) were put into the autoclave together with a spinner, and then, the reactor was purged and pressurized with CO2 (Shimakyu Co. Ltd., >99.5percent). Gas line was closed, and then, the reactor was heated to the reaction temperature. The time when the temperature reached the desired reaction temperature is defined as zero reaction time. The mixture was constantly stirred during the reaction. After the specific reaction time, the reactor was cooled to room temperature and the gas was collected. Ethanol (30 ml, Wako Pure Chemical Industries, 99.5percent min.) and 1-hexanol (0.2 ml, Tokyo ChemicalIndustry Co., Ltd., 98.0percent min.) were added to the liquid phase asa solvent and an internal standard substance for a quantitativeanalysis, respectively. Products in the liquid and gas phases were analyzed by using a gas chromatograph equipped with FID(Shimadzu GC-2014) and GC–MS (Shimadzu QP-2020) with a CP-Sil5 capillary column (length 50 m, i.d. 0.25 mm, film thickness0.25 μm). For the synthesis of various carbonates from CO2 and the corresponding alcohols, the procedures are the same as the case of the reaction of CO2 + methanol with 2-cyanopyridine. After the reaction time, 30 ml of ethanol or acetone (Wako Pure Chemical Industries,99.5percent min.) was added to the liquid phase as a solvent, and 0.2 ml of 1-hexanol or 1-propanol (Wako Pure Chemical Industries,99.5percent min.) was added to the liquid phase as an internal standard substance for a quantitative analysis. The products in the liquid and gas phases were analyzed by gas chromatography equippedwith an FID or quadrupole mass spectrometer (GC–MS) using a CP-Sil5 capillary column (length 50 m, i.d. 0.25 mm, film thickness 0.25 μm) or TC-WAX capillary column (length 30 m, i.d. 0.25 mm, film thickness 0.25 μm).
40% at 130℃; for 288 h; Heating Into a two-necked flask equipped with a condenser was inserted an injection tube which had connected thereto a glass ball filter (G2) (manufactured and sold by Vidrex Co., Ltd., Japan). Further, a stirrer was placed in the flask. Into the two-necked flask were charged 0.75 g of the above-obtained liquid (containing an organometal compound) and 41 g of n-hexanol. Then, introduction of a high purity carbon dioxide gas into the flask through the injection tube was started at a flow rate of 100 ml/min. The flask was heated using an oil bath (which was maintained at 130 °C) while stirring the contents of the flask and introducing a high purity carbon dioxide gas into the flask, thereby producing dihexyl carbonate. 288 hours after the start of the heating of the flask, the yield of dihexyl carbonate was 40 percent.
18% at 120℃; for 100 h; Production of dihexyl carbonate from dibutyltin dihexyloxide Into a 100-ml autoclave (manufactured and sold by Toyo Koatsu Co., Ltd., Japan) were charged about 2.2 g of an organometal compound containing about 5 mmol of dibutyltin dihexyloxide (wherein the organometal compound was contained in the above-obtained reaction mixture) and 25.5 g (250 mmol) of hexanol (manufactured and sold by Aldrich, U.S.A.; a dehydrated grade). The autoclave was sealed. Then, from a carbon dioxide gas bomb, carbon dioxide gas, the pressure of which was lowered to 4 MPa by means of a pressure regulator connected to the carbon dioxide gas bomb, was introduced into the autoclave. Stirring of the contents of the autoclave was started. 10 Minutes after the start of the stirring, the valve of the carbon dioxide gas bomb was closed. Then, the internal temperature of the autoclave was elevated to 120 °C while stirring. Thereafter, carbon dioxide gas was gradually withdrawn from the autoclave through a purge line so as to adjust the internal pressure of the autoclave to 4 MPa. Then, a reaction was performed for 100 hours while maintaining the internal pressure of the autoclave at 4 MPa. After that period, the inside of the autoclave was cooled to about 30 °C, and the internal pressure of the autoclave was returned to atmospheric pressure by gently purging the carbon dioxide gas through a purge line, and there was obtained a transparent reaction mixture. In the reaction mixture, dihexyl carbonate was obtained in a yield of 18 percent.
17% at 120℃; for 100 h; Into a 100-ml autoclave (manufactured and sold by Toyo Koatsu Co., Ltd., Japan) were charged about 2.2 g of an organometal compound containing about 5 mmol of dibutyltin dihexyloxide (wherein the organometal compound was contained in the above-obtained reaction mixture) and 25.5 g (250 mmol) of hexanol (manufactured and sold by Aldrich, U.S.A.; a dehydrated grade). The autoclave was sealed. Then, from a carbon dioxide gas bomb, carbon dioxide gas, the pressure of which was lowered to 4 MPa by means of a pressure regulator connected to the carbon dioxide gas bomb, was introduced into the autoclave. Stirring of the contents of the autoclave was started. 10 Minutes after the start of the stirring, the valve of the carbon dioxide gas bomb was closed. Then, the internal temperature of the autoclave was elevated to 120 °C while stirring. Thereafter, carbon dioxide gas was gradually withdrawn from the autoclave through a purge line so as to adjust the internal pressure of the autoclave to 4 MPa. Then, a reaction was performed for 100 hours while maintaining the internal pressure of the autoclave at 4 MPa. After that period, the inside of the autoclave was cooled to about 30 °C, and the internal pressure of the autoclave was returned to atmospheric pressure by gently purging the carbon dioxide gas through a purge line, and there was obtained a transparent reaction mixture. In the reaction mixture, dihexyl carbonate was obtained in a yield of 17 percent.
14% at 180℃; for 6.16667 h; Into the above-mentioned 200-ml autoclave containing the reaction mixture (containing an organometal compound having a hexyloxy group) was charged 61.5 g (602 mmol) of hexanol (manufactured and sold by Aldrich, U.S.A.; a dehydrated grade), and the autoclave was sealed. Then, from a carbon dioxide gas bomb, carbon dioxide gas, the pressure of which was lowered to 5 MPa by means of a pressure regulator connected to the carbon dioxide gas bomb, was introduced into the autoclave. Stirring of the contents of the autoclave was started. 10 Minutes after the start of the stirring, the valve of the carbon dioxide gas bomb was closed. Then, the internal temperature of the autoclave was elevated to 180 °C while stirring. In this instant, the internal pressure of the autoclave was about 7.5 MPa. Then, a reaction was performed for 6 hours while maintaining the internal pressure of the autoclave at about 7.5 MPa. Thereafter, the inside of the autoclave was cooled to about 30 °C and the internal pressure of the autoclave was returned to atmospheric pressure by gently purging the carbon dioxide gas, and there was obtained a transparent reaction mixture. In the reaction mixture, dihexyl carbonate was obtained in a yield of about 14 percent.
14% at 180℃; for 6.16667 h; Subsequently, the same procedures as in step (1) and step (2) were successively performed as follows. Step (1): Production of dihexyl carbonate from the organometal compound obtained in step (3) Into the above-mentioned autoclave in which step (3) was performed was charged 61.5 g (602 mmol) of hexanol (manufactured and sold by Aldrich, U.S.A.; a dehydrated grade), and the autoclave was sealed. Then, from a carbon dioxide gas bomb, carbon dioxide gas, the pressure of which was lowered to 5 MPa by means of a pressure regulator connected to the carbon dioxide gas bomb, was introduced into the autoclave. Stirring of the contents of the autoclave was started. 10 Minutes after the start of the stirring, the valve of the carbon dioxide gas bomb was closed. Then, the internal temperature of the autoclave was elevated to 180 °C while stirring. In this instant, the internal pressure of the autoclave was about 7.5 MPa. Then, a reaction was performed for 6 hours while maintaining the internal pressure of the autoclave at about 7.5 MPa. Thereafter, the inside of the autoclave was cooled to about 30 °C and the internal pressure of the autoclave was returned to atmospheric pressure by gently purging the carbon dioxide gas through the purge line, and there was obtained a transparent reaction mixture. In the reaction mixture, dihexyl carbonate was obtained in a yield of about 14 percent.

Reference: [1] Journal of Catalysis, 2014, vol. 318, p. 95 - 107
[2] Patent: EP1460056, 2004, A1, . Location in patent: Page 32
[3] Journal of the Chemical Society - Perkin Transactions 1, 1999, # 15, p. 2205 - 2208
[4] Patent: EP1460056, 2004, A1, . Location in patent: Page 29
[5] Patent: EP1460056, 2004, A1, . Location in patent: Page 29-30
[6] Patent: EP1460056, 2004, A1, . Location in patent: Page 27
[7] Patent: EP1460056, 2004, A1, . Location in patent: Page 28
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  • [ 111-27-3 ]
  • [ 7523-15-1 ]
YieldReaction ConditionsOperation in experiment
92.3% at 140 - 170℃; for 20 h; The reaction apparatus was the same as in Example 1. Take 10g urea, 68g n-hexanol, 0.5g nickel acetate, 2g triphenylphosphine in a three-neck bottle, heat in 170 ° C oil bath, vacuum, system vacuum 10Kpa, system maintain 140 ° C, slightly boiling, stirring reflux Reaction for 20 hr.Gas chromatography analysis showed that the yield of di-n-hexyl carbonate was 92.3percent based on the amount of urea charged.
Reference: [1] Patent: CN108358786, 2018, A, . Location in patent: Paragraph 0048
  • 22
  • [ 111-27-3 ]
  • [ 7523-15-1 ]
YieldReaction ConditionsOperation in experiment
17% for 0.5 h; After step (1), 10 g of hexanol containing 1 percent by weight of water was gently added to the reaction mixture obtained in step (1), and the resultant mixture was stirred for about 30 minutes. Then, the autoclave was opened, and it was found that the mixture in the autoclave had turned into a white slurry. The white slurry was subjected to filtration using a membrane filter (H020A142C, manufactured and sold by Advantec Toyo Kaisha, Ltd., Japan) to thereby obtain white solids and a filtrate. The white solids were washed 2 times with 20 ml of hexanol. The filtrate was transferred into a 1-liter eggplant-shaped flask and subjected to distillation under heating. By the distillation, hexanol and dihexyl carbonate were recovered. The yield of dihexyl carbonate was 17 percent.
16% for 0.5 h; After step (1), 10 g of hexanol containing 1 percent by weight of water was gently added to the reaction mixture obtained in step (1), and the resultant mixture was stirred for about 30 minutes. Then, the autoclave was opened, and it was found that the mixture in the autoclave had turned into a white slurry. The white slurry was subjected to filtration using a membrane filter (H020A142C, manufactured and sold by Advantec Toyo Kaisha, Ltd., Japan) to thereby obtain white solids and a filtrate. The white solids were washed 2 times with 20 ml of hexanol. The filtrate was transferred into a 1-liter eggplant-shaped flask and subjected to distillation under heating. By the distillation, hexanol and dihexyl carbonate were recovered. The yield of dihexyl carbonate was 16 percent.
13% at 150℃; for 0.5 h; Heating After step (1), 10 g of hexanol containing 1 percent by weight of water was gently added to the reaction mixture obtained in step (1), and the resultant mixture was stirred for about 30 minutes. Then, the autoclave was opened, and it was found that the mixture in the autoclave had turned into a white slurry. The white slurry was subjected to filtration using a membrane filter (H020A142C, manufactured and sold by Advantec Toyo Kaisha, Ltd., Japan) to thereby obtain white solids and a filtrate. The white solids were washed 2 times with 20 ml of hexanol. The filtrate was transferred into a 1-liter eggplant-shaped flask and subjected to distillation under heating in an oil bath at 150 °C and under a pressure of 1 KPa. By the distillation, hexanol and dihexyl carbonate were recovered. The yield of dihexyl carbonate was 13 percent.
13% for 0.5 h; After step (1), 10 g of hexanol containing 1 percent by weight of water was gently added to the reaction mixture obtained in step (1), and the resultant mixture was stirred for about 30 minutes. Then, the autoclave was opened, and it was found that the mixture in the autoclave had turned into a white slurry. The white slurry was subjected to filtration using a membrane filter (H020A142C, manufactured and sold by Advantec Toyo Kaisha, Ltd., Japan) to thereby obtain white solids and a filtrate. The white solids were washed 2 times with 20 ml of hexanol. The filtrate was transferred into a 1-liter eggplant-shaped flask and subjected to distillation under heating. By the distillation, hexanol and dihexyl carbonate were recovered. The yield of dihexyl carbonate was 13 percent.

Reference: [1] Patent: EP1460056, 2004, A1, . Location in patent: Page 29
[2] Patent: EP1460056, 2004, A1, . Location in patent: Page 30
[3] Patent: EP1460056, 2004, A1, . Location in patent: Page 28
[4] Patent: EP1460056, 2004, A1, . Location in patent: Page 28
[5] Synthesis, 1989, # 8, p. 636 - 638
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  • [ 111-27-3 ]
  • [ 7523-15-1 ]
Reference: [1] Patent: US4349486, 1982, A,
  • 24
  • [ 108-32-7 ]
  • [ 111-27-3 ]
  • [ 7523-15-1 ]
YieldReaction ConditionsOperation in experiment
62.5 - 74 %Chromat. at 170℃; for 8 h; This example describes the preparation of dihexyl carbonate from propylene carbonate and hexanol. Propylene carbonate (1.02 g; 10 mmol), hexanol (100 mmol), catalyst (250 mg) were charged in a 100 ml stainless steal autoclave having a Teflon-liner. The autoclave was closed and then placed in a rotating synthesis reactor (Hiro Co., Japan, Model-KH 02, rotating speed=30 rpm). The reaction was conducted at 170° C. for 8 h. The contents were allowed to cool to room temperature. Catalyst was separated by filtration from the reaction mixture. The products were isolated and analyzed as described in EXAMPLE 2. Results are tabulated in table-2.
Reference: [1] Patent: US2007/83062, 2007, A1, . Location in patent: Page/Page column 3; 4
  • 25
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  • [ 111-27-3 ]
  • [ 7523-15-1 ]
YieldReaction ConditionsOperation in experiment
74 %Chromat. at 170℃; for 8 h; EXAMPLE 8 This example describes the preparation of dihexyl carbonate from propylene carbonate and hexanol. Propylene carbonate (1.02 g; 10 mmol), hexanol (100 mmol), catalyst (250 mg) were charged in a 100 ml stainless steal autoclave having a Teflon-liner. The autoclave was closed and then placed in a rotating synthesis reactor (Hiro Co., Japan, Model-KH 02, rotating speed = 30 rpm). The reaction was conducted at 170 C for 8 h. The contents were allowed to cool to room temperature. Catalyst was separated by filtration from the reaction mixture. The products were isolated and analyzed as described in EXAMPLE 2. Results are tabulated in table-2.
Reference: [1] Patent: EP1777212, 2007, A1, . Location in patent: Page/Page column 5-6
  • 26
  • [ 96-49-1 ]
  • [ 111-27-3 ]
  • [ 7523-15-1 ]
YieldReaction ConditionsOperation in experiment
68 mol at 80℃; for 4 h; Autoclave General procedure: EC (10 mmol), alcohol (100 mmol), and catalyst (5 wtpercent 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 40–100°C for 0.5–6 h. After completion of the reaction, the autoclave was cooled to 25°C, 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 80–170°C.
Reference: [1] Journal of Molecular Catalysis A: Chemical, 2015, vol. 398, p. 42 - 49
  • 27
  • [ 616-38-6 ]
  • [ 111-27-3 ]
  • [ 7523-15-1 ]
  • [ 39511-75-6 ]
YieldReaction ConditionsOperation in experiment
4 %Chromat. at 80℃; for 6 h; Dimethyl carbonate (3.06 g) and 1-hexanol (6.94 g) in a molar ratio of 1:2 were mixed together with in each case a constant quantity (5.7.x.10-6 mol) of a catalyst (see Table 1) in a 20 ml rolled flange glass vessel, which was closed with a natural rubber septum including a gas outlet. If the catalyst used was present at room temperature in solid aggregate state, it was first dissolved in one of the educts. The reaction mixture was heated for 6 hours to 80° C., with stirring. After cooling to room temperature, analysis of the product spectrum was performed by gas chromatography, optionally coupled with mass spectrometric examination. The reaction product contents, namely methylhexyl carbonate or dihexyl carbonate, which can be taken as a measure of the activity of the transesterification catalyst used, were quantified by integration of the respective gas chromatograms
5.1 %Chromat. at 80℃; for 6 h; Dimethyl carbonate (3.06 g) and 1-hexanol (6.94 g) in a molar ratio of 1:2 were mixed together with in each case a constant quantity (5.7.x.10-6 mol) of a catalyst (see Table 1) in a 20 ml rolled flange glass vessel, which was closed with a natural rubber septum including a gas outlet. If the catalyst used was present at room temperature in solid aggregate state, it was first dissolved in one of the educts. The reaction mixture was heated for 6 hours to 80° C., with stirring. After cooling to room temperature, analysis of the product spectrum was performed by gas chromatography, optionally coupled with mass spectrometric examination. The reaction product contents, namely methylhexyl carbonate or dihexyl carbonate, which can be taken as a measure of the activity of the transesterification catalyst used, were quantified by integration of the respective gas chromatograms
3.4 %Chromat. at 80℃; for 6 h; Dimethyl carbonate (3.06 g) and 1-hexanol (6.94 g) in a molar ratio of 1:2 were mixed together with in each case a constant quantity (5.7.x.10-6 mol) of a catalyst (see Table 1) in a 20 ml rolled flange glass vessel, which was closed with a natural rubber septum including a gas outlet. If the catalyst used was present at room temperature in solid aggregate state, it was first dissolved in one of the educts. The reaction mixture was heated for 6 hours to 80° C., with stirring. After cooling to room temperature, analysis of the product spectrum was performed by gas chromatography, optionally coupled with mass spectrometric examination. The reaction product contents, namely methylhexyl carbonate or dihexyl carbonate, which can be taken as a measure of the activity of the transesterification catalyst used, were quantified by integration of the respective gas chromatograms
23.5 %Chromat. at 80℃; for 6 h; Dimethyl carbonate (3.06 g) and 1-hexanol (6.94 g) in a molar ratio of 1:2 were mixed together with in each case a constant quantity (5.7.x.10-6 mol) of a catalyst (see Table 1) in a 20 ml rolled flange glass vessel, which was closed with a natural rubber septum including a gas outlet. If the catalyst used was present at room temperature in solid aggregate state, it was first dissolved in one of the educts. The reaction mixture was heated for 6 hours to 80° C., with stirring. After cooling to room temperature, analysis of the product spectrum was performed by gas chromatography, optionally coupled with mass spectrometric examination. The reaction product contents, namely methylhexyl carbonate or dihexyl carbonate, which can be taken as a measure of the activity of the transesterification catalyst used, were quantified by integration of the respective gas chromatograms
2.1 %Chromat. at 80℃; for 6 h; Dimethyl carbonate (3.06 g) and 1-hexanol (6.94 g) in a molar ratio of 1:2 were mixed together with in each case a constant quantity (5.7.x.10-6 mol) of a catalyst (see Table 1) in a 20 ml rolled flange glass vessel, which was closed with a natural rubber septum including a gas outlet. If the catalyst used was present at room temperature in solid aggregate state, it was first dissolved in one of the educts. The reaction mixture was heated for 6 hours to 80° C., with stirring. After cooling to room temperature, analysis of the product spectrum was performed by gas chromatography, optionally coupled with mass spectrometric examination. The reaction product contents, namely methylhexyl carbonate or dihexyl carbonate, which can be taken as a measure of the activity of the transesterification catalyst used, were quantified by integration of the respective gas chromatograms

Reference: [1] Patent: US2004/230069, 2004, A1, . Location in patent: Page 2
[2] Patent: US2004/230069, 2004, A1, . Location in patent: Page 2
[3] Patent: US2004/230069, 2004, A1, . Location in patent: Page 2
[4] Patent: US2004/230069, 2004, A1, . Location in patent: Page 2
[5] Patent: US2004/230069, 2004, A1, . Location in patent: Page 2
  • 28
  • [ 64401-37-2 ]
  • [ 181116-34-7 ]
  • [ 124-38-9 ]
  • [ 62774-20-3 ]
  • [ 111-27-3 ]
  • [ 7523-15-1 ]
YieldReaction ConditionsOperation in experiment
13% at 180℃; for 6.16667 h; Into the above-mentioned 200-ml autoclave containing the reaction mixture (containing an organometal compound having a hexyloxy group) was charged 61.5 g (602 mmol) of hexanol (manufactured and sold by Aldrich, U.S.A.; a dehydrated grade), and the autoclave was sealed. Then, from a carbon dioxide gas bomb which was connected to the autoclave through a SUS tube and a valve, carbon dioxide gas having a pressure of 5 MPa was introduced into the autoclave. Stirring of the contents of the autoclave was started. 10 Minutes after the start of the stirring, the valve of the carbon dioxide gas bomb was closed. Then, the internal temperature of the autoclave was elevated to 180 °C while stirring. In this instant, the internal pressure of the autoclave was about 7.5 MPa. Then, a reaction was performed for 6 hours while maintaining the internal pressure of the autoclave at about 7.5 MPa. Thereafter, the inside of the autoclave was cooled to about 30 °C and the internal pressure of the autoclave was returned to atmospheric pressure by gently purging the carbon dioxide gas, and there was obtained a transparent reaction mixture. In the reaction mixture, dihexyl carbonate was obtained in a yield of 14 percent.; Step (2) After step (1), 10 g of hexanol containing 1 percent of water was gently added to the reaction mixture obtained in step (1), and the resultant mixture was stirred for about 1 minute. Then, the autoclave was opened, and it was found that the mixture in the autoclave had turned into a white slurry. The white slurry was subjected to filtration using a membrane filter (H020A142C, manufactured and sold by Advantec Toyo Kaisha, Ltd., Japan) to thereby obtain white solids and a filtrate. The white solids were washed 2 times with 20 ml of hexanol. The filtrate was transferred into a 1-liter eggplant-shaped flask and subjected to a distillation under heating in an oil bath at 160 °C and under reduced pressure. By the distillation, hexanol, tributyltin hexyloxide and dihexyl carbonate were recovered as a distillate. The yield of dihexyl carbonate was 13 percent. It was found that the distillate contained about 2 mmol of tributyltin hexyloxide. On the other hand, a viscous liquid remained in the flask after completion of the distillation.
13% at 180℃; for 6.16667 h; The white solids obtained in step (2) and the residual viscous liquid which remained in the flask after the distillation performed in step (2), were charged into a 200-ml autoclave (manufactured and sold by Toyo Koatsu Co., Ltd., Japan). Further, 51.1 g (500 mmol) of hexanol (manufactured and sold by Aldrich, U.S.A.; a dehydrated grade) was charged into the autoclave, and the autoclave was sealed. The atmosphere in the autoclave was purged with nitrogen gas. Then, stirring of the contents of the autoclave was started, and the internal temperature of the autoclave was elevated to 160 °C. Then, the stirring was continued for about 30 minutes. Thereafter, the purge line of the autoclave was opened, and water and hexanol were distilled off through the purge line over 4 hours while blowing a small amount of nitrogen gas into the bottom of the autoclave. After that period, there was almost no distillate any more. Then, the inside of the autoclave was cooled to about 30 °C, and there was obtained a reaction mixture. 1H-, 13C- and 119Sn-NMR analyses of the reaction mixture was performed. The NMR analyses showed that the reaction mixture contained about 40 mmol of 1,1,3,3-tetrabutyl-1,3-di-hexyloxy-distannoxane, about 7 mmol of dibutyltin dihexyloxide and about 4 mmol of tributyltin hexyloxide. After step (3), step (1) was performed as follows. Into the above-mentioned autoclave in which step (3) was performed was charged 61.5 g (602 mmol) of hexanol (manufactured and sold by Aldrich, U.S.A.; a dehydrated grade). The autoclave was sealed. Then, from a carbon dioxide gas bomb which was connected to the autoclave through a SUS tube and a valve, carbon dioxide gas having a pressure of 5 MPa was introduced into the autoclave. Stirring of the contents of the autoclave was started. 10 Minutes after the start of the stirring, the valve of the carbon dioxide gas bomb was closed. Then, the internal temperature of the autoclave was elevated to 180 °C while stirring. In this instant, the internal pressure of the autoclave was about 7.5 MPa. Then, a reaction was performed for 6 hours while maintaining the internal pressure of the autoclave at about 7.5 MPa. Thereafter, the inside of the autoclave was cooled to about 30 °C and the internal pressure of the autoclave was returned to atmospheric pressure by gently purging the carbon dioxide gas through the purge line, and there was obtained a transparent reaction mixture. In the reaction mixture, dihexyl carbonate was obtained in a yield of 14 percent. After step (1), 10 g of hexanol containing 1 percent of water was gently added to the reaction mixture obtained in step (1), and the resultant mixture was stirred for about 1 minute. Then, the autoclave was opened, and it was found that the mixture in the autoclave had turned into a white slurry. The white slurry was subjected to filtration using a membrane filter (H020A142C, manufactured and sold by Advantec Toyo Kaisha, Ltd., Japan) to thereby obtain white solids and a filtrate. The white solids were washed 2 times with 20 ml of hexanol. The filtrate was transferred into a 1-liter eggplant-shaped flask and subjected to a distillation under heating in an oil bath at 160 °C and under reduced pressure. The resultant flask was subjected to distillation under heating and under reduced pressure. By the distillation, hexanol, tributyltin hexyloxide and dihexyl carbonate were recovered as a distillate. The yield of dihexyl carbonate was 13 percent. It was found that the distillate contained about 2 mmol of tributyltin hexyloxide.
Reference: [1] Patent: EP1535896, 2005, A1, . Location in patent: Page/Page column 30-31
[2] Patent: EP1535896, 2005, A1, . Location in patent: Page/Page column 31
  • 29
  • [ 105-58-8 ]
  • [ 111-27-3 ]
  • [ 60-29-7 ]
  • [ 64-17-5 ]
  • [ 5756-43-4 ]
  • [ 112-58-3 ]
  • [ 87494-31-3 ]
  • [ 7523-15-1 ]
Reference: [1] Catalysis Science and Technology, 2015, vol. 5, # 4, p. 2238 - 2250
  • 30
  • [ 105-58-8 ]
  • [ 111-27-3 ]
  • [ 7523-15-1 ]
Reference: [1] Zhurnal Fizicheskoi Khimii, 1953, vol. 27, p. 790[2] Chem.Abstr., 1955, p. 2828
[3] Uchenye Zapiski, Kazanskii Gosudarstvennyi Universitet, 1952, vol. 112, # 4, p. 35,100
  • 31
  • [ 6092-54-2 ]
  • [ 111-27-3 ]
  • [ 7523-15-1 ]
Reference: [1] Journal of the Chemical Society, 1952, p. 514,540
  • 32
  • [ 281-23-2 ]
  • [ 111-27-3 ]
  • [ 5001-18-3 ]
  • [ 99181-50-7 ]
YieldReaction ConditionsOperation in experiment
70% With hydrogenchloride; sodium hydroxide; sodium hypochlorite In water; ethyl acetate EXAMPLE 1
Into a 10-L five-necked jacketed flask equipped with a stirring device, a thermometer, a Dimroth condenser and a pH electrode, were charged 408 g (3 mol) of adamantane, 3000 mL of ethyl acetate, 20 g of ruthenium chloride n-hydrate (corresponding to 82 mmol of dihydrate) and 500 g of water.
After heating to 46° C, the pH was adjusted to 4.
Then, a 12percent aqueous solution of sodium hypochlorite was started to be added dropwise.
The dropping speed was regulated so as to add 4120 g (7.5 mol) of the aqueous solution of sodium hypochlorite over 400 min as calculated from the reaction rate previously measured.
The content of the free alkali in the aqueous solution of sodium hypochlorite was 0.5percent.
The reaction was continued by maintaining the pH of the reaction system at 4.0 to 4.5 by adding a 5percent hydrochloric acid in an amount equivalent to the free alkali in the aqueous solution of sodium hypochlorite.
During the reaction, the hypochlorite concentration in the water phase varied between 0.03 and 0.09 mmol/g.
After the addition of the sodium hypochlorite was completed, 80 g of a 25 wt percent NaOH aqueous solution and 3000 mL of hexanol were added to separate the reaction mixture into the organic phase and the water phase.
The gas chromatographic analysis on each phase showed that the conversion of adamantane was 100percent, the yield of 1-adanantanol was 9percent, the yield of 1,3-adamantanediol was 70percent, and the yield of 1,3,5-adamantanetriol was 14percent.
The ruthenium catalyst was recovered as black precipitates by filtering the water phase.
Reference: [1] Patent: US2002/40170, 2002, A1,
  • 33
  • [ 281-23-2 ]
  • [ 111-27-3 ]
  • [ 5001-18-3 ]
  • [ 99181-50-7 ]
Reference: [1] Patent: US2002/40170, 2002, A1,
  • 34
  • [ 95-48-7 ]
  • [ 108-46-3 ]
  • [ 111-27-3 ]
  • [ 136-77-6 ]
Reference: [1] Patent: US4108909, 1978, A,
  • 35
  • [ 62-53-3 ]
  • [ 111-27-3 ]
  • [ 33228-45-4 ]
Reference: [1] Journal of Experimental Medicine, 1934, vol. 59, p. 751,753,754
[2] Polish Journal of Chemistry, 1983, vol. 57, # 4/5/6, p. 593 - 596
[3] Molecular Crystals and Liquid Crystals (1969-1991), 1987, vol. 151, p. 233 - 242
  • 36
  • [ 589-87-7 ]
  • [ 111-27-3 ]
  • [ 30752-19-3 ]
Reference: [1] Journal of Organic Chemistry, 2008, vol. 73, # 19, p. 7814 - 7817
  • 37
  • [ 106-41-2 ]
  • [ 111-27-3 ]
  • [ 30752-19-3 ]
Reference: [1] ACS Catalysis, 2014, vol. 4, # 11, p. 3881 - 3885
  • 38
  • [ 700-13-0 ]
  • [ 111-27-3 ]
  • [ 148081-72-5 ]
Reference: [1] Chemical and Pharmaceutical Bulletin, 1994, vol. 42, # 3, p. 570 - 575
[2] Chemical and Pharmaceutical Bulletin, 1994, vol. 42, # 3, p. 576 - 579
  • 39
  • [ 131986-59-9 ]
  • [ 111-27-3 ]
  • [ 131986-45-3 ]
Reference: [1] Canadian Journal of Chemistry, 2010, vol. 88, # 12, p. 1222 - 1232
  • 40
  • [ 1295502-53-2 ]
  • [ 111-27-3 ]
  • [ 1190978-94-9 ]
Reference: [1] Journal of the American Chemical Society, 2017, vol. 139, # 35, p. 12175 - 12181
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