6582-52-1|2,2'-Methylenedianiline| Ambeed

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Quality Control of [ 6582-52-1 ] Purity: 95% SDS Specification

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Product Details of [ 6582-52-1 ]

CAS No. :	6582-52-1
Formula :	C₁₃H₁₄N₂
M.W :	198.26
SMILES Code :	NC1=CC=CC=C1CC2=CC=CC=C2N
MDL No. :	MFCD01109641
InChI Key :	OHKOAJUTRVTYSW-UHFFFAOYSA-N
Pubchem ID :	81061

Safety of [ 6582-52-1 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302
Precautionary Statements:	P280-P305+P351+P338

Application In Synthesis of [ 6582-52-1 ]

* 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 [ 6582-52-1 ]
Downstream synthetic route of [ 6582-52-1 ]

[ 6582-52-1 ] Synthesis Path-Upstream 1~15

1
[ 50-00-0 ]
[ 62-53-3 ]
[ 1208-52-2 ]
[ 6582-52-1 ]
[ 101-77-9 ]

Yield	Reaction Conditions	Operation in experiment
44.5%	Stage #1: at 25 - 80℃; Stage #2: at 45 - 140℃; for 2.5 - 2.83333 h; Stage #3: With sodium hydroxide In water at 100℃;	Example 1 a) Preparation of the polyamine mixture: In a stirred vessel, 2600 g of aniline were intimately mixed at 25°C with 1000 g of formalin (30 wt.percent aqueous solution), with stirring until the mixture warmed up to 60°C. The stirrer was stopped and the upper, aqueous phase was separated off. 68 g of 30 wt.percent aqueous hydrochloric acid were then admixed, with renewed stirring and cooling. The temperature was kept at 45°C. After stirring for a further 15 min at this temperature, the cooling was replaced by heating and the mixture was heated uniformly to 140°C over 120 min under 5 bar pressure and then kept at this temperature for 15 min. The mixture was then cooled to 100°C, let down to normal pressure and neutralized by adding 54 g of 50 wt.percent aqueous sodium hydroxide solution, with stirring. After the stirrer had been stopped, the phases were left to settle and the lower, aqueous phase was siphoned off. Excess aniline with residual water was then distilled off, initially under normal pressure, and the aniline residues were removed by distilling the resulting polyamine mixture at 100 mbar and 250°C. This yielded 1900 g of a polyamine mixture having the following composition: 4,4'-MDA: 60.1 wt.percent2,4'-MDA: 6.0 wt.percent2,2'-MDA: 0.2 wt.percenthigher-molecular polyamines: 33.7 wt.percent; Example 2 a) Preparation of the polyamine mixture: In a stirred vessel, 1800 g of aniline were intimately mixed at 30°C with 1000 g of formalin (30 wt.percent aqueous solution), with stirring. The mixture was warmed up to 80°C. The stirrer was stopped and the upper, aqueous phase was separated off. 23 g of 30 wt.percent aqueous hydrochloric acid were then admixed, with renewed stirring and cooling. The temperature was kept at 45°C. After stirring for a further 15 min at this temperature, the cooling was replaced by heating and the mixture was heated uniformly to 140°C over 150 min under 5 bar pressure and then kept at this temperature for 20 min. The mixture was then cooled to 100°C, let down to normal pressure and neutralized by adding 18 g of 50 wt.percent aqueous sodium hydroxide solution, with stirring. After the stirrer had been stopped, the phases were left to settle and the lower, aqueous phase was siphoned off. Excess aniline with residual water was then distilled off, initially under normal pressure, and the aniline residues were removed by distilling the resulting polyamine mixture at 100 mbar and 250°C. This gave 1880 g of a polyamine mixture having the following composition: 4,4'-MDA: 44.5 wt.percent2,4'-MDA: 7.3 wt.percent2,2'-MDA: 0.5 wt.percenthigher-molecular polyamines: 47.7 wt.percent

References: [1] Patent: EP1734035, 2006, A1, . Location in patent: Page/Page column 5-6.

2
[ 50-00-0 ]
[ 62-53-3 ]
[ 1208-52-2 ]
[ 6582-52-1 ]
[ 101-77-9 ]

References: [1] Patent: US2007/117997, 2007, A1, . Location in patent: Page/Page column 3; 4.
[2] Patent: US2007/265465, 2007, A1, . Location in patent: Page/Page column 4.
[3] Applied Catalysis A: General, 2011, vol. 398, # 1-2, p. 143 - 149.

3
[ 50-00-0 ]
[ 62-53-3 ]
[ 6582-52-1 ]
[ 101-77-9 ]

References: [1] Patent: US2009/240077, 2009, A1, . Location in patent: Page/Page column 6.

4
[ 21540-57-8 ]
[ 6582-52-1 ]

References: [1] Journal of Heterocyclic Chemistry, 1988, vol. 25, p. 1095 - 1098.
[2] Tetrahedron Letters, 1959, # 18, p. 5.
[3] Journal of the American Chemical Society, 1962, vol. 84, p. 1020,1025.
[4] Journal of the American Chemical Society, 1962, vol. 84, p. 1020 - 1026.
[5] Tetrahedron Letters, 1959, # 18, p. 5.

5
[ 26946-33-8 ]
[ 6582-52-1 ]

References: [1] Tetrahedron Letters, 1959, # 18, p. 5.
[2] Tetrahedron Letters, 1959, # 18, p. 5.
[3] Journal of the American Chemical Society, 1962, vol. 84, p. 1020 - 1026.

6
[ 50-00-0 ]
[ 98-95-3 ]
[ 62-53-3 ]
[ 1208-52-2 ]
[ 6582-52-1 ]
[ 101-77-9 ]

References: [1] Patent: US2006/183938, 2006, A1, . Location in patent: Page/Page column 4.

7
[ 50-00-0 ]
[ 142-04-1 ]
[ 1208-52-2 ]
[ 6582-52-1 ]
[ 101-77-9 ]

Yield	Reaction Conditions	Operation in experiment
66.75 %Chromat.	Stage #1: at 38 - 90℃; Stage #2: With sodium hydroxide In water	Example 1:; Hydrochloric acid (a concentration percentage by weight is 30.8percent, this hydrochloric acid is a by-product from MDI apparatus) from storage tank 2 and aniline from storage tank 3 are fed into venturi mixer 5 by a pump 6 with a molar ratio of hydrochloric acid/anilin=0.36:1, for mixing and reacting with each other to produce aniline hydrochloride which is then pumped into circulation pipes and mixed with a circulation solution coming from a condensation stirred vessel 1 to obtain a mixed solution. The obtained mixed solution is introduced into a heat exchanger 7 to remove the reaction heat, and the mixed solution, which is cooled to 38°C and left the heat exchanger 7, is introduced into a feeding port of the high gravity rotating bed reactor 8 of rotating packed bed type. Formaldehyde solution (a concentration percentage by weight is 37 wtpercent) stream from storage tank 4 is fed through another feeding port of the high gravity rotating bed reactor 8, the ratio of formaldehyde to aniline is controlled at 0.40:1. The formaldehyde solution is mixed sufficiently with the previously mixed solution phase and conducted a pre-condensation reaction in the high gravity rotating bed reactor 8, the reaction temperature is controlled at 35°C, the reaction time is 0.5 sec, and the rotation speed of the rotor of high gravity rotating bed reactor is 1000rpm. Then the mixed reaction solution flows into the condensation reaction vessel 1 to proceed with the pre-condensation reaction, the temperature of reaction solution is controlled at 42°C, the stirring speed is about 110rpm, and the reaction residence time is about 20 min. Then the temperature of reaction solution is elevated to over 90°C to conduct a molecular rearrangement reaction, the residence time for molecular rearrangement reaction is about 2 hours. Finally a solution of diphenylmethylene diamine hydrochloride and polymethylene polyphenyl polyamines hydrochloride is obtained. 92 vol percent of the reaction mixture from the condensation reaction vessel 1 returns to the circulation pipes, as circulation solution, and flows to heat exchanger 7, the other 8 vol percent of the reaction mixture is discharged and neutralized with a sodium hydroxide solution at a concentration of 42 wtpercent. The salt water phase is separated from the polyamine organic phase, and the polyamines are washed with water and purified to finally obtain a mixture of diphenylmethylene diamine and polymethylene polyphenyl polyamines. The composition of products is listed in table 2.

References: [1] Patent: EP2145874, 2010, A1, . Location in patent: Page/Page column 6.

8
[ 1092-56-4 ]
[ 6582-52-1 ]

References: [1] Journal of Heterocyclic Chemistry, 1969, vol. 6, p. 113 - 114.

9
[ 65177-64-2 ]
[ 6582-52-1 ]

References: [1] Journal of Heterocyclic Chemistry, 1988, vol. 25, p. 1095 - 1098.

10
[ 256-91-7 ]
[ 6582-52-1 ]

References: [1] Tetrahedron Letters, 1959, # 18, p. 5.

11
[ 2225-56-1 ]
[ 6582-52-1 ]
[ 256-91-7 ]

References: [1] Tetrahedron Letters, 1959, # 18, p. 5.

12
[ 1208-52-2 ]
[ 6582-52-1 ]
[ 101-77-9 ]

References: [1] Tetrahedron Letters, 1986, vol. 27, # 17, p. 1887 - 1890.

13
[ 101-77-9 ]
[ 1208-52-2 ]
[ 6582-52-1 ]

References: [1] Tetrahedron Letters, 1986, vol. 27, # 17, p. 1887 - 1890.

14
[ 50-00-0 ]
[ 62-53-3 ]
[ 1208-52-2 ]
[ 6582-52-1 ]
[ 26628-67-1 ]
[ 101-77-9 ]

References: [1] Journal fuer Praktische Chemie (Leipzig), 1986, vol. 328, # 1, p. 142 - 148.

15
[ 21540-57-8 ]
[ 6582-52-1 ]
[ 70035-91-5 ]

References: [1] Collection of Czechoslovak Chemical Communications, 1983, vol. 48, # 2, p. 364 - 378.
[2] Collection of Czechoslovak Chemical Communications, 1983, vol. 48, # 2, p. 364 - 378.

[ 6582-52-1 ] Synthesis Path-Downstream 1~31

1
[ 21540-57-8 ]
[ 6582-52-1 ]

References: [1]Journal of Heterocyclic Chemistry,1988,vol. 25,p. 1095 - 1098.
[2]Tetrahedron Letters,1959,p. 5.
[3]Journal of the American Chemical Society,1962,vol. 84,p. 1020 - 1026.
[4]Tetrahedron Letters,1959,p. 5.

Yield	Reaction Conditions	Operation in experiment
		Methylenedianiline (III) A solution of 59.5 g (0.3 mol) of methylenedianaline (III) in 1200 ml of N,N-dimethylacetamide is cooled to 0 C. and 64.8 g (0.1 mol) of the trisanhydride I is added over 1.5 hrs. in 10 g portions under N2 with vigorous stirring while the temperature is maintained below 0 C. 177.8 g (0.3 mol) of the monoanhydride II is then added and the reaction mixture stirred overnight at room temperature. To the resulting solution, 500 ml of toluene is added and the mixture refluxed with a Dean-Stark trap for 3 hrs. Then, the toluene is distilled off and the solution heated at 163-165 for 5 hrs. After cooling, the solution is precipitated in 5 lt of methanol and the obtained yellow powder is dried in a vacuum-oven. The yield of the polyimide-ester is 178 g. The polymer exhibits a Tg of 223 C. (determined by DSC) and an intrinsic viscosity of 0.08 dl/g (NMP, 25 C.). The polyimide-ester undergoes polymerization upon heating to 300 C.

3
[ 6582-52-1 ]
[ 105-53-3 ]
[ 2121-66-6 ]

References: [1]Chemische Berichte,1898,vol. 31,p. 2593.
Chemisches Zentralblatt,1898,vol. 69,p. 695.

4
[ 2225-56-1 ]
[ 6582-52-1 ]
[ 256-91-7 ]

References: [1]Tetrahedron Letters,1959,p. 5.

5
[ 1208-52-2 ]
[ 6582-52-1 ]
[ 101-77-9 ]

References: [1]Tetrahedron Letters,1986,vol. 27,p. 1887 - 1890.

6
[ 21540-57-8 ]
[ 6582-52-1 ]
[ 70035-91-5 ]

References: [1]Collection of Czechoslovak Chemical Communications,1983,vol. 48,p. 364 - 378.
[2]Collection of Czechoslovak Chemical Communications,1983,vol. 48,p. 364 - 378.

7
[ 6582-52-1 ]
[ 119346-85-9 ]

References: [1]Journal of Heterocyclic Chemistry,1988,vol. 25,p. 1095 - 1098.

8
[ 101-77-9 ]
[ 1208-52-2 ]
[ 6582-52-1 ]

References: [1]Tetrahedron Letters,1986,vol. 27,p. 1887 - 1890.

9
[ 50-00-0 ]
[ 62-53-3 ]
[ 1208-52-2 ]
[ 6582-52-1 ]
[ 26628-67-1 ]
[ 101-77-9 ]

References: [1]Journal fur praktische Chemie (Leipzig 1954),1986,vol. 328,p. 142 - 148.

10
[ 6582-52-1 ]
[ 1034-39-5 ]
[ 159428-07-6 ]

References: [1]Journal of Organic Chemistry,1994,vol. 59,p. 7306 - 7315.

11
[ 1092-56-4 ]
[ 6582-52-1 ]

References: [1]Journal of Heterocyclic Chemistry,1969,vol. 6,p. 113 - 114.

13
[ 6582-52-1 ]
N-(N',N'-Diethylthiocarbamoyl)benzimidoylchlorid [ No CAS ]
2,2'-Bis[N-(diethylaminothiocarbonyl)]benzamidino-N'-yl}diphenylmethan [ No CAS ]

References: [1]Zeitschrift fur Naturforschung, B: Chemical Sciences,2000,vol. 55,p. 253 - 261.

14
[ 6582-52-1 ]
[ 119346-93-9 ]

References: [1]Journal of Heterocyclic Chemistry,1988,vol. 25,p. 1095 - 1098.

15
[ 6582-52-1 ]
[ 119346-89-3 ]

References: [1]Journal of Heterocyclic Chemistry,1988,vol. 25,p. 1095 - 1098.

16
[ 101-77-9 ]
sodium sulfide [ No CAS ]
[ 6582-52-1 ]

References: [1]Journal of Heterocyclic Chemistry,1988,vol. 25,p. 1095 - 1098.

17
[ 65177-64-2 ]
[ 6582-52-1 ]

References: [1]Journal of Heterocyclic Chemistry,1988,vol. 25,p. 1095 - 1098.

18
[ 26946-33-8 ]
[ 6582-52-1 ]

References: [1]Tetrahedron Letters,1959,p. 5.
[2]Tetrahedron Letters,1959,p. 5.
[3]Journal of the American Chemical Society,1962,vol. 84,p. 1020 - 1026.

19
[ 256-91-7 ]
[ 6582-52-1 ]

References: [1]Tetrahedron Letters,1959,p. 5.

20
[ 1208-52-2 ]
[ 6582-52-1 ]
[ 26628-67-1 ]
[ 101-77-9 ]
2,4'-methylene-dicyclohexyldiamine [ No CAS ]
[ 648900-91-8 ]
[ 1761-71-3 ]
[ 70906-77-3 ]

References: [1]Patent: WO2004/7425,2004,A2 .Location in patent: Page 9-12.
[2]Patent: WO2004/7425,2004,A2 .Location in patent: Page 9-12.

21
[ 50-00-0 ]
[ 98-95-3 ]
[ 62-53-3 ]
[ 1208-52-2 ]
[ 6582-52-1 ]
[ 101-77-9 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; at 35 - 103℃; for 11.0833h;Heating / reflux;	Methanol and water were separated from this mixture by distillation. The remaining distillation bottom product (479.0 g) was tempered in a glass stirring apparatus with superimposition of nitrogen at 35 C. At this temperature, 11.4 g of 32.7% hydrochloric acid were added dropwise within 5 min. During this process the temperature was kept at 35 C. by an ice bath and stirring was continued at this temperature for 30 min. The mixture was then heated to 60 C. and stirring continued at this temperature for a further 30 min. The reaction charge was then heated to boiling and refluxed at boiling temperature (103 C.) for 10 h. 14.9 g 32% sodium hydroxide solution and 100 g of distilled water were then added and the two-phase mixture formed was thoroughly intermixed for 15 minutes. The phases were then separated and the organic phase was extracted twice more with 100 g distilled water each time. Excess aniline and also water and nitrobenzene were distilled off from the organic phase in a vacuum (0.1 mbar). The bottom temperature at the end of distillation was 215 C. The MDA produced (=distillation bottom product, 75.0 g) had the following composition: Wt. % Aniline - Nitrobenzene - 4,4'-MDA 38.6 2,4'-MDA 4.46 2,2'-MDA 0.3 N-methyl-MDA 0.65 3-core-MDA 19.9 4-core-MDA 11.2 Higher MDA oligomers 15.3 Other secondary components and unknown 9.59

References: [1]Patent: US2006/183938,2006,A1 .Location in patent: Page/Page column 4.

22
[ 50-00-0 ]
[ 62-53-3 ]
polyamines [ No CAS ]
[ 1208-52-2 ]
[ 6582-52-1 ]
[ 101-77-9 ]

Yield	Reaction Conditions	Operation in experiment
33.7 - 47.7%; 6.0 - 7.3%; 0.2 - 0.5%; 44.5 - 60.1%		Example 1 a) Preparation of the polyamine mixture: In a stirred vessel, 2600 g of aniline were intimately mixed at 25C with 1000 g of formalin (30 wt.% aqueous solution), with stirring until the mixture warmed up to 60C. The stirrer was stopped and the upper, aqueous phase was separated off. 68 g of 30 wt.% aqueous hydrochloric acid were then admixed, with renewed stirring and cooling. The temperature was kept at 45C. After stirring for a further 15 min at this temperature, the cooling was replaced by heating and the mixture was heated uniformly to 140C over 120 min under 5 bar pressure and then kept at this temperature for 15 min. The mixture was then cooled to 100C, let down to normal pressure and neutralized by adding 54 g of 50 wt.% aqueous sodium hydroxide solution, with stirring. After the stirrer had been stopped, the phases were left to settle and the lower, aqueous phase was siphoned off. Excess aniline with residual water was then distilled off, initially under normal pressure, and the aniline residues were removed by distilling the resulting polyamine mixture at 100 mbar and 250C. This yielded 1900 g of a polyamine mixture having the following composition: 4,4'-MDA: 60.1 wt.%2,4'-MDA: 6.0 wt.%2,2'-MDA: 0.2 wt.%higher-molecular polyamines: 33.7 wt.%; Example 2 a) Preparation of the polyamine mixture: In a stirred vessel, 1800 g of aniline were intimately mixed at 30C with 1000 g of formalin (30 wt.% aqueous solution), with stirring. The mixture was warmed up to 80C. The stirrer was stopped and the upper, aqueous phase was separated off. 23 g of 30 wt.% aqueous hydrochloric acid were then admixed, with renewed stirring and cooling. The temperature was kept at 45C. After stirring for a further 15 min at this temperature, the cooling was replaced by heating and the mixture was heated uniformly to 140C over 150 min under 5 bar pressure and then kept at this temperature for 20 min. The mixture was then cooled to 100C, let down to normal pressure and neutralized by adding 18 g of 50 wt.% aqueous sodium hydroxide solution, with stirring. After the stirrer had been stopped, the phases were left to settle and the lower, aqueous phase was siphoned off. Excess aniline with residual water was then distilled off, initially under normal pressure, and the aniline residues were removed by distilling the resulting polyamine mixture at 100 mbar and 250C. This gave 1880 g of a polyamine mixture having the following composition: 4,4'-MDA: 44.5 wt.%2,4'-MDA: 7.3 wt.%2,2'-MDA: 0.5 wt.%higher-molecular polyamines: 47.7 wt.%

References: [1]Patent: EP1734035,2006,A1 .Location in patent: Page/Page column 5-6.

23
[ 75-44-5 ]
polyamines [ No CAS ]
[ 1208-52-2 ]
[ 6582-52-1 ]
[ 101-77-9 ]
polyisocyanates [ No CAS ]
[ 2536-05-2 ]
[ 5873-54-1 ]
[ 101-68-8 ]

Yield	Reaction Conditions	Operation in experiment
35 - 48.2%; 0.2 - 0.5%; 5.5 - 7.2%; 44.1 - 59.3%	In chlorobenzene; at 0℃;Product distribution / selectivity;	b) Preparation of the polyisocyanate mixture: In another stirred reactor, the 1900 g of polyamine mixture were dissolved in 5700 g of chlorobenzene. In a second vessel, a 33 wt.% phosgene solution was prepared by dissolving 3800 g of phosgene in 7600 g of chlorobenzene, with cooling to 0C, and mixing the amine and phosgene solutions with vigorous stirring. The solid suspension formed was then heated slowly and the hydrogen chloride gas produced was withdrawn in appropriate manner. This gave a homogeneous solution of the polyisocyanate. The solvent was then separated off by distillation to give 2370 g of a polyisocyanate mixture having the following composition: 4,4'-MDI: 59.3 wt.%2,4'-MDI: 5.5 wt.%2,2'-MDI: 0.2 wt.%higher-molecular polyisocyanates: 35 wt.% This mixture had a crystallization point below 20C and was suitable for transportation in large barrels and tankers.; b) Preparation of the polyisocyanate mixture: The polyamine mixture was reacted with phosgene in chlorobenzene in the same manner as described in Example 1 to give the polyisocyanate mixture. This gave 2330 g of a polyisocyanate mixture having the following composition: 4,4'-MDI: 44.1 wt.%2,4'-MDI: 7.2 wt.%2,2'-MDI: 0.5 wt.%higher-molecular polyisocyanates: 48.2 wt.% This first polyisocyanate mixture was distilled in a pot still at 10 mbar pressure and 215C bottom temperature until 280 g of distillate had been obtained. This distillate was back-mixed with 420 g of the remaining bottom product. This gave 700 g of a second polyisocyanate mixture having the following composition: 4,4'-MDI: 57.4 wt.%2,4'-MDI: 9.0 wt.%2,2'-MDI: 0.5 wt.%higher-molecular polyisocyanates: 33.1 wt.% This mixture had a crystallization point below 20C and was suitable for transportation in large barrels and tankers.

References: [1]Patent: EP1734035,2006,A1 .Location in patent: Page/Page column 5-6.

24
[ 50-00-0 ]
[ 62-53-3 ]
[ 1208-52-2 ]
[ 6582-52-1 ]
[ 101-77-9 ]

Yield	Reaction Conditions	Operation in experiment
		Example 1; a) Production of a Mixture of Di- and Polyamines; 2,600 g of aniline was mixed intensively with 1,000 g of formalin (30 wt. % aqueous solution of formaldehyde, based on the weight of the solution) in a stirred vessel at 25 C., with stirring, during which the mixture heated up to 60 C. The stirrer was turned off and the aqueous phase settling out at the top was separated off. 680 g of 30 wt. % aqueous hydrochloric acid was mixed in, while stirring again and cooling, maintaining a temperature of 45 C. After stirring at this temperature for a further 15 min, the cooling was replaced by heating and the mixture was uniformly heated to 140 C. in the course of 120 min under 5 bar pressure, and was maintained at this temperature for 15 min. The mixture was cooled to 100 C., depressurized to normal pressure and neutralized by adding 540 g of 50 wt. % aqueous sodium hydroxide solution, while stirring. After turning off the stirrer, the phases were left to settle and the lower aqueous phase was removed by suction. Excess aniline was distilled off with residual water, initially under normal pressure, and the aniline residues were removed by starting to distil the polyamine mixture obtained at 100 mbar and 250 C. 1,900 g of a mixture of di- and polyamines of the following composition were obtained: 4,4-MDA: 60.1 wt. %, 2,4'-MDA: 6.0 wt. %, 2,2'-MDA: 0.2 wt. %, higher molecular weight polyamines: 33.7 wt. %, based on the weight of the mixture.; Example 2; a) Production of a Mixture of Di- and Polyamines; 1,800 g of aniline were mixed intensively with 1,000 g of formalin (30 wt. % aqueous solution of formaldehyde, based on the weight of the solution) in a stirred vessel at 30 C., with stirring, during which the mixture heated up to 80 C. The stirrer was turned off and the aqueous phase settling out at the top was separated off. 230 g of 30 wt. % aqueous hydrochloric acid were mixed in, while stirring again and cooling, maintaining a temperature of 45 C. After stirring at this temperature for a further 15 min, the cooling was replaced by heating and the mixture was uniformly heated to 140 C. in the course of 150 min under 5 bar pressure, and was maintained at this temperature for 20 min. The mixture was cooled to 100 C., depressurized to normal pressure and neutralized by adding 180 g of 50 wt. % aqueous sodium hydroxide solution, while stirring. After turning off the stirrer, the phases were left to settle and the lower aqueous phase was withdrawn by suction. Excess aniline was distilled off with residual water, initially under normal pressure, and the aniline residues were removed by starting to distil the polyamine mixture obtained at 100 mbar and 250 C. 1880 g of a mixture of di- and polyamines of the following composition were obtained: 4,4'-MDA: 44.5 wt. %, 2,4'-MDA: 7.3 wt. %, 2,2'-MDA: 0.5 wt. %, higher molecular weight polyamines: 47.7 wt. %, based on the weight of the mixture.
		In a stirred vessel, 2600 g aniline were thoroughly mixed with 1000 g formalin (30 wt. % aqueous solution of formaldehyde, based on the weight of the solution) at 25 C., with stirring, during which the mixture heated up to 60 C. The stirrer was turned off and the aqueous phase settling out at the top was separated off. 68 g of 30 wt. % aqueous hydrochloric acid were then mixed in, while stirring again and cooling, maintaining a temperature of 45 C. After continuing to stir at this temperature for 15 min, the cooling was replaced by heating and the mixture was uniformly heated to 140 C. in the course of 120 min under a pressure of 5 bar, and was then kept at this temperature for 15 min.The mixture was then cooled to 100 C., depressurized to normal pressure and neutralized by adding 54 g of 50 wt. % aqueous sodium hydroxide solution while stirring. After turning off the stirrer, the phases were allowed to settle and the aqueous phase at the bottom was sucked off. Excess aniline was then distilled off with residual water that remained, initially under normal pressure, and the aniline residues were removed by incipient distillation, at 100 mbar and 250 C., of the polyamine mixture obtained.1900 g of a mixture of diamines and polyamines of the following composition were obtained:4,4'-MDA: 60.1 wt. %2,4'-MDA: 6.0 wt. %2,2'-MDA: 0.2 wt. %higher molecular weight polyamines: 33.7 wt. %, based in each case on the weight of the mixture.

References: [1]Patent: US2007/117997,2007,A1 .Location in patent: Page/Page column 3; 4.
[2]Patent: US2007/265465,2007,A1 .Location in patent: Page/Page column 4.
[3]Applied Catalysis A: General,2011,vol. 398,p. 143 - 149.

25
[ 75-44-5 ]
[ 1208-52-2 ]
[ 6582-52-1 ]
[ 101-77-9 ]
[ 2536-05-2 ]
[ 5873-54-1 ]
[ 101-68-8 ]

Yield	Reaction Conditions	Operation in experiment
	In chlorobenzene; at 0℃;Heating / reflux;Product distribution / selectivity;	b) Production of a Mixture of Di- and Polyisocyanates; The 1,900 g of the mixture of di- and polyamines obtained in Example 1 a) were dissolved in 5,700 g of chlorobenzene in another stirred reactor. In a second vessel, a 33 wt. % (based on the weight of the solution) phosgene solution was prepared by dissolving 3,800 g of phosgene in 7,600 g of chlorobenzene, while cooling to 0 C., and the amine and phosgene solutions were mixed while stirring intensively. The resulting suspension of solids was heated slowly with the formation of hydrogen chloride gas, which was withdrawn in a suitable manner. A homogeneous solution of polyisocyanate was formed during this process. The solvent was separated off by distillation, which resulted in 2,370 g of a mixture of di- and polyisocyanates of the following composition being obtained: 4,4'-MDI: 59.3 wt. %, 2,4'-MDI: 5.5 wt. %, 2,2'-MDI: 0.2 wt. %, higher molecular weight polyisocyanates: 35 wt. %, based on the weight of the mixture.; b) Production of the Polyisocyanate Mixture; The mixture of di- and polyamines obtained in Example 2 a) was reacted with phosgene in chlorobenzene in the same way as described in Example 1, with the same molar ratio of phosgene to amino groups as in Example 1, to form the polyisocyanate mixture. 2,330 g of a polyisocyanate mixture of the following composition were obtained: 4,4'-MDI: 44.1 wt. %, 2,4'-MDI: 7.2 wt. %, 2,2'-MDI: 0.5 wt. %, higher molecular weight polyisocyanates: 48.2 wt. %, based on the weight of the mixture.
	In chlorobenzene; at 0℃;Industry scale;Product distribution / selectivity;	In a stirred reactor, 1900 g of the mixture of diamines and polyamines obtained in Example 1 were dissolved in 5700 g chlorobenzene with a content of 200 ppm phosgene and 200 ppm MDI, based in each case on the weight of the solvent chlorobenzene. In a second vessel made of stainless steel (DIN 1.4571), a 33 wt. % (based on the weight of the solution) phosgene solution was prepared by dissolving 3800 g phosgene in 7600 g chlorobenzene while cooling to 0 C., and the amine and phosgene solutions were mixed while stirring intensively. The resulting suspension of solids was then heated slowly with the formation of hydrogen chloride gas, which was withdrawn by suitable means. During this process, a homogeneous solution of the polyisocyanate was formed. The solvent was now separated off by distillation, as a result of which 2370 g of a mixture of diisocyanates and polyisocyanates of the following composition was obtained:4,4'-MDI: 59.2 wt. %2,4'-MDI: 5.4 wt. %2,2'-MDI: 0.2 wt. %higher molecular weight polyisocyanates: 35.2 wt. %, based in each case on the weight of the mixture.Acidity (ASTM D 1638-74): 180 ppmIron content: 10 ppmExtinction of a 2% solution in chlorobenzene (wavelength 430 nm, film thickness 10 mm): 0.27 Example 3 (Production of a Mixture of Diisocyanates and Polyisocyanates Using Pure Solvent (According to the Invention))In a stirred reactor, 1900 g of the mixture of diamines and polyamines obtained in Example 1 were dissolved in 5700 g chlorobenzene with a content of 20 ppm phosgene and 20 ppm MDI, based in each case on the weight of the solvent chlorobenzene. In a second vessel made of stainless steel (DIN 1.4571), a 33 wt. % (based on the weight of the solution) phosgene solution was prepared by dissolving 3800 g phosgene in 7600 g chlorobenzene while cooling to 0 C., and the amine and phosgene solutions were mixed into this while stirring intensively. The resulting suspension of solids was then heated slowly with the formation of hydrogen chloride gas, which was withdrawn by suitable means. During this process, a homogeneous solution of the polyisocyanate was formed. The solvent was then separated off by distillation, as a result of which 2370 g of a mixture of diisocyanates and polyisocyanates of the following composition was obtained:4,4'-MDI: 59.3 wt. %2,4'-MDI: 5.5 wt. %2,2'-MDI: 0.2 wt. %higher molecular weight polyisocyanates: 35 wt. %, based in each case on the weight of the mixture.Acidity (ASTM D 1638-74): 62 ppmIron content: 4 ppmExtinction of a 2% solution in chlorobenzene (wavelength 430 nm, film thickness 10 mm): 0.13Thus, when the results of Examples 2 and 3 are compared, it is shown that the use of purified solvent for the production of the amine solution in accordance with the process of the present invention results in an isocyanate being obtained with improved quality, which is expressed as a low acidity, a low iron content and a light color (low extinction).

References: [1]Patent: US2007/117997,2007,A1 .Location in patent: Page/Page column 3-4.
[2]Patent: US2007/265465,2007,A1 .Location in patent: Page/Page column 4-5.

26
tetrachloro(η-pentamethylcyclopentadienyl)tungsten(V) [ No CAS ]
[ 6582-52-1 ]
[WCl(C₅(CH₃)5)(NC₆H₄CH₂C₆H₄N)] [ No CAS ]

References: [1]Journal of the Chemical Society, Dalton Transactions,1997,p. 3343 - 3347.

27
sodium molybdate [ No CAS ]
[ 75-77-4 ]
[ 110-71-4 ]
[ 6582-52-1 ]
[MoCl₂(C₄H₁₀O₂)(NC₆H₄CH₂C₆H₄N)] [ No CAS ]

References: [1]Journal of the Chemical Society, Dalton Transactions,1996,p. 4513 - 4516.

28
[ 50-00-0 ]
[ 62-53-3 ]
[ 6582-52-1 ]
[ 101-77-9 ]

Yield	Reaction Conditions	Operation in experiment
	hydrogenchloride; In water; cyclohexanone; at 35 - 80℃;	134 g of a 32 wt. % aqueous formaldehyde solution were added dropwise within 20 minutes, while stirring at 80 C., to 279 g of pure aniline (i.e. aniline containing no measurable amounts of compounds which contain at least one carbonyl group or of compounds formed by reaction of these compounds containing at least one carbonyl group with aniline), to which cyclohexanol, cyclohexanone or N-phenylcyclohexylimine was optionally added (see Table 1). Following the addition, stirring was continued for an additional 5 minutes and a phase separation was performed at 80 C. 91 g of a 30 wt. % aqueous hydrochloric acid were then added to the organic phase, the aminal, within 30 minutes while stirring at 35 C. After stirring for 30 minutes at 35 C., the reaction mixture was heated to 60 C. and stirring was continued for a further 30 minutes at 60 C. The reaction temperature was then raised to 104 C. The reaction mixture was then stirred for a further 10 hours at this temperature to complete the reaction.72 g of a 50 wt. % sodium hydroxide solution and 100 g of water were added to the acid reaction mixture produced in the manner described above, in a stirred-tank reactor at a temperature of 95 to 100 C. while stirring. The two-phase mixture that forms was stirred for a further 15 minutes or so at 95 to 100 C. After separating off the aqueous phase, the organic phase was washed twice with 300 ml of boiling distilled water by heating to reflux temperature for approx. 5 minutes with stirring after adding the water and then separating off the aqueous phase.After the second washing cycle, the organic phase was transferred to a distillation apparatus. Water and aniline were distilled off in the water jet vacuum (approx. 20 mbar). Distillation was stopped when the bottom temperature reaches approx. 280 C. and binuclear MDA begins to distil. The bottoms (product) were cooled, and after venting the distillation apparatus with nitrogen, were transferred to a storage vessel and stored under nitrogen. The MDA obtained had a content of 2-ring MDA (i.e. MMDA, sum of 4,4'-MDA, s,4'-MDA and 2,2'-MDA) of approx. 63%.
7.5%Chromat.; 54.3%Chromat.		General procedure: In a continuous reaction process, 23.20 t/h of feed aniline (containing 90.0% by mass of aniline, 1) and 9.60 t/h of 32% aqueous formaldehyde solution (corresponding to a molar ratio of aniline (1):formaldehyde (2) of 2.25:1) are mixed and converted to the aminal (3) at a temperature of 90.0 C. and a pressure of 1.40 bar (absolute) in a stirred reaction tank (1000). The reaction tank is provided with a cooler having a cooling circuit pump. The reaction mixture leaving the reaction tank is guided into a phase separation apparatus (aminal separator, 2000) (step (A-I)). After the phase separation to remove the aqueous phase (6), the organic phase (5) is admixed in a mixing nozzle with 30% aqueous hydrochloric acid (7) (protonation level 10%, i.e. 0.10 mol of HCl is added per mole of amino groups) and run into the first rearrangement reactor (3000-1). The first rearrangement reactor (called ?vacuum tank?) is operated at 50.0 C., which is ensured by means of evaporative cooling in a reflux condenser at a pressure of 104 mbar (absolute). The reflux condenser is charged with 0.50 t/h of fresh aniline. The rearrangement reaction is conducted to completion in a reactor cascade composed of a total of seven reactors at 50.0 C. to 156.0 C. (i.e. 50.0 C. in reactor 3000-1/60.0 C. in reactor 3000-2/83.0 C. in reactor 3000-3/ 104.0 C. in reactor 3000-4/119.0 C. in reactor 3000-5/148.0 C. in reactor 3000-6/156.0 C. in reactor 3000-7) (step (A-II)). On completion of reaction, the reaction mixture (8-i) obtained is admixed with 32% sodium hydroxide solution in a molar ratio of 1.10:1 sodium hydroxide to HCl and reacted in a stirred neutralization vessel (4000) (step (B-I)). The temperature here is 115.0 C. The absolute pressure is 1.40 bar. The neutralized reaction mixture (10) is then separated in a neutralization separator (5000) into an aqueous lower phase (12), which is guided to a wastewater collection vessel, and into an organic phase (11) (step (B-II)). The organic upper phase (11) is guided to the washing and washed with condensate (13) in a stirred washing vessel (6000) (step (B-III)). After the washing water (15) has been separated from the biphasic mixture (14) obtained in the washing vessel (6000) in a washing water separator (7000, step (B-IV)), the crude MDA (16) thus obtained is freed of water and aniline (removed together as stream 17) by distillation, and 17.00 t/h of MDA (18) were obtained as bottom product (step (B-V)). MDA prepared in this way has an average composition of 45.2% 4,4?-MDA, 5.5% 2,4?-MDA, 0.3% 2,2?-MDA, i.e. a total bicyclic content of 51.0% and also 0.3% N-methyl-4,4?-MDA and 0.3% N-formyl-4,4?-MDA, the remainder to 100% consisting essentially of higher homologs (PMDA) and isomers thereof.

References: [1]Patent: US2009/240077,2009,A1 .Location in patent: Page/Page column 6.
[2]Patent: US2020/115318,2020,A1 .Location in patent: Paragraph 0136-0167.

29
[ 75-44-5 ]
[ 6582-52-1 ]
[ 101-77-9 ]
[ 2536-05-2 ]
[ 101-68-8 ]

Yield	Reaction Conditions	Operation in experiment
	In chlorobenzene;Heating;	MDA obtained by acid-catalysed condensation of aniline with formaldehyde according to the general procedure above Anhydrous chlorobenzene Phosgene 50 g of the MDA prepared according to the above process was dissolved in 255 ml of chlorobenzene, heated to 55 C. and poured into a solution of 105 g of phosgene in 310 ml of chlorobenzene at a temperature of 0 C. within 10 s with intensive stirring. The suspension was heated to 100 C. within 45 minutes by passing through phosgene and then heated to reflux temperature for 10 minutes. After a further 10 minutes at this temperature, the solvent was distilled off under reduced pressure down to a bottom temperature of 100 C. The crude isocyanate was then heated in a distillation apparatus at a pressure of 4 to 6 mbar by means of a hot air blower until the first product starts distilling and then cooled to room temperature within 5 to 10 minutes. Of the isocyanate obtained in this way, 1.0 g was dissolved in chlorobenzene and diluted with chlorobenzene to 50 ml. The absorption of the solution obtained in this way was determined at the two wavelengths of 430 nm and 520 nm. A Dr. Lange LICO 300 photometer was used as the measuring instrument. The results are summarized in Table 1.

References: [1]Patent: US2009/240077,2009,A1 .Location in patent: Page/Page column 6-7.

30
[ 50-00-0 ]
[ 142-04-1 ]
[ 1208-52-2 ]
[ 6582-52-1 ]
[ 101-77-9 ]

Yield	Reaction Conditions	Operation in experiment
4.30%Chromat.; 0.085%Chromat.; 66.75%Chromat.		Example 1:; Hydrochloric acid (a concentration percentage by weight is 30.8%, this hydrochloric acid is a by-product from MDI apparatus) from storage tank 2 and aniline from storage tank 3 are fed into venturi mixer 5 by a pump 6 with a molar ratio of hydrochloric acid/anilin=0.36:1, for mixing and reacting with each other to produce aniline hydrochloride which is then pumped into circulation pipes and mixed with a circulation solution coming from a condensation stirred vessel 1 to obtain a mixed solution. The obtained mixed solution is introduced into a heat exchanger 7 to remove the reaction heat, and the mixed solution, which is cooled to 38C and left the heat exchanger 7, is introduced into a feeding port of the high gravity rotating bed reactor 8 of rotating packed bed type. Formaldehyde solution (a concentration percentage by weight is 37 wt%) stream from storage tank 4 is fed through another feeding port of the high gravity rotating bed reactor 8, the ratio of formaldehyde to aniline is controlled at 0.40:1. The formaldehyde solution is mixed sufficiently with the previously mixed solution phase and conducted a pre-condensation reaction in the high gravity rotating bed reactor 8, the reaction temperature is controlled at 35C, the reaction time is 0.5 sec, and the rotation speed of the rotor of high gravity rotating bed reactor is 1000rpm. Then the mixed reaction solution flows into the condensation reaction vessel 1 to proceed with the pre-condensation reaction, the temperature of reaction solution is controlled at 42C, the stirring speed is about 110rpm, and the reaction residence time is about 20 min. Then the temperature of reaction solution is elevated to over 90C to conduct a molecular rearrangement reaction, the residence time for molecular rearrangement reaction is about 2 hours. Finally a solution of diphenylmethylene diamine hydrochloride and polymethylene polyphenyl polyamines hydrochloride is obtained. 92 vol% of the reaction mixture from the condensation reaction vessel 1 returns to the circulation pipes, as circulation solution, and flows to heat exchanger 7, the other 8 vol% of the reaction mixture is discharged and neutralized with a sodium hydroxide solution at a concentration of 42 wt%. The salt water phase is separated from the polyamine organic phase, and the polyamines are washed with water and purified to finally obtain a mixture of diphenylmethylene diamine and polymethylene polyphenyl polyamines. The composition of products is listed in table 2.

References: [1]Patent: EP2145874,2010,A1 .Location in patent: Page/Page column 6.

31
[ 6582-52-1 ]
[ 260-94-6 ]
[ 92-81-9 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; aniline; In water; at 160 - 180℃;	In a series of experiments, the amount of aqueous 30% hydrochloric acid required in each case to achieve the desired protonation level (see table 3 below) was added to a 2,2?-MDA solution in aniline preheated to 100.0 C. The 2,2?-MDA concentration in each of the individual experiments was 1.0% by mass; in addition, the solutions contained octadecane as an internal standard for gas chromatography (GC) analysis. The resulting mixture was transferred as quickly as possible by means of a peristaltic pump to a Buechi glass autoclave preheated to 120.0 C. and heated to the reaction temperature envisaged (see table 3). On attainment of the desired reaction temperature, the first sample was taken (time=zero). In order to monitor the progress of the reaction, further samples were taken after 30, 60, 120 and 240 minutes and analyzed by means of GC analysis. Reaction conditions and experimental results are collated in table 3 below. It is found that, with rising temperature and rising hydrochloric acid concentration, the formation of the acridine and acridane secondary components from 2,2?-MDA occurs to an increased degree.
	With hydrogenchloride; In water; at 100 - 170℃; for 4h;Autoclave;	General procedure: In a series of experiments, the amount of aqueous 30% hydrochloric acid required in each case to achieve the desired protonation level (see table 3 below) was added to a 2,2?-MDA solution in aniline preheated to 100.0 C. The 2,2?-MDA concentration in each of the individual experiments was 1.0% by mass; in addition, the solutions contained octadecane as an internal standard for gas chromatography (GC) analysis. The resulting mixture was transferred as quickly as possible by means of a peristaltic pump to a Blichi glass autoclave preheated to 120.0 C. and heated to the reaction temperature envisaged (see table 3). On attainment of the desired reaction temperature, the first sample was taken (time=zero). In order to monitor the progress of the reaction, further samples were taken after 30, 60, 120 and 240 minutes and analyzed by means of GC analysis.

References: [1]Patent: US2020/87243,2020,A1 .Location in patent: Paragraph 0160-0161.
[2]Patent: US2020/115318,2020,A1 .Location in patent: Paragraph 0168-0170.

Historical Records

Technical Information

• Buchwald-Hartwig C-N Bond and C-O Bond Formation Reactions • Chan-Lam Coupling Reaction • Hydride Reductions • Leuckart-Wallach Reaction • Mannich Reaction • Petasis Reaction • Preparation of Amines • Reactions of Amines • Reactions of Benzene and Substituted Benzenes • Specialized Acylation Reagents-Vilsmeier Reagent • Ugi Reaction

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[ 6582-52-1 ]

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2,2'-(Ethane-1,2-diyl)dianiline

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H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

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CAS No.: 6582-52-1

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