Adipoyl chloride synthesis
- Product Name:Adipoyl chloride
- CAS Number:111-50-2
- Molecular formula:C6H8Cl2O2
- Molecular Weight:183.03
124-04-9
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111-50-2
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Yield:111-50-2 98.2%
Reaction Conditions:
with phosgene;N,N-dimethyl-formamide in toluene at 50 - 55;
Steps:
1
292.3 g (2.0 mol) of adipic acid is suspended in 292.3 g of toluene, added with 4.39 g (0.06 mol: 3 mol%/adipic acid) of dimethylformamide (DMF), and then heated to 50°C-55°C. A reaction is conducted with maintaining the temperature and injecting phosgene gas through a flowmeter at a rate of 45 g/hr. The phosgene gas is injected for about 10 hr in total (total phosgene: 4.4 mol). Then, nitrogen is injected at 48 L/hr for 2 hr at the same temperature to distill off the dissolved phosgene and hydrochloric acid gas. A Vilsmeier reagent type compound floats in a reaction solution, and a part thereof exists at a bottom of a flask in the form of a paste. Then, 5.26 g (0.036 mol: 1.2 equivalents/DMF) of adipic acid is added and agitated for 1 hr. During the agitation, the flotage of the Vilsmeier reagent type compound and the crystal of the adipic acid are completely dissolved. Then, nitrogen is injected at 48 L/hr to distill off hydrochloric acid gas to obtain 645.4 g of a reaction solution. As a result of a GC analysis, a ratio of adipic acid dichloride is 56.7 wt% (2.0 mol) (reaction yield: 98.2%/total adipic acid). Then, the toluene is distilled off at 10 torr and 70°C in an oil bath. Eventually, an inner temperature reaches 69°C. 371.5 g of a crude adipic acid dichloride is obtained, and as a result of a GC analysis, an adipic acid dichloride content is 97.1 wt%, a toluene content is 1.3 wt%, a DMF content is 0.48 wt%, and an adipic acid monochloride content is 0.43 wt%. A yield of adipic acid dichloride calculated from the purity is 96.8%.
References:
Mitsui Chemicals, Inc. EP2128122, 2009, A1 Location in patent:Page/Page column 5
6066-82-6
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111-50-2
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111-50-2
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