ChemicalBook CAS DataBase List SUCCINYL CHLORIDE

SUCCINYL CHLORIDE synthesis

5synthesis methods

Product Name:SUCCINYL CHLORIDE
CAS Number:543-20-4
Molecular formula:C4H4Cl2O2
Molecular Weight:154.98

110-15-6 Synthesis

110-15-6
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543-20-4
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$18.00/25g

Yield:543-20-4 98.2%

Reaction Conditions:

with phosgene;N,N-dimethyl-formamide in toluene at 55;Product distribution / selectivity;

Steps:

2
236.18 g (2.0 mol) of succinic acid is suspended in 236.2 g of toluene, added with 1.46 g (0.02 mol: 1 mol%/succinic acid) of dimethylformamide (DMF), and then heated to 55°C. A reaction is conducted with maintaining the temperature and injecting phosgene gas through a flowmeter at a rate of 25 g/hr. The phosgene gas is injected for about 16 hr in total (total phosgene: 4.1 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, 2.60 g (0.022 mol: 2.2 equivalents/DMF) of succinic acid is added and agitated for 1 hr. During the agitation, the flotage of the Vilsmeier reagent type compound and the crystal of the succinic acid are completely dissolved. Then, nitrogen is injected at 48 L/hr to distill off hydrochloric acid gas to obtain 553.5 g of a reaction solution. As a result of a GC analysis, a ratio of succinic acid dichloride is 55.62 wt% (1.99 mol) (reaction yield: 98.2%/total succinic acid). Then, the toluene is distilled off at 20 torr and 70°C in an oil bath. Eventually, an inner temperature reaches 70°C. 311.4 g of a crude succinic acid dichloride is obtained, and as a result of a GC analysis, a succinic acid dichloride content is 96.4 wt%, a toluene content is 2.1 wt%, a DMF content is 0.51 wt%, and a succinic acid monochloride content is 0.6 wt%. A yield of succinic acid dichloride calculated from the purity is 95.8%.

References:

Mitsui Chemicals, Inc. EP2128122, 2009, A1 Location in patent:Page/Page column 5

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108-30-5 Synthesis