Dichloroacetyl chloride

Structural formula
General
Surname	Dichloroacetyl chloride
other names	Dichloroethanoyl chloride Dichloroacetic acid chloride
Molecular formula	C 2 HCl 3 O
Brief description	yellowish, air-smoking liquid with a pungent odor
External identifiers / databases
CAS number 79-36-7 EC number 201-199-9 ECHA InfoCard 100.001.091 PubChem 6593 Wikidata Q1209387
properties
Molar mass	147.39 g mol −1
Physical state	liquid
density	1.53 g cm −3
Melting point	−32.5 ° C
boiling point	107 ° C
Vapor pressure	30.6 h Pa at 20 ° C
solubility	Decomposes in water (hydrolysis to dichloroacetic acid and hydrochloric acid ) and ethanol miscible with diethyl ether
Refractive index	1.46-1.462
safety instructions
GHS hazard labeling from  Regulation (EC) No. 1272/2008 (CLP) , expanded if necessary danger H and P phrases H: 314-400 P: 273-280-305 + 351 + 338-310
Toxicological data	2460 mg kg −1 ( LD 50 ,  rat ,  oral ) 996 mg kg −1 ( LD 50 ,  rabbit ,  transdermal )
Thermodynamic properties
ΔH f 0	−280.4 kJ / mol
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . Refractive index: Na-D line , 20 ° C

Dichloroacetyl chloride is a chemical compound from the group of carboxylic acid halides . It is a colorless to yellowish, air-smoking liquid with a pungent odor.

Occurrence

Dichloroacetyl chloride can form during arc welding if the steel has been cleaned with trichlorethylene or 1,1,1-trichloroethane and there are residues of them on the material or in the air.

Extraction and presentation

Dichloroacetyl chloride can be produced by the oxidation of trichloroethene , by the reaction of dichloroacetic acid and thionyl chloride, or by the reaction of chloroform and carbon dioxide in the presence of aluminum chloride.

properties

Dichloroacetyl chloride reacts with alkali hydroxides , alcohols , alkalis and water. In an aqueous medium it hydrolyzes to dichloroacetic acid and hydrochloric acid .

use

Dichloroacetyl chloride is used as an intermediate in the manufacture of pharmaceuticals and plant protection products, as well as for dichloroacetic acid , dichloroacetic anhydride and their esters .

safety instructions

Dichloroacetyl chloride vapors can form explosive mixtures with air at temperatures above the flash point of 66 ° C.

Web links

• Entry on Dichloroacetyl chloride in the Spectral Database for Organic Compounds (SDBS) of the National Institute of Advanced Industrial Science and Technology (AIST)

See also

• Chloroacetic acid chloride C ₂ H ₂ Cl ₂ O
• Trichloroacetyl chloride C ₂ Cl ₄ O

Individual evidence

1. ↑ ^{a b c d e f g h i j} Entry on dichloroacetyl chloride in the GESTIS substance database of the IFA , accessed on January 8, 2018(JavaScript required) .
2. ^ Mark TD Cronin: Predicting Chemical Toxicity and Fate . CRC Press, 2004, ISBN 978-0-203-64262-7 , pp. 399 ( limited preview in Google Book search).
3. ↑ ^{a b c d e f} Toxicological assessment of dichloroacetic acid chloride (PDF) at the professional association raw materials and chemical industry (BG RCI), accessed on August 22, 2012.
4. ↑ ^{a b} Entry on Dichloroacetyl chloride at ChemBlink , accessed on February 4, 2018.
5. ↑ Entry on dichloroacetyl chloride in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on February 1, 2016. Manufacturers or distributors can expand the harmonized classification and labeling .
6. ↑ David R. Lide (Ed.): CRC Handbook of Chemistry and Physics . 90th edition. (Internet version: 2010), CRC Press / Taylor and Francis, Boca Raton, FL, Standard Thermodynamic Properties of Chemical Substances, pp. 5-21.
7. ↑ Google Patents: US3630867A - Process for preparing dichloroacetyl chloride - Google Patents , accessed January 4, 2019