Carbonyl chloride, COCL

P10.5 The thermodynamic functions for solid, liquid, and gaseous carbonyl chloride (COCL) obtained from Third Law and statistical calculations... 

Chlorine forms carbonyl chloride, COCl with carbon monoxide suhuryl chloride SO2CI with sulfur dioxide and chloramines (monochloramine, NH2CI, and dichloramine, NHCI2) with ammonia. Chloramines are often found at trace concentrations in sewage wastewater following chlorine treatment. 

Phosgene (Carbonyl chloride COCl) A colorless poisonous choking agent (gas) used in warfare before more potent agents were discovered. 

When the - COCl group is bonded to a ring Change the suffix -carboxylic acid to -carbonyl chloride. 

Five-membered cyciic ureas (2-imidazoiidinones) react with COCl j exclusiveiy at the nitrogen atom to form cyciic ailophanoyi chlorides, 2-imidazoiidinone-l-(carbonyl chloride). In the presence of a base, dehydrochlorination resuits in the production of isocyanates [2087a] ... 

An acyl chloride such as benzoyl chloride can react with secondary and primary amines and amino acids to form N-substituted benzamide derivatives. Analytical reagents used for precolumn derivatizations are p-nitrobenzene azobenzoyl chloride for LC-UV, o-acetylsalicyloyl chloride for LC-ECD, and 3,4-dihydro-6,7-dimethoxy-4-methyl-3-oxoquinoxa-line-2-carbonyl chloride (DMEQ-COCl) and 4-(4,5-diphenyl-lf/-imidazol-2-yl)benzoyl chloride (DIB-Cl) for LC-FL, respectively. Pentafluorobenzoyl chloride (PFBC) is used as an acylating reagent for GC with electron-capture detection (Figure 4). Many of those described above can also react with hydroxyl and phenol groups. 

The so-called "ene" reaction has not been observed with phosgene, although it occurs readily with the related carbonyl pseudohalide, CO(CN)j [972]. Moreover, no Diels-Alder product is obtained when 1,3-cyclohexadiene is reacted with phosgene. Acyl chlorides are formed at 80 C and very high pressures, but no reaction occurs between 1,3-cyclohexadiene and COCl, at atmospheric pressure [1185]. 

A 4 1 mixture of gaseous SOFj and COCl, when passed through a column consisting of iron(III) chloride on an iron packing at 400 C, and at a contact time of 10 min, resulted in the formation of carbonyl difluoride, accompanied by minor quantities of COCIF and CCljFj [704]. The reaction which forms COCIF may be represented by the equation ... 

Steric and electronic factors are both important in determining reactivity. Sterically, we find within a series ofsimilar acid derivatives that unhindered, accessible carbonyl groups react with nucleophiles more readily than do sterically hindered groups. For example, acetyl chloride, CH COCl, is... 

Carbonylation kinetics of ethanol to propionic acid using Rh/HI catalyst is O, 0.828 and 0.664 order with respect to dissolved [CO], [HI], [ethanol] and [Rh] respectively. A spectroscopic study of the RhCls/Mel/PPha catalysed carbonylation of NeOAc to acetic anhydride reveals initial formation of [Rh(CO)2l2) which enters an equilibrium with [Rhl(CO)(PPh3>2], both complexes can act as starting compounds in catalytic cycles . A catalytic procedure for the preparation of CO-labelled aroyl chlorides (Phl COCl, 2-C1C6H,13C0C1, S-OjNCjH 13COCI etc) employs... 

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