Benzoyl chloride, chlorination

CHARACTERIZATION OF ALCOHOLS 4-(4-Nitrophcnylazo)benzoyl chloride. CHLORINATION Antimony(V) chloride. t-Butyl hypochlorite. 1-Chlorobenzotri-aznle. N-Chloropolymaleimide. Cupric chloride. lodobenzene dichloride. Sulfur-yl chloride. Titanium tetrachloride. Tri-chloramine. 

MAJOR USES Manufacture of other chemicals including dyes, benzoyl chloride, chlorinated toluenes and benzotriflouride. 

Benzophenone is produced by the oxidation of diphenylmethane (350). This free from chlorine (FCC) route is favored for perfume uses. The Friedel-Crafts reaction of benzene and benzoyl chloride in the presence of aluminum chloride is also possible this reaction may proceed in the absence of catalyst at a temperature of 370°C and pressure of 1.4 MPa (351). 

Benzyl Chloride. Benzyl chloride is manufactured by high temperature free-radical chlorination of toluene. The yield of benzyl chloride is maximized by use of excess toluene in the feed. More than half of the benzyl chloride produced is converted by butyl benzyl phthalate by reaction with monosodium butyl phthalate. The remainder is hydrolyzed to benzyl alcohol, which is converted to ahphatic esters for use in soaps, perfume, and davors. Benzyl salicylate is used as a sunscreen in lotions and creams. By-product benzal chloride can be converted to benzaldehyde, which is also produced directiy by oxidation of toluene and as a by-product during formation of benzoic acid. By-product ben zotrichl oride is not hydrolyzed to make benzoic acid but is allowed to react with benzoic acid to yield benzoyl chloride. 

Chlorine can replace the hydrogen to produce benzoyl chloride. 

The only industrially important processes for the manufacturing of synthetic benzaldehyde involve the hydrolysis of benzal chloride [98-87-3] and the air oxidation of toluene. The hydrolysis of benzal chloride, which is produced by the side-chain chlorination of toluene, is the older of the two processes. It is no longer utilized ia the United States. Other processes, including the oxidation of benzyl alcohol, the reduction of benzoyl chloride, and the reaction of carbon monoxide and benzene, have been utilized ia the past, but they no longer have any iadustrial appHcation. 

Nearly all of the benzyl chloride [100-44-7], henzal chloride [98-87-3], and hen zotrichl oride /P< -(97-i manufactured is converted to other chemical intermediates or products by reactions involving the chlorine substituents of the side chain. Each of the compounds has a single primary use that consumes a large portion of the compound produced. Benzyl chloride is utilized in the manufacture of benzyl butyl phthalate, a vinyl resin plasticizer benzal chloride is hydrolyzed to benzaldehyde hen zotrichl oride is converted to benzoyl chloride. Benzyl chloride is also hydrolyzed to benzyl alcohol, which is used in the photographic industry, in perfumes (as esters), and in peptide synthesis by conversion to benzyl chloroformate [501-53-1] (see Benzyl ALCOHOL AND p-PHENETHYL ALCOHOL CARBONIC AND CARBONOCm ORIDIC ESTERS). 

Benzotrichloride is a chemical iatermediate used to produce two significant products. Partial hydrolysis or reaction with benzoic acid yields benzoyl chloride, whereas chlorination and subsequent reaction with hydrogen fluoride yields -chlorobenzotrifluoride [98-56-6]. 

The second most important nucleophilic substitution in pyridazine A-oxides is the replacement of a nitro group. Nitro groups at the 3-, 4-, 5- and 6-position are easily substituted thermally with a chlorine or bromine atom, using acetyl chloride or hydrobromic acid respectively. Phosphorus oxychloride and benzoyl chloride are used less frequently for this purpose. Nitro groups in nitropyridazine A-oxides are easily replaced by alkoxide. The... 

Benzoylacetanilide couplers, 79 253 Benzoyl chloride, 3 595, 634 end use of chlorine, 6 134t physical constants of ring-chlorinated derivatives, 6 333t Benzoylcyclohexane-diones, 73 294 Benzoyloxy radicals, 74 281 Benzoyl peroxide (BPO), 3 634 20 105 hazards associated with, 78 491 uses for, 78 496... 

Aluminum phosphide Amyl trichlorosilane Benzoyl chloride Boron tribromide Boron trifluoride Boron trifluoride etherate Bromine pentafluoride Bromine trifluoride n-Butyl isocyanate Butyllithium Butyric anhydride Calcium Calcium carbide Chlorine trifluoride Chloro silanes Chlorosulfonic acid Chromium oxychloride Cyanamide Decaborane Diborane... 

Benzoylation of )V-(2,2-diethoxycarbonylvinyl)-/3-D-galactopyranosy-lamine and -/3-D-gluco analogue in pyridine with benzoyl chloride afforded mixtures of di-, tri-, and tetra-O-benzoyl derivatives. From 2,3,6-tri-O-benzoyl-N-(2,2-ethoxycarbonylvinyl)-j8-D-galatopyranosylamine and -/3-D-glucopyranosylamine the amines were liberated with bromine or chlorine in chloroform or methylene chloride (89MI4). 

Benzal chloride see also a-Chlorinated toluenes and benzoyl chloride) Benz[a]anthracene... 

Chloroethyl benzoate has been prepared from benzoyl chloride and ethylene chlorohydrin from benzoic acid, ethylene glycol, and hydrogen chloride at 100° from ethylene oxide and benzoyl chloride from benzoyl chloride and dioxane in the presence of titanium tetrachloride from benzoic acid, ethylene, and chlorine in the presence of various catalysts. It has also been obtained by hydrolysis of 2-chloroethyl benzimidate " by the action of bromomagnesium benzoate on 2-chloroethyl -toluene-sulfonate and by the action of sodium benzoate on bis-(2-chloroethyl) sulfate. ... 

Figure 1. Chemical processes associated with the manufacture of chlorinated toluenes and benzoyl chloride...

A mortality study was conducted among 697 male employees (610 whites and 11 assumed to be white) at a chlorination plant in Tennessee (United States) (Wong, 1988). The cohort consisted of all employees at the plant between 1943 and 1980. Almost all of the cohort held jobs with potential exposure to benzotrichloride, benzyl chloride or benzoyl chloride, there being substantial overlap between these groups. The mortality data were compared with the United States national age- and cause-specific rates for five-... 

Combined exposures to a-chlorinated toluenes and benzoyl chloride are probably... 

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