BENZOYL CHLORIDE

CAS No.: 98-88-4
EC No.: 202-710-8

Synonyms:
BENZOYL CHLORIDE; benzoyl chloride; benzoil klorür; BENZOİL KLORÜR; BENZOYL CHLORIDE; 98-88-4; Benzoylchloride; Benzenecarbonyl chloride; Benzoic acid, chloride; alpha-Chlorobenzaldehyde; benzoic acid chloride; benzoylchlorid; Benzaldehyde, alpha-chloro-; CCRIS 802; UNII-VTY8706W36; HSDB 383; EINECS 202-710-8; UN1736; BRN 0471389; Benzaldehyde, .alpha.-chloro-; CHEBI:82275; VTY8706W36; Benzoyl chloride, 99%, pure; Benzoyl chloride, 98+%, ACS reagent; Benzoyl chloride, ReagentPlus(R), >=99%; benzoyl chlorid; benzoyl choride; bezoyl chloride; benzoic chloride; BzCl; benzoyl chloride-; BENZOYL CHLORIDE; benzoyl chloride; benzoil klorür; BENZOİL KLORÜR; BENZOYL CHLORIDE; benzoyl chloride; benzoil klorür; BENZOİL KLORÜR; PhCOCl; Bz-Cl; MFCD00000653; PubChem22045; Benzoyl chloride [UN1736] [Corrosive]; .alpha.-Chlorobenzaldehyde; Benzaldehyde, |A-chloro-; DSSTox_CID_6631; ACMC-20aj01; EC 202-710-8; SCHEMBL1241; BENZOIC ACID,CHLORIDE; BENZOYL CHLORIDE; benzoyl chloride; benzoil klorür; BENZOİL KLORÜR; DSSTox_RID_78168; DSSTox_GSID_26631; 4-09-00-00721 (Beilstein Handbook Reference); KSC486Q7P; Benzoyl Chloride, ACS reagent; CHEMBL2260719; DTXSID9026631; CTK3I6877; KS-00000UUU; Benzoyl chloride, AR, >=99%; Benzoyl chloride, LR, >=99%; OTAVA-BB 1051706; LABOTEST-BB LTBB000456; BENZOYL CHLORIDE; benzoyl chloride; benzoil klorür; BENZOİL KLORÜR; CS-B1785; ZINC2041164; Tox21_200431; ANW-75551; SBB059783; STL264120; Benzoyl chloride, ACS reagent, 99%; AKOS000121308; AS00010; MCULE-3627399529; BENZOYL CHLORIDE; benzoyl chloride; benzoil klorür; BENZOİL KLORÜR; BENZOYL CHLORIDE; benzoyl chloride; benzoil klorür; BENZOİL KLORÜR; UN 1736; CAS-98-88-4; Benzoyl chloride, purum, >=99% (GC); Benzoyl chloride, ReagentPlus(R), 99%; NCGC00248610-01; NCGC00257985-01; Benzoyl chloride [UN1736] [Corrosive]; Benzoyl chloride, p.a., 98-100.5%; LS-42590; PS-10801; SC-76545; DB-002645; DB-051009; B0105; Benzoyl chloride, 99%, pure, AcroSeal(R); FT-0622741; FT-0639824; ST51046056; BENZOYL CHLORIDE; benzoyl chloride; benzoil klorür; BENZOİL KLORÜR; Benzoyl chloride, SAJ first grade, >=98.0%; C19168; 11273-EP2270015A1; 11273-EP2270114A1; 11273-EP2272841A1; 11273-EP2272972A1; BENZOYL CHLORIDE; benzoyl chloride; benzoil klorür; BENZOİL KLORÜR; 11273-EP2272973A1; 11273-EP2275407A1; 11273-EP2275412A1; 11273-EP2277848A1; 11273-EP2277872A1; 11273-EP2277878A1; BENZOYL CHLORIDE; benzoyl chloride; benzoil klorür; BENZOİL KLORÜR; 11273-EP2277880A1; 11273-EP2279750A1; 11273-EP2281813A1; 11273-EP2281815A1; 11273-EP2284157A1; BENZOYL CHLORIDE; benzoyl chloride; benzoil klorür; BENZOİL KLORÜR; 11273-EP2286811A1; 11273-EP2287159A1; Q412825; F2190-0038; 247-558-3 [EINECS]; 471389; 98-88-4 [RN]; a-Chlorobenzaldehyde; Benzaldehyde, α-chloro-; benzoic acid chloride; Benzoic acid, chloride; Benzoyl chloride [ACD/Index Name] [ACD/IUPAC Name] [Wiki]; Benzoyl chloride [UN1736] [Corrosive]; Benzoylchlorid [German] [ACD/IUPAC Name]; BENZOYL CHLORIDE; benzoyl chloride; benzoil klorür; BENZOİL KLORÜR; Chlorure de benzoyle [French] [ACD/IUPAC Name]; DM6600000; VTY8706W36; 100-09-4 [RN]; 2719-27-9 [RN]; 4-09-00-00721 (Beilstein Handbook Reference) [Beilstein]; 43019-90-5 [RN]; 52947-05-4 [RN]; 59748-37-7 [RN]; ANISIC ACID; Benzaldehyde, α-chloro-; Benzenecarbonyl chloride; BENZOYL CHLORIDE-(RING-13C6); Benzoyl Chloride, ACS reagent; BENZOYL CHLORIDE; benzoyl chloride; benzoil klorür; BENZOİL KLORÜR; BENZOYL CHLORIDE|BENZOYL CHLORIDE; benzoylchloride; Benzoyl-d5 Chloride; Cyclohexanecarbonyl chloride [ACD/Index Name] [ACD/IUPAC Name]; EINECS 202-710-8; Hexahydrobenzoyl chloride; InChI=1/C7H5ClO/c8-7(9)6-4-2-1-3-5-6/h1-5; MFCD01865658 [MDL number]; O-CHLOROFORMYLBENZENE; PS-10801; UNII:VTY8706W36; UNII-VTY8706W36; α-Chlorobenzaldehyde; BENZOYL CHLORIDE; benzoyl chloride; benzoil klorür; BENZOİL KLORÜR; α-Chlorobenzaldehyde; 苯甲酰氯 [Chinese]; benzenecarbonyl chloride; benzoic acid;  chloride; benzoylchloride; alpha-chlorobenzaldehyde; benzoic acid chloride; benzoylchlorid; benzaldehyde; alpha-chloro; a-chlorobenzaldehyde; ccris 802; unii-vty8706w36; BzCl; Basic Red 1; BENZOYL CHLORIDE; benzoyl chloride; benzoil klorür; BENZOİL KLORÜR; BENZOXALONE; Benzoylchlorid; BENZOYL CHLORIDE; BenzoylChlorideGr; chloruredebenzoyle;-Chlorobenzaldehyde; Benzoyl Chloride >BENZOYL CHLORIDE, ACS; alpha-Chlorobenzaldehyde; Benzenecarbonyl chloride; BENZOYL CHLORIDE; benzoyl chloride; benzoil klorür; BENZOİL KLORÜR; BENZOIC ACID CHLORIDE; BENZOYL CHLORIDE; LABOTEST-BB LTBB000456; alpha-chloro-benzaldehyd; Benzaldehyde, alpha-chloro-; -Chlorobenzaldehyde; chloruredebenzoyle; BENZOYL CHLORIDE; benzoyl chloride; benzoil klorür; BENZOİL KLORÜR; BENZOYL CHLORIDE, REAGENTPLUS, >=99%; BENZOYL CHLORIDE REAGENTPLUSTM >=99%; BENZOYL CHLORIDE, REAGENTPLUS, 99%; BENZOYL CHLORIDE, 99%, A.C.S. REAGENT; BENZOYL CHLORIDE REAGENTPLUS(TM) 99%; BENZOYL CHLORIDE; benzoyl chloride; benzoil klorür; BENZOİL KLORÜR; BENZOYL CHLORIDE, ACS; BenzoylChlorideGr; Benzoyl chloride, 99+%; BENZOYL CHLORIDE; benzoyl chloride; benzoil klorür; BENZOİL KLORÜR; Benzoyl chloride, for analysis ACS, 98+%; Benzoyl chloride, pure, 99%; BENZOYL CHLORIDE REAGENT (ACS); BENZOYL CHLORIDE; benzoyl chloride; benzoil klorür; BENZOİL KLORÜR

BENZOYL CHLORIDE

Benzoyl chloride
Not to be confused with benzyl chloride.
Benzoyl chloride
Infobox references

Preparation
Benzoyl chloride is produced from benzotrichloride using either water or benzoic acid:

C6H5CCl3 + H2O → C6H5COCl + 2 HCl
C6H5CCl3 + C6H5CO2H → 2 C6H5COCl + HCl
As with other acyl chlorides, it can be generated from the parent acid and other chlorinating agents phosphorus pentachloride, thionyl chloride, or oxalyl chloride. It was first prepared by treatment of benzaldehyde with chlorine.

An early method for production of benzoyl chloride involved chlorination of benzyl alcohol.

Reactions
It reacts with water to produce hydrochloric acid and benzoic acid:

C6H5COCl + H2O → C6H5CO2H + HCl
Benzoyl chloride is a typical acyl chloride. It reacts with alcohols to give the corresponding esters. Similarly, it reacts with amines to give the amide.

It undergoes the Friedel-Crafts acylation with aromatic compounds to give the corresponding benzophenones and related derivatives.With carbanions, it serves again as a source of "PhCO+".

Benzoyl peroxide, a common reagent in polymer chemistry, is produced industrially by treating benzoyl chloride with hydrogen peroxide and sodium hydroxide:

Benzoyl chloride is used in benzoylation treatment to decrease the hydrophobicity of the fiber and to improve fiber–matrix adhesion leading to an increase in the strength of the composite. In benzoylation treatment, the alkali pretreatment is used to activate the hydroxyl groups of the fiber and then the fiber is soaked in benzoyl chloride solution for 15 minutes. Benzoyl chloride which is adhered to the fiber surface is removed by ethanol solution followed by washing with water and drying in an oven. Benzoyl chloride treatment on alkali pretreated sisal fiber exhibits higher thermal stability compared to untreated fiber composites (Joseph et al., 1996).

In this process, the pretreated coir fibers are suspended in 10% NaOH solution and agitated with benzoyl chloride. The mixture is left for 15 min, filtered, washed thoroughly with water and then dried between filter papers. The isolated fibers are then soaked in ethanol for one hour to remove the benzoyl chloride and finally washed with water and dried in the oven at 800°C for 24 h (Chandra Rao et al., 2012).

Acid Chlorides
Linear sweep voltammetry of benzoyl chloride in acetonitrile containing tetra-ethylammonium fluoroborate shows Ep = −1.4 V vs. sce and for heptanoyl chloride Ep = −2.2 V vs. sce The one-electron reduction of acid chlorides at these potentials is a source of carbonyl radicals. Reduction of benzoyl chloride at the peak

potential gives the stilbene derivative 37. In this reaction, benzil is generated by the union of two benzoyl radicals, then further reduction followed by reaction with benzoyl chloride yields the final product .

Hydrolysis of benzoyl chloride was followed by measuring the decrease in solution pH values as HCl and benzoic acid were formed. Benzotrichloride was included in these experiments as a control. Since hydrolysis of benzoyl chloride is expected to be very rapid in the initial stages (0.1 min) and thus not observable by HPLC since a minimum sample preparation and HPLC injection time of 20 sec was needed, estimation based on pH measurements was chosen as method.

The authors tested the hydrolysis of benzoyl chloride by measuring the decrease in pH solution at ~25°C as HCl and benzoic acid are formed. Under these conditions the half-life value was <0.25 min at 25°C. Using the formula t1/2 = ln 2 / (kH20), the hydrolysis rate constants calculated was > 2.77 min-1.
GLP standards are not specified. The study sufficiently describes the materials and methodology used, thus the study can be considered Klimisch 2e as it is well documented, meets generally accepted scientific principles and is acceptable for assessment.
Executive summary:
The authors tested the hydrolysis of benzoyl chloride (CAS n° 98-88-4) by measuring the decrease in pH solution at ~25°C as HCl and benzoic acid are formed. Initial concentration of the test substance was 100 ppm and hydrolysis reaction was monitored till no change in pH was evident. The half-life value was estimated using benzotrichloride which was included in this experiment as a control and aid to interpret the pH plots. Under these conditions the half-life value was 0.25 min at 25°C. Using the formula t1/2 = ln 2 / (kH20), the hydrolysis rate constants calculated was >2.77 min-1.

GLP standards are not specified. As the study sufficiently describes the materials and methodology used, the study can be considered reliable with restrictions as it is well documented, meets generally accepted scientific principles and is acceptable for assessment (Klimisch 2e).

Benzoyl chloride Chemical Properties,Uses,Production
Physical and Chemical Properties
Its pure product is a colorless and transparent flammable liquid, which is smoking exposed to air in the air. In Industry, it is slightly pale yellow, with a strong pungent odor. Its steam has a strong stimulating effect for eye mucous membranes, skin and respiratory tract, by stimulating the mucous membranes and eyes tear. Benzoyl chloride Melting point is-1.0 ℃, boiling point is 197.2 ℃, and the relative density is 1.212 (20 ℃), while a flash point is 72 ℃, and refractive index (n20) is 1.554. It is soluble in the ether, chloroform, benzene and carbon disulfide. It can gradually decomposed in water or ethanol, ammonia, which generates benzoic acid, generating benzamide, ethyl benzoate and hydrogen chloride. In the laboratory, it can be obtained by distillation of benzoic acid and phosphorus pentachloride under anhydrous conditions. Industrial production process can be obtained by the use of thionyl chloride benzaldehyde. Benzoyl chloride is an important intermediate for preparing dyes, perfumes, organic peroxides, resins and drugs. It is also used in photography and artificial tannin production, which was formerly used as an irritant gas in chemical warfare.
Application
Used for dye intermediates, initiator, UV absorbers, rubber additives, medicine etc.
Benzoyl chloride is intermediate of herbicide metamitron, and insecticide propargite, benzene hydrazine or intermediate food.
Benzoyl chloride is used for organic synthesis, dye and pharmaceutical raw material, manufacturing initiator benzoyl peroxide, t-butyl peroxybenzoate, pesticides and herbicides. In pesticides, it is a new insecticide, which is inducible isoxazole parathion (Isoxathion, Karphos) intermediate. Benzoyl chloride is an important benzoyl and benzyl reagent. Most of benzoyl chloride is used in the production of benzoyl peroxide, and secondly for the production of benzophenone, benzyl benzoate, benzyl cellulose. Benzoyl peroxide catalyzes polymerization initiator for the monomer plastic, polyester, epoxy, acrylic resin production, self-curing agent, which is a glass fiber material, fluorine rubber, silicone crosslinking agents, oil refined, bleached flour, fiber decolorizing Wait. Domestic original benzoyl chloride manufacturing enterprises are more than 20. Some of the manufacturers also produce acid chloride, and the production capacity is 10,000t. However, according to the 2003 survey, the profit is too low, because of the use of small polluting production line, while the use of polluting route is controlled by the government restrictions, and a further raw material price increases. Therefore most of the manufacturers stop the production. Further reaction with the acid chloride can also produce acid anhydride,  and benzoic acid anhydride is the main purpose for acylation agents, which can also be used as a bleaching agent and flux of a component, as well as it can also be used for the preparation of benzoyl peroxide over.
Reagents for the analysis, but also for spices, organic synthesis.
Chemical Properties
Transparent, colorless liquid; pungent odor; vapor causes tears. Soluble in ether and carbon disulfide; decomposes in water. Combustible.
Chemical Properties
Benzoyl chloride is a colorless to slight brown liquid with a strong, penetrating odor.
Uses
Benzoyl Chloride is used in the manufacturing of dye intermediates.
Uses
For acylation, i.e., introduction of the benzoyl group into alcohols, phenols, and amines (Schotten-Baumann reaction); in the manufacture of benzoyl peroxide and of dye intermediates. In organic analysis for making benzoyl derivatives for identification purposes.
Definition
A liquid acyl chloride used as a benzoylating agent.
Production Methods
Benzoyl chloride can be prepared from benzoic acid by reaction with PCl5 or SOCl2, from benzaldehyde by treatment with POCl3 or SO2 Cl2, from benzotrichloride by partial hydrolysis in the presence of H2SO4 or FeCl3, from benzal chloride by treatment with oxygen in a radical source, and from several other miscellaneous reactions. Benzoyl chloride can be reduced to benzaldehyde, oxidized to benzoyl peroxide, chlorinated to chlorobenzoyl chloride and sulfonated to m-sulfobenzoic acid. It will undergo various reactions with organic reagents. For example, it will add across an unsaturated (alkene or alkyne) bond in the presence of a catalyst to give the phenylchloroketone:

General Description
A colorless fuming liquid with a pungent odor. Flash point 162°F. Lachrymator, irritating to skin and eyes. Corrosive to metals and tissue. Density 10.2 lb / gal. Used in medicine and in the manufacture of other chemicals.
Reactivity Profile
Benzoyl chloride reacts violently with protic solvents such as alcohols, with amines and amides (for example dimethylformamide [Bretherick 1979 p. 6] ) and with inorganic bases. Causes the violent decomposition of dimethyl sulfoxide [Chem. Eng. News 35(9): 87 1957]. May react vigorously or explosively if mixed with diisopropyl ether or other ethers in the presence of trace amounts of metal salts [J. Haz. Mat., 1981, 4, 291]. Friedel-Crafts acylation of naphthalene using Benzoyl chloride, catalyzed by AlCl3, must be conducted above the melting point of the mixture, or the reaction may be violent [Clar, E. et al., Tetrahedron, 1974, 30, 3296].

Health Hazard
INHALATION: may irritate eyes, nose and throat. INGESTION: causes acute discomfort. SKIN: causes irritation and burning.
Chemical Reactivity
Reactivity with Water Slow reaction with water to produce hydrochloric acid fumes. The reaction is more rapid with steam; Reactivity with Common Materials: Slow corrosion of metals but no immediate danger; Stability During Transport: Not pertinent; Neutralizing Agents for Acids and Caustics: Soda ash and water, lime; Polymerization: Does not occur; Inhibitor of Polymerization: Not pertinent.
Safety Profile
Confirmed carcinogen withexperimental tumorigenic data by skin contact. Humansystemic effects by inhalation: unspecified effects onolfaction and respiratory systems. Corrosive effects on theskin, eyes, and mucous membranes by inhalation.Flammable whe
Potential Exposure
Benzoyl chloride is used as a chemical intermediate; in organic synthesis; to produce other chemicals, dyes, perfumes, herbicides, and medicines.
Shipping
UN 1736 Benzoylchloride, Hazard class: 8; Labels: 8—Corrosive material.
Purification Methods
A solution of benzoyl chloride (300mL) in *C6H6 (200mL) is washed with two 100mL portions of cold 5% NaHCO3 solution, separated, dried with CaCl2 and distilled [Oakwood & Weisgerber Org Synth III 113 1955]. Repeated fractional distillation at 4mm Hg through a glass helices-packed column (avoiding porous porcelain or silicon-carbide boiling chips, and hydrocarbon or silicon greases on the ground joints) gave benzoyl chloride that did not darken on addition of AlCl3. Further purification is achieved by adding 3 mole% each of AlCl3 and toluene, standing overnight, and distilling off the benzoyl chloride at 1-2mm [Brown & Jenzen J Am Chem Soc 80 2291 1958]. Refluxing for 2hours with an equal weight of thionyl chloride before distillation has also been used. [Beilstein 9 IV 721.] Strong IRRITANT. Use in a fume cupboard.
Incompatibilities
May form explosive mixture with air. Contact with heat, hot surfaces, and flames causes decomposition, forming phosgene and hydrogen chloride. Water contact may be violent; forms hydrochloric acid. Reactions with amines, alcohols, alkali metals, dimethyl sulfoxide, strong oxidizers, and metal salts may be violent, causing fire and explosions. Attacks metals in the presence of moisture, forming explosive hydrogen gas. Attacks some plastics, rubber or coatings.
Waste Disposal
Pour into sodium bicarbonate solution and flush to sewer.
Benzoyl chloride Preparation Products And Raw materials

IDENTIFICATION: Benzoyl chloride is a yellow to colorless liquid. It has a fuming pungent odor and is corrosive. It reacts very rapidly with water. USE: Benzoyl chloride is an important commercial chemical. It is used to make many other chemicals, in the production of dyes and in chemical analysis. EXPOSURE: Workers that use benzoyl chloride may breathe in vapors or have direct skin contact. The general population is not likely to be exposed to benzoyl chloride. If benzoyl chloride is released to the environment, it will be broken down in air. It is expected to be broken down by sunlight. It breaks down very quickly in water so will not move into air from moist soil and water surfaces. It may however move from dry soil into the air. Because it reacts with water, is not expected to move through soil, to be broken down by microorganisms, or to build up in fish.

Benzoyl chloride is produced commercially from benzotrichloride, which is available by the chlorination of toluene. The chlorination reaction proceeds stepwise via benzyl chloride and benzal chloride. The benzotrichloride is then partially hydrolyzed with a limited amount of water. This series of reactions consumes a large quantity of chlorine. An alternative process uses benzoic acid. Phosphorous chlorides or iron chlorides are used as catalysts at the solvolytic stage of both processes. Benzoyl chloride can also be made by the reaction of benzoic acid with phosgene, thionyl chloride, or phosphorous pentachloride; chlorination of benzaldehyde, benzyl alcohol, or benzyl benzoate; and direct reaction of benzene with phosgene or the combination of carbon monoxide and chlorine. The benzoyl chloride prepared by the conventional processes may contain trace amounts of chlorobenzoyl chloride, but the product obtained by the reaction of molten phthalic anhydride with hydrogen chloride at 200 °C is free of such impurities.

This action promulgates standards of performance for equipment leaks of Volatile Organic Compounds (VOC) in the Synthetic Organic Chemical Manufacturing Industry (SOCMI). The intended effect of these standards is to require all newly constructed, modified, and reconstructed SOCMI process units to use the best demonstrated system of continuous emission reduction for equipment leaks of VOC, considering costs, non air quality health and environmental impact and energy requirements. Benzoyl chloride is produced, as an intermediate or a final product, by process units covered under this subpart.

Benzoyl chloride's production and use as a reagent in the production of dyes, resins, perfumes, pharmaceuticals, benzoyl peroxide, polymerization catalysts, benzophenone, stabilizers, and as a reagent in organic analyses may result in its release to the environment through various waste streams. If released to air, a vapor pressure of 0.7 mm Hg at 25 °C indicates benzoyl chloride will exist solely as a vapor in the ambient atmosphere. Vapor-phase benzoyl chloride will be degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals; the half-life for this reaction in air is estimated to be 9 days. Benzoyl chloride adsorbs light above 290 nm and, therefore, may be susceptible to direct photolysis by sunlight. Hydrolysis is expected to be the most important environmental fate process for benzoyl chloride based on a hydrolysis rate constant of 4.2X10-2 sec-1 at 25 °C which corresponds to a half-life of 16 seconds. Absorption to soil and sediments, volatilization, biodegradation, leaching, and bioconcentration are not expected to occur in moist soil or water. However, benzoyl chloride has a vapor pressure of 0.7 mm Hg and exists as a liquid under environmental conditions: therefore, benzoyl chloride may volatilize from dry soil. In the absence of water, benzoyl chloride could form a variety of esters upon reaction with common soil constituents. Occupational exposure to benzoyl chloride may occur through inhalation and dermal contact with this compound at workplaces where benzoyl chloride is produced or used. The general population is not likely to be exposed to benzoyl chloride. (SRC)