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EC / List no.: 202-710-8
CAS no.: 98-88-4
Mol. formula: C7H5ClO
Benzoyl chloride, also known as benzenecarbonyl chloride, is an organochlorine compound with the formula C7H5ClO.
Benzoyl chloride is a colourless, fuming liquid with an irritating odour.
Benzoyl chloride is mainly useful for the production of peroxides but is generally useful in other areas such as in the preparation of dyes, perfumes, pharmaceuticals, and resins.
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, Benzoyl chloride can be generated from the parent acid and standard chlorinating agents such as phosphorus pentachloride, thionyl chloride, and oxalyl chloride.
Benzoyl chloride was first prepared by treatment of benzaldehyde with chlorine.
An early method for production of benzoyl chloride involved chlorination of benzyl alcohol.
Reactions
Benzoyl chloride reacts with water to produce hydrochloric acid and benzoic acid:
C6H5COCl + H2O → C6H5CO2H + HCl
Benzoyl chloride is a typical acyl chloride.
Benzoyl chloride reacts with alcohols to give the corresponding esters.
Similarly, Benzoyl chloride reacts with amines to give the amide.
Benzoyl chloride undergoes the Friedel-Crafts acylation with aromatic compounds to give the corresponding benzophenones and related derivatives.
With carbanions, Benzoyl chloride 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:
2 C6H5COCl + H2O2 + 2 NaOH → (C6H5CO)2O2 + 2 NaCl + 2 H2O
Physical and Chemical Properties
Benzoyl chlorides pure product is a colorless and transparent flammable liquid, which is smoking exposed to air in the air.
In Industry, Benzoyl chloride is slightly pale yellow, with a strong pungent odor.
Benzoyl chlorides 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.
Benzoyl chloride is soluble in the ether, chloroform, benzene and carbon disulfide.
Benzoyl chloride can gradually decomposed in water or ethanol, ammonia, which generates benzoic acid, generating benzamide, ethyl benzoate and hydrogen chloride.
In the laboratory, Benzoyl chloride 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.
Benzoyl chloride 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, Benzoyl chloride 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.
Benzoyl chloride may be used in the synthesis of the following organic building blocks:
N,N-diethylbenzamide via condensation with diethylamine
N-2-bromophenylbenzamide by reacting with 2-bromoaniline via N-benzoylation
propargyl benzoate via O-benzoylation of propargyl alcohol
Chemical Properties
Transparent, colorless liquid; pungent odor; vapor causes tears. Soluble in ether and carbon disulfide; decomposes in water. Combustible.
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.
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.
The major industrial use of benzoyl chloride is in the production of benzoyl peroxide. Secondary uses include the formulation of herbicides and the production of drugs, plasticizers, and perfumes.
Chemical intermediate for benzoyl peroxide, a polymerization initiator; chloramben, an herbicide; dyes; Benzophenone, a perfume fixative; other benzoyl derivatives; fastness improver for dyed fibers or fabrics; cellulosic yarn treatment agent; chemical intermediate for benzoate plasticizers (former use), pharmaceuticals (former use)
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.
Benzoyl chloride will undergo various reactions with organic reagents. For example, Benzoyl chloride 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.
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.
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 .
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.
Refluxing for 2hours with an equal weight of thionyl chloride before distillation has also been used.
Benzoyl chloride appears as 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.
Industry Uses
Coatings
Finishing agents
Intermediates
Oxidizing/reducing agents
Paint additives and coating additives not described by other categories
Plasticizers
Processing aids, not otherwise listed
Consumer Uses
Fabric, textile, and leather products not covered elsewhere
Furniture and furnishings not covered elsewhere
Paints and coatings
Personal care products
Plastic and rubber products not covered elsewhere
Methods of Manufacturing
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.
General Manufacturing Information
Industry Processing Sectors
All other basic organic chemical manufacturing
All other chemical product and preparation manufacturing
Furniture and related product manufacturing
Miscellaneous manufacturing
Paint and coating manufacturing
Pharmaceutical and medicine manufacturing
Plastic material and resin manufacturing
Plastics product manufacturing
Textiles, apparel, and leather manufacturing
APPLICATIONS & FEATURES
Production of Benzoyl Peroxide (catalyst for the polymer industry)
Precursor of Benzophenone and several other UV-stabilizers
Precursor of Agrochemicals and Pharmaceutical applications
Dyes and pigments
Uses
Benzyl chloride is used as a chemical intermediate in the manufacture of certain dyes and pharmaceutical, perfume and flavor products.
Benzoyl chloride is also used as a photographic developer.
Benzyl chloride can be used in the manufacture of synthetic tannins and as a gum inhibitor in petrol.
Benzyl chloride has been used as an irritant gas in chemical warfare.
Sources and Potential Exposure
Sources of benzyl chloride emissions into the air include emissions or venting with other gases in industrial settings.
Emissions of benzyl chloride from floor tile plasticized by butyl benzyl phthalate have been reported.
Benzyl chloride has also been detected in emissions from the burning of polyvinyl chloride, neoprene and rigid urethane foam compounds.
Individuals may be exposed to benzyl chloride through breathing contaminated air or from exposure to water or soil that has been contaminated with benzyl chloride.
Physical Properties
Benzyl chloride is a colorless liquid with a very pungent odor.
Benzyl chloride has an odor threshold of 0.044 parts per million (ppm).
Benzyl chloride is insoluble in water.
The chemical formula for benzyl chloride is C7H7Cl, and it has a molecular weight of 126.59 g/mol.
The vapor pressure for benzyl chloride is 1.20 mm Hg at 25 °C, and it has a log octanol/water partition coefficient (log Kow) of 2.70.
About Benzoyl chloride
Helpful information
Benzoyl chloride is registered under the REACH Regulation and is manufactured in and / or imported to the European Economic Area, at ≥ 10 000 tonnes per annum.
Benzoyl chloride is used by professional workers (widespread uses), in formulation or re-packing, at industrial sites and in manufacturing.
Consumer Uses
ECHA has no public registered data indicating whether or in which chemical products the substance might be used. ECHA has no public registered data on the routes by which Benzoyl chloride is most likely to be released to the environment.
Article service life
ECHA has no public registered data on the routes by which Benzoyl chloride is most likely to be released to the environment. ECHA has no public registered data indicating whether or into which articles the substance might have been processed.
Widespread uses by professional workers
Benzoyl chloride is used in the following products: laboratory chemicals and pH regulators and water treatment products.
Benzoyl chloride is used in the following areas: scientific research and development and health services.
Other release to the environment of Benzoyl chloride is likely to occur from: indoor use (e.g. machine wash liquids/detergents, automotive care products, paints and coating or adhesives, fragrances and air fresheners).
Formulation or re-packing
ECHA has no public registered data indicating whether or in which chemical products the substance might be used. Release to the environment of Benzoyl chloride can occur from industrial use: formulation of mixtures.
Uses at industrial sites
Benzoyl chloride is used in the following products: laboratory chemicals and pH regulators and water treatment products.
Benzoyl chloride has an industrial use resulting in manufacture of another substance (use of intermediates).
Benzoyl chloride is used in the following areas: scientific research and development and health services.
Benzoyl chloride is used for the manufacture of: chemicals.
Release to the environment of Benzoyl chloride can occur from industrial use: as an intermediate step in further manufacturing of another substance (use of intermediates), in processing aids at industrial sites, as processing aid and of substances in closed systems with minimal release.
Other release to the environment of Benzoyl chloride is likely to occur from: indoor use (e.g. machine wash liquids/detergents, automotive care products, paints and coating or adhesives, fragrances and air fresheners).
Manufacture
ECHA has no public registered data on the routes by which Benzoyl chloride is most likely to be released to the environment.
Benzoyl chloride is a member of benzoic acids.
Physical Description
Benzoyl chloride appears as 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.
Pharmacology and Biochemistry
Absorption, Distribution and Excretion
Product Applications
Manufacturing of plastics
Polymer auxiliaries
Manufacturing of herbicides
Agriculture
Pesticides
Dyestuffs, pigments and optical brighteners
Manufacturing of textiles dyestuffs
Manufacturing of photochemicals
Manufacturing of textile dyestuffs
Manufacturing of dyestuffs
Photography
Manufacturing of pharmaceutical agents
Flavour and fragances
Textile industry
Pharmaceutical industry / Biotechnology
Plastic- and Rubberpolymers
Chemical synthesis
Chemical Industry
Construction
Antioxidans
Manufacturing of pigments
Pigments
Animal health and feedstuff
Manufacturing of insecticides / acaricides
Manufacturing of fragances
Manufacturing of fungicides
Manufacturing of growth regulators
Textile auxiliaries
PVC
Manufacturing of peroxides
Manufacturing of safeners
Hardener and crosslinking agents for polymeres
Surface-active substances
Manufacturing of veterinarian agents
organic solvent
Textile dyestuffs
Formula: C7H5ClO / C6H5COCl
Molecular mass: 140.57
Boiling point: 197.2°C
Melting point: -1°C
Relative density (water = 1): 1.21
Solubility in water: reaction
Vapour pressure, Pa at 20°C: 50
Relative vapour density (air = 1): 4.88
Flash point: 72°C c.c.
Auto-ignition temperature: 197.2°C
Explosive limits, vol% in air: 2.5-27
Cenzoyl chloride a colorless very pungent liquid compound C6H5COCl made by partial hydrolysis of benzotrichloride and in other ways and used chiefly in organic synthesis (as of dyes)
Benzoyl chloride is a transparent or colorless liquid with a penetrating odor.
Benzoyl chloride is miscible in ether, carbon disulfide, benzene, and oils, and decomposes in water and alcohol.
Benzoyl chloride is flammable and will react with water or steam to produce heat and toxic and corrosive fumes.
Benzoyl chloride can have a violent or explosive reaction with dimethyl sulfoxide, aluminum chloride, and naphthalene.
Benzoyl chloride, also known as benzenecarbonyl chloride, is an organochlorine compound with the formula C6H5COCl.
Benzoyl chloride is a colourless, fuming liquid with an irritating odour.
Benzoyl chloride is mainly useful for the production of peroxides but is generally useful in other areas such as in the preparation of dyes, perfumes, pharmaceuticals, and resins.
I thought this might be worth sharing.
Benzoyl chloride is a highly useful substance due to its action as a chlorinating agent towards short-chain carboxylic acids like acetic acid: when glacial acetic acid is mixed with benzoyl chloride, acetyl chloride can be distilled out of the mixture since benzoyl chloride and acetic acid are in equilibrium with benzoic acid and acetyl chloride.
Acetyl chloride is the lowest boiling of those compounds and the equilibrium can therefore be shifted towards the product side by distilling Benzoyl chloride out.
Benzyl alcohol is available to anyone from e.g. ebay where it is offered frequently.
Benzoyl chloride is also available from pharmacies since it is used a lot in lotions and cosmetic products.
Benzoyl chloride is neither watched nor subject to any government control.
Benzyl alcohol is also useful as a precursor for benzaldehyde and for benzyl chloride (it esterifies readily with concentrated aqueous HCl as outlined in Rhodiums set of benzyl chloride preparations).
Preparation of benzoyl chloride
Benzoyl chloride could be prepared by reacting thionyl chloride or phosphorus pentachloride with benzoic acid.
50 grams of dry benzoic acid are treated in a 500 ml flask, with 90 grams of finely pulverized phosphorus pentachloride.
The mixture is mixed well, upon which, after a short time, the reaction takes place with an energetic evolution of hydrochloric acid, and the reaction mass becomes liquid.
During the reaction, a lot of heat is released. After standing a short time, the completely liquid mixture is twice fractionated by collecting fraction which boils at ~ 200° C, yielding 90 % of benzoyl chloride.
Practical organic chemistry.
A round bottom flask is fitted with a reflux condenser and a gas inlet tube. 100 grams of cold and dry benzaldehyde are added to the flask and saturated with the current of dry chlorine.
The chlorine gas is readily absorbed and the evolution of hydrogen chloride takes place.
When the reaction has moderated, the external heat is applied by keeping gentle boiling.
The stream of chlorine is continued until no more hydrogen chloride is evolved.
A stream of dry air or carbon dioxide is then passed through the apparatus in order to remove an excess of chlorine.
Benzoyl chloride is obtained by distillation as a colorless fuming liquid with a very irritating smell.
Yield is almost quantitative.
Preparation of organic compounds
19 grams of oxalyl chloride and 20 grams of the dry sodium benzoate, with 20-30 ml of dry benzene as a solvent were mixed and gently heated.
19 grams of benzoyl chloride were obtained by fraction distillation with boiling point 198° C yielding 97 %.
IUPAC names
Benzoic acid chloride , Phenylcarbonyl chloride , Phenylcarboxyl chloride
BENZOYL CHLORIDE
Benzoyl Chloride
Benzoyl chloride
benzoyl chloride
Benzoyl Chloride
Benzoyl chloride
benzoyl chloride
Benzoyl chloride
Benzoylchlorid
SYNONYMS:
alpha-Chlorobenzaldehyde
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, ACS
BenzoylChlorideGr
Benzoyl chloride, 99+%
Benzoyl chloride, for analysis ACS, 98+%
Benzoyl chloride, pure, 99%
BENZOYL CHLORIDE REAGENT (ACS)
Benzoylchlorid
BzCl
Basic Red 1
BENZOXALONE
4-Chlorocarbonylpolystyrene
alpha-chloro-benzaldehyd
Benzaldehyde, alpha-chloro-
-Chlorobenzaldehyde
chloruredebenzoyle
LABOTEST-BB LTBB000456
Benzenecarbonyl chloride
BENZOIC ACID CHLORIDE
BENZOYL CHLORIDE
Benzoyl chloride, 99%, pure
Benzoyl chloride, 98+%, for analysis ACS
Benzoyl chloride, for analysis ACS
Benzoyl chloride, 98+%, ACS reagent
Benzoyl chloride, for analysis ACS, 98+% 500GR
Benzoyl chloride, pure, 99% 1LT
Benzoyl chloride, synthesis grade
Benzoyl chloride, 99%, pure, AcroSeal
BENZOYL CHLORIDE FOR SYNTHESIS
Phenylcarbonyl chloride
Benzoyl chloride ReagentPlus(R), >=99%
Benzoyl chloride, ACS,>=99.5%(T)
Benzoyl chloride, ACS reagent
Benzoyl chloride (solina new impurity)
Benzoyl Chloride >
Benzoyl chloride fandachem
Benzoyl chloride ISO 9001：2015 REACH
