Acetyl chloride
- Iupac Name：acetyl chloride
- CAS No.: 75-36-5
- Molecular Weight：78.49762
- Modify Date.: 2022-11-10 15:19
- Introduction: Acetic chloride is a colourless to light yellow liquid with a pungent and chokingodour. Acetic chloride is highly flammable and reacts violently with DMSO, water, loweralcohols, and amines to generate toxic fumes. Along with air, acetic chloride may form anexplosive mixture. It is incompatible with water, alcohols, amines, strong bases, strong oxidisingagents, and most common metals. On decomposition when heated, acetic chlorideproduces carbon monoxide, carbon dioxide, hydrogen chloride, and phosgene.
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1. Names and Identifiers
- 1.1 Name
- Acetyl chloride
- 1.2 Synonyms
1-Chloroethanone acetic acid chloride Acetic chloride acetochlor [ANSI, WSSA] Acetyl chloride, 1M solution in dichloromethane, AcroSeal Acetyl chloride, reagent grade, ACS Acetyl chloride, synthesis grade Acetyl chloride1M solution in dichloromethaneAcroSeal§3 Acetylchlorid acetylchloride313 ACETYLCLORIDE acid chloride CH3COCl EINECS 200-865-6 Ethanoic acid chloride ethanoyl chloride Ethanoylcholride Lidocaine Impurity 38 MFCD00000719
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- 1.3 CAS No.
- 75-36-5
- 1.4 CID
- 6367
- 1.5 EINECS(EC#)
- 200-865-6
- 1.6 Molecular Formula
- C2H3ClO (isomer)
- 1.7 Inchi
- InChI=1S/C2H3ClO/c1-2(3)4/h1H3
- 1.8 InChIkey
- WETWJCDKMRHUPV-UHFFFAOYSA-N
- 1.9 Canonical Smiles
- CC(=O)Cl
- 1.10 Isomers Smiles
- CC(=O)Cl
2. Properties
- 2.1 Density
- 1.104
- 2.1 Melting point
- -112℃
- 2.1 Boiling point
- 51℃
- 2.1 Refractive index
- 1.3876-1.3896
- 2.1 Flash Point
- 4℃
- 2.2 Precise Quality
- 77.98720
- 2.2 PSA
- 17.07000
- 2.2 logP
- 0.77170
- 2.2 Solubility
- Miscible with acetone, chloroform, glacial acetic acid, petroleum ether, ether and benzene.
- 2.3 VaporDensity
- 2.7 (vs air)
- 2.4 Appearance
- colourless to light yellow liquid with a pungent
- 2.5 Atmospheric OH Rate Constant
- 9.10e-15 cm3/molecule*sec
- 2.6 Storage
- Acetic chloride should be stored in a segregated and approved area, away from incompatiblessuch as oxidizing agents, alkalis and moisture. The container of acetic chloride shouldbe kept in a cool, well-ventilated area, tightly sealed until ready for use. Users should avoidall possible sources of ignition, i.e., spark or flames.
- 2.7 Autoignition Temperature
- 734 °F (USCG, 1999)
- 2.8 Chemical Properties
- It appears as colorless fuming liquid with a strong odor and eye irritation effect. The relative density of 1.1051 (20 ° C), the melting point of-112 ° C, the boiling point of 51-52 ° C and the flash point is 4.4 ° C (closed dish). In the wet air, it can slowly undergo decomposition and give white smoke. When coming across water, it can be violently hydrolyzed into acetic acid and hydrogen chloride, and thus should be sealed for storage. It is miscible with benzene, acetone, chloroform, ether, glacial acetic acid and petroleum ether. Liquid is heavier than water with the vapor being heavier than air. Its chemical nature is lively. It can have metathesis reaction with many compounds. Acetyl chloride can bind to the thiol group in the protein, and therefore being toxic to humans. It is an important kind of acetylation agents with its acylation capability being stronger than acetic anhydride. It is widely used in organic synthesis, being also the catalyst for the chlorination of carboxylic acids. It is manufactured through the mixing of glacial acetic acid and phosphorus trichloride in cold condition with further heating, followed by dehydrochloration distillation.
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- 2.9 Color/Form
- Colorless fuming liquid
- 2.10 Corrosivity
- Corrosive
- 2.11 Decomposition
- Hazardous decomposition products formed under fire conditions - Carbon oxides, hydrogen chloride gas.
- 2.12 Heat of Combustion
- -6,000 btu/lb = -3,000 cal/g = -140X10X5 J/kg
- 2.13 Heat of Vaporization
- 160 btu/Lb = 88 cal/g = 3.7X10X5 J/kg
- 2.14 Odor
- Pungent odor
- 2.15 Water Solubility
- Highly flammable
- 2.16 Spectral Properties
- Index of refraction: 1.3898 at 20 deg C/D
MAX ABSORPTION (PETROLEUM ETHER): 220 NM (LOG E= 2.01); SADTLER REF NUMBER: 6030 (IR, PRISM) (GAS)
IR: 6165 (Coblentz Society Spectral Collection)
UV: 420 (Sadtler Research Laboratories Spectral Collection)
NMR: 167 (Varian Associates NMR Spectra Catalogue)
MASS: 97 (Atlas of Mass Spectral Data, John Wiley & Sons, New York)
- 2.17 Stability
- Stability Highly flammable. Reacts violently with DMSO, water, lower alcohols, and amines to generate toxic fumes. May form an explosive mixture with air. Note low flash point. Incompatible with water, alcohols, amines, strong bases, strong oxidizing agents, most common metals.
- 2.18 StorageTemp
- Store below +15°C.
- 2.19 Surface Tension
- 26.7 dynes/cm at 14.8 °C in contact with vapor
3. Use and Manufacturing
- 3.1 Definition
- A liquid acyl chlorideused as an acetylating agent.
- 3.2 General Description
- A colorless, fuming liquid with a pungent odor. Density 9.2 lb / gal. Flash point 40°F. Vapor, which is heavier than air, irritates the eyes and mucous membranes. Corrosive to metals and tissue.Acetyl chloride, CH30CCI, can be prepared by treatment ofacetic acid with various reagents, such as PCl3 SOCl2 or COCI2. It can be prepared by chlorination of acetic anhydride in several different ways, by reaction of methyl chloride with carbon monoxide in the presence of catalysts, by reaction ofketene with HCI, or by partial hydrolysis of 1, 1, l-trichloroethane, Acetyl chloride hydrolyzes in the presence of water to give acetic acid. It reacts with ammonia and amines to give acetamides. Reaction with alcohols gives the corresponding acetate esters. Acetyl chloride will add across unsaturated bonds in the presence ofsuitable catalysts to give halogenated ketones.
- 3.3 Potential Exposure
- Acetyl chloride is used in organic synthesis as an acetylating agent and in testing for water and/ or cholesterol in organic liquids, in the pharmaceutical industry and in pesticide manufacture.
- 3.4 Purification Methods
- Reflux acetyl chloride with PCl5 for several hours to remove traces of acetic acid, then distil it. Redistil it from one-tenth its volume of dimethylaniline or quinoline to remove free HCl. A.R. quality is freed from HCl by pumping it for 1hour at -78o and distilling it into a trap at -196o. [Beilstein 2 IV 395.] LACHRYMATORY.
- 3.5 Shipping
- UN1717 Acetyl chloride, Hazard Class: 3; Labels: 3-Flammable liquid, 8-Corrosive material
- 3.6 Usage
- Acetyl Chloride is a very useful synthetic intermediate. It is a derivative of acetic acid, a weak acid, used as a reagent in numerous industrial processes. It is a chemical for acetylation in the synthesis or derivatization of organic compounds.
4. Safety and Handling
- 4.1 Symbol
- GHS02, GHS05, GHS07
- 4.1 Hazard Codes
- C
- 4.1 Signal Word
- Danger
- 4.1 Risk Statements
- R11;R14;R34
- 4.1 Safety Statements
- S1/2;S9;S16;S26;S45
- 4.1 Packing Group
- II
- 4.1 Other Preventative Measures
- SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.
If material not on fire and not involved in fire: Keep sparks, flames, and other sources of ignition away. Keep material out of water sources and sewers. Build dikes to contain flow as necessary. Attempt to stop leak if without undue personnel hazard. Use water spray to knock-down vapors. Do not use water on material itself. Neutralize spilled material with crushed limestone, soda ash, or lime.
Personnel protection: Avoid breathing vapors. Keep upwind. ... Avoid bodily contact with the material. ... Do not handle broken packages unless wearing appropriate personal protective equipment. Wash away any material which may have contacted the body with copious amounts of water or soap and water.
Evacuation: If material leaking (not on fire) consider evacuation from downwind area based on amount of material spilled, location and weather conditions.
PROTECT FROM WATER. - View all
- 4.2 Hazard Class
- 3
- 4.2 Hazard Declaration
- H225-H302-H314
- 4.2 Cleanup Methods
- Cover any spills with sufficient amt of sodium bicarbonate. Remove the mixture in a container such as a fiber drum, plastic bag or carton box for easy disposal in an incinerator, and dispose by burning in a furnace. Wash the spilled spot thoroughly with water.
Transfer or remove slowly by discharging into a plastic or glass vessel containing sodium bicarbonate. Mix thoroughly and transfer slowly to a large vessel containing water while stirring.
Eliminate all ignition sources. Stop or control the leak, if this can be done without undue risk. Approach release from upwind. Control runoff and isolate discharged material for proper disposal.
Environmental considerations: Land spill: Dig a pit, pond, lagoon, holding area to contain liquid or solid material. /SRP: If time permits, pits, ponds, lagoons, soak holes, or holding areas should be sealed with an impermeable flexible membrane liner./ Dike surface flow using soil, sand bags, foamed polyurethane, or foamed concrete. Absorb bulk liquid with fly ash, cement powder or commercial sorbents. Neutralize with agricultural lime (CaO), crushed limestone (CaCO3) or sodium bicarbonate (NaHCO3). Apply "universal" gelling agent to immobilize spill.
Environmental considerations: Water spill: Neutralize with agricultural lime (CaO), crushed limestone (CaCO3), or sodium bicarbonate (NaHCO3). Use mechanical dredges or lifts to remove immobilized masses of pollutants and precipitates.
Environmental considerations: Air spill: Apply water spray or mist to knock down vapors. Vapor knockdown water is corrosive or toxic and should be diked for containment. - View all
- 4.3 DisposalMethods
- Generators of waste (equal to or greater than 100 kg/mo) containing this contaminant, EPA hazardous waste number U006, must conform with USEPA regulations in storage, transportation, treatment and disposal of waste.
Acetyl chloride is a waste chemical stream constituent which may be subjected to ultimate disposal by controlled incineration.
A potential candidate for liquid injection incineration at a temperture range of 650 to 1,600 deg C and a residence time 0.1 to 2 seconds. A potential candidate for rotary kiln incineration at a temperature range of 820 to 1,600 deg C and residence times of seconds for liquids and gases, and hours for solids. A potential candidate for fluidized bed incineration at a temperature range of 450 to 980 deg C and residence times of seconds for liquids and gases, and longer for solids.
- 4.4 DOT Emergency Guidelines
- If ... THERE IS NO FIRE, go directly to the Table of Initial Isolation and Protective Action Distances /(see table below)/ ... to obtain initial isolation and protective action distances. IF THERE IS A FIRE, or IF A FIRE IS INVOLVED, go directly to the appropriate guide /(see guide(s) below)/ and use the evacuation information shown under PUBLIC SAFETY. Table of Isolation and Protective Action Distances for Acetyl chloride (when spilled in water)
Small Spills (from a small package or small leak from a large package) -------------------- First ISOLATE in all Directions 30 meters (100 feet) Then PROTECT persons Downwind during DAY: 0.1 kilometers (0.1 miles) Then PROTECT persons Downwind during NIGHT: 0.4 kilometers (0.3 miles) ==================== Large Spills (From a large package or from many small packages) -------------------- First ISOLATE in all Directions 120 meters (400 feet) Then PROTECT persons Downwind during DAY: 1.1 kilometers (0.7 miles) Then PROTECT persons Downwind during NIGHT: 3.5 kilometers (2.2 miles)
Table of Water-Reactive Materials Which Produce Toxic Gases Materials Which Produce Large Amounts of Toxic-by-Inhalation (TIH) Gas(es) When Spilled in Water
Name of Material TIH Gas(es) Produced Acetyl chloride Hydrogen chloride (HCl)
/GUIDE 155: SUBSTANCES - TOXIC AND/OR CORROSIVE (FLAMMABLE/WATER-SENSITIVE)/ Fire or Explosion: HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames. Vapors form explosive mixtures with air: indoors, outdoors and sewers explosion hazards. Most vapors are heavier than air. They will spread along ground and collect in low or confined areas (sewers, basements, tanks). Vapors may travel to source of ignition and flash back. Those substances designated with a "P" may polymerize explosively when heated or involved in a fire. Substance will react with water (some violently) releasing flammable, toxic or corrosive gases and runoff. Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated or if contaminated with water.
/GUIDE 155: SUBSTANCES - TOXIC AND/OR CORROSIVE (FLAMMABLE/WATER-SENSITIVE)/ Health: TOXIC; inhalation, ingestion or contact (skin, eyes) with vapors, dusts or substance may cause severe injury, burns, or death. ... Reaction with water or moist air will release toxic, corrosive or flammable gases. Reaction with water may generate much heat which will increase the concentration of fumes in the air. Fire will produce irritating, corrosive and/or toxic gases. Runoff from fire control or dilution water may be corrosive and/or toxic and cause pollution.
/GUIDE 155: SUBSTANCES - TOXIC AND/OR CORROSIVE (FLAMMABLE/WATER-SENSITIVE)/ Public Safety: CALL Emergency Response Telephone Number ... . As an immediate precautionary measure, isolate spill or leak area in all directions for at least 50 meters (150 feet) for liquids and at least 25 meters (75 feet) for solids. Keep unauthorized personnel away. Stay upwind. Keep out of low areas. Ventilate enclosed areas.
/GUIDE 155: SUBSTANCES - TOXIC AND/OR CORROSIVE (FLAMMABLE/WATER-SENSITIVE)/ Protective Clothing: Wear positive pressure self-contained breathing apparatus (SCBA). Wear chemical protective clothing that is specifically recommended by the manufacturer. It may provide little or no thermal protection. Structural firefighters' protective clothing provides limited protection in fire situations ONLY; it is not effective in spill situations where direct contact with the substance is possible.
/GUIDE 155: SUBSTANCES - TOXIC AND/OR CORROSIVE (FLAMMABLE/WATER-SENSITIVE)/ Evacuation: ... Fire: If tank, rail car or tank truck is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions.
/GUIDE 155: SUBSTANCES - TOXIC AND/OR CORROSIVE (FLAMMABLE/WATER-SENSITIVE)/ Fire: Note: Most foams will react with the material and release corrosive/toxic gases. ... Small fires: CO2, dry chemical, dry sand, alcohol-resistant foam. Large fires: Water spray, fog or alcohol-resistant foam. ... Move containers from fire area if you can do it without risk. Use water spray or fog; do not use straight streams. Fire involving tanks or car/trailer loads: Fight fire from maximum distance or use unmanned hose holders or monitor nozzles. Do not get water inside containers. Cool containers with flooding quantities of water until well after fire is out. Withdraw immediately in case of rising sound from venting safety devices or discoloration of tank. ALWAYS stay away from tanks engulfed in fire.
/GUIDE 155: SUBSTANCES - TOXIC AND/OR CORROSIVE (FLAMMABLE/WATER-SENSITIVE)/ Spill or Leak: ELIMINATE all ignition sources (no smoking, flares, sparks or flames in immediate area). All equipment used when handling the product must be grounded. Do not touch damaged containers or spilled material unless wearing appropriate protective clothing. Stop leak if you can do it without risk. A vapor suppressing foam may be used to reduce vapors. ... DO NOT GET WATER on spilled substance or inside containers. Use water spray to reduce vapors or divert vapor cloud drift. Avoid allowing water runoff to contact spilled material. Prevent entry into waterways, sewers, basements or confined areas. Small spills: Cover with DRY earth, DRY sand or other non-combustible material followed with plastic sheet to minimize spreading or contact with rain. Use clean non-sparking tools to collect material and place it into loosely covered plastic containers for later disposal.
/GUIDE 155: SUBSTANCES - TOXIC AND/OR CORROSIVE (FLAMMABLE/WATER-SENSITIVE)/ First Aid: Move victim to fresh air. Call 911 or emergency medical service. Give artificial respiration if victim is not breathing. Do not use mouth-to-mouth method if victim ingested or inhaled the substance; give artificial respiration with the aid of a pocket mask equipped with a one-way valve or other proper respiratory medical device. Administer oxygen if breathing is difficult. Remove and isolate contaminated clothing and shoes. In case of contact with substance, immediately flush skin or eyes with running water for at least 20 minutes. For minor skin contact, avoid spreading material on unaffected skin. Keep victim warm and quiet. Effects of exposure (inhalation, ingestion or skin contact) to substance may be delayed. Ensure that medical personnel are aware of the material(s) involved and take precautions to protect themselves. - View all
- 4.5 RIDADR
- UN 1717
- 4.5 Fire Fighting Procedures
- Evacuate surrounding area.
If material on fire or involved in fire: Do not extinguish fire unless flow can be stopped or safely confined. Use dry chemical or carbon dioxide. Do not use water on material itself. If large quantities of combustibles are involved, use water in flooding quantities as spray and fog. Use water spray to knock-down vapors. Cool all affected containers with flooding quantities of water. Apply water from as far a distance as possible.
DO NOT use water or foam directly on spilled material. Violent reaction may result. Use dry chemical or carbon dioxide only. Approach fire from upwind to avoid hazardous vapors and toxic decomposition products. Fight fire from protected location or maximum possible distance.
Evacuation: If fire becomes uncontrollable or container is exposed to direct flame - consider evacuation of one-third (1/3) mile radius.
- 4.6 FirePotential
- DANGEROUS, WHEN EXPOSED TO HEAT OR FLAME. ...
- 4.7 Safety Profile
- Poison by inhalation. Moderately toxic by ingestion. A human systemic irritant by inhalation. Violent hydrolysis reaction with water or steam produces heat, acetic acid, HCl, and other corrosive chlorides. May decompose during preparation. Dangerous fire hazard when exposed to heat or flame. Explosion hazard by spontaneous chemical reaction with dimethyl sulfoxide or ethanol. Also incompatible with Pcb. When heated to decomposition it emits highly toxic fumes of phosgene and Cl-. To fight fire, use CO2 or dry chemical. See also CHLORIDES
- 4.8 Caution Statement
- P210-P280-P305 + P351 + P338-P310
- 4.8 Formulations/Preparations
- /Many/ grades of purity: commercial
- 4.9 Incompatibilities
- ticide manufacture. Incompatibilities: Avoid contact with moisture, steam, water, alcohols, dimethylsulfoxide, strong bases; phosphorus trichloride; oxidizers, and amines, since violent reactions may occur. Keep away from heat, fire, and welding operations.
- 4.10 WGK Germany
- 1
- 4.10 RTECS
- AO6390000
- 4.10 Protective Equipment and Clothing
- Personnel protection: ... Wear positive pressure self-contained breathing apparatus. ... Wear appropriate chemical protective clothing.
Safety goggles; rubber gloves; self-contained breathing apparatus
SRP: Local exhaust ventilation should be applied wherever there is an incidence of point source emmissions or dispersion of regulated contaminants in the work area. Ventilation control of the contaminant as close to its point of generation is both the most economical and safest method to minimize personnel exposure to airborne contaminants.
- 4.11 Reactivities and Incompatibilities
- Water reactive. Violent exothermic decomposition with water produces corrosive hydrochloric and acetic acids. Reacts violently with alcohols, alkalies, amines, and strong oxidizing materials.
VIOLENT HYDROLYSIS REACTION WITH WATER OR STEAM PRODUCES HEAT, ACETIC ACID, HYDROCHLORIC ACID (HCL), AND OTHER CORROSIVE CHLORIDES. ALSO INCOMPATIBLE WITH PCL3.
Decomposed violently by water or alcohol.
Use of a free flame instead of a heating bath to distill acetyl chloride produced from acetic acid and phosphorus trichloride caused the residual phosphonic (phosphorous) acid to decompose violently to give spontaneously flammable phosphine. Two later explosions in the same preparative system after reflux but before distillation from a water bath may have been due to ingress of air into the cooling flask and ignition of traces of phosphine.
EXPLOSION HAZARD: BY SPONTANEOUS CHEMICAL REACTION, ON CONTACT WITH WATER, DIMETHYL SULFOXIDE OR ETHANOL.
- 4.12 Skin, Eye, and Respiratory Irritations
- Irritating to skin, eyes, and respiratory system.
A human systemic irritant by inhalation.
- 4.13 Safety
- Hazard Codes:F,C
Risk Statements:11-14-34
11:Highly Flammable
14:Reacts violently with water
34:Causes burns
Safety Statements:9-16-26-45-1/2
9:Keep container in a well-ventilated place
16:Keep away from sources of ignition - No smoking
26:In case of contact with eyes, rinse immediately with plenty
of water and seek medical advice
45:In case of accident or if you feel unwell, seek medical
advice immediately (show label where possible)
1/2:Keep locked up and out of the reach of children
RIDADR:UN 1717 3/PG 2
WGK Germany:1
HazardClass:3
PackingGroup:II
HS Code:29159080
Hazardous Substances Data:75-36-5(Hazardous Substances Data)
- 4.14 Sensitive
- Moisture Sensitive
- 4.15 Specification
-
colourless to light yellow liquid with a pungent
Safety Statements:9-16-26-45-1/2
9:Keep container in a well-ventilated place
16:Keep away from sources of ignition - No smoking
26:In case of contact with eyes, rinse immediately with plenty
of water and seek medical advice
45:In case of accident or if you feel unwell, seek medical
advice immediately (show label where possible)
1/2:Keep locked up and out of the reach of children
- 4.16 Toxicity
- Vapor irritates mucous membranes. Ingestion of liquid or contact with eyes or skin causes severe irritation.
5. MSDS
2.Hazard identification
2.1 Classification of the substance or mixture
Flammable liquids, Category 2
Skin corrosion, Category 1B
2.2 GHS label elements, including precautionary statements
| Pictogram(s) |   |
| Signal word | Danger |
| Hazard statement(s) | H225 Highly flammable liquid and vapour H314 Causes severe skin burns and eye damage |
| Precautionary statement(s) | |
| Prevention | P210 Keep away from heat, hot surfaces, sparks, open flames and other ignition sources. No smoking. P233 Keep container tightly closed. P240 Ground and bond container and receiving equipment. P241 Use explosion-proof [electrical/ventilating/lighting/...] equipment. P242 Use non-sparking tools. P243 Take action to prevent static discharges. P280 Wear protective gloves/protective clothing/eye protection/face protection. P260 Do not breathe dust/fume/gas/mist/vapours/spray. P264 Wash ... thoroughly after handling. |
| Response | P303+P361+P353 IF ON SKIN (or hair): Take off immediately all contaminated clothing. Rinse skin with water [or shower]. P370+P378 In case of fire: Use ... to extinguish. P301+P330+P331 IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. P363 Wash contaminated clothing before reuse. P304+P340 IF INHALED: Remove person to fresh air and keep comfortable for breathing. P310 Immediately call a POISON CENTER/doctor/\u2026 P321 Specific treatment (see ... on this label). P305+P351+P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. |
| Storage | P403+P235 Store in a well-ventilated place. Keep cool. P405 Store locked up. |
| Disposal | P501 Dispose of contents/container to ... |
2.3 Other hazards which do not result in classification
none
7. Synthesis Route
75-36-5Total: 136 Synthesis Route
8. Other Information
- 8.0 Usage
- Acetyl chloride acts as a reagent for the preparation of esters and amides of acetic acid. It is also useful an important reactant in Friedel-Crafts reactions as well as the introduction of an acetyl group. It serves as a starting material in the production of pharmaceutical, new plating complexing agent, acylation agent and synthetic organic intermediates.
- 8.1 Usage
- Acetyl chloride acts as a reagent for the preparation of esters and amides of acetic acid. It is also useful as an important reactant in Friedel-Crafts reactions as well as in the introduction of an acetyl group. It serves as a starting material in the production of pharmaceutical, new plating complexing agent, acylation agent and synthetic organic intermediates.
- 8.2 Merck
- 14,85
- 8.3 BRN
- 605303
- 8.4 Uses
- Acetyl Chloride is a very useful synthetic intermediate. It is a derivative of acetic acid, a weak acid, used as a reagent in numerous industrial processes. It is a chemical for acetylation in the synthesis or derivatization of organic compounds.
- 8.5 Physical and chemical properties
- It appears as colorless fuming liquid with a strong odor and eye irritation effect. The relative density of 1.1051 (20 ° C), the melting point of-112 ° C, the boiling point of 51-52 ° C and the flash point is 4.4 ° C (closed dish). In the wet air, it can slowly undergo decomposition and give white smoke. When coming across water, it can be violently hydrolyzed into acetic acid and hydrogen chloride, and thus should be sealed for storage. It is miscible with benzene, acetone, chloroform, ether, glacial acetic acid and petroleum ether. Liquid is heavier than water with the vapor being heavier than air. Its chemical nature is lively. It can have metathesis reaction with many compounds. Acetyl chloride can bind to the thiol group in the protein, and therefore being toxic to humans. It is an important kind of acetylation agents with its acylation capability being stronger than acetic anhydride. It is widely used in organic synthesis, being also the catalyst for the chlorination of carboxylic acids. It is manufactured through the mixing of glacial acetic acid and phosphorus trichloride in cold condition with further heating, followed by dehydrochloration distillation.
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- 8.6 Dangerous situation
- (1) It has corrosive effect against the skin and mucous membranes with strong irritant effect on the eyes.
(2) It is easily flammable with the burning point being 390 ℃ and a greater risk of combustion. Its vapor can form an explosive mixture with air with the explosion limit remaining not be determined. Since the vapor is heavier than air, it can spread to a considerable distance and cause ignition of a source of fire and further propagate the flame back. It can have violent reaction when coming across water and alcohol. When being heated to decomposition, it can release HCl and highly toxic phosgene gas.
- 8.7 The main purpose
- Acetyl chloride is the most commonly used acetylating agent with reaction with alcohol and phenol generating acetate ether. Its reaction with ammonia can generate acetamide with its interaction with primary amine and secondary amine to generate N-substituted acetamide.
It can be used for the manufacturing of pharmaceutical industry, pesticide manufacturing, acetyl derivatives and dyes. It can be used as the reagents for the determination of phosphorus, cholesterol, water content contained in organic solvents, nitroso, hydroxyl and tetraethyl lead.
Acetyl chloride is the most important acyl halide and can be manufactured through the reaction between glacial acetic acid and thionyl chloride or phosphorus trichloride and phosphorus pentachloride.
- 8.8 Harmful effects and symptoms of poisoning
- Acetyl chloride is a kind of stimulant and corrosive with contact with the skin being able to cause burns. Its steam can strongly irritate the eye and mucous membranes. Human’s inhalation of 2 ppm will be able to feel stimulating effect. Short-term exposure to higher concentrations of acetyl chloride may cause death or permanent damage. The poisoning amount of the aquatic animal is estimated to be in the range of 10 to 100 ppm.
- 8.9 Chemical properties
- It appears as colorless transparent liquid smoke with irritating smell. It is miscible with ether, acetic acid and benzene.
- 8.10 Uses
- 1. It is a kind of acetylating agent, being used as raw materials for pesticides and medicine, or the intermediates for the manufacturing of water treatment agent ethylidene diphosphate.
2. It can be used for the analysis of reagents as well as used for the preparation of acetyl derivatives and dyes
3. It can be used for organic synthesis, dyes and pharmaceutical industries
4. It can be used as the raw materials of pesticides and pharmaceutical as well as the intermediate for the manufacture of water treatment agent ethylene diphosphate. Moreover, it can also be used for the manufacture of new electroplating complexing agent. Acetyl chloride is an important acetylating agent with the acylation capability being stronger than acetic anhydride. It is widely used in organic synthesis and dyes. It is also the catalyst for the carboxylic acid to have chlorination reaction as well as being used for hydroxyl and amino quantitative analysis.
5. This product can be used as raw material for organic synthesis, used in the production of pesticides, pharmaceuticals, new electroplating complexing agent, the catalyst for carboxylic acid to have chlorination, acetylation agent, and other kinds of fine organic synthesis intermediates. - View all
- 8.11 Production method
- Industrial, acetyl chloride can be manufactured through the reaction between ethylene with hydrogen chloride, or the reaction between sodium acetate, sulfur dioxide and chlorine. The laboratory can apply acetic acid, sodium acetate or acetic anhydride to have reaction with a variety of chlorination agents. For example, it can be obtained through the reaction between acetic anhydride with chlorosulfonic acid (or hydrogen chloride, carbon tetrachloride, phosgene); or obtained through the reaction between glacial acetic acid and benzoyl chloride (or silicon tetrachloride, phosphorus trichloride, chlorinated sulfurous acid and phosphorus pentachloride,). OPERATION EXAMPLE 1: Ingredient ratio (molar ratio): glacial acetic acid: phosphorus trichloride = 3: 1.2. Glacial acetic acid was added to the reactor and stirred slowly. Phosphorus trichloride was added drop-wise over 10-15 min at room temperature. The reaction mixture is subjecting to heating to increase reaction temperature and subject to reaction being maintained at 40-50 °C for 0.5 h. The reaction product is static with the separation obtaining crude product of acetyl chloride and the yield of about 70%.
Operation Example 2 Into a 3 L three-necked flask, add 360 g (6 mol) of glacial acetic acid and 552 g of toluene; heat to 50 °C, and add dropwise 510 g (3 mol) of silicon tetrachloride over 30 min. Keep the temperature at 50 ° C to until hydrogen chloride gas stops being released. Then apply fractionation, steam to until the temperature of the top of the column reaches 80-85 ℃ to obtain the crude product. The fine product is further subject to re-distillation. Take the 50-65 °C fractions and obtain 400 g of acetyl chloride with the yield being 85%. Fixed consumption amount of raw materials: glacial acetic acid: 850kg/t, phosphorus trichloride: 1950kg/t. - View all
- 8.12 Hazards & Safety Information
- Category Flammable liquids
Toxic grading poisoning
Acute Toxicity Oral-Rat LD50: 910 mg/kg
Dangerous properties of explosives being corrosive to the skin, eyes and mucous membrane;
Flammable and hazardous properties it is flammable in case of fire, high temperature and oxidant; at high temperature, it can be subject to decomposition to release toxic phosgene; it can release toxic chloride when coming across water;
Storage and transportation characteristics Treasury: ventilation, low-temperature and drying; store separately from oxidants and acids;
Extinguishing agent dry powder, dry sand, dry stone powder, carbon dioxide, foam
- 8.13 Description
- Acetic chloride is a colourless to light yellow liquid with a pungent and choking odour. Acetic chloride is highly flammable and reacts violently with DMSO, water, lower alcohols, and amines to generate toxic fumes. Along with air, acetic chloride may form an explosive mixture. It is incompatible with water, alcohols, amines, strong bases, strong oxidising agents, and most common metals. On decomposition when heated, acetic chloride produces carbon monoxide, carbon dioxide, hydrogen chloride, and phosgene.
- 8.14 Chemical Properties
- colourless to light yellow liquid with a pungent
- 8.15 Chemical Properties
- Acetic chloride is a colorless to light yellow liquid with a pungent and choking odor. Acetic chloride is highly flammable, reacts violently with dimethyl sulfoxide (DMSO), water, lower alcohols, and amines to generate toxic fumes. Together with air, acetic chloride may form an explosive mixture. It is incompatible with water, alcohols, amines, strong bases, strong oxidizing agents, and most common metals. On decomposition when heated, acetic chloride produces carbon monoxide, carbon dioxide, hydrogen chloride, and phosgene.
- 8.16 Chemical Properties
- Acetyl chloride is a highly flammable, colorless, fuming liquid with a pungent odor
- 8.17 Uses
-
Acetyl chloride can be used as:
- A degradation agent in the degradation of polyoxyethylene glycol monoalkyl ethers to determine the degree of ethoxylation using chromatography-mass spectrometry (MS).
- A reagent with alcohols for the esterification of carboxylic acids, N-boc deprotection, and phosphoramide solvolysis reactions.
9. Computational chemical data
- Molecular Weight: 78.49762g/mol
- Molecular Formula: C2H3ClO
- Compound Is Canonicalized: True
- XLogP3-AA: 0.8
- Exact Mass: 77.9872424
- Monoisotopic Mass: 77.9872424
- Complexity: 33
- Rotatable Bond Count: 0
- Hydrogen Bond Donor Count: 0
- Hydrogen Bond Acceptor Count: 1
- Topological Polar Surface Area: 17.1
- Heavy Atom Count: 4
- Defined Atom Stereocenter Count: 0
- Undefined Atom Stereocenter Count: 0
- Defined Bond Stereocenter Count: 0
- Undefined Bond Stereocenter Count: 0
- Isotope Atom Count: 0
- Covalently-Bonded Unit Count: 1
- CACTVS Substructure Key Fingerprint: AAADcQBAIAAEAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAGgIAAAAAAAKAgAACAAAAAAAIAEAYAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAA==
10. Question & Answer
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Description Acetyl Chloride is a colorless to pale yellow, fuming liquid with a pungent odor. It is commonly used in the production of pharmaceuticals and pesticides. Acyl halides, like acetyl chlori..
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Are you interested in the pharmaceutical applications of Acetyl chloride? Let's explore its uses in the field of pharmaceuticals. Acetyl chloride is an organic compound that is commonly used as a key ..
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From Arihant Test Drive, JEE Advanced 2020; Ramchaya builiding, Daryanganj, New Delhi, India; January 2019, p. 342: Napthalene gives 1-ethylnapthalene on reaction with ethyl choride in the presence o..
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Introduction Alpha-Acetyl chloride benzene is a molecule with C-2 symmetry, with a center point located on the axis. This compound is commonly used as an intermediate for the production of fine chemic..
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