트라이클로로아세틸 염화물

Trichloroacetyl chloride

HCID 6420CAS 76-02-8

기본 정보

표준 SMILES
O=C(Cl)C(Cl)(Cl)Cl
InChIKey
PVFOMCVHYWHZJE-UHFFFAOYSA-N
분자식
C2Cl4O
평균 분자량
181.8 g/mol
단동위원소 질량
179.87032534

개요

Trichloroacetyl chloride appears as a colorless volatile liquid with a strong odor. Denser than water. Contact severely irritates skin, eyes and mucous membranes. May be very toxic by ingestion and inhalation. May be combustible.

이름 및 식별자

우선 이름
Trichloroacetyl chloride
IUPAC
2,2,2-trichloroacetyl chloride
현지명
트라이클로로아세틸 염화물
영어명
Trichloroacetyl chloride
분자식
C2Cl4O
분자량
181.83

이름 및 동의어

TRICHLOROACETYL CHLORIDE76-02-82,2,2-trichloroacetyl chlorideSuperpaliteAcetyl chloride, trichloro-TrichloroacetochlorideTrichloroacetic acid chlorideDTXSID9034070Acetyl chloride, 2,2,2-trichloro-9SN86T76Y6NSC-190466DTXCID7014070
이름 더 보기
트라이클로로아세틸염화물트라이클로로아세틸 염화물트리클로로아세틸클로라이드Trichloroacetic chlorideGreen cross gastrichloroacetylTrichloroacetyl chlotrichloro-acetylchlorid
RefChem:191002200-926-7CCl3COClNSC 190466trichloroacetylchlorideCCRIS 6764HSDB 6321Trichloro-acetylchloride

데이터베이스 식별자

CAS
76-02-8
PubChem CID
6420
DTXSID
DTXSID9034070
ChEMBL
CHEMBL3186657
UNII
9SN86T76Y6
EC Number
200-926-7
Nikkaji
J1.472I

물성

구조 계산 물성

XLogP
2.6
극성 표면적
17.1 Ų
수소 결합 공여자 수
0
수소 결합 수용자 수
1
회전 가능 결합 수
0
무거운 원자 수
7

실험 및 물리화학적 성질

Chemical Classes · 2건

Toxic Gases & Vapors -> Acid Halides

Corrosives

SpringerMaterials PropertiesSchoenflies notation
Density · 3건

1.654 at 32 °F (EPA, 1998) - Denser than water; will sink

1.6202 at 20 °C/4 °C

1.629 @25 °C

Color/FormLiquid
Solubility · 2건

Sol in ether

Sol in alcohol

Boiling Point · 3건

244 °F at 760 mmHg (EPA, 1998)

244 °F

117.9 °C

물리화학적 성질

녹는점
-57 °C · -57 °C
끓는 점
114 · 114-116 °C(lit.)
밀도
1.629 g/mL · 1.629 g/mL at 25 °C(lit.)
증기압
16 mm · 16 mm Hg ( 20 °C)
굴절률
20 · n20/D 1.470(lit.)
인화점
100 °C · 100 °C
화학적 성질 · 1건

Trichloroacetyl chloride is similar to dichloroacetyl chloride. It is a clear colourless liquid. Decomposes in water; soluble in alcohol.The acid chloride can be hydrolyzed at 75 – 85°C with water to form the free acid and hydrolyzed with ammonium hydroxide or concentrated sodium carbonate solution to form the salts.

안전 및 규제

GHS 분류

GHS Classification · 4건

Danger

H290 (67.5%): May be corrosive to metals [Warning Corrosive to Metals]

P234, P260, P261, P264, P264+P265, P270, P271, P273, P280, P284, P301+P317, P301+P330+P331, P302+P361+P354, P304+P340, P305+P354+P338, P316, P317, P319, P320, P321, P330, P363, P390, P391, P403+P233, P405, P406, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 160 reports by companies from 12 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

유해성 정보

Hazards IdentificationToxic/poison by inhalation (TIH/PIH)
Regulatory Information · 4건

Chemical: Acetyl chloride, trichloro-

Status: Cease Manufacture Update: 28-11-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/11166

Trichloroacetyl chloride: Does not have an individual approval but may be used under an appropriate group standard

The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)

DOT LabelCorrosive Poison Inhalation Hazard
Fire Hazards · 2건

Material may burn but does not ignite readily. Poisonous if inhaled or swallowed; skin contact poisonous. Contact may cause burns to skin and eyes. (EPA, 1998)

· Combustible material: may burn but does not ignite readily.

Health Hazards · 2건

Highly toxic by ingestion and inhalation; strong irritant to skin and tissues. (EPA, 1998)

· TOXIC and/or CORROSIVE; inhalation, ingestion or contact (skin, eyes) with vapors, dusts or substance may cause severe injury, burns or death.

Hazards SummaryExperiments conducted at Argonne showed that no gas is generated upon mixing with water. No apparent evolution of hydrochloric acid after mixing with water; A strong skin irritant; [CAMEO]

안전 및 보호

Fire Fighting · 1건

Move container from fire area if you can do so without risk. Spray cooling water on containers that are exposed to flames until well after fire is out. Keep unnecessary people away; isolate hazard area and deny entry. Stay upwind; keep out of low areas. Wear positive pressure breathing apparatus and special protective clothing.

Accidental Release Measures · 2건

· CALL 911. Then call emergency response telephone number on shipping paper. If shipping paper not available or no answer, refer to appropriate telephone number listed on the inside back cover.

· ELIMINATE all ignition sources (no smoking, flares, sparks or flames) from immediate area.

First Aid · 2건

Warning: Trichloroacetyl chloride is a strong irritant. Direct contact may result in severe dermal or corneal burns.

General First Aid:

Exposure Control and Personal Protection · 2건

· Wear positive pressure self-contained breathing apparatus (SCBA).

TIH (Toxic Inhalation Hazard) - Term used to describe gases and volatile liquids that are toxic when inhaled. Some are TIH materials themselves, e.g., chlorine, and some release TIH gases when spilled in water, e.g., chlorosilanes. [ERG 2016].

Fire Fighting Procedures · 1건

If material on fie or involved in fire: Use water in flooding quantities as fog. Use "alcohol" foam, dry chemical or carbon dioxide. Keep run-off water out of sewers and water sources. Cool all affected containers with flooding quantities of water. Apply water from as far a distance as possible.

Nonfire Spill ResponseExcerpt from ERG Guide 156 [Substances - Toxic and/or Corrosive (Combustible / Water-Sensitive)]:

독성 정보

Environmental Fate · 3건

TERRESTRIAL FATE: Data on the hydrolysis of trichloroacetyl chloride are not available. Hydrolysis of trichloroacetyl chloride is expected to be a major fate process for this compound. Based on analogy to similar compounds, acetyl chloride at 25 °C has a hydrolysis half-life of 0.8 sec(1); dichloroacetyl chloride at -20 °C has a hydrolysis rate of 0.004/min(2). An estimated Koc of 72(4,SRC), based on an estimated log Kow(3,SRC), indicates that trichloroacetyl chloride will have high mobility in soil(1,2,5,SRC); the rate of hydrolysis of trichloroacetyl chloride is expected to be so fast that leaching is unlikely(SRC).

AQUATIC FATE: Data on the hydrolysis of trichloroacetyl chloride are not available. Hydrolysis of trichloroacetyl chloride is expected to be a major fate process for this compound. Based on analogy to similar compounds, acetyl chloride at 25 °C has a half-life of 0.8X10-1/sec(1) and the hydrolysis rate of dichloroacetyl chloride is 0.004/min at -20 °C(2). An estimated BCF value of 3(3,SRC), based on an estimated log Kow(4,SRC), indicates that trichloroacetyl chloride will not bioconcentrate in an aquatic system(3,4,SRC).

ATMOSPHERIC FATE: Based on a vapor pressure of 21 mm Hg at 25 °C obtained from experimentally derived coefficients(1,SRC), trichloroacetyl chloride will exist solely in the vapor phase in the ambient atmosphere(2,SRC). Trichloroacetyl chloride is not expected to degrade appreciably in the vapor phase by reaction with photochemically produced hydroxyl radicals(3,SRC). A hydrolysis half-life of 455 years in the atmosphere was estimated by calculating gas phase hydrolysis rate constants for trichloroacetyl chloride(4). This suggests that gas phase hydrolysis is not an effective removal mechanism for this compound in the atmosphere(4,SRC).

Adverse EffectsToxic Pneumonitis - Inflammation of the lungs induced by inhalation of metal fumes or toxic gases and vapors.
Soil Adsorption/Mobility · 1건

Based on an estimated log Kow of 0.88(1,SRC), the Koc of trichloroacetyl chloride is estimated as approximately 72 using a regression-derived equation(2,SRC). According to a suggested classification scheme(3), this estimated Koc value suggests that trichloroacetyl chloride has high mobility in soil(SRC). This compound's rapid rate of hydrolysis, by analogy to acetyl chloride(4) and dichloroacetyl chloride(5), indicates that hydrolysis should preclude leaching in soil environments(SRC).

Human Toxicity Excerpts · 2건

New labelling processes installed without adequate ventilation control in an electric motor factory exposed production line workers to toxic gases. Symptoms of eye & resp tract irritation & complaints of headache, fever, chills, dizziness, malaise, general weakness, nausea, & vomiting were reported in numerous cases. Chest signs, radiographic abnormalities, reduction in ventilatory function, & blood gas abnormalities were found in some cases. Epidemiological analysis of the spatial & temporal distribution of cases supported an exposure effect relationship. Investigations suggested ozone & possibly phosgene & assoc trichloroacetyl chlorides as the toxic agents that were generated by an ultraviolet print curing arrangement & perchloroethylene used as a cleaning solvent.

Highly toxic by ingestion & inhalation.

Artificial Pollution Sources · 1건

Trichloroacetyl chloride's production and subsequent use as an intermediate in the manufacture of esters and anhydrides of trichloroacetic acid(1) and in the manufacture of the antibiotic, cephacetrile(2) may result in its release to the environment through various waste streams(SRC).

Environmental Bioconcentration · 1건

A BCF of 3 was calculated for trichloroacetyl chloride, using an estimated log Kow of 0.88(1,SRC) and a recommended regression-derived equation(2,SRC). This BCF value suggests that trichloroacetyl chloride will not bioconcentrate in aquatic organisms(2,SRC).

규제 정보

CERCLA Reportable Quantities · 1건

Releases of CERCLA hazardous substances are subject to the release reporting requirement of CERCLA section 103, codified at 40 CFR part 302, in addition to the requirements of 40 CFR part 355. Trichloroacetyl chloride is an extremely hazardous substance (EHS) subject to reporting requirements when stored in amounts in excess of its threshold planning quantity (TPQ) of 500 lbs.

안전 데이터

wgk
3
tsca
TSCA listed
rtecs
AO7140000
ridadr
UN 2442
HS 번호
29159080
risk_code
14-22-26-34-35-29

화학 및 산업

용도 및 제조

Uses · 2건

Used in organic synthesis; [HSDB]

Trichloroacetyl chloride can be used for the manufacture of the esters and the anhydrides of trichloroacetic acid.

Methods of Manufacturing · 1건

Acetyl chloride is prepared from trichloroacetic acid and various inorganic acid chlorides (e.g., SOCl2, PCl3) or with P2O5 and HCl. More useful methods are the oxidation of tetrachloroethylene with fuming sulfuric acid, oxygen, or fuming nitric acid and sulfuric acid at 18-20 °C, or from the reaction of pentachloroethane and dry oxygen under UV light. It has been obtained in 37% yield from carbon tetrachloride and carbon monoxide in the presence of aluminum chloride at 200 °C and high pressure. The most common production method is the gas-phase, photochemical oxidation of tetrachloroethylene with oxygen. The reaction is initiated with UV light, with radioactive irradiation, or it is sensitized with chlorine or iodine.

General Manufacturing InformationAcetyl chloride, 2,2,2-trichloro-: ACTIVE

응용 분야

용도Trichloroacetyl chloride can be used for the manufacture of the esters and the anhydrides of trichloroacetic acid.It was used in the preparation of dihydro-1H-benzindoles. It was also used in the synthesis of 3-alkylbenzoxazolones.

일반 설명A colorless volatile liquid with a strong odor. Denser than water. Contact severely irritates skin, eyes and mucous membranes. May be very toxic by ingestion and inhalation. May be combustible.

제조 방법 · 1건

The acetyl chloride is prepared from trichloroacetic acid and various inorganic acid chlorides (e.g., SOCl2, PCl3) or with P2O5 and HCl. More useful methods are the oxidation of tetrachloroethylene with fuming sulfuric acid, oxygen, or fuming nitric acid and sulfuric acid at 18-20°C, or from the reaction of pentachloroethane and dry oxygen under UV light. It has been obtained in 37 % yield from carbon tetrachloride and carbon monoxide in the presence of aluminum chloride at 200°C and high pressure.The most common production method is the gas-phase, photochemical oxidation of tetrachloroethylene with oxygen. The reaction is initiated with UV light, with radioactive irradiation, or it is sensitized with chlorine or iodine.

관련 반응

519건

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