ケテン

Ketene

HCID 10038CAS 12071-23-7

基本情報

標準SMILES
C=C=O
InChIKey
CCGKOQOJPYTBIH-UHFFFAOYSA-N
分子式
C2H2O
平均分子量
42.04 g/mol
単同位体質量
42.01056468

概要

Ketene appears as a colorless highly reactive gas with a penetrating odor. mp: -150 °C, bp: -56 °C. Reacts violently with water. Soluble in diethyl ether and acetone. Severely irritates the eyes, the skin and the respiratory tract. Used is the manufacture of acetic anhydride, sorbic acid, cinnamic acids, chloroacetyl chloride and other materials. Readily polymerizes and cannot be shipped or stored. Is obtained instead as needed from diketene. DIKETENE (CAS: 674-82-8; Formula: C4H2O2 ) is a colorless liquid with a pungent odor. mp: -6.5 °C; bp: 127 °C. Density 1.08 g/cm3. Reacts violently with water. Is obtained from the dimerization of ketene and can be stored and transported under refrigeration. A severe lachrymator (irritates the eyes, the respiratory tract, and the skin as well). Depolymerizes at 650 °C to give ketene.

名称と識別子

優先名称
Ketene
IUPAC
ethenone
現地名
ケテン
英語名
ketene
分子式
C2H2O
分子量
42.04

名称と別名

EthenoneKETENECarbometheneKeto-ethylene463-51-4LEP3SM032ADTXSID1052113CHEBI:48003KETOETHYLENERefChem:794269DTXCID3030682CHEBI:48002
名称をさらに表示
エテン-1-オンカルボメテンケテンエテノンcarbometeneEthen-1-oneketene ISO 9001:2015 REACH
207-336-9EthylenoneKETEN12071-23-7HSDB 633EINECS 207-336-9UNII-LEP3SM032Aoxoethylene

データベース識別子

CAS
12071-23-7、463-51-4
PubChem CID
10038
DTXSID
DTXSID1052113
ChEBI
CHEBI:48003
UNII
LEP3SM032A
EC Number
207-336-9
Nikkaji
J2.590I

物性

構造計算による物性

XLogP
0.8
極性表面積
17.1 Ų
水素結合供与体数
0
水素結合受容体数
1
回転可能結合数
0
重原子数
3

実験および物理化学的性質

Chemical Classes · 2 件

Toxic Gases & Vapors -> Other Toxic Gases & Vapors

Flammable agents - 3rd degree

SpringerMaterials PropertiesCoriolis coupling
Odor · 2 件

PENETRATING ODOR

Penetrating odor.

TasteDISAGREEABLE TASTE
Density1.45(relative gas density)
Color/Form · 2 件

COLORLESS GAS

Colorless gas.

物理化学的性質

融点
-150 ° · -150°
沸点
-56 ° · bp -56°
比重(密度)
0.66 · 0.6600
屈折率
1.304 · 1.3040 (estimate)
外見
ガス
EPAの化学物質情報
Ketene (463-51-4)

化学的性質

化学的特性Colorless gas with a sharp penetrating odor;liquefies at -56°C (-68.8°F); solidifies at-151°C (-239.8°F); soluble in alcohol andacetone, decomposed by water.

安全と法規制

GHS分類

GHS Classification · 6 件

Danger

H220 (100%): Extremely flammable gas [Danger Flammable gases]

P203, P210, P222, P260, P261, P264, P264+P265, P271, P280, P284, P302+P352, P304+P340, P305+P354+P338, P316, P317, P319, P320, P321, P332+P317, P362+P364, P377, P381, P403, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 111 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Danger

H220: Extremely flammable gas [Danger Flammable gases]

危険有害性情報

Regulatory Information · 3 件

Chemical: Ethenone

Ketene: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.

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 LabelPoison Inhalation Hazard Flammable Liquid
Fire Hazards · 2 件

Excerpt from ERG Guide 131 [Flammable Liquids - Toxic; polymerization hazard]:

Extremely flammable. Gas/air mixtures are explosive.

Health HazardsExcerpt from NIOSH Pocket Guide for Ketene:
Hazards Summary · 1 件

TLV Basis is pulmonary edema, lung damage, and eye irritation. Animal studies show that ketene is an inhalation irritant with toxicity similar to that of phosgene. [ACGIH] A severe irritant of the skin, eyes, and respiratory tract; [CAMEO] Reacts violently with water producing acetic acid; A skin, eye, and respiratory tract irritant; Inhalation may cause pulmonary edema; Chronic or repeated exposure may cause emphysema and fibrosis; [ICSC] Causes acute pulmonary edema, other changes in lungs, thorax, or respiration, convulsions, and dyspnea in lethal-concentration inhalation studies of rodents; [RTECS]

Reactive GroupKetones

安全と保護具

Fire Fighting · 2 件

Excerpt from ERG Guide 131 [Flammable Liquids - Toxic; polymerization hazard]:

Use powder, carbon dioxide. NO water. In case of fire: keep cylinder cool by spraying with water. NO direct contact with water.

First Aid Measures · 3 件

Fresh air, rest. Half-upright position. Artificial respiration may be needed. Refer for medical attention.

Remove contaminated clothes. Rinse skin with plenty of water or shower.

First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.

First Aid · 2 件

Excerpt from NIOSH Pocket Guide for Ketene:

(General first aid procedures)

Safe StorageThe substance cannot be stored or shipped.
Storage Conditions · 2 件

...CANNOT BE...STORED IN A GASEOUS STATE.

Protect containers against physical damage by shock. Outdoor or detached storage is preferable. For indoor storage, use standard combustible liquid storeroom or cabinet.

Cleanup Methods · 1 件

PERSONS NOT WEARING PROTECTIVE EQUIPMENT AND CLOTHING SHOULD BE RESTRICTED FROM AREAS OF LEAKS UNTIL CLEANUP HAS BEEN COMPLETED. IF KETENE IS LEAKED, THE FOLLOWING STEPS SHOULD BE TAKEN: 1. REMOVE ALL IGNITION SOURCES. 2. VENTILATE THE AREA OF LEAK. 3. STOP FLOW OF GAS. DISPOSAL METHODS: KETENE MAY BE DISPOSED OF BY BURNING AT A SAFE LOCATION OR IN A SUITABLE COMBUSTION CHAMBER.

毒性情報

Target OrgansEyes, skin, respiratory system
Adverse EffectsToxic Pneumonitis - Inflammation of the lungs induced by inhalation of metal fumes or toxic gases and vapors.
Exposure Routes · 2 件

The substance can be absorbed into the body by inhalation.

inhalation, skin and/or eye contact

Signs and Symptoms · 4 件

Cough. Shortness of breath. Symptoms may be delayed.

Redness.

Redness. Pain.

irritation eyes, skin, nose, throat, respiratory system; pulmonary edema

Human Toxicity Excerpts · 5 件

SEVERE PULMONARY IRRITANT CAUSING PULMONARY EDEMA IF INHALED.

STRONG IRRITANT TO SKIN & MUCOUS MEMBRANES.

TOXIC BY ... INHALATION ... .

KETENE IS ONE OF THE MOST HIGHLY IRRITANT GASES TO THE RESP TRACT; ITS TOXICITY APPEARS TO BE OF THE SAME ORDER OF MAGNITUDE AS THAT OF PHOSGENE AND ALSO RESEMBLES PHOSGENE IN ITS DELAYED ACTION ON THE RESPIRATORY SYSTEM.

For more Human Toxicity Excerpts (Complete) data for KETENE (8 total), please visit the HSDB record page.

Non-Human Toxicity Excerpts · 4 件

/IN MICE AND RATS/ CONCN OF OVER 100 PPM ... PROVED FATAL WITH DEATH OCCURRING RAPIDLY WITH ... MARKED EYE, NOSE, THROAT, & PULMONARY IRRITATION. AUTOPSIES SHOWED THAT THERE WAS DILATATION OF THE RIGHT HEART & MAJOR DAMAGE TO ALVEOLAR WALLS WITH PULMONARY EDEMA.

... REPEATED INHALATIONS AT 1 PPM IN THE RAT, CAT, & MONKEY ... SHOWED EVIDENCE OF LUNG DAMAGE ... INTERSTITIAL FIBROSIS, CELLULAR INFILTRATION, ATELECTASIS, & EMPHYSEMA /ON AUTOPSY/.

EXPOSURE OF MONKEYS TO 23 PPM IN AIR FOR FOUR HOURS CAUSED THE ANIMALS TO RUB THEIR EYES, COUGH, & BECOME LETHARGIC.

/IN GUINEA PIGS/ CONCN OF OVER 100 PPM ... PROVED FATAL WITH DEATH OCCURRING RAPIDLY WITH ... MARKED EYE, NOSE, THROAT, & PULMONARY IRRITATION. AUTOPSIES SHOWED THAT THERE WAS DILATATION OF THE RIGHT HEART & MAJOR DAMAGE TO ALVEOLAR WALLS WITH PULMONARY EDEMA.

法規制情報

Atmospheric Standards · 1 件

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. Ketene is produced, as an intermediate or a final product, by process units covered under this subpart.

安全データ

OEB
C
OEL
TWA: 0.5 ppm (0.9 mg/m3), STEL: 1.5 ppm (3 mg/m3)
IDLA
5 ppm
tsca
TSCA listed
ridadr
1955
hazard_class
2.3

化学と産業

用途と製造

Uses · 5 件

Used in the synthesis of acetic anhydride and other organic chemicals; [ACGIH] Polymerizes readily and cannot be stored. Obtained from diketene; [CAMEO]

CONVERSION OF HIGHER ACIDS INTO THEIR ANHYDRIDES

ACETYLATION IN MFR OF CELLULOSE ACETATE & ASPIRIN

PRINCIPALLY CHEM INT FOR ACETIC ANHYDRIDE FROM ACETIC ACID; FOR DEHYDROACETIC ACID AND ACETOACETIC ESTERS; FOR ACETOACETANILIDE & N,N-DIALKYLACETOACETAMIDES

Acetylating agent, generally reacting with compounds having an active hydrogen atom; reacts with ammonia to give acetamide. Starting point for making various commercially important products, especially acetic anhydride and acetate esters.

Methods of Manufacturing · 2 件

BY THERMAL DECOMPOSITION OF ACETONE, DIKETENE OR ACETIC ANHYDRIDE.

PYROLYSIS OF ACETONE OR ACETIC ACID BY PASSING ITS VAPOR THROUGH A TUBE AT 500-600 °C.

General Manufacturing InformationEthenone: ACTIVE
応用分野 · 3 件

用途有機合成原料

解説母体となる化合物CH2=CO,C2H2O(42.04)をケテンとよぶ.実験室的にはアセトンの熱分解により,工業的には酢酸の熱分解でつくられる.常温で気体.CH3COCH3 → CH2CO + CH4CH3COOH → CH2CO + H2O融点-151 ℃,沸点-56 ℃.2分子からジケテン(ケテンダイマー)が容易に生じる.ジケテンは熱分解によりケテンに戻る.ケテンはヒドロキシ基,アミノ基,メルカプト基を有する化合物と反応してアセチル誘導体を与える.

使用For the conversion of higher acids into their anhydrides; for acetylation in the manufacture of cellulose acetate and aspirin.

調製方法 · 2 件

Ketene may be prepared also by pyrolysis of acetic anhydride or phenyl acetate or diketene. Other sources are quite unsatisfactory from a standpoint of yield. Small quantities may be made conveniently by heating acetone in a “ketene lamp.” This is a glass apparatus containing a Nichrome filament, heated electrically to red heat. Larger amounts are made by passing acetone or acetic acid through a tube at 700 °C. A very brief contact time is required, so that much of the acetone is undecomposed and has to be condensed and recycled. Also, it is imperative that the reaction tube be of inert material such as porcelain, glass, quartz, copper or stainless steel. A copper tube, if used, should be protected from oxidation by an iron sheath. Inert packing may be used (glass, vanadium pentoxide, porcelain), but just as good yields are obtained with empty tubes. No catalyst is known which accelerates this decomposition at significantly lower temperatures.

純化方法Ketene is prepared by pyrolysis of acetic anhydride. Purify it by passing through a trap at -75o and collecting in a liquid-nitrogen-cooled trap. Ethylene is removed by evacuating the ethylene in an isopentane-liquid-nitrogen slush pack at -160o. Store it at room temperature in a suitable container in the dark or better at -80o, but do not store it under pressure as it may EXPLODE. It is a strong IRRITANT when inhaled and is as poisonous as phosgene. See diketene in “Heterocyclic Compounds”, Chapter 4. [Hurd Org Synth Coll Vol I 330 1941, Andreades & Carlson Org Synth Coll Vol V 679 1973.]

サプライヤー6 社

池州凯隆进出口贸易有限公司[email protected]
深圳振强药物研发有限公司+86-0755-66853366 +86-13670046396 · [email protected]
Shaanxi Didu New Materials Co. Ltd+86-86-17392712779 +86-13289823923 · [email protected]
河南天孚化工有限公司+86-0371-55170693 +86-19937530512 · [email protected]
深圳博泰尔生物技术有限公司13316949107 13316968096 · [email protected]

関連反応

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