무수부틸산

Butyric anhydride

HCID 7798CAS 106-31-0

기본 정보

표준 SMILES
CCCC(=O)OC(=O)CCC
InChIKey
YHASWHZGWUONAO-UHFFFAOYSA-N
분자식
C8H14O3
평균 분자량
158.19 g/mol
단동위원소 질량
158.09429431

개요

Butyric anhydride is a water-white liquid with an odor of rancid butter. Corrosive to metals and tissue. Low toxicity.

이름 및 식별자

우선 이름
Butyric anhydride
IUPAC
butanoyl butanoate
현지명
무수부틸산
영어명
Butyric anhydride
분자식
C8H14O3
분자량
158.2

이름 및 동의어

BUTYRIC ANHYDRIDEn-Butyric anhydrideButanoic anhydridebutanoyl butanoateButanoic acid, anhydrideButyric acid anhydrideButyryl oxiden-Butyric acid anhydrideButyranhydridButyric anhydride NButyranhydrid [Czech]Caswell No. 132A
이름 더 보기
무수부틸산뷰티르산무수물뷰티르산 무수물부티르산무수물butyricButyrloxidebutric anhydridebutylic anhydrideAKOS BBS-00004317
Anhydrid kyseliny maselnen-Butanoic anhydrideButanoic acid, 1,1'-anhydrideDTXSID8026729HSDB 5369Anhydrid kyseliny maselne [Czech]EINECS 203-383-4UNII-A88LE742VX

데이터베이스 식별자

CAS
106-31-0
PubChem CID
7798
DTXSID
DTXSID8026729
ChEMBL
CHEMBL1566369
UNII
A88LE742VX
EC Number
203-383-4
Nikkaji
J5.050D

물성

구조 계산 물성

XLogP
1.6
극성 표면적
43.4 Ų
수소 결합 공여자 수
0
수소 결합 수용자 수
3
회전 가능 결합 수
6
무거운 원자 수
11

실험 및 물리화학적 성질

Chemical Classes · 2건

Other Classes -> Acid Anhydrides, Other

Corrosives

SpringerMaterials PropertiesBoiling point
LogPlog Kow = 1.39 /estimated; value theoretical due to hydrolysis in water/
OdorPUNGENT ODOR
Density0.9668 at 20 °C/4 °C
Viscosity1.59 cP at 20 °C

물리화학적 성질

녹는점
-75 · -75--66 °C (lit.)
끓는 점
198 · 198-199 °C (lit.)
밀도
0.967 g/mL · 0.967 g/mL at 25 °C (lit.)
증기 밀도
5.45 · 5.45 (vs air)
증기압
10 mm · 10 mm Hg ( 79.5 °C)
굴절률
20 · n20/D 1.413(lit.)

화학적 성질

clear liquid

안전 및 규제

GHS 분류

GHS Classification · 6건

This chemical does not meet GHS hazard criteria for 4.8% (21 of 437) of reports.

Danger

H302 (63.4%): Harmful if swallowed [Warning Acute toxicity, oral]

P260, P264, P264+P265, P270, P280, P301+P317, P301+P330+P331, P302+P361+P354, P304+P340, P305+P354+P338, P316, P317, P321, P330, P363, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 437 reports by companies from 10 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Danger

유해성 정보

Regulatory Information · 5건

Chemical: Butanoic acid, anhydride

Butanoic acid, 1,1'-anhydride is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Butanoic acid, 1,1'-anhydride are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

Status: Active Update: 01-08-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/12002

Butyric anhydride: 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
Fire Hazards · 2건

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

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

Health Hazards · 2건

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

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

Hazards Summary · 1건

A skin and eye irritant; [HSDB] A corrosive substance that can react with moisture in the respiratory tract to form butyric acid; Can cause permanent eye damage; Inhalation of high concentrations may cause pulmonary edema; [CHEMINFO] A corrosive substance that can cause injury to the skin, eyes, mucous membranes, and respiratory tract; May cause chemical pneumonitis if inhaled; [MSDSonline]

DOT ID and Guide2739 156

안전 및 보호

Fire FightingExcerpt from ERG Guide 156 [Substances - Toxic and/or Corrosive (Combustible / Water-Sensitive)]:
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

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

General First Aid:

Firefighting Hazards · 1건

... Substance will react with water (some violently) releasing flammable, toxic or corrosive gases and runoff. When heated, vapors may form explosive mixtures with air: indoors, outdoors and sewers explosion hazards. ... Vapors may travel to source of ignition and flash back. Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated or if contaminated with water.

Exposure Control and Personal Protection· Wear positive pressure self-contained breathing apparatus (SCBA).
Fire Fighting Procedures · 1건

Use water in flooding quantities as fog. Solid streams of water may be ineffective. Cool all affected containers with flooding quantities of water. Apply water from as far a distance as possible. Use "alcohol" foam, dry chemical or carbon dioxide. Use water spray to knock-down vapors.

독성 정보

Interactions · 1건

Whole unfractionated heparin can modestly decrease tumor growth, but the dose of heparin is limited by its anticoagulant properties. To overcome this limitation... the chemical structure of heparin /was modified/ and a heparin derivative /was prepared/ by O-acylating low molecular weight heparin with butyric anhydride, producing a more potent antiproliferative compound, which is only weakly anticoagulant so that the dose may be escalated without threat of hemorrhage. ...this study... investigated the effect of this chemically modified heparin, butanoylated heparin, on the growth of lung cancer in vitro and in vivo. /It was/ found that butanoylated heparin a) significantly inhibited lung cancer cell proliferation in vitro and lung cancer growth in mice and rats; b) had very low anticoagulant effect; c) had no significant toxicity on heart, liver, kidney and lung; d) significantly although modestly induced apoptosis and decreased expression of the cell proliferation pathway consisting of mutant p53, phospho-Rb and E2F1 expression in the tumor tissues. /It was/ also found that butanoylated heparin significantly inhibited CXCL12 and CXCR4 expression, suggesting that CXCL12/CXCR4 axis may be involved in regulation of tumor growth inhibition by heparin. /It was/ concluded that chemically modified butanoylated heparin has potent antiproliferative activity against lung cancer and may represent a new chemical therapeutic agent for cancer patients.

Environmental Fate · 3건

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 10(SRC), determined from a structure estimation method(2), indicates that butyric anhydride is expected to have very high mobility in soil(SRC). However, butyric anhydride hydrolyzes to butyric acid in water(3); the neutral hydrolysis half-life at 25 °C is about 4.3 minutes based on analogy to similar anhydrides(2). Therefore leaching in soil due to rain or runoff is not expected to be an important fate process. The potential for volatilization of butyric anhydride from dry soil surfaces may exist(SRC) based upon a vapor pressure of 0.3 mm Hg at 25 °C(4) and its existence as a liquid at ambient temperatures(3).

AQUATIC FATE: Hydrolysis is the dominant fate process for butyric anhydride in water(SRC). In water, butyric anhydride hydrolyzes to butyric acid(1). Based on analogy to similar anhydrides(SRC), the neutral aqueous hydrolysis half-life of butyric anhydride at 25 °C is about 4.3 minutes(2). A base-catalyzed second-order hydrolysis rate constant of 3440 L/mole-sec(SRC) was estimated using a structure estimation method(3); this corresponds to half-lives of 17 and 1.7 minutes at pH values of 7 and 8, respectively(SRC). Due to hydrolysis, bioconcentration and volatilization are not expected to be important fate processes(SRC).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), butyric anhydride, which has a vapor pressure of 0.3 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase butyric anhydride is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 4.8 days(SRC), calculated from its rate constant of 3.34X10-12 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3).

Adverse EffectsDermatotoxin - Skin burns.
Soil Adsorption/Mobility · 1건

Using a structure estimation method based on molecular connectivity indices(1), the Koc of butyric anhydride can be estimated to be 10(SRC). According to a classification scheme(2), this estimated Koc value suggests that butyric anhydride is expected to have very high mobility in soil. However, butyric anhydride hydrolyzes to butyric acid in water(2); the neutral hydrolysis half-life at 25 °C is about 4.3 minutes based on analogy to similar anhydrides(1).

Human Toxicity Excerpts · 2건

/SIGNS AND SYMPTOMS/ BUTYRIC ANHYDRIDE CAUSES PERSISTENT EYE IRRITATION IF CONTACT WITH VAPOR IS REPEATED AND PROLONGED. IT IS ALSO A SKIN IRRITANT.

/SIGNS AND SYMPTOMS/ ...THEY MAY PRODUCE CHRONIC CONJUNCTIVITIS. THEY ARE SLOWLY HYDROLYZED ON CONTACT WITH BODY TISSUES AND MAY OCCASIONALLY CAUSE SENSITIZATION. /ACID ANHYDRIDES/

Artificial Pollution SourcesButyric anhydride's production and use in the manufacture of butyrates, drugs, and tanning agents(1) may result in its release to the environment through various waste streams(SRC).

규제 정보

TSCA Requirements · 2건

Section 8(a) of TSCA requires manufacturers of this chemical substance to report preliminary assessment information concerned with production, exposure, and use to EPA as cited in the preamble in 51 FR 41329. Effective date: 9/30/91; Reporting date: 11/27/91.

Pursuant to section 8(d) of TSCA, EPA promulgated a model Health and Safety Data Reporting Rule. The section 8(d) model rule requires manufacturers, importers, and processors of listed chemical substances and mixtures to submit to EPA copies and lists of unpublished health and safety studies. Butyric anhydride is included on this list. Effective date: 9/30/91; Sunset date: 12/19/95.

Atmospheric Standards · 1건

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

안전 데이터

wgk
1
tsca
TSCA listed
rtecs
ET7090000
ridadr
UN 2739
독성
LD50 orally in Rabbit: 8790 mg/kg LD50 dermal Rabbit 6400 mg/kg
HS 번호
29159000

화학 및 산업

용도 및 제조

Uses · 6건

Used to make drugs, tanning agents, and other organic chemicals; [HSDB]

Manufacture of butyrates, drugs, and tanning agents.

CHEM INT FOR CELLULOSE ACETATE BUTYRATE RESINS

CHEM INT FOR FLAVORING AGENTS, EG, ISOPENTYL BUTYRATE

CHEM INT FOR PERFUMES, EG, GERANYL BUTYRATE

CHEM INT FOR SODIUM TYROPANOATE (ORAL CHOLECYSTOGRAPHIC)

U.S. Exports · 2건

(1979) No Data

(1981) No Data

U.S. Imports · 2건

(1979) No Data

(1981) No Data

U.S. Production · 6건

2023: 150,000,000 - <500,000,000 lb

(1979) PROBABLY GREATER THAN 2.27X10+6 GRAMS

(1981) PROBABLY GREATER THAN 2.27X10+6 GRAMS

Butanoic acid, anhydride is listed as a High Production Volume (HPV) chemical (65FR81686). Chemicals listed as HPV were produced in or imported into the U.S. in >1 million pounds in 1990 and/or 1994. The HPV list is based on the 1990 Inventory Update Rule. (IUR) (40 CFR part 710 subpart B; 51FR21438).

Production volumes for non-confidential chemicals reported under the Inventory Update Rule. [Table#5379]

Production volume for non-confidential chemicals reported under the 2006 Inventory Update Rule. Chemical: Butanoic acid, 1,1'-anhydride. Aggregated National Production Volume: 100 to < 500 million pounds.

Consumer UsesNot Known or Reasonably Ascertainable
Industry UsesNot Known or Reasonably Ascertainable
응용 분야 · 3건

개요Butyric anhydride, or Butanoic anhydride, is a chemical compound with the formula (CH3CH2CH2CO)2O.It is a colorless liquid that smells strongly of butyric acid, formed by its reaction with the moisture in the air.

용도Butyric anhydride is used in the preparation of amidoamine dendron-based co-adsorbents, which finds application in dye- sensitized solar cells improvement. It is also used in the synthesis of butyrate ester, which is used as a perfume and flavor. Further, it acts as a fumigant to drive bees from their hives. In addition to this, it is used in food additives, textile auxiliaries, varnishes, perfumes, pharmaceuticals and disinfectants.

일반 설명Water-white liquid with an odor of rancid butter. Flash point 190°F. Density 8.0 lb / gal. Corrosive to metals and tissue. Low toxicity.

제조 방법 · 1건

To a cooled flask containing 88 gm (1.0 mole) of η-butyric acid at 10°C is added dropwise 28.0 gm (0.5 mole) of methoxyacetylene over a 1-hr period. After stirring the reaction mixture for 16 hr at 20°C the contents are distilled to afford the following three fractions: (1) b.p. 56°C, η& 1.3628, 23 gm (62%), methyl acetate; (2) b.p. 72-73°C (18 mm Hg), n% 1.3990, 10.0 gm (11%), butyric acid; (3) b.p. 91-92°C (18mmHg), 1.4118, 48.0 gm (61%), butyric anhydride.

관련 반응

67건

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