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메타 크릴 산 무수물

Methacrylic anhydride

HCID 12974
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기본 정보개요이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
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기본 정보

CAS
760-93-0
표준 SMILES
C=C(C)C(=O)OC(=O)C(=C)C
InChIKey
DCUFMVPCXCSVNP-UHFFFAOYSA-N
분자식
C8H10O3
평균 분자량
154.16 g/mol
단동위원소 질량
154.06299418

개요

Methacrylic anhydride is a liquid. (EPA, 1998)

이름 및 식별자

우선 이름
Methacrylic anhydride
IUPAC
2-methylprop-2-enoyl 2-methylprop-2-enoate
현지명
메타 크릴 산 무수물
영어명
Methacrylic anhydride
분자식
C8H10O3
분자량
154.17

이름 및 동의어

METHACRYLIC ANHYDRIDEMethacrylic acid anhydrideMethacryloyl anhydride2-Methyl-2-propenoic acid anhydride2-Propenoic acid, 2-methyl-, anhydrideHSDB 6407EINECS 212-084-8NSC 24159UNII-N2RJR03340BRN 1761982N2RJR033402-Propenoic acid, 2-methyl-, 1,1'-anhydride
이름 더 보기
메타크릴산무수물1-Methylacrylic anhydrideMETHACRYLIC ANHTDRIDEmethacrylicacidanhydride2-methyl-2-propenoicacianhydride276685-500MLmethacryloylanhydride
NSC-24159BIS(METHACRYLIC ACID) ANHYDRIDE4-02-00-01537 (Beilstein Handbook Reference)DTXSID60862404EC 212-084-8METHACRYLIC ANHYDRIDE [HSDB]RefChem:1568412Methyl2propenoic acid anhydride

데이터베이스 식별자

CAS
760-93-0
PubChem CID
12974
DTXSID
DTXSID60862404
UNII
N2RJR03340
EC Number
212-084-8
Nikkaji
J38.879C

물성

구조 계산 물성

XLogP
1.8
극성 표면적
43.4 Ų
수소 결합 공여자 수
0
수소 결합 수용자 수
3
회전 가능 결합 수
4
무거운 원자 수
11
형식 전하
0
복잡도
201

실험 및 물리화학적 성질

Chemical ClassesOther Classes -> Acid Anhydrides, Other
SpringerMaterials PropertiesOptical coefficient
Density · 2건

Specific gravity: 1.035

1.035 @25 °C

Viscosity3 mPa
Solubility · 2건

> 10% in ether

> 10% in ethanol

Boiling Point · 3건

192 °F at 5 mmHg (EPA, 1998)

89 °C at 5 mm Hg

240 °C @760 [mm Hg]

DecompositionWhen heated to decomposition it emits acrid smoke and irritating fumes.
Vapor Pressure · 2건

8.83 [mmHg]

0.01 [mm Hg] @25 °C

Refractive Index · 2건

Index of refraction: 1.4540 @ 20 °C

Index of refraction: 1.453 at 25 °C/D

Physical Description · 3건

Methacrylic anhydride is a liquid. (EPA, 1998)

Liquid

안전 및 규제

안전 정보는 참고용이며, 공급업체의 물질안전보건자료(SDS), 관련 법규 및 전문가 평가를 대체하지 않습니다.

GHS 분류

GHS Classification · 5건

This chemical does not meet GHS hazard criteria for 2.7% (5 of 184) of reports.

Danger

H302+H332 (57.6%): Harmful if swallowed or if inhaled [Warning Acute toxicity, oral; acute toxicity, inhalation]

P261, P264, P264+P265, P270, P271, P272, P280, P301+P317, P302+P352, P304+P340, P305+P354+P338, P316, P317, P319, P321, P330, P332+P317, P333+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 184 reports by companies from 14 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

유해성 정보

Regulatory Information · 4건

2-Propenoic acid, 2-methyl-, 1,1'-anhydride is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 2-Propenoic acid, 2-methyl-, 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)

REACH registered substance: Methacrylic anhydride (EC: 212-084-8)

2-Propenoic acid, 2-methyl-, anhydride: 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 LabelCorrosive
Fire Hazards(Non-Specific -- Methacrylic Acid) This material may burn but may not ignite readily. Flammable/ poisonous gases may accumulate in tanks and hopper cars. Some of these materials may ignite combustibles (wood, paper, oil, etc.). (EPA, 1998)
Health HazardsExcerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:

화학 및 산업

용도 및 제조

U.S. Production2023: <75,000 lb
Industry UsesIntermediate
General Manufacturing Information · 3건

Plastics Material and Resin Manufacturing

2-Propenoic acid, 2-methyl-, 1,1'-anhydride: ACTIVE

METHYL METHACRYLATE, AND IN GENERAL THE METHACRYLIC ESTERS, POLYMERIZE MUCH LESS READILY THAN THE CORRESPONDING ORDINARY ACRYLATES. NONE THE LESS, THEY ARE STABILIZED BY ADDING HYDROQUINONE OR PYROGALLOL, PARTICULARLY IN THE PRESENCE OF METALLIC COPPER. /METHACRYLATES/

응용 분야 · 3건

개요Methacrylic anhydride is a reactive monomer used primarily as a monomer in the preparation of polymers, particularly poly(methacrylic acid) and its copolymers. The reaction mechanism involves the formation of covalent bonds between methacrylic acid and acetic anhydride molecules, resulting in the formation of a novel compound. The newly formed compound then undergoes a series of reactions including hydrolysis and polymerisation. Methacrylic anhydride produces polymers with good chemical and thermal stability, which are used in a wide range of applications in various industries such as bio-renewable resins, pH-sensitive hydrogels, thermoset plastics, coatings, adhesives and plastics.

용도Methacrylic anhydride is a reactive monomer used for the preparation of different type of monomers under mild reaction conditions. It finds applications in light-curing coatings, cross-linked materials like synthetic resin. It acts as an intermediate for the preparation of fibers and resins.

일반 설명Liquid.

제조 방법 · 1건

To synthesize Methacrylic anhydride, sodium methacrylate (1 mol), propionyl chloride (3 mol), and a polymerization inhibitor (0.1 mol) were added to a reaction kettle. The mixture was heated to 90-100 ℃ and refluxed for 8 hours. Methacrylic anhydride was then obtained by distilling and collecting fractions at 100-105 ℃. The yield of the product was 98.33%.

관련 반응

16건
반응 기록 만들기
HRID 35980 반응식
HRID 35980반응물로uspto-grants-1995_05
HRID 128839 반응식
HRID 128839생성물로uspto-grants-1995_11
HRID 235679 반응식
HRID 235679반응물로uspto-grants-1987_02
HRID 333112 반응식
HRID 333112반응물로uspto-grants-2014_11
HRID 399884 반응식
HRID 399884반응물로uspto-grants-1998_10
HRID 478979 반응식
HRID 478979반응물로uspto-grants-2003_11
HRID 499946 반응식
HRID 499946반응물로uspto-grants-2010_08
HRID 519257 반응식
HRID 519257반응물로uspto-grants-2015_08
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Liquid; [CAMEO] Colorless liquid; [MSDSonline]

물리화학적 성질

녹는점
-20 °C · -20°C
끓는 점
87 °C13 · 87 °C13 mm Hg(lit.)
밀도
1.04 g/mL · 1.04 g/mL at 20 °C
증기압
90 Pa · 90Pa at 20℃
굴절률
20 · n20/D 1.453(lit.)
인화점
184 °F · 184 °F
저장 조건
2 · under inert gas (nitrogen or Argon) at 2-8°C
용해도
에탄올 및 에테르와 혼합 가능.
물리적 상태
투명한 액체
색상
Colorless to Light yellow to Light orange
수용성
98 g/L · 98g/L at 20℃
BRN
1761982 · 1761982
안정성
안정적인. 가연성. 습기에 민감합니다.
InChI
1S/C8H10O3/c1-5(2)7(9)11-8(10)6(3)4/h1,3H2,2,4H3
InChIKey
DCUFMVPCXCSVNP-UHFFFAOYSA-N
SMILES
CC(=C)C(=O)OC(=O)C(C)=C
LogP
1.23 · 1.23
NIST
Methacrylic anhydride(760-93-0)
EPA
Methacrylic anhydride (760-93-0)

화학적 성질

Methacrylic anhydride is a colorless transparent liquid which reacts with water exothermically. It can also react with hydroxyl- and amino-groups present in some organic compounds leading to covalent attachment of methacryloyl moieties.

Hazards SummaryReacts with water exothermically producing methacrylic acid; [CAMEO] A corrosive substance that can cause injury to the skin, eyes, and respiratory tract; Inhalation may cause chemical pneumonitis; May cause skin sensitization; [MSDSonline]
Reactive GroupHydrocarbons, Aliphatic Unsaturated
Reactivity AlertsWater-Reactive
Reactivity Profile · 1건

METHACRYLIC ANHYDRIDE reacts exothermically with water. The reactions are sometimes slow, but can become violent when local heating accelerates their rate. Acids accelerate the reaction with water. Incompatible with acids, strong oxidizing agents, alcohols, amines, and bases.

Air and Water ReactionsReacts exothermically with water to form methacrylic acid.
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. Methacrylic anhydride 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.

Hazard Classes and CategoriesAcute Tox. 4 (71.7%)
Skin, Eye, and Respiratory IrritationsMethacrylates ... produce slight to moderate skin and eye irritation ... depending upon volatility, these materials also may be sensory irritants. /Methacrylic acid & derivatives/

안전 및 보호

Fire Fighting(Non-Specific -- Methacrylic Acid) Keep unnecessary people away; isolate hazard area and deny entry. Stay upwind; keep out of low areas. Wear self-contained (positive pressure if available) breathing apparatus and full protective clothing.
First AidNote: No information on specific clinical effects of exposure was available.
Storage Conditions · 1건

Temp during storage must be kept low to minimize formation of peroxides and other oxidation products. ... Storage temp below 30 °C are recommended for the polyfunctional methacrylates. ... The methacrylate monomers should not be stored for longer than one year. Shorter storage times are recommended for the aminomethacrylates, ie, three months, and the polyfunctional methacrylates, ie, six months. Many of these cmpd are sensitive to UV light and should, therefore, be stored in the dark. The methacrylic esters may be stored in mild steel, stainless steel, or aluminum. /Methacrylic acid & derivatives/

Nonfire Spill Response · 1건

(Non-Specific -- Methacrylic Acid) Do not touch spilled material; stop leak if you can do so without risk. For small spills, absorb with sand or other noncombustible absorbent material and place into containers for later disposal. For large spills, dike far ahead of spill for later disposal. (EPA, 1998)

Disposal Methods · 1건

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

Preventive Measures · 3건

... Hazard is the generation of considerable exothermic heat in some of the reactions, so that high pressures & temp may develop. This danger ... should be borne in mind when designing plant. Awareness of the dangers and of good engineering design are essential to safety. Employees should be instructed about the necessity of cleansing the skin if it is contaminated by materials which are irritants or skin-absorbed. With careful design, however, and complete enclosure of those processes where toxic chemicals or intermediates occur, dangerous exposures can be avoided. /Acrylic acid & derivatives/

SRP: Contaminated protective clothing should be segregated in such a manner so that there is no direct personal contact by personnel who handle, dispose, or clean the clothing. Quality assurance to ascertain the completeness of the cleaning procedures should be implemented before the decontaminated protective clothing is returned for reuse by the workers. Contaminated clothing should not be taken home at end of shift, but should remain at employee's place of work for cleaning.

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.

Isolation and EvacuationExcerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:
Protective Action Criteria (PAC) · 3건

0.41 [mg/m3]

4.5 [mg/m3]

16 [mg/m3]

Personal Protective Equipment (PPE) · 2건

For emergency situations, wear a positive pressure, pressure-demand, full facepiece self-contained breathing apparatus (SCBA) or pressure- demand supplied air respirator with escape SCBA and a fully-encapsulating, chemical resistant suit. (EPA, 1998)

SUITABLE PROTECTIVE CLOTHING & SELF-CONTAINED RESP PROTECTIVE APPARATUS SHOULD BE AVAILABLE FOR USE OF THOSE WHO MAY HAVE TO RESCUE PERSONS OVERCOME BY FUMES. /ACRYLIC ACID & DERIVATIVES/

독성 정보

Adverse EffectsDermatotoxin - Skin burns.
Antidote and Emergency Treatment · 2건

Basic treatment: Establish a patent airway. Suction if necessary. Watch for signs of respiratory insufficiency and assist respirations if necessary. Administer oxygen by nonrebreather mask at lO to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with normal saline during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 mL/kg up to 200 mL of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool. Activated charcoal is not effective ... . Do not attempt to neutralize because of exothermic reaction. Cover skin burns with dry, sterile dressings after decontamination ... . /Organic acids and related compounds/

Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in respiratory arrest. Early intubation, at the first sign of upper airway obstruction, may be necessary. Positive-pressure ventilation techniques with a bag-valve-mask device may be beneficial. Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start an IV with D5W TKO /SRP: "To keep open", minimal flow rate/. Use lactated Ringer's if signs of hypovolemia are present. Watch for signs of fluid overload. Consider drug therapy for pulmonary edema ... . For hypotension with signs of hypovolemia, administer fluid cautiously. Consider vasopressors if hypotensive with a normal fluid volume. Watch for signs of fluid overload ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Organic acids and related compounds/

Toxicity DataLC50 (mice) = 450 mg/m3/2h
Non-Human Toxicity ValuesLC50 Mouse ihl 450 mg/cu m/2 hr

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. Methacrylic anhydride 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
1
tsca
TSCA listed
rtecs
OZ5700000
ridadr
UN 3265 8/PG 2
HS 번호
29161900
risk_code
20-37/38-41
hazard_code
Xn
safety_code
26-39
포장분류
II
위험 등급
8
기존화학 물질
2014-3-5802
F 고인화성물질
10-21
Hazard Classifications
Acute Tox. 4 InhalationAcute Tox. 4 OralEye Dam. 1Skin Irrit. 2Skin Sens. 1STOT SE 3
스토리지 클래스
10 - Combustible liquids
유해 물질 데이터
760-93-0(Hazardous Substances Data)

상·하류 제품 정보

상류 원료

2-프로펜산,2-메틸-,아세트산무수물4-히드록시-템포POTASSIUM METHACRYLATE메타크릴산 나트륨이소부텐벤조 무수물메타크릴 산무수초산클로로포름산에틸톨루엔

하류 제품

2-Methyl-acrylic acid-2-(4-benzoyl-3-hydroxy-phenoxy)-ethyl ester2-메틸-2-Adamantyl 메타아크릴레이트메타크릴 산4-Benzoylphenyl Methacrylatebeta-Methacryloyloxy-gamma-butyrolactone메타크릴산 2-하이드록시프로필TEMPO메타크릴레이트메타크릴산이소프로필에스테르테트라데실 2-메틸-2-프로펜산메틸메타크릴레이트4-메톡시페닐메타크릴레이트