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ジメタクリル酸無水物

Methacrylic anhydride

HCID 12974
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基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート
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基本情報

CAS
760-93-0
標準SMILES
C=C(C)C(=O)OC(=O)C(=C)C
InChIKey
DCUFMVPCXCSVNP-UHFFFAOYSA-N
分子式
C8H10O3
平均分子量
154.16 g/mol
単同位体質量
154.06299418

概要

Methacrylic anhydride is a liquid. (EPA, 1998)

名称と識別子

優先名称
Methacrylic anhydride
IUPAC
2-methylprop-2-enoyl 2-methylprop-2-enoate
現地名
ジメタクリル酸無水物
英語名
Methacrylic anhydride
分子式
C8H10O3
分子量
154.17

名称と別名

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
名称をさらに表示
二メタクリル酸無水物無水メタクリル酸ジ(メタクリル酸)無水物ビス(メタクリル酸)無水物ジメタクリル酸無水物ビスメタクリル酸無水物メタクリル酸水物メタクリル酸無水物メタクリル酸無水物, 94%, STAB. WITH CA 0.2% 2,4-DIMETHYL-6-TERT-BUTYLPHENOL1-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

データベース識別子

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

物性

構造計算による物性

XLogP
1.8
極性表面積
43.4 Ų
水素結合供与体数
0
水素結合受容体数
3
回転可能結合数
4
重原子数
11
形式電荷
0
複雑度
201

実験および物理化学的性質

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

Specific gravity: 1.035

1.035 @25 °C

Viscosity3 mPa
Solubility · 2 件

> 10% in ether

> 10% in ethanol

Boiling Point · 3 件

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 · 2 件

8.83 [mmHg]

0.01 [mm Hg] @25 °C

Refractive Index · 2 件

Index of refraction: 1.4540 @ 20 °C

Index of refraction: 1.453 at 25 °C/D

Physical Description · 3 件

Methacrylic anhydride is a liquid. (EPA, 1998)

Liquid

Liquid; [CAMEO] Colorless liquid; [MSDSonline]

安全と法規制

安全情報は参考情報です。供給元の安全データシート(SDS)、適用法令、専門家による評価に代わるものではありません。

GHS分類

GHS Classification · 5 件

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.

危険有害性情報

Regulatory Information · 4 件

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)]:

化学と産業

用途と製造

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

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/

応用分野 · 3 件

説明Methacrylic 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.

使用Methacrylic 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.

一般的な説明Liquid.

調製方法 · 2 件

製造方法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%.

関連反応

16 件
反応記録を作成
HRID 35980 の反応式
HRID 35980反応物としてuspto-grants-1995_05
HRID 128839 の反応式
HRID 128839生成物としてuspto-grants-1995_11
HRID 235679 の反応式
HRID 235679反応物としてuspto-grants-1987_02
HRID 333112 の反応式
HRID 333112反応物としてuspto-grants-2014_11
HRID 399884 の反応式
HRID 399884反応物としてuspto-grants-1998_10
HRID 478979 の反応式
HRID 478979反応物としてuspto-grants-2003_11
HRID 499946 の反応式
HRID 499946反応物としてuspto-grants-2010_08
HRID 519257 の反応式
HRID 519257反応物としてuspto-grants-2015_08
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化合物ノート

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物理化学的性質

融点
-20 °C · -20°C
沸点
87 °C13 · 87 °C13 mm Hg(lit.)
比重(密度)
1.04 g/mL · 1.04 g/mL at 20 °C
蒸気圧
90 Pa · 90Pa at 20℃
屈折率
20 · n20/D 1.453(lit.)
闪点
184 °F · 184 °F
貯蔵温度
2 · under inert gas (nitrogen or Argon) at 2-8°C
溶解性
エタノールおよびエーテルと混和します。
外見
clear liquid
色
Colorless to Light yellow to Light orange
水溶解度
98 g/L · 98g/L at 20℃
BRN
1761982 · 1761982
安定性
安定。可燃性。湿気に敏感。
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
CAS データベース
760 · 760-93-0(CAS DataBase Reference)
NISTの化学物質情報
Methacrylic anhydride(760-93-0)
EPAの化学物質情報
Methacrylic anhydride (760-93-0)

化学的性質

化学的特性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 Summary
Reacts 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 · 1 件

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 · 1 件

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/

安全と保護具

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 · 1 件

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 · 1 件

(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 · 1 件

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 · 3 件

... 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) · 3 件

0.41 [mg/m3]

4.5 [mg/m3]

16 [mg/m3]

Personal Protective Equipment (PPE) · 2 件

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/

毒性情報

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

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

法規制情報

CERCLA Reportable Quantities · 1 件

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.

安全データ

F
10-21
wgk
1
tsca
TSCA listed
rtecs
OZ5700000
ridadr
UN 3265 8/PG 2
hs_code
29161900
risk_code
20-37/38-41
化審法
(2)-1026
消防法
危-4-3-III
hazard_code
Xn
safety_code
26-39
hazard_class
8
packing_group
II
Hazard Classifications
Acute Tox. 4 InhalationAcute Tox. 4 OralEye Dam. 1Skin Irrit. 2Skin Sens. 1STOT SE 3
ストレージクラス
10 - Combustible liquids
有毒物質データの
760-93-0(Hazardous Substances Data)

純化方法Distil the anhydride at 2mm pressure, immediately before use, in the presence of hydroquinone. [Beilstein 2 IV 1537.]

上流・下流製品情報

上流原料

メタクリル酸酢酸無水物4-ヒドロキシ-2,2,6,6-テトラメチルピペリジン1-オキシル フリーラジカルメタクリル酸カリウムメタクリル酸ナトリウムイソブテン安息香酸無水物メタクリル酸無水酢酸クロロぎ酸エチルトルエン

下流製品

メタクリル酸2-(4-ベンゾイル-3-ヒドロキシフェノキシ)エチル2-メタクリロイルオキシ-2-メチルアダマンタンメタクリル酸メタクリル酸4-ベンゾイルフェニル5-オキソオキソラン-3-イル=メタクリラート1,2-プロパンジオール1-メタクリラート4-メタクリロイルオキシ-2,2,6,6-テトラメチルピペリジン1-オキシルフリーラジカルメタクリル酸イソプロピル2-メチルプロペン酸テトラデシルメタクリル酸メチル4-メトキシフェニルメタクリラート