ホームMCPワークベンチSkills
ホームワークベンチ通知マイページ
化工社オープンプロジェクト:[email protected]AIアクセス:llms.txt · MCPガイドプライバシーポリシー · 利用規約 · サポートv1.7.8
  1. ホーム
  2. /化合物

2-Hydroxyethyl Methacrylate

HCID 178949525
ノート反応
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
部分構造検索類似構造を探す

基本情報

CAS
141668-69-1
標準SMILES
C=C(C)C(=O)OCCO
InChIKey
WOBHKFSMXKNTIM-UHFFFAOYSA-N
分子式
C6H10O3
平均分子量
130.14 g/mol

概要

2-hydroxyethyl methacrylate is an enoate ester that is the monomethacryloyl derivative of ethylene glycol. It has a role as an allergen and a polymerisation monomer. It is functionally related to a methacrylic acid and an ethylene glycol.

名称と識別子

優先名称
2-Hydroxyethyl Methacrylate
IUPAC
2-hydroxyethyl 2-methylprop-2-enoate
英語名
HEMA
分子式
C6H10O3
分子量
130.1418

名称と別名

2-HYDROXYETHYL METHACRYLATE868-77-9Glycol methacrylateHydroxyethyl methacrylateEthylene glycol methacrylateGlycol monomethacrylate2-(Methacryloyloxy)ethanol2-HydroxyethylmethacrylateMhoromerMonomer MG-1Ethylene glycol monomethacrylate2-Propenoic acid, 2-methyl-, 2-hydroxyethyl ester
名称をさらに表示
DTXSID7022128beta-Hydroxyethyl methacrylateEthylene glycol, monomethacrylateMonomethacrylic ether of ethylene glycol6E1I4IV47VCHEBI:34288NSC-24180DTXCID202128

データベース識別子

CAS
141668-69-1
ChEMBL
CHEMBL1730239
ChEBI
CHEBI:34288
UNII
6E1I4IV47V
EC Number
212-782-2、927-388-2
Nikkaji
J53.687C

物性

構造計算による物性

XLogP
0.5
極性表面積
46.5 Ų
水素結合供与体数
1
水素結合受容体数
3
回転可能結合数
4
重原子数
9
形式電荷
0
複雑度
117

実験および物理化学的性質

PolymersPlastics & Rubber -> (Meth)acrylates
CosmeticsCosmetic ingredients (HEMA) -> CIR (Cosmetic Ingredient Review)
LogP · 3 件

log Kow= 0.47

0.42

0.47

Density · 3 件

1.034 @ 25 °C/4 °C

1.07 g/cm³

1.034 @25 °C

Viscosity8.4 mm²/s at 20 °C
Color/FormClear mobile liquid
Solubility · 2 件

Miscible with water and soluble in common org solvents

Solubility in water: miscible

Flash Point · 2 件

97 °C (closed cup)

97 °C c.c.

Boiling Point · 3 件

67 °C @ 3.5 mm Hg

250 °C (calculated)

67 °C @760 [mm Hg]

DecompositionWhen heated to decomp it emits acrid smoke and irritating fumes.
Melting Point

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 · 6 件

Warning

H315: Causes skin irritation [Warning Skin corrosion/irritation]

P261, P264, P264+P265, P272, P280, P302+P352, P305+P351+P338, P321, P332+P317, P333+P317, P337+P317, P362+P364, and P501 (click each P-code to see the statement)

This chemical does not meet GHS hazard criteria for 0.2% (3 of 1898) of reports.

Warning

H315 (94.3%): Causes skin irritation [Warning Skin corrosion/irritation]

危険有害性情報

Regulatory Information · 4 件

Chemical: 2-Propenoic acid, 2-methyl-, 2-hydroxyethyl ester

2-Propenoic acid, 2-methyl-, 2-hydroxyethyl ester is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 2-Propenoic acid, 2-methyl-, 2-hydroxyethyl ester 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: 16-05-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/15124

2-Hydroxyethyl methacrylate: Does not have an individual approval but may be used under an appropriate group standard

Other Safety InformationIMAP assessments - 2-Propenoic acid, 2-methyl-, 2-hydroxyethyl ester: Human health tier II assessment
Fire HazardsCombustible. Above 97 °C explosive vapour/air mixtures may be formed.
Fire Potential30% GRADE (WITH XYLENE) IS FLAMMABLE; MODERATE FIRE RISK.
Hazards Summary · 1 件

Allergic contact dermatitis reported in a laboratory technician and in the printing industry; A skin and eye irritant; [HSDB] Hydrolyzed forming methacrylic acid and ethylene glycol; A mild skin and moderate eye irritant; Possesses skin sensitizing properties with equivocal results in human patch testing; [Reference #2] A skin and severe eye irritant; May cause skin sensitization; [Alfa Aesar MSDS]

化学と産業

薬理情報

Metabolism/MetabolitesSMALL QUANTITIES OF METHACRYLATES MAY READILY BE METABOLIZED BY SAPONIFICATION INTO THE ALCOHOL AND METHACRYLIC ACID. THE LATTER MAY FORM AN ACETYL-COENZYME DERIVATIVE, WHICH THEN ENTERS THE NORMAL LIPID METABOLISM. /METHACRYLATES/

用途と製造

Uses · 6 件

CIR ingredient: HEMA

Frequently used in UV-curable inks and coatings; also used in adhesives, artificial nails, dental materials, and lacquers; [HSDB] Used in dentistry as one of the main volatile acrylates along with methyl methacrylate; [Reference #1] Used as a monomer in the synthesis of polymers (used in paints, adhesives, coatings, dental adhesive systems, etc.) for dental prosthetics, and for geotechnical grouting in construction work; [Reference #2]

Painting (Pigments, Binders, and Biocides) [Category: Paint]

Acrylic resins; binder for nonwoven fabrics; enamels.

IN OPTOMETRY UTILIZED AS BASIC MATERIAL FOR CONTACT LENSES; AS DENTAL FILLER; IN PHARMACEUTICAL AREAS AS A DRUG RELEASE CONTROL MEDIUM; IN MEDICINE AS A SYNTHETIC WOUND DRESSING COMPONENT; AS A HYDROGEL FOR ORGAN GRAFTING; FOR SURFACE TENSION CONTROL IN BIOENGINEERING.

CROSSLINKING MONOMER FOR THERMOSET & UV CURABLE ACRYLICS.

U.S. Imports(1983) 1.36X10+9 g /Acrylates & Acrylic Acid/
U.S. Production2023: 10,000,000 - <25,000,000 lb
Consumer UsesIntermediate
Industry UsesMonomers
Methods of Manufacturing · 3 件

The methacrylates can be synthesized by catalytic oxidation of isobutylene and subsequent esterification with the appropriate alcohol, or by reacting acetone with hydrocyanic acid and subsequent esterification in sulfuric acid with the appropriate alcohol. /Methacrylic esters/

REACTION OF METHACRYLIC ACID WITH ETHYLENE OXIDE; TRANSESTERIFICATION OR ESTERIFICATION OF ETHYLENE GLYCOL WITH EITHER METHYL METHACRYLATE OR METHACRYLIC ACID.

関連反応

0 件
反応記録を作成

現在のフィルター条件では反応記録がありません。

化合物ノート

読み込み中…

このページの内容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
FP: -12 °C
Vapor DensityRelative vapor density (air = 1): 4.5
FDA RequirementsHomopolymers and copolymers of 2-Hydroxyethyl methacrylate is an indirect food additive for use only as a component of adhesives.
EC ClassificationSymbol: Xi; R: 36/38-43; S: (2)-26-28; Note: D
Chemical Dangers · 1 件

The substance will polymerize due to heating, on contact with peroxides, and under the influence of light. Heating may cause violent combustion or explosion. This produces acrid smoke. The substance may spontaneously polymerize if it is not stabilized.

Hazard Classes and Categories · 6 件

Skin Irrit. 2 (94.3%)

Eye irritation - category 2A

Serious eye damage/eye irritation - Category 2A

Serious eye damage/eye irritation - Category 2

Skin corrosion/irritation - Category 2

Skin Irrit. 2

Skin, Eye, and Respiratory IrritationsIrritating to eyes and skin.

安全と保護具

Fire FightingUse water spray, dry powder, alcohol-resistant foam. In case of fire: keep drums, etc., cool by spraying with water.
First Aid Measures · 4 件

Fresh air, rest. Refer for medical attention.

First rinse with plenty of water for at least 15 minutes, then remove contaminated clothes and rinse again. Refer for medical attention .

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

Rinse mouth. Do NOT induce vomiting. Give one or two glasses of water to drink. Refer immediately for medical attention.

Safe StorageStore only if stabilized. Keep in the dark. Cool. Ventilation along the floor.
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/

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.

Spillage Disposal · 1 件

Personal protection: chemical protection suit and filter respirator for organic gases and vapours adapted to the airborne concentration of the substance. Collect leaking liquid in covered containers. Absorb remaining liquid in sand or inert absorbent. Then store and dispose of according to local regulations.

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.

Eye PreventionWear safety spectacles or eye protection in combination with breathing protection.
Fire PreventionNO open flames. Above 97 °C use a closed system and ventilation.
Inhalation RiskNo indication can be given about the rate at which a harmful concentration of this substance in the air is reached.
Skin PreventionProtective gloves. Protective clothing.
Exposure PreventionPREVENT GENERATION OF MISTS!

毒性情報

Ecotoxicity Values · 1 件

LC50 Pimephales promelas (fathead minnows) 0.99 g/l/96 hr (95% confidence limit 0.90-1.1 g/l); age 30 days old, water hardness 45.6 mg/l calcium carbonate, temp 24.9 °C, pH 7.66, dissolved oxygen 7.1 mg/l, alkalinity 44.4 mg/l (CaCO3), Tank vol: 2.0 l, additions: 18 vol/day (flow-through bioassay)

Environmental Fate · 3 件

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 43(SRC), determined from a log Kow of 0.47(2) and a regression-derived equation(3), indicates that 2-hydroxyethyl methacrylate is expected to have very high mobility in soil(SRC). Volatilization of 2-hydroxyethyl methacrylate from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 4.6X10-9 atm-cu m/mole(SRC), using a fragment constant estimation method(4). 2-Hydroxyethyl methacrylate is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 0.126 mm Hg(5). Screening tests indicate that 2-hydroxyethyl methacrylate is readily biodegradable; it reached 92-100% of its theoretical BOD in 2 weeks using an activated sludge inoculum(6).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 43(SRC), determined from a log Kow of 0.47(2) and a regression-derived equation(3), indicates that 2-hydroxyethyl methacrylate is not expected to adsorb to suspended solids and sediment in water(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 4.6X10-9 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). According to a classification scheme(5), an estimated BCF of 1.3(SRC), from the log Kow(2), suggests the potential for bioconcentration in aquatic organisms is low. Hydrolysis of 2-hydroxyethyl methacrylate may be a significant process under basic conditions based upon a hydrolytic half-life of 4 hours at pH 11 for the structurally similar butyl acrylate(6); half-lives for butyl acrylate at pH 7, 8, and 9 were 4 years, 150 days, and 15 days(SRC), respectively, based upon a hydrolytic rate constant of 0.053 L/mole-sec(8). Screening tests indicate that 2-hydroxyethyl methacrylate is readily biodegradable; it reached 92-100% of its theoretical BOD in 2 weeks using an activated sludge inoculum(7).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 2-hydroxyethyl methacrylate, which has a vapor pressure of 0.126 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase 2-hydroxyethyl methacrylate 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 16 hours(SRC) from its estimated rate constant of 2.4X10-11 cu cm/molecule-sec at 25 °C(3). Because the structurally similar ethyl methacrylate does not absorb light in the environmental spectrum above 290 nm(4), direct photolysis of 2-hydroxyethyl methacrylate is not expected to occur(SRC).

Adverse EffectsSkin Sensitizer - An agent that can induce an allergic reaction in the skin.
Toxicity Summary · 2 件

Based on available data, the CIR Expert Panel concluded that...HEMA is safe as used in nail enhancement products when skin contact is avoided. Products containing these ingredients should be accompanied with directions to avoid skin contact, because of the sensitizing potential of Methacrylates.

Safe for use in cosmetics, with qualifications

Signs and Symptoms · 4 件

Cough. Sore throat.

Redness.

Redness.

Sore throat. Aspiration hazard!

Soil Adsorption/Mobility · 1 件

The Koc of 2-hydroxyethyl methacrylate is estimated as approximately 43(SRC), using a log Kow of 0.47(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that 2-hydroxyethyl methacrylate is expected to have very high mobility in soil.

Human Toxicity Excerpts · 2 件

LAB TECHNICIAN DEVELOPED ALLERGIC CONTACT DERMATITIS ASSOC WITH NAUSEA, DIARRHEA, & PERSISTENT PARESTHESIA OF FINGERTIPS. HYDROXYETHYLMETHACRYLATE WAS DEMONSTRATED TO PASS THROUGH VINYL GLOVES.

2-Hydroxy-ethyl methacrylate and di- and tetra-ethylene glycol dimethacrylates have produced contact sensitization in workers in the printing industry.

Artificial Pollution Sources2-Hydroxyethyl methacrylate's production and use in acrylic resins, enamels, and as a binder for non-woven fabrics(1) may result in its release to the environment through various waste streams(SRC).
Environmental Biodegradation2-Hydroxyethyl methacrylate, present at 100 mg/l, reached 92-100% of its theoretical BOD in 2 weeks using an activated sludge inoculum and the Japanese MITI test(1).
Environmental BioconcentrationAn estimated BCF of 1.3 was calculated for 2-hydroxyethyl methacrylate(SRC), using a log Kow of 0.47(1). According to a classification scheme(2), this BCF suggests the potential for bioconcentration in aquatic organisms is low.
Volatilization from Water/Soil · 1 件

The Henry's Law constant for 2-hydroxyethyl methacrylate is estimated as 4.6X10-9 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that 2-hydroxyethyl methacrylate is expected to be essentially nonvolatile from water surfaces(2) and from moist soil surfaces(SRC). 2-Hydroxyethyl methacrylate is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 0.126 mm Hg(3).

Non-Human Toxicity Excerpts · 5 件

TOXICOLOGICALLY, HYDROXYETHYL METHACRYLATE APPEARS ALMOST THREE TIMES AS TOXIC AS THE METHACRYLIC ETHYL ESTER.

INTRACORNEAL IMPLANTS OF PLASTIC FOILS MADE WITH HYDROXYETHYLMETHACRYLATE OR HYDROXYETHYLACRYLATE PLUS ETHYLENEGLYCOL DIMETHACRYLATE IN RABBITS PRODUCED EDEMA, VASCULARIZATION, NECROSIS, & ULCERATION & EVEN CHANGES IN THE PLASTICS THEMSELVES. CAUSATIVE AGENT NOT IDENTIFIED.

THE TOXICITY OF 6 ACRYLATES AND 6 METHACRYLATES, INCLUDING 2-HYDROXYETHYL METHACRYLATE, WAS DETERMINED IN RATS AND FISH. ALL THE ESTERS WERE LESS TOXIC THAN ACRYLAMIDE AND ACRYLONITRILE. METHACRYLATES WERE APPROXIMATELY 5-FOLD LESS TOXIC THAN ACRYLATES. FOR A GIVEN SERIES, TOXICITY DECREASED WITH INCREASING LENGTH OF THE CARBON CHAIN.

METHACRYLIC ACID ADMIN IV INCR RESPIRATORY RATE, DECR HEART RATE, & PRODUCED ELECTROCARDIOGRAM CHANGES IN ANESTHETIZED DOGS. METHACRYLIC ACID, METHYL, N-PROPYL, N-BUTYL, ISOBUTYL, AND HYDROXYETHYL METHACRYLATES PRODUCED A BIPHASIC RESPONSE, AN ABRUPT FALL IN BLOOD PRESSURE FOLLOWED BY A SECONDARY RISE. 2-ETHYLHEXYL, ISODECYL, LAURYL, AND TERT-BUTYLAMINOETHYL METHACRYLATES PRODUCED ONLY A HYPOTENSIVE EFFECT. DIMETHYLAMINOETHYLMETHACRYLATE PRODUCED ONLY A HYPERTENSIVE EFFECT.

TWENTY-ONE DIFFERENT ACRYLATE & METHACRYLATE COMPOUNDS, INCLUDING 2-HYDROXYETHYL METHACRYLATE, WERE SCANNED FOR THEIR ABILITY TO INDUCE CONTACT SENSITIVITY, USING 5 DIFFERENT SENSITIZATION PROTOCOLS. CONTACT REACTIONS OF VARYING INTENSITIES WERE PRODUCED TO ALL THE MONO-, DI-, AND TRIACRYLATES TESTED. METHACRYLATES DID NOT SENSITIZE GUINEA PIGS.

法規制情報

FDA RequirementsHomopolymers and copolymers of 2-Hydroxyethyl methacrylate is an indirect food additive for use only as a component of adhesives.

Hydroxyalkyl methacrylates are prepared by the addition of methacrylic acid to the epoxide ring of alkylene oxides to form hydroxyalkyl methacrylates, ie, beta-hydroxyethyl and hydroxypropyl methacrylate. Oxides other than ethylene oxide give isomeric products; commercial hydroxypropyl methacrylate has about a 2-to-1 ratio of 2-hydroxypropyl methacrylate to 1-methyl-2-hydroxyethyl methacrylate. Effective catalysts include tertiary amines, anion-exchange resins, ferric chloride, and lithium methacrylate.

Formulations/Preparations · 3 件

The 30% solution is made with xylene. Grades: 30%; 96%.

An inhibitor is usually added to solutions to prolong shelf life.

Commercial products contain hydroquinone methyl ether or similar polymerization inhibitors.

Household ProductsInformation on 4 consumer products that contain 2-Hydroxyethyl methacrylate in the following categories is provided:
General Manufacturing Information · 4 件

Adhesive Manufacturing

2-Propenoic acid, 2-methyl-, 2-hydroxyethyl ester: 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/

In hydrogel contact lenses

サプライヤー6 社

济南万多鑫化工有限公司0531-88770993 13905318421 · [email protected]
武汉欣扬瑞和化学科技有限公司027-83855316 18171155316
金锦乐(湖南)化学有限公司18001959627(微信同号) 18001959627 · [email protected]
武汉弘德悦欣医药科技有限公司027-83850116 18164090116 · [email protected]
山东省立帆化工有限公司13176825516 · [email protected]
Hefei TNJ Chemical Industry Co.,Ltd.+86-0551-65418684 +86-18949823763 · [email protected]