2-하이드록시프로필아크릴레이트

Hydroxypropyl acrylate

HCID 16213126CAS 25584-83-2

기본 정보

표준 SMILES
C=CC(=O)O.CC(O)CO
InChIKey
QZPSOSOOLFHYRR-UHFFFAOYSA-N
분자식
C6H12O4
평균 분자량
148.16 g/mol

개요

Hydroxypropyl acrylate appears as a clear colorless liquid. Toxic by inhalation and skin absorption. Corrosive to tissue. May polymerize exothermically if heated or contaminated. If the polymerization takes place inside a container, the container may rupture violently. Vapors heavier than air. Used to make plastics.

이름 및 식별자

우선 이름
Hydroxypropyl acrylate
IUPAC
propane-1,2-diol;prop-2-enoic acid
현지명
2-하이드록시프로필아크릴레이트
영어명
Hydroxypropyl acrylate
분자식
C6H10O3
분자량
130.14

이름 및 동의어

Propylene glycol acrylate7EFO911SQHAcrylic acid, hydroxypropyl esterAcrylic acid, monoester with 1,2-propanediolAcrylic acid, monoester with propane-1,2-diol2-Propenoic acid, monoester with 1,2-propanediolDTXSID8027878VISCOAT HPARefChem:1087096DTXCID901778603247-118-025584-83-2
이름 더 보기
2-하이드록시프로필아크릴레이트하이드록시프로필아크릴레이트하이드록시프로필아크릴산염하이드록시프로필아크릴산하이드록시프로필아크릴산(아크릴산,모노에스테르,함유1,2-프로판디올)하이드록시프로필아크릴산염하이드록시프로필 아크릴산1,2-프로파네디올, 모노아크릴산1,2-프로파네디올-1-아크릴산1,2-프로페인다이올, 모노아크릴레이트2-프로펜 산, 2-하이드록시프로필 에스터2-프로펜산과 1,2-프로페인다이올의 모노에스터β-하이드록시프로필 아크릴산아크릴산, 2-하이드록시프로필 에스터아크릴산, 모노에스터 함유 1,2-프로필렌 글리콜아크릴산과 프로페인-1,2-다이올의 모노에스터프로프-2-엔산과 1,2-프로페인다이올의 모노에스터프로필렌 글라이콜 아크릴레이트프로필렌 글리콜 모노아크릴산프로필렌 글리콜 아크릴산2-HYDROXYPROYL ACRYLATEHydroxypropylacrylat1,2(or3)-propanediolHydroypropyl acrylatepropyleneglycolacrylate2-HYDROXYPROPYL ACRYALTEHydroxypropyl acrylate,HPAHPA / Hydroxypropyl Acrylate
Hydroxypropyl acrylatepropane-1,2-diol;prop-2-enoic acidAcrylic acid 2-hydroxypropyl esterUNII-7EFO911SQHSCHEMBL153503acrylic acid;propane-1,2-diolCCRIS 7745HSDB 596

데이터베이스 식별자

CAS
25584-83-2
PubChem CID
16213126
EC Number
247-118-0

물성

구조 계산 물성

극성 표면적
77.8 Ų
수소 결합 공여자 수
3
수소 결합 수용자 수
4
회전 가능 결합 수
2
무거운 원자 수
10

실험 및 물리화학적 성질

LogP0.35
OdorFaint unpleasant odor
Density · 4건

1.06 at 77 °F (USCG, 1999) - Denser than water; will sink

1.05 kg/L at 25 °C

1.05 g/cm³

Relative density of the vapour/air-mixture at 20 °C (air = 1): 1.00

Viscosity8.2 mm²/s at 20 °C
Color/FormColorless liquid
Solubility · 3건

Water soluble

Miscible with water and oxygenated solvents

Solubility in water, g/100ml at 25 °C: 30.7 (good)

물리화학적 성질

녹는점
-92 °C · -92°C
끓는 점
77 °C5 · 77 °C5 mm Hg(lit.)
밀도
1.044 g/mL · 1.044 g/mL at 25 °C(lit.)
증기 밀도
4.5 · 4.5 (vs air)
증기압
1 Pa · 1Pa at 20℃
굴절률
20 · n20/D 1.445(lit.)

안전 및 규제

GHS 분류

GHS Classification · 6건

Danger

H301: Toxic if swallowed [Danger Acute toxicity, oral]

P260, P261, P262, P264, P270, P271, P272, P280, P301+P316, P301+P330+P331, P302+P352, P302+P361+P354, P304+P340, P305+P354+P338, P316, P321, P330, P333+P317, P361+P364, P362+P364, P363, P403+P233, P405, and P501 (click each P-code to see the statement)

This chemical does not meet GHS hazard criteria for 0.1% (1 of 800) of reports.

Danger

H301 (95.9%): Toxic if swallowed [Danger Acute toxicity, oral]

유해성 정보

Regulatory Information · 4건

Chemical: 2-Propenoic acid, monoester with 1,2-propanediol

2-Propenoic acid, monoester with 1,2-propanediol is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 2-Propenoic acid, monoester with 1,2-propanediol 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: Acrylic acid, monoester with propane-1,2-diol (EC: 247-118-0)

Propylene glycol monoacrylate: Does not have an individual approval but may be used under an appropriate group standard

DOT LabelCorrosive
Fire Hazards · 2건

Excerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]:

Combustible. Gives off irritating or toxic fumes (or gases) in a fire. Above 97 °C explosive vapour/air mixtures may be formed.

Health Hazards · 1건

Inhalation irritates nose and throat and causes coughing; lung injury may occur. Ingestion causes irritation and burning of mouth and stomach. Vapor irritates eyes. Contact with liquid causes severe burns of eyes and burns of skin. (USCG, 1999)

Reactive GroupAlcohols and Polyols
EC ClassificationSymbol: T; R: 23/24/25-34-43; S: (1/2)-26-36/37/39-45; Note: C, D

안전 및 보호

Fire Fighting · 2건

Excerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]:

Use water spray, dry powder, alcohol-resistant foam, carbon dioxide. In case of fire: keep drums, etc., cool by spraying with water.

First Aid Measures · 4건

Fresh air, rest. Refer for medical attention.

Remove contaminated clothes. Rinse skin with plenty of water or shower. Refer for medical attention .

Rinse with plenty of water (remove contact lenses if easily possible). Refer for medical attention.

Rinse mouth. Do NOT induce vomiting. Refer for medical attention .

First AidINHALATION: if ill effects occur, get patient to fresh air, keep him quiet and warm, and get medical attention; if breathing stops, start artificial respiration.
Safe StorageSeparated from food and feedstuffs, strong bases and strong acids. Store only if stabilized. Cool. Keep in the dark. Store in an area without drain or sewer access. Provision to contain effluent from fire extinguishing.
Fire Fighting Procedures · 3건

Alcohol foam.

If material on fire or involved in fire: Use water in flooding quantities as fog. Solid stream 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.

Suitable extinguishing media: Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide. Advice for firefighters: Wear self-contained breathing apparatus for firefighting if necessary.

Storage Conditions · 2건

Keep container tightly closed in a dry and well-ventilated place. Containers which are opened must be carefully resealed and kept upright to prevent leakage. Storage class (TRGS 510): Non-combustible, acute toxic Cat.3 / toxic hazardous materials or hazardous materials causing chronic effects.

The effectiveness of phenolic inhibitors is dependent on the presence of oxygen and the monomers must be stored under air rather than an inert atmosphere. Temp must be kept low to minimize formation of peroxides and other products ... The acrylic esters may be stored in mild or stainless steel, or aluminum. /Acrylic acid & derivatives/

독성 정보

Ecotoxicity Values · 5건

LC50; Species: Pimephales promelas (fathead minnow) 34 day old; Conditions: flow through, water hardness 45.4 mg/L (CaCO3), temp 24.4 °C, pH 7.55, dissolved oxygen 6.4 mg/L, alkalinity 49.3 mg/L (CaCO3), tank vol 2.0 L, additions 18 vol/day; Concentration: 3.61 mg/L for 96 hr />97% purity/

EC50; Species: Pimephales promelas (fathead minnow) 34 day old; Conditions: flow through, water hardness 45.4 mg/L (CaCO3), temp 24.4 °C, pH 7.55, dissolved oxygen 6.4 mg/L, alkalinity 49.3 mg/L (CaCO3), tank vol 2.0 L, additions 18 vol/day; Concentration: 3.61 mg/L for 96 hr; Effect: Affected fish lost schooling behavior and swam near the tank surface in a corkscrew/spiral pattern. They were hyperactive, had increased respiration, were darkly colored and deformed, had edema, and lost equilibrium prior to death. />97% purity/

LC50; Species: Pimephales promelas (fathead minnow) 33 day old; Conditions: flow through, water hardness 45.9 mg/L (CaCO3), temp 24.7 °C, pH 7.87, dissolved oxygen 6.7 mg/L, alkalinity 45.0 mg/L (CaCO3), tank vol 2.0 L, additions 18 vol/day; Concentration: 3.1 mg/L for 96 hr />97% purity/

EC50; Species: Pimephales promelas (fathead minnow) 33 day old; Conditions: flow through, water hardness 45.9 mg/L (CaCO3), temp 24.7 °C, pH 7.87, dissolved oxygen 6.7 mg/L, alkalinity 45.0 mg/L (CaCO3), tank vol 2.0 L, additions 18 vol/day; Concentration: 1.9 mg/L for 96 hr; Effect: Affected fish lost schooling behavior and swam near the tank surface in a corkscrew/spiral pattern. They were hyperactive and overreactive to external stimuli, had increased respiration and rigid musculature, showed signs of edema, were deformed, and lost equilibrium prior to death. />97% purity/

For more Ecotoxicity Values (Complete) data for Hydroxypropyl acrylate (7 total), please visit the HSDB record page.

Environmental Fate · 3건

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 1.5(SRC), determined from a structure estimation method(2), indicates that hydroxypropyl acrylate is expected to have very high mobility in soil(SRC). Volatilization of hydroxyporpyl acrylate from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 1.7X10-9 atm-cu m/mole(SRC), developed using a fragment constant estimation method(2). Hydroxypropyl acrylate is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 0.12 mm Hg at 25 °C(SRC), determined from a fragment constant method(2). A 83% of Theoretical BOD using activated sludge in the Japanese MITI test(3) suggests that biodegradation is an important environmental fate process in soil(SRC). Using an ecosystem model, degradation rate of hydroxypropyl acrylate in soil was 3.4X10-7/s(4).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 1.5(SRC), determined from a structure estimation method(2), indicates that hydroxypropyl acrylate is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 1.7X10-9 atm-cu m/mole(SRC), developed using a fragment constant estimation method(2). A base-catalyzed second-order hydrolysis rate constant of 0.018 L/mole-sec(SRC) was estimated using a structure estimation method(2); this corresponds to half-lives of 12 and 1.2 years at pH values of 7 and 8, respectively(2). According to a classification scheme(4), an estimated BCF of 3(SRC), from an estimated log Kow of 0.17(2) and a regression-derived equation(2), suggests the potential for bioconcentration in aquatic organisms is low. A 83% of Theoretical BOD using activated sludge in the Japanese MITI test(5) suggests that biodegradation may be an important environmental fate process in water(SRC). Using an ecosystem model, degradation rates of hydroxypropyl acrylate in water and sediment were 6.8X10-7/s and 7.5X10-8/s, respectively(6).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), hydroxypropyl acrylate, which has an estimated vapor pressure of 0.12 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), is expected to exist solely as a vapor. Vapor-phase hydroxypropyl acrylate is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals and ozone(SRC); the half-lives for these reactions in air is estimated to be 22 hours and 6.5 days(SRC), calculated from its respective rate constants of 1.7X10-11 and 1.7X10-18 cu cm/molecule-sec at 25 °C(SRC) that were derived using a structure estimation method(2). Hydroxypropyl acrylate contains chromophores that absorb at wavelengths >290 nm(3) and, therefore, may be susceptible to direct photolysis by sunlight(SRC). The degradation rate of hydroxypropyl acrylate in air was 1.4X10-5/s based on calculations using a chemical pollution footprint methodology(4).

Exposure RoutesThe substance can be absorbed into the body through the skin and by ingestion.
Toxicity Summary · 1건

IDENTIFICATION AND USE: Hydroxypropyl acrylate is a colorless liquid. It is mainly used either as a co-monomer in the manufacture of polymers or as a chemical reactant in the manufacture of chemical intermediates. It is used in food contact substances as indirect additive. HUMAN STUDIES: In human patch tests, three out of 24 patients showing irritation to initial exposure to acrylates including hydroxypropyl acrylate, showed sensitization reactions to hydroxypropyl acrylate exposure. Several cases of occupational contact dermatitis have been reported. ANIMAL STUDIES: In experimental animals, hydroxypropyl acrylates were highly irritating and corrosive to the eyes. Applied to the skin, they caused marked irritation and, occasionally, necrosis. Contact sensitivity was produced in guinea pigs. In rats given up to 2000 mg/kg clinical signs included ataxia, salivation, and passiveness. Animals that died during the study showed stained muzzle, lungs, stomach and intestines red and fluid filled, and enlarged stomach. An inhalation study with rats, mice, rabbits and dogs was conducted with hydroxypropyl acrylate. In rats, a small increase in the number of animals with changes in the lungs at 10 ppm (subacute pneumonitis) and the nasal mucosa was observed. In the mouse study, no mortality was observed. Three of 20 mice exposed to 10 ppm, but none exposed to 5 ppm showed signs of eye irritation. All rabbits exposed to 10 ppm and 2 of 4 animals exposed to 5 ppm developed slight rhinitis and eye irritation (moderate conjunctivitis). The most marked effects were seen in the upper respiratory system of all rabbits, especially those in the 10 ppm group that were characterized by mucopurulent rhinitis with squamous metaplasia and ulceration of the nasal turbinate mucosa. In the dog study, no mortality was observed. At necropsy, exudative rhinitis, tracheitis, and suppurative bronchopneumonia were observed in all hydroxypropyl acrylate-exposed dogs. Therefore, conjunctivitis and inflammatory, degenerative, and/or hyperplastic changes in the (upper) respiratory tract are the key effects following exposure to a mixture of hydroxypropyl acrylate isomers after inhalation exposure. No evidence of carcinogenicity was observed for the closely related, hydroxyethyl acrylate, following 18 months of inhalation exposure. In developmental study in rats exposed by inhalation (1, 5, or 10 ppm) no treatment related increase in embryo/fetal lethality or fetal malformations was observed at any dose level. Hydroxypropyl acrylate was tested in the bacterial reverse mutation assay test with Salmonella typhimurium TA98, TA100, TA1535, and TA1537 at concentrations up to 5000 ug/plate with and without metabolic activation. It was considered not mutagenic under the conditions of the assay .

Signs and Symptoms · 4건

Cough. Sore throat. Burning sensation.

MAY BE ABSORBED! Redness. Pain.

Redness. Pain.

Abdominal pain. Burning sensation in the throat and chest. Vomiting.

Ongoing Test Status · 1건

EPA has released the Interactive Chemical Safety for Sustainability (iCSS) Dashboard. The iCSS Dashboard provides an interactive tool to explore rapid, automated (or in vitro high-throughput) chemical screening data generated by the Toxicity Forecaster (ToxCast) project and the federal Toxicity Testing in the 21st century (Tox21) collaboration. /The title compound was tested by ToxCast and/or Tox21 assays/[USEPA; ICSS Dashboard Application; Available from, as of August 9, 2018: http://actor.epa.gov/dashboard/]

안전 데이터

wgk
1
tsca
TSCA listed
rtecs
UD3610000
ridadr
UN 1760 8/PG 3
HS 번호
29161290
risk_code
23/24/25-34-43

화학 및 산업

약리 정보

Absorption, Distribution and Excretion · 1건

2-hydroxyethyl acrylate (HEA) has been evaluated in a study that examined metabolism and excretion in male Fischer 344 rat using oral, intraperitoneal, dermal and inhalation routes of exposure ... For the oral and intraperitoneal routes of exposure the rats (four animals/dose level/route of exposure) received a single dose of (14)C-HEA at 2.5 or 50 mg/kg bw. For the inhalation exposure, six rats were exposed to a target concentration of 8 ppm (14)C-HEA for six hours in a head only inhalation chamber. For the dermal exposure, four rats were treated with (14)C-HEA at a dose of 50 mg/kg. No qualitative differences in urinary metabolites between routes were observed, indicating no marked route-dependent differences in the metabolic fate of HEA. The results of the study indicate that once the chemical becomes systemically available it is rapidly metabolized and eliminated from the body as either CO2 in the expired air or urinary metabolites with approximately equal percentage of administered/exposed dose eliminated by each route. The half-lives of elimination of radioactivity were approximately 14 hours for urine and 17 hours for CO2. The half-life of elimination of radioactivity from plasma was approximately 26 hours although the label was not associated with parent HEA. The available metabolic data on HEA is consistent with information on studies with other acrylates where hydrolysis of the ester functionality is the primary metabolic pathway. By analogy with ethyl acrylate and acrylic acid, it is expected that a minor metabolic pathway for HEA will be via conjugation with glutathione with the resulting mercapturic acid derivatives being excreted in the urine.

용도 및 제조

Uses · 5건

Comonomer in adhesives, elastomers, inks, and oil additives; viscosity reducer.

Hydroxypropyl acrylate is mainly used either as a co-monomer in the manufacture of polymers or as a chemical reactant in the manufacture of chemical intermediates.

For the manufacture of hydrogel contact lenses. /3-Hydroxypropyl acrylate/

Indirect Additives used in Food Contact Substances: HYDROXYPROPYL ACRYLATE

Hydroxypropyl acrylates, usually as isomer mixtures, are used in the industrial production of acrylate polymers for lacquers and artificial resins, and as a co-monomer in adhesives, elastomers, inks, and oil additives and as a viscosity reducer.

Impurities · 2건

Contains the following stabilizer(s): Mequinol (200 ppm)

A typical commercial sample of hydroxypropyl acrylate may contain acrylic acid (< or = 0.98% w/w), other esters (< or = 1.8% w/w), propylene glycol diacrylate (< or = 0.2% w/w) and propylene oxide (ca. 0.001% w/w). Methyl ethyl hydroquinone may be added at 250 to 650 ppm as an inhibitor of spontaneous polymerization.

U.S. Imports(1983) 1.36X10+9 g /Acrylates & Acrylic Acid/
U.S. Production · 6건

2023: 1,000,000 - <5,000,000 lb

(1972) 4.5X10+9 g (Capacity includes Hydroxyethyl)

(1975) 4.5X10+9 g (Capacity includes Hydroxyethyl)

The worldwide production volume of hydroxypropyl acrylate is estimated to be 6000 to 7000 tons per year. The US production is estimated to be 5000 tons per year.

2-Propenoic acid, monoester with 1,2-propanediol 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).

For more U.S. Production (Complete) data for Hydroxypropyl acrylate (7 total), please visit the HSDB record page.

Consumption Patterns · 2건

US consumption of commodity acrylate esters (2000): surface coatings 44%, adhesives/sealants 18%, textiles 15%, plastics additives 9%, paper 5%, other 9%; Western European consumption of commodity acrylate esters (1984): surface coatings 35-40%, adhesives/sealants 15%, textiles 10-15%, paper coating 15-20%, fibers and plastic comonomers 10%, other 10%

Essentially 100% as monomer.

Consumer UsesBinder
응용 분야 · 2건

용도Hydroxypropyl acrylate is an acrylic monomer for use in UV inks, lacquers, adhesives, etc. [2-Hydroxy-1-propylacrylate (67%)+1-hydroxy-2-propylacrylate(33%).

일반 설명A clear colorless liquid. Toxic by inhalation and skin absorption. Corrosive to tissue. Flash point 136°F. May polymerize exothermically if heated or contaminated. If the polymerization takes place inside a container, the container may rupture violently. Vapors heavier than air. Used to make plastics.

공급사50 곳

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