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2,3-Epoxypropylacrylat

Glycidyl acrylate

HCID 7836
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Grundinformationen

CAS
106-90-1
Standard-SMILES
C=CC(=O)OCC1CO1
InChIKey
RPQRDASANLAFCM-UHFFFAOYSA-N
Summenformel
C6H8O3
Durchschnittliche Molmasse
128,13 g/mol
Monoisotopische Masse
128,04734412

Überblick

Glycidyl acrylate is a light amber liquid. (NTP, 1992)

Namen und Bezeichner

Bevorzugter Name
Glycidyl acrylate
IUPAC
oxiran-2-ylmethyl prop-2-enoate
Lokaler Name
2,3-Epoxypropylacrylat
Englischer Name
Glycidyl acrylate
Summenformel
C6H8O3
Molmasse
128.13

Namen und Synonyme

GLYCIDYL ACRYLATE106-90-12,3-Epoxypropyl acrylateGlycidyl propenateoxiran-2-ylmethyl prop-2-enoateAcrylic acid glycidyl esterAcrylic acid, 2,3-epoxypropyl ester2-Propenoic acid, oxiranylmethyl esterMethacyclic acid, 2,3-epoxypropyl ester1-Propanol, 2,3-epoxy-, acrylateglycidyl propenoateGlycidylester kyseliny akrylove
Weitere Namen anzeigen
glycidylOxiran-2-ylmethyl acrylateSR 378NSC 24151NSC 67196glycidylpropenateacrylatedeglycidyle
M 581epoxypropyl acrylateNSC-24151L8N627D5ZC2-Propenoic acid, 2-oxiranylmethyl esterNSC-67196DTXSID5025360RefChem:143827

Datenbank-Bezeichner

CAS
106-90-1
PubChem CID
7836
DTXSID
DTXSID5025360
UNII
L8N627D5ZC
EC Number
203-440-3
Nikkaji
J33.797H

Eigenschaften

Berechnete Struktureigenschaften

XLogP
0,4
Polarare Oberfläche (TPSA)
38,8 Ų
H-Brücken-Donoren
0
H-Brücken-Akzeptoren
3
Frei drehbare Bindungen
4
Schwere Atome
9
Formalladung
0
Komplexität
130

Experimentelle und physikochemische Eigenschaften

Chemical ClassesFlammable agents - 2nd degree
PolymersPlastics & Rubber -> (Meth)acrylates
Density · 3 Einträge

1.1 (NTP, 1992) - Denser than water; will sink

1.1074 @ 20 °C/20 °C

1.1074 @ 20°C

Color/FormLiquid
Solubility · 2 Einträge

10 to 50 mg/mL at 68.9 °F (NTP, 1992)

Insoluble in water

Flash Point · 2 Einträge

141 °F (NTP, 1992)

141 °F (61 °C) (open cup)

Boiling Point · 3 Einträge

135 °F at 2 mmHg (NTP, 1992)

57 °C @ 2 mm Hg

Polymerization occurs at boiling point

DecompositionWhen heated to decomp it emits acrid smoke and fumes.
Melting PointFreezing point: -41.5 °C

Sicherheit und Regulatorisches

Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.

GHS-Klassifizierung

GHS Classification · 6 Einträge

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)

Danger

H301 (100%): 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)

Gefahrenhinweise

Regulatory Information · 3 Einträge

Chemical: 2-Propenoic acid, oxiranylmethyl ester

TP - indicates a substance that is the subject of a proposed TSCA section 4 test rule.

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.)

Other Safety InformationEvaluation - Glycidyl acrylate and glycidyl methacrylate
DOT LabelFlammable Liquid Poison
Fire HazardsThis chemical is combustible. (NTP, 1992)
Fire PotentialFlammable liquid when exposed to heat or flame.
Health HazardsExcerpt from ERG Guide 131 [Flammable Liquids - Toxic]:
Hazards Summary · 1 Eintrag

Chemie und Industrie

Verwendung und Herstellung

Uses · 5 Einträge

Used as monomer (polymers for adhesives and coatings), crosslinking agent (polymers of trialkyltin esters), and epoxy resin diluent; [HSDB]

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

MONOMER FOR POLYMERS USED IN ADHESIVES & COATINGS

CROSSLINKING AGENT FOR POLYMERS OF TRIALKYLTIN ESTERS

EPOXY RESIN DILUENT

U.S. Imports(1983) 1.36x10+9 g /Acrylates & Acrylic Acid/
U.S. Production(1977) AT LEAST 4.54X10+7 G
Methods of Manufacturing · 3 Einträge

Acrylates can be prepared by ... dehydration of the corresponding hydroxyalkanoic acid, saponification of the alkene nitrile, catalytic hydration of acetylene and carbon monoxide, or the reaction of acetone with hydrocyanic acid. /Acrylates/

In ... propylene oxidation process acrolein is first formed by the catalytic oxidation of propylene vapor at high temp in the presence of steam. The acrolein is then oxidized to acrylic acid. ... The acrylic acid is esterified with alcohol to the ... acrylic ester in a separate process. /Acrylic ester monomers/

Epichlorohydrin + acrylic acid (esterification)

Formulations/Preparations... Hydroquinone or monomethyl ether hydroquinone are added to acrylic monomers to stabilize them ... . /Acrylic ester monomers/
General Manufacturing Information2-Propenoic acid, 2-oxiranylmethyl ester: ACTIVE
Anwendungen · 2 Einträge

BeschreibungGlycidyl acrylate (GA) is a monomer that polymerizes in the presence of a free-radical initiator to form polyacrylic acid. This compound is used as a cross-linking agent for coatings, adhesives, and sealing compounds. GA is an excellent starting material for the preparation of cationic polymers with high reactivity and good stability. It has been used as a control agent in the synthesis of polycarboxylic acids and fatty acids. The hydroxyl group on this molecule allows it to be used as a water-repellent coating or sealant.

Zugehörige Reaktionen

19
Reaktionsaufzeichnung erstellen
Reaktionsgleichung von HRID 126673
HRID 126673als Eduktuspto-grants-1981_03
Reaktionsgleichung von HRID 284367
HRID 284367als EduktTraining data from https://doi.org/10.1039/C8SC04228D (8/10)
Reaktionsgleichung von HRID 293980
HRID 293980als EduktTraining data from https://doi.org/10.1039/C8SC04228D (8/10)
Reaktionsgleichung von HRID 574026
HRID 574026als Eduktuspto-grants-2015_05
Reaktionsgleichung von HRID 850693
HRID 850693als Eduktuspto-grants-2000_01
Reaktionsgleichung von HRID 894937
HRID 894937als Produktuspto-grants-1981_08
Reaktionsgleichung von HRID 936470
HRID 936470als EduktValidation data from https://doi.org/10.1039/C8SC04228D
Reaktionsgleichung von HRID 1089656
HRID 1089656als Produktuspto-grants-1992_01
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Vapor Density · 2 Einträge

4.4 (NTP, 1992) - Heavier than air; will sink (Relative to Air)

4.4 (air= 1)

Vapor Pressure2.97 [mmHg]
Physical Description · 2 Einträge

Glycidyl acrylate is a light amber liquid. (NTP, 1992)

Light amber liquid; [CAMEO] Colorless liquid; [CHEMINFO] Clear deep red liquid; [MSDSonline]

Physikochemische Eigenschaften

Schmelzpunkt
-42 °C · -42 °C
Siedepunkt
60 °C · 60°C 16mm
Dichte
1.1163 g/cm3 · 1.1163 g/cm3
Brechungsindex
1.4508 · 1.4508 (589.3 nm 20℃)
Flammpunkt
61 °C · 61°C(lit.)
storage temp.
-20 °C · -20°C Freezer
Löslichkeit
Chloroform (Sparingly), Methanol (Slightly)
Aggregatzustand
clear liquid
Farbe
Colorless to Light orange to Yellow
Stabilität
Stability Combustible. Incompatible with strong oxidizing agents. May be prone to polymerization.
InChI
InChI=1S/C6H8O3/c1-2-6(7)9-4-5-3-8-5/h2,5H,1,3-4H2
InChIKey
RPQRDASANLAFCM-UHFFFAOYSA-N
SMILES
C(OCC1CO1)(=O)C=C
EPA chemische Informationen
Glycidyl acrylate (106-90-1)

A skin and eye irritant; [Hawley] External application to rabbit eyes scored 10 on a scale of 1-10 (10 being most severe) for degree of injury after 24 hours; [HSDB] May polymerize; [CAMEO] Corrosive to skin and eyes, based on animal studies; [CHEMINFO] Can cause burns; May cause skin sensitization; [eChemPortal: ESIS] A corrosive substance that can cause injury to the skin, eyes, and respiratory tract; May cause skin sensitization; Can be absorbed through skin; Inhalation may cause chemical pneumonitis and pulmonary edema; [MSDSonline] See ACRYLIC RESINS (MONOMERS).

Reactive GroupEpoxides
Reactivity AlertsHighly Flammable
Reactivity ProfileGLYCIDYL ACRYLATE may be sensitive to polymerizing conditions and/or catalysts. This compound will react with oxidizers. (NTP, 1992)
Air and Water ReactionsWater soluble.
NFPA Hazard Classification · 3 Einträge

0 - Materials that, under emergency conditions, would offer no hazard beyond that of ordinary combustible materials.

2 - Materials that must be moderately heated or exposed to relatively high ambient temperatures before ignition can occur. Materials would not under normal conditions form hazardous atmospheres with air, but under high ambient temperatures or under moderate heating could release vapor in sufficient quantities to produce hazardous atmospheres with air.

0 - Materials that in themselves are normally stable, even under fire conditions.

Sicherheit und Schutzausrüstung

Fire FightingFires involving this chemical should be extinguished with a foam, dry chemical or carbon dioxide extinguisher. (NTP, 1992)
First Aid · 1 Eintrag

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.

Storage Conditions · 1 Eintrag

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/

Nonfire Spill Response · 1 Eintrag

SMALL SPILLS AND LEAKAGE: If you spill this chemical, use absorbent paper to pick up all liquid spill material. Your contaminated clothing and absorbent paper should be sealed in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with alcohol followed by washing with a strong soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned.

Disposal Methods · 1 Eintrag

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 Einträge

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 131 [Flammable Liquids - Toxic]:
Protective Action Criteria (PAC) · 3 Einträge

0.081 [ppm]

0.89 [ppm]

5.4 [ppm]

Personal Protective Equipment (PPE) · 3 Einträge

RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with an organic vapor/acid gas cartridge (specific for organic vapors, HCl, acid gas and SO2) with a dust/mist filter. (NTP, 1992)

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/

Protection required for safe handling of acrylic acid and esters commonly includes use of impervious gloves, shoe soles, and clothing; splash-proof goggles ... . /Acrylic acid & derivatives/

Toxikologische Informationen

Adverse EffectsDermatotoxin - Skin burns.
Human Toxicity Excerpts · 1 Eintrag

THE ACUTE TOXICITY OF THE ACRYLATES DECREASES WITH INCREASING MOLECULAR WEIGHT. ... HUMAN SIGNS & SYMPTOMS FOLLOWING INGESTION OF ACRYLIC MONOMERS INCL COLLAPSE, SEVERE RESPIRATORY DIFFICULTIES, & CNS STIMULATION. ACUTE INHALATION OF HIGHER CONCN MAY CAUSE MARKED IRRITATION, SALIVATION, CONJUNCTIVAL IRRITATION, & PRONOUNCED PULMONARY IRRITATION OR EDEMA. PROLONGED SKIN OR EYE CONTACT MAY RESULT IN SEVERE TISSUE DAMAGE. THE PATHOLOGY FROM SINGLE EXPOSURE IS NONSPECIFIC, CONTRARY TO REPEATED EXPOSURE EFFECTS, WHICH INCL PULMONARY CONGESTION OR HEMORRHAGE & CLOUDY SWELLING OF LIVER & KIDNEY. /ACRYLATES/

Non-Human Toxicity Excerpts · 3 Einträge

GLYCIDYL ACRYLATE ADMIN @ 0.5 MG/100 G IP, SHOWED NO INHIBITORY EFFECT ON TRANSPLANTED WALKER TUMORS IN RATS 24 HR AFTER DOSE, BONE MARROW SHOWED 2% ANAPHASES IN EXCESS OF CONTROLS WITH STICKY CHROMOSOME BRIDGES.

Acrylic acid 2,3-epoxypropyl ester has been tested externally on the eyes of rabbits & ... rated 10 on scale of 1 to 10 according to the degree of injury observed after 24 hr. The most severely injurious substances have been rated 10.

Contact sensitivity was produced in guinea pigs with mono-, di-, and tri- acrylate compounds. /Mono-, di-, and tri- acrylate compounds/

Antidote and Emergency Treatment · 2 Einträge

Basic treatment: Establish a patent airway. Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if necessary. Administer oxygen by nonrebreather mask at 10 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. Administer activated charcoal ... . /Esters and related compounds/

Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious. Positive-pressure ventilation techniques with a bag-valve-mask device may be beneficial. Monitor cardiac rhythm and treat arrhythmias if 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. For hypotension with signs of hypovolemia, administer fluid cautiously. Consider vasopressors if patient is hypotensive with a normal fluid volume. Watch for signs of fluid overload ... . Consider drug therapy for pulmonary edema ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Esters and related compounds/

Toxicity DataLCLo (rat) = 125 ppm/4h
Non-Human Toxicity Values · 2 Einträge

LD50 Rat oral 210 mg/kg

LD50 Rabbit skin 400 mg/kg

Sicherheitsdaten

tsca
TSCA listed
ridadr
2810
hs_code
2916.12.5050
RTECS-Nr.
AS9275000
risk_code
23/24/25-34-43
hazard_code
T
safety_code
26-36/37/39-45
hazard_class
6.1(b)
packing_group
III
Giftige Stoffe Daten
106-90-1(Hazardous Substances Data)

VerwendenGlycidyl Acrylate 85% can be used as an adhesive composition.