Grundinformationen
- 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
Weitere Namen anzeigen
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
Density
1.1 (NTP, 1992) - Denser than water; will sink
1.1074 @ 20 °C/20 °C
1.1074 @ 20°C
Solubility
10 to 50 mg/mL at 68.9 °F (NTP, 1992)
Insoluble in water
Flash Point
141 °F (NTP, 1992)
141 °F (61 °C) (open cup)
Boiling Point
135 °F at 2 mmHg (NTP, 1992)
57 °C @ 2 mm Hg
Polymerization occurs at boiling point
Vapor Density
4.4 (NTP, 1992) - Heavier than air; will sink (Relative to Air)
4.4 (air= 1)
Physical Description
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)
Sicherheit und Regulatorisches
GHS-Klassifizierung
GHS Classification
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
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.)
Hazards Summary
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).
NFPA Hazard Classification
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
First Aid
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
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
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
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
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.
Protective Action Criteria (PAC)
0.081 [ppm]
0.89 [ppm]
5.4 [ppm]
Personal Protective Equipment (PPE)
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
Human Toxicity Excerpts
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
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
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/
Non-Human Toxicity Values
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)
Chemie und Industrie
Verwendung und Herstellung
Uses
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
Methods of Manufacturing
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)
Anwendungen
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.
VerwendenGlycidyl Acrylate 85% can be used as an adhesive composition.
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