Ethylhexyl methacrylate
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Ethylhexyl methacrylate
structure -
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CAS No:
688-84-6
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Formula:
C12H22O2
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Chemical Name:
Ethylhexyl methacrylate
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Synonyms:
2-Propenoic acid,2-methyl-,2-ethylhexyl ester;Methacrylic acid,2-ethylhexyl ester;1-Hexanol,2-ethyl-,methacrylate;2-Ethylhexyl methacrylate;NSC 24173;NSC 32647;H 22 (methacrylate);H 22;Acryester EH;Blemmer EHMA 25;Light Ester EH;Ethylhexyl methacrylate;Visiomer EHMA;100242-87-3;118955-12-7;64125-64-0;75577-75-2;94290-92-3;153286-32-9
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CAS No:
Ethylhexyl methacrylate Basic Attributes
198.306
198.30
211-708-6
1289
32647|24173
DTXSID3027293|DTXSID6040797
2916140000
Characteristics
26.3
4.5
Liquid
0.880 g/cm3 @ Temp: 25 °C
-50 °C
110 °C @ Press: 14 Torr
92°C
1.436
H2O: <0.1 g/L
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. Moisture may cause rust-initiated polymerization. /Acrylic acid & derivatives/
Vapour pressure, Pa at 20°C: 133
Relative vapour density (air = 1): 6.8
LD50 orally in Rabbit: > 2000 mg/kg
This material polymerizes exothermically in the presence of heat, contamination, oxygen free atmosphere, free radicals, peroxides, and inhibitor depletion liberating heat. /Formulation >99% 2-ethylhexyl methacrylate/
Henry's Law constant: 1.1X10-3 atm-cu m/mol @ 25 °C /Estimated/
Hydroxyl radical reaction rate constant: 2.9X10-11 cu cm/molecule-sec @ 25 °C /Estimated/
Vapours are uninhibited and may polymerize in vents or flame arresters, causing blockage.
Safety Information
UN 3334 9
1
R36/37/38;R43
S26-S37/39-S24
OZ4630000
Xi:Irritant;
Cool. Store only if stabilized.
Stable, but may polymerize upon exposure to light. Heat sensitive. Incompatible with strong acids, strong oxidizing agents, strong bases.
P280-P305 + P351 + P338
H315-H317-H319-H335-H412
SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.
BIBRA working group; TA:Toxicity profile. BIBRA Toxicology International:19 (1996).
Combustible.
|Warning|H315 (42.54%): Causes skin irritation [Warning Skin corrosion/irritation]|P261, P264, P271, P272, P273, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P333+P313, P337+P313, P362, P363, P403+P233, P405, and P501|Aggregated GHS information provided by 851 companies from 29 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|H227: Combustible liquid [Warning Flammable liquids]|P201, P202, P210, P264, P273, P280, P281, P302+P352, P308+P313, P321, P332+P313, P362, P370+P378, P391, P403+P235, P405, and P501|P201, P202, P210, P261, P264, P272, P280, P281, P302+P352, P308+P313, P321, P332+P313, P333+P313, P362, P363, P370+P378, P403+P235, P405, and P501|Not Classified|P201, P202, P210, P264, P280, P281, P302+P352, P305+P351+P338, P308+P313, P321, P332+P313, P337+P313, P362, P370+P378, P403+P235, P405, and P501
Use water spray, powder, alcohol-resistant foam, carbon dioxide.
Suitable protective clothing and self-contained respiratory protective apparatus should be available for use of those who may have to rescue persons overcome by fumes. /acrylic acid and derivatives/
Combustible.
This material polymerizes exothermically in the presence of heat, contamination, oxygen free atmosphere, free radicals, peroxides, and inhibitor depletion liberating heat. /Formulation >99% 2-ethylhexyl methacrylate/
When designing a safe plant, among other important considerations, it is necessary to be aware of the considerable exothermic heat generated in some reactions. Thus, high pressure and temperatures may develop. Dangerous exposures can be avoided with careful design such as completely enclosing those processes where toxic chemical or intermediates occur.|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.|Employees should be instructed about the necessity of cleansing the skin if it is contaminated by materials which are irritants or skin-absorbed.|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.|Wear protective gloves to prevent skin exposure. If contact occurs, remove contaminated clothes; rinse and then wash skin with water and soap. Wear safety glasses to prevent eye exposure. If contact occurs, first rinse with plenty of water for several minutes (remove contact lenses if easily possible), then take to a doctor. Do not eat, drink, or smoke during work. /From table/
The substance irritates the eyes and the skin.
Personal protection: filter respirator for organic gases and vapours adapted to the airborne concentration of the substance.
Cool. Store only if stabilized.
No indication can be given about the rate at which a harmful concentration of this substance in the air is reached on evaporation at 20 °C.
The substance is irritating to the eyes and skin.
NO open flames.
Use ventilation.
Protective gloves.
Wear safety spectacles.
Drug Information
Small quantities of methacrylates may readily be metabolized by saponification into the alcohol and methacrylic acid. The latter may form an acetyl-coenzyme A derivative, which then enters the normal lipid metabolism. /methacrylates/|Acrylates and methacrylates are detoxified predominantly via conjugation with glutathione via the Michael addition reaction or glutathione-S-transferase. They are also likely to be hydrolyzed via carboxylesterases. The lower molecular weight esters are rapidly metabolized and eliminated, therefore, will not likely cause cumulative toxicity. /Methacrylates/
Fresh air, rest.
Remove contaminated clothes. Rinse and then wash skin with water and soap.
First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.
Basic treatment: Establish a patent airway. Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if needed. 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 ... . Anticipate seizures 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 ... . Cover skin burns with dry sterile dressings after decontamination ... . /Poison A and B/|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. 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 /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. Watch for signs of fluid overload ... . Treat seizures with diazepam (Valium) ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poison A and B/
/HUMAN EXPOSURE STUDIES/ Five male volunteers who developed contact dermatitis to acrylic based adhesive were tested for cross sensitization with other acrylic derivatives. ... None of the subjects had a reaction to methylmethacrylate or 2-ethyl-hexylmethacrylate. 2-Ethyl-hexyl-acrylate induced allergies in all subjects. Two subjects reacted to hydroxy-propyl-methacrylate; the other three subjects were not tested. There were broad cross reaction patterns within the acrylate esters up to octyl-acrylate. There was no reaction to N-tert-butyl-maleamic-acid (NTBM) or acrylonitrile.|/SIGNS AND SYMPTOMS/ Skin and/or eye exposure can cause redness. /From table/
The substance can be absorbed into the body by inhalation of its aerosol.
Redness.
Redness.
Ethylhexyl methacrylate Use and Manufacturing
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/|TRANSESTERIFICATION OR ESTERIFICATION OF 2-ETHYLHEXYL ALCOHOL WITH EITHER METHYL METHACRYLATE OR METHACRYLIC ACID
Adhesives and sealant chemicals
10,000,000 - 50,000,000 lb
2-Propenoic acid, 2-methyl-, 2-ethylhexyl ester, homopolymer: ACTIVE|XU - indicates a substance exempt from reporting under the Chemical Data Reporting Rule, (40 CFR 711).|All other chemical product and preparation manufacturing|2-Propenoic acid, 2-methyl-, 2-ethylhexyl 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/
Thin-layer chromatography (TLC), polarography, and spectrometry are used for soln measurements. Methacrylates in air have been analyzed by TLC, polarography, and colorimetry. Polarography has been used for determination of any residual monomer in the polymer. /Methacrylic acid & derivatives/
Computed Properties
Molecular Weight:198.30
XLogP3:4.5
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:8
Exact Mass:198.161979940
Monoisotopic Mass:198.161979940
Topological Polar Surface Area:26.3
Heavy Atom Count:14
Complexity:185
Undefined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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