Butyl methacrylate
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Butyl methacrylate
structure -
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CAS No:
97-88-1
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Formula:
C8H14O2
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Chemical Name:
Butyl methacrylate
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Synonyms:
2-Propenoic acid,2-methyl-,butyl ester;Methacrylic acid,butyl ester;Butyl methacrylate;n-Butyl methacrylate;Butyl 2-methyl-2-propenoate;Acryester B;Blemmer BMA;Butyl 2-methylacrylate;NSC 20956;2-Methyl-2-propenoic acid butyl ester;N 212;Light Ester NB;Acryester BMA;Visiomer n-BMA;2-Methyl-acrylic acid butyl ester;55922-77-5;159172-35-7;1151915-97-7;1310566-97-2;1343477-79-1
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CAS No:
Description
clear colourless liquid with an ester-like odour Butyl methacrylate is a flammable, colorless liquid with a mild odor.
N-butyl methacrylate appears as a clear colorless liquid. Flash point 130°F. Less dense (7.5 lb / gal) than water and insoluble in water. Hence floats on water. Vapors heavier than air. Used to make resins adhesives, and oil additives.|Liquid|COLOURLESS LIQUID WITH CHARACTERISTIC ODOUR.
N-butyl methacrylate appears as a clear colorless liquid. Flash point 130°F. Less dense (7.5 lb / gal) than water and insoluble in water. Hence floats on water. Vapors heavier than air. Used to make resins adhesives, and oil additives.|Butylmethacrylate is an enoate ester.
Butyl methacrylate Basic Attributes
142.19600
142.20
618-468-5
R5QX287XXU
1018
20956
2227
DTXSID4024696
Colorless liquid
2916140000
Characteristics
26.30000
1.90580
N-butyl methacrylate appears as a clear colorless liquid. Flash point 130°F. Less dense (7.5 lb / gal) than water and insoluble in water. Hence floats on water. Vapors heavier than air. Used to make resins adhesives, and oil additives.
0.8936 g/cm3 @ Temp: 20 °C
-25 °C
160 °C @ Press: 760 Torr
41ºC
1.4225-1.4245
H2O: 3 g/L (20 ºC)
Refrigerator (+4ºC) + Flammables area
2 mm Hg ( 20 °C)
4.91 (15 °C, vs air)
LD50 orally in Rabbit: > 2000 mg/kg LD50 dermal Rabbit > 2000 mg/kg
Lower flammable limit: 2% in air; Upper flammable limit: 8% in air (estimates)
vol% in air: 1
Faint characteristic odor of esters
Henry's Law constant = 4.96X10-4 atm-cu m/mol at 25 °C (est)
Readily polymerized|Liquid water interfacial tension: 35 dynes/cm = 0.035 N/m at 20 °C; Heat of polymerization: -180 BTU/lb = -100 cal/g = -4.2X10+5 J/kg; Reid vapor pressure: low|It weighs about 7.5 lb/gal.|Hydroxyl radical reaction rate constant = 2.3X10-11 cu cm/molec-sec at 25 °C (est)
Flammable. Sensitive to moisture. Insoluble in water.
Acrylates and Acrylic Acids
Highly Flammable
N-BUTYL METHACRYLATE reacts exothermically with acids. Reacts with oxidizing agents. Strong oxidizing acids may cause a reaction that is sufficiently exothermic to ignite the reaction products. Heat is generated with caustic solutions. Generates flammable hydrogen with alkali metals and hydrides. Polymerizes easily (NTP, 1992).
562 °F (USCG, 1999)|562 °F|290 °C
-14,800 BTU/lb = -8,230 cal/g = -344X10+5 J/kg (est)
Lower flammable limit: 2% in air; Upper flammable limit: 8% in air (estimates)
As a result of flow, agitation, etc., electrostatic charges can be generated.
Safety Information
III
3
UN 2227
1
R10; R36/37/38; R43
S16; S36/37/39
OZ3675000
Xi
Fireproof. Separated from oxidants. Cool. Dry. Keep in the dark. Store only if stabilized. Store in an area without drain or sewer access.
Stable (though if no stabilizers are present, it may polymerize; typically stabilized through the addition of HQME). Incompatible with strong reducing agents, strong oxidizing agents. Flammable. Water-reactive at high or low pH.
P261-P280-P305 + P351 + P338
H226-H315-H317-H319-H335
SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity 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 and plant life; and conformance with environmental and public health regulations.|Options for disposal of waste or spilled material: large quantities can be returned to the manufacturer for recycle. Small quantities may be incinerated under controlled conditions in incinerators suitable for methacrylates. Combustion products include carbon monoxide, carbon dioxide, and water. The product must be disposed of as special waste in accordance with regulations for special waste.
May accumulate static electrical charges and cause ignition of its vapors.
Homopolymers and copolymers of butyl methacrylate is an indirect food additive for use only as a component of adhesives.
Organization for Economic Cooperation and Development; Screening Information Data Set for Short Chain Alkyl Methacrylates, CAS Nos. 97-63-2, 97-86-9, 97-88-1, 688-84-6 (April 2004). This OECD Initial Assessment of HPV Chemicals is part of a series of OECD SIDS documents published by UNEP Chemicals to facilitate the access to information needed for health and environmental risk assessments of chemicals.[Available from, as of February 16, 2010: http://www.oecd.org/document/63/0,2340,en_2649_34379_1897983_1_1_1_1,00.html]|European Commission, ESIS; IUCLID Dataset, Butyl methacrylate (97-88-1) (2000 CD-ROM edition) contains information on use, toxicology, and environmental effects of this chemical as supplied to the European Union by industry.[Available from, as of February 22, 2010: http://esis.jrc.ec.europa.eu/]
Behavior in Fire: Containers may explode due to polymerization. (USCG, 1999)|Flammable. Above 50 °C explosive vapour/air mixtures may be formed.|Flammable - 2nd degree, Reactive - 2nd degree
|Warning|H226: Flammable liquid and vapor [Warning Flammable liquids]|P210, P233, P240, P241, P242, P243, P261, P264, P271, P272, P280, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P312, P321, P332+P313, P333+P313, P337+P313, P362, P363, P370+P378, P403+P233, P403+P235, P405, and P501|H226 (99.91%): Flammable liquid and vapor [Warning Flammable liquids]|Aggregated GHS information provided by 1118 companies from 34 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|P210, P233, P240, P241, P242, P243, P260, P261, P271, P273, P280, P303+P361+P353, P304+P340, P312, P314, P370+P378, P403+P233, P403+P235, P405, and P501|H315: Causes skin irritation [Warning Skin corrosion/irritation]|P261, P264, P272, P280, P302+P352, P321, P332+P313, P333+P313, P362, P363, and P501|P201, P202, P210, P233, P240, P241, P242, P243, P260, P261, P264, P271, P280, P281, P303+P361+P353, P304+P340, P305+P351+P338, P308+P313, P312, P314, P332+P313, P337+P313, P370+P378, P403+P233, P403+P235, P405, and P501
Excerpt from ERG Guide 130P [Flammable Liquids (Water-Immiscible / Noxious)]: As an immediate precautionary measure, isolate spill or leak area for at least 50 meters (150 feet) in all directions. LARGE SPILL: Consider initial downwind evacuation for at least 300 meters (1000 feet). FIRE: If tank, rail car or tank truck is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions. (ERG, 2016)
Excerpt from ERG Guide 130P [Flammable Liquids (Water-Immiscible / Noxious)]: ELIMINATE all ignition sources (no smoking, flares, sparks or flames in immediate area). All equipment used when handling the product must be grounded. Do not touch or walk through spilled material. Stop leak if you can do it without risk. Prevent entry into waterways, sewers, basements or confined areas. A vapor-suppressing foam may be used to reduce vapors. Absorb or cover with dry earth, sand or other non-combustible material and transfer to containers. Use clean, non-sparking tools to collect absorbed material. LARGE SPILL: Dike far ahead of liquid spill for later disposal. Water spray may reduce vapor, but may not prevent ignition in closed spaces. (ERG, 2016)
Wear self contained positive pressure breathing apparatus and full protective clothing. (USCG, 1999)|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/|Personnel protection: ... Wear appropriate chemical protective glove, boots and goggles. /Butyl methacrylate, combustible liquid, N.O.S.,and n-butyl methacrylate, stabilized/
Flammable
Lower explosive limit: 2%; Upper explosive limit: 8%.|Forms an explosive mixture with air.|Explosive in the form of vapor when exposed to heat or flame.|Explosive limits , vol% in air: 1-8
Foam, dry chemical, carbon dioxide.|If material on fire or involved in fire: Do not extinguish fire unless flow can be stopped. Use water in flooding quantities as fog. Solid streams of water may spread fire. Cool all affected containers with flooding quantities of water. Apply water from as far a distance as possible. Use foam, dry chemical, or carbon dioxide. /Butyl methacrylate, combustible liquid, N.O.S.,and n-butyl methacrylate, stabilized/
SRP: Wastewater from contaminant suppression, cleaning of protective clothing/equipment, or contaminated sites should be contained and evaluated for subject chemical or decomposition product concentrations. Concentrations shall be lower than applicable environmental discharge or disposal criteria. Alternatively, pretreatment and/or discharge to a permitted wastewater treatment facility is acceptable only after review by the governing authority and assurance that "pass through" violations will not occur. Due consideration shall be given to remediation worker exposure (inhalation, dermal and ingestion) as well as fate during treatment, transfer and disposal. If it is not practicable to manage the chemical in this fashion, it must be evaluated in accordance with EPA 40 CFR Part 261, specifically Subpart B, in order to determine the appropriate local, state and federal requirements for disposal.|Spill Handling: Evacuate and restrict persons not wearing protective equipment from area of spill or leak until cleanup is complete. Remove all ignition sources. Establish forced ventilation to keep levels below explosive limit. Absorb liquids in vermiculite, dry sand, earth, peat, carbon, or a similar material and deposit in sealed containers. Ventilate area of spill or leak after clean-up is complete. It may be necessary to contain and dispose of this chemical as a hazardous waste. If material or contaminated runoff enters waterways, notify downstream users of potentially contaminated waters.
SRP: The scientific literature for the use of contact lenses by industrial workers is inconsistent. The benefits 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.|SRP: Contaminated protective clothing should be segregated in a manner that results in no direct personal contact by personnel who handle, dispose of, or clean the clothing. Quality assurance procedures to confirm the efficacy of the cleaning procedures should be implemented prior to the decontaminated protective clothing being returned for reuse by the workers. Contaminated clothing (including shoes/socks) should not be taken home at end of shift, but should remain at employee's place of work for cleaning.|... 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/|If material not on fire and not involved in fire: Keep sparks, flames, and other sources of ignition away. Keep meterial out of water sources and sewers. Build dikes to contain flow as necessary. Use water spray to knock-down vapors. /Butyl methacrylate, combustible liquid, N.O.S.,and n-butyl methacrylate, stabilized/|For more Preventive Measures (Complete) data for n-Butyl methacrylate (6 total), please visit the HSDB record page.
/GUIDE 130P: FLAMMABLE LIQUIDS (NON-POLAR/WATER-IMMISCIBLE/NOXIOUS)/ Fire or Explosion: HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames. Vapors may form explosive mixtures with air. Vapors may travel to source of ignition and flash back. Most vapors are heavier than air. They will spread along ground and collect in low or confined areas (sewers, basements, tanks). Vapor explosion hazard indoors, outdoors or in sewers. Those substances designated with a "P" may polymerize explosively when heated or involved in a fire. Runoff to sewer may create fire or explosion hazard. Containers may explode when heated. Many liquids are lighter than water. /n-Butyl methacrylate; n-Butyl methacrylate, stabilized/|/GUIDE 130P: FLAMMABLE LIQUIDS (NON-POLAR/WATER-IMMISCIBLE/NOXIOUS)/ Health: May cause toxic effects if inhaled or absorbed through skin. Inhalation or contact with material may irritate or burn skin and eyes. Fire will produce irritating, corrosive and/or toxic gases. Vapors may cause dizziness or suffocation. Runoff from fire control or dilution water may cause pollution. /n-Butyl methacrylate; n-Butyl methacrylate, stabilized/|/GUIDE 130P: FLAMMABLE LIQUIDS (NON-POLAR/WATER-IMMISCIBLE/NOXIOUS)/ Public Safety: CALL Emergency Response Telephone Number ... As an immediate precautionary measure, isolate spill or leak area for at least 50 meters (150 feet) in all directions. Keep unauthorized personnel away. Stay upwind. Keep out of low areas. Ventilate closed spaces before entering. /n-Butyl methacrylate; n-Butyl methacrylate, stabilized/|/GUIDE 130P: FLAMMABLE LIQUIDS (NON-POLAR/WATER-IMMISCIBLE/NOXIOUS)/ Protective Clothing: Wear positive pressure self-contained breathing apparatus (SCBA). Structural firefighters' protective clothing will only provide limited protection. /n-Butyl methacrylate; n-Butyl methacrylate, stabilized/|For more DOT Emergency Guidelines (Complete) data for n-Butyl methacrylate (8 total), please visit the HSDB record page.
No person may /transport,/ offer or accept a hazardous material for transportation in commerce unless that person is registered in conformance ... and the hazardous material is properly classed, described, packaged, marked, labeled, and in condition for shipment as required or authorized by ... /the hazardous materials regulations (49 CFR 171-177)./|The International Air Transport Association (IATA) Dangerous Goods Regulations are published by the IATA Dangerous Goods Board pursuant to IATA Resolutions 618 and 619 and constitute a manual of industry carrier regulations to be followed by all IATA Member airlines when transporting hazardous materials.|The International Maritime Dangerous Goods Code lays down basic principles for transporting hazardous chemicals. Detailed recommendations for individual substances and a number of recommendations for good practice are included in the classes dealing with such substances. A general index of technical names has also been compiled. This index should always be consulted when attempting to locate the appropriate procedures to be used when shipping any substance or article.
Contact can irritate the eyes and skin. Inhalation can irritate the respiratory tract with coughing, wheezing, and/or shortness of breath.|Irritating to eyes, resp system and skin.
Personal protection: filter respirator for organic gases and vapours adapted to the airborne concentration of the substance. Do NOT let this chemical enter the environment. Collect leaking liquid in sealable containers. Absorb remaining liquid in sand or inert absorbent. Then store and dispose of according to local regulations.
Fireproof. Separated from oxidants. Cool. Dry. Keep in the dark. Store only if stabilized. Store in an area without drain or sewer access.
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.
Lachrymation. The substance is irritating to the eyes, skin and respiratory tract. If swallowed the substance may cause vomiting and could result in aspiration pneumonitis. Medical observation is indicated.
Repeated or prolonged contact may cause skin sensitization.
NO open flames, NO sparks and NO smoking. Above 50 °C use a closed system, ventilation and explosion-proof electrical equipment. Prevent build-up of electrostatic charges (e.g., by grounding).
AVOID ALL CONTACT!
Use ventilation, local exhaust or breathing protection.
Protective gloves. Protective clothing.
Wear safety goggles.
| 1 - Materials that, under emergency conditions, can cause significant irritation.| 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.| 2 - Materials that readily undergo violent chemical changes at elevated temperatures and pressures.
INDOOR: n-Butyl methacrylate has been identified as a volatile component of furniture surface coatings, concentration not specified(1).
n-Butyl methacrylate was identified as a volatile component of paint-coated steel plates heated to 350 °C, concentration ranging from 1 to 70 mg/cu m(1).
Toxicity
Some compounds, such as the methyl, ethyl, n-propyl, or butyl methacrylates can produce inhibition of barium chloride-induced contraction of the isolated guinea pig ileum.
LD50 Mouse oral 15,800 mg/kg|LD50 Mouse sc 2,600 mg/kg|LD50 Rat oral 16,000 mg/kg|LD50 Rat oral 22,600 mg/kg|For more Non-Human Toxicity Values (Complete) data for n-Butyl methacrylate (13 total), please visit the HSDB record page.
n-Butyl methacrylate's production and use in dental technology, acrylic surface coatings(1), as a monomer for resins, solvent coatings, adhesives, oil additives, in emulsions for textiles, and in leather and paper finishing(2) may result in its release to the environment through various waste streams(SRC).
TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 55(SRC), determined from a structure estimation method(2), indicates that n-butyl methacrylate is expected to have high mobility in soil(SRC). Volatilization of n-butyl methacrylate from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 5.0X10-4 atm-cu m/mole(SRC), based upon its vapor pressure, 2.12 mm Hg(3), and water solubility, 800 mg/L(4). n-Butyl methacrylate is expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(3). Utilizing the Japanese MITI test, 88% of the theoretical BOD was reached in 4 weeks(5) indicating that biodegradation is an important environmental fate process in soil(SRC).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 55(SRC), determined from a structure estimation method(2), indicates that n-butyl methacrylate is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(3) based upon an estimated Henry's Law constant of 5.0X10-4 atm-cu m/mole(SRC), derived from its vapor pressure, 2.12 mm Hg(4), and water solubility, 800 mg/L(5). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 5.6 hours and 5.4 days, respectively(SRC). According to a classification scheme(6), an estimated BCF of 37(SRC), from its log Kow of 2.88(7) and a regression-derived equation(8), suggests the potential for bioconcentration in aquatic organisms is moderate(SRC). Hydrolysis is not expected to be an important process(SRC) based on estimated hydrolysis half-lives of 80 and 8 years at pHs 7 and 8, respectively(9). Utilizing the Japanese MITI test, 88% of the theoretical BOD was reached in 4 weeks(10) indicating that biodegradation is an important environmental fate process in water(SRC).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), n-butyl methacrylate, which has a vapor pressure of 2.12 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase n-butyl 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 17 hours(SRC), calculated from its rate constant of 2.3X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Vapor-phase n-butyl methacrylate is also degraded in the atmosphere by reaction with ozone(SRC); the half-life for this reaction in air is estimated to be 1 day(SRC), calculated from its rate constant of 1.1X10-17 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). n-Butyl methacrylate does not contain chromophores that absorb at wavelengths >290 nm(4) and therefore is not expected to be susceptible to direct photolysis by sunlight(SRC).
The rate constant for the vapor-phase reaction of n-butyl methacrylate with photochemically-produced hydroxyl radicals has been estimated as 2.3X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 17 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). The rate constant for the vapor-phase reaction of n-butyl methacrylate with ozone has been estimated as 1.1X10-17 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(1). This corresponds to an atmospheric half-life of about 1 day at an atmospheric concentration of 7X10+11 ozone molecules per cu cm(2). A base-catalyzed second-order hydrolysis rate constant of 2.7X10-3 L/mole-sec(SRC) was estimated using a structure estimation method(3); this corresponds to half-lives of 80 and 8 years at pH values of 7 and 8, respectively(3). n-Butyl methacrylate does not contain chromophores that absorb at wavelengths >290 nm(4) and therefore is not expected to be susceptible to direct photolysis by sunlight(SRC).
An estimated BCF of 37 was calculated in fish for n-butyl methacrylate(SRC), using a log Kow of 2.88(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is moderate(SRC).
Using a structure estimation method based on molecular connectivity indices(1), the Koc of n-butyl methacrylate can be estimated to be 55(SRC). According to a classification scheme(2), this estimated Koc value suggests that n-butyl acrylate is expected to have high mobility in soil.
The Henry's Law constant for n-butyl methacrylate is estimated as 5.0X10-4 atm-cu m/mole(SRC) derived from its vapor pressure, 2.12 mm Hg(1), and water solubility, 800 mg/L(2). This Henry's Law constant indicates that n-butyl methacrylate is expected to volatilize from water surfaces(3). Based on this Henry's Law constant, the volatilization half-life from a model river (1 m deep, flowing 1 m/sec, wind velocity of 3 m/sec)(3) is estimated as 5.6 hours(SRC). The volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec)(3) is estimated as 5.4 days(SRC). n-butyl acrylate's estimated Henry's Law constant indicates that volatilization from moist soil surfaces may occur(SRC). The potential for volatilization of n-butyl methacrylate from dry soil surfaces may exist(SRC) based upon its vapor pressure(1).
According to the 2006 TSCA Inventory Update Report, the number of persons reasonably likely to be exposed in the industrial manufacturing, processing, and use for n-butyl methacrylate is 1000 or greater; the data may be greatly underestimated(1).|Occupational exposure to n-butyl methacrylate may occur through inhalation and dermal contact with this compound at workplaces where n-butyl methacrylate is produced or used. Monitoring and use data indicate that the general population may be exposed to n-butyl methacrylate via inhalation and dermal contact with consumer products containing n-butyl methacrylate. (SRC)
Drug Information
Recent studies have confirmed that alkyl-methacrylate esters are rapidly hydrolyzed by ubiquitous carboxylesterases ... First pass (local) hydrolysis of the parent ester has been shown to be significant for all routes of exposure. For example, no parent ester can be measured systemically following skin exposure to EMA and larger esters, as the lower rate of absorption for these esters is within the metabolic capacity of the skin ... Parent ester will also be effectively hydrolyzed within the G.I. tract and within the tissues of the upper respiratory tract (particularly the olfactory tissue). Systemically absorbed parent ester will be effectively removed during the first pass through the liver ... resulting in their relatively rapid elimination from the body ... /Short chain alkyl-methacrylate esters/
n-BMA, like MMA, is rapidly metabolized by body carboxylesterases ... Hydrolysis of n-BMA yields methacrylic acid and n-butanol which are further metabolized by physiological pathways, methacroyl CoA being a physiological substrate of the valine pathway.|Butyl methacrylate interacts with cytochrome P450 to form type 1 spectral complex.|In vitro hydrolysis of n-BMA was studied using a porcine liver esterase preparation. The Michaelis Menten constant, Km, and Vmax were on the order of 30 uM and 1.49 nmol/min, indicating that n-BMA is readily hydrolyzed by liver esterases. When compared to other methacrylic acid esters, increased chain length of the ester increased substrate affinity but decreased the turnover of the enzymatic hydrolysis.|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.|For more Metabolism/Metabolites (Complete) data for n-Butyl methacrylate (7 total), please visit the HSDB record page.
The cause of the lacrimatory action of esters containing unsaturated acids is undoubtedly the result of some mechanism ... in which the neighboring keto group has a polarizing effect on double bond, making it capable of adding /to/ nucleophilic agents such as SH groups /from certain enzymes/. /Unsaturated aliphatic esters/
Typical impurities include Methyl acrylic acid (MAA) (CAS 79-41-4) or MMA (CAS 80-62-6) (depending whether the direct esterification or trans-esterification route is used), the unreacted alcohol and water.
Inhalation may cause nausea because of offensive odor. Contact with liquid causes irritation of eyes and mild irritation of skin. Ingestion causes irritation of mouth and stomach. (USCG, 1999)
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. SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. If symptoms such as redness or irritation develop, IMMEDIATELY call a physician and be prepared to transport the victim to a hospital for treatment. INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. If symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop, call a physician and be prepared to transport the victim to a hospital. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing. INGESTION: DO NOT INDUCE VOMITING. If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center. Be prepared to transport the victim to a hospital if advised by a physician. If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. IMMEDIATELY transport the victim to a hospital. (NTP, 1992)
Fresh air, rest. Half-upright position. Refer for medical attention.
Remove contaminated clothes. Rinse and then wash skin with water and soap. Refer for medical attention .
Rinse with plenty of water (remove contact lenses if easily possible).
Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand-valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR as necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Esters and related compounds/|Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). 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. Provide a low-stimulus environment. 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 0.9% saline (NS) 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 ... . Treat frostbite by rapid rewarming ... . /Esters and related compounds/|Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Positive-pressure ventilation techniques with a bag-valve-mask device may be beneficial. Consider drug therapy for pulmonary edema ... . Monitor cardiac rhythm and treat arrhythmias if necessary ... . Start IV administration of D5W /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's (LR) if signs of hypovolemia are present. 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 ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Esters and related compounds/
/HUMAN EXPOSURE STUDIES/ ... In 542 dermatitis patients given covered patch tests with 1% EMA or 1% nBMA in petrolatum, one individual responded to EMA and another to both EMA and nBMA ... No reactions were seen in 22 contact dermatitis patients given 24-hr covered patch tests with esters within the category at a concentration of 1% in petrolatum ... The contact dermatitis of many of the tested individuals was attributed to (meth)acrylate exposure ... The prevalence of positive clinical challenge responses /was reported/ in dental clinicians that had been referred with dermatitis and suspected of having allergy to (meth)acrylates as 1.2% (51/4221) for MMA, 0.7% (16/2323) for EMA and 0.3% (1/347) for BMA ... The prevalence in a similar, pre-selected clinical cohort /was reported/ as 0.8% (9/1161) for MMA and 0.3% (2/625) for EMA ... The prevalence of positive clinical challenge tests in patients referred with dermatitis with previous contact with (meth)acrylates was reported as 4.8% (17/352) for MMA, 4.4% (11/246) for EMA and 0.6% (2/331) for BMA ... Cross-reactivity with common acrylates (i.e. between methacrylates and acrylates) has not been observed ... and methacrylic acid, the common hydrolysis product for these methacrylate esters, is not a contact allergen ... /Short chain alkyl-methacrylate esters/|/SIGNS AND SYMPTOMS/ Short Term Exposure: Contact can irritate the eyes and skin. Inhalation can irritate the respiratory tract with coughing, wheezing, and/or shortness of breath. Higher exposures can cause pulmonary edema, a medical emergency that can be delayed for several hours. This can cause death. Long Term Exposure: Butyl methacrylate may cause skin allergy.|/SIGNS AND SYMPTOMS/ Although there are notable exceptions to the rule, esters of organic acids are generally of low toxicity. Nonspecific irritative effects are commonly associated with the presence of a double bond in these esters which, if saturated, would be essentially harmless. Conjunctivitis and upper airway symptoms may occur and pulmonary edema is possible in case of massive over-exposure. These irritating unsaturated esters include the acrylates, methacrylates ... /Esters/|For more Human Toxicity Excerpts (Complete) data for n-Butyl methacrylate (10 total), please visit the HSDB record page.
butyl methacrylate monomer
The substance can be absorbed into the body by inhalation.
Sore throat. Cough. Shortness of breath.
Redness.
Watering of the eyes. Redness. Pain.
Butyl methacrylate Use and Manufacturing
Reaction of methacrylic acid or methyl methacrylate with butanol.|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/
Monomer for resins, solvent coatings, adhesives, oil additives, emulsions for textiles, leather & paper finishing.
Intermediates
50,000,000 - 100,000,000 lb|(1972) > 4.54 X 10+5 g|(1975) > 4.54 X 10+5 g|(1993) 2.61 X 10+7 kg (2.61 X 10+10 g)|2-Propenoic acid, 2-methyl-, butyl ester 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 n-Butyl methacrylate (6 total), please visit the HSDB record page.
Automotive coatings 46% (9.5% is after market), toners 28%, lubricants 11%, architectural paints 2%, other lacquers and enamels 2.6%, powder coatings 9.6%, floor polishes 1%
Technical grade (inhibited)|Inhibitor of polymerization: 9-15 ppm monomethyl ether or 90-120 ppm hydroquinone.
Adhesive manufacturing|2-Propenoic acid, 2-methyl-, butyl ester: ACTIVE|Alkyl mercury compounds have been used as seed disinfectants and for fungicides. They have also been used in organic synthesis. /Mercury alkyl compounds/|Methyl methacrylate, and in general the methacrylic esters, polymerize much less readily than the corresponding ordinary acrylates. Nonetheless, they are stabilized by adding hydroquinone or pyrogallol, particularly in the presence of metallic copper. /Methacrylates/
METHOD WAS DEVELOPED FOR GAS CHROMATOGRAPHY DETERMINATION OF METHYL ACRYLATE, METHYL METHACRYLATE, BUTYL ACRYLATE, AND BUTYL METHACRYLATE IN AIR IN PRESENCE OF SOME OTHER CMPD. THE METHOD CONSISTS OF THE DETERMINATION OF METHYL AND BUTYL ESTERS IN PAIRS FROM DIFFERENT SAMPLES UNDER DIFFERENT CONDITIONS OF SEPARATION ON COLUMNS CONTAINING 10% PMS-100 ON CELYTE-545, 10% KEE 60 ON CHROMOSORB-W, AND 7% DDF ON CHROMOSORB-W. THE SENSITIVITY OF THE METHOD IS ... 0.002 MG/CU M FOR BUTYL ACRYLATE AND BUTYL METHACRYLATE.|THE ELECTRON-IMPACT AND METHANE CHEM-IONIZATION MASS SPECTRA OF SELECTED ACRYLATE AND METHACRYLATE MONOMERS, INCLUDING BUTYL METHACRYLATE, COMMONLY USED IN DENTAL MATERIALS ARE REPORTED AND DISCUSSED. THE TWO IONIZATION MODES COMPLEMENT EACH OTHER, AND TOGETHER THE MASS SPECTRA OFFER ADEQUATE INFORMATION FOR IDENTIFICATION PURPOSES. THE APPLICATION OF THE MASS SPECTRAL METHOD IS DEMONSTRATED ON RESIN-BASED DENTAL MATERIALS WITH IDENTIFICATION OF THE MONOMER CONTENT.|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. A variety of spectroscopic techniques, eg, NMR, IR, and Raman spectroscopy also have been used, particularly for analysis of surgical cements and dental restorative resins. /Methacrylic acid & derivatives/
Fire Hazards -> Flammable - 2nd degree, Reactive - 2nd degree|Cosmetics -> Viscosity controlling
Computed Properties
Molecular Weight:142.20
XLogP3:2.9
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:5
Exact Mass:142.099379685
Monoisotopic Mass:142.099379685
Topological Polar Surface Area:26.3
Heavy Atom Count:10
Complexity:127
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
Price Analysis
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