Isobutyl Methacrylate

log Kow = 2.66

2.66

0.8858 at 68 °F (USCG, 1999) - Less dense than water; will float

0.8858 g/cu cm at 20 °C

Bulk density: 0.882 g/mL at 25 °C/25 °C

Insoluble (<1mg/ml) (NTP, 1992)

Miscible with ethanol, ethyl ether

Insoluble in water

In water, 1300 mg/L at 25 °C

120 °F (NTP, 1992)

35 °C (closed cup)

49 °C (Tag open cup)

311 °F at 760 mmHg (NTP, 1992)

155 °C

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, P319, P321, P332+P317, P333+P317, P362+P364, P370+P378, P403+P233, P403+P235, P405, and P501 (click each P-code to see the statement)

This chemical does not meet GHS hazard criteria for < 0.1% (1 of 1406) of reports.

Warning

H226 (> 99.9%): Flammable liquid and vapor [Warning Flammable liquids]

Chemical: 2-Propenoic acid, 2-methyl-, 2-methylpropyl ester

Commission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)

2-Propenoic acid, 2-methyl-, 2-methylpropyl ester is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 2-Propenoic acid, 2-methyl-, 2-methylpropyl ester 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)

Status: Active Update: 30-06-2021 https://echa.europa.eu/registration-dossier/-/registered-dossier/14969

2-Propenoic acid, 2-methyl-, 2-methylpropyl ester: HSNO Approval: HSR001173 Approved with controls

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.)

Special Hazards of Combustion Products: Thermal decomposition may yield oxides of carbon.

· HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames.

May be harmful if inhaled; may cause dizziness or suffocation. Irritating to skin and eyes. Harmful if swallowed. (USCG, 1999)

· May cause toxic effects if inhaled or absorbed through skin.

A lachrymator; [CHEMINFO] A skin, eye, and respiratory tract irritant; [HSDB] A skin, eye, and respiratory tract irritant; May cause skin sensitization; [eChemPortal: ESIS]; An irritant; Potential skin sensitizer; [MSDSonline] Isobutyl methacrylate, stabilized (UN2283) has warning of explosive polymerization; [ERG 2016]

European Commission, ESIS; IUCLID Dataset, Isobutyl methacrylate (97-86-9) (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/]

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]

ISOBUTYL METHACRYLATE is an acrlate ester. Esters react with acids to liberate heat along with alcohols and acids. Strong oxidizing acids may cause a vigorous reaction that is sufficiently exothermic to ignite the reaction products. Heat is also generated by the interaction of esters with caustic solutions. Flammable hydrogen is generated by mixing esters with alkali metals and hydrides. This compound polymerizes readily. (NTP, 1992)

· CALL 911. Then call emergency response telephone number on shipping paper. If shipping paper not available or no answer, refer to appropriate telephone number listed on the inside back cover.

· ELIMINATE all ignition sources (no smoking, flares, sparks or flames) from immediate area.

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.

General First Aid:

If material on fire or involved in fire: Use water in flooding quantities as fog. Do not extinguish fire unless flow can be stopped. 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. /Isobutyl methacrylate, stabilized/

Wear positive pressure self-contained breathing apparatus when fighting fires involving this material. /Isobutyl methacrylate, stabilized/

Temp during storage must be kept low to minimize formation of peroxides and other oxidation products. ... Storage temp below 30 °C are recommended for i-Butylmethacrylate. The methacrylate monomer should not be stored for longer than one year. Isobutyl methacrylate is sensitive to UV light and should, therefore, be stored in the dark. The methacrylic ester may be stored in mild steel, stainless steel, or aluminum.

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.

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 the 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.

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 material out of water sources and sewers. Build dikes to contain flow as necessary. Attempt to stop leak if without undue personnel hazard. /Isobutyl methacrylate, stabilized/

Personnel protection: Avoid breathing vapors. Keep upwind. Avoid bodily contact with the meterial. Do not handle broken packages unless wearing appropriate personal protective equipment. Wash away any material which may have contacted the body with copious amt of water or soap and water ... If contact with the material anticipated, wear appropriate chemical protective clothing. /Isobutyl methacrylate, stabilized/

Excerpt from ERG Guide 130 [Flammable Liquids (Water-Immiscible / Noxious); polymerization hazard]:

Immediate precautionary measure

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/

LC50; Species: Leuciscus idus (ide, freshwater fish); Concentration: 92 mg/L/48 hr; Conditions: static, temp 20 +/- 1 °C, pH 7.0 +/- 0.2, dissolved oxygen >= 4 mg/L, hardness 14 deg dH, purity 88.89 %

LC50; Species: Oncorynchus mykiss (Rainbow trout); Conditions: flow-through, OECD 203; Concentration: 20 mg/L/96 hr

EC50; Species: Daphnia magna (water flea); Conditions: flow-through, OECD 202; Concentration: > 29 mg/L/48 hr; Endpoint: immobilization

EC50; Species: Pseudokirchneriella subcapitata (algae); Conditions: static, closed vessel, OECD 201; Concentration: 44 mg/L/72 hr; Endpoint: growth rate

EC50; Species: Pseudokirchneriella subcapitata (algae); Conditions: static, closed vessel, OECD 201; Concentration: 16 mg/L/72 hr; Endpoint: growth rate

TERRESTRIAL FATE: Based on a classification scheme(1), Koc values of 1480-3920(2) indicate that isobutyl methacrylate is expected to have low to slight mobility in soil(SRC). Volatilization of isobutyl methacrylate from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 5.2X10-4 atm-cu m/mole(SRC), based upon its vapor pressure, 3.63 mm Hg(3), and water solubility, 1300 mg/L(4). Isobutyl methacrylate is expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(3). Data are conflicting using standardized biodegradation tests. Utilizing the modified Japanese MITI test, isobutyl methacrylate reached 33% of its theoretical BOD after 28 days(11), while in the OECD 301D Method (Closed Bottle Test) isobutyl methacrylate was found to biodegrade 74% in 28 days(2).

AQUATIC FATE: Based on a classification scheme(1), Koc values of 1480-3920(2) indicate that isobutyl methacrylate is 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 5.2X10-4 atm-cu m/mole(SRC), derived from its vapor pressure, 3.63 mm Hg(4), and water solubility, 1300 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 5.5 hours and 5.3 days, respectively(SRC). However, volatilization from water surfaces is expected to be attenuated by adsorption to suspended solids and sediment in the water column. The estimated volatilization half-life from a model pond is 15-37 days if adsorption is considered(6). According to a classification scheme(7), an estimated BCF of 27(SRC), from its log Kow of 2.66(8) and a regression-derived equation(9), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Hydrolysis is not expected to be an important process(SRC) based on estimated hydrolysis half-lives of 130 and 13 years at pHs 7 and 8, respectively(10). Data are conflicting using standardized biodegradation tests. Utilizing the modified Japanese MITI test, isobutyl methacrylate reached 33% of its theoretical BOD after 28 days(11). In the OECD 301D Method (Closed Bottle Test) isobutyl methacrylate was found to biodegrade 74% in 28 days using a sewage inoculum(2).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), isobutyl methacrylate, which has a vapor pressure of 3.63 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase isobutyl 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 isobutyl 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). Isobutyl 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).

Based on the available data, the CIR Expert Panel concluded that...Isobutyl Methacrylate is safe as used in nail enhancement products when skin contact is avoided. Products containing these ingredients should be accompanied with directions to avoid skin contact, because of the sensitizing potential of Methacrylates.

Safe for use in cosmetics, with qualifications

/OTHER TOXICITY INFORMATION/ Biologically, methacrylates resemble acrylates, except for lower reactivity and thus decreased toxicity. This is probably due to steric hindrance by its methyl group and in turn decreased rates of membrane transport and systemic translocation. /Methacrylic esters/

AEROBIC: In the modified Japanese MITI test, isobutyl methacrylate reached 33% of its Theoretical BOD after 28 days(1).

AEROBIC: Isobutyl methacrylate was found to biodegrade 74% in 28 days using a sewage inoculum in the OECD 301D Method (Closed Bottle Test), classifying it as readily biodegradable(1).

An estimated BCF of 26 was calculated in fish for isobutyl methacrylate(SRC), using a log Kow of 2.66(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC).

The Henry's Law constant for isobutyl methacrylate is estimated as 5.2X10-4 atm-cu m/mole(SRC) derived from its vapor pressure, 3.63 mm Hg(1), and water solubility, 1300 mg/L(2). This Henry's Law constant indicates that isobutyl 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 5.5 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 5.3 days(SRC). However, volatilization from water surfaces is expected to be attenuated by adsorption to suspended solids and sediment in the water column. The estimated volatilization half-life from a model pond is 15-37 days if adsorption is considered(4). Isobutyl methacrylate's estimated Henry's Law constant indicates that volatilization from moist soil surfaces may occur(SRC). The potential for volatilization of isobutyl methacrylate from dry soil surfaces may exist(SRC) based upon its vapor pressure(1).

/LABORATORY ANIMALS: Acute Exposure/ Recent inhalation studies, in rats (strain and sex unknown), using specialist histopathology techniques to study the nasal tissues have shown that EMA produces lesions in the olfactory region of the nasal cavity following exposure at 200 ppm for 6 hrs, but that alkyl-methacrylate esters larger than EMA do not elicit a toxic response at this dose level, mainly because their physicochemical characteristics prevent significant local uptake of the vapors ... /Short chain alkyl-methacrylate esters/

/LABORATORY ANIMALS: Acute Exposure/ Isobutyl methacrylate causes moderate skin and eye irritation in rabbits (strain unknown). Inhalation of 3600 ppm for 6 hr caused no mortality in rats. /From table/

/LABORATORY ANIMALS: Acute Exposure/ Methacrylic acid administered iv increased respiratory rate, decreased heart rate, and produced electrocardiogram changes in anesthetized dogs (breed unknown). Methacrylic acid, methyl, n-propyl, n-butyl, isobutyl, and hydroxyethyl methacrylates produced a biphasic response, an abrupt fall in blood pressure followed by a secondary rise. 2-Ethylhexyl, isodecyl, lauryl, and tert-butylaminoethyl methacrylates produced only a hypotensive effect. Dimethylaminoethylmethacrylate produced only a hypertensive effect.

/LABORATORY ANIMALS: Developmental or Reproductive Toxicity/ ... Six types of methacrylate esters /were administered/ to pregnant rats (strain unknown) on days 5, 10, and 15 of gestation in doses up to one-third the acute intraperitoneal LD50. The maximum doses used were 0.44, 0.40, 0.78, 0.46, and 0.82 mL/kg for the methyl, ethyl, n-butyl, isobutyl, isodecyl methacrylate respectively. Hemangiomas were increased at the highest doses as were resorptions. The fetal wt was reduced by treatment. Acrylic acid was injected in volumes of up to 0.0075 mL/kg and this was associated with resorptions and hemangiomas. Fetal mortality and an incidence of up to 16% malformations were reported ...

For more Non-Human Toxicity Excerpts (Complete) data for Isobutyl Methacrylate (11 total), please visit the HSDB record page.

The rate constant for the vapor-phase reaction of isobutyl 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 isobutyl 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 1.8X10-3 L/mole-sec(SRC) was estimated using a structure estimation method(3); this corresponds to half-lives of 130 and 13 years at pH values of 7 and 8, respectively(3). Isobutyl 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).

Methyl methacrylate and other short chain alkyl-methacrylate esters are initially hydrolyzed by non-specific carboxylesterases to methacrylic acid and the structurally corresponding alcohol in several tissues. /Short chain alkyl-methacrylate esters/

Methacrylate esters can conjugate with glutathione (GSH) in vitro, although they show a low reactivity, since the addition of a nucleophile at the double bond is hindered by the alpha-methyl side-group ... Hence, ester hydrolysis is considered to be the major metabolic pathway for alkyl-methacrylate esters, with GSH conjugation only playing a minor role in their metabolism, and then possibly only when very high tissue concentrations are achieved. /Short chain alkyl-methacrylate esters/

IBMA, like MMA, is supposed to be rapidly metabolized by body carboxylesterases. Hydrolysis of IBMA yields methacrylic acid and iso-butanol which are further metabolized by physiological pathways, methacroyl CoA being a physiological substrate of the valine pathway.

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 Isobutyl Methacrylate (7 total), please visit the HSDB record page.

CIR ingredient: Isobutyl Methacrylate

Used as a monomer for acrylic resins, in hydrogel contact lenses, and as a water repellant for concrete; [HSDB]

Monomer for acrylic resins

In hydrogel contact lenses

Concrete can ... be made water repellent by the polymerization of vinyl monomers on the surface

2023: 2,500,000 - <4,000,000 lb

(1981) Probably > 2.27 X 10+6 g

(1982) Probably > 2.27 X 10+6 g

2-Propenoic acid, 2-methyl-, 2-methylpropyl 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).

Production volumes for non-confidential chemicals reported under the Inventory Update Rule. [Table#5355]

Production volume for non-confidential chemicals reported under the 2006 Inventory Update Rule. Chemical: 2-Propenoic acid, 2-methyl-, 2-methylpropyl ester. Aggreated National Production Volume: 10 to < 50 million lbs.

Esterification or transesterification of isobutyl alcohol with either methacrylic acid or methyl methacrylate

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/

... Manufactured by direct esterification of methacrylic acid or transesterification of methyl methacrylate

Paint and Coating Manufacturing

2-Propenoic acid, 2-methyl-, 2-methylpropyl 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/

A treatment that may be practical for highway bridge decks is the application of methyl methacrylate, isodecyl methacrylate, or isobutyl methacrylate.