ethylene glycol monobutyl ether
Eastman EB solvent
BH-33 industrial cleaner
|Molar mass||118.17 g·mol−1|
|Appearance||Clear, colourless liquid|
|Density||0.90 g/cm³, liquid|
|Melting point||−77 °C (−107 °F; 196 K)|
|Boiling point||171 °C (340 °F; 444 K)|
|Vapor pressure||0.8 mmHg|
|Acidity (pKa)||high pKa for -OH group|
|Viscosity||2.9 cP at 25 °C (77 °F)|
|MSDS||MSDS by Mallinckrodt Baker|
|EU classification||Harmful (Xn)|
|S-phrases||(S2), S36/37, S46|
|Flash point||67 °C (153 °F; 340 K)|
|245 °C (473 °F; 518 K)|
|US health exposure limits (NIOSH):|
|TWA 50 ppm (240 mg/m3) [skin]|
|TWA 5 ppm (24 mg/m3) [skin]|
IDLH (Immediate danger)
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
|what is: / ?)(|
2-Butoxyethanol is an organic compound with the chemical formula BuOC2H4OH (Bu = CH3CH2CH2CH2). This colorless liquid has a sweet, ether-like odor, as it derives from the family of glycol ethers, and is a butyl ether of ethylene glycol. As a relatively nonvolatile, inexpensive solvent of low toxicity, it is used in many domestic and industrial products because of its properties as a surfactant.
- C2H4O + C4H9OH → C4H9OC2H4OH
In 2006, the European production of butyl glycol ethers amounted to 181 kilotons, of which approximately 50% (90 kt/a) was 2-Butoxyethanol. World production is estimated to be 200 to 500 kt/a, of which 75% is for paints and coatings and 18% for metal cleaners and household cleaners. In the US, it is considered a High Production Volume Chemical because greater than 100 million pounds of this chemical is produced per year.
2-Butoxyethanol is a glycol ether with modest surfactant properties (and it could be used as a mutual solvent). In use since the 1930s, glycol ethers are solvents that dissolve both water soluble and hydrophobic substances. Glycol ethers consist of two components, an alcohol and ether. According to the nature of alcohol, molecules of this class can be divided into two groups: E series and P series which correspond to ethylene and propylene respectively. Glycol ethers are selected for specific purposes, such as solubility, inflammability, and volatility.
2-Butoxyethanol is a solvent for paints and surface coatings, as well as cleaning products and inks. Products that contain 2-butoxyethanol include acrylic resin formulations, asphalt release agents, firefighting foam, leather protectors, oil spill dispersants, degreaser applications, photographic strip solutions, whiteboard cleaners, liquid soaps, cosmetics, dry cleaning solutions, lacquers, varnishes, herbicides, latex paints, enamels, printing paste, and varnish removers, and silicone caulk. Products containing this compound are commonly found at construction sites, automobile repair shops, print shops, and facilities that produce sterilizing and cleaning products. It is the main ingredient of many home, commercial and industrial cleaning solutions. Since the molecule has both non-polar and polar ends, butoxyethanol is useful for removing both polar and non-polar substances, like grease and oils. It is also approved by the U.S. FDA to be used as direct and indirect food additives, which include antimicrobial agents, defoamers, stabilizers, and adhesives.
In the petroleum industry
In the petroleum industry, 2-butoxyethanol is a component of fracturing fluids, drilling stabilizers, and oil slick dispersants for both water-based and oil-based hydraulic fracturing[clarification needed] When liquid is pumped into the well, the fracturing fluids are pumped under extreme pressure, so 2-butoxyethanol is used to stabilize them by lowering the surface tension. The compound is also used to facilitate the release of the gas by preventing congealing. It is also used as a crude oil-water coupling solvent for more general oil well workovers. Because of its surfactant properties, it is a major constituent (30–60% w/w) in the oil spill dispersant Corexit 9527, which was widely used in the aftermath of the 2010 Deepwater Horizon oil spill.
2-Butoxyethanol has a low acute toxicity, with LD50 of 2.5 g/kg in rats. Laboratory tests by the U. S. National Toxicology Program have shown that only sustained exposure to high concentrations (100-500 ppm) of 2-butoxyethanol can cause adrenal tumors in animals. American Conference of Governmental Industrial Hygienists (ACGIH) reports that 2-butoxyethanol is carcinogenic in rodents. These rodent tests may not directly translate to carcinogenicity in humans, as the observed mechanism of cancer involves the rodents' forestomach, which humans lack. OSHA does not regulate 2-butoxyethanol as a carcinogen.
Disposal and degradation
2-Butoxyethanol can be disposed of by incineration. It was shown that disposal occurs faster in the presence of semiconductor particles. 2-Butoxyethanol usually decomposes in the presence of air within a few days by reacting with oxygen radicals. It has not been identified as a major environmental contaminant, nor is it known to bio-accumulate. 2-Butoxyethanol biodegrades in soils and water, with a half life of 1–4 weeks in aquatic environments.
2-butoxyethanol most commonly enters the human body system through dermal absorption, inhalation, or oral consumption of the chemical. The ACGIH threshold limit value (TLV) for worker exposure is 20 ppm, which is well above the odor detection threshold of 0.4 ppm. Blood or urine concentrations of 2-butoxyethanol or the metabolite 2-butoxyacetic acid may be measured using chromatographic techniques. A biological exposure index of 200 mg 2-butoxyacetic acid per g creatinine has been established in an end-of-shift urine specimen for U.S. employees. 2-Butoxyethanol and its metabolites fall to undetectable levels in urine after about 30 hours in human males.
Harmful effects have only been observed in animals exposed to high levels of 2-butoxyethanol. Developmental effects were seen in a study that exposed pregnant Fischer 344 rats, a type of laboratory rat, and New Zealand white rabbits to varying doses of 2-butoxyethanol. At 100 ppm (483 mg/m3) and 200 ppm (966 mg/m3) exposure, statistically significant increases were observed in the number of litters with skeletal defects. Additionally, 2-butoxyethanol was associated with a significant decrease in maternal body weight, uterine weight, and number of total implants. 2-Butoxyethanol is metabolized in animals by the enzyme alcohol dehydrogenase.
Neurological effects have also been observed in animals exposed to 2-butoxyethanol. Fischer 344 rats exposed to 2-butoxyethanol at concentrations of 523 ppm and 867 ppm experienced decreased coordination. Male rabbits showed a loss of coordination and equilibrium after exposure to 400 ppm of 2-butoxyethanol for two days.
When exposed to 2-butoxyethanol in drinking water, both F344/N rats and B63F1 mice showed negative effects. The range of exposure for the two species was between 70 mg/kg body weight per day to 1300 mg/kg body weight per day. Decreased body weight and water consumption were seen for both species. Rats had reduced red blood cell counts and thymus weights, as well as lesions in the liver, spleen, and bone marrow.
Regulation in Canada
Environment and Health Canada recommended that 2-butoxyethanol be added to Schedule 1 of the Canadian Environmental Protection Act, 1999 (CEPA). Under these regulations, products containing 2-butoxyethanol are to be diluted below a certain concentration. Only those in which the user performs the required dilution are required to include it on labelling information.
Regulation in the US
It is approved by the Food and Drug Administration as "an indirect and direct food additive for use as an antimicrobial agent, defoamer, stabilizer and component of adhesives". After it was deleted from a UN list of substances requiring special toxicity labeling in 1994, and a subsequent petition by the American Chemistry Council, 2-Butoxyethanol was removed from the U.S. Environmental Protection Agency's list of hazardous air pollutants in 2004. The safety of products containing 2-Butoxyethanol as normally used is defended by the industry trade groups the American Chemistry Council and the Soap and Detergent Association.
- "NIOSH Pocket Guide to Chemical Hazards #0070". National Institute for Occupational Safety and Health (NIOSH).
- Harris O. et al. (August 1998). Toxicological Profile for 2-Butoxyethanol and 2-butoxyethanol acetate. U.S. Dept of Health and Human Services.
- Siegfried Rebsdat, Dieter Mayer "Ethylene Glycol" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2000.doi:10.1002/14356007.a10_101.
- "Ethylene Glycol Mono-N-Butyl Ether". National Library of Medicine. Retrieved 2014-03-26.
- Elskamp, Carl J. "2-Butoxyethanol (Butyl Cellosolve) & 2-Butoxyethyl Acetate (Butyl Cellosolve Acetate)". United States Department of Labor.
- Dickey, Robert; W. Dickhoff. "Assessment of the potential impact of COREXIT® oil dispersants on seafood safety". Dispersants and Seafood Safety. Retrieved 2014-03-26.
- "SAFETY DATA SHEET - PRODUCT: COREXIT® EC9527A". Nalco Environmental Solutions LLC. 1 March 2012. Retrieved 30 April 2014.
- "Toxicology and Carcinogenesis Studies 2-Butoxyethanol (CAS NO. 111-76-2) in F344/N Rats and B6C3F1 Mice (Inhalation Studies)". National Toxicology Program: Department of Health and Human Services. USA.gov. Archived from the original on 28 May 2010. Retrieved 4 June 2010.
- "Air Foam HD Material Data Safety Sheet". Product Safety. AquaClear, Inc. Retrieved 4 June 2010.
- Gift, J. S. (2005). "U.S. EPA's IRIS assessment of 2-Butoxyethanol: the relationship of noncancer to cancer effects". Toxicol. Lett. 156: 163–178. doi:10.1016/j.toxlet.2003.08.014.
- "Chemical Sampling Information | 2-Butoxyethanol". Occupational Safety & Health Administration.
- Hullar, T.; Anastasio, C. Yields of hydrogen peroxide from the reaction of hydroxyl radical with organic compounds in solution and ice. Atmospheric Chemistry and Physics, 11, 7209.
- Agency for Toxic Substances and Disease Registry ToxFAQs
- 2009 TLVs and BEIs, American Conference of Industrial Hygienists, Cincinnati, Ohio, 2009, p.101.
- R. Baselt (2008). Disposition of Toxic Drugs and Chemicals in Man (8th edition ed.). Foster City, CA: Biomedical Publications. pp. 208–210.
- Franks, S. J.; Spendiff, M. K.; Cocker, J.; Loizou, G. D. (2006). "Physiologically based pharmacokinetic modelling of human exposure to 2-butoxyethanol". Toxicol. Lett. 162: 164–173. doi:10.1016/j.toxlet.2005.09.012.
- Wess, Ms. J., Dr. H. Ahlers, and Dr. S Dobson. "Concise International Chemical Assessment Document 10: 2-Butoxyethanol." World Health Organization, n.d. Web. <http://www.who.int/ipcs/publications/cicad/cicad_10_revised.pdf>
- United States of America. Agency for Toxic Substances and Disease Registry. Department of Health and Human Services. Toxicological Profile for 2-Butoxyethanol and 2-Butoxyethanol Acetate. By Olivia Harris, Sharon Wilbur, Julia George, and Carol Eisenmann. Atlanta: n.p., 1998. Agency for Toxic Substances and Disease Registry. Web. <http://www.atsdr.cdc.gov/toxprofiles/tp118.pdf>
- "Current Use Patterns in Canada, Toxicology Profiles of Alternatives, and the Feasibility of Performing an Exposure Assessment Survey". Environment Canada. Retrieved 15 February 2011.
- "Regulations Amending the 2-Butoxyethanol Regulations". Canada Gazette. Canadian Department of Public Works and Government Services. 23 April 2014. Retrieved 30 April 2014.
- "California Code of Regulations, Title 8, Section 339. The Hazardous Substances List". State of California Department of Labor Relations. Archived from the original on 5 May 2008. Retrieved 2008-04-21.
- "Glycol Ethers Fact Sheet". California Hazard Evaluation and Information Service. Retrieved 29 October 2007.
- "List of Hazardous Air Pollutants, Petition Process, Lesser Quantity Designations, Source Category List; Petition To Delist of Ethylene Glycol Monobutyl Ether". U.S. Environmental Protection Agency. 2004-11-29. Retrieved 23 February 2008.
- "EGBE: A World of Solutions 2000". July 2000. Archived from the original on 3 October 2006. Retrieved 30 April 2014.