2-Butoxyethanol

Chemical compound changed changed 477212899 2-Butoxyethanol 2-butoxyethanol structure.svg 220 2-Butoxyethanol 2-Butoxyethanol-3D-spacefill.png 220 2-Butoxyethanol molecule 2-Butoxyethan-1-ol 2-ButoxyethanolButyl cellosolveButyl glycolButyl monoether glycolEGBE (ethylene glycol monobutyl ether)Dowanol EBEastman EB solvent 2-BE EGMBE Butyl oxitolEktasolve EB Jeffersol EB OCCOCCCC changed EBI 63921 284588 changed chemspider 13836399 8133 203-905-0 1/C6H14O2/c1-2-3-5-8-6-4-7/h7H,2-6H2,1H3 POAOYUHQDCAZBD-UHFFFAOYAB changed chemspider 1S/C6H14O2/c1-2-3-5-8-6-4-7/h7H,2-6H2,1H3 changed chemspider POAOYUHQDCAZBD-UHFFFAOYSA-N correct FDA I0P9XEZ9WV correct CAS 111-76-2 KJ8575000 1993, 2810, 2369 6 14 2 Clear, colorless liquid 0.90 g/cm3, liquid Miscible (and in most organic solvents) -77 171 High pKa for −OH group 2.9 cP at 25 °C F 0.8 mmHg 1.4198 (20 °C)CRC handbook of chemistry and physics : a ready-reference book of chemical and physical data. 2016 William M. Haynes 978-1-4987-5428-6 97th CRC Press Boca Raton, Florida 930681942 2.08 D 2 2 0 06 07 08 Danger 227 302 311 315 319 330 336 361 370 372 201 202 210 260 261 264 270 271 280 281 284 301+312 302+352 304+340 305+351+338 307+311 308+313 310 312 314 320 321 322 330 332+313 337+313 361 362 363 370+378 403+233 403+235 405 501 67 245 TWA 50 ppm (240 mg/m3) [skin]0070 1.1–12.7% 700 ppm TWA 5 ppm (24 mg/m3) [skin] 450 ppm (rat, 4 h)700 ppm (mouse, 7 h)111762 2-Butoxyethanol 1230 mg/kg (mouse, oral)470 mg/kg (rat, oral)300 mg/kg (rabbit, oral)1200 mg/kg (guinea pig, oral)1480 mg/kg (rat, oral) ethers 2-Methoxyethanol2-Ethoxyethanol Ethylene glycol 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, it is used in many domestic and industrial products because of its properties as a surfactant. It is a known respiratory irritanthttps://www.nlm.nih.gov/toxnet/index.html Toxnet Has Moved www.nlm.nih.gov 2020-01-24 and can be acutely toxic, but animal studies have not found it to be mutagenic, and no studies suggest it is a human carcinogen.https://www.atsdr.cdc.gov/phs/phs.asp?id=345&tid=61 Public Health Statement for 2-Butoxyethanol and 2-Butoxyethanol Acetate August 1998 Agency for Toxic Substances and Disease Registry, Center for Disease Control 16 February 2020 18 December 2020 https://web.archive.org/web/20201218041045/https://www.atsdr.cdc.gov/phs/phs.asp?id=345&tid=61 dead A study of 13 classroom air contaminants conducted in Portugal reported a statistically significant association with increased rates of nasal obstruction and a positive association below the level of statistical significance with a higher risk of obese asthma and increased body mass index.10.1111/all.13740 30740706 Exposure to indoor endocrine-disrupting chemicals and childhood asthma and obesity Allergy 74 7 1277–1291 2019 Paciência Inês Cavaleiro Rufo João Silva Diana Martins Carla Mendes Francisca Farraia Mariana Delgado Luís De Oliveira Fernandes Eduardo Padrão Patrícia Moreira Pedro Severo Milton Barros Henrique Moreira André 18 November 2025 73443692 Properties Miscibility with water Miscibility of 2-butoxyethanol with water depends on temperature. Depending on the composition of the mixture, the two liquids are partially miscible. This mixture shows both a lower and an upper critical solution temperature: below around 49 °C (lower critical solution temperature), the liquids are completely miscible. The same is true for temperatures above around 130 °C (upper critical solution temperature). Between these temperatures, however, the liquids do not mix in all proportions and two phases might appear, each of which is formed by various ratios of the two liquids.Christensen Scott P. Donate Felipe A. Frank Timothy C. LaTulip Randy J. Wilson Loren C. 2005-05-01 Mutual Solubility and Lower Critical Solution Temperature for Water + Glycol Ether Systems https://pubs.acs.org/doi/full/10.1021/je049635u Journal of Chemical & Engineering Data 50 3 869–877 10.1021/je049635u 18 November 2025 0021-9568 subscription 2024-12-07 Liquid - Raoult's Law, Intermolecular Forces, Viscosity Britannica https://www.britannica.com/science/liquid-state-of-matter/Raoults-law#ref506848 2025-01-05 www.britannica.com en Production 2-Butoxyethanol is commonly obtained through two processes; the ethoxylation reaction of butanol and ethylene oxide in the presence of a catalyst: C2H4O + C4H9OH → C4H9OC2H4OH or the etherification of butanol with 2-chloroethanol.Toxicological Profile for 2-Butoxyethanol and 2-butoxyethanol acetate August 1998 U.S. Dept of Health and Human Services Harris O. etal 2-Butoxyethanol can be obtained in the laboratory by performing a ring opening of 2-propyl-1,3-dioxolane with boron trichloride.Bonner Trevor Opening of cyclic acetals by trichloro-, dichloro-, and tribromo-borane Journal of the Chemical Society, Perkin Transactions 1 1981 1807–1810 10.1039/p19810001807 It is often produced industrially by combining ethylene glycol and butyraldehyde in a Parr reactor with palladium on carbon. https://patents.google.com/patent/US8829229B2/en Tulchinsky Michael Poly ethers and process for making them 2014 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.Ethylene Glycol Mono-N-Butyl Ether http://toxnet.nlm.nih.gov/cgi-bin/sis/search/f?./temp/~0Bg03b:1 https://archive.today/20140327015818/http://toxnet.nlm.nih.gov/cgi-bin/sis/search/f?./temp/~0Bg03b:1 dead March 27, 2014 National Library of Medicine 2014-03-26 In the US, it is considered a high production volume chemical because more than 100 million pounds of this chemical are produced per year. Uses 2-Butoxyethanol is a glycol ether with modest surfactant properties, which can also be used as a mutual solvent (soluble in both water and oil). Commercial uses 2-Butoxyethanol is a solvent for paints and surface coatings, as well as cleaning products and inks.http://www.sharpie.com/enus/Pages/FAQ.aspx#Q15 Sharpie Frequently Asked Questions sharpie.com 30 June 2015 https://web.archive.org/web/20150526212818/http://www.sharpie.com/enus/Pages/FAQ.aspx#Q15 26 May 2015 dead 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 and glass cleaners, liquid soaps, cosmetics, dry cleaning solutions, lacquers, varnishes, herbicides, latex paints, enamels, printing paste, 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 polar and non-polar ends, 2-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. https://www.crrc.unh.edu/sites/crrc.unh.edu/files/dickeydickhoff.pdf live 2022-08-03 White Paper Dispersants and Seafood Safety Assessment of the potential impact of COREXIT oil dispersants on seafood safety Dickey Robert W. Dickhoff Walton W. 2012-01-30 2011 Coastal Response Research Center (CRRC). Dispersant Initiative and Workshop “The Future of Dispersant Use in Spill Response” (Tuesday, September 20, 2011 to Thursday, September 22, 2011) Mobile, Alabama en-us https://web.archive.org/web/20210412215320if_/https://crrc.unh.edu/sites/crrc.unh.edu/files/dickeydickhoff.pdf 2021-04-12 PDF In the petroleum industry 2-Butoxyethanol is commonly produced for the oil industry because of its surfactant properties.Rogers J A Framework for Identifying Organic Compounds of Concern in Hydraulic Fracturing Fluids Based on Their Mobility and Persistence in Groundwater Environmental Science and Technology Letters 2015 2 6 158–164 10.1021/acs.estlett.5b00090 2015EnSTL...2..158R free 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.April 2014 Toxnet searches expire quickly. It is unclear what source is being referred to from the search. 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. As a surfactant, 2-butoxyethanol absorbs at the oil-water interface of the fracture.Barati Reza A review of fracturing fluid systems used for hydraulic fracturing of oil and gas wells Journal of Applied Polymer Science 2014 131 16 app.40735 n/a 10.1002/app.40735 2014JAPS..13140735B free 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, http://www.nalcoesllc.com/nes/documents/MSDS/NESLLC-COREXIT-_EC9527A-March_2012.pdf https://web.archive.org/web/20140502013531/http://www.nalcoesllc.com/nes/documents/MSDS/NESLLC-COREXIT-_EC9527A-March_2012.pdf dead 2 May 2014 Safety Data Sheet - Product: Corexit EC9527A 30 April 2014 Nalco Environmental Solutions LLC 1 March 2012 which was widely used in the aftermath of the 2010 Deepwater Horizon oil spill. Safety 2-Butoxyethanol has a low acute toxicity, with of 2.5 g/kg in rats.Siegfried Rebsdat, Dieter Mayer "Ethylene Glycol" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2000.10.1002/14356007.a10_101. 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.Toxicology and Carcinogenesis Studies 2-Butoxyethanol (CAS NO. 111-76-2) in F344/N Rats and B6C3F1 Mice (Inhalation Studies) https://ntp.niehs.nih.gov/publications/reports/tr/tr484 National Toxicology Program: Department of Health and Human Services USA.gov 4 June 2010 https://web.archive.org/web/20100528075034/http://ntp.niehs.nih.gov/?objectid=070AC403-B110-CA79-3A23AF79DE7B752A 2010-05-28 live American Conference of Governmental Industrial Hygienists (ACGIH) reports that 2-butoxyethanol is carcinogenic in rodents.Air Foam HD Material Data Safety Sheet https://archive.org/details/AirFoamHdMaterialDataSafetySheetmsds Product Safety AquaClear, Inc 4 June 2010 These rodent tests may not directly translate to carcinogenicity in humans, as the observed mechanism of cancer involves the rodents' forestomach, which humans lack. Gift, J. S. U.S. EPA's IRIS assessment of 2-Butoxyethanol: the relationship of noncancer to cancer effects Toxicol. Lett. 2005 156 1 163–178 10.1016/j.toxlet.2003.08.014 18 November 2025 15705494 2005ToxL..156..163G http://digitalcommons.unl.edu/cgi/viewcontent.cgi?article=1168&context=usepapapers subscription OSHA does not regulate 2-butoxyethanol as a carcinogen.Chemical Sampling Information 2-Butoxyethanol https://www.osha.gov/dts/chemicalsampling/data/CH_222400.html Occupational Safety & Health Administration 2014-04-23 2017-07-31 https://web.archive.org/web/20170731224022/https://www.osha.gov/dts/chemicalsampling/data/CH_222400.html dead 2-Butoxyethanol has not been shown to penetrate shale rock in a study conducted by Manz.Manz K Adsorption of hydraulic fracturing fluid components 2-butoxyethanol and furfural onto granular activated carbon and shale rock Chemosphere 2016 164 585–592 10.1016/j.chemosphere.2016.09.010 18 November 2025 27632795 2016Chmsp.164..585M 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.Hullar T. Anastasio C. 2011-07-22 Yields of hydrogen peroxide from the reaction of hydroxyl radical with organic compounds in solution and ice https://acp.copernicus.org/articles/11/7209/2011/ Atmospheric Chemistry and Physics English 11 14 7209–7222 10.5194/acp-11-7209-2011 18 November 2025 2011ACP....11.7209H 1680-7316 free It has not been identified as a major environmental contaminant, nor is it known to bio-accumulate.https://wwwn.cdc.gov/TSP/ToxFAQs/ToxFAQsLanding.aspx?id=346&tid=61 ATSDR - ToxFAQs: 2-Butoxyethanol and 2-Butoxyethanol Acetate cdc.gov 30 June 2015 2-Butoxyethanol biodegrades in soils and water, with a half life of 1–4 weeks in aquatic environments. Human exposure 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.2009 TLVs and BEIs, American Conference of Industrial Hygienists, Cincinnati, Ohio, 2009, p.101. R. Baselt Disposition of Toxic Drugs and Chemicals in Man 8th Biomedical Publications Foster City, CA 2008 208–210 2-Butoxyethanol and its metabolites fall to undetectable levels in urine after about 30 hours in men. Animal studies Harmful effects have been observed in nonhuman mammals 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.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> 2-Butoxyethanol is metabolized in mammals by the enzyme alcohol dehydrogenase.Franks, S. J. Spendiff, M. K. Cocker, J. Loizou, G. D. Physiologically based pharmacokinetic modelling of human exposure to 2-butoxyethanol Toxicol. Lett. 2006 162 2–3 164–173 10.1016/j.toxlet.2005.09.012 18 November 2025 16246510 2006ToxL..162..164F 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.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> 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). Current Use Patterns in Canada, Toxicology Profiles of Alternatives, and the Feasibility of Performing an Exposure Assessment Survey Environment Canada http://www.chemicalsubstanceschimiques.gc.ca/fact-fait/butoxyethanol-eng.php 15 February 2011 2017-03-12 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. http://www.gazette.gc.ca/rp-pr/p2/2014/2014-04-23/html/sor-dors78-eng.php Regulations Amending the 2-Butoxyethanol Regulations 30 April 2014 23 April 2014 Canadian Department of Public Works and Government Services Canada Gazette Regulation in the US 2-Butoxyethanol is listed in California as a hazardous substance and the state sets an 8 hour average airborne concentration exposure limit at 25 ppm, http://www.dir.ca.gov/title8/339.html California Code of Regulations, Title 8, Section 339. The Hazardous Substances List 2008-04-21 State of California Department of Laboring Relations https://web.archive.org/web/20080505040711/http://www.dir.ca.gov/title8/339.html 5 May 2008 live and in California employers are required to inform employees when they are working with it. Glycol Ethers Fact Sheet California Hazard Evaluation and Information Service http://www.dhs.ca.gov/ohb/HESIS/glycols.htm 29 October 2007 https://web.archive.org/web/20070818004042/http://www.dhs.ca.gov/ohb/HESIS/glycols.htm 18 August 2007 dead dmy-all 2-Butoxyethanol is prohibited from use as a chemical additive in hydraulic fracturing fluids (Rule 437, Table 437-1April 30, 2025 Code of Colorado Regulations 2 CCR 404-1 https://ecmc.state.co.us/documents/reg/Rules/LATEST/complete_rules_100_1300_series_v2.pdf December 3, 2025) in Colorado where all chemicals used in downhole operations are required to be disclosed (§34-60-132 C.R.S.2024 Appendix V - Oil Gas Conservation Act https://ecmc.state.co.us/documents/reg/Rules/LATEST/Appendix%20V%20-%20Oil%20Gas%20Conservation%20Act%20Title%2034%20-%20Article%2060%20-%202024.pdf December 3, 2025) to the Energy and Carbon Management Commission. 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", and also "may be used to wash or assist in the peeling of fruits and vegetables" and "may be safely used as components of articles intended for use in packaging, transporting & holding food".CFR Title 21 - Food and Drugs - URL: http://www.fda.gov (2004). CFR Title: 21 CFR Part Section: 173.315 After its deletion 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. U.S. Environmental Protection Agency https://www3.epa.gov/ttn/atw/pollutants/fr29no04.pdf 2004-11-29 List of Hazardous Air Pollutants, Petition Process, Lesser Quantity Designations, Source Category List; Petition To Delist of Ethylene Glycol Monobutyl Ether 3 August 2024 http://www.egep.org/worldsolutions2000.pdf EGBE: A World of Solutions 2000 30 April 2014 3 October 2006 July 2000 https://web.archive.org/web/20061003060754/http://www.egep.org/worldsolutions2000.pdf 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. References 30em External links International Chemical Safety Card 0059 NIOSH Pocket Guide to Chemical Hazards Inchem SIDS dossier https://web.archive.org/web/20160303210243/http://www.inchem.org/documents/sids/sids/111762.pdf 2016-03-03 Eastman EB solvent info ToxFAQs for 2-Butoxyethanol and 2-Butoxyethanol Acetate from the Centers for Disease Control Category:Glycol ethers Category:Hydroxyethyl compounds Category:Household chemicals Category:Cleaning products Category:Butyl compounds