2-Butoxyethanol
Names | |
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Preferred IUPAC name
2-Butoxyethanol | |
Other names
2-Butoxyethanol
Butyl cellosolve Butyl glycol Butyl monoether glycol EGBE (ethylene glycol monobutyl ether) Dowanol EB Eastman EB solvent 2-BE EGMBE Butyl oxitol Ektasolve EB Jeffersol EB | |
Identifiers | |
3D model (
JSmol ) |
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ChEBI | |
ChEMBL | |
ChemSpider | |
ECHA InfoCard
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100.003.550 |
EC Number |
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PubChem CID
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RTECS number
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UNII | |
UN number | 1993, 2810, 2369 |
CompTox Dashboard (EPA)
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Properties | |
C6H14O2 | |
Molar mass | 118.176 g·mol−1 |
Appearance | Clear, colorless liquid |
Density | 0.90 g/cm3, liquid |
Melting point | −77 °C (−107 °F; 196 K) |
Boiling point | 171 °C (340 °F; 444 K) |
Miscible (and in most organic solvents) | |
Vapor pressure | 0.8 mmHg[1] |
Acidity (pKa) | High pKa for −OH group |
Refractive index (nD)
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1.4198 (20 °C)[2] |
Viscosity | 2.9 cP at 25 °C (77 °F) |
2.08 D[2] | |
Hazards | |
GHS labelling: | |
Danger | |
H227, H302, H311, H315, H319, H330, H336, H361, H370, H372 | |
P201, P202, P210, P260, P261, P264, P270, P271, P280, P281, P284, P301+P312, P302+P352, P304+P340, P305+P351+P338, P307+P311, P308+P313, P310, P312, P314, P320, P321, P322, P330, P332+P313, P337+P313, P361, P362, P363, P370+P378, P403+P233, P403+P235, P405, P501 | |
NFPA 704 (fire diamond) | |
Flash point | 67 °C (153 °F; 340 K) |
245 °C (473 °F; 518 K) | |
Explosive limits
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1.1–12.7%[1] |
Lethal dose or concentration (LD, LC): | |
LD50 (median dose)
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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)[3] |
LC50 (median concentration)
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450 ppm (rat, 4 hr) 700 ppm (mouse, 7 hr)[3] |
NIOSH (US health exposure limits): | |
PEL (Permissible)
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TWA 50 ppm (240 mg/m3) [skin][1] |
REL (Recommended)
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TWA 5 ppm (24 mg/m3) [skin][1] |
IDLH (Immediate danger) |
700 ppm[1] |
Safety data sheet (SDS) | [1] |
Related compounds | |
Related ethers
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2-Methoxyethanol 2-Ethoxyethanol |
Related compounds
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Ethylene glycol |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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 irritant[4] and can be acutely toxic, but animal studies did not find it to be mutagenic, and no studies suggest it is a human carcinogen.[5] 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 child BMI.[6]
Production
2-Butoxyethanol is commonly obtained through two processes; the ethoxylation reaction of butanol and ethylene oxide in the presence of a catalyst:
or the etherification of butanol with 2-chloroethanol.[7] 2-Butoxyethanol can be obtained in the laboratory by performing a ring opening of 2-propyl-1,3-dioxolane with boron trichloride.[8] It is often produced industrially by combining ethylene glycol and butyraldehyde in a Parr reactor with palladium on carbon.[9]
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[10] and 18% for metal cleaners and household cleaners.[11] In the US, it is considered a high production volume chemical because more than 100 million pounds of this chemical are produced per year.[11]
Uses
2-Butoxyethanol is a glycol ether with modest surfactant properties, which can also be used as a mutual solvent.[clarification needed]
Commercial uses
2-Butoxyethanol is a solvent for
In the petroleum industry
2-Butoxyethanol is commonly produced for the oil industry because of its surfactant properties.[14]
In the petroleum industry, 2-butoxyethanol is a component of
Safety
2-Butoxyethanol has a low acute toxicity, with
Disposal and degradation
2-Butoxyethanol can be disposed of by incineration. It was shown that disposal occurs faster in the presence of semiconductor particles.[7] 2-Butoxyethanol usually decomposes in the presence of air within a few days by reacting with oxygen radicals.[22] It has not been identified as a major environmental contaminant, nor is it known to bio-accumulate.[23] 2-Butoxyethanol biodegrades in soils and water, with a half life of 1–4 weeks in aquatic environments.[13]
Human exposure
2-Butoxyethanol most commonly enters the human body system through dermal absorption, inhalation, or oral consumption of the chemical.
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.[27] 2-Butoxyethanol is metabolized in mammals by the enzyme alcohol dehydrogenase.[26]
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.[28]
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.[27]
Regulation in Canada
Environment and Health Canada recommended that 2-butoxyethanol be added to Schedule 1 of the Canadian Environmental Protection Act, 1999 (CEPA).[29] 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.[30]
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,[31] and in California employers are required to inform employees when they are working with it.[32]
It is approved by the
References
- ^ a b c d e NIOSH Pocket Guide to Chemical Hazards. "#0070". National Institute for Occupational Safety and Health (NIOSH).
- ^ )
- ^ a b "2-Butoxyethanol". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
- ^ "TOXNET HAS MOVED". www.nlm.nih.gov. Retrieved 2020-01-24.
- ^ "Public Health Statement for 2-Butoxyethanol and 2-Butoxyethanol Acetate". Agency for Toxic Substances and Disease Registry, Center for Disease Control. August 1998. Retrieved 16 February 2020.
- S2CID 73443692.
- ^ a b c Harris O.; et al. (August 1998). Toxicological Profile for 2-Butoxyethanol and 2-butoxyethanol acetate. U.S. Dept of Health and Human Services.
- .
- ^ Tulchinsky, Michael (2014), Poly ethers and process for making them
- ^ .
- ^ a b c d e f "Ethylene Glycol Mono-N-Butyl Ether". National Library of Medicine. Retrieved 2014-03-26.
- ^ "Sharpie Frequently Asked Questions". sharpie.com. Archived from the original on 26 May 2015. Retrieved 30 June 2015.
- ^ a b c d Dickey, Robert W.; Dickhoff, Walton W. (2012-01-30) [2011]. "Dispersants and Seafood Safety Assessment of the potential impact of COREXIT oil dispersants on seafood safety" (PDF). Coastal Response Research Center (CRRC). (White Paper). Mobile, Alabama: Dispersant Initiative and Workshop “The Future of Dispersant Use in Spill Response” (Tuesday, September 20, 2011 to Thursday, September 22, 2011). Archived (PDF) from the original on 2021-04-12. Retrieved 2022-08-03.
- .
- .
- Nalco Environmental Solutions LLC. 1 March 2012. Archived from the original(PDF) on 2 May 2014. 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 2010-05-28. Retrieved 4 June 2010.
- ^ "Air Foam HD Material Data Safety Sheet". Product Safety. AquaClear, Inc. Retrieved 4 June 2010.
- PMID 15705494.
- ^ "Chemical Sampling Information | 2-Butoxyethanol". Occupational Safety & Health Administration. Archived from the original on 2017-07-31. Retrieved 2014-04-23.
- PMID 27632795.
- ISSN 1680-7316.
- ^ "ATSDR - ToxFAQs: 2-Butoxyethanol and 2-Butoxyethanol Acetate". cdc.gov. Retrieved 30 June 2015.
- ^ 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 ed.). Foster City, CA: Biomedical Publications. pp. 208–210.
- ^ PMID 16246510.
- ^ a b 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. 2017-03-12. 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 Laboring Relations. Archived from the original on 5 May 2008. Retrieved 2008-04-21.
- ^ "Glycol Ethers Fact Sheet". California Hazard Evaluation and Information Service. Archived from the original on 18 August 2007. Retrieved 29 October 2007.
- ^ CFR Title 21 - Food and Drugs - URL: http://www.fda.gov (2004). CFR Title: 21 CFR Part Section: 173.315
- U.S. Environmental Protection Agency. 2004-11-29. Retrieved 23 February 2008.
- ^ a b "EGBE: A World of Solutions 2000" (PDF). July 2000. Archived from the original (PDF) on 3 October 2006. Retrieved 30 April 2014.
External links
- International Chemical Safety Card 0059
- NIOSH Pocket Guide to Chemical Hazards
- Inchem SIDS dossier Archived 2016-03-03 at the Wayback Machine
- Eastman EB solvent info
- ToxFAQs for 2-Butoxyethanol and 2-Butoxyethanol Acetate from the Centers for Disease Control