Misplaced Pages

2-Butoxyethanol

Article snapshot taken from Wikipedia with creative commons attribution-sharealike license. Give it a read and then ask your questions in the chat. We can research this topic together.

This is an old revision of this page, as edited by Uriah923 (talk | contribs) at 14:57, 19 March 2014 (More specific wording of use offshore). The present address (URL) is a permanent link to this revision, which may differ significantly from the current revision.

Revision as of 14:57, 19 March 2014 by Uriah923 (talk | contribs) (More specific wording of use offshore)(diff) ← Previous revision | Latest revision (diff) | Newer revision → (diff)
2-Butoxyethanol
2-Butoxyethanol
2-Butoxyethanol molecule
Names
IUPAC name 2-Butoxyethanol
Other names butyl cellosolve
butyl glycol
ethylene glycol monobutyl ether
Dowanol
Bane-Clene
Eastman EB solvent
BH-33 industrial cleaner
Solvaset
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.003.550 Edit this at Wikidata
RTECS number
  • KJ8575000
UNII
CompTox Dashboard (EPA)
SMILES
  • OCCOCCCC
Properties
Chemical formula C6H14O2
Molar mass 118.176 g·mol
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)
Solubility in water Miscible
Acidity (pKa) high pKa for -OH group
Viscosity 2.9 cP at 25 °C (77 °F)
Hazards
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 2: Must be moderately heated or exposed to relatively high ambient temperature before ignition can occur. Flash point between 38 and 93 °C (100 and 200 °F). E.g. diesel fuelInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
2 2 0
Flash point 67 °C (153 °F; 340 K)
Related compounds
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

2-Butoxyethanol is an organic compound with the formula BuOC2H4OH (Bu = CH3CH2CH2CH2). It is a colorless liquid with a sweet, ether-like odour. It is a butyl ether of ethylene glycol and part of the family of glycol ethers. It is a relatively nonvolatile, inexpensive solvent that is used in many domestic and industrial products.

Production

The main routes to 2-butoxyethanol is the reaction of butanol and ethylene oxide in the presence of a catalyst:

C2H4O + C4H9OH → C4H9OC2H4OH

Like other ethoxylation reactions, this process can yield a distribution of products. The second method of production consists of etherification of butanol with 2-chloroethanol.

Uses

2-Butoxyethanol is a glycol ether with modest surfactant properties. 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 volatibility.

In 2006, the European production of butyl glycol ethers amounted to 181 kilotons. Approximately 50% (90 kt/a) of which was 2-butoxyethanol. World production is estimated to be 200 to 500 kt/a, of which 75% is for paints and coatings.

2-Butoxyethanol was introduced into industry as a solvent for paints and surface coatings, as well as cleaning products and inks. Other 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, and 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 for sterilizing and cleaning. It is the main ingredient of many home, commercial and industrial cleaning solutions. Since it has both a non-polar and a polar end, it is useful for removing both polar and non-polar substances, like grease and oils.

In the petroleum industry, butoxyethanol is a component of fracturing fluids, drilling stabilizers, and oil slick dispersants for both water-based and oil-based hydraulic fracturing - and also serves as a buffer fluid when flushing / commissioning offshore subsea distribution equipment. 2-Butoxyethanol is used to stabilize the fracturing fluid that are being pumped under extreme pressure by lowering the surface tension and to facilitate release of the oil by preventing congealing.

Safety

Butoxyethanol has an low acute toxicity, with LD50 of 2.5g/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 animals. However, these rodent tests may not directly translate to carcinogenicity in humans, as the observed mechanism of cancer involves the rodents' forestomach, which humans do not have. OSHA does not regulate 2-butoxyethanol as a carcinogen; however, it should be handled as a carcinogen with extreme caution.

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.

Human exposure

Moderate respiratory exposure to 2-butoxyethanol often results in irritation of mucous membranes of the eyes, nose and throat. Heavy exposure via respiratory, dermal or oral routes can lead to hypotension, metabolic acidosis, hemolysis, pulmonary edema and coma. The current ACGIH threshold limit value (TLV) for worker exposure is 20 ppm in the industrial atmosphere, which is well above the odor threshold of 0.4 ppm. 2-butoxyethanol is metabolized in animals by the enzyme alcohol dehydrogenase. Blood or urine concentrations of 2-butoxyethanol or its major toxic metabolite, 2-butoxyacetic acid, may be measured using chromatographic techniques to monitor worker exposure or to confirm a diagnosis of poisoning in hospitalized patients. A biological exposure index of 200 mg 2-butoxyacetic acid per g creatinine has been established in an end-of-shift urine specimen for exposed U.S. employees. 2-butoxyethanol and its metabolites fall to undetectable levels in urine after about 30 hours in human males.

Regulation in Canada

2-Butoxyethanol has come under scrutiny in Canada, and Environment and Health Canada recommended that it be added to Schedule 1 of the Canadian Environmental Protection Act (CEPA). These products are not required to list it on the label when diluted to a certain point. The safety of the products as normally used is defended by the American Chemistry Council and the Soap and Detergent Association, industry trade groups.

Regulation in U.S.

U.S. Employers are required to inform employees when they are working with this substance.

Butoxyethanol is listed in the U.S. state of California as a hazardous substance, though it was removed from the U.S. Environmental Protection Agency's list of hazardous air pollutants in 1994.

Animal Studies

Harmful effects have been observed in animals exposed to high levels of 2-butoxyethanol. Developmental effects were seen in a study by Ty et al. This study exposed pregnant Fischer 344 rats and New Zealand white rabbits to varying doses of 2-butoxyethanol. At 100 ppm (483 mg/m) and 200 ppm (966 mg/m) exposure, there were statistically significant increases 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.

Neurological effects have also been observed in animals exposed to 2-butoxyethanol. In a study by Dodd et al., Fischer 344 rats were exposed to 2-butoxyethanol at concentrations of 523 ppm and 867 ppm. Both female and male rats experienced decreased coordination after this exposure. Similarly, in a study by Dow et al., male rabbits showed a loss of coordination and equilibrium after exposure to 400 ppm of 2-butoxyethanol for 2 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. For rats, there were reduced red blood cell counts and thymus weights, as well as lesions in the liver, spleen, and bone marrow.

References

  1. ^ Harris O.; et al. (August 1998). Toxicological Profile for 2-Butoxyethanol and 2-butoxyethanol acetate. U.S. Dept of Health and Human Services. {{cite book}}: Explicit use of et al. in: |author= (help)
  2. Elskamp, Carl J. "2-Butoxyethanol (Butyl Cellosolve) & 2-Butoxyethyl Acetate (Butyl Cellosolve Acetate)". United States Department of Labor.
  3. ^ Siegfried Rebsdat, Dieter Mayer "Ethylene Oxide" in Ullmann's Encyclopedia of Industrial Chemistry Wiley-VCH, Weinheim, 2005.doi:10.1002/14356007.a10_117.
  4. "Ethylene Glycol Mono-N-Butyl Ether". National Library of Medicine HSDB. Retrieved 3/14/14. {{cite web}}: Check date values in: |accessdate= (help)
  5. Jane Kay (2007-07-24). "Hazard warning on home cleaners: Study says many use chemicals linked to fertility problems". San Francisco Chronicle. Archived from the original on 28 February 2008. Retrieved 23 February 2008. {{cite news}}: Unknown parameter |deadurl= ignored (|url-status= suggested) (help)
  6. Alexandra Gorman. "Potential Hazards of Home Cleaning Products" (PDF). Women's Voices for the Earth. Retrieved 24 July 2007.
  7. "Ethylene Glycol Mono-N-Butyl Ether". National Library of Medicine HSDB. Retrieved 3/14/14. {{cite web}}: Check date values in: |accessdate= (help)
  8. "Ethylene Glycol Mono-N-Butyl Ether". National Library of Medicine HSDB. Retrieved 3/14/14. {{cite web}}: Check date values in: |accessdate= (help)
  9. "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. {{cite web}}: Unknown parameter |deadurl= ignored (|url-status= suggested) (help)
  10. "Air Foam HD Material Data Safety Sheet". Product Safety. AquaClear, Inc. Retrieved 4 June 2010.
  11. Gift, J. S. U.S. EPA's IRIS assessment of 2-butoxyethanol: the relationship of noncancer to cancer effects. Toxicol. Lett. 2005, 156, 163-178.
  12. http://nj.gov/health/eoh/rtkweb/documents/fs/0275.pdf
  13. 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.
  14. Agency for Toxic Substances and Disease Registry ToxFAQs
  15. 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, 164-173.
  16. 2009 TLVs and BEIs, American Conference of Industrial Hygienists, Cincinnati, Ohio, 2009, p.101.
  17. R. Baselt, Disposition of Toxic Drugs and Chemicals in Man, 8th edition, Biomedical Publications, Foster City, CA, 2008, pp. 208-210.
  18. 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, 164-173.
  19. "Current Use Patterns in Canada, Toxicology Profiles of Alternatives, and the Feasibility of Performing an Exposure Assessment Survey". Environment Canada. Retrieved 15 February 2011.
  20. "Glycol Ethers Fact Sheet". California Hazard Evaluation and Information Service. Retrieved 29 October 2007.
  21. "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. {{cite web}}: Unknown parameter |deadurl= ignored (|url-status= suggested) (help)
  22. "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.
  23. 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>.
  24. 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>.
  25. 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>.

External links

Categories: