2-Butoxyethanol

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2-Butoxyethanol

Names
IUPAC name
2-Butoxyethanol
Other names
Butyl cellosolve
Butyl glycol
Butyl monoether glycol
EGBE (ethylene glycol monobutyl ether)
Dowanol
Bane-Clene
Eastman EB solvent
BH-33 industrial cleaner
Solvaset
2-BE
EGBE
Butyl oxitol
Ektasolve
Jeffersol EB

Identifiers
CAS Number

111-76-2

ChEBI

CHEBI:63921

ChemSpider

13836399

Jmol 3D model

Interactive image

RTECS number

KJ8575000

UNII

I0P9XEZ9WV

InChI[show]
SMILES[show]
Properties
Chemical formula

C6H14O2

Molar mass

118.18 gmol1

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)

Solubility in water

Miscible (and in most organic

solvents)

Vapor pressure

0.8 mmHg[1]

Acidity (pKa)

high pKa for -OH group

Viscosity

2.9 cP at 25 C (77 F)
Hazards

Safety data sheet

MSDS by Mallinckrodt Baker

EU classification
(DSD)

Harmful (Xn)

R-phrases

R20/21/22-R36/38

S-phrases

(S2)-S36/37-S46

NFPA 704

2
2
0

Flash point

67 C (153 F; 340 K)

Autoignition
temperature

245 C (473 F; 518 K)

Explosive limits

1.1-12.7%[1]

Lethal dose or concentration (LD, LC):

1230 mg/kg (mouse, oral)
470 mg/kg (rat, oral)
LD50 (Median dose)

300 mg/kg (rabbit, oral)

1200 mg/kg (guinea pig, oral)
1480 mg/kg (rat, oral)[2]

LC50 (Median
concentration)

450 ppm (rat, 4 hr)

700 ppm (mouse, 7 hr)[2]

US health exposure limits (NIOSH):

PEL (Permissible)

TWA 50 ppm (240 mg/m3) [skin][1]

REL
(Recommended)

TWA 5 ppm (24 mg/m3) [skin][1]

IDLH (Immediate
danger)

700 ppm[1]

Related compounds
Related ethers
Related compounds

2-Methoxyethanol
2-Ethoxyethanol
Ethylene glycol

Except where otherwise noted, data are given for materials in

their standard state (at 25 C [77 F], 100 kPa).
verify (what is

?)

Infobox references

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.

Contents
[hide]

1 Production

2 Uses
o 2.1 Commercial uses
o 2.2 In the petroleum industry

3 Safety
o 3.1 Disposal and degradation
o 3.2 Human exposure
o 3.3 Animal studies
o 3.4 Regulation in Canada
o 3.5 Regulation in the US

4 References

5 External links

Production[edit]
2-Butoxyethanol is commonly obtained through two processes; the ethoxylation reaction of
butanol and ethylene oxide in the presence of the catalyst:
C2H4O + C4H9OH C4H9OC2H4OH

or the etherification of butanol with 2-chloroethanol.[3]

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[4] and 18% for metal cleaners and household
cleaners.[5] In the US, it is considered a High Production Volume Chemical because greater than
100 million pounds of this chemical is produced per year.[5]

Uses[edit]
2-Butoxyethanol is a glycol ether with modest surfactant properties (and it can be used as a
mutual solvent). In use since the 1930s, glycol ethers are solvents that dissolve both watersoluble 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.[6]

Commercial uses[edit]
2-Butoxyethanol is a solvent for paints and surface coatings, as well as cleaning products and
inks.[4][7] 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.[8]

In the petroleum industry[edit]

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[5]
[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.[5] The
compound is also used to facilitate the release of the gas by preventing congealing.[5] It is also
used as a crude oil-water coupling solvent for more general oil well workovers.[5] Because of its
surfactant properties, it is a major constituent (3060% w/w) in the oil spill dispersant Corexit
9527,[9] which was widely used in the aftermath of the 2010 Deepwater Horizon oil spill.[8]

Safety[edit]

2-Butoxyethanol has a low acute toxicity, with LD of 2.5 g/kg in rats.[4] 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.[10]
American Conference of Governmental Industrial Hygienists (ACGIH) reports that 2butoxyethanol is carcinogenic in rodents.[11] These rodent tests may not directly translate to
carcinogenicity in humans, as the observed mechanism of cancer involves the rodents'
forestomach, which humans lack.[12] OSHA does not regulate 2-butoxyethanol as a carcinogen.[13]
50

Disposal and degradation[edit]

2-Butoxyethanol can be disposed of by incineration. It was shown that disposal occurs faster in
the presence of semiconductor particles.[3] 2-Butoxyethanol usually decomposes in the presence
of air within a few days by reacting with oxygen radicals.[14] It has not been identified as a major
environmental contaminant, nor is it known to bio-accumulate.[15] 2-Butoxyethanol biodegrades
in soils and water, with a half life of 14 weeks in aquatic environments.[8]

Human exposure[edit]
2-butoxyethanol most commonly enters the human body system through dermal absorption,
inhalation, or oral consumption of the chemical.[3] 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 2butoxyacetic acid per g creatinine has been established in an end-of-shift urine specimen for U.S.
employees.[16][17] 2-Butoxyethanol and its metabolites fall to undetectable levels in urine after
about 30 hours in human males.[18]

Animal studies[edit]
Harmful effects have been observed in nonhuman mammals exposed to high levels of 2butoxyethanol. 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 2butoxyethanol. 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, 2butoxyethanol was associated with a significant decrease in maternal body weight, uterine
weight, and number of total implants.[19] 2-Butoxyethanol is metabolized in mammals by the
enzyme alcohol dehydrogenase.[18]
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.[20]
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.[19]

Regulation in Canada[edit]
Environment and Health Canada recommended that 2-butoxyethanol be added to Schedule 1 of
the Canadian Environmental Protection Act, 1999 (CEPA).[21] 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.[22]

Regulation in the US[edit]

2-Butoxyethanol is listed in California as a hazardous substance,[23] and US employers are
required to inform employees when they are working with it.[24]
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".,[8] 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".[25] 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.[26][27] The EPA
currently lists it in the context of pesticides as a "potentially toxic inert, with high priority for
testing".[28] The safety of products containing 2-Butoxyethanol as normally used is defended by
the industry trade groups the American Chemistry Council[27] and the Soap and Detergent
Association.

References[edit]
1.

^ Jump up to: a b c d e "NIOSH Pocket Guide to Chemical Hazards #0070". National Institute for
Occupational Safety and Health (NIOSH).

2.

^ Jump up to: a b "2-Butoxyethanol". Immediately Dangerous to Life and Health. National Institute
for Occupational Safety and Health (NIOSH).

3.

^ Jump up to: 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.

4.

^ Jump up to: a b c Siegfried Rebsdat, Dieter Mayer "Ethylene Glycol" in Ullmann's Encyclopedia
of Industrial Chemistry, Wiley-VCH, Weinheim, 2000.doi:10.1002/14356007.a10_101.

5.

^ Jump up to: a b c d e f "Ethylene Glycol Mono-N-Butyl Ether". National Library of Medicine.

Retrieved 2014-03-26.

6.

Jump up ^ Elskamp, Carl J. "2-Butoxyethanol (Butyl Cellosolve) & 2-Butoxyethyl Acetate (Butyl
Cellosolve Acetate)". United States Department of Labor.

7.

Jump up ^ "Sharpie Frequently Asked Questions". sharpie.com. Retrieved 30 June 2015.

8.

^ Jump up to: a b c d Dickey, Robert; W. Dickhoff. "Assessment of the potential impact of

COREXIT oil dispersants on seafood safety" (PDF). Dispersants and Seafood Safety. Retrieved 2014-0326.

9.

Jump up ^ "SAFETY DATA SHEET - PRODUCT: COREXIT EC9527A" (PDF). Nalco

Environmental Solutions LLC. 1 March 2012. Retrieved 30 April 2014.

10.

Jump up ^ "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.

11.

Jump up ^ "Air Foam HD Material Data Safety Sheet". Product Safety. AquaClear, Inc.
Retrieved 4 June 2010.

12.

Jump up ^ Gift, J. S. (2005). "U.S. EPA's IRIS assessment of 2-Butoxyethanol: the relationship of
noncancer to cancer effects". Toxicol. Lett. 156: 163178. doi:10.1016/j.toxlet.2003.08.014.

13.

Jump up ^ "Chemical Sampling Information | 2-Butoxyethanol". Occupational Safety & Health

Administration.

14.

Jump up ^ 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.

15.

Jump up ^ "ATSDR - ToxFAQs: 2-Butoxyethanol and 2-Butoxyethanol Acetate". cdc.gov.

Retrieved 30 June 2015.

16.

Jump up ^ 2009 TLVs and BEIs, American Conference of Industrial Hygienists, Cincinnati, Ohio,
2009, p.101.

17.

Jump up ^ R. Baselt (2008). Disposition of Toxic Drugs and Chemicals in Man (8th ed.). Foster
City, CA: Biomedical Publications. pp. 208210.

18.

^ Jump up to: a b 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: 164173.
doi:10.1016/j.toxlet.2005.09.012.

19.

^ Jump up to: 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>

20.

Jump up ^ United States of America. Agency for Toxic Substances and Disease Registry.
Department of Health and Human Services. Toxicological Profile for 2-Butoxyethanol and 2Butoxyethanol 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>

21.

Jump up ^ "Current Use Patterns in Canada, Toxicology Profiles of Alternatives, and the
Feasibility of Performing an Exposure Assessment Survey". Environment Canada. Retrieved 15 February
2011.

22.

Jump up ^ "Regulations Amending the 2-Butoxyethanol Regulations". Canada Gazette.

Canadian Department of Public Works and Government Services. 23 April 2014. Retrieved 30 April 2014.

23.

Jump up ^ "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.

24.

Jump up ^ "Glycol Ethers Fact Sheet". California Hazard Evaluation and Information Service.
Retrieved 29 October 2007.

25.

Jump up ^ CFR Title 21 - Food and Drugs - URL: http://www.fda.gov (2004). CFR Title: 21 CFR
Part Section: 173.315

26.

Jump up ^ "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.

27.

^ Jump up to: a b "EGBE: A World of Solutions 2000" (PDF). July 2000. Archived from the original
(PDF) on 3 October 2006. Retrieved 30 April 2014.

28.

Jump up ^ EPA List of Pesticide Product Inert Ingredients (May 1995) Listed Name(s): Butyl
cellosolve. Retrieved Nov 17, 2015.

External links[edit]

International Chemical Safety Card 0059

NIOSH Pocket Guide to Chemical Hazards

Inchem SIDS dossier

Eastman EB solvent info

ToxFAQs for 2-Butoxyethanol and 2-Butoxyethanol Acetate from the Centers for
Disease Control

Authority control

GND: 4830965-5

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This page was last modified on 15 March 2016, at 04:36.