Chemistry:Dibutoxymethane

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Dibutoxymethane or butylal, is an oligoether (more than one -O- grouping) or acetal containing two butyl groups and a methylene grouping.[1]

Uses

Dibutoxymethane is used as a solvent and can be classed as a green solvent, as it contains no halogens, and is not very toxic.[2] It is used in cosmetics, as a cleansing agent, or solvent. It reduces the formation of soot and nitrogen oxides when added to diesel fuel.[3]

A modern dry cleaning machine by Union for use with dibutoxymethane.

It has also been used as a dry-cleaning solvent under the trade name SolvonK4, marketed by the Kreussler Company in 2010. It dissolves both water-based and oil-based stains.[4]

Production

Butylal is produced by the reaction of n-butanol with formaldehyde or formaldehyde derivtives such as 1,3,5-trioxane and paraformaldehyde.[5]

Health and safety

As butylal is a relatively new solvent in use, a little is known about its toxicological and ecological profile. It is a combustible liquid.[4]

Butylal undergoes hydrolysis to produce butanol and formaldehyde. Both compounds have been detected in very low concentrations inside dry-cleaning facilities using the solvent.[6]

References

  1. "Dibutoxymethane" (in en). https://webbook.nist.gov/cgi/cbook.cgi?ID=2568-90-3&Units=SI&cMS=on. 
  2. Spalding, Mark A.; Chatterjee, Ananda (2017) (in en). Handbook of Industrial Polyethylene and Technology: Definitive Guide to Manufacturing, Properties, Processing, Applications and Markets Set. John Wiley & Sons. p. 147,150. ISBN 978-1-119-15978-0. https://books.google.com/books?id=xNk5DwAAQBAJ&pg=PA150. 
  3. Delfort, B.; Durand, I.; Jaecker-Voirol, A.; Lacôme, T.; Paillé, F.; Montagne, X. (2002). "Oxygenated Compounds and Diesel Engine Pollutant Emissions Performances of New Generation of Products". SAE Transactions 111: 1871–1880. ISSN 0096-736X. 
  4. 4.0 4.1 "Acetal" in "Assessment of Alternatives to Perchloroethylene for the Dry Cleaning Industry" Toxics Use Reduction Institute. UMass Lowell. June 2012. page 21-22.
  5. "Process for producing dibutoxymethane, diethoxymethane, dipropoxymethane or dipentoxymethane" (CN103965029B), patented to Li Yunyong, Zhou Tao, Cheng Yehua in China
  6. "Occupational exposures to new dry cleaning solvents: High-flashpoint hydrocarbons and butylal". J Occup Environ Hyg 13 (10): 759–69. October 2016. doi:10.1080/15459624.2016.1177648. PMID 27105306.