Dibutoxymethane

Dibutoxymethane
	source ↗
Names
	Preferred IUPAC name 1-(Butoxymethoxy)butane
	Other names Butylal, formaldehyde dibutyl acetal
Identifiers
CAS Number	2568-90-3;
3D model (JSmol)	Interactive image;
ChemSpider	16443;
ECHA InfoCard	100.018.100
EC Number	219-909-0;
PubChem CID	17379;
UNII	V5WWR58LDU;
CompTox Dashboard (EPA)	DTXSID3062528 ;
	InChI InChI=1S/C9H20O2/c1-3-5-7-10-9-11-8-6-4-2/h3-9H2,1-2H3 Key: QLCJOAMJPCOIDI-UHFFFAOYSA-N;
	SMILES CCCCOCOCCCC;
Properties
Chemical formula	C9H20O2
Molar mass	160.257 g·mol−1
Density	0.838
Melting point	−60 °C (−76 °F; 213 K)
Boiling point	179.2 °C (354.6 °F; 452.3 K)
Solubility in water	insoluble
Refractive index (nD)	1.406
Hazards
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H226, H315, H412
Precautionary statements	P210, P233, P240, P241, P242, P243, P264, P273, P280, P302+P352, P303+P361+P353, P321, P332+P313, P362, P370+P378, P403+P235, P501
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

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. source ↗

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 Formaldehyde is an irritant and a known human carcinogen.

References

"Dibutoxymethane". webbook.nist.gov.
Spalding, Mark A.; Chatterjee, Ananda (2017). 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.
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. JSTOR 44734655.
"Acetal" in "Assessment of Alternatives to Perchloroethylene for the Dry Cleaning Industry" Toxics Use Reduction Institute. UMass Lowell. June 2012. page 21-22.
"Process for producing dibutoxymethane, diethoxymethane, dipropoxymethane or dipentoxymethane" (CN103965029B), patented to Li Yunyong, Zhou Tao, Cheng Yehua in China
Ceballos DM, Whittaker SG, Lee EG, Roberts J, Streicher R, Nourian F, Gong W, Broadwater K (October 2016). "Occupational exposures to new dry cleaning solvents: High-flashpoint hydrocarbons and butylal". J Occup Environ Hyg. 13 (10): 759–69. doi:10.1080/15459624.2016.1177648. PMC 5511734. PMID 27105306.

[1] "Dibutoxymethane". webbook.nist.gov.

[2] Spalding, Mark A.; Chatterjee, Ananda (2017). 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.

[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. JSTOR 44734655.

[turi-4] "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] Ceballos DM, Whittaker SG, Lee EG, Roberts J, Streicher R, Nourian F, Gong W, Broadwater K (October 2016). "Occupational exposures to new dry cleaning solvents: High-flashpoint hydrocarbons and butylal". J Occup Environ Hyg. 13 (10): 759–69. doi:10.1080/15459624.2016.1177648. PMC 5511734. PMID 27105306.

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