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1,3-Propanediol
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changed changed 477186003 1,3-Propanediol-SpaceFillingModel.png bg-transparent correct ?? 150 Ball and stick model of 1,3-propanediol 1,3-Propanediol.svg skin-invert-image correct ?? Skeletal formula of 1,3-propanediol 1,3-Propanediol-Ball&Stick.png bg-transparent correct ?? Spacefill model of 1,3-propanediol Propane-1,3-diol10442 1,3-Propanediol 1,3-DihydroxypropaneTrimethylene glycol PDO 504-63-2 correct CAS 969155 B00444 16109 correct EBI 379652 correct EBI 13839553 correct chemspider 207-997-3 DB02774 correct drugbank C02457 correct kegg 1,3-propanediol 10442 TY2010000 5965N8W85T correct FDA 1S/C3H8O2/c4-2-1-3-5/h4-5H,1-3H2 correct chemspider YPFDHNVEDLHUCE-UHFFFAOYSA-N correct chemspider YPFDHNVEDLHUCE-UHFFFAOYAS OCCCO
CH2(CH2OH)2 3 8 2 Colourless liquid 1.0597 g cm−3 246 484 to 490 Miscible acetone, alcohols, pyridine −1.093 4.5 Pa 1.440 −485.9–−475.7 kJ mol−1 −1848.1–−1837.9 kJ mol−1 sciencelab.com 2 2 0 79.444 400 glycols Ethylene glycol, 1,2-propanediol
1,3-Propanediol is the organic compound with the formula CH2(CH2OH)2. This 3-carbon diol is a colorless viscous liquid that is miscible with water. It is soluble in many common organic solvents, except benzene, carbon tetrachloride, diethyl ether, methyl isobutyl ketone, and nitromethane.Weast, Robert C. (1973). "Miscibility of Organic Solvent Pairs". CRC Handbook of Chemistry and Physics (54th ed.). Ohio, USA: CRC Press. page C-720.
Products
It is mainly used as a building block in the production of polymers such as polytrimethylene terephthalate.Propanediols Carl J. Sullivan Anja Kuenz Klaus-Dieter Vorlop 2018 10.1002/14356007.a22_163.pub2
1,3-Propanediol can be formulated into a variety of industrial products including composites, adhesives, laminates, coatings, moldings, aliphatic polyesters, and copolyesters. It is also a common solvent. It is used as an antifreeze and as a component in wood paint.
Production
1,3-Propanediol is mainly produced by the hydration of acrolein. An alternative route involves the hydroformylation of ethylene oxide to form 3-hydroxypropionaldehyde. The aldehyde is subsequently hydrogenated to give 1,3-propanediol. Biotechnological routes are also known.
Two other routes involve bioprocessing by certain micro-organisms:
Conversion from glucose effected by a genetically modified strain of E. coli by DuPont Tate & Lyle BioProducts (See: bioseparation of 1,3-propanediol). An estimated 120,000 tons were produced in 2007".Werle Peter Alcohols, Polyhydric 2008-07-15 https://onlinelibrary.wiley.com/doi/10.1002/14356007.a01_305.pub2 Ullmann's Encyclopedia of Industrial Chemistry a01_305.pub2 Wiley-VCH Verlag GmbH & Co. KGaA Weinheim, Germany Wiley-VCH Verlag GmbH & Co. KGaA en 10.1002/14356007.a01_305.pub2 978-3-527-30673-2 2022-03-31 Morawietz Marcus Lundmark Stefan Sörensen Kent Karvinen Esko Lehtonen Juha subscription According to DuPont, the Bio-PDO process uses 40% less energy than conventional processes, Biobased 1,3-Propanediol A New Platform Chemical For The 21st Century Carl F. Muska Carina Alles BREW Symposium 2005-05-11 http://www.chem.uu.nl/brew/BREWsymposiumWiesbaden11mei2005/WEBSITEBrewPresentations51105.PDF AZoM.com http://www.azom.com/news.aspx?NewsID=8862 Growing Demand for Products Manufactured from DuPont's Bio-Based Propanediol 2007-06-12 Because of DuPont and Tate & Lyle's success in developing a renewable Bio-PDO process, the American Chemical Society awarded the Bio-PDO research teams the "2007 Heroes of Chemistry" award.
Conversion from glycerol (a by-product of biodiesel production) using Clostridium diolis bacteria and Enterobacteriaceae. Microbial production of 1,3-propanediol H. Biebl K. Menzel A.-P. Zeng W.-D. Deckwer Applied Microbiology and Biotechnology 52 289–297 1999 10531640 10.1007/s002530051523 3 20017229
Safety
1,3-Propanediol does not appear to pose a significant hazard via inhalation of either the vapor or a vapor/aerosol mixture. Inhalation toxicity of 1,3-propanediol in the rat Scott RS, Frame SR, Ross PE, Loveless SE, Kennedy GL Inhal Toxicol 2005 17 9 487–93 10.1080/08958370590964485 16020043 25647781
See also
Butylene glycol
Ethylene glycol
Polylactic acid
Propylene glycol
References
External links
Manufacturer's brochure describing uses of 1,3-propanediol
Category:Alcohol solvents
Category:Alkanediols
Category:1,3-Propanediyl compounds