1,3-Propanediol

1,3-Propanediol
Skeletal formula of 1,3-propanediol	Spacefill model of 1,3-propanediol
	Ball and stick model of 1,3-propanediol
Names
	Preferred IUPAC name Propane-1,3-diol
	Other names 1,3-Dihydroxypropane; Trimethylene glycol
Identifiers
CAS Number	504-63-2 ;
3D model (JSmol)	Interactive image;
Abbreviations	PDO
Beilstein Reference	969155
ChEBI	CHEBI:16109 ;
ChEMBL	ChEMBL379652 ;
ChemSpider	13839553 ;
DrugBank	DB02774 ;
ECHA InfoCard	100.007.271
EC Number	207-997-3;
KEGG	C02457 ;
MeSH	1,3-propanediol
PubChem CID	10442;
RTECS number	TY2010000;
UNII	5965N8W85T ;
CompTox Dashboard (EPA)	DTXSID30897465 DTXSID8041246, DTXSID30897465 ;
	InChI InChI=1S/C3H8O2/c4-2-1-3-5/h4-5H,1-3H2 Key: YPFDHNVEDLHUCE-UHFFFAOYSA-N ; Key: YPFDHNVEDLHUCE-UHFFFAOYAS;
	SMILES OCCCO;
Properties
Chemical formula	CH2(CH2OH)2
Molar mass	76.095 g·mol−1
Appearance	Colourless liquid
Density	1.0597 g cm−3
Melting point	−27 °C; −17 °F; 246 K
Boiling point	211 to 217 °C; 412 to 422 °F; 484 to 490 K
Solubility in water	Miscible
log P	−1.093
Vapor pressure	4.5 Pa
Refractive index (nD)	1.440
Thermochemistry
Std enthalpy of; formation (ΔfH⦵298)	−485.9–−475.7 kJ mol−1
Std enthalpy of; combustion (ΔcH⦵298)	−1848.1–−1837.9 kJ mol−1
Hazards
NFPA 704 (fire diamond)	2 2 0
Flash point	79.444 °C (174.999 °F; 352.594 K)
Autoignition; temperature	400 °C (752 °F; 673 K)
Safety data sheet (SDS)	sciencelab.com
Related compounds
Related glycols	Ethylene glycol, 1,2-propanediol
	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

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.

Products

It is mainly used as a building block in the production of polymers such as polytrimethylene terephthalate.^[2]

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.^[2]

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".^[3] According to DuPont, the Bio-PDO process uses 40% less energy than conventional processes,^[4]^[5] 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.^[5]
Conversion from glycerol (a by-product of biodiesel production) using Clostridium diolis bacteria and Enterobacteriaceae.^[6]

Safety

1,3-Propanediol does not appear to pose a significant hazard via inhalation of either the vapor or a vapor/aerosol mixture.^[7]

References

^ 1,3-Propanediol from PubChem
^ ^a ^b Carl J. Sullivan; Anja Kuenz; Klaus-Dieter Vorlop (2018). "Propanediols". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a22_163.pub2. ISBN 978-3-527-30673-2.
^ Werle, Peter; Morawietz, Marcus; Lundmark, Stefan; Sörensen, Kent; Karvinen, Esko; Lehtonen, Juha (2008-07-15), "Alcohols, Polyhydric", in Wiley-VCH Verlag GmbH & Co. KGaA (ed.), Ullmann's Encyclopedia of Industrial Chemistry, Weinheim, Germany: Wiley-VCH Verlag GmbH & Co. KGaA, pp. a01_305.pub2, doi:10.1002/14356007.a01_305.pub2, ISBN 978-3-527-30673-2, retrieved 2022-03-31
^ Carl F. Muska; Carina Alles (2005-05-11). "Biobased 1,3-Propanediol A New Platform Chemical For The 21st Century" (PDF). BREW Symposium.
^ ^a ^b "Growing Demand for Products Manufactured from DuPont's Bio-Based Propanediol". AZoM.com. 2007-06-12.
^ H. Biebl; K. Menzel; A.-P. Zeng; W.-D. Deckwer (1999). "Microbial production of 1,3-propanediol". Applied Microbiology and Biotechnology. 52 (3): 289–297. doi:10.1007/s002530051523. PMID 10531640. S2CID 20017229.
^ Scott RS, Frame SR, Ross PE, Loveless SE, Kennedy GL (2005). "Inhalation toxicity of 1,3-propanediol in the rat". Inhal Toxicol. 17 (9): 487–93. doi:10.1080/08958370590964485. PMID 16020043. S2CID 25647781.

External links

Manufacturer's brochure describing uses of 1,3-propanediol

[1] 1,3-Propanediol from PubChem

[Ullmann-2] Carl J. Sullivan; Anja Kuenz; Klaus-Dieter Vorlop (2018). "Propanediols". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a22_163.pub2. ISBN 978-3-527-30673-2.

[3] Werle, Peter; Morawietz, Marcus; Lundmark, Stefan; Sörensen, Kent; Karvinen, Esko; Lehtonen, Juha (2008-07-15), "Alcohols, Polyhydric", in Wiley-VCH Verlag GmbH & Co. KGaA (ed.), Ullmann's Encyclopedia of Industrial Chemistry, Weinheim, Germany: Wiley-VCH Verlag GmbH & Co. KGaA, pp. a01_305.pub2, doi:10.1002/14356007.a01_305.pub2, ISBN 978-3-527-30673-2, retrieved 2022-03-31

[chem.uu.nl-4] Carl F. Muska; Carina Alles (2005-05-11). "Biobased 1,3-Propanediol A New Platform Chemical For The 21st Century" (PDF). BREW Symposium.

[azom.com-5] "Growing Demand for Products Manufactured from DuPont's Bio-Based Propanediol". AZoM.com. 2007-06-12.

[6] H. Biebl; K. Menzel; A.-P. Zeng; W.-D. Deckwer (1999). "Microbial production of 1,3-propanediol". Applied Microbiology and Biotechnology. 52 (3): 289–297. doi:10.1007/s002530051523. PMID 10531640. S2CID 20017229.

[7] Scott RS, Frame SR, Ross PE, Loveless SE, Kennedy GL (2005). "Inhalation toxicity of 1,3-propanediol in the rat". Inhal Toxicol. 17 (9): 487–93. doi:10.1080/08958370590964485. PMID 16020043. S2CID 25647781.

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