1,3-Propanediol

1,3-Propanediol
Skeletal formula of 1,3-propanediol	Spacefill model of 1,3-propanediol
Names
	IUPAC name Propane-1,3-diol[1]
	Other names 1,3-Dihydroxypropane; Trimethylene glycol
Identifiers
CAS Number	504-63-2 ;
3D model (JSmol)	Interactive image;
3DMet	B00444;
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)	DTXSID8041246 ;
	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	C3H8O2
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
Safety data sheet	sciencelab.com
S-phrases (outdated)	S23, S24/25
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)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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	Infobox references

1,3-Propanediol is the organic compound with the formula CH₂(CH₂OH)₂. This three-carbon diol is a colorless viscous liquid that is miscible with water.[2]

Products

It is mainly used as a building block in the production of polymers such as polytrimethylene terephthalate.[3]

1,3-Propanediol can be formulated into a variety of industrial products including composites, adhesives, laminates, coatings, moldings, aliphatic polyesters, copolyesters. It is also a solvent and used as an antifreeze and 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 afford 3-hydroxypropionaldehyde. The aldehyde is subsequently hydrogenated to give 1,3-propanediol. Biotechnological routes are also known.[3]

Two other routes involve bioprocessing by certain micro-organisms:

Conversion from corn syrup 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".[4] According to DuPont, the Bio-PDO process uses 40% less energy than conventional processes,[5][6][5][6] 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.[6]
Conversion from glycerol (a by-product of biodiesel production) using Clostridium diolis bacteria and Enterobacteriaceae.[7]

Safety

1,3-Propanediol does not appear to pose a significant hazard via inhalation of either the vapor or a vapor/aerosol mixture.[8]

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References

"1,3-propanediol - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 16 September 2004. Identification and Related Records. Retrieved 20 October 2011.
Merck Index, 11th Edition, 9629.
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.
Peter Werle, Marcus Morawietz, Stefan Lundmark, Kent Sörensen, Esko Karvinen, Juha Lehtonen "Alcohols, Polyhydric" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, 2006, Weinheim.
Carl F. Muska; Carina Alles (2005-05-11). "Biobased 1,3-Propanediol A New Platform Chemical For The 21st Century" (PDF). BREW Symposium.
"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.
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.

External links

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

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[1] "1,3-propanediol - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 16 September 2004. Identification and Related Records. Retrieved 20 October 2011.

[2] Merck Index, 11th Edition, 9629.

[Ullmann-3] 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.

[4] Peter Werle, Marcus Morawietz, Stefan Lundmark, Kent Sörensen, Esko Karvinen, Juha Lehtonen "Alcohols, Polyhydric" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, 2006, Weinheim.

[chem.uu.nl-5] 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-6] "Growing Demand for Products Manufactured from DuPont's Bio-Based Propanediol". AZoM.com. 2007-06-12.

[7] 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.

[8] 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.