propan 1 3 diol

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1,3-Propanediol
Skeletal formula of 1,3-propanediol
Skeletal formula of 1,3-propanediol
Spacefill model 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[1]

Other names

1,3-Dihydroxypropane
Trimethylene glycol

Identifiers

CAS Number
  • 504-63-2 check

3D model (JSmol)
  • Interactive image
3DMet
  • B00444
Abbreviations PDO

Beilstein Reference

 969155
ChEBI
  • CHEBI:16109 check
ChEMBL
  • ChEMBL379652 check
ChemSpider
  • 13839553 check
DrugBank
  • DB02774 check
ECHA InfoCard 100.007.271 Edit this at Wikidata
EC Number
  • 207-997-3
KEGG
  • C02457 check
MeSH 1,3-propanediol

PubChem CID
  • 10442
RTECS number
  • TY2010000
UNII
  • 5965N8W85T check

CompTox Dashboard (EPA)
  • DTXSID8041246 Edit this at Wikidata

InChI

  • InChI=1S/C3H8O2/c4-2-1-3-5/h4-5H,1-3H2 check

    Key: YPFDHNVEDLHUCE-UHFFFAOYSA-N check

  • 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 tát 217 °C; 412 to tát 422 °F; 484 to tát 490 K
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)
NFPA 704 four-colored diamondHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 2: Must be moderately heated or exposed to tát relatively high ambient temperature before ignition can occur. Flash point between 38 and 93 °C (100 and 200 °F). E.g. diesel fuelInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code

2

2

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

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 3-carbon diol is a colorless viscous liquid that is miscible with water.

Products[edit]

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[edit]

1,3-Propanediol is mainly produced by the hydration of acrolein. An alternative route involves the hydroformylation of ethylene oxide to tát size 3-hydroxypropionaldehyde. The aldehyde is subsequently hydrogenated to tát 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 tát DuPont, the Bio-PDO process uses 40% less energy kêu ca 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[edit]

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

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See also[edit]

  • Butylene glycol
  • Ethylene glycol
  • Polylactic acid
  • Propylene glycol

References[edit]

  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. ^ 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.
  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
  4. ^ Carl F. Muska; Carina Alles (2005-05-11). "Biobased 1,3-Propanediol A New Platform Chemical For The 21st Century" (PDF). BREW Symposium.
  5. ^ a b "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.

External links[edit]

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