1,3-Propanediol

Last updated
1,3-Propanediol
Skeletal formula of 1,3-propanediol 1,3-Propanediol.svg
Skeletal formula of 1,3-propanediol
Spacefill model of 1,3-propanediol 1,3-Propanediol-SpaceFillingModel.png
Spacefill model of 1,3-propanediol
1,3-Propanediol-Ball&Stick.png
Names
Preferred IUPAC name
Propane-1,3-diol [1]
Other names
1,3-Dihydroxypropane
Trimethylene glycol
Identifiers
3D model (JSmol)
3DMet
AbbreviationsPDO
969155
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.007.271 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 207-997-3
KEGG
MeSH 1,3-propanediol
PubChem CID
RTECS number
  • TY2010000
UNII
  • InChI=1S/C3H8O2/c4-2-1-3-5/h4-5H,1-3H2 Yes check.svgY
    Key: YPFDHNVEDLHUCE-UHFFFAOYSA-N Yes check.svgY
  • Key: YPFDHNVEDLHUCE-UHFFFAOYAS
  • OCCCO
Properties
C3H8O2
Molar mass 76.095 g·mol−1
AppearanceColourless 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
Miscible
log P −1.093
Vapor pressure 4.5 Pa
1.440
Thermochemistry
−485.9–−475.7 kJ mol−1
−1848.1–−1837.9 kJ mol−1
Hazards
NFPA 704 (fire diamond)
NFPA 704.svgHealth 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 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
0
Flash point 79.444 °C (174.999 °F; 352.594 K)
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).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

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.

Contents

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:

Safety

1,3-Propanediol does not appear to pose a significant hazard via inhalation of either the vapor or a vapor/aerosol mixture. [7] However, like with any chemical exposure should be controlled and maintained.

See also

Related Research Articles

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<span class="mw-page-title-main">Pentaerythritol</span> Chemical compound

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<span class="mw-page-title-main">Tetrahydrofuran</span> Cyclic chemical compound, (CH₂)₄O

Tetrahydrofuran (THF), or oxolane, is an organic compound with the formula (CH2)4O. The compound is classified as heterocyclic compound, specifically a cyclic ether. It is a colorless, water-miscible organic liquid with low viscosity. It is mainly used as a precursor to polymers. Being polar and having a wide liquid range, THF is a versatile solvent.

A diol is a chemical compound containing two hydroxyl groups. An aliphatic diol is also called a glycol. This pairing of functional groups is pervasive, and many subcategories have been identified.

Dihydroxyacetone phosphate (DHAP, also glycerone phosphate in older texts) is the anion with the formula HOCH2C(O)CH2OPO32-. This anion is involved in many metabolic pathways, including the Calvin cycle in plants and glycolysis. It is the phosphate ester of dihydroxyacetone.

<span class="mw-page-title-main">Dimethoxyethane</span> Chemical compound

Dimethoxyethane, also known as glyme, monoglyme, dimethyl glycol, ethylene glycol dimethyl ether, dimethyl cellosolve, and DME, is a colorless, aprotic, and liquid ether that is used as a solvent, especially in batteries. Dimethoxyethane is miscible with water.

<span class="mw-page-title-main">Dicyclopentadiene</span> Chemical compound

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2-Chloroethanol (also called ethylene chlorohydrin or glycol chlorohydrin) is an organic chemical compound with the chemical formula HOCH2CH2Cl and the simplest beta-halohydrin (chlorohydrin). This colorless liquid has a pleasant ether-like odor. It is miscible with water. The molecule is bifunctional, consisting of both an alkyl chloride and an alcohol functional group.

<span class="mw-page-title-main">Polytrimethylene terephthalate</span> Chemical compound

Polytrimethylene terephthalate (PTT), is a polyester synthesized and patented in 1941. It is produced by a method called condensation polymerization or transesterification. The two monomer units used in producing this polymer are: 1,3-propanediol and terephthalic acid or dimethyl terephthalate. Similar to polyethylene terephthalate, the PTT is used to make carpet fibers.

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1,3-Dichloropropene, sold under diverse trade names, is an organochlorine compound with the formula C3H4Cl2. It is a colorless liquid with a sweet smell. It is feebly soluble in water and evaporates easily. It is used mainly in farming as a pesticide, specifically as a preplant fumigant and nematicide. It is widely used in the US and other countries, but is banned in 34 countries.

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1,3-Butanediol is an organic compound with the formula CH3CH(OH)CH2CH2OH. With two alcohol functional groups, the molecule is classified as a diol. The compound is also chiral, but most studies do not distinguish the enantiomers. The compound is a colorless, bittersweet, water-soluble liquid. It is one of four common structural isomers of butanediol. It is used in flavoring.

<span class="mw-page-title-main">Hexachlorobutadiene</span> Chemical compound

Hexachlorobutadiene, (often abbreviated as "HCBD") Cl2C=C(Cl)C(Cl)=CCl2, is a colorless liquid at room temperature that has an odor similar to that of turpentine. It is a chlorinated aliphatic diene with niche applications but is most commonly used as a solvent for other chlorine-containing compounds. Structurally, it has a 1,3-butadiene core, but fully substituted with chlorine atoms.

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<span class="mw-page-title-main">1,2-Butanediol</span> Chemical compound

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References

  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. 1 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   978-3527306732.
  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. 1 2 "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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