1,3-Propanediol

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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
CH2(CH2OH)2
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
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).
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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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Pentaerythritol is an organic compound with the formula C(CH2OH)4. The molecular structure can be described as a neopentane with one hydrogen atom in each methyl group replaced by a hydroxyl (–OH) group. It is therefore a polyol, specifically a tetrol.

In chemistry, a hydration reaction is a chemical reaction in which a substance combines with water. In organic chemistry, water is added to an unsaturated substrate, which is usually an alkene or an alkyne. This type of reaction is employed industrially to produce ethanol, isopropanol, and butan-2-ol.

<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. It is an isomer of another solvent, butanone.

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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

Dicyclopentadiene, abbreviated DCPD, is a chemical compound with formula C10H12. At room temperature, it is a white brittle wax, although lower purity samples can be straw coloured liquids. The pure material smells somewhat of soy wax or camphor, with less pure samples possessing a stronger acrid odor. Its energy density is 10,975 Wh/l. Dicyclopentadiene is a co-produced in large quantities in the steam cracking of naphtha and gas oils to ethylene. The major use is in resins, particularly, unsaturated polyester resins. It is also used in inks, adhesives, and paints.

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<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.

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

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

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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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