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3-Hydroxypropionic acid

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3-Hydroxypropionic acid[1]
Skeletal formula
Ball-and-stick model
Names
IUPAC name
3-Hydroxypropanoic acid
Other names
3-hydroxypropionic acid
hydracrylic acid
ethylene lactic acid
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
DrugBank
ECHA InfoCard 100.007.250 Edit this at Wikidata
KEGG
  • InChI=1S/C3H6O3/c4-2-1-3(5)6/h4H,1-2H2,(H,5,6) checkY
    Key: ALRHLSYJTWAHJZ-UHFFFAOYSA-N checkY
  • InChI=1/C3H6O3/c4-2-1-3(5)6/h4H,1-2H2,(H,5,6)
    Key: ALRHLSYJTWAHJZ-UHFFFAOYAU
  • O=C(O)CCO
Properties
C3H6O3
Molar mass 90.08 g/mol
Melting point <25 °C
143 °C (sodium salt)
Boiling point Decomposes
Very soluble
Related compounds
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

3-Hydroxypropionic acid is a carboxylic acid, specifically a beta hydroxy acid. It is an acidic viscous liquid with a pKa of 4.5.[1] It is very soluble in water, soluble in ethanol, and miscible with diethyl ether. Upon distillation, it dehydrates to form acrylic acid.

3-Hydroxypropionic acid is used in the industrial production of various chemicals such as acrylates. It can be produced by certain microbes.[2]

Applications in producing a biodegradable polymer

A method has been developed by the University of Minnesota to produce a biodegradable polymer polyester known as poly(3-hydroxypropionic acid).[3] The method combines the high-molecular weight and control aspects of ring-opening polymerization with the commercial availability of the beta hydroxy acid, 3-hydroxypropionic acid which is abbreviated as 3-HP. Since 3-HP can be derived from biological sources, the resulting material, poly(3-hydroxypropionic acid) or P(3-HP), is biorenewable. The new method allows direct synthesis of the bio-based polymer P(3-HP) from 3-HP, a commercial monomer that is derived from corn. The method uses a single vessel reactor for simple synthesis and rapid scale up. The method results in a higher molecular weight which makes the polymer more structurally sound using a process with lower toxicity than competing technologies.

See also

  • Lactic acid (2-hydroxypropanoic acid)
  • listed as hydracrylic acid in the Merck index, 12th Edition

References

  1. ^ a b Merck Index, 11th Edition, 4681.
  2. ^ The Biobased Revolution
  3. ^ "3-HP". Retrieved 27 May 2011.
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