3-Hydroxypropionic acid

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3-Hydroxypropionic acid[1]
Skeletal formula
Ball-and-stick model
Identifiers
CAS number 503-66-2 YesY
ChemSpider 61460 YesY
DrugBank DB03688
KEGG C01013 YesY
ChEBI CHEBI:33404 YesY
Jmol-3D images Image 1
Properties
Molecular formula C3H6O3
Molar mass 90.08 g/mol
Melting point <25 °C
143 °C (sodium salt)
Boiling point Decomposes
Solubility in water Very soluble
Related compounds
Related carboxylic acids acetic acid
glycolic acid
propionic acid
lactic acid
malonic acid
butyric acid
hydroxybutyric acid
Related compounds 1-propanol
2-propanol
propionaldehyde
acrolein
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 YesY (verify) (what is: YesY/N?)
Infobox references

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 engineered microbes.[2]

Applications in producing a biodegradable polymer[edit]

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[edit]

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

References[edit]

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