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
503-66-2 YesY
ChEBI CHEBI:33404 YesY
ChemSpider 61460 YesY
DrugBank DB03688 YesY
Jmol-3D images Image
KEGG C01013 YesY
Properties
C3H6O3
Molar mass 90.08 g/mol
Melting point <25 °C
143 °C (sodium salt)
Boiling point Decomposes
Very soluble
Related compounds
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 is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 YesY verify (what isYesY/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.