3-Hydroxypropionic acid
Names | |
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IUPAC name
3-Hydroxypropanoic acid
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Other names
3-hydroxypropionic acid
hydracrylic acid ethylene lactic acid | |
Identifiers | |
3D model (JSmol)
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ChEBI | |
ChemSpider | |
DrugBank | |
ECHA InfoCard | 100.007.250 |
KEGG | |
CompTox Dashboard (EPA)
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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).
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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
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