3-Hydroxypropionic acid
Encyclopedia
3-Hydroxypropionic acid is a carboxylic acid
, specifically a beta hydroxy acid
. It is an acidic viscous liquid with a pKa
of 4.5. 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 acrylate
s. It can be produced by certain microbes.
Applications of 3-Hydroxypropionic acid 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). 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.
Carboxylic acid
Carboxylic acids are organic acids characterized by the presence of at least one carboxyl group. The general formula of a carboxylic acid is R-COOH, where R is some monovalent functional group...
, specifically a beta hydroxy acid
Beta hydroxy acid
A beta hydroxy acid or β-hydroxy acid is an organic compound that contains a carboxylic acid functional group and hydroxy functional group separated by two carbon atoms...
. It is an acidic viscous liquid with a pKa
PKA
PKA, pKa, or other similar variations may stand for:* pKa, the symbol for the acid dissociation constant at logarithmic scale* Protein kinase A, a class of cAMP-dependent enzymes* Pi Kappa Alpha, the North-American social fraternity...
of 4.5. It is very soluble in water, soluble in ethanol
Ethanol
Ethanol, also called ethyl alcohol, pure alcohol, grain alcohol, or drinking alcohol, is a volatile, flammable, colorless liquid. It is a psychoactive drug and one of the oldest recreational drugs. Best known as the type of alcohol found in alcoholic beverages, it is also used in thermometers, as a...
, and miscible with diethyl ether
Diethyl ether
Diethyl ether, also known as ethyl ether, simply ether, or ethoxyethane, is an organic compound in the ether class with the formula . It is a colorless, highly volatile flammable liquid with a characteristic odor...
. Upon distillation, it dehydrates
Dehydration reaction
In chemistry and the biological sciences, a dehydration reaction is usually defined as a chemical reaction that involves the loss of water from the reacting molecule. Dehydration reactions are a subset of elimination reactions...
to form acrylic acid
Acrylic acid
Acrylic acid is an organic compound with the formula CH2=CHCO2H. It is the simplest unsaturated carboxylic acid, consisting of a vinyl group connected directly to a carboxylic acid terminus. This colorless liquid has a characteristic acrid or tart smell. It is miscible with water, alcohols,...
.
3-Hydroxypropionic acid is used in the industrial production of various chemicals such as acrylate
Acrylate
The acrylate ion is the ion of acrylic acid.Acrylates are the salts and esters of acrylic acid. They are also known as propenoates ....
s. It can be produced by certain microbes.
Applications of 3-Hydroxypropionic acid in producing a biodegradable polymerBiodegradable polymerBiodegradable polymers are polymers that break down and lose their initial integrity. Biodegradable polymers are used in medical devices to avoid a second operation to remove them, or to gradually release a drug TYPES OF BIODEGRADABLE POLYMERS1...
A method has been developed by the University of Minnesota to produce a biodegradable polymerBiodegradable polymer
Biodegradable polymers are polymers that break down and lose their initial integrity. Biodegradable polymers are used in medical devices to avoid a second operation to remove them, or to gradually release a drug TYPES OF BIODEGRADABLE POLYMERS1...
polyester
Polyester
Polyester is a category of polymers which contain the ester functional group in their main chain. Although there are many polyesters, the term "polyester" as a specific material most commonly refers to polyethylene terephthalate...
known as poly(3-hydroxypropionic acid). The method combines the high-molecular weight and control aspects of ring-opening polymerization
Ring-opening polymerization
In polymer chemistry, ring-opening polymerization is a form of chain-growth polymerization, in which the terminal end of a polymer acts as a reactive center, where further cyclic monomers join to form a larger polymer chain through ionic propagation...
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.