1,3-Propanediol
Encyclopedia
1,3-Propanediol is the organic compound
with the formula
CH2(CH2OH)2. This three-carbon diol
is a colorless viscous liquid that is miscible with water.
.
1,3-Propanediol can be formulated into a variety of industrial products including composites
, adhesive
s, laminate
s, coating
s, moldings
, aliphatic
polyester
s, copolyesters. It is also a solvent
and used as an antifreeze
and wood paint.
, or by the hydroformylation
of ethylene oxide
to afford 3-hydroxypropionaldehyde. The aldehyde is hydrogenated to give 1,3-propanediol.
Two other routes involve bioprocessing by certain micro-organisms:
Organic compound
An organic compound is any member of a large class of gaseous, liquid, or solid chemical compounds whose molecules contain carbon. For historical reasons discussed below, a few types of carbon-containing compounds such as carbides, carbonates, simple oxides of carbon, and cyanides, as well as the...
with the formula
Chemical formula
A chemical formula or molecular formula is a way of expressing information about the atoms that constitute a particular chemical compound....
CH2(CH2OH)2. This three-carbon diol
Diol
A diol or glycol is a chemical compound containing two hydroxyl groups A geminal diol has two hydroxyl groups bonded to the same atom...
is a colorless viscous liquid that is miscible with water.
Products
It is mainly used as a building block in the production of polymers such as polytrimethylene terephthalatePolytrimethylene terephthalate
Polytrimethylene terephthalate, or PTT, is a polymer synthesized and patented in 1941. It is produced by a method called condensation polymerization or transesterification. The two monomer units used in producing this polymer are: 1,3-propanediol and terephthalic acid or dimethyl terephthalate...
.
1,3-Propanediol can be formulated into a variety of industrial products including composites
Composite material
Composite materials, often shortened to composites or called composition materials, are engineered or naturally occurring materials made from two or more constituent materials with significantly different physical or chemical properties which remain separate and distinct at the macroscopic or...
, adhesive
Adhesive
An adhesive, or glue, is a mixture in a liquid or semi-liquid state that adheres or bonds items together. Adhesives may come from either natural or synthetic sources. The types of materials that can be bonded are vast but they are especially useful for bonding thin materials...
s, laminate
Laminate
A laminate is a material that can be constructed by uniting two or more layers of material together. The process of creating a laminate is lamination, which in common parlance refers to the placing of something between layers of plastic and gluing them with heat and/or pressure, usually with an...
s, coating
Coating
Coating is a covering that is applied to the surface of an object, usually referred to as the substrate. In many cases coatings are applied to improve surface properties of the substrate, such as appearance, adhesion, wetability, corrosion resistance, wear resistance, and scratch resistance...
s, moldings
Molding (process)
Molding or moulding is the process of manufacturing by shaping pliable raw material using a rigid frame or model called a pattern....
, aliphatic
Aliphatic compound
In organic chemistry, aliphatic compounds are acyclic or cyclic, non-aromatic carbon compounds.Thus, aliphatic compounds are opposite to aromatic compounds.- Structure :...
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...
s, copolyesters. It is also a solvent
Solvent
A solvent is a liquid, solid, or gas that dissolves another solid, liquid, or gaseous solute, resulting in a solution that is soluble in a certain volume of solvent at a specified temperature...
and used as an antifreeze
Antifreeze
Antifreeze is a freeze preventive used in internal combustion engines and other heat transfer applications, such as HVAC chillers and solar water heaters....
and wood paint.
Production
1,3-Propanediol may be chemically synthesized by the hydration of acroleinAcrolein
Acrolein is the simplest unsaturated aldehyde. It is produced widely but is most often immediately reacted with other products due to its instability and toxicity...
, or by the hydroformylation
Hydroformylation
Hydroformylation, also known as oxo synthesis or oxo process, is an important industrial process for the production of aldehydes from alkenes. This chemical reaction entails the addition of a formyl group and a hydrogen atom to a carbon-carbon double bond...
of ethylene oxide
Ethylene oxide
Ethylene oxide, also called oxirane, is the organic compound with the formula . It is a cyclic ether. This means that it is composed of two alkyl groups attached to an oxygen atom in a cyclic shape . This colorless flammable gas with a faintly sweet odor is the simplest epoxide, a three-membered...
to afford 3-hydroxypropionaldehyde. The aldehyde is hydrogenated to give 1,3-propanediol.
Two other routes involve bioprocessing by certain micro-organisms:
- Conversion from corn syrupCorn syrupCorn syrup is a food syrup, which is made from the starch of maize and contains varying amounts of maltose and higher oligosaccharides, depending on the grade. Corn syrup is used in foods to soften texture, add volume, prevent crystallization of sugar, and enhance flavor...
effected by a genetically modified strainStrain (biology)In biology, a strain is a low-level taxonomic rank used in three related ways.-Microbiology and virology:A strain is a genetic variant or subtype of a micro-organism . For example, a "flu strain" is a certain biological form of the influenza or "flu" virus...
of E. coli by DuPont Tate & Lyle Bioproducts (See: bioseparation of 1,3-propanediolBioseparation of 1,3-propanediolBioseparation of 1,3-propanediol is a biochemical process for production of 1,3-propanediol. 1,3-Propanediol is an organic chemical that can be used for various ends...
). An estimated 120,000 tons were produced in 2007".. According to DuPont, the Bio-PDO process uses 40% less energy than conventional processes,, and reduces greenhouse gas emissions by 20%., Because of DuPont and Tate & Lyle's success in developing a renewable Bio-PDO process, the American Chemical SocietyAmerican Chemical SocietyThe American Chemical Society is a scientific society based in the United States that supports scientific inquiry in the field of chemistry. Founded in 1876 at New York University, the ACS currently has more than 161,000 members at all degree-levels and in all fields of chemistry, chemical...
awarded the Bio-PDO research teams the "2007 Heroes of Chemistry" award .
- Conversion from glycerolGlycerolGlycerol is a simple polyol compound. It is a colorless, odorless, viscous liquid that is widely used in pharmaceutical formulations. Glycerol has three hydroxyl groups that are responsible for its solubility in water and its hygroscopic nature. The glycerol backbone is central to all lipids...
(a by-product of biodieselBiodieselBiodiesel refers to a vegetable oil- or animal fat-based diesel fuel consisting of long-chain alkyl esters. Biodiesel is typically made by chemically reacting lipids with an alcohol....
production) using ClostridiumClostridiumClostridium is a genus of Gram-positive bacteria, belonging to the Firmicutes. They are obligate anaerobes capable of producing endospores. Individual cells are rod-shaped, which gives them their name, from the Greek kloster or spindle...
diolis bacteria and Enterobacteriaceae .