1,3-Propanediol

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.[2]

1,3-Propanediol
Skeletal formula of 1,3-propanediol
Spacefill model of 1,3-propanediol
Ball and stick model of 1,3-propanediol
Names
IUPAC name
Propane-1,3-diol[1]
Other names
1,3-Dihydroxypropane
Trimethylene glycol
Identifiers
3D model (JSmol)
3DMet B00444
Abbreviations PDO
969155
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.007.271
EC Number 207-997-3
KEGG
MeSH 1,3-propanediol
RTECS number TY2010000
UNII
Properties
C3H8O2
Molar mass 76.095 g·mol−1
Appearance Colourless liquid
Density 1.0597 g cm−3
Melting point −27 °C; −17 °F; 246 K
Boiling point 211 to 217 °C; 412 to 422 °F; 484 to 490 K
Miscible
log P −1.093
Vapor pressure 4.5 Pa
1.440
Thermochemistry
−485.9–−475.7 kJ mol−1
−1848.1–−1837.9 kJ mol−1
Hazards
Safety data sheet sciencelab.com
S-phrases (outdated) S23, S24/25
NFPA 704
Flammability code 2: Must be moderately heated or exposed to relatively high ambient temperature before ignition can occur. Flash point between 38 and 93 °C (100 and 200 °F). E.g., diesel fuelHealth code 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g., chloroformReactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g., liquid nitrogenSpecial hazards (white): no codeNFPA 704 four-colored diamond
2
2
0
Flash point 79.444 °C (174.999 °F; 352.594 K)
400 °C (752 °F; 673 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Products

It is mainly used as a building block in the production of polymers such as polytrimethylene terephthalate.

1,3-Propanediol can be formulated into a variety of industrial products including composites, adhesives, laminates, coatings, moldings, aliphatic polyesters, copolyesters. It is also a solvent and used as an antifreeze and in wood paint.

Production

1,3-Propanediol may be chemically synthesized by the hydration of acrolein, or by the hydroformylation of ethylene oxide to afford 3-hydroxypropionaldehyde. The aldehyde is hydrogenated to give 1,3-propanediol. Moreover, the bioconversion of glycerol to 1,3-propanediol is existent in certain bacteria.

Two other routes involve bioprocessing by certain micro-organisms:

Safety

1,3-Propanediol does not appear to pose a significant hazard via inhalation of either the vapor or a vapor/aerosol mixture.[7]

See also

References

  1. ^ "1,3-propanediol - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 16 September 2004. Identification and Related Records. Retrieved 20 October 2011.
  2. ^ Merck Index, 11th Edition, 9629.
  3. ^ Peter Werle, Marcus Morawietz, Stefan Lundmark, Kent Sörensen, Esko Karvinen, Juha Lehtonen "Alcohols, Polyhydric" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, 2006, Weinheim.
  4. ^ a b Carl F. Muska; Carina Alles (2005-05-11). "Biobased 1,3-Propanediol A New Platform Chemical For The 21st Century" (PDF). BREW Symposium.
  5. ^ a b c "Growing Demand for Products Manufactured from DuPont's Bio-Based Propanediol". AZoM.com. 2007-06-12.
  6. ^ H. Biebl; K. Menzel; A.-P. Zeng; W.-D. Deckwer (1999). "Microbial production of 1,3-propanediol". Applied Microbiology and Biotechnology. 52 (3): 289–297. doi:10.1007/s002530051523. PMID 10531640.
  7. ^ Scott RS, Frame SR, Ross PE, Loveless SE, Kennedy GL (2005). "Inhalation toxicity of 1,3-propanediol in the rat". Inhal Toxicol. 17 (9): 487–93. doi:10.1080/08958370590964485. PMID 16020043.

External links

1,3-Dioxane

1,3-Dioxane or m-dioxane is a chemical compound with the molecular formula C4H8O2, the CAS number 505-22-6 , EC Number 208-005-1 and RTECS JG8224000.1,3-Dioxanes and 1,3-dioxolanes are prepared from carbonyl compounds with 1,3-propanediol or 1,2-ethanediol in the presence of Brönsted or Lewis acid catalysts.

1,3-propanediol dehydrogenase

In enzymology, a 1,3-propanediol dehydrogenase (EC 1.1.1.202) is an enzyme that catalyzes the chemical reaction

propane-1,3-diol + NAD+ 3-hydroxypropanal + NADH + H+

Thus, the two substrates of this enzyme are propane-1,3-diol and NAD+, whereas its 3 products are 3-hydroxypropanal, NADH, and H+.

This enzyme belongs to the family of oxidoreductases, specifically those acting on the CH-OH group of donor with NAD+ or NADP+ as acceptor. The systematic name of this enzyme class is propane-1,3-diol:NAD+ 1-oxidoreductase. Other names in common use include 3-hydroxypropionaldehyde reductase, 1,3-PD:NAD+ oxidoreductase, 1,3-propanediol:NAD+ oxidoreductase, and 1,3-propanediol dehydrogenase. This enzyme participates in ether lipid metabolism as a step in glycerolipid biosynthesis.

3-Nitrooxypropanol

3-Nitrooxypropanol, abbreviated 3NOP, is an organic compound with the formula HOCH2CH2CH2ONO2. It is the mononitrate ester of 1,3-propanediol. The compound is an inhibitor of the enzyme methyl coenzyme M reductase (MCR). MCR catalyzes the final step in methanogenesis. When it is fed to ruminants, their methane production is diminished and they gain weight. Ruminants are some of the greatest contributors of methane, a significant greenhouse gas.

Bioconversion

Bioconversion, also known as biotransformation, is the conversion of organic materials, such as plant or animal waste, into usable products or energy sources by biological processes or agents, such as certain microorganisms. One example is the industrial production of cortisone, which one step is the bioconversion of progesterone to 11-alpha-Hydroxyprogesterone by Rhizopus nigricans. Another example is the bioconversion of glycerol to 1,3-propanediol, which is part of scientific research for many decades.

Another example of bioconversion is the conversion of organic materials, such as plant or animal waste, into usable products or energy sources by biological processes or agents, such as certain microorganisms, some detritivores or enzymes.

In the USA, the Bioconversion Science and Technology group performs multidisciplinary R&D for the Department of Energy's (DOE) relevant applications of bioprocessing, especially with biomass. Bioprocessing combines the disciplines of chemical engineering, microbiology and biochemistry. The Group 's primary role is investigation of the use of microorganism, microbial consortia and microbial enzymes in bioenergy research. New cellulosic ethanol conversion processes have enabled the variety and volume of feedstock that can be bioconverted to expand rapidly. Feedstock now includes materials derived from plant or animal waste such as paper, auto-fluff, tires, fabric, construction materials, municipal solid waste (MSW), sludge, sewage, etc.

Bioseparation of 1,3-propanediol

Bioseparation of 1,3-propanediol is a biochemical process for production of 1,3-propanediol (PDO). PDO is an organic compound with many commercial applications. Conventionally, PDO is produced from crude oil products such as propylene or ethylene oxide. In recent years, however, companies such as DuPont are investing in the biological production of PDO using renewable feedstocks such as corn.

Bronopol

Bronopol (INN) is an organic compound that is used as an antimicrobial. It is a white solid although commercial samples appear yellow.

The first cited synthesis of 2-Bromo-2-nitro-1,3-propanediol is 1897 according to Molbase.

Bronopol was invented by The Boots Company PLC in the early 1960s and first applications were as a preservative for pharmaceuticals. Owing to its low mammalian toxicity (at in-use levels) and high activity against bacteria (especially the troublesome Gram-negative species), bronopol became popular as a preservative in many consumer products such as shampoos and cosmetics. It was subsequently adopted as an antimicrobial in other industrial environments such as paper mills, oil exploration and production facilities, as well as cooling water disinfection plants.

C3H8O2

The molecular formula C3H8O2 may refer to:

Dimethoxymethane

2-Methoxyethanol

Propanediol (disambiguation)

1,2-Propanediol (propylene glycol)

1,3-Propanediol (trimethylene glycol)

Clostridium diolis

Clostridium diolis is a bacterium from the genus of Clostridium which has been isolated from decaying straw in Braunschweig in Germany. Clostridium diolis produces 1,3-Propanediol.

Diol

A diol is a chemical compound containing two hydroxyl groups (–OH groups). An aliphatic diol is also called a glycol. This pairing of functional groups is pervasive, and many subcategories have been identified.

The most common industrial diol is ethylene glycol. Examples of diols in which the hydroxyl functional groups are more widely separated include 1,4-butanediol HO−(CH2)4−OH, and propylene-1,3-diol, or beta propylene glycol, HO−CH2−CH2−CH2−OH.

Doug Cameron (engineer)

Douglas Carlyle Cameron (born March 22, 1957) is an American engineer, inventor, and investor. He is a senior managing director for the U.S.-China Green Fund. He is on the board of the Foundation for Food and Agriculture Research (FFAR) and is a technical and business advisor to organizations including the VTT (Finland), and the Center for Bioenergy Innovation (USA).

Expanding Monomers

Expanding Monomers are monomers which are increasing in volume (expanding) during polymerization. They can be added to monomer formulations to counteract the usual volume shrinking (during polymerization) to manufacture products with higher quality and durability. Volume Shrinkage is in first line for the unmeltable thermosets a problem, since those are of fixed shape after polymerization completed.

Green chemistry

Green chemistry, also called sustainable chemistry, is an area of chemistry and chemical engineering focused on the designing of products and processes that minimize the use and generation of hazardous substances. Whereas environmental chemistry focuses on the effects of polluting chemicals on nature, green chemistry focuses on the environmental impact of chemistry, including technological approaches to preventing pollution and reducing consumption of nonrenewable resources.

The overarching goals of green chemistry—namely, more resource-efficient and inherently safer design of molecules, materials, products, and processes—can be pursued in a wide range of contexts.

PDO

PDO can refer to:

In chemistry:

1,3-Propanediol, an industrial chemical

Palladium(II) oxide (PdO)In climate and weather:

The Pacific decadal oscillation, a pattern of climate variationIn compact discs:

Philips and Dupont Optical, a former joint venture between Philips and DuPont for CD manufacturing; also associated with the Compact Disc bronzing issueIn computing:

Panzer Dragoon Orta, a 3D shooter created by Smilebit on the Xbox

PHP Data Objects, a PHP extension that can be used as a database abstraction layer

Portable Distributed Objects, a version of Cocoa's Distributed Objects for remote use

Process Data Object, a type of protocol frame in some fieldbuses, for instance, CANopenIn food and wine:

Protected Designation of Origin, one of three categories stipulated in the Geographical indications and traditional specialities classifications used in the European Union for protected regional foods, and since 2009 for quality winesIn industry, finance and employment:

Paid day off, an eight-hour-long paid time off

Petroleum Development Oman, an Omani oil company, and the part of the Omani capital region where the company is locatedIn mathematics:

Pseudo-differential operator, a concept in mathematical analysisIn sports:

PDO, an advanced statistic in ice hockeyIn administration:

Panchayat Development Officer, the official in charge of an administrative division in a village or gram panchayat (Panchayat Samiti) of India and some other countries of the Indian subcontinentPension distribution office

Pentaerythritol

Pentaerythritol is an organic compound with the formula C(CH2OH)4. Classified as a polyol, it is a white solid. Pentaerythritol is a building block for the synthesis and production of explosives, plastics, paints, appliances, cosmetics, and many other commercial products.

The word pentaerythritol is a portmanteau of penta- in reference to the number of carbon atoms and erythritol, which also possess 4 alcohol groups.

Polytrimethylene terephthalate

Polytrimethylene terephthalate (PTT), is a polyester 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. Similar to polyethylene terephthalate, the PTT is used to make carpet fibers.

PTT's value as a commercial polymer has improved due to more economical and efficient methods to produce 1,3-propanediol in the 1980s by Degussa, via acrolein, and Shell via the hydroformylation of ethylene oxide. DuPont has successfully commercialized the production of this polymer via 1,3-propanediol obtained by fermentation. These developments may allow PTT to effectively compete against PBT and PET, two polyesters that have been far more successful than PTT to date.

Propanediol

Propanediol may refer to either of three isomeric organic chemical compounds:

1,2-Propanediol (Propylene glycol)

2,2-Propanediol (a geminal diol)

1,1-Propanediol (a geminal diol)

1,3-Propanediol (Trimethylene glycol)

Reuterin

Reuterin (3-hydroxypropionaldehyde) is the organic compound with the formula HOCH2CH2CHO. It is a bifunctional molecule, containing both a hydroxy and aldehyde functional groups.

The name reuterin is derived from Lactobacillus reuteri, which produces the compound biosynthetically from glycerol as a broad-spectrum antibiotic. L. reuteri itself is named after the microbiologist Gerhard Reuter, who did early work in distinguishing it as a district species.

Solventogenesis

Solventogenesis is the biochemical production of solvents (usually acetone and butanol) by Clostridium species. It is the second phase of ABE fermentation.

Sorona

Sorona is DuPont's brand of triexta (polytrimethylene terephthalate). It was named and commercialized in 2000. The fibers are claimed to be both soft and extremely stain resistant, while exhibiting high strength and stiffnessSorona is a co-polymer of 1,3-propanediol (obtained by fermentation) and petroleum-derived terephthalic acid (TPA) or dimethyl terephthalate (DMT). Related polymers in this series include polyethylene terephthalate (2GT) and polybutylene terephthalate (polytetramethylene terephthalate) (4GT).The polymer Sorona has been mentioned by J. Craig Venter in interviews as an example of an application of industrial biotechnology. He was quoted as saying, "DuPont argues that Sorona is going to be the first billion-dollar biotech product other than a pharmaceutical." The renewable resource content of Sorona is 37% by weight. DuPont won a 2003 Presidential Green Chemistry Challenge Award for their development of the fermentation process for production of 1,3-propanediol from corn-derived glucose in recombinant Escherichia coli K-12.

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