1,2-Butanediol

Last updated
1,2-Butanediol
1,2-Butanediol.png
1,2-Butanediol-3D-balls-2.png
Names
Preferred IUPAC name
Butane-1,2-diol
Other names
1,2-Dihydroxybutane
α-Butylene glycol
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.008.663 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 209-527-2
PubChem CID
RTECS number
  • EK0380000
UNII
  • InChI=1S/C4H10O2/c1-2-4(6)3-5/h4-6H,2-3H2,1H3 Yes check.svgY
    Key: BMRWNKZVCUKKSR-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C4H10O2/c1-2-4(6)3-5/h4-6H,2-3H2,1H3
    Key: BMRWNKZVCUKKSR-UHFFFAOYAV
  • OCC(O)CC
  • CCC(CO)O
Properties [1]
C4H10O2
Molar mass 90.121 g/mol
Density 1.0023 g/cm3 (20 °C)
Melting point −50 °C (−58 °F; 223 K) [note 1]
Boiling point 195 to 196.9 °C (383.0 to 386.4 °F; 468.1 to 470.0 K) (96.5 °C at 10 mmHg)
miscible
Solubility soluble in ethanol, acetone; sparingly soluble in esters and ethers; insoluble in hydrocarbons
1.4378 (20 °C)
Viscosity 7.3 mPa·s (20 °C)
Thermochemistry
−532.8 kJ/mol [2]
−2479 kJ/mol
Hazards [3]
Flash point 90 °C (194 °F; 363 K)
Safety data sheet (SDS) ICSC 0395
Related compounds
Related butanediols
1,3-Butanediol
1,4-Butanediol
2,3-Butanediol
Related compounds
 Ethylene glycol
Propylene glycol
2-Hydroxybutyraldehyde
2-Hydroxybutyric acid
α-Ketobutyric acid
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

1,2-Butanediol is the organic compound with the formula HOCH2(HO)CHCH2CH3. It is classified as a vic-diol (glycol). It is chiral, although typically it is encountered as the racemic mixture. It is a colorless liquid.

Contents

Preparation

This diol was first described by Charles-Adolphe Wurtz in 1859. [4]

It is produced industrially by hydration of 1,2-epoxybutane. [5] [6]

Industrial synthesis of 1,2-butanediol.svg

This process requires a ten- to twenty-fold excess of water to suppress the formation of polyethers. Depending on the amount of excess water, the selectivity varies from 70 to 92%. [7] Sulfuric acid or strongly acidic ion exchange resins may be used as catalysts, which allows the reaction to occur under 160 °C and at slightly above atmospheric pressure.

1,2-Butanediol is a byproduct of the production of 1,4-butanediol from butadiene. [8] It is also a byproduct of the catalytic hydrocracking of starches and sugars such as sorbitol to ethylene glycol and propylene glycol. [9]

It can also be obtained from the dihydroxylation of but-1-ene by OsO4.

Applications

It has been patented for the production of polyester resins and plasticizers. [6] [8] It is a potential feedstock for the industrial production of α-ketobutyric acid, a precursor to some amino acids. [10]

Safety

The LD50 (rats, oral) is 16g/kg. [5]

Notes

  1. ↑ The value of −50 °C for the melting point is taken from Ullmann's Encyclopedia of Industrial Chemistry and used by the Hazardous Substances Data Bank and the OECD Screening Information Dataset. Other reported values of the melting point range from −114 °C to −30 °C.

Related Research Articles

Ethylene Chemical compound

Ethylene (IUPAC name: ethene) is a hydrocarbon which has the formula C
2H
4 or H2C=CH2. It is a colorless flammable gas with a faint "sweet and musky" odor when pure. It is the simplest alkene (a hydrocarbon with carbon-carbon double bonds).

Ethylene glycol Chemical compound

Ethylene glycol is an organic compound with the formula (CH2OH)2. It is mainly used for two purposes, as a raw material in the manufacture of polyester fibers and for antifreeze formulations. It is an odorless, colorless, sweet-tasting, flammable, viscous liquid. Ethylene glycol is toxic to humans in high concentrations.

In chemistry, a hydration reaction is a chemical reaction in which a substance combines with water. In organic chemistry, water is added to an unsaturated substrate, which is usually an alkene or an alkyne. This type of reaction is employed industrially to produce ethanol, isopropanol, and butan-2-ol.

Tetrahydrofuran Chemical compound

Tetrahydrofuran (THF), or oxolane, is an organic compound with the formula (CH2)4O. The compound is classified as heterocyclic compound, specifically a cyclic ether. It is a colorless, water-miscible organic liquid with low viscosity. It is mainly used as a precursor to polymers. Being polar and having a wide liquid range, THF is a versatile solvent.

Cumene process Industrial process

The cumene process is an industrial process for synthesizing phenol and acetone from benzene and propylene. The term stems from cumene, the intermediate material during the process. It was invented by R. Ūdris and P. Sergeyev in 1942 (USSR)., and independently by Heinrich Hock in 1944

Epoxide

An epoxide is a cyclic ether with a three-atom ring. This ring approximates an equilateral triangle, which makes it strained, and hence highly reactive, more so than other ethers. They are produced on a large scale for many applications. In general, low molecular weight epoxides are colourless and nonpolar, and often volatile.

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

Propylene oxide Chemical compound

Propylene oxide is an acutely toxic and carcinogenic organic compound with the molecular formula CH3CHCH2O. This colorless volatile liquid with an odor similar to ether, is produced on a large scale industrially. Its major application is its use for the production of polyether polyols for use in making polyurethane plastics. It is a chiral epoxide, although it is commonly used as a racemic mixture.

Dimethoxyethane Chemical compound

Dimethoxyethane, also known as glyme, monoglyme, dimethyl glycol, ethylene glycol dimethyl ether, dimethyl cellosolve, and DME, is a colorless, aprotic, and liquid ether that is used as a solvent, especially in batteries. Dimethoxyethane is miscible with water.

Dicyclopentadiene Chemical compound

Dicyclopentadiene, abbreviated DCPD, is a chemical compound with formula C10H12. At room temperature, it is a white brittle wax, although lower purity samples can be straw coloured liquids. The pure material smells somewhat of soy wax or camphor, with less pure samples possessing a stronger acrid odor. Its energy density is 10,975 Wh/l. Dicyclopentadiene is a co-produced in large quantities in the steam cracking of naphtha and gas oils to ethylene. The major use is in resins, particularly, unsaturated polyester resins. It is also used in inks, adhesives, and paints.

In organic chemistry a halohydrin is a functional group in which a halogen and a hydroxyl are bonded to adjacent carbon atoms, which otherwise bear only hydrogen or hydrocarbyl groups. The term only applies to saturated motifs, as such compounds like 2-chlorophenol would not normally be considered halohydrins. Megatons of some chlorohydrins, e.g. propylene chlorohydrin, are produced annually as precursors to polymers.

Diethylenetriamine Chemical compound

Diethylenetriamine (abbreviated Dien or DETA) and also known as 2,2’-Iminodi(ethylamine)) is an organic compound with the formula HN(CH2CH2NH2)2. This colourless hygroscopic liquid is soluble in water and polar organic solvents, but not simple hydrocarbons. Diethylenetriamine is structural analogue of diethylene glycol. Its chemical properties resemble those for ethylene diamine, and it has similar uses. It is a weak base and its aqueous solution is alkaline. DETA is a byproduct of the production of ethylenediamine from ethylene dichloride.

Polyester Category of polymers, in which the monomers are joined together by ester links.

Polyester is a category of polymers that contain the ester functional group in every repeat unit of their main chain. As a specific material, it most commonly refers to a type called polyethylene terephthalate (PET). Polyesters include naturally occurring chemicals, such as in plants and insects, as well as synthetics such as polybutyrate. Natural polyesters and a few synthetic ones are biodegradable, but most synthetic polyesters are not. Synthetic polyesters are used extensively in clothing.

1,3-Propanediol is the organic compound with the formula CH2(CH2OH)2. This 3-carbon diol is a colorless viscous liquid that is miscible with water.

1,4-Butynediol Chemical compound

1,4-Butynediol is an organic compound that is an alkyne and a diol. It is a colourless, hygroscopic solid that is soluble in water and polar organic solvents. It is a commercially significant compound in its own right and as a precursor to other products.

1,8-Octanediol, also known as octamethylene glycol, is a diol with the molecular formula HO(CH2)8OH. 1,8-Octanediol is a white solid. It is produced by hydrogenation of esters of suberic acid.

2,3-Butanediol Chemical compound

2,3-Butanediol is the organic compound with the formula (CH3CHOH)2. It is classified as a vic-diol (glycol). It exists as three stereoisomers, a chiral pair and the meso isomer. All are colorless liquids. Applications include precursors to various plastics and pesticides.

1,5-Pentanediol is the organic compound with the formula HOCH2CH2CH2CH2CH2OH. Like other diols, this viscous colourless liquid is used as plasticizer and also forms polyesters that are used as emulsifying agents and resin intermediates.

1,3-Butanediol Chemical compound

1,3-Butanediol is an organic compound with the formula CH3CH(OH)CH2CH2OH. With two alcohol functional groups, the molecule is classified as a diol. The compound is a colorless, very bitter, water-soluble liquid. It is one of four common structural isomers of butanediol.

Cyclohexanedimethanol Chemical compound

Cyclohexanedimethanol (CHDM) is a mixture of isomeric organic compounds with formula C6H10(CH2OH)2. It is a colorless low-melting solid used in the production of polyester resins. Commercial samples consist of a mixture of cis and trans isomers. It is a di-substituted derivative of cyclohexane and is classified as a diol, meaning that it has two OH functional groups. Commercial CHDM typically has a cis/trans ratio of 30:70.

References

  1. ↑ Weast, Robert C., ed. (1981). CRC Handbook of Chemistry and Physics (62nd ed.). Boca Raton, FL: CRC Press. p. C-190. ISBN   0-8493-0462-8..
  2. ↑ Moureu, H.; Dode, M. (1937), "Chaleurs de formation de l'oxyde d'ethylene, de l'ethanediol et de quelques homologues", Bull. Soc. Chim. Fr. , 4: 637–47.
  3. ↑ 1,2-Butanediol, International Chemical Safety Card 0395, Geneva: International Programme on Chemical Safety, March 1996.
  4. ↑ Wurtz, A. (1859), "Mémoire sur les glycols ou alcools diatomique" [Dissertation on glycols, or diatomic alcohols], Ann. Chim. Phys. , 55: 400.
  5. 1 2 "Butanediols, Butenediol, and Butynediol". Ullmann's Encyclopedia of Industrial Chemistry . Weinheim: Wiley-VCH. 2005. doi:10.1002/14356007.a04_455.
  6. 1 2 1,2-Butanediol (PDF), SIDS Initial Assessment Report, Geneva: United Nations Environment Programme, February 1995.
  7. ↑ Gräfje, Heinz; Körnig, Wolfgang; Weitz, Hans-Martin; Reiß, Wolfgang; Steffan, Guido; Diehl, Herbert; Bosche, Horst; Schneider, Kurt; Kieczka, Heinz (2019-07-23), "Butanediols, Butenediol, and Butynediol", Ullmann's Encyclopedia of Industrial Chemistry, Weinheim, Germany: Wiley-VCH Verlag GmbH & Co. KGaA, pp. 1–12, doi:10.1002/14356007.a04_455.pub2, ISBN   978-3-527-30673-2 , retrieved 2022-02-18
  8. 1 2 US 4596886,Hasegawa, Ryuichi&Hayashi, Kohji,"Polyester containing impure 1,2-butanediol",published 1986-06-24, assigned to Mitsubishi Monsanto Chemical Company.
  9. ↑ US 4966658,Berg, Lloyd,"Recovery of ethylene glycol from butanediol isomers by azeotropic distillation",published 1990-10-30. US 5423955,Berg, Lloyd,"Separation of propylene glycol from 1,2-butanediol by azeotropic distillation",published 1995-06-13.
  10. ↑ US 5155263,Imanari, Makoto; Iwane, Hiroshi& Suzuki, Masashiet al.,"Process for preparing α-ketobutyric acid",published 1992-10-13, assigned to Mitsubishi Petrochemical Co., Ltd..
This page is based on this Wikipedia article
Text is available under the CC BY-SA 4.0 license; additional terms may apply.
Images, videos and audio are available under their respective licenses.