1,3-Butanediol

Last updated
1,3-Butanediol
1,3-Butanediol.png
Ball and stick model of 1,3-butanediol (S) 1,3-Butanediol-3D-balls.png
Ball and stick model of 1,3-butanediol (S)
Spacefill model of 1,3-butanediol (S) 1,3-Butanediol-3D-spacefill.png
Spacefill model of 1,3-butanediol (S)
Names
Preferred IUPAC name
Butane-1,3-diol
Other names
1,3-butylene glycol, butane-1,3-diol, or 1,3-dihydroxybutane
Identifiers
3D model (JSmol)
1731276

1718944 (R)
1718943 (S)

ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.003.209 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 203-529-7
E number E1502 (additional chemicals)
2409

2493173 (R)
1994384 (S)

KEGG
MeSH 1,3-Butylene+glycol
PubChem CID
RTECS number
  • EK0440000
UNII
  • InChI=1S/C4H10O2/c1-4(6)2-3-5/h4-6H,2-3H2,1H3 X mark.svgN
    Key: PUPZLCDOIYMWBV-UHFFFAOYSA-N X mark.svgN
  • CC(O)CCO
Properties
C4H10O2
Molar mass 90.122 g·mol−1
AppearanceColourless liquid
Density 1.0053 g cm−3
Melting point −50 °C (−58 °F; 223 K)
Boiling point 204 to 210 °C; 399 to 410 °F; 477 to 483 K
1 kg dm−3
log P −0.74
Vapor pressure 8 Pa (at 20 °C)
1.44
Thermochemistry
Std molar
entropy (S⦵298)
227.2 J K−1 mol−1
−501 kJ mol−1
−2.5022 MJ mol−1
Hazards
GHS labelling:
GHS-pictogram-exclam.svg
Warning
H319, H413
P305+P351+P338
NFPA 704 (fire diamond)
1
1
0
Flash point 108 °C (226 °F; 381 K)
394 °C (741 °F; 667 K)
Related compounds
Related butanediol
 1,2-Butanediol

1,4-Butanediol
2,3-Butanediol

Related compounds
 2-Methylpentane
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 ?)

1,3-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 also chiral but most studies do not distiguigh the enantiomers. The compound is a colorless, bittersweet, water-soluble liquid. It is one of four common structural isomers of butanediol. [1] [2] It is used in flavoring.

Contents

Production and uses

Hydrogenation of 3-hydroxybutanal gives 1,3-butanediol: [3]

CH3CH(OH)CH2CHO + H2 → CH3CH(OH)CH2CH2OH

Dehydration of 1,3-butanediol gives 1,3-butadiene:

CH3CH(OH)CH2CH2OH → CH2=CH-CH=CH2 + 2 H2O

Occurrence

1,3-Butanediol is used as a hypoglycaemic agent.

1,3-Butanediol has been detected in green bell peppers, orange bell peppers, pepper ( Capsicum annuum ), red bell peppers, and yellow bell peppers. [4] 1,3 Butanediol, also referred to as 1,3-Butylene glycol, maintains FDA GRAS status as a flavor molecule. [5]

Related Research Articles

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.

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.

In chemistry, a dehydration reaction is a chemical reaction that involves the loss of water from the reacting molecule or ion. Dehydration reactions are common processes, the reverse of a hydration reaction.

<span class="mw-page-title-main">Dimethoxyethane</span> 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.

2-Chloroethanol (also called ethylene chlorohydrin or glycol chlorohydrin) is an organic chemical compound with the chemical formula HOCH2CH2Cl and the simplest beta-halohydrin (chlorohydrin). This colorless liquid has a pleasant ether-like odor. It is miscible with water. The molecule is bifunctional, consisting of both an alkyl chloride and an alcohol functional group.

<span class="mw-page-title-main">1-Butene</span> Chemical compound

But-1-ene (or 1-butylene) is the organic compound with the formula CH3CH2CH=CH2. It is a colorless gas that is easily condensed to give a colorless liquid. It is classified as a linear alpha-olefin. It is one of the isomers of butene (butylene). It is a precursor to diverse products.

Pelargonic acid, also called nonanoic acid, is an organic compound with structural formula CH3(CH2)7CO2H. It is a nine-carbon fatty acid. Nonanoic acid is a colorless oily liquid with an unpleasant, rancid odor. It is nearly insoluble in water, but very soluble in organic solvents. The esters and salts of pelargonic acid are called pelargonates or nonanoates.

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.

<span class="mw-page-title-main">1,4-Butynediol</span> 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.

Undecylenic acid is an organic compound with the formula CH2=CH(CH2)8CO2H. It is an unsaturated fatty acid. It is a colorless oil. Undecylenic acid is mainly used for the production of Nylon-11 and in the treatment of fungal infections of the skin, but it is also a precursor in the manufacture of many pharmaceuticals, personal hygiene products, cosmetics, and perfumes. Salts and esters of undecylenic acid are known as undecylenates.

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.

Methanediol, also known as formaldehyde monohydrate or methylene glycol, is an organic compound with chemical formula CH2(OH)2. It is the simplest geminal diol. In aqueous solutions it coexists with oligomers. The compound is closely related and convertible to the industrially significant derivatives paraformaldehyde, formaldehyde, and 1,3,5-trioxane.

<span class="mw-page-title-main">2,3-Butanediol</span> 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.

3-Hydroxybutanal (acetaldol) is an organic compound with the formula CH3CH(OH)CH2CHO. It is classified as an aldol, formally the product of the dimerization of acetaldehyde. A colorless liquid, it is a versatile and valuable intermediate with diverse impacts. The compound is chiral although this aspect is not often exploited.

<span class="mw-page-title-main">1,2-Butanediol</span> Chemical compound

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.

<span class="mw-page-title-main">2-Methyl-2,4-pentanediol</span> Chemical compound

2-Methyl-2,4-pentanediol (MPD) is an organic compound with the formula (CH3)2C(OH)CH2CH(OH)CH3. This colourless liquid is a chiral diol. It is produced industrially from diacetone alcohol by hydrogenation. Total European and USA production was 15000 tonnes in 2000.

<span class="mw-page-title-main">1-Octanol</span> Chemical compound

1-Octanol, also known as octan-1-ol, is the organic compound with the molecular formula CH3(CH2)7OH. It is a fatty alcohol. Many other isomers are also known generically as octanols. 1-Octanol is manufactured for the synthesis of esters for use in perfumes and flavorings. It has a pungent odor. Esters of octanol, such as octyl acetate, occur as components of essential oils. It is used to evaluate the lipophilicity of pharmaceutical products.

<span class="mw-page-title-main">2,3-Epoxybutane</span> Chemical compound

2,3-Epoxybutane is an organic compound with the formula CH3CH(O)CHCH3. It is an epoxide. The compound exists as three stereoisomers, a pair of enantiomers and the meso isomer. All are colorless liquids.

<span class="mw-page-title-main">Hydroxypivaldehyde</span> Chemical compound

Hydroxypivaldehyde is the organic compound with the formula HOCH2(CH3)2CCHO. A colorless liquid, it is produced by condensation of formaldehyde and isobutyraldehyde:

References

  1. ↑ Gräfje, Heinz; Körnig, Wolfgang; Weitz, Hans-Martin; Reiß, Wolfgang; Steffan, Guido; Diehl, Herbert; Bosche, Horst; Schneider, Kurt; Kieczka (2000). "Butanediols, Butenediol, and Butynediol". Ullmann's Encyclopedia of Industrial Chemistry . Weinheim: Wiley-VCH. doi:10.1002/14356007.a04_455.
  2. ↑ Parchem, fine & specialty chemicals. "1,3 Butylene Glycol".
  3. ↑ Kohlpaintner, Christian; Schulte, Markus; Falbe, Jürgen; Lappe, Peter; Weber, Jürgen (2008). "Aldehydes, Aliphatic". Ullmann's Encyclopedia of Industrial Chemistry . Weinheim: Wiley-VCH. doi:10.1002/14356007.a01_321.pub2.
  4. ↑ "Human Metabolome Database: Showing metabocard for 1,3-Butanediol (HMDB0031320)". hmdb.ca. Retrieved 2022-05-12.
  5. ↑ "FDA GRAS for 1,3 Butanediol for flavoring CFR - Code of Federal Regulations Title 21". www.accessdata.fda.gov. Retrieved 2022-05-12.
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