1,2-Butanediol

1,2-Butanediol
Names
	IUPAC name Butane-1,2-diol
	Other names 1,2-Dihydroxybutane; α-Butylene glycol
Identifiers
CAS Number	584-03-2 ; 40348-66-1 (R) ; 73522-17-5 (S) ;
3D model (JSmol)	Interactive image; Interactive image;
ChEBI	CHEBI:52682 ;
ChemSpider	10948 ;
ECHA InfoCard	100.008.663
EC Number	209-527-2;
PubChem CID	11429;
RTECS number	EK0380000;
UNII	RUN0H01QEU ;
CompTox Dashboard (EPA)	DTXSID6040375 ;
	InChI InChI=1S/C4H10O2/c1-2-4(6)3-5/h4-6H,2-3H2,1H3 Key: BMRWNKZVCUKKSR-UHFFFAOYSA-N ; InChI=1/C4H10O2/c1-2-4(6)3-5/h4-6H,2-3H2,1H3 Key: BMRWNKZVCUKKSR-UHFFFAOYAV;
	SMILES OCC(O)CC; CCC(CO)O;
Properties[1]
Chemical formula	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)
Solubility in water	miscible
Solubility	soluble in ethanol, acetone; sparingly soluble in esters and ethers; insoluble in hydrocarbons
Refractive index (nD)	1.4378 (20 °C)
Viscosity	7.3 mPa s (20 °C)
Thermochemistry
Std enthalpy of; formation (ΔfH⦵298)	−532.8 kJ/mol [2]
Std enthalpy of; combustion (ΔcH⦵298)	−2479 kJ/mol
Hazards[3]
Safety data sheet	ICSC 0395
Flash point	90 °C (194 °F; 363 K)
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).
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	Infobox references

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.

Preparation

It is produced industrially by hydration of 1,2-epoxybutane.[4][5]

1,2-Butanediol is a byproduct of the production of 1,4-butanediol from butadiene,[6] It is also a byproduct of the catalytic hydrocracking of starches and sugars such as sorbitol to ethylene glycol and propylene glycol.[7]

This diol was first described by Charles-Adolphe Wurtz in 1859.[8]

Applications

It has been patented for the production of polyester resins and plasticizers.[5][6] It is a potential feedstock for the industrial production of α-ketobutyric acid, a precursor to some amino acids.[9]

Safety

The LD50 (rats, oral) is 16g/kg.[4]

Notes

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.

References

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..
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.
1,2-Butanediol, International Chemical Safety Card 0395, Geneva: International Programme on Chemical Safety, March 1996.
"Butanediols, Butenediol, and Butynediol". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. 2005. doi:10.1002/14356007.a04_455.
1,2-Butanediol (PDF), SIDS Initial Assessment Report, Geneva: United Nations Environment Programme, February 1995.
US 4596886, Hasegawa, Ryuichi & Kohji Hayashi, "Polyester containing impure 1,2-butanediol", assigned to Mitsubishi Monsanto Chemical Company.
US 4966658, Berg, Lloyd, "Recovery of ethylene glycol from butanediol isomers by azeotropic distillation". US 5423955, Berg, Lloyd, "Separation of propylene glycol from 1,2-butanediol by azeotropic distillation".
Wurtz, A. (1859), Ann. Chim. Phys., 55: 400CS1 maint: untitled periodical (link).
US 5155263, Imanari, Makoto; Hiroshi Iwane & Masashi Suzuki et al., "Process for preparing α-ketobutyric acid", assigned to Mitsubishi Petrochemical Co., Ltd..

External links

International Chemical Safety Card 03
SIDS Initial Assessment Report for 1,2-Butanediol from the Organisation for Economic Co-operation and Development (OECD)

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[2] 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.

[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..

[3] 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.

[ICSC-4] 1,2-Butanediol, International Chemical Safety Card 0395, Geneva: International Programme on Chemical Safety, March 1996.

[Ullmann-5] "Butanediols, Butenediol, and Butynediol". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. 2005. doi:10.1002/14356007.a04_455.

[SIDS-6] 1,2-Butanediol (PDF), SIDS Initial Assessment Report, Geneva: United Nations Environment Programme, February 1995.

[US4596886-7] US 4596886, Hasegawa, Ryuichi & Kohji Hayashi, "Polyester containing impure 1,2-butanediol", assigned to Mitsubishi Monsanto Chemical Company.

[8] US 4966658, Berg, Lloyd, "Recovery of ethylene glycol from butanediol isomers by azeotropic distillation". US 5423955, Berg, Lloyd, "Separation of propylene glycol from 1,2-butanediol by azeotropic distillation".

[9] Wurtz, A. (1859), Ann. Chim. Phys., 55: 400CS1 maint: untitled periodical (link).

[10] US 5155263, Imanari, Makoto; Hiroshi Iwane & Masashi Suzuki et al., "Process for preparing α-ketobutyric acid", assigned to Mitsubishi Petrochemical Co., Ltd..