1,2-Butanediol
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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
This diol was first described by Charles-Adolphe Wurtz in 1859.[2]
It is produced industrially by hydration of 1,2-epoxybutane.[3][4]
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%.[5] 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.[6] It is also a byproduct of the catalytic hydrocracking of starches and sugars such as sorbitol to ethylene glycol and propylene glycol.[7]
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.[4][6] It is a potential feedstock for the industrial production of α-ketobutyric acid, a precursor to some amino acids.[8]
Safety
The LD50 (rats, oral) is 16g/kg.[3]
Notes
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References
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- ↑ a b <templatestyles src="Citation/styles.css"/>Template:Citation/make link, Hasegawa, Ryuichi & Hayashi, Kohji, "Polyester containing impure 1,2-butanediol", published Script error: No such module "auto date formatter"., assigned to Mitsubishi Monsanto Chemical CompanyScript error: No such module "Check for unknown parameters"..
- ↑ <templatestyles src="Citation/styles.css"/>Template:Citation/make link, Berg, Lloyd, "Recovery of ethylene glycol from butanediol isomers by azeotropic distillation", published Script error: No such module "auto date formatter".Script error: No such module "Check for unknown parameters".. <templatestyles src="Citation/styles.css"/>Template:Citation/make link, Berg, Lloyd, "Separation of propylene glycol from 1,2-butanediol by azeotropic distillation", published Script error: No such module "auto date formatter".Script error: No such module "Check for unknown parameters"..
- ↑ <templatestyles src="Citation/styles.css"/>Template:Citation/make link, Imanari, Makoto; Iwane, Hiroshi & Suzuki, Masashi et al., "Process for preparing α-ketobutyric acid", published Script error: No such module "auto date formatter"., assigned to Mitsubishi Petrochemical Co., Ltd.Script error: No such module "Check for unknown parameters"..
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