1,2-Butanediol

changed changed 477203212 1,2-Butanediol 1,2-Butanediol.png Molecular formula of 1,2-Butanediol 1,2-Butanediol-3D-balls-2.png Butanediol molecule Butane-1,2-diol 1,2-Dihydroxybutaneα-Butylene glycol 1/C4H10O2/c1-2-4(6)3-5/h4-6H,2-3H2,1H3 correct chemspider 1S/C4H10O2/c1-2-4(6)3-5/h4-6H,2-3H2,1H3 BMRWNKZVCUKKSR-UHFFFAOYAV correct chemspider BMRWNKZVCUKKSR-UHFFFAOYSA-N correct FDA RUN0H01QEU OCC(O)CC CCC(CO)O 584-03-2 correct CAS changed ?? 40348-66-1 (R) changed ?? 73522-17-5 (S) 209-527-2 correct chemspider correct EBI 52682 10948 EK0380000 11429 C-190. C4H10O2 90.121 g/mol 1.0023 g/cm3 (20 °C) −50 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. 195 to 196.9 (96.5 °C at 10 mmHg) miscible soluble in ethanol, acetone; sparingly soluble in esters and ethers; insoluble in hydrocarbons 1.4378 (20 °C) 7.3 mPa·s (20 °C) −532.8 kJ/mol Moureu H. Dode M. Chaleurs de formation de l'oxyde d'ethylene, de l'ethanediol et de quelques homologues Bull. Soc. Chim. Fr. 1937 4 637–47. −2479 kJ/mol 03 95 1,2-Butanediol March 1996. ICSC 0395 90 1,3-Butanediol1,4-Butanediol2,3-Butanediol butanediols Ethylene glycolPropylene glycol2-Hydroxybutyraldehyde2-Hydroxybutyric acidα-Ketobutyric acid 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.Wurtz A. Mémoire sur les glycols ou alcools diatomique https://gallica.bnf.fr/ark:/12148/bpt6k6567326h/f403.item Ann. Chim. Phys. 55 400 1859 Dissertation on glycols, or diatomic alcohols Charles-Adolphe Wurtz. It is produced industrially by hydration of 1,2-epoxybutane. Butanediols, Butenediol, and Butynediol Heinz Gräfje et al. 2005 10.1002/14356007.a04_455584032 1,2-Butanediol February 1995. 378x378px 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%.Gräfje Heinz Butanediols, Butenediol, and Butynediol 2019-07-23 https://onlinelibrary.wiley.com/doi/10.1002/14356007.a04_455.pub2 Ullmann's Encyclopedia of Industrial Chemistry 1–12 Weinheim, Germany Wiley-VCH Verlag GmbH & Co. KGaA en 10.1002/14356007.a04_455.pub2 978-3-527-30673-2 2022-02-18 Körnig Wolfgang Weitz Hans-Martin Reiß Wolfgang Steffan Guido Diehl Herbert Bosche Horst Schneider Kurt Kieczka Heinz subscription 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. Hasegawa Ryuichi Hayashi Kohji Mitsubishi Monsanto Chemical Company Polyester containing impure 1,2-butanediol US 4596886 1986-06-24. It is also a byproduct of the catalytic hydrocracking of starches and sugars such as sorbitol to ethylene glycol and propylene glycol. Berg Lloyd Recovery of ethylene glycol from butanediol isomers by azeotropic distillation US 4966658 1990-10-30. Berg Lloyd Separation of propylene glycol from 1,2-butanediol by azeotropic distillation US 5423955 1995-06-13. 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. It is a potential feedstock for the industrial production of α-ketobutyric acid, a precursor to some amino acids. Imanari Makoto Iwane Hiroshi Suzuki Masashi Suzuki Naoki Mitsubishi Petrochemical Co., Ltd. Process for preparing α-ketobutyric acid US 5155263 1992-10-13. Safety The (rats, oral) is 16g/kg. Notes "note" References External links 03 95 584032 1,2-Butanediol February 1995 Category:Alkanediols Category:Vicinal diols Category:Substances discovered in the 19th century Category:Butane