2-Butanol

Secondary alcohol CH3CH(OH)CH2CH3 changed 47721284 2-butanol Line-Structure.svg skin-invert correct ?? Skeletal formula of 2-butanol Butan-2-ol 2-butanol - Compound Summary https://pubchem.ncbi.nlm.nih.gov/compound/6568 PubChem Compound National Center for Biotechnology Information 12 October 2011 USA 26 March 2005 Identification and Related Records sec-Butanol Nomenclature of Organic Chemistry (The IUPAC 'Blue Book'), Sections A, B, C, D, E, F, and H 1979 Pergamon Press Oxford Alcohols Rule C-201.1 Designations such as isopropanol, sec-butanol, and tert-butanol are incorrect because there are no hydrocarbons isopropane, sec-butane, and tert-butane to which the suffix "-ol" can be added; such names should be abandoned. Isopropyl alcohol, sec-butyl alcohol, and tert-butyl alcohol are, however, permissible (see Rule C-201.3) because the radicals isopropyl, sec-butyl, and tert-butyl do existsec-Butyl alcohol2-Butanol2-Butyl alcohol 78-92-2 correct CAS correct ?? 14898-79-4 (R) correct ?? 4221-99-2 (S) s-BuOHsBuOHsBuOH correct FDA 0TUL3ENK62 correct FDA DLH38K423J (R) correct FDA 69KXU5NDTO (S) 6568 84682 (R) 444683 (S) 6320 correct chemspider 76392 correct chemspider (R) 392543 correct chemspider (S) 201-158-5 1120 DB02606 correct drugbank 2-butanol 35687 correct EBI 45462 correct EBI EO1750000 773649 1718764 (R) 1718763 (S) 1686 396584 (R) 25655 (S) CCC(C)O CC[C@@H](C)O (R) CC[C@H](C)O (S) 1S/C4H10O/c1-3-4(2)5/h4-5H,3H2,1-2H3 correct chemspider BTANRVKWQNVYAZ-UHFFFAOYSA-N correct chemspider 4 10 1 0.808 g cm−3 158 371 to 373 390 g/L Alger Donald B. The water solubility of butan-2-ol: A widespread error Journal of Chemical Education November 1991 68 11 10.1021/ed068p939.1 939 1991JChEd..68..939A 1.67 kPa (at 20 °C) 0.683 17.6 Serjeant, E.P., Dempsey B.; Ionisation Constants of Organic Acids in Aqueous Solution. International Union of Pure and Applied Chemistry (IUPAC). IUPAC Chemical Data Series No. 23, 1979. New York, New York: Pergamon Press, Inc., p. 989 1.3978 (at 20 °C) -5.7683 -5 cm3 mol−1 −343.3 to −342.1 kJ mol−1 −2.6611 to −2.6601 MJ mol−1 213.1 J K−1 mol−1 197.1 J K−1 mol−1 inchem.org flame exclamation mark WARNING 226 319 335 336 261 305+351+338 1 3 0 22 to 27 405 1.7–9.8% TWA 150 ppm (450 mg/m3)0077 TWA 100 ppm (305 mg/m3) ST 150 ppm (455 mg/m3) 2000 ppm 16,000 ppm (rat, 4 hr)10,670 ppm (mouse, 3.75 hr)16,000 ppm (mouse, 2.67 hr) butanols n-ButanolIsobutanoltert-Butanol Butanone Butan-2-ol, or sec-butanol, is an organic compound with formula CH3CH(OH)CH2CH3. Its structural isomers are 1-butanol, isobutanol, and tert-butanol. 2-Butanol is chiral and thus can be obtained as either of two stereoisomers designated as (R)-(−)-butan-2-ol and (S)-(+)-butan-2-ol. It is normally encountered as a 1:1 mixture of the two stereoisomers — a racemic mixture. This secondary alcohol is a flammable, colorless liquid that is soluble in three parts water and completely miscible with organic solvents. It is produced on a large scale, primarily as a precursor to the industrial solvent methyl ethyl ketone. 160px160px160px160px(R)-(−)-2-butanol(S)-(+)-2-butanol Manufacture and applications Butan-2-ol is manufactured industrially by the hydration of 1-butene or 2-butene: 300px Sulfuric acid is used as a catalyst for this conversion. Heinz-Dieter Hahn Georg Dämbkes Norbert Rupprich Butanols 2005. In the laboratory it can be prepared via Grignard reaction by reacting ethylmagnesium bromide with acetaldehyde in dried diethyl ether or tetrahydrofuran. Although some butan-2-ol is used as a solute, it is mainly converted to butanone (methyl ethyl ketone, MEK), an important industrial solvent and found in many domestic cleaning agents and paint removers. Though most paint removers have ceased using MEK in their products due to health concerns and new laws. Volatile esters of butan-2-ol have pleasant aromas and are used in small amounts as perfumes or in artificial flavors. Solubility The listed solubility of butan-2-ol is often incorrect, including some of the most well-known references such as the Merck Index, the CRC Handbook of Chemistry and Physics, and Lange's Handbook of Chemistry. Even the International Programme on Chemical Safety lists the wrong solubility. This widespread error originated because of Beilstein's Handbuch der Organischen Chemie (Handbook of Organic Chemistry). This work cites a false solubility of 12.5 g/100 g water. Many other sources used this solubility, which has snowballed into a widespread error in the industrial world. The correct data (35.0 g/100 g at 20 °C, 29 g/100 g at 25 °C, and 22 g/100 g at 30 °C) were first published in 1886 by Alexejew and then similar data was reported by other scientists including Dolgolenko and Dryer in 1907 and 1913, respectively. Precautions Like other butanols, butan-2-ol has low acute toxicity. The is 4400 mg/kg (rat, oral). Several explosions have been reportedDoyle, R. R. 2-Butanol safety warning 1986 63 2 186 Journal of Chemical Education 10.1021/ed063p186.2 1986JChEd..63..186D free Peterson Donald Letters: Explosion of 2-butanol Chemical & Engineering News 11 May 1981 59 19 3 10.1021/cen-v059n019.p002 free Watkins Kenneth W. Demonstration hazard Journal of Chemical Education May 1984 61 5 476 10.1021/ed061p476.3 1984JChEd..61..476W free during the conventional distillation of 2-butanol, apparently due to the buildup of peroxides with the boiling point higher than that of pure alcohol (and therefore concentrating in the still pot during distillation). As alcohols, unlike ethers, are not widely known to be capable of forming peroxide impurities, the danger is likely to be overlooked. 2-Butanol is in Class B Peroxide Forming ChemicalsClassification List of Peroxide Forming Chemicals https://ehs.ucsc.edu/lab-safety-manual/specialty-chemicals/peroxide-formers-list.html ehs.ucsc.edu 2020-04-19 2022-12-05 https://web.archive.org/web/20221205150225/https://ehs.ucsc.edu/lab-safety-manual/specialty-chemicals/peroxide-formers-list.html dead References External links 0112 01 0077 65 Butanols: four isomers 004 4 2-Butanol 1987 92-4-154465-1 Category:Alkanols Category:Alcohol solvents Category:Secondary alcohols Category:Sec-Butyl compounds