1,6-hexanediol
Structural formula | ||||||||||||||||||||||
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General | ||||||||||||||||||||||
Surname | 1,6-hexanediol | |||||||||||||||||||||
other names |
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Molecular formula | C 6 H 14 O 2 | |||||||||||||||||||||
Brief description |
colorless crystals |
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properties | ||||||||||||||||||||||
Molar mass | 118.18 g mol −1 | |||||||||||||||||||||
Physical state |
firmly |
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density |
0.96 g cm −3 (20 ° C) |
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Melting point |
45 ° C |
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boiling point |
250 ° C |
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Vapor pressure |
<1 Pa (20 ° C) |
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solubility |
very good in water (5000 g l −1 at 20 ° C) |
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safety instructions | ||||||||||||||||||||||
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Toxicological data | ||||||||||||||||||||||
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . |
1,6-Hexanediol is a chemical compound from the group of alkanediols . It consists of the basic structure of hexane , at the terminal positions of which there are hydroxyl groups .
presentation
There are various synthesis options for 1,6-hexanediol. So it can by reduction of adipic acid with lithium aluminum hydride or their esters with elemental sodium are obtained. The hydrolysis of 1,6-dibromohexane or 1,6-diiodohexane also gives 1,6-hexanediol. Further possibilities are the hydroboration of 1,5-hexadiene and the reducing ring opening of ε-caprolactone .
In industrial synthesis, 1,6-hexanediol is usually produced from adipic acid or its esters by reduction with molecular hydrogen . Temperatures of 170 to 240 ° C. and pressures of 150 to 300 bar are generally used for this purpose. The hydrogenation of ε-caprolactam or 6-hydroxycaproic acid is also used for industrial synthesis.
properties
1,6-Hexanediol is a colorless solid at room temperature that melts at 45 ° C. The boiling point is 250 ° C at normal pressure . 1,6-Hexanediol forms flammable vapor-air mixtures at higher temperatures. The compound has a flash point of 147 ° C. The explosion range is between 6.6% by volume as the lower explosion limit (LEL) and 16% by volume as the upper explosion limit (UEL). The ignition temperature is 320 ° C. The substance therefore falls into temperature class T2.
use
1,6-hexanediol can be used to synthesize oxepane . For this purpose, it is cyclized in DMSO at 190 ° C.
1,6-diaminohexane can be obtained by reacting with ammonia at elevated temperature and pressure.
1,6-Hexanediol is used in the manufacture of plastics such as polyesters and polyurethanes . It is also required as a plasticizer and for the production of lubricants .
Individual evidence
- ↑ Entry on HEXANEDIOL in the CosIng database of the EU Commission, accessed on June 3, 2020.
- ↑ a b c d e f g h i j Entry for CAS no. 629-11-8 in the GESTIS substance database of the IFA , accessed on October 12, 2016(JavaScript required) .
- ↑ a b c d e f data sheet 1,6-hexanediol (PDF) from Merck , accessed on December 26, 2019.
- ↑ E. Bernatek: methylal as a solvent in Lithium Aluminum Hydride Reductions in: . Acta Chem Scand. , 1954 , 8 , pp. 874-875, doi: 10.3891 / acta.chem.scand.08-0874 , pdf .
- ↑ Budesinsky, Z .; Rockova, E .: Anti-tubercular substances XII. Imidazolid-2-thione-4-carboxylic acids in Collect Czech Chem Commun ., 1957 , 22 , pp. 811-813, doi: 10.1135 / cccc19570811 .
- ↑ E. Haworth, WH Perkin: Hexamethylene dibromide and its action on sodium and on ethylic sodio-malonate , in: J. Chem. Soc. 1894 , 65 , pp. 591-602; doi: 10.1039 / CT8946500591 .
- ↑ Hamonet, Bull. Soc. Chim. Fr. 1905 , 33 , p. 530.
- ^ HC Brown, G. Zweifel: The Hydroboration of Dienes , in: J. Am. Chem. Soc. , 1959 , 81 (21) , pp. 5832-5833; doi: 10.1021 / ja01530a071 .
- ↑ S. Kim, KH Ahn: Ate Complex from Diisobutylaluminum Hydride and n-Butyllithium as a Powerful and Selective Reducing Agent for the Reduction of Selected. Organic Compounds Containing Various Functional Groups , in: J. Org. Chem. , 1984 , 49 , pp. 1717-1724; doi: 10.1021 / jo00184a010 .
- ↑ P. Werle, M. Morawietz, S. Lundmark, K. Sörensen, E. Karvinen, J. Lehtonen: Alcohols, Polyhydric , in: Ullmanns Enzyklopädie der Technischen Chemie , Wiley-VCH, Weinheim, 2008, doi : 10.1002 / 14356007 .a01_305.pub2 .
- ↑ a b entry on 1,6-hexanediol. In: Römpp Online . Georg Thieme Verlag, accessed on December 28, 2014.
- ^ E. Brandes, W. Möller: Safety-related parameters - Volume 1: Flammable liquids and gases , Wirtschaftsverlag NW - Verlag für neue Wissenschaft GmbH, Bremerhaven 2003.
- ↑ VJ Traynelis, WL Hergenrother, HT Hanson, JA Valicenti: Dehydration of Alcohols, Diols, and Related Compounds in Dimethyl Sulfoxide , in: J. Org. Chem. , 1964 , 29 (1) , pp. 123-129; doi: 10.1021 / jo01024a028 .
- ↑ U.S. patent, Eastman Kodak Co., US 2412209 1943 .