1,6-hexanediol

Structural formula
General
Surname	1,6-hexanediol
other names	Hexane-1,6-diol 1,6-dihydroxyhexane HEXANEDIOL ( INCI )
Molecular formula	C 6 H 14 O 2
Brief description	colorless crystals
External identifiers / databases
CAS number 629-11-8 EC number 211-074-0 ECHA InfoCard 100.010.068 PubChem 12374 ChemSpider 13839416 DrugBank DB02210 Wikidata Q161563
properties
Molar mass	118.18 g mol −1
Physical state	firmly
density	0.96 g cm −3 (20 ° C)
Melting point	45 ° C
boiling point	250 ° C
Vapor pressure	<1 Pa (20 ° C)
solubility	very good in water (5000 g l −1 at 20 ° C)
safety instructions
GHS labeling of hazardous substances no GHS pictograms H and P phrases H: no H-phrases P: no P-phrases
Toxicological data	3730 mg kg −1 ( LD 50 ,  rat ,  oral )
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.

${\displaystyle \mathrm {HO{-}(CH_{2})_{6}{-}OH\ +\ 2\ NH_{3}\ {\xrightarrow {\Delta T}}\ H_{2}N{-}(CH_{2})_{6}{-}NH_{2}\ +\ 2\ H_{2}O} }$

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

1. ↑ Entry on HEXANEDIOL in the CosIng database of the EU Commission, accessed on June 3, 2020.
2. ↑ ^{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) .
3. ↑ ^{a b c d e f} data sheet 1,6-hexanediol (PDF) from Merck , accessed on December 26, 2019.
4. ↑ 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 .
5. ↑ 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 .
6. ↑ 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 .
7. ↑ Hamonet, Bull. Soc. Chim. Fr. 1905 , 33 , p. 530.
8. ^ HC Brown, G. Zweifel: The Hydroboration of Dienes , in: J. Am. Chem. Soc. , 1959 , 81 (21) , pp. 5832-5833; doi: 10.1021 / ja01530a071 .
9. ↑ 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 .
10. ↑ 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 .
11. ↑ ^{a b} entry on 1,6-hexanediol. In: Römpp Online . Georg Thieme Verlag, accessed on December 28, 2014.
12. ^ E. Brandes, W. Möller: Safety-related parameters - Volume 1: Flammable liquids and gases , Wirtschaftsverlag NW - Verlag für neue Wissenschaft GmbH, Bremerhaven 2003.
13. ↑ 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 .
14. ↑ U.S. patent, Eastman Kodak Co., US 2412209 1943 .