1-ethynyl-1-cyclohexanol
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| General | |||||||||||||||||||
| Surname | 1-ethynyl-1-cyclohexanol | ||||||||||||||||||
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| Molecular formula | C 8 H 12 O | ||||||||||||||||||
| Brief description |
colorless solid with a faint camphor-like odor |
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| properties | |||||||||||||||||||
| Molar mass | 124.18 g mol −1 | ||||||||||||||||||
| Physical state |
firmly |
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| density |
0.976 g cm −3 (20 ° C) |
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| Melting point |
28 ° C |
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| boiling point |
180 ° C |
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| As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . | |||||||||||||||||||
1-Ethynyl-1-cyclohexanol (short: ECH ) is an organic-chemical compound from the group of alcohols , more precisely the alkynols .
Extraction and presentation
The industrial-scale synthesis of 1-ethynyl-1-cyclohexanol is carried out by the Reppe process (ethynylation). Acetylene reacts with cyclohexanone under basic catalysis in the presence of liquid ammonia at low temperatures directly to form 1-ethynyl-1-cyclohexanol. Alkali hydroxides such as sodium or potassium hydroxide are usually used as bases .
Mechanistically speaking, the base initially deprotonates the acetylene. An acetylide ion is formed , which can now nucleophilically attack the positively polarized carbonyl group of the cyclohexanone. An alcoholate is formed as an intermediate , which is now protonated by the previously split off hydrogen atom.
properties
Physical Properties
1-Ethynyl-1-cyclohexanol has a density of 0.976 g / cm 3 at 20 ° C. ECH also has a vapor pressure of 40 Pa at 20 ° C, 80 Pa at 25 ° C and 3.8 hPa at 50 ° C.
Chemical properties
1-Ethynyl-1-cyclohexanol is a flammable, hardly flammable solid from the group of alcohols . It is also sparingly soluble in water (24.5 g / l at 20 ° C). At 20 ° C has an aqueous solution of concentration 1 g / l of a pH of 7, an aqueous solution of concentration 24.5 g / l pH of 5.1-5.8 at.
use
1-ethynyl-1-cyclohexanol is used for the synthesis of hypnotics and sedatives (for example ethinamate ). Furthermore, fragrances and fragrances are made from it . It is also used in a variety of ways in biology and for the production of silicones , plastics , polymers and fibers .
safety instructions
Acute and chronic health risks arise from 1-ethynyl-1-cyclohexanol. It is classified as acutely toxic if swallowed or in contact with skin. In addition, severe irritation to the skin and eyes has been confirmed. 1-Ethynyl-1-cyclohexanol is considered to be slightly hazardous to water. Special ADR regulations apply to road transport as part of the European Agreement on the International Carriage of Dangerous Goods by Road . 1-Ethynyl-1-cyclohexanol falls into ADR class 6.1 for toxic substances and is assigned UN number 2811 and hazard number 60. The designation for international road and rail transport is "Toxic organic solid, nag".
Web links
Individual evidence
- ↑ a b c d e f g h i j k l m n o Entry on 1-ethyn-1-cyclohexanol in the GESTIS substance database of the IFA , accessed on January 28, 2019(JavaScript required) .
- ↑ a b c Entry on 1-ethynylcyclohexanol. In: Römpp Online . Georg Thieme Verlag, accessed on January 28, 2019.
- ↑ Jochem Henkelmann, Alois Kindler, Jan-Dirk Arndt, Katrin Klass: Process for the production of acetylene alcohols. In: Google Patents. BASF AG, July 23, 2003, accessed April 12, 2019 .
- ↑ 1-Ethynyl-1-cyclohexanol. In: BASF product search. BASF SE, 2014, accessed on January 28, 2019 (German, English).