2,6-dimethyl-7-octen-2-ol
| Structural formula | |||||||||||||||||||
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| General | |||||||||||||||||||
| Surname | 2,6-dimethyl-7-octen-2-ol | ||||||||||||||||||
| other names |
Dihydromyrcenol |
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| Molecular formula | C 10 H 20 O | ||||||||||||||||||
| Brief description |
colorless liquid |
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| properties | |||||||||||||||||||
| Molar mass | 156.27 g mol −1 | ||||||||||||||||||
| Physical state |
liquid |
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| density |
0.832 g cm −3 |
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| Melting point |
<−20 ° C |
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| boiling point |
194-197 ° C |
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| Vapor pressure |
20 Pa (25 ° C) |
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| solubility |
very sparingly soluble in water (0.939 g l −1 at 20 ° C) |
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| Refractive index |
1.443 (20 ° 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 . Refractive index: Na-D line , 20 ° C | |||||||||||||||||||
2,6-Dimethyloct-7-en-2-ol is a chemical compound from the group of alcohols .
Extraction and presentation
2,6-Dimethyloct-7-en-2-ol and its carboxylic acid esters are produced from dimethylcyclooctene mixtures ( 1,5-dimethylcyclooctene 1 , 1,6-dimethylcyclooctene and / or 1,4-dimethylcyclooctene ) by (a) thermal isomerization of Dimethylcyclooctene reaction mixture to form an octadiene mixture (2,5-, 2,7- and 2,6-dimethylocta-1,7-diene 2 ), (b) reaction of the octadiene mixture with a carboxylic acid for the selective formation of the ester 3 of 2,6-dimethyloct -7-en-2-ol and (c) optionally hydrolyzing the ester to 2,6-dimethyloct-7-en-2-ol 4 under basic conditions.
An alternative way to prepare 2,6-dimethyloct-7-en-2-ol is the pyrolysis of pinane 5 to 2,6-dimethylocta-2,7-diene 6 , which with glacial acetic acid / sulfuric acid to 2,6-dimethyloct -7-en-2-acetate 3 is implemented. Hydrolysis of the ester with a potassium hydroxide solution gives 2,6-dimethyloct-7-en-2-ol 4 .
properties
2,6-Dimethyloct-7-en-2-ol is a flammable, hardly inflammable, viscous colorless liquid that is very sparingly soluble in water.
use
2,6-Dimethyloct-7-en-2-ol is used in the fragrance industry because of its fresh lime-like and citrus-like smell (e.g. for Drakkar Noir ).
safety instructions
The vapors of 2,6-dimethyloct-7-en-2-ol can form an explosive mixture with air ( flash point 76 ° C).
Individual evidence
- ↑ a b c d e f g h i j k Entry on 2,6-Dimethyloct-7-en-2-ol in the GESTIS substance database of the IFA , accessed on March 4, 2019(JavaScript required) .
- ↑ a b Data sheet dihydromyrcenol, ≥99% from Sigma-Aldrich , accessed on March 4, 2019 ( PDF ).
- ↑ Patent application US4247723 : Preparation of dihydromyrcenol. Applied January 21, 1977 , published January 27, 1981 , Applicant: Shell Oil Company, Inventor: Aaldert J. de Jong.
- ↑ Patent application US2902510 : 2-substituted-2,6-dimethyl-7-octenes and process for preparing same. Applied on April 9, 1959 , published September 1, 1959 , applicant: The Glidden Company, inventor: Robert L. Webb.
- ^ Ernst T. Theimer: Fragrance Chemistry The Science of the Sense of Smell . Elsevier, 2012, ISBN 0-323-13860-8 , pp. 155 ( limited preview in Google Book search).
- ^ Giovanni Dugo, Angelo Di Giacomo: Citrus The Genus Citrus . CRC Press, 2002, ISBN 978-0-203-21661-3 , pp. 564 ( limited preview in Google Book search).