12-hydroxystearic acid
| Structural formula | |||||||||||||||||||
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| Structural formula without stereochemistry | |||||||||||||||||||
| General | |||||||||||||||||||
| Surname | 12-hydroxystearic acid | ||||||||||||||||||
| other names |
12-hydroxyoctadecanoic acid |
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| Molecular formula | C 18 H 36 O 3 | ||||||||||||||||||
| Brief description |
white solid |
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| properties | |||||||||||||||||||
| Molar mass | 300.48 g mol −1 | ||||||||||||||||||
| Physical state |
firmly |
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| Melting point |
80-81 ° C |
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| Vapor pressure |
2.58 × 10 –8 hPa (25 ° C) |
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| solubility |
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| As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . | |||||||||||||||||||
12-hydroxystearic acid is a chemical compound from the group of substituted carboxylic acids and hydroxy fatty acids .
Extraction and presentation
12-hydroxystearic acid can be obtained by catalytic hydrogenation of castor oil or ricinoleic acid or distillation of hydrolyzed, hydrogenated castor oil. For the product made from castor oil, a "typical composition" of the technical product is 84–84.9% 12-hydroxystearic acid, 8.3–9.5% stearic acid , 5% triglycerides (castor oil), <1–2% polyvinyl stearate and 0, 9-1% palmitic acid . 12-hydroxystearic acid can also be obtained from 2-hexylcyclododecanone . For this purpose, this compound is oxidized with a mixture of peracetic and permaleic acid in methylene chloride , which leads to the formation of the lactone of hydroxystearic acid. Subsequent alkaline hydrolysis produces hydroxystearate , from which hydroxystearic acid can be obtained.
properties
12-hydroxystearic acid is a crystalline white solid that is practically insoluble in water.
use
12-hydroxystearic acid can be used to make organogels based on vegetable oil. It is also used in cosmetics, wax blends, high-performance greases, polishes, inks and hot melt adhesives, as a lubricant for natural and synthetic rubbers and as a source of industrial oleochemicals, and also as an intermediate for pharmaceuticals. It is used in the form of their metal salts, the 12-hydroxystearates, e.g. B. as a co-stabilizer in polymer technology.
Individual evidence
- ↑ a b c d e f Entry on 12-hydroxystearic acid in the GESTIS substance database of the IFA , accessed on November 28, 2018(JavaScript required) .
- ↑ a b MAK: 12-hydroxystearic acid , MAK Value Documentation in German language, 2013. In The MAK Collection for Occupational Health and Safety, doi : 10.1002 / 3527600418.mb10614kskd0054 December 8, 2011
- ↑ a b c d Data sheet 12-Hydroxystearic acid, 95% from AlfaAesar, accessed on November 28, 2018 ( PDF )(JavaScript required) .
- ↑ Data sheet 12-Hydroxyoctadecanoic acid, 99% from Sigma-Aldrich , accessed on November 28, 2018 ( PDF ).
- ↑ Entry on 12-hydroxystearic acid. In: Römpp Online . Georg Thieme Verlag, accessed on November 28, 2018.