Cyclododecane
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| General | |||||||||||||||||||
| Surname | Cyclododecane | ||||||||||||||||||
| Molecular formula | C 12 H 24 | ||||||||||||||||||
| Brief description |
colorless solid with a musty odor |
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| properties | |||||||||||||||||||
| Molar mass | 168.33 g mol −1 | ||||||||||||||||||
| Physical state |
firmly |
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| density |
0.830 g cm −3 |
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| Melting point |
61 ° C |
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| boiling point |
243 ° C |
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| Vapor pressure |
9.8 Pa (20 ° C) |
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| solubility |
practically insoluble in water (10 mg l −1 at 20 ° C) |
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| safety instructions | |||||||||||||||||||
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| Toxicological data |
21 mg l −1 ( EC 50 , crustaceans , 48 h ) |
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| As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . | |||||||||||||||||||
Cyclododecane is a chemical compound from the group of alicyclic saturated hydrocarbons (more precisely the cycloalkanes ).
Extraction and presentation
Cyclododecane can be obtained industrially from 1,3-butadiene by catalytic trimerization (conversion to 1,5,9-cyclododecatriene ) and subsequent hydrogenation .
properties
The skeletal formula shown in the info box does not reflect the “real” molecular structure. The twelve carbon atoms are not in one plane. In addition, the molecule is "flexible"; that is, its atoms are in constant motion in the molecular structure ( pseudorotation ). This means that different conformations are possible.
In the crystalline state - as an X-ray crystal structure analysis at low temperature showed - there is a conformer which has D 4 symmetry. It was called "quadratisch" (" square "), because some carbon atoms can be understood as corner points of a square.
Cyclododecane is a colorless, flammable solid with a musty odor, which is practically insoluble in water. Cyclododecane is insoluble in strongly polar solvents and soluble in non-polar solvents such as alkanes or chlorinated hydrocarbons. The compound has the unusual property of sublime at room temperature and thus disappears within a short time. The structure of the solid differs when it is precipitated from solution and solidified from a melt. When precipitated from a solution, cyclododecane can form long crystal needles, this crystal formation being essentially dependent on the evaporation rate of the selected solvent.
use
Cyclododecane is used as a volatile binder, to secure transport and in paper restoration. It is also useful as an intermediate for the production of other chemical compounds such as cyclododecanone , 1,12- dodecanedioic acid or lauric lactam is used.
Individual evidence
- ↑ a b c d e f g h Entry for CAS no. 294-62-2 in the GESTIS substance database of the IFA , accessed on December 22, 2019(JavaScript required) .
- ↑ ECHA: Cyclododecane - Registration Dossier - ECHA , accessed on January 11, 2020
- ↑ Hans-Jürgen Arpe: Industrial Organic Chemistry , p. 291; ISBN 978-3-527-31540-6 .
- ↑ Frank AL Anet, TN Rawdah, J. Am. Chem. Soc. , 100, 7166-7171 (1978), doi : 10.1021 / ja00491a007 .
- ↑ JD Dunitz, HMM Shearer: The structures of the middle ring compounds III. The structure of the cyclododecane , Helvetica Chimica Acta , 43, 18-35 (1960), doi : 10.1002 / hlca.19600430104 .
- ↑ a b Kremer Pigments: Cyclododecane Spray ( Memento of the original from August 8, 2007 in the Internet Archive ) Info: The archive link has been inserted automatically and has not yet been checked. Please check the original and archive link according to the instructions and then remove this notice.
