Cyclodecane (cyclodecane) - organic matter of the class of cycloalkanes . Chemical formula - C 10 H 20 .
| Cyclodecane | |
|---|---|
 | |
 | |
| Are common | |
| Systematic name | cyclodecane |
| Chem. formula | C 10 H 20 |
| Physical properties | |
| condition | colorless liquid |
| Molar mass | 140.266 g / mol |
| Density | 0.871 g / cm³ |
| Thermal properties | |
| T. melt. | 9.5 [1] |
| T. Kip. | 201 ° C |
| Optical properties | |
| Refractive index | 1,471 |
| Classification | |
| Reg. CAS number | 293-96-9 |
| Pubchem | |
| Reg. EINECS number | |
| SMILES | |
| Inchi | |
| Chemspider | |
In nature, it is found in the composition of oil.
Content
Physical Properties
Colorless liquid.
Chemical Properties
On platinized carbon or in the presence of palladium, cyclodecane forms a mixture of naphthalene , azulene and other hydrocarbons when heated in the vapor state [2] [3] .
In the presence of cobalt, manganese, and other catalysts, cyclodecane is oxidized by air to a mixture of cyclodecanol and cyclodecanon [4] . The catalytic transformations of cyclodecane in the presence of a nickel catalyst at 200 ° C were accompanied by the formation of n- decane , n- nonane , isomeric methylnonans, cyclononane, and trans- decalin [5] .
Conformations
Cyclodecane is significantly more stressed than cyclohexane . The reason for this stress is mainly the van der Waals interactions [6] .
In cyclodecane, 14 bonds are oriented outward and are called extranular (two types: eight resemble equatorial bonds in cyclohexane, six - axial). The remaining six connections are intranular, directed inside the ring. In this cyclodecane conformation, not all CH 2 groups are equivalent; in some CH 2 groups, both bonds are oriented extranularly (type I), and in others, one bond is intranular, and the second is extranular, the latter can be oriented either equatorially (type II) or axially (type III). It is the intranular hydrogen atoms that create the “intramolecular tightness” responsible for the increase in the energy of the cyclodecane molecule. The distances between the intranular hydrogen atoms of one layer, determined by the model, are 0.184 nm (with a sum of van der Waals radii of 0.24 nm) [7] .
Toxicity
When applied to the skin, guinea pigs cause an inflammatory reaction - redness and thickening of the epidermis [8] .
Notes
- ↑ General organic chemistry. - T.1, ed. Barton D. and Ollis V.D. - M .: Chemistry, 1981. - p. 74
- ↑ Knunyants I. L. Brief chemical encyclopedia, vol. 1, M .: Soviet encyclopedia, 1967, stlb. 286
- ↑ Fizer L., Fizer M. Organic Chemistry. Advanced Course, Volume 2, Ripol Classic, 2013, p. 154
- ↑ Freidlin G. N. Analytical dicarboxylic acids, p. 193
- ↑ Kazansky B. А. Catalytic transformations of hydrocarbons. 1968, pp. 29, 415
- ↑ Keri, FN. Advanced Course in Organic Chemistry, Book 1, 1981, p. 92
- ↑ Stereochemistry of cycles. Cyclodecane , p. 9
- ↑ Harmful substances in industry. Volume 1, 1976 , p. 32.
Sources
- Diwakar M. Pawar; Sumona V. Smith; Hugh L. Mark; Rhonda M. Odom ,; Eric A. Noe. Spectroscopy and Computational Methods (Eng.) // Journal of the American Chemical Society Conformational Study of Cyclodecane and Substituted Cyclodecanes by Dynamic NMR : journal. - 1998. - Vol. 120 , no. 41 - P. 10715 . - DOI : 10.1021 / ja973116c .
- CharChem. Cyclodecane
- Lazarev N.V. Harmful substances in industry. Volume 1. - L .: Chemistry, 1976. - 592 p.