Comparative thermolysis of beta- and alpha-pinenes in supercritical ethanol: the reaction characterization and enantiomeric ratios of products

Comparative thermolysis of beta- and alpha-pinenes in supercritical ethanol: the reaction characterization and enantiomeric ratios of products Full article

Journal

Russian Chemical Bulletin
ISSN: 1066-5285 , E-ISSN: 1573-9171

Output data

Year: 2007, Volume: 56, Number: 6, Pages: 1234-1238 Pages count : 5 DOI: 10.1007/s11172-007-0186-x

Tags

thermolysis; supercritical media; ethanol; monoterpenes; pinenes; beta-myrcene; limonene

Authors

Chibiryaev A.M. ^1,2 , Yermakova A. ³ , Kozhevnikov I.V. ² , Sal'nikova O.I. ¹ , Anikeev V.I. ³

Affiliations

1	N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, 9 prosp. Akad. Lavrent’eva, 630090, Novosibirsk, Russian Federation
2	Department of Natural Sciences, Novosibirsk State University, 2 ul. Pirogova, 630090, Novosibirsk, Russian Federation
3	G. K. Boreskov Institute of Catalysis, Siberian Branch of the Russian Academy of Sciences, 5 prosp. Akad. Lavrent’eva, 630090, Novosibirsk, Russian Federation

The thermolysis of beta-pinene and the co-thermolysis of an equimolar mixture of beta- and alpha- pinenes in supercritical ethanol were carried out. The reaction of beta-pinene affords myrcene as the major product (> 70%). Considerable differences in the temperature dependence of the reaction rate were revealed for the transformations of beta- pinene into beta-myrcene and of alpha-pinene into limonene. The pre-exponential factors and the activation energies were calculated. The enantiomeric ratios of the thermolysis products of beta- and alpha-inenes and limonene were estimated. The starting monoterpenes do not undergo racemization during thermolysis. The thermolysis of enantiomerically pure alpha-pinene affords racemic (+/-)-limonene, whereas (-)-beta-pinene gives (-)- limonene. The enantiomeric ratio in the latter remains equal to the enantiomeric purity of the starting beta-pinene.

Chibiryaev A.M. , Yermakova A. , Kozhevnikov I.V. , Sal'nikova O.I. , Anikeev V.I.
Comparative thermolysis of beta- and alpha-pinenes in supercritical ethanol: the reaction characterization and enantiomeric ratios of products
Russian Chemical Bulletin. 2007. V.56. N6. P.1234-1238. DOI: 10.1007/s11172-007-0186-x WOS Scopus РИНЦ

Чибиряев А.М. , Ермакова А.И. , Кожевников И.В. , Сальникова О.И. , Аникеев В.И.
Сравнительный термолиз β- и α-пиненов в сверхкритическом этаноле: особенности реакций и энантиомерный состав продуктов
Известия Академии наук. Серия химическая.(RUSS CHEM B+). 2007. №6. С.1188-1192. РИНЦ

Published print:

Jun 1, 2007

Web of science	WOS:000251971700021
Scopus	2-s2.0-36949034959
Elibrary	13547993
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