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GAS–LIQUID CHROMATOGRAPHY OF TERPENES: PART II. THE DEHYDRATION PRODUCTS OF α-TERPINEOL

 

作者: E. Von Rudloff,  

 

期刊: Canadian Journal of Chemistry  (NRC Available online 1961)
卷期: Volume 39, issue 1  

页码: 1-12

 

ISSN:0008-4042

 

年代: 1961

 

DOI:10.1139/v61-001

 

出版商: NRC Research Press

 

数据来源: NRC

 

摘要:

The complex mixture of terpenes obtained on dehydrating α-terpineol with aqueous oxalic acid was almost completely separated by gas–liquid chromatography (GLC), using rapeseed oil as a new liquid phase. Terpinolene, dipentene, α- and γ-terpinene, Δ2,4(8)-p-menthadiene, and 1,8-cineole were identified as the major reaction products; three minor and seven trace constituents were also detected. One of the minor components wasp-cymene, one an oxide, and the third an unidentified hydrocarbon. The yield of these components after different reaction times was determined by GLC. The initial dehydration gives terpinolene and dipentene in the ratio of approximately 2:1. Terpinolene is isomerized to α- and γ-terpinene, Δ2,4,(8)-p-menthadiene, and the unidentified hydrocarbon, but not to dipentene. 1,8-Cineole and the other oxide are formed in a reversible reaction. Dehydration of α-terpineol with several other acidic reagents yielded mixtures of products similar to that obtained with aqueous oxalic acid. With acetic acid or acetic anhydride, however, dipentene was formed preferentially and this reaction appears to proceed via the derived acetate.

 

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