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Process for the preparation of cis- AND trans-3,7-Dimethyl 2,6-Octadiene-1-OL from crude sulphated turpentine stream

Nelson Mandela Metropolitan University

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  • Title:
    Process for the preparation of cis- AND trans-3,7-Dimethyl 2,6-Octadiene-1-OL from crude sulphated turpentine stream
  • Author: Sathikge, Ndavheleseni David
  • Subjects: Sulfate waste liquor ; Turpentine ; Wood-pulp industry -- By-products
  • Description: As part of CSIR Biosciences’ interest in aroma chemicals, the processing of crude sulphated turpentine (CST) into high value aroma products was investigated. The primary target product, linalool, was obtained from a mixture of α- and β-pinene in four steps. It can be transformed into a wide range of high value added aroma chemicals. Isomerisation of linalool in the presence of a transition metal catalyst furnishes geraniol and nerol. The scientific work described in this report was part of a bigger project aimed at developing innovative processes to manufacture aroma, flavour & fragrance chemicals through beneficiation of industrial waste streams and other raw materials, available locally from the Forestry, Paper & Pulp industries. The evaluation of a process for the preparation of precursor aroma, flavour & fragrance compounds, in particular geraniol and nerol, from locally available raw materials and industrial waste streams, was investigated. Preparation of geraniol and nerol from linalool (ex α-pinene stream) was investigated using acids or organometallic complexes as catalysts for the corresponding isomerisation reaction. The investigation was conducted in an effort to find a less costly process utilising milder conditions than via the conventional cleavage of β-pinene to myrcene under extreme pyrolysis conditions (>650°C). The transformation of linalool to geraniol/nerol using mineral acids was found to be dominated by secondary reactions such as dehydration and cyclisation, resulting in poor product selectivities and yields. On the other hand, organometallic complexes, in particular vanadium-based complexes (e.g. (OV(OBu)3) produced satisfactory results in the preliminary assessment (conversion of 79.8 percent and selectivity of 98.3 percent). A set of statistically designed experiments was carried out on the (VO(BuO)3 + [(Bu)4N+]OH¯) catalyst system where three variables were tested, i.e. substrate concentration, temperature, and catalyst loading. The selected model for conversion was significant with the “Probability > F” being < 0.0001. The most important contributing variable to the model for conversion was temperature i.e. 83.9 percent. Temperature was still the most important variable for the selectivity response at 65.0 percent contribution level. The response surface generated for the selectivity response was flat indicating a robust method within the parameter range selected.
  • Publisher: Nelson Mandela Metropolitan University
  • Creation Date: 2008
  • Format: 130 pages
  • Language: English
  • Source: South East Academic Libraries System Digital collections of Nelson Mandela University
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