Synthesis Of 2 - Methylene Glutaronitrile And Trans - 1,2 - Cyclohexanediol

This thesis studies the synthesis methods for the intermediate products of 2-methyleneglutaro-nitrile and trans-1,2-cyclohexanediol. The main results and conclusions are summarized as following two parts:(1) Without using metal elements in phosphine catalysis of organic synthesis reaction, the outcome product would not have metal residues, which is more suitable for the stringent requirements of metal residues in pharmaceutical synthesis. Avoid using a metal catalyst synthesis scheme not only environmentally friendly, but also have a huge research prospects in future. This paper found that tricyclohexylphosphine has effectively catalytic active to let acrylonitrile become dimer, producing the head-to-tail dimerization product which is 2-methyleneglutaronitrile with high selectivity and high yield. Reaction process conditions were investigated, such as:catalyst, reaction temperature, reaction time, solvents, reaction solubility and so on. Have optimized the various reaction parameters of this process. Compared with the reported literature, this reaction used inexpensive non-halogen t-BuOH as solvent, with mild reaction conditions, less of the catalyst and higher concentration of the reagent. So it’s very suitable for industrial production. This paper have successfully expanded this reaction to 50 mL scale. This provided an efficient and clean synthesis method for the intermediates of 2-methylenepentanedinitrile.(2) Unique catalytic properties of organic selenium compounds in the oxidation reaction, Have gradually attracted people’s attention. Explored the organoselenium catalyzed oxidation of cyclohexene to trans-1,2-diol. Reaction process conditions were investigated, such as:catalyst, reaction temperature, reaction time, solvents, and other materials ratio. Screened out of the low-load and recyclable 1,2-bis [3,5-bis (trifluoromethyl) phenyl] diselane-catalyzed. The hydrogen peroxide can efficiently and selectively catalytic cyclohexene oxide to trans-1,2-cycloh-exanediol under this catalyst. The reaction is clean, moderate, low cost, and recyclable which conform to the spirit of green chemistry. At the same time,1,2-cyclohexanediol as an important organic intermediate for adipic acid, it offers a new way to synthesis adipic acid. So, it has a higher value in the future industrial production. Currently, we are trying to further reduce the cost of the catalyst, and develop water-phase reaction, so that it can be applied to actual production in the future soon.