JOURNAL OF NANJING FORESTRY UNIVERSITY ›› 2013, Vol. 37 ›› Issue (04): 127-132.doi: 10.3969/j.issn.1000-2006.2013.04.024

Previous Articles     Next Articles

Synthesis of isobornyloxyethyl methacrylate from camphene

WANG Shikang, XU Xu, XU Xiaowei, WEI Baisong, WANG Shifa*   

  1. Jiangsu Key Lab of Biomass-based Green Fuels and Chemicals, College of Chemical Engineering, Nanjing Forestry University, Nanjing 210037,China
  • Online:2013-08-18 Published:2013-08-18

Abstract: Isobornyloxyethyl methacrylate(IBOEMA), a new type of active diluent for UV-curing coating, was synthesized from camphene as raw material by etherification and transesterification. In the etherification process of camphene and ethylene alcohol, A-15 was used as the catalyst, and theeffects of the amount of A-15, the molar ratios of ethylene glycol to camphene, reaction temperature and time on the yield of isobornyl hydroxyethyl ether were investigated, and the optimum synthesis conditions of isobornyl hydroxyethyl ether were determined based on orthogonal test results as follows: A-15 was used as the catalyst and its dosage was 6.0%(based on the total weight of camphene and ethylene glycol); ethylene glycol/camphene molar ratio was 3.5:1.0; reaction temperature and time were 90 ℃ and 9 h, respectively. The conversion ratio of camphene, reaction selectivity, and the yield of isobornyl hydroxyethyl ether reached 79%, 93%, and 74%, respectively, at aforesaid reaction conditions. In the transesterification process of isobornyl hydroxyethyl ether and methyl methacrylate, cyclohexane was used as the solvent, and the reaction was carried out at the condition of refluxing; the effects of the type and amount of catalyst, the molar ratio of isobornyl hydroxyethyl ether to methyl methacrylate, reaction time, the type and amount of inhibitor on the yield of IBOEMA were examined, and the optimum synthesis conditions of IBOEMA were determined based on the orthogonal test results as follows: methyl methacrylate/isobornyl hydroxyethyl ether molar ratio was 1.25:1.00; KOH was used as the catalyst for transesterification and it dosage was 3%(based on the total weight of methyl methacrylate and isobornyl hydroxyethyl ether); reaction time 8 h; phenothiazine was used as the inhibitor, and its dosage was 1%; cyclohexane was used as the solvent, and cyclohexane/isobornyl hydroxyethyl ether molar ratio was 37:1. The conversion ratio of isobornyl hydroxyethyl ether, reaction selectivity, and the yield of IBOEMA reached 91%, 93%, and 85%, respectively, at the aforesaid reaction conditions. The structures of isobornyl hydroxyethyl ether and IBOEMA were determined with GC-MS and FTIR spectra.

CLC Number: