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[1]奚强,冯薇伟,胡杨,等.β亚甲基苯乙醇的合成工艺[J].武汉工程大学学报,2013,(06):16-19.[doi:103969/jissn16742869201306004]
　XI Qiang,FENG Wei wei,HU Yang,et al.Synthesis of βmethylene phenethyl alcohol[J].Journal of Wuhan Institute of Technology,2013,(06):16-19.[doi:103969/jissn16742869201306004]
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《武汉工程大学学报》[ISSN:1674-2869/CN:42-1779/TQ]

卷:
期数:
2013年06期
页码:
16-19
栏目:
化学与化学工程
出版日期:
2013-06-30

文章信息/Info

Title:
Synthesis of βmethylene phenethyl alcohol
文章编号:
16742869(2013)06001604
作者:
奚强1; 冯薇伟1; 胡杨1; 余利民2; 陈建2
1.武汉工程大学化工与制药学院，湖北 武汉 430074；2.武汉理工大学化学工程学院，湖北 武汉 430070
Author(s):
XI Qiang1; FENG Weiwei1;  HU Yang1; YU Liming2; CHEN Jian2
1. School of Chemical Engineering and Pharmacy, Wuhan Institute of Technology, Wuhan 430074, China；2. Chemical Engineering Institute, Wuhan University of Technology, Wuhan 430070, China
关键词:
苯乙醛; 亚甲基化; 氢转移还原
Keywords:
plenylacetaldehyde;  methylenation;  hydrogen transfer reaction
分类号:
TQ243.4
DOI:
103969/jissn16742869201306004
文献标志码:
A
摘要:
针对β亚甲基苯乙醇合成工艺中反应条件较苛刻、操作较复杂、产物难分离纯化和总收率偏低的问题，以苯乙醛为原料，经亚甲基化反应和均相氢转移还原反应两步合成了β亚甲基苯乙醇.分别考察了两步反应投料比、催化剂的用量和反应温度等条件对产物收率的影响.结果表明,亚甲基化反应在50 ℃，投料比为n(苯乙醛)∶n(甲醛)∶n(二甲胺盐酸盐)=1∶1.2∶0.2的条件下反应16 h最佳，反应液经减压蒸出甲醛、异丙醇和水，中间产物无需进一步纯化，直接用于还原反应；氢转移还原反应于60～65 ℃下反应12 h，投料比n(α亚甲基苯乙醛)∶n(异丙醇铝)=1∶0.1，反应液用乙酸乙酯和水萃取、纯化，得到β亚甲基苯乙醇.产物的总收率可达86%，纯度98.5%以上，其结构经核磁共振氢谱确认.该合成工艺反应条件温和、操作简单、产物易于分离和纯化、收率高，具有一定的工业化价值.
Abstract:
To improve the yield of the βmethylene phenethyl alcohol and avoid the disadvantages including harsh conditions, hard to control the reaction process, difficult purification and low yield in the present routes, an approach to synthesize βmethylene phenethyl alcohol was investigated with phenylacetaldehyde as the raw material by methylenation and hydrogen transfer reaction. The effects of molar ratio of material, amount of catalyst and reaction temperature on the yield of the product were discussed. the yield of βmethylene phenethyl alcohol reached 86% with purity of over 98.5% when the methylenation was carried out at 50 ℃ for 16 h and ratio of n(plenylacetaldehyde)∶n(formaldehyde)∶n(organic amine salt)=1∶1.2∶0.2, formaldehyde, isopropanol and water were distilled from the reaction liquid by vacuum evaporation and the intermediate product was directly used without further purification; the hydrogen transfer reaction was carried out at 60-65 ℃ for 12 h with n(intermediate):n(aluminum isopropoxide)=1∶0.1, the concentrate was extracted by ethyl acetate and water. The structure of the product was confirmed by 1H NMR. This process has the characteristics of mild reaction conditions, simple operation, easy to be isolated and purified, high total yield, which is feasible for industrialization.

参考文献/References:

［1］郭廷翘，刘丽琴，郭雪飞.用α甲基苯乙烯合成龙葵醇系列香料\[J\].精细化工，2001,18(1):3436.GUO Tingqiao, LIU Liqin, GUO Xuefei. Synthesis of hydratropic alcohol series flavors from αmethylstyrene\[J\].Fine Chemicals,2001,18(1):3436.(in chinese)［2］Behenna, Douglas C. Enantioselective decarboxylative alkylations: catalyst development, substrate cope, and mechanistic studies\[J\]. ChemistryA European Journal,2011,17(50): 1419914223.［3］Mo Jun, Ruan Jiwu, Liu Shifang, et al. Regioselective Heck arylation of unsaturated alcohols by catalysis in ionic liquid\[J\]. Chemistry Communication, 2006 (34):35913593.［4］Mark A S, Robert P B. Betaalkylidene phenethyl alcohols, organoleptic uses thereof and processes for preparing same:US,4756840\[P\]. 19880712.［5］刘丽琴，郭廷翘，左宏，等.玫瑰型香料β亚甲基苯乙醇的合成\[J\].精细化工,2000,17(5):258259.LIU Liqin, GUO Tingqiao, ZUO Hong, et al. Synthesis of βmethylene phenethyl alcohol\[J\]. Fine Chemicals, 2000,17(5):258259.(in chinese)［6］Erkkilae A, Pihko P M. Mild organocatalytic αmethylenation of aldehydes\[J\]. Journal of Organic Chemistry, 2006, 71(6):25382541.［7］罗鸽，刘歆文，许宁，等.丙烯醛与异丙醇均相氢转移制烯丙醇反应中催化剂失活及再利用研究\[J\].化学世界,2008,49(1):4245.LUO Ge, LIU Xinwen, XU Ning, et al. Studies on deactivation and recycle of aluminium isopropocide in the homogeneous hydrogen transfer reaction of acrolein to allyl alcohol\[J\]. Chemical World, 2008,49(1):4245.(in chinese)［8］唐培堃，冯亚青.精细有机合成化学与工艺学\[M\]. 2版.北京：化学工业出版社,2006:324325.TANG Peikun, FENG Yaqing. Synthetic Organic Chemistry and Technology of Fine Chemicals\[M\]. 2nd edition. Beijing:Chemical Industry Press,2006:324325.(in chinese)

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备注/Memo

备注/Memo:
收稿日期：20130403作者简介：奚强（1966），男，湖北浠水人，教授，博士，硕士研究生导师.研究方向：有机合成.
更新日期/Last Update: 2013-07-11