A Convenient Synthesis of Acaricide Propargite

doi:10.3696/j.issn.1006-396X.2010.01.012

Journal of Petrochemical Universities ›› 2010, Vol. 23 ›› Issue (1): 47-49.DOI: 10.3696/j.issn.1006-396X.2010.01.012

Previous Articles Next Articles

A Convenient Synthesis of Acaricide Propargite

Provincial Key Laboratory for Functional Compounds Synthesis and Application, Bohai University, Jinzhou Liaoning 121003, P.R.China

Received:2009-05-12 Revised:2009-11-11 Published:2010-03-25 Online:2010-03-25

广谱杀螨剂克螨特的合成研究

刘琳,薛守庆,钱建华,马成乡

渤海大学辽宁省功能化合物的合成与应用重点实验室, 辽宁锦州121003

作者简介::刘琳(1965 -), 女, 河北唐山市, 教授, 博士。
基金资助:
辽宁省自然科学基金(20062169)

Abstract

Abstract:

2-(4-tert-butyl-phenoxy) cyclohexanol was synthesized through the reaction of 4-tert-butylphenol with epoxycyclohexane in the presence of catalyst, and through two steps of thionyl chloride derivatives alcoholysis, neutralization to produce propargite under condition of 15 ℃. 1NMR and IR were performed to determine the structure of intermediates and final product. The results show that the analytical sample is identical to authentic, and the chemical structure and the quality of this compound agreed with those of imported samples. Factors influencing the reaction yield were studied, such as feeding mode and reactions times. The optimum technical condition: 2-(4-tert-butyl-phenoxy) cyclohexanol is prepared from 4-tert-butylphenol and epoxycyclohexane and then thionyl chloride derivatives alcoholysis chlorinated sulfoxides to get intermediates. Intermediates reacted with propargyl alcohol in the presence of toluene to obtain the target material of 2-(4-tert-butyl-phenoxy) cyclohexanol. The total yield can be reach to 82% (based on 4-tert-butyl-phenol) and the purity is 98%.

Key words: ４－ tert － Butylphenol , Propargite , Acaricide , Synthesis

摘要： 以对叔丁基苯酚为原料,首先对叔丁基苯酚与环氧环己烷在自制的催化剂(固体超强碱)存在的条件下通过开环反应,制得2-(4-叔丁基苯氧基)环己醇。其后冷却至 15℃左右,进行两步亚硫酰氯衍生物的醇解、中和得原药克螨特。中间体及克螨特样品进行了核磁共振及红外光谱分析,确证化学结构无误,质量与国外样品基本一致。考察了投料方式、反应时间对收率的影响,得到适宜的工艺条件为 :在120～126℃下,向对叔丁基苯酚中滴加环氧环己烷制备2-(4-叔丁基苯氧基)环己醇,而后向氯化亚砜中滴入此产物,最后向丙炔醇中加入上步反应产物以制备目标产物克螨特。经验证,产物总收率大于82%(以对叔丁基苯酚计),产品纯度大于 98%。

关键词: 对叔丁基苯酚 , 克螨特 , 杀螨剂 , 合成

LIU Lin, XUE Shou-qing, QIAN Jian-hua, MA Cheng-xiang . A Convenient Synthesis of Acaricide Propargite[J]. Journal of Petrochemical Universities, 2010, 23(1): 47-49.

刘琳,薛守庆,钱建华,马成乡. 广谱杀螨剂克螨特的合成研究[J]. 石油化工高等学校学报, 2010, 23(1): 47-49.

[1]	Jie LIAN, Baokuan CHEN, Hongrui TIAN, Yafei GUO, Yanfeng BI. Preparation,Structure and Characterization of Easily Peelable Nickel-Based Two-Dimensional Metal-Organic Frameworks [J]. Journal of Petrochemical Universities, 2024, 37(3): 66-72.
[2]	Shengdi LI, Haicheng XIAO, Zhijie WU. Research Progress of Cobalt⁃Based Catalysts for Fischer⁃Tropsch Synthesis [J]. Journal of Petrochemical Universities, 2024, 37(1): 34-42.
[3]	Lixing Zhang, Xiong Zhang, Chen Li, Zhiyong Wu, Taoming Zeng, Xiangdong Ma. Research Progress of Application of Coal⁃Based Carbon Anode Materials in Lithium⁃Ion Batteries [J]. Journal of Petrochemical Universities, 2022, 35(6): 10-18.
[4]	Lü Yu, Xiaoning Wang, Zhangxiong Wu. Research Progress in Synthesis of Cobalt⁃Based Catalysts and Peroxymonosulfate Activation [J]. Journal of Petrochemical Universities, 2022, 35(5): 12-24.
[5]	Chang Lu, Caishun Zhang, Daosheng Liu, Lei Zhang, Zhixian Gao. Design,Preparation and Performance of CuO⁃SiO₂⁃CeO₂ Catalyst [J]. Journal of Petrochemical Universities, 2022, 35(1): 29-34.
[6]	Yongjuan Qi, Xiaojie Gong, Dan Zhang, Xian Wu, Lihua Li. Preparation and Photocatalytic Performance of MIL⁃53 (Fe) by Single⁃Mode Focused Microwave [J]. Journal of Petrochemical Universities, 2021, 34(5): 24-29.
[7]	Zhu Min, Tang Yingchun, Wang Yanfang, Chen Shujun, Fu Yue. Microstructure and Decarbonization Properties of Modified Ni⁃MOF⁃74 [J]. Journal of Petrochemical Universities, 2020, 33(1): 17-22.
[8]	Chen Wenwen， Peng Yiqi, Liu Dongmei， Wang Haiyan. Effect of pH Value on ZSM⁃5 Molecular Sieve with Multilevel Structure of Nanocrystalline Stacking and Its Thiophene Alkylation Property [J]. Journal of Petrochemical Universities, 2019, 32(3): 28-32.
[9]	WangHongtao,HanJingyu,ZhangLi,LiPing,JinYingjie. Synthesis and Mesoporous Modification of MFI/MOR and BEA/MOR Intergrowth Zeolites [J]. , 2017, 30(1): 8-13.
[10]	Tian Sha,Li Huipeng,Zhao Hua,et al. Synthesis and Characterization of Y/MCM41 Composite Molecular Sieve [J]. Journal of Petrochemical Universities, 2015, 28(6): 20-24.
[11]	Jiang Xingjian,Li Junlong,Li Xuebing,et l. Simulation of Methanol Synthesis Process [J]. Journal of Petrochemical Universities, 2015, 28(5): 1-7.
[12]	Wang Dongmei, An Lei, Zhang Jianzhong,et al. The Synthesis and Application of a Amide Cationic Asphalt Emulsifier [J]. Journal of Petrochemical Universities, 2015, 28(1): 16-19.
[13]	Sun Hongyue，　Gui Jianzhou, Ning Jianmei,et al. Synthesis and Application of Heteropolyacid Ionic Liquids in Esterification [J]. Journal of Petrochemical Universities, 2014, 27(3): 21-24.
[14]	SUN Yueqiao,ZHANG Yuanyuan,DU Xiamei,et al. Synthesis of Pure ZSM22 Zeolites via Suppressing Intergrowths of Competing Phases [J]. Journal of Petrochemical Universities, 2013, 26(4): 21-26.
[15]	ZHANG Yazhou, LIU Limei, et al. Synthesis of WaterSoluble NitrogenContaining Calixarene [J]. Journal of Petrochemical Universities, 2013, 26(3): 13-17.

A Convenient Synthesis of Acaricide Propargite

广谱杀螨剂克螨特的合成研究

PDF

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics