1,8-孟烷二胺的合成方法及其应用的研究进展
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摘要
1,8-孟烷二胺是一种重要的松节油深加工产品,化学性质活泼,在高分子合成方面有着极为广泛的应用。本文简要介绍了1,8-孟烷二胺的一些理化性质,综述了合成1,8-孟烷二胺的几种主要方法(氰化水解法、氰化还原法以及叠氮还原法等),并指出了这些制备方法各自存在的缺陷:氰化水解法所使用的氢氰酸和催化剂硫酸分别具有毒性大和腐蚀性大的特点,易对环境造成严重影响;氰化还原法所使用的硼氢化钾或硼氢化钠属于易爆化合物,具有一定的危险性;叠氮还原法产物分离困难。因此,1,8-孟烷二胺的合成工艺有待进一步优化。同时,也介绍了1,8-孟烷二胺在作为环氧树脂固化剂、交联剂、二氧化碳捕获剂以及合成原料中的应用。最后展望了1,8-孟烷二胺在催化剂和生物活性方面的发展前景。
p-Menthane-1,8-diamine, which has active chemical property, is an important intensive-processing product of turpentine and it is widely used in the synthesis of polymer. In this paper, its physicochemical properties were discussed. Its several synthesis methods were summarized, such as cyanide hydrolysis, cyanide reduction and azide reduction. However, these methods exist some defects. HCN and H_2 SO_4 used in the method of cyanide hydrolysis have high toxcity and high corrosivity. It would be easy to seriously pollute environment. Potassium borohydride and sodium borohydride used in the method of cyanide reduction, which belong to explosive compounds, have a certain dangerous nature. The products are difficult to separate for the method of azide reduction. Therefore, the synthesis technology of p-menthane-1,8-diamine needs a further optimization. At the same time, its applications were discussed, such as using for a curing agent of epoxy resin, a crosslinking agent, a capture agent of carbon dioxide and a synthesis ingredient. Finally, the research prospect of p-menthane-1,8-diamine on catalyst and bioactivity was reviewed.
p-Menthane-1,8-diamine, which has active chemical property, is an important intensive-processing product of turpentine and it is widely used in the synthesis of polymer. In this paper, its physicochemical properties were discussed. Its several synthesis methods were summarized, such as cyanide hydrolysis, cyanide reduction and azide reduction. However, these methods exist some defects. HCN and H_2 SO_4 used in the method of cyanide hydrolysis have high toxcity and high corrosivity. It would be easy to seriously pollute environment. Potassium borohydride and sodium borohydride used in the method of cyanide reduction, which belong to explosive compounds, have a certain dangerous nature. The products are difficult to separate for the method of azide reduction. Therefore, the synthesis technology of p-menthane-1,8-diamine needs a further optimization. At the same time, its applications were discussed, such as using for a curing agent of epoxy resin, a crosslinking agent, a capture agent of carbon dioxide and a synthesis ingredient. Finally, the research prospect of p-menthane-1,8-diamine on catalyst and bioactivity was reviewed.
引文
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[25]ROCHELLE G T.Amine scrubbing for CO2 capture[J].Science,2009,325(5948):1652-1654.
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[28]LEE S S,MUN S M,CHOI W J,et al.Absorption characteristics of new solvent based on a blend of AMP and 1,8-diamino-p-menthane for CO2 absorption[J].Journal of Environmental Sciences,2012,24(5):897-902.
[29]LI J,LIN X,NING P G,et al.Measurement and modelling of the solubility of carbon dioxide in aqueous 1,8-p-menthane-diamine solution[J].The Journal of Chemical Thermodynamics,2014,71(71):64-70.
[30]王海卫.含1,2,4-三氮唑和哌嗪的酰胺类衍生物的合成,表征及生物活性的测定[D].郑州:郑州大学,2013.
[31]曲波.含氮杂环化合物的设计合成[D].青岛:青岛科技大学,2007.
[32]杨鹏.新型杂环并萘酰亚胺化合物的设计合成及生物活性研究[D].大连:大连理工大学,2007.
[33]周杰.席夫碱型钯配合物催化剂在碳酸二苯酯合成中的应用[D].天津:河北工业大学,2013.
[34]张鹏.壳聚糖席夫碱钯催化剂在Heck反应中的催化性能研究[D].郑州:郑州大学,2006.
[35]MORAT C,RASSAT A,REY P.Preparation des dinitro-1,8-p-menthanes Z et E,et determination de leur stereochimie[J].Tetrahedron,1975,31(23):2927-2930.
[2]WEI K,ZHU G,TANG Y,et al.The effects of crosslink density on thermo-mechanical properties of shape-memory hydro-epoxy resin[J].Journal of Materials Research,2013,28(20):2903-2910.
[3]BURITZ R S,BURNHAM J,SCHWIDER A W.Polyester fiber-vacuum impregnated epoxy resin insulation system for high voltage transformers:US3979530[P].1976-09-07.
[4]SABRA A,PASCAULT J P,SEYTRE G.Epoxy thermosetting systems based on cycloaliphatic diamines[J].Journal of Applied Polymer Science,1986,32(5):5147-5160.
[5]魏堃,唐玉生,朱光明,等.氢化环氧树脂体系形状记忆效应的研究[J].航空材料学报,2012,32(3):57-62.
[6]DONNELLAN T,ROYLANCE D.The curing of a bisphenol A‐type epoxy resin with 1,8-diamin-p-menthane[J].Polymer Engineering&Science,1982,22(13):821-825.
[7]BORTNICK N M.Method of preparing 1,8-diamino-p-menthane:US2632022[P].1953-03-17.
[8]赵振东,刘先章.松节油的精细化学利用(Ⅷ)--国内外现状及发展动向[J].林产化工通讯,2002,36(2):37-42.
[9]ZHU S J,XU S C,YI X Q,et al.High value-added application of turpentine as a potential renewable source for the synthesis of heterocyclic Schiff base derivatives of cis-1,8-p-menthane-diamine serving as botanical herbicides[J].Industrial Crops&Products,2018,115(5):111-116.
[10]XU S C,ZHU S J,YI X J,et al.Design,synthesis and evaluation of novel cis-p-menthane type Schiff base compounds as effective herbicides[J].Chinese Chemical Letters,2017,28(7):1509-1513.
[11]任会学,林吉茂,薛云,等.1-乙酰氨基-3,5-二甲基金刚烷的水解反应研究[J].精细化工中间体,2005,35(2):29-31.
[12]张海连,王继宇,刘孝波.聚酯-酰胺的水解降解行为[J].合成化学,2004,12(1):94-96.
[13]BASIUK V A,MONTIEL H M.Glycine amide hydrolysis with water and OH radical:a comparative DFT study[J].Advances in Space Research,2005,36(2):209-213.
[14]GHOSH M,CONROY J L,SETO C T.Hydrolysis of amides catalyzed by 4-heterocyclohexanones:small molecule mimics of serine proteases[J].Angewandte Chemie(International Edition),1999,38(4):514-516.
[15]SAKAKURA M,TAKAYAMA M.Improved sonolytic hydrolysis of peptides in aqueous solution with addition of 1,4-benzenedithiol[J].Ultrasonics Sonochemistry,2012,19(3):615-620.
[16]段培高.近临界水中腈,酰胺的水解反应研究[D].上海:华东师范大学,2009.
[17]苏瑞景.剩余污泥酶法水解制备蛋白质,氨基酸及其机理研究[D].上海:东华大学,2013.
[18]ZHAO Z D,GU Y,LU Y J,et al.Skeletal rearrangement in the Ritter reaction of turpentine:a novel synthesis of p-menthane diamides[J].Fine Chemicals,2008,41(2):124-127.
[19]赵振东,徐士超,陈玉湘,等.一种由松节油制备1,8-孟烷二乙酰胺的方法:CN201510329574.8[P].2015-06-15.
[20]代小妮,李俊锋,唐悫君,等.孟烷二胺的制备方法:CN201010559262.3[P].2011-05-04.
[21]钟兴,吴涛,陈佳,等.一种1,8-萜二胺合成的方法:CN201110103300.9[P].2012-10-24.
[22]赵振东,冯志勇,毕良武,等.由1,8-萜二醇制备孟烷二胺的方法:CN200610096308.6[P].2009-05-13.
[23]WEI K,ZHU G,TANG Y,et al.Shape-memory effects of a hydro-epoxy resin system[J].Journal of Polymer Research,2013,20(5):1-7.
[24]ENGELHARDT F,RIEGEL U.Hydrophilic highly swellable hydmgels:US5668236[P].1997-09-16.
[25]ROCHELLE G T.Amine scrubbing for CO2 capture[J].Science,2009,325(5948):1652-1654.
[26]LI Y G,MATHER A E.Correlation and prediction of the solubility of carbon dioxide in a mixed alkanolamine solution[J].Industrial&Engineering Chemistry Research,1994,33(8):2006-2015.
[27]LI Y,MATHER A E.Correlation and prediction of the solubility of CO2 and H2S in aqueous solutions of methyldiethanolamine[J].Industrial&Engineering Chemistry Research,1997,36(7):2760-2765.
[28]LEE S S,MUN S M,CHOI W J,et al.Absorption characteristics of new solvent based on a blend of AMP and 1,8-diamino-p-menthane for CO2 absorption[J].Journal of Environmental Sciences,2012,24(5):897-902.
[29]LI J,LIN X,NING P G,et al.Measurement and modelling of the solubility of carbon dioxide in aqueous 1,8-p-menthane-diamine solution[J].The Journal of Chemical Thermodynamics,2014,71(71):64-70.
[30]王海卫.含1,2,4-三氮唑和哌嗪的酰胺类衍生物的合成,表征及生物活性的测定[D].郑州:郑州大学,2013.
[31]曲波.含氮杂环化合物的设计合成[D].青岛:青岛科技大学,2007.
[32]杨鹏.新型杂环并萘酰亚胺化合物的设计合成及生物活性研究[D].大连:大连理工大学,2007.
[33]周杰.席夫碱型钯配合物催化剂在碳酸二苯酯合成中的应用[D].天津:河北工业大学,2013.
[34]张鹏.壳聚糖席夫碱钯催化剂在Heck反应中的催化性能研究[D].郑州:郑州大学,2006.
[35]MORAT C,RASSAT A,REY P.Preparation des dinitro-1,8-p-menthanes Z et E,et determination de leur stereochimie[J].Tetrahedron,1975,31(23):2927-2930.