酯基季铵盐的绿色化改进与碳酸二甲酯季铵化反应的研究
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摘要
酯基季铵盐作为一种生物降解性优良的阳离子表面活性剂,已广泛应用于纺织、印染、皮革、合成纤维、造纸和机械行业等领域,是目前“绿色柔软剂”的典型代表。但因其生产工艺的限制,存在产品质量不高、制备工艺有待改进、制备过程中使用剧毒季铵化剂等问题。碳酸二甲酯(DMC)是近年来颇受重视的一种用途广泛的绿色化学品,由于其分子中含有甲基基团,故可作为季铵化试剂使用。本文主要是对酯基季铵盐的制备工艺进行绿色化改进,并对碳酸二甲酯的季铵化反应进行研究,为拓展碳酸二甲酯在阳离子表面活性剂制备中的绿色化应用奠定一定的基础。
开发了环路反应装置制备酯胺的新工艺路线,成功合成了质量较高的酯胺产品。在相同的反应条件下同传统釜式搅拌工艺进行了多方面对比,结果表明环路反应装置具有较高的传质传热效率,不仅使反应时间缩短1/3,而且产品质量高、色泽好,能源及氮气消耗低,它具有的气相自循环特性实现了反应过程的零排放。
为解决传统酯胺化反应催化剂的残留和回用问题,进一步提高酯胺产品的选择性,开发了适用于酯胺化反应的负载硫酸锆(ZS)的SBA-15固体酸催化剂(ZS/SBA-15)。通过ZS/SBA-15与传统催化剂比较,发现当以20%ZS/SBA-15(6)作为酯胺化反应的催化剂时,不仅可有效提高原料的转化率和产品中单双酯含量,而且解决了催化剂的残留和回用问题,提高了酯胺产品的内在质量。
研究了碳酸二甲酯与酯胺的季铵化反应,并确定了其较优的反应条件。1H-NMR表征结果说明成功合成了新的绿色酯基季铵盐产品—双硬脂酸乙酯基羟乙基甲基碳酸甲酯铵(EQDMC)。反应中过量碳酸二甲酯和溶剂回收后不需经过任何处理即可循环使用。通过EQDMC与传统柔软剂—双硬脂酸乙酯基羟乙基甲基碳酸甲酯铵(EQDMS)和D1821的比较,发现EQDMC在性能上可替代EQDMS和D1821,是一种新的绿色柔软剂产品。
研究了碳酸二甲酯与不同碳链长度的单、双烷基叔胺季铵化反应的优化条件。结果表明:相同反应条件下,单烷基叔胺的反应速率和季铵化率与其碳链长度无关,其季铵化率均在99%左右;而双烷基叔胺的反应速率和季铵化率与其碳链长度有很大关系,碳链长度越长反应速率越慢。通过分子空间结构模拟发现,引起这种差异的主要原因是空间位阻的不同。同时,利用甲基碳酸酯季铵盐和盐酸反应合成了1831,证明了甲基碳酸酯季铵盐可以作为合成多种负离子季铵盐的原料,为丰富季铵盐的种类提供了前期试验基础。
Ester quaternary ammonium salt (EQ) as an excellent biodegradable cationic surfactant, has been widely used in textile, printing and dyeing, leather, synthetic fiber, paper making and machinery industries, which is a typical kind of“green softener”. However, some defects, existing in the production process of EQ, cause the product quality and preparation process should be improved. Further more, quaternary ammonium agent used in the production process of EQ was toxic, which should be improved too. Dimethyl carbonate (DMC), which is a kind of green reagent, has received much attention in recent years. The molecule of DMC containing methyl group can be used as a new type of quaternization agent. This article mainly investigated the green improvement of EQ preparation process and the application of dimethyl carbonate as a quaternization agent, which would lay the foundation for the application of dimethyl carbonate in the preparation of green cationic surfactant.
Loop reactor process had been developed to prepare esteramine, and the high quality of esteramine was successfully synthesized. Compared with the conventional stirred tank process under the optimal experimental conditions, the results showed that the loop reactor process not only had higher heat and mass transfer efficiency with 1/3 reaction time being shortened and low consumption of energy and nitrogen, but also obtained higher quality and lighter color of the products. Further more, there was no emission in the reaction process.
To overcome the problems for the homogenous catalysts that catalysts remained in the products and can not be reused, and improve the selectivity of esteramine, zirconium sulfate (ZS) supported on SBA-15 mesoporous molecular sieve solid acid catalyst (ZS/SBA-15) were developed for esteramine synthesis. In comparison with the traditional catalyst, ZS/SBA-15 showed better catalytic activity and selectivity. When 20%ZS/SBA-15(6) was taken as the catalyst of esteramine synthesis, it not only could improve the conversion of raw materials, but also increased the content of mono-esteramine and di-esteramine. Moreover, this kind of improvement could solve the catalyst residues and be reused effectively, and benefit the intrinsic quality of ester amine products.
The quaternization of DMC and esteramine was studied. The reaction conditions were optimized by orthogonal test method. The characterization results of 1H-NMR indicated that the new green EQDMC (Di-alkyl diester hyroxylethyl methyl ammonium methyl carbonate) was synthesized successfully. Excessive dimethyl carbonate and the solvent could be recovered and recycled without any extra-treatment. EQDMC could replace the traditional softener as a new green softener.
The quaternization reaction conditions of dimethyl carbonate and alkyl tertiary amine with different carbon chain lengths of single and double were also optimized. The results showed that: the reaction rate and conversion of the single alkyl tertiary amine had nothing to do with the carbon chain length at the same reaction conditions, and the conversions were about 99%, but the reaction rate and conversion of dual alkyl tertiary amine had a lot to do with carbon chain lengths, and the reaction rate slowed with the longer carbon chain. Based on the molecular space structure simulations, a conclusion was drawn that the difference was mainly due to the space steric hindrance.
At the same time, 1831 was synthesized by the reaction of quaternary ammonium salt methyl carbonate and hydrochloric acid, which proved that quaternary ammonium methyl carbonate could be used as the materials of preparing various counter ion of quaternary ammonium salts. During this, a pre-test foundation has been built for enriching the types of quaternary ammonium salts.
开发了环路反应装置制备酯胺的新工艺路线,成功合成了质量较高的酯胺产品。在相同的反应条件下同传统釜式搅拌工艺进行了多方面对比,结果表明环路反应装置具有较高的传质传热效率,不仅使反应时间缩短1/3,而且产品质量高、色泽好,能源及氮气消耗低,它具有的气相自循环特性实现了反应过程的零排放。
为解决传统酯胺化反应催化剂的残留和回用问题,进一步提高酯胺产品的选择性,开发了适用于酯胺化反应的负载硫酸锆(ZS)的SBA-15固体酸催化剂(ZS/SBA-15)。通过ZS/SBA-15与传统催化剂比较,发现当以20%ZS/SBA-15(6)作为酯胺化反应的催化剂时,不仅可有效提高原料的转化率和产品中单双酯含量,而且解决了催化剂的残留和回用问题,提高了酯胺产品的内在质量。
研究了碳酸二甲酯与酯胺的季铵化反应,并确定了其较优的反应条件。1H-NMR表征结果说明成功合成了新的绿色酯基季铵盐产品—双硬脂酸乙酯基羟乙基甲基碳酸甲酯铵(EQDMC)。反应中过量碳酸二甲酯和溶剂回收后不需经过任何处理即可循环使用。通过EQDMC与传统柔软剂—双硬脂酸乙酯基羟乙基甲基碳酸甲酯铵(EQDMS)和D1821的比较,发现EQDMC在性能上可替代EQDMS和D1821,是一种新的绿色柔软剂产品。
研究了碳酸二甲酯与不同碳链长度的单、双烷基叔胺季铵化反应的优化条件。结果表明:相同反应条件下,单烷基叔胺的反应速率和季铵化率与其碳链长度无关,其季铵化率均在99%左右;而双烷基叔胺的反应速率和季铵化率与其碳链长度有很大关系,碳链长度越长反应速率越慢。通过分子空间结构模拟发现,引起这种差异的主要原因是空间位阻的不同。同时,利用甲基碳酸酯季铵盐和盐酸反应合成了1831,证明了甲基碳酸酯季铵盐可以作为合成多种负离子季铵盐的原料,为丰富季铵盐的种类提供了前期试验基础。
Ester quaternary ammonium salt (EQ) as an excellent biodegradable cationic surfactant, has been widely used in textile, printing and dyeing, leather, synthetic fiber, paper making and machinery industries, which is a typical kind of“green softener”. However, some defects, existing in the production process of EQ, cause the product quality and preparation process should be improved. Further more, quaternary ammonium agent used in the production process of EQ was toxic, which should be improved too. Dimethyl carbonate (DMC), which is a kind of green reagent, has received much attention in recent years. The molecule of DMC containing methyl group can be used as a new type of quaternization agent. This article mainly investigated the green improvement of EQ preparation process and the application of dimethyl carbonate as a quaternization agent, which would lay the foundation for the application of dimethyl carbonate in the preparation of green cationic surfactant.
Loop reactor process had been developed to prepare esteramine, and the high quality of esteramine was successfully synthesized. Compared with the conventional stirred tank process under the optimal experimental conditions, the results showed that the loop reactor process not only had higher heat and mass transfer efficiency with 1/3 reaction time being shortened and low consumption of energy and nitrogen, but also obtained higher quality and lighter color of the products. Further more, there was no emission in the reaction process.
To overcome the problems for the homogenous catalysts that catalysts remained in the products and can not be reused, and improve the selectivity of esteramine, zirconium sulfate (ZS) supported on SBA-15 mesoporous molecular sieve solid acid catalyst (ZS/SBA-15) were developed for esteramine synthesis. In comparison with the traditional catalyst, ZS/SBA-15 showed better catalytic activity and selectivity. When 20%ZS/SBA-15(6) was taken as the catalyst of esteramine synthesis, it not only could improve the conversion of raw materials, but also increased the content of mono-esteramine and di-esteramine. Moreover, this kind of improvement could solve the catalyst residues and be reused effectively, and benefit the intrinsic quality of ester amine products.
The quaternization of DMC and esteramine was studied. The reaction conditions were optimized by orthogonal test method. The characterization results of 1H-NMR indicated that the new green EQDMC (Di-alkyl diester hyroxylethyl methyl ammonium methyl carbonate) was synthesized successfully. Excessive dimethyl carbonate and the solvent could be recovered and recycled without any extra-treatment. EQDMC could replace the traditional softener as a new green softener.
The quaternization reaction conditions of dimethyl carbonate and alkyl tertiary amine with different carbon chain lengths of single and double were also optimized. The results showed that: the reaction rate and conversion of the single alkyl tertiary amine had nothing to do with the carbon chain length at the same reaction conditions, and the conversions were about 99%, but the reaction rate and conversion of dual alkyl tertiary amine had a lot to do with carbon chain lengths, and the reaction rate slowed with the longer carbon chain. Based on the molecular space structure simulations, a conclusion was drawn that the difference was mainly due to the space steric hindrance.
At the same time, 1831 was synthesized by the reaction of quaternary ammonium salt methyl carbonate and hydrochloric acid, which proved that quaternary ammonium methyl carbonate could be used as the materials of preparing various counter ion of quaternary ammonium salts. During this, a pre-test foundation has been built for enriching the types of quaternary ammonium salts.
引文
[1] Anastas P. T., Warner J. C.. Green Chemistry: Theory and Practice [M]. New York: Oxford University Press, Inc, 2000, 45-79.
[2]郭祥峰,贾丽华.阳离子表面活性剂及应用[M].北京:化学工业出版社,2002:7-21.
[3] Sudhir K. S., Bajpai M., Tyagi V. K.. Amine oxides: a review [J]. Journal of Oleo Science, 2006, 55(3): 99-119.
[4] Rolf P., Henkel K.. Cationic surfactants in laundry detergents and laundry aftertreatment aids [J]. Journal of the American Oil Chemists’Society, 1984, 61(2): 367-376.
[5] Waters J., Bebington W.. A new rinse conditioner active with improved environment properties [J]. Tenside Surfactants Detergents, 1991, 28(6): 460-467.
[6]邹文苑.织物柔软剂的发展趋势[J].日用化学工业,1999,5 (108):11-16.
[7]常青春.季铵盐型阳离子表面活性剂的发展及应用[J].佳木斯大学学报(自然科学版), 2003,21(4):503-506.
[8]杨雪萍,蒋文伟.新型柔软剂——硬脂酸三乙醇胺酯季铵盐合成与应用综述[J].皮革与化工,2008,25(6):25-29.
[9] Koto T., Ohtawa Y., Kaneko Y.. Biodegradable fabric compositions [P]. WO: 9964661, 1999-12-16.
[10]赵荣国,周绍箕.合成1-脂肪酰胺乙基-2-烷基咪唑啉的机理探讨[J].精细化工,1992,5(6):64-66.
[11] Gabriel R.. Amidation selective of fatty ester with N-(2-Amidoethy) ethanolamine under base catalysis [J]. Journal of the American Oil Chemists’Society, 1984, 61(5): 965-970.
[12] Friedli F. E., Koehle H. J., Fender M.. Upgrading triethanolamine esterquate performance to new levers [J]. Journal of Surfactants and Detergents, 2002, 5(3): 211-216.
[13] Puchta R., Krings P.. A new generation of softeners [J]. Tenside Surfactants Detergents, 1993, 30(3): 186-191.
[14] Phil S., Friedli F. E.. A study on the long-term stability and removal of quats on treated fabric [J]. Journal of Surfactants and Detergents, 2002, 5(3): 207-210.
[15]陈宗刚,吴赞敏,张爱.环境友好型织物柔软剂的研制[J].染料与染色,2004,41(3): 177-180.
[16]黄俊,曹平.中国衣物柔软剂的现状及对未来发展趋势的思考[J].日用化学品科学,2004,27(8):5-7.
[17]徐长卿,王丰收.铵酯的开发和应用-工业表面活性剂技术经济文集(5)[C].大连:大连出版社,1999:171-176.
[18]柯汉忠,程国娥.新型织物柔软剂PS-501的研制[J].印染助剂,2003,20(4):8-10.
[19]周弟,赵新,陈琳等.织物柔软剂的研究进展[J].化学工程师,2009,169(10):31-35.
[20]王一尘.阳离子表面活性剂的合成[M].北京:轻工业出版社,1984:47-51.
[21]丁忠传.纺织染整助剂[M].北京:化学工业出版社,1988:239-251.
[22]梁梦兰.表面活性剂和洗涤剂制备、性质、应用[M].北京:科技文献出版社,1990,172-174.
[23]索福喜,张万斌,江巩等.N,N-亚烃基脂肪酸双酰胺的合成及其润滑性能[J].华东化工学院学报,1993,1(5):191-197.
[24] Ruback W., Schut J.. Process for preparing fatty acid diesters of trialkanolamines [P]. EP: 295385, 1998-12-21.
[25] Yamamura M., Inokoshi J., Shiratsuchi K.. Fabric softener compositions [P]. EP: 472178, 1992– 02– 26.
[26]刘德荣.表面活性剂的合成与应用[M].成都:四川科学技术出版社,1987:77-78.
[27]赵荣国.咪唑啉及双酰胺类阳离子织物调理剂合成及其应用性能研究[D].北京:北京服装学院,1992.
[28]陈一飞.表面活性剂类柔软剂的柔软作用[J].四川丝绸,2001,(1):27—29.
[29] Zyschka R.,李卓.纺织柔软剂及其巧妙应用[[J].国际纺织导报,2001,(3):71—74.
[30]张平.以油脂为原料的织物柔软剂的现状[J].日用化学品科学, 2000, 23 (5):71-9, 12.
[31] Franklin R., Mendello R.. High di (alkyl fatty ester) quaternary ammonium compounds in fabric softening and personal care compositions [P]. US: 6037315, 2000– 03– 14.
[32] Howard J., Ormandy K. A.. A method of preparing fabric conditioning compositions [P]. WO: 0220706, 2002– 03– 14.
[33] Turner G. A., Emmons S. A.. Fabric softening composition [P]. WO: 9417168, 1994-08-04.
[34] Khan-Lodhi A. N., Whaley C.. Fabric softening composition [P]. WO: 9723590, 1997-07-03.
[35] Dewez J., Thibert E.. Stable fabric softener compositions [P]. WO: 9708285, 1997-03-06.
[36] Jacques A., Laitem L.. Fabric softening compositions providing enhanced performance and containing cationic softeners and fatty amides [P]. US: 6191101, 2001-02-20.
[37] Zappone M., Umstead D. J.. Fabric care composition containing polycarboxylate polymer andcompound derived from urea [P]. WO: 0116262, 2001-09-07.
[38] Ellson K. J., Wright J.. Use of fabric conditioning compositions for ironing benetts [P]. WO: 0146513, 2001-06-28.
[39] Jarvis A. N.. Fabric care composition [P]. EP: 1205538, 2002-05-15.
[40] Sakkab N., Brown D. R., Baker E. S.. Aqueous fabric softener compositions containing highly unsaturated active and chelant [P]. WO: 0134743, 2001-05-17.
[41] Grandmaire J., Hermosilla A.. Clear, concentrated liquid fabric softener compositions [P]. US: 5656585, 1997-08-12.
[42] Buron H. S., Jones C. W., Martinez Escolano. Fabric conditioning compositions [P]. WO: 0104254, 2001-01-18.
[43] Porta N., Weissen. Biodegradable fabric softening composition [P]. EP: 0638639, 1995-02-15.
[44] Chung A. H., Costa J. B., Denutte H. R. G.. Dryer-activated fabric conditioning and antistatic compositions with improved perfume longevity [P]. US: 5559088, 1996-09-24.
[45] Trius A., Humbert M.. Process for preparing quaternary ammonium compounds [P]. WO: 9101295, 1991-02-07.
[46] Wahl E., Bacon D.. Concentrated biodegradable quaternary ammonium fabric softener compositions and compounds containing intermediate iodine value unsaturated fatty acid chains [P]. US: 5562849, 1996-10-08.
[47] Baker E., Bodet J. F. Concentrated fabric softener compositions containing biodegradable fabric softeners [P]. US: 5545350, 1996-08-13.
[48] Naik A. R., Todt K. H., Wells M. A.. Fabric treatment materials [P]. US: 4137180, 1979-01-30.
[49]杨雪萍,蒋文伟,褚钰宇.硬脂酸三乙醇胺酯的合成优化[J].针织工业,2009,(8):64-67.
[50]李秋小,刑英站,周静怡等.环路反应器制备饱和脂肪酸甲酯的研究[J].表面活性剂工业,1998,(2):23～25,32.
[51]江琦.碳酸二甲酯在化工领域中的应用[J].石油化工,2000,29(2):144-147.
[52] Tundo P., Moraglio J.. Selective and continuous-flow mono-methylation of arylacetonitriles with dimethyl carbonate under gas-liquid phase-transfer catalysis conditions [J]. Journal of the Chemical Society, Perkin Transactions 1, 1989, (5): 1070-1071.
[53] Ouk S., Thieband S., Borredou E.. High performance method for O-methylation of phenol with dimethyl carbonate [J]. Applided Catalysis A: General, 2003, 241 (1-2): 227-233.
[54] Fu Z. H., Ono Y.. Selective N-monomethylation of aniline with dimethyl carbonate over Y-zeolites [J]. Catalysis letters, 1993, 22: 277-281.
[55] Selva M., Tundo P.. Selective N-methylation of primary aliphatic amines with dimethyl carbonate in the presence of alkali cation exchanged Y-faujasites [J]. Tetrahedron Letters, 2003, 44 (44): 8139-8142.
[56] Tundo P., Trotta F., Moraglio G.. Continuous-flow processes under gas-liquid phase-yransfer catalysis (GL-PTC) conditions: The reaction of dialkyl carbonates with phenol, alcohols, and mercaptants [J]. Industrial and Engineering Chemistry Research, 1988, 27: 1565-1571.
[57] Hacking M., Rantwijk F. V., Sheldon R. A.. Li-pase catalyzed reactions of aliphatic and arylaliphatic carbonic acid esters [J]. Journal of molecular Catalysis B, 2000, 9: 201-208.
[58] Shaikh Abbas Alli, Sivaram S.. Dialkyl and diaryl carbonates by carbonate interchange reaction with dimethyl carbonate [J]. Industrial and Engineering Chemistry Research, 1992, 31: 1167-1172.
[59] Roger A. G., West C. Pa. Catalytic process for the preparation of polyalkylene carbonates [P]. US: 5171830, 1992-12-15.
[60] Hafauo Y.. Production of diphenyl carbonate [P]. JP: 62277345, 1987-12-01.
[61] Mori S., Ida I., Ue M.. Process for producing quaternary salts [P]. US: 4892944, 1990-01-09.
[62] Werntz J. H.. Monoquaternary ammonium carbonates [P]. US: 2635100, 1953-04-14.
[63] Yagi O., Shimizu S.. Synthesis of pure tetramethylammonium hydroxide solution free from chloride by the electrolysis of its hydrogen carbonate [J]. Chemistry Letters, 1993, 22 (12): 2041-2044.
[64] Gary W. E., Duane E. W., Drew P.. Quaternary methyl carbonates: novel agents for fabric conditioning [J]. Journal of Surfactants and Detergents, 2005, 8 (4): 325-329.
[1]Miao Z. C., Yang J. Z., Wang L., et al. Synthesis of biodegradable lauric acid ester quaternary ammonium salt cationic surfactant and its utilization as calico softener [J]. Materials Letters, 2008, 62: 3450-3452.
[2] Mishra S., Tyagi V. K.. Ester quats: the novel class of cationic fabric softeners [J]. Journal of Oleo Science, 2007, 56(6): 269-276.
[3] Steiger P., Friedli F. E.. A study on the long-term stability and removal of quats on treated fabric [J]. Journal of Surfactants and Detergents, 2002, 5(3): 207-210.
[4] Weissen H. J., Porta N.. Biodegradable fabric softening composition [P]. EP: 0638639, 1995-02- 5.
[5]杨建洲,林里,付志刚等.生物可降解型阳离子酯表面活性剂的研究[J].日用化学工业,2005,35 (1):9-11,48.
[6] Haliza A. A., Parthiban S., Salmiah A.. Scaled-up production and optimization study of the esterification of palm-based fatty acid and triethanolamine [J]. Journal of Oil Palm Research, 2006, 18: 305-311.
[7] Friedli F. E., Koehle H. J., Fender M., et al. Upgrading triethanolamine esterquat performance to new levels [J]. Journal of Surfactants and Detergents, 5(3): 211-216.
[8] Baker Ellens, Bodet Jean-francois. Concentrated fabric softener compositions containing biodegradable fabric softeners [P]. US: 5545350, 1996-08-13.
[9] Rashmi T., Tyagi V. K., Khanna R. K.. Synthesis, Characterization and performance of tallow fatty acids and triethanolamine based esterquats [J]. Journal of Oleo Science, 2006, 55(7): 337-345.
[10]杨雪萍,蒋文伟,褚钰宇.硬脂酸三乙醇胺酯的合成优化[J].针织工业,2009,(8):64-67.
[11] Friedli F. E., Koehle H. J., Fender M.. Upgrading triethanolamine esterquate performance to new levers [J]. Journal of Surfactants and Detergents, 2002, 5(3): 211-216.
[12] Friedli F. E., Robert K., Toney C. J., et al. Novel new ester quaternaries for improved performance benefits as rinse cycle fabric softeners [J]. Journal of Surfactants and Detergents, 2001, 4(4): 401-405.
[13] Ruback W., Schut J.. Process for preparing fatty acid diesters of trialkanolamines [P]. EP: 295385, 1998-12-21.
[14] Sakata Y., Inokoshi J., Katoh T., et al. Liquid softener composition, novel quaternary ammonium salt,and process for the preparation of said salt [P]. US: 5476597, 1995-12-19.
[15] Miller J. H., Sauer J. D., Delaet D. L.. Process for preparing quaternary ammonium compounds [P]. US: 5599990, 1997-02-04.
[16] Laurent L., Dierendinck V., Zahradnik J., et al. Loop reactor-a feasible alternative to stirred tank reactors [J]. Industrial and Engineering Chemistry Research, 1998, 37(3):734-738.
[17] John T.. Reactions and synthesis in surfactant systepns [M]. New York: Marcel Dekkle, Inc., 2001, 7-11.
[18] Urs Geser, Richard Malone, Len Fabiano, Rene Duveen. Novelty in HH Loop Reactor Technologies for Ethoxylations and Propoxylations [C]. 10th International Conference on Surfactant & Detergent (ICSD208), 2008, Shanghai, China.
[19] Rene F D.. New frontiers in reactor design [C]. Billingham, UK: The Royal Society of Chemistry. 1998, 1-14.
[20]张卫民,李秋小,缪列平等.环路反应器工程研究[J].日用化学工业,1999,(6):5-7.
[21]李秋小,刑英站,周静怡等.环路反应器制备饱和脂肪酸甲酯的研究[J].表面活性剂工业,1998,(2):23-25, 32.
[22]聂金泉.用于气固液多相反应的回路反应器[J].化工装备技术,1994,15(3):21-25.
[23]袁少明,周庚生,张高勇.喷射反应器及其应用.日用化学工业,2003,33(1):40-44.
[24]马宝歧.喷射式气-液反应器[J].石油化工,1997,(6):284– 292.
[25]邢英站,李秋小,周静怡等.环路反应器与搅拌釜装置生产十二烷基二甲基叔胺的比较[J].日用化学品科学,2000,23(S1):53– 55.
[26]陆宏圻.喷射技术理论及应用[M].武汉:武汉大学出版社,2004,398-424.
[27] Wilkes A. J., Jacobs C., Walraven G., et al. Characterization of quaternized triethanolamine esters (esterquats) by HPLC, HRCGC and NMR [C]. 4th World Surfactants Congress, Barcelona: Marcel Dekker Inc. 1996, 389-402.
[1] Shilpi M., Tyagi V. K.. Ester quats: The novel class of cationic fabric softeners [J]. Journal of Oleo Science, 2007, 56: 269-276.
[2] Tyagi R., Tyagi V. K.. Synthesis, Characterization and performance of tallow fatty acids and triethanolamine based esterquats [J]. Journal of Oleo Science, 2006, 55: 337-345.
[3] James H. C., Sjack E., Karen W.. Catalysis for green chemistry: ultrahigh loaded mesoporous solid acids [J]. Comptes Rendus de l’Académie des Sciences - Series IIC - Chemistry, 2000, 3(6): 399-404.
[4] Kazuo O., Chen X., Katsumi T.. Water-tolerant catalysis of a silica composite of a sulfonic acid resin, Aciplex [J]. Applied Catalysis A: General, 2000, 190(1-2): 253-260.
[5]曹维良,张敬畅,吕青.CZ固体酸催化剂的应用及最佳反应工艺条件的优化[J].石油化工高等学校学报,2000,13(1):42-46.
[6]张敬畅,孟秀娟,曹维良.新型疏水性固体酸Zr(SO4)2/AC催化剂的制备及其催化性能[J].催化学报,2006,27(2):135-138.
[7]李峰,李隽春,段雪.新型层状表面相锆基固体酸催化酯化反应研究[J].精细化工,2002,19(1):32-35.
[8]李葆,战永复,李连忠等.含水硫酸锆作为酯化催化剂的研究[J].催化学报,1989,10(3):331-333.
[9] Li R. F., Yu F., Li F. X., et al. One-pot synethesis of superacid catalytic material SO42-/ZrO2-SiO2 with thermostable well-ordered mesoporous structure [J]. Journal of Solid State Chemistry, 2009, 182: 991-994.
[10] Wang J. H., Mou C. Y.. Characterizations of aluminum-promoted sulfated zirconia on mesoporous MCM-41 silica: Butane isomerization [J]. Microporous and Mesoporous Materials, 2008, 110: 260-270.
[11] Juan J. C., Jiang Y. J., Zhang J. C.. Supported zirconium sulfate on carbon nanotubes as water-tolerant solid acid catalyst [J]. Materials Research Bulletin, 2007, 42: 1278-1285.
[12]张敬畅,孟秀娟,曹维良.新型疏水性固体酸Zr(SO4)2/AC催化剂的制备及其催化性能[J].催化学报,2006,27(2):135-138.
[13] Jiang Y. J., Juan J. C., Zhang J. C.. Preparation and catalytic application of novel water tolerant solid acid catalysts of zirconium sulfate/HZSM-5 [J]. Chemical Research in Chinese Universities, 2007, 23: 349-354.
[14]张微,徐恒泳,毕亚东等.介孔分子筛SBA-15的改性研究进展[J].化工进展,2007,26(2):152-157.
[15] Li F. X., Yu F., Li Y. L., et al. Direct synthesis of Zr-SBA-15 mesoporous molecular sieves with high zirconium loading: characterization and catalytic performance after sulfated [J]. Microporous and Mesoporous Materials, 2007, 101: 250-255.
[16] Wang X. G., Landau M. V., Rotter H., et al. TiO2 and ZrO2 crystals in SBA-15 silica: performance of Pt/TiO2(ZrO2)/SBA-15 catalyst in ethyl acetate combustion [J]. Journal of Catalysis, 2004, 222: 565-571.
[17] Yang C. M., Kalwei M., Schuth F.. Gold nanoparticles in SBA-15 showing catalytic activity in CO oxidation [J]. Journal of Applied Catalysis, 2003, 254: 289-296.
[18]周丽绘,张利中,刘洪来.晶化温度对介孔材料SBA-15结构与形貌的影响[J].过程工程学报,2006,6(3):499-502.
[19]高波,朱广山,傅学奇等.介孔分子筛SBA-15中α-胰凝乳蛋白酶组装及催化活性研究[J].高等学校化学学报,2003,24(6):1100-1102.
[20] Kim T. H., Jang M., Park J. K.. Bifunctionalized mesoporous molecular sieve for perchlorate removal [J]. Microporous and Mesoporous Materials, 2008, 108: 22-28.
[21] Zhao D. Y., Feng J. L., Huo Q. S.. Triblock copolymer synthesis of mesoporous silica with periodic 50-300 angstrom pore [J]. Science, 1998, 279: 548-552.
[22] Zhao D. Y., Huo Q. S,. Feng J. L., et al. Nonionic triblock and star diblock copolymer and oligomeric surfactant synthese of highly ordered, hydrothermally stable, mesoporous silica structures [J]. Journal of the American Oil Chemists Society, 1998, 120: 6024-6036.
[23]李峰,何静,张保国.四水硫酸锆热分解反应的程序升温动态分析[J].北京化工大学学报,1996,23(2):58-61.
[24] Friedli F. E., Koehle H. J., Fender M.. Upgrading triethanolamine esterquat performance to new levels [J]. Journal of Surfactants and Detergents, 2002, 5: 211-216.
[25]李隽春,张慧,段雪等.Hβ负载锆催化剂的研制及其催化性能和结构性能的研究[J].燃料化学学报,2002,30(4):358-362.
[1] Waters J., Bebington W.. A new rinse conditioner active with improved environmental properties [J]. Tenside Surfactants Detergents, 1991, 28(6): 460～467.
[2] Puchta R., Krings P.. A new generation of softeners [J]. Tenside Surfactants Detergents, 1993, 30(3): 186～191.
[3] Steiger P., Friedli F. E.. A study on the long-term stability and removal of quats on treated fabric [J]. Journal of Surfactants and Detergents, 2002, 5(3): 207～210.
[4] Weissen H. J., Porta N.. Biodegradable fabric softening composition [P]. EP: 0638639, 1995 - 02 - 15.
[5]杨建洲,林里,付志刚等.生物可降解型阳离子酯表面活性剂的研究[J].日用化学工业, 2005, 35 (1) : 9 - 11, 48.
[6] Trius A., Humbert M.. Process for preparing quaternary ammonium compounds [P]. WO: 9101295, 1991-02-07.
[7] Wahl E., Bacon D.. Concentrated biodegradable quaternary ammonium fabric softener compositions and compounds containing intermediate iodine value unsaturated fatty acid chains [P]. US: 5562849, 1996-10-08.
[8] Baker E., Bodet J. F.. Concentrated fabric softener compositions containing biodegradable fabric softeners [P]. US: 5545350, 1996-08-13.
[9] Naik A. R., Todt K. H., Wells M. A.. Fabric treatment materials [P]. US: 4137180, 1979-01-30.
[10]耿涛,李秋小,李运玲.硬脂酸三乙醇胺酯季按盐的合成[J].皮革化工, 2004, 21(4): 21-27.
[11]徐宝财,聂红艳,水金环.碳酸二甲酯与阳离子表面活性剂合成[J].第十届中国科协年会第18分会场:二氧化碳减排和绿色化利用与发展研讨会,2008:88-91.
[12] Yoshio O.. Dimethyl carbonate for environmentally benign reactions [J]. Catalysis today, 1997, 35: 15-25.
[13] Pietro T., Manurizio S.. The chemistry of dimethyl carbonate [J]. Accounts of Chemical Research, 2002, 35(9): 706-716.
[14]张建西,张大洋,赵鸣玉等.用碳酸二甲酯和环戊二烯制备甲基环戊二烯的研究[J].沈阳化工学院学报,2003,17(1):1-3.
[15] Ouk S., Thiebaud S., Borredon E., et al. O-Methylation of phenolic commounds with dimethylcarbonate under solid/liquid phase transfer system [J]. Tettahedron Letter, 2002, 43: 2661-2663.
[16]宋锡瑾,王常申.合成苯甲醚的新工艺[J].精细化工,2000,17(1):42-44.
[17]郭俊胜.合成间甲基苯甲醚的新方法[J].河南化工,2001,2:12-13.
[18] Jiang X. L., Tiwari A., Thompson M., et al. A practical method for N-Methylation of indoles using dimethyl carbonate [J]. Oraganic Process Reseach and Development, 2001, 5: 604-608.
[19] Bomben A., Selva M., Tundo P.. Dimethylcarbonate as a methylating agent [J]. Journal of Chemical Research, 1997, 448-449.
[20]吴如春,谢涛,李媚.碳酸二甲酯合成体系的气相色谱分析法[J].广西民族大学学报(自然科学版),2008,14(4):73-75.
[21]汪正范等.色谱定性与定量[M].北京:化学工业出版社,2001:11- 13.
[22]陈延辉,李萍.尿素与甲醇合成碳酸二甲酯的气相色谱分析[J].哈尔滨师范大学自然科学学报,2006,22(2):97-99.
[23]李光兴,许汉昌,陈兵等.合成碳酸二甲酯产物气相色谱分析[J].湖北化工,1995,12 (4):56-58.
[24]王华,许红云,吴砚会.甲醇氧化羰化制碳酸二甲酯产物气相色谱分析[J].天然气化工,2002,27 (4):50-52.
[25]王高升,余晓峰,汪列敏.气相法合成的碳酸二甲酯的色谱分析[J].浙江化工,2002,33 (1):54-55.
[26]莫婉玲,熊辉,黄荣生等.甲醇液相氧化羰化合成碳酸二甲酯的色谱分析[J].江西科学,2003,21 (1):15-17.
[27]熊冬生,林福兰.气相色谱法测定碳酸二甲酯的含量[J].化学分析计量,2003,12 (4):19-21.
[28] Choi J. C., He L. N., Yasuda H., et al. Selective and high yield synthesis of dimethyl carbonate directly from carbon dioxide and methanol [J]. Green Chemistry, 2002(4): 230 - 234.
[29] Isaacs N., Sullivan B. O., Verhaelen C.. High pressure routes to dimethyl carbonate from supercritical carbondioxide [J]. Tetrahedron, 1999, 55: 11949-11959.
[30]潘鹤林,徐志珍,宋新杰等.合成碳酸二甲酯的技术进展[J].浙江化工,1999,30(1):32– 35.
[31]王建军,朱红军.碳酸二甲酯国内外生产及技术发展概况[J].化学工程师,2003(4):41- 42,45.
[32]钟顺和,黎汉生,王建伟等.用二氧化碳和甲醇直接合成碳酸二甲酯的研究[J].石油炼制与化工,2000,31(6):51– 55.
[1]蒋兴材,金康生.纺织品柔软剂[J].宁波化工,1990,(2):8- 12.
[2]倪捷.织物用柔软剂的现状和发展新课题[J].上海染料,1996,(5):11- 20.
[3]冯亚青,王利军,陈立功等.助剂化学及工艺学[M].北京:化学工业出版社,1997:344-359.
[4]杨栋梁.织物的柔软整理(三) [J].印染助剂,1999,16(3):33- 34.
[5]刘昌龄.纺织品柔软整理和柔软剂[J].河南纺织科技,1996,4:6- 9.
[6]唐增荣.纺织品柔软整理剂的应用研究(下) [J].染整科技,2000,2:19- 23.
[7]郭志军.织物柔软整理与柔软剂[J].纺织装饰织物,1997,2:21- 23.
[8]黄茂福.纺织助剂的基本特性、检测与应用(二)[J].染整科技,1996,4:46- 55.
[9]陈荣圻.纺织品柔软剂(一)[J].印染,1993,19(3):38- 41.
[10]张先亮,陈新兰,唐红定.精细化学品化学[M].武汉大学出版社,2008:247- 248.
[11]王丰收.新型柔软剂—烷基咪唑啉酯及其季铵盐的性能[J].日用化学工业,2000,2: 9-10.
[12] Jeannene A.. How to choose cationics for fabric softeners [J]. Journal of the American Oil Chemists’Society, 1983(60):1166-1169.
[13] Egan R. R.. Cationic surface active agents as fabric softeners [J]. Journal of the American Oil Chemists’Society, 1978(55): 118-121.
[1] Ralph F., Michael D. H., Joseph Z.. Cationic and amine-based surfactants [J]. Oleo Chemical Manufacture and Applications, 2001, 11: 23-54.
[2] Franklin R., Mendello R.. High di (alkyl fatty ester) quaternary ammonium compounds in fabric softening and personal care compositions [P]. US: 6037315, 2000-03-14.
[3] Howard Jane, Ormandy Kevin Anthony. A method of preparing fabric conditioning compositions [P]. WO: 0220706, 2002-03-14.
[4] Turner G. A., Emmons S. A.. Fabric softening composition [P]. WO: 9417168, 1994-08-04.
[5] Khan-Lodhi A. N., Whaley C.. Fabric softening composition [P]. WO: 9723590, 1997-07-03.
[6] Dewez J., Thibert E.. Stable fabric softener compositions [P]. WO: 9708285, 1997-03-06.
[7] Jacques A., Laitem L.. Fabric softening compositions providing enhanced performance and containing cationic softeners and fatty amides [P]. US: 6191101, 2001-02-20.
[8] Zappone M., Umstead D. J.. Fabric care composition containing polycarboxylate polymer and compound derived from Urea [P]. WO: 0116262, 2001-09-07.
[9] Ellson K. J., Wright J.. Use of fabric conditioning compositions for ironing benetts [P]. WO: 0146513, 2001-06-28.
[10]徐宝财,聂红艳,水金环.碳酸二甲酯与阳离子表面活性剂合成[J].第十届中国科协年会第18分会场:二氧化碳减排和绿色化利用与发展研讨会,2008:88-91.
[11]舒婷,李光兴.碳酸二甲酯作甲基化试剂的研究进展[J].化工中间体,2008,1:20-23.
[12] Yoshio O.. Dimethyl carbonate for environmentally benign reactions [J]. Catalysis Today, 1997, 35: 15-25.
[13] Pietro T., Manurizio S.. The chemistry of dimethyl carbonate [J]. Accounts of Chemical Research, 2002, 35(9): 706-716.
[14]张建西,张大洋,赵鸣玉等.用碳酸二甲酯和环戊二烯制备甲基环戊二烯的研究[J].沈阳化工学院学报,2003,17(1):1-3.
[15] Ouk S., Thiebaud S., Borredon E., et al. O-Methylation of phenolic commounds with dimethyl carbonate under solid/liquid phase transfer system [J].Tettahedron Letter, 2002, 43: 2661-2663.
[16]宋锡瑾,王常申.合成苯甲醚的新工艺[J].精细化工,2000,17(1):42-44.
[17]郭俊胜.合成间甲基苯甲醚的新方法[J].河南化工,2001,2:12-13.
[18] Jiang X. L., Tiwari A., Thompson M., et al. A practical method for N-methylation of indoles using dimethyl carbonate [J]. Oraganic Process Reseach and Development, 2001, 5: 604-608.
[19] Bomben A., Selva M., Tundo P.. Dimethyl carbonate as a methylating agent [J]. Journal of Chemical Research, 1997, 448-449.
[20] Gary W. E., Weisshaar D. E., Paulson D.. Quaternary methyl carbonates: novel agents for fabric conditioning [J]. Journal of Surfactants and Detergents, 2005, 8 (4): 325-329.
[21] Mori S., Ida I.. Process for producing quaternary salts [P]. US: 4892944, 1990-01-09.
[22] Shumpei S., Moses L., Toshitsura C.. Method for production of aqueous quaternary ammonium hydroxide solution [P]. US: 4634509, 1987-01-06.
[23] Tetsuo A., Eiji S., Jiro I.. Process for production of quaternary ammonium hydroxides [P]. US: 4776929, 1988-10-11.
[24]郑卓群.咪唑类离子液体催化下合成季铵盐的研究[D].浙江:浙江师范大学,2006.
[25]蒋波,詹晓力,陈丰秋.季铵化反应中的溶剂效应[J].化学通报,2006,69:1-6.
[26]唐红萍,杨明德,何培炯.季铵盐N263的非水滴定分析[J].冶金分析,2002,22(2):51-53.
[2]郭祥峰,贾丽华.阳离子表面活性剂及应用[M].北京:化学工业出版社,2002:7-21.
[3] Sudhir K. S., Bajpai M., Tyagi V. K.. Amine oxides: a review [J]. Journal of Oleo Science, 2006, 55(3): 99-119.
[4] Rolf P., Henkel K.. Cationic surfactants in laundry detergents and laundry aftertreatment aids [J]. Journal of the American Oil Chemists’Society, 1984, 61(2): 367-376.
[5] Waters J., Bebington W.. A new rinse conditioner active with improved environment properties [J]. Tenside Surfactants Detergents, 1991, 28(6): 460-467.
[6]邹文苑.织物柔软剂的发展趋势[J].日用化学工业,1999,5 (108):11-16.
[7]常青春.季铵盐型阳离子表面活性剂的发展及应用[J].佳木斯大学学报(自然科学版), 2003,21(4):503-506.
[8]杨雪萍,蒋文伟.新型柔软剂——硬脂酸三乙醇胺酯季铵盐合成与应用综述[J].皮革与化工,2008,25(6):25-29.
[9] Koto T., Ohtawa Y., Kaneko Y.. Biodegradable fabric compositions [P]. WO: 9964661, 1999-12-16.
[10]赵荣国,周绍箕.合成1-脂肪酰胺乙基-2-烷基咪唑啉的机理探讨[J].精细化工,1992,5(6):64-66.
[11] Gabriel R.. Amidation selective of fatty ester with N-(2-Amidoethy) ethanolamine under base catalysis [J]. Journal of the American Oil Chemists’Society, 1984, 61(5): 965-970.
[12] Friedli F. E., Koehle H. J., Fender M.. Upgrading triethanolamine esterquate performance to new levers [J]. Journal of Surfactants and Detergents, 2002, 5(3): 211-216.
[13] Puchta R., Krings P.. A new generation of softeners [J]. Tenside Surfactants Detergents, 1993, 30(3): 186-191.
[14] Phil S., Friedli F. E.. A study on the long-term stability and removal of quats on treated fabric [J]. Journal of Surfactants and Detergents, 2002, 5(3): 207-210.
[15]陈宗刚,吴赞敏,张爱.环境友好型织物柔软剂的研制[J].染料与染色,2004,41(3): 177-180.
[16]黄俊,曹平.中国衣物柔软剂的现状及对未来发展趋势的思考[J].日用化学品科学,2004,27(8):5-7.
[17]徐长卿,王丰收.铵酯的开发和应用-工业表面活性剂技术经济文集(5)[C].大连:大连出版社,1999:171-176.
[18]柯汉忠,程国娥.新型织物柔软剂PS-501的研制[J].印染助剂,2003,20(4):8-10.
[19]周弟,赵新,陈琳等.织物柔软剂的研究进展[J].化学工程师,2009,169(10):31-35.
[20]王一尘.阳离子表面活性剂的合成[M].北京:轻工业出版社,1984:47-51.
[21]丁忠传.纺织染整助剂[M].北京:化学工业出版社,1988:239-251.
[22]梁梦兰.表面活性剂和洗涤剂制备、性质、应用[M].北京:科技文献出版社,1990,172-174.
[23]索福喜,张万斌,江巩等.N,N-亚烃基脂肪酸双酰胺的合成及其润滑性能[J].华东化工学院学报,1993,1(5):191-197.
[24] Ruback W., Schut J.. Process for preparing fatty acid diesters of trialkanolamines [P]. EP: 295385, 1998-12-21.
[25] Yamamura M., Inokoshi J., Shiratsuchi K.. Fabric softener compositions [P]. EP: 472178, 1992– 02– 26.
[26]刘德荣.表面活性剂的合成与应用[M].成都:四川科学技术出版社,1987:77-78.
[27]赵荣国.咪唑啉及双酰胺类阳离子织物调理剂合成及其应用性能研究[D].北京:北京服装学院,1992.
[28]陈一飞.表面活性剂类柔软剂的柔软作用[J].四川丝绸,2001,(1):27—29.
[29] Zyschka R.,李卓.纺织柔软剂及其巧妙应用[[J].国际纺织导报,2001,(3):71—74.
[30]张平.以油脂为原料的织物柔软剂的现状[J].日用化学品科学, 2000, 23 (5):71-9, 12.
[31] Franklin R., Mendello R.. High di (alkyl fatty ester) quaternary ammonium compounds in fabric softening and personal care compositions [P]. US: 6037315, 2000– 03– 14.
[32] Howard J., Ormandy K. A.. A method of preparing fabric conditioning compositions [P]. WO: 0220706, 2002– 03– 14.
[33] Turner G. A., Emmons S. A.. Fabric softening composition [P]. WO: 9417168, 1994-08-04.
[34] Khan-Lodhi A. N., Whaley C.. Fabric softening composition [P]. WO: 9723590, 1997-07-03.
[35] Dewez J., Thibert E.. Stable fabric softener compositions [P]. WO: 9708285, 1997-03-06.
[36] Jacques A., Laitem L.. Fabric softening compositions providing enhanced performance and containing cationic softeners and fatty amides [P]. US: 6191101, 2001-02-20.
[37] Zappone M., Umstead D. J.. Fabric care composition containing polycarboxylate polymer andcompound derived from urea [P]. WO: 0116262, 2001-09-07.
[38] Ellson K. J., Wright J.. Use of fabric conditioning compositions for ironing benetts [P]. WO: 0146513, 2001-06-28.
[39] Jarvis A. N.. Fabric care composition [P]. EP: 1205538, 2002-05-15.
[40] Sakkab N., Brown D. R., Baker E. S.. Aqueous fabric softener compositions containing highly unsaturated active and chelant [P]. WO: 0134743, 2001-05-17.
[41] Grandmaire J., Hermosilla A.. Clear, concentrated liquid fabric softener compositions [P]. US: 5656585, 1997-08-12.
[42] Buron H. S., Jones C. W., Martinez Escolano. Fabric conditioning compositions [P]. WO: 0104254, 2001-01-18.
[43] Porta N., Weissen. Biodegradable fabric softening composition [P]. EP: 0638639, 1995-02-15.
[44] Chung A. H., Costa J. B., Denutte H. R. G.. Dryer-activated fabric conditioning and antistatic compositions with improved perfume longevity [P]. US: 5559088, 1996-09-24.
[45] Trius A., Humbert M.. Process for preparing quaternary ammonium compounds [P]. WO: 9101295, 1991-02-07.
[46] Wahl E., Bacon D.. Concentrated biodegradable quaternary ammonium fabric softener compositions and compounds containing intermediate iodine value unsaturated fatty acid chains [P]. US: 5562849, 1996-10-08.
[47] Baker E., Bodet J. F. Concentrated fabric softener compositions containing biodegradable fabric softeners [P]. US: 5545350, 1996-08-13.
[48] Naik A. R., Todt K. H., Wells M. A.. Fabric treatment materials [P]. US: 4137180, 1979-01-30.
[49]杨雪萍,蒋文伟,褚钰宇.硬脂酸三乙醇胺酯的合成优化[J].针织工业,2009,(8):64-67.
[50]李秋小,刑英站,周静怡等.环路反应器制备饱和脂肪酸甲酯的研究[J].表面活性剂工业,1998,(2):23～25,32.
[51]江琦.碳酸二甲酯在化工领域中的应用[J].石油化工,2000,29(2):144-147.
[52] Tundo P., Moraglio J.. Selective and continuous-flow mono-methylation of arylacetonitriles with dimethyl carbonate under gas-liquid phase-transfer catalysis conditions [J]. Journal of the Chemical Society, Perkin Transactions 1, 1989, (5): 1070-1071.
[53] Ouk S., Thieband S., Borredou E.. High performance method for O-methylation of phenol with dimethyl carbonate [J]. Applided Catalysis A: General, 2003, 241 (1-2): 227-233.
[54] Fu Z. H., Ono Y.. Selective N-monomethylation of aniline with dimethyl carbonate over Y-zeolites [J]. Catalysis letters, 1993, 22: 277-281.
[55] Selva M., Tundo P.. Selective N-methylation of primary aliphatic amines with dimethyl carbonate in the presence of alkali cation exchanged Y-faujasites [J]. Tetrahedron Letters, 2003, 44 (44): 8139-8142.
[56] Tundo P., Trotta F., Moraglio G.. Continuous-flow processes under gas-liquid phase-yransfer catalysis (GL-PTC) conditions: The reaction of dialkyl carbonates with phenol, alcohols, and mercaptants [J]. Industrial and Engineering Chemistry Research, 1988, 27: 1565-1571.
[57] Hacking M., Rantwijk F. V., Sheldon R. A.. Li-pase catalyzed reactions of aliphatic and arylaliphatic carbonic acid esters [J]. Journal of molecular Catalysis B, 2000, 9: 201-208.
[58] Shaikh Abbas Alli, Sivaram S.. Dialkyl and diaryl carbonates by carbonate interchange reaction with dimethyl carbonate [J]. Industrial and Engineering Chemistry Research, 1992, 31: 1167-1172.
[59] Roger A. G., West C. Pa. Catalytic process for the preparation of polyalkylene carbonates [P]. US: 5171830, 1992-12-15.
[60] Hafauo Y.. Production of diphenyl carbonate [P]. JP: 62277345, 1987-12-01.
[61] Mori S., Ida I., Ue M.. Process for producing quaternary salts [P]. US: 4892944, 1990-01-09.
[62] Werntz J. H.. Monoquaternary ammonium carbonates [P]. US: 2635100, 1953-04-14.
[63] Yagi O., Shimizu S.. Synthesis of pure tetramethylammonium hydroxide solution free from chloride by the electrolysis of its hydrogen carbonate [J]. Chemistry Letters, 1993, 22 (12): 2041-2044.
[64] Gary W. E., Duane E. W., Drew P.. Quaternary methyl carbonates: novel agents for fabric conditioning [J]. Journal of Surfactants and Detergents, 2005, 8 (4): 325-329.
[1]Miao Z. C., Yang J. Z., Wang L., et al. Synthesis of biodegradable lauric acid ester quaternary ammonium salt cationic surfactant and its utilization as calico softener [J]. Materials Letters, 2008, 62: 3450-3452.
[2] Mishra S., Tyagi V. K.. Ester quats: the novel class of cationic fabric softeners [J]. Journal of Oleo Science, 2007, 56(6): 269-276.
[3] Steiger P., Friedli F. E.. A study on the long-term stability and removal of quats on treated fabric [J]. Journal of Surfactants and Detergents, 2002, 5(3): 207-210.
[4] Weissen H. J., Porta N.. Biodegradable fabric softening composition [P]. EP: 0638639, 1995-02- 5.
[5]杨建洲,林里,付志刚等.生物可降解型阳离子酯表面活性剂的研究[J].日用化学工业,2005,35 (1):9-11,48.
[6] Haliza A. A., Parthiban S., Salmiah A.. Scaled-up production and optimization study of the esterification of palm-based fatty acid and triethanolamine [J]. Journal of Oil Palm Research, 2006, 18: 305-311.
[7] Friedli F. E., Koehle H. J., Fender M., et al. Upgrading triethanolamine esterquat performance to new levels [J]. Journal of Surfactants and Detergents, 5(3): 211-216.
[8] Baker Ellens, Bodet Jean-francois. Concentrated fabric softener compositions containing biodegradable fabric softeners [P]. US: 5545350, 1996-08-13.
[9] Rashmi T., Tyagi V. K., Khanna R. K.. Synthesis, Characterization and performance of tallow fatty acids and triethanolamine based esterquats [J]. Journal of Oleo Science, 2006, 55(7): 337-345.
[10]杨雪萍,蒋文伟,褚钰宇.硬脂酸三乙醇胺酯的合成优化[J].针织工业,2009,(8):64-67.
[11] Friedli F. E., Koehle H. J., Fender M.. Upgrading triethanolamine esterquate performance to new levers [J]. Journal of Surfactants and Detergents, 2002, 5(3): 211-216.
[12] Friedli F. E., Robert K., Toney C. J., et al. Novel new ester quaternaries for improved performance benefits as rinse cycle fabric softeners [J]. Journal of Surfactants and Detergents, 2001, 4(4): 401-405.
[13] Ruback W., Schut J.. Process for preparing fatty acid diesters of trialkanolamines [P]. EP: 295385, 1998-12-21.
[14] Sakata Y., Inokoshi J., Katoh T., et al. Liquid softener composition, novel quaternary ammonium salt,and process for the preparation of said salt [P]. US: 5476597, 1995-12-19.
[15] Miller J. H., Sauer J. D., Delaet D. L.. Process for preparing quaternary ammonium compounds [P]. US: 5599990, 1997-02-04.
[16] Laurent L., Dierendinck V., Zahradnik J., et al. Loop reactor-a feasible alternative to stirred tank reactors [J]. Industrial and Engineering Chemistry Research, 1998, 37(3):734-738.
[17] John T.. Reactions and synthesis in surfactant systepns [M]. New York: Marcel Dekkle, Inc., 2001, 7-11.
[18] Urs Geser, Richard Malone, Len Fabiano, Rene Duveen. Novelty in HH Loop Reactor Technologies for Ethoxylations and Propoxylations [C]. 10th International Conference on Surfactant & Detergent (ICSD208), 2008, Shanghai, China.
[19] Rene F D.. New frontiers in reactor design [C]. Billingham, UK: The Royal Society of Chemistry. 1998, 1-14.
[20]张卫民,李秋小,缪列平等.环路反应器工程研究[J].日用化学工业,1999,(6):5-7.
[21]李秋小,刑英站,周静怡等.环路反应器制备饱和脂肪酸甲酯的研究[J].表面活性剂工业,1998,(2):23-25, 32.
[22]聂金泉.用于气固液多相反应的回路反应器[J].化工装备技术,1994,15(3):21-25.
[23]袁少明,周庚生,张高勇.喷射反应器及其应用.日用化学工业,2003,33(1):40-44.
[24]马宝歧.喷射式气-液反应器[J].石油化工,1997,(6):284– 292.
[25]邢英站,李秋小,周静怡等.环路反应器与搅拌釜装置生产十二烷基二甲基叔胺的比较[J].日用化学品科学,2000,23(S1):53– 55.
[26]陆宏圻.喷射技术理论及应用[M].武汉:武汉大学出版社,2004,398-424.
[27] Wilkes A. J., Jacobs C., Walraven G., et al. Characterization of quaternized triethanolamine esters (esterquats) by HPLC, HRCGC and NMR [C]. 4th World Surfactants Congress, Barcelona: Marcel Dekker Inc. 1996, 389-402.
[1] Shilpi M., Tyagi V. K.. Ester quats: The novel class of cationic fabric softeners [J]. Journal of Oleo Science, 2007, 56: 269-276.
[2] Tyagi R., Tyagi V. K.. Synthesis, Characterization and performance of tallow fatty acids and triethanolamine based esterquats [J]. Journal of Oleo Science, 2006, 55: 337-345.
[3] James H. C., Sjack E., Karen W.. Catalysis for green chemistry: ultrahigh loaded mesoporous solid acids [J]. Comptes Rendus de l’Académie des Sciences - Series IIC - Chemistry, 2000, 3(6): 399-404.
[4] Kazuo O., Chen X., Katsumi T.. Water-tolerant catalysis of a silica composite of a sulfonic acid resin, Aciplex [J]. Applied Catalysis A: General, 2000, 190(1-2): 253-260.
[5]曹维良,张敬畅,吕青.CZ固体酸催化剂的应用及最佳反应工艺条件的优化[J].石油化工高等学校学报,2000,13(1):42-46.
[6]张敬畅,孟秀娟,曹维良.新型疏水性固体酸Zr(SO4)2/AC催化剂的制备及其催化性能[J].催化学报,2006,27(2):135-138.
[7]李峰,李隽春,段雪.新型层状表面相锆基固体酸催化酯化反应研究[J].精细化工,2002,19(1):32-35.
[8]李葆,战永复,李连忠等.含水硫酸锆作为酯化催化剂的研究[J].催化学报,1989,10(3):331-333.
[9] Li R. F., Yu F., Li F. X., et al. One-pot synethesis of superacid catalytic material SO42-/ZrO2-SiO2 with thermostable well-ordered mesoporous structure [J]. Journal of Solid State Chemistry, 2009, 182: 991-994.
[10] Wang J. H., Mou C. Y.. Characterizations of aluminum-promoted sulfated zirconia on mesoporous MCM-41 silica: Butane isomerization [J]. Microporous and Mesoporous Materials, 2008, 110: 260-270.
[11] Juan J. C., Jiang Y. J., Zhang J. C.. Supported zirconium sulfate on carbon nanotubes as water-tolerant solid acid catalyst [J]. Materials Research Bulletin, 2007, 42: 1278-1285.
[12]张敬畅,孟秀娟,曹维良.新型疏水性固体酸Zr(SO4)2/AC催化剂的制备及其催化性能[J].催化学报,2006,27(2):135-138.
[13] Jiang Y. J., Juan J. C., Zhang J. C.. Preparation and catalytic application of novel water tolerant solid acid catalysts of zirconium sulfate/HZSM-5 [J]. Chemical Research in Chinese Universities, 2007, 23: 349-354.
[14]张微,徐恒泳,毕亚东等.介孔分子筛SBA-15的改性研究进展[J].化工进展,2007,26(2):152-157.
[15] Li F. X., Yu F., Li Y. L., et al. Direct synthesis of Zr-SBA-15 mesoporous molecular sieves with high zirconium loading: characterization and catalytic performance after sulfated [J]. Microporous and Mesoporous Materials, 2007, 101: 250-255.
[16] Wang X. G., Landau M. V., Rotter H., et al. TiO2 and ZrO2 crystals in SBA-15 silica: performance of Pt/TiO2(ZrO2)/SBA-15 catalyst in ethyl acetate combustion [J]. Journal of Catalysis, 2004, 222: 565-571.
[17] Yang C. M., Kalwei M., Schuth F.. Gold nanoparticles in SBA-15 showing catalytic activity in CO oxidation [J]. Journal of Applied Catalysis, 2003, 254: 289-296.
[18]周丽绘,张利中,刘洪来.晶化温度对介孔材料SBA-15结构与形貌的影响[J].过程工程学报,2006,6(3):499-502.
[19]高波,朱广山,傅学奇等.介孔分子筛SBA-15中α-胰凝乳蛋白酶组装及催化活性研究[J].高等学校化学学报,2003,24(6):1100-1102.
[20] Kim T. H., Jang M., Park J. K.. Bifunctionalized mesoporous molecular sieve for perchlorate removal [J]. Microporous and Mesoporous Materials, 2008, 108: 22-28.
[21] Zhao D. Y., Feng J. L., Huo Q. S.. Triblock copolymer synthesis of mesoporous silica with periodic 50-300 angstrom pore [J]. Science, 1998, 279: 548-552.
[22] Zhao D. Y., Huo Q. S,. Feng J. L., et al. Nonionic triblock and star diblock copolymer and oligomeric surfactant synthese of highly ordered, hydrothermally stable, mesoporous silica structures [J]. Journal of the American Oil Chemists Society, 1998, 120: 6024-6036.
[23]李峰,何静,张保国.四水硫酸锆热分解反应的程序升温动态分析[J].北京化工大学学报,1996,23(2):58-61.
[24] Friedli F. E., Koehle H. J., Fender M.. Upgrading triethanolamine esterquat performance to new levels [J]. Journal of Surfactants and Detergents, 2002, 5: 211-216.
[25]李隽春,张慧,段雪等.Hβ负载锆催化剂的研制及其催化性能和结构性能的研究[J].燃料化学学报,2002,30(4):358-362.
[1] Waters J., Bebington W.. A new rinse conditioner active with improved environmental properties [J]. Tenside Surfactants Detergents, 1991, 28(6): 460～467.
[2] Puchta R., Krings P.. A new generation of softeners [J]. Tenside Surfactants Detergents, 1993, 30(3): 186～191.
[3] Steiger P., Friedli F. E.. A study on the long-term stability and removal of quats on treated fabric [J]. Journal of Surfactants and Detergents, 2002, 5(3): 207～210.
[4] Weissen H. J., Porta N.. Biodegradable fabric softening composition [P]. EP: 0638639, 1995 - 02 - 15.
[5]杨建洲,林里,付志刚等.生物可降解型阳离子酯表面活性剂的研究[J].日用化学工业, 2005, 35 (1) : 9 - 11, 48.
[6] Trius A., Humbert M.. Process for preparing quaternary ammonium compounds [P]. WO: 9101295, 1991-02-07.
[7] Wahl E., Bacon D.. Concentrated biodegradable quaternary ammonium fabric softener compositions and compounds containing intermediate iodine value unsaturated fatty acid chains [P]. US: 5562849, 1996-10-08.
[8] Baker E., Bodet J. F.. Concentrated fabric softener compositions containing biodegradable fabric softeners [P]. US: 5545350, 1996-08-13.
[9] Naik A. R., Todt K. H., Wells M. A.. Fabric treatment materials [P]. US: 4137180, 1979-01-30.
[10]耿涛,李秋小,李运玲.硬脂酸三乙醇胺酯季按盐的合成[J].皮革化工, 2004, 21(4): 21-27.
[11]徐宝财,聂红艳,水金环.碳酸二甲酯与阳离子表面活性剂合成[J].第十届中国科协年会第18分会场:二氧化碳减排和绿色化利用与发展研讨会,2008:88-91.
[12] Yoshio O.. Dimethyl carbonate for environmentally benign reactions [J]. Catalysis today, 1997, 35: 15-25.
[13] Pietro T., Manurizio S.. The chemistry of dimethyl carbonate [J]. Accounts of Chemical Research, 2002, 35(9): 706-716.
[14]张建西,张大洋,赵鸣玉等.用碳酸二甲酯和环戊二烯制备甲基环戊二烯的研究[J].沈阳化工学院学报,2003,17(1):1-3.
[15] Ouk S., Thiebaud S., Borredon E., et al. O-Methylation of phenolic commounds with dimethylcarbonate under solid/liquid phase transfer system [J]. Tettahedron Letter, 2002, 43: 2661-2663.
[16]宋锡瑾,王常申.合成苯甲醚的新工艺[J].精细化工,2000,17(1):42-44.
[17]郭俊胜.合成间甲基苯甲醚的新方法[J].河南化工,2001,2:12-13.
[18] Jiang X. L., Tiwari A., Thompson M., et al. A practical method for N-Methylation of indoles using dimethyl carbonate [J]. Oraganic Process Reseach and Development, 2001, 5: 604-608.
[19] Bomben A., Selva M., Tundo P.. Dimethylcarbonate as a methylating agent [J]. Journal of Chemical Research, 1997, 448-449.
[20]吴如春,谢涛,李媚.碳酸二甲酯合成体系的气相色谱分析法[J].广西民族大学学报(自然科学版),2008,14(4):73-75.
[21]汪正范等.色谱定性与定量[M].北京:化学工业出版社,2001:11- 13.
[22]陈延辉,李萍.尿素与甲醇合成碳酸二甲酯的气相色谱分析[J].哈尔滨师范大学自然科学学报,2006,22(2):97-99.
[23]李光兴,许汉昌,陈兵等.合成碳酸二甲酯产物气相色谱分析[J].湖北化工,1995,12 (4):56-58.
[24]王华,许红云,吴砚会.甲醇氧化羰化制碳酸二甲酯产物气相色谱分析[J].天然气化工,2002,27 (4):50-52.
[25]王高升,余晓峰,汪列敏.气相法合成的碳酸二甲酯的色谱分析[J].浙江化工,2002,33 (1):54-55.
[26]莫婉玲,熊辉,黄荣生等.甲醇液相氧化羰化合成碳酸二甲酯的色谱分析[J].江西科学,2003,21 (1):15-17.
[27]熊冬生,林福兰.气相色谱法测定碳酸二甲酯的含量[J].化学分析计量,2003,12 (4):19-21.
[28] Choi J. C., He L. N., Yasuda H., et al. Selective and high yield synthesis of dimethyl carbonate directly from carbon dioxide and methanol [J]. Green Chemistry, 2002(4): 230 - 234.
[29] Isaacs N., Sullivan B. O., Verhaelen C.. High pressure routes to dimethyl carbonate from supercritical carbondioxide [J]. Tetrahedron, 1999, 55: 11949-11959.
[30]潘鹤林,徐志珍,宋新杰等.合成碳酸二甲酯的技术进展[J].浙江化工,1999,30(1):32– 35.
[31]王建军,朱红军.碳酸二甲酯国内外生产及技术发展概况[J].化学工程师,2003(4):41- 42,45.
[32]钟顺和,黎汉生,王建伟等.用二氧化碳和甲醇直接合成碳酸二甲酯的研究[J].石油炼制与化工,2000,31(6):51– 55.
[1]蒋兴材,金康生.纺织品柔软剂[J].宁波化工,1990,(2):8- 12.
[2]倪捷.织物用柔软剂的现状和发展新课题[J].上海染料,1996,(5):11- 20.
[3]冯亚青,王利军,陈立功等.助剂化学及工艺学[M].北京:化学工业出版社,1997:344-359.
[4]杨栋梁.织物的柔软整理(三) [J].印染助剂,1999,16(3):33- 34.
[5]刘昌龄.纺织品柔软整理和柔软剂[J].河南纺织科技,1996,4:6- 9.
[6]唐增荣.纺织品柔软整理剂的应用研究(下) [J].染整科技,2000,2:19- 23.
[7]郭志军.织物柔软整理与柔软剂[J].纺织装饰织物,1997,2:21- 23.
[8]黄茂福.纺织助剂的基本特性、检测与应用(二)[J].染整科技,1996,4:46- 55.
[9]陈荣圻.纺织品柔软剂(一)[J].印染,1993,19(3):38- 41.
[10]张先亮,陈新兰,唐红定.精细化学品化学[M].武汉大学出版社,2008:247- 248.
[11]王丰收.新型柔软剂—烷基咪唑啉酯及其季铵盐的性能[J].日用化学工业,2000,2: 9-10.
[12] Jeannene A.. How to choose cationics for fabric softeners [J]. Journal of the American Oil Chemists’Society, 1983(60):1166-1169.
[13] Egan R. R.. Cationic surface active agents as fabric softeners [J]. Journal of the American Oil Chemists’Society, 1978(55): 118-121.
[1] Ralph F., Michael D. H., Joseph Z.. Cationic and amine-based surfactants [J]. Oleo Chemical Manufacture and Applications, 2001, 11: 23-54.
[2] Franklin R., Mendello R.. High di (alkyl fatty ester) quaternary ammonium compounds in fabric softening and personal care compositions [P]. US: 6037315, 2000-03-14.
[3] Howard Jane, Ormandy Kevin Anthony. A method of preparing fabric conditioning compositions [P]. WO: 0220706, 2002-03-14.
[4] Turner G. A., Emmons S. A.. Fabric softening composition [P]. WO: 9417168, 1994-08-04.
[5] Khan-Lodhi A. N., Whaley C.. Fabric softening composition [P]. WO: 9723590, 1997-07-03.
[6] Dewez J., Thibert E.. Stable fabric softener compositions [P]. WO: 9708285, 1997-03-06.
[7] Jacques A., Laitem L.. Fabric softening compositions providing enhanced performance and containing cationic softeners and fatty amides [P]. US: 6191101, 2001-02-20.
[8] Zappone M., Umstead D. J.. Fabric care composition containing polycarboxylate polymer and compound derived from Urea [P]. WO: 0116262, 2001-09-07.
[9] Ellson K. J., Wright J.. Use of fabric conditioning compositions for ironing benetts [P]. WO: 0146513, 2001-06-28.
[10]徐宝财,聂红艳,水金环.碳酸二甲酯与阳离子表面活性剂合成[J].第十届中国科协年会第18分会场:二氧化碳减排和绿色化利用与发展研讨会,2008:88-91.
[11]舒婷,李光兴.碳酸二甲酯作甲基化试剂的研究进展[J].化工中间体,2008,1:20-23.
[12] Yoshio O.. Dimethyl carbonate for environmentally benign reactions [J]. Catalysis Today, 1997, 35: 15-25.
[13] Pietro T., Manurizio S.. The chemistry of dimethyl carbonate [J]. Accounts of Chemical Research, 2002, 35(9): 706-716.
[14]张建西,张大洋,赵鸣玉等.用碳酸二甲酯和环戊二烯制备甲基环戊二烯的研究[J].沈阳化工学院学报,2003,17(1):1-3.
[15] Ouk S., Thiebaud S., Borredon E., et al. O-Methylation of phenolic commounds with dimethyl carbonate under solid/liquid phase transfer system [J].Tettahedron Letter, 2002, 43: 2661-2663.
[16]宋锡瑾,王常申.合成苯甲醚的新工艺[J].精细化工,2000,17(1):42-44.
[17]郭俊胜.合成间甲基苯甲醚的新方法[J].河南化工,2001,2:12-13.
[18] Jiang X. L., Tiwari A., Thompson M., et al. A practical method for N-methylation of indoles using dimethyl carbonate [J]. Oraganic Process Reseach and Development, 2001, 5: 604-608.
[19] Bomben A., Selva M., Tundo P.. Dimethyl carbonate as a methylating agent [J]. Journal of Chemical Research, 1997, 448-449.
[20] Gary W. E., Weisshaar D. E., Paulson D.. Quaternary methyl carbonates: novel agents for fabric conditioning [J]. Journal of Surfactants and Detergents, 2005, 8 (4): 325-329.
[21] Mori S., Ida I.. Process for producing quaternary salts [P]. US: 4892944, 1990-01-09.
[22] Shumpei S., Moses L., Toshitsura C.. Method for production of aqueous quaternary ammonium hydroxide solution [P]. US: 4634509, 1987-01-06.
[23] Tetsuo A., Eiji S., Jiro I.. Process for production of quaternary ammonium hydroxides [P]. US: 4776929, 1988-10-11.
[24]郑卓群.咪唑类离子液体催化下合成季铵盐的研究[D].浙江:浙江师范大学,2006.
[25]蒋波,詹晓力,陈丰秋.季铵化反应中的溶剂效应[J].化学通报,2006,69:1-6.
[26]唐红萍,杨明德,何培炯.季铵盐N263的非水滴定分析[J].冶金分析,2002,22(2):51-53.