电子级没食子酸制备过程中若干基础问题研究
|
摘要
没食子酸及以其为原料制备的没食子酸酯、多羟基二苯甲酮等多羟基化合物均为重要的化工原料,广泛应用于食品、医药、化工等领域。近年来,美国等发达国家开始使用高纯度没食子酸、没食子酸丙酯等化合物替代邻苯二酚来洗涤大规模集成电路板,从而克服了邻苯二酚在清洗过程中易损害电板的缺点。由于知识产权保护及国际竞争等原因,国外一直未见与电子级没食子酸制备工艺相关的文献报道。尽管国内有少数学者对电子级没食子酸的制备工艺进行了初步研究,但缺乏全面的研究和理论方面的探索。
本文对电子没食子酸制备过程中的若干基础问题进行了研究,并对树脂吸附+结晶相结合的制备工艺进行了初步探索,以期能够为电子级没食子酸的制备提供理论依据和实验基础。主要内容概括如下:
首先,本文建立了一种同时分析含单宁生物质(五倍子粉和塔拉粉)水解产物中没食子酸和焦性没食子酸的液相色谱新方法。而后,利用高压反应釜首次系统研究了413.15 K-463.15 K范围内高温液态水中五倍子单宁和塔拉单宁及其水解中间产物没食子酸的无催化分解反应动力学。实验结果表明,在没有任何催化剂的情况下,五倍子单宁和塔拉单宁能够顺利水解生成没食子酸,没食子酸可进一步脱羧生成焦性没食子酸,通过控制反应条件可以选择性地得到中间产物没食子酸。采用一级连续反应动力学模型对实验数据进行拟合,得到五倍子单宁和塔拉单宁水解反应的表观活化能。
其次,本文采用平衡法首次测定了没食子酸、没食子酸甲酯、没食子酸丙酯、没食子酸辛酯、2,4-二羟基二苯甲酮、2,3,4-三羟基二苯甲酮、2,3,4,4′-四羟基二苯甲酮和2,2′,4,4′-四羟基二苯甲酮等多羟基化合物在水+乙醇混合溶剂中的溶解度。结果表明,溶解度随温度升高、溶剂中乙醇含量的增加而增加;一般情况下,溶解度亦随溶质分子极性的增加而增加。
接着,本文利用pH电位滴定法测定了没食子酸与多种金属离子所形成配合物的稳定常数,其中Fe(Ⅱ)、Al(Ⅲ)、Ni(Ⅱ)及Pb(Ⅱ)等金属离子与没食子酸
所形成配合物的稳定常数未见其他文献报道。实验结果表明,没食子酸对多种金属离子具有较强的配位作用,主要形成ML型配合物,配合物稳定常数顺序符合经典的Irving-Williams顺序:Ca(Ⅱ)＜Mg(Ⅱ)＜Mn(Ⅱ)＜Fe(Ⅱ)＜Ni(Ⅱ)＜Zn(Ⅱ)＜Cu(Ⅱ)＜Fe(Ⅲ)＜Pb(Ⅱ)＜Al(Ⅲ)。
同时,还利用紫外-可见光谱法对没食子酸与Fe(Ⅱ)、Zn(Ⅱ)、Al(Ⅲ)、Mn(Ⅱ)及Pb(Ⅱ)等金属离子在水溶液中的配位现象进行了研究,并着重从动力学和热力学角度对没食子酸和亚铁离子的配位现象进行了探讨。结果表明,没食子酸对这些金属离子有较强的配位作用,其中,没食子酸与Fe(Ⅱ)主要形成ML的配合物,反应为二级反应,根据Arrhenius方程和Absolute-rate理论得到该反应的表观活化能以及自由能,并基于实验现象提出了较为合理的反应机理。
最后,本文对树脂吸附+结晶相结合制备电子级没食子酸的工艺过程进行了初步研究。采用超纯水为溶剂结晶提纯工业没食子酸,能够有效提高没食子酸纯度,并降低其中金属离子的含量,三次结晶即可将没食子酸含量从96.05%提高至99.77%,且使铁、钙、钠和钾等金属离子含量均降至1ppm左右,但继续增加结晶次数对提高没食子酸纯度和降低金属离子含量无明显效果。实验所用三种电子级树脂对目标金属离子均有一定的去除效果,其中,ZGC-ER80的效果较佳。部分普通树脂也可以有效地降低没食子酸中目标金属离子中的一种或全部,尤以氨基羧酸螯合树脂XSC-800效果较佳。
本课题研究结果能为电子级没食子酸的制备提供大量基础数据和理论依据。
Gallic acid(GA,3,4,5-trihydroxybenzoic acid) and several polyhydroxy-compounds synthesized by it are industrially important chemicals widely used in many fields such as organic synthesis, pharmaceutical and food.Recently;ultrahigh-purity gallic acid and propyl gallate have been used in electronics industry for replacing catechol(1,2-dihydroxybenzene) to remove the photoresist,other polymeric material or residue from the substrate.With the development of economics and the enhancement of environmental protection consciousness,gallic acid will certainly replace 1,2-dihydroxybenzene used currently in China.Due to the international competition and the protection of intellectual property rights,literature about the preparation process of ultrahigh-purity gallic acid is quite scarce. Accordingly,systematical exploration and theoretical study are currently unavailable as well.
In the present study,several fundamental problems related to the preparation of ultrahigh-purity gallic acid were investigated.In addition,the preparation process combining the resin absorption and crystallization has been studied particularly.The main contents are summarized as follows.
Firstly,in the non-catalyzed hydrolysis of gallotannin and tara tannin in high temperature liquid water(HTLW),after establishing a new high-performance liquid chromatography(HPLC) method for the analysis of tannin hydrolysis products,the decomposition reaction kinetics of tannins and their intermediate gallic acid were systematically studied for the first time in the temperature range from 413.15 K to 463.15 K. It was found that gallotannin and tara tannin could be hydrolyzed easily without catalysts and the reaction was indicated to be a typical consecutive first-order one in which gallic acid formed as a main intermediate product and pyrogallol as the final product.Additionally, selective decomposition of tannin in HTLW was proved to be possible by adjusting reaction temperature and time.Based on the assumption of first order kinetics equation,the apparent activation energies were evaluated.
Next,the solubilities of several polyhydroxy-compounds,including gallic acid,methyl gallate,propyl gallate,octyl gallate, 2,4-dihydroxybenzophenone,2,3,4-trihydroxybenzophenone, 2,3,4,4'-tetrahydroxybenzophenone and 2,2',4,4'-tetrahydroxybenzophenone,in ethanol+water mixture were determined by a static analytical method in the temperature range from 273.15 K to 363.15 K.As shown in the results,the solubilities increase as the temperature and the concentration of ethanol in the mixture solvent increase.In addition,the solubilities increase with the increasing molecular polarity generally.The simplifiedλ-h equation and two empirical equations were proposed to correlate the experimental data with good agreement.
Then,the complexation of gallic acid with several metal ions was studied by means of acid-base potentiometric titration.The stability constants between gallic acid and Fe(Ⅱ),Al(Ⅲ),Ni(Ⅱ) and Pb(Ⅱ) were determined for the first time.Results showed that gallic acid can form stable complexes with metal ions involved in this study,and the sequence of stability constants is:Ca(Ⅱ)＜Mg(Ⅱ)＜Mn(Ⅱ)＜Fe(Ⅱ)＜Ni(Ⅱ)＜Zn(Ⅱ)＜Cu(Ⅱ)＜Fe(Ⅲ)＜Pb(Ⅱ)＜Al(Ⅲ).
Simultaneously,the complexation between gallic acid and several metal ions was investigated by using UV-vis spectroscopy.Also, theoretical and experimental study on the complexation reaction of gallic acid with ferrous ion was performed systematically.The results showed that gallic acid can form stable complexes with metal ions investigated in this study,which makes the red shift of gallic acid in the presence of metal ions.The stoichiometric composition of GA-Fe(Ⅱ) complex was 1:1 under the adopted experimental conditions.The complexation reaction of gallic acid with ferrous ion was found to be a second order reaction. According to the Arrhenius equation and the Absolute-rate theory,the activation energy and free energy of activation of the complexation reaction were calculated.To understand the kinetic results obtained,a three step reaction mechanism was proposed,which can satisfactorily explain the dependence of the rate constant on the temperature,ionic strength and permittivity of the reaction medium.
Finally,the preparationprocess of ultrahigh-purity gallic acid combining resin absorbance and crystallization was investigated particularly.As shown in the results,crystallization with ultrahigh-purity water can not only improve the purity of gallic acid but also decrease the concentration of metal ions effectively.After three times of crystallization,the purity of gallic acid increased from 96.05% to 99.77%,while the concentration of calcium,iron,sodium and kalium ions were all reduced to around 1 ppm.Different resins have different effects on the removement of metal ions.The three ultra-cleaning resins with high purity all have good effects,especially ZGC-ER80.Treating with several resins with common purity,such as XSC-800 and 001×10,the concentration of metal ions in gallic acid can also be reduced effectively.
The information yielded from this work will provide essential basic data and theoretical instruction for the preparation process of ultrahigh-purity gallic acid.
本文对电子没食子酸制备过程中的若干基础问题进行了研究,并对树脂吸附+结晶相结合的制备工艺进行了初步探索,以期能够为电子级没食子酸的制备提供理论依据和实验基础。主要内容概括如下:
首先,本文建立了一种同时分析含单宁生物质(五倍子粉和塔拉粉)水解产物中没食子酸和焦性没食子酸的液相色谱新方法。而后,利用高压反应釜首次系统研究了413.15 K-463.15 K范围内高温液态水中五倍子单宁和塔拉单宁及其水解中间产物没食子酸的无催化分解反应动力学。实验结果表明,在没有任何催化剂的情况下,五倍子单宁和塔拉单宁能够顺利水解生成没食子酸,没食子酸可进一步脱羧生成焦性没食子酸,通过控制反应条件可以选择性地得到中间产物没食子酸。采用一级连续反应动力学模型对实验数据进行拟合,得到五倍子单宁和塔拉单宁水解反应的表观活化能。
其次,本文采用平衡法首次测定了没食子酸、没食子酸甲酯、没食子酸丙酯、没食子酸辛酯、2,4-二羟基二苯甲酮、2,3,4-三羟基二苯甲酮、2,3,4,4′-四羟基二苯甲酮和2,2′,4,4′-四羟基二苯甲酮等多羟基化合物在水+乙醇混合溶剂中的溶解度。结果表明,溶解度随温度升高、溶剂中乙醇含量的增加而增加;一般情况下,溶解度亦随溶质分子极性的增加而增加。
接着,本文利用pH电位滴定法测定了没食子酸与多种金属离子所形成配合物的稳定常数,其中Fe(Ⅱ)、Al(Ⅲ)、Ni(Ⅱ)及Pb(Ⅱ)等金属离子与没食子酸
所形成配合物的稳定常数未见其他文献报道。实验结果表明,没食子酸对多种金属离子具有较强的配位作用,主要形成ML型配合物,配合物稳定常数顺序符合经典的Irving-Williams顺序:Ca(Ⅱ)＜Mg(Ⅱ)＜Mn(Ⅱ)＜Fe(Ⅱ)＜Ni(Ⅱ)＜Zn(Ⅱ)＜Cu(Ⅱ)＜Fe(Ⅲ)＜Pb(Ⅱ)＜Al(Ⅲ)。
同时,还利用紫外-可见光谱法对没食子酸与Fe(Ⅱ)、Zn(Ⅱ)、Al(Ⅲ)、Mn(Ⅱ)及Pb(Ⅱ)等金属离子在水溶液中的配位现象进行了研究,并着重从动力学和热力学角度对没食子酸和亚铁离子的配位现象进行了探讨。结果表明,没食子酸对这些金属离子有较强的配位作用,其中,没食子酸与Fe(Ⅱ)主要形成ML的配合物,反应为二级反应,根据Arrhenius方程和Absolute-rate理论得到该反应的表观活化能以及自由能,并基于实验现象提出了较为合理的反应机理。
最后,本文对树脂吸附+结晶相结合制备电子级没食子酸的工艺过程进行了初步研究。采用超纯水为溶剂结晶提纯工业没食子酸,能够有效提高没食子酸纯度,并降低其中金属离子的含量,三次结晶即可将没食子酸含量从96.05%提高至99.77%,且使铁、钙、钠和钾等金属离子含量均降至1ppm左右,但继续增加结晶次数对提高没食子酸纯度和降低金属离子含量无明显效果。实验所用三种电子级树脂对目标金属离子均有一定的去除效果,其中,ZGC-ER80的效果较佳。部分普通树脂也可以有效地降低没食子酸中目标金属离子中的一种或全部,尤以氨基羧酸螯合树脂XSC-800效果较佳。
本课题研究结果能为电子级没食子酸的制备提供大量基础数据和理论依据。
Gallic acid(GA,3,4,5-trihydroxybenzoic acid) and several polyhydroxy-compounds synthesized by it are industrially important chemicals widely used in many fields such as organic synthesis, pharmaceutical and food.Recently;ultrahigh-purity gallic acid and propyl gallate have been used in electronics industry for replacing catechol(1,2-dihydroxybenzene) to remove the photoresist,other polymeric material or residue from the substrate.With the development of economics and the enhancement of environmental protection consciousness,gallic acid will certainly replace 1,2-dihydroxybenzene used currently in China.Due to the international competition and the protection of intellectual property rights,literature about the preparation process of ultrahigh-purity gallic acid is quite scarce. Accordingly,systematical exploration and theoretical study are currently unavailable as well.
In the present study,several fundamental problems related to the preparation of ultrahigh-purity gallic acid were investigated.In addition,the preparation process combining the resin absorption and crystallization has been studied particularly.The main contents are summarized as follows.
Firstly,in the non-catalyzed hydrolysis of gallotannin and tara tannin in high temperature liquid water(HTLW),after establishing a new high-performance liquid chromatography(HPLC) method for the analysis of tannin hydrolysis products,the decomposition reaction kinetics of tannins and their intermediate gallic acid were systematically studied for the first time in the temperature range from 413.15 K to 463.15 K. It was found that gallotannin and tara tannin could be hydrolyzed easily without catalysts and the reaction was indicated to be a typical consecutive first-order one in which gallic acid formed as a main intermediate product and pyrogallol as the final product.Additionally, selective decomposition of tannin in HTLW was proved to be possible by adjusting reaction temperature and time.Based on the assumption of first order kinetics equation,the apparent activation energies were evaluated.
Next,the solubilities of several polyhydroxy-compounds,including gallic acid,methyl gallate,propyl gallate,octyl gallate, 2,4-dihydroxybenzophenone,2,3,4-trihydroxybenzophenone, 2,3,4,4'-tetrahydroxybenzophenone and 2,2',4,4'-tetrahydroxybenzophenone,in ethanol+water mixture were determined by a static analytical method in the temperature range from 273.15 K to 363.15 K.As shown in the results,the solubilities increase as the temperature and the concentration of ethanol in the mixture solvent increase.In addition,the solubilities increase with the increasing molecular polarity generally.The simplifiedλ-h equation and two empirical equations were proposed to correlate the experimental data with good agreement.
Then,the complexation of gallic acid with several metal ions was studied by means of acid-base potentiometric titration.The stability constants between gallic acid and Fe(Ⅱ),Al(Ⅲ),Ni(Ⅱ) and Pb(Ⅱ) were determined for the first time.Results showed that gallic acid can form stable complexes with metal ions involved in this study,and the sequence of stability constants is:Ca(Ⅱ)＜Mg(Ⅱ)＜Mn(Ⅱ)＜Fe(Ⅱ)＜Ni(Ⅱ)＜Zn(Ⅱ)＜Cu(Ⅱ)＜Fe(Ⅲ)＜Pb(Ⅱ)＜Al(Ⅲ).
Simultaneously,the complexation between gallic acid and several metal ions was investigated by using UV-vis spectroscopy.Also, theoretical and experimental study on the complexation reaction of gallic acid with ferrous ion was performed systematically.The results showed that gallic acid can form stable complexes with metal ions investigated in this study,which makes the red shift of gallic acid in the presence of metal ions.The stoichiometric composition of GA-Fe(Ⅱ) complex was 1:1 under the adopted experimental conditions.The complexation reaction of gallic acid with ferrous ion was found to be a second order reaction. According to the Arrhenius equation and the Absolute-rate theory,the activation energy and free energy of activation of the complexation reaction were calculated.To understand the kinetic results obtained,a three step reaction mechanism was proposed,which can satisfactorily explain the dependence of the rate constant on the temperature,ionic strength and permittivity of the reaction medium.
Finally,the preparationprocess of ultrahigh-purity gallic acid combining resin absorbance and crystallization was investigated particularly.As shown in the results,crystallization with ultrahigh-purity water can not only improve the purity of gallic acid but also decrease the concentration of metal ions effectively.After three times of crystallization,the purity of gallic acid increased from 96.05% to 99.77%,while the concentration of calcium,iron,sodium and kalium ions were all reduced to around 1 ppm.Different resins have different effects on the removement of metal ions.The three ultra-cleaning resins with high purity all have good effects,especially ZGC-ER80.Treating with several resins with common purity,such as XSC-800 and 001×10,the concentration of metal ions in gallic acid can also be reduced effectively.
The information yielded from this work will provide essential basic data and theoretical instruction for the preparation process of ultrahigh-purity gallic acid.
引文
[1]Zheng,J.H.;Hou,H.S.Development trends of China's electric chemicals during the period of "the 11th five-year plan"(Ⅰ)[J].Fine and Specialty Chemicals.2007,15(19):5-9.
[2]Zheng,J.H.;Hou,H.S.Development trends of China's electric chemicals during the period of "the 11th five-year plan"(Ⅱ)[J].Fine and Specialty Chemicals.2007,15(20):4-9.
[3]科技部主编.化学试剂分类指南[M].北京:化学工业出版社.1999:22-27.
[4]孙忠贤主编.电子化学品[M].北京:化学工业出版社.2001:158.
[5]孙忠贤主编.电子化学品[M].北京:化学工业出版社.2001:159.
[6]孙忠贤主编.电子化学品[M].北京:化学工业出版社.2001:161.
[7]Wu,Y.;Zhang,C.Status and trends of electronic chemicals in China[J].Fine and Specialty Chemicals.2005,13(23):1-7.
[8]Jenczewski,T.J.;Sturtevant,R.L.;Morgan,T.R.;et al.Manufacture of high purity low arsenic anhydrous hydrogen fluoride[P].US A 4756899,1988.
[9]Signorini,L.;Glinos,K.Process for obtaining purified aqueous hydrogen peroxide solution[P].US A 5296104,1994.
[10]Inaba,Y.;Ueno,Y.;Watanabe,M.;et al.Process for preparing high purity hydrogen peroxide aqueous solution[P].US A 5670028,1997.
[11]Sun,Y.C.;Cao,Z.L.;Li,C.Y.;.et al.Method for preparing and purifing propyl acetate[P].CN A 1733685,2006.
[12]Chaurasia,S.C.;Sahayam,A.C.;Mishra,R.K.;et al.A combined isopiestic and sub-boiling distillation method for the purification of hydrofluoric acid used for ICP-MS elemental analysis[J].Atomic Spectroscopy.2006,27(4):134-137.
[13]Niu,C.Y.;Wan,X.S.;Zhang,H.Y.;et al.Simultaneous determination of lead and cadmium in tap water after pre-concentration using quartz sub-boiling distiller by flame atomic absorption spectrometry[J].Chinese Journal of Spectroscopy Laboratoty.2006,23(5):1006-1008.
[14]Fan,Q.;Chen,Q.R.;Xu,Z.G.;et al.Study on the production technology of super-high purity hydrochloric acid[J].Fine and Specialty Chemicals.2004,12(7):14-16.
[15]Sun,J.P.;Fang,F.;Xu,Z.G.;et al.Studies on the process conditions for preparing super-clean and high-pure hydrochloric acid by sub-boiling distillation[J].Chlor-Alkali Industry.2006,(1):30-34.
[16]钱庭宝,刘维林主编.离子交换树脂应用手册[M].天津:南开大学出版社.1989:35-39.
[17]Burton,P.E.;Davoren,D.J.;Dean,T.P.;et al.Process for producing ultra-high purity isopropanol[P].US A 6733637,2004.
[18]Sugihara,Y.;Shigeki,S.Method for purifying impure aqueous hydrogen peroxide solution[P].US A 4999179,1991.
[19]Sugihara,Y.;Tanaka K.;Sakaitani,H.Process for purification-of hydrogen peroxide[P].US A 5614165,1997.
[20]Juda,W.;McRae,W.A.Coherent ion-exchange gels and membranes[J].Journal of the American Society 1950,72(2):1044.
[21]Walter,J.B.;Thomas,R.K.Chemical enrichment and exclusionwith ion exchange membranes[J].Analytical Chemistry.1972,44(12):2109-2011.
[22]Yang,H.W.;Viera,C.;Fischer,J.;et al.Purification of a large protein using ion-exchange membranes[J].Industry and Engineering Chemistry Research.2002,41(6):1597-1602.
[23]gelizarov,S.;Crespo,J.G.;Reis,M.A.Ion exchange membrane bioreactor for selective removal of nitrate from drinking water:control of ion fluxes and process performance[J].Biotechnology Progress.2002,18(2):296-302.
[24]Fonseca,A.D.;Crespo,J.G.;Almeida,J.S.;et al.Drinking water denitrification using a novel ion-exchange membrane bioreactor[J].Environmental Science Technology.2000,34(8):1557-1562.
[25]Vieira,N.E.;Yergey,A.L.Extraction of serum and urine calcium with ion exchange membrane filters for isotope enrichment determination using thermal ionization mass spectrometry[J].Analytical Chemistry.1995,67(22):4217-4219.
[26]Kwon,J.S.;Mayer,B.;Yun,S.T.;et al.The use of ion exchange membranes for isotope analyses on soil water sulfate:laboratory experiments[J].Journal of Environmental Quality.2008,37(2):501-508.
[27]Shimamune,T.;Nakamatsu,H.;Tanaka,M.;et al.Appartus for production of hydrogen peroxide water and method therefor[P].JP A 10280180,1998.
[28]Wilkins,F.C.;McConnelee,P.A.Continuous deionization in the prepatation of microelectronics-grade water[J].Solid State Technology.1988,31(8):87-92.
[29]Giuffrida,A.J.;Jha,A.D;Ganzi,G.C.Electrodeionization Apparatus[P].US A 4632745,1986.
[30]Zhao,Y.;Wang,N.;Sun,X.J.;et al:EDI technology and its application in high-purity water production[J].Journal of North China Electric Power University.2007,34(3):72-76.
[31]Wu,G.F.;Zhang,G.L.;Qu,J.X.;et al.Development of CDI technology and equipment[J].Technology of Water Treatment.2002,28(2):75-77.
[32]Meng,H.;Peng,C.S.;Lu,S.C.Method and apparatus for preparing pure water by continuous electricity deionizing[P].CN A 1504428,2004.
[33]Wang,F.Method and apparatus for.preparing soft water by electrodialysis and ion exchange[P].CN A 1172077,1998.
[34]Akahori,M.;Konishi,S.Development of electrodeionization apparatus containing novel ion-exchange materials[J].Nippon Ion Kokan Gakkaishi.1999,10(2):60-69.
[35]Nishide,Y.;Minamikawa,Y.;Kokubu,J.Method of producing purified aqueous solution of hydrogen peroxide[P].US A 5851505,1998.
[36]Jing,W.H.;Wang,C.H.;Xu,N.P.;et al.Manufacture of high purity hydrogen peroxide by using macroporous resin[J].Journal of Nanjing University of Chemical Technology.2001,23(1):10-13.
[37]Morisaki,A.;Sawaguri,Y.;Matsuda Y.Apparatus and method for removing impurities from aqueous hydrogen peroxide[P].US A 5906738,1999.
[38]Ma,J.H.;Liu,J.Q.;Wang,H.J.;et al.Applicationof purity hydrogen peroxide by using ion-exchange resin and microfilication membrane[J].Ion Exchange and Adsorption.2002,18(4):349-354.
[39]溶液中金属及其他有用成分的提取》编委会主编.溶液中金属及其他有用成分的提取[M].北京:冶金工业出版社.1995:393-475.
[40]Mullin,J.W.主编.结晶工艺[M].大连:大连理工大学出版社.1991:3-5.
[41]Jadhav,V.K.;Chlvate,M.R.;Tavare,N.S.Separation of phenol from its mxture with o-cresol by adductive crystallization[J].Journal of Chemical and Engineering Data.1992,37(2):232-235.
[42]Gaikar,V.G.;Mahapatra,A.;Sharma,M.M.Separation of close boiling point mxtures(p-cresol/m-cresol,guaiacol/alkylphenols,3-picoline/4-picoline,substituted anilines) through dissociation extractive crystallization[J].Industrial and Engineering Chemistry Research.1989,28(2):199-204.
[43]Le,Q.H.;Su,J.X.;Tu,J.L.Separation of p-dichlorobenzene from isomer mixtures by "solventing-out" process[J].Journal of Chemical Engineering of Chinese University.2001,15(1):11-16.
[44]Chatterjee,M.;Ray,J.;Chatterjee,A.;et al.High purity zirconia powders via wet chemical processing:a comparative study[J].Ceramics International.1992,18(5):337-342.
[45]Zhao,J.;Wang,J.;Yang,X.Y.Production of high-purity oxalic acid by recrystallization[J].Henan Chemical Industry.2001,(1):15,25.
[46]Zhang,W.;Zhang,Q.;Ma,F.B.;et al.Study on the high-purity gallic acid [J].Journal of Gulzhou University Technology(Natural Science Edition).2000,29(3):70-74.
[47]Watzenberger,O;Schelling,H.;Pfab,P.;et al.Production of high-purity aqueous hydroxylamine solutions[P].WO A 9857886,1998.
[48]Mao,J.Q.;Mao,Q.L.;Sun,H.H;et al.Manufacture of ultrapure chemicals [P].CN A 1300634,2001.
[49]Saprykin,A.I.;Shelpakova,I.R.Methods for the analysis of high-purity materials with preconcentration of impurities[J].Ukrainskii Khimicheskii Zhurnal.2005,71(9-10):104-112.
[50]Xie,Y.Determination of trace impurity elements in pure indium by ICP-AES[J].Chemical Analysis and meterage.2007,16(3):28-30.
[51]Liu,C.H.Development trend of trace elements analysis for high purity materials[J].Sichuan Nonferrous Metals.2002,14(3):17-19.
[52]Zhu,F.C.;Wu,Q.The analysis of metal impurity in high purity chemical reagents[J].Spectroscopy and Spectral Analysis.1994,14(3):71-78.
[53]Meng,R.;Li,H.H.;Huang,Z.Q.Determination of trace metal in nitric acid of highly purity by ICP-MS[J].Chinese Journal of Analysis Laboratory.2001,20(6):67-69.
[54]Meng,R.;Zheng,L.C.;Tong,S.L.Determination of trace metals in 2-propanol of high purity by ICP-MS.[J].Chemical Reagents.2004,26(5):275-276.
[55]Chen,Q.Application of graphite furnace atomic absorption spectrometry in chemical reagent analysis of the electronic industry[J].Liaoning Chemical Industry.2007,36(12):839-841.
[56]Chen,Q.Determination of iron in super-pure chemical reagents absolute alcohol [J].Guangzhou Chemical Industry.2006,34(4):63-64.
[57]Li,K.;Wei,S.A.Determination of molecular weight and distribution of PLA by means of laser light scattering[J].Journal of Founctional Materials.2007,38A(5):1877-1879.
[58]Tsutsui,K.;Kato,T.Particle size analysis using continuous-angle laser light scattering[J].International Journal of Polymer Analysis and Characterization.1999,5(3):257-265.
[59]Stefanovic,S.C.;Bolanca,T.;Curkovic,L.Simultaneous determination of six inorganic anions in drinking water by non-suppressed ion chromatography[J].Journal of Chromatography A.2001,918(2):325-334.
[60]Liu,Y.;Kaiser,E.;Avdalovic,N.Determination of trace-level anions in high-purity water samples by ion chromatography with an automated on-line fluent generation system[J].Microchemical Journal 1999,62(1):164-173.
[61]Song,L.J.;Di,Y.;Shi,B.Significance and developmental trends in research on plant polyphenols[J].Progress in Chemistry..2000,12(2):161-170.
[62]万素英主编.食品抗氧化剂[M].北京:中国轻工业出版社.1998:29-31.
[63]郑春源主编.水产品保鲜与加工[M].广州:广东科技出版社.1987:54-59.
[64]Wang,Z.D.An important fine chemical-gallic acid[J].Natural Gas Chemical Industry.1995,20(1):38-43.
[65]章思规主编.精细有机化学品技术手册(下)[M].北京:科学出版社.1991:1064-1065.
[66]Inoue,M.;Suzuki,R.;Sakaguchi,N.;et al.Selective induction of cell death in cancer cells by gallic acid[J].Biological & Pharmaceutical Bulletin.1995,18(11):1526-1530.
[67]Koide,T.;Nose,M.;Inoue,M.;et al.Trypanocidal effects of gallic acid and related compounds[J].Planta Medica.1998,64(1):27-30.
[68]Anand,K.K.;Singh,B.;Saxena,A.K.;et al.3,4,5-trihydroxy benzoic acid (gallic acid),the hepatoprotective principle in the fruits of terminalia belerica-bioassay guided activity[J].Pharmacological Research.1997,36(4):315-321.
[69]Yang,G.W.;Zeng,X.J.;Zhou,J.X.Catalytic synthesis of propyl gallate with cation exchange resins[J].Advances in Fine Petrochemicals.2003,4(7):7-9.
[70]Yu,X.W.;Li,Y.Q.;Zhou,S.M.;et al.Synthesis of propyl gallate by mycelium-bound tannase from aspergillus niger in organic solvent[J].World Journal of Microbiology & Biotechnology.2007,23(8):1091-1098.
[71]Ajay,K.R.;Arul,J.;Manickam,L.Bioconversion of gallic acid into pyrogallol by immobilized citrobacter freundii TB_3[J].Journal of Fermentation and Bioengineering.I992,74(3):159-162.
[72]Chen,C.Q.;Wang,Y.B.;Lu,G.A.Study on new technology to prepare pyrogallol [J].Chemistry and Industry of Forest Products.1994,14(4):15-18.
[73]Zhang,F.X.;Zhang,G.X.;Li,X.G.;et al.Synthesis of 3,4,5-trimethoxybenzoic acid from gallic acid waste[J].Journal of Southwest Agricultural University.1997,19(1):13-16.
[74]Dai,Y.Improvement of the synthetic process of 3,4,5-trimethoxy benzaldehyde [J].Journal of Yancheng Institute of Technology(Natural Science Edition).2007,20(4):1-3.
[75]Lee,W.M.Process using hydroxylamine-gallic acid composition[P].US A 6276372,2001.
[76]Liu,Z.Researches on the picking inhibition of gallic acid to carbon steel [J].Industrial Water Treatment.2000,20(2):26-28.
[77]Kong,Z.W.;Huang,H.;You,Z.L.;et al.Study on synthesis of polyphenol type epoxy resin from gallic acid[J].Chemistry and Industry of Forest Products.2005,25(1):33-36.
[78]狄莹,石碧主编.植物多酚[M].北京:科学出版社.2000:11-12.
[79]Li,L.Y.;Li,Y.X.;Yang,X.H.The preparation and application of pyrogallol.[J].Hunan Chemical Industry.1991,21(4):13-15.
[80]Zhou,X.D.;Liu,X.F.Isolation of gallic acid from maple leaves[P].CN A 1022561,1993.
[81]Huang,J.L.;Zhang.Z.H.;Gu,S.H.;et al.Study on preparation of gallic acid from gall-flower extract by alkaline hydrolysis[J].Chemistry and Industry of Forest Products.1997,17(2):23-27.
[82]Chen,J.H.;Zhang,Z.H.;Wang,Y.M.;et al.Study ondirect alkaline hydrolysis to manufacture gallic acid from tara powder[J].Chemistry and Industry of Forest Products.1995,15(1):1-7.
[83]Misro,S.K.;Kumar,M.R.;Banerjee,R.;et al.Production of gallic acid by immobilization of rhizopus oryzae[J].Bioprocess Engineering.1997,16(5): 257-260.
[84]Yang,S.K.;Yang,Y.L.Enzymatic synthesis of gallic acid from tannic acid [J].Fine and Specialty Chemicals.2005,13(5):12-14.
[85]Yang,Y.L.;Yang,W.L.;Liu,C.J.;et al.Studies on enzymatic production of gallic acid with the tannase from aspergillus niger[J].Natural Product Research and Development.2002,14(2):58-60.
[86]Chen,L.Y.;Zhang,X.C.;Yu,L.J.A Study on extracting gallic acid by butanol [J].Journal of Northwest University(Natural Science Edition).1999,29(5):403-405.
[87]Liang,H.L.;Liang,Y.R.;Dong,J.J.;et al.Tea extraction methods in relation to control of epimerization of tea catechins[J].Journal of the Science of Food and Agriculture.2007,87(9):1748-1752.
[88]Zhang,Z.H.;Huang,J.L.;Qin,Q.Eliminating metal ion impurity in industrial gallic acid[P].CN A 1556091,2004.
[89]Zhang,Z.H.;Huang,J.L.;Oin,Q.Eliminating metal ion impurity in industrial gallic acid[P].CN A 1556091,2004.
[90]Maishall,W.L.;Frank,E.U.Ion product of water substances,0-1000℃,1-10000 bar,new international formulation and background[J].Journal of Physical and Chemical Reference Data.1981,10(2):295-304.
[91]Connolly,J.F.Solubility of hydrocarbons in water near the critical solution temperatures[J].Journal of Chemical and Engineering Data.1966,11(1):13-16.
[92]Chandler,K.;Deng,F.H.;Dillow,A.K.;et al.Alkylation reactions in near-critical water in the absence of acid catalysts[J].Industrial and Engineering Chemistry Research.1997,36(12):5175-5179.
[93]Li,C.J.;Chan,T.H.Organic reactions in aqueous media[M].New York:Wiley.1997:132-133.
[94]Zhang,Y.;Wang,M.X.;Wang,D.;et al.Advances in organometalic reactions in aqueous media[J].Progress in Chemistry.1999,11(4):394-402.
[95]Siskin,M.;Katritzky,A.R.Reactivity of organic compounds in hot water: geochemical and technological implications[J].Science.1991,254(5209):231-237.
[96]Savage,P.E.Organic chemical reactions in supercritical water[J].Chemical Reviews.1999,99(2):603-621.
[97]Hunter,S.E.;Savage,P.E.Recent advances in acid- and base-catalyzed organic synthesis in high temperature liquid water[J].Chemical Engineering Science.2004,59(22-23):4903-4909.
[98]Akerlof,G.C.;Oshry,H.I.The dielectric constant of water at high temperatures and in equilibrium with its vapor[J].Journal of the American Chemical Society.1950,72(7):2844-2847.
[99]Lu,X.Y.;He,L.;Zheng,Z.S.;et al.Green chemical processes in near critical water[J].Chemical Industry and Engineering Progress.2003,22(5):477-481.
[100]Lu,X.Y.;Li,Z.;Gao,F.Base-catalyzed reactions in NH_3-enriched near-critical water[J].Industrial aad Engineering Chemistry Research.2006,45(12):4145-4149.
[101]Jing,Q.;Lu,X.Y.Kinetics of non-catalyzed decomposition of D-xylose in high temperature liquid water[J].Chinese Journal of Chemical Engineering.2007 15(5):666-669.
[102]Stephen,H.;Stephen,T.Solubilities of inorganic and organic compounds[M].Oxford:Pergamon Press.1963,1(1):250..
[103]Wan,L.S.;Hwang,C.L.Antioxidant solubility and efficiency[J].Journal of Pharmaceutical Sciences.1969,58(7):889-891.
[104]Wang,L.H.;Cheng,Y.Y.Solubility of puerarin in water,ethanol,and acetone from(288.2 to 328.2) K[J].Journal of Chemical and Engineering Data.2005,50(4):1375-1376.
[105]Wu,J.H.;Wang,J.K.;Zhang,M.J.;et al.Solubility of cefazolin sodium pentahydrate in binary system of ethanol+water mixtures[J].Journal of Chemical and Engineering Data.2006,51(4):1404-1405.
[106]Prausnitz,J.M.;Lichtenthaler,R.N.;Azevedo,E.G.Molecular thermodynamics of fluid-phase equilibria,Second edition[M].Englewood Cliffs:Prentice-Hall.1986:230-266.
[107]Li,Y.H.;Duan,X.F.Study on the adsorptive stripping voltammetry of tin-propyl gallate complex[J].Chinese Journal of Analytical Chemistry.1990,18(5):447-450.
[108]Tomiyasua,T.;Yonehara,N.;Teshima,N.;et al.Kinetic method for the determination of iron(Ⅱ,Ⅲ) by its catalytic effect on the oxidation of 3-methyl-2-benzothiazolinone hydrazone with hydrogen peroxide[J].Analytica Chimica Acts.1999,394(1):55-63.
[109]Zhang,W.Y.;Wang,Z.Q.;Wang,S.X.;et al.The investigation and application of vegetal inhibitor[J].Industrial Water Treatment.1996,16(1):22-23.
[110]Yang,S.J.;Tan,S.Y.;Zhang,Y.Progress of research on biologic inhibitor [J].Surface Technology.2006,35(1):12-14.
[111]Mairtin,O.C.;Michael,J.H.The kinetics and mechanisms of the reactions of aluminium(Ⅲ) with gallic acid,gallic acid methyl ester and adrenaline [J].Journal of Inorganic Biochemistry.2001,84(1-2):1-12.
[112]Michael,J.H.;Mairtin,O.C.The kinetics and mechanisms of the reactions of iron(Ⅲ) with gallic acid,gallic acid methyl ester and catechin[J].Journal of Inorganic Biochemistry.2001,85(2-3):131-142.
[113]Kipton,H.;Powell,J.;Taylor,M.C.Interactions of iron(Ⅱ) and iron(Ⅲ)with gallic acid and its homologues:a potentiometric and spectrophotometric study[J].Australian Journal of Chemistry.1982,35(4):739-756.
[114]Huang,J.L.;Sun,D.W.;Ma,X.L.;et al.Study on protonation constants and coordination compounds stability constants of tannins[J].Journal of Nanjing Forestry University.1992,16(1):13-18.
[115]Sandmann,B.J.;Chien,M.H.;Sandmann,R.A.Stability constants of calcum,magnesium and zinc gallate using divalent ion-selective electrode[J].Analytical letters.1985,18(A2):149-159.
[116]Andjelkovi□,M.;Camp,J.V.;Meulenaer,B.D.;et al.Iron-chaelation properties of phenolic acids bearing catechol and galloyl groups[J].Food Chemistry.2006,98(1):23-31.
[117]Kazmi,S.A.;Qureshi,M.S.;Maqsood,Z.Reactivity of an iron(Ⅲ) complex of gallic acid[J].Inorganic Chimica Acta.1987,137(3):151-154.
[118]Zhang,L.R.;Chen,K.L.;Lin,L.;et al.Study on the complexes of gallic acid-Zn(Ⅱ) and the interaction with DNA[J].Journal of Wuhan University (National Science Edition).2004,50(2):234-238.
[119]Zhang,L.R.Study on the water soluble polysaccharide,polyphenols and volatility components of limonium bicolor[D].Wuhan:College Life Sciences of Wuhan University.2004.
[120]张祥麟,康衡主编.配位化学[M].长沙:中南工业大学出版社.1985:143-145.
[121]Bjerrum,J.Metal ammine formation in aqueous solution.Theory of the reversible step reactions[M].Copenhagen:Haase.I957:296.
[122]蒲希比,R.主编.EDTA及同类化合物的分析应用[M].北京:地质出版社.1982:10.
[123]Ivring,H.M.;Williams,R.J.Stability of transition metal complexes[J].Journal of the Chemical Society.1953,3192-3210.
[124]张祥麟,康衡主编.配位化学[M].长沙:中南工业大学出版社.1986:227.
[125]□□ska,B.□.;Ka□u□na,I.;Gierczyk,B.;et al.Kinetic studies of complexation reaction of polyoxaalkyl phosphates with Fe(Ⅲ) in ethanol[J].Journal of Molecular Structure(Theochem).2002,643(1-3):9-19.
[126]Samy,S.A.Kinetics and mechanism of complex formation between chromium(Ⅲ)and ethylenediamine-N,N′-diacetric acid[J].Materials Chemistry and Physics.2001,72(1):88-92.
[127]Blanco,S.E.;Almandoz,M.C.;Castro,G.T.;et al.Kinetics and structure study on complexes of Al(Ⅲ) with o-hydroxy-benzophenones[J].Journal of Molecular Structure(Theochem).2002,586(1-3):177-192.
[128]Sancho,M.I.;Almandoz,M.C.;Blanco,S.E.;et al.Mechanism of the complexation of aluminum chloride with o-hydroxy-benzophenone[J].Journal of Molecular Structure(Theochem).2003,634(1-3):107-120.
[129]武汉大学主编.分析化学[M].,第五版.北京:高等教育出版社.2006:386.
[130]Van Acker,S.A.;van den Berg,D.J.;Tromp,M.N.;et al.Structural aspects of antioxidant activity of flavonoids[J].Free radical biology & medicine.1996,20(3):331-342.
[131]Job,P.Formation and stability of inorganic complexes in solution[J].Annali di Chimica Applicata.1928,9:113-203.
[132]Ruff,F.;Csizmadia,I.G.Organic reactions.Equilibria,kinetics and mechanism[M].London:Elsevier.1994:46-47.
[133]Laidler,K.J.Chemical kinetics,third edition[M].HarperCollins,1987:198.
[134]Isaacs,N.S.Physical organic chemistry,second edition.[M].England:Longman.1996:213-245.
[135]Ruff,F.;Csizmadia,I.G.Organic reactions.Equilibria,kinetics and mechanism[M].London:Elsevier.1994:257-289.
[136]Luan,G.Y.;Gao,W.P.;Yao,P.J.Progress on the preparation of ultra-pure hydrogen peroxide[J].Journal of Industrial and Engineering Chemistry.2007,13(7):1047-1053.
[137]Feasey,N.D.;Morris,G.W.Purification of hydrogen peroxide[P].US A 5262058,1993.
[2]Zheng,J.H.;Hou,H.S.Development trends of China's electric chemicals during the period of "the 11th five-year plan"(Ⅱ)[J].Fine and Specialty Chemicals.2007,15(20):4-9.
[3]科技部主编.化学试剂分类指南[M].北京:化学工业出版社.1999:22-27.
[4]孙忠贤主编.电子化学品[M].北京:化学工业出版社.2001:158.
[5]孙忠贤主编.电子化学品[M].北京:化学工业出版社.2001:159.
[6]孙忠贤主编.电子化学品[M].北京:化学工业出版社.2001:161.
[7]Wu,Y.;Zhang,C.Status and trends of electronic chemicals in China[J].Fine and Specialty Chemicals.2005,13(23):1-7.
[8]Jenczewski,T.J.;Sturtevant,R.L.;Morgan,T.R.;et al.Manufacture of high purity low arsenic anhydrous hydrogen fluoride[P].US A 4756899,1988.
[9]Signorini,L.;Glinos,K.Process for obtaining purified aqueous hydrogen peroxide solution[P].US A 5296104,1994.
[10]Inaba,Y.;Ueno,Y.;Watanabe,M.;et al.Process for preparing high purity hydrogen peroxide aqueous solution[P].US A 5670028,1997.
[11]Sun,Y.C.;Cao,Z.L.;Li,C.Y.;.et al.Method for preparing and purifing propyl acetate[P].CN A 1733685,2006.
[12]Chaurasia,S.C.;Sahayam,A.C.;Mishra,R.K.;et al.A combined isopiestic and sub-boiling distillation method for the purification of hydrofluoric acid used for ICP-MS elemental analysis[J].Atomic Spectroscopy.2006,27(4):134-137.
[13]Niu,C.Y.;Wan,X.S.;Zhang,H.Y.;et al.Simultaneous determination of lead and cadmium in tap water after pre-concentration using quartz sub-boiling distiller by flame atomic absorption spectrometry[J].Chinese Journal of Spectroscopy Laboratoty.2006,23(5):1006-1008.
[14]Fan,Q.;Chen,Q.R.;Xu,Z.G.;et al.Study on the production technology of super-high purity hydrochloric acid[J].Fine and Specialty Chemicals.2004,12(7):14-16.
[15]Sun,J.P.;Fang,F.;Xu,Z.G.;et al.Studies on the process conditions for preparing super-clean and high-pure hydrochloric acid by sub-boiling distillation[J].Chlor-Alkali Industry.2006,(1):30-34.
[16]钱庭宝,刘维林主编.离子交换树脂应用手册[M].天津:南开大学出版社.1989:35-39.
[17]Burton,P.E.;Davoren,D.J.;Dean,T.P.;et al.Process for producing ultra-high purity isopropanol[P].US A 6733637,2004.
[18]Sugihara,Y.;Shigeki,S.Method for purifying impure aqueous hydrogen peroxide solution[P].US A 4999179,1991.
[19]Sugihara,Y.;Tanaka K.;Sakaitani,H.Process for purification-of hydrogen peroxide[P].US A 5614165,1997.
[20]Juda,W.;McRae,W.A.Coherent ion-exchange gels and membranes[J].Journal of the American Society 1950,72(2):1044.
[21]Walter,J.B.;Thomas,R.K.Chemical enrichment and exclusionwith ion exchange membranes[J].Analytical Chemistry.1972,44(12):2109-2011.
[22]Yang,H.W.;Viera,C.;Fischer,J.;et al.Purification of a large protein using ion-exchange membranes[J].Industry and Engineering Chemistry Research.2002,41(6):1597-1602.
[23]gelizarov,S.;Crespo,J.G.;Reis,M.A.Ion exchange membrane bioreactor for selective removal of nitrate from drinking water:control of ion fluxes and process performance[J].Biotechnology Progress.2002,18(2):296-302.
[24]Fonseca,A.D.;Crespo,J.G.;Almeida,J.S.;et al.Drinking water denitrification using a novel ion-exchange membrane bioreactor[J].Environmental Science Technology.2000,34(8):1557-1562.
[25]Vieira,N.E.;Yergey,A.L.Extraction of serum and urine calcium with ion exchange membrane filters for isotope enrichment determination using thermal ionization mass spectrometry[J].Analytical Chemistry.1995,67(22):4217-4219.
[26]Kwon,J.S.;Mayer,B.;Yun,S.T.;et al.The use of ion exchange membranes for isotope analyses on soil water sulfate:laboratory experiments[J].Journal of Environmental Quality.2008,37(2):501-508.
[27]Shimamune,T.;Nakamatsu,H.;Tanaka,M.;et al.Appartus for production of hydrogen peroxide water and method therefor[P].JP A 10280180,1998.
[28]Wilkins,F.C.;McConnelee,P.A.Continuous deionization in the prepatation of microelectronics-grade water[J].Solid State Technology.1988,31(8):87-92.
[29]Giuffrida,A.J.;Jha,A.D;Ganzi,G.C.Electrodeionization Apparatus[P].US A 4632745,1986.
[30]Zhao,Y.;Wang,N.;Sun,X.J.;et al:EDI technology and its application in high-purity water production[J].Journal of North China Electric Power University.2007,34(3):72-76.
[31]Wu,G.F.;Zhang,G.L.;Qu,J.X.;et al.Development of CDI technology and equipment[J].Technology of Water Treatment.2002,28(2):75-77.
[32]Meng,H.;Peng,C.S.;Lu,S.C.Method and apparatus for preparing pure water by continuous electricity deionizing[P].CN A 1504428,2004.
[33]Wang,F.Method and apparatus for.preparing soft water by electrodialysis and ion exchange[P].CN A 1172077,1998.
[34]Akahori,M.;Konishi,S.Development of electrodeionization apparatus containing novel ion-exchange materials[J].Nippon Ion Kokan Gakkaishi.1999,10(2):60-69.
[35]Nishide,Y.;Minamikawa,Y.;Kokubu,J.Method of producing purified aqueous solution of hydrogen peroxide[P].US A 5851505,1998.
[36]Jing,W.H.;Wang,C.H.;Xu,N.P.;et al.Manufacture of high purity hydrogen peroxide by using macroporous resin[J].Journal of Nanjing University of Chemical Technology.2001,23(1):10-13.
[37]Morisaki,A.;Sawaguri,Y.;Matsuda Y.Apparatus and method for removing impurities from aqueous hydrogen peroxide[P].US A 5906738,1999.
[38]Ma,J.H.;Liu,J.Q.;Wang,H.J.;et al.Applicationof purity hydrogen peroxide by using ion-exchange resin and microfilication membrane[J].Ion Exchange and Adsorption.2002,18(4):349-354.
[39]溶液中金属及其他有用成分的提取》编委会主编.溶液中金属及其他有用成分的提取[M].北京:冶金工业出版社.1995:393-475.
[40]Mullin,J.W.主编.结晶工艺[M].大连:大连理工大学出版社.1991:3-5.
[41]Jadhav,V.K.;Chlvate,M.R.;Tavare,N.S.Separation of phenol from its mxture with o-cresol by adductive crystallization[J].Journal of Chemical and Engineering Data.1992,37(2):232-235.
[42]Gaikar,V.G.;Mahapatra,A.;Sharma,M.M.Separation of close boiling point mxtures(p-cresol/m-cresol,guaiacol/alkylphenols,3-picoline/4-picoline,substituted anilines) through dissociation extractive crystallization[J].Industrial and Engineering Chemistry Research.1989,28(2):199-204.
[43]Le,Q.H.;Su,J.X.;Tu,J.L.Separation of p-dichlorobenzene from isomer mixtures by "solventing-out" process[J].Journal of Chemical Engineering of Chinese University.2001,15(1):11-16.
[44]Chatterjee,M.;Ray,J.;Chatterjee,A.;et al.High purity zirconia powders via wet chemical processing:a comparative study[J].Ceramics International.1992,18(5):337-342.
[45]Zhao,J.;Wang,J.;Yang,X.Y.Production of high-purity oxalic acid by recrystallization[J].Henan Chemical Industry.2001,(1):15,25.
[46]Zhang,W.;Zhang,Q.;Ma,F.B.;et al.Study on the high-purity gallic acid [J].Journal of Gulzhou University Technology(Natural Science Edition).2000,29(3):70-74.
[47]Watzenberger,O;Schelling,H.;Pfab,P.;et al.Production of high-purity aqueous hydroxylamine solutions[P].WO A 9857886,1998.
[48]Mao,J.Q.;Mao,Q.L.;Sun,H.H;et al.Manufacture of ultrapure chemicals [P].CN A 1300634,2001.
[49]Saprykin,A.I.;Shelpakova,I.R.Methods for the analysis of high-purity materials with preconcentration of impurities[J].Ukrainskii Khimicheskii Zhurnal.2005,71(9-10):104-112.
[50]Xie,Y.Determination of trace impurity elements in pure indium by ICP-AES[J].Chemical Analysis and meterage.2007,16(3):28-30.
[51]Liu,C.H.Development trend of trace elements analysis for high purity materials[J].Sichuan Nonferrous Metals.2002,14(3):17-19.
[52]Zhu,F.C.;Wu,Q.The analysis of metal impurity in high purity chemical reagents[J].Spectroscopy and Spectral Analysis.1994,14(3):71-78.
[53]Meng,R.;Li,H.H.;Huang,Z.Q.Determination of trace metal in nitric acid of highly purity by ICP-MS[J].Chinese Journal of Analysis Laboratory.2001,20(6):67-69.
[54]Meng,R.;Zheng,L.C.;Tong,S.L.Determination of trace metals in 2-propanol of high purity by ICP-MS.[J].Chemical Reagents.2004,26(5):275-276.
[55]Chen,Q.Application of graphite furnace atomic absorption spectrometry in chemical reagent analysis of the electronic industry[J].Liaoning Chemical Industry.2007,36(12):839-841.
[56]Chen,Q.Determination of iron in super-pure chemical reagents absolute alcohol [J].Guangzhou Chemical Industry.2006,34(4):63-64.
[57]Li,K.;Wei,S.A.Determination of molecular weight and distribution of PLA by means of laser light scattering[J].Journal of Founctional Materials.2007,38A(5):1877-1879.
[58]Tsutsui,K.;Kato,T.Particle size analysis using continuous-angle laser light scattering[J].International Journal of Polymer Analysis and Characterization.1999,5(3):257-265.
[59]Stefanovic,S.C.;Bolanca,T.;Curkovic,L.Simultaneous determination of six inorganic anions in drinking water by non-suppressed ion chromatography[J].Journal of Chromatography A.2001,918(2):325-334.
[60]Liu,Y.;Kaiser,E.;Avdalovic,N.Determination of trace-level anions in high-purity water samples by ion chromatography with an automated on-line fluent generation system[J].Microchemical Journal 1999,62(1):164-173.
[61]Song,L.J.;Di,Y.;Shi,B.Significance and developmental trends in research on plant polyphenols[J].Progress in Chemistry..2000,12(2):161-170.
[62]万素英主编.食品抗氧化剂[M].北京:中国轻工业出版社.1998:29-31.
[63]郑春源主编.水产品保鲜与加工[M].广州:广东科技出版社.1987:54-59.
[64]Wang,Z.D.An important fine chemical-gallic acid[J].Natural Gas Chemical Industry.1995,20(1):38-43.
[65]章思规主编.精细有机化学品技术手册(下)[M].北京:科学出版社.1991:1064-1065.
[66]Inoue,M.;Suzuki,R.;Sakaguchi,N.;et al.Selective induction of cell death in cancer cells by gallic acid[J].Biological & Pharmaceutical Bulletin.1995,18(11):1526-1530.
[67]Koide,T.;Nose,M.;Inoue,M.;et al.Trypanocidal effects of gallic acid and related compounds[J].Planta Medica.1998,64(1):27-30.
[68]Anand,K.K.;Singh,B.;Saxena,A.K.;et al.3,4,5-trihydroxy benzoic acid (gallic acid),the hepatoprotective principle in the fruits of terminalia belerica-bioassay guided activity[J].Pharmacological Research.1997,36(4):315-321.
[69]Yang,G.W.;Zeng,X.J.;Zhou,J.X.Catalytic synthesis of propyl gallate with cation exchange resins[J].Advances in Fine Petrochemicals.2003,4(7):7-9.
[70]Yu,X.W.;Li,Y.Q.;Zhou,S.M.;et al.Synthesis of propyl gallate by mycelium-bound tannase from aspergillus niger in organic solvent[J].World Journal of Microbiology & Biotechnology.2007,23(8):1091-1098.
[71]Ajay,K.R.;Arul,J.;Manickam,L.Bioconversion of gallic acid into pyrogallol by immobilized citrobacter freundii TB_3[J].Journal of Fermentation and Bioengineering.I992,74(3):159-162.
[72]Chen,C.Q.;Wang,Y.B.;Lu,G.A.Study on new technology to prepare pyrogallol [J].Chemistry and Industry of Forest Products.1994,14(4):15-18.
[73]Zhang,F.X.;Zhang,G.X.;Li,X.G.;et al.Synthesis of 3,4,5-trimethoxybenzoic acid from gallic acid waste[J].Journal of Southwest Agricultural University.1997,19(1):13-16.
[74]Dai,Y.Improvement of the synthetic process of 3,4,5-trimethoxy benzaldehyde [J].Journal of Yancheng Institute of Technology(Natural Science Edition).2007,20(4):1-3.
[75]Lee,W.M.Process using hydroxylamine-gallic acid composition[P].US A 6276372,2001.
[76]Liu,Z.Researches on the picking inhibition of gallic acid to carbon steel [J].Industrial Water Treatment.2000,20(2):26-28.
[77]Kong,Z.W.;Huang,H.;You,Z.L.;et al.Study on synthesis of polyphenol type epoxy resin from gallic acid[J].Chemistry and Industry of Forest Products.2005,25(1):33-36.
[78]狄莹,石碧主编.植物多酚[M].北京:科学出版社.2000:11-12.
[79]Li,L.Y.;Li,Y.X.;Yang,X.H.The preparation and application of pyrogallol.[J].Hunan Chemical Industry.1991,21(4):13-15.
[80]Zhou,X.D.;Liu,X.F.Isolation of gallic acid from maple leaves[P].CN A 1022561,1993.
[81]Huang,J.L.;Zhang.Z.H.;Gu,S.H.;et al.Study on preparation of gallic acid from gall-flower extract by alkaline hydrolysis[J].Chemistry and Industry of Forest Products.1997,17(2):23-27.
[82]Chen,J.H.;Zhang,Z.H.;Wang,Y.M.;et al.Study ondirect alkaline hydrolysis to manufacture gallic acid from tara powder[J].Chemistry and Industry of Forest Products.1995,15(1):1-7.
[83]Misro,S.K.;Kumar,M.R.;Banerjee,R.;et al.Production of gallic acid by immobilization of rhizopus oryzae[J].Bioprocess Engineering.1997,16(5): 257-260.
[84]Yang,S.K.;Yang,Y.L.Enzymatic synthesis of gallic acid from tannic acid [J].Fine and Specialty Chemicals.2005,13(5):12-14.
[85]Yang,Y.L.;Yang,W.L.;Liu,C.J.;et al.Studies on enzymatic production of gallic acid with the tannase from aspergillus niger[J].Natural Product Research and Development.2002,14(2):58-60.
[86]Chen,L.Y.;Zhang,X.C.;Yu,L.J.A Study on extracting gallic acid by butanol [J].Journal of Northwest University(Natural Science Edition).1999,29(5):403-405.
[87]Liang,H.L.;Liang,Y.R.;Dong,J.J.;et al.Tea extraction methods in relation to control of epimerization of tea catechins[J].Journal of the Science of Food and Agriculture.2007,87(9):1748-1752.
[88]Zhang,Z.H.;Huang,J.L.;Qin,Q.Eliminating metal ion impurity in industrial gallic acid[P].CN A 1556091,2004.
[89]Zhang,Z.H.;Huang,J.L.;Oin,Q.Eliminating metal ion impurity in industrial gallic acid[P].CN A 1556091,2004.
[90]Maishall,W.L.;Frank,E.U.Ion product of water substances,0-1000℃,1-10000 bar,new international formulation and background[J].Journal of Physical and Chemical Reference Data.1981,10(2):295-304.
[91]Connolly,J.F.Solubility of hydrocarbons in water near the critical solution temperatures[J].Journal of Chemical and Engineering Data.1966,11(1):13-16.
[92]Chandler,K.;Deng,F.H.;Dillow,A.K.;et al.Alkylation reactions in near-critical water in the absence of acid catalysts[J].Industrial and Engineering Chemistry Research.1997,36(12):5175-5179.
[93]Li,C.J.;Chan,T.H.Organic reactions in aqueous media[M].New York:Wiley.1997:132-133.
[94]Zhang,Y.;Wang,M.X.;Wang,D.;et al.Advances in organometalic reactions in aqueous media[J].Progress in Chemistry.1999,11(4):394-402.
[95]Siskin,M.;Katritzky,A.R.Reactivity of organic compounds in hot water: geochemical and technological implications[J].Science.1991,254(5209):231-237.
[96]Savage,P.E.Organic chemical reactions in supercritical water[J].Chemical Reviews.1999,99(2):603-621.
[97]Hunter,S.E.;Savage,P.E.Recent advances in acid- and base-catalyzed organic synthesis in high temperature liquid water[J].Chemical Engineering Science.2004,59(22-23):4903-4909.
[98]Akerlof,G.C.;Oshry,H.I.The dielectric constant of water at high temperatures and in equilibrium with its vapor[J].Journal of the American Chemical Society.1950,72(7):2844-2847.
[99]Lu,X.Y.;He,L.;Zheng,Z.S.;et al.Green chemical processes in near critical water[J].Chemical Industry and Engineering Progress.2003,22(5):477-481.
[100]Lu,X.Y.;Li,Z.;Gao,F.Base-catalyzed reactions in NH_3-enriched near-critical water[J].Industrial aad Engineering Chemistry Research.2006,45(12):4145-4149.
[101]Jing,Q.;Lu,X.Y.Kinetics of non-catalyzed decomposition of D-xylose in high temperature liquid water[J].Chinese Journal of Chemical Engineering.2007 15(5):666-669.
[102]Stephen,H.;Stephen,T.Solubilities of inorganic and organic compounds[M].Oxford:Pergamon Press.1963,1(1):250..
[103]Wan,L.S.;Hwang,C.L.Antioxidant solubility and efficiency[J].Journal of Pharmaceutical Sciences.1969,58(7):889-891.
[104]Wang,L.H.;Cheng,Y.Y.Solubility of puerarin in water,ethanol,and acetone from(288.2 to 328.2) K[J].Journal of Chemical and Engineering Data.2005,50(4):1375-1376.
[105]Wu,J.H.;Wang,J.K.;Zhang,M.J.;et al.Solubility of cefazolin sodium pentahydrate in binary system of ethanol+water mixtures[J].Journal of Chemical and Engineering Data.2006,51(4):1404-1405.
[106]Prausnitz,J.M.;Lichtenthaler,R.N.;Azevedo,E.G.Molecular thermodynamics of fluid-phase equilibria,Second edition[M].Englewood Cliffs:Prentice-Hall.1986:230-266.
[107]Li,Y.H.;Duan,X.F.Study on the adsorptive stripping voltammetry of tin-propyl gallate complex[J].Chinese Journal of Analytical Chemistry.1990,18(5):447-450.
[108]Tomiyasua,T.;Yonehara,N.;Teshima,N.;et al.Kinetic method for the determination of iron(Ⅱ,Ⅲ) by its catalytic effect on the oxidation of 3-methyl-2-benzothiazolinone hydrazone with hydrogen peroxide[J].Analytica Chimica Acts.1999,394(1):55-63.
[109]Zhang,W.Y.;Wang,Z.Q.;Wang,S.X.;et al.The investigation and application of vegetal inhibitor[J].Industrial Water Treatment.1996,16(1):22-23.
[110]Yang,S.J.;Tan,S.Y.;Zhang,Y.Progress of research on biologic inhibitor [J].Surface Technology.2006,35(1):12-14.
[111]Mairtin,O.C.;Michael,J.H.The kinetics and mechanisms of the reactions of aluminium(Ⅲ) with gallic acid,gallic acid methyl ester and adrenaline [J].Journal of Inorganic Biochemistry.2001,84(1-2):1-12.
[112]Michael,J.H.;Mairtin,O.C.The kinetics and mechanisms of the reactions of iron(Ⅲ) with gallic acid,gallic acid methyl ester and catechin[J].Journal of Inorganic Biochemistry.2001,85(2-3):131-142.
[113]Kipton,H.;Powell,J.;Taylor,M.C.Interactions of iron(Ⅱ) and iron(Ⅲ)with gallic acid and its homologues:a potentiometric and spectrophotometric study[J].Australian Journal of Chemistry.1982,35(4):739-756.
[114]Huang,J.L.;Sun,D.W.;Ma,X.L.;et al.Study on protonation constants and coordination compounds stability constants of tannins[J].Journal of Nanjing Forestry University.1992,16(1):13-18.
[115]Sandmann,B.J.;Chien,M.H.;Sandmann,R.A.Stability constants of calcum,magnesium and zinc gallate using divalent ion-selective electrode[J].Analytical letters.1985,18(A2):149-159.
[116]Andjelkovi□,M.;Camp,J.V.;Meulenaer,B.D.;et al.Iron-chaelation properties of phenolic acids bearing catechol and galloyl groups[J].Food Chemistry.2006,98(1):23-31.
[117]Kazmi,S.A.;Qureshi,M.S.;Maqsood,Z.Reactivity of an iron(Ⅲ) complex of gallic acid[J].Inorganic Chimica Acta.1987,137(3):151-154.
[118]Zhang,L.R.;Chen,K.L.;Lin,L.;et al.Study on the complexes of gallic acid-Zn(Ⅱ) and the interaction with DNA[J].Journal of Wuhan University (National Science Edition).2004,50(2):234-238.
[119]Zhang,L.R.Study on the water soluble polysaccharide,polyphenols and volatility components of limonium bicolor[D].Wuhan:College Life Sciences of Wuhan University.2004.
[120]张祥麟,康衡主编.配位化学[M].长沙:中南工业大学出版社.1985:143-145.
[121]Bjerrum,J.Metal ammine formation in aqueous solution.Theory of the reversible step reactions[M].Copenhagen:Haase.I957:296.
[122]蒲希比,R.主编.EDTA及同类化合物的分析应用[M].北京:地质出版社.1982:10.
[123]Ivring,H.M.;Williams,R.J.Stability of transition metal complexes[J].Journal of the Chemical Society.1953,3192-3210.
[124]张祥麟,康衡主编.配位化学[M].长沙:中南工业大学出版社.1986:227.
[125]□□ska,B.□.;Ka□u□na,I.;Gierczyk,B.;et al.Kinetic studies of complexation reaction of polyoxaalkyl phosphates with Fe(Ⅲ) in ethanol[J].Journal of Molecular Structure(Theochem).2002,643(1-3):9-19.
[126]Samy,S.A.Kinetics and mechanism of complex formation between chromium(Ⅲ)and ethylenediamine-N,N′-diacetric acid[J].Materials Chemistry and Physics.2001,72(1):88-92.
[127]Blanco,S.E.;Almandoz,M.C.;Castro,G.T.;et al.Kinetics and structure study on complexes of Al(Ⅲ) with o-hydroxy-benzophenones[J].Journal of Molecular Structure(Theochem).2002,586(1-3):177-192.
[128]Sancho,M.I.;Almandoz,M.C.;Blanco,S.E.;et al.Mechanism of the complexation of aluminum chloride with o-hydroxy-benzophenone[J].Journal of Molecular Structure(Theochem).2003,634(1-3):107-120.
[129]武汉大学主编.分析化学[M].,第五版.北京:高等教育出版社.2006:386.
[130]Van Acker,S.A.;van den Berg,D.J.;Tromp,M.N.;et al.Structural aspects of antioxidant activity of flavonoids[J].Free radical biology & medicine.1996,20(3):331-342.
[131]Job,P.Formation and stability of inorganic complexes in solution[J].Annali di Chimica Applicata.1928,9:113-203.
[132]Ruff,F.;Csizmadia,I.G.Organic reactions.Equilibria,kinetics and mechanism[M].London:Elsevier.1994:46-47.
[133]Laidler,K.J.Chemical kinetics,third edition[M].HarperCollins,1987:198.
[134]Isaacs,N.S.Physical organic chemistry,second edition.[M].England:Longman.1996:213-245.
[135]Ruff,F.;Csizmadia,I.G.Organic reactions.Equilibria,kinetics and mechanism[M].London:Elsevier.1994:257-289.
[136]Luan,G.Y.;Gao,W.P.;Yao,P.J.Progress on the preparation of ultra-pure hydrogen peroxide[J].Journal of Industrial and Engineering Chemistry.2007,13(7):1047-1053.
[137]Feasey,N.D.;Morris,G.W.Purification of hydrogen peroxide[P].US A 5262058,1993.