萘二磺酸钠转化产物催化合成双酚S及精制
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摘要
采用阳离子交换树脂将2,6-萘二磺酸钠转化为2,6-萘二磺酸并用于双酚S(BPS)合成,研究了转化时间、温度、树脂用量等条件对反应的影响。较优的转化条件为:将2,6-萘二磺酸钠完全溶解后,加入用量为理论值37倍的001×7型强酸性聚苯乙烯系阳离子交换树脂,常温转化24 h,用转化产物催化合成的BPS粗品收率为93.5%,BPS质量分数为92.3%。采用水-吸附剂体系进行精制,不添加有机试剂,BPS产品质量分数高,操作简单,易于工业化。较优的精制条件为:7 g BPS粗品加热溶于300 g去离子水后,加入0.5 g海泡石、0.2 g活性炭,回流搅拌1 h,过滤后潮品再加热溶于180 g去离子水中,加入0.3 g海泡石,回流搅拌1 h,得白色产品,BPS质量分数可达99.7%。精制水可循环套用且可提高BPS产品收率至82.9%。
Transformation of disodium 2,6-naphthalenedisulfonate into 2,6-naphthalenedisulfonic acid was catalyzed by cationic exchange resin and the 2,6-naphthalenedisulfonic acid was used to catalyze the synthesis of bisphenol S( BPS). The effects of the reaction time,temperature and the amount of resin were investigated.The optimized exchange process was applied as follows: After disodium 2,6-naphthalenedisulfonate was completely dissolved,37 times of 001 × 7 strong acidic polystyrene type cationic exchange resin were added into the system. The converted products were used to catalyze the synthesis of BPS. The yield of crude product BPS reached 93. 5% and the mass fraction of BPS was 92. 3%. Crude BPS was purified by adsorbent without organic solvent. The mass fraction of the product obtained by the process is high. The improved process is easy to be operated and industrialized. The improved purification process was applied as follows:Firstly 7 g of crude BPS was dissolved in 300 g hot water. Then 0. 5 g sepiolite and 0. 2 g active carbon were added under stirring. The wet product was dissolved in 180 g hot water again and another 0. 3 g sepiolite was added. After1 hour of stirring,a white product was obtained and the purity of BPS reached 99. 7%. The water could be recycled,resulting in increasing yield of product BPS to 82. 9% at the same time.
Transformation of disodium 2,6-naphthalenedisulfonate into 2,6-naphthalenedisulfonic acid was catalyzed by cationic exchange resin and the 2,6-naphthalenedisulfonic acid was used to catalyze the synthesis of bisphenol S( BPS). The effects of the reaction time,temperature and the amount of resin were investigated.The optimized exchange process was applied as follows: After disodium 2,6-naphthalenedisulfonate was completely dissolved,37 times of 001 × 7 strong acidic polystyrene type cationic exchange resin were added into the system. The converted products were used to catalyze the synthesis of BPS. The yield of crude product BPS reached 93. 5% and the mass fraction of BPS was 92. 3%. Crude BPS was purified by adsorbent without organic solvent. The mass fraction of the product obtained by the process is high. The improved process is easy to be operated and industrialized. The improved purification process was applied as follows:Firstly 7 g of crude BPS was dissolved in 300 g hot water. Then 0. 5 g sepiolite and 0. 2 g active carbon were added under stirring. The wet product was dissolved in 180 g hot water again and another 0. 3 g sepiolite was added. After1 hour of stirring,a white product was obtained and the purity of BPS reached 99. 7%. The water could be recycled,resulting in increasing yield of product BPS to 82. 9% at the same time.
引文
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[17]ZHANG Tianyong,LIU Qian,LI Bin,et al.Process for the Purification of Bisphenol S by Mixed Solvents[J].Fine Chem,2015,32(7):817-820(in Chinese).张天永,刘茜,李彬,等.混合溶剂法精制双酚S的工艺研究[J].精细化工,2015,32(7):817-820.
[18]Hidaka T.Method for Preparation of 4,4'-Bisphenol Sulfone by Reaction of Phenol with Sulfuric Acid:WO,2003078388[P],2003-09-25.
[19]Kitamura H,Shimizu Y,Ohura O.Process for Isolating 4,4'-Dihydroxydiphenylsulfone from a Mixture of Dihydroxydiphenylsulfone Isomers:US,4382147[P],1983-05-03.
[20]Kuznetsov L L,Belyaev A N,Gromov K V.Method for Separation of 2,4'-and 4,4'-Dihydroxydi-phenylsulfone:RU,2307122[P],2007-09-27.
[21]Coruh S,Geyikci F,Elevli S.Adsorption of Neutral Red Dye from an Aqueous Solution onto Natural Sepiolite Using Full Factorial Design[J].Clays Clay Miner,2011,59(6):617-625.
[22]LU Yi,QIU Dan,ZHANG Kaili.Research Progress on Application of Sepiolite Absorbent[J].J Ningbo Univ Technol,2016,28(1):17-22(in Chinese).鲁旖,仇丹,章凯丽.海泡石吸附剂的应用研究进展[J].宁波工程学院学报,2016,28(1):17-22.
[2]YU Lijuan,SUN Peng,LI Guangyi,et al.Research Progress in Flame Retardants[J].Shanghai Plast,2013,(3):21-24(in Chinese).于立娟,孙鹏,李广义,等.阻燃剂的研究进展[J].上海塑料,2013,(3):21-24.
[3]CHEN Xiaofang,LI Dong,GU Xu.Study on Synthesis and Application of Bisphenol S[J].Guangzhou Chem Ind,2016,44(5):26-28(in Chinese).陈小芳,李东,固旭.双酚类化合物的合成及应用进展研究[J].广州化工,2016,44(5):26-28.
[4]MA Haihong,ZHANG Shaojun,SHI Jianming.Recent Research Progress on Preparation of Bisphenol S[J].Chem Ind Eng Prog,2001,20(8):22-26(in Chinese).马海洪,张绍军,石建明.制备双酚S研究的新进展[J].化工进展,2001,20(8):22-26.
[5]QIU Mingyan,ZHANG Tianyong.Progress in the Synthesis and Purification of Dihydroxydiphenylsulfone[J].Dyest Color,2005,42(5):35-37(in Chinese).邱明艳,张天永.二羟基二苯砜的研究进展[J].染料与染色,2005,42(5):35-37.
[6]QIU Mingyan.Study on Synthesis and Purification of Developer Dihydroxydiphenylsulfone[D].Tianjin:Tianjin University,2005(in Chinese).邱明艳.显色剂二羟基二苯砜的合成及精制研究[D].天津:天津大学,2005.
[7]SHAO Hongfei.Synthesis of Developer Dihydroxydiphenylsulfone[D].Tianjin:Tianjin University,2006(in Chinese).邵红飞.二羟基二苯砜显色剂的合成[D].天津:天津大学,2006.
[8]Ogata E,One K,Nate K.Process for Preparing 4,4'-Dihydroxydiphenyl Sulfone Having High Purity:US,4820831[P],1989-04-11.
[9]SUN Jiale.Preparation Method of High Purity 4,4'-Dihydroxydiphenylsulfone:CN,1508127[P],2004-06-30(in Chinese).孙家乐.高纯度4,4'-二羟基二苯酚的制备方法:CN,1508127[P],2004-06-30.
[10]Ogata E,Oi F,Yanase N,et al.Process for Preparation of High-purity 4,4'-Dihydroxydiphenylsulfone:WO,2004029020[P],2004-04-08.
[11]ZHANG Tianyong,ZHU Jiayou,LI Bin,et al.A New Process for Preparation of 4,4'-Dihydroxydiphenylsulfone[J].Chem Ind Eng Prog,2013,32(11):2719-2722(in Chinese).张天永,朱佳佑,李彬,等.4,4'-二羟基二苯砜合成新工艺的研究[J].化工进展,2013,32(11):2719-2722.
[12]ZHANG Tianyong,LIU Qian,LI Bin,et al.Study on Water Removal Control in Synthesis and Purification of Bisphenol S[J].Chemistry,2016,79(3):259-263(in Chinese).张天永,刘茜,李彬,等.双酚S合成过程脱水控制和精制工艺研究[J].化学通报,2016,79(3):259-263.
[13]Oi F,Yanase N,Kitahara T,et al.Process for Producing Dihydroxydiphenylsulfone:EP,1498412[P],2005-01-19.
[14]Walsingham R W.Preparation of 4,4'-Dihydroxydiphenylsulphone:EP,326320[P],1989-08-02.
[15]Arient J.Process for the Purification and Isolation of Mixtures of 4,4'-and 2,4'-Dihydroxydiphenylsulfone:CS,257071[P],1988-04-15.
[16]ZHANG Tianyong,ZHU Jiayou,LI Bin,et al.Process for Production of High-purity 4,4'-Dihydroxydiphenylsulfone[J].Mod Chem Ind,2014,34(20):113-116(in Chinese).张天永,朱佳佑,李彬,等.高纯度双酚S的精制工艺研究[J].现代化工,2014,34(20):113-116.
[17]ZHANG Tianyong,LIU Qian,LI Bin,et al.Process for the Purification of Bisphenol S by Mixed Solvents[J].Fine Chem,2015,32(7):817-820(in Chinese).张天永,刘茜,李彬,等.混合溶剂法精制双酚S的工艺研究[J].精细化工,2015,32(7):817-820.
[18]Hidaka T.Method for Preparation of 4,4'-Bisphenol Sulfone by Reaction of Phenol with Sulfuric Acid:WO,2003078388[P],2003-09-25.
[19]Kitamura H,Shimizu Y,Ohura O.Process for Isolating 4,4'-Dihydroxydiphenylsulfone from a Mixture of Dihydroxydiphenylsulfone Isomers:US,4382147[P],1983-05-03.
[20]Kuznetsov L L,Belyaev A N,Gromov K V.Method for Separation of 2,4'-and 4,4'-Dihydroxydi-phenylsulfone:RU,2307122[P],2007-09-27.
[21]Coruh S,Geyikci F,Elevli S.Adsorption of Neutral Red Dye from an Aqueous Solution onto Natural Sepiolite Using Full Factorial Design[J].Clays Clay Miner,2011,59(6):617-625.
[22]LU Yi,QIU Dan,ZHANG Kaili.Research Progress on Application of Sepiolite Absorbent[J].J Ningbo Univ Technol,2016,28(1):17-22(in Chinese).鲁旖,仇丹,章凯丽.海泡石吸附剂的应用研究进展[J].宁波工程学院学报,2016,28(1):17-22.