间氨基苯酚在间苯二胺-水溶液中溶解度的测定
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摘要
水解法生产间氨基苯酚(MAP)的过程中需采用结晶来实现产品和原料间苯二胺(MPD)的分离。利用激光动态法,常压、温度288.15～335.15K下测定了间氨基苯酚在间苯二胺-水溶液中溶解度。结果表明:间氨基苯酚的溶解度随着温度的升高和间苯二胺质量含量的增加而相应增大。运用经验方程、Apelblat方程、λh方程对实验数据进行关联,获得相应的模型参数,模型计算值与实验值的最大总平均相对误差分别为3.25%、1.65%、4.05%。并根据λh方程的关联参数结果,解释了间苯二胺的加入对间氨基苯酚在水中溶解过程的影响规律。本工作可为间苯二胺水解生产间氨基苯酚的结晶工艺设计提供数据支持,同时对间氨基苯酚的分离过程提供指导。
The separation of the raw material m-phenylene diamine(MPD)and the product maminophenol(MAP)is carried out by crystallization on synthesis of MAP by hydrolysis of MPD.The solubility data of MAP in m-phenylene diamine-water solution were measured over the temperature range from 288.15 Kto 335.15 Kby using a laser monitoring observation technique at atmospheric pressure.The results showed that the solubility of MAP increases with the increase of temperature and the content of MPD.The experimental results were correlated with empirical equation,Apelblat equation andλhequation.The maximum average relative deviations of the calculated values and experimental values were 3.25%,1.65%and 4.05% for three equations respectively.And the influence of MPD on the dissolution process of MAP in water was explained according to the correlation parameters of λh equation.This paper provides data support for the engineering design of crystallizationprocess of MAP by hydrolysis of m-phenylene diamine,and provides guidance for MAP separation process.
The separation of the raw material m-phenylene diamine(MPD)and the product maminophenol(MAP)is carried out by crystallization on synthesis of MAP by hydrolysis of MPD.The solubility data of MAP in m-phenylene diamine-water solution were measured over the temperature range from 288.15 Kto 335.15 Kby using a laser monitoring observation technique at atmospheric pressure.The results showed that the solubility of MAP increases with the increase of temperature and the content of MPD.The experimental results were correlated with empirical equation,Apelblat equation andλhequation.The maximum average relative deviations of the calculated values and experimental values were 3.25%,1.65%and 4.05% for three equations respectively.And the influence of MPD on the dissolution process of MAP in water was explained according to the correlation parameters of λh equation.This paper provides data support for the engineering design of crystallizationprocess of MAP by hydrolysis of m-phenylene diamine,and provides guidance for MAP separation process.
引文
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[19]BUCHOWSKI H,KSLAZCAK A,PLETRZYK S.Solvent activity along a saturation line and solubility of hydrogen bonding solids[J].Journal of Physical Chemistry,1980,84(91):975-979.
[20]MANGZUROLA E,APELBLAT A.Solubilities of L-glutamic acid,3-nitrobenzoic acid,p-toluic acid,calcium-L-lactate,calcium gluconate,magnesium-DL-aspartate,and magnesium-Llactate in water[J].Journal of Chemical Thermodynamics,2002,34(7):1127-1136.
[21]周彩荣,石晓华,冯伟,等.新戊二醇在溶剂中溶解度的测定及关联[J].高校化学工程学报,2010,24(3):365-369.ZHOU Cairong,SHI Xiaohua,FENG Wei,et al.Measurement and correlation of solubilities of neopentyl glycol in solvents[J].Journal of Chemical Engineering of Chinese Universities,2010,24(3):365-369.
[22]陈超,杨毅,金建平,等.硝基胍结晶热力学[J].化工进展,2012(增1):486-489.CHEN Chao,YANG Yi,JIN Jianping,et al.Study on the thermodynamics of crystallization of nitroguanidine[J].Chemical Industry and Engineering Progress,2012(Sup1):486-489.
[23]张磊,应汉杰,吕浩,等.乙醇-水混合溶剂中5′-尿苷酸二钠的结晶介稳区[J].化工学报,2008,59(6):1348-1353.ZHANG Lei,YING Hanjie,LYU Hao,et al.Metastable zone of 5′-UMPNa2 in ethanol-aqueous mixture[J].Journal of Chemical Industry and Engineering,2008,59(6):1348-1353.
[2]王晓艳.间氨基苯酚合成方法及其工业应用[J].辽宁化工,1995(5):35-36.WANG Xiaoyan.Synthesis of m-aminophenol and its industrial application[J].Liaoning Chemical Industry,1995(5):35-36.
[3]KIRIMURA K,YANASO S,KOSAKA S,et al.Production of p-aminosalicylic acid through enzymatic Kolbe-Schmitt reaction catalyzed by reversible salicylic acid decarboxylase[J].Chemistry Letters,2011,40(2):206-208.
[4]ZHENG Y,MA K,WANG H,et al.A green reduction of aromatic nitro compounds to aromatic amines over a novel Ni/SiO2,catalyst passivated witha gas mixture[J].Catalysis Letters,2008,124(3):268-276.
[5]陈黎明,杜艳芳,王欢,等.电化学还原间硝基苯酚的研究[J].精细化工,2003,20(11):673-675.CHEN Liming,DU Yanfang,WANG Huan,et al.Electrochemical reduction of m-nitrophenol[J].Fine Chemicals,2003,124(3):673-675.
[6]HARUHISA H,HIROSHI M,SHIGERU S.Process for the production of a-minophenols:DE,3561550[P].1988.
[7]李付刚,白雪松,李文骁.间苯二胺催化水解制间氨基苯酚[J].染料与染色,2013(2):36-40.LI Fugang,BAI Xuesong,LI Wenxiao.Preparation of m-aminophenol by hydrolyzation[J].Dyestuffs and Coloration,2013(2):36-40.
[8]吕咏梅.间氨基酚生产与发展[J].化工技术与开发,2001,30(3):28-30.LYU Yongmei.Product of o-aminephenol and its development[J].Technology and Development of Chemical Industry,2001,30(3):28-30.
[9]郭海林.间苯二胺法联产间苯二酚和间氨基苯酚的工艺研究[D].青岛:青岛科技大学,2017.GUO Hailin.The Research on Synthesis of Producing Resorcinol and m-Aminophenol by Hydrolysisof m-Phenylenediamine[D].Qingdao:Qingdao University of Science and Technology,2017.
[10]滕俊江,李英春,王现稳.间二硝基苯催化加氢制备间苯二胺[J].青岛科技大学学报(自然科学版),2003,24(增1):16-17.TENG Junjiang,LI Yingchun,WANG Xianwen.Study on preparation of m-phenylenediamine by catalytic hydrogenation of m-dinitrobenzene[J].Journal of Qingdao University of Science and Technology(Natural Science Edition),2003,24(Sup1):16-17.
[11]MATSUNAGA F,KATO E,KIMURA T,et al.Process for producing a-minophenols:EP,0224625[P].1987.
[12]张敏,李丽霞,李乃瑄,等.间苯二胺水解合成间氨基苯酚工艺的研究[J].天津理工大学学报,2009,25(1):45-48.ZHANG Min,LI Lixia,LI Naixuan,et al.Research on synthesis of m-aminophenol by hydrolysis of m-phenylenediamine[J].Journal of Tianjin University of Technology,2009,25(1):45-48.
[13]杨秀芬.间苯二胺水解制备间氨基苯酚的工艺研究[D].天津:天津理工大学,2008.YANG Xiufen.Research on Synthesis of m-Aminophenol by Hydrolysis of m-Phenylenediamine[D].Tianjin:Tianjin University of Technology,2008.
[14]王清清,孙勤,杨阿三,等.缬沙坦在丁酮-异丙醚混合溶剂中溶解度测定及关联[J].化学工程,2016,44(10):37-41.WANG Qingqing,SUN Qin,YANG Asan,et al.Measurement and correlation of the solubility of valsartan in butanone-isopropyl ether mixed solvents[J].Chemical Engineering,2016,44(10):37-41.
[15]沈乐,李惠萍,高江涛,等.1-苄基-4-羟甲基-1H-1,2,3-三氮唑溶解度的测定及关联[J].高校化学工程学报,2016,30(1):1-6.SHEN Le,LI Huiping,GAO Jiangtao,et al.Measurement and correlation of 1-benzyl-4-hydroxymethyl-1H-1,2,3-triazole solubility[J].Journal of Chemical Engineering of Chinese Universities,2016,30(1):1-6.
[16]STEPHEN E H.Solubilities of Inorganic and Organic Compounds[M].Oxford:Pergamon Press,1963.
[17]YAWS C.Chemical Properties Handbook[M].Beijing:World Publishing Corporation,1999.
[18]APELBLAT A,MANZUROLA E.Solubulities of o-acetylsalicylic,3,5-dinit rosalicylic,and p-toluicacid,and magnesiumDL-aspartate in water from T=(278to 348)K[J].Journal of Chemical Thermodynamics,1999,31(1):85-91.
[19]BUCHOWSKI H,KSLAZCAK A,PLETRZYK S.Solvent activity along a saturation line and solubility of hydrogen bonding solids[J].Journal of Physical Chemistry,1980,84(91):975-979.
[20]MANGZUROLA E,APELBLAT A.Solubilities of L-glutamic acid,3-nitrobenzoic acid,p-toluic acid,calcium-L-lactate,calcium gluconate,magnesium-DL-aspartate,and magnesium-Llactate in water[J].Journal of Chemical Thermodynamics,2002,34(7):1127-1136.
[21]周彩荣,石晓华,冯伟,等.新戊二醇在溶剂中溶解度的测定及关联[J].高校化学工程学报,2010,24(3):365-369.ZHOU Cairong,SHI Xiaohua,FENG Wei,et al.Measurement and correlation of solubilities of neopentyl glycol in solvents[J].Journal of Chemical Engineering of Chinese Universities,2010,24(3):365-369.
[22]陈超,杨毅,金建平,等.硝基胍结晶热力学[J].化工进展,2012(增1):486-489.CHEN Chao,YANG Yi,JIN Jianping,et al.Study on the thermodynamics of crystallization of nitroguanidine[J].Chemical Industry and Engineering Progress,2012(Sup1):486-489.
[23]张磊,应汉杰,吕浩,等.乙醇-水混合溶剂中5′-尿苷酸二钠的结晶介稳区[J].化工学报,2008,59(6):1348-1353.ZHANG Lei,YING Hanjie,LYU Hao,et al.Metastable zone of 5′-UMPNa2 in ethanol-aqueous mixture[J].Journal of Chemical Industry and Engineering,2008,59(6):1348-1353.