烷基萘磺酸盐的合成及其在三次采油中的应用
摘要
本文以AlCl_3为催化剂合成了系列烷基萘磺酸盐的异构体
纯的表面活性剂，以液相色谱和两相滴定法测定了产物的纯度，
并用气相色谱、质谱、核磁共振谱等对产物和其中间体进行了
结构表征。采用Model-500型旋转滴超低界面张力仪测定了表
面活性剂/碱体系的油水界面张力，讨论了表面活性剂浓度、碱
度及表面活性剂结构对油水界面张力的影响。另外，考虑到环
境友好及工业化的问题，本文筛选了HY型和Hβ型分子筛作
为催化剂进行萘的烷基化反应，初步认为HY型分子筛活性较
高。
A series of alkylnaphthalenes were prepared by alkylation with
aluminium chloride as catalyst and their sulfonates by sulfonation.
These products and intermediates were identified through MS,
NMR and HPLC. Interfacial tensions of surfactants/alkali and
crude oil were determined by Model-500 spinning drop
tensiometer. The effects of concetrations and structures of
surfactants and alkality on interfacial tensions were discussed.
HY and H P zeolites were choosed as catalysts for the
alkylation of naphthelene, considering friendly environment and
industrialization HY was confirmed to have higher activity.
纯的表面活性剂，以液相色谱和两相滴定法测定了产物的纯度，
并用气相色谱、质谱、核磁共振谱等对产物和其中间体进行了
结构表征。采用Model-500型旋转滴超低界面张力仪测定了表
面活性剂/碱体系的油水界面张力，讨论了表面活性剂浓度、碱
度及表面活性剂结构对油水界面张力的影响。另外，考虑到环
境友好及工业化的问题，本文筛选了HY型和Hβ型分子筛作
为催化剂进行萘的烷基化反应，初步认为HY型分子筛活性较
高。
A series of alkylnaphthalenes were prepared by alkylation with
aluminium chloride as catalyst and their sulfonates by sulfonation.
These products and intermediates were identified through MS,
NMR and HPLC. Interfacial tensions of surfactants/alkali and
crude oil were determined by Model-500 spinning drop
tensiometer. The effects of concetrations and structures of
surfactants and alkality on interfacial tensions were discussed.
HY and H P zeolites were choosed as catalysts for the
alkylation of naphthelene, considering friendly environment and
industrialization HY was confirmed to have higher activity.
引文
[1]绳池强，油田化学，1992，9，(1)，86-93
[2]Squires F.,US1238355
[3]崔正刚，碱驱提高石油采收率综述，无锡轻工业学院，1986，7
[4]赵国玺，表面活性剂物理化学(修订版)，241-249，北京大学出版社，1991
[5]Schuler P.,Lerner R.M.,Improving chemical flood efficiency with micellar/alkaline/polymer process, SPE 14934,1985
[6]J.C. Melrose and C.F.Brandner,J.Canadian Petr. Tech., 58, Oct.-Dec., 1974
[7]惠晓霞，油田化学，1984，1，22-38
[8]李殿文，油田化学，1993，10(2)：188-194
[9]李干佐，林元，王秀文等，油田化学，1994，11(2)：152-156
[10]陈茂淘，刘斌丽，油田化学，1991，8(3)：240-244
[11]王桂芝，赵成才，油田化学，1991，8(3)：253-258
[12]Gale W.W.Sandvick E.I.,Soc.Petrol.Eng.J.,1973:191-199
[13]崔正刚，张天林，邹文华等，表面活性剂／洗涤剂技术与经济进展(第五届国际表面活性剂／洗涤剂研讨会论文集)，95-102，山西经济出版社，1998
[14]王绍辉，大连理工大学硕士学位论文，1997
[15]Duda J.L., Synthesis, solution properties and corefllood performance of Penn.State surfactant for EOR, Paper presented at 3rd European meeting improved oil recovery, Rome, 1985
[16]黄宏度，杨又震等，油田化学，1991，8 (3)：235-239
[17]Son J.E. Neale G. Hornof V., The Canadian Journal of Chemical Engineering, 1982, 60 (5): 684-691
[18]Kalfoglou G., U S 4007779, 1977
[19]Kalfoglou G, U S 4133385, 1979
[20]Neale G. Hornof V. Chiwetelu C., Can. J. Chem., 1981, 59 (13): 1938-1943
[21]Debons F E Whitting L E. Pedersen L D., U S 4548721, 1985
[22]娆蒙正、程侣伯、王家儒，精细化工合成原理，304，中国石化出版社，1992
[23]娆蒙正、程侣伯、王家儒，精细化工合成原理，305，中国石化出版社，1992
[24]王桂儒、李书纹，催化剂与催化作用，191-192，大连理工大学出版社，1994
[25]D.Fraenkel,M.cherniavsky, B.Ittah. M.Levy, J.catal,1986,(101),273.
[26]Komatsu,Y. Araki,S,Namba and T. Yashima,Stud. Sury. Sci. Catal 1994,(84),1821
[27]A. Katayama, M. Toba, G. Tskcuchi, F.Mizukami, etal, J. Soc. Chem. Commun. 1991, 39
[28]J.A.Horsley. J.D.Fellman,E.G.Derouanceand C.M.Freeman,J,catal. 1992,(147), 231
[29]J.D.Fellman,R.J. Saxon,P.R.Wentreck,E.G.Derouane.and.P.Massiani,Pct. Int, Appl. Wo 90,03961
[30]P.Moreau,A. Finiels,P.Geneste,et.catal Today, 1996,(31),11
[31]Y. Sugi,T. Matsizaki,T.Hanaoko,Y. Kubota,J.H.Kim,etal,Stud. Surf. Sci.catal. 1991,(60), 303
[32]D.Andrew, C. Song,Catal. Today, 1996,(31), 19
[33]J H.Kim. Y. Sugi,T.Matsizaki,T.Hanaoka,etal,Appl. Catal.,1995,(131),15
[34]D.Andrew, Schmitz and C.Song,Catal,Letters, 1996,(40),59
[35]J,Catalysis 67 218-222 (1981)
[36]US. 5,034,563
[37]US. 5,191,135
[38]WO 95/18083
[39]R.L.Wadlinger etal. USP, 3,308.069 (1967)
[40]陈连璋，沸石分子筛催化，203，1991
[41]娆蒙正、程侣伯、王家儒，精细化工合成原理，305，中国石化出版社，1992
[42]娆蒙正、程侣伯、王家儒，精细化工合成原理，200，中国石化出版社，1992
[43]Ger.(East)P.,129324(1978);C.A.,89,59798(1978)
[44]Czech CS,208603(1983)
[2]Squires F.,US1238355
[3]崔正刚，碱驱提高石油采收率综述，无锡轻工业学院，1986，7
[4]赵国玺，表面活性剂物理化学(修订版)，241-249，北京大学出版社，1991
[5]Schuler P.,Lerner R.M.,Improving chemical flood efficiency with micellar/alkaline/polymer process, SPE 14934,1985
[6]J.C. Melrose and C.F.Brandner,J.Canadian Petr. Tech., 58, Oct.-Dec., 1974
[7]惠晓霞，油田化学，1984，1，22-38
[8]李殿文，油田化学，1993，10(2)：188-194
[9]李干佐，林元，王秀文等，油田化学，1994，11(2)：152-156
[10]陈茂淘，刘斌丽，油田化学，1991，8(3)：240-244
[11]王桂芝，赵成才，油田化学，1991，8(3)：253-258
[12]Gale W.W.Sandvick E.I.,Soc.Petrol.Eng.J.,1973:191-199
[13]崔正刚，张天林，邹文华等，表面活性剂／洗涤剂技术与经济进展(第五届国际表面活性剂／洗涤剂研讨会论文集)，95-102，山西经济出版社，1998
[14]王绍辉，大连理工大学硕士学位论文，1997
[15]Duda J.L., Synthesis, solution properties and corefllood performance of Penn.State surfactant for EOR, Paper presented at 3rd European meeting improved oil recovery, Rome, 1985
[16]黄宏度，杨又震等，油田化学，1991，8 (3)：235-239
[17]Son J.E. Neale G. Hornof V., The Canadian Journal of Chemical Engineering, 1982, 60 (5): 684-691
[18]Kalfoglou G., U S 4007779, 1977
[19]Kalfoglou G, U S 4133385, 1979
[20]Neale G. Hornof V. Chiwetelu C., Can. J. Chem., 1981, 59 (13): 1938-1943
[21]Debons F E Whitting L E. Pedersen L D., U S 4548721, 1985
[22]娆蒙正、程侣伯、王家儒，精细化工合成原理，304，中国石化出版社，1992
[23]娆蒙正、程侣伯、王家儒，精细化工合成原理，305，中国石化出版社，1992
[24]王桂儒、李书纹，催化剂与催化作用，191-192，大连理工大学出版社，1994
[25]D.Fraenkel,M.cherniavsky, B.Ittah. M.Levy, J.catal,1986,(101),273.
[26]Komatsu,Y. Araki,S,Namba and T. Yashima,Stud. Sury. Sci. Catal 1994,(84),1821
[27]A. Katayama, M. Toba, G. Tskcuchi, F.Mizukami, etal, J. Soc. Chem. Commun. 1991, 39
[28]J.A.Horsley. J.D.Fellman,E.G.Derouanceand C.M.Freeman,J,catal. 1992,(147), 231
[29]J.D.Fellman,R.J. Saxon,P.R.Wentreck,E.G.Derouane.and.P.Massiani,Pct. Int, Appl. Wo 90,03961
[30]P.Moreau,A. Finiels,P.Geneste,et.catal Today, 1996,(31),11
[31]Y. Sugi,T. Matsizaki,T.Hanaoko,Y. Kubota,J.H.Kim,etal,Stud. Surf. Sci.catal. 1991,(60), 303
[32]D.Andrew, C. Song,Catal. Today, 1996,(31), 19
[33]J H.Kim. Y. Sugi,T.Matsizaki,T.Hanaoka,etal,Appl. Catal.,1995,(131),15
[34]D.Andrew, Schmitz and C.Song,Catal,Letters, 1996,(40),59
[35]J,Catalysis 67 218-222 (1981)
[36]US. 5,034,563
[37]US. 5,191,135
[38]WO 95/18083
[39]R.L.Wadlinger etal. USP, 3,308.069 (1967)
[40]陈连璋，沸石分子筛催化，203，1991
[41]娆蒙正、程侣伯、王家儒，精细化工合成原理，305，中国石化出版社，1992
[42]娆蒙正、程侣伯、王家儒，精细化工合成原理，200，中国石化出版社，1992
[43]Ger.(East)P.,129324(1978);C.A.,89,59798(1978)
[44]Czech CS,208603(1983)