丙烯酸十八酯的合成及其与丙烯酰胺聚合性能研究
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摘要
以丙烯酸和十八醇为原料合成丙烯酸十八酯。探讨了反应时间、反应温度、催化剂用量对酯化率的影响。用红外光谱仪、核磁共振仪、气相色谱仪、质谱仪等对产物的结构进行了表征。根据所设计的因素和水平，采用正交试验方法统计，寻找了该合成反应的最佳合成工艺条件。将产品作为疏水单体与丙烯酰胺共聚，采用胶束聚合法，以十二烷基磺酸钠为乳化剂、过氧化苯甲酰为引发剂，在氮气保护下反应，得到疏水改性聚丙烯酰胺。并研究聚合反应的影响因素：物料配比、表面活性剂、引发剂、反应温度和时间、旋转速度的影响，用旋转粘度计测定聚合物的表观粘度，以膨润土溶液为废水水样，考察聚合物的絮凝性能及相关应用。
Octadecyl acrylate was synthesized with acrylic acid and octadecanol as raw materials. Theinfluences of reaction time, reaction temperature, amount of catalyst on esterification wereinvestigated by orthogonal design. The IR spectra and ~1H-NMR spectra characteristics ofthe product were in good agreement with that of literatures. Hydrophobic modifiedpolyacrylamide was synthesized by the copolymerization of octadecyl acrylate(ashydrophobic monomer) and acrylamide. The reaction was proceeded under nitrogen gas,using sodium dodecanesulphonate as emulsifier, Benzoyl Peroxide(BPO) as initiator.Apparent viscosity was determined by rotational viscometers. Porcelain clay solution wasused as waste water sample to determine the flocculation property of the hydrophobicmodified polyacrylamide.
Octadecyl acrylate was synthesized with acrylic acid and octadecanol as raw materials. Theinfluences of reaction time, reaction temperature, amount of catalyst on esterification wereinvestigated by orthogonal design. The IR spectra and ~1H-NMR spectra characteristics ofthe product were in good agreement with that of literatures. Hydrophobic modifiedpolyacrylamide was synthesized by the copolymerization of octadecyl acrylate(ashydrophobic monomer) and acrylamide. The reaction was proceeded under nitrogen gas,using sodium dodecanesulphonate as emulsifier, Benzoyl Peroxide(BPO) as initiator.Apparent viscosity was determined by rotational viscometers. Porcelain clay solution wasused as waste water sample to determine the flocculation property of the hydrophobicmodified polyacrylamide.
引文
1．周凤山，王世虎，李继勇等．一种新的丙烯酸高级酯制备方法[J]．精细化工，2002，19(1)：45-47
2．宋昭峥，张贵才，葛际江等．丙烯酸十八酯的合成[J]．石油大学学报．2000，24(6)：49-51
3．丁伟，李柏林，肖翠玲等．丙烯酸十八酯的合成[J]．大庆石油学院学报．1998，22(2)，79-81
4．戚国荣，胡合贵，杨云松．丙烯酸与十八醇酯化反应动力学研究[J]．科技通报．1999，15(5)：325-329
5．周凤山，王世虎，卢凤纪．丙烯酸十八酯制各方法研究[J]．化学世界．2002，(3)：143-147
6．唐蜀忠，王强，刘振军等．丙烯酰胺-丙烯酸十八脂胶束聚合及其共聚物水溶液粘度与温度、矿化度、剪切速率的关系[J]．石油与天然气化工．2000，30(2)：89-91
7．黄承哲，朴哲，孟万等．丙烯酸混合高级酯的制备[J]．延边大学学报．1998，24(3)：73-75
8．李学东，张锡鹏．丙烯酸高级酯的合成[J]．石油化工高等学校学报．2002，9(1)：18-22
9．王科军．在微波作用下正交设计合成丙烯酸十八酯[J]．赣南师范学院学报．2004，(6)：51-53
10．王科军，刘芳，周晓莲等．微波辅助合成丙烯酸十八酯[J]．化工科技．2005，13(5)：13-16
11．章云祥，方勤．水溶性高聚物的研究进展[J]．功能高分子学报．1997，10(1)：102-109
12．罗开富，张熙，黄荣华．疏水缔合水溶性聚合物的合成[J]．油田化学．1999，16(3)：282-295
13．曾钫，童真，沈家瑞．疏水缔合性水溶性高分子的合成与表征[J]．高分子通报．1996，(4)：204-209
14．黄婷．含DMDAC的疏水缔合水溶性高分子的研究．硕士学位论文．2005．6
15．徐福贵，董晓臣．聚丙烯酰胺疏水缔合衍生物研究进展[J]．化学推进剂与高分子材料．2003，1(2)：25-28
16．陈民助，王茜，曾宪城等．胶束溶液中丙稀酰胺聚合反应的研究[J]．四川大学学报．1997，34(6)：822～827
17．赵立芳，姜波．酯化反应中催化剂研究新进展[J]．江苏化工．2004，32(4)：17-20
18．刘祥义，徐晓军，杨宇明．固体超强酸催化制备丙稀酸十八酯[J]．云南大学学报． 2006，28(1)：64-67
19．周海峰．固体酸催化酯化反应的研究进展[J]．精细与专用化学品．2004，12(23)：1-5
20．成战胜，行春丽，田京城等．固体超强酸催化剂的研究进展[J]．应用化工，2004，33(6)：5-8
21．郭睿威，宁海宾，戚桂村等．疏水改性丙稀酰胺的胶束聚合法制备及表征研究进展[J]．化工进展．2006，25(1)：25-30
22. Alain H, Francoise C, Joseph. Selb,Propertises of Hydrophobically Associating Polyacrylamides: Influence of the Method of Synthesis[J]. Macromolecules, 1993, 26:4521-4532
23. Raffaello M, William T A, Juergen W. Preparation of imidazo[1,5-a]pyrimido[5,4-d] [1] benzazepine derivatives as GABA A 5 receptor modulators for treating cognitive disorders[P]. WO : 2002 094 834 A1, 2002-11-28
24. Glass J E. Associative Polymers in Aqueous Media, ACS Symposium Series 753[J]. Washington D C: American Chemical Society, 1999
25. CamahanM A,Grinstaff M W.Synthesis and characterization of poly(glycerol-succinic acid)Dendrimers[J]. Macromolecules. 2001, 34:7468-7655
26. Iohnson D W, Brink H J, Jakobs C. Cholesterol and dehydrocholesterol[J]. Journal of Liquid Resaerch. 2001, 42(10): 1699-1705
27. Leena H, Johannson N, Koskimies P, et al. Preparation of benzothienopyrimidinones as inhibitors of 17-hydroxysteroid dehydrogenase[P]. US: 2005 038 053 A1, 2005-02-17
28. Pandey A, Seroogy J, Volkots D, et al. Spirocyclic non-peptide glycoprotein Ⅱb-Ⅲa antagonists[J]. Bioorganic & Medicinal Chemistry Letters. 2001, 11 (10) : 1293-1296
29. anuela M, Kirsch, G.. A combination of Friedel-Crafts and Lawesson reactions to 5-substituted 2,2'-bithiophenes[J]. Heterocycles. 2001, 55(8): 1487-1498
30. Xu Z P, Chuang K T. Kinetics of Acetic Esterification over Ion Exchange Catalysts[J]. The Canadian Journal of Chemical Engnineering, 1996,74(8): 493-500
31. Throl T S,Yadav V M,Yadav G D.Esterification phthalic anhydride with 2-ethylhexnol by solid superacid catalysts[J]. Apple Catalo, 1992, 90:73-96
32. Sommer J, Jost R.Carbenium and carbenium ions in liquid and solid superacid activation of small catalyzed alkanes[J]. Pur Appl Chem, 2000, 72(12): 2309-2318
33. Fischer A, Houzelle M C, Hubert P, etal. Detection of intramolecular associations in hydrophobically modified pectin derivatives using fluorescent probes[J]. Langmuir, 1998,16:4482
34. Tanaka F.Polymer-surfavtant interaction in thermoreversible gels[J]. Macromolecules, 1998, 31 (2): 384-393
35. Sakamoto K. Effect of polymer size on the polyelectrolyte-surfactany complex formation[J]. J Phys Chem B, 1997,101:7520
36. Volpert E, Selb J , Candau F, etal, Adsorption of hydrophobically associating polyacrylamides on clay[J]. Langmuir,1998, 7:1870
37. Wang Y L, Lu D H, Long C F, etal. Interractions between sodium dodecyl sulfate and hydrophobically modified poly(acrylamide)s studied by electron spin resonance and transmission electron microscropy[J]. Langmuir, 1998, 8:2050-2054
38. Wirmik M, Sudarshi T A, Goddard R, etal. Interactions of an anionic surfactant with a fluorescent-dye-labeled hydrophobically- modified cationic cellulose ether[J]. Langmuir, 1997,13:111-114
39. Kulicke W M, Arendt O, Berger M.Rheological characterization of the dilatant flow behavior of highly substituted bydroxypropylmethyl-cellulose solutions in the presence of sodium lauryl sulfate[J]. Colloid Polymer Sci, 1998, 276(7): 617-626
40. Nilsson S, Thuresson K, Hansson P, etal.Mixed solutions of surfactant and hydrophobically modified polymer controlling viscosity with micellar size[J]. Phys Chem B, 1998,102(37): 7099-7105
41. Bromberg L,Temchenko M,Colby R H.Interactions among hydrophobically modified polyelectrolytes and surfactants of the same charge[J]. Langmuir, 2000,16(6): 2609-2614
42. Ruckenstein E. Surfactant aggregation in nonionic polymer solutions[J]. Langmuir, 1999,15:8086
43. Varga 1.Aggregation number of ionic surfactants in complex with polymer via mersurements of trace probe electrolyte[J]. Langmuir, 1998,14:7397
44. Lianos P. Investigation of neutral polymer-ionic surfactant interactions by flurescence in conjunction with viscosity measurements[J]. Langmuir,1998,14:6320
45．张会展，周健，方春玉．絮凝剂在废水处理中的应用[J]．四川理工学院学报．2006．19(2)：84-89
46．刘睿，周启星，张兰英等．水处理絮凝剂研究与应用进展[J]．应用生态学报．2005．16(8)：1558-1562
47．王东贤，王琳，宫清涛等．疏水缔合聚合物的合成、表征及其溶液性能研究[J]．胶体与聚合物，2005，23(2)：34-40
48．王东贤，王琳，宫清涛等．改性聚丙烯酰胺水溶液的疏水缔合性质[J]．感光科学与光化学，2005，23(3)：197-202
49．徐福贵，董晓臣．聚丙烯酰胺疏水缔合衍生物研究进展[J]．化学推进剂与高分子材料，2003，1(2)：25-28
50．卢时，王凤贺，夏明珠等．AMPS-AM反相微乳液聚合及其絮凝性能研究[J]．水处理信息报导，2006，(2)：19-21
51．孙红杰，张万忠，谷晓昱．几种絮凝剂的絮凝效果研究[J]．沈阳化工学院学报，2005，19(4)：314-317
52．张文艺，郑明东，李琴．聚铁改性絮凝剂的合成与水处理试验[J]．水文地质工程地质，2005，(5)：6-8
2．宋昭峥，张贵才，葛际江等．丙烯酸十八酯的合成[J]．石油大学学报．2000，24(6)：49-51
3．丁伟，李柏林，肖翠玲等．丙烯酸十八酯的合成[J]．大庆石油学院学报．1998，22(2)，79-81
4．戚国荣，胡合贵，杨云松．丙烯酸与十八醇酯化反应动力学研究[J]．科技通报．1999，15(5)：325-329
5．周凤山，王世虎，卢凤纪．丙烯酸十八酯制各方法研究[J]．化学世界．2002，(3)：143-147
6．唐蜀忠，王强，刘振军等．丙烯酰胺-丙烯酸十八脂胶束聚合及其共聚物水溶液粘度与温度、矿化度、剪切速率的关系[J]．石油与天然气化工．2000，30(2)：89-91
7．黄承哲，朴哲，孟万等．丙烯酸混合高级酯的制备[J]．延边大学学报．1998，24(3)：73-75
8．李学东，张锡鹏．丙烯酸高级酯的合成[J]．石油化工高等学校学报．2002，9(1)：18-22
9．王科军．在微波作用下正交设计合成丙烯酸十八酯[J]．赣南师范学院学报．2004，(6)：51-53
10．王科军，刘芳，周晓莲等．微波辅助合成丙烯酸十八酯[J]．化工科技．2005，13(5)：13-16
11．章云祥，方勤．水溶性高聚物的研究进展[J]．功能高分子学报．1997，10(1)：102-109
12．罗开富，张熙，黄荣华．疏水缔合水溶性聚合物的合成[J]．油田化学．1999，16(3)：282-295
13．曾钫，童真，沈家瑞．疏水缔合性水溶性高分子的合成与表征[J]．高分子通报．1996，(4)：204-209
14．黄婷．含DMDAC的疏水缔合水溶性高分子的研究．硕士学位论文．2005．6
15．徐福贵，董晓臣．聚丙烯酰胺疏水缔合衍生物研究进展[J]．化学推进剂与高分子材料．2003，1(2)：25-28
16．陈民助，王茜，曾宪城等．胶束溶液中丙稀酰胺聚合反应的研究[J]．四川大学学报．1997，34(6)：822～827
17．赵立芳，姜波．酯化反应中催化剂研究新进展[J]．江苏化工．2004，32(4)：17-20
18．刘祥义，徐晓军，杨宇明．固体超强酸催化制备丙稀酸十八酯[J]．云南大学学报． 2006，28(1)：64-67
19．周海峰．固体酸催化酯化反应的研究进展[J]．精细与专用化学品．2004，12(23)：1-5
20．成战胜，行春丽，田京城等．固体超强酸催化剂的研究进展[J]．应用化工，2004，33(6)：5-8
21．郭睿威，宁海宾，戚桂村等．疏水改性丙稀酰胺的胶束聚合法制备及表征研究进展[J]．化工进展．2006，25(1)：25-30
22. Alain H, Francoise C, Joseph. Selb,Propertises of Hydrophobically Associating Polyacrylamides: Influence of the Method of Synthesis[J]. Macromolecules, 1993, 26:4521-4532
23. Raffaello M, William T A, Juergen W. Preparation of imidazo[1,5-a]pyrimido[5,4-d] [1] benzazepine derivatives as GABA A 5 receptor modulators for treating cognitive disorders[P]. WO : 2002 094 834 A1, 2002-11-28
24. Glass J E. Associative Polymers in Aqueous Media, ACS Symposium Series 753[J]. Washington D C: American Chemical Society, 1999
25. CamahanM A,Grinstaff M W.Synthesis and characterization of poly(glycerol-succinic acid)Dendrimers[J]. Macromolecules. 2001, 34:7468-7655
26. Iohnson D W, Brink H J, Jakobs C. Cholesterol and dehydrocholesterol[J]. Journal of Liquid Resaerch. 2001, 42(10): 1699-1705
27. Leena H, Johannson N, Koskimies P, et al. Preparation of benzothienopyrimidinones as inhibitors of 17-hydroxysteroid dehydrogenase[P]. US: 2005 038 053 A1, 2005-02-17
28. Pandey A, Seroogy J, Volkots D, et al. Spirocyclic non-peptide glycoprotein Ⅱb-Ⅲa antagonists[J]. Bioorganic & Medicinal Chemistry Letters. 2001, 11 (10) : 1293-1296
29. anuela M, Kirsch, G.. A combination of Friedel-Crafts and Lawesson reactions to 5-substituted 2,2'-bithiophenes[J]. Heterocycles. 2001, 55(8): 1487-1498
30. Xu Z P, Chuang K T. Kinetics of Acetic Esterification over Ion Exchange Catalysts[J]. The Canadian Journal of Chemical Engnineering, 1996,74(8): 493-500
31. Throl T S,Yadav V M,Yadav G D.Esterification phthalic anhydride with 2-ethylhexnol by solid superacid catalysts[J]. Apple Catalo, 1992, 90:73-96
32. Sommer J, Jost R.Carbenium and carbenium ions in liquid and solid superacid activation of small catalyzed alkanes[J]. Pur Appl Chem, 2000, 72(12): 2309-2318
33. Fischer A, Houzelle M C, Hubert P, etal. Detection of intramolecular associations in hydrophobically modified pectin derivatives using fluorescent probes[J]. Langmuir, 1998,16:4482
34. Tanaka F.Polymer-surfavtant interaction in thermoreversible gels[J]. Macromolecules, 1998, 31 (2): 384-393
35. Sakamoto K. Effect of polymer size on the polyelectrolyte-surfactany complex formation[J]. J Phys Chem B, 1997,101:7520
36. Volpert E, Selb J , Candau F, etal, Adsorption of hydrophobically associating polyacrylamides on clay[J]. Langmuir,1998, 7:1870
37. Wang Y L, Lu D H, Long C F, etal. Interractions between sodium dodecyl sulfate and hydrophobically modified poly(acrylamide)s studied by electron spin resonance and transmission electron microscropy[J]. Langmuir, 1998, 8:2050-2054
38. Wirmik M, Sudarshi T A, Goddard R, etal. Interactions of an anionic surfactant with a fluorescent-dye-labeled hydrophobically- modified cationic cellulose ether[J]. Langmuir, 1997,13:111-114
39. Kulicke W M, Arendt O, Berger M.Rheological characterization of the dilatant flow behavior of highly substituted bydroxypropylmethyl-cellulose solutions in the presence of sodium lauryl sulfate[J]. Colloid Polymer Sci, 1998, 276(7): 617-626
40. Nilsson S, Thuresson K, Hansson P, etal.Mixed solutions of surfactant and hydrophobically modified polymer controlling viscosity with micellar size[J]. Phys Chem B, 1998,102(37): 7099-7105
41. Bromberg L,Temchenko M,Colby R H.Interactions among hydrophobically modified polyelectrolytes and surfactants of the same charge[J]. Langmuir, 2000,16(6): 2609-2614
42. Ruckenstein E. Surfactant aggregation in nonionic polymer solutions[J]. Langmuir, 1999,15:8086
43. Varga 1.Aggregation number of ionic surfactants in complex with polymer via mersurements of trace probe electrolyte[J]. Langmuir, 1998,14:7397
44. Lianos P. Investigation of neutral polymer-ionic surfactant interactions by flurescence in conjunction with viscosity measurements[J]. Langmuir,1998,14:6320
45．张会展，周健，方春玉．絮凝剂在废水处理中的应用[J]．四川理工学院学报．2006．19(2)：84-89
46．刘睿，周启星，张兰英等．水处理絮凝剂研究与应用进展[J]．应用生态学报．2005．16(8)：1558-1562
47．王东贤，王琳，宫清涛等．疏水缔合聚合物的合成、表征及其溶液性能研究[J]．胶体与聚合物，2005，23(2)：34-40
48．王东贤，王琳，宫清涛等．改性聚丙烯酰胺水溶液的疏水缔合性质[J]．感光科学与光化学，2005，23(3)：197-202
49．徐福贵，董晓臣．聚丙烯酰胺疏水缔合衍生物研究进展[J]．化学推进剂与高分子材料，2003，1(2)：25-28
50．卢时，王凤贺，夏明珠等．AMPS-AM反相微乳液聚合及其絮凝性能研究[J]．水处理信息报导，2006，(2)：19-21
51．孙红杰，张万忠，谷晓昱．几种絮凝剂的絮凝效果研究[J]．沈阳化工学院学报，2005，19(4)：314-317
52．张文艺，郑明东，李琴．聚铁改性絮凝剂的合成与水处理试验[J]．水文地质工程地质，2005，(5)：6-8