萘的选择性羰基化
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摘要
2,6-萘二甲酸是制备新型聚酯PEN的主要原料。以萘为起始原料，经2-位选择性羰化、6-位的定位羰化和有限氧化的步骤合成2,6-萘二甲酸是一条有竞争力的工艺路线。本文对萘的选择性羰基化进行研究，考察[bmim]Br／AlCl_3离子液体以及[bmim]Br／AlCl_3离子液体-分子筛复合体系在Friedel-Crafts反应中的催化性能。
合成了[bmim]Br离子液体，考察了反应温度对离子液体产率的影响。[bmim]Br离子液体在100～110℃下反应产率达到96％以上。
测定了CO在[bmim]Br／AlCl_3离子液体中的平衡溶解度，考察了温度、压力、离子液体配比对CO平衡溶解度的影响。CO在[bmim]Br／AlCl_3离子液体中溶解性能优于[bmim]BF_4等离子液体。CO在[bmim]Br／AlCl_3离子液体中的平衡溶解度随着AlCl_3含量的升高而增大，随着温度的升高而减小，随着压力的升高而增大。
研究了萘在离子液体中的Friedel-Crafts选择性羰化反应。[bmim]Br／AlCl_3催化体系中，萘能有效转化为α-萘甲醛。在反应最优条件(CO压力为1．5MPa，室温，[bmim]Br／AlCl)_3(1：2)为催化剂)下反应2h后，萘的转化率达到40％，且得到单一产物α位萘甲醛，选择性达到100％。在[bmim]Br/AlCl_3(1：2)-ZSM分子筛复合体系中，萘的羰基产物出现β位萘甲醛。在CO压力为1．5MPa，室温下反应2h后，产物中β位萘甲醛选择性达到50％以上。
用HyperChem软件对反应中间体进行模拟分析，结合实验结果得到以下结论：[bmim]Br／AlCl_3离子液体的活性基团为Al_2Cl_6，其不仅具备活化羰基化试剂(CO)的作用，还能活化芳环，提高了萘的转化率。
离子液体比传统无水三氯化铝催化性能更好且绿色环保，是Friedel-Crafts反应的优良催化剂，但其不具有β位选择催化性能。脱铝ZSM型分子筛分散在[bmim]Br／AlCl_3离子液体中形成的复合催化体系具有β位选择性，选择性达到50％以上。
2, 6-naphthalenedicarboxylic acid is the main raw material to produce the novel polyester PEN. It is a advanced route to synthesize 2, 6-naphthalenedicarboxylic acid from naphthalene in 3 steps: 2-position selected acylation, 6-position oriented acylation and controlled oxidation. The selective Friedel-Crafts acylations of naphthalene in ionic liquid [bmim]Br/AlCl3 and the [bmim]Br/AlCl3-zeolite composite system were investigated.
Firstly, ionic liquids ([bmim]Br) were synthesized and the influence of the reaction temperature on the reaction yield was studied. Secondly, the influence of temperature, pressure and ionic liquid composition on the solubility of carbon monoxide in ionic liquids ([bmim]Br/AlCl_3) were investigated. Finally, the Friedel-Crafts acylations of naphthalene in ionic liquid [bmim]Br/AlCl_3 and the [bmim]Br/AlCl_3-zeolite composite system were proceeded at room temperature under CO pressure of 1.5 MPa.
The optimal yield over 96% can be achieved in the synthesis of [bmim]Br at 100-110℃. Carbon monoxide has higher solubility in ionic liquid [bmim]Br/AlCl_3 than in [bmim]BF_4. Its solubility increased as the fraction of AlCl_3 and the pressure increased, but decreased as the temperature increased. In the presence of ionic liquid [bmim]Br/AlCl_3, naphthalene can convert into 100%α-naphthaldehyde with a conversion over 40% under the optimum condition (CO pressure was 1.5 MPa, room temperature, [bmim]Br/AlCl_3(1:2) was used as catalyst, 2 hours). When the reaction was carried out in the composite system of [bmim]Br/AlCl_3(1:2) and ZSM zeolite, also under CO pressure of 1.5 MPa and at room temperature,β-naphthaldehyde can be obtained with a selectivity over 50%.
Combined the expeimental results with the simulation using HyperChem, we can draw the following conclusions: Al_2Cl_6 is the active group in [bmim]Br/AlCl_3, which can activate not only the acylation agent (CO) but the aromatic ring (naphthalene) as well. As a result, the conversion of naphthalene can be greatly increased. Apart from the high activity, Ionic liquid is a green Friedel-Crafts catalyst compared with the traditional anhydr-AlCl_3. Ionic liquid catalyst leads to 100%α-naphthaldehyde, but when it is mixed with ZSM zeolite,halfα-naphthaldehyde and halfβ-naphthaldehyde can be obtained.
合成了[bmim]Br离子液体，考察了反应温度对离子液体产率的影响。[bmim]Br离子液体在100～110℃下反应产率达到96％以上。
测定了CO在[bmim]Br／AlCl_3离子液体中的平衡溶解度，考察了温度、压力、离子液体配比对CO平衡溶解度的影响。CO在[bmim]Br／AlCl_3离子液体中溶解性能优于[bmim]BF_4等离子液体。CO在[bmim]Br／AlCl_3离子液体中的平衡溶解度随着AlCl_3含量的升高而增大，随着温度的升高而减小，随着压力的升高而增大。
研究了萘在离子液体中的Friedel-Crafts选择性羰化反应。[bmim]Br／AlCl_3催化体系中，萘能有效转化为α-萘甲醛。在反应最优条件(CO压力为1．5MPa，室温，[bmim]Br／AlCl)_3(1：2)为催化剂)下反应2h后，萘的转化率达到40％，且得到单一产物α位萘甲醛，选择性达到100％。在[bmim]Br/AlCl_3(1：2)-ZSM分子筛复合体系中，萘的羰基产物出现β位萘甲醛。在CO压力为1．5MPa，室温下反应2h后，产物中β位萘甲醛选择性达到50％以上。
用HyperChem软件对反应中间体进行模拟分析，结合实验结果得到以下结论：[bmim]Br／AlCl_3离子液体的活性基团为Al_2Cl_6，其不仅具备活化羰基化试剂(CO)的作用，还能活化芳环，提高了萘的转化率。
离子液体比传统无水三氯化铝催化性能更好且绿色环保，是Friedel-Crafts反应的优良催化剂，但其不具有β位选择催化性能。脱铝ZSM型分子筛分散在[bmim]Br／AlCl_3离子液体中形成的复合催化体系具有β位选择性，选择性达到50％以上。
2, 6-naphthalenedicarboxylic acid is the main raw material to produce the novel polyester PEN. It is a advanced route to synthesize 2, 6-naphthalenedicarboxylic acid from naphthalene in 3 steps: 2-position selected acylation, 6-position oriented acylation and controlled oxidation. The selective Friedel-Crafts acylations of naphthalene in ionic liquid [bmim]Br/AlCl3 and the [bmim]Br/AlCl3-zeolite composite system were investigated.
Firstly, ionic liquids ([bmim]Br) were synthesized and the influence of the reaction temperature on the reaction yield was studied. Secondly, the influence of temperature, pressure and ionic liquid composition on the solubility of carbon monoxide in ionic liquids ([bmim]Br/AlCl_3) were investigated. Finally, the Friedel-Crafts acylations of naphthalene in ionic liquid [bmim]Br/AlCl_3 and the [bmim]Br/AlCl_3-zeolite composite system were proceeded at room temperature under CO pressure of 1.5 MPa.
The optimal yield over 96% can be achieved in the synthesis of [bmim]Br at 100-110℃. Carbon monoxide has higher solubility in ionic liquid [bmim]Br/AlCl_3 than in [bmim]BF_4. Its solubility increased as the fraction of AlCl_3 and the pressure increased, but decreased as the temperature increased. In the presence of ionic liquid [bmim]Br/AlCl_3, naphthalene can convert into 100%α-naphthaldehyde with a conversion over 40% under the optimum condition (CO pressure was 1.5 MPa, room temperature, [bmim]Br/AlCl_3(1:2) was used as catalyst, 2 hours). When the reaction was carried out in the composite system of [bmim]Br/AlCl_3(1:2) and ZSM zeolite, also under CO pressure of 1.5 MPa and at room temperature,β-naphthaldehyde can be obtained with a selectivity over 50%.
Combined the expeimental results with the simulation using HyperChem, we can draw the following conclusions: Al_2Cl_6 is the active group in [bmim]Br/AlCl_3, which can activate not only the acylation agent (CO) but the aromatic ring (naphthalene) as well. As a result, the conversion of naphthalene can be greatly increased. Apart from the high activity, Ionic liquid is a green Friedel-Crafts catalyst compared with the traditional anhydr-AlCl_3. Ionic liquid catalyst leads to 100%α-naphthaldehyde, but when it is mixed with ZSM zeolite,halfα-naphthaldehyde and halfβ-naphthaldehyde can be obtained.
引文
[1]徐兆瑜．21世纪的新型高分子材料-聚萘二甲酸乙二醇酯(PEN)．化学推进剂与高分子材料，2002：11-15
[2]L. D. Lillwitz. Production of dimethyl-2-6-naphthalenedicarboxylate precursor to polyethylene naphthalene.Appl. Catal.A, 2001, 221:337-358
[3]刘万治，谢刚．PEN及其中间体2，6-萘二甲酸简介．聚酯工业，2006，19：7-10
[4]许杰，铁大华，王吕东．聚酯用萘系衍生物的开发技术进展．合成技术及应用，2002，17：22-26
[5]J.Allen, E.Malmberg. Recovery of 2,6-dialkyl-naphthalene isomers. US,4900717 (15 February1966) to Sun oil
[6]Chem Systems' PERP report. 2, 6-Naphthalene Dicarboxylic Acid. January 1991
[7]Manfred T. Reetz, Johannes G. de Vries. Ligand-free Heck reactions using low Pd-loading.Chem.Comm, 2004: 1559
[8] K.Sumitani,K,Shimada. JP 0413637( January 1997)
[9]孙绪江，张军，齐彦伟．分子筛吸附分离2，6-二甲基荼．精细石油化工．1999：4-6
[10] Jung-Nam Park, Jun Wang, Suk-In Hong, Chul Wee Lee. Effect of dealumination of zeolite catalysts on methylation of 2-methylnaphthalene in a high-pressure fixed-bed reactor. Appl. Catal. A, 2005, 292:68-75
[11]吴伟，魏晓丽，武光，李凌飞，张密林．酸性离子液体高选择性催化合成2，6-二甲基萘．催化学报，2007，28：572-578
[12]叶启亮，郭世卓，曹发海，房鼎业．2，6-萘二甲酸制备工艺进展．化学世界，2005：181-185
[13]涂根国，陈海平，汪杰，刘丽莉，乔迁．2，6-荼二甲酸的合成与纯化技术进展．河南化工，2007，24：10-12
[14]开万龙．2，6-萘二甲酸纯化技术进展．金山油化纤，2000：22-28
[15]赵卡克，陈建定，愈三传，吴叙勤．2，6-萘二甲酸的化学精制法．高分子材料1995：33-36
[1]Tom Welton. Ionic liquids in catalysis. Coord. Chem. Rev, 2004, 248: 2459-2477
[2]Peter Wasserscheid, Wilhelm Keim. Ionic liquids-New"Solutions"for transition metal catalysis.Angew. Chem. Int. Ed, 39: 3772-3789
[3]Nidhi Jain, Anil Kumar, Sushma Chauhan, S.M.S. Chauhan. Chemial and biochemicaltransformation in ionic liquids. Tetra, 2005, 61:1015-1060
[4]Paulo A.Z. Suarez, Jeane E.L.Dullius, Sandra Einloft, Roberto F. De Souza, Jairton Dupont.The use of new ionic liquids in two-phase catalytic hydrogenation reaction by rhodium complexes.Polyhedron, 1996, 15:1217-1219
[5]Adrian J. Carmichael, Martyn J.Earle, John D. Holbrey, Paul B. McCormac, Kenneth R.Seddon. The Heck Reactidn in Ionic Liquids: A Multiphasic Catalyst System. Org. Lett, 1999, 1:997-1000
[6]Joshua Howath, Keith Hanlon , Darren Fayne , Paul McCormac. Moisture StableDialkylimidazolium Salts as Heterogeneous and Homogenous Lewis Acids in the Diels-AlderReaction. Tetra. Lett, 1997, 38:3097-3100
[7]Choong Eui Song, Eun Joo Roh. Practical method to recycle a chiral(salen)Mn epoxidationcatalyst by using an ionic liquid. Chem.Comm, 2000, 837-838
[8]Eiichiro Mizushima, Teruyuki Hayashi, Masato Tanaka. Palladium-catalysed carbonylation ofaryl halides in ionic liquid media: high catalyst stability and significant rate-enhancement inalkoxycarbonylation. Green Chemisry, 2001, 3: 76
[9]Wei Wu, Guang Wu, Minlin Zhang. Highly selective synthesis of 2,6-Dimethylnaphthanlene bygreen catalysts: N-alkyl-pyridinium halides-aluminum chloride ionic liquids. Appl. Cata, 2007,326:189-193
[10]Zhongkui Zhao, Zongshi Li, Guiru Wang, Weihong Qiao, Lvbo Cheng. Friedel-Craftsalkylation of 2-methylnaphthalene in room temperature ionic liquids. Appl. Cata, 2004, 262:69-73
[11]乔煜，邓友全．超强酸性室温离子液体反应介质中烷烃羰化研究．化学学报，60(8)：1520-1523
[12]Christopher J.Adams, Martyn J. Earle, Glyn Roberts, Kenneth R. Seddon. Friedel-Crafts??reactions in room temperature ionic liquids. Chem. Commun, 1998. 2097-2098
[13]章维超．甲苯选择性羰基化合成对甲基苯甲醛研究：[学位论文]．杭州：浙江大学理学院化学系，2006
[14]Nidhi Jain, Anil Kumar, Sushma Chauhan, et al. Chemical and biochemical transformationsin ionic liquids. Tetra, 2005, 61:1015-1060
[15] Vasudevan V, Namboodiri, Rajender S. Varma. Microwave-assisted preparation ofdialkylimidazolium tetrachloroaluminates and their use as catalysts in the solvent-freetetrahydropyranylation of alcohols and phenols. Chem. Comm, 2002: 342-343
[16]Vasudevan V, Namboodiri, Rajender S. Varma. Solvent-Free Sonochemicl Preparation ofIonic liquids. Org. lett, 2002, 4:3161-3163
[1]王一平，张国建，黄群武，刘卫兵．UNIFAC发估算甲烷在常三柴油中的高压溶解度．计算机与应用化学，2007，24：1315-1318
[2]Hua Chao, Xu Shi-min, Li Xin-gang, Ma Pei-sheng. Apparatus of Measuring Gas Solubility Under High Pressure. Journal of Tianjin Universiby, 2006. 39:25-30
[3]白亮，赵玉龙，张碧江．高压搅拌釜中H_2、CO住不同液体介质中的溶解度和体积传质系数的研究．化学反应工程与工艺，1996，12：190-194
[4]Dean Camper , Paul Scovazzo , Carl Koval , Richard Noble. Gas Solubilities inRoom-Temperature Ionic Liquids. Ind. Eng. Chem. Res. 2004, 43: 3049-3054
[5]Jennifer L. Anthony, Jessica L. Anderson, Edward J. Maginn, Joan F. Brennecke. Anion Effectson Gas Solubility in Ionic Liquids. J. Phys. Chem. B, 2005, 109: 6366-6374
[6]Jacek Kumelan, Alvaro Perez-Salado Kamps, Dirk Tuma, Gerd Maurer. Solubility of CO in theionic liquid [bmim][PF_6]. Fluid. Phase. Equilib, 2005: 207-211
[7]C. Andre Ohlin, Paul J. Dyson, Gabor Laurenczy. Carbon monoxide solubility in ionic liquids:determination, prediction and relevance to hydroformylation. Chem. Comm, 2004, 1070-1071
[1]Matter L.M.Bonati, Richard W.Joyner, Michael Stockenhuber. On the mechanism of aromaticacylation over zeolites. Microporous Mesoporous Mater, 2007, 104: 217-224
[2]Bing Yuan, Zongshi Li, Yongjun Liu, Shusheng Zhang. Liquid phase acylation of2-methylnaphthalene catalyzed. J. Mol. Catal, 2008, 280: 210-218
[3]Libor Cerveny, Katerina Mikulcova, Jiri Cejka. Shape-selective synthesis of2-acetylnaphthalene via naphthalene acylation with acetic anhydride over large pore zeolites. Appl.Catal.A, 2002, 223:65-72
[4]Manuela Casagrande, Loretta Storaro, Maurizio Lenarda, Renzo Ganzerla. Highly selectiveFriedel-Crafts acylation of 2-metyoxynaphthlene catalyzed by H-BEA zeolite. Appl. Catal. A,2000, 201:263-270
[5]Wei Wu, Guang Wu, Minlin Zhang. Highly selective synthesis of 2,6-Dimethylnaphthanlene bygreen catalysts: N-alkyl-pyridinium halides-aluminum chloride ionic liquids. Appl. Catal, 2007,326:189-193
[6]吴伟，魏晓丽，武光，李凌飞，张密林．酸性离子液体高选择性催化合成2，6-二甲基萘．催化学报，2007，28：572-578
[7]赵卫娟．芳烃羰基化和氧化反应新催化体系研究：[学位论文]．杭州：浙江大学理学院化学系，2007
[8] Yukihide Shiraishi, Naoki Toshima, Tokiji Kawamura, Hisashi Mihori, Hiroaki Shirai, Hidefumi Hirai. Selective synthesis of 2,6-naphthalenedicarboxylic acid by use of cyclodextrin as catalyst. J.Mol.Catal.A, 1999, 139:149-158
[9]Hidefumi Hirai. Selective Synthesis of Aromatic Dicarboxylic Acid Using Cyclodextrin as Catalyst. Polymers for Advanced Technologies, 1997, 8:666-673
[2]L. D. Lillwitz. Production of dimethyl-2-6-naphthalenedicarboxylate precursor to polyethylene naphthalene.Appl. Catal.A, 2001, 221:337-358
[3]刘万治，谢刚．PEN及其中间体2，6-萘二甲酸简介．聚酯工业，2006，19：7-10
[4]许杰，铁大华，王吕东．聚酯用萘系衍生物的开发技术进展．合成技术及应用，2002，17：22-26
[5]J.Allen, E.Malmberg. Recovery of 2,6-dialkyl-naphthalene isomers. US,4900717 (15 February1966) to Sun oil
[6]Chem Systems' PERP report. 2, 6-Naphthalene Dicarboxylic Acid. January 1991
[7]Manfred T. Reetz, Johannes G. de Vries. Ligand-free Heck reactions using low Pd-loading.Chem.Comm, 2004: 1559
[8] K.Sumitani,K,Shimada. JP 0413637( January 1997)
[9]孙绪江，张军，齐彦伟．分子筛吸附分离2，6-二甲基荼．精细石油化工．1999：4-6
[10] Jung-Nam Park, Jun Wang, Suk-In Hong, Chul Wee Lee. Effect of dealumination of zeolite catalysts on methylation of 2-methylnaphthalene in a high-pressure fixed-bed reactor. Appl. Catal. A, 2005, 292:68-75
[11]吴伟，魏晓丽，武光，李凌飞，张密林．酸性离子液体高选择性催化合成2，6-二甲基萘．催化学报，2007，28：572-578
[12]叶启亮，郭世卓，曹发海，房鼎业．2，6-萘二甲酸制备工艺进展．化学世界，2005：181-185
[13]涂根国，陈海平，汪杰，刘丽莉，乔迁．2，6-荼二甲酸的合成与纯化技术进展．河南化工，2007，24：10-12
[14]开万龙．2，6-萘二甲酸纯化技术进展．金山油化纤，2000：22-28
[15]赵卡克，陈建定，愈三传，吴叙勤．2，6-萘二甲酸的化学精制法．高分子材料1995：33-36
[1]Tom Welton. Ionic liquids in catalysis. Coord. Chem. Rev, 2004, 248: 2459-2477
[2]Peter Wasserscheid, Wilhelm Keim. Ionic liquids-New"Solutions"for transition metal catalysis.Angew. Chem. Int. Ed, 39: 3772-3789
[3]Nidhi Jain, Anil Kumar, Sushma Chauhan, S.M.S. Chauhan. Chemial and biochemicaltransformation in ionic liquids. Tetra, 2005, 61:1015-1060
[4]Paulo A.Z. Suarez, Jeane E.L.Dullius, Sandra Einloft, Roberto F. De Souza, Jairton Dupont.The use of new ionic liquids in two-phase catalytic hydrogenation reaction by rhodium complexes.Polyhedron, 1996, 15:1217-1219
[5]Adrian J. Carmichael, Martyn J.Earle, John D. Holbrey, Paul B. McCormac, Kenneth R.Seddon. The Heck Reactidn in Ionic Liquids: A Multiphasic Catalyst System. Org. Lett, 1999, 1:997-1000
[6]Joshua Howath, Keith Hanlon , Darren Fayne , Paul McCormac. Moisture StableDialkylimidazolium Salts as Heterogeneous and Homogenous Lewis Acids in the Diels-AlderReaction. Tetra. Lett, 1997, 38:3097-3100
[7]Choong Eui Song, Eun Joo Roh. Practical method to recycle a chiral(salen)Mn epoxidationcatalyst by using an ionic liquid. Chem.Comm, 2000, 837-838
[8]Eiichiro Mizushima, Teruyuki Hayashi, Masato Tanaka. Palladium-catalysed carbonylation ofaryl halides in ionic liquid media: high catalyst stability and significant rate-enhancement inalkoxycarbonylation. Green Chemisry, 2001, 3: 76
[9]Wei Wu, Guang Wu, Minlin Zhang. Highly selective synthesis of 2,6-Dimethylnaphthanlene bygreen catalysts: N-alkyl-pyridinium halides-aluminum chloride ionic liquids. Appl. Cata, 2007,326:189-193
[10]Zhongkui Zhao, Zongshi Li, Guiru Wang, Weihong Qiao, Lvbo Cheng. Friedel-Craftsalkylation of 2-methylnaphthalene in room temperature ionic liquids. Appl. Cata, 2004, 262:69-73
[11]乔煜，邓友全．超强酸性室温离子液体反应介质中烷烃羰化研究．化学学报，60(8)：1520-1523
[12]Christopher J.Adams, Martyn J. Earle, Glyn Roberts, Kenneth R. Seddon. Friedel-Crafts??reactions in room temperature ionic liquids. Chem. Commun, 1998. 2097-2098
[13]章维超．甲苯选择性羰基化合成对甲基苯甲醛研究：[学位论文]．杭州：浙江大学理学院化学系，2006
[14]Nidhi Jain, Anil Kumar, Sushma Chauhan, et al. Chemical and biochemical transformationsin ionic liquids. Tetra, 2005, 61:1015-1060
[15] Vasudevan V, Namboodiri, Rajender S. Varma. Microwave-assisted preparation ofdialkylimidazolium tetrachloroaluminates and their use as catalysts in the solvent-freetetrahydropyranylation of alcohols and phenols. Chem. Comm, 2002: 342-343
[16]Vasudevan V, Namboodiri, Rajender S. Varma. Solvent-Free Sonochemicl Preparation ofIonic liquids. Org. lett, 2002, 4:3161-3163
[1]王一平，张国建，黄群武，刘卫兵．UNIFAC发估算甲烷在常三柴油中的高压溶解度．计算机与应用化学，2007，24：1315-1318
[2]Hua Chao, Xu Shi-min, Li Xin-gang, Ma Pei-sheng. Apparatus of Measuring Gas Solubility Under High Pressure. Journal of Tianjin Universiby, 2006. 39:25-30
[3]白亮，赵玉龙，张碧江．高压搅拌釜中H_2、CO住不同液体介质中的溶解度和体积传质系数的研究．化学反应工程与工艺，1996，12：190-194
[4]Dean Camper , Paul Scovazzo , Carl Koval , Richard Noble. Gas Solubilities inRoom-Temperature Ionic Liquids. Ind. Eng. Chem. Res. 2004, 43: 3049-3054
[5]Jennifer L. Anthony, Jessica L. Anderson, Edward J. Maginn, Joan F. Brennecke. Anion Effectson Gas Solubility in Ionic Liquids. J. Phys. Chem. B, 2005, 109: 6366-6374
[6]Jacek Kumelan, Alvaro Perez-Salado Kamps, Dirk Tuma, Gerd Maurer. Solubility of CO in theionic liquid [bmim][PF_6]. Fluid. Phase. Equilib, 2005: 207-211
[7]C. Andre Ohlin, Paul J. Dyson, Gabor Laurenczy. Carbon monoxide solubility in ionic liquids:determination, prediction and relevance to hydroformylation. Chem. Comm, 2004, 1070-1071
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