中文
Earlier issues
Announcement
More
Progress in Chemistry 1998, Vol. 10 Issue (02): 146- Previous Articles   Next Articles

• Review •

Advances of Aqueous Biphasic Catalysis by Wa ter-Soluble Phosphine Transition-Metal Complexes

Chen Hua;Li Yaozhong;Li Dongwen;Cheng Puming;Li Xianjun   

  1. Department of Chemistry, Sichuan University, Chengdu 610064, China
  • Received: Revised: Online: Published:
  • Contact: Li Xianjun
PDF ( 2251 ) Cited
Export

EndNote

Ris

BibTeX

This paper describes the advances in the syntheses of water soluble phosphines and aqueous biphasic catalysis by water soluble phosphine transition metal complexes, especially in the hydroformylation of olefins and the hydrogenation of A, B2unsaturated carbonyl compounds, and also in the asymmetric catalytic synthesis. The problems to be overcome in the applications of aqueous biphasic catalysis are discussed.

Key words: biphasic catalysis, water soluble phosphines, hydroformylation, hydrogenation, asymmetric synthesis

CLC Number: 

[1 ] Chatt J , Leigh G J , Stade R M , J. Chem. Soc. , Dalton Trans. , 1973, 2021.
[2 ] Joo F, Beck M T , React. Kin. Catal. Lett. , 1975, 2, 257- 263.
[3 ] Joo F, Toth Z, Beck M T , Inorg. Chem. Acta, 1977, 25, L 61- L 62.
[4 ] Kuntz E G, Chemtech, 1987, 15, 570- 575.
[5 ] Cornils B, Wiebus E, Chemtech, 1995, 23, 33- 38.
[6 ] Wiebus E, Cornils B, Hydrocarbon Processing , 1996, 63- 66.
[7 ] Cornils B, Kuntz E G, J. Organomet. Chem. , 1995, 502, 177- 186.
[8 ] Cornils B, Herrmann W F, Eckl R W , J. Mol. Catal. A : Chemical, 1997, 116, 27- 33.
[9 ] Haggin J , C & EN , 1994, 72 (Oct. 10) , 29- 36.
[10 ] Horvath I T , Joo F, Aqueous Organometallic Chemistryand Catalysis, Kluwer Academic Publishers,Dordrecht/Boston/London, 1995.
[11 ] 209th Meetingofthe American Chemical Society , Abstracts of Papers, Anaheim, CA , 1995.
[12 ] Barton M , Atwood J D, J. Coord. Chem. , 1991, 24, 43.
[13 ] Kalck P, Monteil F, Adv. Organomet. Chem. , 1992, 34, 219- 283.
[14 ] Herrmann W A , Kohlpaintner C W , Angew. Chem. Int. Ed. Engl. , 1993, 32, 1524- 1544.
[15 ] 陈华, 刘海超, 黎耀忠, 李贤均, 化学研究与应用, 1993, 5 (1) , 14- 21 .
[16 ] Roundhill D M , Adv. Organomet. Chem. , 1995, 38, 155- 188.
[17 ] Beller M , Cornils B, Frohning C D et al. , J. Mol. Catal. A : Chemical, 1995, 104, 17- 85.
[18 ] Cornils B, Angew. Chem. Inter. Ed. Engl. , 1995, 34 (15) , 1575- 1577.
[19 ] 殷元骐主编, 羰基合成化学, 化学工业出版社, 北京, 1996, 44- 63.
[20 ] 郑晓来, 王艳华, 左焕培, 分子催化, 1996, 10 (1) , 70- 80.
[21 ] Joo F, Katho A , J. Mol. Catal. A : Chemical, 1997, 116, 3- 26.
[22 ] 方志平, 石油化工, 1997, 26 (7) , 479- 486.
[23 ] 郑晓来, 蒋景阳, 王兵, 金子林, 化学进展, 1997, 9 (2) , 111- 122.
[24 ] Larpent C, Dabard R, Patin H, Inorg. Chem. , 1987, 26, 2922- 3003.
[25 ] Grosslin J M , Mercier C, J. Mol. Catal. , 1990, 63, L 25- L 27.
[26 ] Grosslin J M , Mercier C, Allmang G, Grass F, Organometallics, 1991, 10, 2122- 2133.
[27 ] Fache E, Santini C, Senocq F, Basset J M , J. Mol. Catal. , 1992, 73, 331- 336.
[28 ] Kuntz E G, FR 2 366 237, 1976.
[29 ] Kuntz E G, D E 2 733 516, 1978 (Chem. Abstr. , 1978, 88, 152026t).
[30 ] Tokytoh Y, Yoshimura N , US 4 808 756, 1989.
[31 ] Yoshimura N , Tamura M , E P 04 362 226, 1990.
[32 ] Homogeneous Catalysis (Eds. Parshall GW , Ittel S D) , 2nded. , Wiley, New York, 1992, 126-128.
[33 ] Kuntz E G, FR 2 338 253, 1976.
[34 ] Kuntz E G, D E 2 700 904, 1977 (Chem. Abstr. , 1977, 87, 117602k).
[35 ] Kohlpaintner C W , Beller M , J. Mol. Catal. A : Chemical, 1997, 116, 259- 267.
[36 ] Madden T D, PeelW E, Quinn P J et al. , J. Biochem. Biophys. Methods, 1980, 2, 19.
[37 ] Farin F, Van Gaal H L M , Bonting S L et al. , J. Biochem. Biophys. Acta, 1982, 711, 336- 344.
[38 ] Vigh L , Joo F, Van Hasselt P R, Kuiper P J C, J. Mol. Catal. , 1983, 22, 15- 19.
[39 ] Mercier C, Chabardes P, Pure &Appl. Chem. , 1994, 66 (7) , 1509- 1518.
[40 ] ChauvelA , Delmen B, Holderich W F, Appl. Catal. , 1994, 115, 173- 178.
[41 ] Ahrland S, Chatt J , Davies R M , Williams A A , J. Chem. Soc. , 1958, 276- 279.
[42 ] Herrmann W A , Albanese G P, Manetsberger R B et al. , Angew. Chem. Int. Ed. Engl. , 1995, 34(7) , 811- 813.
[43 ] Herrmann W A , Kohlpaintner C W , Manetsberger R B et al. , J. Mol. Catal. A : Chemical, 1995,97, 65- 72.
[44 ] Herrmann W A , Manetsberger R B, Bahrmann H et al. , J. Mol. Catal. , 1992, 73, 191- 201.
[45 ] Wan K T , Davis M E, J. Chem. Soc. , Chem. Commun. , 1993, 1262- 1264.
[46 ] Ding H, Hanson B E, Bakos J , Angew. Chem. Int. Ed. Engl. , 1995, 34 (15) , 1645- 1647.
[47 ] Bartik T , Ding H, Bartik B, Hanson B E, J. Mol. Catal. A : Chemical, 1995, 98, 117- 122.
[48 ] Bartik T , Bartik B, Hanson B E et al. , Organometallics, 1993, 12, 164- 170.
[49 ] Ding H, Hanson B E, Bartik T , Bartik B, Organometallics, 1994, 13, 3761- 3763.
[50 ] Alario F, Amrani Y, Colleuille Y et al. , J. Chem. Soc. , Chem. Commun. , 1986, 202- 203.
[51 ] Armrani Y, Lecomte L , Sinou D et al. , Organometallics, 1989, 8 (2) , 542- 547.
[52 ] Lecomte L , Sinou D, Phosphorus, Sulfur,and Silicon, 1990, 53, 239- 251.
[53 ] Kuntz E G, FR 2 314 910, 1975.
[54 ] Kuntz E G, FR 2 349 562, 1976.
[55 ] Kuntz E G, FR 2 338 253, 1976.
[56 ] Cornils B, Lappe P, Gartner R, Springer H, E P 0 107 006, 1983 (Chem. Abstr. , 1984, 101,55331t).
[57 ] Varre C, Desbois M , Novel J , FR 2 561 650, 1985.
[58 ] Herrmann W A , Kulpe J A , Kellner J et al. , Angew. Chem. Int. Ed. Engl. , 1990, 29 (4) , 391-393.
[59 ] Lensink C,de Vries J D, Tetrahedron: Asymmetry , 1992, 3, 235.
[60 ] Herd O , Langhans K P, Stelzer O et al. , Angew. Chem. Int. Ed. Engl. , 1993, 32 (7) , 1058-1059.
[61 ] Herd O , Hebler A , Langhans K P et al. , J. Organomet. Chem. , 1994, 475, 99- 111.
[62 ] Avey A , Schurt D M , Weakley T J R, Tyler D R, Inorg. Chem. , 1993, 32, 233- 236.
[63 ] Schull T L , Fettinger J C, Knight D A , J. Chem. Soc. , Chem. Commun. , 1995, 1487- 1488.
[64 ] Malmstrom T , Andersson C, Chem. Commun. , 1996, 1135- 1136.
[65 ] Malmstrom T , Andersson C, J. Mol. Catal. A : Chemical, 1997, 116, 237- 245.
[66 ] Fremy G, Castanet Y, Grzybek R et al. , J. Organomet. Chem. , 1995, 505, 11- 16.
[67 ] Ganguly S, Mague J T , Rondhill D M , Inorg. Chem. , 1992, 31, 3500- 3501.
[68 ] Ganguly S, Roundhill D M , Organometallics, 1993, 12, 4825.
[69 ] Baxley G T , Weakley T J R, Miller W K et al. , J. Mol. Catal. A : Chemical, 1997, 116, 191-198.
[70 ] Mohr B, Lynn D M , Grubbs R H, Organometallics, 1996, 15, 4317- 4325.
[71 ] Lavenot L , Bortoletto M H, Roucoux A et al. , J. Organomet. Chem. , 1996, 509, 9- 14.
[72 ] Mercier F, Mathey F, J. Organomet. Chem. , 1993, 462, 103- 106.
[73 ] Mitchell T N , Heeshe-Wagner K, J. Organomet. Chem. , 1992, 436, 43- 53.
[74 ] Heesche-Wagner K, Mitchell T N , J. Organomet. Chem. , 1994, 468, 99- 106.
[75 ] Herd O , HeBler A , Hingst M et al. , J. Organomet. Chem. , 1996, 522, 69- 76.
[76 ] Mudalige D C, Rempel G L , J. Mol. Catal. A : Chemical, 1997, 116, 309- 316.
[77 ] Jin Z, Zheng X, Fell B, J. Mol. Catal. A : Chemical, 1997, 116, 55- 58.
[78 ] Bahrmann H, Bergrath K, Kleiner H et al. , J. Organomet. Chem. , 1996, 520, 97- 100.
[79 ] Bahrmann H, Bach H, Frohning C D et al. , J. Mol. Catal. A : Chemical, 1997, 116, 49- 53.
[80 ] Herrmann W H, Manetsberger R, Bahrmann H et al. , E P 0 571 829, 1993; D E 2OS 4 217 803,1992; D E 2OS 4 244 274, 1992; E P 0 491 240, 1990.
[81 ] Kuntz E G, US 4 248 802, 1981.
[82 ] 吴己丑, 袁刚, 周启召, 石油化工, 1991, 20 (2) , 79- 85.
[83 ] 陈华, 黎耀忠, 程溥明, 扬清, 李贤均, 分子催化, 1994, 8 (5) , 347- 352.
[84 ] 陈华, 刘海超, 黎耀忠, 程溥明, 李贤均, 分子催化, 1995, 9 (2) , 145- 151.
[85 ] Bach F, Bahrmann H, Cornils B et al. , E P 2PS 0 302 375, 1987.
[86 ] Russell M J H, Platinum Met. Rev. , 1988, 32 (4) , 179- 186.
[87 ] 刘海超, 四川大学硕士论文, 1993.
[88 ] 陈华, 四川大学硕士论文, 1994.
[89 ] 黎耀忠, 陈华, 祝庆等, 第五届全国均相络合催化会议论文集, 暨南大学, 广州, 1997, 104- 105.
[90 ] Li X, L I Y, Chen H et al. , Abstractsof 36th IU PA C Proc. , Geneva, Switzerland, 1997, PO STER SESS ION II, CS224.
[91 ] Fell B, Schobben C, Papadogianakis G, J. Mol. Catal. A : Chemical, 1995, 101, 179- 186.
[92 ] Bartik T , Bartik B, Hanson B E, J. Mol. Catal. , 1994, 88, 43- 56.
[93 ] Ding H, HansonB E, J. Chem. Soc. , Chem. Commun. , 1994, 27472748.
[94 ] Ding H, Hanson B E, Glass T E, Inorg. Chim. Acta, 1995, 229, 329- 333.
[95 ] Ding H, Hanson B E, J. Mol. Catal. A : Chemical, 1995, 99, 131- 137.
[96 ] Darensbourg D J , Bischoff C J , Inorg. Chem. , 1993, 32, 47.
[97 ] 黎耀忠, 黄裕林, 陈华等, 第五届全国均相络合催化会议论文集, 暨南大学, 广州, 1997, 106- 107.
[98 ] 黄裕林, 黎耀忠, 游丹等, 第五届全国均相络合催化会议论文集, 暨南大学, 广州, 1997, 108- 109.
[99 ] 李贤均, 陈华, 黎耀忠等, 中国石化总公司鉴定材料, 四川大学化学系络合催化研究室, 1996.
[100 ] Buhling A , Kamer P C J , Van Leeuwen P W N M , J. Mol. Catal. A : Chemical, 1995, 98, 69-80.
[101 ] Buhling A , Kamer P C J , Van Leeuwen P W N M et al. , J. Mol. Catal. A : Chemical, 1997, 116,297- 308.
[102 ] Bahrmann H, Frohning C D, Heymanns P et al. , J. Mol. Catal. A : Chemical, 1997, 116, 35-37.
[103 ] 刘玉鑫, 韩银仙, 陈华等, 羰基合成精细化学品技术研讨会论文摘要集, 成都, 1994, 73- 74.
[104 ] 王艳华, 蒋景阳, 何菲等, 催化学报, 1997, 18 (4) , 335- 337.
[105 ] Fremy G, Monflier E, Carpentier J et al. , Angew. Chem. Int. Ed. Engl. , 1995, 34 (13?14) , 1474- 1476.
[106 ] Davis M E, Chemtech, 1992, 498- 502.
[107 ] Bunn B B, Bartik T , Bartik B et al. , J. Mol. Catal. , 1994, 94, 157- 161.
[108 ] Yuan Y Z, Xu J L , Zhang H B, Tsai K R, Catal. Lett. , 1994, 29, 387- 389.
[109 ] 刘海超, 陈华, 黎耀忠, 李贤均, 分子催化, 1994, 8 (1) , 22- 28.
[110 ] Borowski A F, Cole-Hamilton D J , Wilkinson G, Nouv. J. Chim. , 1978, 2, 137- 144.
[111 ] Smith R T , Ungar R K, Sandersion L J , Baird M C, Organometallics, 1983, 2, 1138- 1144.
[112 ] Renaud E, Russell R B, Fortier S et al. , J. Organomet. Chem. , 1991, 419, 403- 415.
[113 ] 陈华, 黎耀忠, 李贤均, 分子催化, 1993, 7 (5) , 377- 384.
[114 ] 李瑞祥, 陈骏如, 李贤均, 分子催化, 1996, 10 (2) , 115- 119.
[115 ] 黎耀忠, 程溥明, 李贤均等, 分子催化, 1996, 10 (3) , 171- 177.
[116 ] Dror Y, Manassen J , J. Mol. Catal. , 1977, 2, 219- 222.
[117 ] Grosslin J M , Mercier C, J. Mol. Catal. , 1990, 63, L 25- L 27.
[118 ] Grosslin J M , Mercier C, Organometallics, 1991, 10, 2126- 2133.
[119 ] 王祥智, 陈华, 黎耀忠, 胡家元, 李贤均, 分子催化, 1995, 9 (3) , 207- 213.
[120 ] 王祥智, 陈华, 李贤均, 分子催化, 1996, 10 (5) , 351- 356.
[121 ] Herrmann W A , Kellner J , Riepl H, J. Organomet. Chem. , 1990, 389, 103- 128.
[122 ] Fache E, Santini C, Senocq F, Basset J M , J. Mol. Catal. , 1992, 72, 331- 336.
[123 ] Hernandez M , Kalck Ph, J. Mol. Catal. A : Chemical, 1997, 116, 117- 130.
[124 ] Fache E, Santini C, Senocq F, Basset J M , J. Mol. Catal. , 1992, 72, 337- 350.
[125 ] Hernandez M , Kalck Ph, J. Mol. Catal. A : Chemical, 1997, 116, 131- 146.
[126 ] Sanchez-Delgado R A , Medina M , Lopez-Linares F et al. , J. Mol. Catal. A : Chemical, 1997,116, 167- 177.
[127 ] Andriollo A , Carrasquel J , Marano J et al. , J. Mol. Catal. A : Chemical, 1997, 116, 157- 165.
[128 ] Toth I, Hanson B E, Davis M E, Tetrahedron: Asymmetry , 1990, 1 (12) , 913- 930.
[129 ] Amrani Y, Sinou D, J. Mol. Catal. , 1986, 36, 319- 327.
[130 ] Lecomte L , Sinou D, J. Organomet. Chem. , 1989, 370, 277- 284.
[131 ] Laghmari M , Sinou D, J. Mol. Catal. , 1991, 66, L 15- L 18.
[132 ] Oehme G, Paetzold E, Selke R, J. Mol. Catal. , 1992, 71, L 1- L 5.
[133 ] Kumar A , Oehme G, Roque J P, Schwarze M , Selke R, Angew. Chem. Int. Ed. Engl. , 1994, 33(21) , 2197- 2199.
[134 ] Herrmaan W A , Kulpe J A , Kellner J et al. , Angew. Chem. Int. Ed. Engl. , 1990, 29 (4) , 391-393.
[135 ] Lensink C, Rijnberg E,de Vries J G, J. Mol. Catal. A : Chemical, 1997, 116, 199- 207.
[136 ] Grassert I, Vill V , Oehme G, J. Mol. Catal. A : Chemical, 1997, 116, 231- 236.
[137 ] Wan K T , Davis M E, Tetrahedron: Asymmetry , 1993, 4 (12) , 2461- 2468.
[138 ] Wan K T , Davis M E, J. Catal. , 1994, 148, 1- 8.
[139 ] Wan K T , Davis M E, Nature, 1994, 370, 449- 450.
[140 ] Wan K T , Davis M E, J. Catal. , 1995, 152, 25- 30.
[141 ] Bakos J , Orosz A , Heil B et al. , J. Chem. Soc. , Chem. Commun. , 1991, 1684- 1685.
[142 ] Bakos J , Orosz A , Cserepi S et al. , J. Mol. Catal. A : Chemical, 1997, 116, 85- 97.
[143 ] Monteil F, Kalck Ph, J. Organomet. Chem. , 1994, 482, 45- 51.
[144 ] Mohr B, Lynn D M , Grubbs R H, Organometallics, 1996, 15, 4317- 4325.
[145 ] Haggin J , C & EN , 1994, 72 (38) , 28- 36.
[146 ] Horvath I T , Rabai J , Science, 1994, 266, 72- 75.
[147 ] Naughton M J , Dragol R S, J. Catal. , 1995, 155, 383- 389.
[1] Yuewen Shao, Qingyang Li, Xinyi Dong, Mengjiao Fan, Lijun Zhang, Xun Hu. Heterogeneous Bifunctional Catalysts for Catalyzing Conversion of Levulinic Acid to γ-Valerolactone [J]. Progress in Chemistry, 2023, 35(4): 593-605.
[2] Peng Wang, Huan Liu, Da Yang. Recent Advances on Tandem Hydroformylation of Olefins [J]. Progress in Chemistry, 2022, 34(5): 1076-1087.
[3] Xin Lin, Fanfu Guan, Jialin Wen, Pan-Lin Shao, Xumu Zhang. Synthesis of Chiral Tridentate Ligands with a Ferrocene Framework and Their Applications in Ir-Catalyzed Asymmetric Hydrogenation [J]. Progress in Chemistry, 2020, 32(11): 1680-1696.
[4] Lihua Qian, Guojun Lan, Xiaoyan Liu, Qingfeng Ye, Ying Li. Heterogeneous Catalysts for Biomass-Based Molecules Aqueous-Phase Catalytic Hydrogenation [J]. Progress in Chemistry, 2019, 31(8): 1075-1085.
[5] Dongya Bai, Junyao He, Bin Ouyang, Jin Huang, Pu Wang. Biocatalytic Asymmetric Synthesis of Chiral Aryl Alcohols [J]. Progress in Chemistry, 2017, 29(5): 491-501.
[6] He Qiao, Yin Zhongqiong, Chen Huabao, Zhang Zumin, Wang Xianxiang, Yue Guizhou. Catalytic Asymmetric Syntheses of Indenes and Their Derivatives [J]. Progress in Chemistry, 2016, 28(6): 801-813.
[7] Zhang Lei, Tu Qian, Chen Xuenian, Liu Pu. Nano Metal Catalysts in Dehydrogenation of Ammonia Borane [J]. Progress in Chemistry, 2014, 26(05): 749-755.
[8] Tang Xing, Hu Lei, Sun Yong, Zeng Xianhai, Lin Lu. Conversion of Biomass to Novel Platform Chemical γ-Valerolactone by Selective Reduction of Levulinic Acid [J]. Progress in Chemistry, 2013, 25(11): 1906-1914.
[9] Zhang Shufang, Bai Ying, Peng Jiajian, Hu Yingqian*, Lai Guoqiao*. Application of Polystyrene Immobilized Transition Metals as Catalysts for Hydrosilylation and Hydrogenation [J]. Progress in Chemistry, 2013, 25(05): 707-716.
[10] Xu Yingying, Li Zhao, Maxim Borzov, Nie Wanli. Application of Frustrated Lewis Pairs in the Activation of Small Molecules [J]. Progress in Chemistry, 2012, 24(08): 1526-1532.
[11] Chen Ping, Xie Guanqun, Luo Mengfei. Catalysts for Vapor-Phase Selective Hydrogenation of Crotonaldehyde to Crotyl Alcohol [J]. Progress in Chemistry, 2012, 24(01): 17-30.
[12] Liu Xiang, Pan Zhengguang, Xu Jianhe. Asymmetric Synthesis of Chiral Aryl Vicinal Diols [J]. Progress in Chemistry, 2011, 23(5): 903-913.
[13] . Organocatalytic Asymmetric α-Functionalization of β-Ketoesters [J]. Progress in Chemistry, 2010, 22(09): 1679-1686.
[14] Zhu Yingguang, Di Changwei, Hu Wenhao. Asymmetric Multicomponent Reactions [J]. Progress in Chemistry, 2010, 22(07): 1380-1396.
[15] Jin Zilin Liu Ning Liu Chun. Thermoregulated Liquid/Liquid Biphasic Catalysis [J]. Progress in Chemistry, 2010, 22(07): 1295-1309.