Journal of University of Chinese Academy of Sciences >
Some Progress in the Selenium-Catalyzed Carbonylation Reaction
Received date: 2004-02-04
Revised date: 2002-06-04
Online published: 2003-01-18
Using cheap catalysis to substitute expensive metal and low cost carbon monoxide to replace hydrogen or phosgene has been pursuing by the people for many years. The paper reviewed the selenium catalyzed carbonylation reaction such as the carbonylation of carbon, nitrogen, oxygen and sulfur containing compounds and high selective reduction of some compounds based on the Se/CO/H2O system and introduced some new progress. Catalytic amount selenium readily activated carbon monoxide under very mild conditions to synthesize a series of fine chemicals and biochemicals directly. Catalyst selenium combined advantages from heterogeneous catalysis and homogeneous catalysis is a typical example of reaction process transfer catalysis. Selenium catalyzed carbonylation reaction has been characterized by high conversion, atom economical selectivity and environmentally benign and is superior to the traditional multi step method which involves the use of phosgene.
Chen Jinzhu , Peng Aidong , LU Shiwei . Some Progress in the Selenium-Catalyzed Carbonylation Reaction[J]. Journal of University of Chinese Academy of Sciences, 2003 , 20(1) : 73 -84 . DOI: 10.7523/j.issn.2095-6134.2003.1.012
[1] R A Franz, F Applegath. A New Urea Synthesis. Ⅰ. The Reaction of Ammonia, Carbon Monoxide, and Sulfur. J Org Chem, 1961,26: 3304~3305
[2] R A Franz, F Applegath, F V Morriss, F Baiocchi. A New Synthesis of Urea. Ⅱ. The Reaction of Primary Aliphatic Amines with Carbon Monoxide and Sulfur. J Org Chem, 1961, 26:3306~3308
[3] R A Franz, F Applegath, F V Morriss, F Baiocchi, C Bolze. A New Synthesis of Urea. Ⅲ. The Reaction of Aromatic Amines with Carbon Monoxide and Sulfur. J Org Chem, 1961, 26:3309~3312
[4] 黄宪,杜灿屏.有机硒碲化合物在高选择性合成反应中的应用.化学通报,1999,9:21~29
[5] 陈家威,黄锦霞.有机硒化学研究进展.湖北大学学报,1994,16:86~96
[6] 吴军,刘秀芳,徐汉生.硒试剂在有机合成中的应用.化学试剂,1999,21(3):145~153;158
[7] N Sonoda, T Yashuhara, K Kondo, T Ikeda, S Tsutsumi. A New Synthesis of Urea. The Reaction of Ammonia or Aliphatic Amines with Carbon Monoxide in the Presence of Selenium. J Am Chem Soc, 1971, 93(23):6344
[8] N Sonoda. Selenium Assisted Carbonylation with Carbon Monoxide. Pure & Appl Chem, 1993, 65(4):699~706
[9] K Kondo, M Takarada, S Murai, N Sonoda. Synthesis of Selenolcarbamates. Synthesis, 1979, 597~598
[10] K Kondo, S Yokoyama, N Miyoshi, S Murai N Sonoda. A New Synthesis of Carbonyl Selenide. Angew Chem Int Ed Engl, 1979,18(9):691
[11] A Ogawa, N Kambe, S Murai, N Sonoda. Selenium Assisted Carbonylation of Alkyl Aryl Ketones with Carbon Monoxide. Tetrahedron, 1985, 41(21):4813~4819
[12] A Ogawa, K Kondo, S Murai, N Sonoda. Selenium-Assisted Carbonylation of o-Hydroxyacetophenone with Carbon Monoxide. J Chem Soc Chem Commun, 1982, 21:1283~1284
[13] K kondo, N Sonoda, S Tsutsumi. A New Seleniun-Triethylamine Catalysed Synthesis of Arylureas from Carbon Monoxide and Aromatic Amines. J Chem Soc Chem Commun, 1972, 307~308
[14] K Kondo, K Murate, N Miyoshi, S Murai, N Sonoda. Selenium-Catalyzed Synthesis of Urea Derivatives from Amino Acid Esters,Carbon Monoxide, and Oxygen. Synthesis, 1972, 735~736
[15] T Yoshida, N Kambe, S Murai, N Sonoda. A New Synthesis of Cyclc Urea, Cyclic Urethanes, and a Quinazolinedione. Bull Chem Soc Jpn, 1987, 60:1793~1799
[16] T Yoshida, N Kambe, S Murai, N Sonoda. A New Synthesis of Cyclic Ureas from Aromatic Diamines by Selenium-Assisted Carbonylation with Carbon Monoxide. Tetrahedron Lett, 1986, 27(26):3037~3040
[17] 杨瑛,陆世维.硒催化的乙二胺、乙醇胺和环胺的氧化羰基化反应.催化学报,2000,21(4):355~357
[18] S Cenini, M Pizzotti,C Crotti. Metal Catalyzed Deoxygenation Reactions by Carbon Monoxide of Nitroso and Nitro Compounds.Aspects of Homogeneous Catalysis, 1988, 6:97~198
[19] J J McCoy, J G Zajacek, K E Fuger. Production of Oximes or Carbonyl Compounds or Both Oximes and Carbonyl Compounds.1975, Ger Offen, DE2,428,536
[20] J J McCoy, J G Zajacek, K E Fuger. Production of Oximes by the Reaction of Carbon Monoxide with Nitrocompouods. 1976, US3,989,755
[21] J G Zajacek, J J McCoy, K E Fuger. Process for the Manufacture of Ureas. Swiss, 1978, CH605, 699
[22] H J School, A Zenner. Process for the Preparation of Urethanes. 1980, Ger Offen, (Bayer A.-G. ) 2,808,980
[23] H J School, A Zenner. Transportation Systems and Electric Cables for Use Therein. 1980, Ger Offen (Bayer A.-G. ) 2,808,900
[24] F Mweger, F Towae. Preparation of N-Aryloxazolicline-2,4-diones. 1981, Ger Offen 2,913,522
[25] Mitsubishi Chemical Industries Co Ltd, Preparation of Aromatic Urethane. Jpn Kokai Tokkyo Kobo, 1983, JP 57,175,157
[26] 杨瑛,陆世维.硒催化硝基苯的还原羰基化生成苯胺基甲酸酯.催化学报,1999,20(3):224~226
[27] V I Manov-Yuvenskii, S L Kuznetsov. Preparation of Anilines and Dialkylureas from Nitrobenzenes, Alkylamines, and Carbon Monoxide. Zh Prikll Khim, 1991, 64(12):2480~2489
[28] V I Manov-Yuvenskii, S L Kuznetsov, Y I Dergunov. Carbonylation of Amines and Nitro Compounds in an Alcohol Medium. Zh Prikll Khim, 1992, 65(9):2091~2096
[29] V I Manov-Yuvenskii, S L Kuznetsov. Synthesis and Composition of Salts of Thiolcarbamic andSelenolcarbamic Acids. Zh Prikll Khim, 1993, 66(1):159~167
[30] V I Manov-Yuvenskii, S Lkuznetsov. Characteristics of Synthesis of N-Arylcarbamothioic Acid Salts. Zh Prikll Khim, 1993, 66(7):1584~1588
[31] V I Manov-Yuvenskii. Oxidative Carbonylation of Alkylamines Combined with Reduction of Nitrobenzenes. Zh Prikll Khim, 1994,67( 1 1): 1840~1845
[32] V I Manov-Yuvenskii. Initiation of Catalytic Carbonylation of Cydohexylamine with Reduction of 3-Trifluoromethylnitrobenzene.Zh Fiz Khim, 1994, 68(8): 1520~1522
[33] V I Manov-Yuvenskii. Initiation of the Catalytic Carbonylation of Butylamine. Zh Fiz Khim, 1995, 69(5):791~796
[34] V I Manov-Yuvenskii. Effect of Selenolcarbamates on Synthesis of Ureas. Zh Obshch Khim, 1995, 65(1): 102~105
[35] V I Manov-Yuvenskii. Anomalous Effect of Catalyst Concentration on Oxidative Carbonylation of Butylamine. Zh Fiz Khim, 1997,71(5):822~827
[36] V I Manov-Yuvenskii. Stepwise Changes in the Rate of A Steady-State Catalytic Processes at Critical Values of the Initial Reagent Concentrations, Temperature, and Intensity of Stirring. Zh Fiz Khim, 2000, 4(5): 947~949
[37] 张善言,郑焰.硝基芳基化合物和芳胺羰基化合成N,N'-二芳基脲.天然气化工,1992,17(2):27~29
[38] 郑焰,贾朝霞,张善言.硒催化羰基化反应合成碳酸衍生物.西南石油学院学报,2000,22(1):70~73
[39] 何建,张善言.芳香族硝基化合物还原羰基化合成二芳基脲.天然气化工,1994,19(1):26~29
[40] Ying Yang, Shiwei Lu. Selenium-Catalyzed Reductive Carbonization of Nitrobenzene with Amines as Coreagents to Give Unsymmetric Phenylureas. Tetrahedron Lett, 1999, 40(26):4845~4846
[41] 杨瑛,陆世维.一种不对称苯基取代脲的制备方法,中国专利,申请号99112869.9.1999
[42] 杨瑛,陆世维.一种不对称取代脲类除草剂的合成方法.中国专利,申请号99112921.0.1999
[43] 薛燕,陆世维.硒催化法合成2-吡啶脲的研究.催化学报,2001,22(4):387~389
[44] 薛燕,陆世维.一种非对称苯基吡啶基脲类物质的制备方法.中国专利,申请号01103688.5.2001
[45] 薛燕,陆世维.一种苯并咪唑酮及其衍生物的合成方法.中国专利,申请号01113966.8.2001
[46] 陆世维,杨瑛,薛燕,梅建庭.硒催化羰基化合成环脲类化合物.见:中国石油和化工催化剂开发与应用技术交流会暨第十届分子筛协作网年会论文集.黄山,2001.31~34
[47] 陆世维,杨瑛,薛燕,梅建庭.硒催化羰基化合成非对称脲类化合物.见:中国石油和化工催化剂开发与应用技术交流会暨第十届分子筛协作网年会论文集.黄山,2001.25~30
[48] Jianting Mei, Shiwei Lu. Selenium-Catalyzed Selective Oxidative-Reductive Carbonylation to Give Monuron. In: 8th International SPACC Symposium.--Chemistry for Selective Reactions--Coordination Chemistry in Harmony with Other Field of Chemistry.Beijng, 2001. 71~72
[49] K Kondo, N Sonoda, S Tsutsumi. A New Synthesis of Carbamates. The Reaction of Carbon Monoxide with Amine and Alcohol in the Co-Presence of Selenium and Triethylamine. Chem Lett, 1972, 373~374
[50] N Sonoda, G Yamamoto, K Natsukawa, K Kondo, S Murai. A New Synthesis of Heterocycles by the Reaction of Amino Alcohols or Amino Thiols with Carbon Monoxide in the Presence of Selenium. Tetrahedron Lett, 1975, 24:1969~1972
[51] K Kondo, S Yokoyama, N Miyoshi, S Murai, N Sonoda. Reactions of Carbonyl Selenide with Amines and Aminoalcohols to Produce Ureas and Carbamates. Angew Chem Int Ed Engl, 1979, 18(9):692
[52] K Kondo, N Sonoda, S Tsutsumi. A New Synthesis of Carbonate. The Reaction of Carbon Monoxide with Alkolates in the Presence of Selenium. Tetrahdron lett, 1971, 51:4885~4886
[53] K kondo, N Sonoda, H Sakurai. Selenium Catalyzed Synthesis of Carbonates. The Reaction of Alkoxide with Carbon Monoxide and Oxygen in the Presence of Selenium. Bull Chem Soc Jpn, 1975, 48(1): 108~111
[54] N Sonoda, S Murai. Process for the Preparation of Carbonates. Jpn Kokai Tokkyo Kobo, 1979.54-36217
[55] K Kondo, N Sonoda, H Sekurai. Selenium as A Novel Oxidizing Agent. Selenium Catalyzed Synthesis of Carbonates by the Reaction of Formates with Alkoxides. Tetrahedron lett, 1974, 10:803~804
[56] Asahi Chemical Industry Co Ltd. Process for the Preparation of Aromatic Carbonates. Jpn Kokai Tokkyo Koho, 1980.55-92732
[57] N Sonoda, T Mizuno, S Murakami, K Kondo, A Ogawa, I Ryu, N Kambe. Selenium-Catalyzed Synthesis of S-Alkyl Thiocarbamates from Amines, Carbon Monoxide, Sulfur, and Alkyl Hal ides. Angew Chem Int Ed Engl, 1989, 28(4):452~453
[58] T Mizuno, I Nishiguchi, N Sonoda. Novel Synthesis of S-Alkyl Thiocarbamates from Amines, Carbon Monoxide, Elemental Sulfur, and Alkyl Halides in the Presence of Selenium Catalyst. Tetrahedron, 1994,50(19):5669~5680
[59] T Mizuno, I Nishiguchi, T Hirashima, A Ogawa, N Kambe, N Sonoda. A New Selenium Catalyzed Synthesis of S-Alkyl Carbonothioates from Alcohols, Carbon Monoxide, Sulfur and Alkyl Halides. Tetrahedron Lett, 1990, 31(33):4773~4776
[60] N Sonoda, G Yamamoto, S Tsutsumi. Synthesis of Aliphatic Isoselenocyanates by the Reaction of Aliphatic Isocyanides with Selenium in the Presence of Triethylamine. Bull Chem Soc Jpn, 1972, 45:2937~2938
[61] S I Fujiwara, T Shin-Ike, N Sonoda, M Aoki, K Okada, N Miyoshi, N Kambe. Novel Selenium Catalyzed Synthesis of Isothiocyanates from Isocyanates and Elemental Sulfur. Tetrahedron Lett, 1991, 32(29):3503~3506
[62] P Koch, E Perrotti. Synthesis of Hetrocycles by Selenium Catalyzed Carbonylation of Bifunctional Compounds. Tetrahedron Lett,1974, 34:2899~2900
[63] N Sonoda, K Kondo, K Nagano, N Kambe, F Morimoto. Carbon Monoxide/Water as A Reducing Agent: Formation of Selane from Selenium. Angew Chem Int Ed Engl, 1980, 19(4):308~309
[64] N Kambe, F Morimoto, K Kondo, N Sonoda. Water Gas Shift Reaction with the Aid of Selenium/Platinum Catalyst. Angew Chem Int Ed Engl, 1980, 19(12): 1007
[65] T Miyata, K Kondo, S Murai, T Hirashima, N Sonoda. Selenium-Catalyzed Reduction of Aromatic Nitro Compounds to Amines by CO/H2O in the Presence of Triethylamine. Angew Chem Int Ed Engl, 1980, 19(12): 1008
[66] J Skupinska, G Smolka. Reduction of Nitrobenzene to Aniline with Carbon Monoxide and Water. React Kinet Catal Lett, 1998, 63(2):313~316
[67] 彭爱东,陆世维.硒催化下CO/H2O还原硝基苯制苯胺.催化学报,2002,23(5):457~459
[68] 彭爱东,陆世维,梅建庭.一种合成芳胺类化合物的方法.中国专利,申请号02107742.8.2002
[69] A Ogawa, J Miyake, Y Karasaki, S Murai, N Sonoda. Synthesis Utilizing Reducing Ability of Carbon Monoxide. A New Method for Synthesis of Selenocarboxamides: Reaction of Nitriles with Selenium, Carbon Monoxide, and Water. J Org Chem, 1985, 50:384~386
[70] A Ogawa, J Miyake, Y Karasaki, S Murai, N Sonoda. Synthesis Utilizing Reducing Ability of Carbon Monoxide. New Methods for Synthesis of N-Substituted Selenoamides. Bull Chem Soc Jpn, 1985, 58:1448~1451
[71] A Ogawa, Y Nishiyama, N Kambe, S Murai, N Sonoda. Selenium, Carbon Monoxide, and Water as A New Reduction System: Reductive Cleavage of Disulfides and Diselenides to Thiols and Selenols. Tetrahedron Lett, 1987, 28(28): 3271~3274
[72] Y Nishiyama, S Hamanaka. Reductive Selenation of Aliphatic Ketones and Aldehydes by Selenation, Carbon Monoxide, and Water Leading to Symmetrical Diselenides. Synthesis Commun, 1986, 16(9): 1059~1066
[73] Y Nishiyama, S Hamanaka. Carbonyl to Methylene Conversion: Selenium-Assisted Reduction of Aromatic Ketones with Carbon Monoxide and Water. J Org Chem, 1988, 53:1326~1329
[74] Y Nishiyama, Y Makino, S Hamanaka, A Ogawa, N Sonoda. Selective Reduction of α, β-Unsaturated Carbonyl Compounds with Carbon Monoxide and Water Assisted by Selenium. Bull Chem Soc Jpn, 1989, 62(5): 1682~1684
[75] K Kondo, N Sonoda, K Yoshida, M Koishi, S Tsutsumi. A New Route for the Synthesis of Tetraalkylureas. The Reaction of Carbon Monoxide with Selenium and Dialkylamines. Chem Lett, 1972,401~404
[76] W F Souza, N Kambe, N Sonoda. A Theoretical Study on the Generation Process of Carbonyl Selenide in Selenium Catalyzed Carbonylation of Amines. Chem Lett, 1996, 155~156
[77] 薛燕.[硕士学位论文].大连:中国科学院大连化学物理研究所(Xue Y.[MD Dissertation].Dalian Inst Chem Phys).2001.57~69
[78] Mei Jian-Ting, Lu Shi-Wei. Reaction Process Transfer Catalysis for Selective Oxidative-Reductive Carbonylation to Muron. Chinese Journal of Catalysis, 2000, 1:1~2
/
| 〈 |
|
〉 |