首次在亲水性离子液体[Rmim][p-CH3C6H4SO3](1-烷基-3-甲基咪唑对甲苯磺酸盐,R=甲基、乙基、正丁基、正己基和正辛基)中,以水溶性的[RuCl2(TPPTS)2]2(TPPTS:间磺酸钠基三苯基膦)为催化剂,分别考察了温度、压力、不同的离子液体、水和碘的加入等因素对喹啉加氢反应的影响.在100℃和氧气压力为3.0 MPa时,喹啉加氢生成1,2,3,4-四氧喹啉的选择性超过99%,转化率达到95.3%.利用环己烷萃取反应产物,即可实现催化剂与产物的分离,催化剂循环使用6次后反应的转化率仍可达86.0%.
参考文献
[1] | Katritzky A R;Rachwal S;Rachwal B .[J].Tetrahedron,1996,52(48):15031. |
[2] | 赵玉军,汪游清,周永贵.二茂铁衍生的手性硫膦配体在铱催化喹啉不对称氢化中的应用[J].催化学报,2005(09):737-739. |
[3] | Wen-Bo Wang;Sheng-Mei Lu;Peng-Yu Yang;Xiu-Wen Han;Yong-Gui Zhou .Highly Enantioselective Iridim-Catalyzed Hydrogenation of Heteroaromatic Compounds, Quinolines[J].Journal of the American Chemical Society,2003(35):10536-10537. |
[4] | Avemaria F.;Vanderheiden S.;Brase S. .The aza-xylylene Diels-Alder approach for the synthesis of naturally occurring 2-alkyl tetrahydroquinolines[J].Tetrahedron,2003(35):6785-6796. |
[5] | Campanati M;Vaccari A;Piccolo O .[J].Journal of Molecular Catalysis A:Chemical,2002,179(1-2):287. |
[6] | YONG-GUI ZHOU .Asymmetric Hydrogenation of Heteroaromatic Compounds[J].Accounts of Chemical Research,2007(12):1357-1366. |
[7] | Ken-ichi Fujita;Chihiro Kitatsuji;Shigetoyo Furukawa;Ryohei Yamaguchi .Regio- and chemoselective transfer hydrogenation of quinolines catalyzed by a Cp~*Ir complex[J].Tetrahedron letters: The International Journal for the Rapid Publication of Preliminary Communications in Organic Chemistry,2004(16):3215-3217. |
[8] | Busolo M A;L6pez-Linares E;Andriollo A;Paez D E .[J].J Mol CatalA,2002,189(02):211. |
[9] | Frediani P;Pistolesi V;Frediani M;Rosi L .Catalytic activity of dihydride ruthenium complexes in the hydrogenation of nitrogen containing heterocycles[J].Inorganica Chimica Acta,2006(3):917-925. |
[10] | Sanchez-Delgado R A;Rond6n D;Andriollo A;Herrera V Martin G Chaudret B .[J].ORGANOMETALLICS,1993,12(11):4291. |
[11] | Campanati M;Casagrande M;Fagiolino I;Lenarda M Storaro L Battagliarin M Vaccari A .[J].Journal of Molecular Catalysis A:Chemical,2002,184(1-2):267. |
[12] | Okazaki H;Onishi K;Soeda M;Ikefuji Y Tamura R Mochida I .[J].Bulletin of the Chemical Society of Japan,1990,63(11):3167. |
[13] | 陈骏,薛芳,付海燕,樊光银,袁茂林,陈华,李贤均.纳米Ru催化剂催化喹啉加氢反应[J].催化学报,2007(11):975-979. |
[14] | 张瑞敏,樊光银,李诚,王瑛瑛,李瑞祥,陈华,李贤均.Ru/ZrO2·xH2O催化喹啉加氢反应[J].物理化学学报,2008(06):965-970. |
[15] | Welton T .[J].Chemical Reviews,1999,99(08):2071. |
[16] | 郑宏杰,李敏,陈华,李瑞祥,李贤均.高活性离子液体-铑膦络合物体系催化1-己烯氢甲酰化反应[J].催化学报,2005(01):4-6. |
[17] | Sanchez-Delgado R A;Medina M;Lapez-Linares F;Fuentes A .[J].JMol CataiA,1997,116(1-2):167. |
[18] | Lin Q;Jiang WD;Fu HY;Chen H;Li XJ .Hydroformylation of higher olefin in halogen-free ionic liquids catalyzed by water-soluble rhodium-phosphine complexes[J].Applied Catalysis, A. General: An International Journal Devoted to Catalytic Science and Its Applications,2007(1):83-87. |
[19] | Wang J B;Feng J;Qin R X;Fu H Y Yuan M L Chen H Li X J .[J].Tetrahedron:Asymmetry,2007,18(14):1643. |
[20] | Fish R H;Kim H S;Fong R H .[J].Organometallics,1989,8(05):1375. |
[21] | Fish R H;Baralt E;Kim H S .[J].Organometallics,1991,10(06):1965. |
[22] | Roberto A.Sanchez-Delgado;Nataliya Machalaba;Nkechia Ng-a-qui .Hydrogenation of quinoline by ruthenium nanoparlicles immobilized on poly(4-vinylpyridine)[J].Catalysis Communications,2007(12):2115-2118. |
[23] | Browen R A;Poller E;McKoon E;Eckert C A Liotta C L Jessop PG .[J].Journal of the American Chemical Society,2001,123(06):1254. |
上一张
下一张
上一张
下一张
计量
- 下载量()
- 访问量()
文章评分
- 您的评分:
-
10%
-
20%
-
30%
-
40%
-
50%