Metal-Catalysed Reactions of Hydrocarbons / 07-Hydrogenation of Alkenes and Related Processes

HYDROGENATION OF ALKENES AND RELATED PROCESSES

351

77.R.L. Moss, D. Pope and B.J. Davis, J. Catal. 62 (1980) 161.

78.M.K. Gharpurey and P.H. Emmett, J. Phys. Chem. 65 (1961) 1182.

79.J.S. Campbell and P.H. Emmett, J. Catal. 7 (1967) 232.

80.W.K. Hall, L.G. Christner and J.G. Larson, Preprints ACS Mtg., Divn. Petroleum Chem. 11 (1966) paper A9.

81.J. Tuul and H.E. Farnsworth, J.Am. Chem. Soc. 83 (1961) 2247.

82.S. Naito and M. Tanimoto, J. Chem. Soc. Chem. Comm.(1987) 363; G. Ghiotti, F. Boccuzzi and

A.Chiorino, SSSC 48 (1989) 415.

83.T. Takeuchi, M. Sakaguchi, I. Miyoshi and T. Takatabate, Bull. Chem. Soc. Japan 35 (1962) 1390;

T.Takeuchi. Bull. Chem. Soc. Japan 38 (1965) 322.

84.R.J. Best and W.W. Russell, J. Am. Chem. Soc. 76 (1954) 838.

85.J. Tuul and H.E. Farnsworth, J. Am. Chem. Soc. 83 (1061) 2253.

86.E.A. Alexander and W.W. Russell, J. Catal. 4 (1965) 184.

87.W.K. Hall and P.H. Emmett, J. Phys. Chem. 68 (1959) 1102.

88.T. Takeuchi, Y. Tezuka and O. Takayasu, J. Catal. 14 (1969) 126.

89.H.E. Farnsworth, Adv. Catal. 15 (1964) 31.

90.S. Bhatia, X. Wu, D.K. Sanders, B.C. Gerstein, M. Pruski and T.S. King, Catal. Today 12 (1992) 165.

91.M. Masai, K. Honda, A. Kubota, S. Ohnaka, Y. Nishikawa, K. Nakahara, K. Kishi and S. Ikeda,

J.Catal. 50 (1977) 419.

92.Yong-Ki Park, F.H. Ribeiro and G.A. Somorjai, J. Catal. 178 (1995) 66.

93.H. Imamura, K. Igawa, Y. Kasuga and S. Tsuchiya, J. Chem. Soc. Faraday Trans. 90 (1994) 2119.

94.R.L. Moss, D. Pope and H.R. Gibbens, J. Catal. 46 (1977) 204.

95.G.C. Bond and D.E. Webster, Ann. New York Acad. Sci. 158 (1969)540.

96.H. Imamura, K. Fujita, Y. Sakata and S. Tsuchiya, Catal. Lett. 28 (1996) 231.

97.K. Soga, H. Imamura and S. Ikeda, J. Catal. 56 (1979) 119.

98.J. Barbier, E. Lamy-Pitara, P. Mar´ecot, J.P. Boitiaux, J. Cosyns and F. Verna, Adv. Catal. 37 (1990) 279.

99.P.B. Wells in: Surface Chemistry and Catalysis (A.F. Carley, P.R. Davies, G.J. Hutchings and M.S. Spencer, eds.), Kluwer: Dordrecht (2003).

100.J. Turkevich, F. Bonner, D.O. Schissler and A.P. Irsa, Discuss. Faraday Soc. 8 (1950) 352.

101.J. Turkevich, D.O. Schissler and A.P. Irsa, J. Phys. Coll. Chem. 55 (1951) 1078.

102.D. Briggs, J. Dewing, A.G. Burden, R.B. Moyes and P.B. Wells J. Catal. 65 (1980) 31.

103.G.C. Bond, J.J. Phillipson, P.B. Wells and J.M. Winterbottom, Trans. Faraday Soc. 60 (1964) 1847.

104.C. Kemball, J. Chem. Soc. (1956) 735.

105.C. Kemball and P.B. Wells, J. Chem. Soc. A (1968) 444.

106.D.O. Schissler, S.O. Thompson and J. Turkevich, Adv. Catal. 9 (1957) 37.

107.V.H. Dibeler and T.I. Taylor, J. Chem. Phys. 16 (1948) 1008.

108.G.C. Bond, G. Webb and P.B. Wells, Trans. Faraday Soc. 64 (1968) 3077.

109.G.C. Bond and J. Addy, Trans. Faraday Soc. 53 (1957) 377.

110.P.A. Sermon, G.C. Bond and P.B. Wells, J. Chem. Soc. Faraday Trans. 1 75 (1979) 385.

111.G.C. Bond, J.J. Phillipson, P.B. Wells and J.M. Winterbottom, Trans. Faraday Soc. 62 (1966) 443.

112.G.H. Twigg, Discuss. Faraday Soc. 8 (1950) 152.

113.H. Yoshitake, K. Akasura and Y. Iwasawa, J. Chem. Soc. Faraday Trans. 1 84 (1988) 4337.

114.T. Ichijima, Catal. Today 28 (1996) 105.

115.H. Yoshitake and Y. Iwasawa, J. Phys. Chem. 95 (1991) 7368.

116.K. Tamaru and S. Naito in: Handbook of Heterogeneous Catalysis, Vol. 3 ( G. Ertl, H. Knozinger¨ amd J. Weitkamp, eds.), Wiley-VCH: Weinheim (1997), p. 1005.

117.Z. Schay and P. T´et´enyi, J. Chem. Soc. Faraday Trans. I 75 (1979) 1001.

352

CHAPTER 7

118.Z. Pa´al and S.J. Thomson, J. Catal. 30 (1973) 96. .

119.F. Zaera, Langmuir 12 (1996) 88.

120.K.R. McCrea and G.A. Somorjai, J. Molec. Catal. A: Chem. 163 (2000) 43.

121.F. Zaera, J. Phys. Chem. 94 (1990) 5090.

122.T. Ohtani, J. Kubota, J.N. Kondo, C. Hirose and K. Domen, J. Phys. Chem. B 103 (1999) 4562.

123.Y. Chen, Nature 337 (1989) 519.

124.G.A. Somorjai, Cat. Tech. (5) (1999) 84.

125.G.A. Somorjai and K.R. McCrea, Adv. Catal. 45 (2000) 385.

126.G.A. Somorjai, Chem. Rev. 96 (1996) 1223.

127.G.A. Somorjai, Appl. Surf. Sci. 121/122 (1997) 1.

128.G.A. Somorjai, J. Molec. Catal. A: Chem. 107 (1996) 39.

129.P.S. Cremer and G.A. Somorjai, J. Chem. Soc. Faraday Trans. 91 (1995) 3671.

130.M. Neurock and R.A. van Santen, J. Phys. Chem. B 104 (2000) 11127.

¨

131. H. Ofner and F. Zaera, J. Phys. Chem. B 101 (1997) 396.

132. F. Zaera and D. Crysostomou, Surf. Sci. 457 (2000) 89.

133. T.V.W. Janssens, D. Stone, J.C. Heminger and F. Zaera, J. Catal. 177 (1998) 284. 134. P. Berlowitz, C. Megins, J.B. Butt and H.H. Kung, Langmuir 1 (1985) 206.

135. C. Egawa, H. Iwai and S. Oki, Surf. Sci. 454–456 (2000) 347. 136. C. Egawa, S. Endo, H. Iwai and S. Oki, Surf. Sci. 474 (2001) 14. 137. C. Egawa, Surf. Sci. 454–456 (2000) 222.

138. M. Bowker, J.L. Gland, R.W. Joyner, X.-Y. Li, M.M. Slin’ko and R. Whyman, Catal. Lett. 25 (1994) 293.

139. Xingcai Guo and R.J. Madix, J. Catal. 155 (1995) 336.

140. T. Sekitani, T. Takaoka, M. Fujisawa and M. Nishijima, J. Phys. Chem. 96 (1992) 8462; M. Nishijima, J. Yoshinobu, T. Sekitani and M. Onchi, J. Chem. Phys. 90 (1989) 5114.

141. J. R. Engstrom, D.W. Goodman and W.H. Weinberg, J. Phys, Chem. 94 (1990) 396. 142. R.E. Cunningham and A.T. Gwathmey, Adv. Catal. 9 (1957) 25.

143. S.P. Daly, A.L. Utz, T.R. Trautman and S.T. Ceyer, J. Am. Chem. Soc. 116 (1994) 6001. 144. E.K. Rideal, Adv. Catal. 9 (1957) 8.

145. G. Barone, D. Duca and G. La Manna, Recent Res. Devel. Quantum Chem. 2 (2001) 71. 146. D. Duca, L. Bot´ar and T. Vidoczy´ . J. Catal. 162 (1996) 260.

147. A.S. McLeod in: Catalysis in Application (S.D. Jackson, J.S.J. Hargreaves and D. Lennon, eds.), Roy. Soc. Chem.: London (2003), p. 86.

148. D.H. Mei, E.W. Hansen and M. Neurock, J. Phys. Chem. B 107 (2003) 798. 149. A.S. McLeod and L.F. Gladden, J. Chem. Phys. 110 (1999) 4000.

150. A.S. McLeod and L.F. Gladden, J. Catal. 173 (1998) 43. 151. A.S. McLeod and L.F. Gladden, Catal. Lett. 43 (1997) 189.

152. D. Duca, G. La Manna and M.R. Russo, Phys. Chem. Chem. Phys. 1 (1999) 1375. 153. P. Ellison and M. Feinberg, J. Molec. Catal. A: Chem. 154 (2000) 155.

154. O.N. Temkin, A.V. Zeigarnik, R.E. Vald´es-P´erez and L.G. Bruk, Kinet. Catal. 41 (2000) 298. 155. D.A. Dowden: in Specialist Periodical Reports: Catalysis (C. Kemball and D.A. Dowden, eds.),

Roy. Soc. Chem. 3 (1980), p. 136.

156. M.S.W. Lau and P.A. Sermon, J. Chem. Soc. Chem. Comm. (1978) 791.

157. W.C. Conner Jr. in: New Aspects of Spillover Catalysis (T.Inui, K. Fujimoto, T. Uchijima and M. Masai, eds.) Studies in Surface Science and Catalysis, Elsevier: Amsterdam 77 (1993) 61.

158. J.F. Cevallos-Candau and W.C. Conner Jr., J. Catal. 106 (1987) 378.

159. E. Kikuchi and T. Matsuda in: New Aspects of Spillover Catalysis (T. Inui. K. Fujimoto, Y. Uchijima and M. Masai, eds.) Studies in Surface Science and Catalysis, Elsevier: Amsterdam 77 (1993) 53.

HYDROGENATION OF ALKENES AND RELATED PROCESSES

353

160.F. Roessner, V. Roland and T. Braunschweig, J. Chem. Soc. Faraday Trans. 91 (1995) 1539.

161.F. Roessner and V. Roland, J. Molec. Catal. A: Chem. 112 (1996) 401. .

162.J.P. Marcq. G. Poncelet and J.J. Fripiat, J. Catal. 87 (1984) 339.

163.N.I. Il’chenko, Kinet. Katal. 8 (1967) 215.

164.R. Benali, C. Hoang-Van and P. Vergnon, Bull. Soc. Chim. Frnace (1985) 417.

165.J.P. Marck, G. Poncelet and J.J. Fripiat, J. Catal. 87 (1984) 339.

166.G.C. Bond and P.A. Sermon, J. Chem. Soc. Faraday Trans. I 72 (1976) 233.

167.J.P. Marcq, X. Wispenninckx, G. Poncelet, D. Keravis and J.J. Fripiat, J. Catal.73 (1982)

309.1

168.D. Tinet and J.J. Fripiat, Rev. Chim. Minerale´ 19 (1982) 612.

169.G.C. Bond, P.A. Sermon and C.J. Wright, Mater. Res. Bull.19 (1984) 701.

170.G.C. Bond and M.A. Duarte, J. Catal. 111 (1988) 189.

171.S.H. Inami, B.J. Wood and H. Wise, J. Catal. 13 (1969) 397.

172.R.S. Yolles, B.J. Wood and H. Wise, J. Catal. 21 (1971) 66.

173.M. Boutonnet, J. Kizling, V. Mintsa-Eya, A. Choplin, R. Touroude, G. Maire and P. Stenius, J. Catal. 103 (1987) 95.

174.M. Boutonnet, J. Kizling, R. Touroude, G. Maire and P. Stenius, Appl. Catal. 20 (1986) 163.

175.Cheonho Yoon, M.X. Yang and G.A. Somorjai, J. Catal. 176 (1998) 35.

176.V. Mintsa-Eya, L. Hilaire, A. Choplin, R. Touroude and F.G. Gault, J. Catal. 82 (1983) 267.

177.V. Mintsa-Eya, L. Hilaire, R. Touroude, F.G. Gault, B. Moraweck and A. Renouprez, J. Catal.

76(1982) 169.

178.T.I. Taylor and V.H. Dibeler, J. Phys. Chem. 55 (1951) 1036.

179.K.J. Klabunde and Y. Tanaka, J. Molec. Catal. 21 (1983) 67.

180.J. Goetz, M.A. Volpe and R. Touroude, J. Catal. 164 (1996) 369.

181.G.C. Bond and J.M. Winterbottom, Trans. Faraday Soc. 65 (1969) 2779.

182.J.P. Boitiaux, J. Cosyns and S. Vasudevan, Appl. Catal. 6 (1983) 41; 15 (1985) 317.

183.J.P. Boitiaux, J. Cosyns and E. Robert, Appl. Catal. 35 (1987) 193; 32 (1987) 145.

184.S. Hub, L. Hilaire and R. Touroude, Appl. Catal. 36 (1988) 307.

185.K.S. Sim, L. Hilaire, F. Le Normand, R. Touroude, V. Paul-Boncour and A. Percheron-Guegan,

J. Chem. Soc. Faraday Trans. 87 (1991) 1453.

186.J. I. McNab and G. Webb, J. Catal. 10 (1965) 19.

187.E. Rodrignez, M. Leconte and J.M. Basset, J. Catal. 131 (1991) 457.

188.J. Toyir, M. Leconte, G.P. Niccolai and J.M. Basset, J. Catal. 152 (1995) 306.

189.R.L. Augustine, Heterogeneous Catalysis for the Synthetic Chemist, Dekker: New York (1996), Chs. 3 and 4.

190.R.L. Augustine, D.R. Baun, K.G. High, L.S. Szivos and S.T. O’Leary, J. Catal. 127 (1991) 675; R.L. Augustine, Catal. Today 12 (1992) 139.

191.R.L. Augustine and R.W. Warner, J. Catal. 80 (1983) 358.

192.R.L. Augustine and M.E. Lenczyk, J. Catal. 97 (1986) 269.

193.S. Siegel and M. Dunkel, Adv. Catal. 9 (1957) 15.

194.S. Siegel, J. Outlaw Jr. and N. Garti, J. Catal. 52 (1978) 102.

195.A.F. Carley, H.A. Edwards, B. Mile, M.W. Roberts, C.C. Rowlands, F.E. Hancock and S.D. Jackson, J. Chem. Soc. Faraday Trans. 90 (1994) 3341.

196.S. Tsuchiya and N. Yoshioka, J. Catal. 87 (1984) 144.

197.R.D. Cortright, E. Bergene, P. Levin, M. Natal-Santiago, in: Proc. 11t h Internat. Congr. Catal. (J.W. Hightower, W.N. Delgass, E. Iglesia and A.T. Bell, eds.), Elsevier: Amsterdam B (1996) 1185.

198.P.S. Cremer, Xingcai Su, Y.R. Chen and G. Somorjai, J. Chem. Soc. Faraday Trans. 92 (1996) 4717.

199.R. Brown, C. Kemball and I.H. Sadler, Proc. Roy. Soc. A 424 (1989) 39.

354

CHAPTER 7

200.R.D. Cortright, E. Bergene, P. Levin, M. Natal-Santiago and J.A. Dumesic, Proc. 11t h . Internat. Cong. Catal. (J.W. Hightower, W.N. Delgass, E. Iglesia and A.T. Bell, eds.), Elsevier: Amsterdam B (1996) 1185.

201.V. Mintsa-Eya, R. Touroude and F.G. Gault, J. Catal. 66 (1980) 412.

202.R.L. Arnett and B.L. Crawford Jr., J. Phys. Chem. 18 (1950) 118.

203.T.M. Gentle and E. L. Muetterties, J. Phys. Chem. 87 (1983) 2469.

204.P.B. Wells and G.R. Wilson, Discuss. Faraday Soc. 41 (1966) 237.

205.P.N. Rylander, Catalytic Hydrogenation over Platinum Metals, Academic Press: New York (1967).

206.M. Bartok, Sterochemistry of Heterogeneous Metal Catalysis, Wiley: New York (1983).

207.M. Kraus, in Handbook 3p.1051.

208.G.C. Bond and J.S. Rank, Proc. 3r d . Internat. Congr. Catalysis, II (1964) 1.

209.O.M. Poltorak and V.S. Boronin, Russ. J. Phys. Chem. 39 (1965) 781, 1329; 40 (1966) 1436.

210.Z. Pa´al, M. R¨ath, B. Brose and W. Gombler, React. Kinet. Catal. Lett. 47 (1992) 43.

211.G.V. Smith and R.L. Burwell Jr., J. Am. Chem. Soc. 84 (1962) 925.

212.R.L. Burwell Jr. and R.H. Tuxworth, J. Phys. Chem. 60 (1956) 1043.

213.L. Horner, Ann. New York Acad. Sci. 158 (1969) 456.

214.J.J. Phillipson and R.L. Burwell Jr., J. Am. Chem. Soc. 92 (1970) 6125.

215.A.W. Weitkamp, Preprints ACS Mtg. New York 1967, 11 (4), paper A.13; J. Catal. 6 (1966) 431.

216.E. Selke et al., Preprints ACS Meeting, Divn. Petroleum Chem., 11 (4) (1966) A63.

217.S. Siegel, Adv. Catal. 16 (1966) 123.

218.G.C. Bond and D.T. Thompson, Catal. Rev.- Sci. Eng. 41 (1999) 319.

219.L.G. Tejuca and J. Turkevich, J. Chem. Soc. Faraday Trans. I 74 (1978) 1064.

220.X.-C. Su, K.Y. Kung, J. Lahtinen, Y.R. Shen and G.A. Somorjai, J. Molec. Catal. A: Chem. 141 (1999) 9.

221.S.M. Davis and G.A. Somorjai, J. Catal. 65 (1980) 78.

222.M.A. Aramend´ıa, V. Bor´au, I.M. Garc´ıa, C. Jim´enez, A. Marinas, J.M. Marinas, and F.J. Urbano,

J. Molec Catal. A: Chem. 151 (2000) 261.

223.A. Farkas and L. Farkas, Trans. Faraday Soc. 35 (1939) 917.

224.M.S.W. Vong and P.A. Sermon in: Catalyst Deactivation 1991(C.H. Bartholomew and J.B. Butt, eds.), Studies in Surface Science and Catalysis Elsevier: Amsterdam 68 (1991) 235.

225.D.E. Gardin, Xingcai Su, P.S. Cremer and G.A. Somorjai, J. Catal 158 (1996) 193.

226.M. Boudart and W.C. Cheng, J. Catal. 106 (1987) 134.

227.A. F´asi, I. P´alinko,´ T. Katona and M. Bartok,´ J. Catal. 167 (1997) 215.

228.E.E. Gonzo and M. Boudart, J. Catal. 52 (1978) 462.

229.M. Boudart and D.J. Sajkowski, Faraday Soc. Gen. Discuss. 92 (1991) 57.

230.G.V. Smith, O. Zahraa, A. Moln´ar, M.M. Khan, B. Rihter and W.E. Brower, J. Catal. 83 (1983) 238.

231.G.V. Smith and M.C. Menon, Ann. New York Acad. Sci. 158 (1969) 501.

232.I. Jardine and F.H. McQuillin. J. Chem. Soc. (C) (1966) 458.

233.L. Hilaire and F.G. Gault, J. Catal. 20 (1971) 267.

234.R.L. Burwell Jr., Chem. Rev. 57 (1957) 895.

235.G.V. Smith, J. Catal. 181 (1999) 302.

236.R.L. Augustine and P. Techasauvapak, J. Molec. Catal. 87 (1994) 95.

237.S. Siegel and G.V. Smith, J. Am. Chem. Soc. 82 (1960) 6082, 6087.

238.J. T. Kiss, I. P´alinko´ and A. Moln´ar, J. Molec. Struct. 293 (1993) 373.

239.R.L. Augustine, F. Yaghmail and J.F. Van Peppen, J. Org. Chem. 49 (1984) 1865.

240.H.H. Kung, R.J. Pellet and R.L. Burwell Jr., J. Am. Chem. Soc. 98 (1976) 5603.

241.R.L. Augustine and J. van Peppen, Ann. New York Acad. Sci. 158 (1969) 482.

242.G.V. Smith in: Catalysis of Organic Reactions (R.E. Malz Jr., ed.), Dekker: New York (1996), p. 1.

HYDROGENATION OF ALKENES AND RELATED PROCESSES

355

243.F. Notheisz, M. Bartok,´ D. Ostgard and G.V. Smith, J. Catal. 101 (1986) 212; G.V. Smith, F. Notheisz, A.G. Zsigmond and M. Bartok, Proc. 10t h . Internat. Congr. Catal. (L. Guczi, F.

Solymosi and P. T´et´enyi, eds.), Akad´emiai Kiado:´ Budapest C (1992) 2463.

244.G.V. Smith, Y. Wang, R. Song and M. Jackson, Catal. Today 44 (1998) 119.

245.A. Couper and D.D. Eley, Discuss. Faraday Soc. 8 (1950) 172.

246.R.L. Augustine and H.P. Bentelman, J. Catal. 97 (1986) 59.

247.G.V. Smith and J.R. Swoap, J. Org. Chem. 31 (1966) 3094.

248.G.C. Bond, Chem. Soc. Rev. 20 (1991) 441.

249.Physical Properties of Hydrocarbons (R.W. Gallant and C.L. Yaws, eds.), 2nd edn. Gulf. Co.: Houston (1992).

250.G.H. Aylward and T.J.V. Findlay, S I Chemical Data, 2nd edn., Wiley: Milton, Queensland (1991).

251.J.H.. Sinfelt, J. Phys. Chem. 68 (1964) 856.

252.S. Siegel and M. Dunkel, Adv. Catal. 9 (1957) 15.

253.J-F. Sauvage, R.H. Baker and A.S. Hussey, J. Am. Chem. Soc. 82 (1960) 6090.

254.S. Siegel and B. Dmuchousky, J. Am. Chem. Soc. 84 (1962) 3132.