The Production of Propene Oxide: Catalytic Processes and Recent Developments

Propene oxide, which is one of the major commodity chemicals used in chemical industry, desperately requires a new process for its production, because of the disadvantages that are encountered with the currently available processes. This paper discusses the existing processes used for the production of propene oxidethe chlorohydrin and hydroperoxide processesand their advantages and disadvantages. Furthermore, the new processes and catalysts under development for the propene oxide production are discussed, as well as the challenges that are still limiting the applications of some of those prospects. The most important new developments for the production of propene oxide discussed in this paper are:  the hydrogen peroxide combination process, the ethene oxide alike silver catalysts, the molten salt systems, and the gold−titania catalyst systems.

[1]  Гетц-Петер Шиндлер,et al.  Process for producing a propylene oxide , 2006 .

[2]  B. Weckhuysen,et al.  The role of water in the epoxidation over gold-titania catalysts. , 2005, Chemical communications.

[3]  Tracy Q. Gardner,et al.  Modeling of kinetics and deactivation in the direct epoxidation of propene over gold–titania catalysts , 2005 .

[4]  Alex Tullo,et al.  BASF, Dow Plan More Propylene Oxide Units , 2005 .

[5]  G. Hutchings,et al.  Tunable gold catalysts for selective hydrocarbon oxidation under mild conditions , 2005, Nature.

[6]  V. Parmon,et al.  Nitrous Oxide in Oxidation Chemistry and Catalysis: Application and Production , 2005 .

[7]  B. Weckhuysen,et al.  Mechanistic study into the direct epoxidation of propene over gold/titania catalysts. , 2005, The journal of physical chemistry. B.

[8]  T. Ishihara,et al.  Synthesis of hydrogen peroxide by direct oxidation of H2 with O2 on Au/SiO2 catalyst , 2005 .

[9]  Richard M. Lambert,et al.  Heterogeneous Alkene Epoxidation: Past, Present and Future , 2005 .

[10]  David G. Barton,et al.  Kinetic study of a direct water synthesis over silica-supported gold nanoparticles. , 2005, The journal of physical chemistry. B.

[11]  B. Weckhuysen,et al.  The role of gold in gold-titania epoxidation catalysts. , 2005, Angewandte Chemie.

[12]  J. Lange Economics of Alkane Conversion , 2005 .

[13]  A. Reitzmann,et al.  Direct gas-phase epoxidation of propene with nitrous oxide over modified silica supported FeOx catalysts , 2004 .

[14]  Xiaoxing Wang,et al.  Iron-Catalyzed Propylene Epoxidation by Nitrous Oxide: Dramatic Shift of Allylic Oxidaton to Epoxidation by the Modification with Alkali Metal Salts. , 2004 .

[15]  Charles T. Campbell,et al.  The Active Site in Nanoparticle Gold Catalysis , 2004, Science.

[16]  M. S. Chen,et al.  The Structure of Catalytically Active Gold on Titania , 2004, Science.

[17]  Alex Tullo,et al.  DOW, BASF TO BUILD PROPYLENE OXIDE , 2004 .

[18]  M. Crocker,et al.  Propylene epoxidation over titanium-on-silica catalyst—the heart of the SMPO process , 2004 .

[19]  Xinwen Guo,et al.  Gas-phase epoxidation of propylene over Ag/Ti-containing catalysts , 2004 .

[20]  J. Moulijn,et al.  Increasing the low propene epoxidation product yield of gold/titania-based catalysts , 2004 .

[21]  R. P. Andres,et al.  Reactivity and stability of Au in and on TS-1 for epoxidation of propylene with H2 and O2 , 2004 .

[22]  M. Gordon,et al.  Binding of propene on small gold clusters and on Au(111): simple rules for binding sites and relative binding energies. , 2004, The Journal of chemical physics.

[23]  B. Gates,et al.  Activation of Au/γ-Al2O3 Catalysts for CO Oxidation: Characterization by X-ray Absorption Near Edge Structure and Temperature Programmed Reduction , 2004 .

[24]  W. Delgass,et al.  Formation of hydrogen peroxide from H2 and O2 over a neutral gold trimer: a DFT study , 2004 .

[25]  R. Behm,et al.  Kinetics, mechanism, and the influence of H2 on the CO oxidation reaction on a Au/TiO2 catalyst , 2004 .

[26]  Xiaoxing Wang,et al.  Iron-catalysed propylene epoxidation by nitrous oxide: dramatic shift of allylic oxidation to epoxidation by the modification with alkali metal salts. , 2004, Chemical communications.

[27]  T. Akita,et al.  Vapor-phase epoxidation of propylene using H2/O2 mixture over gold catalysts supported on non-porous and mesoporous titania-silica: effect of preparation conditions and pretreatments prior to reaction , 2004 .

[28]  C. Louis,et al.  Crotonaldehyde hydrogenation by gold supported on TiO2: structure sensitivity and mechanism , 2004 .

[29]  M. Haruta,et al.  Vital role of moisture in the catalytic activity of supported gold nanoparticles. , 2004, Angewandte Chemie.

[30]  Núria López,et al.  On the origin of the catalytic activity of gold nanoparticles for low-temperature CO oxidation , 2004 .

[31]  M. Haruta,et al.  A three-dimensional mesoporous titanosilicate support for gold nanoparticles: vapor-phase epoxidation of propene with high conversion. , 2004, Angewandte Chemie.

[32]  フアン・ブロエクホーフエン,ヨハンネス・アドリアヌス・マリア,et al.  Process for the preparation of styrene , 2004 .

[33]  B. Gates,et al.  Catalysis by supported gold: correlation between catalytic activity for CO oxidation and oxidation states of gold. , 2004, Journal of the American Chemical Society.

[34]  R. Mitrić,et al.  Reactivity of atomic gold anions toward oxygen and the oxidation of CO: experiment and theory. , 2004, Journal of the American Chemical Society.

[35]  D. Meier,et al.  The influence of metal cluster size on adsorption energies: CO adsorbed on Au clusters supported on TiO2. , 2004, Journal of the American Chemical Society.

[36]  Juergen Eckert,et al.  The nature of the surface species formed on Au/TiO2 during the reaction of H2 and O2: an inelastic neutron scattering study. , 2004, Journal of the American Chemical Society.

[37]  F. Morfin,et al.  Oxidation of CO on gold supported catalysts prepared by laser vaporization: direct evidence of support contribution. , 2004, Journal of the American Chemical Society.

[38]  M. Bononi,et al.  Ethylene oxide. , 2004, Report on carcinogens : carcinogen profiles.

[39]  K. Burgess,et al.  Metal-catalyzed epoxidations of alkenes with hydrogen peroxide. , 2003, Chemical reviews.

[40]  T. Akita,et al.  Vapor phase propylene epoxidation over Au/Ti-MCM-41 catalysts prepared by different Ti incorporation modes , 2003 .

[41]  G. Hutchings,et al.  Direct formation of hydrogen peroxide from H2/O2 using a gold catalyst. , 2002, Chemical communications.

[42]  Richard M. Lambert,et al.  Propene Epoxidation over K-Promoted Ag/CaCO3 Catalysts: The Effect of Metal Particle Size , 2002 .

[43]  A. Zwijnenburg Propene epoxidation over gold/titania and silver catalysts , 2002 .

[44]  Masatake Haruta,et al.  Advances in the catalysis of Au nanoparticles , 2001 .

[45]  Jean-Paul Lange,et al.  Fuels and Chemicals Manufacturing; Guidelines for Understanding and Minimizing the Production Costs , 2001 .

[46]  J. Moulijn,et al.  Stability and Selectivity of Au/TiO2 and Au/TiO2/SiO2 Catalysts in Propene Epoxidation: An in Situ FT-IR Study , 2001 .

[47]  J. Lange,et al.  Mass transport limitations in zeolite catalysts: the dehydration of 1-phenyl-ethanol to styrene , 2001 .

[48]  A. Baiker,et al.  Continuous epoxidation of propylene with oxygen and hydrogen on a Pd–Pt/TS-1 catalyst , 2001 .

[49]  G. Paparatto,et al.  Process for producing olefin oxides , 2000 .

[50]  R. P. Andres,et al.  Characterization of Gold–Titania Catalysts via Oxidation of Propylene to Propylene Oxide , 2000 .

[51]  J. Moulijn,et al.  The direct epoxidation of propene by molten salts , 2000 .

[52]  M. Haruta,et al.  Effect of physical mixing of CsCl with Au/Ti-MCM-41 on the gas-phase epoxidation of propene using H2 and O2:: Drastic depression of H2 consumption , 2000 .

[53]  J. Moulijn,et al.  Direct Epoxidation of Propene Using Gold Dispersed on TS-1 and Other Titanium-Containing Supports , 1999 .

[54]  Toshio Hayashi,et al.  Selective Vapor-Phase Epoxidation of Propylene over Au/TiO2Catalysts in the Presence of Oxygen and Hydrogen , 1998 .

[55]  하워드 제이. 클라크,et al.  Process for the direct oxidation of olefins to olefin oxides , 1997 .

[56]  アンドゥルー カーン,et al.  Gas-phase oxidation of propylene to propylene oxide , 1997 .

[57]  J. Monnier The selective epoxidation of non-allylic olefins over supported silver catalysts , 1997 .

[58]  Moray S. Stark,et al.  Oxidation of propene in the gas phase , 1995 .

[59]  G. Wells Propylene oxide. , 2018, IARC monographs on the evaluation of carcinogenic risks to humans.

[60]  H. Sellers,et al.  Hydrogen peroxide synthesis over metallic catalysts , 1994 .

[61]  Jeffrey T. Roberts,et al.  The Rate-Limiting Step for Olefin Combustion on Silver: Experiment Compared to Theory , 1993 .

[62]  M. Clerici,et al.  Epoxidation of Lower Olefins with Hydrogen Peroxide and Titanium Silicalite , 1993 .

[63]  P. Dagaut,et al.  A Kinetic Modeling Study of Propene Oxidation in JSR and Flame , 1992 .

[64]  V. Romannikov,et al.  Oxidation of benzene to phenol by nitrous oxide over Fe-ZSM-5 zeolites , 1992 .

[65]  G. Bellussi,et al.  Synthesis of propylene oxide from propylene and hydrogen peroxide catalyzed by titanium silicalite , 1991 .

[66]  N. W. Cant,et al.  Ethylene oxidation over silver catalysts: A study of mechanism using nitrous oxide and isotopically labeled oxygen , 1990 .

[67]  J. Haber,et al.  Metal-dependent reactivity of some metalloporphyrins in oxidation with dioxygen , 1989 .

[68]  Nicholas P. Cernansky,et al.  Propene oxidation at low and intermediate temperatures: A detailed chemical kinetic study☆ , 1989 .

[69]  K. A. Joergensen Transition-metal-catalyzed epoxidations , 1989 .

[70]  Masatake Haruta,et al.  Gold catalysts prepared by coprecipitation for low-temperature oxidation of hydrogen and of carbon monoxide , 1989 .

[71]  W. Goddard,et al.  The surface atomic oxyradical mechanism for Ag-catalyzed olefin epoxidation☆ , 1988 .

[72]  R. Vansanten The mechanism of ethylene epoxidation , 1986 .

[73]  J. Ross Ullman's encyclopedia of industrial chemistry , 1986 .

[74]  M. Rálek,et al.  Direct liquid phase oxidation of propene to propene oxide , 1983 .

[75]  P. V. Geenen,et al.  A study of the vapor-phase epoxidation of propylene and ethylene on silver and silver-gold alloy catalysts , 1982 .

[76]  V. Santen,et al.  The mechanism of ethylene epoxidation , 1986 .

[77]  R. Sheldon Chapter 3 – Metal Catalysis in Peroxide Reactions , 1981 .

[78]  R. Sheldon Synthetic and mechanistic aspects of metal-catalysed epoxidations with hydroperoxides , 1980 .

[79]  K. Takamatsu,et al.  Study of the partial oxidation of propene by O2 and N2O over fixed Mo catalysts. Essential factors for catalysis and reaction mechanisms , 1980 .

[80]  John J. McKetta,et al.  Encyclopedia of Chemical Processing and Design , 1976 .