The Halcon Sd Group, Inc.

Halcon Research and Development Corp.

Atlantic Richfield Company

Halcon International, Inc.

Arco Chemical Company

Sargis Khoobiar

Arnold J Shapiro

Isobutane is dehydrogenated to isobutylene with minimal, preferably no more than 15%, loss of the fresh feed isobutane by structural isomerization or cracking, even when the dehydrogenation feed contains substantial amounts of isobutylene. The catalysts employed comprise platinum and promoting amounts of at least one of indium, neodymium, and tin on a nonacidic support, such as zinc aluminate. The reaction is carried out at a pressure of 0.14 to 2 bar, and an outlet temperature, .sup.o K, minimum residence time, sec., defined by the equation

Dehydrogenation of isobutane

Unsaturated nitriles, particularly acrylonitrile or methacrylonitrile, are produced in a process which integrates dehydrogenation of an alkane, particularly propane or isobutane, to the corresponding olefin, followed by ammoxidation of the olefin in the dehydrogenation reactor effluent to the corresponding nitrile. After recovery of the nitrile product, the residual gases are processed to remove hydrogen, oxygen, and carbon oxides, after which the gases are recycled to the dehydrogenation reactor. By operating with relatively low conversion of olefin to nitrile in each pass, the overall efficiency of the process is improved despite the need to recirculate substantial amounts of unreacted hydrocarbons.

Process for preparing unsaturated nitriles from alkanes

Unsaturated nitriles, particularly acrylonitrile, are produced in a process which integrates dehydrogenation of an alkane, particularly propane, to the corresponding olefin, followed by ammoxidation of the olefin in the dehydrogenation reactor effluent to the corresponding nitrile. After recovery of the nitrile product, the residual gases are processed to remove hydrogen, oxygen, and carbon oxides, after which the gases are recycled to the dehydrogenation reactor. By operating with relatively low conversion of olefin to nitrile in each pass, the overall efficiency of the process is improved despite the need to recirculate substantial amounts of unreacted hydrocarbons.

A catalyst composition useful for the oxidation of unsaturated aldehydes, particularly the oxidation of methacrolein to produce methacrylic acid, comprises the combination of oxides of molybdenum, copper, phosphorus, antimony, and cesium and/or calcium and optionally may include one or more of the elements Ni, Zn, Ru, Rh, Pd, Pt, As, K, Rb, Sr, Ba, Cr, V, Nb, W, Mn, Re, and rare earth metals including La.

Process for producing methacrylic acid

Isobutane in a C.sub.4 hydrocarbon feed stream is converted to methacrolein in an integrated two-step process. Isobutane is dehydrogenated in a first step to isobutylene, hydrogen, and by-products and the reaction effluent is passed directly into a second step where isobutylene is oxidized to methacrolein without significant oxidation of the hydrogen and by-products. Any normal butenes present are converted to butadiene. The methacrolein and by-products may be separated and the unreacted isobutylene and isobutane recycled to the first step. Alternatively, the effluent from the second step may be used as feed to a further oxidation step for conversion of methacrolein to methacrylic acid.

Conversion of isobutane to methacrolein

Alkanes, particularly propane and isobutane are converted to unsaturated aldehydes, particularly acrolein and methacrolein in an integrated two-step process wherein the alkane is dehydrogenated in a first step to the corresponding olefin, hydrogen, and by-products and the reaction effluent is passed directly into a second step where the olefin is oxidized to the corresponding unsaturated aldehyde without significant oxidation of the hydrogen and by-products. The aldehydes and by-products may be separated and the unreacted olefin and alkane recycled to the first step. Alternatively, the effluent from the second step may be used as feed to a further oxidation step for conversion of the unsaturated aldehyde to the corresponding unsaturated acid.

Conversion of alkanes to unsaturated aldehydes

A catalyst composition useful for the oxidation of unsaturated aldehydes, particularly the oxidation of methacrolein to produce methacrylic acid, comprises the combination of oxides of molybdenum, copper, phosphorus, antimony, cesium and rhenium in predetermined relative atomic ratios.

A catalyst composition useful for the oxidation of olefins, particularly the vapor phase oxidation of isobutylene and/or tertiary butyl alcohol to produce methacrolein, consists essentially of the combination of oxides of molybdenum, cobalt, iron, bismuth, thallium, antimony, silicon, and nickel, along with one or more members of the groups consisting of the alkali metals, the alkaline earth metals, the rare earth metals including lanthanum, tungsten, and mixtures thereof. The catalyst has a BET surface area within the range of about 0.5-10 m.sup.2 /gm and preferably within the range of about 2-6 m.sup.2 /gm. Preferably, the catalyst has no more than about 3% of the surface area associated with pores smaller than about 100 .ANG.. The catalyst is heated during its preparation to a temperature above 525.degree. C., preferably above 550.degree. C., most preferably to about 600.degree. C., for a time sufficient to achieve the desired surface area and pore size distribution and thereby to improve selectivity to methacrolein.

Catalyst and process for unsaturated aldehydes

A catalyst composition useful for the oxidation of unsaturated aldehydes, particularly the oxidation of methacrolein to produce methacrylic acid, comprises the combination of oxides of molybdenum, copper, phosphorus, antimony, and cesium in predetermined relative atomic ratios.

Isobutane is converted to methacrolein in an integrated two-step process wherein isobutane is dehydrogenated in a first step to isobutylene, hydrogen, and by-products and the reaction effluent is passed directly into a second step where isobutylene is oxidized to methacrolein without significant oxidation of the hydrogen and by-products. The methacrolein and by-products may be separated and the unreacted isobutylene and isobutane recycled to the first step. Alternatively, the effluent from the second step may be used as feed to a further oxidation step for conversion of methacrolein to methacrylic acid. In one embodiment, the hydrogen produced in the first step is oxidized using the excess oxygen from the second step under conditions selected to avoid loss of the C.sub.4 components. In an alternative embodiment, the unreacted isobutane and isobutylene are absorbed and separated from the remaining components before being recycled to the first step.

Catalyst and process for producing methacrylic acid

A catalyst composition useful for the oxidation of olefins, particularly the vapor phase oxidation of isobutylene and/or tertiary butyl alcohol to produce methacrolein, consists essentially of the combination of oxides of molybdenum, cobalt, iron, bismuth, thallium, antimony, silicon, and nickel, along with one or more members of the groups consisting of the alkali metals, the alkaline earth metals, the rare earth metals including lanthanum, tungsten, and mixtures thereof. The catalyst has a BET surface area within the range of about 0.5-10 m.sup.2 /gm and preferably within the range of about 2-6 m.sup.2 /gm. Preferably, the catalyst has no more than about 3% of the surface area associated with pores smaller than about 100 A.degree.. The catalyst is heated during its preparation to a temperature above 525.degree. C., preferably above 550.degree. C., most preferably to about 600.degree. C., for a time sufficient to achieve the desired surface area and pore size distribution and thereby to improve selectivity to methacrolein.

Catalysts and process for unsaturated aldehydes

A catalyst composition useful for the oxidation of unsaturated aldehydes, particularly the oxidation of methacrolein to produce methacrylic acid, comprises the combination of oxides of molybdenum, copper, phosphorus, antimony, and calcium in predetermined relative atomic ratios.

A catalyst composition useful for the oxidation of unsaturated aldehydes, particularly the oxidation of methacrolein to produce methacrylic acid, comprises the combination of oxides of molybdenum, copper, phosphorus, antimony, calcium, tungsten and optionally arsenic in predetermined relative atomic ratios.

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Kinnelon, NJ, United States of America

Sargis Khoobiar