US20060100469A1 - Process for converting gaseous alkanes to olefins and liquid hydrocarbons - Google Patents
Process for converting gaseous alkanes to olefins and liquid hydrocarbons Download PDFInfo
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- US20060100469A1 US20060100469A1 US11/254,438 US25443805A US2006100469A1 US 20060100469 A1 US20060100469 A1 US 20060100469A1 US 25443805 A US25443805 A US 25443805A US 2006100469 A1 US2006100469 A1 US 2006100469A1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2/00—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
- C10G29/00—Refining of hydrocarbon oils, in the absence of hydrogen, with other chemicals
- C10G29/02—Non-metals
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- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
- C01B7/00—Halogens; Halogen acids
- C01B7/09—Bromine; Hydrogen bromide
- C01B7/093—Hydrogen bromide
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- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
- C01B7/00—Halogens; Halogen acids
- C01B7/09—Bromine; Hydrogen bromide
- C01B7/096—Bromine
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- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
- C01B9/00—General methods of preparing halides
- C01B9/04—Bromides
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B61/00—Other general methods
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C1/00—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon
- C07C1/26—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from organic compounds containing only halogen atoms as hetero-atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
- C07C17/10—Preparation of halogenated hydrocarbons by replacement by halogens of hydrogen atoms
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
- C10G50/00—Production of liquid hydrocarbon mixtures from lower carbon number hydrocarbons, e.g. by oligomerisation
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
- C10L3/00—Gaseous fuels; Natural gas; Synthetic natural gas obtained by processes not covered by subclass C10G, C10K; Liquefied petroleum gas
- C10L3/06—Natural gas; Synthetic natural gas obtained by processes not covered by C10G, C10K3/02 or C10K3/04
- C10L3/10—Working-up natural gas or synthetic natural gas
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
- C10L3/00—Gaseous fuels; Natural gas; Synthetic natural gas obtained by processes not covered by subclass C10G, C10K; Liquefied petroleum gas
- C10L3/06—Natural gas; Synthetic natural gas obtained by processes not covered by C10G, C10K3/02 or C10K3/04
- C10L3/10—Working-up natural gas or synthetic natural gas
- C10L3/101—Removal of contaminants
- C10L3/102—Removal of contaminants of acid contaminants
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2529/00—Catalysts comprising molecular sieves
- C07C2529/04—Catalysts comprising molecular sieves having base-exchange properties, e.g. crystalline zeolites, pillared clays
- C07C2529/06—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof
- C07C2529/08—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of the faujasite type, e.g. type X or Y
Definitions
- the present invention relates to a process for converting lower molecular weight, gaseous alkanes to olefins that are useful as monomers and intermediaries in the production of chemicals, such as lubricant and fuel additives, and higher molecular weight hydrocarbons, and more particularly, to a process wherein a gas containing lower molecular weight alkanes is reacted with a dry bromine vapor to form alkyl bromides and hydrobromic acid which in turn are reacted over a crystalline alumino-silicate catalyst to form olefins and higher molecular weight hydrocarbons.
- Natural gas which is primarily composed of methane and other light alkanes has been discovered in large quantities throughout the world. Many of the locales in which natural gas has been discovered are far from populated regions which have significant gas pipeline infrastructure or market demand for natural gas. Due to the low density of natural gas, transportation thereof in gaseous form by pipeline or as compressed gas in vessels is expensive. Accordingly, practical and economic limits exist to the distance over which natural gas may be transported in gaseous form exist. Cryogenic liquefaction of natural gas (LNG) is often used to more economically transport natural gas over large distances. However, this LNG process is expensive and there are limited regasification facilities in only a few countries that are equipped to import LNG.
- LNG ryogenic liquefaction of natural gas
- Methanol is made commercially via conversion of methane to synthesis gas (CO and H 2 ) at high temperatures (approximately 1000° C.) followed by synthesis at high pressures (approximately 100 atmospheres).
- synthesis gas CO and H 2
- SMR steam-methane reforming
- POX partial oxidation
- ATR autothermal reforming
- GHR gas-heated reforming
- SMR and GHR operate at high pressures and temperatures, generally in excess of 600° C., and require expensive furnaces or reactors containing special heat and corrosion-resistant alloy tubes filled with expensive reforming catalyst.
- POX and ATR processes operate at high pressures and even higher temperatures, generally in excess of 1000° C.
- complex and costly refractory-lined reactors and high-pressure waste-heat boilers to quench & cool the synthesis gas effluent are required.
- significant capital cost and large amounts of power are required for compression of oxygen or air to these high-pressure processes.
- synthesis gas technology is expensive, resulting in a high cost methanol product which limits higher-value uses thereof, such as for chemical feedstocks and solvents.
- production of synthesis gas is thermodynamically and chemically inefficient, producing large excesses of waste heat and unwanted carbon dioxide, which tends to lower the conversion efficiency of the overall process.
- Fischer-Tropsch Gas-to-Liquids (GTL) technology can also be used to convert synthesis gas to heavier liquid hydrocarbons, however investment cost for this process is even higher. In each case, the production of synthesis gas represents a large fraction of the capital costs for these methane conversion processes.
- halogenation of methane using chlorine as the preferred halogen results in poor selectivity to the monomethyl halide (CH 3 Cl), resulting in unwanted by-products such as CH 2 Cl 2 and CHCl 3 which are difficult to convert or require severe limitation of conversion per pass and hence very high recycle rates.
- substituted alkanes in particular methanol
- olefins and gasoline boiling-range hydrocarbons over various forms of crystalline alumino-silicates also known as zeolites.
- MEG Methanol to Gasoline
- ZSM-5 shape selective zeolite catalyst
- Coal or methane gas can thus be converted to methanol using conventional technology and subsequently converted to gasoline.
- the MTG process is not considered economically viable.
- one characterization of the present invention is a process is provided for converting gaseous alkanes to to olefins and liquid hydrocarbons.
- a gaseous feed having lower molecular weight alkanes is reacted with bromine vapor to form alkyl bromides and hydrobromic acid.
- the alkyl bromides and hydrobromic acid are then reacted in the presence of a synthetic crystalline alumino-silicate catalyst and at a temperature sufficient to form olefins and hydrobromic acid vapor.
- a process for converting gaseous lower molecular weight alkanes to olefins which comprises reacting a gaseous feed containing lower molecular weight alkanes with bromine vapor to form alkyl bromides and hydrobromic acid.
- the alkyl bromides and hydrobromic acid are then reacted in the presence of a synthetic crystalline alumino-silicate catalyst to form olefins and hydrobromic acid.
- the process also includes converting the hydrobromic acid to bromine.
- a process for converting gaseous alkanes to olefins.
- a gaseous feed having lower molecular weight alkanes is reacted with bromine vapor to form alkyl bromides and hydrobromic acid.
- the alkyl bromides are reacted with hydrobromic acid in the presence of a synthetic crystalline alumino-silicate catalyst and at a temperature sufficient to form olefins and hydrobromic acid vapor.
- Hydrobromic acid vapor is removed from the olefins by reacting the hydrobromic acid vapor with a metal oxide to form a metal bromide and steam.
- FIG. 1 is a simplified block flow diagram of the process of the present invention
- FIG. 2 is a schematic view of one embodiment of the process of the present invention.
- FIG. 3 is a schematic view of another embodiment of process of the present invention.
- FIG. 4A is schematic view of another embodiment of the process of the present invention.
- FIG. 4B is a schematic view of the embodiment of the process of the present invention illustrated in FIG. 4A depicting an alternative processing scheme which may be employed when oxygen is used in lieu of air in the oxidation stage;
- FIG. 5A is a schematic view of the embodiment of the process of the present invention illustrated in FIG. 4A with the flow through the metal oxide beds being reversed;
- FIG. 5B is a schematic view of the embodiment of the process of the present invention illustrated in FIG. 5A depicting an alternative processing scheme which may be employed when oxygen is used in lieu of air in the oxidation stage;
- FIG. 6A is a schematic view of another embodiment of the process of the present invention.
- FIG. 6B is a schematic view of the embodiment of the process of the present invention illustrated in FIG. 6A depicting an alternative processing scheme which may be employed when oxygen is used in lieu of air in the oxidation stage;
- FIG. 7 is a schematic view of another embodiment of the process of the present invention.
- FIG. 8 is a schematic view of the embodiment of the process of the present invention illustrated in FIG. 7 with the flow through the metal oxide beds being reversed;
- FIG. 9 is a schematic view of another embodiment of the process of the present invention.
- the term “lower molecular weight alkanes” refers to methane, ethane, propane, butane, pentane or mixtures thereof.
- alkyl bromides refers to mono, di, and tri brominated alkanes.
- the feed gas in lines 11 and 111 in the embodiments of the process of the present invention as illustrated in FIGS. 2 and 3 , respectively is preferably natural gas which may be treated to remove sulfur compounds and carbon dioxide. In any event, it is important to note that small amounts of carbon dioxide, e.g. less than about 2 mol %, can be tolerated in the feed gas to the process of the present invention.
- FIG. 1 A block flow diagram generally depicting the process of the present invention is illustrated in FIG. 1 , while specific embodiments of the process of the present invention are illustrated in FIGS. 2 and 3 .
- a gas stream containing lower molecular weight alkanes comprised of a mixture of a feed gas plus a recycled gas stream at a pressure in the range of about 1 bar to about 30 bar, is transported or conveyed via line, pipe or conduit 62 , mixed with dry bromine liquid transported via line 25 and pump 24 , and passed to heat exchanger 26 wherein the liquid bromine is vaporized.
- the mixture of lower molecular weight alkanes and dry bromine vapor is fed to reactor 30 .
- the molar ratio of lower molecular weight alkanes to dry bromine vapor in the mixture introduced into reactor 30 is in excess of 2.5:1.
- Reactor 30 has an inlet pre-heater zone 28 which heats the mixture to a reaction initiation temperature in the range of about 250° C. to about 400° C.
- first reactor 30 the lower molecular weight alkanes are reacted exothermically with dry bromine vapor at a relatively low temperature in the range of about 250° C. to about 600° C., and at a pressure in the range of about 1 bar to about 30 bar to produce gaseous alkyl bromides and hydrobromic acid vapors.
- the upper limit of the operating temperature range is greater than the upper limit of the reaction initiation temperature range to which the feed mixture is heated due to the exothermic nature of the bromination reaction.
- methane the formation of methyl bromide occurs in accordance with the following general reaction: CH 4 (g)+Br 2 (g) ⁇ CH 3 Br (g)+HBr (g)
- This reaction occurs with a significantly high degree of selectivity to methyl bromide.
- a methane to bromine ratio of about 4.5:1 increases the selectivity to the mono-halogenated methyl bromide.
- Small amounts of dibromomethane and tribromomethane are also formed in the bromination reaction.
- Higher alkanes, such as ethane, propane and butane, are also readily brominated resulting in mono and multiple brominated species such as ethyl bromides, propyl bromides and butyl bromides.
- first reactor 30 If an alkane to bromine ratio of significantly less than about 2.5 to 1 is utilized, a lower selectivity to methyl bromide occurs and significant formation of undesirable carbon soot is observed. Further, the dry bromine vapor that is feed into first reactor 30 is substantially water-free. Applicant has discovered that elimination of substantially all water vapor from the bromination step in first reactor 30 substantially eliminates the formation of unwanted carbon dioxide thereby increasing the selectivity of alkane bromination to alkyl bromides and eliminating the large amount of waste heat generated in the formation of carbon dioxide from alkanes.
- the effluent that contains alkyl bromides and hydrobromic acid is withdrawn from the first reactor via line 31 and is partially cooled to a temperature in the range of about 150° C. to about 450° C. in heat exchanger 32 before flowing to a second reactor 34 .
- the alkyl bromides are reacted exothermically at a temperature range of from about 250° C. to about 500° C., and a pressure in the range of about 1 to 20 bar, over a fixed bed 33 of crystalline alumino-silicate catalyst, preferably a zeolite catalyst, and most preferably an X type or Y type zeolite catalyst.
- a preferred zeolite is 10 X or Y type zeolite, although other zeolites with differing pore sizes and acidities, which are synthesized by varying the alumina-to-silica ratio may be used in the process of the present invention as will be evident to a skilled artisan.
- the zeolite catalyst is preferably used in a protonic form, a sodium form or a mixed protonic/sodium form, the zeolite may also be modified by ion exchange with other alkali metal cations, such as Li, K or Cs, with alkali-earth metal cations, such as Mg, Ca, Sr or Ba, or with transition metal cations, such as Ni, Mn, V, W, or to the hydrogen form.
- the temperature at which the second reactor 34 is operated is an important parameter in determining the selectivity of the reaction to olefins and various higher molecular weight hydrocarbons. It is preferred to operated second reactor 34 at a temperature within the range of about 250° to 500° C. Temperatures above about 450° C. in the second reactor result in increased yields of light hydrocarbons, such as undesirable methane and also deposition of coke, whereas lower temperatures increase yields of ethylene, propylene, butylene and heavier molecular weight hydrocarbon products. Also it is noted that methyl bromide appears to be more reactive over a lower temperature range relative to methyl chloride or other substituted methyl compounds such as methanol.
- the catalyst may be periodically regenerated in situ, by isolating reactor 34 from the normal process flow, purging with an inert gas via line 70 at a pressure in a range from about 1 to about 5 bar at an elevated temperature in the range of about 400° C. to about 650° C. to remove unreacted material adsorbed on the catalyst insofar as is practical, and then subsequently oxidizing the deposited carbon to CO 2 by addition of air or inert gas-diluted oxygen to reactor 34 via line 70 at a pressure in the range of about 1 bar to about 5 bar at an elevated temperature in the range of about 400° C. to about 650° C. Carbon dioxide and residual air or inert gas is vented from reactor 34 via line 75 during the regeneration period.
- the effluent which comprises olefins, the higher molecular weight hydrocarbons and hydrobromic acid is withdrawn from the second reactor 34 via line 35 and is cooled to a temperature in the range of 0° C. to about 100° C. in exchanger 36 and combined with vapor effluent in line 12 from hydrocarbon stripper 47 , which contains feed gas and residual hydrocarbons stripped-out by contact with the feed gas in hydrocarbon stripper 47 .
- the combined vapor mixture is passed to a scrubber 38 and contacted with a concentrated aqueous partially-oxidized metal bromide salt solution containing metal hydroxide and/or metal oxide and/or metal oxy-bromide species, which is transported to scrubber 38 via line 41 .
- the preferred metal of the bromide salt is Fe(III), Cu(II) or Zn(II), or mixtures thereof, as these are less expensive and readily oxidize at lower temperatures in the range of about 120° C. to about 180° C., allowing the use of glass-lined or fluorpolymer-lined equipment; although Co(II), Ni(II), Mn(II), V(II), Cr(II) or other transition-metals which form oxidizable bromide salts may be used in the process of the present invention.
- alkaline-earth metals which also form oxidizable bromide salts such as Ca (II) or Mg(II) may be used.
- Any liquid hydrocarbons condensed in scrubber 38 may be skimmed and withdrawn in line 37 and added to liquid hydrocarbons exiting the product recovery unit 52 in line 54 .
- Hydrobromic acid is dissolved in the aqueous solution and neutralized by the metal hydroxide and/or metal oxide and/or metal oxy-bromide species to yield metal bromide salt in solution and water which is removed from the scrubber 38 via line 44 .
- the residual vapor phase containing olefins and the higher molecular weight hydrocarbons that is removed as effluent from the scrubber 38 is forwarded via line 39 to dehydrator 50 to remove substantially all water via line 53 from the vapor stream. The water is then removed from the dehydrator 50 via line 53 .
- the dried vapor stream containing olefins and the higher molecular weight hydrocarbons is further passed via line 51 to product recovery unit 52 to recover olefins and the C 5 + gasoline-range hydrocarbon fraction as a liquid product in line 54 .
- any conventional method of dehydration and liquids recovery such as solid-bed dessicant adsorption followed by refrigerated condensation, cryogenic expansion, or circulating absorption oil or other solvent, as used to process natural gas or refinery gas streams, and to recover olefinic hydrocarbons, as will be evident to a skilled artisan, may be employed in the process of the present invention.
- the residual vapor effluent from product recovery unit 52 is then split into a purge stream 57 which may be utilized as fuel for the process and a recycled residual vapor which is compressed via compressor 58 .
- the recycled residual vapor discharged from compressor 58 is split into two fractions.
- a first fraction that is equal to at least 2.5 times the feed gas molar volume is transported via line 62 and is combined with dry liquid bromine conveyed by pump 24 , heated in exchanger 26 to vaporize the bromine and fed into first reactor 30 .
- the second fraction is drawn off of line 62 via line 63 and is regulated by control valve 60 , at a rate sufficient to dilute the alkyl bromide concentration to reactor 34 and absorb the heat of reaction such that reactor 34 is maintained at the selected operating temperature, preferably in the range of about 300° C. to about 450° C. in order to maximize conversion versus selectivity and to minimize the rate of catalyst deactivation due to the deposition of carbon.
- the dilution provided by the recycled vapor effluent permits selectivity of bromination in the first reactor 30 to be controlled in addition to moderating the temperature in second reactor 34 .
- Water containing metal bromide salt in solution which is removed from scrubber 38 via line 44 is passed to hydrocarbon stripper 47 wherein residual dissolved hydrocarbons are stripped from the aqueous phase by contact with incoming feed gas transported via line 11 .
- the stripped aqueous solution is transported from hydrocarbon stripper 47 via line 65 and is cooled to a temperature in the range of about 0° C. to about 70° C. in heat exchanger 46 and then passed to absorber 48 in which residual bromine is recovered from vent stream in line 67 .
- the aqueous solution effluent from scrubber 48 is transported via line 49 to a heat exchanger 40 to be preheated to a temperature in the range of about 100° C. to about 600° C., and most preferably in the range of about 120° C.
- Oxygen or air is delivered via line 10 by blower or compressor 13 at a pressure in the range of about ambient to about 5 bar to bromine stripper 14 to strip residual bromine from water which is removed from stripper 14 in line 64 and is combined with water stream 53 from dehydrator 50 to form water effluent stream in line 56 which is removed from the process.
- the oxygen or air leaving bromine stripper 14 is fed via line 15 to reactor 16 which operates at a pressure in the range of about ambient to about 5 bar and at a temperature in the range of about 100° C. to about 600° C., but most preferably in the range of about 120° C. to about 180° C.
- the preferred metal of the bromide salt is Fe(III), Cu(II), or Zn(II), or mixtures thereof, as these are less expensive and readily oxidize at lower temperatures in the range of about 120° C. to about 180° C., allowing the use of glass-lined or fluorpolymer-lined equipment.
- alkaline-earth metals which also form oxidizable bromide salts such as Ca (II) or Mg(II) could be used.
- Hydrobromic acid reacts with the metal hydroxide and/or metal oxide and/or metal oxy-bromide species so formed to once again yield the metal bromide salt and water.
- Heat exchanger 18 in reactor 16 supplies heat to vaporize water and bromine.
- the overall reactions result in the net oxidation of hydrobromic acid produced in first reactor 30 and second reactor 34 to elemental bromine and steam in the liquid phase catalyzed by the metal bromide/metal oxide or metal hydroxide operating in a catalytic cycle.
- three-phase separator 22 since liquid water has a limited solubility for bromine, on the order of about 3% by weight, any additional bromine which is condensed forms a separate, denser liquid bromine phase.
- the liquid bromine phase however, has a notably lower solubility for water, on the order of less than 0.1%.
- a substantially dry bromine vapor can be easily obtained by condensing liquid bromine and water, decanting water by simple physical separation and subsequently re-vaporizing liquid bromine.
- Liquid bromine is pumped in line 25 from three-phase separator 22 via pump 24 to a pressure sufficient to mix with vapor stream 62 .
- bromine is recovered and recycled within the process.
- the residual oxygen or nitrogen and any residual bromine vapor which is not condensed exits three-phase separator 22 and is passed via line 23 to bromine scrubber 48 , wherein residual bromine is recovered by solution into and by reaction with reduced metal bromides in the aqueous metal bromide solution stream 65 .
- Water is removed from separator 22 via line 27 and introduced into stripper 14 .
- a gas stream containing lower molecular weight alkanes comprised of mixture of a feed gas plus a recycled gas stream at a pressure in the range of about 1 bar to about 30 bar, is transported or conveyed via line, pipe or conduit 162 , mixed with dry bromine liquid transported via pump 124 and passed to heat exchanger 126 wherein the liquid bromine is vaporized.
- the mixture of lower molecular weight alkanes and dry bromine vapor is fed to reactor 130 .
- the molar ratio of lower molecular weight alkanes to dry bromine vapor in the mixture introduced into reactor 130 is in excess of 2.5:1
- Reactor 130 has an inlet pre-heater zone 128 which heats the mixture to a reaction initiation temperature in the range of about 250° C. to about 400° C.
- the lower molecular weight alkanes are reacted exothermically with dry bromine vapor at a relatively low temperature in the range of about 250° C. to about 600° C., and at a pressure in the range of about 1 bar to about 30 bar to produce gaseous alkyl bromides and hydrobromic acid vapors.
- the upper limit of the operating temperature range is greater than the upper limit of the reaction initiation temperature range to which the feed mixture is heated due to the exothermic nature of the bromination reaction.
- methane the formation of methyl bromide occurs in accordance with the following general reaction: CH 4 (g)+Br 2 (g) ⁇ CH 3 Br (g)+HBr (g)
- This reaction occurs with a significantly high degree of selectivity to methyl bromide.
- a high selectivity to the mono-halogenated methyl bromide occurs.
- Small amounts of dibromomethane and tribromomethane are also formed in the bromination reaction.
- alkanes such as ethane, propane and butane
- ethane propane and butane
- mono and multiple brominated species such as ethyl bromides, propyl bromides and butyl bromides. If an alkane to bromine ratio of significantly less than 2.5 to 1 is utilized, substantially lower selectivity to methyl bromide substantially occurs and significant formation of undesirable carbon soot is observed. Further, the dry bromine vapor that is feed into first reactor 130 is substantially water-free.
- the effluent that contains alkyl bromides and hydrobromic acid is withdrawn from the first reactor 130 via line 131 and is partially cooled to a temperature in the range of about 150° C. to 450° C. in heat exchanger 132 before flowing to a second reactor 134 .
- the alkyl bromides are reacted exothermically at a temperature range of from about 250° C. to about 500° C., and a pressure in the range of about 1 bar to 30 bar, over a fixed bed of crystalline alumino-silicate catalyst, preferably a zeolite catalyst, and most preferably an X type or Y type zeolite catalyst.
- a preferred zeolite is 10 X or Y type zeolite, although other zeolites with differing pore sizes and acidities, which are synthesized by varying the alumina-to-silica ratio may be used in the process of the present invention as will be evident to a skilled artisan.
- the zeolite catalyst is preferably used in a protonic form, a sodium form or a mixed protonic/sodium form, such as Li, K or Cs, with alkali-earth metal cations, such as Mg, Ca, Sr or Ba, or with transition metal cations, such as Ni, Mn, V, W, or to the hydrogen form. These various alternative cations have an effect of shifting reaction selectivity.
- zeolite catalysts having varying pore sizes and acidities, which are synthesized by varying the alumina-to-silica ratio may be used in the second reactor 134 as will be evident to a skilled artisan.
- the alkyl bromides are reacted to produce a mixture of olefins and higher molecular weight hydrocarbons and additional hydrobromic acid vapor.
- the temperature at which the second reactor 134 is operated is an important parameter in determining the selectivity of the reaction to olefins and various higher molecular weight liquid hydrocarbons. It is preferred to operate second reactor 134 at a temperature within the range of about 250° C. to 500° C. , but more preferably within the range of about 300° C. to 450° C. Temperatures above about 450° C. in the second reactor result in increased yields of light hydrocarbons, such as undesirable methane and carbonaceous coke, whereas lower temperatures increase yields of olefins such as ethylene, propylene and butylene and heavier molecular weight hydrocarbon products.
- the catalyst may be periodically regenerated in situ, by isolating reactor 134 from the normal process flow, purging with an inert gas via line 170 at a pressure in the range of about 1 bar to about 5 bar and an elevated temperature in the range of 400° C. to 650° C. to remove unreacted material adsorbed on the catalyst insofar as is practical, and then subsequently oxidizing the deposited carbon to CO 2 by addition of air or inert gas-diluted oxygen via line 170 to reactor 134 at a pressure in the range of about 1 bar to about 5 bar and an elevated temperature in the range of 400° C. to 650° C. Carbon dioxide and residual air or inert gas are vented from reactor 134 via line 175 during the regeneration period.
- the effluent which comprises olefins, the higher molecular weight hydrocarbons and hydrobromic acid is withdrawn from the second reactor 134 via line 135 , cooled to a temperature in the range of about 0° C. to about 100° C. in exchanger 136 , and combined with vapor effluent in line 112 from hydrocarbon stripper 147 .
- the mixture is then passed to a scrubber 138 and contacted with a stripped, recirculated water that is transported to scrubber 138 in line 164 by any suitable means, such as pump 143 , and is cooled to a temperature in the range of about 0° C. to about 50° C. in heat exchanger 155 .
- Any liquid hydrocarbon product condensed in scrubber 138 may be skimmed and withdrawn as stream 137 and added to liquid hydrocarbon product 154 .
- Hydrobromic acid is dissolved in scrubber 138 in the aqueous solution which is removed from the scrubber 138 via line 144 , and passed to hydrocarbon stripper 147 wherein residual hydrocarbons dissolved in the aqueous solution are stripped-out by contact with feed gas 111 .
- the stripped aqueous phase effluent from hydrocarbon stripper 147 is cooled to a temperature in the range of about 0° C. to about 50° C. in heat exchanger 146 and then passed via line 165 to absorber 148 in which residual bromine is recovered from vent stream 167 .
- the residual vapor phase containing olefins and the higher molecular weight hydrocarbon is removed as effluent from the scrubber 138 and forwarded to dehydrator 150 to remove substantially all water from the gas stream.
- the water is then removed from the dehydrator 150 via line 153 .
- the dried gas stream containing olefins and the higher molecular weight hydrocarbons is further passed via line 151 to product recovery unit 152 to recover olefins and the C 5 + gasoline range hydrocarbon fraction as a liquid product in line 154 .
- any conventional method of dehydration and liquids recovery such as solid-bed dessicant adsorption followed by, for example, refrigerated condensation, cryogenic expansion, or circulating absorption oil, or other solvents as used to process natural gas or refinery gas streams and recover olefinic hydrocarbons, as known to a skilled artisan, may be employed in the implementation of this invention.
- the residual vapor effluent from product recovery unit 152 is then split into a purge stream 157 that may be utilized as fuel for the process and a recycled residual vapor which is compressed via compressor 158 .
- the recycled residual vapor discharged from compressor 158 is split into two fractions.
- a first fraction that is equal to at least 2.5 times the feed gas volume is transported via line 162 , combined with the liquid bromine conveyed in line 125 and passed to heat exchanger 126 wherein the liquid bromine is vaporized and fed into first reactor 130 .
- the second fraction which is drawn off line 162 via line 163 and is regulated by control valve 160 , at a rate sufficient to dilute the alkyl bromide concentration to reactor 134 and absorb the heat of reaction such that reactor 134 is maintained at the selected operating temperature, preferably in the range of about 300° C. to about 450° C. in order to maximize conversion vs. selectivity and to minimize the rate of catalyst deactivation due to the deposition of carbon.
- the dilution provided by the recycled vapor effluent permits selectivity of bromination in the first reactor 130 to be controlled in addition to moderating the temperature in second reactor 134 .
- Oxygen, oxygen enriched air or air 110 is delivered via blower or compressor 113 at a pressure in the range of about ambient to about 5 bar to bromine stripper 114 to strip residual bromine from water which leaves stripper 114 via line 164 and is divided into two portions.
- the first portion of the stripped water is recycled via line 164 , cooled in heat exchanger 155 to a temperature in the range of about 20° C. to about 50° C., and maintained at a pressure sufficient to enter scrubber 138 by any suitable means, such as pump 143 .
- the portion of water that is recycled is selected such that the hydrobromic acid solution effluent removed from scrubber 138 via line 144 has a concentration in the range from about 10% to about 50% by weight hydrobromic acid, but more preferably in the range of about 30% to about 48% by weight to minimize the amount of water which must be vaporized in exchanger 141 and preheater 119 and to minimize the vapor pressure of HBr over the resulting acid.
- a second portion of water from stripper 114 is removed from line 164 and the process via line 156 .
- the dissolved hydrobromic acid that is contained in the aqueous solution effluent from scrubber 148 is transported via line 149 and is combined with the oxygen, oxygen enriched air or air leaving bromine stripper 114 in line 115 .
- the combined aqueous solution effluent and oxygen, oxygen enriched air or air is passed to a first side of heat exchanger 141 and through preheater 119 wherein the mixture is preheated to a temperature in the range of about 100° C. to about 600° C. and most preferably in the range of about 120° C. to about 180° C. and passed to third reactor 117 that contains a metal bromide salt or metal oxide.
- the preferred metal of the bromide salt or metal oxide is Fe(III), Cu(II) or Zn(II) although Co(II), Ni(II), Mn(II), V(II), Cr(II) or other transition-metals which form oxidizable bromide salts can be used.
- alkaline-earth metals which also form oxidizable bromide salts, such as Ca (II) or Mg(II) could be used.
- the metal bromide salt in the oxidation reactor 117 can be utilized as a concentrated aqueous solution or preferably, the concentrated aqueous salt solution may be imbibed into a porous, high surface area, acid resistant inert support such as a silica gel.
- the oxide form of the metal in a range of 10 to 20% by weight is deposited on an inert support such as alumina with a specific surface area in the range of 50 to 200 m2/g.
- the oxidation reactor 117 operates at a pressure in the range of about ambient to about 5 bar and at a temperature in the range of about 100° C. to 600° C., but most preferably in the range of about 120° C. to 180° C.; therein, the metal bromide is oxidized by oxygen, yielding elemental bromine and metal hydroxide, metal oxide or metal oxy-bromide species or, metal oxides in the case of the supported metal bromide salt or metal oxide operated at higher temperatures and lower pressures at which water may primarily exist as a vapor.
- the hydrobromic acid reacts with the metal hydroxide, metal oxy-bromide or metal oxide species and is neutralized, restoring the metal bromide salt and yielding water.
- the overall reaction results in the net oxidation of hydrobromic acid produced in first reactor 130 and second reactor 134 to elemental bromine and steam, catalyzed by the metal bromide/metal hydroxide or metal oxide operating in a catalytic cycle.
- the elemental bromine and water and any residual oxygen or nitrogen (if air or oxygen enriched air is utilized as the oxidant) leaving as vapor from the outlet of third reactor 117 are cooled in the second side of exchanger 141 and condenser 120 to a temperature in the range of about 0° C. to about 70° C. wherein the bromine and water are condensed and passed to three-phase separator 122 .
- three-phase separator 122 since liquid water has a limited solubility for bromine, on the order of about 3% by weight, any additional bromine which is condensed forms a separate, denser liquid bromine phase.
- the liquid bromine phase however, has a notably lower solubility for water, on the order of less than 0.1%.
- a substantially dry bromine vapor can be easily obtained by condensing liquid bromine and water, decanting water by simple physical separation and subsequently re-vaporizing liquid bromine. It is important to operate at conditions that result in the near complete reaction of HBr so as to avoid significant residual HBr in the condensed liquid bromine and water, as HBr increases the miscibility of bromine in the aqueous phase, and at sufficiently high concentrations, results in a single ternary liquid phase.
- Liquid bromine is pumped from three-phase separator 122 via pump 124 to a pressure sufficient to mix with vapor stream 162 .
- the residual air, oxygen enriched air or oxygen and any bromine vapor which is not condensed exits three-phase separator 122 and is passed via line 123 to bromine scrubber 148 , wherein residual bromine is recovered by dissolution into hydrobromic acid solution stream conveyed to scrubber 148 via line 165 .
- Water is removed from the three-phase separator 122 via line 129 and passed to stripper 114 .
- the metal bromide/metal hydroxide, metal oxy-bromide or metal oxide operates in a catalytic cycle allowing bromine to be easily recycled within the process.
- the metal bromide is readily oxidized by oxygen, oxygen enriched air or air either in the aqueous phase or the vapor phase at temperatures in the range of about 100° C. to about 600° C. and most preferably in the range of about 120° C. to about 180° C. to yield elemental bromine vapor and metal hydroxide, metal oxy-bromide or metal oxide. Operation at temperatures below about 180° C. is advantageous, thereby allowing the use of low-cost corrosion-resistant fluoropolymer-lined equipment. Hydrobromic acid is neutralized by reaction with the metal hydroxide or metal oxide yielding steam and the metal bromide.
- the elemental bromine vapor and steam are condensed and easily separated in the liquid phase by simple physical separation, yielding substantially dry bromine.
- the absence of significant water allows selective bromination of alkanes, without production of CO 2 and the subsequent efficient and selective reactions of alkyl bromides to primarily C 2 to C 4 olefins and heavier products, the C 5 + fraction of which contains substantial branched alkanes and substituted aromatics.
- Byproduct hydrobromic acid vapor from the bromination reaction and subsequent reaction in reactor 134 are readily dissolved into an aqueous phase and neutralized by the metal hydroxide or metal oxide species resulting from oxidation of the metal bromide.
- the alkyl bromination and alkyl bromide conversion stages are operated in a substantially similar manner to those corresponding stages described with respect to FIGS. 2 and 3 above. More particularly, a gas stream containing lower molecular weight alkanes, comprised of mixture of a feed gas and a recycled gas stream at a pressure in the range of about 1 bar to about 30 bar, is transported or conveyed via line, pipe or conduits 262 and 211 , respectively, and mixed with dry bromine liquid in line 225 . The resultant mixture is transported via pump 224 and passed to heat exchanger 226 wherein the liquid bromine is vaporized.
- the mixture of lower molecular weight alkanes and dry bromine vapor is fed to reactor 230 .
- the molar ratio of lower molecular weight alkanes to dry bromine vapor in the mixture introduced into reactor 230 is in excess of 2.5:1.
- Reactor 230 has an inlet pre-heater zone 228 which heats the mixture to a reaction initiation temperature in the range of 250° C. to 400° C.
- the lower molecular weight alkanes are reacted exothermically with dry bromine vapor at a relatively low temperature in the range of about 250° C.
- methyl bromide occurs in accordance with the following general reaction: CH 4 (g)+Br 2 (g) ⁇ CH 3 Br (g)+HBr (g) This reaction occurs with a significantly high degree of selectivity to methyl bromide.
- the dry bromine vapor that is feed into first reactor 230 is substantially water-free. Applicant has discovered that elimination of substantially all water vapor from the bromination step in first reactor 230 substantially eliminates the formation of unwanted carbon dioxide thereby increasing the selectivity of alkane bromination to alkyl bromides and eliminating the large amount of waste heat generated in the formation of carbon dioxide from alkanes.
- the effluent that contains alkyl bromides and hydrobromic acid is withdrawn from the first reactor 230 via line 231 and is partially cooled to a temperature in the range of about 150° C. to 450° C. in heat exchanger 232 before flowing to a second reactor 234 .
- the alkyl bromides are reacted exothermically at a temperature range of from about 250° C. to about 500° C., and a pressure in the range of about 1 bar to 30 bar, over a fixed bed of crystalline alumino-silicate catalyst, preferably a zeolite catalyst, and most preferably, an X type or Y type zeolite catalyst.
- a preferred zeolite is 10 X or Y type zeolite, although other zeolites with differing pore sizes and acidities, which are synthesized by varying the alumina-to-silica ratio may be used in the process of the present invention as will be evident to a skilled artisan.
- the zeolite catalyst is preferably used in a protonic form, a sodium form or a mixed protonic/sodium form, the zeolite may also be modified by ion exchange with other alkali metal cations, such as Li, K or Cs, with alkali-earth metal cations, such as Mg, Ca, Sr or Ba, with transition metal cations, such as Ni, Mn, V, W, or to the hydrogen form.
- the temperature at which the second reactor 234 is operated is an important parameter in determining the selectivity of the reaction to olefins and various higher molecular weight liquid hydrocarbons. It is preferred to operate second reactor 234 at a temperature within the range of about 250° C. to about 500° C., but more preferably within the range of about 300° C. to about 450° C. Temperatures above about 450° C. in the second reactor result in increased yields of light hydrocarbons, such as undesirable methane and carbonaceous coke, whereas lower temperatures increase yields of olefins and heavier molecular weight hydrocarbon products.
- the catalyst may be periodically regenerated in situ, by isolating reactor 234 from the normal process flow, purging with an inert gas via line 270 at a pressure in the range of about 1 bar to about 5 bar and an elevated temperature in the range of about 400° C. to about 650° C. to remove unreacted material adsorbed on the catalyst insofar as is practical, and then subsequently oxidizing the deposited carbon to CO 2 by addition of air or inert gas-diluted oxygen via line 270 to reactor 234 at a pressure in the range of about 1 bar to about 5 bar and an elevated temperature in the range of about 400° C. to about 650° C. Carbon dioxide and residual air or inert gas are vented from reactor 234 via line 275 during the regeneration period.
- the effluent which comprises olefins, the higher molecular weight hydrocarbons and hydrobromic acid is withdrawn from the second reactor 234 via line 235 and cooled to a temperature in the range of about 100° C. to about 600° C. in exchanger 236 .
- the cooled effluent is transported via lines 235 and 241 with valve 238 in the opened position and valves 239 and 243 in the closed position and introduced into a vessel or reactor 240 containing a bed 298 of a solid phase metal oxide.
- the metal of the metal oxide is selected form magnesium (Mg), calcium (Ca), vanadium (V), chromium (Cr), manganese (Mn), iron (Fe), cobalt (Co), nickel (Ni), copper (Cu), zinc (Sn), or tin (Sn).
- the metal is selected for the impact of its physical and thermodynamic properties relative to the desired temperature of operation, and also for potential environmental and health impacts and cost.
- magnesium, copper and iron are employed as the metal, with magnesium being the most preferred.
- These metals have the property of not only forming oxides but bromide salts as well, with the reactions being reversible in a temperature range of less than about 500° C.
- the solid metal oxide is preferably immobilized on a suitable attrition-resistant support, for example a synthetic amorphous silica, such as Davicat Grade 57, manufactured by Davison Catalysts of Columbia, Md. Or more preferably, an alumina support with a specific surface area of about 50 to 200 m2/g.
- a suitable attrition-resistant support for example a synthetic amorphous silica, such as Davicat Grade 57, manufactured by Davison Catalysts of Columbia, Md.
- an alumina support with a specific surface area of about 50 to 200 m2/g.
- hydrobromic acid is reacted with the metal oxide at temperatures below about 600° C. and preferably between about 100° C. to about 500° C.
- the dried gas stream containing olefins and the higher molecular weight hydrocarbons is further passed via line 251 to product recovery unit 252 to recover olefins and the C 5 + fraction as a liquid product in line 254 .
- product recovery unit 252 Any conventional method of dehydration and liquids recovery such as solid-bed dessicant adsorption followed by, for example, refrigerated condensation, cryogenic expansion, or circulating absorption oil or other solvent, as used to process natural gas or refinery gas streams and recover olefinic hydrocarbons, as known to a skilled artisan, may be employed in the implementation of this invention.
- the residual vapor effluent from product recovery unit 252 is then split into a purge stream 257 that may be utilized as fuel for the process and a recycled residual vapor which is compressed via compressor 258 .
- the recycled residual vapor discharged from compressor 258 is split into two fractions. A first fraction that is equal to at least 1.5 times the feed gas volume is transported via line 262 , combined with the liquid bromine and feed gas conveyed in line 225 and passed to heat exchanger 226 wherein the liquid bromine is vaporized and fed into first reactor 230 in a manner as described above.
- the dilution provided by the recycled vapor effluent permits selectivity of bromination in the first reactor 230 to be controlled in addition to moderating the temperature in second reactor 234 .
- Oxygen, oxygen enriched air or air 210 is delivered via blower or compressor 213 at a pressure in the range of about ambient to about 10 bar to bromine via line 214 , line 215 and valve 249 through heat exchanger 215 , wherein oxygen, oxygen enriched air or air is preheated to a temperature in the range of about 100° C. to about 500° C. to a second vessel or reactor 246 containing a bed 299 of a solid phase metal bromide.
- Oxygen reacts with the metal bromide in accordance with the following general reaction wherein M represents the metal: MBr 2 +1/2O 2 ⁇ MO+Br 2 In this manner, a dry, substantially HBr free bromine vapor is produced thereby eliminating the need for subsequent separation of water or hydrobromic acid from the liquid bromine.
- Reactor 246 is operated below 600° C., and more preferably between about 300° C. to about 500° C.
- the resultant bromine vapor is transported from reactor 246 via line 247 , valve 248 and line 242 to heat exchanger or condenser 221 where the bromine is condensed into a liquid.
- the liquid bromine is transported via line 242 to separator 222 wherein liquid bromine is removed via line 225 and transported via line 225 to heat exchanger 226 and first reactor 230 by any suitable means, such as by pump 224 .
- the residual air or unreacted oxygen is transported from separator 222 via line 227 to a bromine scrubbing unit 223 , such as venturi scrubbing system containing a suitable solvent, or suitable solid adsorbant medium, as selected by a skilled artisan, wherein the remaining bromine is captured.
- the captured bromine is desorbed from the scrubbing solvent or adsorbant by heating or other suitable means and the thus recovered bromine transported via line 212 to line 225 .
- the scrubbed air or oxygen is vented via line 229 . In this manner, nitrogen and any other substantially non-reactive components are removed from the system of the present invention and thereby not permitted to enter the hydrocarbon-containing portion of the process; also loss of bromine to the surrounding environment is avoided.
- Reactors 240 and 246 may be operated in a cyclic fashion. As illustrated in FIG. 4A , valves 238 and 219 are operated in the open mode to permit hydrobromic acid to be removed from the effluent that is withdrawn from the second reactor 234 , while valves 248 and 249 are operated in the open mode to permit air, oxygen enriched air or oxygen to flow through reactor 246 to oxidize the solid metal bromide contained therein. Once significant conversion of the metal oxide and metal bromide in reactors 240 and 246 , respectively, has occurred, these valves are closed. At this point, bed 299 in reactor 246 is a bed of substantially solid metal bromide, while bed 298 in reactor 240 is substantially solid metal oxide. As illustrated in FIG.
- valves 245 and 243 are then opened to permit oxygen, oxygen enriched air or air to flow through reactor 240 to oxidize the solid metal bromide contained therein, while valves 239 and 217 are opened to permit effluent which comprises olefins, the higher molecular weight hydrocarbons and hydrobromic acid that is withdrawn from the second reactor 234 to be introduced into reactor 246 .
- the reactors are operated in this manner until significant conversion of the metal oxide and metal bromide in reactors 246 and 240 , respectively, has occurred and then the reactors are cycled back to the flow schematic illustrated in FIG. 4A by opening and closing valves as previously discussed.
- FIGS. 4A and 5A When oxygen is utilized as the oxidizing gas transported in via line 210 to the reactor being used to oxidize the solid metal bromide contained therein, the embodiment of the process of the present invention illustrated in FIGS. 4A and 5A can be modified such that the bromine vapor produced from either reactor 246 ( FIG. 4B ) or 240 ( FIG. 5B ) is transported via lines 242 and 225 directly to first reactor 230 . Since oxygen is reactive and will not build up in the system, the need to condense the bromine vapor to a liquid to remove unreactive components, such as nitrogen, is obviated. Compressor 213 is not illustrated in FIGS. 4B and 5B as substantially all commercial sources of oxygen, such as a commercial air separator unit, will provide oxygen to line 210 at the required pressure. If not, a compressor 213 could be utilized to achieve such pressure as will be evident to a skilled artisan.
- the beds of solid metal oxide particles and solid metal bromide particles contained in reactors 240 and 246 , respectively, are fluidized and are connected in the manner described below to provide for continuous operation of the beds without the need to provide for equipment, such as valves, to change flow direction to and from each reactor.
- the effluent which comprises olefins, the higher molecular weight hydrocarbons and hydrobromic acid is withdrawn from the second reactor 234 via line 235 , cooled to a temperature in the range of about 100° C. to about 500° C. in exchanger 236 , and introduced into the bottom of reactor 240 which contains a bed 298 of solid metal oxide particles.
- oxygen, oxygen enriched air or air 210 is delivered via blower or compressor 213 at a pressure in the range of about ambient to about 10 bar, transported via line 214 through heat exchanger 215 , wherein the oxygen, oxygen enriched air or air is preheated to a temperature in the range of about 100° C. to about 500° C. and introduced into second vessel or reactor 246 below bed 299 of a solid phase metal bromide.
- Oxygen reacts with the metal bromide in the manner described above with respect to FIG. 4A to produce a dry, substantially HBr free bromine vapor.
- the flow of this introduced gas induces the particles in bed 299 to flow upwardly within reactor 246 as oxygen is reacted with the metal bromide.
- reactors 240 and 246 can be operated continuously without changing the parameters of operation.
- oxygen is utilized as the oxidizing gas and is transported in via line 210 to reactor 246 .
- the embodiment of the process of the present invention illustrated in FIG. 6A is modified such that the bromine vapor produced from reactor 246 is transported via lines 242 and 225 directly to first reactor 230 . Since oxygen is reactive and will not build up in the system, the need to condense the bromine vapor to a liquid to remove unreactive components, such as nitrogen, is obviated.
- Compressor 213 is not illustrated in FIG. 6B as substantially all commercial sources of oxygen, such as a commercial air separator unit, will provide oxygen to line 210 at the required pressure. If not, a compressor 213 could be utilized to achieve such pressure as will be evident to a skilled artisan.
- the alkyl bromination and alkyl bromide conversion stages are operated in a substantially similar manner to those corresponding stages described in detail with respect to FIG. 4A except as discussed below.
- Residual air or oxygen and bromine vapor emanating from reactor 246 is transported via line 247 , valve 248 and line 242 and valve 300 to heat exchanger or condenser 221 wherein the bromine-containing gas is cooled to a temperature in the range of about 30° C. to about 300° C.
- the bromine-containing vapor is then transported via line 242 to vessel or reactor 320 containing a bed 322 of a solid phase metal bromide in a reduced valence state.
- the metal of the metal bromide in a reduced valence state is selected from copper (Cu), iron (Fe), or molybdenum (Mo).
- the metal is selected for the impact of its physical and thermodynamic properties relative to the desired temperature of operation, and also for potential environmental and health impacts and cost.
- copper or iron are employed as the metal, with copper being the most preferred.
- the solid metal bromide is preferably immobilized on a suitable attrition-resistant support, for example a synthetic amorphous silica, such as Davicat Grade 57, manufactured by Davison Catalysts of Columbia, Md.
- the metal is deposited in oxide form in a range of about 10 to 20 wt % on an alumina support with a specific surface area in the range of about 50 to 200 m2/g
- bromine vapor is reacted with the solid phase metal bromide, preferably retained on a suitable attrition-resistant support at temperatures below about 300° C. and preferably between about 30° C. to about 200° C. in accordance with the following general formula wherein M 2 represents the metal: 2M 2 Br n +Br 2 ⁇ 2M 2 Br n+1
- bromine is stored as a second metal bromide, i.e. 2M 2 Br n+1 , in reactor 320 while the resultant vapor containing residual air or oxygen is vented from reactor 320 via line 324 , valve 326 and line 318 .
- the gas stream containing lower molecular weight alkanes comprised of mixture of a feed gas (line 211 ) and a recycled gas stream, is transported or conveyed via line 262 , heat exchanger 352 , wherein the gas stream is preheated to a temperature in the range of about 150° C. to about 600° C., valve 304 and line 302 to a second vessel or reactor 310 containing a bed 312 of a solid phase metal bromide in an oxidized valence state.
- the metal of the metal bromide in an oxidized valence state is selected from copper (Cu), iron (Fe), or molybdenum (Mo).
- the metal is selected for the impact of its physical and thermodynamic properties relative to the desired temperature of operation, and also for potential environmental and health impacts and cost.
- copper or iron are employed as the metal, with copper being the most preferred.
- the solid metal bromide in an oxidized state is preferably immobilized on a suitable attrition-resistant support, for example a synthetic amorphous silica such as Davicat Grade 57, manufactured by Davison Catalysts of Columbia, Md. More preferably the metal is deposited in an oxide state in a range of 10 to 20 wt % supported on an alumina support with a specific surface area of about 50 to 200 m2/g.
- the temperature of the gas stream is from about 150° C.
- the temperature of the gas stream thermally decomposes the solid phase metal bromide in an oxidized valence state to yield elemental bromine vapor and a solid metal bromide in a reduced state in accordance with the following general formula wherein M 2 represents the metal: 2M 2 Br n+1 ⁇ 2M 2 Br n +Br 2
- M 2 represents the metal: 2M 2 Br n+1 ⁇ 2M 2 Br n +Br 2
- the resultant bromine vapor is transported with the gas stream containing lower molecular weight alkanes via lines 314 , 315 , valve 317 , line 330 , heat exchanger 226 prior to being introduced into alkyl bromination reactor 230 .
- Reactors 310 and 320 may be operated in a cyclic fashion. As illustrated in FIG. 7 , valve 304 is operated in the open mode to permit the gas stream containing lower molecular weight alkanes to be transported to the second reactor 310 , while valve 317 is operated in the open mode to permit this gas stream with bromine vapor that is generated in reactor 310 to be transported to alkyl bromination reactor 230 . Likewise, valve 306 is operated in the open mode to permit bromine vapor from reactor 246 to be transported to reactor 320 , while valve 326 is operated in the open mode to permit residual air or oxygen to be vented from reactor 320 .
- valves 304 , 317 , 306 and 326 are closed, and then valves 308 and 332 are opened to permit the gas stream containing lower molecular weight alkanes to be transported or conveyed via lines 262 , heat exchanger 352 , wherein gas stream is heated to a range of about 150° C. to about 600° C., valve 308 and line, 309 to reactor 320 to thermally decompose the solid phase metal bromide in an oxidized valence state to yield elemental bromine vapor and a solid metal bromide in a reduced state.
- Valve 332 is also opened to permit the resultant bromine vapor to be transported with the gas stream containing lower molecular weight alkanes via lines 324 and 330 and heat exchanger 226 prior to being introduced into alkyl bromination reactor 230 .
- valve 300 is-opened to permit bromine vapor emanating from reactor 246 to be transported via line 242 through exchanger 221 into reactor 310 wherein the solid phase metal bromide in a reduced valence state reacts with bromine to effectively store bromine as a metal bromide.
- valve 316 is opened to permit the resulting gas, which is substantially devoid of bromine to be vented via lines 314 and 318 .
- the reactors are operated in this manner until significant conversion of the beds of reduced metal bromide and oxidized metal bromide in reactors 310 and 320 , respectively, to the corresponding oxidized and reduced states has occurred and then the reactors are cycled back to the flow schematic illustrated in FIG. 7 by opening and closing valves as previously discussed.
- the beds 312 and 322 contained in reactors 310 and 320 are fluidized and are connected in the manner described below to provide for continuous operation of the beds without the need to provide for equipment, such as valves, to change flow direction to and from each reactor.
- the bromine-containing gas withdrawn from the reactor 246 via line 242 is cooled to a temperature in the range of about 30° C. to about 300° C. in exchangers 370 and 372 , and introduced into the bottom of reactor 320 which contains a moving solid bed 322 in a fluidized state.
- this introduced fluid induces the particles in bed 322 to flow upwardly within reactor 320 as the bromine vapor is reacted with the reduced metal bromide entering the bottom of bed 322 in the manner as described above with respect to FIG. 7 .
- the particles which contain substantially oxidized metal bromide on the attrition-resistant support due to the substantially complete reaction of the reduced metal bromide with bromine vapor in reactor 320 are withdrawn via a weir, cyclone or other conventional means of solid/gas separation, flow by gravity down line 359 and are introduced at or near the bottom of the bed 312 in reactor 310 .
- a weir, cyclone or other conventional means of solid/gas separation flow by gravity down line 359 and are introduced at or near the bottom of the bed 312 in reactor 310 .
- the gas stream containing lower molecular weight alkanes comprised of mixture of a feed gas (line 211 ) and a recycled gas stream, is transported or conveyed via line 262 and heat exchanger 352 wherein the gas stream is heated to a range of about 150° C. to about 600° C. and introduced into reactor 310 .
- the heated gas stream thermally decomposes the solid phase metal bromide in an oxidized valence state present entering at or near the bottom of bed 312 to yield elemental bromine vapor and a solid metal bromide in a reduced state.
- the flow of this introduced gas induces the particles in bed 312 to flow upwardly within reactor 310 as the oxidized metal bromide is thermally decomposed.
- reactors 310 and 320 can be operated continuously with changing the parameters of operation.
- the process of the present invention is less expensive than conventional process since it operates at low pressures in the range of about 1 bar to about 30 bar and at relatively low temperatures in the range of about 20° C. to about 600° C. for the gas phase, and preferably about 20° C. to about 180° C. for the liquid phase.
- These operating conditions permit the use of less expensive equipment of relatively simple design that are constructed from readily available metal alloys or glass-lined equipment for the gas phase and polymer-lined or glass-lined vessels, piping and pumps for the liquid phase.
- the process of the present invention is also more efficient because less energy is required for operation and the production of excessive carbon dioxide as an unwanted byproduct is minimized.
- the process is capable of directly producing a mixed hydrocarbon product containing various molecular-weight components in the liquefied petroleum gas (LPG), olefin and motor gasoline fuels range that have substantial aromatic content thereby significantly increasing the octane value of the gasoline-range fuel components.
- LPG liquefied petroleum gas
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Priority Applications (29)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US11/254,438 US20060100469A1 (en) | 2004-04-16 | 2005-10-19 | Process for converting gaseous alkanes to olefins and liquid hydrocarbons |
PCT/US2006/035788 WO2007046986A2 (en) | 2005-10-19 | 2006-09-13 | Process for converting gaseous alkanes to olefins and liquid hydrocarbons |
BRPI0617707-7A BRPI0617707A2 (pt) | 2005-10-19 | 2006-09-13 | processo para a conversão de alcanos gasosos em olefinas e hidrocarbonetos lìquidos |
MYPI20081159 MY151088A (en) | 2005-10-19 | 2006-09-13 | Process for converting gaseous alkanes to olefins and liquid hydrocarbons |
CN2006800390646A CN101291891B (zh) | 2005-10-19 | 2006-09-13 | 将气态烷烃转化为烯烃和液态烃的方法 |
UAA200806734A UA105476C2 (uk) | 2005-10-19 | 2006-09-13 | Спосіб перетворення газоподібних алканів в олефіни і рідкі вуглеводні |
EA200801115A EA022696B1 (ru) | 2005-10-19 | 2006-09-13 | Способ превращения газообразных алканов в олефины и жидкие углеводороды |
ZA200803330A ZA200803330B (en) | 2005-10-19 | 2006-09-13 | Process for converting gaseous alkanes to olefins and liquid hydrocarbons |
AU2006302939A AU2006302939B2 (en) | 2005-10-19 | 2006-09-13 | Process for converting gaseous alkanes to olefins and liquid hydrocarbons |
AP2008004417A AP2008004417A0 (en) | 2005-10-19 | 2006-09-13 | Process for converting gaseous alkanes to olefins and liquid hydrocarbons |
NZ567480A NZ567480A (en) | 2005-10-19 | 2006-09-13 | Process for converting gaseous alkanes to olefins and liquid hydrocarbons |
JP2008536583A JP5396082B2 (ja) | 2005-10-19 | 2006-09-13 | ガス状アルカンをプロセスオレフィン及び液体炭化水素に転換するプロセス |
EP06814642A EP1945598A4 (en) | 2005-10-19 | 2006-09-13 | PROCESS FOR CONVERTING GASEOUS ALKANES TO OLEFINS AND LIQUID HYDROCARBONS |
CA2625459A CA2625459C (en) | 2005-10-19 | 2006-09-13 | Process for converting gaseous alkanes to olefins and liquid hydrocarbons |
KR1020087009389A KR101363300B1 (ko) | 2005-10-19 | 2006-09-13 | 가스상 알칸의 올레핀 및 액상 탄화수소로의 전환방법 |
PE2006001251A PE20070737A1 (es) | 2005-10-19 | 2006-10-16 | Procedimiento para convertir alcanos gaseosos a olefinas e hidrocarburos liquidos |
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US12/123,924 US20080275284A1 (en) | 2004-04-16 | 2008-05-20 | Process for converting gaseous alkanes to liquid hydrocarbons |
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US12/957,036 US20110071326A1 (en) | 2004-04-16 | 2010-11-30 | Process for converting gaseous alkanes to liquid hydrocarbons |
US13/117,785 US8642822B2 (en) | 2004-04-16 | 2011-05-27 | Processes for converting gaseous alkanes to liquid hydrocarbons using microchannel reactor |
US13/679,600 US20130079564A1 (en) | 2004-04-16 | 2012-11-16 | Process for converting gaseous alkanes to liquid hydrocarbons |
US14/255,549 US9206093B2 (en) | 2004-04-16 | 2014-04-17 | Process for converting gaseous alkanes to liquid hydrocarbons |
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Citations (64)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2168260A (en) * | 1934-11-11 | 1939-08-01 | Ig Farbenindustrie Ag | Process of preparing monohalogenation products |
US2246082A (en) * | 1939-08-22 | 1941-06-17 | Shell Dev | Preparation of alkyl halides |
US2488083A (en) * | 1946-06-18 | 1949-11-15 | Socony Vacuum Oil Co Inc | Manufacture of liquid hydrocarbons |
US2677598A (en) * | 1953-01-19 | 1954-05-04 | Dow Chemical Co | Oxidation of ferrous halides to form ferric halides |
US2941014A (en) * | 1954-08-06 | 1960-06-14 | Hoechst Ag | Manufacture of alkyl chlorination products |
US3172915A (en) * | 1965-03-09 | Preparation of oxygenated methane derivatives | ||
US3246043A (en) * | 1962-12-12 | 1966-04-12 | Universal Oil Prod Co | Preparation of olefinic hydrocarbons |
US3273964A (en) * | 1963-02-28 | 1966-09-20 | Universal Oil Prod Co | Process for producing bromine from a mixture of hydrogen bromide and olefinic hydrocarbon |
US3310380A (en) * | 1964-02-13 | 1967-03-21 | Universal Oil Prod Co | Bromine recovery |
US3353916A (en) * | 1966-04-25 | 1967-11-21 | Universal Oil Prod Co | Quantitative recovery of bromine by two stage catalytic oxidation of hydrogen bromide |
US3562321A (en) * | 1961-10-10 | 1971-02-09 | Sun Oil Co | Preparation of oxygenated hydrocarbons |
US3598876A (en) * | 1967-11-13 | 1971-08-10 | Universal Oil Prod Co | Selective halogenation of hydrocarbons |
US3702886A (en) * | 1969-10-10 | 1972-11-14 | Mobil Oil Corp | Crystalline zeolite zsm-5 and method of preparing the same |
US3876715A (en) * | 1972-12-01 | 1975-04-08 | Gulf Research Development Co | Process for preparing 2,3-dibromo-2-alkylalkanes |
US3894107A (en) * | 1973-08-09 | 1975-07-08 | Mobil Oil Corp | Conversion of alcohols, mercaptans, sulfides, halides and/or amines |
US3894105A (en) * | 1973-08-09 | 1975-07-08 | Mobil Oil Corp | Production of durene |
US4006169A (en) * | 1976-02-26 | 1977-02-01 | Smithkline Corporation | Epoxidation of α,β-ethylenic ketones |
US4197420A (en) * | 1977-07-18 | 1980-04-08 | Sebastiano Cesca | Method for producing oligomers from straight-chain alpha olefins, subsequently hydrogenating such oligomers and saturated products so obtained |
US4301253A (en) * | 1980-09-25 | 1981-11-17 | Union Carbide Corporation | Process for the selective production of ethanol and methanol directly from synthesis gas |
US4333852A (en) * | 1980-09-25 | 1982-06-08 | Union Carbide Corporation | Catalyst for the selective production of ethanol and methanol directly from synthesis gas |
US4347391A (en) * | 1973-06-11 | 1982-08-31 | Stauffer Chemical Company | Process for preparing ethylene dichloride |
US4373109A (en) * | 1981-08-05 | 1983-02-08 | Olah George A | Bifunctional acid-base catalyzed conversion of hetero-substituted methanes into olefins |
US4440871A (en) * | 1982-07-26 | 1984-04-03 | Union Carbide Corporation | Crystalline silicoaluminophosphates |
US4465893A (en) * | 1982-08-25 | 1984-08-14 | Olah George A | Oxidative condensation of natural gas or methane into gasoline range hydrocarbons |
US4467130A (en) * | 1981-09-01 | 1984-08-21 | Olah George A | Condensation of natural gas or methane into gasoline-range hydrocarbons |
US4489210A (en) * | 1981-08-19 | 1984-12-18 | Bayer Aktiengesellschaft | Process for the halogenation of organic compounds |
US4496752A (en) * | 1979-05-03 | 1985-01-29 | The Lummus Company | Production of epoxy compounds from olefinic compounds |
US4513092A (en) * | 1984-01-04 | 1985-04-23 | Mobil Oil Corporation | Composite catalyst for halogenation and condensation of alkanes |
US4523040A (en) * | 1981-09-01 | 1985-06-11 | Olah George A | Methyl halides and methyl alcohol from methane |
US4652688A (en) * | 1984-04-24 | 1987-03-24 | The British Petroleum Company, P.L.C. | Process for the production of hydrocarbons from hetero-substituted methanes |
US4654449A (en) * | 1982-12-09 | 1987-03-31 | Mobil Oil Corporation | Formation of halogenated hydrocarbons from hydrocarbons |
US4655893A (en) * | 1983-02-07 | 1987-04-07 | Battelle Development Corporation | Cubic boron nitride preparation utilizing a boron and nitrogen bearing gas |
US4665270A (en) * | 1983-12-16 | 1987-05-12 | The British Petroleum Company, P.L.C. | Process for the production of hydrocarbons from hetero-substituted alkanes |
US4748013A (en) * | 1985-04-17 | 1988-05-31 | Toyo Soda Manufacturing Co., Ltd. | Adsorbent for recovery of bromine and bromine-recovering process using same |
US4769504A (en) * | 1987-03-04 | 1988-09-06 | The United States Of America As Represented By The United States Department Of Energy | Process for converting light alkanes to higher hydrocarbons |
US4795843A (en) * | 1985-08-26 | 1989-01-03 | Uop Inc. | Conversion of methane into larger organic hydrocarbons |
US4804797A (en) * | 1987-08-24 | 1989-02-14 | Gas Research Institute | Production of commodity chemicals from natural gas by methane chlorination |
US4973786A (en) * | 1987-10-19 | 1990-11-27 | Karra Sankaram B | Process for the pyrolytic oxidation of methane to higher molecular weight hydrocarbons and synthesis gas |
US4982024A (en) * | 1989-12-26 | 1991-01-01 | Ethyl Corporation | Process for the selective dehydrohalogenation of an admixture of alkylhalides |
US5001293A (en) * | 1990-04-25 | 1991-03-19 | Amoco Corporation | Halocarbon conversion |
US5087786A (en) * | 1990-04-25 | 1992-02-11 | Amoco Corporation | Halogen-assisted conversion of lower alkanes |
US5157189A (en) * | 1987-10-19 | 1992-10-20 | Karra Sankaram B | Conversion of light hydrocarbons to higher hydrocarbons |
US5243098A (en) * | 1992-11-04 | 1993-09-07 | Energia Andina Ltd. | Conversion of methane to methanol |
US5276240A (en) * | 1991-10-18 | 1994-01-04 | Board Of Regents, The University Of Texas System | Catalytic hydrodehalogenation of polyhalogenated hydrocarbons |
US5486627A (en) * | 1994-12-02 | 1996-01-23 | The Dow Chemical Company | Method for producing epoxides |
US5705728A (en) * | 1990-12-06 | 1998-01-06 | Occidental Chemical Corporation | Process for the production of ethylene and mixture containing ethylene |
US5969195A (en) * | 1997-05-21 | 1999-10-19 | Basf Aktiengesellschaft | Hydrolysis of alkyl monohalides |
US5998679A (en) * | 1998-05-20 | 1999-12-07 | Jlm Technology, Ltd. | Methods for converting lower alkanes and alkanes to alcohols and diols |
US6403840B1 (en) * | 2001-06-20 | 2002-06-11 | Grt, Inc. | Process for synthesizing olefin oxides |
US6452058B1 (en) * | 2001-05-21 | 2002-09-17 | Dow Global Technologies Inc. | Oxidative halogenation of C1 hydrocarbons to halogenated C1 hydrocarbons and integrated processes related thereto |
US6465699B1 (en) * | 2001-06-20 | 2002-10-15 | Gri, Inc. | Integrated process for synthesizing alcohols, ethers, and olefins from alkanes |
US6486368B1 (en) * | 2001-06-20 | 2002-11-26 | Grt, Inc. | Integrated process for synthesizing alcohols, ethers, and olefins from alkanes |
US6525230B2 (en) * | 2001-04-18 | 2003-02-25 | Grt, Inc. | Zone reactor |
US20030069452A1 (en) * | 2001-06-20 | 2003-04-10 | Sherman Jeffrey H. | Method and apparatus for synthesizing from alcohols and ethers from alkanes, alkenes, and aromatics |
US20030078456A1 (en) * | 2001-06-20 | 2003-04-24 | Aysen Yilmaz | Integrated process for synthesizing alcohols, ethers, aldehydes, and olefins from alkanes |
US20040006246A1 (en) * | 2001-06-20 | 2004-01-08 | Sherman Jeffrey H. | Method and apparatus for synthesizing olefins, alcohols, ethers, and aldehydes |
US6713087B2 (en) * | 1999-05-28 | 2004-03-30 | Alkermes Controlled Therapeutics, Inc. | Method of producing submicron particles of a labile agent and use thereof |
US20050038310A1 (en) * | 2003-07-15 | 2005-02-17 | Lorkovic Ivan M. | Hydrocarbon synthesis |
US20050171393A1 (en) * | 2003-07-15 | 2005-08-04 | Lorkovic Ivan M. | Hydrocarbon synthesis |
US20050192468A1 (en) * | 2001-06-20 | 2005-09-01 | Sherman Jeffrey H. | Hydrocarbon conversion process improvements |
US7019182B2 (en) * | 2001-04-18 | 2006-03-28 | Grt, Inc. | Method of hydrocarbon preservation and environmental protection |
US20060229475A1 (en) * | 2005-04-11 | 2006-10-12 | Weiss Michael J | Synthesis of hydroxylated hydrocarbons |
US20060229228A1 (en) * | 2005-04-11 | 2006-10-12 | Zachary John Anthony Komon | Method of making alkoxylates |
US7230150B2 (en) * | 2001-04-18 | 2007-06-12 | Grt, Inc. | Zone reactor |
Family Cites Families (691)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB156122A (en) | 1919-12-08 | 1922-03-30 | Otto Traun S Forschungslaborat | Process for the manufacture of diolefines and derivatives thereof |
GB294100A (en) | 1927-07-16 | 1929-06-27 | Curt Epner | Improvements in and relating to the production of liquid polymerisation products from gases containing hydrocarbons |
GB363009A (en) | 1930-09-19 | 1931-12-17 | John Philip Baxter | Production of acetylene and vinyl chloride from ethylene dichloride |
FR745544A (zh) | 1931-11-11 | 1933-05-12 | ||
GB474922A (en) | 1936-05-14 | 1937-11-15 | Ig Farbenindustrie Ag | Process for chlorinating and brominating hydrocarbons |
GB536491A (en) | 1939-09-28 | 1941-05-16 | Bataafsche Petroleum | A process for the production of aromatic hydrocarbons from unsaturated hydrocarbons |
GB553950A (en) | 1941-09-09 | 1943-06-11 | Du Pont | Improvements in or relating to the manufacture of halogenated hydrocarbons |
GB586483A (en) | 1944-07-05 | 1947-03-20 | Standard Oil Dev Co | Process for the conversion of normally gaseous olefins to liquid hydrocarbons |
GB775590A (en) | 1953-11-27 | 1957-05-29 | Standard Oil Co | Improvements in or relating to production of ethyl toluenes |
GB793214A (en) | 1955-02-18 | 1958-04-09 | Bataafsche Petroleum | Process for the conversion of hydrocarbons containing acyclic carbon atoms |
GB796085A (en) | 1955-12-22 | 1958-06-04 | Bataafsche Petroleum | Hydrocarbon conversion process |
GB796048A (en) | 1956-02-06 | 1958-06-04 | Bataafsche Petroleum | Conversion of hydrocarbons |
DE1037137B (de) | 1957-01-25 | 1958-08-21 | Bayer Ag | Verfahren zur Herstellung halogenhaltiger, aromatisch-aliphatischer Polyaether |
GB883256A (en) | 1958-05-02 | 1961-11-29 | Columbia Southern Chem Corp | Halogenation process |
BE623466A (zh) | 1961-10-13 | |||
GB950976A (en) | 1961-10-13 | 1964-03-04 | British Hydrocarbon Chem Ltd | Improvements in and relating to the production of olefines |
GB991303A (en) | 1962-07-26 | 1965-05-05 | British Hydrocarbon Chem Ltd | The production of olefines by the dehydrochlorination of alkyl chlorides |
US3294846A (en) | 1962-10-10 | 1966-12-27 | Dow Chemical Co | Process for preparing metaaryloxy phenols |
GB1015033A (en) | 1963-01-31 | 1965-12-31 | Shell Int Research | Preparation of olefin oxides |
NL125428C (zh) | 1963-02-27 | |||
US4011278A (en) | 1963-02-27 | 1977-03-08 | Mobil Oil Corporation | Conversion of polar compounds using a zsm-5 zeolite catalyst |
GB1104294A (en) | 1963-12-10 | 1968-02-21 | Ralph William King | Production of lower alkanols and lower alkyl bromides |
US3923913A (en) | 1964-05-12 | 1975-12-02 | Pechiney Saint Gobain | Process for obtaining chlorinated derivatives of ethylene |
US3254023A (en) * | 1964-06-08 | 1966-05-31 | Socony Mobil Oil Co Inc | Method of heat balancing in organic catalytic reactions |
US3353919A (en) | 1964-07-23 | 1967-11-21 | Air Preheater | Apparatus for the elimination of odors from noxious gases |
BE672377A (zh) | 1964-11-24 | 1966-05-16 | ||
DE1618686B1 (de) | 1966-04-28 | 1971-08-26 | Marathon Oil Co | Tieftemperatur-Verfahren für die Chlorierung oder Bromierung von Kohlenwasserstoffen |
US3346340A (en) | 1966-08-11 | 1967-10-10 | Universal Oil Prod Co | Production of bromine by oxidation of hydrogen bromide |
DE1807780B2 (de) | 1968-11-08 | 1976-11-04 | Henkel & Cie GmbH, 4000 Düsseldorf | Verfahren zur herstellung von aether- und polyaetheralkoholen |
DE1618254B1 (de) | 1967-06-29 | 1971-07-08 | Kalk Chemische Fabrik Gmbh | Verfahren zur Herstellung von Bromverbindungen aus Alkoholen aus Brom |
US3496242A (en) | 1967-08-30 | 1970-02-17 | Fmc Corp | Oxychlorination of mixed hydrocarbons |
US3879480A (en) | 1967-12-07 | 1975-04-22 | Lummus Co | Vinyl chloride process |
US3679758A (en) | 1968-02-05 | 1972-07-25 | Sun Oil Co | Dihalogenation of branched alkanes |
GB1253618A (en) | 1968-03-28 | 1971-11-17 | Perstorp Ab | Process for the production of dry semi-formals |
CA920775A (en) | 1968-05-13 | 1973-02-13 | Vadekar Mohan | Oxidation of hydrogen chloride using molecular sieve catalysts |
US3673264A (en) | 1968-05-21 | 1972-06-27 | Dow Chemical Co | Method of preparing optically active propylene chlorohydrins and propylene oxides |
US3920764A (en) | 1968-10-23 | 1975-11-18 | Lummus Co | Dehydrogenation process |
US3657367A (en) | 1968-10-31 | 1972-04-18 | Stauffer Chemical Co | Oxychlorination of saturated and unsaturated hydrocarbons in the presence of a fluidized catalyst containing lanthanum and didymium |
US3670037A (en) | 1969-02-19 | 1972-06-13 | Exxon Research Engineering Co | Catalyst system |
US3883651A (en) | 1969-08-08 | 1975-05-13 | Boehringer Sohn Ingelheim | Pharmaceutical compositions containing a 2-(aminoalkylamino)-4-amino-thieno{8 3,2-d{9 pyrimidine and method of use |
US3705196A (en) | 1969-10-31 | 1972-12-05 | Sun Oil Co | Synthesis of aliphatic and alicyclic ethers |
US3799997A (en) | 1971-11-08 | 1974-03-26 | Universal Oil Prod Co | Preparation of alkenynes |
US3968200A (en) | 1972-03-27 | 1976-07-06 | The Lummus Company | Reactor effluent quench system |
US4172099A (en) | 1972-05-30 | 1979-10-23 | Stauffer Chemical Company | Process for chlorination of ethylene |
GB1395926A (en) | 1972-07-27 | 1975-05-29 | Bp Chem Int Ltd | Process for the production of isoprene by the chlorination/ dehydrochlorination of 2-methylbutene-2 |
JPS5231022B2 (zh) | 1972-10-06 | 1977-08-12 | ||
IT982662B (it) | 1973-03-30 | 1974-10-21 | Montedison Spa | Procedimento di bromofluorurazio ne del metano |
US3865886A (en) | 1973-06-20 | 1975-02-11 | Lummus Co | Production of allyl chloride |
US3894104A (en) | 1973-08-09 | 1975-07-08 | Mobil Oil Corp | Aromatization of hetero-atom substituted hydrocarbons |
US3894103A (en) | 1973-08-09 | 1975-07-08 | Mobil Oil Corp | Aromatization reactions |
US3879473A (en) | 1973-08-14 | 1975-04-22 | Phillips Petroleum Co | Preparation of ethers from alcohols and olefins catalyzed by iodine |
US3987119A (en) | 1973-10-23 | 1976-10-19 | Allied Chemical Corporation | Production of vinyl chloride from ethane |
US3919336A (en) | 1973-10-23 | 1975-11-11 | Allied Chem | Method of preparing vinyl chloride from liquid ethylene dichloride |
US4092368A (en) | 1974-03-13 | 1978-05-30 | General Electric Company | Vapor phase transesterification |
US4046825A (en) | 1974-05-15 | 1977-09-06 | Mobil Oil Corporation | Conversion of oxygenated compounds to gasoline |
US4117251A (en) | 1974-05-15 | 1978-09-26 | Chemische Werke Huls Ag | Method for preparing straight chain primary alcohols from 1-bromoalkanes |
US4035285A (en) | 1974-05-28 | 1977-07-12 | Mobil Oil Corporation | Hydrocarbon conversion process |
US3965205A (en) | 1974-06-10 | 1976-06-22 | Mobil Oil Corporation | Conversion of low octane hydrocarbons to high octane gasoline |
US4169862A (en) | 1974-07-22 | 1979-10-02 | The B. F. Goodrich Company | Low temperature catalytic combustion of chlorohydrocarbons |
US4058576A (en) | 1974-08-09 | 1977-11-15 | Mobil Oil Corporation | Conversion of methanol to gasoline components |
US4138440A (en) | 1974-08-14 | 1979-02-06 | Mobil Oil Corporation | Conversion of liquid alcohols and ethers with a fluid mass of ZSM-5 type catalyst |
US3928483A (en) | 1974-09-23 | 1975-12-23 | Mobil Oil Corp | Production of gasoline hydrocarbons |
US4044061A (en) | 1974-09-23 | 1977-08-23 | Mobil Oil Corporation | Preheating methanol effects steady state operation of conversion to gasoline |
US3974062A (en) | 1974-10-17 | 1976-08-10 | Mobil Oil Corporation | Conversion of full range crude oils with low molecular weight carbon-hydrogen fragment contributors over zeolite catalysts |
US4071753A (en) | 1975-03-31 | 1978-01-31 | Gte Laboratories Incorporated | Transducer for converting acoustic energy directly into optical energy |
US4049734A (en) | 1975-04-08 | 1977-09-20 | Mobil Oil Corporation | Conversion of coal to high octane gasoline |
US4025576A (en) | 1975-04-08 | 1977-05-24 | Mobil Oil Corporation | Process for manufacturing olefins |
US4025575A (en) | 1975-04-08 | 1977-05-24 | Mobil Oil Corporation | Process for manufacturing olefins |
US4133838A (en) | 1975-05-15 | 1979-01-09 | Pearson Research Corp. | Process for preparing hydrocarbons from methanol and phosphorus pentoxide |
ZA763551B (en) | 1975-07-02 | 1978-01-25 | Mobil Oil Corp | Manufacture of gasoline |
US4039600A (en) | 1975-07-02 | 1977-08-02 | Mobil Oil Corporation | Conversion of synthesis gas to aromatic hydrocarbons |
US4087475A (en) | 1975-07-03 | 1978-05-02 | Robert Kenneth Jordan | Carbonyl fluorination process |
US4052471A (en) | 1975-08-06 | 1977-10-04 | Pearsall Chemical Corporation | Process for chlorinating C8 to C30 linear hydrocarbons |
US3992466A (en) | 1975-08-13 | 1976-11-16 | Mobil Oil Corporation | Hydrocarbon conversion |
US4052472A (en) | 1976-01-16 | 1977-10-04 | Mobil Oil Corporation | Mordenite conversion of alkanols to penta- and hexamethyl benzenes |
US4049573A (en) | 1976-02-05 | 1977-09-20 | Mobil Oil Corporation | Zeolite catalyst containing oxide of boron or magnesium |
US4060568A (en) | 1976-03-31 | 1977-11-29 | Mobil Oil Corporation | Silica-modified zeolite catalyst and conversion therewith |
US4072733A (en) | 1976-04-02 | 1978-02-07 | Ethyl Corporation | Conversion of methanol and dimethyl ether |
US4110180A (en) | 1976-04-28 | 1978-08-29 | Diamond Shamrock Technologies S.A. | Process for electrolysis of bromide containing electrolytes |
IT1075503B (it) | 1976-05-08 | 1985-04-22 | Basf Ag | Processo per la preparazione di glicolesteri |
US4025571A (en) | 1976-05-12 | 1977-05-24 | Mobil Oil Corporation | Manufacture of hydrocarbons |
US4025572A (en) | 1976-05-12 | 1977-05-24 | Mobil Oil Corporation | Manufacture of hydrocarbons |
GB1542112A (en) | 1976-06-11 | 1979-03-14 | Shell Int Research | Process for the preparation of 2-phenylethanol or derivatives thereof |
US4143084A (en) | 1976-07-19 | 1979-03-06 | Mobil Oil Corporation | Di-alkylbenzene isomer mixtures |
US4035430A (en) | 1976-07-26 | 1977-07-12 | Mobil Oil Corporation | Conversion of methanol to gasoline product |
CA1089632A (en) | 1976-08-20 | 1980-11-18 | Alfred J. Darnell | Hydrogen production |
US4194990A (en) | 1977-02-11 | 1980-03-25 | Allied Chemical Corporation | Catalyst and process for the production of chlorofluorinated hydrocarbons |
US4380682A (en) | 1977-03-30 | 1983-04-19 | Diamond Shamrock Corporation | Balanced chlorination process |
US4156698A (en) | 1977-05-05 | 1979-05-29 | Mobil Oil Corporation | Conversion of alcohols or ethers using rare earth crystalline aluminosilicate in an alumina matrix |
NL7710901A (nl) | 1977-10-05 | 1979-04-09 | Esmil B V Stationsstraat 48 | Werkwijze voor het gelijktijdig verwerken van gebruikt metaal en/of metaalafval van gehaloge- neerde koolwaterstoffen. |
US4300005A (en) | 1977-12-02 | 1981-11-10 | Monsanto Co. | Preparation of vinyl chloride |
US4191618A (en) | 1977-12-23 | 1980-03-04 | General Electric Company | Production of halogens in an electrolysis cell with catalytic electrodes bonded to an ion transporting membrane and an oxygen depolarized cathode |
US4133966A (en) | 1977-12-23 | 1979-01-09 | Gulf Research & Development Company | Selective formation of ethanol from methanol, hydrogen and carbon monoxide |
GB1604081A (en) * | 1978-01-20 | 1981-12-02 | Gallaher Ltd | Production of catalysts from activated supports |
SU694483A1 (ru) | 1978-05-22 | 1979-10-30 | Уфимский Нефтяной Институт | Способ переработки побочных галоидуглеводородов производства хлористого аллила и металлилхлорида |
US4282159A (en) | 1978-06-19 | 1981-08-04 | Wisconsin Alumni Research Foundation | Preparation of alkylene oxides |
DE2832532A1 (de) | 1978-07-25 | 1980-02-07 | Hoechst Ag | Verfahren zur gewinnung von reinen 2-(perfluoralkyl)-aethanolen aus ihren gemischen mit 2-(perfluoralkyl)-aethylenen und gegebenenfalls 2-(perfluoralkyl)- aethylestern |
US4187255A (en) | 1978-08-21 | 1980-02-05 | Conoco, Inc. | Process for methylating naphthalene |
FR2434861A1 (fr) | 1978-08-31 | 1980-03-28 | Inst Francais Du Petrole | Procede de production d'essence a haut indice d'octane et en particulier d'essence utilisable sans plomb |
US4849573A (en) | 1978-09-05 | 1989-07-18 | Mobil Oil Corporation | Process for manufacturing light olefins |
US4300009A (en) | 1978-12-28 | 1981-11-10 | Mobil Oil Corporation | Conversion of biological material to liquid fuels |
JPS55130923A (en) * | 1979-03-30 | 1980-10-11 | Mitsubishi Heavy Ind Ltd | Condensation of methyl chloride through dehydrochlorination |
US4311865A (en) | 1979-04-04 | 1982-01-19 | Mobil Oil Corporation | Manufacture of hydrocarbons from oxygenates |
NL7902886A (nl) | 1979-04-12 | 1980-10-14 | Shell Int Research | Werkwijze voor de bereiding van een koolwaterstof- mengsel. |
US4410714A (en) | 1979-05-03 | 1983-10-18 | The Lummus Company | Production of epoxy compounds from olefinic compounds |
US4443620A (en) | 1979-05-03 | 1984-04-17 | The Lummus Company | Production of epoxy compounds from olefinic compounds |
US4272338A (en) | 1979-06-06 | 1981-06-09 | Olin Corporation | Process for the treatment of anolyte brine |
US4371716A (en) | 1979-09-04 | 1983-02-01 | Shell Oil Company | β-(Sec-alkoxy) ethanol process |
US4462814A (en) | 1979-11-14 | 1984-07-31 | Koch Process Systems, Inc. | Distillative separations of gas mixtures containing methane, carbon dioxide and other components |
EP0031200B1 (en) | 1979-12-13 | 1984-08-29 | Imperial Chemical Industries Plc | Method of recovering bromine from methyl bromide |
US4307261A (en) | 1980-02-19 | 1981-12-22 | Vulcan Materials Company | Process for separating ferric iron from chlorinated hydrocarbons |
US4412086A (en) | 1980-02-19 | 1983-10-25 | Vulcan Materials Company | Process for separating ferric iron from chlorinated hydrocarbons |
US4350511A (en) | 1980-03-18 | 1982-09-21 | Koch Process Systems, Inc. | Distillative separation of carbon dioxide from light hydrocarbons |
DE3164837D1 (en) | 1980-05-01 | 1984-08-23 | Ici Plc | Halogenation process using a halide carrier and process for regeneration of the halide carrier |
US4302619A (en) | 1980-06-04 | 1981-11-24 | Mobil Oil Corporation | Control of CO emissions in a process for producing gasoline from methanol |
US4317934A (en) | 1980-08-15 | 1982-03-02 | Ethyl Corporation | Preparation of carbonyl compounds |
US4320241A (en) | 1980-08-28 | 1982-03-16 | Occidental Research Corporation | Process for converting oxygenated hydrocarbons into hydrocarbons |
US4308403A (en) | 1980-09-12 | 1981-12-29 | Texaco Inc. | Process for preparing glycol ethers |
US4317943A (en) | 1980-09-12 | 1982-03-02 | Texaco Inc. | Process for preparing glycol ethers |
US4431856A (en) | 1980-09-29 | 1984-02-14 | Mobil Oil Corporation | Fluid zeolite catalyst conversion of alcohols and oxygenated derivatives to hydrocarbons |
DE3037093C1 (de) | 1980-10-01 | 1981-11-12 | Chemische Werke Hüls AG, 4370 Marl | Verfahren zur Herstellung von Cycloocten-4-ol-1 aus Cyclooctadien-1,5 |
US4543434A (en) | 1981-01-28 | 1985-09-24 | Mobil Oil Corporation | Process for producing liquid hydrocarbon fuels |
US4690903A (en) | 1981-02-02 | 1987-09-01 | Mobil Oil Corporation | Process for preparing organic fuels and chemicals from biomass |
GB2095245A (en) | 1981-03-19 | 1982-09-29 | Ici Plc | Chlorination of alkanes |
GB2095243A (en) | 1981-03-19 | 1982-09-29 | Ici Plc | Production of methylene chloride |
IN157669B (zh) | 1981-03-23 | 1986-05-17 | Pfizer | |
DE3117135A1 (de) | 1981-04-30 | 1982-11-18 | Bayer Ag, 5090 Leverkusen | Kristallines alumosilicat, verfahren zu dessen herstellung sowie dessen verwendung zur katalytischen umwandlung von methanol und/oder dimethylether in kohlenwasserstoffe |
US4389391A (en) | 1981-06-28 | 1983-06-21 | Dunn Jr Wendell E | Process for beneficiating titaniferous ores |
US4433192A (en) | 1981-09-01 | 1984-02-21 | Olah George A | Condensation of natural gas or methane into gasoline range hydrocarbons |
US4513164A (en) | 1981-09-01 | 1985-04-23 | Olah George A | Condensation of natural gas or methane into gasoline range hydrocarbons |
AU563307B2 (en) | 1981-09-01 | 1987-07-02 | G.A. Olah | Methyl halides and methyl alcohol from methane |
DE3137751A1 (de) | 1981-09-23 | 1983-03-31 | Metallgesellschaft Ag, 6000 Frankfurt | Verfahren zum erzeugen von benzinkohlenwasserstoffen aus methanol |
US4605803A (en) | 1981-11-21 | 1986-08-12 | Mobil Oil Corporation | Acid-catalyzed organic compound conversion |
CA1186345A (en) | 1981-12-14 | 1985-04-30 | Martin M.Y. Chang | Hydrocarbon production |
US4568660A (en) | 1982-01-25 | 1986-02-04 | Hercules Incorporated | Cycloolefin polymerization catalyst composition |
US4489211A (en) | 1982-02-04 | 1984-12-18 | Onoda Cement Co., Ltd. | Process for producing 2,2,2-trifluoroethanol |
US4538015A (en) | 1982-03-08 | 1985-08-27 | Mobil Oil Corporation | Catalysis over activated zeolites |
US4538014A (en) | 1982-03-08 | 1985-08-27 | Mobil Oil Corporation | Catalysis over activated zeolites |
IT1150678B (it) | 1982-03-12 | 1986-12-17 | Anic Spa | Procedimento per la produzione di eteri alchil terbutilici in presenza di butadiene |
US4384159A (en) | 1982-03-12 | 1983-05-17 | The Dow Chemical Company | Catalytic dehydrohalogenation process |
US4433189A (en) | 1982-03-18 | 1984-02-21 | Mobil Oil Corporation | Catalytic conversion of methanol to light olefins |
US4588835A (en) | 1982-03-29 | 1986-05-13 | Otsuka Kagaku Yakuhin Kabushiki Kaisha | Process for preparing alkoxyphenols |
US4499314A (en) | 1982-03-31 | 1985-02-12 | Imperial Chemical Industries Plc | Methanol conversion to hydrocarbons with zeolites and cocatalysts |
DE3216722A1 (de) | 1982-05-05 | 1983-11-10 | Hoechst Ag, 6230 Frankfurt | 4-halomethylbenzoesaeure-alkylester-imine und verfahren zu deren herstellung |
GB2120249B (en) | 1982-05-15 | 1985-11-27 | British Petroleum Co Plc | Process for the production of methyl or ethyl mono-halide |
US4467133A (en) | 1982-06-21 | 1984-08-21 | Mobil Oil Corporation | Conversion of alcohols and ethers to distillate range hydrocarbons |
FR2529883A1 (fr) | 1982-07-06 | 1984-01-13 | Ugine Kuhlmann | Procede de fabrication de chlorure de vinyle |
US4509955A (en) | 1982-08-09 | 1985-04-09 | The Lubrizol Corporation | Combinations of carboxylic acylating agents substituted with olefin polymers of high and low molecular weight mono-olefins, derivatives thereof, and fuels and lubricants containing same |
US4465884A (en) | 1982-08-17 | 1984-08-14 | Mobil Oil Corporation | Olefin processing |
US4814527A (en) | 1982-10-18 | 1989-03-21 | The Dow Chemical Company | Catalytic process for ethylene dichloride |
US4788377A (en) | 1983-04-22 | 1988-11-29 | Mobil Oil Corporation | Process for manufacturing olefins |
US4547612A (en) | 1984-09-25 | 1985-10-15 | Mobil Oil Corporation | Production of lubricant and/or heavy distillate range hydrocarbons by light olefin upgrading |
US4720600A (en) | 1983-06-29 | 1988-01-19 | Mobil Oil Corporation | Production of middle distillate range hydrocarbons by light olefin upgrading |
US4675410A (en) | 1983-07-11 | 1987-06-23 | Nepera Inc. | Process for the production of pyridine or alkyl substituted pyridines |
US4540826A (en) | 1983-08-12 | 1985-09-10 | Phillips Petroleum Company | Process for preparing olefinic aldehydes |
CA1202610A (en) | 1983-08-15 | 1986-04-01 | Ralph M. Dessau | Activity enhancement of high silica zeolites |
EP0134464B1 (de) | 1983-08-25 | 1988-04-20 | Hüls Aktiengesellschaft | Verfahren zur Herstellung von 3,3- bzw. 2,3-Dimethylbuten und 2,3-Dimethylbutadien bzw. zur gleichzeitigen Herstellung dieser Olefine und Glykol- bzw. Polyglykol-n-alkyl-3,3- bzw. -2,3-dimethylbutylether aus Mono- und Dichlor-dimethylbutan |
US5175382A (en) | 1983-09-22 | 1992-12-29 | Werner Hebgen | Preparation of 1,2-Dichloroethane |
US4524228A (en) | 1983-09-29 | 1985-06-18 | Mobil Oil Corporation | Production of durene and gasoline from synthesis gas |
US4524227A (en) | 1983-09-29 | 1985-06-18 | Mobil Oil Corporation | Coproduction of durene and gasoline from synthesis gas and alcohols and separation of durene-gasoline mixtures |
US4524231A (en) | 1983-09-29 | 1985-06-18 | Mobil Oil Corporation | Production of durene from alcohols and ethers |
US4704493A (en) | 1983-10-31 | 1987-11-03 | Chevron Corporation | Conversions of low molecular weight hydrocarbons to higher molecular weight hydrocarbons using a metal compound-containing catalyst (II-A) |
US4599474A (en) | 1983-10-31 | 1986-07-08 | Chevron Research Company | Conversions of low molecular weight hydrocarbons to higher molecular weight hydrocarbons using a metal-containing catalyst |
US4704488A (en) | 1983-10-31 | 1987-11-03 | Chevron Research Company | Conversions of low molecular weight hydrocarbons to higher molecular weight hydrocarbons using a metal compound-containing catalyst (111-A) |
US4709108A (en) | 1983-10-31 | 1987-11-24 | Chevron Research Company | Conversions of low molecular weight hydrocarbons to higher molecular weight hydrocarbons using a metal compound-containing catalyst |
GB8331982D0 (en) | 1983-11-30 | 1984-01-04 | British Petroleum Co Plc | Hydrocarbons from c1 to c4 alkyl monohalides |
GB8333613D0 (en) * | 1983-12-16 | 1984-01-25 | British Petroleum Co Plc | Production of hydrocarbons from c1 to c4 alkyl monohalides |
JPS60136525A (ja) | 1983-12-26 | 1985-07-20 | Agency Of Ind Science & Technol | エタノ−ルの製造法 |
US4621161A (en) | 1984-01-23 | 1986-11-04 | Mobil Oil Corporation | Oxygenate conversion over activated zeolite catalyst |
US4642404A (en) | 1984-01-23 | 1987-02-10 | Mobil Oil Corporation | Conversion of olefins and paraffins to higher hydrocarbons |
US4550218A (en) | 1984-03-05 | 1985-10-29 | Mobil Oil Corporation | Hydrocarbon synthesis with zeolite catalyst of improved hydrothermal stability |
LU85285A1 (fr) | 1984-04-03 | 1985-11-27 | Labofina Sa | Procede d'isomerisation d'olefines |
US4634800A (en) | 1984-04-16 | 1987-01-06 | Atlantic Richfield Company | Methane conversion process |
US4497967A (en) | 1984-06-15 | 1985-02-05 | The Halcon Sd Group, Inc. | Process for the preparation of ethanol from methanol, carbon monoxide _and hydrogen |
US4590310A (en) | 1984-08-02 | 1986-05-20 | The Boc Group, Inc. | Process for the preparation of 2,2,2-trifluoroethanol |
US4550217A (en) | 1984-08-29 | 1985-10-29 | Mobil Oil Corporation | Conversion of methanol to olefins using large size catalyst particles |
US4696985A (en) | 1984-11-16 | 1987-09-29 | Hercules Incorporated | Catalyst composition for polymerization of cycloolefins |
GB8429007D0 (en) | 1984-11-16 | 1984-12-27 | British Petroleum Co Plc | Aromatics from ethane/ethylene |
US4579977A (en) | 1984-12-20 | 1986-04-01 | Phillips Petroleum Company | Process for the oxidation of organic halides to organic aldehydes |
US4764356A (en) | 1984-12-21 | 1988-08-16 | Exxon Research & Engineering Co. | Process for synthesizing a zeolite catalyst on a pH controlled basis to improve catalyst life |
US4544781A (en) | 1985-01-09 | 1985-10-01 | Mobil Oil Corporation | Control of temperature exotherms in the conversion of methanol to gasoline hydrocarbons |
DE194931T1 (de) | 1985-03-14 | 1987-02-26 | Societe Nationale Elf Aquitaine (Production), Courbevoie, Fr | Verfahren und vorrichtung zur photochemischen sulfochlorinierung von gasfoermigen alkanen. |
US4658077A (en) | 1985-06-07 | 1987-04-14 | Phillips Petroleum Company | Composition of matter and method of oxidative conversion of organic compounds therewith |
US5210357A (en) | 1985-06-07 | 1993-05-11 | Phillips Petroleum Company | Composition of matter and method of oxidative conversion of organic compounds therewith |
US5093542A (en) | 1985-05-24 | 1992-03-03 | Atlantic Richfield Company | Methane conversion process |
US5146027A (en) | 1985-05-24 | 1992-09-08 | Atlantic Richfield Co. | Methane conversion process |
US5959170A (en) | 1985-05-24 | 1999-09-28 | Atlantic Richfield Company | Methane conversion process |
US4774216A (en) | 1985-06-07 | 1988-09-27 | Phillips Petroleum Company | Composition of matter for oxidative conversion of organic compounds |
US5105045A (en) | 1985-06-07 | 1992-04-14 | Phillips Petroleum Company | Method of oxidative conversion |
US4724275A (en) | 1985-07-01 | 1988-02-09 | National Distillers And Chemical Corporation | Crystalline aluminosilicates and their use in the conversion of methanol to low molecular weight hydrocarbons |
GB8518820D0 (en) | 1985-07-25 | 1985-08-29 | British Petroleum Co Plc | Chemical process |
GB8520977D0 (en) | 1985-08-21 | 1985-09-25 | British Petroleum Co Plc | Production of aromatics |
US4665259A (en) | 1985-08-28 | 1987-05-12 | The Standard Oil Company | Methane conversion process using phosphate-containing catalysts |
US4658073A (en) | 1985-09-23 | 1987-04-14 | Mobil Oil Corporation | Control system for multistage chemical upgrading |
US4633027A (en) | 1985-09-23 | 1986-12-30 | Mobil Oil Corporation | Process for converting olefins to gasoline, distillate and alkylate liquid hydrocarbons |
CA1322768C (en) | 1988-12-29 | 1993-10-05 | John E. Stauffer | Process for the chlorination of ethane |
US4788369A (en) | 1985-12-31 | 1988-11-29 | Mobil Oil Corporation | Conversion of methanol to gasoline |
LU86280A1 (fr) | 1986-01-29 | 1987-09-03 | Labofina Sa | Procede de production d'essence |
GB8613673D0 (en) | 1986-06-05 | 1986-07-09 | Bp Benzin Und Petroleum Ag | Chemical process |
ZA874948B (en) | 1986-07-07 | 1989-02-22 | Mobil Oil Corp | Aromatisation of aliphatics over gallium-containing zeolites |
US4781733A (en) | 1986-07-23 | 1988-11-01 | Bend Research, Inc. | Semipermeable thin-film membranes comprising siloxane, alkoxysilyl and aryloxysilyl oligomers and copolymers |
US4814532A (en) | 1986-08-04 | 1989-03-21 | Chemical Company, Ltd. Asahi | Process for producing alkylcyclopentadiene derivatives |
US4795848A (en) | 1986-08-28 | 1989-01-03 | The Standard Oil Company | Method for upgrading a low molecular weight alkane with a lead-zirconate catalyst |
US5082816A (en) | 1986-08-28 | 1992-01-21 | The Standard Oil Company | Lead-zirconate catalysts |
US4720602A (en) | 1986-09-08 | 1988-01-19 | Mobil Oil Corporation | Process for converting C2 to C12 aliphatics to aromatics over a zinc-activated zeolite |
US5120332A (en) | 1986-11-06 | 1992-06-09 | The Haser Company Limited | Gas resonance device |
US5118899A (en) | 1986-12-22 | 1992-06-02 | Phillips Petroleum Company | Composition of matter and method of oxidative conversion of organic compounds therewith |
US5160502A (en) | 1986-12-22 | 1992-11-03 | Phillips Petroleum Company | Composition of matter and method of oxidative conversion of organic compounds therewith |
US5087787A (en) | 1986-12-29 | 1992-02-11 | Phillips Petroleum Company | Method of oxidative conversion |
DE3700132A1 (de) | 1987-01-03 | 1988-07-14 | Dow Chemical Gmbh | Verfahren zum herstellen von ethylendichlorid |
US4792642A (en) | 1987-03-25 | 1988-12-20 | Eastman Kodak Company | Process for preparing iodinated aromatic compounds |
US4795737A (en) | 1987-03-25 | 1989-01-03 | Eastman Kodak Company | Process for the iodination of aromatic compounds over solid catalysts |
US4886932A (en) | 1987-03-30 | 1989-12-12 | Atlantic Richfield Company | Thin bed cofeed reaction system for methane conversion |
CA1322769C (en) | 1988-12-30 | 1993-10-05 | John E. Stauffer | Process for the chlorination of ethane |
US4777321A (en) | 1987-04-29 | 1988-10-11 | Mobil Oil Corporation | Feedstock preparation and conversion of oxygenates to olefins |
US4775462A (en) | 1987-06-22 | 1988-10-04 | Uop Inc. | Non-oxidative method of sweetening a sour hydrocarbon fraction |
US4808763A (en) | 1987-08-05 | 1989-02-28 | Amoco Corporation | Process for upgrading light paraffins |
US4783566A (en) | 1987-08-28 | 1988-11-08 | Uop Inc. | Hydrocarbon conversion process |
GB8724373D0 (en) | 1987-10-17 | 1987-11-18 | British Petroleum Co Plc | Chemical process |
US4814535A (en) | 1987-12-15 | 1989-03-21 | Mobil Oil Corporation | Conversion of oxygenates to gasoline at variable inlet temperature |
US4814536A (en) | 1987-12-15 | 1989-03-21 | Mobil Oil Corporation | Conversion of oxygenates to gasoline at variable space velocity |
GB8802731D0 (en) | 1988-02-06 | 1988-03-09 | British Petroleum Co Plc | Chemical process |
US5059744A (en) | 1988-03-03 | 1991-10-22 | Mobil Oil Corporation | Reactor and recovery system for upgrading lower olefins |
GB8806675D0 (en) | 1988-03-21 | 1988-04-20 | Shell Int Research | Process for preparing liquid hydrocarbons |
US4851602A (en) | 1988-04-11 | 1989-07-25 | Mobil Oil Corporation | Alkanes and alkenes conversion to high octane gasoline |
US4851606A (en) | 1988-04-25 | 1989-07-25 | Mobil Oil Corporation | Control of waste water chemical oxygen demand in an oxygenate to hydrocarbon conversion process |
US4886925A (en) | 1988-05-02 | 1989-12-12 | Mobil Oil Corp | Olefins interconversion and etherification process |
JPH07106998B2 (ja) | 1988-05-17 | 1995-11-15 | ダイキン工業株式会社 | 1,1,1−トリフルオロ−2,2−ジクロロエタンの製造方法 |
US5013793A (en) | 1990-07-26 | 1991-05-07 | Exxon Chemical Patents Inc. | Dynamically cured thermoplastic olefin polymers and process for producing the same |
US4990711A (en) | 1988-06-23 | 1991-02-05 | Mobil Oil Corporation | Synthetic polyolefin lubricant blends having high viscosity indices |
US4950822A (en) | 1988-06-27 | 1990-08-21 | Ethyl Corporation | Olefin oligomer synlube process |
US4899002A (en) | 1988-07-25 | 1990-02-06 | Mobil Oil Corp. | Integrated staged conversion of methanol to gasoline and distillate |
FR2635101B1 (fr) | 1988-08-05 | 1990-09-28 | Rhone Poulenc Chimie | Procede de preparation du trifluoroethanol par hydrolyse, en phase gazeuse, du chlorotrifluoroethane |
US4939311A (en) | 1988-08-17 | 1990-07-03 | Amoco Corporation | Catalysts for the oxidative conversion of methane to higher hydrocarbons |
US5055633A (en) | 1988-10-06 | 1991-10-08 | Uop | Adsorption and isomerization of normal and mono-methyl paraffins |
US4956521A (en) | 1988-10-06 | 1990-09-11 | Uop | Adsorption and isomerization of normal and mono-methyl paraffins |
US5055634A (en) | 1988-10-06 | 1991-10-08 | Uop | Adsorption and isomerization of normal and mono-methyl paraffins |
US5215648A (en) | 1988-10-20 | 1993-06-01 | Chevron Research And Technology Company | Hydrocarbon conversion processes using SSZ-31 |
US4899001A (en) | 1988-11-21 | 1990-02-06 | Uop | Process for the simultaneous hydroconversion of a first feedstock comprising unsaturated, halogenated organic compounds and a second feedstock comprising saturated, halogenated organic compounds |
US5194244A (en) | 1988-11-23 | 1993-03-16 | Shell Oil Company | Basic alkali metal-zeolite compositions |
US4929781A (en) | 1988-11-30 | 1990-05-29 | Uop | Process for the simultaneous hydroconversion of a first feedstock comprising unsaturated, halogenated organic compounds and a second feedstock comprising saturated, halogenated organic compounds |
US4895995A (en) | 1988-12-02 | 1990-01-23 | Uop | Process for the simultaneous hydroconversion of a first feedstock comprising unsaturated, halogenated organic compounds and a second feedstock comprising saturated, halogenated organic compounds |
EP0372183B1 (en) | 1988-12-07 | 1997-01-22 | Sumitomo Chemical Company, Limited | Process for the production of 2,3-dimethylbutenes |
US4939314A (en) | 1988-12-19 | 1990-07-03 | Mobil Oil Corporation | Method for on-stream low-pressure regeneration of an oligomerization catalyst from a fluid-bed reactor operating at high pressure with hydrocarbons in a non-liquid phase |
CA1304419C (en) | 1988-12-22 | 1992-06-30 | Raj N. Pandey | Conversion of methane to gasoline-range hydrocarbons via isobutene |
GB8829923D0 (en) | 1988-12-22 | 1989-02-15 | Ici Plc | Zeolites |
US5178748A (en) | 1988-12-22 | 1993-01-12 | Imperial Chemical Industries | Catalytic reactions using zeolites |
US4990696A (en) | 1988-12-29 | 1991-02-05 | Stauffer John E | Methyl alcohol process |
US4899000A (en) | 1989-01-27 | 1990-02-06 | Stauffer John E | Production of allyl chloride |
US5436378A (en) | 1989-02-16 | 1995-07-25 | Atochem | Drying of hydrocarbon/hydrochloric acid/water admixtures |
US5107051A (en) | 1989-03-14 | 1992-04-21 | Exxon Chemical Patents Inc. | Halogen resistant hydrotreating process and catalyst |
US4945175A (en) | 1989-05-26 | 1990-07-31 | Uop | Dehydrocyclodimerization process start-up procedure |
US5202511A (en) | 1989-08-16 | 1993-04-13 | The Dow Chemical Company | Catalyst diluent for oxychlorination process |
US5071815A (en) | 1989-09-01 | 1991-12-10 | British Columbia Research Corporation | Method for producing catalysts |
US5073657A (en) | 1989-09-19 | 1991-12-17 | Union Carbide Chemicals And Plastics Company Inc. | Vapor phase modifiers for oxidative coupling |
ZA907446B (en) | 1989-09-19 | 1991-07-31 | Union Carbide Chem Plastic | Silver-containing catalysts for oxidative coupling |
US5073656A (en) | 1989-09-19 | 1991-12-17 | Union Carbide Chemicals And Plastics Company, Inc. | High ethylene to ethane processes for oxidative coupling |
AU6259890A (en) | 1989-09-19 | 1991-03-28 | Union Carbide Chemicals And Plastics Company Inc. | Low temperature catalysts for oxidative coupling processes |
DE3933656A1 (de) | 1989-10-09 | 1991-04-11 | Basf Ag | Verdunstungsarme polyesterharze |
US5093533A (en) | 1989-12-08 | 1992-03-03 | Interstate Chemical, Inc. | Blended gasolines and process for making same |
US5208402A (en) | 1989-12-08 | 1993-05-04 | Interstate Chemical, Inc. | Liquid fuels for internal combustion engines and process and apparatus for making same |
US5026944A (en) | 1989-12-20 | 1991-06-25 | Energy Mines And Resources Canada | Synthesis of isobutene from methane and acetylene |
US5004847A (en) | 1989-12-27 | 1991-04-02 | Ethyl Corporation | Recovery of hexabromocyclododecane particles |
US5026937A (en) | 1989-12-29 | 1991-06-25 | Uop | Aromatization of methane using zeolite incorporated in a phosphorus-containing alumina |
US4982041A (en) | 1990-01-10 | 1991-01-01 | Union Carbide Chemicals And Plastics Company Inc. | Double perovskite catalysts for oxidative coupling |
US5055625A (en) | 1990-02-06 | 1991-10-08 | Fred Neidiffer | Gasoline additive composition and method for using same |
US5026934A (en) | 1990-02-12 | 1991-06-25 | Lyondell Petrochemical Company | Method for converting light hydrocarbons to olefins, gasoline and methanol |
US5043502A (en) | 1990-03-16 | 1991-08-27 | Uop | Production of xylenes from light aliphatic hydrocarbons via dehydrocyclodimerization and methylation |
US5228888A (en) | 1990-03-23 | 1993-07-20 | The Boc Group, Inc. | Economical air separator |
US5107061A (en) | 1990-04-06 | 1992-04-21 | Exxon Chemical Patents Inc. | Removal of organochlorides from hydrocarbon feed streams |
US5087779A (en) | 1990-04-25 | 1992-02-11 | Amoco Corporation | Hydrocarbon halogenation |
US5019652A (en) | 1990-04-30 | 1991-05-28 | The United States As Represented By The United States Department Of Energy | Catalysts and method |
US5139991A (en) | 1990-04-30 | 1992-08-18 | The United States Of American As Represented By The United States Department Of Energy | Oxyhydrochlorination catalyst |
US5068478A (en) | 1990-05-25 | 1991-11-26 | Energia Andina, Ltd. | Producing alkenes and alkynes from alkanes and alkenes |
GB9013859D0 (en) | 1990-06-21 | 1990-08-15 | Ici Plc | Zeolites |
GB9013916D0 (en) | 1990-06-22 | 1990-08-15 | Ici Plc | Zeolites |
US4988660A (en) | 1990-06-25 | 1991-01-29 | Union Carbide Chemicals And Plastics Company Inc. | Double perovskite catalysts for oxidative coupling |
US5096469A (en) | 1990-07-23 | 1992-03-17 | Keefer Bowie | Adsorptive gas separator with inertial energy exchange |
US5082473A (en) | 1990-07-23 | 1992-01-21 | Keefer Bowie | Extraction and concentration of a gas component |
US5013424A (en) | 1990-07-30 | 1991-05-07 | Uop | Process for the simultaneous hydrogenation of a first feedstock comprising hydrocarbonaceous compounds and having a non-distillable component and a second feedstock comprising halogenated organic compounds |
US5401890A (en) | 1990-07-30 | 1995-03-28 | Albemarle Corporation | Process and apparatus for heat treating halogenated compounds |
US5138112A (en) | 1990-08-31 | 1992-08-11 | Uop | Process for converting a C2 -C6 aliphatic hydrocarbon to high octane transportable fuel |
DE4029875A1 (de) | 1990-09-21 | 1992-03-26 | Hoechst Ag | Verfahren zur inhibierung und zerstoerung von peroxiden in dialkylethern |
JP2970683B2 (ja) | 1990-10-12 | 1999-11-02 | 日石三菱株式会社 | 水素化脱アルキル触媒を用いた水素化脱アルキル法 |
US5085674A (en) | 1990-10-25 | 1992-02-04 | Union Carbide Industrial Gases Technology Corporation | Duplex adsorption process |
US5071449A (en) | 1990-11-19 | 1991-12-10 | Air Products And Chemicals, Inc. | Gas separation by rapid pressure swing adsorption |
US5107032A (en) | 1990-11-20 | 1992-04-21 | Noramco, Inc. | Process for the preparation of o-phthalaldehydes |
US5105046A (en) | 1990-12-12 | 1992-04-14 | Amoco Corporation | Oxidative conversion of lower alkanes to higher hydrocarbons via fluorine-containing materials |
US5055235A (en) | 1990-12-12 | 1991-10-08 | Ethyl Corporation | Bromination process |
US5223471A (en) | 1990-12-12 | 1993-06-29 | Amoco Corporation | Fluorine-containing materials |
US5306855A (en) | 1991-02-15 | 1994-04-26 | Catalytica, Inc. | Catalytic process for converting lower alkanes to esters, alcohols, and to hydrocarbons |
US5233113A (en) | 1991-02-15 | 1993-08-03 | Catalytica, Inc. | Process for converting lower alkanes to esters |
GB9105167D0 (en) | 1991-03-12 | 1991-04-24 | Ici Plc | Chemical process |
US5188725A (en) | 1991-03-15 | 1993-02-23 | Mobil Oil Corporation | Fluidized catalyst process for production and etherification of olefins |
US5237115A (en) | 1991-03-15 | 1993-08-17 | Phillips Petroleum Company | Integrated olefin processing |
FR2674769B1 (fr) | 1991-04-04 | 1994-04-29 | Inst Francais Du Petrole | Catalyseur du type galloaluminosilicate contenant du gallium, un metal noble de la famille du platine et au moins un metal additionnel, et son utilisation en aromatisation des hydrocarbures. |
EP0510238A1 (en) | 1991-04-26 | 1992-10-28 | NOVAMONT S.p.A. | Process for producing lower poliols and mixtures thereof |
US5288677A (en) | 1991-06-28 | 1994-02-22 | Exxon Chemical Patents Inc. | Immobilized Lewis acid catalysts |
GB9116172D0 (en) | 1991-07-26 | 1991-09-11 | Thames Water Utilities | A method of and apparatus for treating a fluid |
US5399258A (en) | 1991-08-15 | 1995-03-21 | Mobil Oil Corporation | Hydrocarbon upgrading process |
MY108348A (en) | 1991-08-16 | 1996-09-30 | Exxon Chemical Patents Inc | Ester free ethers. |
US5264635A (en) | 1991-10-03 | 1993-11-23 | Mobil Oil Corporation | Selective cracking and etherification of olefins |
US5245109A (en) | 1991-10-11 | 1993-09-14 | Amoco Corporation | Hydrocarbon conversion |
JP3120292B2 (ja) | 1991-10-18 | 2000-12-25 | イハラケミカル工業株式会社 | 脂肪族カルボン酸ハロメチルエステル類の製造法 |
US5385650A (en) | 1991-11-12 | 1995-01-31 | Great Lakes Chemical Corporation | Recovery of bromine and preparation of hypobromous acid from bromide solution |
US5268518A (en) | 1991-11-15 | 1993-12-07 | The Dow Chemical Company | Reactor feed pipe design |
US5191142A (en) | 1991-12-23 | 1993-03-02 | Amoco Corporation | Process for converting methanol to olefins or gasoline |
JPH07503404A (ja) | 1992-02-04 | 1995-04-13 | カタリティカ,インコーポレイテッド | CeBr↓3触媒,および臭素生成のプロセス |
US6169218B1 (en) | 1992-02-10 | 2001-01-02 | Catalytic Distillation Technologies | Selective hydrogenation of highly unsaturated compounds in hydrocarbon streams |
US5354916A (en) | 1992-03-10 | 1994-10-11 | Exxon Research And Engineering Company | Low temperature conversion of alkanes |
CA2088939A1 (en) | 1992-03-10 | 1993-09-11 | Istvan T. Horvath | Low temperature conversion of alkanes |
US5202506A (en) | 1992-04-02 | 1993-04-13 | E. I. Du Pont De Nemours And Company | Oxidative drown process for 2-perfluoroalkylethyl alcohols |
US5185479A (en) | 1992-04-21 | 1993-02-09 | Stauffer John E | Process for methyl alcohol |
CA2097090A1 (en) | 1992-06-02 | 1993-12-03 | Quang N. Le | Process for the production of tertiary alkyl ether rich fcc gasoline |
US5395981A (en) | 1992-06-22 | 1995-03-07 | Uop | Hydrocarbon conversion by catalytic distillation |
US5254790A (en) | 1992-07-01 | 1993-10-19 | Phillips Petroleum Company | Integrated process for producing motor fuels |
US5284990A (en) | 1992-07-16 | 1994-02-08 | Stratco, Inc. | Method for converting a hydrogen fluoride alkylation unit to a sulfuric acid alkylation unit |
US5276242A (en) | 1992-08-26 | 1994-01-04 | Phillips Petroleum Company | Alkylation process |
US5243114A (en) | 1992-09-08 | 1993-09-07 | Mobil Oil Corporation | Oligomerization of alpha-olefins over layered silicate compositions containing pillars of silica and group VIB metal oxide |
US5430214A (en) | 1992-10-01 | 1995-07-04 | The Dow Chemical Company | Hydrodehalogenation process and catalyst for use therein |
IT1255710B (it) | 1992-10-01 | 1995-11-10 | Snam Progetti | Procedimento integrato per produrre olefine da miscele gassose contenenti metano |
US5453557A (en) | 1992-10-01 | 1995-09-26 | The Dow Chemical Company | Processes for converting chlorinated byproducts and waste products to useful materials |
US5276226A (en) | 1992-10-05 | 1994-01-04 | Exxon Research & Engineering Company | Low temperature halogenation of alkanes |
US5300126A (en) | 1992-10-19 | 1994-04-05 | Mobil Oil Corporation | Process for improving olefin etherification catalyst life |
US5744669A (en) | 1992-11-25 | 1998-04-28 | Uop | Process for the conversion of a halogenated organic stream containing trace quantities of organic nitrates |
US5817904A (en) | 1992-12-11 | 1998-10-06 | Repsol Petroleo S.A. | Method for the conversion of methane into longer chain hydrocarbons |
TW291486B (zh) | 1992-12-17 | 1996-11-21 | Exxon Chemical Patents Inc | |
US5470377A (en) | 1993-03-08 | 1995-11-28 | Whitlock; David R. | Separation of solutes in gaseous solvents |
US5354931A (en) | 1993-03-10 | 1994-10-11 | Uop | Process for hydrotreating an organic feedstock containing oxygen compounds and a halogen component |
US5994604A (en) | 1993-03-17 | 1999-11-30 | Lockheed Martin Idaho Technologies Company | Method and apparatus for low temperature destruction of halogenated hydrocarbons |
GB9407257D0 (en) | 1993-04-22 | 1994-06-08 | Ici Plc | Vaporisation of liquids |
US5382743A (en) | 1993-04-26 | 1995-01-17 | Mobil Oil Corporation | Skeletal isomerization of n-pentenes using ZSM-35 in the presence of hydrogen |
US5465699A (en) | 1993-06-01 | 1995-11-14 | Volkswagen Ag | Intake pipe arrangement for an internal combustion engine having individual arc-shaped cylinder intake pipes |
US5382704A (en) | 1993-06-30 | 1995-01-17 | E. I. Du Pont De Nemours And Company | Fluorinated methyl ethers |
US5382744A (en) | 1993-07-12 | 1995-01-17 | Phillips Petroleum Company | Control of synthetic isopentane production during alkylation of amylenes |
US5510525A (en) | 1993-07-22 | 1996-04-23 | Gas Research Institute | Direct catalytic oxidative carbonylation of lower alkanes to acids |
IT1265051B1 (it) | 1993-08-06 | 1996-10-28 | Eniricerche Spa | Processo per l'alchilazione di idrocarburi alifatici con olefine |
US5500297A (en) | 1993-08-09 | 1996-03-19 | The Trustees Of Princeton University | Electron acceptor compositions technical field |
US5695890A (en) | 1993-08-09 | 1997-12-09 | The Trustees Of Princeton University | Heterolamellar photoelectrochemical films and devices |
US5906892A (en) | 1993-08-09 | 1999-05-25 | The Trustees Of Princeton University | Electron acceptor compositions on polymer templates |
US5430210A (en) | 1993-08-27 | 1995-07-04 | Mobil Oil Corporation | Selective hydrogen combustion processes |
GB9318505D0 (en) | 1993-09-07 | 1993-10-20 | Evc Tech Ag | By-product recycling in oxychlorination process |
GB9318507D0 (en) | 1993-09-07 | 1993-10-20 | Evc Tech Ag | Vinyl chloride production process |
US5371313A (en) | 1993-11-24 | 1994-12-06 | Polysar Rubber Corporation | Purification of hydrocarbon streams |
US5600045A (en) | 1993-12-02 | 1997-02-04 | The Dow Chemical Company | Process for conversion of crude hydrocarbon mixtures |
US5414173A (en) | 1993-12-22 | 1995-05-09 | The Dow Chemical Company | Process of preparing cyclopentadiene and substituted derivatives thereof |
GB9400569D0 (en) | 1994-01-13 | 1994-03-09 | Rhone Poulenc Chemicals | Process for the production of substituted aromatic hydrocarbons from corresponding anilines by dediazoniation |
EP0746529B1 (en) | 1994-02-18 | 2000-01-05 | Chevron Chemical Company LLC | Zeolite ssz-42 |
US5565092A (en) | 1994-03-16 | 1996-10-15 | Exxon Chemical Patents Inc. | Halogen resistant hydrogenation process and catalyst |
US5780703A (en) | 1994-05-02 | 1998-07-14 | Mobil Oil Corporation | Process for producing low aromatic diesel fuel with high cetane index |
US5565616A (en) | 1994-05-09 | 1996-10-15 | Board Of Regents, The University Of Texas System | Controlled hydrothermal processing |
US5444168A (en) | 1994-05-16 | 1995-08-22 | Mobil Oil Corporation | Process for the production of symmetrical ethers from secondary alcohols |
US5401894A (en) | 1994-06-07 | 1995-03-28 | Uop | Process for the treatment of halogenated organic feedstocks |
US5591421A (en) | 1994-07-11 | 1997-01-07 | Chevron U.S.A. Inc. | Zeolite SSZ-41 |
US5523503A (en) | 1994-07-13 | 1996-06-04 | Uop | Cocurrent simulated moving bed hydrocarbon alkylation process |
GB9414972D0 (en) | 1994-07-26 | 1994-09-14 | Bnfl Fluorchem Ltd | Halogenation reactions |
US5661097A (en) | 1994-08-12 | 1997-08-26 | The Dow Chemical Company | Supported olefin polymerization catalyst |
US6015867A (en) | 1994-09-28 | 2000-01-18 | Showa Denko K.K. | 3-alkoxypropionic ester derivative, olefin polymerization catalyst, and process for preparation of polyolefin |
WO1996011227A1 (en) | 1994-10-05 | 1996-04-18 | Great Lakes Chemical Corporation | Continuous bromination process and products thereof |
US6117371A (en) | 1994-10-05 | 2000-09-12 | Great Lakes Chemical Corporation | Continuous bromination process and products thereof |
CA2203115C (en) | 1994-10-20 | 2006-09-19 | Pierluigi Fatutto | Single stage fixed bed oxychlorination of ethylene |
GB2294262B (en) | 1994-10-20 | 1998-07-08 | Evc Tech Ag | Single stage fixed bed oxychlorination of ethylene |
US5489727A (en) | 1994-10-28 | 1996-02-06 | Phillips Petroleum Company | Isopentane disproportionation |
US5693191A (en) | 1994-11-23 | 1997-12-02 | The Dow Chemical Company | Process for recovery of anhydrous hydrogen chloride from mixtures with non-condensable gases |
RU2141937C1 (ru) | 1994-11-24 | 1999-11-27 | Солвей (Сосьете Аноним) | Способ превращения хлорированного алкана в менее хлорированный алкен |
US5639930A (en) | 1995-01-04 | 1997-06-17 | Penick; Joe E. | Process of producing alkylates |
DK171707B1 (da) | 1995-02-03 | 1997-04-01 | Topsoe Haldor As | Fremgangsmåde til fremstilling af dimetylæter i brændstofkvalitet |
US5905169A (en) | 1995-03-20 | 1999-05-18 | E. I. Du Pont De Nemours And Company | Process for producing polyfluoroacyl compositions |
US5600043A (en) | 1995-03-27 | 1997-02-04 | The Geon Company | Oxychlorination process |
DE69614844T2 (de) | 1995-04-21 | 2002-04-11 | Procter & Gamble | Shampoos mit konditionierungsmittel aus unlöslichen silikon, und kationischem polymer |
FR2734172B1 (fr) | 1995-05-19 | 1997-06-20 | Air Liquide | Dispositif et procede de separation de gaz par adsorption |
DE19520612A1 (de) | 1995-06-06 | 1996-12-12 | Bayer Ag | Verfahren zur Herstellung von Benzylalkohol |
US5847224A (en) | 1995-06-23 | 1998-12-08 | Global Octanes Corporation | Method for improving the color of MTBE, ETBE and TAME |
FR2736911A1 (fr) | 1995-07-20 | 1997-01-24 | Inst Francais Du Petrole | Catalyseur liquide d'alkylation aliphatique |
US5977402A (en) | 1995-07-20 | 1999-11-02 | Sumitomo Chemical Company, Limited | Processes for preparing 4-tert.-butylcyclohexanol and 4-tert.-butylcyclohexyl acetate |
US5675052A (en) | 1995-09-15 | 1997-10-07 | The Boc Group, Inc. | Hydrocarbon alkylation process |
US5705712A (en) | 1995-10-05 | 1998-01-06 | Uop | Integrated process for producing diisopropyl ether, an isopropyl tertiary alkyl ether and isopropyl alcohol |
US5705729A (en) | 1995-11-22 | 1998-01-06 | Mobil Oil Corporation | Isoparaffin-olefin alkylation process |
FR2743079B1 (fr) | 1995-12-27 | 1998-02-06 | Inst Francais Du Petrole | Procede et dispositif d'hydrogenation selective par distillation catalytique comportant une zone reactionnelle a co-courant ascendant liquide-gaz |
DE19548876A1 (de) | 1995-12-27 | 1997-07-03 | Bayer Ag | Verfahren zur kontinuierlichen Herstellung von Benzylalkohol |
FR2743510B1 (fr) | 1996-01-11 | 1998-04-03 | Total Raffinage Distribution | Nouveau catalyseur d'alkylation, son procede de preparation et son utilisation dans des procedes d'alkylation |
US6090312A (en) | 1996-01-31 | 2000-07-18 | Ziaka; Zoe D. | Reactor-membrane permeator process for hydrocarbon reforming and water gas-shift reactions |
AU692723B2 (en) | 1996-02-01 | 1998-06-11 | Phillips Petroleum Company | Catalyst composition and process for selecting hydrogenation of diolefins |
US6096933A (en) | 1996-02-01 | 2000-08-01 | Phillips Petroleum Company | Hydrocarbon hydrogenation and catalyst therefor |
DE19603901A1 (de) | 1996-02-03 | 1997-08-07 | Krupp Uhde Gmbh | Verfahren zur Gewinnung von Reinaromaten aus Reformatbenzin und Vorrichtung zur Durchführung des Verfahrens |
SE517561C2 (sv) | 1996-03-04 | 2002-06-18 | Aga Ab | Förfarande och anordning för framställning av en gas genom separation från en gasblandning |
US5663474A (en) | 1996-03-07 | 1997-09-02 | Alliedsignal Inc. | Alkylation process using hydrogen fluoride-containing alkylation catalysts |
US5684213A (en) | 1996-03-25 | 1997-11-04 | Chemical Research & Licensing Company | Method for the preparation of dialkyl ethers |
US5675046A (en) | 1996-04-10 | 1997-10-07 | Showa Denko K.K. | Process for producing perfluorocarbon |
US5898086A (en) | 1996-04-19 | 1999-04-27 | Henkel Corporation | Process for making alkyl ether glycerols |
USRE38493E1 (en) | 1996-04-24 | 2004-04-13 | Questair Technologies Inc. | Flow regulated pressure swing adsorption system |
US6191324B1 (en) | 1996-04-24 | 2001-02-20 | Union Carbide Chemicals & Plastics Technology Corporation | Processes for producing unsaturated alcohols |
US5998686A (en) | 1996-05-29 | 1999-12-07 | Exxon Chemical Patents Inc. | Process for producing aromatic compounds from aliphatic hydrocarbons |
AU3232997A (en) | 1996-06-07 | 1998-01-05 | Chevron U.S.A. Inc. | Zeolite me-utd-1 |
US5720858A (en) | 1996-07-17 | 1998-02-24 | The United States Of America As Represented By The United States Department Of Energy | Method for the photocatalytic conversion of methane |
US5708246A (en) | 1996-08-28 | 1998-01-13 | Battelle Memorial Institute | Method of photocatalytic conversion of C-H organics |
AU4910697A (en) * | 1996-10-17 | 1998-05-11 | Exxon Chemical Patents Inc. | Hydrocarbon conversion using large crystal zeolite catalyst |
HU220573B1 (hu) | 1996-11-18 | 2002-03-28 | AGRO-CHEMIE Növényvédőszer Gyártó, Értékesítő és Forgalmazó Kft. | Eljárás benzil-éterek előállítására |
CN1088449C (zh) | 1996-11-27 | 2002-07-31 | 阿克佐诺贝尔公司 | 烃烷基化方法 |
US5895831A (en) | 1996-12-04 | 1999-04-20 | Uop Llc | Solid catalyst alkylation process |
US6669846B2 (en) | 1996-12-17 | 2003-12-30 | Global Biosciences, Inc. | Wastewater treatment with alkanes |
US7182871B2 (en) | 1996-12-17 | 2007-02-27 | Global Biosciences, Inc. | Wastewater treatment with alkanes |
US5952538A (en) | 1996-12-31 | 1999-09-14 | Exxon Chemical Patents Inc. | Use of short contact time in oxygenate conversion |
JP2001514636A (ja) | 1997-03-07 | 2001-09-11 | ビーエーエスエフ アクチェンゲゼルシャフト | シクロプロピルアセチレンを製造するための改善法 |
US6093306A (en) | 1997-04-07 | 2000-07-25 | Solar Reactor Technologies Inc. | Comprehensive system for utility load leveling, hydrogen production, stack gas cleanup, greenhouse gas abatement, and methanol synthesis |
US5782936A (en) | 1997-04-23 | 1998-07-21 | Suburban Propane, L.P. | Additive compositions for LPG fuel |
SG74047A1 (en) | 1997-04-30 | 2000-07-18 | Mitsubishi Chem Corp | Process for producing alkylene glycol |
US6018088A (en) | 1997-05-07 | 2000-01-25 | Olah; George A. | Superacid catalyzed formylation-rearrangement of saturated hydrocarbons |
US6056804A (en) | 1997-06-30 | 2000-05-02 | Questor Industries Inc. | High frequency rotary pressure swing adsorption apparatus |
EP1004143B1 (en) | 1997-07-11 | 2012-09-05 | University of Southern California | Charge generators in heterolamellar multilayer thin films |
US6465969B1 (en) | 1997-08-04 | 2002-10-15 | Lumimove, Inc. | Electroluminescent display intelligent controller |
US5856584A (en) | 1997-08-06 | 1999-01-05 | The Nutrasweet Company | Preparation of 3,3-dimethylbutyraldehyde by oxidation of 3, 3-dimethylbutanol |
US5928488A (en) | 1997-08-26 | 1999-07-27 | David S. Newman | Electrolytic sodium sulfate salt splitter comprising a polymeric ion conductor |
DK128697A (da) | 1997-11-12 | 1999-05-13 | Niels J Bjerrum | Katalyseproces |
DE19755636A1 (de) | 1997-12-15 | 1999-06-17 | Bayer Ag | Verfahren zur elektrochemischen Aufarbeitung von HCl-Gas zu hochreinem Chlor |
FR2773496B1 (fr) | 1998-01-14 | 2000-03-03 | Inst Francais Du Petrole | Procede de separation par decantation dans plusieurs zones distinctes |
US5882614A (en) * | 1998-01-23 | 1999-03-16 | Exxon Research And Engineering Company | Very low sulfur gas feeds for sulfur sensitive syngas and hydrocarbon synthesis processes |
US5968236A (en) | 1998-02-20 | 1999-10-19 | Bassine; Stuart | Valve free oxygen concentrator |
US6187983B1 (en) | 1998-04-29 | 2001-02-13 | Exxon Chemical Patents Inc | Converting oxygenates to olefins in the presence of electromagnetic energy |
US5983476A (en) | 1998-06-09 | 1999-11-16 | Uop Llc | Conversion of an HF alkylation unit |
US6096932A (en) | 1999-07-27 | 2000-08-01 | E. I. Du Pont De Nemours And Company | Fluorocarbon manufacturing process |
EP0976705A1 (en) | 1998-07-30 | 2000-02-02 | Ube Industries, Ltd. | Method of producing a phenolalkylether compound |
IT1302003B1 (it) | 1998-08-05 | 2000-07-20 | Enitecnologie Spa | Procedimento per la trasformazione selettiva di idrocarburi. |
US6087294A (en) | 1998-08-12 | 2000-07-11 | Kansas State University Research Foundation | Dispersion and stabilization of reactive atoms on the surface of metal oxides |
FR2782280B1 (fr) | 1998-08-12 | 2000-09-22 | Inst Francais Du Petrole | Catalyseurs supportes utilisables dans des reactions de transformation de composes organiques |
US6921597B2 (en) | 1998-09-14 | 2005-07-26 | Questair Technologies Inc. | Electrical current generation system |
AU6291999A (en) | 1998-10-05 | 2000-04-26 | B.F. Goodrich Company, The | Catalyst and methods for polymerizing cycloolefins |
US6903171B2 (en) | 1998-10-05 | 2005-06-07 | Promerus, Llc | Polymerized cycloolefins using transition metal catalyst and end products thereof |
WO2000021912A1 (en) | 1998-10-12 | 2000-04-20 | Great Lakes (Uk) Limited | Preparation of cyclopropylethyne and intermediates for preparation of cyclopropylethyne |
US6127588A (en) | 1998-10-21 | 2000-10-03 | Phillips Petroleum Company | Hydrocarbon hydrogenation catalyst and process |
US6002059A (en) | 1998-10-28 | 1999-12-14 | Mobil Oil Corporation | Process for upgrading natural gas |
DK0999182T3 (da) | 1998-11-02 | 2003-07-14 | Inst Francais Du Petrole | Fremgangsmåde til fremstilling af en zeolit af strukturtypen EUO ved hjælp af kim af zeolitiske materialer og anvendelse heraf som katalysator til isomerisering af aromatiske forbindelser med otte carbonatomer |
EP0999183B1 (fr) | 1998-11-02 | 2003-06-18 | Institut Francais Du Petrole | Procédé de préparation d'une zéolithe de type structural EUO a l'aide de precurseurs du structurant et son utilisation comme catalyseur d'isomerisation des AC8 |
US6130260A (en) | 1998-11-25 | 2000-10-10 | The Texas A&M University Systems | Method for converting natural gas to liquid hydrocarbons |
US6936565B2 (en) | 1999-01-12 | 2005-08-30 | Hyperion Catalysis International, Inc. | Modified carbide and oxycarbide containing catalysts and methods of making and using thereof |
US6239057B1 (en) | 1999-01-15 | 2001-05-29 | Uop Llc | Catalyst for the conversion of low carbon number aliphatic hydrocarbons to higher carbon number hydrocarbons, process for preparing the catalyst and process using the catalyst |
US6114593A (en) | 1999-01-27 | 2000-09-05 | Phillips Petroleum Company | Method for reducing organic fluoride levels in hydrocarbons |
US6417422B1 (en) | 1999-02-22 | 2002-07-09 | Symyx Technologies, Inc. | Ni catalysts and methods for alkane dehydrogenation |
US6143939A (en) | 1999-02-26 | 2000-11-07 | The United States Of America As Represented By The United States Department Of Energy | Method of dehalogenation using diamonds |
DE60024605T2 (de) | 1999-03-23 | 2006-08-24 | Carnegie Mellon University | Katalytische prozesse für die kontrollierte polymerisation von freiradikalischen, copolymerisierbaren monomeren und funktionellpolymersysteme hergestellt davon |
US6248218B1 (en) | 1999-03-25 | 2001-06-19 | Clovis A. Linkous | Closed cycle photocatalytic process for decomposition of hydrogen sulfide to its constituent elements |
US7220391B1 (en) | 1999-03-25 | 2007-05-22 | University Of Central Florida Research Foundation, Inc. | UV photochemical option for closed cycle decomposition of hydrogen sulfide |
US7273957B2 (en) | 1999-05-04 | 2007-09-25 | Catalytic Distillation Technologies | Process for the production of gasoline stocks |
US6545192B2 (en) | 1999-05-11 | 2003-04-08 | Shell Oil Company | Process for separating olefins from saturated hydrocarbons |
FR2793706B1 (fr) | 1999-05-18 | 2001-08-03 | Total Raffinage Distribution | Support catalytique a base d'oxyde d'un metal du groupe ivb de la classification periodique des elements, sa preparation et ses utilisations |
US6727400B2 (en) | 1999-06-08 | 2004-04-27 | Triosyn Holdings, Inc. | Deactivation of toxic chemical agents |
US6406523B1 (en) | 1999-06-09 | 2002-06-18 | Questair Technologies, Inc. | Rotary pressure swing adsorption apparatus |
US6248931B1 (en) | 1999-06-30 | 2001-06-19 | Uop Llc | Membrane process for the recovery of halides from hydrocarbon-containing streams |
SE520971C2 (sv) | 1999-08-20 | 2003-09-16 | Perstorp Ab | Förfarande för tillverkning av en eteralkohol |
US6309453B1 (en) | 1999-09-20 | 2001-10-30 | Xerox Corporation | Colorless compounds, solid inks, and printing methods |
FR2798922B1 (fr) | 1999-09-29 | 2001-12-14 | Inst Francais Du Petrole | Procede de preparation d'une zeolithe de type structural mtt utilisant des germes de materiaux zeolithiques |
FR2798923B1 (fr) | 1999-09-29 | 2001-12-14 | Inst Francais Du Petrole | Procede de preparation d'une zeolithe de type structural mtt utilisant des precurseurs specifiques du structurant |
US20020102672A1 (en) | 1999-10-04 | 2002-08-01 | Joseph Mizrahi | Process for producing a purified lactic acid solution |
DE19949211A1 (de) | 1999-10-13 | 2001-05-31 | Veba Oel Ag | Verfahren zur Herstellung von n-Alkanen aus Mineralölfraktionen und Katalysator zur Durchführung des Verfahrens |
US6372949B1 (en) | 1999-10-15 | 2002-04-16 | Mobil Oil Corporation | Single stage process for converting oxygenates to gasoline and distillate in the presence of undimensional ten member ring zeolite |
US6265505B1 (en) | 1999-11-18 | 2001-07-24 | Univation Technologies, Llc | Catalyst system and its use in a polymerization process |
US6380328B1 (en) | 1999-12-10 | 2002-04-30 | Univation Technologies, Llc | Catalyst systems and their use in a polymerization process |
US6518474B1 (en) | 1999-10-29 | 2003-02-11 | Huntsman International Llc | Process for producing isobutylene from tertiary butyl alcohol |
MXPA02005142A (es) | 1999-11-22 | 2002-11-07 | Dow Chemical Co | Un proceso para la conversion de etileno en cloruro de vinilo, y composiciones catalizadoras novedosas utiles para este proceso. |
US6797845B1 (en) | 1999-11-22 | 2004-09-28 | Dow Global Technologies Inc. | Process for vinyl chloride manufacture from ethane and ethylene with immediate HCl recovery from reactor effluent |
US6909024B1 (en) | 1999-11-22 | 2005-06-21 | The Dow Chemical Company | Process for the conversion of ethylene to vinyl chloride and novel catalyst compositions useful for such process |
US6933417B1 (en) | 1999-11-22 | 2005-08-23 | Dow Global Technologies Inc. | Process for vinyl chloride manufacture from ethane and ethylene with partial CHl recovery from reactor effluent |
US6680415B1 (en) | 1999-11-22 | 2004-01-20 | Dow Global Technologies Inc. | Oxyhalogenation process using catalyst having porous rare earth halide support |
US6514319B2 (en) | 1999-12-09 | 2003-02-04 | Questair Technologies Inc. | Life support oxygen concentrator |
US6956140B2 (en) | 1999-12-14 | 2005-10-18 | Halocarbon Products Corporation | Hydrothermal hydrolysis of halogenated compounds |
EP1108701B1 (en) | 1999-12-14 | 2003-04-23 | Sumitomo Chemical Company Limited | Process for preparing ketone, alcohol and hydroperoxide |
US6376731B1 (en) | 2000-01-14 | 2002-04-23 | Arco Chemical Technology, L.P. | Selective olefin oligomerization |
WO2001056961A1 (fr) | 2000-02-02 | 2001-08-09 | Daikin Industries, Ltd. | Procede de production d'hydrofluorocarbones |
IT1317757B1 (it) | 2000-02-03 | 2003-07-15 | Enitecnologie Spa | Metodo per la preparazione di idrocarburi idrogenati. |
FR2805255B1 (fr) | 2000-02-21 | 2002-04-12 | Inst Francais Du Petrole | Zeolithe mtt comprenant des cristaux et des agregats de cristaux de granulometries specifiques et son utilisation comme catalyseur d'isomerisation des paraffines lineaires |
US6566572B2 (en) | 2000-03-06 | 2003-05-20 | Wako Pure Chemical Industries, Ltd. | Process for producing 9,10-diphenylanthracene |
US6475463B1 (en) | 2000-03-07 | 2002-11-05 | Chevron U.S.A. Inc. | Zeolite SSZ-55 |
US6395945B1 (en) | 2000-03-31 | 2002-05-28 | Phillips Petroleum Company | Integrated hydroisomerization alkylation process |
US6710213B2 (en) | 2000-03-31 | 2004-03-23 | Showa Denko K.K. | Production process and use for propargyl alcohol and its intermediate |
CA2306311C (en) | 2000-04-20 | 2007-04-10 | Quest Air Gases Inc. | Absorbent laminate structures |
FR2808533B1 (fr) | 2000-05-02 | 2002-08-16 | Inst Francais Du Petrole | Huile synthetique a haut indice de viscosite et faible point d'ecoulement |
EP1151980A1 (en) | 2000-05-03 | 2001-11-07 | Solvias AG | Catalytic halogenation of activated methylene and methine compound |
CN100491253C (zh) | 2000-05-31 | 2009-05-27 | 切夫里昂美国公司 | Ssz-53沸石 |
WO2002002490A2 (en) | 2000-06-30 | 2002-01-10 | Chevron U.S.A. Inc. | Synthesis of high quality normal alpha olefins |
FR2812301B1 (fr) | 2000-07-26 | 2003-04-04 | Inst Francais Du Petrole | Procede flexible de production de bases huiles et de distillats moyens a partir de charge contenant des heteroatomes |
IT1318682B1 (it) | 2000-08-11 | 2003-08-27 | Enichem Spa | Procedimento integrato per la preparazione di ossidi olefinici. |
IT1318680B1 (it) | 2000-08-11 | 2003-08-27 | Enichem Spa | Processo per la produzione in continuo di ossidi olefinici. |
US6495484B1 (en) | 2000-08-28 | 2002-12-17 | Univation Technologies, Llc | Catalyst system and its use in a polymerization process |
US6585953B2 (en) | 2000-09-07 | 2003-07-01 | Wisconsin Alumni Research Foundation | Synthesis of 17F labeled fluoroalkanes |
FR2813809B1 (fr) | 2000-09-11 | 2003-07-25 | Air Liquide | Colonne a garnissage d'echange de chaleur et/ou de matiere |
US6518476B1 (en) | 2000-09-18 | 2003-02-11 | Union Carbide Chemicals & Plastics Technology Corporation | Methods for manufacturing olefins from lower alkans by oxidative dehydrogenation |
ZA200108461B (en) | 2000-10-27 | 2002-06-06 | Celanese Chem Europe Gmbh | Process of telomerizing conjugated dienes. |
US6552241B1 (en) | 2000-10-31 | 2003-04-22 | Conocophillips Company | Alkylation process |
TR200401073T4 (tr) | 2000-11-29 | 2004-08-23 | Vinnolit Gmbh & Co. Kg | 1,2-dikloretan'ın hazırlanmasına ilişkin yöntem. |
CA2430271A1 (en) | 2000-12-08 | 2002-06-13 | Questair Technologies Inc. | Methods and apparatuses for gas separation by pressure swing adsorption with partial gas product feed to fuel cell power source |
CA2329475A1 (en) | 2000-12-11 | 2002-06-11 | Andrea Gibbs | Fast cycle psa with adsorbents sensitive to atmospheric humidity |
FR2818284B1 (fr) | 2000-12-15 | 2006-08-04 | Inst Francais Du Petrole | Procede flexible ameliore de production de bases huiles et distillats moyens avec une conversion-hydroisomerisation suivie d'un deparaffinage catalytique |
US6511526B2 (en) | 2001-01-12 | 2003-01-28 | Vbox, Incorporated | Pressure swing adsorption gas separation method and apparatus |
US6538162B2 (en) | 2001-01-30 | 2003-03-25 | Exxonmobil Chemical Patents Inc. | Method for converting alkanes to oxygenates |
US6509485B2 (en) | 2001-02-22 | 2003-01-21 | Sri International | Preparation of epoxides from alkanes using lanthanide-promoted silver catalysts |
KR100519140B1 (ko) | 2001-02-23 | 2005-10-04 | 쇼와 덴코 가부시키가이샤 | 퍼플루오로탄소의 제조방법 및 그 용도 |
US20030196680A1 (en) | 2002-04-19 | 2003-10-23 | Dielectric Systems, Inc | Process modules for transport polymerization of low epsilon thin films |
WO2002094749A1 (en) | 2001-05-23 | 2002-11-28 | Dow Global Technologies Inc. | Production of vinyl halide from single carbon feedstocks |
US6984763B2 (en) | 2001-05-23 | 2006-01-10 | Dow Global Technologies Inc. | Oxidative halogenation and optional dehydrogenation of c3+hydrocarbons |
WO2002094752A1 (en) | 2001-05-23 | 2002-11-28 | Dow Global Technologies Inc. | Process for vinyl chloride manufacture from ethane and ethylene with air feed and alternative hcl processing methods |
EP1527035B1 (en) | 2001-06-08 | 2015-03-04 | Albemarle Netherlands B.V. | Continuous process for the alkylation of hydrocarbons |
US7001872B2 (en) | 2001-06-11 | 2006-02-21 | Halliburton Energy Services, Inc. | Subterranean formation treating fluid and methods of fracturing subterranean formations |
US6440894B1 (en) | 2001-06-25 | 2002-08-27 | Exxonmobil Chemical Patents, Inc. | Methods of removing halogen from non-zeolitic molecular sieve catalysts |
US6518471B1 (en) | 2001-06-25 | 2003-02-11 | Exxonmobil Chemical Patents Inc. | Selective production of meta-diisopropylbenzene |
DE02744727T1 (de) | 2001-06-28 | 2005-02-10 | Honeywell International Inc. | Verfahren zur herstellung eines fluorierungskatalysators |
US20030065239A1 (en) | 2001-06-29 | 2003-04-03 | Peter Zhu | Non-hazardous basic neutralization of aldehydes |
US6646102B2 (en) | 2001-07-05 | 2003-11-11 | Dow Global Technologies Inc. | Process for manufacturing an alpha-dihydroxy derivative and epoxy resins prepared therefrom |
US6616830B2 (en) | 2001-07-13 | 2003-09-09 | Chevron U.S.A. Inc. | Hydrocarbon conversion using zeolite SSZ-57 |
US6547958B1 (en) | 2001-07-13 | 2003-04-15 | Chevron U.S.A. Inc. | Hydrocarbon conversion using zeolite SSZ-59 |
US6540905B1 (en) | 2001-07-13 | 2003-04-01 | Chevron U.S.A. Inc. | Hydrocarbon conversion using zeolite SSZ-58 |
US6867302B2 (en) | 2001-07-13 | 2005-03-15 | Board Of Trustees Of Michigan State University | Process for the catalytic synthesis of biaryls and polymers from aryl compounds |
US7094936B1 (en) | 2001-07-20 | 2006-08-22 | Great Lakes Chemical Corporation | Process for preparing halogenated alkanes |
FR2828193B1 (fr) | 2001-08-03 | 2004-04-02 | Atofina | Nouveau procede de preparation du 1,1,1,-trifluoro-2,2-dichloroethane |
WO2003018524A1 (en) | 2001-08-03 | 2003-03-06 | Eastman Chemical Company | Vapor phase carbonylation process using iridium-gold co-catalysts |
US6858770B2 (en) | 2001-08-21 | 2005-02-22 | Catalytic Distillation Technologies | Paraffin alkylation |
US6797851B2 (en) | 2001-08-30 | 2004-09-28 | Exxonmobil Chemical Patents Inc. | Two catalyst process for making olefin |
US6632971B2 (en) | 2001-08-30 | 2003-10-14 | Exxonmobil Chemical Patents Inc. | Process for converting natural gas to higher value products using a methanol refinery remote from the natural gas source |
US6552238B1 (en) | 2001-08-31 | 2003-04-22 | Vulcan Chemicals | Separation of heavy ends from streams of halogenated alkanes |
WO2003022827A1 (en) | 2001-09-11 | 2003-03-20 | Grt, Inc. | Process for synthesizing olefin oxides |
CN1286788C (zh) | 2001-09-14 | 2006-11-29 | 东曹氟技术株式会社 | 2,2,2-三氟乙醇的制造方法 |
JP4014856B2 (ja) | 2001-11-14 | 2007-11-28 | 株式会社トクヤマ | ジハロゲン化アダマンタンの製造方法 |
AU2002365968A1 (en) | 2001-11-19 | 2003-06-10 | Merck And Co., Inc. | Process for the synthesis of (r)-1-(3,5-bis(trifluoromethyl)-phenyl)ethan-1-ol and esters thereof by dynamic kinetic resolution |
ZA200209011B (en) | 2001-11-20 | 2003-05-26 | Rohm & Haas | Electroactive catalysis. |
DE10159615A1 (de) | 2001-12-05 | 2003-06-12 | Basf Ag | Verfahren zur Herstellung von 1,2-Dichlorethan |
US7199255B2 (en) | 2001-12-18 | 2007-04-03 | Univation Technologies, Llc | Imino-amide catalysts for olefin polymerization |
US6844447B2 (en) | 2001-12-18 | 2005-01-18 | Metabolix Inc. | Methods of making intermediates from polyhydroxyalkanoates |
CA2471295C (en) | 2002-01-24 | 2010-08-10 | Grt, Inc. | Integrated process for synthesizing alcohols, ethers, and olefins from alkanes |
WO2003062143A1 (en) | 2002-01-25 | 2003-07-31 | Council Of Scientific And Industrial Research | Preparation of non-hazardous brominating reagents |
US7091270B2 (en) | 2002-01-31 | 2006-08-15 | Bromine Compounds Ltd. | Pentabromobenzyl alkyl ethers and their use as fire retardants |
WO2003078366A1 (en) | 2002-03-13 | 2003-09-25 | University Of Florida | Process for trifluoromethylation of sulfates |
AU2003209894A1 (en) | 2002-03-14 | 2003-09-22 | Questair Technologies Inc. | Gas separation by combined pressure swing and displacement purge |
US20040152929A1 (en) | 2002-05-08 | 2004-08-05 | Clarke William D | Process for vinyl chloride manufacture from ethane and ethylene with air feed and alternative hcl processing methods |
WO2004039918A2 (en) | 2002-05-10 | 2004-05-13 | Wisconsin Alumni Research Foundation | Low-temperature hydrocarbon production from oxygenated hydrocarbons |
US6545191B1 (en) | 2002-06-13 | 2003-04-08 | John E. Stauffer | Process for preparing ethanol |
EP1386664B1 (en) | 2002-07-31 | 2016-05-11 | Ineos Technologies (Vinyls) Limited | A hollow parallelepiped pellet suitable as carrier of catalysts for selective exothermic reactions |
KR100986958B1 (ko) | 2002-07-31 | 2010-10-11 | 다이소 가부시키가이샤 | 광학활성 할로게노히드록시프로필 화합물 및 글리시딜화합물의 제조법 |
US7238846B2 (en) | 2002-08-14 | 2007-07-03 | Exxonmobil Chemical Patents Inc. | Conversion process |
US6831032B2 (en) | 2002-08-19 | 2004-12-14 | Novolen Technology Holdings C.V. | Ziegler-Natta catalyst and methods of making and using same |
AU2003265591A1 (en) | 2002-08-22 | 2004-03-11 | E.I. Du Pont De Nemours And Company | Cobalt-substituted chromium oxide compositions, their preparation, and their use as catalysts and catalyst precursors |
US6953870B2 (en) | 2002-08-26 | 2005-10-11 | Tsoung Y Yan | Self-propelled liquid fuel |
US6753390B2 (en) | 2002-09-04 | 2004-06-22 | Univation Technologies, Llc | Gas phase polymerization process |
DE10242223A1 (de) | 2002-09-12 | 2004-03-25 | Clariant Gmbh | Verfahren zur Hydrodechlorierung von kernchlorierten ortho-Xylolen |
US6740146B2 (en) | 2002-09-12 | 2004-05-25 | Edward L. Simonds | Oxygen concentrator |
KR100531128B1 (ko) | 2002-09-26 | 2005-11-28 | 한국화학연구원 | 분리막 반응기를 이용한 디메틸에테르의 제조방법 |
FR2845077A1 (fr) | 2002-09-26 | 2004-04-02 | Atofina | Procede d'abaissement de la teneur en matieres organiques et produits azotes contenus dans des effluents bromures |
US6852896B2 (en) | 2002-10-11 | 2005-02-08 | John E. Stauffer | Concerted process for the production of an alkenyl substituted aromatic compound |
US6869903B2 (en) | 2002-11-07 | 2005-03-22 | Univation Technologies, Llc | Synthesis of polymerization catalyst components |
US7060865B2 (en) | 2002-11-12 | 2006-06-13 | Exxonmobil Chemical Patents Inc. | Recovery of C4 olefins from a product stream comprising C4 olefins, dimethyl ether and C5+ hydrocarbons |
CN1203032C (zh) | 2002-11-12 | 2005-05-25 | 石油大学(北京) | 以复合离子液体为催化剂制备烷基化油剂的方法 |
US7199083B2 (en) | 2002-12-06 | 2007-04-03 | Self Generating Foam Incoporated | Self-generating foamed drilling fluids |
DE10257499A1 (de) | 2002-12-10 | 2004-07-01 | Oxeno Olefinchemie Gmbh | Verfahren zur Herstellung von 1-Olefinen durch katalytische Spaltung von 1-Alkoxyalkanen |
US7232872B2 (en) | 2002-12-20 | 2007-06-19 | Exxonmobil Chemical Patents Inc. | Polymerization processes |
CA2510864C (en) | 2002-12-20 | 2013-01-22 | Exxonmobil Chemical Patents Inc. | Polymers substantially free of long chain branching |
EP1440939A1 (en) | 2003-01-07 | 2004-07-28 | Humboldt-Universität zu Berlin | Method for the preparation of amorphous metal fluorides |
DE10303304A1 (de) | 2003-01-28 | 2004-07-29 | Ruhrgas Ag | Verfahren zum Herstellen nichtaromatischer Kohlenwassersstoffe |
US7265193B2 (en) | 2003-01-31 | 2007-09-04 | Exxonmobil Chemical Patents Inc. | Polymerization process |
US20040158108A1 (en) | 2003-02-06 | 2004-08-12 | Snoble Karel A.J. | Purification of alcohol |
KR100501922B1 (ko) | 2003-02-19 | 2005-07-18 | 에스케이 주식회사 | 메탄올로부터 디메틸에테르의 제조방법 |
US6875339B2 (en) | 2003-03-07 | 2005-04-05 | Conocophillips Company | Octane improvement of a hydrocarbon stream |
US7091391B2 (en) | 2003-03-19 | 2006-08-15 | Stauffer John E | Methane to olefins |
FR2852866B1 (fr) | 2003-03-25 | 2006-07-14 | Bp Lavera Snc | Compose metallique fixe sur un support, procede de preparation et utilisation du compose dans des reactions de metathese d'hydrocarbure |
US7083714B2 (en) | 2003-03-26 | 2006-08-01 | Chevron U.S.A. Inc. | Hydrocarbon conversion using molecular sieve SSZ-65 |
US7011811B2 (en) | 2003-03-26 | 2006-03-14 | Chevron U.S.A. Inc. | Molecular sieve SSZ-65 composition of matter and synthesis thereof |
US20040188324A1 (en) | 2003-03-26 | 2004-09-30 | Saleh Elomari | Hydrocarbon conversion using molecular sieve SSZ-65 |
US20040187684A1 (en) | 2003-03-26 | 2004-09-30 | Saleh Elomari | Using molecular sieve SSZ-65 for reduction of oxides of nitrogen in a gas stream |
US7301060B2 (en) | 2003-03-28 | 2007-11-27 | Ab-Cwt, Llc | Process for conversion of organic, waste, or low-value materials into useful products |
US20040220433A1 (en) | 2003-03-28 | 2004-11-04 | Evert Van Der Heide | Process for the preparation of propylene glycol |
JP4111035B2 (ja) | 2003-03-31 | 2008-07-02 | 日本ゼオン株式会社 | 重合トナーの製造方法 |
US6822123B2 (en) | 2003-04-02 | 2004-11-23 | John E. Stauffer | Formaldehyde process |
EP1622857B1 (en) | 2003-04-09 | 2011-10-05 | Shell Internationale Research Maatschappij B.V. | Process for the preparation of alkanediol |
US7057081B2 (en) | 2003-05-09 | 2006-06-06 | Conocophillips Company | Method for treating alkanes |
US6953868B2 (en) | 2003-06-05 | 2005-10-11 | Dow Global Technologies Inc. | Oxyfunctionalization of polyolefins |
WO2005069751A2 (en) | 2003-06-21 | 2005-08-04 | Richards Alan K | Anhydrous processing of methane into methane-sulfonic acid, methanol, and other compounds |
US7193093B2 (en) | 2003-06-30 | 2007-03-20 | Shell Oil Company | Process for producing alkylene oxide |
UA84436C2 (ru) | 2003-08-08 | 2008-10-27 | Солвей (Сосьетэ Аноним) | Способ регенерации катализатора гидрирования и способ получения мономера винилхлорида |
DE10338581A1 (de) | 2003-08-22 | 2005-03-17 | Oxeno Olefinchemie Gmbh | Verfahren zur Erzeugung von tert.-Butanol |
US6958306B2 (en) | 2003-08-28 | 2005-10-25 | Univation Technologies, Llc | Activated catalyst systems from substituted dialuminoxane complexes |
GB0320684D0 (en) | 2003-09-03 | 2003-10-01 | Bp Chem Int Ltd | Process |
US7045670B2 (en) | 2003-09-03 | 2006-05-16 | Synfuels International, Inc. | Process for liquid phase hydrogenation |
US6825383B1 (en) | 2003-09-22 | 2004-11-30 | Council Of Scientific And Industrial Research | Catalytic process for regiospecific chlorination of alkanes, alkenes and arenes |
US7105710B2 (en) | 2003-09-26 | 2006-09-12 | Shell Oil Company | Process of preparing an alkylene glycol |
US7479575B2 (en) | 2003-10-13 | 2009-01-20 | Laboratoires Serono Sa | Method for preparing para-phenyl alkynyl benzaldehydes |
US7335802B2 (en) | 2003-10-15 | 2008-02-26 | Shell Oil Company | Methods of preparing branched aliphatic alcohols |
WO2005035121A2 (en) | 2003-10-16 | 2005-04-21 | Universiteit Gent | Schiff base metal complexes for use as catalysts in organic synthesis |
US6838576B1 (en) | 2003-10-23 | 2005-01-04 | 3M Innovative Properties Company | Process for preparing functional group-containing olefinic compounds |
US7196239B2 (en) | 2003-11-19 | 2007-03-27 | Exxonmobil Chemical Patents Inc. | Methanol and ethanol production for an oxygenate to olefin reaction system |
EP1689728B1 (en) | 2003-11-28 | 2007-04-11 | Firmenich Sa | Musk odorant compounds |
WO2005054120A2 (en) | 2003-12-05 | 2005-06-16 | Idaho Research Foundation, Inc. | Polymer-supported metal nanoparticles and method for their manufacture and use |
US7244795B2 (en) | 2003-12-08 | 2007-07-17 | Univation Technologies, Llc | Polymerization process using metallocene catalyst systems |
WO2005056525A2 (en) | 2003-12-09 | 2005-06-23 | Bio-Technical Resources | Deacetylation of n-acetylglucosamine |
CN1894183B (zh) | 2003-12-18 | 2010-09-08 | 埃克森美孚化学专利公司 | 氢化或相关方面的改进 |
US7064238B2 (en) | 2004-01-02 | 2006-06-20 | Marathon Oil Company | Conversion of alkanes to oxygenates |
FR2865731B1 (fr) | 2004-01-30 | 2007-09-07 | Solvay | Procede de fabrication d'un hydrofluoroalcane |
FR2866023B1 (fr) | 2004-02-05 | 2007-10-12 | Rhodia Chimie Sa | Procede de preparation d'un compose fluoaromatique a partir d'un compose aminoaromatique |
EP1723093A4 (en) | 2004-03-12 | 2008-03-12 | Univ Utah | CYCLONE REACTOR AND ASSOCIATED PROCEDURES |
WO2005095310A2 (en) | 2004-03-23 | 2005-10-13 | Shell Internationale Research Maatschappij B.V. | The utilization of zirconium and zirconium based alloys for the containment of halogen containing environments used in the production of olefins, alcohols, ethers, ethoxylates glycols, and olefin oxides from alkanes |
JP4452130B2 (ja) | 2004-04-05 | 2010-04-21 | 東洋エンジニアリング株式会社 | 液化天然ガスからの炭化水素分離方法および分離装置 |
US20080275284A1 (en) | 2004-04-16 | 2008-11-06 | Marathon Oil Company | Process for converting gaseous alkanes to liquid hydrocarbons |
US20060100469A1 (en) | 2004-04-16 | 2006-05-11 | Waycuilis John J | Process for converting gaseous alkanes to olefins and liquid hydrocarbons |
US8173851B2 (en) | 2004-04-16 | 2012-05-08 | Marathon Gtf Technology, Ltd. | Processes for converting gaseous alkanes to liquid hydrocarbons |
US7674941B2 (en) | 2004-04-16 | 2010-03-09 | Marathon Gtf Technology, Ltd. | Processes for converting gaseous alkanes to liquid hydrocarbons |
KR101170773B1 (ko) | 2004-04-16 | 2012-08-03 | 마라톤 지티에프 테크놀로지 엘티디. | 기체상 알칸을 액상 탄화수소로 전환시키는 방법 |
US7244867B2 (en) | 2004-04-16 | 2007-07-17 | Marathon Oil Company | Process for converting gaseous alkanes to liquid hydrocarbons |
EP1742875A1 (en) | 2004-04-20 | 2007-01-17 | Uop Llc | Crystalline aluminosilicate zeolitic composition: uzm-15 |
US7462752B2 (en) | 2004-04-21 | 2008-12-09 | Shell Oil Company | Process to convert linear alkanes into alpha olefins |
US7091387B2 (en) | 2004-04-21 | 2006-08-15 | Shell Oil Company | Process to convert alkanes into primary alcohols |
DE602004028766D1 (de) | 2004-04-23 | 2010-09-30 | Uop Llc | Siliciumreiche zeolithe uzm-5hs |
WO2005110953A1 (en) | 2004-04-30 | 2005-11-24 | Shell Internationale Research Maatschappij B.V. | Derivatives of alcohols and olefins |
US7435760B2 (en) | 2004-05-14 | 2008-10-14 | Battelle Memorial Institute | Method of generating hydrocarbon reagents from diesel, natural gas and other logistical fuels |
EP1765489B1 (en) | 2004-06-16 | 2009-11-11 | Dow Global Technologies Inc. | Apparatus and method for ziegler-natta research |
KR100888124B1 (ko) | 2004-06-23 | 2009-03-11 | 가부시끼가이샤 도꾸야마 | 폴리할로겐화 디아만탄류 및 그의 유도체의 제조 방법 |
DE102004030943B4 (de) | 2004-06-26 | 2013-10-02 | Evonik Oxeno Gmbh | Verfahren zur Herstellung von tert.-Butanol aus Isobuten-haltigen Kohlenwasserstoffgemischen |
KR101226291B1 (ko) | 2004-07-21 | 2013-01-25 | 다우 글로벌 테크놀로지스 엘엘씨 | 다중히드록시화-지방족 탄화수소 또는 그의 에스테르의 클로로히드린으로의 전환 |
US7429683B2 (en) | 2004-07-27 | 2008-09-30 | Eastman Kodak Company | Process of maing naphthacene from propargyl alcohol |
US7671248B2 (en) | 2004-08-13 | 2010-03-02 | Exxonmobil Chemical Patents Inc. | Process for producing sec-butyl benzene |
US7371916B1 (en) | 2004-09-16 | 2008-05-13 | Uop Llc | Conversion of an alcoholic oxygenate to propylene using moving bed technology and an etherification step |
US7271303B1 (en) | 2004-09-22 | 2007-09-18 | Uop Llc | Multi-zone process for the production of diesel and aromatic compounds |
JP2008514540A (ja) | 2004-09-30 | 2008-05-08 | シェブロン ユー.エス.エー. インコーポレイテッド | モレキュラーシーブssz−65 |
DE602005019081D1 (de) | 2004-10-15 | 2010-03-11 | Toagosei Co Ltd | Verfahren zur herstellung eines metalloxidkatalysators |
GB0423586D0 (en) | 2004-10-22 | 2004-11-24 | United States Borax Inc | Selective oxidation of organic compounds |
CA2586971C (en) | 2004-11-12 | 2013-07-23 | Velocys Inc. | Process using microchannel technology for conducting alkylation or acylation reaction |
TWI332418B (en) | 2004-11-18 | 2010-11-01 | Rohm & Haas | Hybrid catalyst systems and hybrid process for converting alkanes to alkenes and to their corresponding oxygenated products |
EP1824599B1 (en) | 2004-12-21 | 2020-06-17 | Albemarle Netherlands B.V. | Attrition-resistant catalyst, a process for its preparation and its use |
EP3456409B1 (en) | 2004-12-22 | 2020-05-13 | Chemtor, Lp | Use of fiber film reactors to produce biodiesel |
EP1843839A2 (en) | 2004-12-22 | 2007-10-17 | E.I. Dupont De Nemours And Company | Copolymers of perfluoro (alkyl venyl ether) for photochemical reactor, process for increasing fluorine content and production of olefinic compound by photochlorination |
AU2005318152B2 (en) | 2004-12-23 | 2011-10-13 | Solvay (Societe Anonyme) | Process for the manufacture of 1,2-dichloroethane |
BRPI0518650A2 (pt) | 2004-12-23 | 2008-12-02 | Solvay | processos para a manufatura de 1, 2-dicloro-etano partindo de uma fonte de hidrocarbonetos, para a manufatura de cloreto de vinila, e de poli(cloreto de vinila) |
JP2008525377A (ja) | 2004-12-23 | 2008-07-17 | ソルヴェイ(ソシエテ アノニム) | 1,2−ジクロロエタンの製造方法 |
CN103396287B (zh) | 2004-12-23 | 2015-10-07 | 索维公司 | 制造1,2-二氯乙烷的方法 |
US7537685B2 (en) | 2004-12-23 | 2009-05-26 | Chevron U.S.A. Inc. | Hydrocarbon conversion using molecular sieve SSZ-71 |
WO2006071354A1 (en) | 2004-12-23 | 2006-07-06 | Chevron U.S.A. Inc. | Molecular sieve ssz-70 composition of matter and synthesis thereof |
ZA200705543B (en) | 2004-12-23 | 2009-01-28 | Chevron Usa Inc | Molecular sieve SSZ-70 composition of matter and synthesis thereof |
DE102005003109B4 (de) | 2005-01-22 | 2015-02-12 | Air Liquide Global E&C Solutions Germany Gmbh | Verfahren zur Herstellung von synthetischen Kraftstoffen aus Oxigenaten |
US7253328B2 (en) | 2005-01-24 | 2007-08-07 | John Stauffer | Method for producing vinyl chloride monomer |
WO2006104909A2 (en) | 2005-03-28 | 2006-10-05 | Shell Internationale Research Maatschappij B.V. | Catalytic distillation process for primary haloalkanes |
JP5155852B2 (ja) | 2005-04-15 | 2013-03-06 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | アリール−エチレン置換芳香族化合物および有機半導体としてのその使用 |
ITMI20050723A1 (it) | 2005-04-21 | 2006-10-22 | Consiglio Nazionale Ricerche | Metodo di produzione del biodiesel |
KR20080009707A (ko) | 2005-05-04 | 2008-01-29 | 다우 글로벌 테크놀로지스 인크. | C1 탄화수소를 할로겐화 c1 탄화수소로 산화성할로겐화시키는 방법 |
US20080194850A1 (en) | 2005-05-20 | 2008-08-14 | Solvay (Societe Anonyme) | Method for Making an Epoxide Starting with a Polyhydroxylated Aliphatic Hydrocarbon and a Chlorinating Agent |
WO2007017900A2 (en) | 2005-05-26 | 2007-02-15 | Sisir Kumar Mandal | Preparation of para dichlorobenzene from benzene or mono chlorobenzene |
US20060270863A1 (en) | 2005-05-27 | 2006-11-30 | Amyris Biotechnologies | Conversion of amorpha-4,11-diene to artemisinin and artemisinin precursors |
CA2510093C (en) | 2005-06-16 | 2009-09-29 | Apotex Pharmachem Inc. | Novel process for the preparation of.alpha.-chlorovinyl, .alpha.,.alpha.-dichloro, and acetylenes from ketones |
US7390395B2 (en) | 2005-06-23 | 2008-06-24 | Saleh Elomari | Hydrocarbon conversion using molecular sieve SSZ-56 |
US7226576B2 (en) | 2005-06-23 | 2007-06-05 | Chevron U.S.A. Inc. | Molecular sieve SSZ-56 composition of matter and synthesis thereof |
US7442354B2 (en) | 2005-06-23 | 2008-10-28 | Chevron U.S.A. Inc. | Treatment of engine exhaust using molecular sieve SSZ-56 |
US7226569B2 (en) | 2005-06-23 | 2007-06-05 | Chevron U.S.A. Inc. | Reduction of oxides of nitrogen in a gas stream using molecular sieve SSZ-56 |
WO2007001934A2 (en) | 2005-06-23 | 2007-01-04 | Chevron U.S.A. Inc. | Molecular sieve ssz-56 composition of matter and synthesis thereof |
US7084308B1 (en) | 2005-07-29 | 2006-08-01 | Stauffer John E | Manufacture of formaldehyde from methyl bromide |
US8957259B2 (en) | 2005-09-30 | 2015-02-17 | Battelle Memorial Institute | Dimethyl ether production from methanol and/or syngas |
WO2007044139A1 (en) | 2005-10-07 | 2007-04-19 | Badger Licensing Llc | Bisphenol-a plant yield enhancement |
US7683230B2 (en) | 2005-10-27 | 2010-03-23 | Stauffer John E | Methyl bromide to olefins |
US20070118007A1 (en) | 2005-10-28 | 2007-05-24 | Fong Howard L | Internal olefins process |
WO2007071046A1 (en) | 2005-12-21 | 2007-06-28 | University Of Saskatchewan | Process for the preparation of biodiesel |
US20070213545A1 (en) | 2005-12-22 | 2007-09-13 | Bolk Jeroen W | Method Of Installing An Epoxidation Catalyst In A Reactor, A Method Of Preparing An Epoxidation Catalyst, An Epoxidation Catalyst, A Process For The Preparation Of An Olefin Oxide Or A Chemical Derivable From An Olefin Oxide, And A Reactor Suitable For Such A Process |
US20070197801A1 (en) | 2005-12-22 | 2007-08-23 | Bolk Jeroen W | Method of installing an epoxidation catalyst in a reactor, a method of preparing an epoxidation catalyst, an epoxidation catalyst, a process for the preparation of an olefin oxide or a chemical derivable from an olefin oxide, and a reactor suitables for such a process |
WO2007079038A2 (en) | 2005-12-28 | 2007-07-12 | Chevron U.S.A Inc. | Molecular sieve ssz-74 composition of matter and synthesis thereof |
US7473807B2 (en) | 2005-12-28 | 2009-01-06 | Chevron Usa, Inc. | Acylation using molecular sieve SSZ-74 |
US7432402B2 (en) | 2005-12-28 | 2008-10-07 | Chevron U.S.A. | Partial oxidation using molecular sieve SSZ-74 |
US7762059B2 (en) | 2005-12-28 | 2010-07-27 | Chevron U.S.A. Inc. | Treatment of engine exhaust using molecular sieve SSZ-74 |
US7422732B2 (en) | 2005-12-28 | 2008-09-09 | Chevron U.S.A. Inc | Synthesis of amines using molecular sieve SSZ-74 |
US7357904B2 (en) | 2005-12-28 | 2008-04-15 | Chevron Corporation | Reduction of oxides of nitrogen in a gas stream using molecular sieve SSZ-74 |
US7510697B2 (en) | 2005-12-28 | 2009-03-31 | Chevron U.S.A. Inc. | Molecular sieve SSZ-74 composition of matter and synthesis thereof |
US20080115666A1 (en) | 2005-12-28 | 2008-05-22 | Chevron U.S.A. Inc. | Gas separation using molecular sieve ssz-74 |
US20070149778A1 (en) | 2005-12-28 | 2007-06-28 | Chevron U.S.A. Inc. | Beckmann rearrangement using molecular sieve ssz-74 |
EA020442B1 (ru) | 2006-02-03 | 2014-11-28 | ДжиАрТи, ИНК. | Способ превращения углеводородного сырья (варианты) и система для его осуществления |
GB0602424D0 (en) | 2006-02-07 | 2006-03-22 | Sinclair Pharmaceuticals Ltd | Compounds |
CA2645218C (en) | 2006-03-23 | 2014-10-07 | Anna Lee Tonkovich | Process for making styrene using microchannel process technology |
EP1837320A1 (en) | 2006-03-23 | 2007-09-26 | ETH Zürich | Production of saturated C2 to C5 hydrocarbons |
JP2007269708A (ja) | 2006-03-31 | 2007-10-18 | Sumitomo Chemical Co Ltd | 第3級オレフィンおよび脂肪族アルコールの製造方法 |
US20070238905A1 (en) | 2006-04-05 | 2007-10-11 | Victor Manuel Arredondo | Processes for converting glycerol to glycerol ethers |
BRPI0601460B1 (pt) | 2006-04-26 | 2015-11-10 | Petroleo Brasileiro Sa | processo para hidroconversão de mistura de óleos orgânicos de diferentes origens |
JP5322307B2 (ja) | 2006-05-08 | 2013-10-23 | エクソンモービル・ケミカル・パテンツ・インク | 改善された触媒組成物 |
EP2029511A1 (en) | 2006-05-08 | 2009-03-04 | ExxonMobil Chemical Patents Inc. | Organic compound conversion process |
US7268263B1 (en) | 2006-05-18 | 2007-09-11 | Uop Llc | Integrated process for aromatics production |
US7304193B1 (en) | 2006-05-18 | 2007-12-04 | Uop Llc | Integrated process for aromatics production |
WO2007141295A1 (en) | 2006-06-08 | 2007-12-13 | High Point Pharmaceuticals, Llc | Process for preparing phenoxy acetic acid derivatives |
WO2007146622A2 (en) | 2006-06-08 | 2007-12-21 | Chevron U.S.A. Inc. | Molecular sieve ssz-75 composition of matter and synthesis thereof |
US7906099B2 (en) | 2006-06-09 | 2011-03-15 | Exxonmobil Chemical Patents Inc. | Intergrown molecular sieve, its synthesis and its use in the conversion of oxygenates to olefins |
RU2009114847A (ru) | 2006-09-21 | 2010-10-27 | Альбермарл Корпорейшн (Us) | Способы превращения метана в пригодные углеводороды, катализаторы для применения в таких способах и регенерация катализаторов |
US20090247804A1 (en) | 2006-09-21 | 2009-10-01 | Albemarle Corporation | Methods for conversion of methane to useful hydrocarbons and catalysts for use therein |
BRPI0810060A2 (pt) | 2007-02-28 | 2014-10-21 | Albemarle Corp | Processos para produizir hidrocarbonetos mais altos de metano e bromo |
WO2008157045A1 (en) | 2007-06-14 | 2008-12-24 | Albemarle Corporation | Processes for producing higher hydrocarbons from hydrocarbon feed sources |
WO2008157044A1 (en) | 2007-06-14 | 2008-12-24 | Albemarle Corporation | Processes for producing higher hydrocarbons from methane |
WO2008157047A1 (en) | 2007-06-14 | 2008-12-24 | Albemarle Corporation | Processes for producing hydrogen from hydrocarbon feed sources |
WO2008157046A1 (en) | 2007-06-14 | 2008-12-24 | Albemarle Corporation | Processes for producing higher hydrocarbons from methane |
WO2008157043A1 (en) | 2007-06-14 | 2008-12-24 | Albemarle Corporation | Processes for producing higher hydrocarbons from methane |
US8282810B2 (en) | 2008-06-13 | 2012-10-09 | Marathon Gtf Technology, Ltd. | Bromine-based method and system for converting gaseous alkanes to liquid hydrocarbons using electrolysis for bromine recovery |
US20090312586A1 (en) | 2008-06-13 | 2009-12-17 | Marathon Gtf Technology, Ltd. | Hydrogenation of multi-brominated alkanes |
AU2009302627A1 (en) | 2008-10-07 | 2010-04-15 | Shell Internationale Research Maatschappij B.V. | An integrated process to coproduce aromatic hydrocarbons and ethylene and propylene |
BRPI1008335A2 (pt) * | 2009-02-10 | 2016-02-23 | Ind Origami Inc | folha de material com estruturas de controle de curvatura e método |
US20110015458A1 (en) | 2009-07-15 | 2011-01-20 | Marathon Gtf Technology, Ltd. | Conversion of hydrogen bromide to elemental bromine |
-
2005
- 2005-10-19 US US11/254,438 patent/US20060100469A1/en not_active Abandoned
-
2006
- 2006-09-13 NZ NZ567480A patent/NZ567480A/en not_active IP Right Cessation
- 2006-09-13 ZA ZA200803330A patent/ZA200803330B/xx unknown
- 2006-09-13 JP JP2008536583A patent/JP5396082B2/ja not_active Expired - Fee Related
- 2006-09-13 MY MYPI20081159 patent/MY151088A/en unknown
- 2006-09-13 UA UAA200806734A patent/UA105476C2/uk unknown
- 2006-09-13 EA EA200801115A patent/EA022696B1/ru not_active IP Right Cessation
- 2006-09-13 AU AU2006302939A patent/AU2006302939B2/en not_active Ceased
- 2006-09-13 BR BRPI0617707-7A patent/BRPI0617707A2/pt not_active Application Discontinuation
- 2006-09-13 AP AP2008004417A patent/AP2008004417A0/xx unknown
- 2006-09-13 CA CA2625459A patent/CA2625459C/en not_active Expired - Fee Related
- 2006-09-13 WO PCT/US2006/035788 patent/WO2007046986A2/en active Application Filing
- 2006-09-13 EP EP06814642A patent/EP1945598A4/en not_active Withdrawn
- 2006-09-13 CN CN2006800390646A patent/CN101291891B/zh not_active Expired - Fee Related
- 2006-09-13 KR KR1020087009389A patent/KR101363300B1/ko not_active IP Right Cessation
- 2006-10-16 PE PE2006001251A patent/PE20070737A1/es not_active Application Discontinuation
- 2006-10-19 AR ARP060104577A patent/AR058123A1/es unknown
-
2008
- 2008-04-10 EC EC2008008361A patent/ECSP088361A/es unknown
- 2008-04-16 EG EG2008040622A patent/EG26651A/en active
- 2008-04-18 TN TNP2008000176A patent/TNSN08176A1/en unknown
- 2008-04-30 US US12/112,926 patent/US8008535B2/en not_active Expired - Lifetime
- 2008-05-16 NO NO20082252A patent/NO20082252L/no not_active Application Discontinuation
Patent Citations (74)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3172915A (en) * | 1965-03-09 | Preparation of oxygenated methane derivatives | ||
US2168260A (en) * | 1934-11-11 | 1939-08-01 | Ig Farbenindustrie Ag | Process of preparing monohalogenation products |
US2246082A (en) * | 1939-08-22 | 1941-06-17 | Shell Dev | Preparation of alkyl halides |
US2488083A (en) * | 1946-06-18 | 1949-11-15 | Socony Vacuum Oil Co Inc | Manufacture of liquid hydrocarbons |
US2677598A (en) * | 1953-01-19 | 1954-05-04 | Dow Chemical Co | Oxidation of ferrous halides to form ferric halides |
US2941014A (en) * | 1954-08-06 | 1960-06-14 | Hoechst Ag | Manufacture of alkyl chlorination products |
US3562321A (en) * | 1961-10-10 | 1971-02-09 | Sun Oil Co | Preparation of oxygenated hydrocarbons |
US3246043A (en) * | 1962-12-12 | 1966-04-12 | Universal Oil Prod Co | Preparation of olefinic hydrocarbons |
US3273964A (en) * | 1963-02-28 | 1966-09-20 | Universal Oil Prod Co | Process for producing bromine from a mixture of hydrogen bromide and olefinic hydrocarbon |
US3310380A (en) * | 1964-02-13 | 1967-03-21 | Universal Oil Prod Co | Bromine recovery |
US3353916A (en) * | 1966-04-25 | 1967-11-21 | Universal Oil Prod Co | Quantitative recovery of bromine by two stage catalytic oxidation of hydrogen bromide |
US3598876A (en) * | 1967-11-13 | 1971-08-10 | Universal Oil Prod Co | Selective halogenation of hydrocarbons |
US3702886A (en) * | 1969-10-10 | 1972-11-14 | Mobil Oil Corp | Crystalline zeolite zsm-5 and method of preparing the same |
US3876715A (en) * | 1972-12-01 | 1975-04-08 | Gulf Research Development Co | Process for preparing 2,3-dibromo-2-alkylalkanes |
US4347391A (en) * | 1973-06-11 | 1982-08-31 | Stauffer Chemical Company | Process for preparing ethylene dichloride |
US3894107A (en) * | 1973-08-09 | 1975-07-08 | Mobil Oil Corp | Conversion of alcohols, mercaptans, sulfides, halides and/or amines |
US3894105A (en) * | 1973-08-09 | 1975-07-08 | Mobil Oil Corp | Production of durene |
US4006169A (en) * | 1976-02-26 | 1977-02-01 | Smithkline Corporation | Epoxidation of α,β-ethylenic ketones |
US4197420A (en) * | 1977-07-18 | 1980-04-08 | Sebastiano Cesca | Method for producing oligomers from straight-chain alpha olefins, subsequently hydrogenating such oligomers and saturated products so obtained |
US4496752A (en) * | 1979-05-03 | 1985-01-29 | The Lummus Company | Production of epoxy compounds from olefinic compounds |
US4333852A (en) * | 1980-09-25 | 1982-06-08 | Union Carbide Corporation | Catalyst for the selective production of ethanol and methanol directly from synthesis gas |
US4301253A (en) * | 1980-09-25 | 1981-11-17 | Union Carbide Corporation | Process for the selective production of ethanol and methanol directly from synthesis gas |
US4373109A (en) * | 1981-08-05 | 1983-02-08 | Olah George A | Bifunctional acid-base catalyzed conversion of hetero-substituted methanes into olefins |
US4489210A (en) * | 1981-08-19 | 1984-12-18 | Bayer Aktiengesellschaft | Process for the halogenation of organic compounds |
US4467130A (en) * | 1981-09-01 | 1984-08-21 | Olah George A | Condensation of natural gas or methane into gasoline-range hydrocarbons |
US4523040A (en) * | 1981-09-01 | 1985-06-11 | Olah George A | Methyl halides and methyl alcohol from methane |
US4440871A (en) * | 1982-07-26 | 1984-04-03 | Union Carbide Corporation | Crystalline silicoaluminophosphates |
US4465893A (en) * | 1982-08-25 | 1984-08-14 | Olah George A | Oxidative condensation of natural gas or methane into gasoline range hydrocarbons |
US4654449A (en) * | 1982-12-09 | 1987-03-31 | Mobil Oil Corporation | Formation of halogenated hydrocarbons from hydrocarbons |
US4655893A (en) * | 1983-02-07 | 1987-04-07 | Battelle Development Corporation | Cubic boron nitride preparation utilizing a boron and nitrogen bearing gas |
US4665270A (en) * | 1983-12-16 | 1987-05-12 | The British Petroleum Company, P.L.C. | Process for the production of hydrocarbons from hetero-substituted alkanes |
US4513092A (en) * | 1984-01-04 | 1985-04-23 | Mobil Oil Corporation | Composite catalyst for halogenation and condensation of alkanes |
US4652688A (en) * | 1984-04-24 | 1987-03-24 | The British Petroleum Company, P.L.C. | Process for the production of hydrocarbons from hetero-substituted methanes |
US4748013A (en) * | 1985-04-17 | 1988-05-31 | Toyo Soda Manufacturing Co., Ltd. | Adsorbent for recovery of bromine and bromine-recovering process using same |
US4795843A (en) * | 1985-08-26 | 1989-01-03 | Uop Inc. | Conversion of methane into larger organic hydrocarbons |
US4769504A (en) * | 1987-03-04 | 1988-09-06 | The United States Of America As Represented By The United States Department Of Energy | Process for converting light alkanes to higher hydrocarbons |
US4804797A (en) * | 1987-08-24 | 1989-02-14 | Gas Research Institute | Production of commodity chemicals from natural gas by methane chlorination |
US5157189A (en) * | 1987-10-19 | 1992-10-20 | Karra Sankaram B | Conversion of light hydrocarbons to higher hydrocarbons |
US4973786A (en) * | 1987-10-19 | 1990-11-27 | Karra Sankaram B | Process for the pyrolytic oxidation of methane to higher molecular weight hydrocarbons and synthesis gas |
US4982024A (en) * | 1989-12-26 | 1991-01-01 | Ethyl Corporation | Process for the selective dehydrohalogenation of an admixture of alkylhalides |
US5001293A (en) * | 1990-04-25 | 1991-03-19 | Amoco Corporation | Halocarbon conversion |
US5087786A (en) * | 1990-04-25 | 1992-02-11 | Amoco Corporation | Halogen-assisted conversion of lower alkanes |
US5705728A (en) * | 1990-12-06 | 1998-01-06 | Occidental Chemical Corporation | Process for the production of ethylene and mixture containing ethylene |
US5276240A (en) * | 1991-10-18 | 1994-01-04 | Board Of Regents, The University Of Texas System | Catalytic hydrodehalogenation of polyhalogenated hydrocarbons |
US5243098A (en) * | 1992-11-04 | 1993-09-07 | Energia Andina Ltd. | Conversion of methane to methanol |
US5334777A (en) * | 1992-11-04 | 1994-08-02 | Energia Andina Ltd. | Conversion of alkanes to alkanols and glycols |
US5486627A (en) * | 1994-12-02 | 1996-01-23 | The Dow Chemical Company | Method for producing epoxides |
US5969195A (en) * | 1997-05-21 | 1999-10-19 | Basf Aktiengesellschaft | Hydrolysis of alkyl monohalides |
US5998679A (en) * | 1998-05-20 | 1999-12-07 | Jlm Technology, Ltd. | Methods for converting lower alkanes and alkanes to alcohols and diols |
US6713087B2 (en) * | 1999-05-28 | 2004-03-30 | Alkermes Controlled Therapeutics, Inc. | Method of producing submicron particles of a labile agent and use thereof |
US7230150B2 (en) * | 2001-04-18 | 2007-06-12 | Grt, Inc. | Zone reactor |
US7019182B2 (en) * | 2001-04-18 | 2006-03-28 | Grt, Inc. | Method of hydrocarbon preservation and environmental protection |
US20030125589A1 (en) * | 2001-04-18 | 2003-07-03 | Grt, Inc. | Zone reactor |
US6525230B2 (en) * | 2001-04-18 | 2003-02-25 | Grt, Inc. | Zone reactor |
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US20030069452A1 (en) * | 2001-06-20 | 2003-04-10 | Sherman Jeffrey H. | Method and apparatus for synthesizing from alcohols and ethers from alkanes, alkenes, and aromatics |
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UA105476C2 (uk) | 2014-05-26 |
CA2625459C (en) | 2014-11-04 |
AU2006302939B2 (en) | 2013-03-14 |
AR058123A1 (es) | 2008-01-23 |
MY151088A (en) | 2014-04-15 |
US20080200740A1 (en) | 2008-08-21 |
EA200801115A1 (ru) | 2008-10-30 |
AU2006302939A1 (en) | 2007-04-26 |
ECSP088361A (es) | 2008-05-30 |
KR101363300B1 (ko) | 2014-02-18 |
US8008535B2 (en) | 2011-08-30 |
EP1945598A2 (en) | 2008-07-23 |
JP5396082B2 (ja) | 2014-01-22 |
CN101291891B (zh) | 2013-03-27 |
JP2009512754A (ja) | 2009-03-26 |
EG26651A (en) | 2014-05-04 |
CN101291891A (zh) | 2008-10-22 |
EA022696B1 (ru) | 2016-02-29 |
EP1945598A4 (en) | 2011-07-06 |
NO20082252L (no) | 2008-05-16 |
ZA200803330B (en) | 2009-11-25 |
CA2625459A1 (en) | 2007-04-26 |
WO2007046986A3 (en) | 2007-06-07 |
TNSN08176A1 (en) | 2009-10-30 |
WO2007046986A2 (en) | 2007-04-26 |
BRPI0617707A2 (pt) | 2011-08-02 |
KR20080063329A (ko) | 2008-07-03 |
AP2008004417A0 (en) | 2008-04-30 |
NZ567480A (en) | 2011-08-26 |
PE20070737A1 (es) | 2007-08-02 |
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