WO2011008464A1 - Process for the oxidative coupling of methane - Google Patents
Process for the oxidative coupling of methane Download PDFInfo
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- WO2011008464A1 WO2011008464A1 PCT/US2010/039887 US2010039887W WO2011008464A1 WO 2011008464 A1 WO2011008464 A1 WO 2011008464A1 US 2010039887 W US2010039887 W US 2010039887W WO 2011008464 A1 WO2011008464 A1 WO 2011008464A1
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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
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2/00—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms
- C07C2/76—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by condensation of hydrocarbons with partial elimination of hydrogen
- C07C2/82—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by condensation of hydrocarbons with partial elimination of hydrogen oxidative coupling
- C07C2/84—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by condensation of hydrocarbons with partial elimination of hydrogen oxidative coupling catalytic
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/02—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the alkali- or alkaline earth metals or beryllium
- B01J23/04—Alkali metals
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/10—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of rare earths
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/16—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
- B01J23/32—Manganese, technetium or rhenium
- B01J23/36—Rhenium
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J6/00—Heat treatments such as Calcining; Fusing ; Pyrolysis
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C11/00—Aliphatic unsaturated hydrocarbons
- C07C11/02—Alkenes
- C07C11/04—Ethylene
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J21/00—Catalysts comprising the elements, oxides, or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium, or hafnium
- B01J21/10—Magnesium; Oxides or hydroxides thereof
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/02—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the alkali- or alkaline earth metals or beryllium
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2521/00—Catalysts comprising the elements, oxides or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium or hafnium
- C07C2521/10—Magnesium; Oxides or hydroxides thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2523/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00
- C07C2523/02—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of the alkali- or alkaline earth metals or beryllium
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2523/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00
- C07C2523/10—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of rare earths
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2523/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00
- C07C2523/16—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
- C07C2523/32—Manganese, technetium or rhenium
- C07C2523/36—Rhenium
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S585/00—Chemistry of hydrocarbon compounds
- Y10S585/8995—Catalyst and recycle considerations
- Y10S585/906—Catalyst preservation or manufacture, e.g. activation before use
Definitions
- the present invention is related to co-pending applications titled: Catalysts For Oxidative Coupling of Hydrocarbons; and Process For The Oxidative Coupling of Hydrocarbons, both filed by Fina Technology, Inc. on the same date as the present application.
- the present invention generally relates to the oxidative coupling of methane.
- Methane is a primary component of natural gas. Although natural gas can be useful as a fuel, natural gas sources can be remote, and often, it is not cost effective to transport the methane. One method of transporting natural gas is by liquefying the gas, however, the boiling point of methane is low enough that liquefaction can be difficult and expensive. Research has been conducted to find new and cost-effective ways of utilizing this resource.
- Ethylene and higher hydrocarbons can be more easily liquefied and transported from remote sites and can also be valuable products.
- Ethylene, for one, can be a valuable product, as it can be used for the production of styrene, and has many other uses, such as the production of polyethylene, ethanol, ethylene glycol, and polyvinyl chloride.
- ethylene is obtained predominantly from the thermal cracking of hydrocarbons, such as ethane, propane, butane, or naphtha.
- Ethylene can also be produced and recovered from various refinery processes. Ethylene from these sources can also include a variety of undesired products, including diolefms and acetylene, which can be costly to separate from the ethylene. Separation methods can include, for example, extractive distillation and selective hydrogenation of the acetylene back to ethylene.
- Thermal cracking and separation technologies for the production of relatively pure ethylene can result in significant production costs. Thus, the production of ethylene from methane rather than by some of the traditional routes could decrease ethylene production costs.
- Embodiments of the present invention generally include a method for the oxidative coupling of hydrocarbons, such as the oxidative coupling of methane.
- the method can include the steps of preparing oxidative catalysts and running the oxidative coupling reaction inside the reactor over the oxidative catalyst, according to a set of reaction conditions.
- An embodiment of the present invention is the preparation and/or use of a catalyst that includes (A) at least one element selected from the group consisting of the Lanthanoid group, Mg, Ca, and the elements of Group 4 of the periodic table (Ti, Zr, and Hf).
- the catalyst further includes (B) at least one element selected from the group consisting of the Group 1 elements of Li, Na, K, Rb, Cs, and the elements of Group 3 (including La and Ac) and Groups 5 - 15 of the periodic table and (C) at least one element selected from the group consisting of the Group 1 elements of Li, Na, K, Rb, Cs, and the elements Ca, Sr, and Ba; along with (D) oxygen.
- the catalyst can then be dried, calcined, and meshed before being placed in a reactor.
- the catalyst can be calcined by heating the catalyst to elevated temperatures, such as above 75O 0 C.
- the element(s) selected from (A) can range from 40 to 90 wt% of the catalyst.
- the element(s) selected from (B) can range from 0.01 to 40 wt% of the catalyst.
- the element(s) selected from (C) can range from 0.01 to 40 wt% of the catalyst.
- the oxygen in (D) can range from 10 to 45 wt% of the catalyst.
- the oxidative coupling reaction includes supplying the hydrocarbons, such as methane, along with an oxygen source to the reactor.
- the catalyst can be used in a reactor for the oxidative coupling of methane (OCM).
- OCM the temperature can be from 500 0 C to 75O 0 C, optionally from 600 0 C to 75O 0 C.
- the molar ratio of methane to oxygen can be from 1 :1 to 100:1, optionally from 4:1 to 80:1.
- the product distribution of the oxidative coupling reaction can be altered by adjusting the temperature of the reactor. Adjusting the temperature can also alter the exotherm produced by oxidative coupling.
- An embodiment of the invention is a method for the oxidative coupling of methane that includes providing a hydrocarbon feedstream including methane and providing an oxidative catalyst within a reactor.
- the catalyst includes (A) at least one element selected from the group consisting of the Lanthanoid group, Mg, Ca, and the elements of Group 4 of the periodic table (Ti, Zr, and Hf) the elements from (A) ranging from 40 to 90 wt% of the catalyst; (B) at least one element selected from the group consisting of the Group 1 elements of Li, Na, K, Rb, Cs, and the elements of Group 3 (including La and Ac) and Groups 5 - 15 of the periodic table, the elements from (B) ranging from 0.01 to 40 wt% of the catalyst; (C) at least one element selected from the group consisting of the Group 1 elements of Li, Na, K, Rb, Cs, and the elements Ca, Sr, and Ba, the elements from (C) ranging from 0.01 to 40 wt%
- the reactor temperature can range from 500 0 C to 75O 0 C and the molar ratio of methane to oxygen can range from 1 :1 to 100:1. Alternately the temperature can range from 600 0 C to 75O 0 C and the molar ratio of methane to oxygen from 4:1 to 80:1.
- the catalyst can be pretreated in the reactor before it is used for the oxidative coupling of hydrocarbons, the pretreatment consisting of heating the catalyst to above 75O 0 C.
- the composition of the product hydrocarbons can be adjusted by adjusting the temperature of the reaction. The composition can also be adjusted by adjusting the space velocity of the reaction.
- Figure 1 is a graph displaying data, including methane conversion and selectivity of product hydrocarbons, of the OCM trials from Example B.
- the results of oxidative coupling reactions can be influenced by many factors, such as reaction conditions, source and contents of the feed, and reactor design.
- the catalyst used for the reaction can be one of the most important factors.
- the effectiveness of the reaction can be measured in terms of conversion, selectivity, and yield. Conversion refers to the percentage of reactant (e.g. methane) that undergoes a chemical reaction.
- Selectivity refers to the relative activity of a catalyst in reference to a particular compound in a mixture. Selectivity is quantified as the proportion of a particular product relative to all others.
- An embodiment of the present invention is a process of OCM.
- the process can include steps such as preparing an oxidative catalyst, pretreating the oxidative catalyst inside a reactor, and carrying out the oxidative coupling reaction inside the reactor, according to a set of reaction conditions. Preparation and pretreatment of the catalyst and reaction conditions can influence the conversion, selectivity, and yield of OCM and other coupling reactions.
- a catalyst of the present invention generally includes a substrate, one or more metal promoters and oxygen.
- the catalyst can vary in terms of its activity, useful run life, and others characteristics. This variation can influence the selection of the substrate and the combination of metal promoters supported by the substrate.
- the catalyst of the present invention can include a substrate that ranges from 40 to 90 wt% of the catalyst, the substrate made of one or more of the elements of Set A consisting of: the Lanthanoid group (La, Ce, Pr, Nd, Sm, Eu, Gd, Tb, Dy, Ho, Er, Th, Yb, Lu), Mg, Ca, and the elements of Group 4 of the periodic table (Ti, Zr, and Hf).
- the Lanthanoid group La, Ce, Pr, Nd, Sm, Eu, Gd, Tb, Dy, Ho, Er, Th, Yb, Lu
- Mg the elements of Group 4 of the periodic table
- the substrate supports a first promoter that ranges from 0.01 to 40 wt% of the catalyst chosen from one or more of the elements of Set B consisting of: Li, Na, K, Rb, Cs, and the elements of Group 3 (including La and Ac) and Groups 5 - 15 of the periodic table.
- the substrate further supports a second promoter that ranges from 0.01 to 40 wt% of the catalyst chosen from one or more of the elements of Set C consisting of: Li, Na, K, Rb, Cs, Ca, Sr, and Ba. If an element from Group 1 of the periodic table (Li, Na, K, Rb, Cs) is used as a catalytic element from Set B it cannot be used as a catalytic element from Set C.
- the catalyst further includes Set D, which consists of oxygen, in a range of 10 to 45 wt%. All percentages are for the catalyst after calcination.
- the catalyst contains at least one element from each of the Sets A, B, C, and D in the ranges given above. At least 90 wt% of the catalyst is made of the elements of Sets A, B, C and oxygen in the final catalyst composition after a calcination procedure. Optionally at least 95 wt% of the catalyst is made of the elements of Sets A, B, C and D in the final catalyst after a calcination procedure. Residual anions may be present in the final catalyst, e.g. nitrate, halide, sulfate and acetate.
- the catalyst can vary in terms of its activity, its basicity, its lifetime, and other characteristics. This variation can be influenced by the selection of the elements chosen from Sets A, B, C and D and their respective content in the catalyst.
- the various elements that make up the catalyst can be derived from any suitable source, such as in their elemental form, or in compounds or coordination complexes of an organic or inorganic nature, such as carbonates, oxides, hydroxides, nitrates, acetates, chlorides, phosphates, sulfides and sulfonates.
- the elements and/or compounds can be prepared by any suitable method, known in the art, for the preparation of such materials.
- substrate as used herein is not meant to indicate that this component is necessarily inactive, while the other metals and/or promoters are the active species. On the contrary, the substrate can be an active part of the catalyst.
- substrate would merely imply that the substrate makes up a significant quantity, generally 40% or more by weight, of the entire catalyst.
- the promoters individually can range from 0.01% to 40% by weight of the catalyst, optionally from 0.01% to 10%. If more than one promoters are combined, they together generally can range from 0.01% up to 50% by weight of the catalyst.
- the elements of the catalyst composition can be provided from any suitable source, such as in its elemental form, as a salt, as a coordination compound, etc.
- Binder material, extrusion aids or other additives can be added to the catalyst composition or the final catalyst composition can be added to a structured material that provides a support structure.
- the final catalyst composition can be supported by a structured material comprising an alumina or aluminate framework.
- the content of such a binder material, extrusion aids, structured material, or other additives, and their respective calcination products, will not be taken into consideration within the stated percentage ranges of Sets A - D stated herein.
- a binder material which can contain elements that are contained within Sets A - D, can be added to the catalyst composition.
- binder material elements and the calcination products are not taken into consideration within the stated percentage ranges of Sets A - D stated herein.
- additional elements such as a binder, extrusion aid, structured material, or other additives, and their respective calcination products, are included within the scope of the invention.
- the invention is a method for the preparation of an oxidative catalyst for OCM, or another oxidative coupling reaction.
- the catalyst can be prepared by combining a substrate chosen from at least one element from Set A with at least one promoter element chosen from Set B, at least one promoter element chosen from Set C, and oxygen from Set D.
- the present invention is not limited by the method of catalyst preparation, and all suitable methods should be considered to fall within the scope herein. Particularly effective techniques are those utilized for the preparation of solid catalysts. Conventional methods include coprecipitation from an aqueous, an organic or a combination solution-dispersion, impregnation, dry mixing, wet mixing or the like, alone or in various combinations.
- any method can be used which provides compositions of matter containing the prescribed components in effective amounts.
- the substrate is charged with promoter via an incipient wetness impregnation.
- Other impregnation techniques such as by soaking, pore volume impregnation, or percolation can optionally be used.
- Alternate methods such as ion exchange, wash coat, precipitation, and gel formation can also be used.
- Various methods and procedures for catalyst preparation are listed in the technical report Manual of Methods and Procedures for Catalyst Characterization by J. Haber, J. H. Block and B. Dolmon, published in the International Union of Pure and Applied Chemistry, Volume 67, Nos 8/9, pp. 1257-1306, 1995, incorporated herein in its entirety.
- the substrate can be a metal oxide of one or more elements of Set A.
- an oxide substrate useful for the present invention is magnesium oxide, MgO.
- the oxide substrate can be either obtained commercially or produced in the lab.
- a metal oxide can be made by thermal decomposition of its corresponding salt at elevated temperatures up to 75O 0 C.
- the choice of precursor salt from which the oxide substrate is produced can have some effect on the performance of the eventual catalyst.
- the dried composition is generally calcined in the presence of a free oxygen-containing gas, usually at temperatures between about 300 0 C and about 900 0 C for a period of time such as from 1 to 24 hours.
- the calcination can be in a reducing or inert atmosphere or an oxygen- containing atmosphere.
- a pretreatment of the catalyst may, or may not, be necessary.
- the invention involves the pretreatment of an oxidative catalyst for OCM, OMT, or another oxidative coupling reaction.
- the prepared catalyst can be ground, pressed and sieved and loaded into a reactor.
- the reactor can be any type known in the art to make catalyst particles, such as a fixed bed, fluidized bed, or swing bed reactor.
- the reactor set-up can optionally include a recycle stream.
- an inert material such as quartz chips, can be used to support the catalyst bed and to place the catalyst within the bed.
- the reactor can be heated to elevated temperatures, such as 800 0 C to 900 0 C with an air flow, such as 100 niL/min, and held at these conditions for a length of time, such as 1 to 3 hours. Then, the reactor can be cooled down to a temperature of around the operating temperature of the reactor, for example 500 0 C to 65O 0 C, or optionally down to atmospheric or other desired temperature.
- the reactor can be kept under an inert purge, such as under helium.
- Another aspect of the process of the present invention is a set of reaction conditions used in OCM and other coupling reactions.
- Several parameters including feed composition, molar ratio of hydrocarbon reactant to oxygen, temperature, pressure, time on stream, preparation method, particle size, porosity, surface area, contact time and others can influence the outcome of the reaction.
- contents of the feed can include methane and an oxygen source.
- Oxygen is a required component of the feed for oxidative coupling.
- Methane can be obtained from natural gas, or from organic sources, such as the decomposition of waste through fermentation.
- the oxygen source can be any source suitable for providing oxygen to the reaction zone such as pure oxygen, oxygen- enriched air, or air.
- the gas containing oxygen should not contain any contaminants that might significantly interfere with the oxidative coupling reaction.
- Alternate sources of oxygen may also be used, such as nitrobenzene, nitrous oxide or other oxygen containing compounds.
- reaction modulators can be used for the control or alteration of conversion, selectivity, or activity of a particular catalyst or in response to certain reaction conditions.
- Non-limiting examples of possible reaction modulators include chlorine, ethylene and carbon monoxide.
- Inert diluents such as helium and nitrogen may be included in the feed to adjust the gas partial pressures.
- CO 2 or water (steam) can be included in the feed stream as these components may have beneficial properties, such as in the prevention of coke deposits.
- the pressure for oxidative coupling reactions can generally range from 1 psia to 200 psia or more. The reaction pressure is not a limiting factor regarding the present invention and any suitable condition is considered to be within the scope of the invention.
- the temperature for oxidative coupling reactions can generally range from 500 0 C to 800 0 C, optionally from 600 0 C to 75O 0 C.
- the reaction temperature is not a limiting factor regarding the present invention and any suitable condition is considered to be within the scope of the invention.
- the methane to oxygen molar ratio can range from 1 :1 to 100:1, optionally from 4:1 to 80:1.
- space velocity [feed flow as vapor (cm 3 /h)] / [catalyst weight (g)].
- the space velocity can generally range from 15,000 cm 3 g ⁇ V to 100,000 cm 3 g ⁇ V, optionally from 20,000 cm 3 g ⁇ V to 85,000 cm 3 g "1 h "1' This range is an indication of possible space velocities, such as for a fixed bed reactor. Of course altering the catalyst composition, the amount of inert material, etc can alter the space velocity outside of this range.
- Equations 1-2 are reactions that can take place in the reactor over the OCM catalyst.
- the equations are shown along with their change in enthalpy, or heat of reaction. As Equations 1-2 demonstrates the reactions that occur during OCM are exothermic.
- An oxidative catalyst was prepared comprising a MgO substrate that was promoted with Ba.
- the Ba/MgO catalyst was used in the oxidative coupling of methane and the oxidative methylation of toluene.
- the catalyst included 5% Ba by weight and was prepared from barium nitrate (6.53g) (Sigma Aldrich, 98.0%) and MgO (23.46g) (Fisher, 99%) by incipient wetness impregnation methodology in aqueous solution. The mixture was dried at 12O 0 C for 3 h and then calcined at 85O 0 C in air for 1 h.
- the catalyst was ground, pressed and sieved to 20 - 40 mesh size (420 - 841 ⁇ m) and 0.577 g of catalyst was loaded into a quartz reactor using quartz wool plugs and quartz chips to hold the catalyst bed in place.
- the reactor was heated to 85O 0 C under 100 ml/min of air and held for 2 hours. The reactor was then cooled down to 600 0 C under helium to prepare for the OCM experiments.
- An oxidative catalyst was prepared comprising an oxide substrate, MgO, that was promoted with Sr and La.
- the Sr/La/MgO catalyst was used in the oxidative coupling of methane.
- the catalyst included 5% Sr by weight from strontium nitrate (3.62g) and 5% La by weight from lanthanum oxide (3.5Ig) and was prepared from Sr(NOs) 2 salt, La 2 O 3 (Sigma Aldrich, 98.0%) and MgO (22.85g) (Fisher, 99%) by incipient wetness impregnation methodology in aqueous solution.
- the mixture was dried at 12O 0 C for 3 hours and then calcined at 85O 0 C in air for 1 hour.
- the catalyst was ground and sieved to 20 - 40 mesh size and 0.855 g of catalyst was loaded in a quartz reactor using quartz wool plugs and quartz chips to hold the catalyst bed in place.
- the reactor was heated to 85O 0 C under 100 ml/min of air and held for 2 hours.
- the reactor was then cooled down to 600 0 C under helium to prepare for the OCM experiments.
- Figure 1 is a graphical representation of the data shown in Table 7. At a temperature between 55O 0 C and 600 0 C, methane conversion and C 2 selectivity increased suddenly, while CO selectivity drops dramatically.
- An oxidative catalyst was prepared comprising a MgO substrate that was promoted with Na, Cs, and Re.
- the Na/Cs/Re/MgO catalyst was used in the oxidative coupling of methane.
- the catalyst included 5% Na by weight (3.811 g) of sodium chloride, 5% Cs by weight (2.199 g) of cesium nitrate, and 0.01% Re by weight (0.5856 g) of rhenium chloride and MgO (23.4033 g) (Fisher, 99%) by incipient wetness impregnation methodology in aqueous solution.
- the mixture was dried at 12O 0 C for 3 h and then calcined at 85O 0 C in air for 1 h.
- the catalyst was ground and sieved to 20 - 40 mesh size (420 - 841 ⁇ m) and 0.597 g of catalyst was loaded into a quartz reactor using quartz wool plugs and quartz chips to hold the catalyst bed in place.
- the reactor was heated to 85O 0 C under 100 ml/min of air and held for 2 hours.
- the reactor was then cooled down to 600 0 C under helium to prepare for the OCM and OMT experiments.
- Figures are used herein to illustrate data, which are shown as data points on a graph. Lines connecting the data points are used to guide the eye and assist in illustrating general trends of the data. The lines are not intended as a predictor of where additional data points would necessarily fall, if they were available.
- C 2 selectivity is the cumulative selectivity of acetylene, ethane, and ethylene.
- OCM oxidative coupling of methane. For instance, methane can couple with methane to form higher hydrocarbons such as ethane or ethylene.
- space velocity [feed flow as vapor (cm /K)] I [catalyst weight (g)].
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Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP10800251.0A EP2448888A4 (en) | 2009-06-29 | 2010-06-25 | PROCESS FOR OXIDATIVE COUPLING OF METHANE |
| EA201270073A EA201270073A1 (ru) | 2009-06-29 | 2010-06-25 | Способ окислительного сочетания метана |
| CN2010800290822A CN102471181A (zh) | 2009-06-29 | 2010-06-25 | 甲烷的氧化偶联方法 |
| AU2010273876A AU2010273876A1 (en) | 2009-06-29 | 2010-06-25 | Process for the oxidative coupling of methane |
| JP2012517752A JP2012532104A (ja) | 2009-06-29 | 2010-06-25 | メタンの酸化カップリング方法 |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US12/494,117 US8912381B2 (en) | 2009-06-29 | 2009-06-29 | Process for the oxidative coupling of methane |
| US12/494,117 | 2009-06-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO2011008464A1 true WO2011008464A1 (en) | 2011-01-20 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/US2010/039887 Ceased WO2011008464A1 (en) | 2009-06-29 | 2010-06-25 | Process for the oxidative coupling of methane |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US8912381B2 (enExample) |
| EP (1) | EP2448888A4 (enExample) |
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|---|---|---|---|---|
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20020173420A1 (en) * | 2000-09-18 | 2002-11-21 | Cantrell Rick David | Catalysts for the oxidative dehydrogenation of hydrocarbons |
| US20070055083A1 (en) * | 2003-04-29 | 2007-03-08 | Ebrahim Bagherzadeh | Preparation of catalyst and use for high yield conversion of methane to ethylene |
Family Cites Families (63)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4239658A (en) | 1979-04-05 | 1980-12-16 | Exxon Research & Engineering Co. | Catalysts for the conversion of relatively low molecular weight hydrocarbons to higher molecular weight hydrocarbons and the regeneration of the catalysts |
| EP0054249B2 (en) | 1980-12-09 | 1993-04-21 | Toray Industries, Inc. | Immunoparticles and process for preparing the same |
| US4523049A (en) | 1984-04-16 | 1985-06-11 | Atlantic Richfield Company | Methane conversion process |
| US4547611A (en) * | 1983-08-12 | 1985-10-15 | Atlantic Richfield Company | Methane conversion |
| 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) |
| US4704487A (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 (IV-B) |
| US4547610A (en) | 1984-04-16 | 1985-10-15 | Atlantic Richfield Company | Methane conversion |
| ATE81606T1 (de) * | 1984-04-16 | 1992-11-15 | Atlantic Richfield Co | Traegerkatalysatoren und ihre verwendung zur umwandlung von methan und zur dehydrogenierung von kohlenwasserstoffen. |
| US4672145A (en) | 1985-03-19 | 1987-06-09 | Phillips Petroleum Company | Composition of matter and method of oxidative conversion of organic compounds therewith |
| US4658076A (en) | 1985-03-19 | 1987-04-14 | Phillips Petroleum Company | Composition of matter and method of oxidative conversion of organic compounds therewith |
| US4658077A (en) * | 1985-06-07 | 1987-04-14 | Phillips Petroleum Company | Composition of matter and method of oxidative conversion of organic compounds therewith |
| US5157188A (en) | 1985-03-19 | 1992-10-20 | Phillips Petroleum Company | Methane conversion |
| US4982038A (en) | 1985-03-19 | 1991-01-01 | Phillips Petroleum Company | Oxidative methylation of organic compounds |
| US4895823A (en) | 1985-03-19 | 1990-01-23 | Phillips Petroleum Company | Composition of matter for oxidative conversion of organic compounds |
| US5210357A (en) | 1985-06-07 | 1993-05-11 | Phillips Petroleum Company | Composition of matter and method of oxidative conversion of organic compounds therewith |
| US4950836A (en) | 1985-06-07 | 1990-08-21 | Phillips Petroleum Company | Oxidative methylation of organic compounds |
| US4775654A (en) | 1985-03-19 | 1988-10-04 | Phillips Petroleum Company | Composition of matter |
| 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 |
| US4620057A (en) * | 1985-06-07 | 1986-10-28 | Phillips Petroleum Company | Methane conversion |
| 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 |
| US4780449A (en) * | 1985-06-14 | 1988-10-25 | W. R. Grace & Co.-Conn. | Catalyst for the conversion of methane |
| US4822944A (en) * | 1986-07-11 | 1989-04-18 | The Standard Oil Company | Energy efficient process for upgrading light hydrocarbons and novel oxidative coupling catalysts |
| 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 |
| US5068215A (en) | 1987-06-04 | 1991-11-26 | Standard Oil Company | Catalyst for upgrading low molecular weight hydrocarbons |
| US4886931A (en) * | 1987-06-04 | 1989-12-12 | The Standard Oil Company | Upgrading low molecular weight hydrocarbons |
| JPH0674215B2 (ja) * | 1987-12-11 | 1994-09-21 | 宇部興産株式会社 | 炭化水素の製造方法 |
| GB8802731D0 (en) | 1988-02-06 | 1988-03-09 | British Petroleum Co Plc | Chemical process |
| US4826796A (en) | 1988-03-28 | 1989-05-02 | Institute Of Gas Technology | Mixed basic metal oxide catalyst for oxidative coupling of methane |
| US4950827A (en) | 1988-03-28 | 1990-08-21 | Institute Of Gas Technology | Oxidative coupling of aliphatic and alicyclic hydrocarbons with aliphatic and alicyclic substituted aromatic hydrocarbons |
| US4956327A (en) | 1989-05-31 | 1990-09-11 | Institute Of Gas Technology | Mixed basic metal oxide/sulfide catalyst |
| US4935572A (en) * | 1988-03-28 | 1990-06-19 | Institute Of Gas Technology | Mixed basic metal oxide catalyst for oxidative coupling of methane |
| US4950830A (en) | 1988-03-28 | 1990-08-21 | Institute Of Gas Technology | Dehydration of aliphatic and alicyclic hydrocarbons and aliphatic and alicyclic substituted aromatic hydrocarbons |
| EP0335130A1 (en) * | 1988-03-28 | 1989-10-04 | Institute of Gas Technology | Mixed basic metal oxide catalyst |
| FR2629451B1 (fr) * | 1988-04-05 | 1991-07-12 | Inst Francais Du Petrole | Procede de production d'olefines a partir du gaz naturel |
| US5028577A (en) | 1989-01-11 | 1991-07-02 | Amoco Corporation | Lower alkane conversion catalysts |
| JPH02225425A (ja) * | 1989-02-28 | 1990-09-07 | Ube Ind Ltd | マグネシアを触媒の一成分とする炭化水素の製造方法 |
| US5026945A (en) * | 1989-09-19 | 1991-06-25 | Union Carbide Chemicals And Plastics Technology Corporation | Perovskite catalysts for oxidative coupling |
| US5238898A (en) | 1989-12-29 | 1993-08-24 | Mobil Oil Corp. | Catalyst and process for upgrading methane to higher hydrocarbons |
| CA2016675A1 (en) | 1990-05-14 | 1991-11-14 | Kevin James Smith | Process for the oxidative coupling of methane to higher hydrocarbons |
| US5132482A (en) | 1990-06-14 | 1992-07-21 | Alberta Research Council | Process for the oxidative coupling of methane to higher hydrocarbons |
| IT1244484B (it) * | 1990-12-21 | 1994-07-15 | Eniricerche Spa | Procedimento e catalizzatore per la trasformazione del metano in prodotti idrocarburici superiori |
| US5097086A (en) | 1991-05-31 | 1992-03-17 | Institute Of Gas Technology | Liquid catalyst for oxidative coupling reactions |
| JPH04368342A (ja) * | 1991-06-17 | 1992-12-21 | Sekiyu Shigen Kaihatsu Kk | メタンを原料とするエタン、エチレンの製造方法 |
| CN1044094C (zh) * | 1991-06-20 | 1999-07-14 | 中国科学院兰州化学物理研究所 | 将甲烷转化成较高级烃的催化剂及其用途 |
| JPH059133A (ja) * | 1991-06-28 | 1993-01-19 | Sekiyu Shigen Kaihatsu Kk | メタンからエタン、エチレンの製造方法 |
| US5118654A (en) * | 1991-08-22 | 1992-06-02 | Council Of Scientific & Industrial Research | Process for the preparation of an improved Li-promoted MgO catalyst useful for oxidative coupling of methane to ethane and ethylene |
| CN1072615A (zh) * | 1991-11-28 | 1993-06-02 | 中国科学院兰州化学物理研究所 | 甲烷氧化偶联制乙烯催化剂 |
| IT1255945B (it) * | 1992-10-30 | 1995-11-17 | Eniricerche Spa | Procedimento e catalizzatore per la trasformazione del metano in prodotti idrocarburici superiori. |
| US5763722A (en) * | 1992-12-11 | 1998-06-09 | Repsol Petroleo S.A. | Method for the methane chemical conversion into C2 hydrocarbons |
| US5712217A (en) * | 1995-06-05 | 1998-01-27 | Council Of Scientific & Industrial Research | Supported catalyst with mixed lanthanum and other rare earth oxides |
| JPH1025257A (ja) * | 1996-07-12 | 1998-01-27 | Toyota Motor Corp | メチル基をビニル基に転化する方法 |
| US5780003A (en) | 1996-08-23 | 1998-07-14 | Uop Llc | Crystalline manganese phosphate compositions |
| DE19829300B4 (de) * | 1997-06-30 | 2006-05-18 | Hyundai Electronics Industries Co., Ltd., Ichon | Ferroelektrische Speichereinrichtung mit elektrischer Verbindung zwischen einer unteren Kondensatorelektrode und einem Kontaktstopfen sowie Verfahren zu deren Herstellung |
| US6096934A (en) | 1998-12-09 | 2000-08-01 | Uop Llc | Oxidative coupling of methane with carbon conservation |
| RU2007119938A (ru) * | 2004-12-09 | 2009-01-20 | Хрд Корп. (Us) | Катализатор и способ преобразования парафиновых углеводородов с низким молекулярным весом в алкены |
| RU2478426C2 (ru) | 2007-04-25 | 2013-04-10 | Хрд Корп. | Катализатор и способ конвертации природного газа в высокоуглеродистые соединения |
| US9089832B2 (en) * | 2009-06-29 | 2015-07-28 | Fina Technology, Inc. | Catalysts for oxidative coupling of hydrocarbons |
| US8450546B2 (en) * | 2009-06-29 | 2013-05-28 | Fina Technology, Inc. | Process for the oxidative coupling of hydrocarbons |
| US8399726B2 (en) | 2010-04-20 | 2013-03-19 | Fina Technology Inc | Reactors and processes for the oxidative coupling of hydrocarbons |
-
2009
- 2009-06-29 US US12/494,117 patent/US8912381B2/en not_active Expired - Fee Related
-
2010
- 2010-06-23 TW TW099120467A patent/TW201119979A/zh unknown
- 2010-06-25 EA EA201270073A patent/EA201270073A1/ru unknown
- 2010-06-25 WO PCT/US2010/039887 patent/WO2011008464A1/en not_active Ceased
- 2010-06-25 JP JP2012517752A patent/JP2012532104A/ja active Pending
- 2010-06-25 CN CN2010800290822A patent/CN102471181A/zh active Pending
- 2010-06-25 KR KR1020117030878A patent/KR20120109998A/ko not_active Withdrawn
- 2010-06-25 AU AU2010273876A patent/AU2010273876A1/en not_active Abandoned
- 2010-06-25 EP EP10800251.0A patent/EP2448888A4/en not_active Withdrawn
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20020173420A1 (en) * | 2000-09-18 | 2002-11-21 | Cantrell Rick David | Catalysts for the oxidative dehydrogenation of hydrocarbons |
| US20070055083A1 (en) * | 2003-04-29 | 2007-03-08 | Ebrahim Bagherzadeh | Preparation of catalyst and use for high yield conversion of methane to ethylene |
Non-Patent Citations (1)
| Title |
|---|
| See also references of EP2448888A4 * |
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| US9469577B2 (en) | 2012-05-24 | 2016-10-18 | Siluria Technologies, Inc. | Oxidative coupling of methane systems and methods |
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Also Published As
| Publication number | Publication date |
|---|---|
| CN102471181A (zh) | 2012-05-23 |
| EA201270073A1 (ru) | 2012-05-30 |
| AU2010273876A1 (en) | 2011-12-22 |
| EP2448888A1 (en) | 2012-05-09 |
| EP2448888A4 (en) | 2013-11-27 |
| US20100331595A1 (en) | 2010-12-30 |
| US8912381B2 (en) | 2014-12-16 |
| TW201119979A (en) | 2011-06-16 |
| JP2012532104A (ja) | 2012-12-13 |
| KR20120109998A (ko) | 2012-10-09 |
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