US20060084830A1 - Selective hydrogenation process and catalyst - Google Patents

Selective hydrogenation process and catalyst Download PDF

Info

Publication number
US20060084830A1
US20060084830A1 US10/969,613 US96961304A US2006084830A1 US 20060084830 A1 US20060084830 A1 US 20060084830A1 US 96961304 A US96961304 A US 96961304A US 2006084830 A1 US2006084830 A1 US 2006084830A1
Authority
US
United States
Prior art keywords
catalyst
support
catalyst according
alumina
surface area
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Abandoned
Application number
US10/969,613
Other languages
English (en)
Inventor
J. Ryu
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Catalytic Distillation Technologies
Original Assignee
Catalytic Distillation Technologies
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Catalytic Distillation Technologies filed Critical Catalytic Distillation Technologies
Priority to US10/969,613 priority Critical patent/US20060084830A1/en
Assigned to CATALYTIC DISTILLATION TECHNOLOGIES reassignment CATALYTIC DISTILLATION TECHNOLOGIES ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: RYU, J. YONG
Priority to PCT/US2005/025606 priority patent/WO2006044005A2/en
Priority to CNA2005800317059A priority patent/CN101432247A/zh
Priority to KR1020077008829A priority patent/KR20070074568A/ko
Priority to RU2007114902/04A priority patent/RU2355670C2/ru
Priority to JP2007537874A priority patent/JP2008516765A/ja
Priority to MX2007003207A priority patent/MX2007003207A/es
Priority to TW094126451A priority patent/TW200613060A/zh
Publication of US20060084830A1 publication Critical patent/US20060084830A1/en
Priority to US12/539,229 priority patent/US7838710B2/en
Abandoned legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C7/00—Purification; Separation; Use of additives
    • C07C7/148—Purification; Separation; Use of additives by treatment giving rise to a chemical modification of at least one compound
    • C07C7/163—Purification; Separation; Use of additives by treatment giving rise to a chemical modification of at least one compound by hydrogenation
    • C07C7/167—Purification; Separation; Use of additives by treatment giving rise to a chemical modification of at least one compound by hydrogenation for removal of compounds containing a triple carbon-to-carbon bond
    • 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
    • B01J23/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
    • B01J23/54—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
    • B01J23/56—Platinum group metals
    • B01J23/58—Platinum group metals with alkali- or alkaline earth 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
    • B01J21/00—Catalysts comprising the elements, oxides, or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium, or hafnium
    • B01J21/005—Spinels
    • 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
    • B01J21/02—Boron or aluminium; Oxides or hydroxides thereof
    • B01J21/04—Alumina
    • 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
    • B01J23/005—Spinels
    • 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
    • B01J23/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
    • B01J23/40—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals of the platinum group metals
    • B01J23/44—Palladium
    • 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
    • B01J23/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper
    • B01J23/89—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with noble metals
    • B01J23/892—Nickel and noble 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
    • B01J23/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper
    • B01J23/89—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with noble metals
    • B01J23/8926—Copper and noble 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
    • B01J23/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper
    • B01J23/89—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with noble metals
    • B01J23/8933—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with noble metals also combined with metals, or metal oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
    • B01J23/8946—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with noble metals also combined with metals, or metal oxides or hydroxides provided for in groups B01J23/02 - B01J23/36 with alkali or alkaline earth 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
    • B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
    • B01J37/02—Impregnation, coating or precipitation
    • B01J37/0201—Impregnation
    • B01J37/0207—Pretreatment of the support
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C5/00—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms
    • C07C5/02—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by hydrogenation
    • C07C5/03—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by hydrogenation of non-aromatic carbon-to-carbon double bonds
    • 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
    • C10G45/00—Refining of hydrocarbon oils using hydrogen or hydrogen-generating compounds
    • C10G45/32—Selective hydrogenation of the diolefin or acetylene compounds
    • C10G45/34—Selective hydrogenation of the diolefin or acetylene compounds characterised by the catalyst used
    • C10G45/36—Selective hydrogenation of the diolefin or acetylene compounds characterised by the catalyst used containing nickel or cobalt metal, or compounds thereof
    • 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
    • C10G45/00—Refining of hydrocarbon oils using hydrogen or hydrogen-generating compounds
    • C10G45/32—Selective hydrogenation of the diolefin or acetylene compounds
    • C10G45/34—Selective hydrogenation of the diolefin or acetylene compounds characterised by the catalyst used
    • C10G45/40—Selective hydrogenation of the diolefin or acetylene compounds characterised by the catalyst used containing platinum group metals or compounds thereof
    • 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
    • B01J35/00—Catalysts, in general, characterised by their form or physical properties
    • B01J35/60—Catalysts, in general, characterised by their form or physical properties characterised by their surface properties or porosity
    • B01J35/61—Surface area
    • B01J35/613—10-100 m2/g
    • 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
    • B01J35/00—Catalysts, in general, characterised by their form or physical properties
    • B01J35/60—Catalysts, in general, characterised by their form or physical properties characterised by their surface properties or porosity
    • B01J35/63—Pore volume
    • B01J35/633—Pore volume less than 0.5 ml/g
    • 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
    • B01J35/00—Catalysts, in general, characterised by their form or physical properties
    • B01J35/60—Catalysts, in general, characterised by their form or physical properties characterised by their surface properties or porosity
    • B01J35/64—Pore diameter
    • B01J35/647—2-50 nm

Definitions

  • the present invention relates to the selective removal of acetylenic compounds from hydrocarbon streams using specific Ni-based catalysts and the process of making the catalysts.
  • the process is particularly useful in cleaning up MAPD (methyl acetylene and propadiene) and acetylene in crude mixed olefin streams or phenylacetylene in crude styrene streams by selective hydrogenation in the presence of the Ni-based catalyst.
  • MAPD methyl acetylene and propadiene
  • Acetylenic impurities such as acetylene, methyl acetylene, vinyl acetylene, ethyl acetylene, and 2-methyl-1-buten-3-yne are found in various crude mixed C 2 -C 5 streams, for example in the manufacture of olefins such as ethylene, propylene, butadiene and isoprene.
  • olefins such as ethylene, propylene, butadiene and isoprene.
  • These acetylenic impurities need to be removed with a minimum loss of the useful olefinic materials, i.e., ethylene, propylene, butenes, butadiene, isoprene and the like.
  • 1,3-butadiene is an important raw material used to produce various polymers such as butadiene-styrene copolymer.
  • One of the processes for producing 1,3-butadiene is co-production of various olefins by steam cracking of petroleum fractions.
  • the crude mixed C 4 stream from a steam cracker is selectively hydrogenated to partially remove C 4 acetylenic compounds.
  • the selectively hydrogenated stream is sent to the 1,3-butadiene recovery unit where solvent extractive distillation techniques are used to separate 1,3-butadiene from the rest of components in the mixed stream.
  • Solvent extractive distillation is expensive to operate and energy consumption is intensive.
  • the preferred technique for the purification in commercial practice is the selective hydrogenation of acetylenic compounds over hydrogenation catalysts.
  • Supported Pd, Ni, Cu and Co catalysts are known as useful for the hydrogenation of acetylenes (Handbook of Commercial Catalysts, pp. 105-138, Howard F. Rase, CRC Press, 2000).
  • the most preferred catalysts in prior commercial applications of selective hydrogenation of acetylenes are palladium-based catalysts such as Pd, Pd/Pb, Pd/Ag or Pd/Au on a support such as alumina and the copper catalysts on a support such as alumina.
  • Pd catalysts were the most preferred catalysts because of high activity and higher selectivity compared with other known metal catalysts.
  • palladium-based catalysts are not selective enough to completely remove C 4 acetylenes without an unacceptable amount of 1,3-butadiene loss due to over-hydrogenation.
  • Another inherent problem of palladium-based catalysts is the loss and migration of palladium due to the formation of soluble Pd complex compounds by the reaction of Pd atoms on the catalyst surface with vinyl acetylene, if the hydrogenation is carried out with a liquid phase.
  • Silver and gold have been used to minimize the loss of palladium and reduce catalytic polymerization of acetylenic compounds.
  • the copper-based catalysts are very selective so that the recovery of 1,3-butadiene from the mixed stream is very high compared with palladium-base catalysts.
  • the activity of copper catalysts is very low compared with palladium-based catalysts, and a large volume of catalyst and large reactor are required. Also because the deposition of heavy carbonaceous materials on the catalyst occurs quickly, frequent regeneration of catalysts necessitates multiple reactors.
  • Ni catalysts in any form are very active catalysts for selective hydrogenation of acetylenes and dienes.
  • Ni and Ni—Cu alloy catalysts are effective for methyl acetylene hydrogenation.
  • the catalytic activity rapidly increases with addition of copper to nickel up to 25 wt. % in alloy catalyst.
  • the selectivity to propylene and extent of polymerization increase with the increase of copper in the alloy.
  • Nickel-based catalysts have been used in commercial processes for the selective hydrogenation of acetylenic impurities in mixed steams of olefins and diolefins.
  • the present catalyst is a supported catalyst for selective hydrogenation of acetylenes comprising Ni deposited with a promoting amount of Pd on an aluminum oxide support, which contains mixed oxides of MAI 2 O 4 with spinel structures, where M is any divalent cation, preferably comprising 3-15 wt. % Ni promoted with 0.005-0.2 Pd on a support.
  • the catalysts are prepared by depositing nickel promoted with palladium on a support, containing one or more optional elements from copper, silver, Group IA (Li, Na, K, Rb, Cs, Fr) and Group IIA (Be, Mg, Ca, Sr, Ba, Ra) and B (Zn, Cd) of the periodic table of elements and characterized as: Range of component Preferably Component wt. % wt. % Ni 3-15 4-11 Cu 0-1 0.01-0.6 Pd 0.005-0.2 0.01-0.1 Ag 0-10 0-5 Group IA 0-2.5 0-1.5 Group IIA & B 0-25 0.1-5 Where the weight % of the active components are based on the total weight of active components and support.
  • a promoting amount of Pd means an amount less than 10% of the Ni present.
  • the catalysts are useful for hydrogenation reactions such as selective hydrogenation to remove acetylenic impurities in various mixed streams of C 2 -C 12 olefins, diolefins and styrene, and hydrogenation of benzene to cyclohexane. Passing a mixture of a hydrocarbon feed stream and hydrogen gas through a catalytic reaction zone or a series of two catalytic reaction zones which carries out hydrogenation reactions such as the selective hydrogenation of acetylenic compounds.
  • a catalytic reaction zone may contain one catalyst or several different catalysts. If the selective hydrogenation is carried out in a series of two catalytic reaction zones, optionally the catalyst in the second reaction zone may contain Cu as a promoter and modifier.
  • the poisoning effects of organic mercaptans and organo-mercuric compounds for the nickel catalysts promoted with Cu in the second catalytic reaction zone are neutralized in the first catalytic reaction zone.
  • a portion of the catalyst in the first catalytic reaction zone is sacrificed as a guard bed for the poisonous impurities.
  • the improvement made for the hydrogenation process in this invention is higher selectivity or higher recovery of the useful materials such as mono-olefins, diolefins, or both, than those processes based on conventional nickel catalysts or conventional palladium-based catalysts.
  • the C 4 acetylenic impurities in a mixed crude butadiene stream can be completely removed by selective hydrogenation with higher recovery of 1,3-butadiene in the present process, than prior art nickel catalysts. Therefore, this invention allows elimination of one of two extractive distillation columns, resulting in simpler and cheaper separation of 1,3-butadiene from the mixed stream.
  • the catalyst is particularly useful for removing MAPD or acetylene in crude mixed C 2 -C 3 olefin streams and phenyl acetylene in crude styrene stream by selective hydrogenation.
  • MAPD Methyl acetylene/propadiene
  • the improvement is made by depositing Ni promoted with palladium and preferably copper on a support.
  • the catalyst may contain one or more optional elements from Group I and Group II, such as Ag, Ca, Mg, etc.
  • silver is deposited on a support in any of following methods; prior-deposition or post-deposition to deposition of nickel, co-deposition with nickel, combinations of two or all of these.
  • the optional components, other than Ag are deposited on alumina prior to deposition of active metal components Ni, Cu, Pd and Ag. Deposition of Ni on a support can be carried out by performing either a single or multiple impregnations in any method.
  • a preferred catalyst is a supported catalyst for selective hydrogenation of acetylenes selected from the group consisting of 3-15 wt. % Ni, 0.005-0.2 Pd, 0.0-1 wt. % copper, 0.0-10 wt. % Ag, 0-1.5 of at least one member of Group IA and 0.0-25 wt. % of at least one member of Group IIA and IIB deposited on a support, more preferably selected from the group consisting of 4-11 wt. % Ni, 0.01-0.1 Pd, 0.01-0.6 wt. % copper, 0.0-5 wt. % Ag, 0.0-1.5 of at least one member of Group IA and 0.1-5 wt. % of at least one member of Group IIA and IIB deposited on a support.
  • the preferred support will have BET surface area from about 10 to 100 m 2/g, preferably from about 12 to 75 m 2/g.
  • supports are alumina, silica, beta-silicon carbide, carbon, mixed metal oxides, ceramics, various structured materials for column packing, etc.
  • the preferred alumina is prepared by calcining at a temperature from about 1000 to 1250° C.
  • the diameter of a preferred shaped support is from 0.2 mm to 3 mm, preferably from 0.4 to 2.5 mm, most preferably from 0.7 mm to 1.5 mm.
  • the preferred alumina is alpha, theta, delta-alumina or a mixture of these, which have BET surface area, preferably from 10 to about 75 m 2/g. Additional optional elements are any elements from Group 1 and 11 in the Periodic Table.
  • a preferred support is aluminum oxide, which contains mixed oxides of MAI 2 O 4 with spinel structures, where M is any divalent cation, such as Mg, Ca, Zn, Ni, Co, Cu, Mn, etc. Also, up to 30% of aluminum in mixed oxides can be replaced with Ga or In.
  • the content of spinel in aluminum oxide support can be any amount, but preferably from 0.1% to 50%, most preferably from 0.2% to 20%.
  • catalyst containing optional elements are prepared with alumina support
  • one or more elements from Group II is deposited on preferably gamma or eta-alumina and then calcined at from about 900 to 1250° C. to prepare a spinel containing alumina support.
  • the selective hydrogenation can be carried out in any physical device in the presence of one or two catalysts, which have different compositions within this invention or are a combination of catalysts in this invention and other Ni-based catalysts or palladium-based catalysts.
  • Examples of such devices are fixed bed reactors, catalytic distillation reactors, boiling point reactors, extractive distillation reactors, divided wall distillation reactors, moving bed reactors, stirred tank reactors, and trickle bed reactors.
  • a combination of two or three of these physical devices can be used for multi-step selective hydrogenation.
  • the crude feed stream may be partially hydrogenated to remove acetylenic compounds in a catalytic distillation column reactor or extractive distillation column reactor as first reaction zone.
  • the reaction product stream from the first reaction zone may be further hydrogenated to remove remaining acetylenic compounds in a fixed bed reactor as a second reaction zone.
  • the catalyst deactivates slowly while in service.
  • Partially deactivated catalyst is treated by washing with a solvent from about 170 to 600° F., preferably from 200 to 400° F. in the presence or absence of hydrogen to recover the catalyst activity.
  • suitable solvent for the catalyst washing are ethers, hydrocarbons, organic carbonates and ketones such as diethyl ether, tetrahydrofuran, furfural, gamma-butyrolactone, dimethyl carbonate, ethylene carbonate, alkyl nitriles, amides, methylpyrrolidinone, formylmorpholine, benzene, toluene, cyclohexane, ethylene glycol dimethyl ether, diethylene glycol dimethyl ether, dioxane, etc.
  • a solvent is fed to the reactor together with a hydrocarbon feed stream and hydrogen.
  • a solvent is occasionally co-fed to the reactor with hydrocarbon feed.
  • the solvent is recovered from the reactor effluent stream for the recycle.
  • Still another option is, after interrupting the hydrocarbon feed, washing the catalyst with a solvent at temperature from about 100 to 450° F. and under a pressure from ambient to about 350 psig preferentially in the presence of a small amount of or in the absence of hydrogen depending on the washing temperature and the nature of the chosen solvent.
  • the washed catalyst may be subjected to a post-washing thermal treatment at a temperature from about 170 to about 800° F. in a flow of hydrogen gas under a pressure from ambient to about 350 psig.
  • a solvent is introduced into the column either at a position above the catalyst bed or a position in the middle of the catalytic reaction zone with no reflux or minimum reflux of the overhead product stream.
  • the solvent is recovered from the bottom stream or by sidedraw from the lower section of the column for recycle.
  • the catalyst washing with solvent can be either continuous or occasional.
  • the evaluation of the catalyst performance is carried out by comparing recovery of a desired product for a given feedstock at a given conversion of acetylenic compounds or at the conversion required to meet specific product qualifications. For example, when acetylenic compounds in a crude mixed C 3 olefin feed stream are selectively hydrogenated, propylene is the desired product to be recovered from the product stream.
  • the following mathematical formula defines the recovery of propylene.
  • MAPD can be converted to propylene by selective hydrogenation, the recovery of propylene can be larger than 100 mole %.
  • a commercial eggshell type Pd catalyst supported on alpha-alumina (2.5 mm spheres) was used to remove MAPD in a mixed C 3 stream by selective hydrogenation.
  • 40 grams of the catalyst were loaded in a vertically mounted up-flow stainless steel fixed bed reactor (1 inch diameter ⁇ 20 inches long). Two thermocouples at each end of the catalyst zone are installed to control the reactor temperature.
  • the catalyst was activated at 220° F. by passing hydrogen at 350 cc per minutes for 2 hours.
  • the selective hydrogenation of MAPD impurities in a C 3 feed stream was carried out at a fixed flow rate of 4.5 ml/min and hydrogen flow rate of from 20 to 110 sccm/min under 380 psig total reactor pressure.
  • the feed comprised of 2.01 wt.
  • Another commercial eggshell type catalyst (0.3 wt. %) supported on alpha-alumina (3 ⁇ 3 mm pellets) was used to remove MAPD in the same feed used in the Control Example 1 by selective hydrogenation. 40 grams of the catalyst were loaded in the same reactor used in the Control Example 1. The catalyst was activated in an identical manner to the Control Example 1. The selective hydrogenation of MAPD impurities in the same feed used in the Control Example 1 was carried out at a constant flow rate of 4.5 ml/min and hydrogen flow rate of from 60 to 111 sccm/min under 380 psig total reactor pressure. The temperatures of the hydrogenation were about 135° F. at the end of the catalyst bed and 68-70° F. at the beginning of the catalyst bed. The test result is listed in Table 1. The performance of the catalyst was inferior to the palladium catalyst in the Control Example 1. The average MAPD content in the product at the highest MAPD conversion was 57 wt.ppm MAPD with 34.7 mole % of the average selectivity of MAPD to propylene.
  • a Ni catalyst supported on a transition alumina was prepared.
  • a gamma alumina trilope extrudate (1.3 mm diameter) was calcined at about 1000° C. for 3 hours in air.
  • a solution of nickel nitrate was prepared by dissolving 183.6 g Ni(NO 3 ) 2 .6H 2 O in 300 g water.
  • 300 grams of the calcined alumina support were placed in a rotary impregnator and then the nickel nitrate solution was poured on tumbling alumina extrudate support in the rotary impregnator. After 15 minutes cold roll, the contents in the rotary impregnator were dried at about 200° C. by blowing hot air into the rotary dryer.
  • the dried product was calcined at 380° C. for 2 hours. Based on the amount of nickel nitrate used to prepare this catalyst, the finished catalyst would have 11 wt. % Ni on alumina support. Measurement of the physical properties of the finished catalyst indicated 133 m 2 /g BET surface area, a total nitrogen adsorption pore volume of 0.669 cc/g and an average pore diameter of 18.6 nm.
  • This example demonstrates the preparation technique of a nickel-based catalyst promoted with copper and palladium supported on a nickel spinel containing alumina support. A double impregnation technique was used.
  • the gamma-alumina (1.3 mm diameter trilope extrudate) support used in the Control Example 3 was calcined at 1100° C. in air for 3 hours.
  • the calcined alumina had 96.6 m 2/g BET surface area, a total nitrogen adsorption pore volume of 0.622 cc/g and an average pore diameter of 27.7 nm.
  • this calcined alumina was not used to prepare the nickel catalyst.
  • the spinel containing calcined alumina had 26 m 2/g BET, a total nitrogen pore volume of 0.167 cc/g and an average pore diameter of 25.2 nm. This material was used to prepare a nickel-based catalyst as follows.
  • a mixed solution of nickel nitrate and copper nitrate was prepared by dissolving 106 g Ni(NO 3 ) 2 .6H 2 O and 4.5 g Cu(NO 3 ) 2 .2.5H 2 O in 300 g water.
  • 300 grams of the calcined nickel spinel containing alumina support were placed in a rotary impregnator and then the mixed solution was poured on tumbling extrudate support in the rotary impregnator. After 15 minutes cold roll, the content in a rotary impregnator was dried at about 200° C. by blowing hot air into the rotary impregnator. The dried product was calcined at 350° C. for 2 hours.
  • Another mixed solution of nickel nitrate, copper nitrate and palladium nitrate was prepared by dissolving 60 g Ni(NO 3 ) 2 .6H 2 O, 2.54 g Cu(NO 3 ) 2 .2.5H 2 O and 0.74 g Pd(NO 3 ) 2 .xH 2 O (42.8% Pd) in 300 grams of water.
  • a second impregnation was performed with this mixed solution on the first impregnation product in similar manner to the first impregnation.
  • the impregnation product was calcined at 380° C. for 2 hours. Based on the amounts of materials used in two impregnations to prepare this catalyst, the finished catalyst would have 9.98 wt. % Ni, 0.57 wt. % Cu and 0.094 wt % Pd.
  • This example demonstrates the preparation technique of a nickel-based catalyst promoted with copper and palladium supported on a nickel spinel containing alumina support. Double impregnation technique was used.
  • nickel spinel containing alumina support 1 wt. % nickel was deposited on the gamma-alumina used in the Control Example 3 and then was calcined at 1125° C. for 3 hours in air.
  • the physical properties of the spinel containing calcined alumina were 24.4 m 2 /g BET, a total nitrogen adsorption pore volume of 0.145 cc/g and an average pore diameter of 23.7 nm. This material was used to prepare a nickel-based catalyst.
  • a mixed solution of nickel nitrate and copper nitrate was prepared by dissolving 127.2 g Ni(NO 3 ) 2 .6H 2 O and 5.41 g Cu(NO 3 ) 2 .2.5H 2 O in 300 grams of water.
  • 300 grams of the calcined nickel spinel containing alumina support were placed in a rotary impregnator and then the mixed solution was poured on tumbling alumina extrudate support in the rotary impregnator. After 15 minutes cold roll, the content in the rotary impregnator was dried at about 200° C. by blowing hot air into the rotary impregnator. The dried product was calcined at 350° C. for 2 hours.
  • Another mixed solution of nickel nitrate, copper nitrate and palladium nitrate was prepared by dissolving 38.8 g Ni(NO 3 ) 2 .6H 2 O, 1.63 g Cu(NO 3 ) 2 .2.5H 2 O and 0.44 g Pd(NO 3 ) 2 .xH 2 O (42.8% Pd) in 300 g water.
  • a second impregnation was performed with this mixed solution on the first impregnation product in similar manner to the first impregnation.
  • the impregnation product was calcined at 380° C. for 2 hours. Based on the amounts of materials used in two impregnations to prepare this catalyst, the finished catalyst would have 9.99 wt. % Ni, 0.57 wt. % Cu and 0.056 wt % Pd.
  • This example demonstrates the preparation technique of a nickel-based catalyst promoted with copper and palladium supported on a nickel spinel containing alumina support. A single impregnation was performed.
  • nickel spinel containing alumina support 1 wt. % nickel was deposited on the gamma-alumina used in the Control Example 3 and then was calcined at 1150° C. for 3 hours in air.
  • the spinel containing calcined alumina had 16.8 m 2 /g BET, a total nitrogen adsorption pore volume of 0.09 cc/g and an average pore diameter of 21.1 nm.
  • XRD indicates about 95% alpha-alumina, about 5% delta and trace theta. This material was used to prepare a nickel catalyst as follows.
  • a mixed solution of nickel nitrate, copper nitrate and palladium nitrate was prepared by dissolving 166 g Ni(NO 3 ) 2 .6H 2 O, 7.04 g Cu(NO 3 ) 2 .2.5H 2 O and 0.74 g Pd(NO 3 ) 2 .xH 2 O (42.8% Pd) in 305 g water.
  • 300 grams of the calcined nickel spinel containing alumina support were placed in a rotary impregnator, and then the mixed solution was poured on tumbling alumina extrudate support in a rotary impregnator. After 15 minutes cold roll, the content in the rotary impregnator was dried at about 200° C.
  • the finished catalyst would have 9.98 wt. % Ni, 0.57 wt. % Cu and 0.094 wt % Pd.
  • the finished catalyst had 9.4 m 2/g BET, a total nitrogen adsorption pore volume of 0.035 cc/g and an average pore diameter of 14.8 nm.
  • the analysis of the catalyst indicates the following composition; 10.4 wt. % Ni, 0.55 wt. % Cu and 0.074 wt. % Pd.
  • This example demonstrates the preparation technique of a nickel-based catalyst promoted with copper and palladium supported on magnesium-spinel alumina.
  • a magnesium nitrate solution was prepared by dissolving 6 grams of Mg(NO3)2.6H20 in 320 grams water. 300 grams of gamma-alumina were impregnated with this magnesium nitrate solution. After drying the impregnated alumina at about 200° C. for 2 hours, the dried product was calcined at 1100° C. for 3 hours and then at 1150° C.
  • the support had 60.4 m 2 /g BET surface area, a total nitrogen pore volume of 0.548 cc/g and an average pore diameter of 37.3 nm.
  • a mixed solution of nickel nitrate and copper nitrate was prepared by dissolving 9681 grams of Ni(NO3)2.6H20 and 4.11 grams of Cu(NO3)2.2.5H20 in 300 grams of water. 274 grams of the magnesium-spinel/alumina were placed in a rotary impregnator and then the mixed solution was poured on the support. After 10 minutes cold rolling, the content in the impregnator was dried at about 200° C. by blowing hot air into the rotary impregnator. The dried product was calcined at 350° C. for two hours.
  • Another mixed solution of nickel nitrate, copper nitrate and palladium nitrate was prepared by dissolving 54.8 grams of Ni(NO 3 ) 2 .6H 2 O, 2.32 grams of Cu(NO 3 ) 2 .2.5H 2 O and 0.66 grams of Pd(NO 3 ) 2 .xH 2 O (42.8 wt % Pd) in 300 grams of water. Second impregnation of the first impregnation product with the second mixed solution was performed in similar manner. The dried impregnation product was calcined at 380° C. for 2 hours.
  • the active metal compositions on the support are 9.96 wt % Ni, 0.57 wt % Cu and 0.09 wt % Pd.
  • the finished catalyst had 59.3 M/g BET surface area, a total nitrogen pore volume of 0.457 cc/g and an average pore diameter of 31.8 nm.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Materials Engineering (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • General Chemical & Material Sciences (AREA)
  • Analytical Chemistry (AREA)
  • Water Supply & Treatment (AREA)
  • Catalysts (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
US10/969,613 2004-10-20 2004-10-20 Selective hydrogenation process and catalyst Abandoned US20060084830A1 (en)

Priority Applications (9)

Application Number Priority Date Filing Date Title
US10/969,613 US20060084830A1 (en) 2004-10-20 2004-10-20 Selective hydrogenation process and catalyst
MX2007003207A MX2007003207A (es) 2004-10-20 2005-07-19 Proceso y catalizador de hidrogenacion selectiva.
RU2007114902/04A RU2355670C2 (ru) 2004-10-20 2005-07-19 Способ селективного гидрирования и катализатор
CNA2005800317059A CN101432247A (zh) 2004-10-20 2005-07-19 选择加氢工艺和催化剂
KR1020077008829A KR20070074568A (ko) 2004-10-20 2005-07-19 선택적 수소화 방법 및 촉매
PCT/US2005/025606 WO2006044005A2 (en) 2004-10-20 2005-07-19 Selective hydrogenation process and catalyst
JP2007537874A JP2008516765A (ja) 2004-10-20 2005-07-19 選択的水素化方法及び触媒
TW094126451A TW200613060A (en) 2004-10-20 2005-08-03 Selective hydrogenation process and catalyst
US12/539,229 US7838710B2 (en) 2004-10-20 2009-08-11 Selective hydrogenation process and catalyst

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US10/969,613 US20060084830A1 (en) 2004-10-20 2004-10-20 Selective hydrogenation process and catalyst

Related Child Applications (1)

Application Number Title Priority Date Filing Date
US12/539,229 Division US7838710B2 (en) 2004-10-20 2009-08-11 Selective hydrogenation process and catalyst

Publications (1)

Publication Number Publication Date
US20060084830A1 true US20060084830A1 (en) 2006-04-20

Family

ID=36181643

Family Applications (2)

Application Number Title Priority Date Filing Date
US10/969,613 Abandoned US20060084830A1 (en) 2004-10-20 2004-10-20 Selective hydrogenation process and catalyst
US12/539,229 Active US7838710B2 (en) 2004-10-20 2009-08-11 Selective hydrogenation process and catalyst

Family Applications After (1)

Application Number Title Priority Date Filing Date
US12/539,229 Active US7838710B2 (en) 2004-10-20 2009-08-11 Selective hydrogenation process and catalyst

Country Status (8)

Country Link
US (2) US20060084830A1 (zh)
JP (1) JP2008516765A (zh)
KR (1) KR20070074568A (zh)
CN (1) CN101432247A (zh)
MX (1) MX2007003207A (zh)
RU (1) RU2355670C2 (zh)
TW (1) TW200613060A (zh)
WO (1) WO2006044005A2 (zh)

Cited By (24)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20070105964A1 (en) * 2005-11-10 2007-05-10 Martinis Jorge M Hydrogenation catalyst with improved textural properties
US20080139383A1 (en) * 2006-03-27 2008-06-12 Catalytic Distillation Technologies Hydrogenation of aromatic compounds
EP2177267A1 (en) * 2007-08-13 2010-04-21 Asahi Kasei Chemicals Corporation Catalyst for carboxylic acid ester production, method for producing the same, and method for producing carboxylic acid ester
US20100125037A1 (en) * 2008-11-19 2010-05-20 Antoine Negiz Layered Sphere Catalyst Formulations for Selective Hydrogenation Performance
US20100125158A1 (en) * 2008-11-19 2010-05-20 Antoine Negiz Methods for Selective Hydrogenation Performance Using a Layered Sphere Catalyst With New Formulations
WO2010074798A1 (en) * 2008-12-16 2010-07-01 Uop Llc Layered sphere catalysts with high accessibility indexes
EP2210664A1 (en) * 2007-10-26 2010-07-28 Asahi Kasei Chemicals Corporation Composite particle-loaded article, method for producing the composite particle-loaded article, and method for producing compound using the composite particle-loaded article as chemical synthesis catalyst
US20100331588A1 (en) * 2009-06-29 2010-12-30 Gajda Gregory J Process for Using Layered Sphere Catalysts with High Accessibility Indexes
WO2011008310A1 (en) * 2009-06-29 2011-01-20 Uop Llc Layered sphere catalysts with high accessibility indexes
FR3011844A1 (fr) * 2013-10-16 2015-04-17 IFP Energies Nouvelles Procede d'hydrogenation selective mettant en œuvre un catalyseur contenant du cuivre et au moins un metal choisi parmi le nickel ou le cobalt
TWI486330B (zh) * 2009-12-18 2015-06-01 China Petro Chemical Technologydevelopment Company Selective Hydrogenation of Phenylene Acetylene in the Presence of
US9084984B2 (en) 2008-12-18 2015-07-21 China Petroleum & Chemical Corporation Method for selective hydrogenation of phenylacetylene in the presence of styrene
US20150353448A1 (en) * 2014-06-06 2015-12-10 Uop Llc Process for the selective hydrogenation of acetylene to ethylene
CN106608805A (zh) * 2015-10-23 2017-05-03 中国石油化工股份有限公司 一种碳三馏分液相选择加氢的方法
FR3080300A1 (fr) * 2018-04-18 2019-10-25 IFP Energies Nouvelles Procede de preparation d'un catalyseur bimetallique a base de nickel et de platine ou de palladium
FR3091658A1 (fr) * 2019-01-15 2020-07-17 IFP Energies Nouvelles Procédé de préparation d’un catalyseur d’hydrogénation des aromatiques comprenant une étape de formation d’un alliage de NiCu en post-imprégnation
FR3091659A1 (fr) * 2019-01-15 2020-07-17 IFP Energies Nouvelles Procédé de préparation d’un catalyseur d’hydrogénation des aromatiques comprenant une étape de formation d’un alliage de NiCu en pré-imprégnation
FR3091660A1 (fr) * 2019-01-15 2020-07-17 IFP Energies Nouvelles Procédé de préparation d’un catalyseur d’hydrogénation sélective comprenant une étape de formation d’un alliage de NiCu en post-imprégnation
FR3091657A1 (fr) * 2019-01-15 2020-07-17 IFP Energies Nouvelles Procédé de préparation d’un catalyseur d’hydrogénation sélective comprenant une étape de formation d’un alliage de NiCu en pré-imprégnation
WO2022002674A1 (fr) * 2020-07-03 2022-01-06 IFP Energies Nouvelles Procede de preparation d'un catalyseur d'hydrogenation de composes aromatiques obtenu a partir de sels fondus et un alliage nickel cuivre
WO2022002675A1 (fr) * 2020-07-03 2022-01-06 IFP Energies Nouvelles Procede de preparation d'un catalyseur d'hydrogenation selective obtenu a partir de sels fondus et un alliage nickel cuivre
CN114181032A (zh) * 2020-09-15 2022-03-15 中国石油天然气股份有限公司 一种碳八馏分选择加氢除苯乙炔的方法
CN114950472A (zh) * 2022-03-31 2022-08-30 大连理工大学 苯酞加氢制备六氢苯酞催化剂的制备方法及用于苯酞加氢制备六氢苯酞的方法
CN115888727A (zh) * 2022-11-28 2023-04-04 浙江卫星能源有限公司 用于丙炔选择性加氢合成丙烯的镍基耐硫催化剂、制备方法及其应用

Families Citing this family (39)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20060084830A1 (en) 2004-10-20 2006-04-20 Catalytic Distillation Technologies Selective hydrogenation process and catalyst
US20060173224A1 (en) * 2005-02-01 2006-08-03 Catalytic Distillation Technologies Process and catalyst for selective hydrogenation of dienes and acetylenes
US20100152507A1 (en) * 2008-12-16 2010-06-17 Gajda Gregory J Process for Using Layered Sphere Catalysts with High Accessibility Indexes
US9133079B2 (en) 2012-01-13 2015-09-15 Siluria Technologies, Inc. Process for separating hydrocarbon compounds
AU2013266250B2 (en) 2012-05-24 2017-07-06 Lummus Technology Llc Oxidative coupling of methane systems and methods
CN102728386B (zh) * 2012-06-25 2014-08-06 合肥工业大学 一种Pd-Ni/Al2O3催化剂及其制备方法和用途
US9670113B2 (en) 2012-07-09 2017-06-06 Siluria Technologies, Inc. Natural gas processing and systems
WO2014089479A1 (en) 2012-12-07 2014-06-12 Siluria Technologies, Inc. Integrated processes and systems for conversion of methane to multiple higher hydrocarbon products
US8962897B2 (en) * 2012-12-19 2015-02-24 Celanese International Corporation Catalysts and processes for producing butanol
US9540241B2 (en) * 2013-03-18 2017-01-10 Enerkem, Inc. Catalysts for producing hydrogen and synthesis gas
WO2015081122A2 (en) 2013-11-27 2015-06-04 Siluria Technologies, Inc. Reactors and systems for oxidative coupling of methane
CN103910596B (zh) * 2013-12-04 2016-02-10 徐州龙辉化工科技有限公司 全馏分粗苯加氢方法及催化剂
CN104689830B (zh) * 2013-12-09 2018-09-21 中国石油化工股份有限公司 一种用于混合烯烃中炔烃和二烯烃选择加氢的催化剂
CN104016824A (zh) * 2014-01-02 2014-09-03 徐州龙辉化工科技有限公司 全馏分粗苯加氢方法及催化剂
CA2935937A1 (en) 2014-01-08 2015-07-16 Siluria Technologies, Inc. Ethylene-to-liquids systems and methods
CA3148421C (en) 2014-01-09 2024-02-13 Lummus Technology Llc Oxidative coupling of methane implementations for olefin production
US10377682B2 (en) 2014-01-09 2019-08-13 Siluria Technologies, Inc. Reactors and systems for oxidative coupling of methane
US10793490B2 (en) 2015-03-17 2020-10-06 Lummus Technology Llc Oxidative coupling of methane methods and systems
US9334204B1 (en) 2015-03-17 2016-05-10 Siluria Technologies, Inc. Efficient oxidative coupling of methane processes and systems
US20160289143A1 (en) 2015-04-01 2016-10-06 Siluria Technologies, Inc. Advanced oxidative coupling of methane
US9328297B1 (en) 2015-06-16 2016-05-03 Siluria Technologies, Inc. Ethylene-to-liquids systems and methods
WO2016205411A2 (en) 2015-06-16 2016-12-22 Siluria Technologies, Inc. Ethylene-to-liquids systems and methods
CN106582704B (zh) * 2015-10-14 2019-06-11 中国石油化工股份有限公司 两段复合镍基催化剂床
CN106582456B (zh) * 2015-10-14 2019-07-09 中国石油化工股份有限公司 复合加氢催化剂床
CN106582636B (zh) * 2015-10-14 2019-04-12 中国石油化工股份有限公司 复合催化剂床
WO2017065947A1 (en) 2015-10-16 2017-04-20 Siluria Technologies, Inc. Separation methods and systems for oxidative coupling of methane
CN106928002B (zh) * 2015-12-31 2019-12-06 中国石油天然气股份有限公司 一种碳二后加氢除炔方法
CN106928014B (zh) * 2015-12-31 2019-12-10 中国石油天然气股份有限公司 一种甲醇制低碳烯烃的除炔方法
CN106928006B (zh) * 2015-12-31 2020-04-10 中国石油天然气股份有限公司 一种加氢制取聚合级乙烯的方法
EP4071131A1 (en) 2016-04-13 2022-10-12 Lummus Technology LLC Apparatus and method for exchanging heat
WO2018118105A1 (en) 2016-12-19 2018-06-28 Siluria Technologies, Inc. Methods and systems for performing chemical separations
CN107051543B (zh) * 2017-05-08 2019-12-17 大连圣得环保新材料有限公司 一种脱炔氢催化剂及其制备方法与应用
CN108863700B (zh) * 2017-05-15 2021-05-28 中国石油天然气股份有限公司 一种苯乙烯存在下选择加氢脱除苯乙炔的方法
HUE064375T2 (hu) 2017-05-23 2024-03-28 Lummus Technology Inc Metán oxidatív csatolási folyamatainak integrálása
WO2019010498A1 (en) 2017-07-07 2019-01-10 Siluria Technologies, Inc. SYSTEMS AND METHODS FOR OXIDIZING METHANE COUPLING
WO2019175731A1 (en) * 2018-03-13 2019-09-19 Nova Chemicals (International) S.A. Mitigating oxygen, carbon dioxide and/or acetylene output from an odh process
FR3080299B1 (fr) * 2018-04-18 2020-07-10 IFP Energies Nouvelles Procede de preparation d'un catalyseur bimetallique d'hydrogenation selective a base de nickel et de cuivre
FR3080298B1 (fr) * 2018-04-18 2020-07-10 IFP Energies Nouvelles Procede de preparation d’un catalyseur bimetallique a base de nickel et de cuivre pour l’hydrogenation de composes aromatiques
CN113797907A (zh) * 2021-10-13 2021-12-17 润和科华催化剂(上海)有限公司 一种具有尖晶石结构的选择加氢催化剂及其制备方法和应用

Citations (42)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2620314A (en) * 1950-03-08 1952-12-02 Universal Oil Prod Co Spheroidal alumina
US3076858A (en) * 1958-06-16 1963-02-05 Dow Chemical Co Selective hydrogenation in the presence of copper catalysts
US3471583A (en) * 1968-10-03 1969-10-07 Catalysts & Chem Inc Palladium catalysts
US3641182A (en) * 1969-05-28 1972-02-08 Phillips Petroleum Co Highly calcined support for catalytic dehydrogenation
US3751508A (en) * 1970-02-25 1973-08-07 Nippon Oil Co Ltd Catalyst for selective hydrogenation of acetylenic hydrocarbon in the concurrent presence of diolefin
US3793388A (en) * 1972-05-30 1974-02-19 Phillips Petroleum Co Selective hydrogenation of acetylene from olefins with a nickel on alumina catalyst
US3883444A (en) * 1971-07-20 1975-05-13 Grace W R & Co Auto exhaust catalyst
US4169815A (en) * 1973-11-15 1979-10-02 Phillips Petroleum Company Catalyst for dehydrogenation process
US4172810A (en) * 1978-05-08 1979-10-30 Exxon Research & Engineering Co. Catalysts for the conversion of relatively low molecular weight hydrocarbons to high molecular weight hydrocarbons and the regeneration of the catalysts
US4179408A (en) * 1977-03-25 1979-12-18 W. R. Grace & Co. Process for preparing spheroidal alumina particles
US4261862A (en) * 1979-07-06 1981-04-14 Toyota Jidosha Kogyo Kabushiki Kaisha Catalyst for purifying exhaust gas and a process for manufacturing thereof
US4263020A (en) * 1980-01-02 1981-04-21 Exxon Research & Engineering Co. Removal of sulfur from process streams
US4273735A (en) * 1977-08-03 1981-06-16 Rhone-Poulenc Industries Production of spheroidal alumina shaped articles
US4274981A (en) * 1979-07-06 1981-06-23 Toyota Jidosha Kogyo Kabushiki Kaisha Catalyst for purifying exhaust gas and the process for manufacturing thereof
US4425312A (en) * 1982-07-02 1984-01-10 Exxon Research And Engineering Co. Removal of sulfur from process streams
US4440956A (en) * 1982-10-25 1984-04-03 The Dow Chemical Company Selective hydrogenation of acetylenes in the presence of butadiene and catalyst used in the hydrogenation
US4581343A (en) * 1983-05-19 1986-04-08 Pro-Catalyse Process for the preparation of a pollution control catalyst for internal combustion engine exhaust system/catalytic converter
US4690806A (en) * 1986-05-01 1987-09-01 Exxon Research And Engineering Company Removal of sulfur from process streams
US5028665A (en) * 1989-01-09 1991-07-02 The Dow Chemical Company Polymer hydrogenation catalysts
US5258340A (en) * 1991-02-15 1993-11-02 Philip Morris Incorporated Mixed transition metal oxide catalysts for conversion of carbon monoxide and method for producing the catalysts
US5352337A (en) * 1992-04-14 1994-10-04 Kabushiki Kaisha Toyota Chuo Kenkyusho Method for reducing nitrogen oxides
US5756420A (en) * 1996-11-05 1998-05-26 Exxon Research And Engineering Company Supported hydroconversion catalyst and process of preparation thereof
US5767040A (en) * 1992-12-21 1998-06-16 Amoco Corporation Catalyst prepared from nickel-containing hydrotalcite-like precursor compound
US5866734A (en) * 1996-09-05 1999-02-02 Aktiengesellschaft Hydrogenation process
US6127310A (en) * 1997-02-27 2000-10-03 Phillips Petroleum Company Palladium containing hydrogenation catalysts
US6218326B1 (en) * 1998-07-29 2001-04-17 University Of Iowa Research Foundation Supported molten-metal catalysts
US6350717B1 (en) * 1998-09-04 2002-02-26 Basf Aktiengesellschaft Catalyst and process for the selective hydrogenation of unsaturated compounds in hydrocarbon streams
US6388150B1 (en) * 1999-01-21 2002-05-14 Abb Lummus Global Inc. Selective hydrogenation process and catalyst therefor
US6417419B1 (en) * 2001-02-16 2002-07-09 Uop Llc Process for hydrogenating acetylenes
US6437206B1 (en) * 1998-08-29 2002-08-20 Basf Aktiengesellschaft Catalyst and processes for the selective hydrogenation of unsaturated compounds in hydrocarbon streams
US6509292B1 (en) * 2001-03-30 2003-01-21 Sud-Chemie Inc. Process for selective hydrogenation of acetylene in an ethylene purification process
US6576588B2 (en) * 2000-04-07 2003-06-10 Catalytic Distillation Technologies Process for selective hydrogenation of alkynes and catalyst therefor
US6607678B2 (en) * 1999-08-17 2003-08-19 Battelle Memorial Institute Catalyst and method of steam reforming
US6627578B2 (en) * 2000-04-30 2003-09-30 China Petro-Chemical Corporation Catalyst for selective hydrogenation
US20040176651A1 (en) * 2003-03-04 2004-09-09 Michel Molinier Catalysts for selective hydrogenation of alkynes and alkadienes
US6794552B2 (en) * 1999-09-17 2004-09-21 Phillips Petroleum Company Hydrocarbon hydrogenation catalyst and process
US20050033099A1 (en) * 2003-08-04 2005-02-10 Catalytic Distillation Technologies Ni hydrogenation catalysts, manufacture and use
US20050048658A1 (en) * 2003-09-03 2005-03-03 Synfuels International, Inc. Catalyst formulation for hydrogenation
US20050096217A1 (en) * 2003-10-29 2005-05-05 Sud-Chemie, Inc. Selective hydrogenation catalyst
US6903046B2 (en) * 2002-05-01 2005-06-07 Air Products And Chemicals, Inc. Metal modified Pd/Ni catalysts
US20050203320A1 (en) * 2001-10-15 2005-09-15 Catalytic Distillation Technologies Hydrogenation catalyst and hydrogenation process
US20050209491A1 (en) * 2004-03-19 2005-09-22 Catalytic Distillation Technologies Ni catalyst, process for making catalysts and selective hydrogenation process

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3679763A (en) * 1970-07-28 1972-07-25 Catalysts & Chem Inc Purification of process gas streams by hydrogenation
NL1009014C2 (nl) 1998-04-28 1999-10-29 Dsm Nv Werkwijze voor de hydrogenering van fenylacetyleen in een styreenbevattend medium met behulp van een katalysator.
JP2001172211A (ja) 1999-10-04 2001-06-26 Ube Ind Ltd シクロドデカノン及びシクロドデカノールの製造法
JP4154111B2 (ja) * 2000-06-09 2008-09-24 富士フイルム株式会社 磁気記録媒体
JP4573320B2 (ja) * 2000-09-08 2010-11-04 昭和電工株式会社 亜酸化窒素分解触媒、その製造方法及び亜酸化窒素の分解方法
US20060084830A1 (en) 2004-10-20 2006-04-20 Catalytic Distillation Technologies Selective hydrogenation process and catalyst

Patent Citations (49)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2620314A (en) * 1950-03-08 1952-12-02 Universal Oil Prod Co Spheroidal alumina
US3076858A (en) * 1958-06-16 1963-02-05 Dow Chemical Co Selective hydrogenation in the presence of copper catalysts
US3471583A (en) * 1968-10-03 1969-10-07 Catalysts & Chem Inc Palladium catalysts
US3641182A (en) * 1969-05-28 1972-02-08 Phillips Petroleum Co Highly calcined support for catalytic dehydrogenation
US3751508A (en) * 1970-02-25 1973-08-07 Nippon Oil Co Ltd Catalyst for selective hydrogenation of acetylenic hydrocarbon in the concurrent presence of diolefin
US3883444A (en) * 1971-07-20 1975-05-13 Grace W R & Co Auto exhaust catalyst
US3793388A (en) * 1972-05-30 1974-02-19 Phillips Petroleum Co Selective hydrogenation of acetylene from olefins with a nickel on alumina catalyst
US4169815A (en) * 1973-11-15 1979-10-02 Phillips Petroleum Company Catalyst for dehydrogenation process
US4179408A (en) * 1977-03-25 1979-12-18 W. R. Grace & Co. Process for preparing spheroidal alumina particles
US4273735A (en) * 1977-08-03 1981-06-16 Rhone-Poulenc Industries Production of spheroidal alumina shaped articles
US4172810A (en) * 1978-05-08 1979-10-30 Exxon Research & Engineering Co. Catalysts for the conversion of relatively low molecular weight hydrocarbons to high molecular weight hydrocarbons and the regeneration of the catalysts
US4261862A (en) * 1979-07-06 1981-04-14 Toyota Jidosha Kogyo Kabushiki Kaisha Catalyst for purifying exhaust gas and a process for manufacturing thereof
US4274981A (en) * 1979-07-06 1981-06-23 Toyota Jidosha Kogyo Kabushiki Kaisha Catalyst for purifying exhaust gas and the process for manufacturing thereof
US4263020A (en) * 1980-01-02 1981-04-21 Exxon Research & Engineering Co. Removal of sulfur from process streams
US4425312A (en) * 1982-07-02 1984-01-10 Exxon Research And Engineering Co. Removal of sulfur from process streams
US4440956A (en) * 1982-10-25 1984-04-03 The Dow Chemical Company Selective hydrogenation of acetylenes in the presence of butadiene and catalyst used in the hydrogenation
US4581343A (en) * 1983-05-19 1986-04-08 Pro-Catalyse Process for the preparation of a pollution control catalyst for internal combustion engine exhaust system/catalytic converter
US4690806A (en) * 1986-05-01 1987-09-01 Exxon Research And Engineering Company Removal of sulfur from process streams
US5028665A (en) * 1989-01-09 1991-07-02 The Dow Chemical Company Polymer hydrogenation catalysts
US5258340A (en) * 1991-02-15 1993-11-02 Philip Morris Incorporated Mixed transition metal oxide catalysts for conversion of carbon monoxide and method for producing the catalysts
US5352337A (en) * 1992-04-14 1994-10-04 Kabushiki Kaisha Toyota Chuo Kenkyusho Method for reducing nitrogen oxides
US5767040A (en) * 1992-12-21 1998-06-16 Amoco Corporation Catalyst prepared from nickel-containing hydrotalcite-like precursor compound
US5866734A (en) * 1996-09-05 1999-02-02 Aktiengesellschaft Hydrogenation process
US5756420A (en) * 1996-11-05 1998-05-26 Exxon Research And Engineering Company Supported hydroconversion catalyst and process of preparation thereof
US6127310A (en) * 1997-02-27 2000-10-03 Phillips Petroleum Company Palladium containing hydrogenation catalysts
US6218326B1 (en) * 1998-07-29 2001-04-17 University Of Iowa Research Foundation Supported molten-metal catalysts
US6437206B1 (en) * 1998-08-29 2002-08-20 Basf Aktiengesellschaft Catalyst and processes for the selective hydrogenation of unsaturated compounds in hydrocarbon streams
US6350717B1 (en) * 1998-09-04 2002-02-26 Basf Aktiengesellschaft Catalyst and process for the selective hydrogenation of unsaturated compounds in hydrocarbon streams
US6388150B1 (en) * 1999-01-21 2002-05-14 Abb Lummus Global Inc. Selective hydrogenation process and catalyst therefor
US6607678B2 (en) * 1999-08-17 2003-08-19 Battelle Memorial Institute Catalyst and method of steam reforming
US6958310B2 (en) * 1999-08-17 2005-10-25 Battelle Memorial Institute Catalyst and method of steam reforming
US6794552B2 (en) * 1999-09-17 2004-09-21 Phillips Petroleum Company Hydrocarbon hydrogenation catalyst and process
US6576588B2 (en) * 2000-04-07 2003-06-10 Catalytic Distillation Technologies Process for selective hydrogenation of alkynes and catalyst therefor
US20030171629A1 (en) * 2000-04-07 2003-09-11 Catalytic Distillation Technologies Process for selective hydrogenation of alkynes and catalyst therefor
US6627578B2 (en) * 2000-04-30 2003-09-30 China Petro-Chemical Corporation Catalyst for selective hydrogenation
US6417419B1 (en) * 2001-02-16 2002-07-09 Uop Llc Process for hydrogenating acetylenes
US6509292B1 (en) * 2001-03-30 2003-01-21 Sud-Chemie Inc. Process for selective hydrogenation of acetylene in an ethylene purification process
US20050203320A1 (en) * 2001-10-15 2005-09-15 Catalytic Distillation Technologies Hydrogenation catalyst and hydrogenation process
US6903046B2 (en) * 2002-05-01 2005-06-07 Air Products And Chemicals, Inc. Metal modified Pd/Ni catalysts
US20040176651A1 (en) * 2003-03-04 2004-09-09 Michel Molinier Catalysts for selective hydrogenation of alkynes and alkadienes
US20050033099A1 (en) * 2003-08-04 2005-02-10 Catalytic Distillation Technologies Ni hydrogenation catalysts, manufacture and use
US20050272964A1 (en) * 2003-08-04 2005-12-08 Catalytic Distillation Technologies Ni hydrogenation catalysts, manufacture and use
US20060030482A1 (en) * 2003-08-04 2006-02-09 Catalytic Distillation Technologies Ni hydrogenation catalysts, manufacture and use
US7022645B2 (en) * 2003-08-04 2006-04-04 Catalytic Distillation Technologies Ni hydrogenation catalysts, manufacture and use
US7196035B2 (en) * 2003-08-04 2007-03-27 Catalytic Distillation Technologies Ni hydrogenation catalysts, manufacture and use
US20050048658A1 (en) * 2003-09-03 2005-03-03 Synfuels International, Inc. Catalyst formulation for hydrogenation
US20050096217A1 (en) * 2003-10-29 2005-05-05 Sud-Chemie, Inc. Selective hydrogenation catalyst
US20050209491A1 (en) * 2004-03-19 2005-09-22 Catalytic Distillation Technologies Ni catalyst, process for making catalysts and selective hydrogenation process
US20080119354A1 (en) * 2004-03-19 2008-05-22 Catalytic Distillation Technologies Ni catalyst, process for making catalysts and selective hydrogenation process

Cited By (51)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20070105964A1 (en) * 2005-11-10 2007-05-10 Martinis Jorge M Hydrogenation catalyst with improved textural properties
US20070105713A1 (en) * 2005-11-10 2007-05-10 Intevep, S.A. Hydrogenation catalyst with improved textural properties
US7256220B2 (en) 2005-11-10 2007-08-14 Intevep, S.A. Hydrogenation catalyst with improved textural properties
US20100075828A1 (en) * 2005-11-10 2010-03-25 Intevep, S.A. Hydrogenation catalyst with improved textural properties
US8022008B2 (en) 2005-11-10 2011-09-20 Intevep, S.A. Hydrogenation catalyst with improved textural properties
US20080139383A1 (en) * 2006-03-27 2008-06-12 Catalytic Distillation Technologies Hydrogenation of aromatic compounds
EP2177267A4 (en) * 2007-08-13 2011-12-07 Asahi Kasei Chemicals Corp CATALYST FOR THE PRODUCTION OF CARBOXYLIC ACID ESTER, PROCESS FOR PRODUCING THE SAME, AND PROCESS FOR PRODUCING CARBOXYLIC ACID ESTER
CN105214683A (zh) * 2007-08-13 2016-01-06 旭化成化学株式会社 羧酸酯制造用催化剂、其制造方法、以及羧酸酯的制造方法
US8461373B2 (en) 2007-08-13 2013-06-11 Asahi Kasei Chemicals Corporation Catalyst for producing carboxylic acid esters, process for producing same and process for producing carboxylic acid esters
EP2177267A1 (en) * 2007-08-13 2010-04-21 Asahi Kasei Chemicals Corporation Catalyst for carboxylic acid ester production, method for producing the same, and method for producing carboxylic acid ester
US20110184206A1 (en) * 2007-08-13 2011-07-28 Ken Suzuki Catalyst for producing carboxylic acid esters, process for producing same and process for producing carboxylic acid esters (as amended)
US20100249448A1 (en) * 2007-10-26 2010-09-30 Ken Suzuki Supported composite particle material, production process of same and process for producing compounds using supported composite particle material as catalyst for chemical synthesis
EP2210664A1 (en) * 2007-10-26 2010-07-28 Asahi Kasei Chemicals Corporation Composite particle-loaded article, method for producing the composite particle-loaded article, and method for producing compound using the composite particle-loaded article as chemical synthesis catalyst
EP2210664A4 (en) * 2007-10-26 2011-12-21 Asahi Kasei Chemicals Corp COMPOSITE-LOADED ARTICLE, METHOD FOR PRODUCING THE COMPOSITE-RELATED ARTICLE, AND METHOD FOR PRODUCING THE COMPOUND FROM THE COMPOSITE-RELATED ARTICLE AS A CHEMICAL SYNTHETIC CATALYST
EP2500093A1 (en) * 2007-10-26 2012-09-19 Asahi Kasei Chemicals Corporation Supported composite particle material, production process of same and process for producing compounds using supported composite particle material as catalyst for chemical synthesis
US8450235B2 (en) 2007-10-26 2013-05-28 Asahi Kasei Chemicals Corporation Supported composite particle material, production process of same and process for producing compounds using supported composite particle material as catalyst for chemical synthesis
US20100125037A1 (en) * 2008-11-19 2010-05-20 Antoine Negiz Layered Sphere Catalyst Formulations for Selective Hydrogenation Performance
US20100125158A1 (en) * 2008-11-19 2010-05-20 Antoine Negiz Methods for Selective Hydrogenation Performance Using a Layered Sphere Catalyst With New Formulations
US8026194B2 (en) 2008-11-19 2011-09-27 Uop Llc Layered sphere catalyst formulations for selective hydrogenation performance
US8772561B2 (en) 2008-11-19 2014-07-08 Uop Llc Methods for selective hydrogenation performance using a layered sphere catalyst with new formulations
WO2010059273A1 (en) * 2008-11-19 2010-05-27 Uop Llc Layered sphere catalyst formulations for selective hydrogenation performance
WO2010074798A1 (en) * 2008-12-16 2010-07-01 Uop Llc Layered sphere catalysts with high accessibility indexes
RU2501604C2 (ru) * 2008-12-16 2013-12-20 Юоп Ллк Слоистые сферические катализаторы с высоким коэффициентом доступности
US9084984B2 (en) 2008-12-18 2015-07-21 China Petroleum & Chemical Corporation Method for selective hydrogenation of phenylacetylene in the presence of styrene
US20100331588A1 (en) * 2009-06-29 2010-12-30 Gajda Gregory J Process for Using Layered Sphere Catalysts with High Accessibility Indexes
WO2011008311A1 (en) * 2009-06-29 2011-01-20 Uop Llc Process for using layered sphere catalysts with high accessibility indexes
WO2011008310A1 (en) * 2009-06-29 2011-01-20 Uop Llc Layered sphere catalysts with high accessibility indexes
TWI486330B (zh) * 2009-12-18 2015-06-01 China Petro Chemical Technologydevelopment Company Selective Hydrogenation of Phenylene Acetylene in the Presence of
FR3011844A1 (fr) * 2013-10-16 2015-04-17 IFP Energies Nouvelles Procede d'hydrogenation selective mettant en œuvre un catalyseur contenant du cuivre et au moins un metal choisi parmi le nickel ou le cobalt
WO2015055380A1 (fr) * 2013-10-16 2015-04-23 IFP Energies Nouvelles Procede d'hydrogenation selective mettant en œuvre un catalyseur contenant du cuivre et au moins un metal choisi parmi le nickel ou le cobalt
US9783745B2 (en) 2013-10-16 2017-10-10 IFP Energies Nouvelles Method for selective hydrogenation using a catalyst containing copper and at least one metal selected from between nickel or cobalt
US20150353448A1 (en) * 2014-06-06 2015-12-10 Uop Llc Process for the selective hydrogenation of acetylene to ethylene
CN106608805A (zh) * 2015-10-23 2017-05-03 中国石油化工股份有限公司 一种碳三馏分液相选择加氢的方法
FR3080300A1 (fr) * 2018-04-18 2019-10-25 IFP Energies Nouvelles Procede de preparation d'un catalyseur bimetallique a base de nickel et de platine ou de palladium
FR3091657A1 (fr) * 2019-01-15 2020-07-17 IFP Energies Nouvelles Procédé de préparation d’un catalyseur d’hydrogénation sélective comprenant une étape de formation d’un alliage de NiCu en pré-imprégnation
US11779915B2 (en) 2019-01-15 2023-10-10 IFP Energies Nouvelles Process for preparing selective hydrogenation catalyst, comprising a step of forming a Ni—Cu alloy in pre-impregnation
FR3091660A1 (fr) * 2019-01-15 2020-07-17 IFP Energies Nouvelles Procédé de préparation d’un catalyseur d’hydrogénation sélective comprenant une étape de formation d’un alliage de NiCu en post-imprégnation
FR3091658A1 (fr) * 2019-01-15 2020-07-17 IFP Energies Nouvelles Procédé de préparation d’un catalyseur d’hydrogénation des aromatiques comprenant une étape de formation d’un alliage de NiCu en post-imprégnation
WO2020148134A1 (fr) * 2019-01-15 2020-07-23 IFP Energies Nouvelles Procede de preparation d'un catalyseur d'hydrogenation des aromatiques comprenant une etape de formation d'un alliage de ni-cu en post-impregnation
WO2020148132A1 (fr) * 2019-01-15 2020-07-23 IFP Energies Nouvelles Procede de preparation d'un catalyseur d'hydrogenation selective comprenant une etape de formation d'un alliage de ni-cu en post-impregnation
WO2020148133A1 (fr) * 2019-01-15 2020-07-23 IFP Energies Nouvelles Procede de preparation d'un catalyseur d'hydrogenation des aromatiques comprenant une etape de formation d'un alliage de ni-cu en pre-impregnation
WO2020148131A1 (fr) * 2019-01-15 2020-07-23 IFP Energies Nouvelles Procede de preparation d'un catalyseur d'hydrogenation selective comprenant une etape de formation d'un alliage de ni-cu en pre-impregnation
US11951456B2 (en) 2019-01-15 2024-04-09 IFP Energies Nouvelles Process for preparing a catalyst for the hydrogenation of aromatics, comprising a step of forming a Ni—Cu alloy in pre-impregnation
FR3091659A1 (fr) * 2019-01-15 2020-07-17 IFP Energies Nouvelles Procédé de préparation d’un catalyseur d’hydrogénation des aromatiques comprenant une étape de formation d’un alliage de NiCu en pré-imprégnation
WO2022002675A1 (fr) * 2020-07-03 2022-01-06 IFP Energies Nouvelles Procede de preparation d'un catalyseur d'hydrogenation selective obtenu a partir de sels fondus et un alliage nickel cuivre
FR3112087A1 (fr) * 2020-07-03 2022-01-07 IFP Energies Nouvelles Procede de preparation d’un catalyseur d’hydrogenation de composes aromatiques obtenu a partir de sels fondus et un alliage nickel cuivre
FR3112088A1 (fr) * 2020-07-03 2022-01-07 IFP Energies Nouvelles Procede de preparation d’un catalyseur d’hydrogenation selective obtenu a partir de sels fondus et un alliage nickel cuivre
WO2022002674A1 (fr) * 2020-07-03 2022-01-06 IFP Energies Nouvelles Procede de preparation d'un catalyseur d'hydrogenation de composes aromatiques obtenu a partir de sels fondus et un alliage nickel cuivre
CN114181032A (zh) * 2020-09-15 2022-03-15 中国石油天然气股份有限公司 一种碳八馏分选择加氢除苯乙炔的方法
CN114950472A (zh) * 2022-03-31 2022-08-30 大连理工大学 苯酞加氢制备六氢苯酞催化剂的制备方法及用于苯酞加氢制备六氢苯酞的方法
CN115888727A (zh) * 2022-11-28 2023-04-04 浙江卫星能源有限公司 用于丙炔选择性加氢合成丙烯的镍基耐硫催化剂、制备方法及其应用

Also Published As

Publication number Publication date
US7838710B2 (en) 2010-11-23
TW200613060A (en) 2006-05-01
US20090299114A1 (en) 2009-12-03
KR20070074568A (ko) 2007-07-12
CN101432247A (zh) 2009-05-13
WO2006044005A2 (en) 2006-04-27
JP2008516765A (ja) 2008-05-22
RU2007114902A (ru) 2008-10-27
WO2006044005A3 (en) 2009-04-16
RU2355670C2 (ru) 2009-05-20
MX2007003207A (es) 2007-05-16

Similar Documents

Publication Publication Date Title
US7838710B2 (en) Selective hydrogenation process and catalyst
US7737079B2 (en) Ni catalyst, process for making catalysts and selective hydrogenation process
EP1537062B1 (en) Selective hydrogenation of acetylenes
RU2333796C2 (ru) Никелевые катализаторы гидрирования, способ их получения и применение
US6717022B2 (en) Process for selective hydrogenation of alkynes and catalyst therefor
EP1773739B1 (en) Process for the selective hydrogenation of alkynes and/or dienes in an olefin-containing hydrocarbon stream
US20060155154A1 (en) Process for the selective hydrogenation of alkynes

Legal Events

Date Code Title Description
AS Assignment

Owner name: CATALYTIC DISTILLATION TECHNOLOGIES, CALIFORNIA

Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNOR:RYU, J. YONG;REEL/FRAME:015923/0561

Effective date: 20041018

STCB Information on status: application discontinuation

Free format text: ABANDONED -- FAILURE TO RESPOND TO AN OFFICE ACTION