KR960003799A - 수소첨가에 유용한 고체 촉매 조성물의 제조방법 - Google Patents
수소첨가에 유용한 고체 촉매 조성물의 제조방법 Download PDFInfo
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- KR960003799A KR960003799A KR1019950018768A KR19950018768A KR960003799A KR 960003799 A KR960003799 A KR 960003799A KR 1019950018768 A KR1019950018768 A KR 1019950018768A KR 19950018768 A KR19950018768 A KR 19950018768A KR 960003799 A KR960003799 A KR 960003799A
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- 239000000203 mixture Substances 0.000 title claims abstract 14
- 238000005984 hydrogenation reaction Methods 0.000 title claims 2
- 238000004519 manufacturing process Methods 0.000 title claims 2
- 239000011949 solid catalyst Substances 0.000 title claims 2
- 238000000034 method Methods 0.000 claims abstract 18
- 239000003638 chemical reducing agent Substances 0.000 claims abstract 10
- 239000007788 liquid Substances 0.000 claims abstract 10
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims abstract 8
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims abstract 8
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims abstract 6
- 150000001339 alkali metal compounds Chemical class 0.000 claims abstract 6
- 229910052783 alkali metal Inorganic materials 0.000 claims abstract 5
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims abstract 5
- 239000000463 material Substances 0.000 claims abstract 5
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims abstract 4
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims abstract 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims abstract 4
- CPRMKOQKXYSDML-UHFFFAOYSA-M rubidium hydroxide Chemical compound [OH-].[Rb+] CPRMKOQKXYSDML-UHFFFAOYSA-M 0.000 claims abstract 4
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims abstract 3
- 239000005977 Ethylene Substances 0.000 claims abstract 3
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims abstract 3
- HUCVOHYBFXVBRW-UHFFFAOYSA-M caesium hydroxide Chemical compound [OH-].[Cs+] HUCVOHYBFXVBRW-UHFFFAOYSA-M 0.000 claims abstract 3
- 229910052763 palladium Inorganic materials 0.000 claims abstract 3
- 229910052709 silver Inorganic materials 0.000 claims abstract 3
- 239000004332 silver Substances 0.000 claims abstract 3
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims abstract 2
- 239000002253 acid Substances 0.000 claims abstract 2
- 235000019253 formic acid Nutrition 0.000 claims abstract 2
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 claims abstract 2
- 239000008247 solid mixture Substances 0.000 claims 7
- 229910010277 boron hydride Inorganic materials 0.000 claims 4
- -1 boron hydride alkali metal Chemical class 0.000 claims 4
- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 claims 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 3
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims 3
- 150000001299 aldehydes Chemical class 0.000 claims 3
- 125000004432 carbon atom Chemical group C* 0.000 claims 3
- 150000001735 carboxylic acids Chemical class 0.000 claims 3
- 150000002576 ketones Chemical class 0.000 claims 3
- 229910052751 metal Inorganic materials 0.000 claims 3
- 239000002184 metal Substances 0.000 claims 3
- 235000000346 sugar Nutrition 0.000 claims 3
- 229910052725 zinc Inorganic materials 0.000 claims 3
- 239000011701 zinc Substances 0.000 claims 3
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 claims 2
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 claims 2
- XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Chemical compound [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 claims 2
- 239000007789 gas Substances 0.000 claims 2
- 230000001590 oxidative effect Effects 0.000 claims 2
- 239000011698 potassium fluoride Substances 0.000 claims 2
- 235000003270 potassium fluoride Nutrition 0.000 claims 2
- AHLATJUETSFVIM-UHFFFAOYSA-M rubidium fluoride Chemical compound [F-].[Rb+] AHLATJUETSFVIM-UHFFFAOYSA-M 0.000 claims 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 claims 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 229910002651 NO3 Inorganic materials 0.000 claims 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 claims 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims 1
- 125000003172 aldehyde group Chemical group 0.000 claims 1
- 229910001515 alkali metal fluoride Inorganic materials 0.000 claims 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical group OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 claims 1
- 150000007942 carboxylates Chemical class 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- 238000001035 drying Methods 0.000 claims 1
- 150000004820 halides Chemical class 0.000 claims 1
- 238000010438 heat treatment Methods 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims 1
- 239000012535 impurity Substances 0.000 claims 1
- 229910052700 potassium Inorganic materials 0.000 claims 1
- 239000011591 potassium Substances 0.000 claims 1
- 229910000033 sodium borohydride Inorganic materials 0.000 claims 1
- 239000012279 sodium borohydride Substances 0.000 claims 1
- 150000008163 sugars Chemical class 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 abstract 1
- 150000001340 alkali metals Chemical class 0.000 abstract 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 239000008121 dextrose Substances 0.000 abstract 1
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- 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
- C07C5/08—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by hydrogenation of carbon-to-carbon triple bonds
- C07C5/09—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by hydrogenation of carbon-to-carbon triple bonds to carbon-to-carbon double bonds
-
- 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
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- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
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- 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
- B01J23/66—Silver or gold
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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
- B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
- B01J37/16—Reducing
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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
- B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
- B01J37/16—Reducing
- B01J37/18—Reducing with gases containing free hydrogen
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- 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
- C07C5/08—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by hydrogenation of carbon-to-carbon triple bonds
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- 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
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- C07C2521/02—Boron or aluminium; Oxides or hydroxides thereof
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Abstract
팔라듐, 은 및 지지물질(바람직하게 알루미나)을 포함하는 초갬 조성물을 비교적 낮은 온도에서(약 60℃이상) 효율적인 환원제(바람직하게는 알칼리 금속 수소화 붕소, 히드라진, 포름알데히드, 포름산, 아스크로빈산, 덱스트로스, 알루미늄 분말)를 포함하는 액체 조성물과 접촉시킨다. 바람직하게, 하나 이상의 알칼리 금속 화합물(보다 바람직하게 KOH, RbOH, CsOH, KF)이 또한 액체 조성물내 존재한다. 아세틸렌을 (에틸렌으로)선택적으로 수소 첨가하기 위한 개선된 방법은 상기 습식－환원된 촉매 조성물을 사용하다.
Description
내용없음
Claims (15)
- 하기로 구성되는, 수소 첨가에 유용한 고체 촉매 조성물의 제조방법 : (1) 팔라듐, 은 및 무기지지 물질을 포함하는 고체 조성물(a), 및 (i) 하나 이상의 환원제가 히드라진, 수소화 붕소 알칼리 금속, 분자당 1－6개 탄소 원자를 함유한 알데히드, 분자당 1－6개의 탄소원자를 함유한 케톤, 분자당 1－6개 탄소원자를 함유한 카르복실산, 알데히드기 또는－히드록시케톤기를 함유한 당, 알루미늄 금속 또는 아연 금속인 하나 이상의 환원제, 및 (ⅱ) 하나 이상의 비－환원 액체 성분을 포함하는 액체 환원 조성물 (b)를 약 1초 이상의 기간동안 약 60℃이하의 온도에서 접촉시켜 습식－환원된 고체 조성물을 생성시키고; (2) 단계 (1) 내 생성된 상기 습식－환원된 고체 조성물을 상기 액체 환원 조성물로부터 실질적으로 분리하고; 및 (3) 단계 (2)에서 얻은 실질적으로 분리된 습식－환원된 고체 조성물을 건조시키고, 환원제 (i)가 상기 알데히드, 상기 케톤, 상기 카르복실산, 상기 당, 상기 알루미늄 금속 또는 상기 아연 금속인 경우, 상기 액체 환원 조성물은 알칼리 금속 수산화물 또는 알칼리 금속 플루오르화물인 하나 이상의 용해된 알카리 금속 화합물을 더 포함하고, 및 부가로 환원제가 상기 당이라면, 상기 방법은 부가로 하기를 포함한다; (4) 단계 (3)에서 얻은 건조된 습식－환원된 고체 조성물을 약 10분 이상의 시간동안 약 300℃－약 700℃의 온도에서 산화 가스 분위기내에서 가열한다.
- 제1항에 있어서, 상기 액체 환원 조성물이 본질적으로 상기 하나 이상의 환원제, 상기 하나 이상의 비－환원 액체 성분, 및 상기 하나 이상의 알칼리 금속 화합물로 구성되는 방법.
- 제1항에 있어서, 상기 환원제가 상기 히드라진, 상기 수소화 붕소 알칼리 금속, 상기 알데히드, 상기 케톤, 상기 카르복실산, 상기 알루미늄 금속 또는 상기 아연 금속이고, 상기 방법은 단계 (3)에서 얻은 건조된 습식－환원된 고체 조성물을 약 10분 이상의 시간동안 약 300℃－700℃의 온도에서 산화 가스 분위기내에 가열하는 상기 단계(4)를 부가로 포함하는 방법.
- 제1항에 있어서, 상기 하나 이상의 환원제가 상기 히드라진 또는 상기 수소화 붕소 알칼리 금속이고 상기 액체 환원 조성물이 할로겐화물, 수산화물, 탄산염, 중탄산염, 질산염 또는 카르복실산염인 하나 이상의 알칼리 금속 화합물을 포함하는 방법.
- 제1항에 있어서, 수소화 붕소 알칼리 금속이 수소화붕소나트륨 또는 수소화붕소 칼륨인 방법.
- 제1항에 있어서, 상기 하나 이상의 환원제가 텍스트로스, 포름알데히드, 포름산, 아스크로빈산 또는 알루미늄 금속이고, 상기 하나 이상의 알칼리 금속화합물이 수산화칼륨, 플루오르화칼륨, 수산화 루비듐, 플루오르화 루비듐, 수산화 세슘 또는 플르오르화 세슘인 방법.
- 제6항에 있어서, 상기 하나 이상의 알칼리 금속 화합물이 수산화칼륨 또는 플루오르화칼륨인 방법.
- 제1－7항 중 임의의 한 항에 있어서, 상기 무기 지지 물질이 알루미나, 티타니아, 지르코니아 또는 임의의 두개 이상의 상기 지지 물질의 혼합물이고; 상기 하나 이상의 비－환원 액체 성분이 물, 메탄올 또는 상기의 혼합물이고; 상기 접촉 온도는 약 10℃－60℃이고; 및 상기 접촉시간은 약 10초－약 10시간인 방법.
- 제8항에 있어서, 상기 접촉 온도가 약 20℃－50℃이고, 상기 시간 기간이 약 0.02－2시간이고, 및 상기 접촉중에 압력이 대략 대기압인 방법.
- 제8항에 있어서, 상기 무기 지지 물질이－알루미나이고, 및 상기 고체 조성물이 약 0.01－0.2중량% 팔라듐 및 약 0.02－2중량%의 은을 함유하는 방법.
- 제1－7항 중 임의의 한 항에 있어서, 단계 (4)를 약 0.2－20시간의 기간동안 약 400℃－600℃의 온도에서 공기중에서 수행하는 방법.
- 제1－7항 중 임의의 한 항에 있어서, 상기 액체 환원 조성물내 상기 하나 이상의 환원제의 중량%가 약 0.5－50중량%인 방법.
- 제1－7항 중 임의의 한 항에 따른 방법에 의해 제조된 조성물과 상기 아세틸렌을 접촉시키는 것으로 구성되는, 수소 가스를 사용하여 아세틸렌을 에틸렌으로 선택적으로 수소 첨가하기 위한 방법.
- 제13항에 있어서, 상기 아세틸렌이 에틸렌 스트림내 불순물로서, C2H2약 1－50,000 ppm 양으로 존재하는 방법.
- 제13항에 있어서, 약 0℃－150℃의 반응 온도에서 수행하는 방법.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US8/269723 | 1994-07-01 | ||
| US08/269723 | 1994-07-01 | ||
| US08/269,723 US5488024A (en) | 1994-07-01 | 1994-07-01 | Selective acetylene hydrogenation |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR960003799A true KR960003799A (ko) | 1996-02-23 |
| KR100379870B1 KR100379870B1 (ko) | 2003-08-19 |
Family
ID=23028412
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019950018768A KR100379870B1 (ko) | 1994-07-01 | 1995-06-30 | 수소첨가에유용한고체촉매조성물의제조방법 |
| KR1020020065187A KR100414260B1 (en) | 1994-07-01 | 2002-10-24 | Selective acetylene hydrogenation |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020020065187A KR100414260B1 (en) | 1994-07-01 | 2002-10-24 | Selective acetylene hydrogenation |
Country Status (11)
| Country | Link |
|---|---|
| US (2) | US5488024A (ko) |
| EP (2) | EP0689872B2 (ko) |
| JP (1) | JP4040700B2 (ko) |
| KR (2) | KR100379870B1 (ko) |
| AU (1) | AU667678B2 (ko) |
| CA (1) | CA2151414C (ko) |
| DE (2) | DE69522053T3 (ko) |
| ES (2) | ES2242660T3 (ko) |
| GR (1) | GR3037067T3 (ko) |
| MY (1) | MY113893A (ko) |
| SG (1) | SG32384A1 (ko) |
Families Citing this family (56)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5475173A (en) * | 1994-07-19 | 1995-12-12 | Phillips Petroleum Company | Hydrogenation process and catalyst therefor |
| FR2724390B1 (fr) * | 1994-09-08 | 1996-12-13 | Inst Francais Du Petrole | Hydrogenation selective de coupes hydrocarbonees renfermant des hydrocarbures monoinsatures et polyinsatures |
| US5583274A (en) † | 1995-01-20 | 1996-12-10 | Phillips Petroleum Company | Alkyne hydrogenation process |
| US5587348A (en) * | 1995-04-19 | 1996-12-24 | Phillips Petroleum Company | Alkyne hydrogenation catalyst and process |
| US6096933A (en) * | 1996-02-01 | 2000-08-01 | Phillips Petroleum Company | Hydrocarbon hydrogenation and catalyst therefor |
| AU692723B2 (en) * | 1996-02-01 | 1998-06-11 | Phillips Petroleum Company | Catalyst composition and process for selecting hydrogenation of diolefins |
| US6254894B1 (en) * | 1996-04-05 | 2001-07-03 | Zodiac Pool Care, Inc. | Silver self-regulating water purification compositions and methods |
| US5859304A (en) * | 1996-12-13 | 1999-01-12 | Stone & Webster Engineering Corp. | Chemical absorption process for recovering olefins from cracked gases |
| GB9720333D0 (en) * | 1997-09-25 | 1997-11-26 | Ici Plc | Selective hydrogenation |
| FR2770421B1 (fr) * | 1997-10-31 | 1999-12-10 | Inst Francais Du Petrole | Procede de preparation de catalyseurs utilisables dans les reactions de transformation de composes organiques |
| FR2770521B1 (fr) * | 1997-10-31 | 1999-12-10 | Inst Francais Du Petrole | Procede de deshydrogenation d'hydrocarbures aliphatiques satures en hydrocarbures olefiniques |
| FR2770520B1 (fr) * | 1997-10-31 | 1999-12-10 | Inst Francais Du Petrole | Procede d'hydrogenation selective des composes insatures |
| EP1058924B1 (en) * | 1998-01-26 | 2012-06-13 | Apple Inc. | Method and apparatus for integrating manual input |
| US6127588A (en) | 1998-10-21 | 2000-10-03 | Phillips Petroleum Company | Hydrocarbon hydrogenation catalyst and process |
| US6130260A (en) * | 1998-11-25 | 2000-10-10 | The Texas A&M University Systems | Method for converting natural gas to liquid hydrocarbons |
| US6602920B2 (en) * | 1998-11-25 | 2003-08-05 | The Texas A&M University System | Method for converting natural gas to liquid hydrocarbons |
| US5958823A (en) * | 1999-01-26 | 1999-09-28 | Phillips Petroleum Company | Hydrocarbon conversion catalyst composition and processes therefor and therewith |
| CA2371774A1 (en) * | 1999-02-18 | 2000-08-24 | Phillips Petroleum Company | Alkyne hydrogenation process |
| US6417136B2 (en) | 1999-09-17 | 2002-07-09 | Phillips Petroleum Company | Hydrocarbon hydrogenation catalyst and process |
| US6258989B1 (en) | 1999-09-30 | 2001-07-10 | Phillips Petroleum Company | Hydrocarbon upgrading process |
| US6297414B1 (en) | 1999-10-08 | 2001-10-02 | Stone & Webster Process Technology, Inc. | Deep selective hydrogenation process |
| DE10048219A1 (de) * | 2000-02-10 | 2002-04-11 | Sued Chemie Ag | Katalysator für die Hydrierung von ungesättigten Kohlenwasserstoffen |
| US6465391B1 (en) * | 2000-08-22 | 2002-10-15 | Phillips Petroleum Company | Selective hydrogenation catalyst and processes therefor and therewith |
| KR100838549B1 (ko) * | 2001-02-13 | 2008-06-17 | 가부시키가이샤 구라레 | 복합체 및 그 제조방법 |
| US6509292B1 (en) | 2001-03-30 | 2003-01-21 | Sud-Chemie Inc. | Process for selective hydrogenation of acetylene in an ethylene purification process |
| US6734130B2 (en) * | 2001-09-07 | 2004-05-11 | Chvron Phillips Chemical Company Lp | Hydrocarbon hydrogenation catalyst composition, a process of treating such catalyst composition, and a process of using such catalyst composition |
| CN1281720C (zh) * | 2001-10-15 | 2006-10-25 | 催化蒸馏技术公司 | 加氢催化剂和加氢方法 |
| US20030096880A1 (en) * | 2001-11-02 | 2003-05-22 | Conoco Inc. | Combustion deposited metal-metal oxide catalysts and process for producing synthesis gas |
| KR20050008675A (ko) * | 2002-04-08 | 2005-01-21 | 즈도케미 쇼쿠바이 가부시키가이샤 | 금속수소화물 함유 배기가스 처리제 및 금속수소화물 함유배기가스 처리방법 |
| MY137042A (en) * | 2002-06-14 | 2008-12-31 | Chevron Phillips Chemical Co | Hydrogenation palladium-silver catalyst and methods |
| US20040192983A1 (en) * | 2003-02-18 | 2004-09-30 | Chevron Phillips Chemical Co. | Acetylene hydrogenation catalyst with segregated palladium skin |
| US7115789B2 (en) * | 2003-03-28 | 2006-10-03 | Exxon Mobil Chemical Patents Inc. | Process for removal of alkynes and/or dienes from an olefin stream |
| GB0312769D0 (en) * | 2003-06-04 | 2003-07-09 | Johnson Matthey Plc | Process for selective hydrogenation of acetylenic compounds and catalyst therefor |
| US20040260131A1 (en) * | 2003-06-23 | 2004-12-23 | Chevron Phillips Chemical Company ("Cpchem") | Selective hydrocarbon hydrogenation catalyst and process |
| US7045670B2 (en) * | 2003-09-03 | 2006-05-16 | Synfuels International, Inc. | Process for liquid phase hydrogenation |
| US20050096217A1 (en) * | 2003-10-29 | 2005-05-05 | Sud-Chemie, Inc. | Selective hydrogenation catalyst |
| US7199076B2 (en) * | 2003-12-19 | 2007-04-03 | Chevron Phillips Chemical Company Lp | Methods of making and using a selective hydrogenation catalyst |
| WO2005103025A1 (en) * | 2004-04-21 | 2005-11-03 | Novogen Research Pty Ltd | Isoflavene synthetic method and catalyst |
| US7521393B2 (en) * | 2004-07-27 | 2009-04-21 | Süd-Chemie Inc | Selective hydrogenation catalyst designed for raw gas feed streams |
| CN100379492C (zh) * | 2005-01-10 | 2008-04-09 | 顾明兰 | 用Sol－gel法制备超细KF/Al2O3超强碱复合催化剂 |
| CA2616481C (en) | 2005-07-27 | 2016-06-14 | Chevron Phillips Chemical Company Lp | A selective hydrogenation catalyst and methods of making and using same |
| US20110288353A1 (en) | 2008-11-26 | 2011-11-24 | Wei Dai | Metal loaded catalyst and preparation method thereof |
| US20100152022A1 (en) * | 2008-12-17 | 2010-06-17 | Qi Sun | Catalyst regeneration method |
| US8921631B2 (en) | 2008-12-18 | 2014-12-30 | Saudi Basic Industries Corporation | Selective catalytic hydrogenation of alkynes to corresponding alkenes |
| CN102811807B (zh) | 2010-03-19 | 2016-05-18 | 国际壳牌研究有限公司 | 加氢催化剂 |
| US8648225B2 (en) | 2010-04-12 | 2014-02-11 | Chevron Phillips Chemical Company Lp | Process for hydrogenating highly unsaturated hydrocarbons and catalyst therefor |
| US20120209042A1 (en) * | 2011-02-10 | 2012-08-16 | Saudi Basic Industries Corporation | Liquid Phase Hydrogenation of Alkynes |
| PL215952B1 (pl) | 2011-05-05 | 2014-02-28 | Politechnika Lodzka | Sposób wytwarzania trójskladnikowej mieszanki naweglajacej i urzadzenie do wytwarzania trójskladnikowej mieszanki naweglajacej |
| US9617153B2 (en) * | 2011-10-11 | 2017-04-11 | Solvay Sa | Process for producing hydrogen peroxide |
| JP6333249B2 (ja) * | 2012-08-01 | 2018-05-30 | ビーエーエスエフ ソシエタス・ヨーロピアＢａｓｆ Ｓｅ | 酸化的脱水素化又はエポキシ化のための貴金属含有担持触媒 |
| CN105732263B (zh) * | 2014-12-12 | 2018-10-16 | 中国石油天然气股份有限公司 | 甲醇制烯烃装置中微量乙炔的选择加氢方法 |
| US9758446B2 (en) | 2015-11-16 | 2017-09-12 | Chevron Phillips Chemical Company Lp | Selective hydrogenation using a flow index |
| CN106944070A (zh) * | 2017-02-27 | 2017-07-14 | 北京神雾环境能源科技集团股份有限公司 | 一种高浓度乙炔选择加氢制乙烯的非贵金属催化剂的合成及应用方法 |
| US10232360B1 (en) * | 2017-09-12 | 2019-03-19 | Chevron Phillips Chemical Company, Lp | Use of organic dopants to enhance acetylene hydrogenation catalysts |
| WO2020150354A1 (en) | 2019-01-17 | 2020-07-23 | Shell Oil Company | A bimetallic nanoparticle-based catalyst, its use in selective hydrogenation, and a method of making the catalyst |
| US20240034699A1 (en) | 2022-07-28 | 2024-02-01 | Chevron Phillips Chemical Company, Lp | Flexible Benzene Production Via Selective-Higher-Olefin Oligomerization of Ethylene |
Family Cites Families (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3325556A (en) * | 1964-05-18 | 1967-06-13 | Universal Oil Prod Co | Selective hydrogenation of acetylene in a mixture of acetylene and other unsaturated hydrocarbons |
| US3477962A (en) * | 1966-05-06 | 1969-11-11 | Pfizer & Co C | Palladium-lead catalysts |
| US3489809A (en) * | 1968-04-17 | 1970-01-13 | Engelhard Min & Chem | Selective hydrogenation with a catalyst on a honeycomb support |
| US3651167A (en) * | 1970-08-03 | 1972-03-21 | Universal Oil Prod Co | Selective hydrogenation of c4-acetylenic hydrocarbons |
| AU475486B2 (en) * | 1971-11-19 | 1976-08-26 | Mitsubishi Chemical Industries Limited | Process for hydrating an unsaturated nitrile |
| JPS5412435B2 (ko) * | 1971-11-22 | 1979-05-23 | ||
| US4009126A (en) * | 1974-02-19 | 1977-02-22 | Petro-Tex Chemical Corporation | Catalyst for removing acetylenic impurities |
| US4658080A (en) * | 1974-02-19 | 1987-04-14 | Petro-Tex Chemical Corporation | Acetylene removal process |
| US4513159A (en) * | 1974-02-19 | 1985-04-23 | Petro-Tex Chemical Corporation | Acetylene removal process |
| US4644088A (en) * | 1974-02-19 | 1987-02-17 | Petro-Tex Chemical Corporation | Acetylene removal process |
| JPS5136413A (en) * | 1974-09-10 | 1976-03-27 | Kuraray Co | Fuhowaesuteru no seizoho |
| US4226809A (en) * | 1979-08-07 | 1980-10-07 | Phillips Petroleum Company | Hydrogenation of unsaturated dinitriles using catalyst comprising reaction products of nickel compound and of a palladium compound each with an alkali metal borohydride |
| US4484015A (en) * | 1981-05-06 | 1984-11-20 | Phillips Petroleum Company | Selective hydrogenation |
| US4404124A (en) * | 1981-05-06 | 1983-09-13 | Phillips Petroleum Company | Selective hydrogenation catalyst |
| JPS58177153A (ja) * | 1982-04-12 | 1983-10-17 | Nissan Motor Co Ltd | メタノ−ル改質用触媒 |
| FR2536410B1 (fr) * | 1982-11-24 | 1985-10-11 | Pro Catalyse | Procede d'hydrogenation selective des hydrocarbures acetyleniques d'une coupe d'hydrocarbures c4 renfermant du butadiene |
| KR900001368B1 (ko) * | 1987-03-11 | 1990-03-09 | 한국과학 기술원 | 산화티탄 담지 팔라듐 촉매의 제조방법 |
| FR2619391B1 (fr) * | 1987-08-14 | 1990-01-12 | Eurecat Europ Retrait Catalys | Procede de reduction d'un catalyseur de raffinage avant sa mise en oeuvre |
| DE3736557A1 (de) * | 1987-10-28 | 1989-05-11 | Sued Chemie Ag | Katalysator zur selektiven hydrierung von mehrfach ungesaettigten kohlenwasserstoffen |
| FR2642670B1 (fr) * | 1989-02-07 | 1991-05-24 | Eurecat Europ Retrait Catalys | Procede de reduction d'un catalyseur de raffinage avant sa mise en oeuvr |
-
1994
- 1994-07-01 US US08/269,723 patent/US5488024A/en not_active Expired - Lifetime
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1995
- 1995-05-19 US US08/445,441 patent/US5510550A/en not_active Expired - Lifetime
- 1995-06-09 CA CA002151414A patent/CA2151414C/en not_active Expired - Fee Related
- 1995-06-26 AU AU23246/95A patent/AU667678B2/en not_active Ceased
- 1995-06-29 SG SG1995000756A patent/SG32384A1/en unknown
- 1995-06-30 ES ES01100090T patent/ES2242660T3/es not_active Expired - Lifetime
- 1995-06-30 DE DE69522053.5T patent/DE69522053T3/de not_active Expired - Lifetime
- 1995-06-30 DE DE69534206T patent/DE69534206T2/de not_active Expired - Lifetime
- 1995-06-30 KR KR1019950018768A patent/KR100379870B1/ko not_active IP Right Cessation
- 1995-06-30 EP EP95110256.5A patent/EP0689872B2/en not_active Expired - Lifetime
- 1995-06-30 JP JP16651295A patent/JP4040700B2/ja not_active Expired - Fee Related
- 1995-06-30 EP EP01100090A patent/EP1110606B1/en not_active Expired - Lifetime
- 1995-06-30 ES ES95110256T patent/ES2159585T3/es not_active Expired - Lifetime
- 1995-06-30 MY MYPI95001820A patent/MY113893A/en unknown
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Also Published As
| Publication number | Publication date |
|---|---|
| DE69522053D1 (de) | 2001-09-13 |
| SG32384A1 (en) | 1996-08-13 |
| DE69534206D1 (de) | 2005-06-16 |
| DE69534206T2 (de) | 2006-01-12 |
| ES2159585T3 (es) | 2001-10-16 |
| JPH08173807A (ja) | 1996-07-09 |
| AU667678B2 (en) | 1996-04-04 |
| MY113893A (en) | 2002-06-29 |
| KR100379870B1 (ko) | 2003-08-19 |
| DE69522053T2 (de) | 2002-03-21 |
| EP0689872B2 (en) | 2013-12-11 |
| AU2324695A (en) | 1996-01-18 |
| EP1110606B1 (en) | 2005-05-11 |
| EP0689872B1 (en) | 2001-08-08 |
| DE69522053T3 (de) | 2014-07-03 |
| ES2242660T3 (es) | 2005-11-16 |
| GR3037067T3 (en) | 2002-01-31 |
| EP0689872A1 (en) | 1996-01-03 |
| KR100414260B1 (en) | 2004-01-07 |
| EP1110606A1 (en) | 2001-06-27 |
| CA2151414C (en) | 2000-01-25 |
| US5488024A (en) | 1996-01-30 |
| US5510550A (en) | 1996-04-23 |
| JP4040700B2 (ja) | 2008-01-30 |
| CA2151414A1 (en) | 1996-01-02 |
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