JP4355289B2 - ビニル芳香族炭化水素の製造法における触媒の延命法 - Google Patents
ビニル芳香族炭化水素の製造法における触媒の延命法 Download PDFInfo
- Publication number
- JP4355289B2 JP4355289B2 JP2004534345A JP2004534345A JP4355289B2 JP 4355289 B2 JP4355289 B2 JP 4355289B2 JP 2004534345 A JP2004534345 A JP 2004534345A JP 2004534345 A JP2004534345 A JP 2004534345A JP 4355289 B2 JP4355289 B2 JP 4355289B2
- Authority
- JP
- Japan
- Prior art keywords
- catalyst
- catalyst life
- aromatic hydrocarbons
- prolonging agent
- agent
- 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.)
- Expired - Fee Related
Links
- 239000003054 catalyst Substances 0.000 title claims description 95
- -1 vinyl aromatic hydrocarbons Chemical class 0.000 title claims description 50
- 229920002554 vinyl polymer Polymers 0.000 title claims description 27
- 238000004519 manufacturing process Methods 0.000 title claims description 17
- 238000000034 method Methods 0.000 claims description 58
- 239000003795 chemical substances by application Substances 0.000 claims description 43
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 25
- 238000006356 dehydrogenation reaction Methods 0.000 claims description 21
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 12
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 claims description 11
- 238000006243 chemical reaction Methods 0.000 claims description 10
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical group [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- 235000011056 potassium acetate Nutrition 0.000 claims description 3
- JLBJTVDPSNHSKJ-UHFFFAOYSA-N 4-Methylstyrene Chemical compound CC1=CC=C(C=C)C=C1 JLBJTVDPSNHSKJ-UHFFFAOYSA-N 0.000 claims description 2
- 241001385733 Aesculus indica Species 0.000 claims 4
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 16
- 229910052700 potassium Inorganic materials 0.000 description 14
- 239000011591 potassium Substances 0.000 description 14
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 9
- 230000003197 catalytic effect Effects 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 235000013980 iron oxide Nutrition 0.000 description 5
- 150000001339 alkali metal compounds Chemical class 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 229910000287 alkaline earth metal oxide Inorganic materials 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 229910052742 iron Inorganic materials 0.000 description 2
- 238000012423 maintenance Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000002574 poison Substances 0.000 description 2
- 231100000614 poison Toxicity 0.000 description 2
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical group [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 150000000703 Cerium Chemical class 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 239000004606 Fillers/Extenders Substances 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 229910000423 chromium oxide Inorganic materials 0.000 description 1
- 239000003426 co-catalyst Substances 0.000 description 1
- 238000010960 commercial process Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000011010 flushing procedure Methods 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 230000002452 interceptive effect Effects 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 235000000396 iron Nutrition 0.000 description 1
- VBMVTYDPPZVILR-UHFFFAOYSA-N iron(2+);oxygen(2-) Chemical class [O-2].[Fe+2] VBMVTYDPPZVILR-UHFFFAOYSA-N 0.000 description 1
- 229910052747 lanthanoid Inorganic materials 0.000 description 1
- 150000002602 lanthanoids Chemical class 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 150000002763 monocarboxylic acids Chemical class 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920005990 polystyrene resin Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 150000003112 potassium compounds Chemical class 0.000 description 1
- CHWRSCGUEQEHOH-UHFFFAOYSA-N potassium oxide Chemical compound [O-2].[K+].[K+] CHWRSCGUEQEHOH-UHFFFAOYSA-N 0.000 description 1
- 229910001950 potassium oxide Inorganic materials 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- UMPKMCDVBZFQOK-UHFFFAOYSA-N potassium;iron(3+);oxygen(2-) Chemical compound [O-2].[O-2].[K+].[Fe+3] UMPKMCDVBZFQOK-UHFFFAOYSA-N 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000001172 regenerating effect Effects 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 239000003923 scrap metal Substances 0.000 description 1
- 239000011949 solid catalyst Substances 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 150000003440 styrenes Chemical class 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000011144 upstream manufacturing Methods 0.000 description 1
- 238000009834 vaporization Methods 0.000 description 1
- 230000008016 vaporization Effects 0.000 description 1
- 229910000859 α-Fe Inorganic materials 0.000 description 1
- 229910006540 α-FeOOH Inorganic materials 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/02—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the alkali- or alkaline earth metals or beryllium
- B01J23/04—Alkali metals
-
- 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
- C07C5/32—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by dehydrogenation with formation of free hydrogen
- C07C5/327—Formation of non-aromatic carbon-to-carbon double bonds only
- C07C5/333—Catalytic processes
- C07C5/3332—Catalytic processes with metal oxides or metal sulfides
-
- 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
- B01J23/74—Iron group metals
- B01J23/745—Iron
-
- 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
- B01J3/00—Processes of utilising sub-atmospheric or super-atmospheric pressure to effect chemical or physical change of matter; Apparatus therefor
- B01J3/06—Processes using ultra-high pressure, e.g. for the formation of diamonds; Apparatus therefor, e.g. moulds or dies
- B01J3/08—Application of shock waves for chemical reactions or for modifying the crystal structure of substances
-
- 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
- B01J23/76—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
- B01J23/78—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36 with alkali- or alkaline earth metals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2523/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00
- C07C2523/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of the iron group metals or copper
- C07C2523/74—Iron group metals
- C07C2523/745—Iron
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Crystallography & Structural Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10/235,279 US6936743B2 (en) | 2002-09-05 | 2002-09-05 | Method for extending catalyst life in processes for preparing vinyl aromatic hydrocarbons |
| PCT/US2003/026947 WO2004022212A2 (en) | 2002-09-05 | 2003-08-28 | A method for extending catalyst life in processes for preparing vinyl aromatic hydrocarbons |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2006511467A JP2006511467A (ja) | 2006-04-06 |
| JP2006511467A5 JP2006511467A5 (enExample) | 2006-10-12 |
| JP4355289B2 true JP4355289B2 (ja) | 2009-10-28 |
Family
ID=31977541
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2004534345A Expired - Fee Related JP4355289B2 (ja) | 2002-09-05 | 2003-08-28 | ビニル芳香族炭化水素の製造法における触媒の延命法 |
Country Status (9)
| Country | Link |
|---|---|
| US (2) | US6936743B2 (enExample) |
| EP (1) | EP1545758B1 (enExample) |
| JP (1) | JP4355289B2 (enExample) |
| KR (1) | KR100980652B1 (enExample) |
| CN (1) | CN1301942C (enExample) |
| AU (1) | AU2003260118A1 (enExample) |
| CA (1) | CA2493486C (enExample) |
| ES (1) | ES2602177T3 (enExample) |
| WO (1) | WO2004022212A2 (enExample) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20060224029A1 (en) * | 2005-03-29 | 2006-10-05 | Fina Technology, Inc. | Method of extending catalyst life in vinyl aromatic hydrocarbon formation |
| EP2000450A1 (en) * | 2007-06-05 | 2008-12-10 | Total Petrochemicals France | Regeneration and stabilization of dehydrogenation catalyst |
| US7981377B2 (en) * | 2007-11-06 | 2011-07-19 | Fina Technology, Inc. | Dehydrogenation of alkyl aromatics |
| US9138706B2 (en) | 2008-04-22 | 2015-09-22 | Fina Technology, Inc. | Method and apparatus for addition of an alkali metal promoter to a dehydrogenation catalyst |
| US8648007B2 (en) | 2008-04-22 | 2014-02-11 | Fina Technology, Inc. | Vaporization and transportation of alkali metal salts |
| CN101623643B (zh) * | 2008-07-08 | 2011-07-20 | 中国石油化工股份有限公司 | 失活乙苯脱氢制苯乙烯催化剂的再生方法 |
| CN101992129B (zh) * | 2009-08-31 | 2013-03-06 | 中国石油化工股份有限公司 | 乙苯脱氢制备苯乙烯催化剂的补钾方法 |
| US8912110B2 (en) | 2012-03-29 | 2014-12-16 | Uop Llc | Catalyst for conversion of hydrocarbons |
| US9266091B2 (en) | 2012-03-29 | 2016-02-23 | Uop Llc | Reforming catalysts with tuned acidity for maximum aromatics yield |
| US11124439B2 (en) | 2015-12-07 | 2021-09-21 | The University Of North Carolina At Charlotte | Devices, systems, and methods for heterogeneous catalytic quenching of hydrogen peroxide in a water source |
| WO2020214181A1 (en) | 2019-04-18 | 2020-10-22 | Lummus Technology Llc | Systems and processes for maintaining ethylbenzene dehydrogenation catalyst activity |
| US10961169B2 (en) | 2019-04-18 | 2021-03-30 | Lummus Technology Llc | Systems and processes for maintaining ethylbenzene dehydration catalyst activity |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2518354A (en) * | 1943-03-24 | 1950-08-08 | Standard Oil Dev Co | Method of maintaining catalyst activity in a dehydrogenation process |
| US4590324A (en) * | 1985-03-11 | 1986-05-20 | Amoco Corporation | Dehydrogenation of alkylaromatics |
| DD298353A5 (de) * | 1989-08-10 | 1992-02-20 | Buna Ag,De | Verfahren zur regenerierung von kaliumpromotierten dehydrierkatalysatoren |
| US5503163A (en) * | 1991-06-20 | 1996-04-02 | Boyd; Lynn | Neurosurgical drape pack |
| US5739071A (en) * | 1993-07-07 | 1998-04-14 | Raytheon Engineers & Constructors, Inc. | Method and apparatus for regeneratinig and stabilizing dehydrogenation catalysts |
| US5461179A (en) * | 1993-07-07 | 1995-10-24 | Raytheon Engineers & Constructors, Inc. | Regeneration and stabilization of dehydrogenation catalysts |
| US5689027A (en) * | 1994-11-18 | 1997-11-18 | Mobil Oil Corporation | Selective ethylbenzene conversion |
| AU696088B2 (en) * | 1994-12-14 | 1998-09-03 | Shell Internationale Research Maatschappij B.V. | Large particle dehydrogenation catalyst and process |
| IT1293531B1 (it) * | 1997-08-01 | 1999-03-01 | Sud Chemie Mt S R L Ex Monteca | Catalizzatori per la deidrogenazione dell'etilbenzene a stirene |
-
2002
- 2002-09-05 US US10/235,279 patent/US6936743B2/en not_active Expired - Lifetime
-
2003
- 2003-08-28 KR KR1020057002584A patent/KR100980652B1/ko not_active Expired - Fee Related
- 2003-08-28 WO PCT/US2003/026947 patent/WO2004022212A2/en not_active Ceased
- 2003-08-28 CN CNB038211955A patent/CN1301942C/zh not_active Expired - Fee Related
- 2003-08-28 EP EP03794519.3A patent/EP1545758B1/en not_active Expired - Lifetime
- 2003-08-28 CA CA2493486A patent/CA2493486C/en not_active Expired - Fee Related
- 2003-08-28 AU AU2003260118A patent/AU2003260118A1/en not_active Abandoned
- 2003-08-28 ES ES03794519.3T patent/ES2602177T3/es not_active Expired - Lifetime
- 2003-08-28 JP JP2004534345A patent/JP4355289B2/ja not_active Expired - Fee Related
-
2005
- 2005-06-03 US US11/145,345 patent/US20050222477A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| US6936743B2 (en) | 2005-08-30 |
| WO2004022212A3 (en) | 2004-07-29 |
| ES2602177T3 (es) | 2017-02-20 |
| WO2004022212A2 (en) | 2004-03-18 |
| KR100980652B1 (ko) | 2010-09-07 |
| EP1545758B1 (en) | 2016-08-10 |
| KR20050049481A (ko) | 2005-05-25 |
| AU2003260118A8 (en) | 2004-03-29 |
| EP1545758A4 (en) | 2010-03-10 |
| CN1301942C (zh) | 2007-02-28 |
| US20050222477A1 (en) | 2005-10-06 |
| CN1681751A (zh) | 2005-10-12 |
| CA2493486C (en) | 2011-10-18 |
| US20040049091A1 (en) | 2004-03-11 |
| EP1545758A2 (en) | 2005-06-29 |
| JP2006511467A (ja) | 2006-04-06 |
| AU2003260118A1 (en) | 2004-03-29 |
| CA2493486A1 (en) | 2004-03-18 |
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