DE3020698C2 - - Google Patents
Info
- Publication number
- DE3020698C2 DE3020698C2 DE3020698A DE3020698A DE3020698C2 DE 3020698 C2 DE3020698 C2 DE 3020698C2 DE 3020698 A DE3020698 A DE 3020698A DE 3020698 A DE3020698 A DE 3020698A DE 3020698 C2 DE3020698 C2 DE 3020698C2
- Authority
- DE
- Germany
- Prior art keywords
- catalyst
- pressure
- temperature
- reaction
- activity
- 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 - Lifetime
Links
- 239000003054 catalyst Substances 0.000 claims description 43
- 238000006243 chemical reaction Methods 0.000 claims description 33
- 238000000034 method Methods 0.000 claims description 25
- 239000000126 substance Substances 0.000 claims description 16
- 239000012530 fluid Substances 0.000 claims description 15
- 230000000694 effects Effects 0.000 claims description 13
- 230000008021 deposition Effects 0.000 claims description 7
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 6
- 239000002638 heterogeneous catalyst Substances 0.000 claims description 6
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims description 6
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 claims description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 claims description 4
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims description 4
- 229910002092 carbon dioxide Inorganic materials 0.000 claims description 3
- 238000007086 side reaction Methods 0.000 claims description 3
- 229910052786 argon Inorganic materials 0.000 claims description 2
- 239000001273 butane Substances 0.000 claims description 2
- 239000001569 carbon dioxide Substances 0.000 claims description 2
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 238000004375 physisorption Methods 0.000 claims description 2
- 239000001294 propane Substances 0.000 claims description 2
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 18
- 230000008569 process Effects 0.000 description 15
- 230000007420 reactivation Effects 0.000 description 12
- 239000000047 product Substances 0.000 description 9
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 8
- 230000009849 deactivation Effects 0.000 description 8
- 238000006317 isomerization reaction Methods 0.000 description 8
- 230000003197 catalytic effect Effects 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000000571 coke Substances 0.000 description 4
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 4
- 150000001336 alkenes Chemical class 0.000 description 3
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 229910052593 corundum Inorganic materials 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- 229910001845 yogo sapphire Inorganic materials 0.000 description 3
- GLCIPJOIEVLTPR-UHFFFAOYSA-N 2-chlorohexane Chemical compound CCCCC(C)Cl GLCIPJOIEVLTPR-UHFFFAOYSA-N 0.000 description 2
- QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical compound CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 230000032683 aging Effects 0.000 description 2
- 238000005804 alkylation reaction Methods 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 238000004939 coking Methods 0.000 description 2
- 238000003795 desorption Methods 0.000 description 2
- 238000002845 discoloration Methods 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 2
- 239000000314 lubricant Substances 0.000 description 2
- 238000004949 mass spectrometry Methods 0.000 description 2
- 239000002574 poison Substances 0.000 description 2
- 231100000614 poison Toxicity 0.000 description 2
- 231100000572 poisoning Toxicity 0.000 description 2
- 230000000607 poisoning effect Effects 0.000 description 2
- 238000001179 sorption measurement Methods 0.000 description 2
- 230000007306 turnover Effects 0.000 description 2
- RYPKRALMXUUNKS-HYXAFXHYSA-N (z)-hex-2-ene Chemical compound CCC\C=C/C RYPKRALMXUUNKS-HYXAFXHYSA-N 0.000 description 1
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 1
- RYPKRALMXUUNKS-UHFFFAOYSA-N 2-Hexene Natural products CCCC=CC RYPKRALMXUUNKS-UHFFFAOYSA-N 0.000 description 1
- RYPKRALMXUUNKS-HWKANZROSA-N 2E-hexene Chemical compound CCC\C=C\C RYPKRALMXUUNKS-HWKANZROSA-N 0.000 description 1
- XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 238000007259 addition reaction Methods 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- -1 amines Ethylene oxide Chemical class 0.000 description 1
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000012876 carrier material Substances 0.000 description 1
- 238000004523 catalytic cracking Methods 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000005336 cracking Methods 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 230000002140 halogenating effect Effects 0.000 description 1
- 125000004836 hexamethylene group Chemical class [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 230000036571 hydration Effects 0.000 description 1
- 238000006703 hydration reaction Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 229910052961 molybdenite Inorganic materials 0.000 description 1
- CWQXQMHSOZUFJS-UHFFFAOYSA-N molybdenum disulfide Chemical compound S=[Mo]=S CWQXQMHSOZUFJS-UHFFFAOYSA-N 0.000 description 1
- 229910052982 molybdenum disulfide Inorganic materials 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000003348 petrochemical agent Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000012958 reprocessing Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000005245 sintering Methods 0.000 description 1
- 238000006277 sulfonation reaction Methods 0.000 description 1
- 238000003878 thermal aging Methods 0.000 description 1
- ZQDPJFUHLCOCRG-AATRIKPKSA-N trans-3-hexene Chemical compound CC\C=C\CC ZQDPJFUHLCOCRG-AATRIKPKSA-N 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2/00—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms
- C07C2/54—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition of unsaturated hydrocarbons to saturated hydrocarbons or to hydrocarbons containing a six-membered aromatic ring with no unsaturation outside the aromatic ring
- C07C2/64—Addition to a carbon atom of a six-membered aromatic ring
- C07C2/66—Catalytic processes
-
- 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
- B01J23/90—Regeneration or reactivation
-
- 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
- C07C5/22—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by isomerisation
- C07C5/23—Rearrangement of carbon-to-carbon unsaturated bonds
- C07C5/25—Migration of carbon-to-carbon double bonds
- C07C5/2506—Catalytic processes
- C07C5/2512—Catalytic processes with metal oxides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2521/00—Catalysts comprising the elements, oxides or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium or hafnium
- C07C2521/02—Boron or aluminium; Oxides or hydroxides thereof
- C07C2521/04—Alumina
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/584—Recycling of catalysts
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19803020698 DE3020698A1 (de) | 1980-05-31 | 1980-05-31 | Verfahren zur wiederherstellung oder aufrechterhaltung der aktivitaet von heterogenen katalysatoren fuer normal- und niederdruckreaktionen |
| JP8119181A JPS5721939A (en) | 1980-05-31 | 1981-05-29 | Method of recovering or maintaining activity of heterogeneous system catalyst for reaction at normal pressure and low pressure |
| US06/731,348 US4605811A (en) | 1980-05-31 | 1985-05-06 | Process for restoring or maintaining the activity of heterogeneous catalysts for reactions at normal and low pressures |
| US06/849,131 US4721826A (en) | 1980-05-31 | 1986-04-07 | Process for restoring or maintaining the activity of heterogeneous catalysts for reactions at normal and low pressures |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19803020698 DE3020698A1 (de) | 1980-05-31 | 1980-05-31 | Verfahren zur wiederherstellung oder aufrechterhaltung der aktivitaet von heterogenen katalysatoren fuer normal- und niederdruckreaktionen |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE3020698A1 DE3020698A1 (de) | 1982-05-19 |
| DE3020698C2 true DE3020698C2 (enExample) | 1991-08-29 |
Family
ID=6103646
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19803020698 Granted DE3020698A1 (de) | 1980-05-31 | 1980-05-31 | Verfahren zur wiederherstellung oder aufrechterhaltung der aktivitaet von heterogenen katalysatoren fuer normal- und niederdruckreaktionen |
Country Status (3)
| Country | Link |
|---|---|
| US (2) | US4605811A (enExample) |
| JP (1) | JPS5721939A (enExample) |
| DE (1) | DE3020698A1 (enExample) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3020698A1 (de) * | 1980-05-31 | 1982-05-19 | Kurt Prof. Dr. 8000 München Dialer | Verfahren zur wiederherstellung oder aufrechterhaltung der aktivitaet von heterogenen katalysatoren fuer normal- und niederdruckreaktionen |
| US5191146A (en) * | 1989-11-29 | 1993-03-02 | Uop | Olefin isomerization process |
| US5725756A (en) * | 1995-04-18 | 1998-03-10 | Center For Research, Inc. | In situ mitigation of coke buildup in porous catalysts with supercritical reaction media |
| US6294194B1 (en) * | 1997-10-14 | 2001-09-25 | Boehringer Ingelheim Pharmaceuticals, Inc. | Method for extraction and reaction using supercritical fluids |
| US6103948A (en) * | 1997-12-24 | 2000-08-15 | Bechtel Bwxt Idaho, Llc | Solid catalyzed isoparaffin alkylation at supercritical fluid and near-supercritical fluid conditions |
| US6606855B1 (en) * | 1999-06-08 | 2003-08-19 | Bechtel Bwxt Idaho, Llc | Plasma reforming and partial oxidation of hydrocarbon fuel vapor to produce synthesis gas and/or hydrogen gas |
| KR20020007385A (ko) * | 1999-06-15 | 2002-01-26 | 토니 알 콜링우드 | 메탄올 염화수소첨가반응 촉매로서 알칼리 금속이 도핑된에타-알루미나의 이용 |
| US7407905B2 (en) * | 2000-06-14 | 2008-08-05 | Battelle Energy Alliance, Llc | Method for reactivating catalysts and a method for recycling supercritical fluids used to reactivate the catalysts |
| US6579821B1 (en) | 2000-06-14 | 2003-06-17 | Bechtel Bwxt Idaho, Llc | Method for reactivating solid catalysts used in alkylation reactions |
| US7268264B2 (en) * | 2002-10-04 | 2007-09-11 | Fina Technology, Inc. | Critical phase alkylation process |
| US20040138511A1 (en) * | 2003-01-10 | 2004-07-15 | James Butler | Aromatic alkylation process with direct recycle |
| US7592282B2 (en) * | 2004-11-11 | 2009-09-22 | Battelle Energy Alliance, Llc | Enhancement of alkylation catalysts for improved supercritical fluid regeneration |
| US7297827B2 (en) * | 2004-11-29 | 2007-11-20 | Fina Technology, Inc. | Use of monolith catalyst to prepare ethylbenzene |
| CN101611125A (zh) * | 2006-09-14 | 2009-12-23 | 生物燃料箱公司 | 细胞类脂向生物燃料的充分且高效的转换的方法 |
| WO2009002878A1 (en) * | 2007-06-22 | 2008-12-31 | Biofuelbox Corporation | System for production and purification of biofuel |
| WO2009002880A1 (en) * | 2007-06-22 | 2008-12-31 | Biofuelbox Corporation | Vessels and methods for synthesis of biofuel |
| US8134036B2 (en) * | 2008-03-13 | 2012-03-13 | Fina Technology Inc | Process for liquid phase alkylation |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2166160A (en) * | 1935-04-10 | 1939-07-18 | Atlantic Refining Co | Treatment of hydrocarbon oils |
| US2353552A (en) * | 1942-07-13 | 1944-07-11 | Phillips Petroleum Co | Process and catalyst for the isomerization of hydrocarbons |
| US2587425A (en) * | 1949-04-30 | 1952-02-26 | Standard Oil Dev Co | Reforming naphtha with activated carbon catalyst |
| DE1493190C3 (de) * | 1963-04-16 | 1980-10-16 | Studiengesellschaft Kohle Mbh, 4330 Muelheim | Verfahren zur Trennung von Stoffgemischen |
| US3654181A (en) * | 1970-10-21 | 1972-04-04 | Dow Chemical Co | Method for activation of iron oxide containing dehydrogenation catalysts |
| US3914328A (en) * | 1971-05-17 | 1975-10-21 | Stauffer Chemical Co | Catalyst regeneration |
| JPS5131679A (en) * | 1974-09-11 | 1976-03-17 | Hitachi Ltd | Mukikyuchakuzai no saiseiho oyobi sonosochi |
| DE2853065A1 (de) * | 1978-12-08 | 1980-06-19 | Varta Batterie | Verfahren zur extraktion der reaktionsprodukte aus altkatalysatoren |
| US4291185A (en) * | 1978-12-14 | 1981-09-22 | Mobil Oil Corporation | Alkylation of benzene in petroleum |
| JPS5621651A (en) * | 1979-07-23 | 1981-02-28 | Kureha Chem Ind Co Ltd | Separating catalyst from homogeneous catalytic reaction system |
| DE3020698A1 (de) * | 1980-05-31 | 1982-05-19 | Kurt Prof. Dr. 8000 München Dialer | Verfahren zur wiederherstellung oder aufrechterhaltung der aktivitaet von heterogenen katalysatoren fuer normal- und niederdruckreaktionen |
-
1980
- 1980-05-31 DE DE19803020698 patent/DE3020698A1/de active Granted
-
1981
- 1981-05-29 JP JP8119181A patent/JPS5721939A/ja active Pending
-
1985
- 1985-05-06 US US06/731,348 patent/US4605811A/en not_active Expired - Fee Related
-
1986
- 1986-04-07 US US06/849,131 patent/US4721826A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| US4721826A (en) | 1988-01-26 |
| JPS5721939A (en) | 1982-02-04 |
| DE3020698A1 (de) | 1982-05-19 |
| US4605811A (en) | 1986-08-12 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |