JP2002510303A - 二酸化炭素および／または他の助溶剤を用いる改良固体酸超臨界アルキル化反応 - Google Patents
二酸化炭素および／または他の助溶剤を用いる改良固体酸超臨界アルキル化反応Info
- Publication number
- JP2002510303A JP2002510303A JP50286199A JP50286199A JP2002510303A JP 2002510303 A JP2002510303 A JP 2002510303A JP 50286199 A JP50286199 A JP 50286199A JP 50286199 A JP50286199 A JP 50286199A JP 2002510303 A JP2002510303 A JP 2002510303A
- Authority
- JP
- Japan
- Prior art keywords
- reaction mixture
- catalyst
- olefin
- diluent
- isoparaffin
- 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.)
- Ceased
Links
- 238000005804 alkylation reaction Methods 0.000 title claims abstract description 36
- 239000006184 cosolvent Substances 0.000 title claims abstract description 23
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 title claims abstract description 18
- 229910002092 carbon dioxide Inorganic materials 0.000 title claims abstract description 9
- 239000001569 carbon dioxide Substances 0.000 title claims abstract description 9
- 239000011973 solid acid Substances 0.000 title 1
- 239000003054 catalyst Substances 0.000 claims abstract description 48
- 238000000034 method Methods 0.000 claims abstract description 47
- 239000011541 reaction mixture Substances 0.000 claims abstract description 34
- 238000006243 chemical reaction Methods 0.000 claims abstract description 29
- 150000001336 alkenes Chemical class 0.000 claims abstract description 26
- 230000029936 alkylation Effects 0.000 claims abstract description 26
- 239000003085 diluting agent Substances 0.000 claims abstract description 19
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims abstract description 17
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims abstract description 8
- 239000000376 reactant Substances 0.000 claims abstract description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 5
- 239000000203 mixture Substances 0.000 claims abstract description 5
- 150000002978 peroxides Chemical class 0.000 claims abstract description 5
- 239000001257 hydrogen Substances 0.000 claims abstract description 4
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 4
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 claims description 20
- 238000004519 manufacturing process Methods 0.000 claims description 12
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 claims description 10
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 claims description 9
- 239000010457 zeolite Substances 0.000 claims description 9
- 229910021536 Zeolite Inorganic materials 0.000 claims description 8
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 claims description 8
- 239000011148 porous material Substances 0.000 claims description 8
- 239000012530 fluid Substances 0.000 claims description 6
- 239000007787 solid Substances 0.000 claims description 5
- 239000002994 raw material Substances 0.000 claims 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 1
- 239000000571 coke Substances 0.000 abstract description 7
- 239000000463 material Substances 0.000 abstract description 5
- 230000009849 deactivation Effects 0.000 abstract description 4
- 239000011949 solid catalyst Substances 0.000 abstract description 3
- 239000002904 solvent Substances 0.000 abstract description 3
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 abstract 1
- 239000012071 phase Substances 0.000 description 11
- 239000007789 gas Substances 0.000 description 5
- NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 description 4
- 101710112672 Probable tape measure protein Proteins 0.000 description 4
- 101710204224 Tape measure protein Proteins 0.000 description 4
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 4
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical class CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 4
- FLTJDUOFAQWHDF-UHFFFAOYSA-N trimethyl pentane Natural products CCCCC(C)(C)C FLTJDUOFAQWHDF-UHFFFAOYSA-N 0.000 description 4
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 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
- 230000008021 deposition Effects 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000001282 iso-butane Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- IVORCBKUUYGUOL-UHFFFAOYSA-N 1-ethynyl-2,4-dimethoxybenzene Chemical compound COC1=CC=C(C#C)C(OC)=C1 IVORCBKUUYGUOL-UHFFFAOYSA-N 0.000 description 1
- DJSRTBYADDKVHH-UHFFFAOYSA-N 2,2-dimethylbutane Chemical compound CCC(C)(C)C.CCC(C)(C)C DJSRTBYADDKVHH-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 238000010306 acid treatment Methods 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 125000000217 alkyl group Chemical class 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 238000003442 catalytic alkylation reaction Methods 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000005336 cracking Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 230000002427 irreversible effect Effects 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000035772 mutation Effects 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- 238000006384 oligomerization reaction Methods 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000000725 suspension 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
- C07C2/56—Addition to acyclic hydrocarbons
- C07C2/58—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
- B01J3/00—Processes of utilising sub-atmospheric or super-atmospheric pressure to effect chemical or physical change of matter; Apparatus therefor
- B01J3/008—Processes carried out under supercritical conditions
-
- 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
- C07C2521/06—Silicon, titanium, zirconium or hafnium; Oxides or hydroxides thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2529/00—Catalysts comprising molecular sieves
- C07C2529/04—Catalysts comprising molecular sieves having base-exchange properties, e.g. crystalline zeolites, pillared clays
- C07C2529/06—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof
-
- 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
- Y02P20/54—Improvements relating to the production of bulk chemicals using solvents, e.g. supercritical solvents or ionic liquids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/872,865 US5907075A (en) | 1997-06-11 | 1997-06-11 | Solid acid supercritical alkylation reactions using carbon dioxide and/or other co-solvents |
| US08/872,865 | 1997-06-11 | ||
| PCT/US1998/011538 WO1998056739A1 (en) | 1997-06-11 | 1998-06-04 | Improved solid acid supercritical alkylation reactions using carbon dioxide and/or other co-solvents |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2002510303A true JP2002510303A (ja) | 2002-04-02 |
| JP2002510303A5 JP2002510303A5 (https=) | 2005-12-08 |
Family
ID=25360469
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP50286199A Ceased JP2002510303A (ja) | 1997-06-11 | 1998-06-04 | 二酸化炭素および／または他の助溶剤を用いる改良固体酸超臨界アルキル化反応 |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US5907075A (https=) |
| EP (1) | EP0994832A4 (https=) |
| JP (1) | JP2002510303A (https=) |
| AU (1) | AU740582B2 (https=) |
| CA (1) | CA2293827A1 (https=) |
| WO (1) | WO1998056739A1 (https=) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2005162626A (ja) * | 2003-11-28 | 2005-06-23 | Kaoru Fujimoto | イソパラフィン−オレフィンアルキル化法 |
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6103948A (en) * | 1997-12-24 | 2000-08-15 | Bechtel Bwxt Idaho, Llc | Solid catalyzed isoparaffin alkylation at supercritical fluid and near-supercritical fluid conditions |
| DE19915904A1 (de) * | 1999-04-08 | 2000-10-12 | Studiengesellschaft Kohle Mbh | Verfahren zur übergangsmetallkatalysierten Dimerisierung oder Codimerisierung von Alkenen in komprimiertem Kohlendioxid als Lösungsmittel |
| US6914105B1 (en) * | 1999-11-12 | 2005-07-05 | North Carolina State University | Continuous process for making polymers in carbon dioxide |
| US6806332B2 (en) * | 1999-11-12 | 2004-10-19 | North Carolina State University | Continuous method and apparatus for separating polymer from a high pressure carbon dioxide fluid stream |
| 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 |
| US7090830B2 (en) | 2001-05-24 | 2006-08-15 | Alexza Pharmaceuticals, Inc. | Drug condensation aerosols and kits |
| US7645442B2 (en) | 2001-05-24 | 2010-01-12 | Alexza Pharmaceuticals, Inc. | Rapid-heating drug delivery article and method of use |
| US7458374B2 (en) | 2002-05-13 | 2008-12-02 | Alexza Pharmaceuticals, Inc. | Method and apparatus for vaporizing a compound |
| US7766013B2 (en) | 2001-06-05 | 2010-08-03 | Alexza Pharmaceuticals, Inc. | Aerosol generating method and device |
| US7585493B2 (en) | 2001-05-24 | 2009-09-08 | Alexza Pharmaceuticals, Inc. | Thin-film drug delivery article and method of use |
| US20070122353A1 (en) | 2001-05-24 | 2007-05-31 | Hale Ron L | Drug condensation aerosols and kits |
| US6924407B2 (en) * | 2001-08-27 | 2005-08-02 | The University Of Kansas | Pressure-tuned solid catalyzed heterogeneous chemical reactions |
| US20040105818A1 (en) | 2002-11-26 | 2004-06-03 | Alexza Molecular Delivery Corporation | Diuretic aerosols and methods of making and using them |
| US7913688B2 (en) | 2002-11-27 | 2011-03-29 | Alexza Pharmaceuticals, Inc. | Inhalation device for producing a drug aerosol |
| EP1625333A1 (en) | 2003-05-21 | 2006-02-15 | Alexza Pharmaceuticals, Inc. | Self-contained heating unit and drug-supply unit employing same |
| US7540286B2 (en) | 2004-06-03 | 2009-06-02 | Alexza Pharmaceuticals, Inc. | Multiple dose condensation aerosol devices and methods of forming condensation aerosols |
| EP2246086A3 (en) | 2004-08-12 | 2012-11-21 | Alexza Pharmaceuticals, Inc. | Aerosol drug delivery device incorporating percussively activated heating unit |
| US7592282B2 (en) * | 2004-11-11 | 2009-09-22 | Battelle Energy Alliance, Llc | Enhancement of alkylation catalysts for improved supercritical fluid regeneration |
| EP2121088B1 (en) | 2007-03-09 | 2016-07-13 | Alexza Pharmaceuticals, Inc. | Heating unit for use in a drug delivery device |
| US20110028773A1 (en) * | 2009-07-29 | 2011-02-03 | Bala Subramaniam | Deoxygenation of Bio-Oils and Other Compounds to Hydrocarbons in Supercritical Media |
| WO2015168683A1 (en) | 2014-05-02 | 2015-11-05 | University Of Tennessee Research Foundation | Novel glycerol dehydration methods and products thereof |
| EP3746138B1 (en) | 2018-02-02 | 2025-12-10 | Alexza Pharmaceuticals, Inc. | Electrical condensation aerosol device |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5304698A (en) * | 1992-08-10 | 1994-04-19 | Mobil Oil Corporation | Solid catalyzed supercritical isoparaffin-olefin alkylation process |
| US5639930A (en) * | 1995-01-04 | 1997-06-17 | Penick; Joe E. | Process of producing alkylates |
-
1997
- 1997-06-11 US US08/872,865 patent/US5907075A/en not_active Expired - Fee Related
-
1998
- 1998-06-04 AU AU78162/98A patent/AU740582B2/en not_active Ceased
- 1998-06-04 EP EP98926289A patent/EP0994832A4/en not_active Withdrawn
- 1998-06-04 JP JP50286199A patent/JP2002510303A/ja not_active Ceased
- 1998-06-04 WO PCT/US1998/011538 patent/WO1998056739A1/en not_active Ceased
- 1998-06-04 CA CA002293827A patent/CA2293827A1/en not_active Abandoned
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2005162626A (ja) * | 2003-11-28 | 2005-06-23 | Kaoru Fujimoto | イソパラフィン−オレフィンアルキル化法 |
Also Published As
| Publication number | Publication date |
|---|---|
| EP0994832A1 (en) | 2000-04-26 |
| US5907075A (en) | 1999-05-25 |
| EP0994832A4 (en) | 2000-09-20 |
| AU7816298A (en) | 1998-12-30 |
| WO1998056739A1 (en) | 1998-12-17 |
| AU740582B2 (en) | 2001-11-08 |
| CA2293827A1 (en) | 1998-12-17 |
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