ES2224308T3 - Procedimiento mejorado para la produccion de alfa-olefinas lineales. - Google Patents
Procedimiento mejorado para la produccion de alfa-olefinas lineales.Info
- Publication number
- ES2224308T3 ES2224308T3 ES98107311T ES98107311T ES2224308T3 ES 2224308 T3 ES2224308 T3 ES 2224308T3 ES 98107311 T ES98107311 T ES 98107311T ES 98107311 T ES98107311 T ES 98107311T ES 2224308 T3 ES2224308 T3 ES 2224308T3
- Authority
- ES
- Spain
- Prior art keywords
- ethylene
- olefins
- water
- weight
- procedure
- 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
- 238000000034 method Methods 0.000 title claims abstract description 35
- 238000004519 manufacturing process Methods 0.000 title description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 57
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims abstract description 55
- 239000005977 Ethylene Substances 0.000 claims abstract description 55
- 239000003054 catalyst Substances 0.000 claims abstract description 42
- 229910052723 transition metal Inorganic materials 0.000 claims abstract description 17
- 150000003624 transition metals Chemical group 0.000 claims abstract description 17
- 239000007788 liquid Substances 0.000 claims abstract description 14
- 239000004711 α-olefin Substances 0.000 claims description 31
- 238000006384 oligomerization reaction Methods 0.000 claims description 30
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 claims description 26
- 230000003197 catalytic effect Effects 0.000 claims description 19
- 239000012190 activator Substances 0.000 claims description 15
- 239000003446 ligand Substances 0.000 claims description 15
- 239000012071 phase Substances 0.000 claims description 12
- 150000002430 hydrocarbons Chemical class 0.000 claims description 8
- 229930195733 hydrocarbon Natural products 0.000 claims description 7
- 239000004215 Carbon black (E152) Substances 0.000 claims description 6
- 229910052751 metal Inorganic materials 0.000 claims description 5
- 239000002184 metal Substances 0.000 claims description 5
- 230000007704 transition Effects 0.000 claims description 5
- 150000003623 transition metal compounds Chemical class 0.000 claims description 5
- 239000007791 liquid phase Substances 0.000 claims description 3
- 150000002739 metals Chemical class 0.000 claims description 3
- JXLHNMVSKXFWAO-UHFFFAOYSA-N azane;7-fluoro-2,1,3-benzoxadiazole-4-sulfonic acid Chemical compound N.OS(=O)(=O)C1=CC=C(F)C2=NON=C12 JXLHNMVSKXFWAO-UHFFFAOYSA-N 0.000 claims description 2
- 238000009826 distribution Methods 0.000 abstract description 19
- 239000002904 solvent Substances 0.000 abstract description 17
- 239000000203 mixture Substances 0.000 abstract description 9
- 238000010348 incorporation Methods 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 24
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 20
- 239000000047 product Substances 0.000 description 17
- 150000001336 alkenes Chemical class 0.000 description 16
- 230000000694 effects Effects 0.000 description 14
- 229910052759 nickel Inorganic materials 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 8
- 230000008569 process Effects 0.000 description 8
- 239000002798 polar solvent Substances 0.000 description 7
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- 230000007423 decrease Effects 0.000 description 6
- AFFLGGQVNFXPEV-UHFFFAOYSA-N n-decene Natural products CCCCCCCCC=C AFFLGGQVNFXPEV-UHFFFAOYSA-N 0.000 description 6
- -1 polyethylene Polymers 0.000 description 5
- 239000004698 Polyethylene Substances 0.000 description 4
- 229920000573 polyethylene Polymers 0.000 description 4
- 159000000000 sodium salts Chemical class 0.000 description 4
- 238000006277 sulfonation reaction Methods 0.000 description 4
- GGQQNYXPYWCUHG-RMTFUQJTSA-N (3e,6e)-deca-3,6-diene Chemical compound CCC\C=C\C\C=C\CC GGQQNYXPYWCUHG-RMTFUQJTSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 230000009286 beneficial effect Effects 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 239000003599 detergent Substances 0.000 description 3
- 150000002815 nickel Chemical class 0.000 description 3
- 239000003495 polar organic solvent Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- IDYLMOYUCOPIRT-UHFFFAOYSA-L 4-methylbenzenesulfonate;nickel(2+) Chemical compound [Ni+2].CC1=CC=C(S([O-])(=O)=O)C=C1.CC1=CC=C(S([O-])(=O)=O)C=C1 IDYLMOYUCOPIRT-UHFFFAOYSA-L 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical class OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- 150000002009 diols Chemical class 0.000 description 2
- 230000006870 function Effects 0.000 description 2
- 238000007037 hydroformylation reaction Methods 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- FGQZHFZBGIQUJO-UHFFFAOYSA-N 2-(2-butylphenyl)phosphanyl-4-methylbenzenesulfonic acid Chemical compound CCCCC1=CC=CC=C1PC1=CC(C)=CC=C1S(O)(=O)=O FGQZHFZBGIQUJO-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 230000003139 buffering effect Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000013522 chelant Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000006356 dehydrogenation reaction Methods 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- ALDOUWLIYKWJTN-UHFFFAOYSA-N fluoro(dioxido)borane;nickel(2+) Chemical compound [Ni+2].[O-]B([O-])F ALDOUWLIYKWJTN-UHFFFAOYSA-N 0.000 description 1
- 229920001903 high density polyethylene Polymers 0.000 description 1
- 239000004700 high-density polyethylene Substances 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 229920000092 linear low density polyethylene Polymers 0.000 description 1
- 239000004707 linear low-density polyethylene Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 1
- 150000005673 monoalkenes Chemical class 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 150000003138 primary alcohols Chemical class 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- VOITXYVAKOUIBA-UHFFFAOYSA-N triethylaluminium Chemical compound CC[Al](CC)CC VOITXYVAKOUIBA-UHFFFAOYSA-N 0.000 description 1
- 239000012808 vapor phase Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 229910052726 zirconium Inorganic materials 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
- C07C2/02—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons
- C07C2/04—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons by oligomerisation of well-defined unsaturated hydrocarbons without ring formation
- C07C2/06—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons by oligomerisation of well-defined unsaturated hydrocarbons without ring formation of alkenes, i.e. acyclic hydrocarbons having only one carbon-to-carbon double bond
- C07C2/08—Catalytic processes
- C07C2/26—Catalytic processes with hydrides or organic compounds
- C07C2/36—Catalytic processes with hydrides or organic compounds as phosphines, arsines, stilbines or bismuthines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2531/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- C07C2531/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- C07C2531/24—Phosphines
-
- 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
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
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)
- Catalysts (AREA)
Applications Claiming Priority (11)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/775,051 US5744679A (en) | 1996-12-27 | 1996-12-27 | Using water concentration to control ethylene oligomerization |
| CA002235552A CA2235552C (en) | 1996-12-27 | 1998-04-21 | Improved process for the production of linear alpha-olefins |
| ZA983354A ZA983354B (en) | 1996-12-27 | 1998-04-21 | Process for the production of linear alpha-olefins |
| EP98107311A EP0953556B1 (en) | 1996-12-27 | 1998-04-22 | Improved process for the production of linear alpha-olefines |
| AU63576/98A AU751343B2 (en) | 1996-12-27 | 1998-04-23 | Improved process for the production of linear alpha-olefins |
| SG1998000851A SG71107A1 (en) | 1996-12-27 | 1998-04-23 | Improved process for the production of linear alpha-olefins |
| JP10115200A JPH11302203A (ja) | 1996-12-27 | 1998-04-24 | 直鎖状α−オレフィンの改良された製造方法 |
| RU98108155/04A RU2197459C2 (ru) | 1996-12-27 | 1998-04-27 | Усовершенствованный способ получения линейных альфа-олефинов (варианты) |
| CZ981285A CZ128598A3 (cs) | 1996-12-27 | 1998-04-27 | Zlepšený způsob přípravy lineárních alfa-olefinů |
| BR9801496-0A BR9801496A (pt) | 1996-12-27 | 1998-04-28 | Processo para a oligomerização contínua de etileno. |
| CNB981094473A CN1195712C (zh) | 1996-12-27 | 1998-04-28 | 线性α－链烯的改良工艺 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2224308T3 true ES2224308T3 (es) | 2005-03-01 |
Family
ID=31499747
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES98107311T Expired - Lifetime ES2224308T3 (es) | 1996-12-27 | 1998-04-22 | Procedimiento mejorado para la produccion de alfa-olefinas lineales. |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US5744679A (2) |
| EP (1) | EP0953556B1 (2) |
| JP (1) | JPH11302203A (2) |
| CN (1) | CN1195712C (2) |
| AU (1) | AU751343B2 (2) |
| BR (1) | BR9801496A (2) |
| CA (1) | CA2235552C (2) |
| CZ (1) | CZ128598A3 (2) |
| ES (1) | ES2224308T3 (2) |
| RU (1) | RU2197459C2 (2) |
| SG (1) | SG71107A1 (2) |
| ZA (1) | ZA983354B (2) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6291387B1 (en) * | 1998-03-20 | 2001-09-18 | Penn State Research Foundation | Transition metal-free olefin polymerization catalyst |
| WO2005058787A1 (en) * | 2003-12-18 | 2005-06-30 | Exxonmobil Chemical Patents Inc. | Improvements in or relating to hydroformylation |
| US7586017B2 (en) * | 2003-12-18 | 2009-09-08 | Exxonmobil Chemical Patents Inc. | Hydrogenation |
| JP2007514702A (ja) * | 2003-12-18 | 2007-06-07 | エクソンモービル・ケミカル・パテンツ・インク | 触媒反応の改良 |
| US8598396B2 (en) * | 2005-06-13 | 2013-12-03 | Exxonmobil Chemical Patents Inc. | Oligomerisation of olefins |
| EP2225033B1 (en) * | 2007-12-12 | 2017-10-04 | Saudi Basic Industries Corporation | Catalyst composition for oligomerization of ethylene oligomerization process and method for its preparation |
| ZA201402828B (en) * | 2013-04-17 | 2014-12-23 | China Petroleum & Chem Corp | Catalyst compositions and process for ethylene oligomerization |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3676523A (en) * | 1971-07-16 | 1972-07-11 | Shell Oil Co | Alpha-olefin production |
| US4472522A (en) * | 1983-06-06 | 1984-09-18 | Shell Oil Company | Ethylene oligomerization process |
| EP0177999B1 (en) * | 1984-10-09 | 1989-01-18 | Shell Internationale Researchmaatschappij B.V. | Ethylene oligomerization process carried out in a diol-based solvent containing monohydric alcohol or water |
| US4689437A (en) * | 1986-07-21 | 1987-08-25 | Union Carbide Corporation | Oligomerization to alpha-olefins |
| US4711969A (en) * | 1986-08-25 | 1987-12-08 | Chevron Research Company | Oligomerization of ethylene in methanol and water |
| SU1432970A1 (ru) * | 1986-11-28 | 1999-08-27 | Научно-исследовательский институт мономеров для синтетического каучука | Способ получения олефиновых углеводородов с-с |
-
1996
- 1996-12-27 US US08/775,051 patent/US5744679A/en not_active Expired - Fee Related
-
1998
- 1998-04-21 ZA ZA983354A patent/ZA983354B/xx unknown
- 1998-04-21 CA CA002235552A patent/CA2235552C/en not_active Expired - Fee Related
- 1998-04-22 EP EP98107311A patent/EP0953556B1/en not_active Expired - Lifetime
- 1998-04-22 ES ES98107311T patent/ES2224308T3/es not_active Expired - Lifetime
- 1998-04-23 AU AU63576/98A patent/AU751343B2/en not_active Ceased
- 1998-04-23 SG SG1998000851A patent/SG71107A1/en unknown
- 1998-04-24 JP JP10115200A patent/JPH11302203A/ja active Pending
- 1998-04-27 RU RU98108155/04A patent/RU2197459C2/ru not_active IP Right Cessation
- 1998-04-27 CZ CZ981285A patent/CZ128598A3/cs unknown
- 1998-04-28 BR BR9801496-0A patent/BR9801496A/pt not_active Application Discontinuation
- 1998-04-28 CN CNB981094473A patent/CN1195712C/zh not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| US5744679A (en) | 1998-04-28 |
| AU751343B2 (en) | 2002-08-15 |
| EP0953556A1 (en) | 1999-11-03 |
| SG71107A1 (en) | 2000-03-21 |
| RU2197459C2 (ru) | 2003-01-27 |
| CZ128598A3 (cs) | 1999-11-17 |
| BR9801496A (pt) | 1999-11-09 |
| CA2235552C (en) | 2008-12-30 |
| AU6357698A (en) | 1999-11-04 |
| JPH11302203A (ja) | 1999-11-02 |
| CN1195712C (zh) | 2005-04-06 |
| CA2235552A1 (en) | 1999-10-21 |
| ZA983354B (en) | 1999-01-27 |
| CN1233608A (zh) | 1999-11-03 |
| EP0953556B1 (en) | 2004-09-29 |
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