CA2383924C - Oligomerization of olefins - Google Patents
Oligomerization of olefins Download PDFInfo
- Publication number
- CA2383924C CA2383924C CA002383924A CA2383924A CA2383924C CA 2383924 C CA2383924 C CA 2383924C CA 002383924 A CA002383924 A CA 002383924A CA 2383924 A CA2383924 A CA 2383924A CA 2383924 C CA2383924 C CA 2383924C
- Authority
- CA
- Canada
- Prior art keywords
- range
- oligomers
- accordance
- heavy
- light olefin
- 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
- 150000001336 alkenes Chemical class 0.000 title claims abstract description 83
- 238000006384 oligomerization reaction Methods 0.000 title claims abstract description 35
- 150000002430 hydrocarbons Chemical class 0.000 claims abstract description 52
- 229930195733 hydrocarbon Natural products 0.000 claims abstract description 49
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims abstract description 49
- 238000000034 method Methods 0.000 claims abstract description 28
- 238000006243 chemical reaction Methods 0.000 claims abstract description 26
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 25
- 230000003606 oligomerizing effect Effects 0.000 claims abstract description 13
- 239000003054 catalyst Substances 0.000 claims description 33
- 239000004215 Carbon black (E152) Substances 0.000 claims description 19
- 239000003377 acid catalyst Substances 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- YFSUTJLHUFNCNZ-UHFFFAOYSA-N perfluorooctane-1-sulfonic acid Chemical group OS(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F YFSUTJLHUFNCNZ-UHFFFAOYSA-N 0.000 claims description 4
- -1 propylene, butylene, isobutylene Chemical group 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 239000000460 chlorine Chemical group 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 229910052740 iodine Chemical group 0.000 claims description 2
- 239000011630 iodine Chemical group 0.000 claims description 2
- 229910006069 SO3H Inorganic materials 0.000 claims 2
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims 2
- 239000002253 acid Substances 0.000 claims 1
- 239000007795 chemical reaction product Substances 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 239000000463 material Substances 0.000 abstract description 31
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 abstract description 23
- 239000002283 diesel fuel Substances 0.000 description 12
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- 239000007789 gas Substances 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 238000010998 test method Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 239000012153 distilled water Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 229910000831 Steel Inorganic materials 0.000 description 2
- QWTDNUCVQCZILF-UHFFFAOYSA-N isopentane Chemical compound CCC(C)C QWTDNUCVQCZILF-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000010959 steel Substances 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 229920000557 Nafion® Polymers 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 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
- 239000007900 aqueous suspension Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 230000001276 controlling effect Effects 0.000 description 1
- AFABGHUZZDYHJO-UHFFFAOYSA-N dimethyl butane Natural products CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 150000002431 hydrogen Chemical group 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 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
-
- 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
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2531/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- C07C2531/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- C07C2531/025—Sulfonic acids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/397,571 US6281401B1 (en) | 1999-09-16 | 1999-09-16 | Oligomerization of olefins |
| US09/397,571 | 1999-09-16 | ||
| PCT/US2000/024995 WO2001019762A1 (en) | 1999-09-16 | 2000-09-13 | Oligomerization of olefins |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2383924A1 CA2383924A1 (en) | 2001-03-22 |
| CA2383924C true CA2383924C (en) | 2006-07-18 |
Family
ID=23571733
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002383924A Expired - Fee Related CA2383924C (en) | 1999-09-16 | 2000-09-13 | Oligomerization of olefins |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US6281401B1 (https=) |
| EP (1) | EP1218321A4 (https=) |
| JP (1) | JP4537637B2 (https=) |
| KR (1) | KR20020029133A (https=) |
| CN (1) | CN1174942C (https=) |
| AU (1) | AU754080B2 (https=) |
| CA (1) | CA2383924C (https=) |
| RU (1) | RU2234487C2 (https=) |
| WO (1) | WO2001019762A1 (https=) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20050016899A1 (en) * | 2003-07-21 | 2005-01-27 | Syntroleum Corporation | Synthetic lubricant basestock and an integrated fischer-tropsch process for its production |
| US7667086B2 (en) | 2005-01-31 | 2010-02-23 | Exxonmobil Chemical Patents Inc. | Olefin oligomerization and biodegradable compositions therefrom |
| US8481796B2 (en) | 2005-01-31 | 2013-07-09 | Exxonmobil Chemical Patents Inc. | Olefin oligomerization and compositions therefrom |
| US7692049B2 (en) | 2005-01-31 | 2010-04-06 | Exxonmobil Chemical Patents Inc. | Hydrocarbon compositions useful for producing fuels and methods of producing the same |
| US7678953B2 (en) | 2005-01-31 | 2010-03-16 | Exxonmobil Chemical Patents Inc. | Olefin oligomerization |
| WO2006084286A2 (en) | 2005-01-31 | 2006-08-10 | Exxonmobil Chemical Patents Inc. | Hydrocarbon compositions useful for producing fuels |
| DE602005019239D1 (de) * | 2005-10-20 | 2010-03-25 | Linde Ag | Verfahren zur Oligomerisierung von Ethylen und Reaktorsystem dafür mit Kühlvorrichtung |
| US7741526B2 (en) | 2006-07-19 | 2010-06-22 | Exxonmobil Chemical Patents Inc. | Feedstock preparation of olefins for oligomerization to produce fuels |
| US7956227B2 (en) * | 2007-12-06 | 2011-06-07 | Conocophillips Company | Oligomerization of hydrocarbons |
| WO2014073006A1 (en) | 2012-11-09 | 2014-05-15 | Council Of Scientific & Industrial Research | A single step catalytic process for the conversion of n-paraffins and naphtha to diesel range hydrocarbons |
| US9447346B2 (en) * | 2013-12-11 | 2016-09-20 | Saudi Arabian Oil Company | Two-step process for production of RON-enhanced mixed butanols and diisobutenes |
| WO2022081641A1 (en) * | 2020-10-13 | 2022-04-21 | Phillips 66 Company | Metal organic framework |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1129809B (it) * | 1979-03-26 | 1986-06-11 | Ugine Kuhlmann | Composizione catalitica per la conversione di idrocarburi e procedimento per la disidratazione di acidi perfluoroalcansolfonici destinati a fare parte bella composizione |
| FR2504123A1 (fr) * | 1981-04-21 | 1982-10-22 | Inst Francais Du Petrole | Procede de production de nonenes ou de production simultanee de nonenes et de dodecenes a partir de propene |
| US4400565A (en) | 1982-04-28 | 1983-08-23 | Texaco Inc. | Co-catalyst for use with boron trifluoride in olefin oligomerization |
| JPS5921629A (ja) * | 1982-07-29 | 1984-02-03 | Toshinobu Higashimura | Ｃ↓４−オレフイン三量体の製造方法 |
| US4740652A (en) | 1985-05-23 | 1988-04-26 | Uop Inc. | Process for the oligomerization of olefins |
| US4777316A (en) * | 1987-11-10 | 1988-10-11 | Mobil Oil Corporation | Manufacture of distillate hydrocarbons from light olefins in staged reactors |
| US4788366A (en) * | 1987-12-28 | 1988-11-29 | Mobil Oil Corporation | Production of heavier hydrocarbons from light olefins in multistage catalytic reactors |
| IT1226550B (it) * | 1988-07-29 | 1991-01-24 | Enichem Anic Spa | Processo di oligomerizzazione selettiva di olefine e nuovo catalizzatore per tale processo. |
| US4935575A (en) * | 1988-12-12 | 1990-06-19 | Uop | Process for the oligomerization of olefins and a catalyst thereof |
| US5094995A (en) | 1989-08-02 | 1992-03-10 | E. I. Du Pont De Nemours And Company | Supported perfluorinated ion-exchange polymers |
| US5639931A (en) | 1993-10-18 | 1997-06-17 | Mobil Oil Corporation | Process for producing low aromatic diesel fuel with high cetane index |
| US5811608A (en) * | 1995-12-15 | 1998-09-22 | Uop Llc | Process for oligomer production and saturation |
| RU2136642C1 (ru) * | 1998-08-21 | 1999-09-10 | ОАО "Нижнекамскнефтехим" | Способ получения тримеров и тетрамеров пропилена |
-
1999
- 1999-09-16 US US09/397,571 patent/US6281401B1/en not_active Expired - Lifetime
-
2000
- 2000-09-13 KR KR1020027003492A patent/KR20020029133A/ko not_active Ceased
- 2000-09-13 EP EP00963384A patent/EP1218321A4/en not_active Withdrawn
- 2000-09-13 CN CNB008129347A patent/CN1174942C/zh not_active Expired - Fee Related
- 2000-09-13 WO PCT/US2000/024995 patent/WO2001019762A1/en not_active Ceased
- 2000-09-13 JP JP2001523343A patent/JP4537637B2/ja not_active Expired - Lifetime
- 2000-09-13 AU AU74806/00A patent/AU754080B2/en not_active Ceased
- 2000-09-13 RU RU2002110125/04A patent/RU2234487C2/ru not_active IP Right Cessation
- 2000-09-13 CA CA002383924A patent/CA2383924C/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| JP2003509390A (ja) | 2003-03-11 |
| CN1174942C (zh) | 2004-11-10 |
| JP4537637B2 (ja) | 2010-09-01 |
| RU2234487C2 (ru) | 2004-08-20 |
| AU754080B2 (en) | 2002-11-07 |
| CA2383924A1 (en) | 2001-03-22 |
| EP1218321A1 (en) | 2002-07-03 |
| US6281401B1 (en) | 2001-08-28 |
| WO2001019762A1 (en) | 2001-03-22 |
| EP1218321A4 (en) | 2005-04-20 |
| CN1374934A (zh) | 2002-10-16 |
| AU7480600A (en) | 2001-04-17 |
| KR20020029133A (ko) | 2002-04-17 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed | ||
| MKLA | Lapsed |
Effective date: 20080915 |