CA2723423C - Diisobutylene process - Google Patents
Diisobutylene process Download PDFInfo
- Publication number
- CA2723423C CA2723423C CA2723423A CA2723423A CA2723423C CA 2723423 C CA2723423 C CA 2723423C CA 2723423 A CA2723423 A CA 2723423A CA 2723423 A CA2723423 A CA 2723423A CA 2723423 C CA2723423 C CA 2723423C
- Authority
- CA
- Canada
- Prior art keywords
- isobutylene
- stream
- water
- diisobutylene
- tertiary butyl
- 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.)
- Active
Links
- FXNDIJDIPNCZQJ-UHFFFAOYSA-N 2,4,4-trimethylpent-1-ene Chemical group CC(=C)CC(C)(C)C FXNDIJDIPNCZQJ-UHFFFAOYSA-N 0.000 title claims abstract description 52
- 238000000034 method Methods 0.000 title claims abstract description 37
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 claims abstract description 75
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims abstract description 58
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 58
- 238000006243 chemical reaction Methods 0.000 claims abstract description 29
- 229920005989 resin Polymers 0.000 claims abstract description 24
- 239000011347 resin Substances 0.000 claims abstract description 24
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims abstract description 16
- 239000004215 Carbon black (E152) Substances 0.000 claims description 11
- 229930195733 hydrocarbon Natural products 0.000 claims description 10
- 150000002430 hydrocarbons Chemical class 0.000 claims description 10
- NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 claims description 8
- JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 claims description 8
- 238000010908 decantation Methods 0.000 claims description 7
- 230000018044 dehydration Effects 0.000 claims description 4
- 238000006297 dehydration reaction Methods 0.000 claims description 4
- 238000004064 recycling Methods 0.000 claims 2
- 238000004821 distillation Methods 0.000 description 31
- 238000006384 oligomerization reaction Methods 0.000 description 23
- 239000003054 catalyst Substances 0.000 description 19
- 239000000047 product Substances 0.000 description 13
- 239000003085 diluting agent Substances 0.000 description 8
- 238000005984 hydrogenation reaction Methods 0.000 description 8
- 238000010992 reflux Methods 0.000 description 7
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 6
- 238000001035 drying Methods 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 239000012071 phase Substances 0.000 description 5
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- 238000006471 dimerization reaction Methods 0.000 description 4
- 239000007791 liquid phase Substances 0.000 description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 238000005260 corrosion Methods 0.000 description 3
- 230000007797 corrosion Effects 0.000 description 3
- 230000009849 deactivation Effects 0.000 description 3
- 230000001627 detrimental effect Effects 0.000 description 3
- 230000009977 dual effect Effects 0.000 description 3
- 230000002708 enhancing effect Effects 0.000 description 3
- 239000003607 modifier Substances 0.000 description 3
- 238000005191 phase separation Methods 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 2
- DRHABPMHZRIRAH-UHFFFAOYSA-N 2,4,4,6,6-pentamethylhept-2-ene Chemical group CC(C)=CC(C)(C)CC(C)(C)C DRHABPMHZRIRAH-UHFFFAOYSA-N 0.000 description 2
- AMIMRNSIRUDHCM-UHFFFAOYSA-N Isopropylaldehyde Chemical compound CC(C)C=O AMIMRNSIRUDHCM-UHFFFAOYSA-N 0.000 description 2
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 description 2
- 229920001429 chelating resin Polymers 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 239000003456 ion exchange resin Substances 0.000 description 2
- 229920003303 ion-exchange polymer Polymers 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 229910052759 nickel Inorganic materials 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- 229910052697 platinum Inorganic materials 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- 229920002125 Sokalan® Polymers 0.000 description 1
- 239000003463 adsorbent Substances 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 230000005484 gravity Effects 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- 230000003606 oligomerizing effect Effects 0.000 description 1
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000005057 refrigeration Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 238000001179 sorption measurement Methods 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
-
- 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
- C07C2/28—Catalytic processes with hydrides or organic compounds with ion-exchange resins
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C11/00—Aliphatic unsaturated hydrocarbons
- C07C11/02—Alkenes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C7/00—Purification; Separation; Use of additives
- C07C7/04—Purification; Separation; Use of additives by distillation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C9/00—Aliphatic saturated hydrocarbons
- C07C9/14—Aliphatic saturated hydrocarbons with five to fifteen carbon atoms
- C07C9/16—Branched-chain hydrocarbons
-
- 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
- C07C2531/06—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing polymers
- C07C2531/08—Ion-exchange resins
- C07C2531/10—Ion-exchange resins sulfonated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Analytical Chemistry (AREA)
- Water Supply & Treatment (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US12/156,004 | 2008-05-29 | ||
| US12/156,004 US8067655B2 (en) | 2008-05-29 | 2008-05-29 | Diisobutylene process |
| PCT/US2009/002468 WO2009145861A1 (en) | 2008-05-29 | 2009-04-21 | Diisobutylene process |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2723423A1 CA2723423A1 (en) | 2009-12-03 |
| CA2723423C true CA2723423C (en) | 2016-01-05 |
Family
ID=40929680
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2723423A Active CA2723423C (en) | 2008-05-29 | 2009-04-21 | Diisobutylene process |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US8067655B2 (enExample) |
| EP (1) | EP2279156B1 (enExample) |
| JP (1) | JP5444333B2 (enExample) |
| KR (1) | KR101600113B1 (enExample) |
| CN (1) | CN102046567B (enExample) |
| CA (1) | CA2723423C (enExample) |
| WO (1) | WO2009145861A1 (enExample) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102012105879A1 (de) * | 2012-07-02 | 2014-01-02 | Oxea Gmbh | Verfahren zur Herstellung von Isononylderivaten |
| FR2995306B1 (fr) * | 2012-09-12 | 2014-10-10 | IFP Energies Nouvelles | Procede de production de kerosene a partir de butanols |
| CN104030877B (zh) * | 2013-12-19 | 2015-12-09 | 武汉优立克新材料科技有限公司 | 一种丙烯二聚物的制备方法 |
| EP2949636B1 (en) | 2014-05-31 | 2018-05-09 | Indian Oil Corporation Limited | Process for simultaneous production of alcohols and oligomer product from hydrocarbon feed stock |
| CN107457001B (zh) * | 2016-06-03 | 2019-09-20 | 万华化学集团股份有限公司 | 一种聚苯乙烯磺酸树脂催化剂及其制备方法和应用 |
| CN107473917B (zh) * | 2016-06-07 | 2020-10-27 | 中国石油化工股份有限公司 | 混合碳四生产二异丁烯的工艺 |
| CN107663147B (zh) * | 2016-07-29 | 2019-07-23 | 万华化学集团股份有限公司 | 一种分离叔丁醇与二异丁烯的方法和系统 |
| CN107056576B (zh) * | 2017-01-16 | 2020-04-28 | 重庆邮电大学 | 一种2,4,4-三甲基-1-戊烯的制备方法 |
| CN110759801B (zh) * | 2018-07-27 | 2022-12-27 | 中国石油化工股份有限公司 | 一种混合c4生产二异丁烯的方法 |
| CN109293466A (zh) * | 2018-09-25 | 2019-02-01 | 安徽海德化工科技有限公司 | 利用异丁烯制备异辛烷的方法 |
| CN110551893B (zh) * | 2019-09-16 | 2020-12-15 | 中国原子能科学研究院 | 稀释剂及其制备方法 |
| CN112745184B (zh) * | 2019-10-31 | 2022-08-12 | 中国石油化工股份有限公司 | 一种高烯烃含量的混合c4原料叠合生产异辛烯的方法 |
| SA121430097B1 (ar) | 2020-09-05 | 2023-10-18 | انديان اويل كوربوريشن ليمتد | عملية وجهاز لإنتاج وفصل كحولات وتحويل خام تغذية هيدروكربوني إلى أوليجومر |
Family Cites Families (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3351635A (en) * | 1966-03-14 | 1967-11-07 | Halcon International Inc | Epoxidation process |
| US3510538A (en) * | 1967-12-15 | 1970-05-05 | Atlantic Richfield Co | Continuous process for dehydration of tertiary butyl alcohol |
| US4100220A (en) * | 1977-06-27 | 1978-07-11 | Petro-Tex Chemical Corporation | Dimerization of isobutene |
| US4155945A (en) * | 1978-07-24 | 1979-05-22 | Cities Service Company | Continuous process for dehydration of tertiary butyl alcohol |
| US4165343A (en) * | 1978-07-28 | 1979-08-21 | Cities Service Conmpany | Dehydration of tertiary butyl alcohol |
| CA1179291A (en) * | 1981-10-30 | 1984-12-11 | David T. Ahlberg | Distillation apparatus |
| US4447668A (en) * | 1982-03-29 | 1984-05-08 | Chemical Research & Licensing Company | Process for producing high purity isoolefins and dimers thereof by dissociation of ethers |
| JPS58225030A (ja) * | 1982-06-22 | 1983-12-27 | Nippon Oil Co Ltd | 高純度ブテン−１の分離回収方法 |
| US5625109A (en) * | 1994-11-21 | 1997-04-29 | Gupta; Vijai P. | Liquid phase dehydration of tertiary butyl alcohol |
| JPH1160510A (ja) * | 1997-08-15 | 1999-03-02 | Tonen Chem Corp | ジイソブチレンの精製方法 |
| US5877372A (en) * | 1997-11-21 | 1999-03-02 | Arco Chemical Technology, L.P. | Isobutylene oligomerization using isooctane diluent |
| US6376731B1 (en) * | 2000-01-14 | 2002-04-23 | Arco Chemical Technology, L.P. | Selective olefin oligomerization |
| US6936742B2 (en) * | 2002-03-15 | 2005-08-30 | Catalytic Distillation Technologies | Production of diisobutene from tertiary butyl alcohol |
| US6863778B2 (en) * | 2002-07-25 | 2005-03-08 | Catalytic Distillation Technologies | Separation of tertiary butyl alcohol from diisobutylene |
| JP3929916B2 (ja) * | 2002-08-01 | 2007-06-13 | 出光興産株式会社 | ブテンオリゴマーの製造方法 |
| DE10238370A1 (de) * | 2002-08-22 | 2004-03-04 | Oxeno Olefinchemie Gmbh | Verfahren zur Herstellung von Isobuten aus technischen Methyl-tert.-butylether |
| DE10327215A1 (de) * | 2003-06-17 | 2005-01-13 | Oxeno Olefinchemie Gmbh | Verfahren zur Herstellung von Isobuten aus tert.-Butanol |
| US7012167B2 (en) * | 2003-10-08 | 2006-03-14 | Lyondell Chemical Technology, L.P. | Diisobutylene process |
| ITMI20031951A1 (it) * | 2003-10-10 | 2005-04-11 | Snam Progetti | Procedimento per la produzione di miscele idrocarburiche altoottaniche mediante idrogenazione di miscele idrocarburiche contenenti tagli oleifinici ramificati |
| DE102006040434A1 (de) * | 2006-08-29 | 2008-03-06 | Oxeno Olefinchemie Gmbh | Verfahren zur Spaltung von MTBE |
-
2008
- 2008-05-29 US US12/156,004 patent/US8067655B2/en active Active
-
2009
- 2009-04-21 EP EP09755224A patent/EP2279156B1/en active Active
- 2009-04-21 CA CA2723423A patent/CA2723423C/en active Active
- 2009-04-21 CN CN200980119662.8A patent/CN102046567B/zh active Active
- 2009-04-21 KR KR1020107026532A patent/KR101600113B1/ko active Active
- 2009-04-21 WO PCT/US2009/002468 patent/WO2009145861A1/en not_active Ceased
- 2009-04-21 JP JP2011511590A patent/JP5444333B2/ja active Active
Also Published As
| Publication number | Publication date |
|---|---|
| CN102046567A (zh) | 2011-05-04 |
| KR101600113B1 (ko) | 2016-03-04 |
| WO2009145861A1 (en) | 2009-12-03 |
| EP2279156A1 (en) | 2011-02-02 |
| KR20110037942A (ko) | 2011-04-13 |
| EP2279156B1 (en) | 2013-03-13 |
| JP5444333B2 (ja) | 2014-03-19 |
| JP2011521946A (ja) | 2011-07-28 |
| US8067655B2 (en) | 2011-11-29 |
| CN102046567B (zh) | 2013-12-25 |
| US20090299117A1 (en) | 2009-12-03 |
| CA2723423A1 (en) | 2009-12-03 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request |
Effective date: 20140415 |