JP5670874B2 - ポリイソブチレンの液相重合方法 - Google Patents
ポリイソブチレンの液相重合方法 Download PDFInfo
- Publication number
- JP5670874B2 JP5670874B2 JP2011289168A JP2011289168A JP5670874B2 JP 5670874 B2 JP5670874 B2 JP 5670874B2 JP 2011289168 A JP2011289168 A JP 2011289168A JP 2011289168 A JP2011289168 A JP 2011289168A JP 5670874 B2 JP5670874 B2 JP 5670874B2
- Authority
- JP
- Japan
- Prior art keywords
- reactor
- catalyst
- reaction
- reaction mixture
- reaction zone
- 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
- 238000006116 polymerization reaction Methods 0.000 title claims description 34
- 229920002367 Polyisobutene Polymers 0.000 title description 72
- 238000000034 method Methods 0.000 title description 60
- 239000007791 liquid phase Substances 0.000 title description 8
- 238000006243 chemical reaction Methods 0.000 claims description 98
- 239000003054 catalyst Substances 0.000 claims description 87
- 239000011541 reaction mixture Substances 0.000 claims description 68
- 239000000203 mixture Substances 0.000 claims description 48
- 150000001336 alkenes Chemical class 0.000 claims description 38
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 33
- 239000002994 raw material Substances 0.000 claims description 21
- 239000003607 modifier Substances 0.000 claims description 11
- 239000012530 fluid Substances 0.000 claims 3
- 239000000047 product Substances 0.000 description 84
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 42
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 33
- 125000002573 ethenylidene group Chemical group [*]=C=C([H])[H] 0.000 description 30
- 230000008569 process Effects 0.000 description 29
- 239000008139 complexing agent Substances 0.000 description 26
- 238000004519 manufacturing process Methods 0.000 description 22
- 229920000098 polyolefin Polymers 0.000 description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 14
- 229920000642 polymer Polymers 0.000 description 10
- 150000001412 amines Chemical class 0.000 description 9
- 239000000463 material Substances 0.000 description 9
- IAQRGUVFOMOMEM-UHFFFAOYSA-N but-2-ene Chemical compound CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 7
- 239000003085 diluting agent Substances 0.000 description 7
- 239000000543 intermediate Substances 0.000 description 7
- 150000003138 primary alcohols Chemical class 0.000 description 7
- 230000035484 reaction time Effects 0.000 description 7
- 238000005755 formation reaction Methods 0.000 description 6
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 6
- 238000012546 transfer Methods 0.000 description 6
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 229930195733 hydrocarbon Natural products 0.000 description 5
- 150000002430 hydrocarbons Chemical class 0.000 description 5
- 239000000178 monomer Substances 0.000 description 5
- 230000009257 reactivity Effects 0.000 description 5
- 239000003507 refrigerant Substances 0.000 description 5
- 239000004711 α-olefin Substances 0.000 description 5
- 239000004215 Carbon black (E152) Substances 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 238000013461 design Methods 0.000 description 4
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 4
- 238000006317 isomerization reaction Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 150000001298 alcohols Chemical class 0.000 description 3
- 238000013459 approach Methods 0.000 description 3
- XNMQEEKYCVKGBD-UHFFFAOYSA-N dimethylacetylene Natural products CC#CC XNMQEEKYCVKGBD-UHFFFAOYSA-N 0.000 description 3
- 238000009826 distribution Methods 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 230000003134 recirculating effect Effects 0.000 description 3
- AFFLGGQVNFXPEV-UHFFFAOYSA-N 1-decene Chemical compound CCCCCCCCC=C AFFLGGQVNFXPEV-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 239000001282 iso-butane Substances 0.000 description 2
- 239000000314 lubricant Substances 0.000 description 2
- 230000007246 mechanism Effects 0.000 description 2
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 2
- 238000006384 oligomerization reaction Methods 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 229920000570 polyether Polymers 0.000 description 2
- 230000000379 polymerizing effect Effects 0.000 description 2
- 230000008707 rearrangement Effects 0.000 description 2
- VKCPLONERNXWAQ-UHFFFAOYSA-N 4-methylpenta-1,2,4-triene Chemical group CC(=C)C=C=C VKCPLONERNXWAQ-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 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
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- 150000008065 acid anhydrides Chemical group 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 239000002168 alkylating agent Substances 0.000 description 1
- 229940100198 alkylating agent Drugs 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 238000005576 amination reaction Methods 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000010923 batch production Methods 0.000 description 1
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 238000010538 cationic polymerization reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000003426 co-catalyst Substances 0.000 description 1
- 230000000536 complexating effect Effects 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002118 epoxides Chemical class 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 239000002816 fuel additive Substances 0.000 description 1
- 125000000524 functional group Chemical class 0.000 description 1
- 125000003827 glycol group Chemical group 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 239000008240 homogeneous mixture Substances 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000010687 lubricating oil Substances 0.000 description 1
- KPSSIOMAKSHJJG-UHFFFAOYSA-N neopentyl alcohol Chemical compound CC(C)(C)CO KPSSIOMAKSHJJG-UHFFFAOYSA-N 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 239000002985 plastic film Substances 0.000 description 1
- 229920006255 plastic film Polymers 0.000 description 1
- 229920013639 polyalphaolefin Polymers 0.000 description 1
- -1 polyethers Chemical class 0.000 description 1
- 239000002685 polymerization catalyst Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- IAQRGUVFOMOMEM-ONEGZZNKSA-N trans-but-2-ene Chemical compound C\C=C\C IAQRGUVFOMOMEM-ONEGZZNKSA-N 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
- 239000004034 viscosity adjusting agent Substances 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Images
Landscapes
- Polymerisation Methods In General (AREA)
- Polymerization Catalysts (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Applications Claiming Priority (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US15426399P | 1999-09-16 | 1999-09-16 | |
| US60/154,263 | 1999-09-16 | ||
| US16035799P | 1999-10-19 | 1999-10-19 | |
| US60/160,357 | 1999-10-19 | ||
| US09/515,790 | 2000-02-29 | ||
| US09/515,790 US6562913B1 (en) | 1999-09-16 | 2000-02-29 | Process for producing high vinylidene polyisobutylene |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2007121874A Division JP5064878B2 (ja) | 1999-09-16 | 2007-05-02 | ポリイソブチレンの液相重合方法 |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014183170A Division JP5844864B2 (ja) | 1999-09-16 | 2014-09-09 | ポリイソブチレンの液相重合方法 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2012082439A JP2012082439A (ja) | 2012-04-26 |
| JP2012082439A5 JP2012082439A5 (enExample) | 2012-07-19 |
| JP5670874B2 true JP5670874B2 (ja) | 2015-02-18 |
Family
ID=46241634
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2011289168A Expired - Lifetime JP5670874B2 (ja) | 1999-09-16 | 2011-12-28 | ポリイソブチレンの液相重合方法 |
| JP2014183170A Expired - Lifetime JP5844864B2 (ja) | 1999-09-16 | 2014-09-09 | ポリイソブチレンの液相重合方法 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014183170A Expired - Lifetime JP5844864B2 (ja) | 1999-09-16 | 2014-09-09 | ポリイソブチレンの液相重合方法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (2) | JP5670874B2 (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20180133410A (ko) * | 2016-04-08 | 2018-12-14 | 이네오스 유럽 아게 | 중합 장치 및 중합 방법 |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109012504B (zh) * | 2018-09-17 | 2024-02-02 | 丹东明珠特种树脂有限公司 | 联产法由碳四获得高含量丁烯-1制备原料的方法及其系统装置 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2904314A1 (de) * | 1979-02-05 | 1980-08-14 | Basf Ag | Verfahren zur herstellung von polyisobutenen |
| DE19520078A1 (de) * | 1995-06-07 | 1996-12-12 | Basf Ag | Verfahren zur Herstellung von niedermolekularem, hochreaktivem Polyisobuten |
| JP3795666B2 (ja) * | 1997-03-07 | 2006-07-12 | 新日本石油化学株式会社 | ブテンポリマーの製造方法 |
| WO2001019873A1 (en) * | 1999-09-16 | 2001-03-22 | Texas Petrochemicals Lp | Process for preparing polyolefin products |
-
2011
- 2011-12-28 JP JP2011289168A patent/JP5670874B2/ja not_active Expired - Lifetime
-
2014
- 2014-09-09 JP JP2014183170A patent/JP5844864B2/ja not_active Expired - Lifetime
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20180133410A (ko) * | 2016-04-08 | 2018-12-14 | 이네오스 유럽 아게 | 중합 장치 및 중합 방법 |
| KR102287128B1 (ko) | 2016-04-08 | 2021-08-09 | 이네오스 유럽 아게 | 중합 장치 및 중합 방법 |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2015007250A (ja) | 2015-01-15 |
| JP5844864B2 (ja) | 2016-01-20 |
| JP2012082439A (ja) | 2012-04-26 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP5064878B2 (ja) | ポリイソブチレンの液相重合方法 | |
| EP2284198A2 (en) | Process for preparing polyolefin products | |
| KR100926605B1 (ko) | 중간-범위 비닐리덴 함량의 폴리이소부틸렌 및 그의 제조 | |
| US6884858B2 (en) | Process for preparing polyolefin products | |
| JP5844864B2 (ja) | ポリイソブチレンの液相重合方法 | |
| HK1152058A (en) | Process for preparing polyolefin products | |
| HK1152056A (en) | Process for preparing polyolefin products | |
| HK1152057A (en) | Process for preparing polyolefin products |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A521 | Written amendment |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20120127 |
|
| A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20120127 |
|
| A521 | Written amendment |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20120531 |
|
| A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A132 Effective date: 20131008 |
|
| A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20140107 |
|
| A602 | Written permission of extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A602 Effective date: 20140110 |
|
| A02 | Decision of refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A02 Effective date: 20140513 |
|
| A521 | Written amendment |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20140909 |
|
| A521 | Written amendment |
Free format text: JAPANESE INTERMEDIATE CODE: A821 Effective date: 20140910 |
|
| A911 | Transfer to examiner for re-examination before appeal (zenchi) |
Free format text: JAPANESE INTERMEDIATE CODE: A911 Effective date: 20141027 |
|
| TRDD | Decision of grant or rejection written | ||
| A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20141118 |
|
| A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20141218 |
|
| R150 | Certificate of patent or registration of utility model |
Ref document number: 5670874 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| EXPY | Cancellation because of completion of term |