CA2438068A1 - Mid-range vinylidene content polyisobutylene and production thereof - Google Patents
Mid-range vinylidene content polyisobutylene and production thereof Download PDFInfo
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- CA2438068A1 CA2438068A1 CA002438068A CA2438068A CA2438068A1 CA 2438068 A1 CA2438068 A1 CA 2438068A1 CA 002438068 A CA002438068 A CA 002438068A CA 2438068 A CA2438068 A CA 2438068A CA 2438068 A1 CA2438068 A1 CA 2438068A1
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F110/00—Homopolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
- C08F110/04—Monomers containing three or four carbon atoms
- C08F110/08—Butenes
- C08F110/10—Isobutene
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F10/00—Homopolymers and copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F10/00—Homopolymers and copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
- C08F10/04—Monomers containing three or four carbon atoms
- C08F10/08—Butenes
- C08F10/10—Isobutene
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F110/00—Homopolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
- C08F110/14—Monomers containing five or more carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F210/00—Copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
- C08F210/04—Monomers containing three or four carbon atoms
- C08F210/08—Butenes
- C08F210/10—Isobutene
-
- 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
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S525/00—Synthetic resins or natural rubbers -- part of the class 520 series
- Y10S525/911—Polymer from ethylenic monomers only, having terminal functional group other than unsaturation
Abstract
A relatively low molecular weight, mid-range vinylidene content PIB polymer product and a process for making the same. At least about 90 % of the PIB
molecules present in the product comprise alpha or beta position isomers. The vinylidene (alpha) isomer content of the product may range from 20 % to 70 %
thereof and the content of tetra-substituted internal double bonds is very low, preferably less than about 5 % and ideally less than about 1-2 %. The mid-range vinylidene content PIB polymer products are prepared by a liquid phase polymerization process conducted in a loop reactor (10, 100) at a temperature of at least 60 ~F using a BF3/methanol catalyst complex and a contact time of no more than 4 minutes.
molecules present in the product comprise alpha or beta position isomers. The vinylidene (alpha) isomer content of the product may range from 20 % to 70 %
thereof and the content of tetra-substituted internal double bonds is very low, preferably less than about 5 % and ideally less than about 1-2 %. The mid-range vinylidene content PIB polymer products are prepared by a liquid phase polymerization process conducted in a loop reactor (10, 100) at a temperature of at least 60 ~F using a BF3/methanol catalyst complex and a contact time of no more than 4 minutes.
Claims (29)
1. A mid-range vinylidene content PIB polymer composition comprising PIB
molecules, wherein a first portion of said PIB molecules have alpha position double bonds and a second portion of said PIB molecules have beta position double bonds, wherein said first and second portions together include at least 90% of the PIB molecules of the composition, wherein said first portion includes less than 70% of the PIB molecules of the composition, and wherein no more than about 10% of the PIB molecules of the composition have tetra-substituted internal double bonds.
molecules, wherein a first portion of said PIB molecules have alpha position double bonds and a second portion of said PIB molecules have beta position double bonds, wherein said first and second portions together include at least 90% of the PIB molecules of the composition, wherein said first portion includes less than 70% of the PIB molecules of the composition, and wherein no more than about 10% of the PIB molecules of the composition have tetra-substituted internal double bonds.
2. A mid-range vinylidene content PIB polymer composition as set forth in claim 1, wherein said first portion includes at least about 20% of the molecules of the composition.
3. A mid-range vinylidene content PIB polymer composition as set forth in claim 1 or 2, wherein no more than about 5% of the PIB molecules of the composition have tetra-substituted internal double bonds.
4. A mid-range vinylidene content PIB polymer composition as set forth in claim 1 or 2, wherein no more than about 2% of the PIB molecules of the composition have tetra-substituted internal double bonds.
5. A mid-range vinylidene content PIB polymer composition as set forth in claim 1 or 2 having an M N in the range of from about 350 to about 5000.
6. A mid-range vinylidene content PIB polymer composition as set forth in claim 5 having an M N in the range of from about 950 to about 1050.
7. A liquid phase polymerization process for preparing a mid-range vinylidene content PIB polymer composition comprising PIB molecules, wherein a first portion of said PIB molecules have alpha position double bonds and a second portion of said PIB
molecules have beta position double bonds, wherein said first and second portions together include at least 90% of the PIB molecules of the composition, wherein said first portion includes less than 70% of the PIB molecules of the composition, and wherein no more than about 10% of the PIB molecules of the composition have tetra-substituted internal double bonds, said process comprising:
providing a liquid feedstock comprising isobutylene;
providing a catalyst composition comprising a stable complex of BF3 and a catalyst complexing agent, wherein the ratio of complexing agent to BF3 in said complex is no more than about 1.3:1;
introducing said feedstock and said catalyst composition into a residual reaction mixture in a loop reactor reaction zone;
recirculating the residual reaction mixture in said zone at a recirculation rate sufficient to cause intimate intermixing of the residual reaction mixture, the feedstock and the catalyst composition to thereby present a recirculating, intimately intermixed reaction admixture in said reaction zone;
maintaining the recirculating intimately intermixed reaction admixture in its intimately intermixed condition and removing heat of reaction from the reaction admixture at a rate calculated to provide a substantially constant reaction temperature in the reaction admixture while the same is recirculating in said reaction zone;
withdrawing a product stream comprising said mid-range vinylidene content PIB
polymer composition; and controlling the introduction of said feedstock into said reaction zone and the withdrawal of said product stream from the reaction zone such that the residence time of the isobutylene components undergoing polymerization in the reaction zone is no more than about 4 minutes.
molecules have beta position double bonds, wherein said first and second portions together include at least 90% of the PIB molecules of the composition, wherein said first portion includes less than 70% of the PIB molecules of the composition, and wherein no more than about 10% of the PIB molecules of the composition have tetra-substituted internal double bonds, said process comprising:
providing a liquid feedstock comprising isobutylene;
providing a catalyst composition comprising a stable complex of BF3 and a catalyst complexing agent, wherein the ratio of complexing agent to BF3 in said complex is no more than about 1.3:1;
introducing said feedstock and said catalyst composition into a residual reaction mixture in a loop reactor reaction zone;
recirculating the residual reaction mixture in said zone at a recirculation rate sufficient to cause intimate intermixing of the residual reaction mixture, the feedstock and the catalyst composition to thereby present a recirculating, intimately intermixed reaction admixture in said reaction zone;
maintaining the recirculating intimately intermixed reaction admixture in its intimately intermixed condition and removing heat of reaction from the reaction admixture at a rate calculated to provide a substantially constant reaction temperature in the reaction admixture while the same is recirculating in said reaction zone;
withdrawing a product stream comprising said mid-range vinylidene content PIB
polymer composition; and controlling the introduction of said feedstock into said reaction zone and the withdrawal of said product stream from the reaction zone such that the residence time of the isobutylene components undergoing polymerization in the reaction zone is no more than about 4 minutes.
8. A process as set forth in claim 7, wherein said reaction temperature is at least about 60° F.
9. A process as set forth in claim 7, wherein said agent is methanol.
10. A process as set forth in claim 8, wherein said agent is methanol.
11. A process as set forth in claim 10, wherein said residence time is no more than about 1 minute.
12. A process as set forth in claim 11, wherein said residence time is less than 1 minute.
13. A process as set forth in claim 10, wherein said mid-range vinylidene content PIB polymer composition in said product stream has a molecular weight in the range of from about 350 to about 5000.
14. A process as set forth in claim 13, wherein said mid-range vinylidene content PIB polymer composition in said product stream has a molecular weight in the range of from about 950 to about 1050.
15. A process as set forth in claim 10, wherein from about 0.1 to about 10 millimoles of BF3 are introduced into said reaction admixture with said catalyst composition for each mole of isobutylene introduced into said admixture in said feedstock.
16. A process as set forth in claim 10, wherein from about 0.5 to about 2 millimoles of BF3 are introduced into said reaction admixture with said catalyst composition for each mole of isobutylene introduced into said admixture in said feedstock.
17. A process as set forth in claim 10, wherein the polydispersity of said mid-range vinylidene content PIB polymer composition in said product stream is no more than about 2Ø
-23a
-23a
18. A process as set forth in claim 10, wherein the polydispersity of said mid-range vinylidene content PIB polymer composition in said product stream no more than about 1.65.
19. A process as set forth in claim 10, wherein a reaction temperature of at least 90 °F is maintained in the reaction admixture while the same is recirculating in said reaction zone.
20. A liquid phase polymerization process for preparing a mid-range vinylidene content PIB polymer composition, said process comprising:
providing a feedstock comprising isobutylene;
providing a catalyst composition comprising a complex of BF3 and a complexing agent therefor;
introducing said feedstock and said catalyst composition into a residual reaction mixture in a reaction zone;
intimately intermixing said residual reaction mixture, said feedstock and said catalyst composition to present an intimately intermixed reaction admixture in said reaction zone;
maintaining the intimately intermixed reaction admixture in its intimately intermixed condition and keeping it at a temperature of at least about 0° C. while the same is in said reaction zone, to thereby cause the isobutylene therein to undergo polymerization to form said polyisobutylene;
withdrawing a product stream comprising polyisobutylene having an alpha plus beta isomer content of at least about 90% from said reaction zone; and controlling the introduction of said feedstock into said reaction zone and the withdrawal of said product stream from the reaction zone such that the residence time of the isobutylene undergoing polymerization in the reaction zone is no greater than about 4 minutes.
providing a feedstock comprising isobutylene;
providing a catalyst composition comprising a complex of BF3 and a complexing agent therefor;
introducing said feedstock and said catalyst composition into a residual reaction mixture in a reaction zone;
intimately intermixing said residual reaction mixture, said feedstock and said catalyst composition to present an intimately intermixed reaction admixture in said reaction zone;
maintaining the intimately intermixed reaction admixture in its intimately intermixed condition and keeping it at a temperature of at least about 0° C. while the same is in said reaction zone, to thereby cause the isobutylene therein to undergo polymerization to form said polyisobutylene;
withdrawing a product stream comprising polyisobutylene having an alpha plus beta isomer content of at least about 90% from said reaction zone; and controlling the introduction of said feedstock into said reaction zone and the withdrawal of said product stream from the reaction zone such that the residence time of the isobutylene undergoing polymerization in the reaction zone is no greater than about 4 minutes.
21. A process as set forth in claim 20, wherein said polyisobutylene in said product stream has a number average molecular weight in the range of from about 350 to about 5000.
-23b-
-23b-
22. A mid-range vinylidene content PIB polymer composition comprising PIB
molecules, wherein a first portion of said PIB molecules have alpha position double bonds and a second portion of said PIB molecules have beta position double bonds, wherein said first and second portions together include at least 90% of the PIB molecules of the composition, and wherein no more than about 10% of the PIB molecules of the composition have tetra-substituted internal double bonds.
molecules, wherein a first portion of said PIB molecules have alpha position double bonds and a second portion of said PIB molecules have beta position double bonds, wherein said first and second portions together include at least 90% of the PIB molecules of the composition, and wherein no more than about 10% of the PIB molecules of the composition have tetra-substituted internal double bonds.
23. A liquid phase polymerization process for preparing a mid-range vinylidene content PIB polymer composition comprising PIB molecules, wherein a first portion of said PIB molecules have alpha position double bonds and a second portion of said PIB
molecules have beta position double bonds, wherein said first and second portions together include at least 90% of the PIB molecules of the composition, and wherein no more than about 10% of the PIB molecules of the composition have tetra-substituted internal double bonds, said process comprising:
providing a liquid feedstock comprising isobutylene;
providing a catalyst composition comprising a stable complex of HF3 and a catalyst complexing agent, wherein the ratio of complexing agent to BF3 in said complex is no more than about 1.3:1;
introducing said feedstock and said catalyst composition into a residual reaction mixture in a loop reactor reaction zone;
recirculating the residual reaction mixture in said zone at a recirculation rate sufficient to cause intimate intermixing of the residual reaction mixture, the feedstock and the catalyst composition to thereby present a recirculating, intimately intermixed reaction admixture in said reaction zone;
maintaining the recirculating intimately intermixed reaction admixture in its intimately intermixed condition and removing heat of reaction from the reaction admixture at a rate calculated to provide a substantially constant reaction temperature in the reaction admixture while the same is recirculating in said reaction zone;
withdrawing a product stream comprising said mid-range vinylidene content PIB
polymer composition; and controlling the introduction of said feedstock into said reaction zone and the withdrawal of said product stream from the reaction zone such that the residence time of the -23c-isobutylene components undergoing polymerization in the reaction zone is no more than about 4 minutes.
molecules have beta position double bonds, wherein said first and second portions together include at least 90% of the PIB molecules of the composition, and wherein no more than about 10% of the PIB molecules of the composition have tetra-substituted internal double bonds, said process comprising:
providing a liquid feedstock comprising isobutylene;
providing a catalyst composition comprising a stable complex of HF3 and a catalyst complexing agent, wherein the ratio of complexing agent to BF3 in said complex is no more than about 1.3:1;
introducing said feedstock and said catalyst composition into a residual reaction mixture in a loop reactor reaction zone;
recirculating the residual reaction mixture in said zone at a recirculation rate sufficient to cause intimate intermixing of the residual reaction mixture, the feedstock and the catalyst composition to thereby present a recirculating, intimately intermixed reaction admixture in said reaction zone;
maintaining the recirculating intimately intermixed reaction admixture in its intimately intermixed condition and removing heat of reaction from the reaction admixture at a rate calculated to provide a substantially constant reaction temperature in the reaction admixture while the same is recirculating in said reaction zone;
withdrawing a product stream comprising said mid-range vinylidene content PIB
polymer composition; and controlling the introduction of said feedstock into said reaction zone and the withdrawal of said product stream from the reaction zone such that the residence time of the -23c-isobutylene components undergoing polymerization in the reaction zone is no more than about 4 minutes.
24. A process as set forth in claim 7, wherein said feedstock comprises at least about 30% isobutylene by weight.
25. A process as set forth in claim 20, wherein said feedstock comprises at least about 30% isobutylene by weight.
26. A process as set forth in claim 23, wherein said feedstock comprises at least about 30% isobutylene by weight.
27. A process as set forth in claim 7, wherein said feedstock comprises a raff-stream.
28. A process as set forth in claim 20, wherein said feedstock comprises a raff 1 stream.
29. A process as set forth in claim 23, wherein said feedstock comprises a raff 1 stream.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US27930501P | 2001-03-28 | 2001-03-28 | |
| US60/279,305 | 2001-03-28 | ||
| PCT/US2002/008684 WO2002079283A1 (en) | 2001-03-28 | 2002-03-21 | Mid-range vinylidene content polyisobutylene and production thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2438068A1 true CA2438068A1 (en) | 2002-10-10 |
| CA2438068C CA2438068C (en) | 2011-01-04 |
Family
ID=23068415
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2438068A Expired - Lifetime CA2438068C (en) | 2001-03-28 | 2002-03-21 | Mid-range vinylidene content polyisobutylene and production thereof |
Country Status (14)
| Country | Link |
|---|---|
| US (5) | US7037999B2 (en) |
| EP (3) | EP1997836B1 (en) |
| JP (1) | JP2005507435A (en) |
| KR (2) | KR100889147B1 (en) |
| CN (2) | CN101230115B (en) |
| AT (1) | ATE413420T1 (en) |
| CA (1) | CA2438068C (en) |
| DE (1) | DE60229735D1 (en) |
| DK (1) | DK1381637T4 (en) |
| ES (2) | ES2608680T3 (en) |
| MX (1) | MXPA03007868A (en) |
| PT (1) | PT1381637E (en) |
| TW (1) | TW589327B (en) |
| WO (1) | WO2002079283A1 (en) |
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2002
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- 2002-03-21 JP JP2002578298A patent/JP2005507435A/en active Pending
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- 2002-03-21 WO PCT/US2002/008684 patent/WO2002079283A1/en active Search and Examination
- 2002-03-21 KR KR1020037010614A patent/KR100889147B1/en active IP Right Grant
- 2002-03-21 KR KR1020087032256A patent/KR100926605B1/en active IP Right Grant
- 2002-03-21 EP EP08075716.4A patent/EP1997836B1/en not_active Expired - Lifetime
- 2002-03-21 EP EP02728532.9A patent/EP1381637B2/en not_active Expired - Lifetime
- 2002-03-21 EP EP08075717.2A patent/EP1997837B1/en not_active Expired - Lifetime
- 2002-03-21 ES ES02728532.9T patent/ES2316562T5/en not_active Expired - Lifetime
- 2002-03-21 AT AT02728532T patent/ATE413420T1/en active
- 2002-03-21 MX MXPA03007868A patent/MXPA03007868A/en active IP Right Grant
- 2002-03-21 PT PT02728532T patent/PT1381637E/en unknown
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- 2004-10-19 US US10/968,630 patent/US7056990B2/en not_active Expired - Lifetime
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