GB1030306A - Process for the catalytic hydrogenation of polymers of dienes - Google Patents
Process for the catalytic hydrogenation of polymers of dienesInfo
- Publication number
- GB1030306A GB1030306A GB31435/64A GB3143564A GB1030306A GB 1030306 A GB1030306 A GB 1030306A GB 31435/64 A GB31435/64 A GB 31435/64A GB 3143564 A GB3143564 A GB 3143564A GB 1030306 A GB1030306 A GB 1030306A
- Authority
- GB
- United Kingdom
- Prior art keywords
- compound
- organic
- metal
- hydrogenation
- cobalt
- 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
Links
- 150000001993 dienes Chemical class 0.000 title abstract 2
- 229920000642 polymer Polymers 0.000 title abstract 2
- 238000009903 catalytic hydrogenation reaction Methods 0.000 title 1
- 238000000034 method Methods 0.000 title 1
- 229910052751 metal Inorganic materials 0.000 abstract 6
- 239000002184 metal Substances 0.000 abstract 6
- 150000001875 compounds Chemical class 0.000 abstract 5
- 238000005984 hydrogenation reaction Methods 0.000 abstract 5
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 abstract 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 abstract 4
- 150000002894 organic compounds Chemical class 0.000 abstract 4
- 239000010941 cobalt Substances 0.000 abstract 3
- 229910017052 cobalt Inorganic materials 0.000 abstract 3
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 abstract 3
- -1 hydrocarbyl compound Chemical class 0.000 abstract 3
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 abstract 3
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 abstract 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 abstract 2
- 125000004429 atom Chemical group 0.000 abstract 2
- 239000003054 catalyst Substances 0.000 abstract 2
- 238000006243 chemical reaction Methods 0.000 abstract 2
- 238000007720 emulsion polymerization reaction Methods 0.000 abstract 2
- 150000002148 esters Chemical class 0.000 abstract 2
- 150000002500 ions Chemical class 0.000 abstract 2
- 229910052759 nickel Inorganic materials 0.000 abstract 2
- 125000004430 oxygen atom Chemical group O* 0.000 abstract 2
- 239000002904 solvent Substances 0.000 abstract 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 abstract 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 abstract 1
- 239000004411 aluminium Substances 0.000 abstract 1
- 229910052782 aluminium Inorganic materials 0.000 abstract 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 abstract 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 abstract 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 abstract 1
- 238000007334 copolymerization reaction Methods 0.000 abstract 1
- 239000000839 emulsion Substances 0.000 abstract 1
- 238000010528 free radical solution polymerization reaction Methods 0.000 abstract 1
- 229930195733 hydrocarbon Natural products 0.000 abstract 1
- 150000002430 hydrocarbons Chemical class 0.000 abstract 1
- 229910052742 iron Inorganic materials 0.000 abstract 1
- 229910052744 lithium Inorganic materials 0.000 abstract 1
- 150000002736 metal compounds Chemical class 0.000 abstract 1
- 150000002815 nickel Chemical class 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-M phenolate Chemical compound [O-]C1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-M 0.000 abstract 1
- 229940031826 phenolate Drugs 0.000 abstract 1
- 229920001195 polyisoprene Polymers 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08C—TREATMENT OR CHEMICAL MODIFICATION OF RUBBERS
- C08C19/00—Chemical modification of rubber
- C08C19/02—Hydrogenation
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/04—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing carboxylic acids or their salts
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/12—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing organo-metallic compounds or metal hydrides
- B01J31/14—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing organo-metallic compounds or metal hydrides of aluminium or boron
- B01J31/143—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing organo-metallic compounds or metal hydrides of aluminium or boron of aluminium
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/22—Organic complexes
- B01J31/2204—Organic complexes the ligands containing oxygen or sulfur as complexing atoms
- B01J31/2208—Oxygen, e.g. acetylacetonates
- B01J31/2226—Anionic ligands, i.e. the overall ligand carries at least one formal negative charge
- B01J31/2252—Sulfonate ligands
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B35/00—Reactions without formation or introduction of functional groups containing hetero atoms, involving a change in the type of bonding between two carbon atoms already directly linked
- C07B35/02—Reduction
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C5/00—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms
- C07C5/02—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by hydrogenation
- C07C5/03—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by hydrogenation of non-aromatic carbon-to-carbon double bonds
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
- B01J2231/60—Reduction reactions, e.g. hydrogenation
- B01J2231/64—Reductions in general of organic substrates, e.g. hydride reductions or hydrogenations
- B01J2231/641—Hydrogenation of organic substrates, i.e. H2 or H-transfer hydrogenations, e.g. Fischer-Tropsch processes
- B01J2231/645—Hydrogenation of organic substrates, i.e. H2 or H-transfer hydrogenations, e.g. Fischer-Tropsch processes of C=C or C-C triple bonds
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/80—Complexes comprising metals of Group VIII as the central metal
- B01J2531/84—Metals of the iron group
- B01J2531/842—Iron
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/80—Complexes comprising metals of Group VIII as the central metal
- B01J2531/84—Metals of the iron group
- B01J2531/845—Cobalt
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/80—Complexes comprising metals of Group VIII as the central metal
- B01J2531/84—Metals of the iron group
- B01J2531/847—Nickel
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2540/00—Compositional aspects of coordination complexes or ligands in catalyst systems
- B01J2540/40—Non-coordinating groups comprising nitrogen
-
- 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
-
- 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
- C07C2531/04—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing carboxylic acids or their salts
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- General Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Inorganic Chemistry (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Catalysts (AREA)
Abstract
Polymers of dienes are hydrogenated, optionally in the solutions in which they are formed, using a catalyst which is the product of reaction of a metal hydrocarbyl compound and an organic compound of iron, cobalt or nickel, the organic compound containing at least one organic radical attached to the metal atom through an oxygen atom, the atomic ratio C: O in the compound being at least 3, and the compound being dissolved in an organic solvent to a concentration of at least 10 m.gms. of metal per litre. Examples relate to hydrogenation of polyisoprene; solution and emulsion polymerization of butadiene and hydrogenation of the product; emulsion polymerization preparation and hydrogenation of SBR; emulsion copolymerization of butadiene and methyl acrylate and hydrogenation of the products.ALSO:A hydrogenation catalyst comprises the product of reaction of (a) a metal hydrocarbyl compound with (b) an organic compound of ion, cobalt, or nickel, the organic compound containing at least one organic radial attached to the metal atom through an oxygen atom, the atomic C : O ratio is the compound being at least 3, and the compound being dissolved in an organic oxygen-free solvent to a concentration of at least 10 mgm metal per litre. The hydrocarbyl compound (a) may be a Group I, II or III metal compound; lithium, aluminium, and lithium-aluminium alkyl compounds are referred to. Compound (b) may be an ion, cobalt or nickel salt of a carboxylic acid, an enolate or phenolate, or a salt of sulphonic acid, sulphonic acid, half ester of sulphonic acid or half ester of sulphurous acid. The solvents may be hydrocarbons or chlorinated hydrocarbons.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL296137 | 1963-08-02 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1030306A true GB1030306A (en) | 1966-05-18 |
Family
ID=19754924
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB31435/64A Expired GB1030306A (en) | 1963-08-02 | 1964-08-04 | Process for the catalytic hydrogenation of polymers of dienes |
Country Status (5)
| Country | Link |
|---|---|
| BE (1) | BE651281A (en) |
| DE (1) | DE1215372B (en) |
| GB (1) | GB1030306A (en) |
| NL (1) | NL296137A (en) |
| SE (1) | SE305324B (en) |
Cited By (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4788361A (en) * | 1987-10-30 | 1988-11-29 | Shell Oil Company | Polymeric viscosity index improver and oil composition comprising the same |
| US4851474A (en) * | 1987-09-29 | 1989-07-25 | Shell Oil Company | Block copolymer and method of preparing same |
| US4859737A (en) * | 1987-11-24 | 1989-08-22 | Shell Oil Company | Polymeric composition |
| US4898784A (en) * | 1987-12-30 | 1990-02-06 | Shell Oil Company | Tie layer composition and laminated structures containing same |
| US4980331A (en) * | 1988-11-09 | 1990-12-25 | Shell Oil Company | Hydrogenation catalyst and hydrogenation process wherein said catalyst is used |
| EP0368419A3 (en) * | 1988-11-09 | 1991-02-06 | Shell Internationale Researchmaatschappij B.V. | Hydrogenation catalyst and hydrogenation process wherein said catalyst is used |
| US5030779A (en) * | 1989-06-08 | 1991-07-09 | Shell Oil Company | Hydrogenation catalyst and hydrogenation process wherein said catalyst is used |
| US5057582A (en) * | 1988-12-23 | 1991-10-15 | Shell Oil Company | Hydrogenation catalyst and hydrogenation process wherein said catalyst is used |
| EP2363454A1 (en) | 2010-02-23 | 2011-09-07 | Infineum International Limited | A lubricating oil composition |
| EP2607466A2 (en) | 2011-12-21 | 2013-06-26 | Infineum International Limited | Viscosity index improvers for lubricating oil compositions |
| EP2607461A1 (en) | 2011-12-21 | 2013-06-26 | Infineum International Limited | Marine engine lubrication |
| EP2781587A1 (en) | 2013-03-21 | 2014-09-24 | Infineum International Limited | Marine engine lubrication |
| EP2891704A1 (en) | 2014-01-02 | 2015-07-08 | Infineum International Limited | Viscosity index improver concentrates for lubricating oil compositions |
| US9951160B2 (en) | 2014-05-16 | 2018-04-24 | Kraton Polymers U.S. Llc | Polyalkenyl coupling agent and conjugated diene polymers prepared therefrom |
| EP3378877A1 (en) | 2017-02-28 | 2018-09-26 | Evonik Oil Additives GmbH | Hydrogenated polybutadienes useful as lubricant additives |
| WO2020099079A1 (en) | 2018-11-13 | 2020-05-22 | Evonik Operations Gmbh | Process for preparing random copolymers |
| WO2020099078A1 (en) | 2018-11-13 | 2020-05-22 | Evonik Operations Gmbh | Random copolymers for use as base oils or lubricant additives |
| EP3831913A1 (en) | 2019-12-05 | 2021-06-09 | Infineum International Limited | Triblock copolymer concentrates for lubricating oil compositions |
| EP3907269A1 (en) | 2020-05-05 | 2021-11-10 | Evonik Operations GmbH | Hydrogenated linear polydiene copolymers as base stock or lubricant additives for lubricant compositions |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1268210A (en) * | 1968-04-23 | 1972-03-22 | Bridgestone Tire Co Ltd | Process for hydrogenating polymers |
-
0
- NL NL296137D patent/NL296137A/xx unknown
-
1964
- 1964-07-31 DE DES92410A patent/DE1215372B/en active Pending
- 1964-07-31 SE SE9338/64A patent/SE305324B/xx unknown
- 1964-07-31 BE BE651281D patent/BE651281A/xx unknown
- 1964-08-04 GB GB31435/64A patent/GB1030306A/en not_active Expired
Cited By (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4851474A (en) * | 1987-09-29 | 1989-07-25 | Shell Oil Company | Block copolymer and method of preparing same |
| US4788361A (en) * | 1987-10-30 | 1988-11-29 | Shell Oil Company | Polymeric viscosity index improver and oil composition comprising the same |
| US4859737A (en) * | 1987-11-24 | 1989-08-22 | Shell Oil Company | Polymeric composition |
| US4898784A (en) * | 1987-12-30 | 1990-02-06 | Shell Oil Company | Tie layer composition and laminated structures containing same |
| US4980331A (en) * | 1988-11-09 | 1990-12-25 | Shell Oil Company | Hydrogenation catalyst and hydrogenation process wherein said catalyst is used |
| EP0368419A3 (en) * | 1988-11-09 | 1991-02-06 | Shell Internationale Researchmaatschappij B.V. | Hydrogenation catalyst and hydrogenation process wherein said catalyst is used |
| US5057582A (en) * | 1988-12-23 | 1991-10-15 | Shell Oil Company | Hydrogenation catalyst and hydrogenation process wherein said catalyst is used |
| US5030779A (en) * | 1989-06-08 | 1991-07-09 | Shell Oil Company | Hydrogenation catalyst and hydrogenation process wherein said catalyst is used |
| EP2363454A1 (en) | 2010-02-23 | 2011-09-07 | Infineum International Limited | A lubricating oil composition |
| EP2607461A1 (en) | 2011-12-21 | 2013-06-26 | Infineum International Limited | Marine engine lubrication |
| EP2607466A2 (en) | 2011-12-21 | 2013-06-26 | Infineum International Limited | Viscosity index improvers for lubricating oil compositions |
| EP2781587A1 (en) | 2013-03-21 | 2014-09-24 | Infineum International Limited | Marine engine lubrication |
| EP2891704A1 (en) | 2014-01-02 | 2015-07-08 | Infineum International Limited | Viscosity index improver concentrates for lubricating oil compositions |
| US9951160B2 (en) | 2014-05-16 | 2018-04-24 | Kraton Polymers U.S. Llc | Polyalkenyl coupling agent and conjugated diene polymers prepared therefrom |
| US10787623B2 (en) | 2017-02-28 | 2020-09-29 | Evonik Operations Gmbh | Hydrogenated polybutadienes useful as lubricant additives |
| EP3378877A1 (en) | 2017-02-28 | 2018-09-26 | Evonik Oil Additives GmbH | Hydrogenated polybutadienes useful as lubricant additives |
| RU2676472C1 (en) * | 2017-02-28 | 2018-12-29 | Эвоник Оил Эддитивс Гмбх | Hydrogenized polybutadienes suitable as additives to lubricating materials |
| WO2020099079A1 (en) | 2018-11-13 | 2020-05-22 | Evonik Operations Gmbh | Process for preparing random copolymers |
| WO2020099078A1 (en) | 2018-11-13 | 2020-05-22 | Evonik Operations Gmbh | Random copolymers for use as base oils or lubricant additives |
| US11453837B2 (en) | 2018-11-13 | 2022-09-27 | Evonik Operations Gmbh | Random copolymers for use as base oils or lubricant additives |
| EP3831913A1 (en) | 2019-12-05 | 2021-06-09 | Infineum International Limited | Triblock copolymer concentrates for lubricating oil compositions |
| EP3907269A1 (en) | 2020-05-05 | 2021-11-10 | Evonik Operations GmbH | Hydrogenated linear polydiene copolymers as base stock or lubricant additives for lubricant compositions |
| US11603425B2 (en) | 2020-05-05 | 2023-03-14 | Evonik Operations Gmbh | Hydrogenated linear polydiene copolymers as base stock or lubricant additives for lubricant compositions |
Also Published As
| Publication number | Publication date |
|---|---|
| BE651281A (en) | 1965-02-01 |
| DE1215372B (en) | 1966-04-28 |
| NL296137A (en) | 1900-01-01 |
| SE305324B (en) | 1968-10-21 |
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