EP2785763A1 - Fonctionnalisation de polymères à terminaison vinyle par métathèse croisée par ouverture de cycle - Google Patents
Fonctionnalisation de polymères à terminaison vinyle par métathèse croisée par ouverture de cycleInfo
- Publication number
- EP2785763A1 EP2785763A1 EP20120854390 EP12854390A EP2785763A1 EP 2785763 A1 EP2785763 A1 EP 2785763A1 EP 20120854390 EP20120854390 EP 20120854390 EP 12854390 A EP12854390 A EP 12854390A EP 2785763 A1 EP2785763 A1 EP 2785763A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- mol
- propylene
- group
- oligomer
- polymer
- 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.)
- Withdrawn
Links
- 229920000642 polymer Polymers 0.000 title claims abstract description 147
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 title claims abstract description 130
- 229920002554 vinyl polymer Polymers 0.000 title claims abstract description 98
- 238000005686 cross metathesis reaction Methods 0.000 title description 14
- 238000007142 ring opening reaction Methods 0.000 title description 8
- 238000007306 functionalization reaction Methods 0.000 title description 5
- -1 cyclic olefin Chemical class 0.000 claims abstract description 118
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims abstract description 111
- 238000000034 method Methods 0.000 claims abstract description 76
- 230000008569 process Effects 0.000 claims abstract description 47
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 116
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 104
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 102
- 239000003054 catalyst Substances 0.000 claims description 96
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 95
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 82
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 80
- 239000005977 Ethylene Substances 0.000 claims description 80
- 239000001257 hydrogen Substances 0.000 claims description 73
- 229910052739 hydrogen Inorganic materials 0.000 claims description 73
- 150000001336 alkenes Chemical class 0.000 claims description 69
- 125000004122 cyclic group Chemical group 0.000 claims description 49
- 229920001577 copolymer Polymers 0.000 claims description 48
- 239000003446 ligand Substances 0.000 claims description 43
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 41
- 125000004432 carbon atom Chemical group C* 0.000 claims description 41
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 40
- 238000005649 metathesis reaction Methods 0.000 claims description 38
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 37
- LPIQUOYDBNQMRZ-UHFFFAOYSA-N cyclopentene Chemical group C1CC=CC1 LPIQUOYDBNQMRZ-UHFFFAOYSA-N 0.000 claims description 36
- 125000000746 allylic group Chemical group 0.000 claims description 32
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 30
- 125000000217 alkyl group Chemical group 0.000 claims description 29
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 29
- 239000000203 mixture Substances 0.000 claims description 29
- 229910052707 ruthenium Inorganic materials 0.000 claims description 29
- 229910052799 carbon Inorganic materials 0.000 claims description 27
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 27
- 150000004820 halides Chemical class 0.000 claims description 26
- 229910052751 metal Inorganic materials 0.000 claims description 26
- 239000002184 metal Substances 0.000 claims description 26
- 125000003118 aryl group Chemical group 0.000 claims description 24
- 229920000098 polyolefin Polymers 0.000 claims description 24
- JFNLZVQOOSMTJK-KNVOCYPGSA-N norbornene Chemical group C1[C@@H]2CC[C@H]1C=C2 JFNLZVQOOSMTJK-KNVOCYPGSA-N 0.000 claims description 22
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical group C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 claims description 21
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 21
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 claims description 19
- 239000004913 cyclooctene Chemical group 0.000 claims description 19
- 239000000178 monomer Substances 0.000 claims description 19
- 229910052762 osmium Inorganic materials 0.000 claims description 19
- DCTOHCCUXLBQMS-UHFFFAOYSA-N 1-undecene Chemical group CCCCCCCCCC=C DCTOHCCUXLBQMS-UHFFFAOYSA-N 0.000 claims description 18
- 125000000129 anionic group Chemical group 0.000 claims description 18
- ZGEGCLOFRBLKSE-UHFFFAOYSA-N methylene hexane Chemical group CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 claims description 18
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Chemical group C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 claims description 18
- URYYVOIYTNXXBN-UPHRSURJSA-N cyclooctene Chemical group C1CCC\C=C/CC1 URYYVOIYTNXXBN-UPHRSURJSA-N 0.000 claims description 17
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 17
- 125000005842 heteroatom Chemical group 0.000 claims description 17
- SJYNFBVQFBRSIB-UHFFFAOYSA-N norbornadiene Chemical group C1=CC2C=CC1C2 SJYNFBVQFBRSIB-UHFFFAOYSA-N 0.000 claims description 17
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 16
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical group CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 claims description 15
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Chemical group CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 claims description 15
- 150000004696 coordination complex Chemical class 0.000 claims description 15
- 229910052736 halogen Inorganic materials 0.000 claims description 15
- 150000002367 halogens Chemical class 0.000 claims description 15
- 229910052757 nitrogen Inorganic materials 0.000 claims description 15
- WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 claims description 15
- 230000007935 neutral effect Effects 0.000 claims description 14
- RRKODOZNUZCUBN-CCAGOZQPSA-N (1z,3z)-cycloocta-1,3-diene Chemical group C1CC\C=C/C=C\C1 RRKODOZNUZCUBN-CCAGOZQPSA-N 0.000 claims description 13
- YCNYCBYHUAGZIZ-UHFFFAOYSA-N 7-oxabicyclo[2.2.1]hept-2-ene Chemical group O1C2CCC1C=C2 YCNYCBYHUAGZIZ-UHFFFAOYSA-N 0.000 claims description 13
- YKCNBNDWSATCJL-UHFFFAOYSA-N 7-oxabicyclo[2.2.1]hepta-2,5-diene Chemical group C1=CC2C=CC1O2 YKCNBNDWSATCJL-UHFFFAOYSA-N 0.000 claims description 13
- HYPABJGVBDSCIT-UPHRSURJSA-N cyclododecene Chemical group C1CCCCC\C=C/CCCC1 HYPABJGVBDSCIT-UPHRSURJSA-N 0.000 claims description 13
- ZXIJMRYMVAMXQP-UHFFFAOYSA-N cycloheptene Chemical group C1CCC=CCC1 ZXIJMRYMVAMXQP-UHFFFAOYSA-N 0.000 claims description 13
- 239000000314 lubricant Substances 0.000 claims description 13
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical group CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 claims description 12
- 229910052782 aluminium Inorganic materials 0.000 claims description 12
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 12
- 229910052760 oxygen Inorganic materials 0.000 claims description 12
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical group CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 claims description 11
- YAYGSLOSTXKUBW-UHFFFAOYSA-N ruthenium(2+) Chemical compound [Ru+2] YAYGSLOSTXKUBW-UHFFFAOYSA-N 0.000 claims description 11
- 238000006471 dimerization reaction Methods 0.000 claims description 10
- CRSBERNSMYQZNG-UHFFFAOYSA-N 1 -dodecene Chemical group CCCCCCCCCCC=C CRSBERNSMYQZNG-UHFFFAOYSA-N 0.000 claims description 9
- 125000003963 dichloro group Chemical group Cl* 0.000 claims description 9
- 229940069096 dodecene Drugs 0.000 claims description 9
- AFFLGGQVNFXPEV-UHFFFAOYSA-N n-decene Chemical group CCCCCCCCC=C AFFLGGQVNFXPEV-UHFFFAOYSA-N 0.000 claims description 9
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical group CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 claims description 9
- 150000001993 dienes Chemical class 0.000 claims description 7
- KNDQHSIWLOJIGP-UMRXKNAASA-N (3ar,4s,7r,7as)-rel-3a,4,7,7a-tetrahydro-4,7-methanoisobenzofuran-1,3-dione Chemical compound O=C1OC(=O)[C@@H]2[C@H]1[C@]1([H])C=C[C@@]2([H])C1 KNDQHSIWLOJIGP-UMRXKNAASA-N 0.000 claims description 6
- 229920000089 Cyclic olefin copolymer Polymers 0.000 claims description 5
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 5
- UCPDHOTYYDHPEN-UPHRSURJSA-N (4z)-cyclooct-4-en-1-ol Chemical compound OC1CCC\C=C/CC1 UCPDHOTYYDHPEN-UPHRSURJSA-N 0.000 claims description 4
- VYXHVRARDIDEHS-UHFFFAOYSA-N 1,5-cyclooctadiene Chemical compound C1CC=CCCC=C1 VYXHVRARDIDEHS-UHFFFAOYSA-N 0.000 claims description 4
- 239000004912 1,5-cyclooctadiene Substances 0.000 claims description 4
- CXOZQHPXKPDQGT-UHFFFAOYSA-N 3-Methylcyclopentene Chemical compound CC1CCC=C1 CXOZQHPXKPDQGT-UHFFFAOYSA-N 0.000 claims description 4
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 claims description 3
- 239000000853 adhesive Substances 0.000 claims description 3
- 230000001070 adhesive effect Effects 0.000 claims description 3
- 125000000649 benzylidene group Chemical group [H]C(=[*])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 3
- PNPBGYBHLCEVMK-UHFFFAOYSA-L benzylidene(dichloro)ruthenium;tricyclohexylphosphane Chemical compound Cl[Ru](Cl)=CC1=CC=CC=C1.C1CCCCC1P(C1CCCCC1)C1CCCCC1.C1CCCCC1P(C1CCCCC1)C1CCCCC1 PNPBGYBHLCEVMK-UHFFFAOYSA-L 0.000 claims description 3
- 150000001649 bromium compounds Chemical class 0.000 claims description 3
- KMKCJXPECJFQPQ-UHFFFAOYSA-L dichloro-[(2-propan-2-yloxyphenyl)methylidene]ruthenium;tricyclohexylphosphane Chemical compound CC(C)OC1=CC=CC=C1C=[Ru](Cl)Cl.C1CCCCC1P(C1CCCCC1)C1CCCCC1 KMKCJXPECJFQPQ-UHFFFAOYSA-L 0.000 claims description 3
- 239000002816 fuel additive Substances 0.000 claims description 3
- ATQYNBNTEXNNIK-UHFFFAOYSA-N imidazol-2-ylidene Chemical group [C]1NC=CN1 ATQYNBNTEXNNIK-UHFFFAOYSA-N 0.000 claims description 3
- 125000001841 imino group Chemical group [H]N=* 0.000 claims description 3
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 3
- OSFBJERFMQCEQY-UHFFFAOYSA-N propylidene Chemical group [CH]CC OSFBJERFMQCEQY-UHFFFAOYSA-N 0.000 claims description 3
- 239000004034 viscosity adjusting agent Substances 0.000 claims description 3
- HVJJUDAMOHYMRL-UHFFFAOYSA-L dichloro-[(2-propan-2-yloxyphenyl)methylidene]ruthenium Chemical compound CC(C)OC1=CC=CC=C1C=[Ru](Cl)Cl HVJJUDAMOHYMRL-UHFFFAOYSA-L 0.000 claims description 2
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 6
- NYPYPOZNGOXYSU-UHFFFAOYSA-N 3-bromopyridine Chemical compound BrC1=CC=CN=C1 NYPYPOZNGOXYSU-UHFFFAOYSA-N 0.000 claims 1
- UNOMOKBVBBHHMU-UHFFFAOYSA-N benzylidene-dicyclohexyl-(4,4-dichlorocyclohexyl)-lambda5-phosphane ruthenium Chemical compound [Ru].ClC1(Cl)CCC(CC1)P(=Cc1ccccc1)(C1CCCCC1)C1CCCCC1 UNOMOKBVBBHHMU-UHFFFAOYSA-N 0.000 claims 1
- UZAFZWUWHHFWOK-UHFFFAOYSA-L dichloro-(3-phenylinden-1-ylidene)ruthenium;tricyclohexylphosphane Chemical compound C12=CC=CC=C2C(=[Ru](Cl)Cl)C=C1C1=CC=CC=C1.C1CCCCC1P(C1CCCCC1)C1CCCCC1.C1CCCCC1P(C1CCCCC1)C1CCCCC1 UZAFZWUWHHFWOK-UHFFFAOYSA-L 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 abstract description 3
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 54
- 238000005481 NMR spectroscopy Methods 0.000 description 41
- 239000000047 product Substances 0.000 description 31
- 238000006243 chemical reaction Methods 0.000 description 29
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 29
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 28
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 27
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 26
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 25
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 24
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 21
- 150000001875 compounds Chemical class 0.000 description 21
- 238000006116 polymerization reaction Methods 0.000 description 17
- 239000002904 solvent Substances 0.000 description 17
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 15
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 15
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 15
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 15
- 150000004703 alkoxides Chemical class 0.000 description 13
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 13
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- 238000005984 hydrogenation reaction Methods 0.000 description 12
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 12
- 239000000377 silicon dioxide Substances 0.000 description 12
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 10
- 125000002573 ethenylidene group Chemical group [*]=C=C([H])[H] 0.000 description 10
- ADLVDYMTBOSDFE-UHFFFAOYSA-N 5-chloro-6-nitroisoindole-1,3-dione Chemical compound C1=C(Cl)C([N+](=O)[O-])=CC2=C1C(=O)NC2=O ADLVDYMTBOSDFE-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 150000008052 alkyl sulfonates Chemical class 0.000 description 9
- 239000000460 chlorine Substances 0.000 description 9
- 150000003003 phosphines Chemical class 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 8
- 150000001412 amines Chemical class 0.000 description 8
- 150000008064 anhydrides Chemical class 0.000 description 8
- 229910052801 chlorine Inorganic materials 0.000 description 8
- AFABGHUZZDYHJO-UHFFFAOYSA-N dimethyl butane Natural products CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 8
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 8
- 239000000376 reactant Substances 0.000 description 8
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 7
- 230000015572 biosynthetic process Effects 0.000 description 7
- 150000002466 imines Chemical class 0.000 description 7
- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 description 7
- 239000003921 oil Substances 0.000 description 7
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical group [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 description 7
- 239000007858 starting material Substances 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- 238000003786 synthesis reaction Methods 0.000 description 7
- RELMFMZEBKVZJC-UHFFFAOYSA-N 1,2,3-trichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1Cl RELMFMZEBKVZJC-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- 239000000654 additive Substances 0.000 description 6
- 229940045714 alkyl sulfonate alkylating agent Drugs 0.000 description 6
- 229910052794 bromium Inorganic materials 0.000 description 6
- 239000007795 chemical reaction product Substances 0.000 description 6
- 239000003085 diluting agent Substances 0.000 description 6
- 239000000539 dimer Substances 0.000 description 6
- 125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 0.000 description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 6
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 235000019198 oils Nutrition 0.000 description 6
- 239000002002 slurry Substances 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 5
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 description 5
- 101150065749 Churc1 gene Proteins 0.000 description 5
- 102100038239 Protein Churchill Human genes 0.000 description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 5
- 125000000753 cycloalkyl group Chemical group 0.000 description 5
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 5
- 235000019441 ethanol Nutrition 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 125000000524 functional group Chemical group 0.000 description 5
- 125000000654 isopropylidene group Chemical group C(C)(C)=* 0.000 description 5
- 229910052759 nickel Inorganic materials 0.000 description 5
- 238000001228 spectrum Methods 0.000 description 5
- 125000001424 substituent group Chemical group 0.000 description 5
- 229910052717 sulfur Inorganic materials 0.000 description 5
- QVLAWKAXOMEXPM-DICFDUPASA-N 1,1,1,2-tetrachloro-2,2-dideuterioethane Chemical compound [2H]C([2H])(Cl)C(Cl)(Cl)Cl QVLAWKAXOMEXPM-DICFDUPASA-N 0.000 description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 4
- 238000005865 alkene metathesis reaction Methods 0.000 description 4
- 125000000304 alkynyl group Chemical group 0.000 description 4
- DMEGYFMYUHOHGS-UHFFFAOYSA-N cycloheptane Chemical compound C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 4
- 229930195733 hydrocarbon Natural products 0.000 description 4
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 4
- QWTDNUCVQCZILF-UHFFFAOYSA-N isopentane Chemical compound CCC(C)C QWTDNUCVQCZILF-UHFFFAOYSA-N 0.000 description 4
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 4
- 238000007152 ring opening metathesis polymerisation reaction Methods 0.000 description 4
- 239000000523 sample Substances 0.000 description 4
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- 230000009466 transformation Effects 0.000 description 1
- 238000000844 transformation Methods 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003623 transition metal compounds Chemical class 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 150000008648 triflates Chemical class 0.000 description 1
- MCULRUJILOGHCJ-UHFFFAOYSA-N triisobutylaluminium Chemical compound CC(C)C[Al](CC(C)C)CC(C)C MCULRUJILOGHCJ-UHFFFAOYSA-N 0.000 description 1
- LFXVBWRMVZPLFK-UHFFFAOYSA-N trioctylalumane Chemical compound CCCCCCCC[Al](CCCCCCCC)CCCCCCCC LFXVBWRMVZPLFK-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 230000007306 turnover Effects 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000002025 wood fiber Substances 0.000 description 1
- 150000003738 xylenes Chemical class 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
- 239000004711 α-olefin Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G61/02—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes
- C08G61/04—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes only aliphatic carbon atoms
- C08G61/06—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes only aliphatic carbon atoms prepared by ring-opening of carbocyclic compounds
- C08G61/08—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes only aliphatic carbon atoms prepared by ring-opening of carbocyclic compounds of carbocyclic compounds containing one or more carbon-to-carbon double bonds in the ring
-
- 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
- C08F297/00—Macromolecular compounds obtained by successively polymerising different monomer systems using a catalyst of the ionic or coordination type without deactivating the intermediate polymer
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G61/12—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/30—Monomer units or repeat units incorporating structural elements in the main chain
- C08G2261/33—Monomer units or repeat units incorporating structural elements in the main chain incorporating non-aromatic structural elements in the main chain
- C08G2261/332—Monomer units or repeat units incorporating structural elements in the main chain incorporating non-aromatic structural elements in the main chain containing only carbon atoms
- C08G2261/3324—Monomer units or repeat units incorporating structural elements in the main chain incorporating non-aromatic structural elements in the main chain containing only carbon atoms derived from norbornene
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/30—Monomer units or repeat units incorporating structural elements in the main chain
- C08G2261/33—Monomer units or repeat units incorporating structural elements in the main chain incorporating non-aromatic structural elements in the main chain
- C08G2261/334—Monomer units or repeat units incorporating structural elements in the main chain incorporating non-aromatic structural elements in the main chain containing heteroatoms
- C08G2261/3342—Monomer units or repeat units incorporating structural elements in the main chain incorporating non-aromatic structural elements in the main chain containing heteroatoms derived from cycloolefins containing heteroatoms
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/40—Polymerisation processes
- C08G2261/41—Organometallic coupling reactions
- C08G2261/418—Ring opening metathesis polymerisation [ROMP]
Definitions
- Polyolefin means an oligomer or polymer of two or more olefin mer units and specifically includes oligomers and polymers as defined below.
- An “olefin,” alternatively referred to as “alkene,” is a linear, branched, or cyclic compound of carbon and hydrogen having at least one double bond.
- a “mono-olefin” has one double bond, for example, an alpha, omega, pendant, or internal double bond.
- a “polymer” has two or more of the same or different mer units.
- a “homopolymer” is a polymer having mer units that are the same.
- a “copolymer” is a polymer having two or more mer units that are different from each other.
- a “terpolymer” is a polymer having three mer units that are different from each other.
- the term “different” as used to refer to mer units indicates that the mer units differ from each other by at least one atom or are different isomerically. Accordingly, the definition of copolymer, as used herein, includes terpolymers and the like.
- Ri is represented by the formula (C):
- X is C, N, or O (preferably C or O, preferably C); n is an integer from 1 to 10,000 (preferably from 1 to 5,000, from 1 to 2,500, from 1 to 1,000, from 1 to 500, or from 1 to 50); Cm is a C3 to C40 olefin derived unit (preferably Cm is one or more derived units of propylene, butene, pentene, hexene, heptene, octene, nonene, decene, undecene, dodecene, norbornene, norbornadiene, dicyclopentadiene, cyclopentene, cycloheptene, cyclooctene, cyclooctadiene, cyclododecene, 7-oxanorbornene, 7-oxanorbornadiene, substituted derivatives thereof, and isomers thereof); m is an integer from 2 to 39 (preferably from 2 to 29, preferably from 3 to 19,
- a novel lubricant comprises the polymers produced in this invention, alone or together with one or more other base stocks, including Group I to Group V base stocks with kinematic viscosity (ASTM D445) range from 1.5 cSt to 100 cSt at 100°C to formulate suitable viscosity grades.
- additives of one or more of: thickeners, viscosity index improvers, antioxidants, anti-wear additives, detergent/dispersant/inhibitor packages, and/or anti-rust additives may be added.
- n is an integer from 1 to 10,000;
- a cyclic olefin will undergo a ring opening reaction in the presence of the catalyst at a rate constant k RQ
- the vinyl terminated macromonomer will undergo a cross-metathesis reaction with the ring opened cyclic olefin at a rate constant k ⁇ .
- k CM is greater than or equal to k R0
- the ROCM product is predominantly a monomer, dimer, and/or oligomer. More specifically, when k CM is approximately equal to k R0 , the ROCM product is predominantly a dimer, while when k RQ is greater than ⁇ M , the ROCM product is predominantly higher Mw.
- the process produces the metathesis product (polymers having the formula A disclosed herein) in good yield (greater than 50%).
- the process produces little or no dimerization.
- the extent of dimerization is determined by the comparison of the degree of polymerization (ROCM) as obtained from methods A and B, described in the Examples.
- the degree of ROCM obtained from Method A differs from that obtained from Method B by less than 25%, preferably less than 20%, preferably less than 15%, and most preferably less than 10%.
- Suitable cyclic olefins include, but are not limited to norbornene, norbomadiene, dicyclopentadiene, cyclopentene, cycloheptene, cyclooctene, cyclooctadiene, cyclododecene, 7-oxanorbornene, 7-oxanorbornadiene, and substituted derivatives therefrom.
- the "allyl chain end to vinylidene chain end ratio” is defined to be the ratio of the percentage of allyl chain ends to the percentage of vinylidene chain ends.
- the “allyl chain end to vinylene chain end ratio” is defined to be the ratio of the percentage of allyl chain ends to the percentage of vinylene chain ends.
- M* is a Group 8 metal, preferably Ru or Os, preferably Ru;
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Abstract
L'invention concerne un polymère d'une oléfine cyclique et d'un macromonomère à terminaison vinyle, ainsi que des procédés pour sa préparation.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP12854390.7A EP2785763A4 (fr) | 2011-11-29 | 2012-10-08 | Fonctionnalisation de polymères à terminaison vinyle par métathèse croisée par ouverture de cycle |
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US13/306,263 US8604148B2 (en) | 2011-11-29 | 2011-11-29 | Functionalization of vinyl terminated polymers by ring opening cross metathesis |
| EP12152367 | 2012-01-25 | ||
| PCT/US2012/059191 WO2013081726A1 (fr) | 2011-11-29 | 2012-10-08 | Fonctionnalisation de polymères à terminaison vinyle par métathèse croisée par ouverture de cycle |
| EP12854390.7A EP2785763A4 (fr) | 2011-11-29 | 2012-10-08 | Fonctionnalisation de polymères à terminaison vinyle par métathèse croisée par ouverture de cycle |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| EP2785763A1 true EP2785763A1 (fr) | 2014-10-08 |
| EP2785763A4 EP2785763A4 (fr) | 2015-06-03 |
Family
ID=48535934
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP12854390.7A Withdrawn EP2785763A4 (fr) | 2011-11-29 | 2012-10-08 | Fonctionnalisation de polymères à terminaison vinyle par métathèse croisée par ouverture de cycle |
Country Status (3)
| Country | Link |
|---|---|
| EP (1) | EP2785763A4 (fr) |
| CN (1) | CN103987755B (fr) |
| WO (1) | WO2013081726A1 (fr) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2826802B1 (fr) * | 2012-03-16 | 2021-03-10 | Zeon Corporation | Procédé de production de polymère hydrogéné par métathèse avec ouverture de cycle, et composition de résine |
| CN104003926B (zh) * | 2014-05-30 | 2016-06-15 | 天津大学 | 基于烷基铵盐的侧链型磁性单体、聚合物及其制备方法和应用 |
| EP3546495A1 (fr) * | 2018-03-29 | 2019-10-02 | Evonik Degussa GmbH | Procédé de production de polyalcénamères thermostables |
| WO2022008946A1 (fr) * | 2020-07-08 | 2022-01-13 | Centre National De La Recherche Scientifique | Énantiomères optiquement purs de complexes de ruthénium et leurs utilisations |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6487652A (en) | 1987-09-29 | 1989-03-31 | Toyota Motor Corp | Impact-resistant polypropylene resin composition |
| TW291486B (fr) | 1992-12-17 | 1996-11-21 | Exxon Chemical Patents Inc | |
| US5512635A (en) * | 1993-05-27 | 1996-04-30 | Amoco Corporation | Process for preparing linear monofunctional and telechelic difunctional polymers and compositions obtained thereby |
| US6177464B1 (en) | 1997-03-14 | 2001-01-23 | Sepracor, Inc. | Ring opening metathesis of alkenes |
| EP0921129A1 (fr) * | 1997-12-03 | 1999-06-09 | Studiengesellschaft Kohle mbH | Complexes de ruthénium et d'osmium cationiques hautement actifs pour les réactions de métathèse des oléfines |
| WO2000012572A1 (fr) | 1998-08-26 | 2000-03-09 | Exxon Chemical Patents Inc. | Compositions de polypropylène ramifié |
| WO2002079127A1 (fr) | 2001-03-30 | 2002-10-10 | California Institute Of Technology | Metathese croisee a ouverture du cycle selective de cyclo-olefines |
| ATE384029T1 (de) | 2005-02-22 | 2008-02-15 | Miltitz Aromatics Gmbh | Verfahren und anlage zur durchführung einer ringöffnenden kreuzmetathesereaktion zwischen cyclischen und acyclischen olefinen |
| JPWO2006101069A1 (ja) * | 2005-03-22 | 2008-09-04 | 日本ゼオン株式会社 | 熱可塑性樹脂、その製造方法および成形材料 |
| EP2046719B1 (fr) | 2006-07-12 | 2013-09-04 | Elevance Renewable Sciences, Inc. | Réaction de métathèse par ouverture de cycle d'oléfines cycliques avec des huiles végétales et similaires |
| JP5666902B2 (ja) * | 2007-05-23 | 2015-02-12 | ビーエーエスエフ ソシエタス・ヨーロピアＢａｓｆ Ｓｅ | 反応性基を有するイソタクチックポリスチレン |
| CN102234364A (zh) * | 2010-04-30 | 2011-11-09 | 青岛伊科思新材料股份有限公司 | 聚(环戊二烯-双环戊二烯)共聚物及其合成方法 |
-
2012
- 2012-10-08 WO PCT/US2012/059191 patent/WO2013081726A1/fr active Application Filing
- 2012-10-08 CN CN201280056901.1A patent/CN103987755B/zh not_active Expired - Fee Related
- 2012-10-08 EP EP12854390.7A patent/EP2785763A4/fr not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| EP2785763A4 (fr) | 2015-06-03 |
| WO2013081726A1 (fr) | 2013-06-06 |
| CN103987755A (zh) | 2014-08-13 |
| CN103987755B (zh) | 2016-08-17 |
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