RU2623223C2 - Амидоэфирный внутренний донор электронов и способ - Google Patents
Амидоэфирный внутренний донор электронов и способ Download PDFInfo
- Publication number
- RU2623223C2 RU2623223C2 RU2012141060A RU2012141060A RU2623223C2 RU 2623223 C2 RU2623223 C2 RU 2623223C2 RU 2012141060 A RU2012141060 A RU 2012141060A RU 2012141060 A RU2012141060 A RU 2012141060A RU 2623223 C2 RU2623223 C2 RU 2623223C2
- Authority
- RU
- Russia
- Prior art keywords
- composition
- procatalytic
- benzoate
- component
- electron donor
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 58
- 239000000203 mixture Substances 0.000 claims abstract description 155
- 229920000642 polymer Polymers 0.000 claims abstract description 76
- 150000001336 alkenes Chemical class 0.000 claims abstract description 69
- 239000003054 catalyst Substances 0.000 claims abstract description 51
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims abstract description 43
- 239000011777 magnesium Substances 0.000 claims abstract description 41
- 239000010936 titanium Substances 0.000 claims abstract description 37
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 36
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims abstract description 36
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims abstract description 35
- 229910052749 magnesium Inorganic materials 0.000 claims abstract description 34
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims abstract description 33
- 229910052719 titanium Inorganic materials 0.000 claims abstract description 33
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims abstract description 31
- 230000003197 catalytic effect Effects 0.000 claims abstract description 29
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims abstract description 27
- 230000002140 halogenating effect Effects 0.000 claims abstract description 25
- 239000011541 reaction mixture Substances 0.000 claims abstract description 22
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 21
- 238000004519 manufacturing process Methods 0.000 claims abstract description 21
- 230000000694 effects Effects 0.000 claims abstract description 20
- -1 amide ester Chemical class 0.000 claims description 118
- 239000002243 precursor Substances 0.000 claims description 63
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 39
- 150000001875 compounds Chemical class 0.000 claims description 31
- MTZQAGJQAFMTAQ-UHFFFAOYSA-N ethyl benzoate Chemical compound CCOC(=O)C1=CC=CC=C1 MTZQAGJQAFMTAQ-UHFFFAOYSA-N 0.000 claims description 30
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 17
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 claims description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims description 15
- 239000001257 hydrogen Substances 0.000 claims description 15
- 239000012035 limiting reagent Substances 0.000 claims description 13
- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- 229910052736 halogen Inorganic materials 0.000 claims description 10
- 150000002367 halogens Chemical class 0.000 claims description 10
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 9
- 229910001629 magnesium chloride Inorganic materials 0.000 claims description 7
- 239000011954 Ziegler–Natta catalyst Substances 0.000 claims description 5
- 150000007942 carboxylates Chemical class 0.000 claims description 5
- 150000001733 carboxylic acid esters Chemical class 0.000 claims description 5
- 229920001296 polysiloxane Polymers 0.000 claims description 5
- NWBJLLHFWVYOHR-UHFFFAOYSA-N 1-methoxypropan-2-yl benzoate Chemical compound COCC(C)OC(=O)C1=CC=CC=C1 NWBJLLHFWVYOHR-UHFFFAOYSA-N 0.000 claims description 4
- 150000005690 diesters Chemical class 0.000 claims description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 4
- 150000001412 amines Chemical class 0.000 claims description 3
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 3
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 claims description 3
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 claims 1
- 238000005658 halogenation reaction Methods 0.000 abstract description 19
- 230000026030 halogenation Effects 0.000 abstract description 18
- 230000008569 process Effects 0.000 abstract description 11
- 239000000126 substance Substances 0.000 abstract description 11
- 238000009826 distribution Methods 0.000 abstract description 7
- 239000012018 catalyst precursor Substances 0.000 abstract 2
- 238000001914 filtration Methods 0.000 description 25
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 18
- 239000007787 solid Substances 0.000 description 18
- 125000003118 aryl group Chemical group 0.000 description 16
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 15
- 125000000217 alkyl group Chemical group 0.000 description 14
- 239000000047 product Substances 0.000 description 14
- 239000000243 solution Substances 0.000 description 13
- 238000003756 stirring Methods 0.000 description 13
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 12
- 239000005977 Ethylene Substances 0.000 description 12
- 239000000178 monomer Substances 0.000 description 12
- 239000012071 phase Substances 0.000 description 12
- 239000012046 mixed solvent Substances 0.000 description 11
- JWCYDYZLEAQGJJ-UHFFFAOYSA-N dicyclopentyl(dimethoxy)silane Chemical compound C1CCCC1[Si](OC)(OC)C1CCCC1 JWCYDYZLEAQGJJ-UHFFFAOYSA-N 0.000 description 10
- 230000003993 interaction Effects 0.000 description 10
- HIQIXEFWDLTDED-UHFFFAOYSA-N 4-hydroxy-1-piperidin-4-ylpyrrolidin-2-one Chemical compound O=C1CC(O)CN1C1CCNCC1 HIQIXEFWDLTDED-UHFFFAOYSA-N 0.000 description 9
- 238000005481 NMR spectroscopy Methods 0.000 description 9
- 125000004429 atom Chemical group 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 9
- 125000005842 heteroatom Chemical group 0.000 description 9
- 239000007788 liquid Substances 0.000 description 9
- 229910052751 metal Inorganic materials 0.000 description 9
- 239000002184 metal Substances 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 8
- 125000003710 aryl alkyl group Chemical group 0.000 description 8
- 230000008901 benefit Effects 0.000 description 8
- 229920001577 copolymer Polymers 0.000 description 8
- 229910052760 oxygen Inorganic materials 0.000 description 8
- NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 description 7
- 238000000354 decomposition reaction Methods 0.000 description 7
- JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 description 7
- 229930195733 hydrocarbon Natural products 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- 239000008096 xylene Substances 0.000 description 7
- 239000004215 Carbon black (E152) Substances 0.000 description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 229920001400 block copolymer Polymers 0.000 description 6
- 239000000460 chlorine Substances 0.000 description 6
- 230000000875 corresponding effect Effects 0.000 description 6
- 239000000706 filtrate Substances 0.000 description 6
- 125000000524 functional group Chemical group 0.000 description 6
- 150000002430 hydrocarbons Chemical class 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- HRAQMGWTPNOILP-UHFFFAOYSA-N 4-Ethoxy ethylbenzoate Chemical compound CCOC(=O)C1=CC=C(OCC)C=C1 HRAQMGWTPNOILP-UHFFFAOYSA-N 0.000 description 5
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 5
- 125000003545 alkoxy group Chemical group 0.000 description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 5
- 229910052799 carbon Inorganic materials 0.000 description 5
- 229910052801 chlorine Inorganic materials 0.000 description 5
- 150000004820 halides Chemical group 0.000 description 5
- 150000008282 halocarbons Chemical class 0.000 description 5
- 239000001301 oxygen Substances 0.000 description 5
- 239000002245 particle Substances 0.000 description 5
- 229920001384 propylene homopolymer Polymers 0.000 description 5
- 125000001424 substituent group Chemical group 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- UBOXGVDOUJQMTN-UHFFFAOYSA-N 1,1,2-trichloroethane Chemical compound ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 4
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 4
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- 125000002877 alkyl aryl group Chemical group 0.000 description 4
- 229910052782 aluminium Inorganic materials 0.000 description 4
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 4
- 150000001408 amides Chemical class 0.000 description 4
- 229910052794 bromium Inorganic materials 0.000 description 4
- 229940125904 compound 1 Drugs 0.000 description 4
- VHPUZTHRFWIGAW-UHFFFAOYSA-N dimethoxy-di(propan-2-yl)silane Chemical compound CO[Si](OC)(C(C)C)C(C)C VHPUZTHRFWIGAW-UHFFFAOYSA-N 0.000 description 4
- 125000005843 halogen group Chemical group 0.000 description 4
- 239000005457 ice water Substances 0.000 description 4
- XDKQUSKHRIUJEO-UHFFFAOYSA-N magnesium;ethanolate Chemical group [Mg+2].CC[O-].CC[O-] XDKQUSKHRIUJEO-UHFFFAOYSA-N 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 230000000737 periodic effect Effects 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- 238000010998 test method Methods 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- 229910052723 transition metal Inorganic materials 0.000 description 4
- 150000003624 transition metals Chemical class 0.000 description 4
- NBXZNTLFQLUFES-UHFFFAOYSA-N triethoxy(propyl)silane Chemical compound CCC[Si](OCC)(OCC)OCC NBXZNTLFQLUFES-UHFFFAOYSA-N 0.000 description 4
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- BOTDANWDWHJENH-UHFFFAOYSA-N Tetraethyl orthosilicate Chemical compound CCO[Si](OCC)(OCC)OCC BOTDANWDWHJENH-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 125000003342 alkenyl group Chemical group 0.000 description 3
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 3
- 238000005660 chlorination reaction Methods 0.000 description 3
- 125000000753 cycloalkyl group Chemical group 0.000 description 3
- SJJCABYOVIHNPZ-UHFFFAOYSA-N cyclohexyl-dimethoxy-methylsilane Chemical compound CO[Si](C)(OC)C1CCCCC1 SJJCABYOVIHNPZ-UHFFFAOYSA-N 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 229910052740 iodine Inorganic materials 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
- 235000019341 magnesium sulphate Nutrition 0.000 description 3
- 239000000155 melt Substances 0.000 description 3
- 229910052698 phosphorus Inorganic materials 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 229910052710 silicon Inorganic materials 0.000 description 3
- 229910052717 sulfur Inorganic materials 0.000 description 3
- VOITXYVAKOUIBA-UHFFFAOYSA-N triethylaluminium Chemical compound CC[Al](CC)CC VOITXYVAKOUIBA-UHFFFAOYSA-N 0.000 description 3
- 125000006659 (C1-C20) hydrocarbyl group Chemical group 0.000 description 2
- ZGEGCLOFRBLKSE-UHFFFAOYSA-N 1-Heptene Chemical compound CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 description 2
- AFFLGGQVNFXPEV-UHFFFAOYSA-N 1-decene Chemical compound CCCCCCCCC=C AFFLGGQVNFXPEV-UHFFFAOYSA-N 0.000 description 2
- CRSBERNSMYQZNG-UHFFFAOYSA-N 1-dodecene Chemical compound CCCCCCCCCCC=C CRSBERNSMYQZNG-UHFFFAOYSA-N 0.000 description 2
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 2
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 2
- RKMGAJGJIURJSJ-UHFFFAOYSA-N 2,2,6,6-tetramethylpiperidine Chemical compound CC1(C)CCCC(C)(C)N1 RKMGAJGJIURJSJ-UHFFFAOYSA-N 0.000 description 2
- WSSSPWUEQFSQQG-UHFFFAOYSA-N 4-methyl-1-pentene Chemical compound CC(C)CC=C WSSSPWUEQFSQQG-UHFFFAOYSA-N 0.000 description 2
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- FHUODBDRWMIBQP-UHFFFAOYSA-N Ethyl p-anisate Chemical compound CCOC(=O)C1=CC=C(OC)C=C1 FHUODBDRWMIBQP-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical class CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 125000002015 acyclic group Chemical group 0.000 description 2
- 238000005917 acylation reaction Methods 0.000 description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
- 150000001414 amino alcohols Chemical class 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- 238000000149 argon plasma sintering Methods 0.000 description 2
- 150000001558 benzoic acid derivatives Chemical class 0.000 description 2
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical class ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 2
- 239000012267 brine Substances 0.000 description 2
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 2
- 229910052804 chromium Inorganic materials 0.000 description 2
- 239000011651 chromium Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 125000000392 cycloalkenyl group Chemical group 0.000 description 2
- 238000013480 data collection Methods 0.000 description 2
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 229920001971 elastomer Polymers 0.000 description 2
- WHTXVXOOSUKFJP-UHFFFAOYSA-N ethyl 2-cyano-3-methyl-2-propan-2-ylbutanoate Chemical compound CCOC(=O)C(C#N)(C(C)C)C(C)C WHTXVXOOSUKFJP-UHFFFAOYSA-N 0.000 description 2
- CTUUCCARKOOGPO-UHFFFAOYSA-N ethyl 2-cyano-4-methyl-2-(2-methylpropyl)pentanoate Chemical compound CCOC(=O)C(CC(C)C)(CC(C)C)C#N CTUUCCARKOOGPO-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 125000000592 heterocycloalkyl group Chemical group 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 239000012280 lithium aluminium hydride Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 2
- 239000010452 phosphate Substances 0.000 description 2
- 125000003367 polycyclic group Chemical group 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 229920001155 polypropylene Polymers 0.000 description 2
- 238000010926 purge Methods 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 238000000518 rheometry Methods 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
- 125000000547 substituted alkyl group Chemical group 0.000 description 2
- 150000003900 succinic acid esters Chemical class 0.000 description 2
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 2
- 150000003457 sulfones Chemical class 0.000 description 2
- 150000003462 sulfoxides Chemical class 0.000 description 2
- 229920001897 terpolymer Polymers 0.000 description 2
- HQYALQRYBUJWDH-UHFFFAOYSA-N trimethoxy(propyl)silane Chemical compound CCC[Si](OC)(OC)OC HQYALQRYBUJWDH-UHFFFAOYSA-N 0.000 description 2
- 229910052720 vanadium Inorganic materials 0.000 description 2
- 150000003738 xylenes Chemical class 0.000 description 2
- FTSXVYQZLNPTCM-UHFFFAOYSA-N (3-benzoyloxy-2,2,4-trimethylpentyl) benzoate Chemical compound C=1C=CC=CC=1C(=O)OCC(C)(C)C(C(C)C)OC(=O)C1=CC=CC=C1 FTSXVYQZLNPTCM-UHFFFAOYSA-N 0.000 description 1
- 125000006652 (C3-C12) cycloalkyl group Chemical group 0.000 description 1
- ITYXDCHVYRDZDC-UHFFFAOYSA-N 1,1,1,2-tetrachlorooctane Chemical compound CCCCCCC(Cl)C(Cl)(Cl)Cl ITYXDCHVYRDZDC-UHFFFAOYSA-N 0.000 description 1
- DAIRXERGRJFMSC-UHFFFAOYSA-N 1,1,2-trichlorocyclohexane Chemical compound ClC1CCCCC1(Cl)Cl DAIRXERGRJFMSC-UHFFFAOYSA-N 0.000 description 1
- PAAZPARNPHGIKF-UHFFFAOYSA-N 1,2-dibromoethane Chemical compound BrCCBr PAAZPARNPHGIKF-UHFFFAOYSA-N 0.000 description 1
- GHKFGRVGAQYZNT-UHFFFAOYSA-N 1,2-dibutoxybenzene Chemical compound CCCCOC1=CC=CC=C1OCCCC GHKFGRVGAQYZNT-UHFFFAOYSA-N 0.000 description 1
- QZYDOKBVZJLQCK-UHFFFAOYSA-N 1,2-diethoxybenzene Chemical compound CCOC1=CC=CC=C1OCC QZYDOKBVZJLQCK-UHFFFAOYSA-N 0.000 description 1
- GLVIMRBXUNCALJ-UHFFFAOYSA-N 1-ethoxy-2-pentoxybenzene Chemical compound CCCCCOC1=CC=CC=C1OCC GLVIMRBXUNCALJ-UHFFFAOYSA-N 0.000 description 1
- CPXKOSDOYBLVCD-UHFFFAOYSA-N 2-(aminomethyl)-3-methyl-2-propan-2-ylbutan-1-ol Chemical compound CC(C)C(CN)(CO)C(C)C CPXKOSDOYBLVCD-UHFFFAOYSA-N 0.000 description 1
- GEBNLXZFNUZDPO-UHFFFAOYSA-N 2-(aminomethyl)-4-methyl-2-(2-methylpropyl)pentan-1-ol Chemical compound CC(C)CC(CN)(CO)CC(C)C GEBNLXZFNUZDPO-UHFFFAOYSA-N 0.000 description 1
- RGHIYOCUMCUWAQ-UHFFFAOYSA-N 3,3-bis(methoxymethyl)-2,5-dimethylhexane Chemical compound COCC(COC)(CC(C)C)C(C)C RGHIYOCUMCUWAQ-UHFFFAOYSA-N 0.000 description 1
- FICAQKBMCKEFDI-UHFFFAOYSA-N 3,5-dimethyl-1,2-oxazole Chemical compound CC=1C=C(C)ON=1 FICAQKBMCKEFDI-UHFFFAOYSA-N 0.000 description 1
- PVWCLOAAEFMTLH-UHFFFAOYSA-N 4,4-bis(methoxymethyl)-2,6-dimethylheptane Chemical compound COCC(COC)(CC(C)C)CC(C)C PVWCLOAAEFMTLH-UHFFFAOYSA-N 0.000 description 1
- RTFVYTOTESLFBG-UHFFFAOYSA-N 4-aminopentan-2-ol Chemical compound CC(N)CC(C)O RTFVYTOTESLFBG-UHFFFAOYSA-N 0.000 description 1
- COQGNYVGVVVZGY-UHFFFAOYSA-N 4-benzamidopentan-2-yl benzoate Chemical compound C=1C=CC=CC=1C(=O)NC(C)CC(C)OC(=O)C1=CC=CC=C1 COQGNYVGVVVZGY-UHFFFAOYSA-N 0.000 description 1
- GXFABAKJWJZNCZ-UHFFFAOYSA-N 4-chloro-2-[3-[(4-chlorobenzoyl)amino]-2,2-dimethylpropyl]benzoic acid Chemical compound CC(C)(CC1=C(C=CC(=C1)Cl)C(=O)O)CNC(=O)C2=CC=C(C=C2)Cl GXFABAKJWJZNCZ-UHFFFAOYSA-N 0.000 description 1
- IBEWZIJJGAGHGX-UHFFFAOYSA-N 4-fluoro-2-[3-[(4-fluorobenzoyl)amino]-2,2-dimethylpropyl]benzoic acid Chemical compound CC(C)(CC1=C(C=CC(=C1)F)C(=O)O)CNC(=O)C2=CC=C(C=C2)F IBEWZIJJGAGHGX-UHFFFAOYSA-N 0.000 description 1
- ZWINORFLMHROGF-UHFFFAOYSA-N 9,9-bis(methoxymethyl)fluorene Chemical compound C1=CC=C2C(COC)(COC)C3=CC=CC=C3C2=C1 ZWINORFLMHROGF-UHFFFAOYSA-N 0.000 description 1
- 229910000838 Al alloy Inorganic materials 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- UQGDQQJDWICEAN-UHFFFAOYSA-N CC(C)(CC1=CC=CC=C1C(=O)O)CNC(=O)C2=CC=CC=C2 Chemical compound CC(C)(CC1=CC=CC=C1C(=O)O)CNC(=O)C2=CC=CC=C2 UQGDQQJDWICEAN-UHFFFAOYSA-N 0.000 description 1
- UKIHGLQQNZCGQT-UHFFFAOYSA-N CC(C)C(CC1=CC=CC=C1C(=O)O)(CNC(=O)C2=CC=CC=C2)C(C)C Chemical compound CC(C)C(CC1=CC=CC=C1C(=O)O)(CNC(=O)C2=CC=CC=C2)C(C)C UKIHGLQQNZCGQT-UHFFFAOYSA-N 0.000 description 1
- ZFSSRXIEFGQEPZ-UHFFFAOYSA-N CC(C)CC(CC1=CC=CC=C1C(=O)O)(CC(C)C)CNC(=O)C2=CC=CC=C2 Chemical compound CC(C)CC(CC1=CC=CC=C1C(=O)O)(CC(C)C)CNC(=O)C2=CC=CC=C2 ZFSSRXIEFGQEPZ-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical class CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- 238000000333 X-ray scattering Methods 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 238000005054 agglomeration Methods 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 1
- 150000004996 alkyl benzenes Chemical class 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 125000000304 alkynyl group Chemical group 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 229910052790 beryllium Inorganic materials 0.000 description 1
- ATBAMAFKBVZNFJ-UHFFFAOYSA-N beryllium atom Chemical compound [Be] ATBAMAFKBVZNFJ-UHFFFAOYSA-N 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 238000000071 blow moulding Methods 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 238000012662 bulk polymerization Methods 0.000 description 1
- XSIFPSYPOVKYCO-UHFFFAOYSA-N butyl benzoate Chemical compound CCCCOC(=O)C1=CC=CC=C1 XSIFPSYPOVKYCO-UHFFFAOYSA-N 0.000 description 1
- 229910052793 cadmium Inorganic materials 0.000 description 1
- BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 description 1
- CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical class [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 239000012986 chain transfer agent Substances 0.000 description 1
- 239000012320 chlorinating reagent Substances 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 230000006835 compression Effects 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 230000003750 conditioning effect Effects 0.000 description 1
- 230000002596 correlated effect Effects 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 125000001485 cycloalkadienyl group Chemical group 0.000 description 1
- 238000013500 data storage Methods 0.000 description 1
- FJBFPHVGVWTDIP-UHFFFAOYSA-N dibromomethane Chemical compound BrCBr FJBFPHVGVWTDIP-UHFFFAOYSA-N 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- 150000004816 dichlorobenzenes Chemical class 0.000 description 1
- UMNKXPULIDJLSU-UHFFFAOYSA-N dichlorofluoromethane Chemical compound FC(Cl)Cl UMNKXPULIDJLSU-UHFFFAOYSA-N 0.000 description 1
- 229940099364 dichlorofluoromethane Drugs 0.000 description 1
- AVLHXEDOBYYTGV-UHFFFAOYSA-N diethyl 2,3-bis(2-methylpropyl)butanedioate Chemical compound CCOC(=O)C(CC(C)C)C(CC(C)C)C(=O)OCC AVLHXEDOBYYTGV-UHFFFAOYSA-N 0.000 description 1
- WGFNXLQURMLAGC-UHFFFAOYSA-N diethyl 2,3-di(propan-2-yl)butanedioate Chemical compound CCOC(=O)C(C(C)C)C(C(C)C)C(=O)OCC WGFNXLQURMLAGC-UHFFFAOYSA-N 0.000 description 1
- JJQZDUKDJDQPMQ-UHFFFAOYSA-N dimethoxy(dimethyl)silane Chemical compound CO[Si](C)(C)OC JJQZDUKDJDQPMQ-UHFFFAOYSA-N 0.000 description 1
- WSBCVSVJXVVUFU-UHFFFAOYSA-N dimethoxy-bis(trimethylsilylmethyl)silane Chemical compound C[Si](C)(C)C[Si](OC)(C[Si](C)(C)C)OC WSBCVSVJXVVUFU-UHFFFAOYSA-N 0.000 description 1
- YQGOWXYZDLJBFL-UHFFFAOYSA-N dimethoxysilane Chemical compound CO[SiH2]OC YQGOWXYZDLJBFL-UHFFFAOYSA-N 0.000 description 1
- POULHZVOKOAJMA-UHFFFAOYSA-M dodecanoate Chemical compound CCCCCCCCCCCC([O-])=O POULHZVOKOAJMA-UHFFFAOYSA-M 0.000 description 1
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical class CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 1
- 229940069096 dodecene Drugs 0.000 description 1
- 238000001508 electron transmission spectroscopy Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- ZIUSEGSNTOUIPT-UHFFFAOYSA-N ethyl 2-cyanoacetate Chemical compound CCOC(=O)CC#N ZIUSEGSNTOUIPT-UHFFFAOYSA-N 0.000 description 1
- TVODIPKBEMSROH-UHFFFAOYSA-N ethyl 3-methoxy-2-methylpropanoate Chemical compound CCOC(=O)C(C)COC TVODIPKBEMSROH-UHFFFAOYSA-N 0.000 description 1
- RWBYCMPOFNRISR-UHFFFAOYSA-N ethyl 4-chlorobenzoate Chemical compound CCOC(=O)C1=CC=C(Cl)C=C1 RWBYCMPOFNRISR-UHFFFAOYSA-N 0.000 description 1
- 229920001038 ethylene copolymer Polymers 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000003818 flash chromatography Methods 0.000 description 1
- 238000004401 flow injection analysis Methods 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 238000012685 gas phase polymerization Methods 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 229910052735 hafnium Inorganic materials 0.000 description 1
- 125000001188 haloalkyl group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 229940070765 laurate Drugs 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- 150000002680 magnesium Chemical class 0.000 description 1
- IVAUOVGUCLHZTN-UHFFFAOYSA-L magnesium;benzoate;chloride Chemical group [Mg+2].[Cl-].[O-]C(=O)C1=CC=CC=C1 IVAUOVGUCLHZTN-UHFFFAOYSA-L 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 230000007257 malfunction Effects 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- 229910001507 metal halide Inorganic materials 0.000 description 1
- 150000005309 metal halides Chemical class 0.000 description 1
- 150000002737 metalloid compounds Chemical class 0.000 description 1
- LYLUAHKXJUQFDG-UHFFFAOYSA-N methyl 3-methoxy-2-methylpropanoate Chemical compound COCC(C)C(=O)OC LYLUAHKXJUQFDG-UHFFFAOYSA-N 0.000 description 1
- BDJSOPWXYLFTNW-UHFFFAOYSA-N methyl 3-methoxypropanoate Chemical compound COCCC(=O)OC BDJSOPWXYLFTNW-UHFFFAOYSA-N 0.000 description 1
- RNHXTCZZACTEMK-UHFFFAOYSA-N methyl 4-ethoxybenzoate Chemical compound CCOC1=CC=C(C(=O)OC)C=C1 RNHXTCZZACTEMK-UHFFFAOYSA-N 0.000 description 1
- BPRXBIQOOGJPER-UHFFFAOYSA-N methyl 4-methoxybicyclo[2.2.1]hept-2-ene-5-carboxylate Chemical compound C1C2(OC)C(C(=O)OC)CC1C=C2 BPRXBIQOOGJPER-UHFFFAOYSA-N 0.000 description 1
- 229940095102 methyl benzoate Drugs 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 150000002763 monocarboxylic acids Chemical class 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 229910052758 niobium Inorganic materials 0.000 description 1
- ZWLPBLYKEWSWPD-UHFFFAOYSA-M o-toluate Chemical compound CC1=CC=CC=C1C([O-])=O ZWLPBLYKEWSWPD-UHFFFAOYSA-M 0.000 description 1
- AUONHKJOIZSQGR-UHFFFAOYSA-N oxophosphane Chemical compound P=O AUONHKJOIZSQGR-UHFFFAOYSA-N 0.000 description 1
- 150000002942 palmitic acid derivatives Chemical class 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 description 1
- ACVYVLVWPXVTIT-UHFFFAOYSA-M phosphinate Chemical compound [O-][PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-M 0.000 description 1
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- 125000005498 phthalate group Chemical class 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
- 229920005646 polycarboxylate Polymers 0.000 description 1
- 229920002959 polymer blend Polymers 0.000 description 1
- 239000002685 polymerization catalyst Substances 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 238000004886 process control Methods 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 229910052706 scandium Inorganic materials 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 125000005346 substituted cycloalkyl group Chemical group 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229920006029 tetra-polymer Polymers 0.000 description 1
- TUNFSRHWOTWDNC-UHFFFAOYSA-N tetradecanoic acid Chemical class CCCCCCCCCCCCCC(O)=O TUNFSRHWOTWDNC-UHFFFAOYSA-N 0.000 description 1
- 238000003856 thermoforming Methods 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 150000003609 titanium compounds Chemical class 0.000 description 1
- DQWPFSLDHJDLRL-UHFFFAOYSA-N triethyl phosphate Chemical compound CCOP(=O)(OCC)OCC DQWPFSLDHJDLRL-UHFFFAOYSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- ORYGRKHDLWYTKX-UHFFFAOYSA-N trihexylalumane Chemical compound CCCCCC[Al](CCCCCC)CCCCCC ORYGRKHDLWYTKX-UHFFFAOYSA-N 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
- WVLBCYQITXONBZ-UHFFFAOYSA-N trimethyl phosphate Chemical compound COP(=O)(OC)OC WVLBCYQITXONBZ-UHFFFAOYSA-N 0.000 description 1
- JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical compound C[Al](C)C JLTRXTDYQLMHGR-UHFFFAOYSA-N 0.000 description 1
- QOPBTFMUVTXWFF-UHFFFAOYSA-N tripropyl phosphite Chemical compound CCCOP(OCCC)OCCC QOPBTFMUVTXWFF-UHFFFAOYSA-N 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 229940035658 visco-gel Drugs 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052726 zirconium Inorganic materials 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
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F4/00—Polymerisation catalysts
- C08F4/42—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors
- C08F4/44—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides
- C08F4/60—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides together with refractory metals, iron group metals, platinum group metals, manganese, rhenium technetium or compounds thereof
- C08F4/62—Refractory metals or compounds thereof
- C08F4/64—Titanium, zirconium, hafnium or compounds thereof
- C08F4/65—Pretreating the metal or compound covered by group C08F4/64 before the final contacting with the metal or compound covered by group C08F4/44
- C08F4/651—Pretreating with non-metals or metal-free compounds
-
- 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
- C08F10/06—Propene
-
- 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
- C08F4/00—Polymerisation catalysts
- C08F4/42—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors
- C08F4/44—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides
- C08F4/60—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides together with refractory metals, iron group metals, platinum group metals, manganese, rhenium technetium or compounds thereof
- C08F4/62—Refractory metals or compounds thereof
- C08F4/64—Titanium, zirconium, hafnium or compounds thereof
- C08F4/65—Pretreating the metal or compound covered by group C08F4/64 before the final contacting with the metal or compound covered by group C08F4/44
- C08F4/652—Pretreating with metals or metal-containing compounds
- C08F4/654—Pretreating with metals or metal-containing compounds with magnesium or compounds thereof
-
- 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
- C08F110/06—Propene
-
- 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
- C08F2500/00—Characteristics or properties of obtained polyolefins; Use thereof
- C08F2500/04—Broad molecular weight distribution, i.e. Mw/Mn > 6
-
- 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
- C08F2500/00—Characteristics or properties of obtained polyolefins; Use thereof
- C08F2500/18—Bulk density
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US30854310P | 2010-02-26 | 2010-02-26 | |
| US61/308,543 | 2010-02-26 | ||
| PCT/US2011/026036 WO2011106500A1 (en) | 2010-02-26 | 2011-02-24 | Amide ester internal electron and process |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU2012141060A RU2012141060A (ru) | 2014-04-10 |
| RU2623223C2 true RU2623223C2 (ru) | 2017-06-23 |
Family
ID=44209862
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2012141060A RU2623223C2 (ru) | 2010-02-26 | 2011-02-24 | Амидоэфирный внутренний донор электронов и способ |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US8551903B2 (https=) |
| EP (1) | EP2539379B1 (https=) |
| JP (1) | JP5779193B2 (https=) |
| KR (1) | KR101824747B1 (https=) |
| CN (1) | CN102918068B (https=) |
| BR (1) | BR112012021519B1 (https=) |
| MY (1) | MY181149A (https=) |
| RU (1) | RU2623223C2 (https=) |
| SG (1) | SG183813A1 (https=) |
| WO (1) | WO2011106500A1 (https=) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2850411C1 (ru) * | 2020-10-15 | 2025-11-11 | Чайна Петролеум Энд Кемикал Корпорейшн | Пропилен-бутеновый сополимер, способ его получения и его применение |
Families Citing this family (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2723780B1 (en) | 2011-06-24 | 2017-04-26 | Basell Poliolefine Italia S.r.l. | Catalyst components for the polymerization of olefins |
| IN2014DN10763A (https=) * | 2012-06-29 | 2015-09-04 | Saudi Basic Ind Corp | |
| BR112015017749B1 (pt) * | 2013-01-31 | 2021-01-12 | Saudi Basic Industries Corporation | composição de catalisador para a polimerização de olefinas, seu processo para a preparação e seu uso, sistema de catalisador e processo de produção de uma poliolefina |
| US9790291B2 (en) * | 2013-03-14 | 2017-10-17 | Formosa Plastics Corporation, Usa | Non-phthalate compounds as electron donors for polyolefin catalysts |
| EP3044239B9 (en) * | 2013-09-09 | 2019-08-28 | Basell Poliolefine Italia S.r.l. | Catalyst components for the polymerization of olefins |
| BR112016013951B1 (pt) * | 2013-12-20 | 2022-02-22 | Sabic Global Technologies B.V. | Processo para a preparação de um pró-catalisador para polimerização de uma olefina, uso de uma benzamida, composição de catalisador, pró-catalisador e processo para a preparação de poliolefinas compreendendo o mesmo |
| KR102365377B1 (ko) | 2013-12-20 | 2022-02-21 | 사우디 베이식 인더스트리즈 코포레이션 | 올레핀 중합용 촉매 시스템 |
| KR20160102018A (ko) | 2013-12-20 | 2016-08-26 | 사우디 베이식 인더스트리즈 코포레이션 | 올레핀 중합용 전구 촉매 |
| US10059656B2 (en) | 2013-12-20 | 2018-08-28 | Sabic Global Technologies B.V. | Catalyst composition for polymerization of olefins |
| EP3083723B1 (en) | 2013-12-20 | 2022-01-19 | Saudi Basic Industries Corporation | Catalyst system for polymerisation of an olefin |
| EP3083722B1 (en) | 2013-12-20 | 2021-11-10 | Saudi Basic Industries Corporation | Catalyst system for polymerisation of an olefin |
| MX2016008039A (es) * | 2013-12-20 | 2017-05-12 | Saudi Basic Ind Corp | Sistema catalizador para polimerizacion de una olefina. |
| EP3149054A1 (en) * | 2014-06-02 | 2017-04-05 | SABIC Global Technologies B.V. | Procatalyst for polymerization of olefins comprising a monoester and an amidobenzoate internal donor |
| US9593184B2 (en) * | 2014-10-28 | 2017-03-14 | Formosa Plastics Corporation, Usa | Oxalic acid diamides as modifiers for polyolefin catalysts |
| KR101872195B1 (ko) | 2015-03-10 | 2018-06-28 | 바셀 폴리올레핀 이탈리아 에스.알.엘 | 올레핀 중합용 촉매 성분 |
| WO2017079940A1 (zh) * | 2015-11-12 | 2017-05-18 | 营口市向阳催化剂有限责任公司 | 含有磷酸酯类外给电子体的聚丙烯聚合用催化体系及其应用 |
| US10836847B2 (en) | 2015-12-02 | 2020-11-17 | Sabic Global Technologies B.V. | Procatalyst for polymerization of olefins |
| WO2017093132A1 (en) * | 2015-12-02 | 2017-06-08 | Sabic Global Technologies B.V. | Process for preparing a procatalyst for polymerization of olefins |
| EA038377B1 (ru) * | 2015-12-02 | 2021-08-18 | Сабик Глоубл Текнолоджиз Б.В. | Прокатализатор для полимеризации олефинов |
| EP3697755B1 (en) * | 2017-10-20 | 2021-09-15 | SABIC Global Technologies B.V. | Novel synthesis method for the preparation of dibenzoate compounds, such as 4-[benzoyl(methyl)amino]pentane-2-yl dibenzoate |
| JP7130301B2 (ja) | 2018-05-04 | 2022-09-05 | エルジー・ケム・リミテッド | オレフィン系共重合体及びその製造方法 |
| JPWO2024204845A1 (https=) * | 2023-03-30 | 2024-10-03 | ||
| WO2024204847A1 (ja) * | 2023-03-30 | 2024-10-03 | 三井化学株式会社 | アミド化合物 |
| WO2024204846A1 (ja) * | 2023-03-31 | 2024-10-03 | 三井化学株式会社 | カルバメート化合物 |
| KR20250139411A (ko) * | 2023-03-31 | 2025-09-23 | 미쓰이 가가쿠 가부시키가이샤 | 고체상 타이타늄 촉매 성분, 올레핀 중합용 촉매, 올레핀의 중합 방법 |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20030064882A1 (en) * | 2001-05-29 | 2003-04-03 | Kilty Peter A. | Olefin polymerization catalyst compositions and method of preparation |
| WO2006110234A2 (en) * | 2005-03-08 | 2006-10-19 | Ineos Usa Llc | Propylene polymer catalyst donor component |
| RU2298014C2 (ru) * | 2002-02-07 | 2007-04-27 | Чайна Петролеум Энд Кемикал Корпорейшн | Твердый каталитический компонент для полимеризации олефинов, содержащий его катализатор и его применение |
| CN101104589A (zh) * | 2006-07-13 | 2008-01-16 | 中国石油化工股份有限公司 | 用于制备烯烃聚合催化剂的氨酯化合物 |
| CN101104656A (zh) * | 2006-07-13 | 2008-01-16 | 中国石油化工股份有限公司 | 用于烯烃聚合反应的催化剂组分及其催化剂 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1141093A (en) * | 1979-05-17 | 1983-02-08 | Brian L. Goodall | Olefin polymerization catalyst compositions and a process for the polymerization of olefins employing such compositions |
| JPS5665008A (en) * | 1979-10-31 | 1981-06-02 | Denki Kagaku Kogyo Kk | Catalyst component for olefin polymerization |
| IN163585B (https=) * | 1983-09-20 | 1988-10-15 | Shell Int Research | |
| US5567665A (en) | 1994-03-31 | 1996-10-22 | Union Carbide Chemicals & Plastics Technology Corporation | Shape-shifted magnesium alkoxide component for polymerizing olefins |
| GB9300318D0 (en) | 1993-01-08 | 1993-03-03 | Oxford Analytical Instr Ltd | Improvements relating to sample monitoring |
| CN100441561C (zh) | 2002-02-07 | 2008-12-10 | 中国石油化工股份有限公司 | 用于制备烯烃聚合催化剂的多酯化合物 |
| CN1213080C (zh) * | 2003-04-21 | 2005-08-03 | 中国石油化工股份有限公司 | 用于烯烃聚合反应的催化剂组分及其催化剂 |
| US7351778B2 (en) | 2004-04-30 | 2008-04-01 | China Petroleum & Chemical Corporation | Catalyst component for olefin polymerization and catalyst comprising the same |
| WO2011106494A1 (en) | 2010-02-26 | 2011-09-01 | Dow Global Technologies Llc | Procatalyst composition with substituted amide ester internal electron donor |
| MY159696A (en) | 2010-02-26 | 2017-01-13 | W R Grace & Co -Conn | Halogenated amide ester and internal electron donor with same |
-
2011
- 2011-02-24 MY MYPI2012003806A patent/MY181149A/en unknown
- 2011-02-24 BR BR112012021519-1A patent/BR112012021519B1/pt not_active IP Right Cessation
- 2011-02-24 KR KR1020127025017A patent/KR101824747B1/ko not_active Expired - Fee Related
- 2011-02-24 JP JP2012555140A patent/JP5779193B2/ja not_active Expired - Fee Related
- 2011-02-24 EP EP11707529.1A patent/EP2539379B1/en not_active Not-in-force
- 2011-02-24 US US13/580,414 patent/US8551903B2/en not_active Expired - Fee Related
- 2011-02-24 CN CN201180020873.3A patent/CN102918068B/zh not_active Expired - Fee Related
- 2011-02-24 SG SG2012062998A patent/SG183813A1/en unknown
- 2011-02-24 RU RU2012141060A patent/RU2623223C2/ru not_active IP Right Cessation
- 2011-02-24 WO PCT/US2011/026036 patent/WO2011106500A1/en not_active Ceased
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20030064882A1 (en) * | 2001-05-29 | 2003-04-03 | Kilty Peter A. | Olefin polymerization catalyst compositions and method of preparation |
| RU2298014C2 (ru) * | 2002-02-07 | 2007-04-27 | Чайна Петролеум Энд Кемикал Корпорейшн | Твердый каталитический компонент для полимеризации олефинов, содержащий его катализатор и его применение |
| WO2006110234A2 (en) * | 2005-03-08 | 2006-10-19 | Ineos Usa Llc | Propylene polymer catalyst donor component |
| CN101104589A (zh) * | 2006-07-13 | 2008-01-16 | 中国石油化工股份有限公司 | 用于制备烯烃聚合催化剂的氨酯化合物 |
| CN101104656A (zh) * | 2006-07-13 | 2008-01-16 | 中国石油化工股份有限公司 | 用于烯烃聚合反应的催化剂组分及其催化剂 |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2850411C1 (ru) * | 2020-10-15 | 2025-11-11 | Чайна Петролеум Энд Кемикал Корпорейшн | Пропилен-бутеновый сополимер, способ его получения и его применение |
Also Published As
| Publication number | Publication date |
|---|---|
| JP5779193B2 (ja) | 2015-09-16 |
| EP2539379A1 (en) | 2013-01-02 |
| BR112012021519B1 (pt) | 2019-12-17 |
| EP2539379B1 (en) | 2017-09-06 |
| RU2012141060A (ru) | 2014-04-10 |
| BR112012021519A2 (pt) | 2016-07-05 |
| KR20130020771A (ko) | 2013-02-28 |
| CN102918068B (zh) | 2016-01-06 |
| US20120316299A1 (en) | 2012-12-13 |
| KR101824747B1 (ko) | 2018-03-14 |
| JP2013521341A (ja) | 2013-06-10 |
| US8551903B2 (en) | 2013-10-08 |
| CN102918068A (zh) | 2013-02-06 |
| WO2011106500A1 (en) | 2011-09-01 |
| SG183813A1 (en) | 2012-10-30 |
| MY181149A (en) | 2020-12-19 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| RU2623223C2 (ru) | Амидоэфирный внутренний донор электронов и способ | |
| JP6061908B2 (ja) | 置換アミドエステル内部電子供与体を有するプロ触媒組成物 | |
| CN103140510B (zh) | 卤化酰胺酯和包含其的内电子给体 | |
| US8383540B2 (en) | Catalyst composition with halo-malonate internal electron donor and polymer from same |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| HZ9A | Changing address for correspondence with an applicant | ||
| MM4A | The patent is invalid due to non-payment of fees |
Effective date: 20200225 |