TWI262196B

TWI262196B - A catalytic composition and its preparation and use for preparing polymers from ethylenically unsaturated monomers

A catalytic composition and its preparation and use for preparing polymers from ethylenically unsaturated monomers Download PDF

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Publication number: TWI262196B
Authority: TW; Taiwan
Prior art keywords: group; metal; complex; ligand; pair
Prior art date: 2003-08-21

Application number

TW093123928A

Other languages

English (en)

Chinese (zh)

Other versions

TW200514795A (en

Inventor

Brian Leslie Goodall

Jennifer Lynn Petoff

Han Shen

Original Assignee

Rohm & Haas

Priority date

2003-08-21

Filing date

2004-08-10

Publication date

2006-09-21

2004-08-10 Application filed by Rohm & Haas filed Critical Rohm & Haas

2005-05-01 Publication of TW200514795A publication Critical patent/TW200514795A/zh

2006-09-21 Application granted granted Critical

2006-09-21 Publication of TWI262196B publication Critical patent/TWI262196B/zh

Links

239000000178 monomer Substances 0.000 title claims abstract description 134
239000000203 mixture Substances 0.000 title claims abstract description 122
229920000642 polymer Polymers 0.000 title claims abstract description 105
230000003197 catalytic effect Effects 0.000 title claims abstract description 10
238000002360 preparation method Methods 0.000 title abstract description 39
125000002091 cationic group Chemical group 0.000 claims abstract description 95
238000000034 method Methods 0.000 claims abstract description 79
238000006116 polymerization reaction Methods 0.000 claims abstract description 70
229910052751 metal Inorganic materials 0.000 claims description 298
239000002184 metal Substances 0.000 claims description 297
239000003446 ligand Substances 0.000 claims description 183
-1 sharp Chemical compound 0.000 claims description 157
239000003054 catalyst Substances 0.000 claims description 123
239000002243 precursor Substances 0.000 claims description 94
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 56
239000000126 substance Substances 0.000 claims description 54
150000001875 compounds Chemical class 0.000 claims description 46
150000001336 alkenes Chemical class 0.000 claims description 44
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 42
229930195733 hydrocarbon Natural products 0.000 claims description 41
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 32
239000004215 Carbon black (E152) Substances 0.000 claims description 31
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 28
150000002430 hydrocarbons Chemical group 0.000 claims description 28
229910052763 palladium Inorganic materials 0.000 claims description 28
239000012190 activator Substances 0.000 claims description 27
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PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 claims description 25
239000010931 gold Substances 0.000 claims description 25
NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 24
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125000000129 anionic group Chemical group 0.000 claims description 20
150000001450 anions Chemical class 0.000 claims description 20
229910052707 ruthenium Inorganic materials 0.000 claims description 20
125000004122 cyclic group Chemical group 0.000 claims description 16
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239000004332 silver Substances 0.000 claims description 14
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229910052759 nickel Inorganic materials 0.000 claims description 12
239000011572 manganese Substances 0.000 claims description 11
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 10
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JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 claims description 9
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229910017052 cobalt Inorganic materials 0.000 claims description 9
239000010941 cobalt Substances 0.000 claims description 9
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125000000217 alkyl group Chemical group 0.000 description 41
125000001183 hydrocarbyl group Chemical group 0.000 description 41
239000002585 base Substances 0.000 description 40
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IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 32
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125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 28
238000006243 chemical reaction Methods 0.000 description 27
239000002253 acid Substances 0.000 description 26
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 25
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 25
239000002002 slurry Substances 0.000 description 25
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 24
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
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210000002966 serum Anatomy 0.000 description 24
239000001257 hydrogen Substances 0.000 description 22
229910052739 hydrogen Inorganic materials 0.000 description 22
239000002245 particle Substances 0.000 description 22
229920001519 homopolymer Polymers 0.000 description 21
WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 description 21
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 20
239000000463 material Substances 0.000 description 20
238000004458 analytical method Methods 0.000 description 19
238000002474 experimental method Methods 0.000 description 19
229910052736 halogen Inorganic materials 0.000 description 18
229910052757 nitrogen Inorganic materials 0.000 description 18
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 17
238000010521 absorption reaction Methods 0.000 description 17
TWKVUTXHANJYGH-UHFFFAOYSA-L allyl palladium chloride Chemical class Cl[Pd]CC=C.Cl[Pd]CC=C TWKVUTXHANJYGH-UHFFFAOYSA-L 0.000 description 17
239000000539 dimer Substances 0.000 description 17
150000002367 halogens Chemical class 0.000 description 17
150000002431 hydrogen Chemical class 0.000 description 17
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 17
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 16
238000003756 stirring Methods 0.000 description 16
239000005977 Ethylene Substances 0.000 description 15
150000001412 amines Chemical class 0.000 description 15
NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 14
BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 14
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150000002148 esters Chemical class 0.000 description 14
125000000524 functional group Chemical group 0.000 description 14
238000005227 gel permeation chromatography Methods 0.000 description 14
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 14
238000006467 substitution reaction Methods 0.000 description 14
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KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 13
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240000005373 Panax quinquefolius Species 0.000 description 13
235000003140 Panax quinquefolius Nutrition 0.000 description 13
229910052731 fluorine Inorganic materials 0.000 description 13
235000008434 ginseng Nutrition 0.000 description 13
239000007788 liquid Substances 0.000 description 13
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 13
230000007935 neutral effect Effects 0.000 description 13
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239000002689 soil Substances 0.000 description 13
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238000005481 NMR spectroscopy Methods 0.000 description 12
229910052782 aluminium Chemical group 0.000 description 12
239000000460 chlorine Substances 0.000 description 12
230000000052 comparative effect Effects 0.000 description 12
238000010168 coupling process Methods 0.000 description 12
238000005859 coupling reaction Methods 0.000 description 12
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YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 12
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MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 11
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235000019439 ethyl acetate Nutrition 0.000 description 11
238000001914 filtration Methods 0.000 description 11
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 11
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YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 10
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CKDOCTFBFTVPSN-UHFFFAOYSA-N borneol Natural products C1CC2(C)C(C)CC1C2(C)C CKDOCTFBFTVPSN-UHFFFAOYSA-N 0.000 description 10
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GGCZERPQGJTIQP-UHFFFAOYSA-N sodium;9,10-dioxoanthracene-2-sulfonic acid Chemical compound [Na+].C1=CC=C2C(=O)C3=CC(S(=O)(=O)O)=CC=C3C(=O)C2=C1 GGCZERPQGJTIQP-UHFFFAOYSA-N 0.000 description 9
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238000005160 1H NMR spectroscopy Methods 0.000 description 4
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