WO2004035636A2

WO2004035636A2 - Polymerized cycloolefins using transition metal catalyst and end products thereof

Polymerized cycloolefins using transition metal catalyst and end products thereof Download PDF

Info

Publication number: WO2004035636A2
Authority: WO; WIPO (PCT)
Prior art keywords: branched; group; linear; alkyl; norbornene
Prior art date: 2002-10-15

Application number

PCT/US2003/032474

Other languages

English (en)

French (fr)

Other versions

WO2004035636A3 (en

Inventor

Larry F. Rhodes

Andrew Bell

R. Ravikiran

John C. Fondran

Saikumar Jayaraman

Brian L. Goodall

Richard A. Mimna

John-Henry Lipian

Original Assignee

Promerus, Llc

Priority date

2002-10-15

Filing date

2003-10-14

Publication date

2004-04-29

2003-10-14 Application filed by Promerus, Llc filed Critical Promerus, Llc

2003-10-14 Priority to AU2003287068A priority Critical patent/AU2003287068A1/en

2004-04-29 Publication of WO2004035636A2 publication Critical patent/WO2004035636A2/en

2005-01-13 Publication of WO2004035636A3 publication Critical patent/WO2004035636A3/en

Links

239000003054 catalyst Substances 0.000 title claims abstract description 147
229910052723 transition metal Inorganic materials 0.000 title claims abstract description 57
150000003624 transition metals Chemical class 0.000 title claims abstract description 52
150000001925 cycloalkenes Chemical class 0.000 title claims abstract description 13
239000007795 chemical reaction product Substances 0.000 title description 2
229920000642 polymer Polymers 0.000 claims abstract description 203
239000003446 ligand Substances 0.000 claims abstract description 124
230000003287 optical effect Effects 0.000 claims abstract description 122
150000001768 cations Chemical class 0.000 claims abstract description 77
150000001450 anions Chemical class 0.000 claims abstract description 56
230000007935 neutral effect Effects 0.000 claims abstract description 53
125000003367 polycyclic group Chemical group 0.000 claims abstract description 23
239000000203 mixture Substances 0.000 claims description 367
-1 alkyl norbornene Chemical compound 0.000 claims description 348
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical group [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 243
239000000178 monomer Substances 0.000 claims description 200
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 147
125000000217 alkyl group Chemical group 0.000 claims description 137
229910052763 palladium Inorganic materials 0.000 claims description 109
125000003118 aryl group Chemical group 0.000 claims description 106
VEEKCIOFMIAGSF-UHFFFAOYSA-N 4-butylbicyclo[2.2.1]hept-2-ene Chemical group C1CC2C=CC1(CCCC)C2 VEEKCIOFMIAGSF-UHFFFAOYSA-N 0.000 claims description 86
125000004432 carbon atom Chemical group C* 0.000 claims description 83
229910052751 metal Inorganic materials 0.000 claims description 66
239000002904 solvent Substances 0.000 claims description 65
229910052739 hydrogen Inorganic materials 0.000 claims description 63
239000001257 hydrogen Substances 0.000 claims description 63
239000002184 metal Substances 0.000 claims description 57
BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 claims description 55
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 55
150000003839 salts Chemical class 0.000 claims description 55
229910052736 halogen Inorganic materials 0.000 claims description 54
150000002367 halogens Chemical class 0.000 claims description 54
125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 54
238000000034 method Methods 0.000 claims description 54
125000001188 haloalkyl group Chemical group 0.000 claims description 53
239000000460 chlorine Substances 0.000 claims description 51
125000000753 cycloalkyl group Chemical group 0.000 claims description 49
150000004645 aluminates Chemical class 0.000 claims description 47
229910052731 fluorine Inorganic materials 0.000 claims description 46
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 45
125000003545 alkoxy group Chemical group 0.000 claims description 44
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 43
239000011737 fluorine Substances 0.000 claims description 43
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical group [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 42
229920003050 poly-cycloolefin Polymers 0.000 claims description 40
239000004065 semiconductor Substances 0.000 claims description 40
125000001424 substituent group Chemical group 0.000 claims description 40
239000000853 adhesive Substances 0.000 claims description 39
230000001070 adhesive effect Effects 0.000 claims description 39
125000003710 aryl alkyl group Chemical group 0.000 claims description 38
150000001875 compounds Chemical class 0.000 claims description 37
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical group [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 33
125000004122 cyclic group Chemical group 0.000 claims description 31
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 28
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 28
229910052744 lithium Inorganic materials 0.000 claims description 28
JFNLZVQOOSMTJK-KNVOCYPGSA-N norbornene Chemical compound C1[C@@H]2CC[C@H]1C=C2 JFNLZVQOOSMTJK-KNVOCYPGSA-N 0.000 claims description 26
125000004430 oxygen atom Chemical group O* 0.000 claims description 24
239000000758 substrate Substances 0.000 claims description 24
229910052760 oxygen Inorganic materials 0.000 claims description 23
239000001301 oxygen Substances 0.000 claims description 23
238000001914 filtration Methods 0.000 claims description 22
125000000262 haloalkenyl group Chemical group 0.000 claims description 22
229910052697 platinum Inorganic materials 0.000 claims description 21
125000003342 alkenyl group Chemical group 0.000 claims description 20
230000000694 effects Effects 0.000 claims description 19
239000010408 film Substances 0.000 claims description 19
229910052757 nitrogen Inorganic materials 0.000 claims description 19
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 18
238000000576 coating method Methods 0.000 claims description 18
229910052759 nickel Chemical group 0.000 claims description 17
229910052717 sulfur Inorganic materials 0.000 claims description 17
125000000392 cycloalkenyl group Chemical group 0.000 claims description 16
125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims description 16
230000000379 polymerizing effect Effects 0.000 claims description 16
125000004104 aryloxy group Chemical group 0.000 claims description 15
239000012788 optical film Substances 0.000 claims description 15
CBVRSAWYUWTDDH-UHFFFAOYSA-N 4-bicyclo[2.2.1]hept-2-enyl(trimethoxy)silane Chemical group C1CC2C=CC1([Si](OC)(OC)OC)C2 CBVRSAWYUWTDDH-UHFFFAOYSA-N 0.000 claims description 14
XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims description 14
230000005693 optoelectronics Effects 0.000 claims description 14
229910052710 silicon Chemical group 0.000 claims description 14
JZEPSDIWGBJOEH-UHFFFAOYSA-N 4-decylbicyclo[2.2.1]hept-2-ene Chemical compound C1CC2C=CC1(CCCCCCCCCC)C2 JZEPSDIWGBJOEH-UHFFFAOYSA-N 0.000 claims description 13
239000011248 coating agent Substances 0.000 claims description 13
239000005022 packaging material Substances 0.000 claims description 13
229910052698 phosphorus Inorganic materials 0.000 claims description 13
XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 12
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 12
239000003990 capacitor Substances 0.000 claims description 12
239000008393 encapsulating agent Substances 0.000 claims description 12
125000005842 heteroatom Chemical group 0.000 claims description 12
239000012212 insulator Substances 0.000 claims description 12
239000011593 sulfur Chemical group 0.000 claims description 12
ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 11
229910052782 aluminium Chemical group 0.000 claims description 11
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical group [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 11
150000001412 amines Chemical class 0.000 claims description 11
229910052796 boron Inorganic materials 0.000 claims description 11
238000000746 purification Methods 0.000 claims description 11
125000006374 C2-C10 alkenyl group Chemical group 0.000 claims description 10
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 10
125000000746 allylic group Chemical group 0.000 claims description 10
125000004469 siloxy group Chemical group [SiH3]O* 0.000 claims description 10
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 10
125000000129 anionic group Chemical group 0.000 claims description 9
RBFQJDQYXXHULB-UHFFFAOYSA-N arsane Chemical class [AsH3] RBFQJDQYXXHULB-UHFFFAOYSA-N 0.000 claims description 9
238000001723 curing Methods 0.000 claims description 9
125000005843 halogen group Chemical group 0.000 claims description 9
238000005286 illumination Methods 0.000 claims description 9
239000013307 optical fiber Substances 0.000 claims description 9
210000001525 retina Anatomy 0.000 claims description 9
239000010703 silicon Chemical group 0.000 claims description 9
OUULRIDHGPHMNQ-UHFFFAOYSA-N stibane Chemical class [SbH3] OUULRIDHGPHMNQ-UHFFFAOYSA-N 0.000 claims description 9
125000006729 (C2-C5) alkenyl group Chemical group 0.000 claims description 8
125000000304 alkynyl group Chemical group 0.000 claims description 8
239000000463 material Substances 0.000 claims description 8
239000011574 phosphorus Substances 0.000 claims description 8
150000003222 pyridines Chemical class 0.000 claims description 8
150000004292 cyclic ethers Chemical class 0.000 claims description 7
125000004342 dicyclopropylmethyl group Chemical group [H]C1([H])C([H])([H])C1([H])C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 7
125000000962 organic group Chemical group 0.000 claims description 7
229910000073 phosphorus hydride Inorganic materials 0.000 claims description 7
239000011253 protective coating Substances 0.000 claims description 7
150000003568 thioethers Chemical class 0.000 claims description 7
229910007161 Si(CH3)3 Inorganic materials 0.000 claims description 6
229960004132 diethyl ether Drugs 0.000 claims description 6
125000003106 haloaryl group Chemical group 0.000 claims description 6
239000012939 laminating adhesive Substances 0.000 claims description 6
125000006527 (C1-C5) alkyl group Chemical group 0.000 claims description 5
125000003358 C2-C20 alkenyl group Chemical group 0.000 claims description 5
125000005915 C6-C14 aryl group Chemical group 0.000 claims description 5
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
125000002704 decyl group Chemical group [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])* 0.000 claims description 5
239000000835 fiber Substances 0.000 claims description 5
238000004519 manufacturing process Methods 0.000 claims description 5
125000004433 nitrogen atom Chemical group N* 0.000 claims description 5
125000004437 phosphorous atom Chemical group 0.000 claims description 5
125000004434 sulfur atom Chemical group 0.000 claims description 5
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
150000001993 dienes Chemical class 0.000 claims description 4
150000001642 boronic acid derivatives Chemical group 0.000 claims description 3
125000005347 halocycloalkyl group Chemical group 0.000 claims description 3
238000002156 mixing Methods 0.000 claims description 3
150000002903 organophosphorus compounds Chemical class 0.000 claims description 3
125000005389 trialkylsiloxy group Chemical group 0.000 claims description 3
LFMFPKKYRXFHHZ-UHFFFAOYSA-N R24 Chemical group C1=C(Cl)C(C)=CC=C1NC1=NC(N)=C(C=CC=C2)C2=N1 LFMFPKKYRXFHHZ-UHFFFAOYSA-N 0.000 claims description 2
229920000636 poly(norbornene) polymer Polymers 0.000 claims description 2
125000005369 trialkoxysilyl group Chemical group 0.000 claims description 2
RGGBKNFGPFEDRC-UHFFFAOYSA-N 4-bicyclo[2.2.1]hept-2-enyl(triethoxy)silane Chemical compound C1CC2C=CC1([Si](OCC)(OCC)OCC)C2 RGGBKNFGPFEDRC-UHFFFAOYSA-N 0.000 claims 13
KMRASZKMNHTING-UHFFFAOYSA-N 4-hexylbicyclo[2.2.1]hept-2-ene Chemical compound C1CC2C=CC1(CCCCCC)C2 KMRASZKMNHTING-UHFFFAOYSA-N 0.000 claims 13
125000005865 C2-C10alkynyl group Chemical group 0.000 claims 8
238000001228 spectrum Methods 0.000 claims 4
125000000008 (C1-C10) alkyl group Chemical group 0.000 claims 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 2
JJWKPURADFRFRB-UHFFFAOYSA-N carbonyl sulfide Chemical compound O=C=S JJWKPURADFRFRB-UHFFFAOYSA-N 0.000 claims 2
238000001429 visible spectrum Methods 0.000 claims 2
229910000074 antimony hydride Inorganic materials 0.000 claims 1
VIQRCOQXIHFJND-UHFFFAOYSA-N bicyclo[2.2.2]oct-2-ene Chemical compound C1CC2CCC1C=C2 VIQRCOQXIHFJND-UHFFFAOYSA-N 0.000 claims 1
238000002329 infrared spectrum Methods 0.000 claims 1
229920005567 polycyclic polymer Polymers 0.000 claims 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 1
238000002211 ultraviolet spectrum Methods 0.000 claims 1
125000002091 cationic group Chemical group 0.000 abstract description 12
238000012644 addition polymerization Methods 0.000 abstract description 3
150000004696 coordination complex Chemical class 0.000 abstract description 2
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 811
239000000243 solution Substances 0.000 description 220
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 123
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 105
WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 description 102
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 87
HHKDWDAAEFGBAC-UHFFFAOYSA-N 5-bicyclo[2.2.1]hept-2-enyl(triethoxy)silane Chemical compound C1C2C([Si](OCC)(OCC)OCC)CC1C=C2 HHKDWDAAEFGBAC-UHFFFAOYSA-N 0.000 description 71
WLTSXAIICPDFKI-FNORWQNLSA-N (E)-3-dodecene Chemical compound CCCCCCCC\C=C\CC WLTSXAIICPDFKI-FNORWQNLSA-N 0.000 description 56
PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical class Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 55
ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 55
238000006243 chemical reaction Methods 0.000 description 53
NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 53
125000001183 hydrocarbyl group Chemical group 0.000 description 44
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 44
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 42
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 32
238000006116 polymerization reaction Methods 0.000 description 31
239000007787 solid Substances 0.000 description 31
150000002431 hydrogen Chemical class 0.000 description 28
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 28
YMWUJEATGCHHMB-DICFDUPASA-N dichloromethane-d2 Chemical compound [2H]C([2H])(Cl)Cl YMWUJEATGCHHMB-DICFDUPASA-N 0.000 description 24
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 23
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 22
229910052801 chlorine Inorganic materials 0.000 description 22
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 21
229910052794 bromium Inorganic materials 0.000 description 21
150000003254 radicals Chemical group 0.000 description 21
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 20
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 20
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 19
125000005394 methallyl group Chemical group 0.000 description 19
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
238000001035 drying Methods 0.000 description 18
238000003756 stirring Methods 0.000 description 18
COIOYMYWGDAQPM-UHFFFAOYSA-N tris(2-methylphenyl)phosphane Chemical compound CC1=CC=CC=C1P(C=1C(=CC=CC=1)C)C1=CC=CC=C1C COIOYMYWGDAQPM-UHFFFAOYSA-N 0.000 description 17
238000004132 cross linking Methods 0.000 description 16
ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 16
239000012429 reaction media Substances 0.000 description 16
YHESWXAODSYVCO-UHFFFAOYSA-N 5-but-1-enylbicyclo[2.2.1]hept-2-ene Chemical compound C1C2C(C=CCC)CC1C=C2 YHESWXAODSYVCO-UHFFFAOYSA-N 0.000 description 15
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 15
239000000047 product Substances 0.000 description 15
229910052716 thallium Inorganic materials 0.000 description 15
BKVIYDNLLOSFOA-UHFFFAOYSA-N thallium Chemical compound [Tl] BKVIYDNLLOSFOA-UHFFFAOYSA-N 0.000 description 15
238000005160 1H NMR spectroscopy Methods 0.000 description 14
229920001577 copolymer Polymers 0.000 description 14
230000008569 process Effects 0.000 description 14
229910010199 LiAl Inorganic materials 0.000 description 13
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 12
239000007983 Tris buffer Substances 0.000 description 12
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 12
125000000524 functional group Chemical group 0.000 description 12
238000002360 preparation method Methods 0.000 description 12
229910052709 silver Inorganic materials 0.000 description 12
239000004332 silver Substances 0.000 description 12
239000011734 sodium Substances 0.000 description 12
OTTZHAVKAVGASB-UHFFFAOYSA-N 2-heptene Natural products CCCCC=CC OTTZHAVKAVGASB-UHFFFAOYSA-N 0.000 description 11
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 11
DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 description 11
229910052805 deuterium Inorganic materials 0.000 description 11
239000000706 filtrate Substances 0.000 description 11
LJKNRSBEKUSSIE-UHFFFAOYSA-N hept-2-ene Chemical compound [CH2]CCCC=CC LJKNRSBEKUSSIE-UHFFFAOYSA-N 0.000 description 11
229910052708 sodium Inorganic materials 0.000 description 11
IGNTWNVBGLNYDV-UHFFFAOYSA-N triisopropylphosphine Chemical compound CC(C)P(C(C)C)C(C)C IGNTWNVBGLNYDV-UHFFFAOYSA-N 0.000 description 11
YWWDBCBWQNCYNR-UHFFFAOYSA-N trimethylphosphine Chemical compound CP(C)C YWWDBCBWQNCYNR-UHFFFAOYSA-N 0.000 description 11
238000004679 31P NMR spectroscopy Methods 0.000 description 10
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
239000002841 Lewis acid Substances 0.000 description 10
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 10
239000012190 activator Substances 0.000 description 10
150000007517 lewis acids Chemical class 0.000 description 10
229910052749 magnesium Inorganic materials 0.000 description 10
239000011777 magnesium Substances 0.000 description 10
239000000843 powder Substances 0.000 description 10
239000011541 reaction mixture Substances 0.000 description 10
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
239000002253 acid Substances 0.000 description 9
125000001145 hydrido group Chemical group *[H] 0.000 description 9
239000003999 initiator Substances 0.000 description 9
150000002902 organometallic compounds Chemical class 0.000 description 9
239000002002 slurry Substances 0.000 description 9
DHWBYAACHDUFAT-UHFFFAOYSA-N tricyclopentylphosphane Chemical compound C1CCCC1P(C1CCCC1)C1CCCC1 DHWBYAACHDUFAT-UHFFFAOYSA-N 0.000 description 9
ZXMGHDIOOHOAAE-UHFFFAOYSA-N 1,1,1-trifluoro-n-(trifluoromethylsulfonyl)methanesulfonamide Chemical compound FC(F)(F)S(=O)(=O)NS(=O)(=O)C(F)(F)F ZXMGHDIOOHOAAE-UHFFFAOYSA-N 0.000 description 8
HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 description 8
YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 8
150000001335 aliphatic alkanes Chemical class 0.000 description 8
230000015572 biosynthetic process Effects 0.000 description 8
238000011065 in-situ storage Methods 0.000 description 8
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VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 8
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125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
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238000010525 oxidative degradation reaction Methods 0.000 description 1
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RVVWLPDCSZPLER-UHFFFAOYSA-N oxolan-2-yl bicyclo[2.2.1]hept-2-ene-5-carboxylate Chemical compound C1C(C=C2)CC2C1C(=O)OC1CCCO1 RVVWLPDCSZPLER-UHFFFAOYSA-N 0.000 description 1
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PKHWBIKUPQIKGK-UHFFFAOYSA-N tricyclohexylsilanylium Chemical compound C1CCCCC1[Si+](C1CCCCC1)C1CCCCC1 PKHWBIKUPQIKGK-UHFFFAOYSA-N 0.000 description 1
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POHPFVPVRKJHCR-UHFFFAOYSA-N tris(2,3,4,5,6-pentafluorophenyl)alumane Chemical compound FC1=C(F)C(F)=C(F)C(F)=C1[Al](C=1C(=C(F)C(F)=C(F)C=1F)F)C1=C(F)C(F)=C(F)C(F)=C1F POHPFVPVRKJHCR-UHFFFAOYSA-N 0.000 description 1
FQLSDFNKTNBQLC-UHFFFAOYSA-N tris(2,3,4,5,6-pentafluorophenyl)phosphane Chemical compound FC1=C(F)C(F)=C(F)C(F)=C1P(C=1C(=C(F)C(F)=C(F)C=1F)F)C1=C(F)C(F)=C(F)C(F)=C1F FQLSDFNKTNBQLC-UHFFFAOYSA-N 0.000 description 1
IDXDWPWXHTXJMZ-UHFFFAOYSA-N tris(2,4,6-trimethylphenyl)phosphane Chemical compound CC1=CC(C)=CC(C)=C1P(C=1C(=CC(C)=CC=1C)C)C1=C(C)C=C(C)C=C1C IDXDWPWXHTXJMZ-UHFFFAOYSA-N 0.000 description 1
CMLWFCUAXGSMBB-UHFFFAOYSA-N tris(2,6-dimethoxyphenyl)phosphane Chemical compound COC1=CC=CC(OC)=C1P(C=1C(=CC=CC=1OC)OC)C1=C(OC)C=CC=C1OC CMLWFCUAXGSMBB-UHFFFAOYSA-N 0.000 description 1
LZTKJXHKOLJIHI-UHFFFAOYSA-N tris(2-fluorophenyl)phosphane Chemical compound FC1=CC=CC=C1P(C=1C(=CC=CC=1)F)C1=CC=CC=C1F LZTKJXHKOLJIHI-UHFFFAOYSA-N 0.000 description 1
IIOSDXGZLBPOHD-UHFFFAOYSA-N tris(2-methoxyphenyl)phosphane Chemical compound COC1=CC=CC=C1P(C=1C(=CC=CC=1)OC)C1=CC=CC=C1OC IIOSDXGZLBPOHD-UHFFFAOYSA-N 0.000 description 1
NURJXHUITUPBOD-UHFFFAOYSA-N tris(2-methylpropyl) phosphite Chemical compound CC(C)COP(OCC(C)C)OCC(C)C NURJXHUITUPBOD-UHFFFAOYSA-N 0.000 description 1
QAPGHLJQIVDTPT-UHFFFAOYSA-N tris(3-chlorophenyl)phosphane Chemical compound ClC1=CC=CC(P(C=2C=C(Cl)C=CC=2)C=2C=C(Cl)C=CC=2)=C1 QAPGHLJQIVDTPT-UHFFFAOYSA-N 0.000 description 1
CUTRINLXFPIWQB-UHFFFAOYSA-N tris(3-fluorophenyl)phosphane Chemical compound FC1=CC=CC(P(C=2C=C(F)C=CC=2)C=2C=C(F)C=CC=2)=C1 CUTRINLXFPIWQB-UHFFFAOYSA-N 0.000 description 1
CCXTYQMZVYIQRP-UHFFFAOYSA-N tris(3-methoxyphenyl)phosphane Chemical compound COC1=CC=CC(P(C=2C=C(OC)C=CC=2)C=2C=C(OC)C=CC=2)=C1 CCXTYQMZVYIQRP-UHFFFAOYSA-N 0.000 description 1
APRCRSUXFGXHEL-UHFFFAOYSA-N tris(3-methoxypropyl)phosphane Chemical compound COCCCP(CCCOC)CCCOC APRCRSUXFGXHEL-UHFFFAOYSA-N 0.000 description 1
IQKSLJOIKWOGIZ-UHFFFAOYSA-N tris(4-chlorophenyl)phosphane Chemical compound C1=CC(Cl)=CC=C1P(C=1C=CC(Cl)=CC=1)C1=CC=C(Cl)C=C1 IQKSLJOIKWOGIZ-UHFFFAOYSA-N 0.000 description 1
FEVFLQDDNUQKRY-UHFFFAOYSA-N tris(4-methylphenyl) phosphite Chemical compound C1=CC(C)=CC=C1OP(OC=1C=CC(C)=CC=1)OC1=CC=C(C)C=C1 FEVFLQDDNUQKRY-UHFFFAOYSA-N 0.000 description 1
MXLDRFIVBLWESA-UHFFFAOYSA-N tris(trifluoromethyl)phosphane Chemical compound FC(F)(F)P(C(F)(F)F)C(F)(F)F MXLDRFIVBLWESA-UHFFFAOYSA-N 0.000 description 1
OUMZKMRZMVDEOF-UHFFFAOYSA-N tris(trimethylsilyl)phosphane Chemical compound C[Si](C)(C)P([Si](C)(C)C)[Si](C)(C)C OUMZKMRZMVDEOF-UHFFFAOYSA-N 0.000 description 1
SWPCNGVHIJTPJJ-UHFFFAOYSA-N tris(trimethylsilyl)silanylium Chemical compound C[Si](C)(C)[Si+]([Si](C)(C)C)[Si](C)(C)C SWPCNGVHIJTPJJ-UHFFFAOYSA-N 0.000 description 1
BPKXQSLAVGBZEM-UHFFFAOYSA-N tris[3,5-bis(trifluoromethyl)phenyl]borane Chemical compound FC(F)(F)C1=CC(C(F)(F)F)=CC(B(C=2C=C(C=C(C=2)C(F)(F)F)C(F)(F)F)C=2C=C(C=C(C=2)C(F)(F)F)C(F)(F)F)=C1 BPKXQSLAVGBZEM-UHFFFAOYSA-N 0.000 description 1
ITJHLZVYLDBFOJ-UHFFFAOYSA-N tris[3,5-bis(trifluoromethyl)phenyl]phosphane Chemical compound FC(F)(F)C1=CC(C(F)(F)F)=CC(P(C=2C=C(C=C(C=2)C(F)(F)F)C(F)(F)F)C=2C=C(C=C(C=2)C(F)(F)F)C(F)(F)F)=C1 ITJHLZVYLDBFOJ-UHFFFAOYSA-N 0.000 description 1
RWVACGVJXRKMIZ-UHFFFAOYSA-N tris[4-(trifluoromethyl)phenyl] phosphite Chemical compound C1=CC(C(F)(F)F)=CC=C1OP(OC=1C=CC(=CC=1)C(F)(F)F)OC1=CC=C(C(F)(F)F)C=C1 RWVACGVJXRKMIZ-UHFFFAOYSA-N 0.000 description 1
NZIQBDROTUFRHZ-UHFFFAOYSA-N tritert-butyl phosphite Chemical compound CC(C)(C)OP(OC(C)(C)C)OC(C)(C)C NZIQBDROTUFRHZ-UHFFFAOYSA-N 0.000 description 1
KUCPTMZJPDVWJL-UHFFFAOYSA-N trithiophen-2-ylphosphane Chemical compound C1=CSC(P(C=2SC=CC=2)C=2SC=CC=2)=C1 KUCPTMZJPDVWJL-UHFFFAOYSA-N 0.000 description 1
238000004017 vitrification Methods 0.000 description 1
239000003039 volatile agent Substances 0.000 description 1
150000003738 xylenes Chemical class 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
239000011701 zinc Substances 0.000 description 1
239000011787 zinc oxide Substances 0.000 description 1
229910052984 zinc sulfide Inorganic materials 0.000 description 1
DRDVZXDWVBGGMH-UHFFFAOYSA-N zinc;sulfide Chemical compound [S-2].[Zn+2] DRDVZXDWVBGGMH-UHFFFAOYSA-N 0.000 description 1