IL126567A - Purification process of TETRAKIS (FLUOROARYL) BORATEO MAGNESIUM HALIDE and derivative production process of TETRAKIS (FLUOROARYL) BORATE - Google Patents

Purification process of TETRAKIS (FLUOROARYL) BORATEO MAGNESIUM HALIDE and derivative production process of TETRAKIS (FLUOROARYL) BORATE

Info

Publication number: IL126567A
Authority: IL; Israel
Prior art keywords: tetrakis; borate; fluoroaryl; compound; cations
Prior art date: 1997-03-10

Application number

IL12656798A

Other languages

English (en)

Hebrew (he)

Other versions

IL126567A0 (en

Inventor

Hitoshi Mitsui

Tsunemasa Ueno

Ikuyo Ikeno

Naoko Yamamoto

Original Assignee

Nippon Catalytic Chem Ind

Priority date (The priority date 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 date listed.)

1997-03-10

Filing date

1998-03-09

Publication date

2002-05-23

1998-03-09 Application filed by Nippon Catalytic Chem Ind filed Critical Nippon Catalytic Chem Ind

1998-03-09 Priority to IL14447798A priority Critical patent/IL144477A/xx

1999-08-17 Publication of IL126567A0 publication Critical patent/IL126567A0/xx

2001-07-20 Priority to IL14447701A priority patent/IL144477A0/xx

2002-05-23 Publication of IL126567A publication Critical patent/IL126567A/en

Links

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 title claims abstract description 392
125000004407 fluoroaryl group Chemical group 0.000 title claims abstract description 305
-1 magnesium halide Chemical class 0.000 title claims abstract description 286
238000000034 method Methods 0.000 title claims abstract description 197
229910052749 magnesium Inorganic materials 0.000 title claims abstract description 59
239000011777 magnesium Substances 0.000 title claims abstract description 59
BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 title claims description 142
150000001642 boronic acid derivatives Chemical class 0.000 title claims description 67
229910052784 alkaline earth metal Inorganic materials 0.000 claims abstract description 52
125000001153 fluoro group Chemical group F* 0.000 claims abstract description 44
229910052731 fluorine Inorganic materials 0.000 claims abstract description 43
229910052783 alkali metal Inorganic materials 0.000 claims abstract description 34
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 19
125000003545 alkoxy group Chemical group 0.000 claims abstract description 17
229910052801 chlorine Inorganic materials 0.000 claims abstract description 9
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 7
125000001309 chloro group Chemical group Cl* 0.000 claims abstract description 7
125000001183 hydrocarbyl group Chemical group 0.000 claims abstract 9
150000001875 compounds Chemical class 0.000 claims description 89
150000001768 cations Chemical class 0.000 claims description 83
150000003839 salts Chemical class 0.000 claims description 54
239000002253 acid Substances 0.000 claims description 46
LWNGJAHMBMVCJR-UHFFFAOYSA-N (2,3,4,5,6-pentafluorophenoxy)boronic acid Chemical compound OB(O)OC1=C(F)C(F)=C(F)C(F)=C1F LWNGJAHMBMVCJR-UHFFFAOYSA-N 0.000 claims description 27
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 27
JOXNNISDIMLBKW-UHFFFAOYSA-M [Br-].[Mg+2].B(OC1=C(C(=C(C(=C1F)F)F)F)F)([O-])O Chemical compound [Br-].[Mg+2].B(OC1=C(C(=C(C(=C1F)F)F)F)F)([O-])O JOXNNISDIMLBKW-UHFFFAOYSA-M 0.000 claims description 25
OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 18
WOAZEKPXTXCPFZ-UHFFFAOYSA-N dimethyl(phenyl)azanium;chloride Chemical compound Cl.CN(C)C1=CC=CC=C1 WOAZEKPXTXCPFZ-UHFFFAOYSA-N 0.000 claims description 15
JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 claims description 10
229910052751 metal Inorganic materials 0.000 claims description 10
239000002184 metal Substances 0.000 claims description 10
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 9
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 9
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 8
125000001931 aliphatic group Chemical class 0.000 claims description 8
125000003118 aryl group Chemical class 0.000 claims description 8
OTCKOJUMXQWKQG-UHFFFAOYSA-L magnesium bromide Chemical compound [Mg+2].[Br-].[Br-] OTCKOJUMXQWKQG-UHFFFAOYSA-L 0.000 claims description 8
229910001623 magnesium bromide Inorganic materials 0.000 claims description 8
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 8
150000005325 alkali earth metal hydroxides Chemical class 0.000 claims description 7
150000008044 alkali metal hydroxides Chemical class 0.000 claims description 7
150000004694 iodide salts Chemical group 0.000 claims description 6
MDICIVRGHCTEQJ-UHFFFAOYSA-N 1-methyl-1,2-dihydropyridin-1-ium iodide Chemical compound [I-].C[NH+]1CC=CC=C1 MDICIVRGHCTEQJ-UHFFFAOYSA-N 0.000 claims description 5
PSXRWZBTVAZNSF-UHFFFAOYSA-N hydron;quinoline;chloride Chemical compound Cl.N1=CC=CC2=CC=CC=C21 PSXRWZBTVAZNSF-UHFFFAOYSA-N 0.000 claims description 5
150000003856 quaternary ammonium compounds Chemical class 0.000 claims description 5
150000004023 quaternary phosphonium compounds Chemical class 0.000 claims description 5
KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims description 5
VFJYIHQDILEQNR-UHFFFAOYSA-M trimethylsulfanium;iodide Chemical compound [I-].C[S+](C)C VFJYIHQDILEQNR-UHFFFAOYSA-M 0.000 claims description 5
JBWKIWSBJXDJDT-UHFFFAOYSA-N triphenylmethyl chloride Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(Cl)C1=CC=CC=C1 JBWKIWSBJXDJDT-UHFFFAOYSA-N 0.000 claims description 5
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 4
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 4
BRKFQVAOMSWFDU-UHFFFAOYSA-M tetraphenylphosphanium;bromide Chemical compound [Br-].C1=CC=CC=C1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 BRKFQVAOMSWFDU-UHFFFAOYSA-M 0.000 claims description 4
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 3
235000011054 acetic acid Nutrition 0.000 claims description 3
235000019253 formic acid Nutrition 0.000 claims description 3
235000006408 oxalic acid Nutrition 0.000 claims description 3
KLBOFRLEHJAXIU-UHFFFAOYSA-N tributylazanium;chloride Chemical compound Cl.CCCCN(CCCC)CCCC KLBOFRLEHJAXIU-UHFFFAOYSA-N 0.000 claims description 3
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 2
229910000147 aluminium phosphate Inorganic materials 0.000 claims description 2
BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 claims description 2
229910017604 nitric acid Inorganic materials 0.000 claims description 2
235000019260 propionic acid Nutrition 0.000 claims description 2
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims description 2
239000001384 succinic acid Substances 0.000 claims description 2
150000001735 carboxylic acids Chemical class 0.000 claims 6
RSJLWBUYLGJOBD-UHFFFAOYSA-M diphenyliodanium;chloride Chemical compound [Cl-].C=1C=CC=CC=1[I+]C1=CC=CC=C1 RSJLWBUYLGJOBD-UHFFFAOYSA-M 0.000 claims 4
IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 claims 2
241000947840 Alteromonadales Species 0.000 claims 1
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims 1
PMOIAJVKYNVHQE-UHFFFAOYSA-N phosphanium;bromide Chemical compound [PH4+].[Br-] PMOIAJVKYNVHQE-UHFFFAOYSA-N 0.000 claims 1
150000001732 carboxylic acid derivatives Chemical class 0.000 abstract description 22
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 abstract 1
229910052740 iodine Inorganic materials 0.000 abstract 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 244
239000000243 solution Substances 0.000 description 118
238000006243 chemical reaction Methods 0.000 description 84
239000012044 organic layer Substances 0.000 description 83
239000002904 solvent Substances 0.000 description 53
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 51
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 42
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 41
238000003756 stirring Methods 0.000 description 33
239000010410 layer Substances 0.000 description 27
238000002156 mixing Methods 0.000 description 27
239000007864 aqueous solution Substances 0.000 description 26
150000007942 carboxylates Chemical class 0.000 description 26
DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 24
239000012535 impurity Substances 0.000 description 24
LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 21
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 21
PAYRUJLWNCNPSJ-UHFFFAOYSA-O phenylazanium Chemical compound [NH3+]C1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-O 0.000 description 21
239000007810 chemical reaction solvent Substances 0.000 description 20
239000013078 crystal Substances 0.000 description 20
125000001424 substituent group Chemical group 0.000 description 20
239000006227 byproduct Substances 0.000 description 19
239000007788 liquid Substances 0.000 description 19
SFSPUVKCNQHXPP-UHFFFAOYSA-N disodium dioxido-(2,3,4,5,6-pentafluorophenoxy)borane Chemical compound [Na+].B(OC1=C(C(=C(C(=C1F)F)F)F)F)([O-])[O-].[Na+] SFSPUVKCNQHXPP-UHFFFAOYSA-N 0.000 description 18
150000004820 halides Chemical class 0.000 description 18
229910052943 magnesium sulfate Inorganic materials 0.000 description 15
CSNNHWWHGAXBCP-UHFFFAOYSA-L magnesium sulphate Substances [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 15
235000019341 magnesium sulphate Nutrition 0.000 description 15
238000000926 separation method Methods 0.000 description 15
150000002430 hydrocarbons Chemical group 0.000 description 14
238000001914 filtration Methods 0.000 description 13
239000011259 mixed solution Substances 0.000 description 13
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 12
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 12
JLTDJTHDQAWBAV-UHFFFAOYSA-O dimethyl(phenyl)azanium Chemical compound C[NH+](C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-O 0.000 description 12
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
239000000047 product Substances 0.000 description 12
239000012968 metallocene catalyst Substances 0.000 description 11
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 10
239000000203 mixture Substances 0.000 description 10
238000005406 washing Methods 0.000 description 10
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 9
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
239000003054 catalyst Substances 0.000 description 9
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 8
RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 8
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 8
229910001514 alkali metal chloride Inorganic materials 0.000 description 8
150000001340 alkali metals Chemical class 0.000 description 8
RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 8
239000003426 co-catalyst Substances 0.000 description 8
239000006103 coloring component Substances 0.000 description 8
VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 8
239000000347 magnesium hydroxide Substances 0.000 description 8
229910001862 magnesium hydroxide Inorganic materials 0.000 description 8
239000004215 Carbon black (E152) Substances 0.000 description 7
125000004432 carbon atom Chemical group C* 0.000 description 7
239000004210 ether based solvent Substances 0.000 description 7
238000010438 heat treatment Methods 0.000 description 7
229930195733 hydrocarbon Natural products 0.000 description 7
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 6
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
238000003747 Grignard reaction Methods 0.000 description 6
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
239000001257 hydrogen Substances 0.000 description 6
229910052739 hydrogen Inorganic materials 0.000 description 6
229920001296 polysiloxane Polymers 0.000 description 6
238000010992 reflux Methods 0.000 description 6
229910000029 sodium carbonate Inorganic materials 0.000 description 6
WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 5
238000005481 NMR spectroscopy Methods 0.000 description 5
150000001338 aliphatic hydrocarbons Chemical class 0.000 description 5
150000004945 aromatic hydrocarbons Chemical class 0.000 description 5
238000009835 boiling Methods 0.000 description 5
125000002091 cationic group Chemical group 0.000 description 5
239000003153 chemical reaction reagent Substances 0.000 description 5
WJZSXQSWXGBZIQ-UHFFFAOYSA-N dilithium;dioxido-(2,3,4,5,6-pentafluorophenoxy)borane Chemical compound [Li+].[Li+].[O-]B([O-])OC1=C(F)C(F)=C(F)C(F)=C1F WJZSXQSWXGBZIQ-UHFFFAOYSA-N 0.000 description 5
238000000605 extraction Methods 0.000 description 5
238000006116 polymerization reaction Methods 0.000 description 5
229940074404 sodium succinate Drugs 0.000 description 5
ZDQYSKICYIVCPN-UHFFFAOYSA-L sodium succinate (anhydrous) Chemical compound [Na+].[Na+].[O-]C(=O)CCC([O-])=O ZDQYSKICYIVCPN-UHFFFAOYSA-L 0.000 description 5
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 4
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 4
239000007818 Grignard reagent Substances 0.000 description 4
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 4
239000005456 alcohol based solvent Substances 0.000 description 4
MTHSVFCYNBDYFN-UHFFFAOYSA-N anhydrous diethylene glycol Natural products OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 4
229910052796 boron Inorganic materials 0.000 description 4
238000004821 distillation Methods 0.000 description 4
239000003759 ester based solvent Substances 0.000 description 4
150000004795 grignard reagents Chemical class 0.000 description 4
DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 4
239000005453 ketone based solvent Substances 0.000 description 4
SGZHLLQPCVCEDC-UHFFFAOYSA-L magnesium;bromide;chloride Chemical compound Cl[Mg]Br SGZHLLQPCVCEDC-UHFFFAOYSA-L 0.000 description 4
OVCLXQXUDAEKFN-UHFFFAOYSA-L magnesium;bromide;fluoride Chemical compound [F-].[Mg+2].[Br-] OVCLXQXUDAEKFN-UHFFFAOYSA-L 0.000 description 4
UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
XEKTVXADUPBFOA-UHFFFAOYSA-N 1-bromo-2,3,4,5,6-pentafluorobenzene Chemical compound FC1=C(F)C(F)=C(Br)C(F)=C1F XEKTVXADUPBFOA-UHFFFAOYSA-N 0.000 description 3
WRWPPGUCZBJXKX-UHFFFAOYSA-N 1-fluoro-4-methylbenzene Chemical compound CC1=CC=C(F)C=C1 WRWPPGUCZBJXKX-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 3
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 3
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 3
IGURZGCFZZUZSD-UHFFFAOYSA-N [Li]c1c(F)c(F)c(F)c(F)c1F Chemical compound [Li]c1c(F)c(F)c(F)c(F)c1F IGURZGCFZZUZSD-UHFFFAOYSA-N 0.000 description 3
KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 3
150000007513 acids Chemical class 0.000 description 3
125000000217 alkyl group Chemical group 0.000 description 3
239000001110 calcium chloride Substances 0.000 description 3
229910001628 calcium chloride Inorganic materials 0.000 description 3
239000012295 chemical reaction liquid Substances 0.000 description 3
230000000694 effects Effects 0.000 description 3
235000019441 ethanol Nutrition 0.000 description 3
125000000524 functional group Chemical group 0.000 description 3
150000002642 lithium compounds Chemical class 0.000 description 3
159000000003 magnesium salts Chemical class 0.000 description 3
150000005309 metal halides Chemical class 0.000 description 3
125000000538 pentafluorophenyl group Chemical group FC1=C(F)C(F)=C(*)C(F)=C1F 0.000 description 3
229910052700 potassium Inorganic materials 0.000 description 3
239000011591 potassium Substances 0.000 description 3
230000035484 reaction time Effects 0.000 description 3
239000001632 sodium acetate Substances 0.000 description 3
235000017281 sodium acetate Nutrition 0.000 description 3
239000011780 sodium chloride Substances 0.000 description 3
LZDKZFUFMNSQCJ-UHFFFAOYSA-N 1,2-diethoxyethane Chemical compound CCOCCOCC LZDKZFUFMNSQCJ-UHFFFAOYSA-N 0.000 description 2
WPBRSJSZQSTTPX-UHFFFAOYSA-N 1-(2-heptoxyethoxy)heptane Chemical compound CCCCCCCOCCOCCCCCCC WPBRSJSZQSTTPX-UHFFFAOYSA-N 0.000 description 2
KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 2
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
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 2
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 2
OKIZCWYLBDKLSU-UHFFFAOYSA-M N,N,N-Trimethylmethanaminium chloride Chemical compound [Cl-].C[N+](C)(C)C OKIZCWYLBDKLSU-UHFFFAOYSA-M 0.000 description 2
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
239000001747 Potassium fumarate Substances 0.000 description 2
YDSUVZDWSFKZJZ-UHFFFAOYSA-M [Br-].[Mg+2].B([O-])(O)O Chemical compound [Br-].[Mg+2].B([O-])(O)O YDSUVZDWSFKZJZ-UHFFFAOYSA-M 0.000 description 2
230000002378 acidificating effect Effects 0.000 description 2
125000004423 acyloxy group Chemical group 0.000 description 2
239000003513 alkali Substances 0.000 description 2
125000003342 alkenyl group Chemical group 0.000 description 2
125000004414 alkyl thio group Chemical group 0.000 description 2
150000001450 anions Chemical class 0.000 description 2
ITHZDDVSAWDQPZ-UHFFFAOYSA-L barium acetate Chemical compound [Ba+2].CC([O-])=O.CC([O-])=O ITHZDDVSAWDQPZ-UHFFFAOYSA-L 0.000 description 2
AYJRCSIUFZENHW-UHFFFAOYSA-L barium carbonate Chemical compound [Ba+2].[O-]C([O-])=O AYJRCSIUFZENHW-UHFFFAOYSA-L 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
239000004305 biphenyl Substances 0.000 description 2
UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 2
150000004649 carbonic acid derivatives Chemical class 0.000 description 2
239000000460 chlorine Substances 0.000 description 2
125000006165 cyclic alkyl group Chemical group 0.000 description 2
125000004122 cyclic group Chemical group 0.000 description 2
239000002274 desiccant Substances 0.000 description 2
125000004663 dialkyl amino group Chemical group 0.000 description 2
SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 2
SHPKCSFVQGSAJU-UAIGNFCESA-L dipotassium;(z)-but-2-enedioate Chemical compound [K+].[K+].[O-]C(=O)\C=C/C([O-])=O SHPKCSFVQGSAJU-UAIGNFCESA-L 0.000 description 2
GIGWNNOCCCHECH-UHFFFAOYSA-L dipotassium;benzene-1,3-dicarboxylate Chemical compound [K+].[K+].[O-]C(=O)C1=CC=CC(C([O-])=O)=C1 GIGWNNOCCCHECH-UHFFFAOYSA-L 0.000 description 2
CVOQYKPWIVSMDC-UHFFFAOYSA-L dipotassium;butanedioate Chemical compound [K+].[K+].[O-]C(=O)CCC([O-])=O CVOQYKPWIVSMDC-UHFFFAOYSA-L 0.000 description 2
IRXRGVFLQOSHOH-UHFFFAOYSA-L dipotassium;oxalate Chemical compound [K+].[K+].[O-]C(=O)C([O-])=O IRXRGVFLQOSHOH-UHFFFAOYSA-L 0.000 description 2
HCDITHVDEPPNIL-UHFFFAOYSA-L dipotassium;propanedioate Chemical compound [K+].[K+].[O-]C(=O)CC([O-])=O HCDITHVDEPPNIL-UHFFFAOYSA-L 0.000 description 2
LRUDDHYVRFQYCN-UHFFFAOYSA-L dipotassium;terephthalate Chemical compound [K+].[K+].[O-]C(=O)C1=CC=C(C([O-])=O)C=C1 LRUDDHYVRFQYCN-UHFFFAOYSA-L 0.000 description 2
MSJMDZAOKORVFC-SEPHDYHBSA-L disodium fumarate Chemical compound [Na+].[Na+].[O-]C(=O)\C=C\C([O-])=O MSJMDZAOKORVFC-SEPHDYHBSA-L 0.000 description 2
MSJMDZAOKORVFC-UAIGNFCESA-L disodium maleate Chemical compound [Na+].[Na+].[O-]C(=O)\C=C/C([O-])=O MSJMDZAOKORVFC-UAIGNFCESA-L 0.000 description 2
GZCKIUIIYCBICZ-UHFFFAOYSA-L disodium;benzene-1,3-dicarboxylate Chemical compound [Na+].[Na+].[O-]C(=O)C1=CC=CC(C([O-])=O)=C1 GZCKIUIIYCBICZ-UHFFFAOYSA-L 0.000 description 2
HQWKKEIVHQXCPI-UHFFFAOYSA-L disodium;phthalate Chemical compound [Na+].[Na+].[O-]C(=O)C1=CC=CC=C1C([O-])=O HQWKKEIVHQXCPI-UHFFFAOYSA-L 0.000 description 2
VIQSRHWJEKERKR-UHFFFAOYSA-L disodium;terephthalate Chemical compound [Na+].[Na+].[O-]C(=O)C1=CC=C(C([O-])=O)C=C1 VIQSRHWJEKERKR-UHFFFAOYSA-L 0.000 description 2
125000005842 heteroatom Chemical group 0.000 description 2
150000004678 hydrides Chemical class 0.000 description 2
229910052744 lithium Inorganic materials 0.000 description 2
XGZVUEUWXADBQD-UHFFFAOYSA-L lithium carbonate Chemical compound [Li+].[Li+].[O-]C([O-])=O XGZVUEUWXADBQD-UHFFFAOYSA-L 0.000 description 2
229910052808 lithium carbonate Inorganic materials 0.000 description 2
UBJFKNSINUCEAL-UHFFFAOYSA-N lithium;2-methylpropane Chemical compound [Li+].C[C-](C)C UBJFKNSINUCEAL-UHFFFAOYSA-N 0.000 description 2
AMQDBUIQKQUCKY-UHFFFAOYSA-M magnesium;1,2,3,4,5-pentafluorobenzene-6-ide;bromide Chemical compound [Mg+2].[Br-].FC1=[C-]C(F)=C(F)C(F)=C1F AMQDBUIQKQUCKY-UHFFFAOYSA-M 0.000 description 2
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
150000007522 mineralic acids Chemical class 0.000 description 2
150000007524 organic acids Chemical class 0.000 description 2
125000002524 organometallic group Chemical group 0.000 description 2
125000004430 oxygen atom Chemical group O* 0.000 description 2
SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
229910000027 potassium carbonate Inorganic materials 0.000 description 2
SHPKCSFVQGSAJU-SEPHDYHBSA-L potassium fumarate Chemical compound [K+].[K+].[O-]C(=O)\C=C\C([O-])=O SHPKCSFVQGSAJU-SEPHDYHBSA-L 0.000 description 2
235000019295 potassium fumarate Nutrition 0.000 description 2
AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 2
239000011734 sodium Substances 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
PRWXGRGLHYDWPS-UHFFFAOYSA-L sodium malonate Chemical compound [Na+].[Na+].[O-]C(=O)CC([O-])=O PRWXGRGLHYDWPS-UHFFFAOYSA-L 0.000 description 2
ZNCPFRVNHGOPAG-UHFFFAOYSA-L sodium oxalate Chemical compound [Na+].[Na+].[O-]C(=O)C([O-])=O ZNCPFRVNHGOPAG-UHFFFAOYSA-L 0.000 description 2
229940039790 sodium oxalate Drugs 0.000 description 2
239000007787 solid Substances 0.000 description 2
239000007858 starting material Substances 0.000 description 2
FAQYAMRNWDIXMY-UHFFFAOYSA-N trichloroborane Chemical compound ClB(Cl)Cl FAQYAMRNWDIXMY-UHFFFAOYSA-N 0.000 description 2
NFMWFGXCDDYTEG-UHFFFAOYSA-N trimagnesium;diborate Chemical compound [Mg+2].[Mg+2].[Mg+2].[O-]B([O-])[O-].[O-]B([O-])[O-] NFMWFGXCDDYTEG-UHFFFAOYSA-N 0.000 description 2
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
WACNXHCZHTVBJM-UHFFFAOYSA-N 1,2,3,4,5-pentafluorobenzene Chemical compound FC1=CC(F)=C(F)C(F)=C1F WACNXHCZHTVBJM-UHFFFAOYSA-N 0.000 description 1
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GDXHBFHOEYVPED-UHFFFAOYSA-N 1-(2-butoxyethoxy)butane Chemical compound CCCCOCCOCCCC GDXHBFHOEYVPED-UHFFFAOYSA-N 0.000 description 1
HOPNGFMODYIPJK-UHFFFAOYSA-N 1-(2-decoxyethoxy)decane Chemical compound CCCCCCCCCCOCCOCCCCCCCCCC HOPNGFMODYIPJK-UHFFFAOYSA-N 0.000 description 1
ITZAHBOREXAZFQ-UHFFFAOYSA-N 1-(2-hexoxyethoxy)hexane Chemical compound CCCCCCOCCOCCCCCC ITZAHBOREXAZFQ-UHFFFAOYSA-N 0.000 description 1
XDFQEFFBRPGSMC-UHFFFAOYSA-N 1-(2-methoxyethoxy)butane Chemical compound CCCCOCCOC XDFQEFFBRPGSMC-UHFFFAOYSA-N 0.000 description 1
RJUOZXIPZCACCT-UHFFFAOYSA-N 1-(2-nonoxyethoxy)nonane Chemical compound CCCCCCCCCOCCOCCCCCCCCC RJUOZXIPZCACCT-UHFFFAOYSA-N 0.000 description 1
SJMBETQHZHCXGR-UHFFFAOYSA-N 1-(2-octoxyethoxy)octane Chemical compound CCCCCCCCOCCOCCCCCCCC SJMBETQHZHCXGR-UHFFFAOYSA-N 0.000 description 1
LNVSOMKWPGPNOJ-UHFFFAOYSA-N 1-(2-pentoxyethoxy)pentane Chemical compound CCCCCOCCOCCCCC LNVSOMKWPGPNOJ-UHFFFAOYSA-N 0.000 description 1
HQSLKNLISLWZQH-UHFFFAOYSA-N 1-(2-propoxyethoxy)propane Chemical compound CCCOCCOCCC HQSLKNLISLWZQH-UHFFFAOYSA-N 0.000 description 1
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VOIWQNVWCVIHPK-UHFFFAOYSA-N 1-[2-(2-decoxyethoxy)ethoxy]decane Chemical compound CCCCCCCCCCOCCOCCOCCCCCCCCCC VOIWQNVWCVIHPK-UHFFFAOYSA-N 0.000 description 1
SQMGATPYMSUPSP-UHFFFAOYSA-N 1-[2-(2-heptoxyethoxy)ethoxy]heptane Chemical compound CCCCCCCOCCOCCOCCCCCCC SQMGATPYMSUPSP-UHFFFAOYSA-N 0.000 description 1
QRUDYUQVHZEMPL-UHFFFAOYSA-N 1-[2-(2-hexoxyethoxy)ethoxy]hexane Chemical compound CCCCCCOCCOCCOCCCCCC QRUDYUQVHZEMPL-UHFFFAOYSA-N 0.000 description 1
DIFUQOVFDQFPBC-UHFFFAOYSA-N 1-[2-(2-nonoxyethoxy)ethoxy]nonane Chemical compound CCCCCCCCCOCCOCCOCCCCCCCCC DIFUQOVFDQFPBC-UHFFFAOYSA-N 0.000 description 1
MMVAEMFNVQIXIP-UHFFFAOYSA-N 1-[2-(2-octoxyethoxy)ethoxy]octane Chemical compound CCCCCCCCOCCOCCOCCCCCCCC MMVAEMFNVQIXIP-UHFFFAOYSA-N 0.000 description 1
YXOUPUFJBBFWNL-UHFFFAOYSA-N 1-[2-(2-pentoxyethoxy)ethoxy]pentane Chemical compound CCCCCOCCOCCOCCCCC YXOUPUFJBBFWNL-UHFFFAOYSA-N 0.000 description 1
KTSVVTQTKRGWGU-UHFFFAOYSA-N 1-[2-[2-(2-butoxyethoxy)ethoxy]ethoxy]butane Chemical compound CCCCOCCOCCOCCOCCCC KTSVVTQTKRGWGU-UHFFFAOYSA-N 0.000 description 1
AJUPTXPBZVRCQU-UHFFFAOYSA-N 1-[2-[2-(2-decoxyethoxy)ethoxy]ethoxy]decane Chemical compound CCCCCCCCCCOCCOCCOCCOCCCCCCCCCC AJUPTXPBZVRCQU-UHFFFAOYSA-N 0.000 description 1
HCPHTHRRUHDXNQ-UHFFFAOYSA-N 1-[2-[2-(2-heptoxyethoxy)ethoxy]ethoxy]heptane Chemical compound CCCCCCCOCCOCCOCCOCCCCCCC HCPHTHRRUHDXNQ-UHFFFAOYSA-N 0.000 description 1
VBHMJWLHXICEGS-UHFFFAOYSA-N 1-[2-[2-(2-hexoxyethoxy)ethoxy]ethoxy]hexane Chemical compound CCCCCCOCCOCCOCCOCCCCCC VBHMJWLHXICEGS-UHFFFAOYSA-N 0.000 description 1
PNUGRVLEGLTCJN-UHFFFAOYSA-N 1-[2-[2-(2-nonoxyethoxy)ethoxy]ethoxy]nonane Chemical compound CCCCCCCCCOCCOCCOCCOCCCCCCCCC PNUGRVLEGLTCJN-UHFFFAOYSA-N 0.000 description 1
FTVMYCYPAGFMOX-UHFFFAOYSA-N 1-[2-[2-(2-octoxyethoxy)ethoxy]ethoxy]octane Chemical compound CCCCCCCCOCCOCCOCCOCCCCCCCC FTVMYCYPAGFMOX-UHFFFAOYSA-N 0.000 description 1
POCXWZAVSAVPBV-UHFFFAOYSA-N 1-[2-[2-(2-pentoxyethoxy)ethoxy]ethoxy]pentane Chemical compound CCCCCOCCOCCOCCOCCCCC POCXWZAVSAVPBV-UHFFFAOYSA-N 0.000 description 1
NDZFNTHGIIQMQI-UHFFFAOYSA-N 1-benzylpyridin-1-ium Chemical compound C=1C=CC=C[N+]=1CC1=CC=CC=C1 NDZFNTHGIIQMQI-UHFFFAOYSA-N 0.000 description 1
RRQYJINTUHWNHW-UHFFFAOYSA-N 1-ethoxy-2-(2-ethoxyethoxy)ethane Chemical compound CCOCCOCCOCC RRQYJINTUHWNHW-UHFFFAOYSA-N 0.000 description 1
KIAMPLQEZAMORJ-UHFFFAOYSA-N 1-ethoxy-2-[2-(2-ethoxyethoxy)ethoxy]ethane Chemical compound CCOCCOCCOCCOCC KIAMPLQEZAMORJ-UHFFFAOYSA-N 0.000 description 1
CAQYAZNFWDDMIT-UHFFFAOYSA-N 1-ethoxy-2-methoxyethane Chemical compound CCOCCOC CAQYAZNFWDDMIT-UHFFFAOYSA-N 0.000 description 1
IKOGEPVQXKWROD-UHFFFAOYSA-N 1-methyl-2H-quinoline hydroiodide Chemical compound I.C1=CC=C2N(C)CC=CC2=C1 IKOGEPVQXKWROD-UHFFFAOYSA-N 0.000 description 1
CCHRVFZBKRIKIX-UHFFFAOYSA-N 1-nitro-3-(3-nitrophenyl)benzene Chemical compound [O-][N+](=O)C1=CC=CC(C=2C=C(C=CC=2)[N+]([O-])=O)=C1 CCHRVFZBKRIKIX-UHFFFAOYSA-N 0.000 description 1
RWYRUDPAALLKPX-UHFFFAOYSA-N 2,2-difluoro-n-methylethanamine;hydrochloride Chemical compound Cl.CNCC(F)F RWYRUDPAALLKPX-UHFFFAOYSA-N 0.000 description 1
GDKBMZHEWBEYRO-UHFFFAOYSA-N 2-(2-butan-2-yloxyethoxy)butane Chemical compound CCC(C)OCCOC(C)CC GDKBMZHEWBEYRO-UHFFFAOYSA-N 0.000 description 1
WFTWWOCWRSUGAW-UHFFFAOYSA-N 2-(2-ethoxyethoxy)ethyl 2-methylprop-2-enoate Chemical compound CCOCCOCCOC(=O)C(C)=C WFTWWOCWRSUGAW-UHFFFAOYSA-N 0.000 description 1
FPZWZCWUIYYYBU-UHFFFAOYSA-N 2-(2-ethoxyethoxy)ethyl acetate Chemical compound CCOCCOCCOC(C)=O FPZWZCWUIYYYBU-UHFFFAOYSA-N 0.000 description 1
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PICKZMGDVSSGSC-UHFFFAOYSA-N 2-(2-phenoxyethoxy)ethoxybenzene Chemical compound C=1C=CC=CC=1OCCOCCOC1=CC=CC=C1 PICKZMGDVSSGSC-UHFFFAOYSA-N 0.000 description 1
MGZCLRWCEUBEGO-UHFFFAOYSA-N 2-(2-propan-2-yloxyethoxy)propane Chemical compound CC(C)OCCOC(C)C MGZCLRWCEUBEGO-UHFFFAOYSA-N 0.000 description 1
UJVWKSNORBRUEC-UHFFFAOYSA-N 2-[2-(2-phenoxyethoxy)ethoxy]ethoxybenzene Chemical compound C=1C=CC=CC=1OCCOCCOCCOC1=CC=CC=C1 UJVWKSNORBRUEC-UHFFFAOYSA-N 0.000 description 1
JHOOWURXQGAXHL-UHFFFAOYSA-N 2-[2-(2-propan-2-yloxyethoxy)ethoxy]propane Chemical compound CC(C)OCCOCCOC(C)C JHOOWURXQGAXHL-UHFFFAOYSA-N 0.000 description 1
AHTTUKMNYVZLFF-UHFFFAOYSA-N 2-[2-[2-(2-propan-2-yloxyethoxy)ethoxy]ethoxy]propane Chemical compound CC(C)OCCOCCOCCOC(C)C AHTTUKMNYVZLFF-UHFFFAOYSA-N 0.000 description 1
LGKBIIKPZIIDHT-UHFFFAOYSA-N 2-cyclobutyloxyethoxycyclobutane Chemical compound C1CCC1OCCOC1CCC1 LGKBIIKPZIIDHT-UHFFFAOYSA-N 0.000 description 1
FHLUMPZKGGHIST-UHFFFAOYSA-N 2-cyclodecyloxyethoxycyclodecane Chemical compound C1CCCCCCCCC1OCCOC1CCCCCCCCC1 FHLUMPZKGGHIST-UHFFFAOYSA-N 0.000 description 1
BZMBUESLPUFNLJ-UHFFFAOYSA-N 2-cyclohexyloxyethoxycyclohexane Chemical compound C1CCCCC1OCCOC1CCCCC1 BZMBUESLPUFNLJ-UHFFFAOYSA-N 0.000 description 1
MLHQCGDKZKPWGA-UHFFFAOYSA-N 2-cyclononyloxyethoxycyclononane Chemical compound C1CCCCCCCC1OCCOC1CCCCCCCC1 MLHQCGDKZKPWGA-UHFFFAOYSA-N 0.000 description 1
WPNGNEXOCBFJME-UHFFFAOYSA-N 2-cyclooctyloxyethoxycyclooctane Chemical compound C1CCCCCCC1OCCOC1CCCCCCC1 WPNGNEXOCBFJME-UHFFFAOYSA-N 0.000 description 1
NQIJAAURIDJBPB-UHFFFAOYSA-N 2-cyclopentyloxyethoxycyclopentane Chemical compound C1CCCC1OCCOC1CCCC1 NQIJAAURIDJBPB-UHFFFAOYSA-N 0.000 description 1
OZFRHKYRLXXBHW-UHFFFAOYSA-N 2-cyclopropyloxyethoxycyclopropane Chemical compound C1CC1OCCOC1CC1 OZFRHKYRLXXBHW-UHFFFAOYSA-N 0.000 description 1
PWNZQSUHTOQNEK-UHFFFAOYSA-N 2-methyl-1-[2-(2-methylpropoxy)ethoxy]propane Chemical compound CC(C)COCCOCC(C)C PWNZQSUHTOQNEK-UHFFFAOYSA-N 0.000 description 1
KWGJJEBPCVMBIG-UHFFFAOYSA-N 2-methyl-2-[2-[(2-methylpropan-2-yl)oxy]ethoxy]propane Chemical compound CC(C)(C)OCCOC(C)(C)C KWGJJEBPCVMBIG-UHFFFAOYSA-N 0.000 description 1
CRWNQZTZTZWPOF-UHFFFAOYSA-N 2-methyl-4-phenylpyridine Chemical compound C1=NC(C)=CC(C=2C=CC=CC=2)=C1 CRWNQZTZTZWPOF-UHFFFAOYSA-N 0.000 description 1
VAPQAGMSICPBKJ-UHFFFAOYSA-N 2-nitroacridine Chemical compound C1=CC=CC2=CC3=CC([N+](=O)[O-])=CC=C3N=C21 VAPQAGMSICPBKJ-UHFFFAOYSA-N 0.000 description 1
XCSGHNKDXGYELG-UHFFFAOYSA-N 2-phenoxyethoxybenzene Chemical compound C=1C=CC=CC=1OCCOC1=CC=CC=C1 XCSGHNKDXGYELG-UHFFFAOYSA-N 0.000 description 1
REVVFBIOIFGJRH-JTQLQIEISA-N 4-[[(2s)-1-hydroxybutan-2-yl]amino]benzaldehyde Chemical compound CC[C@@H](CO)NC1=CC=C(C=O)C=C1 REVVFBIOIFGJRH-JTQLQIEISA-N 0.000 description 1
OURWKHLDAVYMGO-UHFFFAOYSA-N 7-thiophen-2-ylpyrazolo[1,5-a]pyrimidine-3-carboxylic acid Chemical compound C=1C=NC2=C(C(=O)O)C=NN2C=1C1=CC=CS1 OURWKHLDAVYMGO-UHFFFAOYSA-N 0.000 description 1
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
CBOCVOKPQGJKKJ-UHFFFAOYSA-L Calcium formate Chemical compound [Ca+2].[O-]C=O.[O-]C=O CBOCVOKPQGJKKJ-UHFFFAOYSA-L 0.000 description 1
239000001749 Calcium fumarate Substances 0.000 description 1
BCZXFFBUYPCTSJ-UHFFFAOYSA-L Calcium propionate Chemical compound [Ca+2].CCC([O-])=O.CCC([O-])=O BCZXFFBUYPCTSJ-UHFFFAOYSA-L 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
PQBAWAQIRZIWIV-UHFFFAOYSA-N N-methylpyridinium Chemical compound C[N+]1=CC=CC=C1 PQBAWAQIRZIWIV-UHFFFAOYSA-N 0.000 description 1
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
239000004280 Sodium formate Substances 0.000 description 1
239000001744 Sodium fumarate Substances 0.000 description 1
DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 description 1
239000007983 Tris buffer Substances 0.000 description 1
230000004913 activation Effects 0.000 description 1
150000001447 alkali salts Chemical class 0.000 description 1
125000002947 alkylene group Chemical group 0.000 description 1
125000005336 allyloxy group Chemical group 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
125000005110 aryl thio group Chemical group 0.000 description 1
125000004104 aryloxy group Chemical group 0.000 description 1
229910052788 barium Inorganic materials 0.000 description 1
229940112016 barium acetate Drugs 0.000 description 1
DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical compound [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 description 1
229910001863 barium hydroxide Inorganic materials 0.000 description 1
GXUARMXARIJAFV-UHFFFAOYSA-L barium oxalate Chemical compound [Ba+2].[O-]C(=O)C([O-])=O GXUARMXARIJAFV-UHFFFAOYSA-L 0.000 description 1
229940094800 barium oxalate Drugs 0.000 description 1
YXUUWXPIZZLNIO-TYYBGVCCSA-L barium(2+);(e)-but-2-enedioate Chemical compound [Ba+2].[O-]C(=O)\C=C\C([O-])=O YXUUWXPIZZLNIO-TYYBGVCCSA-L 0.000 description 1
YXUUWXPIZZLNIO-ODZAUARKSA-L barium(2+);(z)-but-2-enedioate Chemical compound [Ba+2].[O-]C(=O)\C=C/C([O-])=O YXUUWXPIZZLNIO-ODZAUARKSA-L 0.000 description 1
AQWQXYNDBMAJES-UHFFFAOYSA-L barium(2+);benzene-1,3-dicarboxylate Chemical compound [Ba+2].[O-]C(=O)C1=CC=CC(C([O-])=O)=C1 AQWQXYNDBMAJES-UHFFFAOYSA-L 0.000 description 1
HFAQXXPQBRIXGD-UHFFFAOYSA-L barium(2+);butanedioate Chemical compound [Ba+2].[O-]C(=O)CCC([O-])=O HFAQXXPQBRIXGD-UHFFFAOYSA-L 0.000 description 1
MJIAXOYYJWECDI-UHFFFAOYSA-L barium(2+);dibenzoate Chemical compound [Ba+2].[O-]C(=O)C1=CC=CC=C1.[O-]C(=O)C1=CC=CC=C1 MJIAXOYYJWECDI-UHFFFAOYSA-L 0.000 description 1
UXFOSWFWQAUFFZ-UHFFFAOYSA-L barium(2+);diformate Chemical compound [Ba+2].[O-]C=O.[O-]C=O UXFOSWFWQAUFFZ-UHFFFAOYSA-L 0.000 description 1
MTZOKGSUOABQEO-UHFFFAOYSA-L barium(2+);phthalate Chemical compound [Ba+2].[O-]C(=O)C1=CC=CC=C1C([O-])=O MTZOKGSUOABQEO-UHFFFAOYSA-L 0.000 description 1
NINLDBMTAAKRTR-UHFFFAOYSA-L barium(2+);propanedioate Chemical compound [Ba+2].[O-]C(=O)CC([O-])=O NINLDBMTAAKRTR-UHFFFAOYSA-L 0.000 description 1
SEOKMRXFVOVAIL-UHFFFAOYSA-L barium(2+);terephthalate Chemical compound [Ba+2].[O-]C(=O)C1=CC=C(C([O-])=O)C=C1 SEOKMRXFVOVAIL-UHFFFAOYSA-L 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
235000010290 biphenyl Nutrition 0.000 description 1
125000006267 biphenyl group Chemical group 0.000 description 1
229910000085 borane Inorganic materials 0.000 description 1
HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 1
KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
QOQHDJZWGSAHFL-UHFFFAOYSA-N butylphosphanium;bromide Chemical compound [Br-].CCCC[PH3+] QOQHDJZWGSAHFL-UHFFFAOYSA-N 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
239000011575 calcium Substances 0.000 description 1
VSGNNIFQASZAOI-UHFFFAOYSA-L calcium acetate Chemical compound [Ca+2].CC([O-])=O.CC([O-])=O VSGNNIFQASZAOI-UHFFFAOYSA-L 0.000 description 1
235000011092 calcium acetate Nutrition 0.000 description 1
239000001639 calcium acetate Substances 0.000 description 1
229960005147 calcium acetate Drugs 0.000 description 1
235000010237 calcium benzoate Nutrition 0.000 description 1
239000004301 calcium benzoate Substances 0.000 description 1
229910000019 calcium carbonate Inorganic materials 0.000 description 1
AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
239000004281 calcium formate Substances 0.000 description 1
235000019255 calcium formate Nutrition 0.000 description 1
229940044172 calcium formate Drugs 0.000 description 1
235000019296 calcium fumarate Nutrition 0.000 description 1
239000000920 calcium hydroxide Substances 0.000 description 1
229910001861 calcium hydroxide Inorganic materials 0.000 description 1
QXDMQSPYEZFLGF-UHFFFAOYSA-L calcium oxalate Chemical compound [Ca+2].[O-]C(=O)C([O-])=O QXDMQSPYEZFLGF-UHFFFAOYSA-L 0.000 description 1
235000010331 calcium propionate Nutrition 0.000 description 1
239000004330 calcium propionate Substances 0.000 description 1
HDRTWMBOUSPQON-ODZAUARKSA-L calcium;(z)-but-2-enedioate Chemical compound [Ca+2].[O-]C(=O)\C=C/C([O-])=O HDRTWMBOUSPQON-ODZAUARKSA-L 0.000 description 1
OAKHANKSRIPFCE-UHFFFAOYSA-L calcium;2-methylprop-2-enoate Chemical compound [Ca+2].CC(=C)C([O-])=O.CC(=C)C([O-])=O OAKHANKSRIPFCE-UHFFFAOYSA-L 0.000 description 1
MZQHAPMLAQRTTD-UHFFFAOYSA-L calcium;benzene-1,3-dicarboxylate Chemical compound [Ca+2].[O-]C(=O)C1=CC=CC(C([O-])=O)=C1 MZQHAPMLAQRTTD-UHFFFAOYSA-L 0.000 description 1
PBUBJNYXWIDFMU-UHFFFAOYSA-L calcium;butanedioate Chemical compound [Ca+2].[O-]C(=O)CCC([O-])=O PBUBJNYXWIDFMU-UHFFFAOYSA-L 0.000 description 1
HZQXCUSDXIKLGS-UHFFFAOYSA-L calcium;dibenzoate;trihydrate Chemical compound O.O.O.[Ca+2].[O-]C(=O)C1=CC=CC=C1.[O-]C(=O)C1=CC=CC=C1 HZQXCUSDXIKLGS-UHFFFAOYSA-L 0.000 description 1
PYSZASIZWHHPHJ-UHFFFAOYSA-L calcium;phthalate Chemical compound [Ca+2].[O-]C(=O)C1=CC=CC=C1C([O-])=O PYSZASIZWHHPHJ-UHFFFAOYSA-L 0.000 description 1
TXTCTCUXLQYGLA-UHFFFAOYSA-L calcium;prop-2-enoate Chemical compound [Ca+2].[O-]C(=O)C=C.[O-]C(=O)C=C TXTCTCUXLQYGLA-UHFFFAOYSA-L 0.000 description 1
MLMODXBPCNLAGP-UHFFFAOYSA-L calcium;propanedioate Chemical compound [Ca+2].[O-]C(=O)CC([O-])=O MLMODXBPCNLAGP-UHFFFAOYSA-L 0.000 description 1
AAEHPKIXIIACPQ-UHFFFAOYSA-L calcium;terephthalate Chemical compound [Ca+2].[O-]C(=O)C1=CC=C(C([O-])=O)C=C1 AAEHPKIXIIACPQ-UHFFFAOYSA-L 0.000 description 1
125000005517 carbenium group Chemical group 0.000 description 1
238000010538 cationic polymerization reaction Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
239000012043 crude product Substances 0.000 description 1
125000000000 cycloalkoxy group Chemical group 0.000 description 1
125000000753 cycloalkyl group Chemical group 0.000 description 1
125000002933 cyclohexyloxy group Chemical group C1(CCCCC1)O* 0.000 description 1
239000012955 diaryliodonium Substances 0.000 description 1
229940019778 diethylene glycol diethyl ether Drugs 0.000 description 1
HASCQPSFPAKVEK-UHFFFAOYSA-O dimethyl(phenyl)phosphanium Chemical compound C[PH+](C)C1=CC=CC=C1 HASCQPSFPAKVEK-UHFFFAOYSA-O 0.000 description 1
OZLBDYMWFAHSOQ-UHFFFAOYSA-N diphenyliodanium Chemical compound C=1C=CC=CC=1[I+]C1=CC=CC=C1 OZLBDYMWFAHSOQ-UHFFFAOYSA-N 0.000 description 1
GOMCKELMLXHYHH-UHFFFAOYSA-L dipotassium;phthalate Chemical compound [K+].[K+].[O-]C(=O)C1=CC=CC=C1C([O-])=O GOMCKELMLXHYHH-UHFFFAOYSA-L 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
125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
229920001002 functional polymer Polymers 0.000 description 1
125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
SMWDFEZZVXVKRB-UHFFFAOYSA-O hydron;quinoline Chemical compound [NH+]1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-O 0.000 description 1
150000004679 hydroxides Chemical class 0.000 description 1
125000002510 isobutoxy group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])O* 0.000 description 1
125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 1
AWJUIBRHMBBTKR-UHFFFAOYSA-O isoquinolin-2-ium Chemical compound C1=[NH+]C=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-O 0.000 description 1
ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
239000001095 magnesium carbonate Substances 0.000 description 1
229910000021 magnesium carbonate Inorganic materials 0.000 description 1
229910001629 magnesium chloride Inorganic materials 0.000 description 1
BLQJIBCZHWBKSL-UHFFFAOYSA-L magnesium iodide Chemical compound [Mg+2].[I-].[I-] BLQJIBCZHWBKSL-UHFFFAOYSA-L 0.000 description 1
229910001641 magnesium iodide Inorganic materials 0.000 description 1
150000002739 metals Chemical class 0.000 description 1
AFBPFSWMIHJQDM-UHFFFAOYSA-O methyl(phenyl)azanium Chemical compound C[NH2+]C1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-O 0.000 description 1
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
239000000178 monomer Substances 0.000 description 1
OSFCMRGOZNQUSW-UHFFFAOYSA-N n-[4-[2-(6,7-dimethoxy-3,4-dihydro-1h-isoquinolin-2-yl)ethyl]phenyl]-5-methoxy-9-oxo-10h-acridine-4-carboxamide Chemical compound N1C2=C(OC)C=CC=C2C(=O)C2=C1C(C(=O)NC1=CC=C(C=C1)CCN1CCC=3C=C(C(=CC=3C1)OC)OC)=CC=C2 OSFCMRGOZNQUSW-UHFFFAOYSA-N 0.000 description 1
125000006606 n-butoxy group Chemical group 0.000 description 1
125000003506 n-propoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 description 1
239000002798 polar solvent Substances 0.000 description 1
239000003505 polymerization initiator Substances 0.000 description 1
229920000098 polyolefin Polymers 0.000 description 1
235000011056 potassium acetate Nutrition 0.000 description 1
229960004109 potassium acetate Drugs 0.000 description 1
XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
235000010235 potassium benzoate Nutrition 0.000 description 1
239000004300 potassium benzoate Substances 0.000 description 1
229940103091 potassium benzoate Drugs 0.000 description 1
WFIZEGIEIOHZCP-UHFFFAOYSA-M potassium formate Chemical compound [K+].[O-]C=O WFIZEGIEIOHZCP-UHFFFAOYSA-M 0.000 description 1
IWZKICVEHNUQTL-UHFFFAOYSA-M potassium hydrogen phthalate Chemical compound [K+].OC(=O)C1=CC=CC=C1C([O-])=O IWZKICVEHNUQTL-UHFFFAOYSA-M 0.000 description 1
BWILYWWHXDGKQA-UHFFFAOYSA-M potassium propanoate Chemical compound [K+].CCC([O-])=O BWILYWWHXDGKQA-UHFFFAOYSA-M 0.000 description 1
235000010332 potassium propionate Nutrition 0.000 description 1
239000004331 potassium propionate Substances 0.000 description 1
LLLCSBYSPJHDJX-UHFFFAOYSA-M potassium;2-methylprop-2-enoate Chemical compound [K+].CC(=C)C([O-])=O LLLCSBYSPJHDJX-UHFFFAOYSA-M 0.000 description 1
230000001737 promoting effect Effects 0.000 description 1
JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 description 1
125000005920 sec-butoxy group Chemical group 0.000 description 1
125000004469 siloxy group Chemical group [SiH3]O* 0.000 description 1
229960004249 sodium acetate Drugs 0.000 description 1
229940047670 sodium acrylate Drugs 0.000 description 1
WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
235000010234 sodium benzoate Nutrition 0.000 description 1
239000004299 sodium benzoate Substances 0.000 description 1
HLBBKKJFGFRGMU-UHFFFAOYSA-M sodium formate Chemical compound [Na+].[O-]C=O HLBBKKJFGFRGMU-UHFFFAOYSA-M 0.000 description 1
235000019254 sodium formate Nutrition 0.000 description 1
235000019294 sodium fumarate Nutrition 0.000 description 1
229940005573 sodium fumarate Drugs 0.000 description 1
JXKPEJDQGNYQSM-UHFFFAOYSA-M sodium propionate Chemical compound [Na+].CCC([O-])=O JXKPEJDQGNYQSM-UHFFFAOYSA-M 0.000 description 1
235000010334 sodium propionate Nutrition 0.000 description 1
239000004324 sodium propionate Substances 0.000 description 1
229960003212 sodium propionate Drugs 0.000 description 1
SONHXMAHPHADTF-UHFFFAOYSA-M sodium;2-methylprop-2-enoate Chemical compound [Na+].CC(=C)C([O-])=O SONHXMAHPHADTF-UHFFFAOYSA-M 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
238000000967 suction filtration Methods 0.000 description 1
125000004434 sulfur atom Chemical group 0.000 description 1
230000004083 survival effect Effects 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
230000002194 synthesizing effect Effects 0.000 description 1
125000005207 tetraalkylammonium group Chemical group 0.000 description 1
125000005497 tetraalkylphosphonium group Chemical group 0.000 description 1
DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 1
CBXCPBUEXACCNR-UHFFFAOYSA-N tetraethylammonium Chemical compound CC[N+](CC)(CC)CC CBXCPBUEXACCNR-UHFFFAOYSA-N 0.000 description 1
SZWHXXNVLACKBV-UHFFFAOYSA-N tetraethylphosphanium Chemical compound CC[P+](CC)(CC)CC SZWHXXNVLACKBV-UHFFFAOYSA-N 0.000 description 1
125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
USFPINLPPFWTJW-UHFFFAOYSA-N tetraphenylphosphonium Chemical compound C1=CC=CC=C1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 USFPINLPPFWTJW-UHFFFAOYSA-N 0.000 description 1
125000005208 trialkylammonium group Chemical group 0.000 description 1
IMFACGCPASFAPR-UHFFFAOYSA-O tributylazanium Chemical compound CCCC[NH+](CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-O 0.000 description 1
ZMANZCXQSJIPKH-UHFFFAOYSA-O triethylammonium ion Chemical compound CC[NH+](CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-O 0.000 description 1
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
YFNKIDBQEZZDLK-UHFFFAOYSA-N triglyme Chemical compound COCCOCCOCCOC YFNKIDBQEZZDLK-UHFFFAOYSA-N 0.000 description 1
GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 1
125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 1
125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
NRZWQKGABZFFKE-UHFFFAOYSA-N trimethylsulfonium Chemical compound C[S+](C)C NRZWQKGABZFFKE-UHFFFAOYSA-N 0.000 description 1
RIOQSEWOXXDEQQ-UHFFFAOYSA-O triphenylphosphanium Chemical compound C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-O 0.000 description 1
WLOQLWBIJZDHET-UHFFFAOYSA-N triphenylsulfonium Chemical compound C1=CC=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 WLOQLWBIJZDHET-UHFFFAOYSA-N 0.000 description 1
239000012953 triphenylsulfonium Substances 0.000 description 1
ANEFWEBMQHRDLH-UHFFFAOYSA-N tris(2,3,4,5,6-pentafluorophenyl) borate Chemical compound FC1=C(F)C(F)=C(F)C(F)=C1OB(OC=1C(=C(F)C(F)=C(F)C=1F)F)OC1=C(F)C(F)=C(F)C(F)=C1F ANEFWEBMQHRDLH-UHFFFAOYSA-N 0.000 description 1
BSVBQGMMJUBVOD-UHFFFAOYSA-N trisodium borate Chemical compound [Na+].[Na+].[Na+].[O-]B([O-])[O-] BSVBQGMMJUBVOD-UHFFFAOYSA-N 0.000 description 1
OLFPYUPGPBITMH-UHFFFAOYSA-N tritylium Chemical compound C1=CC=CC=C1[C+](C=1C=CC=CC=1)C1=CC=CC=C1 OLFPYUPGPBITMH-UHFFFAOYSA-N 0.000 description 1
238000004876 x-ray fluorescence Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
- C07F5/027—Organoboranes and organoborohydrides

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)

IL12656798A 1997-03-10 1998-03-09 Purification process of TETRAKIS (FLUOROARYL) BORATEO MAGNESIUM HALIDE and derivative production process of TETRAKIS (FLUOROARYL) BORATE IL126567A (en)

Priority Applications (2)

Application Number	Priority Date	Filing Date	Title
IL14447798A IL144477A (en)	1997-03-10	1998-03-09	Purifying process of tetrakis (fluoroaryl) borate. magnesium halide, tetrakis (fluoroaryl) borate-ether complex and producing process of the same, and producing process of tetrakis (fluoroaryl) borate derivative
IL14447701A IL144477A0 (en)	1998-03-09	2001-07-20	Purifying process of tetrakis (fluoroaryl) borate-magnesium halide, tetrakis (fluoroaryl) borate-ether complex and producing process of the same, and producing process of tetrakis (fluoraryl) borate derivative

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
JP5531297		1997-03-10
JP5531097		1997-03-10
JP5531197		1997-03-10
PCT/JP1998/000946 WO1998040389A1 (fr)	1997-03-10	1998-03-09	Procede pour purifier le borate de tetrakis(fluoroaryle)/halogenure de magnesium, complexe borate de tetrakis(fluoroaryle)/ether, procede de preparation associe, et procede pour preparer leurs derives

Publications (2)

Publication Number	Publication Date
IL126567A0 IL126567A0 (en)	1999-08-17
IL126567A true IL126567A (en)	2002-05-23

Family

ID=27295562

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL12656798A IL126567A (en)	1997-03-10	1998-03-09	Purification process of TETRAKIS (FLUOROARYL) BORATEO MAGNESIUM HALIDE and derivative production process of TETRAKIS (FLUOROARYL) BORATE

Country Status (6)

Country	Link
US (3)	US6215025B1 (fr)
EP (3)	EP1400525B1 (fr)
DE (3)	DE69832645T2 (fr)
ES (3)	ES2206895T3 (fr)
IL (1)	IL126567A (fr)
WO (1)	WO1998040389A1 (fr)

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ES2205658T3 (es)	1998-09-07	2004-05-01	Nippon Shokubai Co., Ltd.	Metodo para purificar compuestos tetrakis (fluoroaril) borato.
US6169208B1 (en)	1999-12-03	2001-01-02	Albemarle Corporation	Process for producing a magnesium di[tetrakis(Faryl)borate] and products therefrom
US6162950A (en) *	1999-12-03	2000-12-19	Albemarle Corporation	Preparation of alkali metal tetrakis(F aryl)borates
US6476271B2 (en)	2000-06-19	2002-11-05	Honeywell International, Inc.	Process for the preparation of ether-free salts of tetrakis(pentafluorophenyl) borate
US6831200B2 (en)	2002-10-03	2004-12-14	Albemarle Corporation	Process for producing tetrakis(Faryl)borate salts
JP4999180B2 (ja) *	2004-04-01	2012-08-15	アルベマール・コーポレーシヨン	テトラキス（フルオロアリール）ホウ酸塩の製造方法
KR101602756B1 (ko) *	2007-11-01	2016-03-11	가부시키가이샤 아데카	염 화합물, 양이온 중합 개시제 및 양이온 중합성 조성물
CN105283459B (zh) *	2013-05-15	2018-01-02	广荣化学工业株式会社	新型四芳基硼酸盐化合物及其制备方法
US10147970B2 (en) *	2014-04-28	2018-12-04	Toyota Motor Engineering & Manufacturing North America, Inc.	Chloride-free electrolyte for a magnesium battery and a method to convert a magnesium electrolyte to a chloride-free electrolyte
CN110240610A (zh) *	2019-05-27	2019-09-17	珠海市赛纬电子材料股份有限公司	一种多元醇双硼酸酯二氟硼酸盐的制备方法

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US3055943A (en) *	1958-12-29	1962-09-25	Ethyl Corp	Production of metal organoboron compounds
US3078308A (en) *	1959-08-31	1963-02-19	Herbert C Brown	Process for the production of organoboron compounds
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JPH0615552B2 (ja) *	1987-03-25	1994-03-02	セントラル硝子株式会社	新規なテトラアリ−ルホウ酸塩
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JP2790605B2 (ja) *	1992-12-28	1998-08-27	東ソー・アクゾ株式会社	ペンタフルオロフェニルマグネシウム誘導体を用いたテトラキス（ペンタフルオロフェニル）ボレート誘導体の製造方法
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1998
- 1998-03-09 US US09/171,832 patent/US6215025B1/en not_active Expired - Lifetime
- 1998-03-09 IL IL12656798A patent/IL126567A/en not_active IP Right Cessation
- 1998-03-09 ES ES98905805T patent/ES2206895T3/es not_active Expired - Lifetime
- 1998-03-09 EP EP03025809A patent/EP1400525B1/fr not_active Expired - Lifetime
- 1998-03-09 EP EP03025808A patent/EP1400524B1/fr not_active Expired - Lifetime
- 1998-03-09 DE DE69832645T patent/DE69832645T2/de not_active Expired - Fee Related
- 1998-03-09 ES ES03025809T patent/ES2254855T3/es not_active Expired - Lifetime
- 1998-03-09 EP EP98905805A patent/EP0913400B1/fr not_active Expired - Lifetime
- 1998-03-09 DE DE69832646T patent/DE69832646T2/de not_active Expired - Fee Related
- 1998-03-09 WO PCT/JP1998/000946 patent/WO1998040389A1/fr not_active Ceased
- 1998-03-09 ES ES03025808T patent/ES2254854T3/es not_active Expired - Lifetime
- 1998-03-09 DE DE69819656T patent/DE69819656T2/de not_active Expired - Fee Related
2001
- 2001-02-09 US US09/779,673 patent/US6380435B2/en not_active Expired - Lifetime
- 2001-12-21 US US10/024,306 patent/US6624329B2/en not_active Expired - Fee Related

Also Published As

Publication number	Publication date
WO1998040389A1 (fr)	1998-09-17
ES2254855T3 (es)	2006-06-16
DE69832646D1 (de)	2006-01-05
EP1400524A1 (fr)	2004-03-24
IL126567A0 (en)	1999-08-17
EP0913400A1 (fr)	1999-05-06
US20020107419A1 (en)	2002-08-08
US20010014739A1 (en)	2001-08-16
US6624329B2 (en)	2003-09-23
ES2254854T3 (es)	2006-06-16
EP1400524B1 (fr)	2005-11-30
DE69819656D1 (de)	2003-12-18
ES2206895T3 (es)	2004-05-16
EP1400525A1 (fr)	2004-03-24
DE69832645T2 (de)	2006-08-24
EP0913400B1 (fr)	2003-11-12
US6380435B2 (en)	2002-04-30
US6215025B1 (en)	2001-04-10
EP1400525B1 (fr)	2005-11-30
DE69832646T2 (de)	2006-08-10
DE69819656T2 (de)	2004-10-07
EP0913400A4 (fr)	2000-10-04
DE69832645D1 (de)	2006-01-05

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