ES2525547T3 - Procedimiento para la preparación de ácidos dialquil-fosfínicos mono-funcionalizados con amino o de sus ésteres y sales por medio de acrilonitrilos y su utilización - Google Patents

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Publication number

ES2525547T3

ES2525547T3 ES09751775.9T ES09751775T ES2525547T3 ES 2525547 T3 ES2525547 T3 ES 2525547T3 ES 09751775 T ES09751775 T ES 09751775T ES 2525547 T3 ES2525547 T3 ES 2525547T3

Authority

ES

Spain

Prior art keywords

acid

bis

amino

salts

functionalized

Prior art date

2008-11-07

Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)

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• 150000003839 salts Chemical class 0.000 title claims abstract description 83
• 238000000034 method Methods 0.000 title claims abstract description 77
• 230000008569 process Effects 0.000 title claims abstract description 71
• 150000002148 esters Chemical class 0.000 title claims abstract description 67
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 title claims abstract description 50
• 238000002360 preparation method Methods 0.000 title claims abstract description 19
• 150000008360 acrylonitriles Chemical class 0.000 title claims abstract description 7
• 150000003009 phosphonic acids Chemical class 0.000 title claims description 12
• 239000003054 catalyst Substances 0.000 claims abstract description 56
• 239000002253 acid Substances 0.000 claims abstract description 39
• ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical compound O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 claims abstract description 31
• NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims abstract description 30
• 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 18
• 239000001257 hydrogen Substances 0.000 claims abstract description 13
• 150000007513 acids Chemical class 0.000 claims abstract description 12
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 10
• 239000003638 chemical reducing agent Substances 0.000 claims abstract description 10
• -1 alkyl phosphonous acid Chemical compound 0.000 claims description 158
• 238000006243 chemical reaction Methods 0.000 claims description 66
• 229910052751 metal Inorganic materials 0.000 claims description 65
• 239000002184 metal Substances 0.000 claims description 65
• LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 52
• 150000001875 compounds Chemical class 0.000 claims description 44
• ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 claims description 38
• 229910052723 transition metal Inorganic materials 0.000 claims description 38
• 150000003624 transition metals Chemical class 0.000 claims description 38
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 33
• PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 29
• 239000000047 product Substances 0.000 claims description 28
• 150000003003 phosphines Chemical class 0.000 claims description 26
• 150000002739 metals Chemical class 0.000 claims description 25
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 24
• 239000003795 chemical substances by application Substances 0.000 claims description 24
• 239000003063 flame retardant Substances 0.000 claims description 24
• 229910052700 potassium Inorganic materials 0.000 claims description 23
• 229910052782 aluminium Inorganic materials 0.000 claims description 21
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 21
• XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims description 20
• 229920000642 polymer Polymers 0.000 claims description 20
• 229910052725 zinc Inorganic materials 0.000 claims description 19
• XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 18
• ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 17
• BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 17
• 239000011591 potassium Substances 0.000 claims description 17
• 229910052791 calcium Inorganic materials 0.000 claims description 16
• 229910052742 iron Inorganic materials 0.000 claims description 16
• 229910052759 nickel Inorganic materials 0.000 claims description 16
• UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical class B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 claims description 15
• 239000003446 ligand Substances 0.000 claims description 15
• 229910052719 titanium Inorganic materials 0.000 claims description 15
• 229910052708 sodium Inorganic materials 0.000 claims description 14
• 239000011734 sodium Substances 0.000 claims description 14
• 229910052718 tin Inorganic materials 0.000 claims description 14
• 229910052726 zirconium Inorganic materials 0.000 claims description 14
• RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 claims description 13
• OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 claims description 13
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 13
• 239000000654 additive Substances 0.000 claims description 13
• 125000002947 alkylene group Chemical group 0.000 claims description 13
• 229910052749 magnesium Inorganic materials 0.000 claims description 13
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 13
• 229920000728 polyester Polymers 0.000 claims description 13
• PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 12
• 150000001298 alcohols Chemical class 0.000 claims description 12
• 229910000073 phosphorus hydride Inorganic materials 0.000 claims description 12
• CHQMHPLRPQMAMX-UHFFFAOYSA-L sodium persulfate Substances [Na+].[Na+].[O-]S(=O)(=O)OOS([O-])(=O)=O CHQMHPLRPQMAMX-UHFFFAOYSA-L 0.000 claims description 12
• 238000000465 moulding Methods 0.000 claims description 10
• 150000003623 transition metal compounds Chemical class 0.000 claims description 10
• QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 9
• 229910052684 Cerium Inorganic materials 0.000 claims description 9
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 8
• 229910052697 platinum Inorganic materials 0.000 claims description 8
• XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 7
• WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 7
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 7
• 229910052744 lithium Inorganic materials 0.000 claims description 7
• 150000007522 mineralic acids Chemical class 0.000 claims description 7
• 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 7
• 229910052763 palladium Inorganic materials 0.000 claims description 7
• 239000002841 Lewis acid Substances 0.000 claims description 6
• KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 claims description 6
• 125000002877 alkyl aryl group Chemical group 0.000 claims description 6
• 125000000217 alkyl group Chemical group 0.000 claims description 6
• 229910052787 antimony Inorganic materials 0.000 claims description 6
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 6
• 125000003118 aryl group Chemical group 0.000 claims description 6
• 229920002678 cellulose Polymers 0.000 claims description 6
• 150000007517 lewis acids Chemical class 0.000 claims description 6
• 238000004519 manufacturing process Methods 0.000 claims description 6
• 229910052987 metal hydride Inorganic materials 0.000 claims description 6
• 150000004681 metal hydrides Chemical group 0.000 claims description 6
• 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 6
• 229910052757 nitrogen Inorganic materials 0.000 claims description 6
• MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical group [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims description 6
• 229910052712 strontium Inorganic materials 0.000 claims description 6
• AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 claims description 5
• 229910052732 germanium Inorganic materials 0.000 claims description 5
• MHAJPDPJQMAIIY-UHFFFAOYSA-N hydrogen peroxide Substances OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 5
• 229910052748 manganese Inorganic materials 0.000 claims description 5
• 229910052703 rhodium Inorganic materials 0.000 claims description 5
• 239000010948 rhodium Substances 0.000 claims description 5
• 239000003381 stabilizer Substances 0.000 claims description 5
• LCPVQAHEFVXVKT-UHFFFAOYSA-N 2-(2,4-difluorophenoxy)pyridin-3-amine Chemical compound NC1=CC=CN=C1OC1=CC=C(F)C=C1F LCPVQAHEFVXVKT-UHFFFAOYSA-N 0.000 claims description 4
• POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 claims description 4
• GYCMBHHDWRMZGG-UHFFFAOYSA-N Methylacrylonitrile Chemical compound CC(=C)C#N GYCMBHHDWRMZGG-UHFFFAOYSA-N 0.000 claims description 4
• USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 claims description 4
• 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 3
• 239000004342 Benzoyl peroxide Substances 0.000 claims description 3
• OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 claims description 3
• ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 3
• KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 3
• MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 claims description 3
• 235000019400 benzoyl peroxide Nutrition 0.000 claims description 3
• 229910052796 boron Inorganic materials 0.000 claims description 3
• 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 3
• 239000001913 cellulose Substances 0.000 claims description 3
• 229910052802 copper Inorganic materials 0.000 claims description 3
• 239000003431 cross linking reagent Substances 0.000 claims description 3
• LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 claims description 3
• 239000003822 epoxy resin Substances 0.000 claims description 3
• LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 claims description 3
• 150000004678 hydrides Chemical class 0.000 claims description 3
• HPGPEWYJWRWDTP-UHFFFAOYSA-N lithium peroxide Chemical compound [Li+].[Li+].[O-][O-] HPGPEWYJWRWDTP-UHFFFAOYSA-N 0.000 claims description 3
• 150000007524 organic acids Chemical class 0.000 claims description 3
• JRKICGRDRMAZLK-UHFFFAOYSA-N peroxydisulfuric acid Chemical compound OS(=O)(=O)OOS(O)(=O)=O JRKICGRDRMAZLK-UHFFFAOYSA-N 0.000 claims description 3
• 229920000647 polyepoxide Polymers 0.000 claims description 3
• 229920002635 polyurethane Polymers 0.000 claims description 3
• 239000004814 polyurethane Substances 0.000 claims description 3
• 229910052707 ruthenium Inorganic materials 0.000 claims description 3
• PFUVRDFDKPNGAV-UHFFFAOYSA-N sodium peroxide Chemical compound [Na+].[Na+].[O-][O-] PFUVRDFDKPNGAV-UHFFFAOYSA-N 0.000 claims description 3
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
• 229920006337 unsaturated polyester resin Polymers 0.000 claims description 3
• 125000006702 (C1-C18) alkyl group Chemical group 0.000 claims description 2
• ZWKNLRXFUTWSOY-QPJJXVBHSA-N (e)-3-phenylprop-2-enenitrile Chemical compound N#C\C=C\C1=CC=CC=C1 ZWKNLRXFUTWSOY-QPJJXVBHSA-N 0.000 claims description 2
• IHXNSHZBFXGOJM-UHFFFAOYSA-N 2-methylbut-2-enenitrile Chemical compound CC=C(C)C#N IHXNSHZBFXGOJM-UHFFFAOYSA-N 0.000 claims description 2
• YEYKMVJDLWJFOA-UHFFFAOYSA-N 2-propoxyethanol Chemical compound CCCOCCO YEYKMVJDLWJFOA-UHFFFAOYSA-N 0.000 claims description 2
• JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims description 2
• 230000000996 additive effect Effects 0.000 claims description 2
• 239000011230 binding agent Substances 0.000 claims description 2
• 239000012459 cleaning agent Substances 0.000 claims description 2
• 238000000576 coating method Methods 0.000 claims description 2
• 230000007797 corrosion Effects 0.000 claims description 2
• 238000005260 corrosion Methods 0.000 claims description 2
• 239000004744 fabric Substances 0.000 claims description 2
• CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 claims description 2
• 238000005470 impregnation Methods 0.000 claims description 2
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
• 239000002480 mineral oil Substances 0.000 claims description 2
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
• 230000000737 periodic effect Effects 0.000 claims description 2
• 239000003352 sequestering agent Substances 0.000 claims description 2
• 238000003786 synthesis reaction Methods 0.000 claims description 2
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• 238000005406 washing Methods 0.000 claims description 2
• 239000002023 wood Substances 0.000 claims description 2
• QYZFTMMPKCOTAN-UHFFFAOYSA-N n-[2-(2-hydroxyethylamino)ethyl]-2-[[1-[2-(2-hydroxyethylamino)ethylamino]-2-methyl-1-oxopropan-2-yl]diazenyl]-2-methylpropanamide Chemical compound OCCNCCNC(=O)C(C)(C)N=NC(C)(C)C(=O)NCCNCCO QYZFTMMPKCOTAN-UHFFFAOYSA-N 0.000 claims 2
• SMBRHGJEDJVDOB-UHFFFAOYSA-N 2-methylpropanimidamide;dihydrochloride Chemical compound Cl.Cl.CC(C)C(N)=N SMBRHGJEDJVDOB-UHFFFAOYSA-N 0.000 claims 1
• PGFZYOCLSPEKSN-UHFFFAOYSA-N 5,5-dimethyl-1,3-diazabicyclo[2.2.0]hex-3-ene dihydrochloride Chemical compound Cl.Cl.CC1(C)CN2CN=C12 PGFZYOCLSPEKSN-UHFFFAOYSA-N 0.000 claims 1
• FGBJXOREULPLGL-UHFFFAOYSA-N ethyl cyanoacrylate Chemical compound CCOC(=O)C(=C)C#N FGBJXOREULPLGL-UHFFFAOYSA-N 0.000 claims 1
• 239000013067 intermediate product Substances 0.000 claims 1
• 239000011814 protection agent Substances 0.000 claims 1
• 238000004513 sizing Methods 0.000 claims 1
• 150000001336 alkenes Chemical class 0.000 abstract description 11
• PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 52
• 239000002904 solvent Substances 0.000 description 38
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 33
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 23
• 239000000203 mixture Substances 0.000 description 22
• 239000004952 Polyamide Substances 0.000 description 20
• UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 20
• 229920002647 polyamide Polymers 0.000 description 20
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 19
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 19
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 18
• 239000000243 solution Substances 0.000 description 18
• 239000007983 Tris buffer Substances 0.000 description 17
• 125000003837 (C1-C20) alkyl group Chemical group 0.000 description 16
• 239000011701 zinc Substances 0.000 description 16
• 239000011575 calcium Substances 0.000 description 14
• LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 13
• 150000001412 amines Chemical class 0.000 description 13
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 12
• KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 12
• ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 12
• 239000011135 tin Substances 0.000 description 12
• 239000010936 titanium Substances 0.000 description 12
• OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 11
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• 239000012752 auxiliary agent Substances 0.000 description 11
• 239000011777 magnesium Substances 0.000 description 11
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• 229920002857 polybutadiene Polymers 0.000 description 11
• FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 9
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• 235000010290 biphenyl Nutrition 0.000 description 9
• 150000001735 carboxylic acids Chemical class 0.000 description 9
• XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 9
• 239000007789 gas Substances 0.000 description 9
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• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical group Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
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• 238000004821 distillation Methods 0.000 description 8
• LYYXRDZATAMURV-UHFFFAOYSA-N ethylphosphonous acid Chemical compound CCP(O)O LYYXRDZATAMURV-UHFFFAOYSA-N 0.000 description 8
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• 150000004677 hydrates Chemical class 0.000 description 8
• BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 8
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• VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 7
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• 239000005977 Ethylene Substances 0.000 description 6
• VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 6
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• YFNKIDBQEZZDLK-UHFFFAOYSA-N triglyme Chemical compound COCCOCCOCCOC YFNKIDBQEZZDLK-UHFFFAOYSA-N 0.000 description 1
• JDUSEMYGYCYQSK-UHFFFAOYSA-L trimagnesium;dioxido(oxidooxy)borane Chemical compound [Mg+2].[Mg+2].[Mg+2].[O-]OB([O-])[O-].[O-]OB([O-])[O-] JDUSEMYGYCYQSK-UHFFFAOYSA-L 0.000 description 1
• CYTQBVOFDCPGCX-UHFFFAOYSA-N trimethyl phosphite Chemical compound COP(OC)OC CYTQBVOFDCPGCX-UHFFFAOYSA-N 0.000 description 1
• HYWCXWRMUZYRPH-UHFFFAOYSA-N trimethyl(prop-2-enyl)silane Chemical compound C[Si](C)(C)CC=C HYWCXWRMUZYRPH-UHFFFAOYSA-N 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
• 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 1
• RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
• 229960004418 trolamine Drugs 0.000 description 1
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• 239000010937 tungsten Substances 0.000 description 1
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• 239000008096 xylene Substances 0.000 description 1
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• 229940105296 zinc peroxide Drugs 0.000 description 1
• XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical class [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 1
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• 229910000368 zinc sulfate Inorganic materials 0.000 description 1
• 229960001763 zinc sulfate Drugs 0.000 description 1
• CITILBVTAYEWKR-UHFFFAOYSA-L zinc trifluoromethanesulfonate Substances [Zn+2].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F CITILBVTAYEWKR-UHFFFAOYSA-L 0.000 description 1
• ZMLPZCGHASSGEA-UHFFFAOYSA-M zinc trifluoromethanesulfonate Chemical compound [Zn+2].[O-]S(=O)(=O)C(F)(F)F ZMLPZCGHASSGEA-UHFFFAOYSA-M 0.000 description 1
• MFMKGXZULQONRI-UHFFFAOYSA-L zinc;diiodate Chemical compound [Zn+2].[O-]I(=O)=O.[O-]I(=O)=O MFMKGXZULQONRI-UHFFFAOYSA-L 0.000 description 1
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• RNWHGQJWIACOKP-UHFFFAOYSA-N zinc;oxygen(2-) Chemical class [O-2].[Zn+2] RNWHGQJWIACOKP-UHFFFAOYSA-N 0.000 description 1
• 150000003754 zirconium Chemical class 0.000 description 1
• 150000003755 zirconium compounds Chemical class 0.000 description 1
• 229910001928 zirconium oxide Inorganic materials 0.000 description 1
• DUNKXUFBGCUVQW-UHFFFAOYSA-J zirconium tetrachloride Chemical compound Cl[Zr](Cl)(Cl)Cl DUNKXUFBGCUVQW-UHFFFAOYSA-J 0.000 description 1
• IPCAPQRVQMIMAN-UHFFFAOYSA-L zirconyl chloride Chemical compound Cl[Zr](Cl)=O IPCAPQRVQMIMAN-UHFFFAOYSA-L 0.000 description 1