ES2532548T3 - Procedimiento para la preparación de ácidos alquil-fosfónicos y de sus ésteres y sales, mediante oxidación de ácidos alquil-fosfonosos, y su utilización - Google Patents

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Publication number

ES2532548T3

ES2532548T3 ES09778842.6T ES09778842T ES2532548T3 ES 2532548 T3 ES2532548 T3 ES 2532548T3 ES 09778842 T ES09778842 T ES 09778842T ES 2532548 T3 ES2532548 T3 ES 2532548T3

Authority

ES

Spain

Prior art keywords

salts

acid

alkyl

esters

agents

Prior art date

2008-12-18

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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• -1 alkyl phosphonic acids Chemical class 0.000 title claims abstract description 240
• 150000003839 salts Chemical class 0.000 title claims abstract description 89
• 238000000034 method Methods 0.000 title claims abstract description 56
• 150000002148 esters Chemical class 0.000 title claims abstract description 48
• 230000003647 oxidation Effects 0.000 title claims abstract description 21
• 238000007254 oxidation reaction Methods 0.000 title claims abstract description 21
• 238000002360 preparation method Methods 0.000 title claims abstract description 17
• 238000006243 chemical reaction Methods 0.000 claims abstract description 62
• 239000003795 chemical substances by application Substances 0.000 claims abstract description 56
• 239000000203 mixture Substances 0.000 claims abstract description 48
• LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims abstract description 46
• 229910052751 metal Inorganic materials 0.000 claims abstract description 44
• 239000002184 metal Substances 0.000 claims abstract description 44
• 229910052723 transition metal Inorganic materials 0.000 claims abstract description 42
• 150000003624 transition metals Chemical class 0.000 claims abstract description 42
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 40
• 239000003054 catalyst Substances 0.000 claims abstract description 33
• 150000001875 compounds Chemical class 0.000 claims abstract description 28
• 229910052700 potassium Inorganic materials 0.000 claims abstract description 24
• 229910052708 sodium Inorganic materials 0.000 claims abstract description 22
• 239000011734 sodium Substances 0.000 claims abstract description 22
• 150000001336 alkenes Chemical class 0.000 claims abstract description 20
• 229910052791 calcium Inorganic materials 0.000 claims abstract description 19
• 229910052749 magnesium Inorganic materials 0.000 claims abstract description 19
• ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical compound O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 claims abstract description 19
• 229910052725 zinc Inorganic materials 0.000 claims abstract description 18
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 16
• WOCIAKWEIIZHES-UHFFFAOYSA-N ruthenium(iv) oxide Chemical compound O=[Ru]=O WOCIAKWEIIZHES-UHFFFAOYSA-N 0.000 claims abstract description 16
• JQWHASGSAFIOCM-UHFFFAOYSA-M sodium periodate Chemical compound [Na+].[O-]I(=O)(=O)=O JQWHASGSAFIOCM-UHFFFAOYSA-M 0.000 claims abstract description 16
• PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims abstract description 15
• 229910052742 iron Inorganic materials 0.000 claims abstract description 15
• 229910052744 lithium Inorganic materials 0.000 claims abstract description 15
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 15
• 229910052759 nickel Inorganic materials 0.000 claims abstract description 15
• 229910052719 titanium Inorganic materials 0.000 claims abstract description 15
• 125000002947 alkylene group Chemical group 0.000 claims abstract description 14
• 239000003446 ligand Substances 0.000 claims abstract description 13
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims abstract description 11
• 150000003623 transition metal compounds Chemical class 0.000 claims abstract description 11
• WQYVRQLZKVEZGA-UHFFFAOYSA-N hypochlorite Chemical compound Cl[O-] WQYVRQLZKVEZGA-UHFFFAOYSA-N 0.000 claims abstract description 10
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 10
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 9
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims abstract description 9
• NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical group O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 claims abstract description 8
• 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims abstract description 8
• 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims abstract description 8
• KMUONIBRACKNSN-UHFFFAOYSA-N potassium dichromate Chemical compound [K+].[K+].[O-][Cr](=O)(=O)O[Cr]([O-])(=O)=O KMUONIBRACKNSN-UHFFFAOYSA-N 0.000 claims abstract description 8
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims abstract description 8
• 229910052726 zirconium Inorganic materials 0.000 claims abstract description 8
• 229910052787 antimony Inorganic materials 0.000 claims abstract description 7
• 229910052732 germanium Inorganic materials 0.000 claims abstract description 7
• WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims abstract description 7
• 229910052712 strontium Inorganic materials 0.000 claims abstract description 7
• 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims abstract description 6
• WGLPBDUCMAPZCE-UHFFFAOYSA-N chromium trioxide Inorganic materials O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 claims abstract description 6
• 229910052748 manganese Inorganic materials 0.000 claims abstract description 6
• 239000011572 manganese Substances 0.000 claims abstract description 6
• 229910052718 tin Inorganic materials 0.000 claims abstract description 6
• POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 claims abstract description 5
• 239000003810 Jones reagent Substances 0.000 claims abstract description 5
• 239000002585 base Substances 0.000 claims abstract description 5
• 229940117975 chromium trioxide Drugs 0.000 claims abstract description 5
• GAMDZJFZMJECOS-UHFFFAOYSA-N chromium(6+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[Cr+6] GAMDZJFZMJECOS-UHFFFAOYSA-N 0.000 claims abstract description 5
• YBCAZPLXEGKKFM-UHFFFAOYSA-K ruthenium(iii) chloride Chemical compound [Cl-].[Cl-].[Cl-].[Ru+3] YBCAZPLXEGKKFM-UHFFFAOYSA-K 0.000 claims abstract description 5
• CQMJEZQEVXQEJB-UHFFFAOYSA-N 1-hydroxy-1,3-dioxobenziodoxole Chemical compound C1=CC=C2I(O)(=O)OC(=O)C2=C1 CQMJEZQEVXQEJB-UHFFFAOYSA-N 0.000 claims abstract description 4
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 4
• 239000012027 Collins reagent Substances 0.000 claims abstract description 4
• JWIPGAFCGUDKEY-UHFFFAOYSA-L O[Cr](Cl)(=O)=O.C1=CC=NC=C1 Chemical compound O[Cr](Cl)(=O)=O.C1=CC=NC=C1 JWIPGAFCGUDKEY-UHFFFAOYSA-L 0.000 claims abstract description 4
• 239000003153 chemical reaction reagent Substances 0.000 claims abstract description 4
• 239000000460 chlorine Substances 0.000 claims abstract description 4
• 229910052801 chlorine Inorganic materials 0.000 claims abstract description 4
• BNSOYWDFFBDEFB-UHFFFAOYSA-L hydroxy-(hydroxy(dioxo)chromio)oxy-dioxochromium;pyridine Chemical compound C1=CC=NC=C1.O[Cr](=O)(=O)O[Cr](O)(=O)=O BNSOYWDFFBDEFB-UHFFFAOYSA-L 0.000 claims abstract description 4
• 150000004965 peroxy acids Chemical class 0.000 claims abstract description 4
• NPRDHMWYZHSAHR-UHFFFAOYSA-N pyridine;trioxochromium Chemical compound O=[Cr](=O)=O.C1=CC=NC=C1.C1=CC=NC=C1 NPRDHMWYZHSAHR-UHFFFAOYSA-N 0.000 claims abstract description 4
• 229910001927 ruthenium tetroxide Inorganic materials 0.000 claims abstract description 4
• YEYKMVJDLWJFOA-UHFFFAOYSA-N 2-propoxyethanol Chemical compound CCCOCCO YEYKMVJDLWJFOA-UHFFFAOYSA-N 0.000 claims abstract description 3
• 229910052802 copper Inorganic materials 0.000 claims abstract description 3
• 125000000864 peroxy group Chemical group O(O*)* 0.000 claims abstract description 3
• 230000007704 transition Effects 0.000 claims abstract description 3
• 229920000642 polymer Polymers 0.000 claims description 43
• 239000002253 acid Substances 0.000 claims description 42
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 30
• PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 26
• BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 22
• 150000002739 metals Chemical class 0.000 claims description 19
• 239000011575 calcium Substances 0.000 claims description 18
• XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 18
• 239000011777 magnesium Substances 0.000 claims description 18
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 16
• 150000001298 alcohols Chemical class 0.000 claims description 16
• 239000000654 additive Substances 0.000 claims description 13
• PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 claims description 12
• 239000010931 gold Substances 0.000 claims description 12
• 229910052782 aluminium Inorganic materials 0.000 claims description 11
• 239000003063 flame retardant Substances 0.000 claims description 11
• 229910052697 platinum Inorganic materials 0.000 claims description 11
• 229910052737 gold Inorganic materials 0.000 claims description 10
• 150000002736 metal compounds Chemical class 0.000 claims description 10
• 229910052763 palladium Inorganic materials 0.000 claims description 9
• 239000002516 radical scavenger Substances 0.000 claims description 9
• 229910052739 hydrogen Inorganic materials 0.000 claims description 8
• KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 7
• 238000000465 moulding Methods 0.000 claims description 7
• 229910052707 ruthenium Inorganic materials 0.000 claims description 7
• 239000000463 material Substances 0.000 claims description 6
• 239000007800 oxidant agent Substances 0.000 claims description 6
• 229910052703 rhodium Inorganic materials 0.000 claims description 6
• 239000010948 rhodium Substances 0.000 claims description 6
• MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical group [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims description 6
• 239000003381 stabilizer Substances 0.000 claims description 6
• 229920001169 thermoplastic Polymers 0.000 claims description 6
• 239000004416 thermosoftening plastic Substances 0.000 claims description 6
• 150000007513 acids Chemical class 0.000 claims description 5
• 230000007797 corrosion Effects 0.000 claims description 5
• 238000005260 corrosion Methods 0.000 claims description 5
• 239000000945 filler Substances 0.000 claims description 5
• 239000004814 polyurethane Substances 0.000 claims description 5
• 229920006395 saturated elastomer Polymers 0.000 claims description 5
• 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 4
• 239000000835 fiber Substances 0.000 claims description 4
• 239000011230 binding agent Substances 0.000 claims description 3
• 239000003431 cross linking reagent Substances 0.000 claims description 3
• 239000002480 mineral oil Substances 0.000 claims description 3
• 229910017464 nitrogen compound Inorganic materials 0.000 claims description 3
• 150000002830 nitrogen compounds Chemical class 0.000 claims description 3
• 229920002635 polyurethane Polymers 0.000 claims description 3
• 229920001187 thermosetting polymer Polymers 0.000 claims description 3
• 229920006337 unsaturated polyester resin Polymers 0.000 claims description 3
• 230000000996 additive effect Effects 0.000 claims description 2
• 239000012459 cleaning agent Substances 0.000 claims description 2
• 239000010949 copper Substances 0.000 claims description 2
• 239000003822 epoxy resin Substances 0.000 claims description 2
• 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 2
• 230000000737 periodic effect Effects 0.000 claims description 2
• 229920000647 polyepoxide Polymers 0.000 claims description 2
• 239000011814 protection agent Substances 0.000 claims description 2
• 239000003352 sequestering agent Substances 0.000 claims description 2
• 238000003786 synthesis reaction Methods 0.000 claims description 2
• 238000005406 washing Methods 0.000 claims description 2
• 150000002829 nitrogen Chemical class 0.000 claims 2
• 239000000543 intermediate Substances 0.000 claims 1
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 abstract description 3
• 238000006646 Dess-Martin oxidation reaction Methods 0.000 abstract 1
• NKLCNNUWBJBICK-UHFFFAOYSA-N dess–martin periodinane Chemical compound C1=CC=C2I(OC(=O)C)(OC(C)=O)(OC(C)=O)OC(=O)C2=C1 NKLCNNUWBJBICK-UHFFFAOYSA-N 0.000 abstract 1
• PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 58
• 239000002904 solvent Substances 0.000 description 29
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
• 239000004952 Polyamide Substances 0.000 description 21
• 229920002647 polyamide Polymers 0.000 description 21
• VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 20
• 239000005977 Ethylene Substances 0.000 description 20
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 18
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 18
• LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 16
• 239000000047 product Substances 0.000 description 16
• 239000000243 solution Substances 0.000 description 16
• 125000003837 (C1-C20) alkyl group Chemical group 0.000 description 14
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
• 239000011701 zinc Substances 0.000 description 14
• 229920001577 copolymer Polymers 0.000 description 13
• 229910052760 oxygen Inorganic materials 0.000 description 13
• 239000005062 Polybutadiene Substances 0.000 description 12
• 239000007983 Tris buffer Substances 0.000 description 12
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 12
• 239000012752 auxiliary agent Substances 0.000 description 12
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• 229920002857 polybutadiene Polymers 0.000 description 12
• 239000010936 titanium Substances 0.000 description 12
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
• ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 11
• LYYXRDZATAMURV-UHFFFAOYSA-N ethylphosphonous acid Chemical compound CCP(O)O LYYXRDZATAMURV-UHFFFAOYSA-N 0.000 description 11
• NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 10
• XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 10
• ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 10
• 239000007789 gas Substances 0.000 description 10
• 239000000725 suspension Substances 0.000 description 10
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
• KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 9
• IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 9
• WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 9
• MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 9
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
• ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 9
• 239000012071 phase Substances 0.000 description 9
• VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 8
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
• VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 8
• XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 8
• UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 8
• 239000007795 chemical reaction product Substances 0.000 description 8
• XEPOMWMUIRPRMP-UHFFFAOYSA-N hexadecylphosphonous acid Chemical compound CCCCCCCCCCCCCCCCP(O)O XEPOMWMUIRPRMP-UHFFFAOYSA-N 0.000 description 8
• 229920001684 low density polyethylene Polymers 0.000 description 8
• 239000004702 low-density polyethylene Substances 0.000 description 8
• 229910052757 nitrogen Inorganic materials 0.000 description 8
• 239000011591 potassium Substances 0.000 description 8
• 239000011343 solid material Substances 0.000 description 8
• 229910052784 alkaline earth metal Inorganic materials 0.000 description 7
• 239000004700 high-density polyethylene Substances 0.000 description 7
• 150000004677 hydrates Chemical class 0.000 description 7
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• 239000000377 silicon dioxide Substances 0.000 description 7
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
• LVEYOSJUKRVCCF-UHFFFAOYSA-N 1,3-bis(diphenylphosphino)propane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)CCCP(C=1C=CC=CC=1)C1=CC=CC=C1 LVEYOSJUKRVCCF-UHFFFAOYSA-N 0.000 description 6
• ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
• 239000004743 Polypropylene Substances 0.000 description 6
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
• XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 6
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• 125000004429 atom Chemical group 0.000 description 6
• 238000010533 azeotropic distillation Methods 0.000 description 6
• TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 6
• JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 6
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• 238000004821 distillation Methods 0.000 description 6
• 150000002170 ethers Chemical class 0.000 description 6
• 229920001903 high density polyethylene Polymers 0.000 description 6
• DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
• JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 6
• 150000003003 phosphines Chemical class 0.000 description 6
• NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 description 6
• QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 6
• 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 6
• KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 5
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