JPH0348208B2 - - Google Patents

Info

Publication number

JPH0348208B2

JPH0348208B2 JP22599482A JP22599482A JPH0348208B2 JP H0348208 B2 JPH0348208 B2 JP H0348208B2 JP 22599482 A JP22599482 A JP 22599482A JP 22599482 A JP22599482 A JP 22599482A JP H0348208 B2 JPH0348208 B2 JP H0348208B2

Authority

JP

Japan

Prior art keywords

magnesium

catalyst component

polymerization

titanium

solid

Prior art date

1982-12-24

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.)

Expired

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• 239000003054 catalyst Substances 0.000 claims description 39
• FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 17
• 229910052749 magnesium Inorganic materials 0.000 claims description 17
• 239000011777 magnesium Substances 0.000 claims description 17
• ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 claims description 14
• 239000001095 magnesium carbonate Substances 0.000 claims description 14
• 229910000021 magnesium carbonate Inorganic materials 0.000 claims description 14
• 150000001336 alkenes Chemical class 0.000 claims description 12
• 235000014113 dietary fatty acids Nutrition 0.000 claims description 10
• 239000000194 fatty acid Substances 0.000 claims description 10
• 229930195729 fatty acid Natural products 0.000 claims description 10
• 150000004665 fatty acids Chemical class 0.000 claims description 10
• WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 9
• 229910052736 halogen Inorganic materials 0.000 claims description 4
• 230000000379 polymerizing effect Effects 0.000 claims description 4
• 239000007795 chemical reaction product Substances 0.000 claims description 3
• 150000002367 halogens Chemical class 0.000 claims description 3
• 238000004519 manufacturing process Methods 0.000 claims description 3
• 238000006555 catalytic reaction Methods 0.000 claims 1
• 125000005843 halogen group Chemical group 0.000 claims 1
• IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 30
• 229910052719 titanium Inorganic materials 0.000 description 22
• -1 dialkoxymagnesium Chemical compound 0.000 description 21
• 238000006116 polymerization reaction Methods 0.000 description 21
• 239000010936 titanium Substances 0.000 description 21
• 229920000642 polymer Polymers 0.000 description 18
• 239000007787 solid Substances 0.000 description 18
• 229940091250 magnesium supplement Drugs 0.000 description 16
• RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 15
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 12
• TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 12
• 239000000460 chlorine Substances 0.000 description 12
• 229910052801 chlorine Inorganic materials 0.000 description 12
• 239000000203 mixture Substances 0.000 description 11
• 238000006243 chemical reaction Methods 0.000 description 10
• MTZQAGJQAFMTAQ-UHFFFAOYSA-N ethyl benzoate Chemical compound CCOC(=O)C1=CC=CC=C1 MTZQAGJQAFMTAQ-UHFFFAOYSA-N 0.000 description 10
• 238000000034 method Methods 0.000 description 10
• 238000005406 washing Methods 0.000 description 10
• 239000007788 liquid Substances 0.000 description 9
• HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 8
• 238000003756 stirring Methods 0.000 description 8
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 7
• 229910001873 dinitrogen Inorganic materials 0.000 description 7
• 230000037048 polymerization activity Effects 0.000 description 7
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
• 230000000694 effects Effects 0.000 description 6
• 229910001629 magnesium chloride Inorganic materials 0.000 description 6
• FHUODBDRWMIBQP-UHFFFAOYSA-N Ethyl p-anisate Chemical compound CCOC(=O)C1=CC=C(OC)C=C1 FHUODBDRWMIBQP-UHFFFAOYSA-N 0.000 description 4
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
• 239000012876 carrier material Substances 0.000 description 4
• 230000000052 comparative effect Effects 0.000 description 4
• 238000002474 experimental method Methods 0.000 description 4
• 235000019359 magnesium stearate Nutrition 0.000 description 4
• XDKQUSKHRIUJEO-UHFFFAOYSA-N magnesium;ethanolate Chemical compound [Mg+2].CC[O-].CC[O-] XDKQUSKHRIUJEO-UHFFFAOYSA-N 0.000 description 4
• 239000000843 powder Substances 0.000 description 4
• 239000000126 substance Substances 0.000 description 4
• 239000000725 suspension Substances 0.000 description 4
• 229920000576 tactic polymer Polymers 0.000 description 4
• 239000012298 atmosphere Substances 0.000 description 3
• NWPWRAWAUYIELB-UHFFFAOYSA-N ethyl 4-methylbenzoate Chemical compound CCOC(=O)C1=CC=C(C)C=C1 NWPWRAWAUYIELB-UHFFFAOYSA-N 0.000 description 3
• 230000005484 gravity Effects 0.000 description 3
• 239000001257 hydrogen Substances 0.000 description 3
• 229910052739 hydrogen Inorganic materials 0.000 description 3
• 239000002904 solvent Substances 0.000 description 3
• WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
• WSSSPWUEQFSQQG-UHFFFAOYSA-N 4-methyl-1-pentene Chemical compound CC(C)CC=C WSSSPWUEQFSQQG-UHFFFAOYSA-N 0.000 description 2
• 230000002411 adverse Effects 0.000 description 2
• 238000009835 boiling Methods 0.000 description 2
• 150000001875 compounds Chemical class 0.000 description 2
• NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 2
• 238000010908 decantation Methods 0.000 description 2
• 239000007789 gas Substances 0.000 description 2
• 238000009776 industrial production Methods 0.000 description 2
• 239000007791 liquid phase Substances 0.000 description 2
• UEGPKNKPLBYCNK-UHFFFAOYSA-L magnesium acetate Chemical compound [Mg+2].CC([O-])=O.CC([O-])=O UEGPKNKPLBYCNK-UHFFFAOYSA-L 0.000 description 2
• 239000011654 magnesium acetate Substances 0.000 description 2
• 235000011285 magnesium acetate Nutrition 0.000 description 2
• 229940069446 magnesium acetate Drugs 0.000 description 2
• WWRYOAYBSQIWNU-UHFFFAOYSA-L magnesium;decanoate Chemical compound [Mg+2].CCCCCCCCCC([O-])=O.CCCCCCCCCC([O-])=O WWRYOAYBSQIWNU-UHFFFAOYSA-L 0.000 description 2
• HPBJPFJVNDHMEG-UHFFFAOYSA-L magnesium;octanoate Chemical compound [Mg+2].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O HPBJPFJVNDHMEG-UHFFFAOYSA-L 0.000 description 2
• WNJYXPXGUGOGBO-UHFFFAOYSA-N magnesium;propan-1-olate Chemical compound CCCO[Mg]OCCC WNJYXPXGUGOGBO-UHFFFAOYSA-N 0.000 description 2
• 239000003960 organic solvent Substances 0.000 description 2
• 229920000098 polyolefin Polymers 0.000 description 2
• 238000002360 preparation method Methods 0.000 description 2
• QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 2
• 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 2
• 238000010992 reflux Methods 0.000 description 2
• 239000006228 supernatant Substances 0.000 description 2
• VOITXYVAKOUIBA-UHFFFAOYSA-N triethylaluminium Chemical compound CC[Al](CC)CC VOITXYVAKOUIBA-UHFFFAOYSA-N 0.000 description 2
• JXPHLUCMHXXHEJ-UHFFFAOYSA-N 2-(aminomethyl)-4-bromoaniline Chemical compound NCC1=CC(Br)=CC=C1N JXPHLUCMHXXHEJ-UHFFFAOYSA-N 0.000 description 1
• GWYFCOCPABKNJV-UHFFFAOYSA-M 3-Methylbutanoic acid Natural products CC(C)CC([O-])=O GWYFCOCPABKNJV-UHFFFAOYSA-M 0.000 description 1
• 239000005711 Benzoic acid Substances 0.000 description 1
• XDOCKYACOWXTGO-UHFFFAOYSA-N C(CC=O)=O.[Mg] Chemical compound C(CC=O)=O.[Mg] XDOCKYACOWXTGO-UHFFFAOYSA-N 0.000 description 1
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
• RKISEVNXKKNWSU-UHFFFAOYSA-N [Mg].C(CCCCCC(=O)O)(=O)O Chemical compound [Mg].C(CCCCCC(=O)O)(=O)O RKISEVNXKKNWSU-UHFFFAOYSA-N 0.000 description 1
• 239000004480 active ingredient Substances 0.000 description 1
• 229910052782 aluminium Inorganic materials 0.000 description 1
• SMZOGRDCAXLAAR-UHFFFAOYSA-N aluminium isopropoxide Chemical compound [Al+3].CC(C)[O-].CC(C)[O-].CC(C)[O-] SMZOGRDCAXLAAR-UHFFFAOYSA-N 0.000 description 1
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
• 235000010233 benzoic acid Nutrition 0.000 description 1
• 239000002738 chelating agent Substances 0.000 description 1
• 230000007797 corrosion Effects 0.000 description 1
• 238000005260 corrosion Methods 0.000 description 1
• LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 description 1
• 230000018044 dehydration Effects 0.000 description 1
• 238000006297 dehydration reaction Methods 0.000 description 1
• 230000006866 deterioration Effects 0.000 description 1
• GDVKFRBCXAPAQJ-UHFFFAOYSA-A dialuminum;hexamagnesium;carbonate;hexadecahydroxide Chemical compound [OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Al+3].[Al+3].[O-]C([O-])=O GDVKFRBCXAPAQJ-UHFFFAOYSA-A 0.000 description 1
• HUKIJZIDGFUNMG-UHFFFAOYSA-N dimethyl 4-oxocyclohexane-1,2-dicarboxylate Chemical compound COC(=O)C1CCC(=O)CC1C(=O)OC HUKIJZIDGFUNMG-UHFFFAOYSA-N 0.000 description 1
• 238000001035 drying Methods 0.000 description 1
• ZQPPMHVWECSIRJ-MDZDMXLPSA-M elaidate Chemical compound CCCCCCCC\C=C\CCCCCCCC([O-])=O ZQPPMHVWECSIRJ-MDZDMXLPSA-M 0.000 description 1
• 239000011521 glass Substances 0.000 description 1
• 238000005469 granulation Methods 0.000 description 1
• 230000003179 granulation Effects 0.000 description 1
• 150000008282 halocarbons Chemical class 0.000 description 1
• 229960001545 hydrotalcite Drugs 0.000 description 1
• 229910001701 hydrotalcite Inorganic materials 0.000 description 1
• GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 1
• VMPHSYLJUKZBJJ-UHFFFAOYSA-N lauric acid triglyceride Natural products CCCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCCCC)COC(=O)CCCCCCCCCCC VMPHSYLJUKZBJJ-UHFFFAOYSA-N 0.000 description 1
• DTOSIQBPPRVQHS-PDBXOOCHSA-M linolenate Chemical compound CC\C=C/C\C=C/C\C=C/CCCCCCCC([O-])=O DTOSIQBPPRVQHS-PDBXOOCHSA-M 0.000 description 1
• 229940040452 linolenate Drugs 0.000 description 1
• 229960005336 magnesium citrate Drugs 0.000 description 1
• 235000002538 magnesium citrate Nutrition 0.000 description 1
• 239000004337 magnesium citrate Substances 0.000 description 1
• CQQJGTPWCKCEOQ-UHFFFAOYSA-L magnesium dipropionate Chemical compound [Mg+2].CCC([O-])=O.CCC([O-])=O CQQJGTPWCKCEOQ-UHFFFAOYSA-L 0.000 description 1
• JVJHKCKGIBIFKH-UHFFFAOYSA-L magnesium docos-2-enoate Chemical compound C(C=CCCCCCCCCCCCCCCCCCCC)(=O)[O-].[Mg+2].C(C=CCCCCCCCCCCCCCCCCCCC)(=O)[O-] JVJHKCKGIBIFKH-UHFFFAOYSA-L 0.000 description 1
• 229940105112 magnesium myristate Drugs 0.000 description 1
• HVMSIOAHCBSRNO-UHFFFAOYSA-L magnesium nonanedioate Chemical compound [Mg+2].[O-]C(=O)CCCCCCCC([O-])=O HVMSIOAHCBSRNO-UHFFFAOYSA-L 0.000 description 1
• UHNWOJJPXCYKCG-UHFFFAOYSA-L magnesium oxalate Chemical compound [Mg+2].[O-]C(=O)C([O-])=O UHNWOJJPXCYKCG-UHFFFAOYSA-L 0.000 description 1
• 235000012245 magnesium oxide Nutrition 0.000 description 1
• 229940063002 magnesium palmitate Drugs 0.000 description 1
• 229940057948 magnesium stearate Drugs 0.000 description 1
• 229940095060 magnesium tartrate Drugs 0.000 description 1
• ZSMRTTMJRRECKC-RJNTXXOISA-L magnesium;(2e,4e)-hexa-2,4-dienoate Chemical compound [Mg+2].C\C=C\C=C\C([O-])=O.C\C=C\C=C\C([O-])=O ZSMRTTMJRRECKC-RJNTXXOISA-L 0.000 description 1
• MUZDLCBWNVUYIR-ZVGUSBNCSA-L magnesium;(2r,3r)-2,3-dihydroxybutanedioate Chemical compound [Mg+2].[O-]C(=O)[C@H](O)[C@@H](O)C([O-])=O MUZDLCBWNVUYIR-ZVGUSBNCSA-L 0.000 description 1
• QUIOHQITLKCGNW-TYYBGVCCSA-L magnesium;(e)-but-2-enedioate Chemical compound [Mg+2].[O-]C(=O)\C=C\C([O-])=O QUIOHQITLKCGNW-TYYBGVCCSA-L 0.000 description 1
• QUIOHQITLKCGNW-ODZAUARKSA-L magnesium;(z)-but-2-enedioate Chemical compound [Mg+2].[O-]C(=O)\C=C/C([O-])=O QUIOHQITLKCGNW-ODZAUARKSA-L 0.000 description 1
• RTKCPZYOLXPARI-UHFFFAOYSA-N magnesium;2-methylpropan-2-olate Chemical compound [Mg+2].CC(C)(C)[O-].CC(C)(C)[O-] RTKCPZYOLXPARI-UHFFFAOYSA-N 0.000 description 1
• VDUQUWCVENWCNL-UHFFFAOYSA-L magnesium;2-methylpropanoate Chemical compound [Mg+2].CC(C)C([O-])=O.CC(C)C([O-])=O VDUQUWCVENWCNL-UHFFFAOYSA-L 0.000 description 1
• WXPNTKUIDRYHOP-UHFFFAOYSA-L magnesium;3-oxobutanoate Chemical compound [Mg+2].CC(=O)CC([O-])=O.CC(=O)CC([O-])=O WXPNTKUIDRYHOP-UHFFFAOYSA-L 0.000 description 1
• FMIZEELUXKHREU-UHFFFAOYSA-L magnesium;but-2-ynedioate Chemical compound [Mg+2].[O-]C(=O)C#CC([O-])=O FMIZEELUXKHREU-UHFFFAOYSA-L 0.000 description 1
• HFTSQAKJLBPKBD-UHFFFAOYSA-N magnesium;butan-1-olate Chemical compound [Mg+2].CCCC[O-].CCCC[O-] HFTSQAKJLBPKBD-UHFFFAOYSA-N 0.000 description 1
• XLQMOUZWUAUZJX-UHFFFAOYSA-N magnesium;butan-2-olate Chemical compound [Mg+2].CCC(C)[O-].CCC(C)[O-] XLQMOUZWUAUZJX-UHFFFAOYSA-N 0.000 description 1
• NCRZJKMYPDVONB-UHFFFAOYSA-L magnesium;decanedioate Chemical compound [Mg+2].[O-]C(=O)CCCCCCCCC([O-])=O NCRZJKMYPDVONB-UHFFFAOYSA-L 0.000 description 1
• OBQVOBQZMOXRAL-UHFFFAOYSA-L magnesium;docosanoate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCCCCCC([O-])=O OBQVOBQZMOXRAL-UHFFFAOYSA-L 0.000 description 1
• BJZBHTNKDCBDNQ-UHFFFAOYSA-L magnesium;dodecanoate Chemical compound [Mg+2].CCCCCCCCCCCC([O-])=O.CCCCCCCCCCCC([O-])=O BJZBHTNKDCBDNQ-UHFFFAOYSA-L 0.000 description 1
• NYKBOLCRGNSBBC-UHFFFAOYSA-L magnesium;heptanoate Chemical compound [Mg+2].CCCCCCC([O-])=O.CCCCCCC([O-])=O NYKBOLCRGNSBBC-UHFFFAOYSA-L 0.000 description 1
• ABSWXCXMXIZDSN-UHFFFAOYSA-L magnesium;hexadecanoate Chemical compound [Mg+2].CCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCC([O-])=O ABSWXCXMXIZDSN-UHFFFAOYSA-L 0.000 description 1
• QXNFATVALXHNRJ-UHFFFAOYSA-L magnesium;hexanedioate Chemical compound [Mg+2].[O-]C(=O)CCCCC([O-])=O QXNFATVALXHNRJ-UHFFFAOYSA-L 0.000 description 1
• FKZRUGSMXUERAD-UHFFFAOYSA-L magnesium;hexanoate Chemical compound [Mg+2].CCCCCC([O-])=O.CCCCCC([O-])=O FKZRUGSMXUERAD-UHFFFAOYSA-L 0.000 description 1
• IBBBJHKSXOSPDK-UHFFFAOYSA-L magnesium;nonanoate Chemical compound [Mg+2].CCCCCCCCC([O-])=O.CCCCCCCCC([O-])=O IBBBJHKSXOSPDK-UHFFFAOYSA-L 0.000 description 1
• FFSLFHVETCMQBM-UHFFFAOYSA-L magnesium;octanedioate Chemical compound [Mg+2].[O-]C(=O)CCCCCCC([O-])=O FFSLFHVETCMQBM-UHFFFAOYSA-L 0.000 description 1
• AHPWAMGCMMEWNF-UHFFFAOYSA-L magnesium;oxaldehydate Chemical compound [Mg+2].[O-]C(=O)C=O.[O-]C(=O)C=O AHPWAMGCMMEWNF-UHFFFAOYSA-L 0.000 description 1
• AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical class [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
• NKBDSFGVUTVKAD-UHFFFAOYSA-L magnesium;pentanedioate Chemical compound [Mg+2].[O-]C(=O)CCCC([O-])=O NKBDSFGVUTVKAD-UHFFFAOYSA-L 0.000 description 1
• PWDTYUOSZRLLEV-UHFFFAOYSA-L magnesium;pentanoate Chemical compound [Mg+2].CCCCC([O-])=O.CCCCC([O-])=O PWDTYUOSZRLLEV-UHFFFAOYSA-L 0.000 description 1
• DWLAVVBOGOXHNH-UHFFFAOYSA-L magnesium;prop-2-enoate Chemical compound [Mg+2].[O-]C(=O)C=C.[O-]C(=O)C=C DWLAVVBOGOXHNH-UHFFFAOYSA-L 0.000 description 1
• ORPJQHHQRCLVIC-UHFFFAOYSA-N magnesium;propan-2-olate Chemical compound CC(C)O[Mg]OC(C)C ORPJQHHQRCLVIC-UHFFFAOYSA-N 0.000 description 1
• AICDYVDWYUUUGL-UHFFFAOYSA-L magnesium;propanedioate Chemical compound [Mg+2].[O-]C(=O)CC([O-])=O AICDYVDWYUUUGL-UHFFFAOYSA-L 0.000 description 1
• DMRBHZWQMKSQGR-UHFFFAOYSA-L magnesium;tetradecanoate Chemical compound [Mg+2].CCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCC([O-])=O DMRBHZWQMKSQGR-UHFFFAOYSA-L 0.000 description 1
• JAGIVJJGHDMBSN-UHFFFAOYSA-L magnesium;undec-2-enoate Chemical compound [Mg+2].CCCCCCCCC=CC([O-])=O.CCCCCCCCC=CC([O-])=O JAGIVJJGHDMBSN-UHFFFAOYSA-L 0.000 description 1
• 239000000463 material Substances 0.000 description 1
• 239000000178 monomer Substances 0.000 description 1
• 238000000465 moulding Methods 0.000 description 1
• 239000012299 nitrogen atmosphere Substances 0.000 description 1
• JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
• 239000001301 oxygen Substances 0.000 description 1
• 229910052760 oxygen Inorganic materials 0.000 description 1
• 238000011084 recovery Methods 0.000 description 1
• 230000008929 regeneration Effects 0.000 description 1
• 238000011069 regeneration method Methods 0.000 description 1
• 150000004671 saturated fatty acids Chemical class 0.000 description 1
• 239000008247 solid mixture Substances 0.000 description 1
• OKUCEQDKBKYEJY-UHFFFAOYSA-N tert-butyl 3-(methylamino)pyrrolidine-1-carboxylate Chemical compound CNC1CCN(C(=O)OC(C)(C)C)C1 OKUCEQDKBKYEJY-UHFFFAOYSA-N 0.000 description 1
• 150000003623 transition metal compounds Chemical class 0.000 description 1
• PLSARIKBYIPYPF-UHFFFAOYSA-H trimagnesium dicitrate Chemical compound [Mg+2].[Mg+2].[Mg+2].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O.[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O PLSARIKBYIPYPF-UHFFFAOYSA-H 0.000 description 1
• PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
• 238000004383 yellowing Methods 0.000 description 1