DE1145360B - Verfahren zur Oxydation von Phenolen mit Sauerstoff - Google Patents
Verfahren zur Oxydation von Phenolen mit SauerstoffInfo
- Publication number
- DE1145360B DE1145360B DEG27341A DEG0027341A DE1145360B DE 1145360 B DE1145360 B DE 1145360B DE G27341 A DEG27341 A DE G27341A DE G0027341 A DEG0027341 A DE G0027341A DE 1145360 B DE1145360 B DE 1145360B
- Authority
- DE
- Germany
- Prior art keywords
- phenol
- reaction
- oxygen
- oxidation
- hydrogen
- Prior art date
- 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.)
- Pending
Links
- 238000007254 oxidation reaction Methods 0.000 title claims description 24
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 title claims description 20
- 229910052760 oxygen Inorganic materials 0.000 title claims description 20
- 239000001301 oxygen Substances 0.000 title claims description 20
- 238000000034 method Methods 0.000 title claims description 18
- 230000003647 oxidation Effects 0.000 title claims description 17
- 150000002989 phenols Chemical class 0.000 title claims description 12
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 24
- 150000003839 salts Chemical class 0.000 claims description 18
- 229920000090 poly(aryl ether) Polymers 0.000 claims description 16
- 150000003512 tertiary amines Chemical class 0.000 claims description 16
- 150000001875 compounds Chemical class 0.000 claims description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 229930195733 hydrocarbon Natural products 0.000 claims description 8
- 239000004215 Carbon black (E152) Substances 0.000 claims description 6
- 230000015572 biosynthetic process Effects 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- -1 hydrocarbon radical Chemical class 0.000 description 31
- 238000006243 chemical reaction Methods 0.000 description 26
- 239000003054 catalyst Substances 0.000 description 16
- 239000007795 chemical reaction product Substances 0.000 description 16
- 125000001424 substituent group Chemical group 0.000 description 16
- 239000000047 product Substances 0.000 description 15
- 229920000642 polymer Polymers 0.000 description 13
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 12
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 12
- 150000001412 amines Chemical class 0.000 description 11
- 239000011541 reaction mixture Substances 0.000 description 11
- 239000002904 solvent Substances 0.000 description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- 125000003118 aryl group Chemical group 0.000 description 9
- 229910052802 copper Inorganic materials 0.000 description 8
- 239000010949 copper Substances 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- 238000004519 manufacturing process Methods 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000006227 byproduct Substances 0.000 description 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
- 239000007858 starting material Substances 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 239000000835 fiber Substances 0.000 description 5
- 239000003607 modifier Substances 0.000 description 5
- 239000000376 reactant Substances 0.000 description 5
- 230000035484 reaction time Effects 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 150000005208 1,4-dihydroxybenzenes Chemical class 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 125000004104 aryloxy group Chemical group 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 4
- KDTZBYPBMTXCSO-UHFFFAOYSA-N 2-phenoxyphenol Chemical compound OC1=CC=CC=C1OC1=CC=CC=C1 KDTZBYPBMTXCSO-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 230000002411 adverse Effects 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 239000003957 anion exchange resin Substances 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 150000001879 copper Chemical class 0.000 description 3
- 239000000945 filler Substances 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 150000002367 halogens Chemical class 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 150000002978 peroxides Chemical class 0.000 description 3
- 239000000057 synthetic resin Substances 0.000 description 3
- 229920003002 synthetic resin Polymers 0.000 description 3
- CNHDIAIOKMXOLK-UHFFFAOYSA-N toluquinol Chemical compound CC1=CC(O)=CC=C1O CNHDIAIOKMXOLK-UHFFFAOYSA-N 0.000 description 3
- IQUPABOKLQSFBK-UHFFFAOYSA-N 2-nitrophenol Chemical class OC1=CC=CC=C1[N+]([O-])=O IQUPABOKLQSFBK-UHFFFAOYSA-N 0.000 description 2
- NURQLCJSMXZBPC-UHFFFAOYSA-N 3,4-dimethylpyridine Chemical compound CC1=CC=NC=C1C NURQLCJSMXZBPC-UHFFFAOYSA-N 0.000 description 2
- BVJWEUYJIHKEJV-UHFFFAOYSA-N 4-(2,6-dimethylphenoxy)-2,6-dimethylphenol Chemical compound CC1=C(O)C(C)=CC(OC=2C(=CC=CC=2C)C)=C1 BVJWEUYJIHKEJV-UHFFFAOYSA-N 0.000 description 2
- ZSBDGXGICLIJGD-UHFFFAOYSA-N 4-phenoxyphenol Chemical compound C1=CC(O)=CC=C1OC1=CC=CC=C1 ZSBDGXGICLIJGD-UHFFFAOYSA-N 0.000 description 2
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 150000001450 anions Chemical class 0.000 description 2
- 229940111121 antirheumatic drug quinolines Drugs 0.000 description 2
- 150000001555 benzenes Chemical class 0.000 description 2
- 238000003490 calendering Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 2
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 2
- 229940045803 cuprous chloride Drugs 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 238000001125 extrusion Methods 0.000 description 2
- 239000004744 fabric Substances 0.000 description 2
- 230000002349 favourable effect Effects 0.000 description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 description 2
- 238000011065 in-situ storage Methods 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- OXNIZHLAWKMVMX-UHFFFAOYSA-N picric acid Chemical compound OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-N 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 235000013824 polyphenols Nutrition 0.000 description 2
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 150000003222 pyridines Chemical class 0.000 description 2
- 150000003248 quinolines Chemical class 0.000 description 2
- 239000012429 reaction media Substances 0.000 description 2
- 239000012262 resinous product Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- PFTAWBLQPZVEMU-DZGCQCFKSA-N (+)-catechin Chemical compound C1([C@H]2OC3=CC(O)=CC(O)=C3C[C@@H]2O)=CC=C(O)C(O)=C1 PFTAWBLQPZVEMU-DZGCQCFKSA-N 0.000 description 1
- UTCOUOISVRSLSH-UHFFFAOYSA-N 1,2-Anthracenediol Chemical compound C1=CC=CC2=CC3=C(O)C(O)=CC=C3C=C21 UTCOUOISVRSLSH-UHFFFAOYSA-N 0.000 description 1
- HTDQSWDEWGSAMN-UHFFFAOYSA-N 1-bromo-2-methoxybenzene Chemical compound COC1=CC=CC=C1Br HTDQSWDEWGSAMN-UHFFFAOYSA-N 0.000 description 1
- ORIUEIWYWDPDHR-UHFFFAOYSA-N 2,6-dimethyl-4-(2-methyl-6-propylphenoxy)phenol Chemical compound CC1=C(C(=CC(=C1)OC1=C(C=CC=C1C)CCC)C)O ORIUEIWYWDPDHR-UHFFFAOYSA-N 0.000 description 1
- BGZLIKKWDSAMSL-UHFFFAOYSA-N 2,6-dimethyl-4-(2-methylphenoxy)phenol Chemical compound CC1=C(C(=CC(=C1)OC1=C(C=CC=C1)C)C)O BGZLIKKWDSAMSL-UHFFFAOYSA-N 0.000 description 1
- KWSXFHAXACMPQC-UHFFFAOYSA-N 2,6-dimethyl-4-(2-phenylphenoxy)phenol Chemical compound CC1=C(C(=CC(=C1)OC1=C(C=CC=C1)C1=CC=CC=C1)C)O KWSXFHAXACMPQC-UHFFFAOYSA-N 0.000 description 1
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical class CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 1
- VBYGHXFBLOWOMS-UHFFFAOYSA-N 2-(2-methylphenoxy)phenol Chemical compound CC1=CC=CC=C1OC1=CC=CC=C1O VBYGHXFBLOWOMS-UHFFFAOYSA-N 0.000 description 1
- NSDLXXGJWFQASN-UHFFFAOYSA-N 2-(4-methylphenoxy)phenol Chemical compound C1=CC(C)=CC=C1OC1=CC=CC=C1O NSDLXXGJWFQASN-UHFFFAOYSA-N 0.000 description 1
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 1
- LQDFLHSBNXIWAJ-UHFFFAOYSA-N 4-(2,4-dimethylphenoxy)-2,6-dimethylphenol Chemical compound CC1=CC(C)=CC=C1OC1=CC(C)=C(O)C(C)=C1 LQDFLHSBNXIWAJ-UHFFFAOYSA-N 0.000 description 1
- ZIYSYIDSHPVKPZ-UHFFFAOYSA-N 4-(2,4-dimethylphenoxy)-2-methylphenol Chemical compound CC1=CC(C)=C(OC2=CC(C)=C(O)C=C2)C=C1 ZIYSYIDSHPVKPZ-UHFFFAOYSA-N 0.000 description 1
- IBOWKGBARGTQCG-UHFFFAOYSA-N 4-[4-(2,6-dimethylphenoxy)-2,6-dimethylphenoxy]-2,6-dimethylphenol Chemical compound CC1=C(O)C(C)=CC(OC=2C(=CC(OC=3C(=CC=CC=3C)C)=CC=2C)C)=C1 IBOWKGBARGTQCG-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
- 238000006887 Ullmann reaction Methods 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 239000002250 absorbent Substances 0.000 description 1
- 230000002745 absorbent Effects 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 239000003463 adsorbent Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- ADRVNXBAWSRFAJ-UHFFFAOYSA-N catechin Natural products OC1Cc2cc(O)cc(O)c2OC1c3ccc(O)c(O)c3 ADRVNXBAWSRFAJ-UHFFFAOYSA-N 0.000 description 1
- 235000005487 catechin Nutrition 0.000 description 1
- 239000002738 chelating agent Substances 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 229950001002 cianidanol Drugs 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 229910052570 clay Inorganic materials 0.000 description 1
- 230000009918 complex formation Effects 0.000 description 1
- 238000000748 compression moulding Methods 0.000 description 1
- 150000004699 copper complex Chemical class 0.000 description 1
- RPJAQOVNRDOGAY-UHFFFAOYSA-L copper(1+);sulfite Chemical compound [Cu+].[Cu+].[O-]S([O-])=O RPJAQOVNRDOGAY-UHFFFAOYSA-L 0.000 description 1
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 1
- 229910000366 copper(II) sulfate Inorganic materials 0.000 description 1
- WIVXEZIMDUGYRW-UHFFFAOYSA-L copper(i) sulfate Chemical compound [Cu+].[Cu+].[O-]S([O-])(=O)=O WIVXEZIMDUGYRW-UHFFFAOYSA-L 0.000 description 1
- 229960003280 cupric chloride Drugs 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 210000003298 dental enamel Anatomy 0.000 description 1
- 239000002274 desiccant Substances 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 238000010292 electrical insulation Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 230000009969 flowable effect Effects 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 125000004438 haloalkoxy group Chemical group 0.000 description 1
- 125000004970 halomethyl group Chemical group 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- IPCSVZSSVZVIGE-UHFFFAOYSA-M hexadecanoate Chemical compound CCCCCCCCCCCCCCCC([O-])=O IPCSVZSSVZVIGE-UHFFFAOYSA-M 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 229910000043 hydrogen iodide Inorganic materials 0.000 description 1
- NWVVVBRKAWDGAB-UHFFFAOYSA-N hydroquinone methyl ether Natural products COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 150000002537 isoquinolines Chemical class 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 238000002074 melt spinning Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- QSRRZKPKHJHIRB-UHFFFAOYSA-N methyl 4-[(2,5-dichloro-4-methylthiophen-3-yl)sulfonylamino]-2-hydroxybenzoate Chemical compound C1=C(O)C(C(=O)OC)=CC=C1NS(=O)(=O)C1=C(Cl)SC(Cl)=C1C QSRRZKPKHJHIRB-UHFFFAOYSA-N 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- DYFFAVRFJWYYQO-UHFFFAOYSA-N n-methyl-n-phenylaniline Chemical compound C=1C=CC=CC=1N(C)C1=CC=CC=C1 DYFFAVRFJWYYQO-UHFFFAOYSA-N 0.000 description 1
- 150000005181 nitrobenzenes Chemical class 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000001741 organic sulfur group Chemical group 0.000 description 1
- 238000013021 overheating Methods 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 229930195143 oxyphenol Natural products 0.000 description 1
- HNMUTKMLCMUDSB-UHFFFAOYSA-N phenanthrene-1,2-diol Chemical class C1=CC=C2C3=CC=C(O)C(O)=C3C=CC2=C1 HNMUTKMLCMUDSB-UHFFFAOYSA-N 0.000 description 1
- KHUXNRRPPZOJPT-UHFFFAOYSA-N phenoxy radical Chemical compound O=C1C=C[CH]C=C1 KHUXNRRPPZOJPT-UHFFFAOYSA-N 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 125000000109 phenylethoxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])O* 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 150000004053 quinones Chemical class 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 125000006850 spacer group Chemical group 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 150000003510 tertiary aliphatic amines Chemical class 0.000 description 1
- STOSPPMGXZPHKP-UHFFFAOYSA-N tetrachlorohydroquinone Chemical compound OC1=C(Cl)C(Cl)=C(O)C(Cl)=C1Cl STOSPPMGXZPHKP-UHFFFAOYSA-N 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- 150000005186 trinitrobenzenes Chemical class 0.000 description 1
- 238000010618 wire wrap Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C50/00—Quinones
- C07C50/24—Quinones containing halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/257—Ethers having an ether-oxygen atom bound to carbon atoms both belonging to six-membered aromatic rings
- C07C43/275—Ethers having an ether-oxygen atom bound to carbon atoms both belonging to six-membered aromatic rings having all ether-oxygen atoms bound to carbon atoms of six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C50/00—Quinones
- C07C50/08—Quinones with polycyclic non-condensed quinoid structure
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C50/00—Quinones
- C07C50/26—Quinones containing groups having oxygen atoms singly bound to carbon atoms
- C07C50/30—Quinones containing groups having oxygen atoms singly bound to carbon atoms with polycyclic non-condensed quinoid structure
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/34—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives
- C08G65/38—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives derived from phenols
- C08G65/44—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives derived from phenols by oxidation of phenols
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Polyethers (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Other Resins Obtained By Reactions Not Involving Carbon-To-Carbon Unsaturated Bonds (AREA)
- Organic Insulating Materials (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US744087A US3134753A (en) | 1958-06-24 | 1958-06-24 | Oxidation of aryloxy-substituted phenols |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1145360B true DE1145360B (de) | 1963-03-14 |
Family
ID=24991380
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEG27341A Pending DE1145360B (de) | 1958-06-24 | 1959-06-23 | Verfahren zur Oxydation von Phenolen mit Sauerstoff |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US3134753A (en, 2012) |
| JP (1) | JPS3714645B1 (en, 2012) |
| DE (1) | DE1145360B (en, 2012) |
| FR (1) | FR1234336A (en, 2012) |
| GB (1) | GB930992A (en, 2012) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0054140A1 (de) * | 1980-12-16 | 1982-06-23 | BASF Aktiengesellschaft | Verfahren zur Herstellung von Polyphenylenäthern |
Families Citing this family (41)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3382212A (en) * | 1959-06-17 | 1968-05-07 | Gen Tire & Rubber Co | Process for preparing polyphenylene ethers |
| US3228910A (en) * | 1960-09-22 | 1966-01-11 | Du Pont | Process for preparing solid poly-1, 4-phenylene ethers |
| US3236807A (en) * | 1961-05-02 | 1966-02-22 | Du Pont | Process for preparing poly(unsymmetri-cally-2, 6-disubstituted phenylene) ether |
| CH401019A (de) * | 1961-06-19 | 1965-10-31 | Gen Electric | Verfahren zur Herstellung von tetrasubstituierten Diphenchinonen |
| US3262911A (en) * | 1961-11-29 | 1966-07-26 | Gen Electric | Substituted polyphenylene ethers |
| US3226361A (en) * | 1961-11-29 | 1965-12-28 | Gen Electric | Functional aromatic substituents in polyphenylene oxides |
| US3378505A (en) * | 1961-11-29 | 1968-04-16 | Gen Electric | Substituted polyphenylene ethers |
| NL287348A (en, 2012) * | 1962-01-02 | |||
| US3260701A (en) * | 1962-12-12 | 1966-07-12 | Sun Oil Co | Preparation of aromatic polyethers with lead dioxide catalyst |
| US3281393A (en) * | 1962-12-28 | 1966-10-25 | Borden Co | Phenylene oxide polymers substituted with epoxidized alkenyl groups |
| US3256243A (en) * | 1962-12-31 | 1966-06-14 | Gen Electric | Process for preparing poly |
| NL302583A (en, 2012) * | 1962-12-31 | 1900-01-01 | ||
| US3257357A (en) * | 1963-04-01 | 1966-06-21 | Du Pont | Copolymers of polyphenylene ethers |
| US3257358A (en) * | 1963-07-02 | 1966-06-21 | Du Pont | 2, 6-dichloro-1, 4-polyphenylene ether |
| US3292061A (en) * | 1963-08-13 | 1966-12-13 | Gen Electric | Electrical capacitor with a polyphenylene ether dielectric |
| US3259520A (en) * | 1963-10-09 | 1966-07-05 | Gen Electric | Antistatic compositions derived from polyphenylene oxides |
| US3262892A (en) * | 1963-11-29 | 1966-07-26 | Gen Electric | Substituted polyphenylene ethers |
| US3422062A (en) * | 1963-11-29 | 1969-01-14 | North American Rockwell | Copolymers of alkenyl phenol |
| US3220979A (en) * | 1964-03-27 | 1965-11-30 | Sun Oil Co | Preparation of aromatic phenols |
| US3342892A (en) * | 1964-08-07 | 1967-09-19 | Eastman Kodak Co | Preparation of linear polyaryl ethers |
| US3350844A (en) * | 1964-09-21 | 1967-11-07 | Gen Electric | Process for the separation or enrichment of gases |
| US3379672A (en) * | 1965-05-17 | 1968-04-23 | Northrop Corp | Substituted polyphenyl ether |
| US3373226A (en) * | 1965-08-02 | 1968-03-12 | Gen Electric | Polymeric films comprising a polyphenylene oxide and blends thereof with polystyrene |
| US3373942A (en) * | 1965-10-05 | 1968-03-19 | Speakman Co | Plastic shower head plungers |
| US3367978A (en) * | 1966-05-03 | 1968-02-06 | Gen Electric | 4-(phenoxy)phenols |
| NL135413C (en, 2012) * | 1966-07-21 | |||
| US3503818A (en) * | 1966-12-01 | 1970-03-31 | Union Carbide Corp | Polyarylene polyether insulated conductors and process for making same |
| US3429850A (en) * | 1967-01-18 | 1969-02-25 | Gen Electric | Stabilized polyphenylene ether compositions |
| US3420792A (en) * | 1967-01-18 | 1969-01-07 | Gen Electric | Stabilized polyphenylene ether |
| US3527665A (en) * | 1967-01-23 | 1970-09-08 | Fmc Corp | Copper-clad laminates of unsaturated thermosetting resins with copper layer coated with polyphenylene oxide resin |
| US3450670A (en) * | 1967-01-27 | 1969-06-17 | Gen Electric | Stabilized polyphenylene ether composition |
| US3465062A (en) * | 1967-02-02 | 1969-09-02 | Gen Electric | Stable polyphenylene ether composition |
| US3925307A (en) * | 1973-04-23 | 1975-12-09 | Raychem Corp | Antioxidants for polyarylether ketones |
| JPS5217559B2 (en, 2012) * | 1973-06-26 | 1977-05-16 | ||
| US4478752A (en) * | 1981-07-20 | 1984-10-23 | Sun Tech, Inc. | Process for oxidizing phenol to p-benzoquinone |
| US4491649A (en) * | 1983-12-01 | 1985-01-01 | Borg-Warner Chemicals, Inc. | High impact polyphenylene ether compositions having improved processability |
| US4485219A (en) * | 1983-12-01 | 1984-11-27 | Borg-Warner Chemicals, Inc. | Phenylene ether copolymer aromatic polycarbonate blends |
| JPS61130340A (ja) * | 1984-11-30 | 1986-06-18 | Mitsubishi Petrochem Co Ltd | ポリフェニレンエーテルの製造方法 |
| US4654405A (en) * | 1985-12-05 | 1987-03-31 | Borg-Warner Chemicals, Inc. | Carboxylated phenylene ether resins |
| DE3629444A1 (de) * | 1986-08-29 | 1988-03-03 | Huels Chemische Werke Ag | Verfahren zur herstellung von polyphenylenethern mit verringerter eigenfarbe |
| CN102807673A (zh) * | 2011-06-03 | 2012-12-05 | 第一毛织株式会社 | 聚亚芳基醚及其制备方法 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE11764C (de) * | Dr. O. BRAUN in Berlin, Wichmannstrafse 18 | Verbesserungen an der durch Patent Nr. 2325 von nagel & kämp geschützten Maschine, um bei Luftabschlufs durch Schlagstiftscheiben Mahlgut zu zerkleinern |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE357756C (de) * | 1920-02-08 | 1922-08-31 | Chemische Werke Grenzach Aktie | Verfahren zur Darstellung von harzartigen Kondensationsprodukten aus Kresolen und Xylenolen |
| FR537335A (en, 2012) * | 1920-06-25 | 1922-05-20 | ||
| US2911380A (en) * | 1955-08-26 | 1959-11-03 | Dow Chemical Co | Poly-(aromatic ether) compositions and method of making same |
| US2961384A (en) * | 1956-12-27 | 1960-11-22 | American Marietta Co | Electrolytic polymerization of phenol |
-
1958
- 1958-06-24 US US744087A patent/US3134753A/en not_active Expired - Lifetime
-
1959
- 1959-06-23 JP JP2073959A patent/JPS3714645B1/ja active Pending
- 1959-06-23 DE DEG27341A patent/DE1145360B/de active Pending
- 1959-06-24 GB GB19526/59A patent/GB930992A/en not_active Expired
- 1959-06-24 FR FR798380A patent/FR1234336A/fr not_active Expired
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE11764C (de) * | Dr. O. BRAUN in Berlin, Wichmannstrafse 18 | Verbesserungen an der durch Patent Nr. 2325 von nagel & kämp geschützten Maschine, um bei Luftabschlufs durch Schlagstiftscheiben Mahlgut zu zerkleinern |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0054140A1 (de) * | 1980-12-16 | 1982-06-23 | BASF Aktiengesellschaft | Verfahren zur Herstellung von Polyphenylenäthern |
Also Published As
| Publication number | Publication date |
|---|---|
| GB930992A (en) | 1963-07-10 |
| US3134753A (en) | 1964-05-26 |
| FR1234336A (fr) | 1960-10-17 |
| JPS3714645B1 (en, 2012) | 1962-09-20 |
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