DE3048992A1 - 4,4'-diphenylether-dialdehyd-bis-dimethylacetal und ein verfahren zu seiner herstellung - Google Patents
4,4'-diphenylether-dialdehyd-bis-dimethylacetal und ein verfahren zu seiner herstellungInfo
- Publication number
- DE3048992A1 DE3048992A1 DE19803048992 DE3048992A DE3048992A1 DE 3048992 A1 DE3048992 A1 DE 3048992A1 DE 19803048992 DE19803048992 DE 19803048992 DE 3048992 A DE3048992 A DE 3048992A DE 3048992 A1 DE3048992 A1 DE 3048992A1
- Authority
- DE
- Germany
- Prior art keywords
- hoechst
- electrolyte
- bis
- graphite
- dialdehyde
- 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.)
- Withdrawn
Links
- 238000000034 method Methods 0.000 title claims abstract description 25
- 238000004519 manufacturing process Methods 0.000 title description 6
- 239000004305 biphenyl Substances 0.000 title description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 42
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 20
- 150000001875 compounds Chemical class 0.000 claims abstract description 19
- 239000003115 supporting electrolyte Substances 0.000 claims abstract description 17
- 229910002804 graphite Inorganic materials 0.000 claims abstract description 13
- 239000010439 graphite Substances 0.000 claims abstract description 13
- 238000006243 chemical reaction Methods 0.000 claims abstract description 12
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims abstract description 12
- 230000003647 oxidation Effects 0.000 claims abstract description 9
- 238000007254 oxidation reaction Methods 0.000 claims abstract description 9
- YWYHGNUFMPSTTR-UHFFFAOYSA-N 1-methyl-4-(4-methylphenoxy)benzene Chemical compound C1=CC(C)=CC=C1OC1=CC=C(C)C=C1 YWYHGNUFMPSTTR-UHFFFAOYSA-N 0.000 claims abstract description 8
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims abstract description 8
- YADSGOSSYOOKMP-UHFFFAOYSA-N dioxolead Chemical compound O=[Pb]=O YADSGOSSYOOKMP-UHFFFAOYSA-N 0.000 claims abstract description 8
- 229910000831 Steel Inorganic materials 0.000 claims abstract description 7
- 239000010959 steel Substances 0.000 claims abstract description 7
- 229910052697 platinum Inorganic materials 0.000 claims abstract description 6
- 229910021397 glassy carbon Inorganic materials 0.000 claims abstract description 5
- 239000000203 mixture Substances 0.000 claims abstract description 5
- QKFFSWPNFCXGIQ-UHFFFAOYSA-M 4-methylbenzenesulfonate;tetraethylazanium Chemical compound CC[N+](CC)(CC)CC.CC1=CC=C(S([O-])(=O)=O)C=C1 QKFFSWPNFCXGIQ-UHFFFAOYSA-M 0.000 claims abstract description 4
- 239000010405 anode material Substances 0.000 claims abstract description 4
- 239000010406 cathode material Substances 0.000 claims abstract description 4
- 229910052759 nickel Inorganic materials 0.000 claims abstract description 4
- 238000002360 preparation method Methods 0.000 claims abstract description 4
- 239000003792 electrolyte Substances 0.000 claims description 18
- 238000005868 electrolysis reaction Methods 0.000 claims description 9
- 229910020808 NaBF Inorganic materials 0.000 claims description 3
- 229910013063 LiBF 4 Inorganic materials 0.000 claims description 2
- 229910021135 KPF6 Inorganic materials 0.000 abstract 1
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 abstract 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract 1
- XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Inorganic materials [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 abstract 1
- 229910001496 lithium tetrafluoroborate Inorganic materials 0.000 abstract 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Inorganic materials [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 abstract 1
- 229910001495 sodium tetrafluoroborate Inorganic materials 0.000 abstract 1
- 235000011149 sulphuric acid Nutrition 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 description 17
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 16
- -1 methoxyl derivatives of toluene Chemical class 0.000 description 14
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 12
- 238000006198 methoxylation reaction Methods 0.000 description 12
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 11
- CHLICZRVGGXEOD-UHFFFAOYSA-N 1-Methoxy-4-methylbenzene Chemical compound COC1=CC=C(C)C=C1 CHLICZRVGGXEOD-UHFFFAOYSA-N 0.000 description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- 239000000047 product Substances 0.000 description 8
- 150000003839 salts Chemical class 0.000 description 7
- 150000001241 acetals Chemical class 0.000 description 6
- 125000003118 aryl group Chemical group 0.000 description 6
- 150000005172 methylbenzenes Chemical class 0.000 description 6
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 6
- 239000000463 material Substances 0.000 description 5
- GQKZBCPTCWJTAS-UHFFFAOYSA-N methoxymethylbenzene Chemical compound COCC1=CC=CC=C1 GQKZBCPTCWJTAS-UHFFFAOYSA-N 0.000 description 5
- 238000006467 substitution reaction Methods 0.000 description 5
- 239000007795 chemical reaction product Substances 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- NNHYAHOTXLASEA-UHFFFAOYSA-N 1-(dimethoxymethyl)-4-methoxybenzene Chemical compound COC(OC)C1=CC=C(OC)C=C1 NNHYAHOTXLASEA-UHFFFAOYSA-N 0.000 description 3
- MKZGLAOLSFUPRT-UHFFFAOYSA-N 1-(dimethoxymethyl)-4-methylbenzene Chemical compound COC(OC)C1=CC=C(C)C=C1 MKZGLAOLSFUPRT-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 239000004698 Polyethylene Substances 0.000 description 3
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 3
- 238000007333 cyanation reaction Methods 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 238000004817 gas chromatography Methods 0.000 description 3
- 238000009905 homogeneous catalytic hydrogenation reaction Methods 0.000 description 3
- ZRSNZINYAWTAHE-UHFFFAOYSA-N p-methoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C=C1 ZRSNZINYAWTAHE-UHFFFAOYSA-N 0.000 description 3
- 229920000573 polyethylene Polymers 0.000 description 3
- 239000010970 precious metal Substances 0.000 description 3
- 238000010626 work up procedure Methods 0.000 description 3
- HEVMDQBCAHEHDY-UHFFFAOYSA-N (Dimethoxymethyl)benzene Chemical compound COC(OC)C1=CC=CC=C1 HEVMDQBCAHEHDY-UHFFFAOYSA-N 0.000 description 2
- SPEUIVXLLWOEMJ-UHFFFAOYSA-N 1,1-dimethoxyethane Chemical compound COC(C)OC SPEUIVXLLWOEMJ-UHFFFAOYSA-N 0.000 description 2
- FETIWDPIODONQB-UHFFFAOYSA-N 1-methyl-4-[(2-methylpropan-2-yl)oxy]benzene Chemical compound CC1=CC=C(OC(C)(C)C)C=C1 FETIWDPIODONQB-UHFFFAOYSA-N 0.000 description 2
- PKZJLOCLABXVMC-UHFFFAOYSA-N 2-Methoxybenzaldehyde Chemical compound COC1=CC=CC=C1C=O PKZJLOCLABXVMC-UHFFFAOYSA-N 0.000 description 2
- DTFKRVXLBCAIOZ-UHFFFAOYSA-N 2-methylanisole Chemical class COC1=CC=CC=C1C DTFKRVXLBCAIOZ-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 238000007259 addition reaction Methods 0.000 description 2
- 150000004996 alkyl benzenes Chemical class 0.000 description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical class COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- 150000003934 aromatic aldehydes Chemical class 0.000 description 2
- 150000001491 aromatic compounds Chemical class 0.000 description 2
- 125000004104 aryloxy group Chemical group 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 125000001891 dimethoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- 230000005611 electricity Effects 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 239000011133 lead Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- MMSLOZQEMPDGPI-UHFFFAOYSA-N p-Mentha-1,3,5,8-tetraene Chemical compound CC(=C)C1=CC=C(C)C=C1 MMSLOZQEMPDGPI-UHFFFAOYSA-N 0.000 description 2
- FXLOVSHXALFLKQ-UHFFFAOYSA-N p-tolualdehyde Chemical compound CC1=CC=C(C=O)C=C1 FXLOVSHXALFLKQ-UHFFFAOYSA-N 0.000 description 2
- LPNBBFKOUUSUDB-UHFFFAOYSA-N p-toluic acid Chemical compound CC1=CC=C(C(O)=O)C=C1 LPNBBFKOUUSUDB-UHFFFAOYSA-N 0.000 description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical class OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 229920000570 polyether Polymers 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- MNWBNISUBARLIT-UHFFFAOYSA-N sodium cyanide Chemical class [Na+].N#[C-] MNWBNISUBARLIT-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 150000003613 toluenes Chemical group 0.000 description 2
- YCCVSCJOXISVEI-UHFFFAOYSA-N 1-(1-methoxy-1-methylethyl)-4-methylbenzene Chemical compound COC(C)(C)C1=CC=C(C)C=C1 YCCVSCJOXISVEI-UHFFFAOYSA-N 0.000 description 1
- HQULKVOWGZVAJP-UHFFFAOYSA-N 1-(dimethoxymethyl)-4-[(2-methylpropan-2-yl)oxy]benzene Chemical compound COC(OC)C1=CC=C(OC(C)(C)C)C=C1 HQULKVOWGZVAJP-UHFFFAOYSA-N 0.000 description 1
- XVFZGTVKQIKOBD-UHFFFAOYSA-N 1-(dimethoxymethyl)-4-phenoxybenzene Chemical compound C1=CC(C(OC)OC)=CC=C1OC1=CC=CC=C1 XVFZGTVKQIKOBD-UHFFFAOYSA-N 0.000 description 1
- KGIRUZVVVUEQGZ-UHFFFAOYSA-N 1-(dimethoxymethyl)-4-phenylmethoxybenzene Chemical compound C1=CC(C(OC)OC)=CC=C1OCC1=CC=CC=C1 KGIRUZVVVUEQGZ-UHFFFAOYSA-N 0.000 description 1
- HNASEWFYPPRNKM-UHFFFAOYSA-N 1-(methoxymethyl)-4-methylbenzene Chemical compound COCC1=CC=C(C)C=C1 HNASEWFYPPRNKM-UHFFFAOYSA-N 0.000 description 1
- RSOYRXBYZFBWFS-UHFFFAOYSA-N 1-methoxy-4-(methoxymethyl)benzene Chemical compound COCC1=CC=C(OC)C=C1 RSOYRXBYZFBWFS-UHFFFAOYSA-N 0.000 description 1
- SSTNIXFHCIOCJI-UHFFFAOYSA-N 1-methyl-4-phenoxybenzene Chemical compound C1=CC(C)=CC=C1OC1=CC=CC=C1 SSTNIXFHCIOCJI-UHFFFAOYSA-N 0.000 description 1
- CHBXCQHBCCLICW-UHFFFAOYSA-N 1-methyl-4-phenylmethoxybenzene Chemical compound C1=CC(C)=CC=C1OCC1=CC=CC=C1 CHBXCQHBCCLICW-UHFFFAOYSA-N 0.000 description 1
- AROCNZZBLCAOPH-UHFFFAOYSA-N 1-methyl-4-prop-2-enoxybenzene Chemical compound CC1=CC=C(OCC=C)C=C1 AROCNZZBLCAOPH-UHFFFAOYSA-N 0.000 description 1
- JXFVMNFKABWTHD-UHFFFAOYSA-N 1-methyl-4-propylbenzene Chemical compound CCCC1=CC=C(C)C=C1 JXFVMNFKABWTHD-UHFFFAOYSA-N 0.000 description 1
- IVBVWDZBOIDWSI-UHFFFAOYSA-N 1-tert-butyl-4-(dimethoxymethyl)benzene Chemical compound COC(OC)C1=CC=C(C(C)(C)C)C=C1 IVBVWDZBOIDWSI-UHFFFAOYSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- KVTOUUODKAHJCM-UHFFFAOYSA-N 2-methoxy-4-methylbenzaldehyde Chemical compound COC1=CC(C)=CC=C1C=O KVTOUUODKAHJCM-UHFFFAOYSA-N 0.000 description 1
- 239000001431 2-methylbenzaldehyde Substances 0.000 description 1
- NWPNXBQSRGKSJB-UHFFFAOYSA-N 2-methylbenzonitrile Chemical compound CC1=CC=CC=C1C#N NWPNXBQSRGKSJB-UHFFFAOYSA-N 0.000 description 1
- 125000005975 2-phenylethyloxy group Chemical group 0.000 description 1
- TYNJQOJWNMZQFZ-UHFFFAOYSA-N 4-prop-2-enoxybenzaldehyde Chemical compound C=CCOC1=CC=C(C=O)C=C1 TYNJQOJWNMZQFZ-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 241000269627 Amphiuma means Species 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- ZNZYKNKBJPZETN-WELNAUFTSA-N Dialdehyde 11678 Chemical compound N1C2=CC=CC=C2C2=C1[C@H](C[C@H](/C(=C/O)C(=O)OC)[C@@H](C=C)C=O)NCC2 ZNZYKNKBJPZETN-WELNAUFTSA-N 0.000 description 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 229910013684 LiClO 4 Inorganic materials 0.000 description 1
- PHXQIAWFIIMOKG-UHFFFAOYSA-N NClO Chemical compound NClO PHXQIAWFIIMOKG-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 150000003935 benzaldehydes Chemical class 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000005352 clarification Methods 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 239000006184 cosolvent Substances 0.000 description 1
- 230000006735 deficit Effects 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 150000001987 diarylethers Chemical class 0.000 description 1
- ZUTDMCQPJTZWDJ-UHFFFAOYSA-M dimethyl phosphate;tetramethylazanium Chemical compound C[N+](C)(C)C.COP([O-])(=O)OC ZUTDMCQPJTZWDJ-UHFFFAOYSA-M 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000006181 electrochemical material Substances 0.000 description 1
- 230000005518 electrochemistry Effects 0.000 description 1
- 238000006056 electrooxidation reaction Methods 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 238000007046 ethoxylation reaction Methods 0.000 description 1
- HCWMUANODLPMEO-UHFFFAOYSA-M ethyl sulfate;tetraethylazanium Chemical compound CCOS([O-])(=O)=O.CC[N+](CC)(CC)CC HCWMUANODLPMEO-UHFFFAOYSA-M 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 150000004673 fluoride salts Chemical class 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 238000007327 hydrogenolysis reaction Methods 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
- 230000000415 inactivating effect Effects 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 238000002386 leaching Methods 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- QSSJZLPUHJDYKF-UHFFFAOYSA-N methyl 4-methylbenzoate Chemical compound COC(=O)C1=CC=C(C)C=C1 QSSJZLPUHJDYKF-UHFFFAOYSA-N 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 125000005186 naphthyloxy group Chemical group C1(=CC=CC2=CC=CC=C12)O* 0.000 description 1
- 125000001477 organic nitrogen group Chemical group 0.000 description 1
- 150000002905 orthoesters Chemical class 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 238000005086 pumping Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- KUCOHFSKRZZVRO-UHFFFAOYSA-N terephthalaldehyde Chemical compound O=CC1=CC=C(C=O)C=C1 KUCOHFSKRZZVRO-UHFFFAOYSA-N 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/30—Compounds having groups
- C07C43/315—Compounds having groups containing oxygen atoms singly bound to carbon atoms not being acetal carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C25—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES; APPARATUS THEREFOR
- C25B—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES FOR THE PRODUCTION OF COMPOUNDS OR NON-METALS; APPARATUS THEREFOR
- C25B3/00—Electrolytic production of organic compounds
- C25B3/20—Processes
- C25B3/23—Oxidation
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Electrochemistry (AREA)
- Materials Engineering (AREA)
- Metallurgy (AREA)
- Electrolytic Production Of Non-Metals, Compounds, Apparatuses Therefor (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Phenolic Resins Or Amino Resins (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
Priority Applications (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19803048992 DE3048992A1 (de) | 1980-12-24 | 1980-12-24 | 4,4'-diphenylether-dialdehyd-bis-dimethylacetal und ein verfahren zu seiner herstellung |
| EP81109003A EP0054698B1 (de) | 1980-12-24 | 1981-10-27 | 4,4'-Diphenylether-dialdehyd-bis-dimethylacetal und ein Verfahren zu seiner Herstellung |
| AT81109003T ATE8039T1 (de) | 1980-12-24 | 1981-10-27 | 4,4'-diphenylether-dialdehyd-bis-dimethylacetal und ein verfahren zu seiner herstellung. |
| DE8181109003T DE3164335D1 (en) | 1980-12-24 | 1981-10-27 | 4,4'-diphenyl ether-dialdehyde-bis-dimethyl acetal, and a method for its preparation |
| CA000392523A CA1184207A (en) | 1980-12-24 | 1981-12-17 | 4,4'-diphenyl ether-dialdehyde-bis-dimethylacetal and a process for its preparation |
| US06/333,013 US4405816A (en) | 1980-12-24 | 1981-12-21 | 4,4'-Diphenyl ether-dialdehyde-bis-dimethylacetal |
| BR8108376A BR8108376A (pt) | 1980-12-24 | 1981-12-23 | 4,4-difenileter-dialdeido-bis-dimetilacetal e um processo para sua preparacao |
| JP56208222A JPS57136538A (en) | 1980-12-24 | 1981-12-24 | 4,4'-diphenylether-dialdehyde-bis-dimethyl acetal and manufacture |
| US06/412,246 US4457810A (en) | 1980-12-24 | 1982-08-27 | 4,4'-Diphenyl ether-dialdehyde-bis-dimethylacetal and a process for its preparation |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19803048992 DE3048992A1 (de) | 1980-12-24 | 1980-12-24 | 4,4'-diphenylether-dialdehyd-bis-dimethylacetal und ein verfahren zu seiner herstellung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE3048992A1 true DE3048992A1 (de) | 1982-07-15 |
Family
ID=6120257
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19803048992 Withdrawn DE3048992A1 (de) | 1980-12-24 | 1980-12-24 | 4,4'-diphenylether-dialdehyd-bis-dimethylacetal und ein verfahren zu seiner herstellung |
| DE8181109003T Expired DE3164335D1 (en) | 1980-12-24 | 1981-10-27 | 4,4'-diphenyl ether-dialdehyde-bis-dimethyl acetal, and a method for its preparation |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE8181109003T Expired DE3164335D1 (en) | 1980-12-24 | 1981-10-27 | 4,4'-diphenyl ether-dialdehyde-bis-dimethyl acetal, and a method for its preparation |
Country Status (7)
| Country | Link |
|---|---|
| US (2) | US4405816A (en, 2012) |
| EP (1) | EP0054698B1 (en, 2012) |
| JP (1) | JPS57136538A (en, 2012) |
| AT (1) | ATE8039T1 (en, 2012) |
| BR (1) | BR8108376A (en, 2012) |
| CA (1) | CA1184207A (en, 2012) |
| DE (2) | DE3048992A1 (en, 2012) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3421976A1 (de) * | 1984-06-14 | 1985-12-19 | Basf Ag, 6700 Ludwigshafen | Verfahren zur herstellung von phthalaldehydacetalen |
| US4871430A (en) * | 1987-02-19 | 1989-10-03 | The Dow Chemical Company | Novel multifunctional compounds and electrolytic oxidative coupling process |
| JP2669732B2 (ja) * | 1990-07-27 | 1997-10-29 | 昭和電工株式会社 | 旋光度検出方法、その検出装置および旋光度検出用セル |
| JPH05294984A (ja) * | 1992-04-15 | 1993-11-09 | Wako Pure Chem Ind Ltd | マルトオリゴ糖誘導体の新規な製造方法 |
| KR20150023709A (ko) * | 2012-06-15 | 2015-03-05 | 바스프 에스이 | 친핵체 존재 하의 유기 기판의 애노드 산화 |
| US10338277B2 (en) * | 2014-12-17 | 2019-07-02 | Fujifilm Corporation | Polarizing plate protective film, polarizing plate, and display |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2848397C2 (de) * | 1978-11-08 | 1982-09-23 | Basf Ag, 6700 Ludwigshafen | Elektrochemische Herstellung von in 4-Stellung substituierten Benzaldehyddialkylacetalen |
| US4318783A (en) * | 1978-11-30 | 1982-03-09 | Bayer Aktiengesellschaft | Process for the preparation of optionally substituted benzaldehyde dialkyl acetals |
| DE2912058A1 (de) * | 1979-03-27 | 1980-10-09 | Bayer Ag | Verfahren zur herstellung von gegebenenfalls substituierten benzaldehyd- dialkylacetalen |
-
1980
- 1980-12-24 DE DE19803048992 patent/DE3048992A1/de not_active Withdrawn
-
1981
- 1981-10-27 EP EP81109003A patent/EP0054698B1/de not_active Expired
- 1981-10-27 AT AT81109003T patent/ATE8039T1/de not_active IP Right Cessation
- 1981-10-27 DE DE8181109003T patent/DE3164335D1/de not_active Expired
- 1981-12-17 CA CA000392523A patent/CA1184207A/en not_active Expired
- 1981-12-21 US US06/333,013 patent/US4405816A/en not_active Expired - Lifetime
- 1981-12-23 BR BR8108376A patent/BR8108376A/pt unknown
- 1981-12-24 JP JP56208222A patent/JPS57136538A/ja active Granted
-
1982
- 1982-08-27 US US06/412,246 patent/US4457810A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| EP0054698A1 (de) | 1982-06-30 |
| DE3164335D1 (en) | 1984-07-26 |
| BR8108376A (pt) | 1982-10-13 |
| ATE8039T1 (de) | 1984-07-15 |
| US4405816A (en) | 1983-09-20 |
| EP0054698B1 (de) | 1984-06-20 |
| US4457810A (en) | 1984-07-03 |
| JPS57136538A (en) | 1982-08-23 |
| CA1184207A (en) | 1985-03-19 |
| JPH0210814B2 (en, 2012) | 1990-03-09 |
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