NO904328L - Fremgangsmaate for fremstilling av benzaldehyder. - Google Patents
Fremgangsmaate for fremstilling av benzaldehyder.Info
- Publication number
- NO904328L NO904328L NO90904328A NO904328A NO904328L NO 904328 L NO904328 L NO 904328L NO 90904328 A NO90904328 A NO 90904328A NO 904328 A NO904328 A NO 904328A NO 904328 L NO904328 L NO 904328L
- Authority
- NO
- Norway
- Prior art keywords
- radical
- carbon atoms
- relation
- hydroxybenzaldehyde
- stands
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 36
- 238000002360 preparation method Methods 0.000 title abstract description 5
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims abstract description 38
- 239000010949 copper Substances 0.000 claims abstract description 32
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims abstract description 31
- 229910052802 copper Inorganic materials 0.000 claims abstract description 31
- 229910052783 alkali metal Inorganic materials 0.000 claims abstract description 24
- 150000001340 alkali metals Chemical class 0.000 claims abstract description 24
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims abstract description 21
- 150000001342 alkaline earth metals Chemical class 0.000 claims abstract description 21
- 239000001569 carbon dioxide Substances 0.000 claims abstract description 19
- 229910002092 carbon dioxide Inorganic materials 0.000 claims abstract description 19
- 150000001875 compounds Chemical class 0.000 claims abstract description 18
- 238000006243 chemical reaction Methods 0.000 claims abstract description 13
- 239000011541 reaction mixture Substances 0.000 claims abstract description 13
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims abstract description 11
- 239000005749 Copper compound Substances 0.000 claims abstract description 8
- 150000001880 copper compounds Chemical class 0.000 claims abstract description 8
- 150000005677 organic carbonates Chemical class 0.000 claims abstract description 7
- 125000002524 organometallic group Chemical group 0.000 claims abstract description 5
- -1 aromatic cyclic radical Chemical class 0.000 claims description 73
- 125000004432 carbon atom Chemical group C* 0.000 claims description 68
- 150000003254 radicals Chemical class 0.000 claims description 58
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical group [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims description 18
- 125000005843 halogen group Chemical group 0.000 claims description 17
- 125000000217 alkyl group Chemical group 0.000 claims description 16
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 claims description 12
- XTVVROIMIGLXTD-UHFFFAOYSA-N copper(II) nitrate Chemical compound [Cu+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O XTVVROIMIGLXTD-UHFFFAOYSA-N 0.000 claims description 12
- 239000000203 mixture Substances 0.000 claims description 11
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 10
- 239000003054 catalyst Substances 0.000 claims description 9
- 238000004519 manufacturing process Methods 0.000 claims description 8
- 125000002950 monocyclic group Chemical group 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 8
- DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 claims description 8
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 7
- KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 claims description 7
- 150000001299 aldehydes Chemical group 0.000 claims description 7
- FZHSPPYCNDYIKD-UHFFFAOYSA-N 5-methoxysalicylaldehyde Chemical compound COC1=CC=C(O)C(C=O)=C1 FZHSPPYCNDYIKD-UHFFFAOYSA-N 0.000 claims description 6
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 6
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 6
- GEZOTWYUIKXWOA-UHFFFAOYSA-L copper;carbonate Chemical compound [Cu+2].[O-]C([O-])=O GEZOTWYUIKXWOA-UHFFFAOYSA-L 0.000 claims description 6
- 229960003280 cupric chloride Drugs 0.000 claims description 6
- 229910052740 iodine Inorganic materials 0.000 claims description 6
- 229910052708 sodium Inorganic materials 0.000 claims description 6
- 229940116318 copper carbonate Drugs 0.000 claims description 5
- TUJKJAMUKRIRHC-UHFFFAOYSA-N hydroxyl Chemical compound [OH] TUJKJAMUKRIRHC-UHFFFAOYSA-N 0.000 claims description 5
- OPHQOIGEOHXOGX-UHFFFAOYSA-N 3,4,5-trimethoxybenzaldehyde Chemical compound COC1=CC(C=O)=CC(OC)=C1OC OPHQOIGEOHXOGX-UHFFFAOYSA-N 0.000 claims description 4
- JJLJMEJHUUYSSY-UHFFFAOYSA-L Copper hydroxide Chemical compound [OH-].[OH-].[Cu+2] JJLJMEJHUUYSSY-UHFFFAOYSA-L 0.000 claims description 4
- OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 claims description 4
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 229910000009 copper(II) carbonate Inorganic materials 0.000 claims description 4
- OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 claims description 4
- 239000011646 cupric carbonate Substances 0.000 claims description 4
- 235000019854 cupric carbonate Nutrition 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical compound COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 229910052700 potassium Inorganic materials 0.000 claims description 4
- 239000011591 potassium Substances 0.000 claims description 4
- 239000011734 sodium Substances 0.000 claims description 4
- 239000004215 Carbon black (E152) Substances 0.000 claims description 3
- 125000004429 atom Chemical group 0.000 claims description 3
- 125000005842 heteroatom Chemical group 0.000 claims description 3
- 229930195733 hydrocarbon Natural products 0.000 claims description 3
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 claims description 3
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 claims description 3
- MWOOGOJBHIARFG-UHFFFAOYSA-N vanillin Chemical compound COC1=CC(C=O)=CC=C1O MWOOGOJBHIARFG-UHFFFAOYSA-N 0.000 claims description 3
- SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 claims description 2
- YUDRVAHLXDBKSR-UHFFFAOYSA-N [CH]1CCCCC1 Chemical compound [CH]1CCCCC1 YUDRVAHLXDBKSR-UHFFFAOYSA-N 0.000 claims description 2
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 claims description 2
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 125000000304 alkynyl group Chemical group 0.000 claims description 2
- 239000013522 chelant Substances 0.000 claims description 2
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 claims description 2
- 229910000366 copper(II) sulfate Inorganic materials 0.000 claims description 2
- 229940076286 cupric acetate Drugs 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 150000002484 inorganic compounds Chemical class 0.000 claims description 2
- 229910010272 inorganic material Inorganic materials 0.000 claims description 2
- 229910052751 metal Inorganic materials 0.000 claims description 2
- 239000002184 metal Substances 0.000 claims description 2
- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 150000002894 organic compounds Chemical class 0.000 claims description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-M phenolate Chemical compound [O-]C1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-M 0.000 claims description 2
- 229940031826 phenolate Drugs 0.000 claims description 2
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- 125000004436 sodium atom Chemical group 0.000 claims description 2
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- DKZBBWMURDFHNE-UHFFFAOYSA-N trans-coniferylaldehyde Natural products COC1=CC(C=CC=O)=CC=C1O DKZBBWMURDFHNE-UHFFFAOYSA-N 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- KCDXJAYRVLXPFO-UHFFFAOYSA-N syringaldehyde Chemical compound COC1=CC(C=O)=CC(OC)=C1O KCDXJAYRVLXPFO-UHFFFAOYSA-N 0.000 description 14
- COBXDAOIDYGHGK-UHFFFAOYSA-N syringaldehyde Natural products COC1=CC=C(C=O)C(OC)=C1O COBXDAOIDYGHGK-UHFFFAOYSA-N 0.000 description 14
- KLSHZDPXXKAHIJ-UHFFFAOYSA-N 3-bromo-4-hydroxy-5-methoxybenzaldehyde Chemical compound COC1=CC(C=O)=CC(Br)=C1O KLSHZDPXXKAHIJ-UHFFFAOYSA-N 0.000 description 13
- 238000003756 stirring Methods 0.000 description 11
- UOTMHAOCAJROQF-UHFFFAOYSA-N 3-bromo-4-hydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C=C1Br UOTMHAOCAJROQF-UHFFFAOYSA-N 0.000 description 9
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000004809 Teflon Substances 0.000 description 5
- 229920006362 Teflon® Polymers 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- SXRHGLQCOLNZPT-UHFFFAOYSA-N 3,5-dibromo-4-hydroxybenzaldehyde Chemical compound OC1=C(Br)C=C(C=O)C=C1Br SXRHGLQCOLNZPT-UHFFFAOYSA-N 0.000 description 4
- MKKSTJKBKNCMRV-UHFFFAOYSA-N 5-bromo-2-hydroxybenzaldehyde Chemical compound OC1=CC=C(Br)C=C1C=O MKKSTJKBKNCMRV-UHFFFAOYSA-N 0.000 description 4
- 239000012153 distilled water Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- 239000007791 liquid phase Substances 0.000 description 3
- MJRJDGKISPWEMD-OEAKJJBVSA-N (2E)-3-(3,5-dibromo-4-hydroxyphenyl)-N-[2-(3,5-dibromo-4-hydroxyphenyl)ethyl]-2-hydroxyiminopropanamide Chemical compound BrC=1C=C(C=C(C=1O)Br)CCNC(/C(/CC1=CC(=C(C(=C1)Br)O)Br)=N/O)=O MJRJDGKISPWEMD-OEAKJJBVSA-N 0.000 description 2
- GVSGSHGXUXLQNS-UHFFFAOYSA-N 3-bromo-4,5-dihydroxybenzaldehyde Chemical compound OC1=CC(C=O)=CC(Br)=C1O GVSGSHGXUXLQNS-UHFFFAOYSA-N 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 2
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 description 2
- 150000001491 aromatic compounds Chemical class 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- TZIHFWKZFHZASV-UHFFFAOYSA-N methyl formate Chemical compound COC=O TZIHFWKZFHZASV-UHFFFAOYSA-N 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- CLFRCXCBWIQVRN-UHFFFAOYSA-N 2,5-dihydroxybenzaldehyde Chemical class OC1=CC=C(O)C(C=O)=C1 CLFRCXCBWIQVRN-UHFFFAOYSA-N 0.000 description 1
- OCBOCCOUCDGNKX-UHFFFAOYSA-N 2-bromo-4-hydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C(Br)=C1 OCBOCCOUCDGNKX-UHFFFAOYSA-N 0.000 description 1
- NDOPHXWIAZIXPR-UHFFFAOYSA-N 2-bromobenzaldehyde Chemical compound BrC1=CC=CC=C1C=O NDOPHXWIAZIXPR-UHFFFAOYSA-N 0.000 description 1
- HWJJTWWMMHEEAK-UHFFFAOYSA-N 2-hydroxy-3-iodobenzaldehyde Chemical compound OC1=C(I)C=CC=C1C=O HWJJTWWMMHEEAK-UHFFFAOYSA-N 0.000 description 1
- PDFVIWFKGYODKD-UHFFFAOYSA-N 2-hydroxy-5-iodobenzaldehyde Chemical compound OC1=CC=C(I)C=C1C=O PDFVIWFKGYODKD-UHFFFAOYSA-N 0.000 description 1
- OOBOMBYQAJXCHV-UHFFFAOYSA-N 3,4-dihydroxy-5-iodobenzaldehyde Chemical compound OC1=CC(C=O)=CC(I)=C1O OOBOMBYQAJXCHV-UHFFFAOYSA-N 0.000 description 1
- WKZWBCVHXZRSHP-UHFFFAOYSA-N 3-bromo-2,5-dihydroxybenzaldehyde Chemical compound OC1=CC(Br)=C(O)C(C=O)=C1 WKZWBCVHXZRSHP-UHFFFAOYSA-N 0.000 description 1
- STBGLXMINLWCNL-UHFFFAOYSA-N 3-bromo-2-hydroxybenzaldehyde Chemical compound OC1=C(Br)C=CC=C1C=O STBGLXMINLWCNL-UHFFFAOYSA-N 0.000 description 1
- GWEFTCNMUHHQLP-UHFFFAOYSA-N 3-bromo-5-ethoxy-4-hydroxybenzaldehyde Chemical compound CCOC1=CC(C=O)=CC(Br)=C1O GWEFTCNMUHHQLP-UHFFFAOYSA-N 0.000 description 1
- SUISZCALMBHJQX-UHFFFAOYSA-N 3-bromobenzaldehyde Chemical compound BrC1=CC=CC(C=O)=C1 SUISZCALMBHJQX-UHFFFAOYSA-N 0.000 description 1
- WFAHCDLEWJKPJS-UHFFFAOYSA-N 3-ethoxy-4-hydroxy-5-iodobenzaldehyde Chemical compound CCOC1=CC(C=O)=CC(I)=C1O WFAHCDLEWJKPJS-UHFFFAOYSA-N 0.000 description 1
- IHLOHISMHMTTAA-UHFFFAOYSA-N 3-hydroxy-4-iodobenzaldehyde Chemical compound OC1=CC(C=O)=CC=C1I IHLOHISMHMTTAA-UHFFFAOYSA-N 0.000 description 1
- USCBCBWUZOPHNV-UHFFFAOYSA-N 4-bromo-3-hydroxybenzaldehyde Chemical compound OC1=CC(C=O)=CC=C1Br USCBCBWUZOPHNV-UHFFFAOYSA-N 0.000 description 1
- ZRYZBQLXDKPBDU-UHFFFAOYSA-N 4-bromobenzaldehyde Chemical compound BrC1=CC=C(C=O)C=C1 ZRYZBQLXDKPBDU-UHFFFAOYSA-N 0.000 description 1
- FSNWAMYECSEIEX-UHFFFAOYSA-N 4-hydroxy-2-iodobenzaldehyde Chemical compound OC1=CC=C(C=O)C(I)=C1 FSNWAMYECSEIEX-UHFFFAOYSA-N 0.000 description 1
- WHLUEIMENHLCMY-UHFFFAOYSA-N 4-hydroxy-3,5-diiodobenzaldehyde Chemical compound OC1=C(I)C=C(C=O)C=C1I WHLUEIMENHLCMY-UHFFFAOYSA-N 0.000 description 1
- KNQVIRRXVOTGGT-UHFFFAOYSA-N 4-hydroxy-3-iodobenzaldehyde Chemical compound OC1=CC=C(C=O)C=C1I KNQVIRRXVOTGGT-UHFFFAOYSA-N 0.000 description 1
- IJIBRSFAXRFPPN-UHFFFAOYSA-N 5-bromo-2-methoxybenzaldehyde Chemical compound COC1=CC=C(Br)C=C1C=O IJIBRSFAXRFPPN-UHFFFAOYSA-N 0.000 description 1
- QNOFBICLSSWXDX-UHFFFAOYSA-N OC(O)=O.CC(C)(C)[Na] Chemical compound OC(O)=O.CC(C)(C)[Na] QNOFBICLSSWXDX-UHFFFAOYSA-N 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 150000001718 carbodiimides Chemical class 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- ODCCJTMPMUFERV-UHFFFAOYSA-N ditert-butyl carbonate Chemical compound CC(C)(C)OC(=O)OC(C)(C)C ODCCJTMPMUFERV-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 125000001634 furandiyl group Chemical group O1C(=C(C=C1)*)* 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 150000004715 keto acids Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000006198 methoxylation reaction Methods 0.000 description 1
- 125000004957 naphthylene group Chemical group 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- SIOXPEMLGUPBBT-UHFFFAOYSA-M picolinate Chemical compound [O-]C(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-M 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- UXWVQHXKKOGTSY-UHFFFAOYSA-N tert-butyl phenyl carbonate Chemical compound CC(C)(C)OC(=O)OC1=CC=CC=C1 UXWVQHXKKOGTSY-UHFFFAOYSA-N 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- FGQOOHJZONJGDT-UHFFFAOYSA-N vanillin Natural products COC1=CC(O)=CC(C=O)=C1 FGQOOHJZONJGDT-UHFFFAOYSA-N 0.000 description 1
- 235000012141 vanillin Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
- C07C45/70—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction with functional groups containing oxygen only in singly bound form
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
- Compounds Of Alkaline-Earth Elements, Aluminum Or Rare-Earth Metals (AREA)
- Catalysts (AREA)
- Investigating Or Analyzing Non-Biological Materials By The Use Of Chemical Means (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8913370A FR2652808B1 (de) | 1989-10-09 | 1989-10-09 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NO904328D0 NO904328D0 (no) | 1990-10-05 |
| NO904328L true NO904328L (no) | 1991-04-10 |
Family
ID=9386345
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO90904328A NO904328L (no) | 1989-10-09 | 1990-10-05 | Fremgangsmaate for fremstilling av benzaldehyder. |
Country Status (13)
| Country | Link |
|---|---|
| EP (1) | EP0423010B1 (de) |
| JP (1) | JPH03193742A (de) |
| AT (1) | ATE95157T1 (de) |
| AU (1) | AU6395790A (de) |
| BR (1) | BR9005018A (de) |
| CA (1) | CA2027014A1 (de) |
| DE (1) | DE69003648T2 (de) |
| FI (1) | FI904950A0 (de) |
| FR (1) | FR2652808B1 (de) |
| IE (1) | IE903608A1 (de) |
| IL (1) | IL95925A0 (de) |
| NO (1) | NO904328L (de) |
| PT (1) | PT95536A (de) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0463946A1 (de) * | 1990-06-27 | 1992-01-02 | Rhone-Poulenc Chimie | Verfahren zur Herstellung von polyalkoxylierten aromatischen Verbindungen |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE723412C (de) * | 1940-05-12 | 1942-09-02 | Fahlberg List Ag Chemische Fab | Verfahren zur Methoxylierung von p-Kresol und p-Oxybenzaldehyd |
| BE789586A (fr) * | 1972-03-27 | 1973-04-02 | Hoffmann La Roche | Procede pour la preparation de 3,4,5-trimethoxy-benzaldehyde |
| US4218567A (en) * | 1978-05-30 | 1980-08-19 | Hoffmann-La Roche Inc. | Process for aromatic ethers |
| GB2089672A (en) * | 1980-12-17 | 1982-06-30 | Sterwin Ag | Processes for substitution of aromatic compounds |
| EP0155335A1 (de) * | 1984-03-21 | 1985-09-25 | LUDWIG HEUMANN & CO GMBH | Verfahren zur Herstellung von 3,5-Dimethoxy-4-alkoxybenzaldehyden |
-
1989
- 1989-10-09 FR FR8913370A patent/FR2652808B1/fr not_active Expired - Fee Related
-
1990
- 1990-10-05 CA CA002027014A patent/CA2027014A1/fr not_active Abandoned
- 1990-10-05 NO NO90904328A patent/NO904328L/no unknown
- 1990-10-05 BR BR909005018A patent/BR9005018A/pt unknown
- 1990-10-08 EP EP90402786A patent/EP0423010B1/de not_active Expired - Lifetime
- 1990-10-08 PT PT95536A patent/PT95536A/pt not_active Application Discontinuation
- 1990-10-08 DE DE90402786T patent/DE69003648T2/de not_active Expired - Fee Related
- 1990-10-08 FI FI904950A patent/FI904950A0/fi not_active Application Discontinuation
- 1990-10-08 AT AT90402786T patent/ATE95157T1/de not_active IP Right Cessation
- 1990-10-09 IL IL9095925A patent/IL95925A0/xx not_active IP Right Cessation
- 1990-10-09 IE IE360890A patent/IE903608A1/en unknown
- 1990-10-09 AU AU63957/90A patent/AU6395790A/en not_active Abandoned
- 1990-10-09 JP JP2269704A patent/JPH03193742A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| ATE95157T1 (de) | 1993-10-15 |
| IE903608A1 (en) | 1991-05-08 |
| EP0423010A1 (de) | 1991-04-17 |
| AU6395790A (en) | 1991-04-11 |
| JPH03193742A (ja) | 1991-08-23 |
| EP0423010B1 (de) | 1993-09-29 |
| FR2652808A1 (de) | 1991-04-12 |
| DE69003648D1 (de) | 1993-11-04 |
| NO904328D0 (no) | 1990-10-05 |
| BR9005018A (pt) | 1991-09-10 |
| IL95925A0 (en) | 1991-07-18 |
| DE69003648T2 (de) | 1994-03-24 |
| FR2652808B1 (de) | 1994-01-28 |
| CA2027014A1 (fr) | 1991-04-10 |
| FI904950A0 (fi) | 1990-10-08 |
| PT95536A (pt) | 1991-08-14 |
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