JPS601294B2 - ３―メトキシ―４―ヒドロキシ―ベンズアルデヒドの製造法 - Google Patents
３―メトキシ―４―ヒドロキシ―ベンズアルデヒドの製造法Info
- Publication number
- JPS601294B2 JPS601294B2 JP51012388A JP1238876A JPS601294B2 JP S601294 B2 JPS601294 B2 JP S601294B2 JP 51012388 A JP51012388 A JP 51012388A JP 1238876 A JP1238876 A JP 1238876A JP S601294 B2 JPS601294 B2 JP S601294B2
- Authority
- JP
- Japan
- Prior art keywords
- vanillin
- molecular weight
- yield
- weight
- lignin
- 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.)
- Expired
Links
- MWOOGOJBHIARFG-UHFFFAOYSA-N vanillin Chemical compound COC1=CC(C=O)=CC=C1O MWOOGOJBHIARFG-UHFFFAOYSA-N 0.000 title claims description 24
- FGQOOHJZONJGDT-UHFFFAOYSA-N vanillin Natural products COC1=CC(O)=CC(C=O)=C1 FGQOOHJZONJGDT-UHFFFAOYSA-N 0.000 title claims description 24
- 238000004519 manufacturing process Methods 0.000 title claims description 20
- 239000002699 waste material Substances 0.000 claims description 22
- 229920005610 lignin Polymers 0.000 claims description 16
- 239000007788 liquid Substances 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 15
- 230000003647 oxidation Effects 0.000 claims description 10
- 238000007254 oxidation reaction Methods 0.000 claims description 10
- 239000012528 membrane Substances 0.000 claims description 6
- 238000000108 ultra-filtration Methods 0.000 claims description 5
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 3
- 238000001914 filtration Methods 0.000 claims description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 33
- 235000012141 vanillin Nutrition 0.000 description 22
- 239000012141 concentrate Substances 0.000 description 13
- 239000011550 stock solution Substances 0.000 description 11
- 230000000052 comparative effect Effects 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- 239000000243 solution Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 238000004140 cleaning Methods 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 238000000855 fermentation Methods 0.000 description 3
- 230000004151 fermentation Effects 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 229910000831 Steel Inorganic materials 0.000 description 2
- 230000001476 alcoholic effect Effects 0.000 description 2
- GBAOBIBJACZTNA-UHFFFAOYSA-L calcium sulfite Chemical compound [Ca+2].[O-]S([O-])=O GBAOBIBJACZTNA-UHFFFAOYSA-L 0.000 description 2
- 235000010261 calcium sulphite Nutrition 0.000 description 2
- JZCCFEFSEZPSOG-UHFFFAOYSA-L copper(II) sulfate pentahydrate Chemical compound O.O.O.O.O.[Cu+2].[O-]S([O-])(=O)=O JZCCFEFSEZPSOG-UHFFFAOYSA-L 0.000 description 2
- 238000005194 fractionation Methods 0.000 description 2
- 229910010272 inorganic material Inorganic materials 0.000 description 2
- 239000012429 reaction media Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000010959 steel Substances 0.000 description 2
- WBIZZNFQJPOKDK-UHFFFAOYSA-N 4-hydroxy-2-methoxybenzaldehyde Chemical compound COC1=CC(O)=CC=C1C=O WBIZZNFQJPOKDK-UHFFFAOYSA-N 0.000 description 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- VRKYGXIGBMGCDB-UHFFFAOYSA-I [Na+].[OH-].[Th+4].[OH-].[OH-].[OH-].[OH-] Chemical compound [Na+].[OH-].[Th+4].[OH-].[OH-].[OH-].[OH-] VRKYGXIGBMGCDB-UHFFFAOYSA-I 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 230000005587 bubbling Effects 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000012295 chemical reaction liquid Substances 0.000 description 1
- 150000001879 copper Chemical class 0.000 description 1
- 229910001882 dioxygen Inorganic materials 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 150000002484 inorganic compounds Chemical class 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- KUNICNFETYAKKO-UHFFFAOYSA-N sulfuric acid;pentahydrate Chemical compound O.O.O.O.O.OS(O)(=O)=O KUNICNFETYAKKO-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C47/00—Compounds having —CHO groups
- C07C47/52—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings
- C07C47/575—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings containing ether groups, groups, groups, or groups
- C07C47/58—Vanillin
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NO750420 | 1975-02-10 | ||
| NO750420A NO135026C (enrdf_load_stackoverflow) | 1975-02-10 | 1975-02-10 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS51101943A JPS51101943A (enrdf_load_stackoverflow) | 1976-09-08 |
| JPS601294B2 true JPS601294B2 (ja) | 1985-01-14 |
Family
ID=19882074
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP51012388A Expired JPS601294B2 (ja) | 1975-02-10 | 1976-02-09 | ３―メトキシ―４―ヒドロキシ―ベンズアルデヒドの製造法 |
Country Status (5)
| Country | Link |
|---|---|
| JP (1) | JPS601294B2 (enrdf_load_stackoverflow) |
| CA (1) | CA1071235A (enrdf_load_stackoverflow) |
| FI (1) | FI57742C (enrdf_load_stackoverflow) |
| NO (1) | NO135026C (enrdf_load_stackoverflow) |
| SE (1) | SE416046B (enrdf_load_stackoverflow) |
-
1975
- 1975-02-10 NO NO750420A patent/NO135026C/no unknown
-
1976
- 1976-02-03 CA CA244,893A patent/CA1071235A/en not_active Expired
- 1976-02-06 SE SE7601330A patent/SE416046B/sv not_active IP Right Cessation
- 1976-02-09 FI FI760303A patent/FI57742C/fi not_active IP Right Cessation
- 1976-02-09 JP JP51012388A patent/JPS601294B2/ja not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FI760303A7 (enrdf_load_stackoverflow) | 1976-08-11 |
| CA1071235A (en) | 1980-02-05 |
| FI57742C (fi) | 1981-07-27 |
| SE7601330L (sv) | 1976-08-11 |
| FI57742B (fi) | 1980-06-30 |
| SE416046B (sv) | 1980-11-24 |
| NO135026B (enrdf_load_stackoverflow) | 1976-10-18 |
| JPS51101943A (enrdf_load_stackoverflow) | 1976-09-08 |
| NO135026C (enrdf_load_stackoverflow) | 1977-01-26 |
| NO750420L (enrdf_load_stackoverflow) | 1976-08-11 |
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