CA1121384A - Methode de preparation de la vanilline - Google Patents
Methode de preparation de la vanillineInfo
- Publication number
- CA1121384A CA1121384A CA000341137A CA341137A CA1121384A CA 1121384 A CA1121384 A CA 1121384A CA 000341137 A CA000341137 A CA 000341137A CA 341137 A CA341137 A CA 341137A CA 1121384 A CA1121384 A CA 1121384A
- Authority
- CA
- Canada
- Prior art keywords
- vanillin
- alcohol
- organic solvent
- solvent
- bisulphite
- 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 abstract description 64
- FGQOOHJZONJGDT-UHFFFAOYSA-N vanillin Natural products COC1=CC(O)=CC(C=O)=C1 FGQOOHJZONJGDT-UHFFFAOYSA-N 0.000 title claims abstract description 64
- 235000012141 vanillin Nutrition 0.000 title claims abstract description 64
- 238000000034 method Methods 0.000 title claims abstract description 24
- 238000002360 preparation method Methods 0.000 title claims abstract description 9
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims abstract description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 12
- 238000000605 extraction Methods 0.000 claims abstract description 12
- 239000003960 organic solvent Substances 0.000 claims abstract description 11
- 238000000354 decomposition reaction Methods 0.000 claims abstract description 9
- 239000000243 solution Substances 0.000 claims abstract description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 8
- 239000004117 Lignosulphonate Substances 0.000 claims abstract description 7
- 235000019357 lignosulphonate Nutrition 0.000 claims abstract description 7
- 239000002994 raw material Substances 0.000 claims abstract description 6
- 229920001732 Lignosulfonate Polymers 0.000 claims abstract description 5
- 230000003647 oxidation Effects 0.000 claims abstract description 5
- 238000007254 oxidation reaction Methods 0.000 claims abstract description 5
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 claims abstract description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 27
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 18
- 239000012535 impurity Substances 0.000 claims description 16
- 238000001704 evaporation Methods 0.000 claims description 10
- 239000002904 solvent Substances 0.000 claims description 7
- 239000007864 aqueous solution Substances 0.000 claims description 6
- 230000008020 evaporation Effects 0.000 claims description 6
- 159000000000 sodium salts Chemical class 0.000 claims description 6
- 238000000926 separation method Methods 0.000 claims description 5
- 239000000284 extract Substances 0.000 claims description 4
- 238000000108 ultra-filtration Methods 0.000 claims description 4
- 239000003513 alkali Substances 0.000 claims description 3
- 239000002699 waste material Substances 0.000 claims description 3
- 238000009835 boiling Methods 0.000 claims description 2
- 239000001913 cellulose Substances 0.000 claims description 2
- 229920002678 cellulose Polymers 0.000 claims description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims 2
- 239000000203 mixture Substances 0.000 claims 2
- 239000011541 reaction mixture Substances 0.000 claims 2
- 238000006243 chemical reaction Methods 0.000 claims 1
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 239000012528 membrane Substances 0.000 claims 1
- 230000001590 oxidative effect Effects 0.000 claims 1
- 230000003134 recirculating effect Effects 0.000 claims 1
- 229910000029 sodium carbonate Inorganic materials 0.000 claims 1
- 238000005406 washing Methods 0.000 claims 1
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 abstract description 10
- 235000010269 sulphur dioxide Nutrition 0.000 abstract description 5
- 239000004291 sulphur dioxide Substances 0.000 abstract description 5
- 238000004537 pulping Methods 0.000 abstract description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 7
- 239000000126 substance Substances 0.000 description 6
- 229920005610 lignin Polymers 0.000 description 5
- RGHHSNMVTDWUBI-UHFFFAOYSA-N 4-hydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C=C1 RGHHSNMVTDWUBI-UHFFFAOYSA-N 0.000 description 4
- PZSJOBKRSVRODF-UHFFFAOYSA-N vanillin acetate Chemical compound COC1=CC(C=O)=CC=C1OC(C)=O PZSJOBKRSVRODF-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 150000001299 aldehydes Chemical class 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 150000003839 salts Chemical group 0.000 description 3
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 2
- -1 acetovanillin Chemical compound 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 239000002021 butanolic extract Substances 0.000 description 2
- LHGVFZTZFXWLCP-UHFFFAOYSA-N guaiacol Chemical compound COC1=CC=CC=C1O LHGVFZTZFXWLCP-UHFFFAOYSA-N 0.000 description 2
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 2
- 239000004289 sodium hydrogen sulphite Substances 0.000 description 2
- 239000012485 toluene extract Substances 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 241000218657 Picea Species 0.000 description 1
- 241000022563 Rema Species 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- DFYRUELUNQRZTB-UHFFFAOYSA-N apocynin Chemical compound COC1=CC(C(C)=O)=CC=C1O DFYRUELUNQRZTB-UHFFFAOYSA-N 0.000 description 1
- 239000003849 aromatic solvent Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-M bisulphate group Chemical group S([O-])(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000010668 complexation reaction Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000005755 formation reaction Methods 0.000 description 1
- 229960001867 guaiacol Drugs 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- JJVNINGBHGBWJH-UHFFFAOYSA-N ortho-vanillin Chemical compound COC1=CC=CC(C=O)=C1O JJVNINGBHGBWJH-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000005185 salting out Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- ZFRVFUWCVYLUIH-UHFFFAOYSA-M sodium vanillate Chemical compound [Na+].COC1=CC(C([O-])=O)=CC=C1O ZFRVFUWCVYLUIH-UHFFFAOYSA-M 0.000 description 1
- 239000011122 softwood Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 239000011269 tar Substances 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Manufacture Of Tobacco Products (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FI783799 | 1978-12-11 | ||
| FI783799A FI58906C (fi) | 1978-12-11 | 1978-12-11 | Foerbaettrat foerfarande foer framstaellning av vanillin |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1121384A true CA1121384A (fr) | 1982-04-06 |
Family
ID=8512218
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000341137A Expired CA1121384A (fr) | 1978-12-11 | 1979-12-04 | Methode de preparation de la vanilline |
Country Status (4)
| Country | Link |
|---|---|
| JP (1) | JPS5851939B2 (fr) |
| CA (1) | CA1121384A (fr) |
| FI (1) | FI58906C (fr) |
| NO (1) | NO794020L (fr) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US10017444B2 (en) | 2013-01-24 | 2018-07-10 | Rhodia Operations | Method for the purification of natural vanillin |
| CN111707754A (zh) * | 2020-06-28 | 2020-09-25 | 上海应用技术大学 | 一种测定香兰素中愈疮木酚、邻位香兰素、5-甲基香兰素及5-醛基香兰素的方法 |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2933974B1 (fr) * | 2008-07-18 | 2010-09-17 | Rhodia Operations | Procede de separation d'un aldehyde aromatique |
| CN113811524A (zh) * | 2019-05-08 | 2021-12-17 | 味之素株式会社 | 香兰素的制造方法 |
-
1978
- 1978-12-11 FI FI783799A patent/FI58906C/fi not_active IP Right Cessation
-
1979
- 1979-12-04 CA CA000341137A patent/CA1121384A/fr not_active Expired
- 1979-12-05 JP JP15793679A patent/JPS5851939B2/ja not_active Expired
- 1979-12-10 NO NO794020A patent/NO794020L/no unknown
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US10017444B2 (en) | 2013-01-24 | 2018-07-10 | Rhodia Operations | Method for the purification of natural vanillin |
| CN111707754A (zh) * | 2020-06-28 | 2020-09-25 | 上海应用技术大学 | 一种测定香兰素中愈疮木酚、邻位香兰素、5-甲基香兰素及5-醛基香兰素的方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| FI58906C (fi) | 1981-05-11 |
| FI58906B (fi) | 1981-01-30 |
| FI783799A (fi) | 1980-06-12 |
| JPS5579337A (en) | 1980-06-14 |
| NO794020L (no) | 1980-06-12 |
| JPS5851939B2 (ja) | 1983-11-19 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |