DE3434038A1 - Verfahren zur herstellung von alkali- und erdalkalisalzen der benzaldehyd-2,4-disulfonsaeure - Google Patents
Verfahren zur herstellung von alkali- und erdalkalisalzen der benzaldehyd-2,4-disulfonsaeureInfo
- Publication number
- DE3434038A1 DE3434038A1 DE19843434038 DE3434038A DE3434038A1 DE 3434038 A1 DE3434038 A1 DE 3434038A1 DE 19843434038 DE19843434038 DE 19843434038 DE 3434038 A DE3434038 A DE 3434038A DE 3434038 A1 DE3434038 A1 DE 3434038A1
- Authority
- DE
- Germany
- Prior art keywords
- sulfite
- alkali
- reaction
- sodium
- production
- 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- Withdrawn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 description 17
- 239000002253 acid Substances 0.000 title claims description 4
- 238000004519 manufacturing process Methods 0.000 title description 4
- 159000000011 group IA salts Chemical class 0.000 title 1
- AQVKVGOTPBBVMS-UHFFFAOYSA-N 2,4-dichloro-1-(dichloromethyl)benzene Chemical compound ClC(Cl)C1=CC=C(Cl)C=C1Cl AQVKVGOTPBBVMS-UHFFFAOYSA-N 0.000 claims description 13
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 claims description 11
- 238000006243 chemical reaction Methods 0.000 claims description 11
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 10
- 229940079826 hydrogen sulfite Drugs 0.000 claims description 9
- UUKHCUPMVISNFW-UHFFFAOYSA-L disodium;4-formylbenzene-1,3-disulfonate Chemical compound [Na+].[Na+].[O-]S(=O)(=O)C1=CC=C(C=O)C(S([O-])(=O)=O)=C1 UUKHCUPMVISNFW-UHFFFAOYSA-L 0.000 claims description 8
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 claims description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical group [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 7
- 239000000243 solution Substances 0.000 claims description 6
- 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 5
- 239000003513 alkali Substances 0.000 claims description 5
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 5
- -1 alkaline earth metal salt Chemical class 0.000 claims description 5
- 239000000126 substance Substances 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 4
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 4
- 235000010265 sodium sulphite Nutrition 0.000 claims description 4
- 239000007864 aqueous solution Substances 0.000 claims description 3
- 229910052708 sodium Inorganic materials 0.000 claims description 2
- 239000011734 sodium Substances 0.000 claims description 2
- 230000002378 acidificating effect Effects 0.000 claims 1
- 239000007858 starting material Substances 0.000 claims 1
- 239000000047 product Substances 0.000 description 9
- 230000035484 reaction time Effects 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- YSFBEAASFUWWHU-UHFFFAOYSA-N 2,4-dichlorobenzaldehyde Chemical compound ClC1=CC=C(C=O)C(Cl)=C1 YSFBEAASFUWWHU-UHFFFAOYSA-N 0.000 description 3
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 3
- 239000012928 buffer substance Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 3
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- 239000005708 Sodium hypochlorite Substances 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 125000003172 aldehyde group Chemical group 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- 235000010216 calcium carbonate Nutrition 0.000 description 2
- 239000000920 calcium hydroxide Substances 0.000 description 2
- 235000011116 calcium hydroxide Nutrition 0.000 description 2
- 238000005119 centrifugation Methods 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 235000001055 magnesium Nutrition 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 235000015424 sodium Nutrition 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 2
- BUXHYMZMVMNDMG-UHFFFAOYSA-N 2,5-dichlorobenzaldehyde Chemical compound ClC1=CC=C(Cl)C(C=O)=C1 BUXHYMZMVMNDMG-UHFFFAOYSA-N 0.000 description 1
- CAHQGWAXKLQREW-UHFFFAOYSA-N Benzal chloride Chemical class ClC(Cl)C1=CC=CC=C1 CAHQGWAXKLQREW-UHFFFAOYSA-N 0.000 description 1
- 238000005705 Cannizzaro reaction Methods 0.000 description 1
- 238000005684 Liebig rearrangement reaction Methods 0.000 description 1
- 229910019093 NaOCl Inorganic materials 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 150000003935 benzaldehydes Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- NKWPZUCBCARRDP-UHFFFAOYSA-L calcium bicarbonate Chemical compound [Ca+2].OC([O-])=O.OC([O-])=O NKWPZUCBCARRDP-UHFFFAOYSA-L 0.000 description 1
- 229910000020 calcium bicarbonate Inorganic materials 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 238000009713 electroplating Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229960003975 potassium Drugs 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 229940086066 potassium hydrogencarbonate Drugs 0.000 description 1
- 229910000160 potassium phosphate Inorganic materials 0.000 description 1
- 235000011009 potassium phosphates Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-M sodium bicarbonate Substances [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
- 229940079827 sodium hydrogen sulfite Drugs 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 229910000162 sodium phosphate Inorganic materials 0.000 description 1
- 238000001256 steam distillation Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical class [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- AAAQKTZKLRYKHR-UHFFFAOYSA-N triphenylmethane Chemical compound C1=CC=CC=C1C(C=1C=CC=CC=1)C1=CC=CC=C1 AAAQKTZKLRYKHR-UHFFFAOYSA-N 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19843434038 DE3434038A1 (de) | 1984-09-17 | 1984-09-17 | Verfahren zur herstellung von alkali- und erdalkalisalzen der benzaldehyd-2,4-disulfonsaeure |
| DE8585111253T DE3560947D1 (en) | 1984-09-17 | 1985-09-06 | Process for the preparation of salts of alkaline or earth-alkaline metals of benzaldehyde-2,4-disulfonic acid |
| EP85111253A EP0175227B1 (de) | 1984-09-17 | 1985-09-06 | Verfahren zur Herstellung von Alkali- und Erdalkalisalzen der Benzaldehyd-2,4-disulfonsäure |
| US06/775,744 US4715995A (en) | 1984-09-17 | 1985-09-13 | Process for the preparation of alkali metal and alkaline earth salts of benzaldehyde-2,4-disulfonic acid |
| JP60202565A JPS6172743A (ja) | 1984-09-17 | 1985-09-14 | ベンズアルデヒド―２，４―ジスルホン酸のアルカリ金属塩およびアルカリ土類金属塩の製造方法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19843434038 DE3434038A1 (de) | 1984-09-17 | 1984-09-17 | Verfahren zur herstellung von alkali- und erdalkalisalzen der benzaldehyd-2,4-disulfonsaeure |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE3434038A1 true DE3434038A1 (de) | 1986-03-27 |
Family
ID=6245566
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19843434038 Withdrawn DE3434038A1 (de) | 1984-09-17 | 1984-09-17 | Verfahren zur herstellung von alkali- und erdalkalisalzen der benzaldehyd-2,4-disulfonsaeure |
| DE8585111253T Expired DE3560947D1 (en) | 1984-09-17 | 1985-09-06 | Process for the preparation of salts of alkaline or earth-alkaline metals of benzaldehyde-2,4-disulfonic acid |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE8585111253T Expired DE3560947D1 (en) | 1984-09-17 | 1985-09-06 | Process for the preparation of salts of alkaline or earth-alkaline metals of benzaldehyde-2,4-disulfonic acid |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US4715995A (enExample) |
| EP (1) | EP0175227B1 (enExample) |
| JP (1) | JPS6172743A (enExample) |
| DE (2) | DE3434038A1 (enExample) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2001051459A1 (en) * | 2000-01-10 | 2001-07-19 | Centaur Phamaceuticals, Inc. | Method for the purification of aryl sulfonic acids and salts |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE98321C (enExample) * | ||||
| DE91818C (enExample) * | ||||
| DE32238C (de) * | Badische Anilin- und Sodafabrik in Ludwigshafen a. Rh | Verfahren zur Darstellung von Tetrachlorindigo | ||
| DE88952C (enExample) * | ||||
| US1531507A (en) * | 1922-07-24 | 1925-03-31 | Nat Aniline & Chem Co Inc | Manufacture of benzaldehyde-2.5-disulfonic acil |
| CH619437A5 (en) * | 1975-08-22 | 1980-09-30 | Hoffmann La Roche | Process for the preparation of polyene compounds. |
-
1984
- 1984-09-17 DE DE19843434038 patent/DE3434038A1/de not_active Withdrawn
-
1985
- 1985-09-06 EP EP85111253A patent/EP0175227B1/de not_active Expired
- 1985-09-06 DE DE8585111253T patent/DE3560947D1/de not_active Expired
- 1985-09-13 US US06/775,744 patent/US4715995A/en not_active Expired - Fee Related
- 1985-09-14 JP JP60202565A patent/JPS6172743A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| EP0175227B1 (de) | 1987-11-11 |
| US4715995A (en) | 1987-12-29 |
| EP0175227A3 (en) | 1986-05-21 |
| DE3560947D1 (en) | 1987-12-17 |
| JPS6172743A (ja) | 1986-04-14 |
| JPH0558430B2 (enExample) | 1993-08-26 |
| EP0175227A2 (de) | 1986-03-26 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8139 | Disposal/non-payment of the annual fee |