CN85102826B - Method for synthesizing amino-aryl-hydroxyethyl sulfone - Google Patents
Method for synthesizing amino-aryl-hydroxyethyl sulfoneInfo
- Publication number
- CN85102826B CN85102826B CN85102826A CN85102826A CN85102826B CN 85102826 B CN85102826 B CN 85102826B CN 85102826 A CN85102826 A CN 85102826A CN 85102826 A CN85102826 A CN 85102826A CN 85102826 B CN85102826 B CN 85102826B
- Authority
- CN
- China
- Prior art keywords
- beta
- amino
- sodium
- hydroxyethyl
- hydrogen peroxide
- 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
- 238000000034 method Methods 0.000 title claims abstract description 14
- 230000002194 synthesizing effect Effects 0.000 title abstract 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims abstract description 52
- 238000006243 chemical reaction Methods 0.000 claims abstract description 22
- XMVONEAAOPAGAO-UHFFFAOYSA-N sodium tungstate Chemical compound [Na+].[Na+].[O-][W]([O-])(=O)=O XMVONEAAOPAGAO-UHFFFAOYSA-N 0.000 claims abstract description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 13
- 150000003457 sulfones Chemical class 0.000 claims abstract description 8
- 239000011734 sodium Substances 0.000 claims description 9
- 229910052708 sodium Inorganic materials 0.000 claims description 8
- APUPEJJSWDHEBO-UHFFFAOYSA-P ammonium molybdate Chemical compound [NH4+].[NH4+].[O-][Mo]([O-])(=O)=O APUPEJJSWDHEBO-UHFFFAOYSA-P 0.000 claims description 6
- 239000011609 ammonium molybdate Substances 0.000 claims description 6
- 229940010552 ammonium molybdate Drugs 0.000 claims description 6
- 235000018660 ammonium molybdate Nutrition 0.000 claims description 6
- -1 aminoaryl hydroxyethyl sulfide Chemical compound 0.000 claims description 5
- TVXXNOYZHKPKGW-UHFFFAOYSA-N sodium molybdate (anhydrous) Chemical compound [Na+].[Na+].[O-][Mo]([O-])(=O)=O TVXXNOYZHKPKGW-UHFFFAOYSA-N 0.000 claims description 5
- 230000003647 oxidation Effects 0.000 claims description 4
- 238000007254 oxidation reaction Methods 0.000 claims description 4
- LVQCLHVCROWONS-UHFFFAOYSA-N 1-(4-aminophenyl)-2-[2-(4-aminophenyl)-2-hydroxyethyl]sulfanylethanol Chemical compound NC1=CC=C(C=C1)C(CSCC(C1=CC=C(C=C1)N)O)O LVQCLHVCROWONS-UHFFFAOYSA-N 0.000 claims 1
- MEFBJEMVZONFCJ-UHFFFAOYSA-N molybdate Chemical compound [O-][Mo]([O-])(=O)=O MEFBJEMVZONFCJ-UHFFFAOYSA-N 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 abstract description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract description 3
- 150000003839 salts Chemical class 0.000 abstract description 3
- 239000003054 catalyst Substances 0.000 abstract description 2
- 150000001875 compounds Chemical class 0.000 abstract description 2
- 230000001590 oxidative effect Effects 0.000 abstract description 2
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 abstract 4
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 abstract 2
- 239000000985 reactive dye Substances 0.000 abstract 2
- 235000011149 sulphuric acid Nutrition 0.000 abstract 1
- 239000001117 sulphuric acid Substances 0.000 abstract 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- 238000004587 chromatography analysis Methods 0.000 description 7
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 6
- 238000010189 synthetic method Methods 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
- 238000001035 drying Methods 0.000 description 5
- 239000000975 dye Substances 0.000 description 5
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 239000000543 intermediate Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 229920002472 Starch Polymers 0.000 description 3
- 238000005576 amination reaction Methods 0.000 description 3
- 239000008367 deionised water Substances 0.000 description 3
- 229910021641 deionized water Inorganic materials 0.000 description 3
- 238000004090 dissolution Methods 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 235000019698 starch Nutrition 0.000 description 3
- 239000008107 starch Substances 0.000 description 3
- 150000003462 sulfoxides Chemical class 0.000 description 3
- QZZSAWGVHXXMID-UHFFFAOYSA-N 1-amino-4-bromo-9,10-dioxoanthracene-2-sulfonic acid Chemical compound C1=CC=C2C(=O)C3=C(Br)C=C(S(O)(=O)=O)C(N)=C3C(=O)C2=C1 QZZSAWGVHXXMID-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 239000004753 textile Substances 0.000 description 2
- YODZTKMDCQEPHD-UHFFFAOYSA-N thiodiglycol Chemical compound OCCSCCO YODZTKMDCQEPHD-UHFFFAOYSA-N 0.000 description 2
- 238000010792 warming Methods 0.000 description 2
- 239000003643 water by type Substances 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 230000005526 G1 to G0 transition Effects 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
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 1
- QQNXPCCFPQRLMK-UHFFFAOYSA-N S(O)(O)(=O)=O.OCCS(=O)(=O)CCO Chemical compound S(O)(O)(=O)=O.OCCS(=O)(=O)CCO QQNXPCCFPQRLMK-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- 230000008034 disappearance Effects 0.000 description 1
- 235000019441 ethanol Nutrition 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 238000007689 inspection Methods 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- VLAPMBHFAWRUQP-UHFFFAOYSA-L molybdic acid Chemical class O[Mo](O)(=O)=O VLAPMBHFAWRUQP-UHFFFAOYSA-L 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000011175 product filtration Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000002912 waste gas Substances 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The present invention provides a synthesizing method for oxidizing an aryl hydrodecemyethyl sulfide containing an amidogen into a corresponding sulfone which can be obtained by a reaction of the corresponding aryl hydrodecemyethyl sulfide containing the amidogen and hydrogen peroxide in a water medium with the catalyst of sodium tungstate or a molybdic salt. With the utilization of the method, dyad-amidogen-benzene-beta-hydrodecemyethyl sulfide can be oxidized to form dyad-amidogen-benzene-beta-dihydroxyethylsulfone, 1-amidogen-4-anilino-(4'-beta-hydrodecemyethyl sulfide)-anthraquinone-2-sodium sulfonate can be oxidized to form 1-amidogen-4-anilino-(4'-beta-dihydroxyethylsulfone)-anthraquinone-2-sodium sulfonate, and both of the obtained compounds can be further esterified by sulphuric acid to form the intermediate of KN-type reactive dyes and the blue KN-type reactive dye.
Description
The invention provides a kind of synthetic method that aminoaryl hydroxyethyl sulfide oxidation becomes corresponding sulfone that contains.
As everyone knows, the intermediate of KN-type reactive dyestuffs-" right-amino-benzene-the beta-hydroxyethyl sulfone sulfate " H
2N-
-SO
2CH
2CH
2OSO
3H(1) synthetic method commonly used mostly is the chlorosulphonation method, and this method needs through chlorosulphonation, reduction, condensation, four reactions steps of hydrolysis esterification.Operation steps is more, and spent acid waste gas is also many.
At present the synthetic method of Reactive blue KN-R-" 1-amino-4-anilino-(4 '-beta-hydroxyethyl sulfone sulfate)-anthraquinone-2-sodium " (2) is generally carried out the aryl amination resterification and is got with bromamine acid and right-amino-benzene-beta-hydroxyethyl sulfuryl hydrochloride.
(Florin Urseanu, the Industria Usoara-Textile such as Rodica Vintila, Tricotaje, Confectii Textile,
31(2), 84-7,1980.) shortcoming of this method is that the aryl amination yield is low, is about 51%.
The invention provides and contain a kind of synthetic method that amino aryl hydroxyethyl sulfide oxidation becomes corresponding sulfone, and be used for the intermediate (1) of above-mentioned KN-type reactive dyestuffs and the building-up process of KN-type Reactive blue (2), thereby overcome the shortcoming of existing these two kinds of synthetic methods.
This law is used for the building-up process of intermediate (1) of KN-type reactive dyestuffs shown in reaction formula (A):
Take right-amino-benzene beta-hydroxyethyl thioether (3) as raw material in water medium take sodium wolframate or molybdic acid salt (Sodium orthomolybdate or ammonium molybdate) as catalyzer and the hydrogen peroxide reaction, obtain right-amino-benzene-beta-hydroxyethyl sulfuryl (4).
The amino that contains amino aromatics is easy to oxidized dose of Oxidative demage.If there is amino more easily oxidized group in compound molecule, or have amino more easily oxidized material in the reaction system, then amino not oxidized destruction is possible.When containing amino aryl hydroxyethyl thioether or sulfoxide becomes corresponding sulfone with hydrogen peroxide oxidation accordingly, if without catalyzer, then slightly excessive hydrogen peroxide can not be oxidized to terminal point with it; Then cause by product to increase if strengthen the molecule proportioning of hydrogen peroxide or improve temperature of reaction, yield reduces.
In reaction (A), the consumption of hydrogen peroxide is right-amino-benzene-beta-hydroxyethyl thioether (3): H
2O
2=1: 2.1～2.2(molecular ratio).Get final product with 30% commercially available hydrogen peroxide.
The consumption of catalyzer seldom but need to have certain concentration at reacting middle catalyst.In reaction (A), (3): sodium wolframate or Sodium orthomolybdate=1: 0.004～0.005(molecular ratio).Or (3): ammonium molybdate=1: 0.0005～0.0006(molecular ratio).Sodium wolframate can be used WO
3Preparation when reaction also can directly be used sodium wolframate, Sodium orthomolybdate, ammonium molybdate reagent.
The pH value of reaction is 5.5～7.
For reaction (A), temperature of reaction can be with 30～90 ℃, take 50～60 ℃ as good.
Useful to reducing other metal ion such as iron, copper etc. to the decomposition of hydrogen peroxide with deionized water.
The concentration of reactant has certain influence to the consumption of hydrogen peroxide, and bigger reactant concn is conducive to reduce the excessive value of hydrogen peroxide.Generally should use 14～20% concentration.In reaction (A), can adopt 20%.
The dripping quantity of hydrogen peroxide and rate of addition will adapt with amount and the speed of response of used catalyzer.
The thin plate chromatography is used in terminal point control, take silica gel G as stationary phase.In reaction (A), use benzene: ethyl acetate: acetic acid=5: 5: the 1(volume ratio) be developping agent.Be developer with right-dimethylaminobenzaldehyde.All change into sulfone as terminal point take thioether through sulfoxide.
This law is used for the building-up process of KN-type Reactive blue shown in reaction formula (B):
1-amino-4-anilino-(4 '-beta-hydroxyethyl thioether)-anthraquinone-2-sodium (5) and hydrogen peroxide react under the normal pressure in water medium take sodium wolframate as catalyzer, obtain 1-amino-4-anilino-(4 '-beta-hydroxyethyl sulfuryl)-anthraquinone-2-sodium (6).(5): H
2O
2=1: 2.2～2.5(molecular ratio).(5) be 1: 0.005～0.008 with the sodium wolframate molecular ratio.Temperature of reaction is 70-75 ℃.Terminal point control thin plate chromatography.
This law is used for reaction (A), obtains corresponding sulfone (4), and yield is 89-92%.So just simplify the synthesis technique of synthetic KN-type reactive dyestuffs intermediates (1), reduced the three wastes.
This law is used for reaction (B), has real meaning for synthetic KN-type Reactive blue (2), and it brings up to two step yields by a step yield 51.7% of document is 82%.
Embodiment (A)
Example 1, in small beaker, add 11.6 milligrams of WO
3With 6.5 ml deionized water, stirring adds 1 30%NaOH, as yellow WO
3Completely dissolve has namely generated sodium wolframate, and it is 5.5-7 that addend drips dilute hydrochloric acid accent pH.Add 1.69 grams (0.01 mole) right-amino-benzene-beta-hydroxyethyl thioether (3), be heated to 52 ℃, in 45 minutes, dripping 1 milliliter of 34% hydrogen peroxide (volumetric concentration, i.e. 34 gram H under this temperature
2O
2/ 100 milliliters) (0.01 mole), be warming up to 58 ℃, in 135 minutes, drip 0.01 mole in 1 milliliter of hydrogen peroxide at 58～60 ℃), keeping pH with 10% sodium carbonate solution in the process is 5.5-7.In 90 minutes, drip then 0.1 milliliter of hydrogen peroxide (0.001 mole).With potassium iodide starch test paper and cooperate the thin plate chromatography to check terminal point.Potassium iodide starch test paper is aobvious blue after adding 1 hydrogen peroxide, reexamines after spending several minutes still to blue, and the thin plate chromatography shows that the sulfoxide spot disappears, and is terminal point simultaneously.Product cooling, filtration, drying get little yellow particle.Analyze with the amino value of diazotization analysis or with the CS910 thin layer chromatography scanner, yield is more than 92%.Use ethyl alcohol recrystallization, get colourless plate crystal.Fusing point 108-109 ℃.Ultimate analysis, C＜`; ; 8`〉H＜`; ; 11`〉NO
3S,
Analytical value %:C47.67, H5.54, N6.96, S15.71
Calculated value %:C47.75, H5.51, N6.96, S15.93
Example 2, in small beaker, add 16.5 milligrams of Sodium orthomolybdates and 13 ml waters, add 2.38 grams (0.02 mole) right-amino-benzene-beta-hydroxyethyl thioether (3), be stirred and heated to 52 ℃, in 45 minutes, dripping 2 milliliter of 34% hydrogen peroxide (concentration expressed in percentage by volume, lower same) (0.02 mole) under this temperature.Be warming up to 58 ℃, dripped 2 milliliters of hydrogen peroxide (0.02 mole) at 58-60 ℃ in 135 minutes, dripping 10% sodium carbonate solution maintenance pH in the process is about 6.5.In 90 minutes, drip then 0.4 milliliter of hydrogen peroxide (0.004 mole).With potassium iodide starch test paper and cooperate the thin plate chromatography to check terminal point.Drying is filtered in the product cooling.Yield is more than 89%.
Example 3, with example 2, catalyzer is (NH
4)
6Mo
7O
24, 4H
2O(ammonium molybdate chemically pure reagent) consumption is 13.7 milligrams, and yield is more than 89%.
〔B〕
Bromamine acid carries out aryl amination with right-amino-benzene-beta-hydroxyethyl thioether (3), with CuSO
4-FeSO
4Be catalyzer, with Na
2CO
3-NaHCO
3Be acid binding agent, in 70 ℃ of reactions two hours.The product filtration of saltouing, filter and with use the hydrochloric acid acid out after the water dissolution, filtration, drying, getting product (5) yield is more than 86%.
Example 4, add dyestuff (5) 4.70 gram (0.01 mole) in 250 milliliters of there-necked flasks, 28 milliliters of deionized waters are 7-7.5 with rare NaOH accent pH.Be stirred and heated to 70 ℃ and make it entirely molten.In test tube, add 11.6 milligrams of WO
3With 1 ml deionized water, add 1 30%NaOH and make yellow the disappearance, generate sodium wolframate, it is 7-7.5 that addend drips dilute hydrochloric acid accent pH.The sodium wolframate that generates is added in the there-necked flask.In 30 minutes, drip 1 milliliter of 34% hydrogen peroxide (concentration expressed in percentage by volume, lower same) (0.01 mole) in 70 ℃.Be heated to 75 ℃, in 165 minutes, drip 0.012～0.015 mole in 1.2～1.5 milliliters of hydrogen peroxide).With thin plate chromatography control terminal point, developping agent: propyl carbinol: Glacial acetic acid=2: 1.Behind terminal point, stop adding hydrogen peroxide, add 28 milliliters in water and stirred 10 minutes, saltout with salt, filter.Filter and with adding the hydrochloric acid acid out after the water dissolution, filter.With the dilute hydrochloric acid washing, filter also obtains dyestuff (6) after drying, and yield is more than 95%.
Dyestuff (6) is used at room temperature esterification of 100% sulfuric acid four hours after crushed, does not have dyestuff (6) when existing with the inspection of thin plate chromatography, and ice is analysed, and filters.Water dissolution is also used in filter, with salt saltout, filter, drying, get final product dyestuff (2), be Reactive blue KN-R.
Claims (1)
1, a kind of aminoaryl hydroxyethyl sulfide oxidation becomes the method for corresponding sulfone, 1. right-amino-benzene-beta-hydroxyethyl thioether particularly, 2. 1-amino-4-anilino-(4 '-beta-hydroxyethyl thioether)-anthraquinone-2-sodium is oxidized to the method for corresponding sulfone, it is characterized in that: 1. right-amino-benzene-beta-hydroxyethyl thioether and hydrogen peroxide obtain right-amino-benzene-beta-hydroxyethyl sulfuryl take sodium wolframate or molybdate (Sodium orthomolybdate or ammonium molybdate) as catalyzer reacts under the normal pressure in water medium, temperature of reaction is 50-60 ℃, the molecular ratio of p-aminophenyl-beta-hydroxyethyl thioether and hydrogen peroxide is 1: 2.1～2.2, with the molecular ratio of sodium wolframate (or Sodium orthomolybdate) be 1: 0.004～0.005, (with the molecular ratio of ammonium molybdate be 1: 0.0005～0.0006), pH is 5.5-7.2. 1-amino-4-anilino-(4 '-beta-hydroxyethyl thioether)-anthraquinone-2-sodium and hydrogen peroxide take sodium wolframate as catalyzer in water medium under the normal pressure reaction obtain 1-amino-4-anilino-(4 '-beta-hydroxyethyl sulfuryl)-anthraquinone-2-sodium, temperature of reaction is 70-75 ℃, 1-amino-4-anilino-(4 '-beta-hydroxyethyl thioether)-anthraquinone-2-sodium and hydrogen peroxide molecular ratio are 1: 2.2～2.5, with the molecular ratio of sodium wolframate be 1: 0.005～0.008, pH is 7-7.5.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN85102826A CN85102826B (en) | 1985-04-01 | 1985-04-01 | Method for synthesizing amino-aryl-hydroxyethyl sulfone |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN85102826A CN85102826B (en) | 1985-04-01 | 1985-04-01 | Method for synthesizing amino-aryl-hydroxyethyl sulfone |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN85102826A CN85102826A (en) | 1986-07-23 |
| CN85102826B true CN85102826B (en) | 1987-07-22 |
Family
ID=4792784
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN85102826A Expired CN85102826B (en) | 1985-04-01 | 1985-04-01 | Method for synthesizing amino-aryl-hydroxyethyl sulfone |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN85102826B (en) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AR061760A1 (en) * | 2006-06-30 | 2008-09-17 | Schering Corp | SYNTHESIS OF THE ACID 3- (5-NITROCICLOHEX-1-ENIL) ACRYLIC AND ITS ESTERS |
| CN101434609B (en) * | 2008-12-19 | 2011-03-30 | 齐鲁天和惠世制药有限公司 | Catalytic oxidation system and use thereof in tazobactam synthesis |
| CN102993066A (en) * | 2011-12-13 | 2013-03-27 | 褚平忠 | Synthetic method of dye intermediate 2,4-bi-(B-ethyl sulfuryl sulphate) phenylamine |
| CN103910658B (en) * | 2013-12-23 | 2016-08-17 | 宁夏大学 | A kind of sulfide oxidation becomes the method for sulfone |
| CN106883154A (en) * | 2017-01-09 | 2017-06-23 | 凯莱英医药集团（天津）股份有限公司 | A kind of method of continuous synthesis sulphones |
| CN113292461A (en) * | 2021-05-26 | 2021-08-24 | 神隆医药（常熟）有限公司 | Synthesis method of etoricoxib intermediate 4-methylsulfonylacetophenone |
| CN114921113B (en) * | 2022-03-23 | 2023-08-11 | 浙江亿得新材料股份有限公司 | Green and environment-friendly production process of active anthraquinone turquoise blue dye |
-
1985
- 1985-04-01 CN CN85102826A patent/CN85102826B/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| CN85102826A (en) | 1986-07-23 |
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