CS259448B1 - Method of 2,6-diaminomesitylene-4-sulphonic acid's preparation - Google Patents
Method of 2,6-diaminomesitylene-4-sulphonic acid's preparation Download PDFInfo
- Publication number
- CS259448B1 CS259448B1 CS869326A CS932686A CS259448B1 CS 259448 B1 CS259448 B1 CS 259448B1 CS 869326 A CS869326 A CS 869326A CS 932686 A CS932686 A CS 932686A CS 259448 B1 CS259448 B1 CS 259448B1
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- CS
- Czechoslovakia
- Prior art keywords
- preparation
- sulfonic acid
- hydrogen
- reaction
- diaminomesitylene
- Prior art date
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- 238000002360 preparation method Methods 0.000 title claims abstract description 8
- 238000000034 method Methods 0.000 title claims abstract description 7
- PKKGGWLTUCMSSD-UHFFFAOYSA-N 3,5-diamino-2,4,6-trimethylbenzenesulfonic acid Chemical compound CC1=C(N)C(C)=C(S(O)(=O)=O)C(C)=C1N PKKGGWLTUCMSSD-UHFFFAOYSA-N 0.000 title claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 9
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims abstract description 9
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims abstract description 8
- 239000001257 hydrogen Substances 0.000 claims abstract description 8
- 239000003054 catalyst Substances 0.000 claims abstract description 7
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims abstract description 6
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 claims abstract description 5
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims abstract description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 5
- 235000011114 ammonium hydroxide Nutrition 0.000 claims abstract description 5
- 229910052697 platinum Inorganic materials 0.000 claims abstract description 5
- 229910052763 palladium Inorganic materials 0.000 claims abstract description 4
- 150000003863 ammonium salts Chemical class 0.000 claims abstract description 3
- 239000011541 reaction mixture Substances 0.000 claims abstract description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 239000000725 suspension Substances 0.000 claims description 5
- 150000002431 hydrogen Chemical class 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 abstract description 9
- RGNRSPQQRBBORA-UHFFFAOYSA-N 2,4,6-trimethyl-3,5-dinitrobenzenesulfonic acid Chemical compound CC1=C([N+]([O-])=O)C(C)=C(S(O)(=O)=O)C(C)=C1[N+]([O-])=O RGNRSPQQRBBORA-UHFFFAOYSA-N 0.000 abstract description 5
- 239000002253 acid Substances 0.000 abstract description 4
- 239000000985 reactive dye Substances 0.000 abstract description 2
- 239000007900 aqueous suspension Substances 0.000 abstract 1
- 229910052799 carbon Inorganic materials 0.000 abstract 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- -1 alkali metal salts Chemical class 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 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 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 230000020477 pH reduction Effects 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 239000003513 alkali Substances 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000012086 standard solution Substances 0.000 description 1
- 230000008719 thickening Effects 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
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- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Způsob přípravy 2,6-diaimlniomesitylen-4- -sulfonové kyseliny tak, že se 2,6-dinitromesitylen-4-sulfonová kyselina převede na velmi jemnou vodnou suspenzi stechiametrickým množstvím vodného: roztoku amoniaku za vzniku amonné soli, a po přídavku 0,1 až 0,25 % hmot. katalyzátoru, jímž je platina netooi paládium suspendované na aktivním uhlí, se do reakční směsi zavede vodík s přetlakem 1 až 2 MPa. Reakce se provádí při teplotě 50 až 120 °C. Efektní způsob přípravy s vysokým výtěžkem uvedeného meziproduktu pro přípravu reaktivních barviv.Process for the Preparation of 2,6-Diaiminomethylitylene-4- sulfonic acid such that the 2,6-dinitromesitylene-4-sulfonic acid acid converts to very a fine aqueous suspension of stoichiometric aqueous ammonia solution to give the ammonium salt, and after the addition of 0.1 to 0.1 0.25 wt. catalyst which is platinum netooi palladium suspended in the active carbon, hydrogen s is introduced into the reaction mixture overpressure 1 to 2 MPa. The reaction is performed at a temperature of 50 to 120 ° C. Effective way of preparation with a high yield of said intermediate for the preparation of reactive dyes.
Description
Vynález se týká způsobu přípravy 2,6-diaminnmesitylen-4-sulfonavé kyseliny. 2,6-diaminiomesitylen-4-sulfonová kyselina je důležitý meziprodukt pro- přípravu reaktivních barviv. Dosud je připravována Béchampovoiu redukcí 2,6-di!nitromesitylen-4-sulfonové kyseliny s výtěžkem cca 80 %.The invention relates to a process for the preparation of 2,6-diamino mesitylene-4-sulfonic acid. 2,6-Diaminiomesitylene-4-sulfonic acid is an important intermediate for the preparation of reactive dyes. To date, it has been prepared by Béchamp's reduction of 2,6-di-nitromesitylene-4-sulfonic acid in about 80% yield.
Nyní bylo zjištěno1, že je možno připravit 1 has now been found that it is possible to prepare
2.6- diamlnomesltylen-4-sulfonovou kyselinu hydrlogenací na paládiovém nebo platinovém katalyzátoru s výtěžkem vyšším než-li 90' %.2,6-diamino-mesylene-4-sulfonic acid by hydrlogenation on a palladium or platinum catalyst in a yield of more than 90%.
Při vývoji pracovního postupu bylo ověřeno·, že hydrogenace vodné, cca 20% suspenze 2,6-dinitromesitylen-4-sulfonové kyseliny prakticky neprobíhá, neboť výchozí surovina i produkt jsou ve vodě špatně rozpustné. Proto bylo třeba navrhnout reakční podmínky tiaik, aby byl produkt v roztoku, čímž by se usnadnila izolace katalyzátoru klerací.During the development of the process, it has been verified that the hydrogenation of the aqueous, about 20% suspension of 2,6-dinitromesitylene-4-sulfonic acid practically does not take place, since both the starting material and the product are poorly soluble in water. Therefore, it was necessary to design reaction conditions for the product to be in solution, thereby facilitating the isolation of the catalyst by clering.
2.6- diaminomesitylen-4-sulfonová kyselina je dobře rozpustná ve formě solí alkalických kovů, ale přídavek stechiometrickébo množství příslušné alkálie k suspenzi 2,6-dinitromesitylen-4-sulfonové kyseliny ve vodě způsobuje značné zhoustnutí suspenze, neboť2,6-diaminomesitylene-4-sulfonic acid is well soluble in the form of alkali metal salts, but the addition of a stoichiometric or amount of the appropriate alkali to a suspension of 2,6-dinitromesitylene-4-sulfonic acid in water causes a considerable thickening of the suspension,
2.6- dinitromesitylen-4-sulfoinová kyselina je ve formě solí alkalických kovů ještě méně rozpustná než-li volná kyselina. Vznik dobře vyvinutých krystalů 2,6-diaminomesitylen-4-sulfonanu sodného nebo draselného neumožňuje vést reakci do vysokého stupně konverze, a proto je 2,6-dinitromesitylen-4-sulfonová kyselina ve formě sodné nebo draselné soli pro tuto reakci nevhodná.2,6-dinitromesitylene-4-sulfoic acid is even less soluble in the form of alkali metal salts than the free acid. The formation of well-developed sodium or potassium 2,6-diaminomesitylene-4-sulfonate crystals does not allow the reaction to proceed to a high degree of conversion, and therefore 2,6-dinithromesitylene-4-sulfonic acid in the form of sodium or potassium salt is unsuitable for this reaction.
Způsob přípravy 2,6-diaminomesitylen-4-sulfonové kyseliny spočívá podle vynálezu v tom, že se 2,6-dinitromesitylen-4-sulfonová kyselina převede na velmi jemnou vadnou suspenzi stechiometrickým množstvím vodného· roztoku amoniaku za vzniku amonné soli a po přídavku 0,1 až 0,25 % hmot.The process for the preparation of 2,6-diaminomesitylene-4-sulfonic acid consists in converting 2,6-dinitromesitylene-4-sulfonic acid into a very fine, defective suspension with a stoichiometric amount of aqueous ammonia solution to form the ammonium salt and after the addition of 0. %, 1 to 0.25 wt.
katalyzátoru, kterými jsou platina nebo paládium suspendované na aktivním uhlí, se do reakční směsi zavede vodíková atmosféra s přetlakem 1 až 2 MPa. Reakce se provádí při teplotě 50 až 120 °C, s výhodou při při 60 °C, po dobu 2 až 5 hodin. Po dokončené reakci, která je detekována konstantním tlakem vodíku v aparatuře, se kvalita produktu· posuzuje tenkovrstvou chromatografií na silufolu v soustavě etylacetát: etanol: čpavek — 5:3:2, proti standardním roztokům výchozí suroviny a produktu. Po klerací je možno 2,6-dianninomesitylen-4-sulfonovou kyselinu izolovat filtrací po vykyselení roztoku kyselinou chlorovodíkovou na p,H 3.A catalyst atmosphere of platinum or palladium suspended on activated carbon is introduced into the reaction mixture with a hydrogen atmosphere at a pressure of 1 to 2 MPa. The reaction is carried out at a temperature of 50 to 120 ° C, preferably at 60 ° C, for 2 to 5 hours. After completion of the reaction, which is detected by constant hydrogen pressure in the apparatus, the product quality is assessed by thin layer chromatography on silufol in ethyl acetate: ethanol: ammonia - 5: 3: 2, against standard solutions of the starting material and product. After clering, 2,6-dianninomesitylene-4-sulfonic acid can be isolated by filtration after acidification of the solution with hydrochloric acid to p, H 3.
Níže uvedené příklady ilustrují provedení způsobů podle vynálezu.The examples below illustrate embodiments of the methods of the invention.
Příklad 1 g 89,83% pasty 2!6-dinitromesitylen-4-sulfanové kyseliny se den před katalytickou hydrogenací suspenduje ve směsi 300 ml vady s 27 g 26% roztoku amoniaku. Druhého dne še k suspenzi v autoklávu přidají 2 g 48% pasty katalyzátoru Pt/C a po vypláchnutí autoklávu vodíkem se uvede vodík v přetlaku 2 MPa. Po vyhřátí na 60 °C se reakce provádí tak dlouho, pokud je indikován pokles tlaku vodíku, obvykle 4 hodiny. Po dokončené reakc-i a izolaci katalyzátoru se produkt získá filtrací po vykyselení klerátu kyselinou chlorovodíkovou na pH 3.Example 1 g 89.83% Paste 2 ! The 6-dinithromesitylene-4-sulfanoic acid was suspended in a mixture of 300 ml of defect with 27 g of a 26% ammonia solution the day before catalytic hydrogenation. The next day, 2 g of 48% Pt / C catalyst paste was added to the autoclave slurry, and after the hydrogen autoclave was purged with hydrogen, at a pressure of 20 bar. After heating to 60 ° C, the reaction is continued for as long as a hydrogen pressure drop is indicated, typically 4 hours. After completion of the reaction and isolation of the catalyst, the product is obtained by filtration after acidification of the clerate with hydrochloric acid to pH 3.
Příklad 2Example 2
Provedení stejné jako u příkladu 1, ale s tím rozdílem,· že: navážku, vodného roztoku amoniaku je třeba upravit na 12,6 % volné kyseliny, sírové v paste výchozí suroviny.Embodiments similar to Example 1, except that the aqueous ammonia solution is adjusted to 12.6% free sulfuric acid in the feedstock paste.
Claims (2)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS869326A CS259448B1 (en) | 1986-12-15 | 1986-12-15 | Method of 2,6-diaminomesitylene-4-sulphonic acid's preparation |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS869326A CS259448B1 (en) | 1986-12-15 | 1986-12-15 | Method of 2,6-diaminomesitylene-4-sulphonic acid's preparation |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CS932686A1 CS932686A1 (en) | 1988-02-15 |
| CS259448B1 true CS259448B1 (en) | 1988-10-14 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS869326A CS259448B1 (en) | 1986-12-15 | 1986-12-15 | Method of 2,6-diaminomesitylene-4-sulphonic acid's preparation |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106995392A (en) * | 2016-01-22 | 2017-08-01 | 济南和润化工科技有限公司 | A kind of method of catalytic hydrogenation production M acid |
| CN110437110A (en) * | 2019-08-26 | 2019-11-12 | 辽宁大学 | A method of synthesis M acid |
-
1986
- 1986-12-15 CS CS869326A patent/CS259448B1/en unknown
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106995392A (en) * | 2016-01-22 | 2017-08-01 | 济南和润化工科技有限公司 | A kind of method of catalytic hydrogenation production M acid |
| CN110437110A (en) * | 2019-08-26 | 2019-11-12 | 辽宁大学 | A method of synthesis M acid |
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| Publication number | Publication date |
|---|---|
| CS932686A1 (en) | 1988-02-15 |
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