CS254748B1 - Process for preparing 1-amino-3-naftol-3,6-disulphonic acid - Google Patents
Process for preparing 1-amino-3-naftol-3,6-disulphonic acid Download PDFInfo
- Publication number
- CS254748B1 CS254748B1 CS866984A CS698486A CS254748B1 CS 254748 B1 CS254748 B1 CS 254748B1 CS 866984 A CS866984 A CS 866984A CS 698486 A CS698486 A CS 698486A CS 254748 B1 CS254748 B1 CS 254748B1
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- Czechoslovakia
- Prior art keywords
- acid
- amino
- preparing
- naftol
- melting
- Prior art date
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- 238000004519 manufacturing process Methods 0.000 title claims abstract description 5
- 239000002253 acid Substances 0.000 title abstract description 8
- 238000002844 melting Methods 0.000 claims abstract description 9
- 230000008018 melting Effects 0.000 claims abstract description 9
- APRRQJCCBSJQOQ-UHFFFAOYSA-N 4-amino-5-hydroxynaphthalene-2,7-disulfonic acid Chemical compound OS(=O)(=O)C1=CC(O)=C2C(N)=CC(S(O)(=O)=O)=CC2=C1 APRRQJCCBSJQOQ-UHFFFAOYSA-N 0.000 claims abstract description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 4
- 239000000706 filtrate Substances 0.000 claims description 4
- 239000000047 product Substances 0.000 claims description 4
- 239000011541 reaction mixture Substances 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 abstract description 4
- 229910052500 inorganic mineral Inorganic materials 0.000 abstract 1
- 238000009413 insulation Methods 0.000 abstract 1
- 239000011707 mineral Substances 0.000 abstract 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- HLVXFWDLRHCZEI-UHFFFAOYSA-N chromotropic acid Chemical compound OS(=O)(=O)C1=CC(O)=C2C(O)=CC(S(O)(=O)=O)=CC2=C1 HLVXFWDLRHCZEI-UHFFFAOYSA-N 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000006396 nitration reaction Methods 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 229910052742 iron Inorganic materials 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 238000010309 melting process Methods 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000010802 sludge Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Řešení se týká přípravy H-kyseliny alkalickým tavením l-amino-3,6,8-naftalentrisulfokyseliny. Podstata spočívá v tom, že se tavení přeruší přídavkem zředěné minerální kyseliny v okamžiku, kdy je 50 až 98 % násady zreagováno. Nezreagovaná l-amino-3,6,8-naftalentrisulfokyselina se po izolaci vrací zpět do výroby.The present invention relates to the preparation of H-acid by alkaline melting of 1-amino-3,6,8-naphthalentrisulfoacid. The essence is that that the melting is interrupted by the addition of dilute mineral acid when it is 50 to 98% of the feed is reacted. Unreacted 1-amino-3,6,8-naphthalentrisulfoacid returns to production after insulation.
Description
Vynález se týká způsobu přípravy l-amino-8-naftol~3,6-disulfonové kyseliny (H-kyseliny) alkalickým tavením l-amino-3,6,8-naftalentrisulfokyseliny, získané z naftalenů trisulfonapí, nitrací a redukcí bu3 Bechampovskou nebo hydrogenační.The present invention relates to a process for the preparation of 1-amino-8-naphthol-3,6-disulfonic acid (H-acid) by the alkaline melting of 1-amino-3,6,8-naphthalentrisulfoic acid obtained from naphthalenes with trisulfonation, nitration and reduction of either Bechamp or hydrogenation. .
Při dosavadním způsobu výroby dochází v posledním stupni procesu tj. při alkalickém taveni ke vzniku kyseliny 1,8-dihydroxy-3,6-naftálendisulfonové tzv. kyseliny chromotropové, jejíž vznik výrazně ovlivňuje výtěžek hlavního produktu. Tato fáze přípravy probíhá ve zředěném roztoku hydroxidu sodného o koncentraci 20 až 30 % hmot. za tlaku do 1 MPa. Rychlost reakce vzniku kyseliny chromotropové vzrůstá se vzrůstem teploty a prodlužováním doby reakce. Na počátku alkalického taveni vzniká nejprve H-kyselina, její koncentrace v reakční směsi prochází maximem a potom pozvolna klesá, přičemž její výtěžek roste ke konci tavení daleko pomaleji. Koncentrace kyseliny chromotropové naproti tomu během celé doby tavení rovnoměrně vzrůstá.In the present process, in the last stage of the process, i.e., in the alkaline melting process, 1,8-dihydroxy-3,6-naphthalenedisulfonic acid, the so-called chromotropic acid, is formed, the formation of which significantly affects the yield of the main product. This preparation stage is carried out in a dilute sodium hydroxide solution at a concentration of 20 to 30% by weight. under pressure up to 1 MPa. The reaction rate of the formation of chromotropic acid increases as the temperature increases and the reaction time increases. At the beginning of the alkaline melting, H-acid is formed first, its concentration in the reaction mixture goes through maximum and then gradually decreases, and its yield increases much more slowly towards the end of melting. In contrast, the concentration of chromotropic acid increases steadily throughout the melting time.
Uvedenou nevýhodu odstraňuje způsob přípravy l-amino-8-naftol-3,6-disulfokyseliny alkalickým tavením l-amino-3,6,8-naftalentrisulfokyseliny podle tohoto vynálezu, jehož podstata spočívá v tom, že se alkalické tavení v okamžiku, kdy je 50 až 98 % násady zreagováno, přeruší, tím, že se reakční směs rozloží účinkem kyseliny sírové nebo chlorovodíkové o koncentraci 10 až 50 % hmot., produkt se odfiltruje a z filtrátu se izoluje nezreagovaná l-naftylamin-3, 6,8-trisulfokyselina.This disadvantage is overcome by the process of preparing 1-amino-8-naphthol-3,6-disulfoacid by alkaline melting of the 1-amino-3,6,8-naphthalentrisulfoacid of the present invention, which is based on the fact that the 50-98% of the batch was reacted, interrupted by quenching the reaction with 10-50 wt.% Sulfuric or hydrochloric acid, filtering off the product, and unreacted 1-naphthylamine-3,6,8-trisulfoacid was isolated from the filtrate.
Výhodou postupu dle vynálezu je ta skutečnost, že vznik kyseliny chromotropové je omezen na minimum a nezreagovaná l-naftylamin-3,6,8-trisulfokyselina se vrací zpět do výroby, čímž vzroste výtěžek hlavního produktu.An advantage of the process according to the invention is that the formation of chromotropic acid is minimized and unreacted 1-naphthylamine-3,6,8-trisulfoacid is returned to production, thereby increasing the yield of the main product.
Pro bližší objasnění podstaty vynálezu je dále uveden příklad provedení:To illustrate the invention in greater detail, an exemplary embodiment is given below:
PříkladExample
375 kg pasty trinatriové soli kyseliny l-naftylamin-3,6,8-trisulfonové obsahující 1 400 kg volné kyseliny se smísí s 2 520 kg 50% roztoku hydroxidu sodného, vyhřeje se na cca 180 °C a na této teplotě se udržuje po dobu až čtyř hodin, podle rychlosti vyhřívání. Reakční směs se pak přetlačí do 3 200 1 vody a získaný roztok H-kyseliny se smísí s 7 600 kg roztoku zředěné nitrační směsi z předchozího stupně přípravy tj. nitrace naftalentrisulfokyseliny. Získaná suspenze h-kyseliny se zahřívá k varu pokud odchází oxid siřičitý, přičemž pH suspenze se upraví na pH menší než 1. Po ochlazení na 40 °C se suspenze zfiltruje a filtrační koláč se promyje vodou. Získá se 917 g H-kyseliny ve formě sodné soli. Filtrát se zredukuje železem a po neutralizaci hydroxidem sodným se železný kal odfiltruje. Filtrát se okyselí kyselinou solnou, přidá se chlorid sodný a vyloučená l-naftylamin-3,6,8-trisulfokyselina se odfiltruje a promyje. Získá se celkem 1 620 kg pasty kyseliny. Výtěžek H-kyseliny s ohledem na izolaci po redukci zpět získanou l-naftylamin-3,6,8-trisulfokyselinu je 87,3 % theorie.375 kg of l-naphthylamine-3,6,8-trisulfonic acid trinatrium salt paste containing 1,400 kg of free acid is mixed with 2,520 kg of 50% sodium hydroxide solution, heated to about 180 ° C and maintained at this temperature for a period of time. up to four hours, depending on the heating rate. The reaction mixture is then forced into 3200 l of water and the resulting H-acid solution is mixed with 7600 kg of a dilute nitration solution from the previous preparation step, i.e. nitration of naphthalentrisulfoacid. The resulting h-acid suspension is heated to boiling while the sulfur dioxide is leaving, adjusting the pH of the suspension to less than 1. After cooling to 40 ° C, the suspension is filtered and the filter cake is washed with water. 917 g of H-acid are obtained in the form of the sodium salt. The filtrate is reduced with iron and, after neutralization with sodium hydroxide, the iron sludge is filtered off. The filtrate was acidified with hydrochloric acid, sodium chloride was added, and the precipitated 1-naphthylamine-3,6,8-trisulfoic acid was filtered off and washed. A total of 1620 kg of acid paste are obtained. The yield of H-acid with respect to isolation after reduction of the recovered 1-naphthylamine-3,6,8-trisulfoacid is 87.3% of theory.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS866984A CS254748B1 (en) | 1986-09-29 | 1986-09-29 | Process for preparing 1-amino-3-naftol-3,6-disulphonic acid |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS866984A CS254748B1 (en) | 1986-09-29 | 1986-09-29 | Process for preparing 1-amino-3-naftol-3,6-disulphonic acid |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CS698486A1 CS698486A1 (en) | 1987-05-14 |
| CS254748B1 true CS254748B1 (en) | 1988-01-15 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS866984A CS254748B1 (en) | 1986-09-29 | 1986-09-29 | Process for preparing 1-amino-3-naftol-3,6-disulphonic acid |
Country Status (1)
| Country | Link |
|---|---|
| CS (1) | CS254748B1 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106748901A (en) * | 2015-11-25 | 2017-05-31 | 江苏扬农化工集团有限公司 | A kind of alkali fusion and aftertreatment technology of H acid |
-
1986
- 1986-09-29 CS CS866984A patent/CS254748B1/en unknown
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106748901A (en) * | 2015-11-25 | 2017-05-31 | 江苏扬农化工集团有限公司 | A kind of alkali fusion and aftertreatment technology of H acid |
| CN106748901B (en) * | 2015-11-25 | 2018-11-06 | 江苏扬农化工集团有限公司 | A kind of alkali fusion and aftertreatment technology of H acid |
Also Published As
| Publication number | Publication date |
|---|---|
| CS698486A1 (en) | 1987-05-14 |
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