PL144803B1 - Process for preparing 4,4'-diaminostilben-2,2'-disulfonic acid - Google Patents

Process for preparing 4,4'-diaminostilben-2,2'-disulfonic acid Download PDF

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Publication number
PL144803B1
PL144803B1 PL25820886A PL25820886A PL144803B1 PL 144803 B1 PL144803 B1 PL 144803B1 PL 25820886 A PL25820886 A PL 25820886A PL 25820886 A PL25820886 A PL 25820886A PL 144803 B1 PL144803 B1 PL 144803B1
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Poland
Prior art keywords
disulfonic acid
catalyst
diaminostilbene
dinitrostilbene
diaminostilben
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Application number
PL25820886A
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Polish (pl)
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Publication of PL144803B1 publication Critical patent/PL144803B1/en

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Description

Przedmiotem wynalazku jest sposób otrzymywania kwasu 4,4'-diaminostilbeno-2,2'-disulfo- nowego, który stanowi wazny pólprodukt w syntezie barwników i wybielaczy fluoroscencyjnych.Znany jest, z opisu patentowego Wielkiej Brytanii nr 1447354, sposób otrzymywania soli disodowej kwasu 4,4'-diaminostilbeno-2,2'-disulfonowego na drodze redukcji soli disodowej kwasu 4,4'-dinitrostilbeno-2,2'-disulfonowego wodorem przy cisnieniu co najmniej 98kPa, w obecnosci katalizatora niklowego, korzystnie niklu Raney'a lub Urushibara, w temperaturze 20-200°C, w srodowisku alkoholowym zawierajacym przed rozpoczeciem redukcji mniej niz 3% wagowych wody, wzglednie w srodowisku wodnym o pH = 5-10, ustalonym w wyniku dodania buforu.Znany jest takze, z opisu patentowego RFN nr 2 362 781, sposób otrzymywania kwasu 4,4'- diaminostilbeno-2,2'-disulfonowego polegajacy na redukcji kwasu 4,4'-dinitrostilbeno-2,2'-disulfo- nowego wodorem przy cisnieniu 4000-8000 kPa,w obecnosci kobaltu Raney'a lub kobaltu osadzo¬ nego na zelu krzemionkowym jako katalizatora, w temperaturze 120°C, przy pH srodowiska reakcji 6-7.Niedogodnoscia sposobów wedlug patentów Wielkiej Brytanii i RFN jest stosowanie pirofo¬ rycznych katalizatorów takich, jak nikiel lub kobalt Raney'a, a takze koniecznosc stosowania buforów utrzymujacych wlasciwe pH srodowiska reakcji.Zjaponskich opisów patentowych nr nr 7 593 952 i 74127 955jest znany sposób otrzymywania kwasu 4,4'-diaminostilbeno-2,2/-disulfonowego na drodze redukcji kwasu 4,4'-dinitrostilbeno-2,2'- disulfonowego wodorem, przy czym redukcje prowadzi sie przy cisnieniu 101-102 kPa, w obec¬ nosci platyny lub palladu osadzonych na nosniku weglowym jako katalizatora, w temperaturze 50°C, w srodowisku wodnym lub metanolu, z dodatkiem jodków lub bromków potasu.Niedogodnoscia tych sposobówjest koniecznosc poddawania stosowanych w tych sposobach katalizatorów wstepnej obróbce parami J2 lub Br2- Sposób otrzymywania kwasu 4,4/-diaminostilbeno-2,2/-disulfonowego na drodze redukcji kwasu 4,4'-dinitrostilbeno-2,2'-disulfonowego wodorem, w obecnosci katalizatora metalicznego, w srodowisku alkoholowym, korzystnie metanolu, wedlug wynalazku polega na tym, ze jako2 144 m katalizator metaliczny stosuje sie pallad osadzony na nosniku krzemionkowym zawierajacym 5% wagowych fazy metalicznej, przy czym redukcje prowadzi sie pod cisnieniem 566,5-618 kPa, w temperaturze 80°C, przy stosunku wagowym substratu do katalizatora od 5:1 do 10:1.Sposób wedlug wynalazku zapewnia otrzymanie kwasu 4,4'-diaminostilbeno-2,2'-disulfo- nowego o wysokiej czystosci i z dobra wydajnoscia. Nadto w sposobie wedlug wynalazku wyelimi¬ nowano stosowanie piroforycznych katalizatorów, a takze koniecznosc wprowadzania do srodo¬ wiska reakcji dodatkowych substancji takich, jak bufory, jodki, bromki.Sposób wedlug wynalazku ilustruje blizej nizej podany przyklad.Przyklad. Reaktor zawierajacy roztwór 5 g kwasu 4,4'-dinitrostilbeno-2,2'-disulfonowego w 120 cm3 metanolu oraz 1 g katalizatora palladowego osadzonego na nosniku krzemionkowym, zawierajacego 0,05 g fazy metalicznej napelniono wodorem do cisnienia 566,5 kPa, po czym pro¬ wadzono reakcje redukcji w temperaturze 80°C w ciagu 4 godzin mieszajac intensywnie zawartosc reaktora. Po zakonczeniu redukcji odfiltrowano katalizator, a kwas 4,4'-diaminostilbeno-2,2'- disulfonowego wytracono w znany sposób przez zakwaszenie 2n kwasem solnym. Otrzymano 4,18 g kwasu 4,4'-diaminostilbeno-2,2'-disulfonowego, co stanowilo 97,38% wydajnosci teore¬ tycznej.Zastrzezenie patentowe Sposób otrzymywania kwasu 4,4'-diaminostilbeno-2,2'-disulfonowego na drodze redukcji kwasu 4,4'-dinitrostilbeno-2,2'-disulfonowego wodorem, w obecnosci katalizatora metalicznego, w srodowisku alkoholowym, korzystnie metanolu, znamienny tym, ze jako katalizator metaliczny stosuje sie pallad osadzony na nosniku krzemionkowym zawierajacym 5% wagowych fazy metali¬ cznej, przy czym redukcje prowadzi sie pod cisnieniem 566,5-618 kPa, w temperaturze 80°C, przy stosunku wagowym substratu do katalizatora od 5:1 do 10:1.Pracownia Poligraficzna UP PRL. Naklad 100 egz.Cena 400 zl PLThe subject of the invention is a method for the preparation of 4,4'-diaminostilbene-2,2'-disulfonic acid, which is an important intermediate in the synthesis of fluorescent dyes and bleaches. It is known from the British Patent No. 1,447,354 to obtain the disodium salt of 4 , 4'-diaminostilbene-2,2'-disulfonic acid by reduction of the disodium salt of 4,4'-dinitrostilbene-2,2'-disulfonic acid with hydrogen at a pressure of at least 98kPa, in the presence of a nickel catalyst, preferably Raney or Urushibara nickel , at a temperature of 20-200 ° C, in an alcoholic environment containing less than 3% by weight of water before the start of the reduction, or in an aqueous environment with a pH = 5-10, determined by adding a buffer. It is also known from German patent specification No. 2 362 781, method of obtaining 4,4'-diaminostilbene-2,2'-disulfonic acid by reducing 4,4'-dinitrostilbene-2,2'-disulfonic acid with hydrogen at a pressure of 4000-8000 kPa, in the presence of Raney cobalt or deposited cobalt on silica gel as a catalyst, at a temperature of 120 ° C, at a pH of the reaction environment of 6-7. The disadvantage of the methods according to the British and German patents is the use of pyrophoric catalysts such as nickel or Raney cobalt, as well as the necessity to use proper pH of the reaction environment. Japanese patents No. 7 593 952 and 74 127 955 is a known method of obtaining 4,4'-diaminostilbene-2,2) -disulfonic acid by reducing 4,4'-dinitrostilbene-2,2'-disulfonic acid hydrogen, the reductions being carried out at a pressure of 101-102 kPa, in the presence of platinum or palladium supported on a carbon carrier as a catalyst, at a temperature of 50 ° C., in an aqueous environment or methanol, with the addition of potassium iodides or bromides. necessity of subjecting the catalysts used in these methods to pre-treatment with J2 or Br2 steam - Method for obtaining 4,4 H-diaminostilbene-2,2 H -disulfonic acid by reducing the acid in 4,4'-dinitrostilbene-2,2'-disulfonic acid with hydrogen, in the presence of a metal catalyst, in an alcoholic environment, preferably methanol, according to the invention, according to the invention, palladium is used as a metal catalyst, deposited on a silica support containing 5% by weight of the metallic phase, the reductions being carried out at a pressure of 566.5-618 kPa, at a temperature of 80 ° C, with a substrate to catalyst weight ratio of 5: 1 to 10: 1. The method according to the invention provides the acid 4.4'- diaminostilbene-2,2'-disulfonic acid with high purity and good performance. In addition, the process according to the invention eliminates the use of pyrophoric catalysts, as well as the need to introduce additional substances into the reaction medium, such as buffers, iodides, bromides. The method according to the invention is illustrated by the following example. The reactor containing a solution of 5 g of 4,4'-dinitrostilbene-2,2'-disulfonic acid in 120 cm3 of methanol and 1 g of a palladium catalyst supported on a silica support, containing 0.05 g of a metallic phase, was filled with hydrogen to a pressure of 566.5 kPa, then The reduction reactions were carried out at a temperature of 80 ° C. for 4 hours while the contents of the reactor were thoroughly stirred. After the reduction was completed, the catalyst was filtered off and the 4,4'-diaminostilbene-2,2'-disulfonic acid was precipitated in a known manner by acidification with 2N hydrochloric acid. 4.18 g of 4,4'-diaminostilbene-2,2'-disulfonic acid were obtained, which was 97.38% of theoretical yield. Patent claim The method of obtaining 4,4'-diaminostilbene-2,2'-disulfonic acid on by reduction of 4,4'-dinitrostilbene-2,2'-disulfonic acid with hydrogen, in the presence of a metal catalyst, in an alcoholic environment, preferably methanol, characterized in that palladium is used as the metal catalyst on a silica support containing 5% by weight of metal phases The reduction is carried out at a pressure of 566.5-618 kPa, at a temperature of 80 ° C, with a substrate / catalyst weight ratio from 5: 1 to 10: 1. Mintage 100 copies Price PLN 400 PL

Claims (1)

1. Zastrzezenie patentowe Sposób otrzymywania kwasu 4,4'-diaminostilbeno-2,2'-disulfonowego na drodze redukcji kwasu 4,4'-dinitrostilbeno-2,2'-disulfonowego wodorem, w obecnosci katalizatora metalicznego, w srodowisku alkoholowym, korzystnie metanolu, znamienny tym, ze jako katalizator metaliczny stosuje sie pallad osadzony na nosniku krzemionkowym zawierajacym 5% wagowych fazy metali¬ cznej, przy czym redukcje prowadzi sie pod cisnieniem 566,5-618 kPa, w temperaturze 80°C, przy stosunku wagowym substratu do katalizatora od 5:1 do 10:1. Pracownia Poligraficzna UP PRL. Naklad 100 egz. Cena 400 zl PL1. Patent claim A method of obtaining 4,4'-diaminostilbene-2,2'-disulfonic acid by reduction of 4,4'-dinitrostilbene-2,2'-disulfonic acid with hydrogen, in the presence of a metal catalyst, in an alcoholic environment, preferably methanol , characterized in that the metal catalyst is palladium deposited on a silica support containing 5% by weight of the metal phase, the reductions being carried out at a pressure of 566.5-618 kPa, at a temperature of 80 ° C, with the weight ratio of the substrate to the catalyst 5: 1 to 10: 1. Printing workshop of the UP PRL. Mintage 100 copies. Price PLN 400 PL
PL25820886A 1986-03-03 1986-03-03 Process for preparing 4,4'-diaminostilben-2,2'-disulfonic acid PL144803B1 (en)

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PL25820886A PL144803B1 (en) 1986-03-03 1986-03-03 Process for preparing 4,4'-diaminostilben-2,2'-disulfonic acid

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Application Number Priority Date Filing Date Title
PL25820886A PL144803B1 (en) 1986-03-03 1986-03-03 Process for preparing 4,4'-diaminostilben-2,2'-disulfonic acid

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PL144803B1 true PL144803B1 (en) 1988-07-30

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102206175A (en) * 2011-04-18 2011-10-05 河北华戈染料化学股份有限公司 Method for preparing DSD (4,4'-Diamino 2,2'-Stilbene Disulphonic) acid by hydrogenating and reducing disodium dinitrosalicylate (DNS) at high temperature
CN102417471A (en) * 2011-10-31 2012-04-18 天津大学 Preparation method of 4-amino-2-sulfonic benzoic acid
CN102675161A (en) * 2011-03-10 2012-09-19 中国中化股份有限公司 Method for preparing DSD acid

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102675161A (en) * 2011-03-10 2012-09-19 中国中化股份有限公司 Method for preparing DSD acid
CN102206175A (en) * 2011-04-18 2011-10-05 河北华戈染料化学股份有限公司 Method for preparing DSD (4,4'-Diamino 2,2'-Stilbene Disulphonic) acid by hydrogenating and reducing disodium dinitrosalicylate (DNS) at high temperature
CN102206175B (en) * 2011-04-18 2014-01-08 河北华戈染料化学股份有限公司 Method for preparing DSD (4,4'-Diamino 2,2'-Stilbene Disulphonic) acid by hydrogenating and reducing disodium dinitrosalicylate (DNS) at high temperature
CN102417471A (en) * 2011-10-31 2012-04-18 天津大学 Preparation method of 4-amino-2-sulfonic benzoic acid
CN102417471B (en) * 2011-10-31 2013-11-20 天津大学 Preparation method of 4-amino-2-sulfonic benzoic acid

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