FR2398727A1 - PROCESS FOR PREPARING TOBIAS ACID OR 2-AMINO-1-NAPHTALENESULPHONIC ACID - Google Patents

PROCESS FOR PREPARING TOBIAS ACID OR 2-AMINO-1-NAPHTALENESULPHONIC ACID

Info

Publication number
FR2398727A1
FR2398727A1 FR7822226A FR7822226A FR2398727A1 FR 2398727 A1 FR2398727 A1 FR 2398727A1 FR 7822226 A FR7822226 A FR 7822226A FR 7822226 A FR7822226 A FR 7822226A FR 2398727 A1 FR2398727 A1 FR 2398727A1
Authority
FR
France
Prior art keywords
acid
degrees
mixture
tobias
c1so3
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.)
Pending
Application number
FR7822226A
Other languages
French (fr)
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Wyeth Holdings LLC
Original Assignee
American Cyanamid Co
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by American Cyanamid Co filed Critical American Cyanamid Co
Publication of FR2398727A1 publication Critical patent/FR2398727A1/en
Pending legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
    • C07C303/32—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of salts of sulfonic acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
    • C07C303/02—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
    • C07C303/02—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof
    • C07C303/04—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof by substitution of hydrogen atoms by sulfo or halosulfonyl groups
    • C07C303/06—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof by substitution of hydrogen atoms by sulfo or halosulfonyl groups by reaction with sulfuric acid or sulfur trioxide
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
    • C07C303/02—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof
    • C07C303/22—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof from sulfonic acids, by reactions not involving the formation of sulfo or halosulfonyl groups; from sulfonic halides by reactions not involving the formation of halosulfonyl groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
    • C07C303/42—Separation; Purification; Stabilisation; Use of additives
    • C07C303/44—Separation; Purification
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
    • C07C309/01—Sulfonic acids
    • C07C309/28—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Dans ce procédé, on fait réagir en I une solution de 2hydroxy-naphtalène BN dans un solvant organique avec de l'acide chlorosulfonique (C1SO3 H), alcalinise le mélange résultant en III, recueille de ce mélange alcalinisé une phase aqueuse contenant un sel alcalin d'acide 2-hydroxy-1-naphtalènesulfonique AA, qui est aminé en VII pour donner un mélange aqueux de sels alcalin et d'ammoniac d'acide de Tobias, lequel est extrait en X au moyen d'un solvant organique non miscible à l'eau, cependant que la phase aqueuse est acidifiée en XI. Selon l'invention, la réaction en I est effectuée à 0-10 degrés C avec un rapport molaire C1SO3 H/BN de 0,85 à 1,15 avec un temps de séjour de 5 à 120 minutes et le mélange réactionnel de I est transféré dans un récipient de réserve II où il séjourne 5 à 60 minutes à 0-10 degrés C; de plus l'acidification en XI est effectuée à 20-80 degrés C jusqu'à pH de 1,8 à 2,5. On obtient ainsi un acide de Tobias contenant une très faible teneur en 2-aminonaphtalène produit carcinogène.In this process, reacting in I a solution of 2hydroxy-naphthalene BN in an organic solvent with chlorosulfonic acid (C1SO3 H), basifying the resulting mixture in III, collecting from this basified mixture an aqueous phase containing an alkali salt 2-hydroxy-1-naphthalenesulfonic acid AA, which is aminated in VII to give an aqueous mixture of alkali and ammonia salts of Tobias acid, which is extracted in X using an organic solvent immiscible with water, while the aqueous phase is acidified in XI. According to the invention, the reaction in I is carried out at 0-10 degrees C with a C1SO3 H / BN molar ratio of 0.85 to 1.15 with a residence time of 5 to 120 minutes and the reaction mixture of I is transferred to a reserve container II where it remains for 5 to 60 minutes at 0-10 degrees C; further the acidification in XI is carried out at 20-80 degrees C up to pH 1.8 to 2.5. This gives a Tobias acid containing a very low content of 2-aminonaphthalene, a carcinogenic product.

FR7822226A 1977-07-29 1978-07-27 PROCESS FOR PREPARING TOBIAS ACID OR 2-AMINO-1-NAPHTALENESULPHONIC ACID Pending FR2398727A1 (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US82005677A 1977-07-29 1977-07-29

Publications (1)

Publication Number Publication Date
FR2398727A1 true FR2398727A1 (en) 1979-02-23

Family

ID=25229772

Family Applications (1)

Application Number Title Priority Date Filing Date
FR7822226A Pending FR2398727A1 (en) 1977-07-29 1978-07-27 PROCESS FOR PREPARING TOBIAS ACID OR 2-AMINO-1-NAPHTALENESULPHONIC ACID

Country Status (4)

Country Link
JP (1) JPS5427553A (en)
DE (1) DE2831966A1 (en)
FR (1) FR2398727A1 (en)
GB (1) GB2001640B (en)

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2398721A1 (en) * 1977-07-29 1979-02-23 American Cyanamid Co PROCESS FOR PREPARING AQUEOUS SOLUTIONS OF ALKALINE SALTS OF 2-HYDROXY-1-NAPHTALENESULPHONIC ACID
FR2398724A1 (en) * 1977-07-29 1979-02-23 American Cyanamid Co IMPROVEMENTS IN THE PREPARATION OF 2-AMINO-1-NAPHTALENESULPHONIC ACID OR TOBIAS ACID
FR2398725A1 (en) * 1977-07-29 1979-02-23 American Cyanamid Co IMPROVEMENTS IN THE PREPARATION OF 2-AMINO-1-NAPHTALENESULPHONIC ACID
FR2398726A1 (en) * 1977-07-29 1979-02-23 American Cyanamid Co 2-AMINO-1-NAPHTHALENESULPHONIC ACID PREPARATION PROCESS
FR2398723A1 (en) * 1977-07-29 1979-02-23 American Cyanamid Co PROCESS FOR PREPARING 2-AMINO-1-NAPHTALENESULPHONIC ACID OR TOBIAS ACID
FR2398722A1 (en) * 1977-07-29 1979-02-23 American Cyanamid Co IMPROVEMENTS FOR THE PREPARATION OF AQUEOUS SOLUTIONS OF ALKALINE SALTS OF 2-HYDROXY-1-NAPHTALENESULPHONIC ACID

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0031299B1 (en) * 1979-12-20 1985-02-13 Ciba-Geigy Ag Process for the preparation of 2-amino-1-naphthalene sulfonic acid
JPH0819264B2 (en) * 1988-06-03 1996-02-28 日本ゼオン株式会社 Vulcanizable rubber composition
CN109810028A (en) * 2019-04-03 2019-05-28 天津市科德化工有限公司 Apparatus system for tobias acid waste liquid purification tobias acid
CN113698323B (en) * 2021-09-02 2023-09-05 昌邑瑞新化学工业有限公司 Method for producing tobias acid by reducing yield of acid precipitation mother liquor wastewater
CN113698324A (en) * 2021-09-02 2021-11-26 昌邑瑞新化学工业有限公司 Method for producing tobias acid and by-producing ammonium sulfate or ammonium chloride by using full ammonium salt system

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2058911A (en) * 1931-12-08 1936-10-27 Nat Aniline & Chem Co Inc Process for the purification of naphthylamine sulphonic acid
FR1182010A (en) * 1956-09-05 1959-06-22 Gen Aniline & Film Corp Process for preparing beta-naphthol-sulfonic acid
DE2330716A1 (en) * 1973-01-12 1974-08-01 Bitterfeld Chemie Equipment for continuous liquid phase reactions - separate compartments in horizontal reactor with axial stirrer shaft carrying required agitators
DE2610545A1 (en) * 1975-03-14 1976-09-30 American Cyanamid Co METHOD FOR MANUFACTURING TOBIAS ACID
FR2398723A1 (en) * 1977-07-29 1979-02-23 American Cyanamid Co PROCESS FOR PREPARING 2-AMINO-1-NAPHTALENESULPHONIC ACID OR TOBIAS ACID
FR2398722A1 (en) * 1977-07-29 1979-02-23 American Cyanamid Co IMPROVEMENTS FOR THE PREPARATION OF AQUEOUS SOLUTIONS OF ALKALINE SALTS OF 2-HYDROXY-1-NAPHTALENESULPHONIC ACID
FR2398721A1 (en) * 1977-07-29 1979-02-23 American Cyanamid Co PROCESS FOR PREPARING AQUEOUS SOLUTIONS OF ALKALINE SALTS OF 2-HYDROXY-1-NAPHTALENESULPHONIC ACID

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2058911A (en) * 1931-12-08 1936-10-27 Nat Aniline & Chem Co Inc Process for the purification of naphthylamine sulphonic acid
FR1182010A (en) * 1956-09-05 1959-06-22 Gen Aniline & Film Corp Process for preparing beta-naphthol-sulfonic acid
DE2330716A1 (en) * 1973-01-12 1974-08-01 Bitterfeld Chemie Equipment for continuous liquid phase reactions - separate compartments in horizontal reactor with axial stirrer shaft carrying required agitators
DE2610545A1 (en) * 1975-03-14 1976-09-30 American Cyanamid Co METHOD FOR MANUFACTURING TOBIAS ACID
FR2398723A1 (en) * 1977-07-29 1979-02-23 American Cyanamid Co PROCESS FOR PREPARING 2-AMINO-1-NAPHTALENESULPHONIC ACID OR TOBIAS ACID
FR2398722A1 (en) * 1977-07-29 1979-02-23 American Cyanamid Co IMPROVEMENTS FOR THE PREPARATION OF AQUEOUS SOLUTIONS OF ALKALINE SALTS OF 2-HYDROXY-1-NAPHTALENESULPHONIC ACID
FR2398721A1 (en) * 1977-07-29 1979-02-23 American Cyanamid Co PROCESS FOR PREPARING AQUEOUS SOLUTIONS OF ALKALINE SALTS OF 2-HYDROXY-1-NAPHTALENESULPHONIC ACID

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2398721A1 (en) * 1977-07-29 1979-02-23 American Cyanamid Co PROCESS FOR PREPARING AQUEOUS SOLUTIONS OF ALKALINE SALTS OF 2-HYDROXY-1-NAPHTALENESULPHONIC ACID
FR2398724A1 (en) * 1977-07-29 1979-02-23 American Cyanamid Co IMPROVEMENTS IN THE PREPARATION OF 2-AMINO-1-NAPHTALENESULPHONIC ACID OR TOBIAS ACID
FR2398725A1 (en) * 1977-07-29 1979-02-23 American Cyanamid Co IMPROVEMENTS IN THE PREPARATION OF 2-AMINO-1-NAPHTALENESULPHONIC ACID
FR2398726A1 (en) * 1977-07-29 1979-02-23 American Cyanamid Co 2-AMINO-1-NAPHTHALENESULPHONIC ACID PREPARATION PROCESS
FR2398723A1 (en) * 1977-07-29 1979-02-23 American Cyanamid Co PROCESS FOR PREPARING 2-AMINO-1-NAPHTALENESULPHONIC ACID OR TOBIAS ACID
FR2398722A1 (en) * 1977-07-29 1979-02-23 American Cyanamid Co IMPROVEMENTS FOR THE PREPARATION OF AQUEOUS SOLUTIONS OF ALKALINE SALTS OF 2-HYDROXY-1-NAPHTALENESULPHONIC ACID

Also Published As

Publication number Publication date
GB2001640A (en) 1979-02-07
JPS5427553A (en) 1979-03-01
GB2001640B (en) 1982-02-10
DE2831966A1 (en) 1979-02-08

Similar Documents

Publication Publication Date Title
FR2398727A1 (en) PROCESS FOR PREPARING TOBIAS ACID OR 2-AMINO-1-NAPHTALENESULPHONIC ACID
FR2398723A1 (en) PROCESS FOR PREPARING 2-AMINO-1-NAPHTALENESULPHONIC ACID OR TOBIAS ACID
US4424390A (en) Process for producing 5-halomethylfurfural
FR2398724A1 (en) IMPROVEMENTS IN THE PREPARATION OF 2-AMINO-1-NAPHTALENESULPHONIC ACID OR TOBIAS ACID
FR2446840A1 (en) FERRIC SALT OF FRUCTOSE-DIPHOSPHATE-1,6, PROCESS FOR ITS OBTAINMENT AND FOR ITS USE IN THE PREPARATION OF FRUCTOSE-DIPHOSPHORIC-1,6 ACID
FR2427319A1 (en) PROCESS FOR THE PREPARATION OF RESORCINOL
FI68809B (en) FOER FARING FRAMSTAELLNING AV P-HYDROXIFENYLGLYCIN
JPS5540613A (en) Preparation of 2, 6-dichloro-4-alkylphenol
EP0487578A1 (en) Method of producing tertiary amine-sulphur trioxide complexes
FR2398726A1 (en) 2-AMINO-1-NAPHTHALENESULPHONIC ACID PREPARATION PROCESS
FR2421144A1 (en) CRUDE PHOSPHATE TRANSFORMER PROCESS CONTAINING MAGNESIUM TO PHOSPHORIC ACID AND A MIXTURE OF MAGNESIUM CARBONATES AND CALCIUM
KR900004678A (en) Method for preparing trisodium salt of isocerine-N, N-diacetic acid
FR2398725A1 (en) IMPROVEMENTS IN THE PREPARATION OF 2-AMINO-1-NAPHTALENESULPHONIC ACID
GB1489036A (en) Process for the continuous preparation of percarboxylic acids in organic solution
FR2398722A1 (en) IMPROVEMENTS FOR THE PREPARATION OF AQUEOUS SOLUTIONS OF ALKALINE SALTS OF 2-HYDROXY-1-NAPHTALENESULPHONIC ACID
FR2373586A1 (en) PREPARATION OF LIQUID COLORANT AND IMPROVED PROCESS FOR THE PRODUCTION OF THE LATTER
US4973688A (en) Process for the production of 1-n-dodecylazacycloheptan-2-one
US3449385A (en) Process for the manufacture of aliphatic alpha-hydroxycarboxylic acids
FR2398721A1 (en) PROCESS FOR PREPARING AQUEOUS SOLUTIONS OF ALKALINE SALTS OF 2-HYDROXY-1-NAPHTALENESULPHONIC ACID
FR2365562A1 (en) CYANURIC ACID PREPARATION PROCESS
Anderson et al. EDTA, Ethylenediaminetetraacetic Acid
CA1111444A (en) Process for production of beta-chloroalanine
SU1559285A1 (en) Method of quantitative determination of 1-nitroso-1-alkylureas
SU133872A1 (en) The method of obtaining the Quaternary ammonium salts
DE1810994C3 (en) Process for the preparation of 6- (alpha-phenoxybutyramido) -penicillanic acid