FR2398724A1 - IMPROVEMENTS IN THE PREPARATION OF 2-AMINO-1-NAPHTALENESULPHONIC ACID OR TOBIAS ACID - Google Patents

IMPROVEMENTS IN THE PREPARATION OF 2-AMINO-1-NAPHTALENESULPHONIC ACID OR TOBIAS ACID

Info

Publication number
FR2398724A1
FR2398724A1 FR7822222A FR7822222A FR2398724A1 FR 2398724 A1 FR2398724 A1 FR 2398724A1 FR 7822222 A FR7822222 A FR 7822222A FR 7822222 A FR7822222 A FR 7822222A FR 2398724 A1 FR2398724 A1 FR 2398724A1
Authority
FR
France
Prior art keywords
acid
degrees
mixture
tobias
preparation
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
FR7822222A
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 FR2398724A1 publication Critical patent/FR2398724A1/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
    • C07C303/42—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)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Pour cette préparation on fait réagir en I une solution de 2-hydroxynaphtalène BN dans un solvant organique avec de l'acide chlorosulfonique (C1SO3 H) à 0-10 degrés C, alcalinise le mélange résultant en III, recueille de ce mélange alcalinisé une phase aqueuse contenant un sel alcalin d'acide 2-hydroxy-1naphtalène-sulfonique AA, qui est aminé en VII pour donner un mélange aqueux de sels alcalins 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, 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 avant alcalinisation; 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.For this preparation, a solution of 2-hydroxynaphthalene BN is reacted in I in an organic solvent with chlorosulfonic acid (C1SO3 H) at 0-10 degrees C, the resulting mixture is made alkaline in III, and a phase is collected from this alkalized mixture. aqueous containing an alkali salt of 2-hydroxy-1naphthalenesulfonic acid AA, which is aminated in VII to give an aqueous mixture of alkali salts and ammonia of Tobias acid, which is extracted in X by means of a organic solvent immiscible with water, while the aqueous phase is acidified in XI. According to the invention, the reaction mixture of I is transferred to a reserve vessel II where it remains for 5 to 60 minutes at 0-10 degrees C before basifying; in addition, the acidification in XI is carried out at 20-80 degrees C up to pH 1.8-2.5. This gives a Tobias acid containing a very low content of 2-aminonaphthalene, a carcinogenic product.

FR7822222A 1977-07-29 1978-07-27 IMPROVEMENTS IN THE PREPARATION OF 2-AMINO-1-NAPHTALENESULPHONIC ACID OR TOBIAS ACID Pending FR2398724A1 (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US82005777A 1977-07-29 1977-07-29

Publications (1)

Publication Number Publication Date
FR2398724A1 true FR2398724A1 (en) 1979-02-23

Family

ID=25229775

Family Applications (1)

Application Number Title Priority Date Filing Date
FR7822222A Pending FR2398724A1 (en) 1977-07-29 1978-07-27 IMPROVEMENTS IN THE PREPARATION OF 2-AMINO-1-NAPHTALENESULPHONIC ACID OR TOBIAS ACID

Country Status (4)

Country Link
JP (1) JPS5427554A (en)
DE (1) DE2831992A1 (en)
FR (1) FR2398724A1 (en)
GB (1) GB2001644B (en)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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
FR2398726A1 (en) * 1977-07-29 1979-02-23 American Cyanamid Co 2-AMINO-1-NAPHTHALENESULPHONIC ACID PREPARATION PROCESS
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
FR2398725A1 (en) * 1977-07-29 1979-02-23 American Cyanamid Co IMPROVEMENTS IN THE PREPARATION OF 2-AMINO-1-NAPHTALENESULPHONIC ACID

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3070185D1 (en) * 1979-12-20 1985-03-28 Ciba Geigy Ag Process for the preparation of 2-amino-1-naphthalene sulfonic acid

Citations (9)

* 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
FR2398725A1 (en) * 1977-07-29 1979-02-23 American Cyanamid Co IMPROVEMENTS IN THE PREPARATION OF 2-AMINO-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
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
FR2398727A1 (en) * 1977-07-29 1979-02-23 American Cyanamid Co PROCESS FOR PREPARING TOBIAS ACID OR 2-AMINO-1-NAPHTALENESULPHONIC ACID
FR2398723A1 (en) * 1977-07-29 1979-02-23 American Cyanamid Co PROCESS FOR PREPARING 2-AMINO-1-NAPHTALENESULPHONIC ACID OR TOBIAS ACID

Patent Citations (9)

* 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
FR2398725A1 (en) * 1977-07-29 1979-02-23 American Cyanamid Co IMPROVEMENTS IN THE PREPARATION OF 2-AMINO-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
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
FR2398727A1 (en) * 1977-07-29 1979-02-23 American Cyanamid Co PROCESS FOR PREPARING TOBIAS ACID OR 2-AMINO-1-NAPHTALENESULPHONIC ACID
FR2398723A1 (en) * 1977-07-29 1979-02-23 American Cyanamid Co PROCESS FOR PREPARING 2-AMINO-1-NAPHTALENESULPHONIC ACID OR TOBIAS ACID

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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
FR2398726A1 (en) * 1977-07-29 1979-02-23 American Cyanamid Co 2-AMINO-1-NAPHTHALENESULPHONIC ACID PREPARATION PROCESS
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
FR2398725A1 (en) * 1977-07-29 1979-02-23 American Cyanamid Co IMPROVEMENTS IN THE PREPARATION OF 2-AMINO-1-NAPHTALENESULPHONIC ACID

Also Published As

Publication number Publication date
JPS5427554A (en) 1979-03-01
GB2001644B (en) 1982-02-10
GB2001644A (en) 1979-02-07
DE2831992A1 (en) 1979-02-08

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