GB278100A - Improved process for the manufacture of dinaphthyldicarboxylic acids - Google Patents

Improved process for the manufacture of dinaphthyldicarboxylic acids

Info

Publication number
GB278100A
GB278100A GB1693126A GB1693126A GB278100A GB 278100 A GB278100 A GB 278100A GB 1693126 A GB1693126 A GB 1693126A GB 1693126 A GB1693126 A GB 1693126A GB 278100 A GB278100 A GB 278100A
Authority
GB
United Kingdom
Prior art keywords
acid
dinaphthyl
solution
dicarboxylic acid
ammoniacal
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.)
Expired
Application number
GB1693126A
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.)
IG Farbenindustrie AG
Original Assignee
IG Farbenindustrie AG
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 IG Farbenindustrie AG filed Critical IG Farbenindustrie AG
Priority to GB1693126A priority Critical patent/GB278100A/en
Publication of GB278100A publication Critical patent/GB278100A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C65/00—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C65/32—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing keto groups
    • C07C65/34—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing keto groups polycyclic
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C63/00—Compounds having carboxyl groups bound to a carbon atoms of six-membered aromatic rings
    • C07C63/33—Polycyclic acids
    • C07C63/337—Polycyclic acids with carboxyl groups bound to condensed ring systems
    • C07C63/42—Polycyclic acids with carboxyl groups bound to condensed ring systems containing three or more condensed rings
    • C07C63/46—Polycyclic acids with carboxyl groups bound to condensed ring systems containing three or more condensed rings containing two carboxyl groups both bound to carbon atoms of the condensed ring system
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C63/00—Compounds having carboxyl groups bound to a carbon atoms of six-membered aromatic rings
    • C07C63/68—Compounds having carboxyl groups bound to a carbon atoms of six-membered aromatic rings containing halogen
    • C07C63/72—Polycyclic acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C65/00—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C65/21—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing ether groups, groups, groups, or groups
    • C07C65/24—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing ether groups, groups, groups, or groups polycyclic

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

Abstract

278,100. Carpmael, W., (I. G. Farbenindustrie Akt.-Ges.). July 6, 1926. Dinaphthyl-dicarboxylic acids and their substitution products are obtained by treating diazo compounds derived from o- or periamino -naphthoic acids or their derivatives with suitable reducing agents. e.g. an ammoniacal solution of cuprous oxide or a neutral solution of sodium sulphite or a ferrous salt. In examples (1) 1 : 1<1>- dinaphthyl-8 : 8<1>-dicarboxylic acid is obtained by reducing diazotized 1: 8-aminonaphthoic acid with an ammoniacal solution of cuprous oxide, made by passing sulphur dioxide through an ammoniacal solution of copper sulphate, or with a cuprous chloride solution obtained by reducing a solution of copper sulphate and common salt with sodium bisulphite; the diethyl ester may be obtained by esterifying with ethyl alcohol in the usual manner, (2) 2 2<1>-dinaphthyl-3 : 3<1>-dicarboxylic acid is similarly obtained from 2 : 3-aminonaphthoic acid; it dissolves in concentrated sulphuric acid with a red colour, probably due to the formation of dibenzofluorenone-3-carboxylic acid, (3) 1 : 1<1>-dinaphthyl-2 : 2'-dicarboxylic acid is similarly obtained from 1 : 2-aminonaphthoic acid, (4) 2 : 3-aminonaphthoic ethyl ester is diazotized and reduced with an ammoniacal solution of copper sulphate and ferrous sulphate; the product is 2 : 2<1>-dinaphthyl-3 : 3<1>-dicarboxylic diethyl ester, which yields the acid when saponified in the usual manner, (5) 1-chlor-2-aminonaphthalene-3- carboxylic acid, obtained by the action of oxidizing agents on 1-chlor-2 : 3-naphthisatin, is diazotized and reduced with ammoniacal cuprous oxide solution, or with a reducing solution obtained by mixing solutions of copper sulphate, ammonia, hydroxylamine hydrochloride and caustic potash ; the product is 1 : 1<1>-dichlor-2 : 2'- dinaphthyl-3 : 3<1>-dicarboxylic acid (6) 4-bromnaphthostyril is saponified to 1-amino-4-bromnaphthalene-8-carboxylic acid, the product is diazotized and reduced with ammoniacal cuprous oxide solution ; 4 : 4<1>-dibrom-1 : 1<1>-dinaplithyl- 8 : 8<1>-dicarboxylic acid is obtained, (7) 4-chlornaphthostyril. which may be obtained by chlorinating naphthostyril, is saponified to 1-amino-4- chlornaphthalene-8-carboxylic acid, diazotized and reduced with ammoniacal cuprous oxide solution, 4 : 4<1>-dichlor-1 : 1<1>-dinaphthyl-8 : 8<1>-dicarboxylic acid being obtained and may be converted into its diethyl ester; 5-chlornaphthostyril (obtained by converting 8-amino-5-chlornaphthalene-1-sulphonic acid into the 8-cyano derivative by Sandmeyer's reaction, and melting the product with caustic alkali as described in Specification 276,126) similarly yields 5: 5<1>-dichlor-1 : 1<1>-dinaphthyl-8 : 8<1>-dicarboxylic acid, (8) naphthostyril-4-sulphonic acid, obtained by sulphonating naphthostyril, yields, on saponification, 1-amino-4- sulphonaphthalene-8-carboxylic acid, from which 1 : 1<1>-dinaphthyl-4 : 4<1>-disulpho-8 : 81-dicarboxylic acid is obtained; and (9) 5-methoxy-1: 8-aminonaphthoic acid, obtained by the process described in Specification 276,126, yields 5 : 5-dimethoxy- 1:1<1>-dinaphthyl-8:8<1>-dicarboxylic acid; the corresponding diethoxy compound can be similarly obtained. Specification 21915/12 also is referred to.
GB1693126A 1926-07-06 1926-07-06 Improved process for the manufacture of dinaphthyldicarboxylic acids Expired GB278100A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB1693126A GB278100A (en) 1926-07-06 1926-07-06 Improved process for the manufacture of dinaphthyldicarboxylic acids

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB1693126A GB278100A (en) 1926-07-06 1926-07-06 Improved process for the manufacture of dinaphthyldicarboxylic acids

Publications (1)

Publication Number Publication Date
GB278100A true GB278100A (en) 1927-10-06

Family

ID=10086232

Family Applications (1)

Application Number Title Priority Date Filing Date
GB1693126A Expired GB278100A (en) 1926-07-06 1926-07-06 Improved process for the manufacture of dinaphthyldicarboxylic acids

Country Status (1)

Country Link
GB (1) GB278100A (en)

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