GB426403A - Process for the manufacture of hydroxydiphenylene compounds and derivatives thereof - Google Patents

Process for the manufacture of hydroxydiphenylene compounds and derivatives thereof

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Publication number
GB426403A
GB426403A GB2717133A GB2717133A GB426403A GB 426403 A GB426403 A GB 426403A GB 2717133 A GB2717133 A GB 2717133A GB 2717133 A GB2717133 A GB 2717133A GB 426403 A GB426403 A GB 426403A
Authority
GB
United Kingdom
Prior art keywords
hydroxydiphenylene
oxide
acid
solution
amino
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
GB2717133A
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 GB2717133A priority Critical patent/GB426403A/en
Publication of GB426403A publication Critical patent/GB426403A/en
Expired legal-status Critical Current

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Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D307/00Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/77Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D307/91Dibenzofurans; Hydrogenated dibenzofurans

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

Abstract

Hydroxydiphenylene compounds of the general formula <FORM:0426403/IV/1> in which X represents O, S, SO or SO2, are obtained by boiling the diazo compounds of the corresponding primary amines in aqueous solution in presence of phosphoric acid and, if desired, in presence of copper or a copper compound as catalyst. The following examples are specified. (1) 2-Aminodiphenylene-oxide in dilute sulphuric acid is diazotized by dropping in at 50--60 DEG C. a concentrated sodium nitrite solution, the solution is filtered, concentrated sulphuric acid is added to the filtrate, the diazonium sulphate, which crystallizes out on cooling, is filtered off and, without drying, mixed with technical phosphoric acid and p dropped into a flask heated to 200 DEG C. supplied with superheated steam; the 2-hydroxydiphenylene-oxide which distils off is purified by dissolving in caustic soda solution and precipitating with hydrochloric acid. (2) 2 - Aminodiphenylene - oxide is dissolved in technical phosphoric acid by heating at 100--110 DEG C. and the solution is cooled to 0--5 DEG C., at which most of the 2 - aminodiphenylene-oxide phosphate crystallizes, and diazotized by addition of dilute sodium nitrite solution; the diazo solution, filtered if necessary, is dropped into a flask, heated to 200--210 DEG C. containing technical phosphoric acid into which superheated steam is passed; 2-hydroxydiphenylene-oxide separates from the distillate. (3)-Aminodiphenylene-oxide is converted by the method of (2) into 3-hydroxydiphenylene-oxide. (4) 2 - Aminodiphenylene - sulphide, dissolved in technical phosphoric acid, is cooled to 0--5 DEG C. and diazotized by addition of dilute sodium nitrite solution; the diazo solution is dropped into a flask, heated to 180--200 DEG C. by the passage therethrough of superheated steam; 2-hydroxydiphenylene-sulphide separates from the distillate. (5) 2-Aminodiphenylene-sulphoxide and 3-aminodiphenylene-sulphone are converted by the method of (4) into 2-hydroxydiphenylene-sulphoxide and 3-hydroxydiphenylene-sulphone respectively. o-Carboxylic acids of the above hydroxydiphenylene compounds are obtained by treating them, in the form of their alkali metal salts or with the addition of an alkali, with carbon dioxide at elevated temperature and pressure. The following examples are specified. (6) The potassium salt of 3-hydroxydiphenylene-oxide is ground with potassium carbonate and the mixture is heated for 8--10 hours in an autoclave at 210--220 DEG C. to which carbon dioxide is supplied under pressure; the reaction mixture is dissolved in hot water, filtered, and the potassium salt of 3-hydroxydiphenylene-oxide-2-carboxylic acid is crystallized out from the filtrate; this is dissolved in hot water and acidified with hydrochloric acid to precipitate the free acid; 2-hydroxydiphenylene-oxide is similarly convertible into the corresponding 3-carboxylic acid. (7) The sodium salt of 3-hydroxydiphenylene-sulphide is treated with carbon dioxide as in (6) to obtain the corresponding 2-carboxylic acid. (8) The potassium salts of 3 - hydroxydiphenylene - sulphone and 3-hydroxydiphenylene - sulphoxide are treated with carbon dioxide as in (6) to obtain the corresponding 2-carboxylic acids. Arylamides of o-hydroxycarboxylic acids of diphenylene compounds are obtained from the acids by methods known per se, e.g. (a) by reaction of the amine with the chloride or an ester of the acid, (b) by heating a solution of the amine and the acid in an inert organic solvent with addition of phosphorous oxychloride or trichloride, (c) by reaction of the acid with the isocyanic ester corresponding to the amine (cf. Specification 289,037, [Class 2 (iii)]). The following examples are specified. (9) 3-Hydroxydiphenylene - oxide - 2 - carboxylic acid and 1 - amino - 2 - methoxy - 4 - chlorobenzene are dissolved in toluene at 60--65 DEG C., phosphorus trichloride is dropped in while stirring and the solution is boiled for 8 hours; the toluene and excess amine are removed by steam, the solution is made alkaline with sodium carbonate and the residue is filtered off, washed with water, dissolved in dilute caustic soda and treated with hydrochloric acid to precipitate the free arylamide; the acid may be replaced by 2 - hydroxyphenylene - oxide - 3 - carboxylic acid. (10) The arylamide from 3-hydroxydiphenylene-sulphide - 2 - carboxylic acid and 1 - amino - 2 - methoxy-4-chlorobenzene is similarly prepared; the acid may be replaced by 3 - hydroxydiphenylene-sulphone-2-carboxylic acid. 3-Aminodiphenylene-oxide is obtained by heating 3-bromodiphenylene oxide with concentrated aqueous ammonia for 10 hours at 200--220 DEG C. in presence of a copper salt. 2-Aminodiphenylene-sulphoxide is obtained by reducing the nitro group of the product of nitration of diphenylene sulphoxide. 3-Aminodiphenylene-sulphone is obtained by reducing the nitro group of the product of oxidation of 3-nitrodiphenylene sulphide with hydrogen peroxide in glacial acetic acid. The Specification as open to inspection under Sect. 91 comprises also additional subject-matter as follows: (a) an alternative to the process of example (2) in which the diazo solution is dropped into a boiling solution of phosphoric acid, until a test portion no longer couples with a component, the solution being then diluted and the product filtered off or extracted with a solvent; (b) an alternative to the process of example (6) in which a mixture of 3-hydroxydiphenylene-oxide and potassium carbonate is heated for 5--6 hours at 150 DEG C. in an autoclave to which carbon dioxide is supplied under pressure; (c) replacement of the amine in example (9) by aniline, 2-toluidine, 2- or 4-anisidine, 2-phenetidine, 2- or 4-chloraniline, 3-nitraniline, 1-amino-2 : 5- or 3 : 5-dimethylbenzene, 1-amino-2- or 3-methyl-4-methoxy benzene, 1 - amino - 2 - methyl - 4 - or 5-chlorobenzene, 1-amino-2 : 4- or 2 : 5-dimethoxybenzene, 1-amino-2-methoxy-5-chlorobenzene, 1 - amino - 2 - sulphondiethylamido - 4 - chlorobenzene, 1-amino-2 : 4 : 5- or 2 : 5 : 4-dimethoxychlorobenzene or 1-naphthylamine; (d) replacement of the amine in example (10) by a number of those specified in (c) or by 4-phenetidine, 2 - nitraniline, 1 - amino - 3 : 4-dichlorobenzene, 2 - amino - 6 - ethoxybenzothiazole or 1 - amino - carbazole; (e) the preparation by the process of example (9) of the arylamide from 3-hydroxydiphenylene - sulphide - 2 - carboxylic acid and dianisidine. This subject - matter does not appear in the Specification as accepted.
GB2717133A 1933-10-03 1933-10-03 Process for the manufacture of hydroxydiphenylene compounds and derivatives thereof Expired GB426403A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB2717133A GB426403A (en) 1933-10-03 1933-10-03 Process for the manufacture of hydroxydiphenylene compounds and derivatives thereof

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
GB2717133A GB426403A (en) 1933-10-03 1933-10-03 Process for the manufacture of hydroxydiphenylene compounds and derivatives thereof
GB2717333 1933-10-03
GB2717233 1933-10-03

Publications (1)

Publication Number Publication Date
GB426403A true GB426403A (en) 1935-04-03

Family

ID=47754224

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2717133A Expired GB426403A (en) 1933-10-03 1933-10-03 Process for the manufacture of hydroxydiphenylene compounds and derivatives thereof

Country Status (1)

Country Link
GB (1) GB426403A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN103833512A (en) * 2014-02-20 2014-06-04 常州市正锋光电新材料有限公司 Method of synthesizing o-dibromobenzene by diazotization in one step at high temperature

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN103833512A (en) * 2014-02-20 2014-06-04 常州市正锋光电新材料有限公司 Method of synthesizing o-dibromobenzene by diazotization in one step at high temperature

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