GB415945A - Manufacture of condensation products from phloroglucinol and aromatic amines - Google Patents
Manufacture of condensation products from phloroglucinol and aromatic aminesInfo
- Publication number
- GB415945A GB415945A GB2181/34A GB218134A GB415945A GB 415945 A GB415945 A GB 415945A GB 2181/34 A GB2181/34 A GB 2181/34A GB 218134 A GB218134 A GB 218134A GB 415945 A GB415945 A GB 415945A
- Authority
- GB
- United Kingdom
- Prior art keywords
- phloroglucinol
- water
- reaction
- hydroxybenzene
- compounds
- 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
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
- C07C215/74—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
- C07C215/76—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton of the same non-condensed six-membered aromatic ring
- C07C215/82—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton of the same non-condensed six-membered aromatic ring having the nitrogen atom of at least one of the amino groups further bound to a carbon atom of another six-membered aromatic ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
415,945. Arylaminophenols. I. G. FARBENINDUSTRIE AKT.-GES., Frankforton-Main, Germany. Jan. 22, 1934, No. 2181. Convention date, Jan. 20, 1933. [Class 2 (iii).] Condensation products of phloroglucinol with aromatic amines, which products still contain at least one hydroxyl group, are manufactured by heating phloroglucinol with an aromatic amine (i.e. any amine containing an aminogroup in an aryl nucleus) in the presence of water, at least a part of which remains in the reaction mixture at the end of the reaction. The reaction, particularly when the amine employed contains a strongly negative substituent, e.g. a nitro-group, may also be effected in the presence of a mineral acid, in which case the proportion of amine and acid and the duration of heating are adjusted so as to avoid the formation of a triarylaminobenzene. The proportion of water used may vary widely, the water of crystallization of the phloroglucinol being sufficient in some cases. The products, in the form of their alkali metal salts, have an affinity for vegetable fibres and may be employed as intermediates for the manufacture of dyestuffs or other organic compounds. In examples : (1) phloroglucinol is refluxed with aniline and water to produce diphenyldiaminohydroxybenzene ; the aniline may be replaced by p- or m-toluidine, p-anisidine or p-chloraniline ; (2) the reaction of (1) is carried out in the absence of water other than the water of crystallization of the phloroglucinol ; (3) phloroglucinol is reacted as in (2) with ptoluidine to produce di-(p-tolylamino)-hydroxybenzene ; (4) the reaction of (2) is carried out in a pressure vessel at 140‹ C. ; (5) the reaction of (3) is similarly carried out ; (6) phloroglucinol is refluxed with aniline oil and dilute hydrochloric acid, yielding the same product as in (1) together with a little 1 : 3 : 5-triphenyltriaminobenzene ; the aniline may be replaced by p-toluidine or p-chloraniline; (7) phloroglucinol is reacted with #-naphthylamine by the method of (6) to produce 1 : 3 : 5-di-(2<1>-naphthylamino)- hydroxybenzene ; (8) phloroglucinol is similarly reacted with m-nitraniline, producing 1 : 3 : 5- di-(3<1>-nitrophenylamino)-hydroxybenzene; (9) p-nitraniline similarly yields 1 : 3 : 5-di-(4<1>- nitrophenylamino)-hydroxybenzene, with or without 1 : 3 : 5-(4'-nitrophenylamino)-dihydroxybenzene, according to the proportion of p-nitraniline employed; in (8) and (9) the amines may be replaced by 4- or 5-nitro-2- aminomethoxybenzene or the corresponding ethoxy- or other alkoxy-compounds, 4- or 5- nitro-2-aminomethylbenzene or the corresponding ethyl- or other alkyl-compounds, or 4- or 6-chloro-3-nitraniline or the corresponding bromine or other halogen compounds; (10) phloroglucinol is refluxed with p-chloraniline and dilute sulphuric acid to produce 1 : 3 : 5-di- (4<1> - chlorophenylamino) - hydroxybenzene and some 1 : 3: 5 - tri - (4<1> - chlorophenylamino) - benzene ; the p-chloraniline may be replaced by 3 : 4- or 2 : 5-dichloraniline or 2 : 4 : 5- trichloraniline, the last two compounds yielding mainly the corresponding arylaminodihydroxybenzenes ; (11) phloroglucinol is refluxed with p-aminoquinoline hydrochloride and water.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DEI46329D DE601996C (en) | 1933-01-21 | 1933-01-21 | Process for the preparation of condensation products from phloroglucine and primary aromatic amines |
DEI48483D DE613516C (en) | 1933-01-21 | 1933-12-02 | Process for the preparation of condensation products |
Publications (1)
Publication Number | Publication Date |
---|---|
GB415945A true GB415945A (en) | 1934-09-06 |
Family
ID=25943635
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB2181/34A Expired GB415945A (en) | 1933-01-21 | 1934-01-22 | Manufacture of condensation products from phloroglucinol and aromatic amines |
GB34699/34A Expired GB448242A (en) | 1933-01-21 | 1934-12-03 | Manufacture of condensation products |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB34699/34A Expired GB448242A (en) | 1933-01-21 | 1934-12-03 | Manufacture of condensation products |
Country Status (4)
Country | Link |
---|---|
BE (1) | BE613516A (en) |
DE (2) | DE601996C (en) |
FR (2) | FR45499E (en) |
GB (2) | GB415945A (en) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5113018A (en) * | 1989-06-16 | 1992-05-12 | Mitsui Petrochemical Industries, Ltd. | Method of producing n-alkylaminophenols |
GB2358867A (en) * | 2000-02-03 | 2001-08-08 | Clive Stephen Delmonte | Three dimensional benzenoid polymer compositions |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE2850391A1 (en) * | 1978-11-21 | 1980-06-04 | Bayer Ag | PROCESS FOR THE PRODUCTION OF HYDROXY DIPHENYLAMINES |
-
0
- FR FR767500D patent/FR767500A/fr not_active Expired
- BE BE613516D patent/BE613516A/xx unknown
-
1933
- 1933-01-21 DE DEI46329D patent/DE601996C/en not_active Expired
- 1933-12-02 DE DEI48483D patent/DE613516C/en not_active Expired
-
1934
- 1934-01-22 GB GB2181/34A patent/GB415945A/en not_active Expired
- 1934-12-03 GB GB34699/34A patent/GB448242A/en not_active Expired
- 1934-12-03 FR FR45499D patent/FR45499E/en not_active Expired
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5113018A (en) * | 1989-06-16 | 1992-05-12 | Mitsui Petrochemical Industries, Ltd. | Method of producing n-alkylaminophenols |
GB2358867A (en) * | 2000-02-03 | 2001-08-08 | Clive Stephen Delmonte | Three dimensional benzenoid polymer compositions |
GB2358867B (en) * | 2000-02-03 | 2004-03-24 | Clive Stephen Delmonte | Three dimensional benzenoid polymer compositions and uses thereof |
Also Published As
Publication number | Publication date |
---|---|
BE613516A (en) | |
DE601996C (en) | 1934-08-29 |
FR45499E (en) | 1935-09-12 |
DE613516C (en) | 1935-05-20 |
GB448242A (en) | 1936-06-03 |
FR767500A (en) | 1934-07-17 |
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