DE1055540B - Process for the preparation of diarylamines - Google Patents
Process for the preparation of diarylaminesInfo
- Publication number
- DE1055540B DE1055540B DEF24590A DEF0024590A DE1055540B DE 1055540 B DE1055540 B DE 1055540B DE F24590 A DEF24590 A DE F24590A DE F0024590 A DEF0024590 A DE F0024590A DE 1055540 B DE1055540 B DE 1055540B
- Authority
- DE
- Germany
- Prior art keywords
- diarylamines
- reaction
- preparation
- phosphoric acid
- mixture
- 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
Links
- 238000000034 method Methods 0.000 title claims description 6
- 125000005266 diarylamine group Chemical group 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title description 2
- 238000006243 chemical reaction Methods 0.000 claims description 11
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 10
- 150000004982 aromatic amines Chemical class 0.000 claims description 6
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 5
- 238000009835 boiling Methods 0.000 claims description 5
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims 1
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 8
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 6
- 238000004821 distillation Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- CDULGHZNHURECF-UHFFFAOYSA-N 2,3-dimethylaniline 2,4-dimethylaniline 2,5-dimethylaniline 2,6-dimethylaniline 3,4-dimethylaniline 3,5-dimethylaniline Chemical class CC1=CC=C(N)C(C)=C1.CC1=CC=C(C)C(N)=C1.CC1=CC(C)=CC(N)=C1.CC1=CC=C(N)C=C1C.CC1=CC=CC(N)=C1C.CC1=CC=CC(C)=C1N CDULGHZNHURECF-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 150000001896 cresols Chemical class 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 150000004992 toluidines Chemical class 0.000 description 1
- 230000007306 turnover Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 150000003739 xylenols Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/04—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups
- C07C209/14—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups by substitution of hydroxy groups or of etherified or esterified hydroxy groups
- C07C209/18—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups by substitution of hydroxy groups or of etherified or esterified hydroxy groups with formation of amino groups bound to carbon atoms of six-membered aromatic rings or from amines having nitrogen atoms bound to carbon atoms of six-membered aromatic rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung von Diarylaminen In der Patentschrift 1 031796 ist ein Verfahren beschrieben, nach dem man N-alkylierte aromatische Amine dadurch herstellen kann, daß man ein aromatisches Amin und einen Alkohol oder Dimethyläther gemeinsam durch auf eine Temperatur oberhalb der Siedepunkte der Reaktionskomponenten erhitzte Phosborsäure leitet.Process for the preparation of diarylamines In patent specification 1 031796 describes a process by which N-alkylated aromatic amines can be prepared by an aromatic amine and an alcohol or dimethyl ether together by to a temperature above the boiling point of the reaction components heated phosphoric acid conducts.
Es wurde nun gefunden, daß sich dieses Verfahren vorteilhaft auch zur Umsetzung aromatischer Amine mit Phenolen zu Diarylaminen anwenden läßt. It has now been found that this process is also advantageous can be used to convert aromatic amines with phenols to diarylamines.
Das neue Verfahren besteht somit darin, ein aromatisches Amin und ein Phenol gemeinsam durch auf eine Temperatur oberhalb der Siedepunkte der Reaktionskomponenten erhitzte Phosphorsäure zu leiten. The new process thus consists in using an aromatic amine and a phenol together by to a temperature above the boiling point of the reaction components conduct heated phosphoric acid.
Geeignete aromatische Amine sind insbesondere solche, deren Siedepunkt unterhalb etwa 2500 C liegt, z. B. Anilin, die Toluidine und die Xylidine. Suitable aromatic amines are in particular those whose boiling point is below about 2500 C, e.g. B. aniline, the toluidines and the xylidines.
Unter den Phenolen, deren Siedepunkte ebenfalls vorzugsweise unterhalb etwa 2500 C liegen sollen, seien beispielsweise das Phenol, die Kresole und die Xylenole genannt. Among the phenols, whose boiling points are also preferably below should be around 2500 C, for example, the phenol, the cresols and the Called xylenols.
Beispiel In ein Reaktionsgefäß von 18 cm Durchmesser und 300 cm Höhe werden 85 kg eines Gemisches von 25 Gewichtsteilen Anilin und 90 Gewichtsteilen konzentrierter Phosphorsäure eingefüllt. Anschließend wird auf 2500 C aufgeheizt, und bei dieser Temperatur werden 4,5 1 (flüssig) eines verdampften Gemisches von 1 Gewichtsteil Phenol und 2,5 Gewichtsteilen Anilin pro Stunde durch die Phosphorsäure hindurchgeleitet. Das Reaktionsgemisch, das kontinuierlich oder diskontinuierlich destillativ aufgearbeitet werden kann, enthält 7,50/0 Diphenylamin, entsprechend einem Umsatz von 14,50/0. Im Destillationsvorlauf findet sich das Reaktionswasser. Das Diphenylamin fällt schon ohne Reindestillation in gelber Farbe an und zeigt einen Erstarrungspunkt von 530 C. Example In a reaction vessel with a diameter of 18 cm and a height of 300 cm 85 kg of a mixture of 25 parts by weight of aniline and 90 parts by weight are concentrated phosphoric acid. Then it is heated to 2500 C, and at this temperature 4.5 l (liquid) of an evaporated mixture of 1 part by weight of phenol and 2.5 parts by weight of aniline per hour by the phosphoric acid passed through. The reaction mixture, which is continuous or discontinuous Can be worked up by distillation, contains 7.50 / 0 diphenylamine, accordingly a turnover of 14.50 / 0. The water of reaction is found in the distillation head. The diphenylamine is obtained in yellow color even without pure distillation and shows a freezing point of 530 C.
Erhöht man die Reaktionstemperatur auf etwa 2700 C, so steigt der Diphenylamingehalt auf 150/0, entsprechend einem Umsatz von 290/0. If the reaction temperature is increased to about 2700 ° C., the temperature rises Diphenylamine content to 150/0, corresponding to a conversion of 290/0.
Bei Verdoppelung der Verweilzeit im Reaktionsgefäß dadurch, daß man z. B. das Reaktionsgefäß vergrößert oder daß man ein einmal durchgesetztes Gemisch noch ein zweites Mal durchsetzt, erhält man bei 2700 C Reaktionstemperatur ein Reaktionsgemisch mit einem Gehalt von 26 bis 27 °/o Diphenylamin, was einem Umsatz von etwa 55 55°/o entspricht. When doubling the residence time in the reaction vessel by the fact that z. B. enlarges the reaction vessel or that you have a mixture that has been enforced once permeated a second time, a reaction mixture is obtained at a reaction temperature of 2700.degree with a content of 26 to 27% diphenylamine, which corresponds to a conversion of about 55 55% is equivalent to.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF24590A DE1055540B (en) | 1957-12-10 | 1957-12-10 | Process for the preparation of diarylamines |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF24590A DE1055540B (en) | 1957-12-10 | 1957-12-10 | Process for the preparation of diarylamines |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1055540B true DE1055540B (en) | 1959-04-23 |
Family
ID=7091280
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEF24590A Pending DE1055540B (en) | 1957-12-10 | 1957-12-10 | Process for the preparation of diarylamines |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE1055540B (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3205265A (en) * | 1961-03-23 | 1965-09-07 | Bayer Ag | Process for the production of diphenylamine |
| DE1289530B (en) | 1962-08-10 | 1969-02-20 | Halcon International Inc | Process for the preparation of aminobenzenes |
-
1957
- 1957-12-10 DE DEF24590A patent/DE1055540B/en active Pending
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3205265A (en) * | 1961-03-23 | 1965-09-07 | Bayer Ag | Process for the production of diphenylamine |
| DE1289530B (en) | 1962-08-10 | 1969-02-20 | Halcon International Inc | Process for the preparation of aminobenzenes |
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