DE1135888B - Process for making urethanes - Google Patents

Process for making urethanes

Info

Publication number
DE1135888B
DE1135888B DEF29887A DEF0029887A DE1135888B DE 1135888 B DE1135888 B DE 1135888B DE F29887 A DEF29887 A DE F29887A DE F0029887 A DEF0029887 A DE F0029887A DE 1135888 B DE1135888 B DE 1135888B
Authority
DE
Germany
Prior art keywords
acid
reaction
urethanes
dimethylaminomethyl
hydroxyl group
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
DEF29887A
Other languages
German (de)
Inventor
Dr Engelbert Kuehle
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.)
Bayer AG
Original Assignee
Bayer 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
Priority to BE585318D priority Critical patent/BE585318A/xx
Priority to US3125598D priority patent/US3125598A/en
Priority to NL246083D priority patent/NL246083A/xx
Priority to DEF27209A priority patent/DE1132117B/en
Application filed by Bayer AG filed Critical Bayer AG
Priority to DEF29887A priority patent/DE1135888B/en
Priority to GB41374/59A priority patent/GB906183A/en
Priority to FR812226A priority patent/FR1250683A/en
Publication of DE1135888B publication Critical patent/DE1135888B/en
Pending legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
    • C07C271/06—Esters of carbamic acids

Landscapes

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

Description

Verfahren zur Herstellung von Urethanen Die Patentanmeldung F 27 209 IVb/12o betrifft ein Verfahren zur Herstellung von Urethanen, das darin besteht, daß man gegebenenfalls weitersubstituierte aromatische Verbindungen, die im Kern wenigstens eine Hydroxylgruppe enthalten und die in o- und/oder p-Stellung zur Hydroxylgruppe wenigstens eine tertiäre Aminomethylgruppe enthalten, mit Isocyanaten umsetzt.Process for the production of urethanes The patent application F 27 209 IVb / 12o relates to a process for the production of urethanes, which consists in that one optionally further substituted aromatic compounds in the core contain at least one hydroxyl group and those in the o- and / or p-position to the hydroxyl group contain at least one tertiary aminomethyl group, reacts with isocyanates.

Der Reaktionsverlauf dieses Verfahrens ist aus folgendem Formelschema am Beispiel der Umsetzung von 2,4,6-Tris-(dimethylaminomethyl)-phenol mit Phenylisocyanat ersichtlich: Es wurde gefunden, daß man stabile Salze organischer Säuren dieser Methane in einfacher Weise dadurch erhält, wenn man diese Umsetzung der basisch substituierten Phenole mit Isocyanaten in niederen, gegebenenfalls substituierten aliphatischen Carbonsäuren ausführt. Nach der Entfernung des überschüssigen Carbonsäureanteils z. B. durch Destillation bleiben die Carbamidsäureester in Form ihrer fettsauren Salze, zumeist als zähflüssige Öle, zurück.The course of the reaction of this process can be seen from the following equation using the example of the reaction of 2,4,6-tris (dimethylaminomethyl) phenol with phenyl isocyanate: It has been found that stable organic acid salts of these methanes are obtained in a simple manner by carrying out this reaction of the basic substituted phenols with isocyanates in lower, optionally substituted aliphatic carboxylic acids. After removing the excess carboxylic acid z. B. by distillation, the carbamic acid esters remain in the form of their fatty acid salts, mostly as viscous oils.

Als für diese Reaktion besonders geeignete aliphatische Carbonsäuren beispielsweise sind Ameisensäure, Essigsäure, Propionsäure, Methoxyessigsäure, die chlorierten Essigsäuren, Fumarsäure, Milchsäure und ähnliche zu erwähnen.Aliphatic carboxylic acids particularly suitable for this reaction for example, formic acid, acetic acid, propionic acid, methoxyacetic acid, the to mention chlorinated acetic acids, fumaric acid, lactic acid and the like.

Man führt die vorbeschriebene Reaktion im allgemeinen bei Raumtemperatur oder schwach erhöhter Temperatur durch. Es ist auch möglich, ein Lösungsmittelgemisch aus einer niederen aliphatischen Carbonsäure und einem anderen beliebigen organischen Lösungsmittel, wie Aceton, Dioxan, Benzol für die Umsetzung zu verwenden.The above-described reaction is generally carried out at room temperature or slightly elevated temperature. It is also possible to use a mixed solvent from a lower aliphatic carboxylic acid and any other organic Use solvents such as acetone, dioxane, benzene for the reaction.

Beispiel 1 40g 1-(Dimethylaminomethyl)-2-naphthol werden in 100 ml Eisessig gelöst und bei etwa 45°C mit 24 g Phenylisocyanat tropfenweise versetzt. Hierbei steigt die Temperatur auf etwa 50°C an. Man rührt kurze Zeit nach, destilliert die überschüssige Essigsäure im Vakuum ab und erhält als Rückstand 73 g des N-Phenylcarbamidsäure-2- [(1-dimethylaminomethyl)-naphthyl]-esters in Form des Acetats.Example 1 40 g of 1- (dimethylaminomethyl) -2-naphthol are in 100 ml Dissolved glacial acetic acid and treated with 24 g of phenyl isocyanate dropwise at about 45 ° C. The temperature rises to around 50 ° C. The mixture is subsequently stirred for a short time and distilled the excess acetic acid in vacuo and 73 g of N-phenylcarbamic acid-2- [(1-dimethylaminomethyl) naphthyl] ester in the form of the acetate.

Beispiel 2 40 g 1-(Dimethylaminomethyl)-2-naphthol werden in 100 ml Eisessig gelöst und bei etwa 45°C mit der Lösung von 31 g p-Chlorphenylisocyanat in 20 ml Aceton versetzt. Die Temperatur steigt auf 48°C an. Man destilliert das Lösungsmittel im Vakuum ab und erhält 72 g des N-(p-Chlorphenyl)-carbamidsäure-2-[(1-dimethylaminomethyl)-naphthyl]-esters in Form des Acetats.Example 2 40 g of 1- (dimethylaminomethyl) -2-naphthol are dissolved in 100 ml of glacial acetic acid, and a solution of 31 g of p-chlorophenyl isocyanate in 20 ml of acetone is added at about 45 ° C. The temperature rises to 48 ° C. The solvent is distilled off in vacuo and 72 g of N- (p-chlorophenyl) carbamic acid 2 - [(1-dimethylaminomethyl) naphthyl] ester are obtained in the form of the acetate.

Beispiel 3 35,8 g 3,5-Dimethyl-6-(dimethylaminomethyl)-phenol werden bei 40°C in 80 ml Eisessig gelöst und mit der Lösung von 31 g p-Chlorphenyl-isocyanat in 20 ml Aceton versetzt. Nach Abdampfen des überschüssigen Lösungsmittels erhält man 72 g N-(p-Chlorphenyl)-carbamidsäure - [3,5 - dimethyl - 6 - (dimethylaminomethyl)-phenyl]-ester als Acetat.Example 3 35.8 g of 3,5-dimethyl-6- (dimethylaminomethyl) phenol become dissolved in 80 ml of glacial acetic acid at 40 ° C. and mixed with the solution of 31 g of p-chlorophenyl isocyanate added in 20 ml of acetone. Obtained after evaporation of the excess solvent 72 g of N- (p-chlorophenyl) carbamic acid - [3,5 - dimethyl - 6 - (dimethylaminomethyl) phenyl] ester as acetate.

Claims (1)

PATENTANSPRUCH: Weitere Ausbildung des Verfahrens zur Herstellung von Urethanen durch die Umsetzung von gegebenenfalls weiter substituierten aromatischen Verbindungen, die im Kern wenigstens eine Hydroxylgruppe enthalten, und die in o- und/oder p-Stellung zur Hydroxylgruppe wenigstens .eine tertiäre Aminomethylgruppe enthalten, mit Isocyanaten nach Patentanmeldung F 27 209 IVb/12o, dadurch gekennzeichnet, daß die Umsetzung in niederen aliphatischen Carbonsäuren durchgeführt wird.PATENT CLAIM: Further training of the manufacturing process of urethanes through the conversion of optionally further substituted aromatic Compounds which contain at least one hydroxyl group in the core, and which in o- and / or at least one tertiary aminomethyl group p to the hydroxyl group contain, with isocyanates according to patent application F 27 209 IVb / 12o, characterized in, that the reaction is carried out in lower aliphatic carboxylic acids.
DEF29887A 1958-12-06 1959-11-20 Process for making urethanes Pending DE1135888B (en)

Priority Applications (7)

Application Number Priority Date Filing Date Title
BE585318D BE585318A (en) 1958-12-06
US3125598D US3125598A (en) 1958-12-06 Dialkylaminoaryl arylcarbamates
NL246083D NL246083A (en) 1958-12-06
DEF27209A DE1132117B (en) 1958-12-06 1958-12-06 Process for making urethanes
DEF29887A DE1135888B (en) 1959-11-20 1959-11-20 Process for making urethanes
GB41374/59A GB906183A (en) 1958-12-06 1959-12-04 New esters of n-substituted carbamic acids
FR812226A FR1250683A (en) 1958-12-06 1959-12-05 Manufacture of condensation products of aromatic compounds and isocyanates

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEF29887A DE1135888B (en) 1959-11-20 1959-11-20 Process for making urethanes

Publications (1)

Publication Number Publication Date
DE1135888B true DE1135888B (en) 1962-09-06

Family

ID=7093500

Family Applications (1)

Application Number Title Priority Date Filing Date
DEF29887A Pending DE1135888B (en) 1958-12-06 1959-11-20 Process for making urethanes

Country Status (1)

Country Link
DE (1) DE1135888B (en)

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