Patent US4105657A successfully refreshed from Google Patents.
← Back to Patent Explorer
US4105657A Expired / Lapsed US ⏱️ 0.0 years remaining

Production of n-alkyl derivatives of cyclic alkylenimines

Assignee: BASF SE
•
Filing: 1977-04-08
•
Granted: 1978-08-08
•
Expires: 1997-04-08
📄 Original PDF 🌐 Google Patents 🔄 Sync Now

Abstract

Abstract Production of N-alkylated cyclic alkylenimines by reaction of cyclic alkylenimines with an alcohol or ether in the gas phase in the presence of a high-area SiO 2 /P 2 O 5 catalyst.

Inventors

  • 👤 Toni Dockner
  • 👤 Herbert Toussaint
  • 👤 Martin Decker

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-08 18:44
CPC Classifications
C; C07; C07D; C07D279/00; C07D279/04; B; B01; B01J; B01J27/00; B01J27/14; B01J27/16

Claims Analysis

Total Claims: 5
Claim 1
Independent Claim 217 words
In a process for the production of an N-alkylated cyclic amine of the formula ##STR3## wherein R is an alkyl radical selected from the group consisting of methyl, ethyl and isopropyl, by reacting in the gas phase at a temperature of from 150° to 350° C an alcohol selected from the group consisting of methanol, ethanol and isopropanol or an ether selected from the group consisting of dimethyl ether, diethyl ether and diisopropyl ether with a cyclic amine of the formula ##STR4## said latter amine being selected from the group consisting of pyrrolidine, 1-methylimidazolidine, oxazolidine, thiazolidine, dihydroisoindole, piperidine, 3-propylpiperidine, piperazine, N-methylpiperazine, perhydro-(1,3)-oxazine, perhydro-(1,3)-thiazine, hexamethylenimine, perhydrothiazepine, decamethylenimine, 3,5-dimethylmorpholine, and morpholine, in the presence of a catalyst containing a phosphorus compound on a carrier, the improvement which comprises carrying out said reaction in the presence of a silicon dioxide catalyst having a specific surface area of from 50 to 500 m 2 /g and containing from 0.1 to 20% by weight of phosphoric acid, said catalyst being obtained by converting an aqueous colloidal sodium silicate solution by addition of sulfuric acid to a silicic acid hydrogel, desalting said hydrogel with ammoniacal water, adding oxalic acid and an appropriate amount of phosphoric acid, milling the mixture so obtained until peptization takes place and spray drying to give a particulate powder.
Claim 2
Dependent Claim 217 words
In a process for the production of an N-alkylated cyclic amine of the formula ##STR3## wherein R is an alkyl radical selected from the group consisting of methyl, ethyl and isopropyl, by reacting in the gas phase at a temperature of from 150° to 350° C an alcohol selected from the group consisting of methanol, ethanol and isopropanol or an ether selected from the group consisting of dimethyl ether, diethyl ether and diisopropyl ether with a cyclic amine of the formula ##STR4## said latter amine being selected from the group consisting of pyrrolidine, 1-methylimidazolidine, oxazolidine, thiazolidine, dihydroisoindole, piperidine, 3-propylpiperidine, piperazine, N-methylpiperazine, perhydro-(1,3)-oxazine, perhydro-(1,3)-thiazine, hexamethylenimine, perhydrothiazepine, decamethylenimine, 3,5-dimethylmorpholine, and morpholine, in the presence of a catalyst containing a phosphorus compound on a carrier, the improvement which comprises carrying out said reaction in the presence of a silicon dioxide catalyst having a specific surface area of from 50 to 500 m 2 /g and containing from 0.1 to 20% by weight of phosphoric acid, said catalyst being obtained by converting an aqueous colloidal sodium silicate solution by addition of sulfuric acid to a silicic acid hydrogel, desalting said hydrogel with ammoniacal water, adding oxalic acid and an appropriate amount of phosphoric acid, milling the mixture so obtained until peptization takes place and spray drying to give a particulate powder.
Claim 3
Dependent Claim 20 words
A process as set forth in claim 1, wherein the catalyst has been obtained by spray drying with smoke gas.
Claim 4
Dependent Claim 23 words
A process as set forth in claim 1 whrein the compound of the formula ##STR5## reacted is morpholine, 3,5-dimethylmorpholine, piperazine, hexamethylenimine or pyrrolidine.
Claim 5
Dependent Claim 27 words
A process as set forth in claim 1 wherein the catalyst is a fluidized bed catalyst having an average particle size of from 60 to 1000 microns.

References Cited (Backward Citations)

US2073671A Cited
US3112317A Cited
US3652581A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1981-08-07 1982-02-06 1982-08-08 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1985-08-07 1986-02-06 1986-08-08 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1989-08-07 1990-02-06 1990-08-08 $7700.00 Window Closed / Lapsed

Assigned Categories & Tags

No categories assigned to this patent yet.

Assign Category Tag