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US4044053A Expired / Lapsed US ⏱️ 0.0 years remaining

Preparation of polyalkylene polyamines

Assignee: Texaco Development Corp
•
Filing: 1976-05-03
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Granted: 1977-08-23
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Expires: 1996-05-03
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Abstract

Abstract An improved process for selectively preparing a predominantly noncyclic polyalkylene polyamine compound is disclosed wherein an alkyleneamine compound is contacted with a diol compound in the presence of a catalytically effective amount of a phosphorus-containing substance at a temperature of from about 250° to about 350° C under a pressure sufficient to maintain the mixture essentially in liquid phase and the polyalkylene polyamine is then recovered from the resultant reaction mixture. In a preferred embodiment ethylenediamine is contacted with monoethylene diol to produce a predominantly linear polyethylene polyamine product with very low yields of heterocyclic amine materials. The desired polyethylene polyamines produced can be directly recovered from the reaction products by known purification procedures.

Inventors

  • 👤 Michael E. Brennan
  • 👤 Philip H. Moss
  • 👤 Ernest L. Yeakey

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-26 17:43
CPC Classifications
C; C08; C08G; C08G73/00; C08G73/02; C08G73/0206; Y; Y02; Y02P; Y02P20/00; Y02P20/50; Y02P20/582

Claims Analysis

Total Claims: 9
Claim 1
Independent Claim 223 words
A process for preparing noncyclic polyalkylene polyamines comprising the steps of: contacting an alkyleneamine compound having two primary amino groups of the formula: ##STR4## wherein R is a hydrogen or a lower alkyl, x is a number from 2 to about 6 and y is a number from 1 to about 4 with a diol having primary or secondary hydroxy groups of the general formula: ##STR5## where R is a hydrogen or a lower alkyl; x is a number from 2 to about 6; and y is a number from 0 to about 3 in the presence of a catalytically effective amount of the phosphoruscontaining substance selected from the group consisting of acidic metal phosphates, phosphoric acid compounds and their anhydrides, phosphorous acid compounds and their anhydrides, alkyl or aryl phosphate esters, alkyl or aryl phosphite esters, alkyl or aryl substituted phosphorous acids and phosphoric acids wherein said alkyl groups have from 1 to about 8 carbon atoms and said aryl groups have from 6 to about 20 carbon atoms, alkali metal monosalts of phosphoric acid and mixtures of the above at temperatures of from about 250° to about 350° C under a pressure sufficient to maintain the mixture essentially in liquid phase wherein said alkyleneamine compound is present in molar excess; and, recovering said polyalkylene polyamine compound from the resultant reaction mixture.
Claim 2
Dependent Claim 223 words
A process for preparing noncyclic polyalkylene polyamines comprising the steps of: contacting an alkyleneamine compound having two primary amino groups of the formula: ##STR4## wherein R is a hydrogen or a lower alkyl, x is a number from 2 to about 6 and y is a number from 1 to about 4 with a diol having primary or secondary hydroxy groups of the general formula: ##STR5## where R is a hydrogen or a lower alkyl; x is a number from 2 to about 6; and y is a number from 0 to about 3 in the presence of a catalytically effective amount of the phosphoruscontaining substance selected from the group consisting of acidic metal phosphates, phosphoric acid compounds and their anhydrides, phosphorous acid compounds and their anhydrides, alkyl or aryl phosphate esters, alkyl or aryl phosphite esters, alkyl or aryl substituted phosphorous acids and phosphoric acids wherein said alkyl groups have from 1 to about 8 carbon atoms and said aryl groups have from 6 to about 20 carbon atoms, alkali metal monosalts of phosphoric acid and mixtures of the above at temperatures of from about 250° to about 350° C under a pressure sufficient to maintain the mixture essentially in liquid phase wherein said alkyleneamine compound is present in molar excess; and, recovering said polyalkylene polyamine compound from the resultant reaction mixture.
Claim 3
Dependent Claim 31 words
The process of claim 1, wherein said phosphorus-containing substance is present in an amount of from about 0.1 to about 10.0 weight percent based upon the amount of said diol present.
Claim 4
Dependent Claim 28 words
The process of claim 2, wherein said mixture is heated in the presence of said phosphorus-containing substance at a temperature of from about 275° to about 325° C.
Claim 5
Dependent Claim 26 words
The process of claim 3, wherein said diol compound and said alkyleneamine compound are contacted in a molar ratio of from about 2:1 to about 1:5.
Claim 6
Dependent Claim 57 words
The process of claim 4 wherein said diol is an ethylene diol of the formula: ##STR6## wherein R is hydrogen, x is 2 and y is 0 to 3 and wherein the alkyleneamine is an ethyleneamine of the formula: ##STR7## wherein R is hydrogen, x is 2 and y is a number from 1 to about 4.
Claim 7
Dependent Claim 25 words
The process of claim 5 wherein said ethylene diol is monoethylene diol, wherein said ethyleneamine is ethylenediamine and wherein said phosphorus-containing substance is phosphorous acid.
Claim 8
Dependent Claim 27 words
The process of claim 5 wherein said phosphorus-containing substance is an acid metal phosphate selected from the group consisting of boron phosphate, ferric phosphate and aluminum phosphate.
Claim 9
Dependent Claim 35 words
The process of claim 5 wherein sid phosphorus compound is selected from a group consisting of phenylphosphinic acid, ethylphosphinic acid, phenylphosphonic acid, naphthaphosphonic acid, methylphosphinic acid, methyl phenylphosphinate, dimethyl phenylphosphonate, ethyl phenylphosphinate and propyl methylphosphonate.

References Cited (Backward Citations)

US3121115A Cited
US3387032A Cited
US3520933A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1980-08-22 1981-02-21 1981-08-23 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1984-08-22 1985-02-21 1985-08-23 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1988-08-22 1989-02-21 1989-08-23 $7700.00 Window Closed / Lapsed

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