# US 4,394,524 A · Preparation of polyalkylene polyamines from ammonia, alkyleneamine, and alkanolamine > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 4,394,524 A - Document ID: US4394524A - Status: Granted - Kind: A - Application number: 06/297,687 - Filed: 1981-08-31 - Granted: 1983-07-19 - Earliest claimed: 1981-08-31 - Assignees: Air Products and Chemicals, Inc. - Inventors: Michael E. Ford; Thomas A. Johnson - Web page: https://patentgrep.com/patent/US4394524A ## CPC - C07C 209/16: with formation of amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings - Y02P 20/582: Recycling of unreacted starting or intermediate materials - C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS - Y02P: CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS ## Abstract A process for preparing noncyclic polyalkylene polyamine compounds is disclosed wherein ammonia, an alkylene polyamine compound and an alkanolamine compound are reacted in the presence of an effective amount of a phosphorus-containing substance or a salt of a sulfur-containing substance or its corresponding acid at a temperature from about 200.degree. to 350.degree. C. under a pressure sufficient to maintain the reaction mixture essentially in liquid phase. The polyalkylene polyamines thus formed are recovered from the reaction mixture. ## Claims ### Claim 1 A process for preparing a noncyclic polyalkylene polyamine which comprises: contacting ammonia, an alkyleneamine compound having two primary amino groups of the general formula: ##STR4## wherein R is hydrogen or a lower alkyl (C.sub.1 -C.sub.4) radical, x is a number from 2 to about 6, and y is a number from 1 to about 4, and an alkanolamine compound having primary or secondary hydroxyl groups of the general formula: ##STR5## wherein R is hydrogen or a lower alkyl (C.sub.1 -C.sub.4) radical, x is a number from 2 to about 6, and y is a number from 0 to about 3; in the presence of an effective amount of a phosphorus-containing substance or a salt of a sulfur-containing substance, or the corresponding acid, at a temperature sufficient to effect reaction between the ammonia, the alkyleneamine compound and the alkanolamine compound under a pressure sufficient to maintain the reaction mixture essentially in liquid phase. ### Claim 2 (depends on 1) The process of claim 1 wherein the ammonia, alkyleneamine and alkanolamine are contacted in the presence of a phosphorus-containing substance which is 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 the alkyl groups have from 1 to about 8 carbon atoms and the aryl groups have from about 6 to about 20 carbon atoms, alkaline metal monosalts of phosphoric acid and mixtures of any of the above. ### Claim 3 (depends on 2) The process of claim 2 wherein the phosphorus-containing substance is an acidic metal phosphate. ### Claim 4 (depends on 2) The process of claim 2 wherein the phosphorus-containing substance is boron phosphate. ### Claim 5 (depends on 2, 3, 4) The process of claims 2, 3 or 4 wherein the level of phosphorus-containing substance is from about 0.1 to 25 mole percent based on alkyleneamine and alkanolamine present in the reaction mixture. ### Claim 6 (depends on 5) The process of claim 5 wherein the level of phosphorus-containing substance is from about 0.1 to 10 mole percent. ### Claim 7 (depends on 5) The process of claim 5 wherein the temperature is from about 200.degree. to 350.degree. C. ### Claim 8 (depends on 7) The process of claim 7 wherein the mole ratio of alkyleneamine to alkanolamine is from 5:1 to 1:5. ### Claim 9 (depends on 7) The process of claim 7 wherein the mole ratio of alkyleneamine to alkanolamine to ammonia is from 1-2:1-2:1-10. ### Claim 10 (depends on 9) The process of claim 9 wherein the alkyleneamine is ethylenediamine and the alkanolamine is monoethanolamine. ### Claim 11 (depends on 1) The process of claim 1 wherein the ammonia, alkyleneamine and alkanolamine are contacted in the presence of a salt of a sulfur-containing substance. ### Claim 12 (depends on 11) The process of claim 11 wherein the sulfur-containing substance is an inorganic sulfate. ### Claim 13 (depends on 12) The process of claim 12 wherein the inorganic sulfate is a sulfate of a Group I, II, IIIa, IV, VIb or VIIIb metal. ### Claim 14 (depends on 13) The process of claim 13 wherein the sulfate is beryllium sulfate, boron sulfate or ammonium sulfate. ### Claim 15 (depends on 11, 12, 13, 14) The process of claims 11, 12, 13 or 14 wherein the level of sulfur-containing substance is from about 0.1 to 25 mole percent based on alkyleneamine and alkanolamine present in the reaction mixture. ### Claim 16 (depends on 15) The process of claim 15 wherein the level of the sulfur-containing substance is from about 0.1 to 10 mole percent. ### Claim 17 (depends on 15) The process of claim 15 wherein the temperature is from about 200.degree. to 350.degree. C. ### Claim 18 (depends on 17) The process of claim 17 wherein the mole ratio of alkyleneamine to alkanolamine is from 5:1 to 1:5. ### Claim 19 (depends on 17) The process of claim 17 wherein the ratio of alkyleneamine to alkanolamine to ammonia is from 1-2:1-2:1-10. ### Claim 20 (depends on 19) The process of claim 19 wherein the alkyleneamine is ethylenediamine and the alkanolamine is monoethanolamine. ### Claim 21 A process for preparing a noncyclic polyethylene polyamine which comprises: contacting ethylenediamine, monoethanolamine and ammonia in the presence of an effective amount of a phosphorus-containing substance at a temperature from about 200.degree. to 350.degree. C. under at least that pressure which is sufficient to maintain the reaction essentially in liquid phase; and recovering a noncyclic polyethyelene polyamine. ### Claim 22 A process for preparing a non-cyclic polyethylene polyamine which comprises: contacting ethylenediamine, monoethanolamine and ammonia in the presence of an effective amount of a salt of a sulfur-containing substance at a temperature from about 200.degree. to 350.degree. C. under at least that pressure which is sufficient to maintain the reaction essentially in liquid phase; and recovering a noncyclic polyethylene polyamine.