# US 2022/0033262 A1 · Synthesis of ammonium dinitramide (adn) > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 2022/0033262 A1 - Document ID: US20220033262A1 - Status: Published application - Kind: A1 - Application number: 17/276,513 - Filed: 2018-09-17 - Published: 2022-02-03 - Earliest claimed: 2018-09-17 - Assignees: Totalforsvarets Forskningsinstitut - Applicants: TotalföRsvarets Forskningsinstitut - Inventors: Stefan EK; Jonas JOHANSSON - Web page: https://patentgrep.com/patent/US20220033262A1 ## CPC - C01B 21/087: containing one or more hydrogen atoms - B01D 9/0054: {Use of anti-solvent} - C07C 277/08: of substituted guanidines - B01D 2009/0086: {Processes or apparatus therefor} - C01B: NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; {METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C} - B01D: SEPARATION (separating solids from solids by wet methods B03B, B03D; by pneumatic jigs or tables B03B; by other dry methods B07; magnetic or electrostatic separation of solid materials from solid materials or fluids, separation by high-voltage electric fields B03C; centrifuges, vortex apparatus B04; presses per se for squeezing-out liquid from liquid-containing material B30B9/02; treatment of water C02F, e.g. softening by ion-exchange C02F1/42; {arrangements of air intake cleaners in gas turbine plants F02C7/05} ; arrangements or mounting of filters in air-conditioning, air-humidification or ventilation F24F13/28) - C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS ## Abstract The invention concerns a method for making ammonium dinitramide from guanylurea dinitramide in one single process step. Guanylurea dinitramide is reacted with an ammonium sulfate in a reaction solution comprising water and acetone and an ion exchange gives ammonium dinitramide. By using acetone the yield is increased compared to known processes as formed guanylurea sulfate is poorly soluable in a water-acetone solution and precipitates, while guanylurea dinitramide has higher solubility in the solution than in only water. The guanylurea sulfate precipitate formed in the reaction solution that contains acetone is less sticky than if formed in water or in a water-alcohol solution and therefore easier to filter off. The use of acetone also allows lower process temperatures to be used than in previously known methods for producing guanylurea dinitramide. Conclusively, the method gives a higher yield, demands considerable smaller amounts of solvent and allows lower process temperatures to be used than in any formerly known process. ## Claims ### Claim 1 Method for producing ammonium dinitramide in which guanylurea dinitramide is reacted with ammonium sulfate in a reaction solution comprising water, and that in said reaction solution ammonium dinitramide and guanylurea sulfate is formed whereby the guanylurea sulfate precipitates characterized in that acetone is added to the reaction solution to increase the precipitation of guanylurea sulfate and also to increase the amount of dissolved guanylurea dinitramide to increase the yield of ammonium dinitramide formed in the reaction solution. ### Claim 2 (depends on 1) Method according to claim 1 characterized in that the reaction solution is filtrated to remove formed precipitated guanylurea sulfate and that the filtrate is concentrated to dryness and then the residue is suspended in acetone whereby the formed ammonium dinitramide is dissolved while any remaining guanylurea dinitramide remains solid and can be filtered off and ammonium dinitramide is obtained by concentration of the filtrate to dryness. ### Claim 3 (depends on 1) Method according to claim 1 characterized in that the reaction solution is filtrated to remove formed precipitated guanylurea sulfate and that the filtrate is concentrated to dryness and then the residue is suspended in 2-propanol whereby the formed ammonium dinitramide is dissolved while any remaining guanylurea dinitramide remains solid and can be filtered off and ammonium dinitramide is obtained by concentration of the filtrate to dryness. ### Claim 4 Method for producing ammonium dinitramide characterized in that guanylurea dinitramide is reacted with ammonium sulfate in a reaction solution comprising water and acetone, in which reaction solution ammonium dinitramide forms and from which solution guanylurea sulfate precipitates. ### Claim 5 (depends on 4) Method according to claim 4 characterized in that the reaction solution is heated and/or refluxed and/or stirred in order to increase the solubility of guanylurea dinitramide and thereby increasing the yield of ammonium dinitramide. ### Claim 6 (depends on 4) Method according to claim 4 characterized in that the reaction solution is cooled to reduce the solubility of the guanylurea sulfate formed and make it precipitate from the reaction solution. ### Claim 7 (depends on 4) Method according to claim 4 characterized in that acetone is added to the reaction solution to reduce the solubility of guanylurea sulfate formed and make it precipitate from the reaction solution. ### Claim 8 (depends on 4) Method according to claim 4 characterized in that the reaction solution is filtrated to remove the precipitated guanylurea sulfate and any possible remaining guanylurea dinitramide and/or ammonium sulfate and that the filtrate, comprising ammonium dinitramide and any remaining guanylurea dinitramide is concentrated to dryness after the filtration. ### Claim 9 (depends on 8) Method according to claim 8 characterized in that the to dryness concentrated filtrate is suspended in acetone whereby the formed ammonium dinitramide is dissolved while any remaining guanylurea dinitramide remains solid and that the solid guanylurea dinitramide is filtered off and that the filtrate is concentrated to dryness whereby ammonium dinitramide is obtained. ### Claim 10 (depends on 8) Method according to claim 8 characterized in that the to dryness concentrated filtrate is suspended in 2-propanol whereby the ammonium dinitramide is dissolved while any remaining guanylurea dinitramide remains solid and can be filtered off and that the filtrate is concentrated to dryness whereby ammonium dinitramide is obtained. ### Claim 11 (depends on 1) Method for producing ammonium dinitramide according to claim 1 characterized in that the acetone in the reaction solution is removed by distillation, whereafter 2-propanol is added to the residue, whereafter the residue with added 2-propanol is concentrated to dryness, whereafter 2-propanol is added to dissolve the formed ammonium dinitramide and any undissolved particles can be filtered off and ammonium dinitramide is obtained from the filtrate by concentrating it to dryness. ### Claim 12 (depends on 1) Method for producing ammonium dinitramide according to claim 1 characterized in that that the acetone in the reaction solution is removed by distillation, whereafter 2-propanol is added to the residue, whereafter the residue with added 2-propanol is evaporated to remove any remaining water, whereafter the residue is filtrated to remove any undissolved particles and ammonium dinitramide is obtained from the filtrate by concentrating it to dryness. ### Claim 13 (depends on 1) Method according to claim 1 characterized in that the reaction solution is filtrated to remove formed precipitated guanylurea sulfate and that the filtrate is concentrated to dryness and then the residue is suspended in acetone whereby the formed ammonium dinitramide is dissolved while any remaining guanylurea dinitramide remains solid and can be filtered off and ammonium dinitramide is obtained by concentration of the filtrate to such an extent that ammonium dinitramide precipitates, either directly or upon cooling of the solution, and is obtained by filtration and drying of the resulting filter cake. ### Claim 14 (depends on 1) Method according to claim 1 characterized in that the reaction solution is filtrated to remove formed precipitated guanylurea sulfate and that the filtrate is concentrated to dryness and then the residue is suspended in 2-propanol whereby the formed ammonium dinitramide is dissolved while any remaining guanylurea dinitramide remains solid and can be filtered off and ammonium dinitramide is obtained by concentration of the filtrate to such an extent that ammonium dinitramide precipitates, either directly or upon cooling of the solution, and is obtained by filtration and drying of the resulting filter cake. ### Claim 15 (depends on 8) Method according to claim 8 characterized in that the to dryness concentrated filtrate is suspended in acetone whereby the formed ammonium dinitramide is dissolved while any remaining guanylurea dinitramide remains solid and that the solid guanylurea dinitramide is filtered off and that ammonium dinitramide is obtained by concentration of the filtrate to such an extent that ammonium dinitramide and any remaining guanylurea dinitramide precipitates, either directly or upon cooling of the solution, and are obtained by filtration and drying of the resulting filter cake. ### Claim 16 (depends on 8) Method according to claim 8 characterized in that the to dryness concentrated filtrate is suspended in 2-propanol whereby the ammonium dinitramide is dissolved while any remaining guanylurea dinitramide remains solid and can be filtered off and that ammonium dinitramide is obtained by concentration of the filtrate to such an extent that ammonium dinitramide precipitates, either directly or upon cooling of the solution, and is obtained by filtration and drying of the resulting filter cake. ### Claim 17 (depends on 1) Method for producing ammonium dinitramide according to claim 1 characterized in that that the acetone in the reaction solution is removed by distillation, whereafter 2-propanol is added to the residue, whereafter the residue with added 2-propanol is concentrated to dryness, whereafter 2-propanol is added to dissolve the formed ammonium dinitramide and any undissolved particles can be filtered off and ammonium dinitramide is obtained by concentration of the filtrate to such an extent that ammonium dinitramide precipitates, either directly or upon cooling of the solution, and is obtained by filtration and drying of the resulting filter cake. ### Claim 18 (depends on 1) Method for producing ammonium dinitramide according to claim 1 characterized in that that the acetone in the reaction solution is removed by distillation, whereafter 2-propanol is added to the residue, whereafter the residue with added 2-propanol is evaporated to remove any remaining water, whereafter the residue is filtrated to remove any undissolved particles and ammonium dinitramide is obtained by concentration of the filtrate to such an extent that ammonium dinitramide precipitates, either directly or upon cooling of the solution, and is obtained by filtration and drying of the resulting filter cake. ### Claim 19 (canceled)