# US 11,078,151 B2 · Process for the preparation of stable toluene diamine residue/water blends, related compositions, and methods of using such blends as a fuel > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 11,078,151 B2 - Document ID: US11078151B2 - Status: Granted - Kind: B2 - Application number: 16/478,181 - Filed: 2018-01-24 - Published: 2019-12-05 - Granted: 2021-08-03 - Earliest claimed: 2017-01-27 - Assignees: Covestro LLC - Applicants: Covestro LLC - Inventors: James William Colbert; Mamadou Yaya Barry; Jeremy Garrett; Ravindra S. Kamath - Web page: https://patentgrep.com/patent/US11078151B2 ## CPC - C07C 209/90: Stabilisation; Use of additives - C07C 209/36: by reduction of nitro groups bound to carbon atoms of six-membered aromatic rings {in presence of hydrogen-containing gases and a catalyst} - C10L 1/328: {Oil emulsions containing water or any other hydrophilic phase} - F23G 5/02: with pretreatment - F23G 7/04: of waste liquors, e.g. sulfite liquors - C10L 2200/0259: Nitrogen containing compounds - C10L 2290/141: of additive or catalyst - C10L 2290/24: Mixing, stirring of fuel components - C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS - C10L: FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS - F23G: CREMATION FURNACES; CONSUMING WASTE PRODUCTS BY COMBUSTION ## Abstract Processes for stabilizing toluenediamine residues are disclosed. These processes include adding a low viscosity, low boiling liquid to a toluenediamine residue composition to form a blend, and optionally, continuously monitoring the viscosity of the blend during addition of the low viscosity, low boiling liquid. The low viscosity, low boiling liquid may be added at 5% to 30% by weight based on the total weight of the blend. Further, the low viscosity, low boiling liquid may be added so that the blend has a viscosity of 10,000 cP or less throughout the temperature range of 40° C. to 95° C. Blends of toluenediamine residue compositions and low viscosity, low boiling liquids such as water, and methods of their use as a fuel are also disclosed. ## Claims ### Claim 1 A process for stabilizing toluenediamine residues, the process comprising: adding a low viscosity, low boiling liquid to a toluenediamine residue composition to form a blend, wherein the blend comprises 5 to 30% by weight of the low viscosity, low boiling liquid, based on the total weight of the blend, and wherein the blend has a viscosity of 10,000 cP or less throughout the temperature range of 40° C. to 95° C., and wherein the toluenediamine residue composition comprises: (a) 25 to 60% by weight of toluenediamine residue and 40 to 75% by weight of meta-toluenediamine isomer, based on the total weight of the toluene diamine residue and the meta-toluenediamine isomer in the composition; (b) 25 to 60% by weight of toluenediamine residue and 40 to 75% by weight of ortho-toluenediamine isomer, based on the total weight of the toluenediamine residue and the ortho-toluenediamine isomer in the composition; or (c) 25 to 60% by weight of toluenediamine residue and 40 to 75% by weight of a mixture of meta-toluenediamine and ortho-toluenediamine isomers, based on the total weight of the toluenediamine residue and the mixture of meta-toluenediamine and ortho-toluenediamine isomers in the composition. ### Claim 2 (depends on 1) The process of claim 1, further comprising: continuously monitoring the viscosity of the blend during addition of the low viscosity, low boiling liquid; and controlling an amount of toluenediamine residue composition and/or controlling an amount of the low viscosity, low boiling liquid added based on the viscosity of the blend. ### Claim 3 (depends on 2) The process of claim 2, further comprising passing the blend through a heat exchanger to bring the temperature of the blend to a target temperature range for use as a liquid fuel. ### Claim 4 (depends on 1) The process of claim 1, wherein the blend has a viscosity of 4,000 cP or less throughout the temperature range of 40° C. to 95° C. ### Claim 5 (depends on 1) The process of claim 1, wherein the blend has a viscosity of 2,000 cP or less throughout the temperature range of 40° C. to 95° C. ### Claim 6 (depends on 1) The process of claim 1, wherein the low viscosity, low boiling liquid comprises water. ### Claim 7 (depends on 6) The process of claim 6, wherein the water comprises water recovered during crude toluenediamine purification to isolate meta-toluenediamine. ### Claim 8 (depends on 6) The process of claim 6, wherein the amount of water in the blend is 10 to 20% by weight, based on the total weight of the blend. ### Claim 9 (depends on 1) The process of claim 1, wherein the toluenediamine residue composition comprises a mixture of toluenediamine isomers and toluenediamine residues, wherein the toluenediamine residues comprise compounds formed during toluenediamine synthesis that have a higher boiling point than the 2,6 TDA isomer. ### Claim 10 A blended composition comprising: 70 to 95% by weight of a toluenediamine residue composition; and 5 to 30% by weight of a low viscosity, low boiling liquid, wherein the weight percents are based on the total weight of the composition, wherein the blended composition has a viscosity of 10,000 cP or less throughout the temperature range of 40° C. to 95° C., and wherein the toluenediamine residue composition comprises: (a) 25 to 60% by weight of toluenediamine residue and 40 to 75% by weight of meta-toluenediamine isomer, based on the total weight of the toluene diamine residue and the meta-toluenediamine isomer in the composition; (b) 25 to 60% by weight of toluenediamine residue and 40 to 75% by weight of ortho-toluenediamine isomer, based on the total weight of the toluenediamine residue and the ortho-toluenediamine isomer in the composition; or (c) 25 to 60% by weight of toluenediamine residue and 40 to 75% by weight of a mixture of meta-toluenediamine and ortho-toluenediamine isomers, based on the total weight of the toluenediamine residue and the mixture of meta-toluenediamine and ortho-toluenediamine isomers in the composition. ### Claim 11 (depends on 10) The blended composition of claim 10, wherein the blended composition has a viscosity of 4,000 cP or less throughout the temperature range of 40° C. to 95° C. ### Claim 12 (depends on 10) The blended composition of claim 10, wherein the blended composition has a viscosity of 2,000 cP throughout the temperature range of 40° C. to 95° C. ### Claim 13 (depends on 10) The blended composition of claim 10, wherein the toluenediamine residue composition comprises a mixture of toluenediamine isomers and toluenediamine residues, wherein the toluenediamine residues comprise compounds formed during toluenediamine synthesis that have a higher boiling point than the 2,6-TDA isomer. ### Claim 14 (depends on 10) The blended composition of claim 10, wherein the low viscosity, low boiling liquid comprises water. ### Claim 15 (depends on 14) The blended composition of claim 14, comprising 80 to 90% by weight of the toluenediamine residue composition and 10 to 20% by weight water. ### Claim 16 A method of using a toluenediamine residue composition, the method comprising: (a) feeding a blend comprising the toluenediamine residue composition to a fuel burning apparatus, wherein the blend comprises 70 to 95% by weight of the toluenediamine residue composition and 5 to 30% by weight of a low viscosity, low boiling liquid, wherein the weight percents are based on the total weight of the blend; and (b) burning the blend in the fuel burning apparatus, wherein the blend has a viscosity of 10,000 cP or less throughout the temperature range of 40° C. to 95° C., and wherein the toluenediamine residue composition comprises: (i) 25 to 60% by weight of toluenediamine residue and 40 to 75% by weight of meta-toluenediamine isomer, based on the total weight of the toluene diamine residue and the meta-toluenediamine isomer in the composition; (ii) 25 to 60% by weight of toluenediamine residue and 40 to 75% by weight of ortho-toluenediamine isomer, based on the total weight of the toluenediamine residue and the ortho-toluenediamine isomer in the composition; or (iii) 25 to 60% by weight of toluenediamine residue and 40 to 75% by weight of a mixture of meta-toluenediamine and ortho-toluenediamine isomers, based on the total weight of the toluenediamine residue and the mixture of meta-toluenediamine and ortho-toluenediamine isomers in the composition. ### Claim 17 (depends on 16) The method of claim 16, wherein the toluenediamine residue composition comprises a mixture of toluenediamine isomers and toluenediamine residues, wherein the toluenediamine residues comprise compounds formed during toluenediamine synthesis that have a higher boiling point than the 2,6-TDA residue. ### Claim 18 (depends on 16) The method of claim 16, wherein the blend comprises 80 to 90% by weight of the toluenediamine residue composition and 10 to 20% by weight of the low viscosity, low boiling liquid, wherein the low viscosity, low boiling liquid comprises water and the weight percents are based on the total weight of the blend. ### Claim 19 (depends on 16) The method of claim 16, wherein the blend has a viscosity of 4,000 cP or less throughout the temperature range of 40° C. to 95° C. ### Claim 20 (depends on 16) The method of claim 16, wherein the fuel burning apparatus comprises a boiler, a rotary kiln incinerator, a liquid injection kiln, a fluidized bed kiln, a cement kiln, or a metals forging furnace. ### Claim 21 (depends on 20) The method of claim 20, wherein the fuel burning apparatus is a cement kiln.