IP Library › Granted Patent US 12,497,341
Granted Patent B2
US 12,497,341 · App. 19/069,544 · Granted Dec 16, 2025

Reaction methods for producing nitrogenous phosphoryl compounds that are in situ fluid compositions

Inventors: Gary David McKnight (High Point, NC); Randall Linwood Rayborn (Burlington, NC)
Assignee: SOILGENIC TECHNOLOGIES, LLC
C05F3/00C05C3/00C05D9/00C07F9/28
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Quick Facts
Patent No.
US 12,497,341
App. No.
19/069,544
Granted
Dec 16, 2025
Kind
B2
Abstract

A method of making one or more alkyl thiophosphoric triamides.

Claims (58)

1 . A composition comprising:

a) animal waste, and

b) a fluid suspension composition;

wherein said fluid suspension composition comprises: i) one or more reaction products of one or more phosphoryl chloride functionalities reacting with one or more nitrogenous compounds within ii) a reaction medium;

wherein said reaction medium comprises organic liquid system one;

wherein said organic liquid system one comprises one or more aprotic liquids, and

wherein properties of said one or more aprotic liquids are a) boiling point of greater than 160° C., b) have a flashpoint greater than 145° F. c) environmentally safe, d) safe for contact with humans and animals, e) serves as the delivery system or components of a delivery system that delivers the desired nitrogenous compound to the surface of a substrate, f) does not degrade the one or more nitrogenous phosphoryl compounds, and g) are not reactive with said one or more phosphoryl chloride functionalities.

2 . The composition of claim 1 , wherein said one or more reaction products comprise one or more members selected from the group consisting of a) one or more nitrogenous phosphoryl particles, b) one or more chloride salt particles, c) one or more fused particles, and d) combinations thereof.

3 . The composition of claim 2 , wherein said one or more nitrogenous phosphoryl particles comprise one or more urease inhibitor particles.

4 . The composition of claim 3 , wherein said one or more urease inhibitor particles comprise one or more alkyl thiophosphoric triamide particles.

5 . The composition of claim 4 , wherein said one or more alkyl thiophosphoric triamide particles comprise NBPT (N-(n-butyl) thiophosphoric triamide) particles.

6 . The composition of claim 2 , wherein said one or more chloride salt particles comprise ammonium chloride, and wherein ammonium chloride is a nitrification inhibitor.

7 . The composition of claim 6 , wherein the one or more chloride salt particles further comprise one or more cations of said one or more chloride salt particles, and wherein said one or more cations are selected from the group consisting of a) one or more metal cations selected from the group consisting of i) Na, ii) K, iii) Mg, iv) Ca, v) Fe, vi) Zn, vii) Mn, viii) Cu, ix) Co, x) Mo, xi) Ni, and xii) combinations thereof.

8 . The composition of claim 2 , wherein said one or more fused particles comprise a) said one or more nitrogenous phosphoryl particles and b) said one or more chloride salt particles, wherein the chloride salt particles adhere to a surface of the one or more nitrogenous phosphoryl particles.

9 . The composition of claim 1 , wherein said one or more nitrogenous compounds are selected from the group consisting of a) one or more alkylamines selected from the group consisting of i) one or more monoalkyl amines, and ii) one or more dialkyl amines, b) ammonia, c) ammonium hydroxide, and d) mixtures thereof.

10 . The composition of claim 9 , wherein the alkyl functionality of the one or more alkylamines are selected from the group consisting of (a) —C 1 H 3 , (b) —C 2 H 5 , (c) —C 3 H 7 , (d) —C 4 H 9 , (e) —C 5 H 11 , (f) —C 6 H 5 , and (g) —C 6 H 13 .

11 . The composition of claim 10 , wherein said alkyl functionalities comprise one or more members selected from the group consisting of a) a linear alkyl functionality, b) a branched alkyl functionality, and c) combinations thereof.

12 . The composition of claim 1 , wherein the fluid suspension composition further comprises a) one or more additional nitrification inhibitors, b) a denitrification inhibitor and c) combinations thereof.

13 . The composition of claim 12 , wherein said one or more additional nitrification inhibitors comprise one or more members selected from the group consisting of a) 2-chloro-6-(trichloromethyl) pyridine, b) 4-amino-1,2,4-triazole-HCl, c) 2,4-diamino-trichloromethyltriazine CL-1580, d) dicyandiamide (DCD), e) thiourea, f) 1-mercapto-1,2,4-triazole, g) ammonium thiosulfate, h) one or more dimethyl pyrazole salts selected from the group consisting of (i) organic salts, (ii) inorganic salts and (iii) combinations thereof and i) 2-amino-4-chloro-6-methylpyrimidine and combinations thereof.

14 . The composition of claim 1 , wherein said one or more phosphoryl chloride functionalities comprise one or more members selected from the group consisting of a) phosphorous trichloride (PCl 3 ), b) phosphoryl trichloride (POCl 3 ), c) thiophosphoryl trichloride (PSCl 3 ), and d) mixtures thereof.

15 . The composition of claim 1 , wherein said one or more aprotic liquids are selected from the group consisting of: a) one or more alkylene carbonates selected from the group consisting of i) ethylene carbonate, ii) propylene carbonate and iii) butylene carbonate b) one or more trialkyl phosphates of structure:

wherein:

R 22 is alkyl radical —C 1 H 3 to —C 6 H 13

R 23 is alkyl radical —C 1 H 3 to —C 6 H 13

R 24 is alkyl radical —C 1 H 3 to —C 6 H 13

c) one or more polyols capped with a C 1 -C 6 organic acid wherein of the one or more polyols comprise: (i) ethylene glycol, (ii) 1,3 propylene glycol, (iii) 1,2 propylene glycol, (iv) butylene glycol, (v) trimethylol propane, (vi) trimethylol ethane, (vii) pentaerythritol, (viii) sorbitol, (ix) sorbitan, (x) glucose, (xi) fructose, (xii) galactose and (xiii) glycerin, d) one or more alkylene glycol alkyl ether acetates selected from the group consisting of (i) dipropylene glycol methyl ether acetate, (ii) tripropylene glycol methyl ether acetate, and (iii) tripropylene glycol butyl ether acetate, e) one or more diesters selected from the group consisting of: (i) C 1 -C 6 dialkylsuccinate, (ii) C 1 -C 6 dialkyladipate, (iii) C 1 -C 6 dialkylmethylglutarate, (iv) C 1 -C 6 dialkyl glutarate, (v) C 1 -C 6 dialkyl ethylsuccinate, and (vi) C 1 -C 6 dialkyl maleate, f) one or more fatty acid alkyl esters comprising a fatty acid functionality and an alkyl functionality wherein the fatty acid functionality comprises C 8 -C 18 fatty acids and wherein the alkyl functionality is one or more C 1 -C 6 alkyl radicals, and g) one or more dialkylene glycol dialkyl ethers of structure:

R 11 —O—(R 12 —O) n —R 13

wherein:

R 11 is one or more alkyl radicals selected from the group consisting of C 1 to C 6 ,

R 12 is one or more alkylene radicals selected from the group consisting of C 1 to C 4 ,

R 13 is one or more alkyl radicals selected from the group consisting of C 1 to C 6 , and n is 1 to 10.

16 . The composition of claim 1 , wherein the composition further comprises organic liquid system two, wherein said organic liquid system two comprises one or more organic liquids selected from the group consisting of a) one or more alkanols selected from the group consisting of C 1 -C 10 alkanols, b) one or more polyols selected from the group consisting of i) trimethylol propane, ii) trimethylol ethane, iii) pentaerythritol, iv) sorbitol, v) sorbitan, vi) glucose, vii) fructose, viii) galactose, and ix) glycerin, c) one or more polyalkylene glycols selected from the group consisting of poly (C 1 -C 10 alkylene) glycols, d) one or more dioxolane compound selected from the group consisting of i) 2,2-dimethyl-1,3-dioxolane-4-methanol and ii) 2,2-diisobutyl-1,3-dioxolane-4-methanol, e) one or more alkylene glycol alkyl ethers of structure:

wherein

R 14 is one or more members selected from the group consisting of CH 3 , C 2 H 5 , C 3 H 7 , C 6 H 5 , and C 4 H 9 ,

R 15 is one or more members selected from the group consisting of H and

wherein

R 17 is one or more members selected from the group consisting of H and CH 3 ,

and f is an integer between 1 and 15, and

R 16 is one or more members selected from the group consisting of H and CH 3 ,

f) one or more alkyl lactates selected from the group consisting of i) ethyl lactate, ii) propyl lactate and iii) butyl lactate, g) one or more alkanolamines of structure:

wherein

R 5 is one or more members selected from the group consisting of CH 3 , C 2 H 5 , C 2 H 4 OR 8 , C(CH 3 ) 2 CH 2 OH, CH(C 2 H 5 )CH 2 OH, CH 3 CH(OH)CH 2 , and C 3 H 6 OH,

R 6 is one or more members selected from the group consisting of H, CH 3 , C 2 H 5 , C 2 H 4 OR 8 and C 3 H 6 OH,

R 7 is one or more members selected from the group consisting of H, C 2 H 4 OR 8 and C 3 H 6 OH,

wherein

R 8 is (C 2 H 4 O) g H

wherein

g is an integer between 1 and 10,

h) glycerol carbonate, i) dimethyl sulfoxide, j) N-methyl pyrrolidone, and k) combinations thereof.

17 . The composition of claim 1 , wherein said fluid suspension composition further comprises one or more members selected from the group consisting of a) one or more colorants, b) b) one or more buffers, c) one or more fragrance/odor masking agents, d) one or more micro-nutrients, and e) organic liquid system three, wherein said organic liquid system three comprises one or more surfactants, comprising one or more functionalities selected from the group consisting of a) one or more anionic functionalities, b) one or more cationic functionalities, c) one or more ampholytic functionalities, d) one or more amphoteric functionalities, e) one or more nonionic functionalities, and f) combinations thereof.

18 . The composition of claim 1 , wherein said fluid suspension composition is configured for direct application to said animal waste by one or more methods selected from the group consisting of: a) an automated spraying system, b) a metering system, c) a manual sprayer, and d) combinations thereof, to slow down the biological degradation of urea and ammonium ions, resulting in stabilization of a nitrogen value of animal waste while simultaneously decreasing formation of N 2 O.

19 . The composition of claim 1 , wherein said fluid suspension composition can further comprise water, wherein the fluid suspension is dispersed in water before being applied to animal waste.

20 . The composition of claim 1 , wherein said fluid suspension composition can undergo mechanical processes to reduce inhibitor particle size to improve one or more physical properties selected from the group consisting of:

a) improving storage stability

b) reducing viscosity,

c) improving the smoothness and homogeneity of fluid suspension compositions,

d) improving the smoothness and homogeneity of fluid suspension compositions when stored, and

e) improving homogeneity of delivery of fluid suspension compositions to animal waste.

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 4, 2025
From: MCKNIGHT, GARY DAVID; RAYBORN, RANDALL LINWOOD
To: MCRAY PRODUCTS, LLC
Reel/Frame 070394/0419 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 4, 2025
From: MCRAY PRODUCTS, LLC
To: SOILGENIC TECHNOLOGIES, LLC
Reel/Frame 070394/0507 →
Continuity (5)
Continuation 18890344 · Sep 19, 2024
Continuation 17888342 · Aug 15, 2022
Continuation In Part 17695783 · Mar 15, 2022
Provisional Application 63161064 · Mar 15, 2021
Related Publication 20250197306A1 · Jun 19, 2025
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