# US 2019/0375993 A1 · Oil soluble sulfide scavengers with low salt corrosion and methods of making and using these scavengers > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 2019/0375993 A1 - Document ID: US20190375993A1 - Status: Published application - Kind: A1 - Application number: 16/462,820 - Filed: 2016-12-07 - Published: 2019-12-12 - Earliest claimed: 2016-12-07 - Applicants: General Electric Company - Inventors: Hitesh Ghanshyam Bagaria; Gregory Kaplan - Web page: https://patentgrep.com/patent/US20190375993A1 ## CPC - C10G 29/20: Organic compounds not containing metal atoms - B01D 53/1468: {Removing hydrogen sulfide} - B01D 53/1493: {Selection of liquid materials for use as absorbents} - B01D 53/48: Sulfur compounds - B01D 53/52: Hydrogen sulfide - B01D 53/78: with gas-liquid contact - C07C 239/10: having nitrogen atoms of hydroxylamino groups further bound to carbon atoms of unsubstituted hydrocarbon radicals or of hydrocarbon radicals substituted by halogen atoms or by nitro or nitroso groups - C07C 239/12: having nitrogen atoms of hydroxylamino groups further bound to carbon atoms of hydrocarbon radicals substituted by singly-bound oxygen atoms - C10G 21/27: Organic compounds not provided for in a single one of groups C10G21/14 - C10G21/26 - C10L 3/103: {Sulfur containing contaminants} - B01D 2251/80: Organic bases or salts - B01D 2252/20405: Monoamines - B01D 2252/20431: Tertiary amines - B01D 2252/20484: with one hydroxyl group - B01D 2252/502: having two or more functionalities in the same molecule other than alkanolamine - B01D 2256/24: Hydrocarbons - B01D 2256/245: Methane - B01D 2257/304: Hydrogen sulfide - B01D 2257/306: Organic sulfur compounds, e.g. mercaptans - B01D 2257/308: Carbonoxysulfide COS - C02F 5/12: containing nitrogen (C02F5/14 takes precedence) - C02F 2101/101: {Sulfur compounds} - C02F 2101/40: {containing sulfur} - C10G 2300/207: Acid gases, e.g. H2S, COS, SO2, HCN - C10L 2290/545: Washing, scrubbing, stripping, scavenging for separating fractions, components or impurities during preparation or upgrading of a fuel - C10G: CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION (cracking to hydrogen or synthesis gas C01B; cracking or pyrolysis of hydrocarbon gases to individual hydrocarbons or mixtures thereof of definite or specified constitution C07C; cracking to cokes C10B); RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES - 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 - 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 - C02F: TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE (separation in general B01D; special arrangements on waterborne vessels of installations for treating water, waste water or sewage, e.g. for producing fresh water, B63J; adding materials to water to prevent corrosion C23F; treating radioactively-contaminated liquids G21F9/04; regeneration of reactants for recirculation into processes, see the relevant places for the processes) ## Abstract Sulfide scavengers useful to reduce sulfide concentration in fluid streams and methods of using these scavengers. The scavengers comprise oil soluble reaction products of formaldehyde/N-substituted hydroxylamines and can be used to reduce, for example, H2S content in viscous hydrocarbon oil streams. ## Claims ### Claim 1 A method for reducing sulfides in a fluid comprising contacting said fluid with a reaction product of a N-substituted hydroxylamine and formaldehyde (AHAF). ### Claim 2 (depends on 1) A method as recited in claim 1 wherein said N-substituted hydroxylamine comprises one or more members selected from the group consisting of N,N-dimethylhydroxylamine, N,N-diethylhydroxylamine, N,N-dibenzylhydroxylamine, N-ethylhydroxylamine, N-propylhydroxylamine, N-isopropylhydroxylamine, N-butylhydroxylamine, N-phenylhydroxylamine, N-cyclohexylhydroxylamine, N-tert-butylhydroxylamine, N-benzylhydroxylamine. ### Claim 3 (depends on 1) A method as recited in claim 1 wherein said reaction product (AHAF) has the formula: wherein n is from about 0-10 and R1 and R2 are each independently chosen from H, C1-C10 linear, branched, and cyclic alkyl, alkenyl, or aryl groups; with the proviso that both R1 and R2 are not H. ### Claim 4 (depends on 1) The method as recited in claim 1 wherein said sulfides comprise one or more members selected from the group consisting of organic sulfides, mercaptans, thiols, COS, and H2S. ### Claim 5 (depends on 1) The method of claim 1 wherein said fluid is (i) a hydrocarbon, (ii) natural gas, (iii) water, or (iv) a multiphase mixture of hydrocarbon. ### Claim at position 6 6-8. (canceled) ### Claim 9 (depends on 5) The method of claim 5 wherein said hydrocarbon is a hydrocarbon oil selected from the group consisting of crude oil, naptha, gas oil, bunker fuel, marine diesel, asphalt, and bitumen. ### Claim 10 (depends on 1) The method of claim 1 wherein from about 1 to 100,000 ppm by volume of said reaction product is brought into contact with said fluid based upon one million parts of said fluid. ### Claim 11 (canceled) ### Claim 12 (depends on 3) The method as recited in claim 3 wherein R1 and R2 are both C1-C10 alkyl. ### Claim 13 (depends on 12) The method as recited in claim 12 wherein both R1 and R2 are ethyl. ### Claim 14 A method for making a dialkylhydroxylamine/formaldehyde reaction product comprising reacting a hydroxylamine of the formula RR′NOH with formaldehyde, wherein R and R′ are each independently chosen from H, linear, branched, and cyclic C1-C10 alkyl, alkenyl, or aryl groups; with the proviso that both R1 and R2 are not H; said method being conducted at a temperature of about above 60° C. for about 0.5-2.0 hours. ### Claim 15 (depends on 14) A method as recited in claim 14 wherein said reaction is conducted in the presence of an organic solvent. ### Claim 16 (depends on 14) A method as recited in claim 14 wherein said reaction is conducted at a temperature of about 80-90° C. ### Claim 17 (depends on 14) A method as recited in claim 14 wherein R and R′ are both C1-C10 alkyl. ### Claim 18 (depends on 17) A method as recited in claim 17 wherein R and R′ are both ethyl. ### Claim 19 (depends on 14) A method as recited in claim 14 wherein the molar ratio of formaldehyde:N-substituted hydroxylamine is from about 0.5-5 moles formaldehyde to about 1 mole of N-substituted hydroxylamine. ### Claim 20 (canceled) ### Claim 21 (depends on 19) A method as recited in claim 19 wherein said formaldehyde is paraformaldehyde. ### Claim 22 An N-substituted hydroxylamine/formaldehyde reaction product having the structure wherein n is an integer from 0-10; R1 and R2 are each independently chosen from H, C1-C10 linear, branched, alkyl, alkenyl, or aryl groups with the proviso that both R1 and R2 are not H. ### Claim 23 (depends on 22) The reaction product as recited in claim 22, wherein said reaction product is oil soluble. ### Claim 24 (depends on 23) The reaction product as recited in claim 23 wherein both R1 and R2 are C1-C10 alkyl. ### Claim 25 (depends on 24) The reaction product as recited in claim 24 wherein both R1 and R2 are ethyl.