US20200017766A1 - Methods of using ionic liquids as corrosion inhibitors - Google Patents

Methods of using ionic liquids as corrosion inhibitors Download PDF

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Publication number
US20200017766A1
US20200017766A1 US16/509,431 US201916509431A US2020017766A1 US 20200017766 A1 US20200017766 A1 US 20200017766A1 US 201916509431 A US201916509431 A US 201916509431A US 2020017766 A1 US2020017766 A1 US 2020017766A1
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Prior art keywords
anionic
group
alkyl
esters
ionic liquid
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US16/509,431
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Inventor
Jerry Weers
Mary Jane Felipe
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Baker Hughes Holdings LLC
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Baker Hughes Inc
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Priority to US16/509,431 priority Critical patent/US20200017766A1/en
Publication of US20200017766A1 publication Critical patent/US20200017766A1/en
Assigned to BAKER HUGHES, A GE COMPANY, LLC reassignment BAKER HUGHES, A GE COMPANY, LLC ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: FELIPE, MARY JANE, WEERS, JERRY
Priority to US17/545,910 priority patent/US11485915B2/en
Assigned to BAKER HUGHES HOLDINGS LLC reassignment BAKER HUGHES HOLDINGS LLC CHANGE OF NAME (SEE DOCUMENT FOR DETAILS). Assignors: BAKER HUGHES, A GE COMPANY, LLC
Abandoned legal-status Critical Current

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    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
    • C10G2300/00—Aspects relating to hydrocarbon processing covered by groups C10G1/00 - C10G99/00
    • C10G2300/40—Characteristics of the process deviating from typical ways of processing
    • C10G2300/4075—Limiting deterioration of equipment
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
    • C10G2300/00—Aspects relating to hydrocarbon processing covered by groups C10G1/00 - C10G99/00
    • C10G2300/80—Additives
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
    • C10G2400/00—Products obtained by processes covered by groups C10G9/00 - C10G69/14
    • C10G2400/02—Gasoline
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
    • C10G2400/00—Products obtained by processes covered by groups C10G9/00 - C10G69/14
    • C10G2400/04—Diesel oil
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L2200/00—Components of fuel compositions
    • C10L2200/04—Organic compounds
    • C10L2200/0407—Specifically defined hydrocarbon fractions as obtained from, e.g. a distillation column
    • C10L2200/0438—Middle or heavy distillates, heating oil, gasoil, marine fuels, residua
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L2200/00—Components of fuel compositions
    • C10L2200/04—Organic compounds
    • C10L2200/0407—Specifically defined hydrocarbon fractions as obtained from, e.g. a distillation column
    • C10L2200/0438—Middle or heavy distillates, heating oil, gasoil, marine fuels, residua
    • C10L2200/0446—Diesel
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L2270/00—Specifically adapted fuels
    • C10L2270/02—Specifically adapted fuels for internal combustion engines
    • C10L2270/026—Specifically adapted fuels for internal combustion engines for diesel engines, e.g. automobiles, stationary, marine

Definitions

  • the disclosure relates to the use of ionic liquids as corrosion inhibitors.
  • Corrosion of metallic surfaces is often an acute problem which arises during the production and refining of hydrocarbon streams as well as in other industries which rely on aqueous fluids for the removal of heat from one medium to another.
  • cooling towers extract waste heat to the atmosphere by cooling of a water stream to a lower temperature.
  • Cooling towers are used in oil refineries, petrochemical and other chemical plants, thermal power stations and power plants, steel mills, natural gas processing plants, food processing plants, semi-conductor plants as well as HVAC systems.
  • Aqueous fluids, including those with high salt content cause corrosion which may lead to equipment failure requiring equipment to be replaced. Corrosion also decreases plant efficiency due to loss of heat transfer. This is often the result of heat exchanger fouling caused by the accumulation of corrosion products.
  • Corrosive aqueous fluids having high salt content are also used in drilling and completion fluids. Marked corrosivity is often seen when such brines are used as packer fluids since they remain in contact with production tubing and casing for extended periods of time.
  • Corrosion of metallic surfaces is evidenced by surface pitting, embrittlement and loss of metal. Pitting occurs when anodic and cathodic sites become stationary due to large differences in surface conditions. Once a pit is formed, the solution inside it is isolated from the environment and becomes increasingly corrosive with time. The high corrosion rate in the pit produces an excess of positively charged metal cations, which attract chloride anions. In addition, hydrolysis produces hydrogen ions. The increase in acidity and concentration within the pit promotes even higher corrosion rates, and the process becomes self-sustaining.
  • zinc salts are known to be unstable in neutral or alkaline water. Scale formation further typically results from the metals in inorganic corrosion inhibitors. For instance, zinc scales typically form by use of zinc containing corrosion inhibitors. The effectiveness of corrosion inhibitors in aqueous systems thus significantly decreases.
  • the disclosure relates to the use of electronically neutral ionic liquids as corrosion inhibitors, the ionic liquids represented by (I):
  • A is or contains nitrogen, a nitrogen containing heterocyclic ring, is or contains phosphorus, or a phosphorus containing heterocycle
  • X is an anion selected from the group consisting of halides; hydroxyl; hydroxyl containing nitrogen or sulfur compounds; sulfonates; sulfates; bisulfites; carbonates; alkyl carbonates; bicarbonates; thiocarbonates; dithiocarbonates; trithiocarbonates; xanthates, thiocyanates; alkoxides; carboxylates; hydroxycarboxylates; amino fatty acids; anionic alkoxylated fatty acids; anionic metallic complexes, sulfur or silicon containing anions; sulfides; polysulfides; anionic phosphate esters, anionic thiophosphate esters; anionic phosphonate esters; anionic thiophosphonate esters; alkyl substituted phosphines; anionic urea; anionic thioure
  • Another embodiment relates to the use of ionic liquids as corrosion inhibitors, the ionic liquids represented by (II) and (Ill):
  • a in formula (II) is or contains nitrogen or phosphorus or a heterocyclic ring thereof and wherein each A in formula (III) is independently selected from nitrogen or phosphorus or a heterocyclic ring thereof;
  • X is an anion selected from the group consisting of halides; hydroxyl; hydroxy containing nitrogen or sulfur compounds; carbonates; alkyl carbonates; bicarbonates; carboxylates; hydroxycarboxylates; dithiocarbonates; trithiocarbonates; xanthates, thiocyanates; alkoxides; anionic urea; anionic alkyl substituted phosphines; anionic amino fatty acids; anionic alkoxylated fatty acids; anionic acrylamido-methyl propane sulfonate/acrylic acid copolymers; anionic phosphated maleic copolymers; anionic homo or copolymers of an oxirane or methyloxirane; anionic metal complexes; sulfur or silicon containing anions; anionic phosphate esters; anionic thiophosphate esters; anionic phosphonate esters; anionic thiophosphonate esters; anionic thiols; anionic natural products; anionic phenol
  • a method of enhancing the performance of a corrosion inhibitor is provided by contacting the corrosion inhibitor with a corrosion inhibiting ionic liquid.
  • the corrosion inhibiting ionic liquid may act as an intensifier for the corrosion inhibitor; the corrosion inhibitor not being an ionic liquid.
  • ionic liquid refers to a neutral molten salt composed entirely of ions and which is liquid at ambient or near ambient temperatures.
  • the phrase shall include the quaternary organic salts of (I), (II) and (Ill).
  • the ionic liquid functions as a corrosion inhibitor.
  • second corrosion inhibitor shall refer to any material (other than an ionic liquid) which enhances the performance of an ionic liquid or whose performance is enhanced by an ionic liquid.
  • treatment composition shall refer to a composition resulting from contact of an ionic liquid with a second corrosion inhibitor.
  • the phrase shall include blends, mixtures, complexes and reactions products of the ionic liquid and second corrosion inhibitor.
  • inhibitor shall include the inhibition, prevention, reduction or control of corrosion of a metallic surface.
  • corrosion inhibitor shall refer to a material capable of inhibiting, preventing or reducing corrosion of a metallic surface.
  • petroleum hydrocarbon fluid shall include crude oil, shale oil, shale gas condensate, bitumen, diluted bitumen (dil-bit), refinery fractions including distillates including gas oil cuts, finished fuel including diesel fuel, petroleum fuel and biofuel, finished petroleum products, residual oil, fuel gas, flare gas, propane, butane, liquefied petroleum gas (LPG), natural gas liquid (NGL) and combinations thereof.
  • LPG liquefied petroleum gas
  • NTL natural gas liquid
  • ionic liquids and treatment compositions described herein are especially useful in the treatment of crude oil, bitumen, diesel fuel, petroleum fuel, biofuel, residual oil, fuel gas, flare gas, propane, butane, liquefied petroleum gas (LPG), natural gas liquid (NGL) and refinery fractions (including gas oil cuts and light lubricating oils) and combinations thereof.
  • LPG liquefied petroleum gas
  • NNL natural gas liquid
  • refinery fractions including gas oil cuts and light lubricating oils
  • any of these may contain water, brines, gases such as hydrocarbon gases, or a combination thereof.
  • the word “conduit” may refer to any pipeline, pipe, tubing, tubular, flow conduit, thoroughfare or other artery in which a chemical, including a petroleum hydrocarbon fluid, travels or contacts.
  • the word “vessel” shall include any equipment or container in which a petroleum hydrocarbon fluid is in contact, such as heat exchangers, etc.
  • the conduit may, but not limited to, those composed of a metal, plastic or glass.
  • the site of the “conduit” or “vessel” shall include, but not be restricted to reservoirs, wells, pipelines, refineries, fluid processing or treatment facilities (including those where gas or oil production or treatment occur, chemical plants, thermal power stations, power plants, steel mills, natural gas processing plants, food processing plants, semi-conductor plants and HVAC systems) as well as thoroughfares leading to or from any of the above.
  • ionic liquids and treatment compositions described herein may be used during the production of crude oil and gas.
  • the ionic liquids and treatment compositions may be used during the recovery of petroleum hydrocarbon fluids from underground reservoirs.
  • the ionic liquids and treatment compositions are most useful during the production of oil and gas from a well and during in a refinery operation including light-ends recovery, solid waste and cooling water treatment, process-water treatment, cooling, storage, and handling, product movement, hydrogen production, acid and tail-gas treatment and sulfur recovery.
  • the ionic liquids and treatment compositions may also be used during the purification or another treatment phase of an industrial product.
  • the ionic liquids and treatment compositions may be used to treat cooling water streams.
  • Such streams include produced water (aqueous fluids produced along with crude oil and natural gas during from reservoirs water naturally present in oil and gas bearing geological formations, aqueous fluids produced or used during the production of oil and gas from reservoirs or an industrial product, aqueous fluids produced during the refining of oil and gas or an industrial product, aqueous fluids used during the refining of oil and gas or an industrial product, aqueous fluids used or produced during transit or storage of petroleum hydrocarbon fluids or an industrial product).
  • Exemplary water streams include flowback water, degassed sour water, boiler blowdown streams, cooling tower bleed-off/blowdown (originating from oil refineries, petrochemical and natural gas processing plants, other chemical plants, thermal power stations, power plants, steel mills, food processing plants, semi-conductor plants and HVAC systems).
  • Wastewater streams from industrial applications include municipal wastewater treatment facilities, streams in transit to or from municipal wastewater treatment facilities, tanning facilities, and the like.
  • Exemplary products removed during water treatments described herein may include inorganic salts, polymers, breakers, friction reducers, lubricants, acids and caustics, bactericides, defoamers, emulsifiers, filtrate reducers, shale control inhibitors, phosphorus ions, ions of calcium, magnesium and carbonates, bacteria as well other production chemicals.
  • the ionic liquids and treatment compositions may also be used within a conduit or vessel or introduced into a conduit or vessel.
  • the ionic liquids and treatment compositions may also be used during transit of petroleum hydrocarbon fluids or an industrial product as well as during storage of petroleum hydrocarbon fluid or an industrial product.
  • the ionic liquid and treatment compositions are typically liquid at relatively low temperature. While the ionic liquids are salts, they typically exhibit high flash points, good solvency for other chemicals and strong basicity.
  • Suitable ionic liquids as PIPPFLI are those of the formula (I):
  • A is or contains nitrogen or phosphorus, a nitrogen containing heterocyclic ring or a phosphorus containing heterocyclic ring; and
  • X is an anion selected from the group consisting of halides; hydroxyl; hydroxy containing nitrogen or sulfur compounds; carbonates; alkyl carbonates; bicarbonates; dithiocarbonates; trithiocarbonates; xanthates, thiocyanates; alkoxides; carboxylates; hydroxycarboxylates; amino fatty acids; anionic alkoxylated fatty acids; anionic metallic complexes, sulfur or silicon containing anions; anionic phosphate esters, anionic thiophosphate esters; anionic phosphonate esters; anionic thiophosphonate esters; alkyl substituted phosphines; anionic urea; anionic thiourea; anionic natural products; anionic thiols; anionic phenols; anionic phenol resins; anionic copolymers of alpha
  • ionic liquids of formula (II) or (III) may be used as the PIPPCFI ionic liquid:
  • a in formula (II) is or contains nitrogen or phosphorus or a heterocyclic ring thereof and wherein each A in formula (III) is independently selected from nitrogen or phosphorus or a heterocyclic ring thereof;
  • X is an anion selected from the group consisting of halides; hydroxyl; hydroxy containing nitrogen or sulfur compounds; carbonates; alkyl carbonates; bicarbonates; carboxylates; hydroxycarboxylates; sulfonates; sulfates; bisulfites; thiocyanates; dithiocarbonates; trithiocarbonates; xanthates, thiocyanates; carbamates; dithiocarbamates; sulfides; polysulfides; alkoxides; anionic urea; anionic alkyl substituted phosphines; anionic amino fatty acids; anionic alkoxylated fatty acids; anionic acrylamido-methyl propane sulfonate/acrylic acid copolymers; anionic phosphated maleic copolymers; anionic homo or copolymers of an oxirane or methyloxirane; anionic metal complexes; sulfur or silicon containing anions; anionic phosphate esters;
  • cation of (I), (II) or (III) is phosphorus or a phosphorus containing ring and X is an anion selected from the group consisting of hydroxyl; hydroxy containing nitrogen or sulfur compounds; bicarbonates; alkoxides; hydroxycarboxylates; silicon containing anions; anionic amino fatty acids; anionic alkoxylated fatty acids; anionic thiophosphonate esters; alkyl substituted phosphines; anionic urea; anionic thiourea; anionic natural products; anionic phenols; anionic phenol resins; anionic copolymers of alpha olefins and maleic anhydride, esters, amides, imides or derivatives thereof; anionic acrylamido-methyl propane sulfonate/acrylic acid copolymers; anionic homopolymers, copolymers and terpolymers of one or more acrylates, methacrylates and acrylamides, optionally
  • cation A of formula (I), (II) or (III) is or contains nitrogen or a nitrogen heterocyclic ring and anion X is selected from the group consisting of silicon containing anions; anionic thiophosphonate esters; anionic natural products; anionic phenol resins; alkoxides; anionic copolymers of alpha olefins and maleic anhydride, esters, amides, imides or derivatives thereof or a mixture thereof; amino fatty acids; anionic alkoxylated fatty acids; alkyl substituted phosphines; anionic urea; anionic thiourea; anionic acrylamido-methyl propane sulfonate/acrylic acid copolymers; anionic homopolymers, copolymers and terpolymers containing acrylamide units; anionic phosphated maleic copolymers; anionic oxirane or methyloxirane homo or copolymers; and mixtures thereof.
  • the ionic liquid represented by (II) or (III) has a cation A of is nitrogen (for II) and each A in (III) is nitrogen as defined herein and wherein X is an anion selected from the group consisting of anionic metallic complexes; sulfur or silicon containing anions; anionic phosphate esters; anionic thiophosphate esters; anionic phosphonate esters; anionic thiophosphonate esters; anionic thiols; anionic natural products; anionic phenols; anionic phenol resins; anionic copolymers of alpha olefins and maleic anhydride, esters, amides, imides or derivatives thereof amino fatty acids; anionic alkoxylated fatty acids; alkyl substituted phosphines; an oxirane or methyloxirane homo or copolymer; anionic urea; anionic thiourea; anionic acrylamido-methyl propane sulfonate/acrylic
  • Preferred ionic liquids are those of (III) having structures R 1 R 2 R 3 R 4 N + ; R 1 R 2 R 3 N + R 8 N + R 5 R 6 R 7 ; S+R 1 R 2 R 3 ; R 1 R 2 R 3 R 4 P + ; and R 1 R 2 R 3 N + R 4 P + R 5 R 6 R 7 .
  • anion X of (I), (II) or (III) is a hydroxide, bicarbonate, carbonate, alkyl carbonate or an alkoxide.
  • R 1 , R 2 , R 3 , R 4 , R 5 , R 6 and R 7 of formula (II) and (III) are independently selected from the group consisting of a straight or branched C 1-30 alkyl group, a C 7-30 alkylbenzyl group, a C 7-30 arylalkyl group, a straight or branched C 3-30 alkenyl group, a C 1-30 hydroxyalkyl group, a C 7-30 hydroxyalkylbenzyl group, a zwitterion (such as those from oxyalkylation of an amine with an alkylene oxide; or a polyoxyalkylene group; and R 8 is a straight or branched C 1-30 alkylene, an alkylene oxyalkylene, or an alkylene polyoxyalkylene or R groups may be joined to form a heterocyclic nitrogen, sulfur or phosphorus ring; and the anion comprises halides, hydroxide, bicarbonate, carbonate, alkyl
  • R 1 , R 2 , R 3 , R 4 , R 5 , R 6 and R 7 of (II) and (III) are independently —H or a C 1-20 alkyl; wherein at least one (or at least two) of R 1 , R 2 , R 3 , R 4 , R 5 , R 6 and R 7 is a C 2-20 alkyl, preferably a C 6-12 alkyl.
  • Exemplary ionic liquids of formulas (I), (II) and (III) include, but are not limited to, those ionic liquids having a cation of dicocodimethyl ammonium and ditallowdimethyl ammonium.
  • Further specific exemplary ionic liquids are dicocodimethyl ammonium hydroxide, benzyltrimethylammonium hydroxide, ditallowdimethyl ammonium hydroxide, tributylmethylammonium methyl carbonate, tetraethylammonium bicarbonate, tetrapropylammonium hydroxide, coco dimethylethylammonium methyl carbonate, dodecyl trimethylammonium hydroxide, (2-hydroxyethyl) cocoalkyl ammonium hydroxide (including dialkyl, trialkyl, tetralkyl derivatives like dicocodimethyl ammonium hydroxide cocotrimethyl ammonium hydroxide), cocodialkylammonium chloride derivative
  • the cation of (III) may be a polyamine, meaning the cation may have two or more nitrogen atoms (and in some cases up to 5 nitrogen atoms).
  • one or more of the nitrogens of the polyamine may be cationic such that the cation of (III) may be a polyamine containing two or more cationic sites (and in some cases up to 5 cationic sites).
  • R 8 may correspond to (—NR 1 R 2 ) y or (—NR 1 R 2 R 3 ) y wherein y corresponds to 1, 2 or 3 to render the number of nitrogen sites and R 1 , R 2 and R 3 are as defined above.
  • y is 1 when A is a triamine
  • y is 2 when A is a tetramine
  • y is 3 when A is a pentamine.
  • Exemplary are cations of diethylenediamine, triethylenetetraamine, tetraethylenepentamine and (bis) hexamethylenetriamine.
  • the cation may consist of multiple cationic sites on the phosphorus wherein R 8 may correspond to (—PR 1 R 2 ) y or (—PR 1 R 2 R 3 ) y wherein y corresponds to 1, 2 or 3 to render the number of phosphorus sites and R 1 , R 2 , and R 3 are as defined above.
  • alkyl refers to a straight or branched chain, saturated monovalent hydrocarbon group regardless whether straight or branched chain is specifically mentioned or not; “aryl” refers to an aromatic monovalent group containing only carbon in the aromatic ring or rings; “arylalkyl” refers to an alkyl group that has been substituted with an aryl group, with benzyl being an exemplary arylalkyl group; “alkylbenzyl” refers to a benzyl group that has been substituted with an alkyl group in the aromatic ring; “hydroxyalkyl” refers to an alkyl group that has been substituted with a hydroxyl group with 2-hydroxyethyl as an exemplary hydroxyalkyl group; “hydroxyalkylbenzyl” refers to a benzyl group that has been substituted with a hydroxyalkyl group as defined herein in the aromatic ring; “alkylene” refers to a straight or branched chain, saturated, divalent
  • substituted means that at least one hydrogen on the designated atom or group is replaced with another group, provided that the designated atom's normal valence is not exceeded.
  • Substituted with a group means substituted with one or more groups.
  • Suitable nitrogen containing heterocyclic rings referenced herein include pyridinium, imidazolinium and a pyrrole cation (including alkylated derivatives thereof). Further reference to “nitrogen” shall include nitrogen containing cations such as an oxyalkylated nitrogen.
  • the cation of (I), (II) or (III) is a quaternary amine salt, triethanolamine methyl chloride, oxyalkylated amine, polyamine, oxyalkylated polyimines, cationic melamine acid colloid or an oxyamine such as those of the formula (CH 3 ) 2 N(CH 2 ) x OH where x is 1 to 6, preferably 2.
  • a polyoxyalkylene group has a formula
  • R 1 is independently a C 1-10 alkylene or C 2-8 alkylene, specifically ethylene, propylene, butylene, or a combination thereof, and z is an integer greater than 1 such as 2 to 30, 4 to 25, or 8 to 25.
  • An alkylene polyoxyalkylene group has a formula
  • R 2 is a 01-30 alkylene
  • each occurrence of R 3 is independently a C 1-10 alkylene or C 2-6 alkylene, specifically ethylene, propylene, butylene, or a combination thereof
  • y is an integer from 1 to 500, such as 2 to 30, 4 to 25, or 8 to 25.
  • An alkylene oxyalkylene group has a formula of —R 7 —O—R 8 —, wherein R 7 and R 8 are each independently a C 1-20 , or C 1-10 , or C 1-5 branched or straight chain alkylene.
  • R 7 and R 8 can be ethylene.
  • Exemplary halides for the anion X ⁇ are —Cl, —Br, —F and —I. In an embodiment —Cl is preferred.
  • Suitable sulfur and phosphorus containing anions include sulfates (SO 4 ⁇ ), bisulfate (HSO 4 ⁇ ), thiocyanate (SCN ⁇ ), thiocarbonate
  • R 1 and R 2 are independently selected from C 1-20 alkyl groups, xanthates
  • R is a C 1-20 alkyl, sulfides (RS ⁇ ) wherein R is a C 1-20 alkyl, anionic polysulfides (RS(S) x S ⁇ ) wherein R is a C 1-20 alkyl and x is one to five, anionic phosphate esters [ROP( ⁇ O)(OH) 2 ] and anionic phosphonate ester [R—P( ⁇ O)(OH) 2 (wherein R is a C 1-20 alkyl or a C 1-20 oxyalkyl-(RO—); anionic thiophosphate esters
  • anionic thiophosphonate esters wherein R is a C 1-20 alkyl or a C 1-20 oxyalkyl- (RO—); sulfonates (RSO 3 ⁇ ) wherein R is C 1-20 alkyl or aryl or alkylaryl group; and anionic thiols (RSH) where R is —(CH) x )H and x is from 1 to 4.
  • Exemplary oxirane or methyloxirane homo or copolymers include those containing units of the structure —(CH 2 CH 2 O) x CH 2 CH(CH 3 )O) y where x and y are independently selected from 1 to 1500.
  • Exemplary anionic metal complexes in formulae (I), (II) and (Ill) may include, but not be limited to Fe (such as Fe containing anions like FeCl 4 ⁇ ), aluminum (such as Al containing anions like AlCl 4 ⁇ ), etc. Further, the anionic metal complex may be formed from copper, zinc, boron, tin and mixtures thereof.
  • the anion may further be an anionic natural products like anions of a polysaccharide, polyphenol or lignin.
  • Suitable anions of polysaccharides include anionic starches (such as mixtures of amylose and amylopectin), anionic polyphenols (such as anionic flavonoids or anionic natural polyphenols and anionic tannins (such as water soluble anionic polyphenols with a molecular weight between 500 and 3,000).
  • Suitable anions may also be anionic phenolics such as anionic phenols, anionic alkyl substituted phenols, anionic phenol oxyalkylates, anionic alkyl substituted phenol oxyalkylates, anionic phenolic or alkylphenol resins and anionic phenol resin oxyalkylates.
  • anionic phenolics such as anionic phenols, anionic alkyl substituted phenols, anionic phenol oxyalkylates, anionic alkyl substituted phenol oxyalkylates, anionic phenolic or alkylphenol resins and anionic phenol resin oxyalkylates.
  • the alkyl groups of the anionic phenolics are C 1-28 .
  • the anion may also be an alkoxide.
  • Suitable alkoxides include those of the formula RO— where R is a C 1-30 alkyl or cycloalkyl group. In an embodiment, R is C 1-18 alkyl, C 6-12 aryl, or C 5-12 cycloalkyl, Exemplary alkoxides are tert-butoxide, n-butoxide, isopropoxide, n-propoxide, isobutoxide, ethoxide, methoxide, n-pentoxide, isopentoxide, 2-ethylhexoxide, 2-propylheptoxide, nonoxide, octoxide, decoxide and isomers thereof.
  • the alkoxides are tert-butoxide, isopropoxide, ethoxide, or methoxide. Tert-butoxide and methoxide are specifically mentioned.
  • the alkoxides may further be anionic ethylene or propylene oxide homopolymers, anionic copolymers or terpolymers (which may optionally be crosslinked). Suitable crosslinking agents include bisphenol A or maleic anhydride.
  • Suitable alkyl carbonates are those of the formula ROCO 2 ⁇ , where R is a halogenated or non-halogenated linear or branched alkyl, or hydroxyl alkyl group, preferably a halogenated or non-halogenated linear or branched C 1-8 or C 1-5 alkyl group.
  • Exemplary carboxylates include formate, acetate, propionate, benzoate, n-butyrate, isobutyrate, pivalate, octanoate and laurate, as well as anions of C 18 fatty acids such as oleate, linolate and stearate.
  • Exemplary hydroxycarboxylates include glycolate, lactate, citrate, glucarate, gluconate and tartrate.
  • Suitable anionic copolymers of alpha olefins and maleic anhydride, esters, amides, imides (and derivatives thereof) include those of the general structure
  • R is a C 1-30 alkyl group.
  • Suitable alkyl carbonates, carboxylates, anionic metal complexes, anionic natural products, anionic phenolics, alkoxides, anionic alpha olefin/maleic anhydride polymers, anionic polymers of acrylates, methacrylates and acrylamides and sulfur cations are those referenced in the paragraphs above.
  • the ionic liquids of (I), (II), and (III) are salts having a melting point range of ⁇ 100° C. to 200° C., typically below 100° C. They are generally non-volatile and exhibit low vapor pressures and are environmentally more benign than other organic solvents, such as volatile aromatics and alkanes. They are thermally stable over a wide temperature range with some having a liquid range of up to 300° C. or higher. Typically they are molten salts of organic compounds or eutectic mixtures of organic and inorganic salts. Stability and other fundamental physical properties of the ionic liquids are influenced by the selection of cation while the selection of anion generally determines the functionality of the ionic liquid.
  • ionic liquids disclosed herein may be prepared by first forming a quaternary salt followed by ion exchange with an acid or salt or by an anionic metathesis reaction with an appropriate anion source to introduce the desired counter anion.
  • a nitrogen or phosphorus containing heterocyclic compound such as an imidazole or pyridine
  • the alkylating agent may be an alkyl chloride providing a broad range of alkyl groups on the nitrogen including straight and branched or cyclic C 1 -C 20 alkyl groups.
  • the quaternary salt may then be subjected to ion exchange with an acid or salt to form the ionic liquid.
  • Ionic liquids (I), (II) and (III) may be tailored by varying the cation and anion pairing may be combined with a second corrosion inhibitor to form a treatment composition.
  • the amount of ionic liquid in the treatment composition may be from about 3 to about 99 weight percent.
  • the anion of the ionic liquid may be the same as the conjugate base of the second corrosion inhibitor.
  • a suitable ionic liquid may be prepared of formula (II) or (Ill) where the cation is nitrogen, each of R 1 , R 2 , R 3 and R 4 are hydrogen and anion A is a phosphonate.
  • the ionic liquid functions as a corrosion inhibitor.
  • the treatment composition may consist of the ionic liquid and the second corrosion inhibitor.
  • the conjugate base of the second corrosion inhibitor is a phosphonate, the same as the anion of the ionic liquid.
  • corrosion inhibition improves when the ionic liquid is used in combination with the second corrosion inhibitor.
  • the presence of the ionic liquid in the treatment composition may boost the corrosion inhibition power of the second corrosion inhibitor.
  • the presence of the second corrosion inhibitor in the treatment composition may boost the corrosion inhibition power of the ionic liquid.
  • the combination of ionic liquid and second corrosion inhibitor may therefore substantially reduce the amount of corrosion and rate of corrosion onto the metallic surface compared to when a fluid containing only one of the ionic liquid or second corrosion inhibitor is used.
  • the presence of the ionic liquid in the treatment composition decreases the rate of corrosion onto a metallic surface by at least 25% and sometimes 50% or higher.
  • ionic liquids and/or treatment compositions described herein may exhibit multiple functions.
  • an ionic liquid(s) or treatment composition(s) may be effective as a scale inhibitor as well as a corrosion inhibitor.
  • One or more ionic liquids and/or treatment compositions may be concurrently used.
  • the second corrosion inhibitor is preferably a liquid material. If the inhibitor is a solid, it may be dissolved in a suitable solvent, thus making it a liquid.
  • the ionic liquid and treatment compositions are typically introduced to their targeted location in an organic solvent or in an aqueous fluid such as fresh water, brackish water, brine as well as salt-containing water solutions such as sodium chloride, potassium chloride and ammonium chloride solutions.
  • Suitable organic solvents include alkyl alcohols such as methyl alcohol, ethyl alcohol, propyl alcohol, isopropyl alcohol and butyl alcohol and alkylene glycols like ethylene glycol, propylene glycol.
  • the fluid containing the ionic liquid or treatment composition may further contain one or more surfactants, mutual solvents, sequestering agents, friction reducers, gelling agents, and other conventional additives as well as mixtures thereof.
  • the amount of ionic liquid or treatment composition in the organic solvent or aqueous fluid is dependent on the corrosive conditions, temperature and intended time of contact. Typically, the amount of ionic liquid or treatment composition in the fluid introduced to the targeted site is from 1 ppm to about 5,000 ppm, or about 1 ppm to about 500 ppm, or about 5 ppm to about 150 ppm.
  • an effective corrosion inhibiting or preventative amount of the ionic liquid or treatment composition is introduced to an acidic fluid prior to introduction of the acidic fluid into a targeted well or conduit. This may especially be the case where the ionic liquid or treatment composition is used during a well treatment operation as discussed below.
  • the ionic liquid and second corrosion inhibitor are first combined and then introduced into the targeted location in the organic solvent or aqueous fluid. At times however, the ionic liquid and second corrosion inhibitor may be introduced in different stages.
  • the ionic liquid and treatment compositions dramatically inhibits the amount of corrosion and the rate of corrosion on metallic surfaced caused by aqueous acids including mineral acids, like hydrochloric acid, hydrofluoric acid, sulfuric and phosphoric acids as well as weak acids, such as formic acid, acetic acid, hydroxyacetic acid, citric acid, phosphonic acid, methanesulfonic acid and propionic acid as well as other acids affecting industrial operations.
  • mineral acids like hydrochloric acid, hydrofluoric acid, sulfuric and phosphoric acids as well as weak acids, such as formic acid, acetic acid, hydroxyacetic acid, citric acid, phosphonic acid, methanesulfonic acid and propionic acid as well as other acids affecting industrial operations.
  • Inhibition of corrosion may be seen on a wide host of metallic surfaces including iron, chromium, ferrous base metals, alloys of steel, alloys of nickel, duplex steels, stainless steel, chrome steel, martensitic alloy steel, ferritic alloy steel, carbon steel, precipitation-hardened stainless steels and the like. Pitting is dramatically reduced when the ionic liquids and treatment compositions are used.
  • the ionic liquids and treatment compositions may be contacted with a hydrocarbon-containing stream under severe conditions of heat, pressure, agitation and/or turbulence. They may be used at a wide variety of temperatures, typically ranging from 120° F. to 180° F. as well as up to 350° F. beyond.
  • the ionic liquids and treatment compositions are very useful in the inhibition of corrosion of metallic surfaces during well treatment operations.
  • the treated well may be a hydrocarbon producing well, such as a gas or oil well, or non-hydrocarbon producing wells, such as water injection wells, water producing wells or geothermal wells. They can be used during various types of treatment operations that occur in or before the wellbore and in subterranean formation applications. For example, they can be used in pickling a tubular, cleaning a wellbore, scale treatment, and coiled tubing applications. They can also be used in matrix acid stimulation, acid fracturing, acid tunneling, drilling mud removal, scale treatment, coiled tubing application, or damage removal.
  • any known method of introducing the ionic liquid(s) or treatment composition(s) into the reservoir can be used.
  • the ionic liquids and treatment compositions protect metal tubulars and alloy surfaces from acidic fluids that are introduced or produced downhole.
  • the ionic liquids and treatment compositions can also be used to inhibit corrosion during refining of hydrocarbon fluids, during transport or storage of the fluids or during any period in between.
  • the ionic liquids and treatment compositions are highly useful in the prevention or inhibition of corrosion attributable to carbon dioxide and hydrogen sulfide.
  • the hydrogen sulfide may be formed when the treating acid contacts a sulfur-containing mineral, such as iron sulfide.
  • the ionic liquids and treatment compositions are further particularly effective in the treatment of cooling towers relying on aqueous fluids for the removal of heat from one medium to another.
  • the ionic liquids and treatment compositions may be used in oil refineries, petrochemical and other chemical plants, thermal power stations and power plants, steel mills, natural gas processing plants, food processing plants, semi-conductor plants as well as HVAC systems.
  • Exemplary ionic liquids as corrosion inhibitors include those wherein X in (I), (II) or (Ill) is an anionic phosphate ester, anionic thiophosphate ester, anionic phosphonate ester; anionic thiophosphonate ester; anionic diphosphonic acid; and anionic carboxylic acids (such as anionic glucaric acid).
  • Exemplary corrosion inhibitors further those wherein the cation is pyridinium or an imidazolinium as well as quat ammonium halides such as quat ammonium chlorides.
  • corrosion inhibitors include hydroxyl containing nitrogen or sulfur compounds such as alkylated thiols such as those of the formula HS(CH 2 ) x OH where x is from 1 to 8, like HSCH 2 CH 2 OH; anionic sulfonyl alcohols such as 2-(methylsulfonyl) ethanol; 2-sulfanylethanol; 2-sulfanyl, propan-1-ol; 2-sulfanylbutan-2-ol; 1-sulfanylbutanol-2-ol and mixtures thereof.
  • alkylated thiols such as those of the formula HS(CH 2 ) x OH where x is from 1 to 8, like HSCH 2 CH 2 OH
  • anionic sulfonyl alcohols such as 2-(methylsulfonyl) ethanol; 2-sulfanylethanol; 2-sulfanyl, propan-1-ol; 2-sulfanylbutan-2-ol; 1-sulfanylbutano
  • Exemplary ionic liquids include those of structure (IV):
  • R is a C 12 -C 18 alkyl or alkenyl group and X is —OH, NH 2 or C( ⁇ O)R;
  • exemplary phosphate esters or thiophosphate esters are those having one of structures (VA) or (VB):
  • R is an alkyl or RO(CH 2 CH 2 O) n CH 2 CH 2 ) and R′′ and R′′′ are independently selected from —H and a C 1 -C 20 alkyl;
  • exemplary quat ammonium chlorides are those of structure (VI):
  • alkyl group may contain from 1 to 20 carbon atoms; and exemplary alkyl pyridine quats are those of structure (VII):
  • R is a C 1 -C 18 alkyl or benzyl.
  • more than one R group can be a substituent to the pyridinyl ring.
  • the second R group is typically a C 1 -C 12 alkyl group.
  • Further exemplary corrosion inhibitors include thiazoles, triazoles and thiadiazoles such as benzotriazole, tolyltriazole, octyltriazole, decyltriazole, dodecyltriazole, 2-mercaptobenzothiazole, 2,5-dimercapto-1,3,4-thiadiazole, 2-mercapto-5-hydrocarbylthio-1,3,4-thiadiazoles, 2-mercapto-5-hydrocarbyldithio-1,3,4-thiadiazoles, 2,5-bis(hydrocarbylthio)-1,3,4-thiadiazoles, and 2,5-(bis)hydrocarbyldithio)-1,3,4-thiadiazoles.
  • benzotriazole tolyltriazole
  • octyltriazole decyltriazole
  • dodecyltriazole 2-mercaptobenzothiazole
  • anionic groups for anion X of formula (I), (II) and (III) include the counter anions of any of the corrosion inhibitors referenced above.
  • anion X of ionic liquid of formula (I), (II) and (III) may be an anionic phosphate ester, anionic thiophosphate ester, anionic phosphonate ester, anionic thiophosphonate ester, an anionic thiol, etc.
  • a treatment composition may be used for the inhibition, prevention or reduction of corrosion of metals; the treatment composition comprising the ionic liquids set forth above and one or more corrosion inhibitors (other than an ionic liquid).
  • Exemplary corrosion inhibitors include those set forth in the paragraphs above.
  • the anion X of the formula (I), (II) and (III) of the treatment composition may be the same anion as the counter anion of the corrosion inhibitor.
  • the treatment composition may contain (as corrosion inhibitor), the ionic liquid of (II) wherein R 1 , R 2 , R 3 and R 4 are hydrogen and anion X is the counter cation of (I) above.
  • corrosion inhibiting treatment compositions have been noted to provide a synergistic effect compared to the ionic liquid or the corrosion inhibitor by themselves. i.e., inhibition, prevention and/or reduction of corrosion significantly increases when fluids are contacted with a corrosion inhibiting treatment composition versus contacting of the metallic surface with the ionic liquid or corrosion inhibitor by themselves.
  • An anion exchange method was followed to prepare sulfur based ionic liquids.
  • a general procedure for the anion exchange method was followed wherein about 1 gram of KOH was dissolved in 5 grams methanol. About 1.36 grams 2-mercaptoethanol was added while stirring at 60° C. for 15 minutes. About 5 grams of a solution of N-benzyl, 2 methyl pyridinium chloride (75%) in methanol (25%) was then added dropwise and the mix stirred at 60° C. After 30 minutes of stirring, the solution was filtered while still hot to remove the potassium chloride by-product. The product was characterized by the replacement of the chloride on the pyridinium by the mercaptide of the 2-mercaptoethanol.
  • a kettle test run was under the conditions of 10 ppm additive in a brine with a carbon dioxide sparge, run for 18 hours at 180° F. and the corrosion rate (CR) monitored using linear polarization resistance (LPR) probes.
  • the results are set forth in Table I.
  • a neutralization procedure was used to prepare ionic liquids.
  • the general procedure for all tests may be represented by preparation of tetra-n-butylammonium bitartrate (1:1 salt) wherein tartaric acid (10 grams, 0.067 moles) was added in portions to a stirred solution of 55% aqueous tetra-n-butylammonium hydroxide (31.6 grams, 0.067 mole). A slight exotherm occurred during the addition. The solution was stirred at room temperature for an additional 30 minutes before testing without further modification. The samples were then subjected to a kettle test using synthetic cooling water and the corrosion rate was monitored using linear polarization resistance (LPR) probes. The results are set forth in Table II.

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