EP3737781A1 - Additives to control hydrogen sulfide release of sulfur containing and/or phosphorus containing corrosion inhibitors - Google Patents
Additives to control hydrogen sulfide release of sulfur containing and/or phosphorus containing corrosion inhibitorsInfo
- Publication number
- EP3737781A1 EP3737781A1 EP19738997.6A EP19738997A EP3737781A1 EP 3737781 A1 EP3737781 A1 EP 3737781A1 EP 19738997 A EP19738997 A EP 19738997A EP 3737781 A1 EP3737781 A1 EP 3737781A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- combinations
- group
- phosphorous
- additive
- reaction product
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C23—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; CHEMICAL SURFACE TREATMENT; DIFFUSION TREATMENT OF METALLIC MATERIAL; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL
- C23F—NON-MECHANICAL REMOVAL OF METALLIC MATERIAL FROM SURFACE; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL; MULTI-STEP PROCESSES FOR SURFACE TREATMENT OF METALLIC MATERIAL INVOLVING AT LEAST ONE PROCESS PROVIDED FOR IN CLASS C23 AND AT LEAST ONE PROCESS COVERED BY SUBCLASS C21D OR C22F OR CLASS C25
- C23F11/00—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent
- C23F11/08—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent in other liquids
- C23F11/10—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent in other liquids using organic inhibitors
- C23F11/167—Phosphorus-containing compounds
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K8/00—Compositions for drilling of boreholes or wells; Compositions for treating boreholes or wells, e.g. for completion or for remedial operations
- C09K8/54—Compositions for in situ inhibition of corrosion in boreholes or wells
-
- C—CHEMISTRY; METALLURGY
- C23—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; CHEMICAL SURFACE TREATMENT; DIFFUSION TREATMENT OF METALLIC MATERIAL; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL
- C23F—NON-MECHANICAL REMOVAL OF METALLIC MATERIAL FROM SURFACE; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL; MULTI-STEP PROCESSES FOR SURFACE TREATMENT OF METALLIC MATERIAL INVOLVING AT LEAST ONE PROCESS PROVIDED FOR IN CLASS C23 AND AT LEAST ONE PROCESS COVERED BY SUBCLASS C21D OR C22F OR CLASS C25
- C23F11/00—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent
- C23F11/08—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent in other liquids
- C23F11/10—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent in other liquids using organic inhibitors
- C23F11/16—Sulfur-containing compounds
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2208/00—Aspects relating to compositions of drilling or well treatment fluids
- C09K2208/32—Anticorrosion additives
Definitions
- the present invention relates to inactivating at least one sulfur-containing and/or at least one phosphorous-containing corrosion inhibitors in a system by introducing at least one additive, such as an aminal, a dialkylamine, and combinations thereof, to the corrosion inhibitor within the system to control or reduce the release of hydrogen sulfide.
- at least one additive such as an aminal, a dialkylamine, and combinations thereof
- One of the most difficult problems in the field of corrosion inhibition is that of preventing and/or inhibiting corrosion in oxygenated aqueous systems, such as in water floods, cooling towers, drilling muds, air drilling, auto radiator systems, etc.
- Many corrosion inhibitors capable of performing in non-aqueous systems and/or non-oxygenated systems perform poorly in aqueous and/or oxygenated systems (i.e. aerobic systems).
- Pyrophosphates are one non-limiting example of a type of corrosion inhibitor used as corrosion inhibitors in oxygenated systems.
- Ethoxylated fatty alcohol may react with phosphorous pentasulfide to form O,O-disubstituted dithiophosphoric acid and pyrophosphates as described in U.S. Patent Application No. 4,075,291 , which is herein incorporated by reference in its entirety.
- The‘291 patent sets forth the following reactions for obtaining the pyrophosphate products:
- the O,O-disubstituted dithiophosphoric acid initially formed may proceed through an anhydride formation and/or an isomerization to yield the pyrophosphates as shown in the above reactions.
- the final reaction yields about 40% O,O-disubstituted dithiophosphoric acid as a final product and 60% pyrophosphates and anhydride products.
- hydrogen sulfide may still form from the anhydride formation and/or isomerization of the O,O-disubstituted dithiophosphoric acid reaction, even after storage and handling of the resulting product.
- hydrogen sulfide may be released into the environment upon usage of the pyrophosphates.
- hydrogen sulfide may be produced form the labile P— S— H linkage in the O,O-disubstituted dithiophosphoric acid.
- the water formed from the pyrophosphate reaction and/or moisture in the storage container, under normal handling conditions, may react with O,O-disubstituted dithiophosphoric acid to form additional hydrogen sulfide.
- This additional hydrogen sulfide tends to accumulate in the headspace of a storage container and has been difficult to remove prior to using the product (e.g. pyrophosphates).
- a system having at least one phosphorous-containing compound and at least one additive.
- the phosphorous-containing compound may be or include 0,0- disubstituted dithiophosphoric acid, pyrophosphates, and combinations thereof.
- the additive may be or may include an aminal, a dialkylamine, and combinations thereof.
- the system may be or include an aqueous system, an aerobic system, an anaerobic system, and combinations thereof.
- the system may further include at least one sulfur species and may have at least one inactivated composition, such as at least one inactivated sulfur species, at least one inactivated phosphorous-containing compounds, and combinations thereof.
- a method comprising introducing at least one additive to a corrosion inhibitor in a system, wherein the corrosion inhibitor comprises at least one phosphorous- containing compound, such as O,O-disubstituted dithiophosphoric acid, pyrophosphates, and combinations thereof.
- the additive may be or include an aminal, a dialkylamine, and combinations thereof.
- the system may be or include an aqueous system, an aerobic system, an anaerobic system, and combinations thereof.
- the corrosion inhibitor may also include at least one sulfur species. The method may further include inactivating the phosphorous-containing compound(s), the sulfur specie(s), and combinations thereof.
- the amount of hydrogen sulfide in a head-space of a container having pyrophosphates may increase during storage even after extended nitrogen purging of the container to remove excess hydrogen sulfide.
- An additive may be introduced to the places within a system that contain a phosphorous-containing and/or sulfur-containing corrosion inhibitor, such as the container or the headspace of the container in a few illustrative non-limiting embodiments, to inactivate inactivate at least a portion of the sulfur specie(s) and/or the phosphorous-containing compound(s) so that it no longer releases H 2 S.
- Inactivate is defined herein to mean that the sulfur species and/or phosphorous-containing compounds may be chemically altered to no longer chemically react with other components in the current system to release H 2 S.
- the inactivated sulfur species and/or inactivated phosphorous-containing compounds are stable products.
- the methods described are considered successful if a majority of the sulfur species and/or phosphorous-containing compounds within the current system are inactivated. ‘Majority’ is defined herein to be an amount greater than about 50% of the sulfur species and/or the phosphorous-containing species within the current system.
- a first additive may be or include, but is not limited to, an aminal, or a dialkylamine.
- Two or more additives may be circulated in formulating the corrosion inhibitor at the same time or at different times. The additives do not need to be added or circulated at the same time in formulating the corrosion inhibitor to be considered effective (but, it is preferred).
- dialkylamine, dialkylamine - O-O-disubstituted dithiophosphoric acid salt, thioformaldehyde, and combinations thereof may be produced within the system as a product of a reaction to inactivate the sulfur species and/or phosphorous- containing compounds.
- the dialkylamine may have or include alkyl group that are straight or branched chain, and each alkyl group may have from 1 carbon to about 5 carbons, or from about 2 carbons to about 4 carbons.
- the aminal may be a linear aminal, or a cyclic aminal, such as but not limited to tetrahydropyrimidine, hexahydropyrimidine, pyrophosphates, and combinations thereof.
- the cyclic aminal may be 5-tetrahydropyrimidine (5-THP) or another cyclic aminal that is formed by reacting a carbonyl compound (ketone or aldehyde) with ammonia, such as those described in U.S. Patent No. 3,904,624, which is herein incorporated by reference in its entirety.
- hexahydropyrimidine may be or include 2,2,4,4-dipentamethylene-5,6- tetramethylene hexahydropyrimidine, such as that described by U.S. Patent No. 3,936,279, which is herein incorporated by reference in its entirety.
- R1 -R4 of the aminal may be or include at least one butyl group; R1 -R4 may be all butyl groups (e.g. (Bu) 2 N- CH 2 -N(BU) 2 ), or only one R group of R1 -R4 may be a butyl group.
- Non-limiting combinations of the additives may be or include (BU) 2 N-CH 2 -N(BU) 2 , and dibutylamine, and combinations thereof; maleic anhydride and dibutylamine; maleic anhydride and (Bu) 2 N-CH 2 - N(BU) 2 , etc.
- ‘first’ and‘second’ with respect to the additives are used as descriptors to distinguish between the additives circulated within system; additives noted as‘first’ or‘second’ additives do not necessarily need to be circulated in the system in a particular order.
- the system may have or include an increased amount of at least one inactivated sulfur species and/or inactivated phosphorous- containing corrosion inhibitor as compared to an otherwise identical system absent the additive(s).
- the phosphorous-containing compound may be or include 0,0- disubstituted dithiophosphoric acid, pyrophosphates, and combinations thereof.
- the system may be an aqueous system, an aerobic system (an oxygenated system), an anaerobic system, and combinations thereof.
- the aerobic system may be or include a water flood, a water-based or brine-based fluid for drilling or exploration, a cooling tower, air drilling, an auto radiator system, and combinations thereof.
- Non-limiting examples of the water-based or brine-based fluid may be or include drilling fluids, completion fluids, stimulation fluids, servicing fluids, and combinations thereof.
- Drilling fluids are typically classified according to their base fluid.
- water-based fluids solid particles are suspended in a continuous phase consisting of water or brine. Oil can be emulsified in the water which is the continuous phase.
- Aqueous-based fluid is used herein to include fluids having an aqueous continuous phase where the aqueous continuous phase can be all water or brine, an oil-in-water emulsion, or an oil-in-brine emulsion.
- Brine-based fluids of course are water-based fluids, in which the aqueous component is brine.
- Completion fluids may be placed in a well to facilitate final operations prior to initiation of production.
- Completion fluids are typically brines, such as chlorides, bromides, formates, but may be any non-damaging fluid having proper density and flow characteristics.
- Suitable salts for forming the brines include, but are not necessarily limited to, sodium chloride, calcium chloride, zinc chloride, potassium chloride, potassium bromide, sodium bromide, calcium bromide, zinc bromide, sodium formate, potassium formate, ammonium formate, cesium formate, and mixtures thereof.
- Chemical compatibility of the completion fluid with the reservoir formation and fluids is key.
- Chemical additives such as polymers and surfactants are known in the art for being introduced to the brines used in well servicing fluids for various reasons that include, but are not limited to, increasing viscosity, and increasing the density of the brine.
- Water-thickening polymers serve to increase the viscosity of the brines and thus retard the migration of the brines into the formation and lift drilled solids from the well-bore.
- Completion fluids also help place certain completion-related equipment, such as gravel packs, without damaging the producing subterranean formation zones.
- Conventional drilling fluids are rarely suitable for completion operations due to their solids content, pH, and ionic composition.
- remediation fluids such as remediation fluids, workover fluids, and the like
- Such fluids may be used for breaking emulsions already formed and for removing formation damage that may have occurred during the drilling, completion and/or production operations.
- the terms "remedial operations” and “remediate” are defined herein to include a lowering of the viscosity of gel damage and/or the partial or complete removal of damage of any type from a subterranean formation.
- the term “remediation fluid” is defined herein to include any fluid that may be useful in remedial operations.
- any tubing-casing packers may be unseated, and then servicing fluids are run down the tubing-casing annulus and up the tubing string. These servicing fluids aid in balancing the pressure of the reservoir and prevent the influx of any reservoir fluids.
- the tubing may be removed from the well once the well pressure is under control.
- the dibutylamine may react with O, O-disubstituted dithiophosphoric acid in a second reaction to produce a stable phosphorous-containing salt, which does not further release hydrogen sulfide, or does not further react within the current system.
- the phosphorous-containing salt is the ‘second reaction product’ for purposes of this example.‘Current system’ is defined as a system having components therein at the time the additive(s) are circulated. [0026] Reactants ‘A’ and ⁇ ’ may form the product ‘stable salt’ where‘stable salt’ is the stable phosphorous-containing salt according to the following reaction:
- first reaction ‘first reaction product’, ‘second reaction’, and‘second reaction product’ are used to distinguish between the two types of reactions and their corresponding reaction products.
- the reactions will proceed in a sequential manner, such as that noted above.
- dialkylamine e.g. dibutylamine
- (R1 ) 2 N-CH 2 -N(R1 ) 2 e.g. (Bu) 2 N- CH 2 -N(BU) 2
- the ‘second reaction’ i.e. where the dibutylamine targets the O, O disubstituted dithiophosphoric acid, may occur in the absence of the‘first reaction’.
- an amount of the (R 1 ) 2 N-CH 2 - N(R I ) 2 [e.g. (BU) 2 N-CH 2 -N(BU) 2 ] to be reacted with the 0,0- disubstituted dithiophosphoric acid may be calculated by using the formula:
- X (0.0019)(acid number)(Y)
- X is the amount of (R 1 ) 2 N-CH 2 -N(R 1 ) 2 [e.g. (Bu) 2 N-CH 2 -N(Bu) 2 ] in grams and where Y is the amount of the O,O-disubstituted dithiophosphoric acid in grams.
- the (R 1 ) 2 N-CH 2 -N(R 1 ) 2 [e.g. (Bu) 2 N- CH 2 -N(BU) 2 ] may target both the sulfur species and the phosphorous- containing compound, if both are present in a current system.
- the mole ratio of (R I ) 2 N-CH 2 -N(R I ) 2 [e.g. (Bu) 2 N-CH 2 - N(BU) 2 ] to the O,O-disubstituted dithiophosphoric acid may range from about 0.1 :1 independently to about 0.5:1 , or alternatively from about 0.3:1 independently to about 1 :2.
- the mole ratio of (R 1 ) 2 N-CH 2 -N(R 1 ) 2 [e.g. (BU) 2 N-CH 2 -N(BU) 2 ] to the hydrogen sulfide may range from about 1 : 1 to about 2:1 , or from about 2:1 independently to about 0.33:1 in a non-limiting embodiment.
- the effective amount of additive within the system may vary depending on the local conditions and the particular system being treated.
- the amount of the additive to be added may range from about 1 wt% independently to about 15 wt% based on the total amount of fluid in the system, alternatively from about 5 wt% independently to about 12 wt%, or from about 8 wt% independently to about 10 wt% in another non-limiting embodiment.
- “independently” means that any threshold may be used together with another threshold to give a suitable alternative range, e.g. about 1 wt% independently to about 5 wt% is also considered a suitable alternative range.
- the temperature and other characteristics of the system may have a bearing on the amount of the additive to be added thereto.
- the temperature of the system may range from about 0 °C independently to about 400 °C, or from about 30 °C independently to about 300 °C in another non-limiting embodiment, or from about 50 °C independently to about 205 °C.
- the compound eliminated the hydrogen sulfide in the headspace, which had a volume of about 30% of the total volume of the container.
- Head-space is defined herein as the unfilled space above the contents within a closed container.
- the additive may also react with 0,0- disubstituted dithiophosphoric acid to form a phosphorous-containing stable salt.
- One mole of the additive reacted with two moles of 0,0- disubstituted dithiophosphoric acid to form the stable salt.
- one mole of the additive inactivated one mole of hydrogen sulfide within the current system.
- Stable is defined herein to mean that the salt or reaction product does not further react within the current system, i.e. no additional hydrogen sulfide or other byproducts are generated from the stable salt or stable reaction product within the current system.
- a C 8 -Cio fatty alcohol reacted with 3 - 4 moles of ethylene oxide (576 g: 2 mol) and was stirred at a temperature between about 25 °C to about 40 °C, while P2S5 (1 1 1 g; 0.5 mol) was added over a period of 2 hours.
- the reaction was heated to a temperature between about 105 °C and 109 °C at a pressure of about 70 mmHg for about 9.5 hrs.
- 657 g was obtained as a pale yellow liquid.
- the acid number was about 35 mg KOH/g for the product.
- Table 1 summarizes the results from additional examples where the efficiency of the aminal with three different corrosion inhibitor batches of O,O-disubstituted dithiophosphoric acid and pyrophosphates in aromatic 100 solvent was measured.
- the first two sets measured the amount of H 2 S levels for each sample within both sets after 2 months.
- the third set measured the amount of H2S levels for each sample within set 3 after 6 days.
- Sets 1 and 2 were left at ambient temperature during the two-month period, while the temperature for the samples within Set 3 was 40°C.
- the increased temperature within Set 3 may have accelerated the release of any H 2 S release remaining within the headspace.
- an increased amount of aminal added to the head space decreases the amount of H 2 S within the headspace.
- increasing the temperature during the reaction and possibly after the reaction may decrease the amount of H 2 S within the headspace.
- the present invention may suitably comprise, consist or consist essentially of the elements disclosed and may be practiced in the absence of an element not disclosed.
- the treated system may consist of or consist essentially of a system, at least one phosphorous-containing compound, and at least one additive.
- the method may consist of or consist essentially introducing an additive to a corrosion inhibitor within a system, wherein the corrosion inhibitor is a phosphorous-containing compound selected from the group consisting of O,O-disubstituted dithiophosphoric acid, pyrophosphates, and combinations thereof and wherein the additive is selected from a group consisting of an aminal, a dialkylamine, and combinations thereof; and the system is an aqueous system, an aerobic system, and/or an anaerobic system.
- the corrosion inhibitor is a phosphorous-containing compound selected from the group consisting of O,O-disubstituted dithiophosphoric acid, pyrophosphates, and combinations thereof
- the additive is selected from a group consisting of an aminal, a dialkylamine, and combinations thereof
- the system is an aqueous system, an aerobic system, and/or an anaerobic system.
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- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Chemistry (AREA)
- Mechanical Engineering (AREA)
- Metallurgy (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Life Sciences & Earth Sciences (AREA)
- Preventing Corrosion Or Incrustation Of Metals (AREA)
Abstract
Description
Claims
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US15/870,297 US10655232B2 (en) | 2014-09-03 | 2018-01-12 | Additives to control hydrogen sulfide release of sulfur containing and/or phosphorus containing corrosion inhibitors |
PCT/US2019/012735 WO2019139910A1 (en) | 2018-01-12 | 2019-01-08 | Additives to control hydrogen sulfide release of sulfur containing and/or phosphorus containing corrosion inhibitors |
Publications (2)
Publication Number | Publication Date |
---|---|
EP3737781A1 true EP3737781A1 (en) | 2020-11-18 |
EP3737781A4 EP3737781A4 (en) | 2021-04-14 |
Family
ID=67219824
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP19738997.6A Withdrawn EP3737781A4 (en) | 2018-01-12 | 2019-01-08 | Additives to control hydrogen sulfide release of sulfur containing and/or phosphorus containing corrosion inhibitors |
Country Status (3)
Country | Link |
---|---|
EP (1) | EP3737781A4 (en) |
CA (1) | CA3086018A1 (en) |
WO (1) | WO2019139910A1 (en) |
Family Cites Families (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4042323A (en) * | 1972-07-17 | 1977-08-16 | Petrolite Corporation | Process of inhibiting corrosion of metal in an aqueous environment with mixtures of thio-, oxygen and thio- oxygen phosphates and pyrophosphates |
US4775458A (en) * | 1986-12-18 | 1988-10-04 | Betz Laboratories, Inc. | Multifunctional antifoulant compositions and methods of use thereof |
GB8910711D0 (en) * | 1989-05-10 | 1989-06-28 | Davy Mckee London | Process |
US5698171A (en) * | 1996-01-10 | 1997-12-16 | Quaker Chemical Corporation | Regenerative method for removing sulfides from gas streams |
US6663841B2 (en) * | 2002-04-18 | 2003-12-16 | Baker Hughes Incorporated | Removal of H2S and/or mercaptans form supercritical and/or liquid CO2 |
US20070119747A1 (en) * | 2005-11-30 | 2007-05-31 | Baker Hughes Incorporated | Corrosion inhibitor |
US8663457B2 (en) * | 2011-11-23 | 2014-03-04 | General Electric Company | Methods and compounds for improving sulfide scavenging activity |
US20160060520A1 (en) * | 2014-09-03 | 2016-03-03 | Baker Hughes Incorporated | Scavengers for sulfur species and/or phosphorus containing compounds |
-
2019
- 2019-01-08 CA CA3086018A patent/CA3086018A1/en not_active Abandoned
- 2019-01-08 WO PCT/US2019/012735 patent/WO2019139910A1/en unknown
- 2019-01-08 EP EP19738997.6A patent/EP3737781A4/en not_active Withdrawn
Also Published As
Publication number | Publication date |
---|---|
CA3086018A1 (en) | 2019-07-18 |
WO2019139910A1 (en) | 2019-07-18 |
EP3737781A4 (en) | 2021-04-14 |
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