WO2013048365A1 - Anti-agglomerate gas hydrate inhibitors for use in petroleum and natural gas systems - Google Patents
Anti-agglomerate gas hydrate inhibitors for use in petroleum and natural gas systems Download PDFInfo
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- WO2013048365A1 WO2013048365A1 PCT/US2011/053284 US2011053284W WO2013048365A1 WO 2013048365 A1 WO2013048365 A1 WO 2013048365A1 US 2011053284 W US2011053284 W US 2011053284W WO 2013048365 A1 WO2013048365 A1 WO 2013048365A1
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- WIPO (PCT)
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- acid
- amine
- agglomerate
- hydrate inhibitor
- organic
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Classifications
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- 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
- C09K8/52—Compositions for preventing, limiting or eliminating depositions, e.g. for cleaning
-
- 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
- C09K2208/22—Hydrates inhibition by using well treatment fluids containing inhibitors of hydrate formers
Definitions
- the systems and methods described herein pertain to the production of petroleum products and natural gas, and particularly to compositions effective as anti- agglomerate low dosage gas hydrate inhibitors ("LDHI's") for the prevention of gas hydrate plugs.
- LDHI's low dosage gas hydrate inhibitors
- Gas hydrates are solids that may form during hydrocarbon production, in particular in pipelines and other equipment, that may impede or completely block flow of hydrocarbons. These blockages not only decrease or stop production, potentially costing millions of dollars in lost production, but are also very difficult and dangerous to mediate. Unless properly handled, gas hydrates may explode, rupturing pipelines, damaging equipment, endangering workers and putting at risk the ocean environment.
- Gas hydrates may form when water molecules become bonded together after coming into contact with certain "guest" gas molecules. Hydrogen bonding causes the water molecules to form a regular lattice structure that is stabilized by the guest gas molecules. The resulting crystalline structure precipitates as a solid gas hydrate.
- Guest molecules can include any number of molecules, including carbon dioxide, methane, butane, propane, hydrogen, helium, freons, halogens, and noble gases.
- Thermodynamic, anti-agglomerate, and kinetic inhibitors are three general classes of hydrate inhibitors.
- Thermodynamic inhibitors are most commonly used.
- Thermodynamic inhibitors such as methanol and ethylene glycol must typically be used at high concentrations to be effective, concentrations that may present environmental concerns. For instance, methanol is used in concentrations of up to 50% methanol to water ratio, with glycol as much as 30% glycol to water. Methanol presents other challenges, as it is flammable and can be corrosive.
- thermodynamic inhibitors are often not appropriate for many drilling operations, particularly environmentally-sensitive drilling operations.
- Kinetic inhibitors and anti-agglomerate inhibitors typically function at lower concentrations than thermodynamic inhibitors and are therefore termed LDHI's.
- Kinetic hydrate inhibitors are polymers that may prevent or delay the nucleation of hydrates. Thus the kinetic hydrate inhibitors limit hydrate crystal size and growth such that hydrate plugs are not allowed to form in tubular goods.
- kinetic hydrate inhibitors are capable of handling only low-to moderate subcooling - typically subcooling of about 10 - 25° F (subcooling is the difference between the operating temperature of the hydrocarbon system and the temperature at which hydrates would form at the same operating pressure).
- subcooling is the difference between the operating temperature of the hydrocarbon system and the temperature at which hydrates would form at the same operating pressure.
- kinetic hydrate inhibitors may not be suitable in deep and ultra-deep wells, where subcooling may be greater than 30°F.
- Anti-agglomerate gas inhibitors are typically more cost effective than thermodynamic inhibitors, as they may be used in much lower concentrations and are typically useful in environments with greater subcooling than would be appropriate for kinetic inhibitors.
- many of the traditional anti-agglomerate LDHI's contain residual halides, such as HC1, HBr, and the like, and residual organic halides. Residual halides have been know to cause corrosion and stress corrosion cracking ("SCC") in metal piping and production equipment.
- SCC corrosion and stress corrosion cracking
- One example of a commonly used anti-agglomerate LDHI is quaternary an ti- agglomerates containing residual organic halides, such as Kelland, 2006. As an example, Milburn et al. U.S. Patent No.
- the present disclosure relates generally to the field of gas and oil production. Other uses may also be made of same. In particular, compositions and methods for inhibiting the formation of gas hydrate plugs are described.
- compositions which are an ti- agglomerate low dosage hydrate inhibitors ("AA-LDHI"s) that are made without the use of organic chlorides or halides to minimize residual organic halides other resultant inorganic halides that are respectively highly toxic and corrosive.
- AA-LDHI ti- agglomerate low dosage hydrate inhibitors
- examples of such halides include HF, HC1, HBr, HI, and the like.
- compositions are structurally similar to quaternary amines, they are reaction products of organic acids and organic amines that eliminate or substantially reduce residual inorganic or organic halides (MX), and/or residual hydrogen halides (HC1, HBr, HI, and the like).
- MX inorganic halides
- HX hydrogen halides
- Inorganic halides (MX), and/or residual HX are often created as byproducts when quaternary salts are produced using chlorinated or halogenated alkylating agents. These agents typically include benzyl chloride, bromide, iodide, or the like, of the structure R-X wherein R is any organic structure. This byproduct formation is due to their reaction with water either during or after the reaction.
- the anti-agglomerate low dosage hydrate inhibitors are mixtures of organic reaction products of organic acids and organic amines, including but not limited to those including fatty acids and fatty amines.
- compositions effectively inhibit the formation of gas hydrates in petroleum and natural gas production systems without the negative effects associated with residual chlorides or other halides, such as high corrosion rates, stress cracking, and potential high toxicity.
- Figure 1 shows a general structure of a quaternary ammonium salt having a chloride or other halide anion, wherein R 1 , R 2 , R 3 , and R 4 are generally and independently H or C 1 -C40, and X is generally F, CI, Br, I, other halides, or similar suitable substituents.
- Figure 2 shows general structures (a) and (b) of organic reaction products of organic acids and organic amines having an organic anion, wherein R 1 , R 2 , and R 3 are independently H or C 1 -C40, including all alkyl and aryl structures and isomers, and wherein R 4 is Q-C40, including all alkyl and aryl structures and isomers.
- Figure 3 shows a preferred embodiment of a general structure of the reaction product of a coconut oil based amine and a fatty coconut oil based acid, wherein n is 8-12.
- Figure 4 shows the results of a comparison of the effectiveness of four anti- agglomerate compositions based on rating criteria.
- the current anti-agglomerate compositions include mixtures of reaction products of non-halide-containing inorganic acids and/or organic acids with organic amines.
- the reaction products are structurally similar to other quaternary amine halide analogs, but the reaction products lack acid halides, inorganic halides, and organic halides.
- Certain embodiments include mixtures of reaction products of organic acids and organic amines, including an anti- agglomerate low dosage hydrate inhibitor that is free of acid halides, inorganic halides, and organic halides and that can be injected continuously with minimized concern for corrosion, stress corrosion cracking, or highly toxic reactants or reaction products.
- FIG. 1 shows a traditional example of a quaternary ammonium salt utilizing a halide as an anion.
- the quaternary ammonium cation is that portion of the molecule that has a positive charge, NRiR 2 R3R4 + .
- the term quaternary amine is often used to refer to the positively charged quaternary ammonium compound.
- R l5 R2, R 3 , and R4 can be any number of suitable constituents, including hydrogen (H), methyl (CH 3 ), ethyl (CH 2 CH 3 ), acetyl (COCH 3 ), other alkyl or aryl groups of varying lengths and structures, and others. Some of the R constituents may also be connected to each other. Those of skill in the art with the benefit of this disclosure will understand the varying natures of the R constituents.
- the anti-agglomerate LDHI is the reaction products of organic acid and organic amines.
- Reaction products of organic acids and organic amines are formed when certain organic acids are partially neutralized, giving them at least a partial negative charge that enables them to serve as anions in a salt.
- Figure 2 shows some general examples of reaction products or organic acids and organic amines having the structure R 1 R 2 R 3 HN + (R 4 COO " ) or R 1 R 2 R 3 HN + (R 4 PhO " ), wherein R 1 , R 2 , and R 3 are independently H or C1-C40, wherein R 4 is Q-C40, and wherein Ph is any phenyl group.
- the substituents C1-C4 0 include all alkyl and aryl structures and isomers within these embodiments.
- the negatively charged anions are anions created by partial or complete neutralization of acids.
- Certain embodiments can include reactions or mixtures that include varying ratios of the organic acid, organic amine, and the resulting salt of the reaction of the organic acid and amine.
- approximately stoichiometric amounts of the organic acid and amine are used to create the resultant salt.
- molar ratios of the reactants are adjusted so as to create a surplus of free organic amine in the resultant reaction product.
- the excess amine is less than about 1% (by mol) of the reaction product.
- the compounds that can be used as cations with the desired acid anions can be any suitable non-halide-containing amines.
- Ri, R 2 , and R 3 can be any suitable substituents, including hydrogen (H), methyl (CH 3 ), ethyl (CH 2 CH 3 ), acetyl (COCH 3 ), and other alkyl or aryl groups of varying lengths.
- Some of the R substituents may also be connected to each other and can include oxygen, nitrogen, and the like.
- Suitable cations include, but are not limited to ammonia, methylamine, di methylamine, tri methylamine, ethylamine, di ethylamine, tri ethylamine, n- propylamine, di-n-proplyamine, tri-n-propylamine, monoethanolamine, di ethanolamine, diethyl ethanaol amine, methyl ethanol amine, tri ethanol amine, methyl diethanol amine, propyl ethanolamine, ethyl diethanol amine, di methyl amino propyl amine, di propyl ethanol amine, din-butyl amine, di butyl propanol amine, dibutyl ethanolamine, morpholine, piperazine, octyl amine, dimethyl octyl amine, decyl amine, di methyl decyl amine, lauryl amine, dimethyl laurylamine, myristyl amine, dimethyl palmity
- R4 can be any suitable constituents, including hydrogen (H), methyl (CH 3 ), ethyl (CH 2 CH 3 ), acetyl (COCH 3 ), and other alkyl or aryl groups of varying lengths, and can include oxygen, nitrogen, and the like.
- Suitable anions include formic acid, acetic acid, lactic acid, cyanuric acid, angelic acid, propionic acid, butyric acid, aspartic acid, glycolic acid, adipic acid, maleic acid, citric acid, phthalic acid, anthranilic acid, octanoic acid, lauric acid, benzoic acid, salicylic acid, fumaric acid, oxalic acid, succinic acid, acrylic acid, cinnamic acid, azelaic acid, neodecanoic acid, benzilic acid, pelargonic acid, stearic acid, dimer acid, trimer acid, varying ratios of dimer-trimer acid blends, methane sulfonic acid, dodecyl benzene sulfonic acid, para- tolunene sulfonic acid, oleic acid, tall oil fatty acid, linoleic acid, abietic acid, rosin acid, napthe
- Examples of salts that meet one or more criteria above include the reaction product of a 1:1 molar ratio of benzoic acid and dimethyl palmitoyl amine, a 2:1 molar ratio of phthalic anhydride and cocodiamine, and a 2: 1 molar ratio of salicylic acid and cocodiamine.
- reaction products of organic acids and organic amines derived from coconut oil have the structure [CH3(CH2)n(CH 3 )2HN+] [CH3(CH 2 )nCOO-].
- Figure 3 shows a general representation of these possible reaction products of a coconut oil based amine and acid in which n can be varied from, for example, 8 to 12. This is an exemplary embodiment that in no way limits the scope of the anti-agglomerate compositions overall.
- Reaction products of organic acids and organic amines are more advantageous than traditional AA-LDHIs made from alkyl or aryl halides in several respects.
- AA-LDHIs In the reaction or manufacturing processes to form quaternary ammonium halides for use as AA-LDHIs it is common to form hydrogen halides and organic alcohols due to residual water present during and left over in the reaction mixtures.
- the reactants and reaction products in the current AA-LDHI compositions are not as corrosive as the likes of HC1 or HX, do not cause halide stress cracking, and are not as toxic. Because of these advantages, the anti-agglomerate compositions can be injected continuously into petroleum and natural gas systems. Methods of continuous injection include via umbilical or cap string.
- anti-agglomerate compositions can be applied at a concentration of about 0.05% to about 10%, and preferably at about 0.2% to about 1.5%.
- anti-agglomerate compositions comprised of mixtures of reaction products of organic acids and organic amines work by helping to emulsify water in oil. It is generally agreed that anti-agglomerate LDHI molecules need hydrocarbon to function and tend to emulsify water as an internal emulsion phase. This limits the growth and size of hydrate crystals to a form and size that does not allow the hydrates formed to plug production equipment.
- the current anti-agglomerate compositions have distinct advantages over those an ti- agglomerate compositions already commercially available, as all of these compositions contain residual chlorides.
- One advantage is the difference in corrosivity, which stems from the basic differences in corrosivity between inorganic acids such as HX or HCl and that of organic acids.
- the pKa associated with HX is much less than that associated with COOH.
- the current AA-LDHIs potentially resolve long term corrosion issues present with chlorides or HCl that are formed or are inherent in the quat type products typically used where continuous anti-agglomerate injection is required.
- Chloride stress corrosion cracking or hydrogen penetration is accelerated by the trace HCl formed in the reaction of R-Cl/R-X in quat manufacturing that has proven to be an issue in continuous versus batch use of quat based AA- LDHI.
- Testing has shown that the current anti-agglomerate compositions are equal to if not superior to the industry standard in performance.
- the current, non-quat anti- agglomerate compositions have greater oil solubility for reduction of water quality issues. This leads to increased "greenness" or environmental compatibility by partitioning more to the oil phase.
- compositions also lack certain inherent chronic or carcinogenic toxicity characteristics associated with residual RC1, RX, and other organic chloride or halide found in traditional AA-LDHIs, including vinyl chloride, benzyl chloride, alkyl bromides, and the like.
- AA-LDHIs made in accordance with the present disclosure have better stability at higher temperatures than traditional AA-LDHIs. In certain applications, it may be necessary for the AA-LDHI to be subjected to temperatures in excess of 250°F. Certain traditional AA-LDHIs, such as those made from quatenary amines, are known to degrade at higher temperatures, resulting in a reduction of efficiency in controlling hydrates. Those AA- LDHIs made in accordance with the present disclosure retain efficacy after exposure to temperatures in excess of 250°F.
- AA-LDHs made in accordance with the present disclosure, function as corrosion inhibitors. Corrosion in the production from oil and gas often is often as a result of the presence of water in the production equipment, either produced from the formation, from condensation, or from water injected into the well, for instance, for lift assist. Hydrogen sulfide (H 2 S) and carbon dioxide (C0 2 ) are often present in produced fluids, which can, in the presence of water, form acids such as sulfuric and carbonic acids (respectively). Oxygen, when present, may also contribute to corrosivity and is sometimes a contaminant in the water used for injection.
- H 2 S Hydrogen sulfide
- C0 2 carbon dioxide
- Oxygen when present, may also contribute to corrosivity and is sometimes a contaminant in the water used for injection.
- the AA-LDHIs of the present disclosure may, in addition to serving as AA- LDHIs, may function as corrosion inhibitors by contacting and coating the exposed metal of the oil and gas production equipment and piping.
- the exposed metal after being coated, by the corrosion inhibitor, prevents subsequent corrosion of the surface by the corrosive agents in the hydrocarbon stream.
- Corrosion inhibitors are normally delivered to through an umbilical to the oil and gas production equipment and piping.
- the additional use of the AA-LDHIs of the present disclosure as corrosion inhibitors has the benefit of both reducing costs to the driller by eliminating an additional on-site chemical, but also by eliminating the umbilical used to deliver the traditional corrosion inhibitor.
- AA-LDHIs made in accordance with the present disclosure were tested and compared to determine their effectiveness to prevent formation of hydrate crystals in gas production systems.
- the four AA-LDHIs tested were benzoic acid/dimethyl palmitoyl amine mixed in a 1:1 molar ratio, maleic anhydride/dimethyl palmitoyl amine mixed in a 1:1 molar ratio, methanesulfonic acid cocodiamine mixed in a 2:1 molar ratio, phthalic anhydride/cocodiamine mixed in a 2:1 molar ratio, and salicylic acid/cocodiamine mixed in a 2:1 molar ratio.
- a rocking cell test was performed on each of the four AA-LDHIs.
- the AA-LDHIs were tested in a bank of high pressure rocking cells. Each cell is outfitted with clear sapphire tubes housed and sealed in a Hastelloy body. The sapphire tubes allow for visual observation of the pressurized, cooled fluids inside the cell.
- the cells were isolated from each other and were equipped with pressure transducers and proximity sensors. A magnetic ball provided agitation as the cells are rocked back and forth at a predetermined angle and rate. The cells were submerged in a temperature controlled bath consisting of glycol and water.
- the gas composition was similar to GOM Green Canyon, a structure II hydrate former: Table 2.
- Type II Gas Composition
- Tests were all conducted at constant volume. Inhibitor concentration varied from 1-5 vol-% based upon the total amount of water.
- the cells were initially pressurized at 20°C to 2200 psig. Rocking was initialized at 15 rocks/min and an angle of +25° off horizontal. At constant temperature of 20°C the cells were rocked for 2 hours to mix the fluids and allow for the gas to saturate the fluids. The temperature was then ramped down continuously to 4°C over a period of 2 hours while rocking.
- Ball is free but resists rolling, moderate to little change in liquid level, large solid crystals, agglomerations that break up with agitation, no visible deposits on tube
- Ball is free, no change in liquid level, viscous liquid, small dispersible agglomerations or crystals, no visible deposits on tube.
- Ball is free, no change in liquid level, little to no change in viscosity, no visible deposits on tube or cylinder, extremely fine easily dispersible crystals.
- Figure 4 shows the results of the performance ranking.
Abstract
Description
Claims
Priority Applications (6)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CA2827471A CA2827471C (en) | 2011-09-26 | 2011-09-26 | Anti-agglomerate gas hydrate inhibitors for use in petroleum and natural gas systems |
EP11873453.2A EP2760965A4 (en) | 2011-09-26 | 2011-09-26 | Anti-agglomerate gas hydrate inhibitors for use in petroleum and natural gas systems |
MX2013009634A MX2013009634A (en) | 2011-09-26 | 2011-09-26 | Anti-agglomerate gas hydrate inhibitors for use in petroleum and natural gas systems. |
BR112013021905A BR112013021905A2 (en) | 2011-09-26 | 2011-09-26 | hydrate anti-caking inhibitor composition, and method for applying an anti-caking hydrate inhibiting composition to a hydrocarbon stream |
AU2011378265A AU2011378265A1 (en) | 2011-09-26 | 2011-09-26 | Anti-agglomerate gas hydrate inhibitors for use in petroleum and natural gas systems |
PCT/US2011/053284 WO2013048365A1 (en) | 2011-09-26 | 2011-09-26 | Anti-agglomerate gas hydrate inhibitors for use in petroleum and natural gas systems |
Applications Claiming Priority (1)
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PCT/US2011/053284 WO2013048365A1 (en) | 2011-09-26 | 2011-09-26 | Anti-agglomerate gas hydrate inhibitors for use in petroleum and natural gas systems |
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WO2013048365A1 true WO2013048365A1 (en) | 2013-04-04 |
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PCT/US2011/053284 WO2013048365A1 (en) | 2011-09-26 | 2011-09-26 | Anti-agglomerate gas hydrate inhibitors for use in petroleum and natural gas systems |
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EP (1) | EP2760965A4 (en) |
AU (1) | AU2011378265A1 (en) |
BR (1) | BR112013021905A2 (en) |
CA (1) | CA2827471C (en) |
MX (1) | MX2013009634A (en) |
WO (1) | WO2013048365A1 (en) |
Cited By (17)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2016070044A1 (en) * | 2014-10-30 | 2016-05-06 | Preferred Technology, Llc | Proppants and methods of use thereof |
US9410073B2 (en) | 2013-11-26 | 2016-08-09 | Ecolab Usa Inc. | Anti-agglomerants for controlling gas hydrates |
US9518214B2 (en) | 2013-03-15 | 2016-12-13 | Preferred Technology, Llc | Proppant with polyurea-type coating |
US9562187B2 (en) | 2012-01-23 | 2017-02-07 | Preferred Technology, Llc | Manufacture of polymer coated proppants |
US9624421B2 (en) | 2011-09-02 | 2017-04-18 | Preferred Technology, Llc | Dual function proppants |
US9725645B2 (en) | 2011-05-03 | 2017-08-08 | Preferred Technology, Llc | Proppant with composite coating |
US9790422B2 (en) | 2014-04-30 | 2017-10-17 | Preferred Technology, Llc | Proppant mixtures |
US9862881B2 (en) | 2015-05-13 | 2018-01-09 | Preferred Technology, Llc | Hydrophobic coating of particulates for enhanced well productivity |
US10006128B2 (en) | 2012-09-28 | 2018-06-26 | Ecolab Usa Inc. | Quaternary and cationic ammonium surfactants as corrosion inhibitors |
US10100247B2 (en) | 2013-05-17 | 2018-10-16 | Preferred Technology, Llc | Proppant with enhanced interparticle bonding |
US10544358B2 (en) | 2011-05-03 | 2020-01-28 | Preferred Technology, Llc | Coated and cured proppants |
US10590337B2 (en) | 2015-05-13 | 2020-03-17 | Preferred Technology, Llc | High performance proppants |
US10696896B2 (en) | 2016-11-28 | 2020-06-30 | Prefferred Technology, Llc | Durable coatings and uses thereof |
WO2020161407A1 (en) | 2019-02-06 | 2020-08-13 | Arkema France | Composition for preventing agglomeration of gas hydrates |
WO2020239339A1 (en) | 2019-05-28 | 2020-12-03 | Clariant International Ltd | Method for inhibiting gas hydrate blockage in oil and gas pipelines |
WO2020239338A1 (en) | 2019-05-28 | 2020-12-03 | Clariant International Ltd | Method for inhibiting gas hydrate blockage in oil and gas pipelines |
US11208591B2 (en) | 2016-11-16 | 2021-12-28 | Preferred Technology, Llc | Hydrophobic coating of particulates for enhanced well productivity |
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WO2012040329A1 (en) * | 2010-09-21 | 2012-03-29 | Multi-Chem Group, Llc | Water removal from anti-agglomerate ldhis |
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- 2011-09-26 MX MX2013009634A patent/MX2013009634A/en not_active Application Discontinuation
- 2011-09-26 BR BR112013021905A patent/BR112013021905A2/en not_active Application Discontinuation
- 2011-09-26 EP EP11873453.2A patent/EP2760965A4/en not_active Withdrawn
- 2011-09-26 AU AU2011378265A patent/AU2011378265A1/en not_active Abandoned
- 2011-09-26 CA CA2827471A patent/CA2827471C/en not_active Expired - Fee Related
- 2011-09-26 WO PCT/US2011/053284 patent/WO2013048365A1/en active Application Filing
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US9725645B2 (en) | 2011-05-03 | 2017-08-08 | Preferred Technology, Llc | Proppant with composite coating |
US10544358B2 (en) | 2011-05-03 | 2020-01-28 | Preferred Technology, Llc | Coated and cured proppants |
US9624421B2 (en) | 2011-09-02 | 2017-04-18 | Preferred Technology, Llc | Dual function proppants |
US10087360B2 (en) | 2011-09-02 | 2018-10-02 | Preferred Technology, Llc | Dual function proppants |
US9562187B2 (en) | 2012-01-23 | 2017-02-07 | Preferred Technology, Llc | Manufacture of polymer coated proppants |
US10006128B2 (en) | 2012-09-28 | 2018-06-26 | Ecolab Usa Inc. | Quaternary and cationic ammonium surfactants as corrosion inhibitors |
US9518214B2 (en) | 2013-03-15 | 2016-12-13 | Preferred Technology, Llc | Proppant with polyurea-type coating |
US10208242B2 (en) | 2013-03-15 | 2019-02-19 | Preferred Technology, Llc | Proppant with polyurea-type coating |
US11760924B2 (en) | 2013-05-17 | 2023-09-19 | Preferred Technology, Llc | Proppant with enhanced interparticle bonding |
US11098242B2 (en) | 2013-05-17 | 2021-08-24 | Preferred Technology, Llc | Proppant with enhanced interparticle bonding |
US10100247B2 (en) | 2013-05-17 | 2018-10-16 | Preferred Technology, Llc | Proppant with enhanced interparticle bonding |
US9410073B2 (en) | 2013-11-26 | 2016-08-09 | Ecolab Usa Inc. | Anti-agglomerants for controlling gas hydrates |
US10281086B2 (en) | 2013-11-26 | 2019-05-07 | Ecolab Usa Inc. | Anti-agglomerants for controlling gas hydrates |
US9790422B2 (en) | 2014-04-30 | 2017-10-17 | Preferred Technology, Llc | Proppant mixtures |
WO2016070044A1 (en) * | 2014-10-30 | 2016-05-06 | Preferred Technology, Llc | Proppants and methods of use thereof |
US10590337B2 (en) | 2015-05-13 | 2020-03-17 | Preferred Technology, Llc | High performance proppants |
US9862881B2 (en) | 2015-05-13 | 2018-01-09 | Preferred Technology, Llc | Hydrophobic coating of particulates for enhanced well productivity |
US11208591B2 (en) | 2016-11-16 | 2021-12-28 | Preferred Technology, Llc | Hydrophobic coating of particulates for enhanced well productivity |
US10696896B2 (en) | 2016-11-28 | 2020-06-30 | Prefferred Technology, Llc | Durable coatings and uses thereof |
WO2020161407A1 (en) | 2019-02-06 | 2020-08-13 | Arkema France | Composition for preventing agglomeration of gas hydrates |
WO2020239339A1 (en) | 2019-05-28 | 2020-12-03 | Clariant International Ltd | Method for inhibiting gas hydrate blockage in oil and gas pipelines |
WO2020239338A1 (en) | 2019-05-28 | 2020-12-03 | Clariant International Ltd | Method for inhibiting gas hydrate blockage in oil and gas pipelines |
US11753577B2 (en) | 2019-05-28 | 2023-09-12 | Clariant International Ltd. | Method for inhibiting gas hydrate blockage in oil and gas pipelines |
US11753576B2 (en) | 2019-05-28 | 2023-09-12 | Clariant International Ltd. | Method for inhibiting gas hydrate blockage in oil and gas pipelines |
Also Published As
Publication number | Publication date |
---|---|
AU2011378265A1 (en) | 2013-08-15 |
CA2827471A1 (en) | 2013-04-04 |
BR112013021905A2 (en) | 2016-11-01 |
EP2760965A1 (en) | 2014-08-06 |
CA2827471C (en) | 2016-11-01 |
MX2013009634A (en) | 2014-01-24 |
EP2760965A4 (en) | 2015-04-22 |
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