WO1993025798A1 - Procede d'inhibition de la formation d'hydrates de gaz - Google Patents
Procede d'inhibition de la formation d'hydrates de gaz Download PDFInfo
- Publication number
- WO1993025798A1 WO1993025798A1 PCT/EP1993/001519 EP9301519W WO9325798A1 WO 1993025798 A1 WO1993025798 A1 WO 1993025798A1 EP 9301519 W EP9301519 W EP 9301519W WO 9325798 A1 WO9325798 A1 WO 9325798A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- vinyl
- pvp
- additive
- pyrrolidone
- water
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 16
- 230000015572 biosynthetic process Effects 0.000 title claims abstract description 13
- NMJORVOYSJLJGU-UHFFFAOYSA-N methane clathrate Chemical compound C.C.C.C.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O NMJORVOYSJLJGU-UHFFFAOYSA-N 0.000 title claims abstract description 11
- 230000002401 inhibitory effect Effects 0.000 title claims abstract description 8
- 239000013078 crystal Substances 0.000 claims abstract description 39
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 claims abstract description 31
- 239000000654 additive Substances 0.000 claims abstract description 23
- 239000000203 mixture Substances 0.000 claims abstract description 23
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 21
- 230000000996 additive effect Effects 0.000 claims abstract description 13
- 229920001577 copolymer Polymers 0.000 claims abstract description 13
- 229930195733 hydrocarbon Natural products 0.000 claims abstract description 12
- 150000002430 hydrocarbons Chemical class 0.000 claims abstract description 12
- 238000009835 boiling Methods 0.000 claims abstract description 9
- 229920000642 polymer Polymers 0.000 claims abstract description 7
- 238000005054 agglomeration Methods 0.000 claims abstract description 5
- 230000002776 aggregation Effects 0.000 claims abstract description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 4
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 claims description 6
- AFFLGGQVNFXPEV-UHFFFAOYSA-N 1-decene Chemical compound CCCCCCCCC=C AFFLGGQVNFXPEV-UHFFFAOYSA-N 0.000 claims description 4
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 claims description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- -1 alkyl diamines Chemical class 0.000 claims description 3
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 claims description 2
- 239000004215 Carbon black (E152) Substances 0.000 claims description 2
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 claims description 2
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 claims description 2
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- 150000007513 acids Chemical class 0.000 claims description 2
- 150000003973 alkyl amines Chemical class 0.000 claims description 2
- 150000002462 imidazolines Chemical class 0.000 claims description 2
- 150000007524 organic acids Chemical class 0.000 claims description 2
- 235000005985 organic acids Nutrition 0.000 claims description 2
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 claims description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 12
- 150000004677 hydrates Chemical class 0.000 description 11
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 11
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 11
- 239000012088 reference solution Substances 0.000 description 11
- 239000000243 solution Substances 0.000 description 10
- 239000007789 gas Substances 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 7
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 6
- 230000002528 anti-freeze Effects 0.000 description 6
- 229920003082 Povidone K 90 Polymers 0.000 description 5
- 230000000903 blocking effect Effects 0.000 description 5
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 239000003345 natural gas Substances 0.000 description 4
- 229920002401 polyacrylamide Polymers 0.000 description 4
- LQIAZOCLNBBZQK-UHFFFAOYSA-N 1-(1,2-Diphosphanylethyl)pyrrolidin-2-one Chemical compound PCC(P)N1CCCC1=O LQIAZOCLNBBZQK-UHFFFAOYSA-N 0.000 description 3
- 108010053481 Antifreeze Proteins Proteins 0.000 description 3
- WSNMPAVSZJSIMT-UHFFFAOYSA-N COc1c(C)c2COC(=O)c2c(O)c1CC(O)C1(C)CCC(=O)O1 Chemical compound COc1c(C)c2COC(=O)c2c(O)c1CC(O)C1(C)CCC(=O)O1 WSNMPAVSZJSIMT-UHFFFAOYSA-N 0.000 description 3
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 3
- 239000002202 Polyethylene glycol Substances 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 239000001273 butane Substances 0.000 description 3
- 230000002452 interceptive effect Effects 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 3
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 3
- 229920001223 polyethylene glycol Polymers 0.000 description 3
- 239000001294 propane Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 239000004094 surface-active agent Substances 0.000 description 3
- 241000251468 Actinopterygii Species 0.000 description 2
- 102000002068 Glycopeptides Human genes 0.000 description 2
- 108010015899 Glycopeptides Proteins 0.000 description 2
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 description 2
- 229920000388 Polyphosphate Polymers 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 150000002334 glycols Chemical class 0.000 description 2
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 description 2
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 2
- 150000003009 phosphonic acids Chemical class 0.000 description 2
- 239000001205 polyphosphate Substances 0.000 description 2
- 235000011176 polyphosphates Nutrition 0.000 description 2
- 102000004196 processed proteins & peptides Human genes 0.000 description 2
- 108090000765 processed proteins & peptides Proteins 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 102000003886 Glycoproteins Human genes 0.000 description 1
- 108090000288 Glycoproteins Proteins 0.000 description 1
- 241000238631 Hexapoda Species 0.000 description 1
- 239000004354 Hydroxyethyl cellulose Substances 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 241001168341 Notothenia neglecta Species 0.000 description 1
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical class OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- 229920003080 Povidone K 25 Polymers 0.000 description 1
- 229920003081 Povidone K 30 Polymers 0.000 description 1
- 101001012040 Pseudomonas aeruginosa (strain ATCC 15692 / DSM 22644 / CIP 104116 / JCM 14847 / LMG 12228 / 1C / PRS 101 / PAO1) Immunomodulating metalloprotease Proteins 0.000 description 1
- 229920002125 Sokalan® Polymers 0.000 description 1
- 101710167605 Spike glycoprotein Proteins 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 235000011089 carbon dioxide Nutrition 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 239000010779 crude oil Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- UVGCAWDXQWPTEK-UHFFFAOYSA-N ethane;hydrate Chemical group O.CC UVGCAWDXQWPTEK-UHFFFAOYSA-N 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000003966 growth inhibitor Substances 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- HYYHQASRTSDPOD-UHFFFAOYSA-N hydroxylamine;phosphoric acid Chemical compound ON.OP(O)(O)=O HYYHQASRTSDPOD-UHFFFAOYSA-N 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 239000001282 iso-butane Substances 0.000 description 1
- 235000013847 iso-butane Nutrition 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 239000004584 polyacrylic acid Substances 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 238000011144 upstream manufacturing Methods 0.000 description 1
- 229920003169 water-soluble polymer Polymers 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C7/00—Purification; Separation; Use of additives
- C07C7/20—Use of additives, e.g. for stabilisation
-
- 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
- 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
- C10L3/00—Gaseous fuels; Natural gas; Synthetic natural gas obtained by processes not covered by subclass C10G, C10K; Liquefied petroleum gas
- C10L3/003—Additives for gaseous fuels
-
- 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
- This invention relates to a process for inhibiting the formation of gas hydrates in systems containing low-boiling hydrocarbons and water.
- Low-boiling hydrocarbons such as methane, ethane, propane, butane and iso-butane
- water is also present in varying amounts, the mixture of low-boiling hydrocarbons and water (such as present in natural gas), under conditions of elevated pressure and reduced temperature, tends to form hydrate crystals (gas hydrate crystals).
- thermodynamic measures are possible in principle: removal of free water, maintaining elevated temperatures and/or reduced pressures or the addition of melting point depressants
- antifreeze In practice, in most cases the last-mentioned measure is applied. However, the antifreezes, such as the lower alcohols and glycols, have to be added in substantial amounts (of the order of 30 per cent by weight of the water present) to be effective. An additional disadvantage of such amounts is that recovery of the added antifreezes is usually required during further processing of the mixture.
- Plants and poikilothermic animals such as insects and cold-water fish are known to protect themselves from freezing, both by antifreezes such as glycols and by special peptides and glycopeptides (termed Antifreeze Proteins, AFP's and Antifreeze Glycoproteins, AFGP's) which interfere with ice crystal growth (A.L. de Vries, Comp. Biochem. Physiol. 73 1982 627).
- antifreezes such as glycols and by special peptides and glycopeptides (termed Antifreeze Proteins, AFP's and Antifreeze Glycoproteins, AFGP's) which interfere with ice crystal growth (A.L. de Vries, Comp. Biochem. Physiol. 73 1982 627).
- the present applicants found such cold-water fish peptides and glycopeptides also to be effective in interfering with the growth of gas-hydrate crystals. However, their production and use for this purpose are currently considered to be uneconomical.
- Polyvinyl pyrrolidone is a well-known water-soluble polymer, currently used in particular in pharmacy. PVP is known to interfere with the growth of different crystals, such as the crystal growth of several drugs in aqueous suspension (K.H. Zillerand H.H. Ruppert, Pharm. Ind. 52 1990 1017), and also with the growth of ice crystals. However, in suppressing the growth of ice crystals PVP has been noted to be much less effective than the glycoproteins isolated from dialysed blood serum of the antarctic fish Notothenia neglecta (F. Frank et al. Nature 325 1987 146).
- PVP polyethylene glycol
- the invention therefore relates to a method for inhibiting the formation, growth and/or agglomeration of gas hydrate crystals in a mixture containing low-boiling hydrocarbons and water, characterized by adding to the mixture an effective amount of at least one additive selected from the group of polymers and copolymers of N-vinyl-2-pyrrolidone, and mixtures thereof.
- a preferred group of additives according to the invention are the homopolymers of N-vinyl-2-pyrrolidone (PVP). These are available commercially, e.g. from BSA under the trade name K0LID0N, in average molecular weights ranging from about 5000 daltons (K12) or less to about 400000 daltons (K90) and more. In general the present inventors found the lower molecular weight PVP's, especially those of between 5000 and 40000 daltons, to be the more effective in inhibiting the formation of gas hydrate crystals.
- PVP N-vinyl-2-pyrrolidone
- copolymers for use as additives according to the invention which are available commercially, are the copolymers of N-vinyl-2-pyrrolidone with 1-butene, with 1-hexene, with 1-decene, with vinyl chloride, with vinyl acetate, with ethyl acrylate, with 2-ethylhexyl acrylate, and with styrene.
- Copolymers of N-vinyl-2-pyrrolidone with mixtures of the above can also be used.
- the copolymers for use according to the invention will contain at least 30 mol% of the N-vinyl-2-pyrrolidone component.
- the amount of additive according to the invention is generally between 0.05 and 4 wt%, preferably between 0.25 and 1 wt%, based on the amount of water in the hydrocarbon-containing mixture.
- the additives according to the invention can be added to the subject mixture of low-boiling hydrocarbons and water, as their dry powder or.preferably, in concentrated aqueous solution. While the polymers and copolymers according to the invention interfere effectively with the growth of hydrate crystals, it may be advantageous also to interfere with agglomeration of any remaining crystallites and with their adhesion to the wall of the conduit. For this purpose film-formers, which are known to prevent water-wetting of metal surfaces, can be added.
- Typical examples of such film-formers are long-chain alkyl amines, alkyl diamines and imidazolines, optionally in combination with high molecular-weight organic acids.
- film-formers are monovalent, but preferably divalent, salts of long-chain alkarylsulphonic acids. These are subject of the present applicant's EP-A-457375.
- an aqueous solution of tetrahydrofurane (THF) was used as a model for wet gas, since tetrahydrofurane in water is known to form hydrate (structure II) crystals at about the same temperature as wet gas, but already at atmospheric pressure - for example, an 18.9 wt% aqueous solution of THF has a hydrate melting point of 4.3 ⁇ C at atmospheric pressure (S.R. Couch and D.W. Davidson, Can. J. Chem. 49 1971 2691).
- field conditions were simulated in an experimental set-up as schematically shown in Figure 2, comprising a two-liter stirred high-pressure autoclave 11 connected via a gear pump 12 to a coiled copper pipeline 13 of 16 m length and 6 mm internal diameter which is immersed in a thermostatically controlled bath 14.
- the pressure difference between the inlet and outlet of the pipeline is continuously monitored by a differential pressure transmitter 15.
- the autoclave was loaded at 13 °C with 400 ml of demineralised water (in which additives could be dissolved and with 800 ml of Shellsol D60 (trade name) , a mixture of paraffinic and naphthenic hydrocarbons mainly in the C. _ - C. publish range.
- the autoclave was loaded with ethane until the pressure (at 13 °C) within the autoclave was 20 bara.
- the stirred mixture was circulated through the system at a rate of 6.1 liters/hour.
- the temperature of the bath was lowered gradually, at a rate of 5 C C per hour.
- a piece of dry ice solid C0 deliberately was continuously held against the inlet of the coiled pipeline.
- the pressure drop over the coiled pipeline and the temperature of the bath were continuously monitored as a function of time.
- the temperature at which the pressure drop between the inlet and outlet of the coiled pipeline exceeded 1 bar was considered to be the blocking temperature.
- the hydrate- temperature of the mixture which is the temperature below which hydrates will form if no hydrate inhibitor is added, was approximately 10 C C, and the mixture was transported through the pipeline at a temperature of 1 C C.
- PVP K17 was added to the mixture at the upstream side thereof. It was found that during a period of approximately 17 hours after start of transportation through the line no significant pressure drop occurred within the pipeline along the length thereof. Thereafter hydrate formation in the line caused a gradually increasing pressure drop, until complete blocking of the line at approximately 37 hours after start of transportation. If no PVP would have been added to the mixture, hydrate formation would have caused complete blocking of the line within a much shorter period.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Engineering & Computer Science (AREA)
- Analytical Chemistry (AREA)
- Materials Engineering (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Life Sciences & Earth Sciences (AREA)
- Water Supply & Treatment (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Procédé d'inhibition de la formation, de la croissance et/ou de l'agglomération de cristaux d'hydrate de gaz dans un mélange contenant des hydrocarbures à faible point d'ébullition et de l'eau, caractérisé par l'addition audit mélange d'une quantité efficace d'au moins un additif sélectionné dans le groupe de polymères et de copolymères de N-vinyle-2-pyrrolidone, et de mélanges de ceux-ci. Un composé filmogène peut également être ajouté facultativement.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
AU43259/93A AU675227B2 (en) | 1992-06-11 | 1993-06-10 | A method for inhibiting gas hydrate formation |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP92201725 | 1992-06-11 | ||
EP92201725.6 | 1992-06-11 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO1993025798A1 true WO1993025798A1 (fr) | 1993-12-23 |
Family
ID=8210684
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/EP1993/001519 WO1993025798A1 (fr) | 1992-06-11 | 1993-06-10 | Procede d'inhibition de la formation d'hydrates de gaz |
Country Status (2)
Country | Link |
---|---|
AU (1) | AU675227B2 (fr) |
WO (1) | WO1993025798A1 (fr) |
Cited By (68)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1994012761A1 (fr) * | 1992-11-20 | 1994-06-09 | Colorado School Of Mines | Procede de regulation d'hydrates de clathrate dans des systemes a fluide |
WO1994024413A1 (fr) * | 1993-04-08 | 1994-10-27 | Bp Chemicals Limited | Procede d'inhibition de la formation de solides et melanges utilises dans ce procede |
WO1994025727A1 (fr) * | 1993-05-04 | 1994-11-10 | Bp Exploration Operating Company Limited | Inhibition de l'hydrate |
WO1995019408A1 (fr) * | 1994-01-13 | 1995-07-20 | Bp Exploration Operating Company Limited | Inhibition de formation d'hydrates |
US5460728A (en) * | 1993-12-21 | 1995-10-24 | Shell Oil Company | Method for inhibiting the plugging of conduits by gas hydrates |
WO1995032356A1 (fr) * | 1994-05-25 | 1995-11-30 | Colorado School Of Mines | Additifs et procede de regulation d'hydrates de clathrate dans des systemes a fluides |
WO1996008456A1 (fr) * | 1994-09-15 | 1996-03-21 | Exxon Production Reserch Company | Procede empechant la formation d'hydrates |
WO1996008672A1 (fr) * | 1994-09-15 | 1996-03-21 | Exxon Production Research Company | Procede d'inhibition de la formation d'hydrates |
WO1996029502A1 (fr) * | 1995-03-23 | 1996-09-26 | Bp Exploration Operating Company Limited | Inhibiteurs d'hydrates |
WO1996029501A1 (fr) * | 1995-03-23 | 1996-09-26 | Bp Exploration Operating Company Limited | Inhibition d'hydrates |
WO1996034177A1 (fr) * | 1995-04-25 | 1996-10-31 | Shell Internationale Research Maatschappij B.V. | Procede destine a empecher le bouchage de conduits par des hydrates de gaz |
WO1996037684A1 (fr) * | 1995-05-26 | 1996-11-28 | Nippon Shokubai Co., Ltd. | Inhibiteur d'hydrates de clathrate et procede permettant d'inhiber la formation des hydrates de clathrate dans lequel il est utilise |
GB2301836A (en) * | 1995-06-08 | 1996-12-18 | Exxon Production Research Co | Inhibiting Clathrate hydrate formation |
GB2301824A (en) * | 1995-10-04 | 1996-12-18 | Exxon Production Research Co | Clathrate hydrate-inhibiting polymers |
WO1996041786A1 (fr) * | 1995-06-08 | 1996-12-27 | Exxon Production Research Company | Procede permettant d'inhiber la formation d'hydrates |
WO1996041784A1 (fr) * | 1995-06-08 | 1996-12-27 | Exxon Production Research Company | Procede visant a empecher la formation d'hydrates |
WO1997007320A1 (fr) * | 1995-08-16 | 1997-02-27 | Exxon Production Research Company | Procede de selection d'un polymere destine a inhiber la formation d'hydrates |
US5648575A (en) * | 1995-01-10 | 1997-07-15 | Shell Oil Company | Method for inhibiting the plugging of conduits by gas hydrates |
EP0812977A1 (fr) * | 1996-06-14 | 1997-12-17 | Institut Francais Du Petrole | Méthode pour réduire la tendance à l'agglomération des hydrates dans les effluents de production contenant des huiles paraffiniques |
US5741758A (en) * | 1995-10-13 | 1998-04-21 | Bj Services Company, U.S.A. | Method for controlling gas hydrates in fluid mixtures |
US5841010A (en) * | 1994-09-15 | 1998-11-24 | Exxon Production Research Company | Surface active agents as gas hydrate inhibitors |
AU707765B2 (en) * | 1993-12-21 | 1999-07-22 | Shell Internationale Research Maatschappij B.V. | Method for inhibiting the plugging of conduits by gas hydrates |
US5936040A (en) * | 1995-06-08 | 1999-08-10 | Exxon Production Research Company | Method for inhibiting hydrate formation using maleimide copolymers |
US6015929A (en) * | 1994-09-15 | 2000-01-18 | Exxon Research And Engineering Co. | Gas hydrate anti-agglomerates |
US6025302A (en) * | 1998-05-18 | 2000-02-15 | Bj Services Company | Quaternized polyether amines as gas hydrate inhibitors |
US6028233A (en) * | 1995-06-08 | 2000-02-22 | Exxon Production Research Company | Method for inhibiting hydrate formation |
US6107531A (en) * | 1995-06-08 | 2000-08-22 | Exxonmobil Upstream Research Company | Method for inhibiting hydrate formation |
US6152993A (en) * | 1997-09-09 | 2000-11-28 | Shell Oil Company | Method for inhibiting the plugging of conduits by gas hydrates |
US6194622B1 (en) | 1998-06-10 | 2001-02-27 | Exxonmobil Upstream Research Company | Method for inhibiting hydrate formation |
US6232273B1 (en) | 1995-06-02 | 2001-05-15 | Nippon Shokubai Co., Ltd. | Clathrate hydrate inhibitor and method of inhibiting the formation of clathrate hydrates using it |
US6319971B1 (en) | 1997-05-22 | 2001-11-20 | Rf-Procom A/S | Composition for controlling clathrate hydrates and a method for controlling clathrate hydrate formation |
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US11148124B2 (en) | 2019-12-04 | 2021-10-19 | Saudi Arabian Oil Company | Hierarchical zeolite Y and nano-sized zeolite beta composite |
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US11753492B2 (en) | 2019-12-09 | 2023-09-12 | Saudi Arabian Oil Company | Acryloyl based polymers with active end cap as corrosion inhibitors |
CN111116797A (zh) * | 2019-12-24 | 2020-05-08 | 中国科学院广州能源研究所 | 一种新型的天然气水合物抑制剂 |
CN111116797B (zh) * | 2019-12-24 | 2021-09-14 | 中国科学院广州能源研究所 | 一种天然气水合物抑制剂 |
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AU4325993A (en) | 1994-01-04 |
AU675227B2 (en) | 1997-01-30 |
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