CA2178364C - Copolymeres a base de maleimide et methode pour empecher la formation d'hydrates - Google Patents

Copolymeres a base de maleimide et methode pour empecher la formation d'hydrates Download PDF

Info

Publication number: CA2178364C
Authority: CA; Canada
Prior art keywords: copolymer; monomeric units; carbon atoms; group; inhibitor
Prior art date: 1995-06-08
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.): Expired - Fee Related

Application number

CA 2178364

Other languages

English (en)

Other versions

CA2178364A1 (fr

Inventor

Christine A. Costello

Enock Berluche

Russell H. Oelfke

Larry D. Talley

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

ExxonMobil Upstream Research Co

Original Assignee

Exxon Production Research Co

Priority date (The priority date 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 date listed.)

1995-06-08

Filing date

1996-06-06

Publication date

2000-09-26

1996-06-06 Application filed by Exxon Production Research Co filed Critical Exxon Production Research Co

1996-12-09 Publication of CA2178364A1 publication Critical patent/CA2178364A1/fr

2000-09-26 Application granted granted Critical

2000-09-26 Publication of CA2178364C publication Critical patent/CA2178364C/fr

2016-06-06 Anticipated expiration legal-status Critical

Status Expired - Fee Related legal-status Critical Current

Links

229920001577 copolymer Polymers 0.000 title claims abstract description 145
230000015572 biosynthetic process Effects 0.000 title claims abstract description 40
230000002401 inhibitory effect Effects 0.000 title claims abstract description 11
238000000034 method Methods 0.000 title claims description 55
239000012530 fluid Substances 0.000 claims abstract description 81
239000003112 inhibitor Substances 0.000 claims abstract description 81
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 60
239000003208 petroleum Substances 0.000 claims abstract description 45
-1 vinyl lactam Chemical class 0.000 claims abstract description 33
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 32
239000007789 gas Substances 0.000 claims abstract description 31
150000004677 hydrates Chemical class 0.000 claims abstract description 29
229910052757 nitrogen Inorganic materials 0.000 claims abstract description 26
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims abstract description 26
125000005439 maleimidyl group Chemical group C1(C=CC(N1*)=O)=O 0.000 claims abstract description 23
125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 15
125000004430 oxygen atom Chemical group O* 0.000 claims abstract description 15
239000000470 constituent Substances 0.000 claims abstract description 7
239000001257 hydrogen Substances 0.000 claims description 42
229910052739 hydrogen Inorganic materials 0.000 claims description 42
125000000753 cycloalkyl group Chemical group 0.000 claims description 36
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 34
HDFGOPSGAURCEO-UHFFFAOYSA-N N-ethylmaleimide Chemical compound CCN1C(=O)C=CC1=O HDFGOPSGAURCEO-UHFFFAOYSA-N 0.000 claims description 32
229920000642 polymer Polymers 0.000 claims description 30
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 27
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 22
239000000203 mixture Substances 0.000 claims description 22
239000002904 solvent Substances 0.000 claims description 22
PNLUGRYDUHRLOF-UHFFFAOYSA-N n-ethenyl-n-methylacetamide Chemical group C=CN(C)C(C)=O PNLUGRYDUHRLOF-UHFFFAOYSA-N 0.000 claims description 21
USICVVZOKTZACS-UHFFFAOYSA-N 3-butylpyrrole-2,5-dione Chemical compound CCCCC1=CC(=O)NC1=O USICVVZOKTZACS-UHFFFAOYSA-N 0.000 claims description 18
PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 claims description 17
MDXKEHHAIMNCSW-UHFFFAOYSA-N 3-propylpyrrole-2,5-dione Chemical compound CCCC1=CC(=O)NC1=O MDXKEHHAIMNCSW-UHFFFAOYSA-N 0.000 claims description 16
239000008346 aqueous phase Substances 0.000 claims description 16
UJTRCPVECIHPBG-UHFFFAOYSA-N 3-cyclohexylpyrrole-2,5-dione Chemical compound O=C1NC(=O)C(C2CCCCC2)=C1 UJTRCPVECIHPBG-UHFFFAOYSA-N 0.000 claims description 14
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
ZLPORNPZJNRGCO-UHFFFAOYSA-N 3-methylpyrrole-2,5-dione Chemical compound CC1=CC(=O)NC1=O ZLPORNPZJNRGCO-UHFFFAOYSA-N 0.000 claims description 9
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 9
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 8
WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 claims description 8
JWYVGKFDLWWQJX-UHFFFAOYSA-N 1-ethenylazepan-2-one Chemical compound C=CN1CCCCCC1=O JWYVGKFDLWWQJX-UHFFFAOYSA-N 0.000 claims description 6
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 6
239000007864 aqueous solution Substances 0.000 claims description 6
WLPAQAXAZQUXBG-UHFFFAOYSA-N 1-pyrrolidin-1-ylprop-2-en-1-one Chemical compound C=CC(=O)N1CCCC1 WLPAQAXAZQUXBG-UHFFFAOYSA-N 0.000 claims description 5
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
OVHHHVAVHBHXAK-UHFFFAOYSA-N n,n-diethylprop-2-enamide Chemical compound CCN(CC)C(=O)C=C OVHHHVAVHBHXAK-UHFFFAOYSA-N 0.000 claims description 5
IXMWJKUCJKVNBJ-UHFFFAOYSA-N n-ethenyl-n-propylpropanamide Chemical compound CCCN(C=C)C(=O)CC IXMWJKUCJKVNBJ-UHFFFAOYSA-N 0.000 claims description 5
SWPMNMYLORDLJE-UHFFFAOYSA-N n-ethylprop-2-enamide Chemical compound CCNC(=O)C=C SWPMNMYLORDLJE-UHFFFAOYSA-N 0.000 claims description 5
QNILTEGFHQSKFF-UHFFFAOYSA-N n-propan-2-ylprop-2-enamide Chemical compound CC(C)NC(=O)C=C QNILTEGFHQSKFF-UHFFFAOYSA-N 0.000 claims description 5
229910052760 oxygen Inorganic materials 0.000 claims description 5
239000001301 oxygen Substances 0.000 claims description 5
LPIQIQPLUVLISR-UHFFFAOYSA-N 2-prop-1-en-2-yl-4,5-dihydro-1,3-oxazole Chemical compound CC(=C)C1=NCCO1 LPIQIQPLUVLISR-UHFFFAOYSA-N 0.000 claims description 4
MXRGSJAOLKBZLU-UHFFFAOYSA-N 3-ethenylazepan-2-one Chemical compound C=CC1CCCCNC1=O MXRGSJAOLKBZLU-UHFFFAOYSA-N 0.000 claims description 4
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
239000012267 brine Substances 0.000 claims description 4
125000005842 heteroatom Chemical group 0.000 claims description 4
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 4
239000013535 sea water Substances 0.000 claims description 4
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 claims description 4
229910052717 sulfur Inorganic materials 0.000 claims description 4
239000011593 sulfur Chemical group 0.000 claims description 4
RESPXSHDJQUNTN-UHFFFAOYSA-N 1-piperidin-1-ylprop-2-en-1-one Chemical compound C=CC(=O)N1CCCCC1 RESPXSHDJQUNTN-UHFFFAOYSA-N 0.000 claims description 3
FCZRAAJZTGOYIC-UHFFFAOYSA-N 2,4-dimethylpent-2-enamide Chemical compound CC(C)C=C(C)C(N)=O FCZRAAJZTGOYIC-UHFFFAOYSA-N 0.000 claims description 3
LVCMKNCJDCTPIB-UHFFFAOYSA-N 2-methyl-1-pyrrolidin-1-ylprop-2-en-1-one Chemical compound CC(=C)C(=O)N1CCCC1 LVCMKNCJDCTPIB-UHFFFAOYSA-N 0.000 claims description 3
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 3
YQIGLEFUZMIVHU-UHFFFAOYSA-N 2-methyl-n-propan-2-ylprop-2-enamide Chemical compound CC(C)NC(=O)C(C)=C YQIGLEFUZMIVHU-UHFFFAOYSA-N 0.000 claims 3
229940088644 n,n-dimethylacrylamide Drugs 0.000 claims 3
YLGYACDQVQQZSW-UHFFFAOYSA-N n,n-dimethylprop-2-enamide Chemical group CN(C)C(=O)C=C YLGYACDQVQQZSW-UHFFFAOYSA-N 0.000 claims 3
DGPVNNMFVYYVDF-UHFFFAOYSA-N 1-prop-2-enoylpyrrolidin-2-one Chemical compound C=CC(=O)N1CCCC1=O DGPVNNMFVYYVDF-UHFFFAOYSA-N 0.000 claims 2
239000000654 additive Substances 0.000 claims 2
230000000996 additive effect Effects 0.000 claims 2
125000002015 acyclic group Chemical group 0.000 claims 1
125000001183 hydrocarbyl group Chemical group 0.000 claims 1
HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 abstract description 14
UYMKPFRHYYNDTL-UHFFFAOYSA-N ethenamine Chemical compound NC=C UYMKPFRHYYNDTL-UHFFFAOYSA-N 0.000 abstract description 10
229920002554 vinyl polymer Polymers 0.000 abstract description 9
125000004122 cyclic group Chemical group 0.000 abstract description 7
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 abstract description 6
125000003342 alkenyl group Chemical group 0.000 abstract description 5
ODUCDPQEXGNKDN-UHFFFAOYSA-N nitroxyl Chemical compound O=N ODUCDPQEXGNKDN-UHFFFAOYSA-N 0.000 abstract description 5
238000005054 agglomeration Methods 0.000 abstract description 4
230000002776 aggregation Effects 0.000 abstract description 4
239000013078 crystal Substances 0.000 abstract description 4
230000006911 nucleation Effects 0.000 abstract description 4
238000010899 nucleation Methods 0.000 abstract description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 75
WHNPOQXWAMXPTA-UHFFFAOYSA-N 3-methylbut-2-enamide Chemical compound CC(C)=CC(N)=O WHNPOQXWAMXPTA-UHFFFAOYSA-N 0.000 description 60
239000000243 solution Substances 0.000 description 45
238000007334 copolymerization reaction Methods 0.000 description 19
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 18
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 16
239000000178 monomer Substances 0.000 description 16
239000011541 reaction mixture Substances 0.000 description 14
OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 12
OZAIFHULBGXAKX-VAWYXSNFSA-N AIBN Substances N#CC(C)(C)\N=N\C(C)(C)C#N OZAIFHULBGXAKX-VAWYXSNFSA-N 0.000 description 12
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
238000001914 filtration Methods 0.000 description 11
238000006243 chemical reaction Methods 0.000 description 9
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 8
238000001460 carbon-13 nuclear magnetic resonance spectrum Methods 0.000 description 8
238000000746 purification Methods 0.000 description 8
150000003923 2,5-pyrrolediones Chemical class 0.000 description 7
239000003921 oil Substances 0.000 description 7
239000002994 raw material Substances 0.000 description 7
ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 6
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 6
229960004132 diethyl ether Drugs 0.000 description 6
229930195733 hydrocarbon Natural products 0.000 description 6
150000002430 hydrocarbons Chemical class 0.000 description 6
NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 6
NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 6
235000002639 sodium chloride Nutrition 0.000 description 6
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 5
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
150000003926 acrylamides Chemical class 0.000 description 5
239000000460 chlorine Substances 0.000 description 5
239000003345 natural gas Substances 0.000 description 5
239000000047 product Substances 0.000 description 5
239000012264 purified product Substances 0.000 description 5
239000011780 sodium chloride Substances 0.000 description 5
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
LXEKPEMOWBOYRF-UHFFFAOYSA-N [2-[(1-azaniumyl-1-imino-2-methylpropan-2-yl)diazenyl]-2-methylpropanimidoyl]azanium;dichloride Chemical compound Cl.Cl.NC(=N)C(C)(C)N=NC(C)(C)C(N)=N LXEKPEMOWBOYRF-UHFFFAOYSA-N 0.000 description 4
238000004090 dissolution Methods 0.000 description 4
238000001035 drying Methods 0.000 description 4
230000000694 effects Effects 0.000 description 4
238000004519 manufacturing process Methods 0.000 description 4
238000001556 precipitation Methods 0.000 description 4
239000004215 Carbon black (E152) Substances 0.000 description 3
239000007795 chemical reaction product Substances 0.000 description 3
239000003999 initiator Substances 0.000 description 3
239000001282 iso-butane Substances 0.000 description 3
235000013847 iso-butane Nutrition 0.000 description 3
239000007788 liquid Substances 0.000 description 3
QYZFTMMPKCOTAN-UHFFFAOYSA-N n-[2-(2-hydroxyethylamino)ethyl]-2-[[1-[2-(2-hydroxyethylamino)ethylamino]-2-methyl-1-oxopropan-2-yl]diazenyl]-2-methylpropanamide Chemical compound OCCNCCNC(=O)C(C)(C)N=NC(C)(C)C(=O)NCCNCCO QYZFTMMPKCOTAN-UHFFFAOYSA-N 0.000 description 3
239000001294 propane Substances 0.000 description 3
230000002829 reductive effect Effects 0.000 description 3
IJDNQMDRQITEOD-UHFFFAOYSA-N sec-butylidene Natural products CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 3
238000003786 synthesis reaction Methods 0.000 description 3
238000012360 testing method Methods 0.000 description 3
RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 2
RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 2
RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 2
230000002528 anti-freeze Effects 0.000 description 2
229910002092 carbon dioxide Inorganic materials 0.000 description 2
239000001569 carbon dioxide Substances 0.000 description 2
150000001875 compounds Chemical class 0.000 description 2
238000010494 dissociation reaction Methods 0.000 description 2
230000005593 dissociations Effects 0.000 description 2
238000011156 evaluation Methods 0.000 description 2
229910000037 hydrogen sulfide Inorganic materials 0.000 description 2
238000002347 injection Methods 0.000 description 2
239000007924 injection Substances 0.000 description 2
230000000670 limiting effect Effects 0.000 description 2
238000012986 modification Methods 0.000 description 2
230000004048 modification Effects 0.000 description 2
CRSOQBOWXPBRES-UHFFFAOYSA-N neopentane Chemical compound CC(C)(C)C CRSOQBOWXPBRES-UHFFFAOYSA-N 0.000 description 2
238000010926 purge Methods 0.000 description 2
239000000126 substance Substances 0.000 description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
PMPVIKIVABFJJI-UHFFFAOYSA-N Cyclobutane Chemical compound C1CCC1 PMPVIKIVABFJJI-UHFFFAOYSA-N 0.000 description 1
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
LVZWSLJZHVFIQJ-UHFFFAOYSA-N Cyclopropane Chemical compound C1CC1 LVZWSLJZHVFIQJ-UHFFFAOYSA-N 0.000 description 1
101001126084 Homo sapiens Piwi-like protein 2 Proteins 0.000 description 1
102100029365 Piwi-like protein 2 Human genes 0.000 description 1
102100035115 Testin Human genes 0.000 description 1
101710070533 Testin Proteins 0.000 description 1
GYMWQLRSSDFGEQ-ADRAWKNSSA-N [(3e,8r,9s,10r,13s,14s,17r)-13-ethyl-17-ethynyl-3-hydroxyimino-1,2,6,7,8,9,10,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-yl] acetate;(8r,9s,13s,14s,17r)-17-ethynyl-13-methyl-7,8,9,11,12,14,15,16-octahydro-6h-cyclopenta[a]phenanthrene-3,17-diol Chemical compound OC1=CC=C2[C@H]3CC[C@](C)([C@](CC4)(O)C#C)[C@@H]4[C@@H]3CCC2=C1.O/N=C/1CC[C@@H]2[C@H]3CC[C@](CC)([C@](CC4)(OC(C)=O)C#C)[C@@H]4[C@@H]3CCC2=C\1 GYMWQLRSSDFGEQ-ADRAWKNSSA-N 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
238000011021 bench scale process Methods 0.000 description 1
238000009835 boiling Methods 0.000 description 1
239000001273 butane Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
238000013461 design Methods 0.000 description 1
239000006185 dispersion Substances 0.000 description 1
238000004821 distillation Methods 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
238000005227 gel permeation chromatography Methods 0.000 description 1
DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 1
238000004128 high performance liquid chromatography Methods 0.000 description 1
229920001519 homopolymer Polymers 0.000 description 1
239000010720 hydraulic oil Substances 0.000 description 1
150000002463 imidates Chemical class 0.000 description 1
230000005764 inhibitory process Effects 0.000 description 1
150000003951 lactams Chemical class 0.000 description 1
238000003760 magnetic stirring Methods 0.000 description 1
239000000463 material Substances 0.000 description 1
OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
230000036961 partial effect Effects 0.000 description 1
239000012071 phase Substances 0.000 description 1
231100000683 possible toxicity Toxicity 0.000 description 1
238000011084 recovery Methods 0.000 description 1
230000002441 reversible effect Effects 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
239000007787 solid Substances 0.000 description 1
229910001220 stainless steel Inorganic materials 0.000 description 1
239000010935 stainless steel Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
238000003860 storage Methods 0.000 description 1
229920001897 terpolymer Polymers 0.000 description 1
238000012956 testing procedure Methods 0.000 description 1
238000012546 transfer Methods 0.000 description 1
238000003828 vacuum filtration Methods 0.000 description 1
229920003169 water-soluble polymer Polymers 0.000 description 1

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Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)

CA 2178364 1995-06-08 1996-06-06 Copolymeres a base de maleimide et methode pour empecher la formation d'hydrates Expired - Fee Related CA2178364C (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US7195P	1995-06-08	1995-06-08
US60/000,071		1995-06-08

Publications (2)

Publication Number	Publication Date
CA2178364A1 CA2178364A1 (fr)	1996-12-09
CA2178364C true CA2178364C (fr)	2000-09-26

Family

ID=21689780

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA 2178364 Expired - Fee Related CA2178364C (fr)	1995-06-08	1996-06-06	Copolymeres a base de maleimide et methode pour empecher la formation d'hydrates

Country Status (1)

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CA (1)	CA2178364C (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
NO972355D0 (no)	1997-05-22	1997-05-22	Rf Procom As	Blanding for regulering av clathrathydrater og en fremgangsmåte for regulering av clathrathydrat-dannelse

1996
- 1996-06-06 CA CA 2178364 patent/CA2178364C/fr not_active Expired - Fee Related

Also Published As

Publication number	Publication date
CA2178364A1 (fr)	1996-12-09

Legal Events

Date	Code	Title	Description
1996-06-06	EEER	Examination request
2004-06-07	MKLA	Lapsed

Publication	Publication Date	Title
US5936040A (en)	1999-08-10	Method for inhibiting hydrate formation using maleimide copolymers
US5744665A (en)	1998-04-28	Maleimide copolymers and method for inhibiting hydrate formation
AU688967B2 (en)	1998-03-19	A method for inhibiting hydrate formation
US6028233A (en)	2000-02-22	Method for inhibiting hydrate formation
US5874660A (en)	1999-02-23	Method for inhibiting hydrate formation
AU684689B2 (en)	1997-12-18	Method for inhibiting clathrate hydrate formation
US5583273A (en)	1996-12-10	Method for inhibiting hydrate formation
AU698215B2 (en)	1998-10-29	Method for inhibiting hydrate formation
AU707292B2 (en)	1999-07-08	Method for inhibiting hydrate formation
US6222083B1 (en)	2001-04-24	Method for inhibiting hydrate formation
GB2301825A (en)	1996-12-18	A polymer for inhibiting hydrate formation
CA2178364C (fr)	2000-09-26	Copolymeres a base de maleimide et methode pour empecher la formation d'hydrates
CA2178367C (fr)	2001-04-17	Methode pour empecher la formation d'hydrates
CA2178371A1 (fr)	1996-12-09	Methode pour empecher la formation d'hydrates