CA2832450C - Additif servant a maintenir la fluidite de fluides contenant des hydrates de gaz - Google Patents
Additif servant a maintenir la fluidite de fluides contenant des hydrates de gaz Download PDFInfo
- Publication number
- CA2832450C CA2832450C CA2832450A CA2832450A CA2832450C CA 2832450 C CA2832450 C CA 2832450C CA 2832450 A CA2832450 A CA 2832450A CA 2832450 A CA2832450 A CA 2832450A CA 2832450 C CA2832450 C CA 2832450C
- Authority
- CA
- Canada
- Prior art keywords
- alkyl
- amine
- compounds
- ch2ch
- agglomerant
- 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.)
- Expired - Fee Related
Links
- 150000004677 hydrates Chemical class 0.000 title claims abstract description 28
- 239000000654 additive Substances 0.000 title description 10
- 239000012530 fluid Substances 0.000 title description 7
- 230000000996 additive effect Effects 0.000 title description 5
- 239000007789 gas Substances 0.000 claims abstract description 38
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 30
- 239000000203 mixture Substances 0.000 claims abstract description 23
- 239000003112 inhibitor Substances 0.000 claims abstract description 20
- 150000003839 salts Chemical class 0.000 claims abstract description 17
- 238000000034 method Methods 0.000 claims abstract description 15
- 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 claims abstract description 13
- 238000005054 agglomeration Methods 0.000 claims abstract description 9
- 230000002776 aggregation Effects 0.000 claims abstract description 9
- 238000005260 corrosion Methods 0.000 claims abstract description 9
- 230000007797 corrosion Effects 0.000 claims abstract description 9
- 125000002252 acyl group Chemical group 0.000 claims abstract description 7
- 230000008021 deposition Effects 0.000 claims abstract description 6
- 239000012188 paraffin wax Substances 0.000 claims abstract description 6
- 230000002401 inhibitory effect Effects 0.000 claims abstract description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 44
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 30
- 229930195733 hydrocarbon Natural products 0.000 claims description 14
- 150000002430 hydrocarbons Chemical class 0.000 claims description 14
- -1 nitrogen-containing compound Chemical class 0.000 claims description 12
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 11
- 239000004215 Carbon black (E152) Substances 0.000 claims description 10
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 5
- 150000001875 compounds Chemical class 0.000 abstract description 59
- 150000001412 amines Chemical group 0.000 abstract description 21
- 150000001408 amides Chemical group 0.000 abstract description 10
- 125000001165 hydrophobic group Chemical group 0.000 abstract description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract description 6
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 abstract description 6
- 125000002768 hydroxyalkyl group Chemical group 0.000 abstract description 5
- 125000001033 ether group Chemical group 0.000 abstract description 2
- 125000000217 alkyl group Chemical group 0.000 description 74
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 36
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 19
- 239000003760 tallow Substances 0.000 description 15
- 238000012360 testing method Methods 0.000 description 15
- 239000007858 starting material Substances 0.000 description 11
- 240000002791 Brassica napus Species 0.000 description 10
- 235000004977 Brassica sinapistrum Nutrition 0.000 description 10
- 150000001242 acetic acid derivatives Chemical class 0.000 description 10
- 235000010469 Glycine max Nutrition 0.000 description 9
- 244000068988 Glycine max Species 0.000 description 9
- 239000013078 crystal Substances 0.000 description 9
- 235000014113 dietary fatty acids Nutrition 0.000 description 9
- 229930195729 fatty acid Natural products 0.000 description 9
- 239000000194 fatty acid Substances 0.000 description 9
- 150000004665 fatty acids Chemical class 0.000 description 9
- 239000002253 acid Substances 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 8
- 239000002270 dispersing agent Substances 0.000 description 8
- 125000001931 aliphatic group Chemical group 0.000 description 7
- 125000001183 hydrocarbyl group Chemical group 0.000 description 7
- KBPLFHHGFOOTCA-UHFFFAOYSA-N caprylic alcohol Natural products CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 6
- 150000004985 diamines Chemical class 0.000 description 6
- 239000013505 freshwater Substances 0.000 description 6
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 6
- 239000003921 oil Substances 0.000 description 6
- 229920000768 polyamine Polymers 0.000 description 6
- QGLWBTPVKHMVHM-KTKRTIGZSA-N (z)-octadec-9-en-1-amine Chemical compound CCCCCCCC\C=C/CCCCCCCCN QGLWBTPVKHMVHM-KTKRTIGZSA-N 0.000 description 5
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 5
- 230000000397 acetylating effect Effects 0.000 description 5
- XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 4
- 125000003277 amino group Chemical group 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 239000006185 dispersion Substances 0.000 description 4
- 230000005764 inhibitory process Effects 0.000 description 4
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 4
- 239000013535 sea water Substances 0.000 description 4
- 239000004094 surface-active agent Substances 0.000 description 4
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 3
- SYWDPPFYAMFYQQ-KTKRTIGZSA-N (z)-docos-13-en-1-amine Chemical compound CCCCCCCC\C=C/CCCCCCCCCCCCN SYWDPPFYAMFYQQ-KTKRTIGZSA-N 0.000 description 3
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 3
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WWZKQHOCKIZLMA-UHFFFAOYSA-N Caprylic acid Natural products CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000005642 Oleic acid Substances 0.000 description 3
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 150000003973 alkyl amines Chemical class 0.000 description 3
- 150000001734 carboxylic acid salts Chemical class 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 238000012216 screening Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- IBUPNDMHIOTKBL-UHFFFAOYSA-N 1,5-diaminopentan-2-ol Chemical compound NCCCC(O)CN IBUPNDMHIOTKBL-UHFFFAOYSA-N 0.000 description 2
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 2
- 244000060011 Cocos nucifera Species 0.000 description 2
- 235000013162 Cocos nucifera Nutrition 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- LHIJANUOQQMGNT-UHFFFAOYSA-N aminoethylethanolamine Chemical compound NCCNCCO LHIJANUOQQMGNT-UHFFFAOYSA-N 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 2
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 239000001282 iso-butane Substances 0.000 description 2
- 235000013847 iso-butane Nutrition 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- ZDGGJQMSELMHLK-UHFFFAOYSA-N m-Trifluoromethylhippuric acid Chemical class OC(=O)CNC(=O)C1=CC=CC(C(F)(F)F)=C1 ZDGGJQMSELMHLK-UHFFFAOYSA-N 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N monoethanolamine hydrochloride Natural products NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 2
- IOQPZZOEVPZRBK-UHFFFAOYSA-N octan-1-amine Chemical compound CCCCCCCCN IOQPZZOEVPZRBK-UHFFFAOYSA-N 0.000 description 2
- 238000005192 partition Methods 0.000 description 2
- 230000002265 prevention Effects 0.000 description 2
- 239000001294 propane Substances 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 231100000167 toxic agent Toxicity 0.000 description 2
- 230000002588 toxic effect Effects 0.000 description 2
- OBETXYAYXDNJHR-SSDOTTSWSA-M (2r)-2-ethylhexanoate Chemical compound CCCC[C@@H](CC)C([O-])=O OBETXYAYXDNJHR-SSDOTTSWSA-M 0.000 description 1
- FJLUATLTXUNBOT-UHFFFAOYSA-N 1-Hexadecylamine Chemical compound CCCCCCCCCCCCCCCCN FJLUATLTXUNBOT-UHFFFAOYSA-N 0.000 description 1
- BMVXCPBXGZKUPN-UHFFFAOYSA-N 1-hexanamine Chemical compound CCCCCCN BMVXCPBXGZKUPN-UHFFFAOYSA-N 0.000 description 1
- LTHNHFOGQMKPOV-UHFFFAOYSA-N 2-ethylhexan-1-amine Chemical compound CCCCC(CC)CN LTHNHFOGQMKPOV-UHFFFAOYSA-N 0.000 description 1
- SSOBBNSVCWLYPH-UHFFFAOYSA-N 2-propylheptan-1-amine Chemical compound CCCCCC(CN)CCC SSOBBNSVCWLYPH-UHFFFAOYSA-N 0.000 description 1
- ZRJOUVOXPWNFOF-UHFFFAOYSA-N 3-dodecoxypropan-1-amine Chemical compound CCCCCCCCCCCCOCCCN ZRJOUVOXPWNFOF-UHFFFAOYSA-N 0.000 description 1
- RDCAZFAKCIEASQ-UHFFFAOYSA-N 3-octoxypropan-1-amine Chemical compound CCCCCCCCOCCCN RDCAZFAKCIEASQ-UHFFFAOYSA-N 0.000 description 1
- XZIIFPSPUDAGJM-UHFFFAOYSA-N 6-chloro-2-n,2-n-diethylpyrimidine-2,4-diamine Chemical compound CCN(CC)C1=NC(N)=CC(Cl)=N1 XZIIFPSPUDAGJM-UHFFFAOYSA-N 0.000 description 1
- DPUOLQHDNGRHBS-UHFFFAOYSA-N Brassidinsaeure Natural products CCCCCCCCC=CCCCCCCCCCCCC(O)=O DPUOLQHDNGRHBS-UHFFFAOYSA-N 0.000 description 1
- MHZGKXUYDGKKIU-UHFFFAOYSA-N Decylamine Chemical compound CCCCCCCCCCN MHZGKXUYDGKKIU-UHFFFAOYSA-N 0.000 description 1
- URXZXNYJPAJJOQ-UHFFFAOYSA-N Erucic acid Natural products CCCCCCC=CCCCCCCCCCCCC(O)=O URXZXNYJPAJJOQ-UHFFFAOYSA-N 0.000 description 1
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 1
- REYJJPSVUYRZGE-UHFFFAOYSA-N Octadecylamine Chemical compound CCCCCCCCCCCCCCCCCCN REYJJPSVUYRZGE-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical group CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- 229920002125 Sokalan® Polymers 0.000 description 1
- PLZVEHJLHYMBBY-UHFFFAOYSA-N Tetradecylamine Chemical compound CCCCCCCCCCCCCCN PLZVEHJLHYMBBY-UHFFFAOYSA-N 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 238000006640 acetylation reaction Methods 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 150000001263 acyl chlorides Chemical class 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- OBETXYAYXDNJHR-UHFFFAOYSA-N alpha-ethylcaproic acid Natural products CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- GONOPSZTUGRENK-UHFFFAOYSA-N benzyl(trichloro)silane Chemical compound Cl[Si](Cl)(Cl)CC1=CC=CC=C1 GONOPSZTUGRENK-UHFFFAOYSA-N 0.000 description 1
- 231100000693 bioaccumulation Toxicity 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000010779 crude oil Substances 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- 235000019329 dioctyl sodium sulphosuccinate Nutrition 0.000 description 1
- YHAIUSTWZPMYGG-UHFFFAOYSA-L disodium;2,2-dioctyl-3-sulfobutanedioate Chemical compound [Na+].[Na+].CCCCCCCCC(C([O-])=O)(C(C([O-])=O)S(O)(=O)=O)CCCCCCCC YHAIUSTWZPMYGG-UHFFFAOYSA-L 0.000 description 1
- JRBPAEWTRLWTQC-UHFFFAOYSA-N dodecylamine Chemical compound CCCCCCCCCCCCN JRBPAEWTRLWTQC-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- DPUOLQHDNGRHBS-KTKRTIGZSA-N erucic acid Chemical compound CCCCCCCC\C=C/CCCCCCCCCCCC(O)=O DPUOLQHDNGRHBS-KTKRTIGZSA-N 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 238000007046 ethoxylation reaction Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 150000002462 imidazolines Chemical class 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- HXASIGVEWQOPLT-UHFFFAOYSA-N n'-(2-ethylhexyl)-n'-methylpropane-1,3-diamine Chemical compound CCCCC(CC)CN(C)CCCN HXASIGVEWQOPLT-UHFFFAOYSA-N 0.000 description 1
- JMKDQQHHEVODCB-UHFFFAOYSA-N n'-(3-aminopropyl)-n'-(2-ethylhexyl)propane-1,3-diamine Chemical compound CCCCC(CC)CN(CCCN)CCCN JMKDQQHHEVODCB-UHFFFAOYSA-N 0.000 description 1
- KERWQZOMYPHPLU-UHFFFAOYSA-N n'-(3-aminopropyl)-n'-(2-propylheptyl)propane-1,3-diamine Chemical compound CCCCCC(CCC)CN(CCCN)CCCN KERWQZOMYPHPLU-UHFFFAOYSA-N 0.000 description 1
- HKEBWESLPJXKAA-UHFFFAOYSA-N n'-(3-aminopropyl)-n'-decylpropane-1,3-diamine Chemical compound CCCCCCCCCCN(CCCN)CCCN HKEBWESLPJXKAA-UHFFFAOYSA-N 0.000 description 1
- NYNKJVPRTLBJNQ-UHFFFAOYSA-N n'-(3-aminopropyl)-n'-dodecylpropane-1,3-diamine Chemical compound CCCCCCCCCCCCN(CCCN)CCCN NYNKJVPRTLBJNQ-UHFFFAOYSA-N 0.000 description 1
- RFGPGSDSMSKVEX-UHFFFAOYSA-N n'-(3-aminopropyl)-n'-hexadecylpropane-1,3-diamine Chemical compound CCCCCCCCCCCCCCCCN(CCCN)CCCN RFGPGSDSMSKVEX-UHFFFAOYSA-N 0.000 description 1
- RQSHNRYXVUXSJC-UHFFFAOYSA-N n'-(3-aminopropyl)-n'-hexylpropane-1,3-diamine Chemical compound CCCCCCN(CCCN)CCCN RQSHNRYXVUXSJC-UHFFFAOYSA-N 0.000 description 1
- FKLAQMPTKFHTBS-UHFFFAOYSA-N n'-(3-aminopropyl)-n'-tetradecylpropane-1,3-diamine Chemical compound CCCCCCCCCCCCCCN(CCCN)CCCN FKLAQMPTKFHTBS-UHFFFAOYSA-N 0.000 description 1
- YQKMBAXPSCHUOL-KHPPLWFESA-N n'-methyl-n'-[(z)-octadec-9-enyl]propane-1,3-diamine Chemical compound CCCCCCCC\C=C/CCCCCCCCN(C)CCCN YQKMBAXPSCHUOL-KHPPLWFESA-N 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N n-hexanoic acid Natural products CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- 239000003345 natural gas Substances 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 230000006911 nucleation Effects 0.000 description 1
- 238000010899 nucleation Methods 0.000 description 1
- HGASFNYMVGEKTF-UHFFFAOYSA-N octan-1-ol;hydrate Chemical compound O.CCCCCCCCO HGASFNYMVGEKTF-UHFFFAOYSA-N 0.000 description 1
- 235000021313 oleic acid Nutrition 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 description 1
- 239000004584 polyacrylic acid Substances 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 229940035044 sorbitan monolaurate Drugs 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000003784 tall oil Substances 0.000 description 1
- 239000004711 α-olefin Substances 0.000 description 1
Classifications
-
- 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
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Preventing Corrosion Or Incrustation Of Metals (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
La présente invention porte sur l'utilisation d'un groupe spécifique de composés non quaternaires contenant de l'azote, alkoxylés et/ou acylatés, comme antiagglomérants pour les hydrates de gaz. Les antiagglomérants sont des composés non quaternaires azotés à surface active ayant de 1 à 5 atomes d'azote, lesquels composés ont au moins un groupe hydrophobique ayant de 6 à 24 atomes de carbone et où le groupe hydrophobique est lié au reste de la molécule par une fraction amine, une fraction éther ou une fraction amide, pour autant que le groupe hydrophobique est relié au moyen d'une fraction amide au reste de la molécule, les composés doivent contenir au total au moins deux atomes d'azote et facultativement contenir 1 à 12 groupes -CH2CH2O- et/ou 1 à 6 groupes hydroxyalkyles ayant 3 à 4 atomes de carbone et lesquels composés ont au moins un groupe acyle en C2-C3 et/ou au moins un groupe hydroxyalkyl avec 3 à 4 atomes de carbone, ou un de ses sels. L'invention porte également sur une méthode visant à empêcher l'agglomération d'hydrates de gaz dans un conduit et des compositions comprenant l'antiagglomérant d'hydrate de gaz, un inhibiteur de corrosion et/ou un inhibiteur de dépôt de paraffine.
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP06111496.3 | 2006-03-21 | ||
| EP06111496 | 2006-03-21 | ||
| US83899206P | 2006-08-21 | 2006-08-21 | |
| US60/838,992 | 2006-08-21 | ||
| CA2646737A CA2646737C (fr) | 2006-03-21 | 2007-03-16 | Additif servant a maintenir la fluidite de fluides contenant des hydrates de gaz |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2646737A Division CA2646737C (fr) | 2006-03-21 | 2007-03-16 | Additif servant a maintenir la fluidite de fluides contenant des hydrates de gaz |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2832450A1 CA2832450A1 (fr) | 2007-09-27 |
| CA2832450C true CA2832450C (fr) | 2014-11-25 |
Family
ID=36695037
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2832452A Expired - Fee Related CA2832452C (fr) | 2006-03-21 | 2007-03-16 | Additif servant a maintenir la fluidite de fluides contenant des hydrates de gaz |
| CA2832450A Expired - Fee Related CA2832450C (fr) | 2006-03-21 | 2007-03-16 | Additif servant a maintenir la fluidite de fluides contenant des hydrates de gaz |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2832452A Expired - Fee Related CA2832452C (fr) | 2006-03-21 | 2007-03-16 | Additif servant a maintenir la fluidite de fluides contenant des hydrates de gaz |
Country Status (7)
| Country | Link |
|---|---|
| CN (1) | CN101405364B (fr) |
| AR (1) | AR059994A1 (fr) |
| BR (1) | BRPI0708852B1 (fr) |
| CA (2) | CA2832452C (fr) |
| DK (1) | DK1996669T3 (fr) |
| MY (1) | MY153425A (fr) |
| RU (1) | RU2439120C2 (fr) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8618025B2 (en) * | 2010-12-16 | 2013-12-31 | Nalco Company | Composition and method for reducing hydrate agglomeration |
| BR112013021905A2 (pt) * | 2011-09-26 | 2016-11-01 | Multi Chem Group Llc | composição inibidora antiaglomerado de hidrato, e, método para aplicar uma composição inibidora antiaglomerado de hidrato a uma corrente de hidrocarboneto |
| CN102784604A (zh) * | 2012-07-24 | 2012-11-21 | 华南理工大学 | 气体水合物生成促进剂及其制法和应用 |
| EP3008283A4 (fr) * | 2013-06-14 | 2017-04-19 | Flotek Chemistry, LLC | Procédés et compositions de stimulation de la production d'hydrocarbures à partir de formations souterraines |
| CN114806528B (zh) * | 2022-05-12 | 2023-07-11 | 中国石油大学(华东) | 一种含低剂量pko的复配型双效水合物抑制剂及其制备方法和应用 |
| CN116200179B (zh) * | 2023-02-17 | 2024-05-28 | 广东海洋大学 | 一种减少硫酸盐还原细菌腐蚀的表面活性剂制剂 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5244878A (en) * | 1987-12-30 | 1993-09-14 | Institut Francais Du Petrole | Process for delaying the formation and/or reducing the agglomeration tendency of hydrates |
| US5741758A (en) * | 1995-10-13 | 1998-04-21 | Bj Services Company, U.S.A. | Method for controlling gas hydrates in fluid mixtures |
| US6015852A (en) * | 1997-11-12 | 2000-01-18 | Air Products And Chemicals, Inc. | Surface tension reduction with alkylated higher polyamines |
| DE60131260T2 (de) * | 2000-04-07 | 2008-08-28 | Shell Internationale Research Maatschappij B.V. | Verfahren zur hemmung von verstopfung von röhren durch gashydrate |
| US6924315B2 (en) * | 2003-03-13 | 2005-08-02 | Air Products And Chemicals, Inc. | Gemini glycidyl ether adducts of polyhydroxyalkyl alkylenediamines |
-
2007
- 2007-03-16 RU RU2008141702/03A patent/RU2439120C2/ru not_active IP Right Cessation
- 2007-03-16 BR BRPI0708852-3A patent/BRPI0708852B1/pt not_active IP Right Cessation
- 2007-03-16 MY MYPI20083664A patent/MY153425A/en unknown
- 2007-03-16 CA CA2832452A patent/CA2832452C/fr not_active Expired - Fee Related
- 2007-03-16 CN CN200780009886.4A patent/CN101405364B/zh not_active Expired - Fee Related
- 2007-03-16 DK DK07726969.4T patent/DK1996669T3/da active
- 2007-03-16 CA CA2832450A patent/CA2832450C/fr not_active Expired - Fee Related
- 2007-03-20 AR ARP070101138A patent/AR059994A1/es active IP Right Grant
Also Published As
| Publication number | Publication date |
|---|---|
| RU2439120C2 (ru) | 2012-01-10 |
| RU2008141702A (ru) | 2010-04-27 |
| CA2832450A1 (fr) | 2007-09-27 |
| BRPI0708852B1 (pt) | 2017-11-28 |
| CA2832452C (fr) | 2014-11-18 |
| CA2832452A1 (fr) | 2007-09-27 |
| MY153425A (en) | 2015-02-13 |
| CN101405364B (zh) | 2014-04-30 |
| DK1996669T3 (da) | 2013-01-14 |
| BRPI0708852A2 (pt) | 2011-06-14 |
| CN101405364A (zh) | 2009-04-08 |
| AR059994A1 (es) | 2008-05-14 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CA2646737C (fr) | Additif servant a maintenir la fluidite de fluides contenant des hydrates de gaz | |
| CA2832450C (fr) | Additif servant a maintenir la fluidite de fluides contenant des hydrates de gaz | |
| CA2821730C (fr) | Composition et procede pour la reduction de l'agglomeration d'hydrate | |
| US6566309B1 (en) | Additives for inhibiting gas hydrate formation | |
| US6015929A (en) | Gas hydrate anti-agglomerates | |
| US6444852B1 (en) | Amines useful in inhibiting gas hydrate formation | |
| WO1996008636A1 (fr) | Tensioactifs utilises en tant qu'inhibiteurs d'hydrates de gaz | |
| CA2983402C (fr) | Anti-agglomerants azotes servant a maintenir la fluidite de fluides contenant des hydrates de gaz | |
| EP2497844A1 (fr) | Composition comprenant des esters quaternaire d'ammonium (esterquats) pour inhiber la corrosion des surfaces métalliques | |
| EP3807382A1 (fr) | Anti-agglomérants à base d'ester carboxyalkylique pour la lutte contre les hydrates de gaz naturel | |
| NO336116B1 (no) | Forbindelser med virkning som korrosjons- og gasshydratinhibitorer samt anvendelse derav. | |
| CA2912507C (fr) | Composes d'ammonium quaternaire et compositions d'inhibiteur d'hydrate gazeux | |
| WO2004111161A1 (fr) | Inhibiteurs d'hydrates de gaz | |
| ES2920701T3 (es) | Sales diamidoamónicas de ácidos dicarboxílicos asimétricamente sustituidas y su uso para la antiaglomeración de hidratos gaseosos | |
| WO2021115973A1 (fr) | Mélanges synergiques d'inhibiteurs d'hydrates de gaz anti-agglomérants avec des n-alcanoyl-polyhydroxyalkylamines | |
| AU2018229946B2 (en) | Method for inhibiting the agglomeration of gas hydrates | |
| OA16452A (en) | Composition and method for reducing hydrate agglomeration. |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request |
Effective date: 20131104 |
|
| EEER | Examination request |
Effective date: 20131104 |
|
| MKLA | Lapsed |
Effective date: 20220316 |