CA2832450C - Additive for preserving the fluidity of fluids containing gas hydrates - Google Patents
Additive for preserving the fluidity of fluids containing gas hydrates 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)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Preventing Corrosion Or Incrustation Of Metals (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP06111496 | 2006-03-21 | ||
| EP06111496.3 | 2006-03-21 | ||
| US83899206P | 2006-08-21 | 2006-08-21 | |
| US60/838,992 | 2006-08-21 | ||
| CA2646737A CA2646737C (en) | 2006-03-21 | 2007-03-16 | Additive for preserving the fluidity of fluids containing gas hydrates |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2646737A Division CA2646737C (en) | 2006-03-21 | 2007-03-16 | Additive for preserving the fluidity of fluids containing gas hydrates |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2832450A1 CA2832450A1 (en) | 2007-09-27 |
| CA2832450C true CA2832450C (en) | 2014-11-25 |
Family
ID=36695037
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2832450A Expired - Fee Related CA2832450C (en) | 2006-03-21 | 2007-03-16 | Additive for preserving the fluidity of fluids containing gas hydrates |
| CA2832452A Expired - Fee Related CA2832452C (en) | 2006-03-21 | 2007-03-16 | Additive for preserving the fluidity of fluids containing gas hydrates |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2832452A Expired - Fee Related CA2832452C (en) | 2006-03-21 | 2007-03-16 | Additive for preserving the fluidity of fluids containing gas hydrates |
Country Status (7)
| Country | Link |
|---|---|
| CN (1) | CN101405364B (pt) |
| AR (1) | AR059994A1 (pt) |
| BR (1) | BRPI0708852B1 (pt) |
| CA (2) | CA2832450C (pt) |
| DK (1) | DK1996669T3 (pt) |
| MY (1) | MY153425A (pt) |
| RU (1) | RU2439120C2 (pt) |
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 |
| WO2013048365A1 (en) * | 2011-09-26 | 2013-04-04 | Multi-Chem Group, Llc | Anti-agglomerate gas hydrate inhibitors for use in petroleum and natural gas systems |
| 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 |
| AU2014278002B2 (en) * | 2013-06-14 | 2017-08-17 | Flotek Chemistry, Llc | Methods and compositions for stimulating the production of hydrocarbons from subterranean formations |
| 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 |
| CN1218022C (zh) * | 2000-04-07 | 2005-09-07 | 国际壳牌研究有限公司 | 抑制管道被气体水合物堵塞的方法 |
| US6924315B2 (en) * | 2003-03-13 | 2005-08-02 | Air Products And Chemicals, Inc. | Gemini glycidyl ether adducts of polyhydroxyalkyl alkylenediamines |
-
2007
- 2007-03-16 CA CA2832450A patent/CA2832450C/en not_active Expired - Fee Related
- 2007-03-16 CA CA2832452A patent/CA2832452C/en not_active Expired - Fee Related
- 2007-03-16 BR BRPI0708852-3A patent/BRPI0708852B1/pt not_active IP Right Cessation
- 2007-03-16 RU RU2008141702/03A patent/RU2439120C2/ru not_active IP Right Cessation
- 2007-03-16 DK DK07726969.4T patent/DK1996669T3/da active
- 2007-03-16 MY MYPI20083664A patent/MY153425A/en unknown
- 2007-03-16 CN CN200780009886.4A patent/CN101405364B/zh not_active Expired - Fee Related
- 2007-03-20 AR ARP070101138A patent/AR059994A1/es active IP Right Grant
Also Published As
| Publication number | Publication date |
|---|---|
| MY153425A (en) | 2015-02-13 |
| CA2832452C (en) | 2014-11-18 |
| BRPI0708852A2 (pt) | 2011-06-14 |
| RU2008141702A (ru) | 2010-04-27 |
| CN101405364A (zh) | 2009-04-08 |
| BRPI0708852B1 (pt) | 2017-11-28 |
| CA2832450A1 (en) | 2007-09-27 |
| CN101405364B (zh) | 2014-04-30 |
| CA2832452A1 (en) | 2007-09-27 |
| RU2439120C2 (ru) | 2012-01-10 |
| DK1996669T3 (da) | 2013-01-14 |
| AR059994A1 (es) | 2008-05-14 |
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| MKLA | Lapsed |
Effective date: 20220316 |