NO347784B1 - A surfactant composition, production and use thereof - Google Patents
A surfactant composition, production and use thereof Download PDFInfo
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- NO347784B1 NO347784B1 NO20160047A NO20160047A NO347784B1 NO 347784 B1 NO347784 B1 NO 347784B1 NO 20160047 A NO20160047 A NO 20160047A NO 20160047 A NO20160047 A NO 20160047A NO 347784 B1 NO347784 B1 NO 347784B1
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- 239000000203 mixture Substances 0.000 title claims description 294
- 239000004094 surface-active agent Substances 0.000 title claims description 237
- 238000004519 manufacturing process Methods 0.000 title description 4
- 239000002736 nonionic surfactant Substances 0.000 claims description 209
- 125000000217 alkyl group Chemical group 0.000 claims description 192
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 139
- 150000001875 compounds Chemical class 0.000 claims description 129
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 114
- -1 halogen ion Chemical class 0.000 claims description 113
- 125000003342 alkenyl group Chemical group 0.000 claims description 112
- 125000002950 monocyclic group Chemical group 0.000 claims description 89
- 239000003093 cationic surfactant Substances 0.000 claims description 82
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims description 74
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 67
- 125000002947 alkylene group Chemical group 0.000 claims description 67
- 238000011084 recovery Methods 0.000 claims description 64
- 238000006243 chemical reaction Methods 0.000 claims description 60
- 239000012530 fluid Substances 0.000 claims description 55
- 239000003054 catalyst Substances 0.000 claims description 46
- 125000003118 aryl group Chemical group 0.000 claims description 45
- 125000001424 substituent group Chemical group 0.000 claims description 31
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims description 25
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 23
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 23
- 229910052783 alkali metal Inorganic materials 0.000 claims description 22
- 150000001340 alkali metals Chemical group 0.000 claims description 22
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 22
- 150000001342 alkaline earth metals Chemical group 0.000 claims description 22
- 238000000034 method Methods 0.000 claims description 18
- 125000004450 alkenylene group Chemical group 0.000 claims description 16
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 16
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 15
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 15
- 230000008569 process Effects 0.000 claims description 15
- 238000002156 mixing Methods 0.000 claims description 14
- 150000003839 salts Chemical class 0.000 claims description 14
- 239000003513 alkali Substances 0.000 claims description 13
- 125000005843 halogen group Chemical group 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 10
- 125000005529 alkyleneoxy group Chemical group 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 174
- 239000003921 oil Substances 0.000 description 163
- 239000000243 solution Substances 0.000 description 143
- 239000010779 crude oil Substances 0.000 description 98
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 80
- 239000007864 aqueous solution Substances 0.000 description 78
- 239000003795 chemical substances by application Substances 0.000 description 70
- 229920001451 polypropylene glycol Polymers 0.000 description 48
- 229940051841 polyoxyethylene ether Drugs 0.000 description 46
- 229920000056 polyoxyethylene ether Polymers 0.000 description 46
- 238000000926 separation method Methods 0.000 description 46
- 229910000029 sodium carbonate Inorganic materials 0.000 description 40
- 235000017550 sodium carbonate Nutrition 0.000 description 40
- 239000008346 aqueous phase Substances 0.000 description 38
- 239000012071 phase Substances 0.000 description 37
- 238000006073 displacement reaction Methods 0.000 description 31
- 238000012360 testing method Methods 0.000 description 31
- 125000004432 carbon atom Chemical group C* 0.000 description 30
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 29
- 239000000047 product Substances 0.000 description 29
- 229910052708 sodium Inorganic materials 0.000 description 29
- 239000011734 sodium Substances 0.000 description 29
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 28
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 28
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 28
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Substances [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 28
- 229940106681 chloroacetic acid Drugs 0.000 description 27
- 238000005406 washing Methods 0.000 description 26
- 238000000605 extraction Methods 0.000 description 25
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
- 239000011575 calcium Substances 0.000 description 24
- 125000004404 heteroalkyl group Chemical group 0.000 description 24
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 21
- 150000007942 carboxylates Chemical class 0.000 description 21
- LVTYICIALWPMFW-UHFFFAOYSA-N diisopropanolamine Chemical compound CC(O)CNCC(C)O LVTYICIALWPMFW-UHFFFAOYSA-N 0.000 description 21
- 229940043276 diisopropanolamine Drugs 0.000 description 21
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 20
- 239000008398 formation water Substances 0.000 description 19
- FDRCDNZGSXJAFP-UHFFFAOYSA-M sodium chloroacetate Chemical compound [Na+].[O-]C(=O)CCl FDRCDNZGSXJAFP-UHFFFAOYSA-M 0.000 description 19
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 18
- 125000001624 naphthyl group Chemical group 0.000 description 18
- 239000003027 oil sand Substances 0.000 description 18
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 18
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 17
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 17
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 17
- 229920002554 vinyl polymer Polymers 0.000 description 17
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 16
- 235000011114 ammonium hydroxide Nutrition 0.000 description 16
- 229910052799 carbon Inorganic materials 0.000 description 16
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 15
- 125000006356 alkylene carbonyl group Chemical group 0.000 description 14
- HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 description 14
- 239000011541 reaction mixture Substances 0.000 description 14
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 13
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 13
- 230000000694 effects Effects 0.000 description 13
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 12
- LZZYPRNAOMGNLH-UHFFFAOYSA-M Cetrimonium bromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[N+](C)(C)C LZZYPRNAOMGNLH-UHFFFAOYSA-M 0.000 description 12
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 12
- 125000005090 alkenylcarbonyl group Chemical group 0.000 description 12
- 125000004448 alkyl carbonyl group Chemical group 0.000 description 12
- 238000005516 engineering process Methods 0.000 description 12
- 238000009987 spinning Methods 0.000 description 12
- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 description 12
- 229910052791 calcium Inorganic materials 0.000 description 10
- 239000003208 petroleum Substances 0.000 description 10
- 229910052700 potassium Inorganic materials 0.000 description 10
- 230000002862 amidating effect Effects 0.000 description 9
- 235000019270 ammonium chloride Nutrition 0.000 description 9
- 150000002191 fatty alcohols Chemical class 0.000 description 9
- 229920000642 polymer Polymers 0.000 description 9
- 239000000725 suspension Substances 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 8
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 8
- 230000003113 alkalizing effect Effects 0.000 description 8
- LHIJANUOQQMGNT-UHFFFAOYSA-N aminoethylethanolamine Chemical compound NCCNCCO LHIJANUOQQMGNT-UHFFFAOYSA-N 0.000 description 8
- 239000007795 chemical reaction product Substances 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 8
- 229910052744 lithium Inorganic materials 0.000 description 8
- 229910052749 magnesium Inorganic materials 0.000 description 8
- 125000004433 nitrogen atom Chemical group N* 0.000 description 8
- 229920002401 polyacrylamide Polymers 0.000 description 8
- NHGXDBSUJJNIRV-UHFFFAOYSA-M tetrabutylammonium chloride Chemical compound [Cl-].CCCC[N+](CCCC)(CCCC)CCCC NHGXDBSUJJNIRV-UHFFFAOYSA-M 0.000 description 8
- 230000002378 acidificating effect Effects 0.000 description 7
- 125000001309 chloro group Chemical group Cl* 0.000 description 7
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 7
- 239000000347 magnesium hydroxide Substances 0.000 description 7
- 235000012254 magnesium hydroxide Nutrition 0.000 description 7
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 7
- 239000011148 porous material Substances 0.000 description 7
- 239000004576 sand Substances 0.000 description 7
- 238000007738 vacuum evaporation Methods 0.000 description 7
- PBLNBZIONSLZBU-UHFFFAOYSA-N 1-bromododecane Chemical compound CCCCCCCCCCCCBr PBLNBZIONSLZBU-UHFFFAOYSA-N 0.000 description 6
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 6
- 125000000129 anionic group Chemical group 0.000 description 6
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 6
- 239000000920 calcium hydroxide Substances 0.000 description 6
- 235000011116 calcium hydroxide Nutrition 0.000 description 6
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 6
- WOWHHFRSBJGXCM-UHFFFAOYSA-M cetyltrimethylammonium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCC[N+](C)(C)C WOWHHFRSBJGXCM-UHFFFAOYSA-M 0.000 description 6
- 229910052801 chlorine Inorganic materials 0.000 description 6
- 230000003472 neutralizing effect Effects 0.000 description 6
- 238000011056 performance test Methods 0.000 description 6
- 230000035699 permeability Effects 0.000 description 6
- 235000017557 sodium bicarbonate Nutrition 0.000 description 6
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- GAWAYYRQGQZKCR-REOHCLBHSA-N (S)-2-chloropropanoic acid Chemical compound C[C@H](Cl)C(O)=O GAWAYYRQGQZKCR-REOHCLBHSA-N 0.000 description 5
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 5
- GQFZYTXZJHSSEA-UHFFFAOYSA-M decyl(triethyl)azanium;hydroxide Chemical compound [OH-].CCCCCCCCCC[N+](CC)(CC)CC GQFZYTXZJHSSEA-UHFFFAOYSA-M 0.000 description 5
- IQDGSYLLQPDQDV-UHFFFAOYSA-N dimethylazanium;chloride Chemical compound Cl.CNC IQDGSYLLQPDQDV-UHFFFAOYSA-N 0.000 description 5
- 230000002708 enhancing effect Effects 0.000 description 5
- 238000000746 purification Methods 0.000 description 5
- 125000001453 quaternary ammonium group Chemical group 0.000 description 5
- MQAYPFVXSPHGJM-UHFFFAOYSA-M trimethyl(phenyl)azanium;chloride Chemical compound [Cl-].C[N+](C)(C)C1=CC=CC=C1 MQAYPFVXSPHGJM-UHFFFAOYSA-M 0.000 description 5
- REYJJPSVUYRZGE-UHFFFAOYSA-N Octadecylamine Chemical compound CCCCCCCCCCCCCCCCCCN REYJJPSVUYRZGE-UHFFFAOYSA-N 0.000 description 4
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 4
- NQGIJDNPUZEBRU-UHFFFAOYSA-N dodecanoyl chloride Chemical compound CCCCCCCCCCCC(Cl)=O NQGIJDNPUZEBRU-UHFFFAOYSA-N 0.000 description 4
- DDXLVDQZPFLQMZ-UHFFFAOYSA-M dodecyl(trimethyl)azanium;chloride Chemical compound [Cl-].CCCCCCCCCCCC[N+](C)(C)C DDXLVDQZPFLQMZ-UHFFFAOYSA-M 0.000 description 4
- 239000011552 falling film Substances 0.000 description 4
- 125000001153 fluoro group Chemical group F* 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 125000004430 oxygen atom Chemical group O* 0.000 description 4
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 4
- 238000002390 rotary evaporation Methods 0.000 description 4
- HKPHUICWPSKEMR-UHFFFAOYSA-M sodium;chloromethanesulfonate Chemical compound [Na+].[O-]S(=O)(=O)CCl HKPHUICWPSKEMR-UHFFFAOYSA-M 0.000 description 4
- SFVFIFLLYFPGHH-UHFFFAOYSA-M stearalkonium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCCCC[N+](C)(C)CC1=CC=CC=C1 SFVFIFLLYFPGHH-UHFFFAOYSA-M 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 150000008054 sulfonate salts Chemical class 0.000 description 4
- 238000006277 sulfonation reaction Methods 0.000 description 4
- SNNIPOQLGBPXPS-UHFFFAOYSA-M tetraoctylazanium;chloride Chemical compound [Cl-].CCCCCCCC[N+](CCCCCCCC)(CCCCCCCC)CCCCCCCC SNNIPOQLGBPXPS-UHFFFAOYSA-M 0.000 description 4
- MYMSJFSOOQERIO-UHFFFAOYSA-N 1-bromodecane Chemical compound CCCCCCCCCCBr MYMSJFSOOQERIO-UHFFFAOYSA-N 0.000 description 3
- HNTGIJLWHDPAFN-UHFFFAOYSA-N 1-bromohexadecane Chemical compound CCCCCCCCCCCCCCCCBr HNTGIJLWHDPAFN-UHFFFAOYSA-N 0.000 description 3
- NQUVCRCCRXRJCK-UHFFFAOYSA-N 4-methylbenzoyl chloride Chemical compound CC1=CC=C(C(Cl)=O)C=C1 NQUVCRCCRXRJCK-UHFFFAOYSA-N 0.000 description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- IHHCUKJSKTUVLZ-UHFFFAOYSA-N CC1=CC=C(C(=O)NCCNCCNCCNCCN)C=C1 Chemical compound CC1=CC=C(C(=O)NCCNCCNCCNCCN)C=C1 IHHCUKJSKTUVLZ-UHFFFAOYSA-N 0.000 description 3
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 230000000996 additive effect Effects 0.000 description 3
- 150000001335 aliphatic alkanes Chemical class 0.000 description 3
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 3
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 3
- 229940073608 benzyl chloride Drugs 0.000 description 3
- AQNQQHJNRPDOQV-UHFFFAOYSA-N bromocyclohexane Chemical compound BrC1CCCCC1 AQNQQHJNRPDOQV-UHFFFAOYSA-N 0.000 description 3
- 125000002091 cationic group Chemical group 0.000 description 3
- HMPHJJBZKIZRHG-UHFFFAOYSA-N chloromethanesulfonic acid Chemical compound OS(=O)(=O)CCl HMPHJJBZKIZRHG-UHFFFAOYSA-N 0.000 description 3
- 229920001577 copolymer Polymers 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 125000000524 functional group Chemical group 0.000 description 3
- 229910052740 iodine Inorganic materials 0.000 description 3
- WTBAHSZERDXKKZ-UHFFFAOYSA-N octadecanoyl chloride Chemical compound CCCCCCCCCCCCCCCCCC(Cl)=O WTBAHSZERDXKKZ-UHFFFAOYSA-N 0.000 description 3
- 239000003129 oil well Substances 0.000 description 3
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 3
- 229920003169 water-soluble polymer Polymers 0.000 description 3
- RRQWVJIFKFIUJU-KTKRTIGZSA-N (z)-1-bromooctadec-9-ene Chemical compound CCCCCCCC\C=C/CCCCCCCCBr RRQWVJIFKFIUJU-KTKRTIGZSA-N 0.000 description 2
- QGLWBTPVKHMVHM-KTKRTIGZSA-N (z)-octadec-9-en-1-amine Chemical compound CCCCCCCC\C=C/CCCCCCCCN QGLWBTPVKHMVHM-KTKRTIGZSA-N 0.000 description 2
- FJLUATLTXUNBOT-UHFFFAOYSA-N 1-Hexadecylamine Chemical compound CCCCCCCCCCCCCCCCN FJLUATLTXUNBOT-UHFFFAOYSA-N 0.000 description 2
- ODNNIPNNVNPOCY-UHFFFAOYSA-N 1-N-[2-[2-[2-(benzylamino)ethylamino]ethylamino]ethyl]-3-phenylpropane-1,2-diamine Chemical compound C(C1=CC=CC=C1)NCCNCCNCCNCC(N)CC1=CC=CC=C1 ODNNIPNNVNPOCY-UHFFFAOYSA-N 0.000 description 2
- WHNBDXQTMPYBAT-UHFFFAOYSA-N 2-butyloxirane Chemical compound CCCCC1CO1 WHNBDXQTMPYBAT-UHFFFAOYSA-N 0.000 description 2
- JBIJLHTVPXGSAM-UHFFFAOYSA-N 2-naphthylamine Chemical compound C1=CC=CC2=CC(N)=CC=C21 JBIJLHTVPXGSAM-UHFFFAOYSA-N 0.000 description 2
- TWBPWBPGNQWFSJ-UHFFFAOYSA-N 2-phenylaniline Chemical compound NC1=CC=CC=C1C1=CC=CC=C1 TWBPWBPGNQWFSJ-UHFFFAOYSA-N 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- HPEUJPJOZXNMSJ-UHFFFAOYSA-N Methyl stearate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC HPEUJPJOZXNMSJ-UHFFFAOYSA-N 0.000 description 2
- LFICZBFFAFTFNL-UHFFFAOYSA-N N-[1-[2-[2-(2-aminoethylamino)ethylamino]ethylamino]dodecan-2-yl]benzamide Chemical compound C(C1=CC=CC=C1)(=O)NC(CNCCNCCNCCN)CCCCCCCCCC LFICZBFFAFTFNL-UHFFFAOYSA-N 0.000 description 2
- BTWLUQWXFMTYSX-UHFFFAOYSA-N N-[2-[2-[2-(dodecanoylamino)ethylamino]ethylamino]ethyl]octadecanamide Chemical compound C(CCCCCCCCCCCCCCCCC)(=O)NCCNCCNCCNC(CCCCCCCCCCC)=O BTWLUQWXFMTYSX-UHFFFAOYSA-N 0.000 description 2
- ZIPLEBUYEGQUNJ-UHFFFAOYSA-N N-[2-[2-[2-[(2-amino-3-oxo-3-phenylpropyl)amino]ethylamino]ethylamino]ethyl]benzamide Chemical compound C(C1=CC=CC=C1)(=O)NCCNCCNCCNCC(N)C(C1=CC=CC=C1)=O ZIPLEBUYEGQUNJ-UHFFFAOYSA-N 0.000 description 2
- ZPMWRUDTTWUWJN-UHFFFAOYSA-N N-[2-[2-[2-[[2-amino-3-(4-methylphenyl)-3-oxopropyl]amino]ethylamino]ethylamino]ethyl]-4-methylbenzamide Chemical compound CC1=CC=C(C(=O)NCCNCCNCCNCC(N)C(C2=CC=C(C=C2)C)=O)C=C1 ZPMWRUDTTWUWJN-UHFFFAOYSA-N 0.000 description 2
- BKZXKHCXHOJLET-UHFFFAOYSA-N N-decyl-N'-[2-(decylamino)ethyl]ethane-1,2-diamine Chemical compound C(CCCCCCCCC)NCCNCCNCCCCCCCCCC BKZXKHCXHOJLET-UHFFFAOYSA-N 0.000 description 2
- PJGQGTLMZMGGMF-UHFFFAOYSA-N N-dodecyl-N'-[2-[2-(dodecylamino)ethylamino]ethyl]ethane-1,2-diamine Chemical compound C(CCCCCCCCCCC)NCCNCCNCCNCCCCCCCCCCCC PJGQGTLMZMGGMF-UHFFFAOYSA-N 0.000 description 2
- HEVITTVYWLQVEZ-UHFFFAOYSA-N N-dodecyl-N'-[2-[2-(hexadecylamino)ethylamino]ethyl]ethane-1,2-diamine Chemical compound C(CCCCCCCCCCC)NCCNCCNCCNCCCCCCCCCCCCCCCC HEVITTVYWLQVEZ-UHFFFAOYSA-N 0.000 description 2
- ZHJGCQGVAFUFRM-UHFFFAOYSA-N N-hexadecyl-N'-[2-(hexadecylamino)ethyl]ethane-1,2-diamine Chemical compound C(CCCCCCCCCCCCCCC)NCCNCCNCCCCCCCCCCCCCCCC ZHJGCQGVAFUFRM-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 125000003172 aldehyde group Chemical group 0.000 description 2
- 125000003368 amide group Chemical group 0.000 description 2
- 239000000908 ammonium hydroxide Substances 0.000 description 2
- 229920001400 block copolymer Polymers 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 125000003493 decenyl group Chemical group [H]C([*])=C([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000005066 dodecenyl group Chemical group C(=CCCCCCCCCCC)* 0.000 description 2
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- JRBPAEWTRLWTQC-UHFFFAOYSA-N dodecylamine Chemical compound CCCCCCCCCCCCN JRBPAEWTRLWTQC-UHFFFAOYSA-N 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 150000004679 hydroxides Chemical class 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- RRHLGOOTLYHTEW-UHFFFAOYSA-N n'-[2-(dodecylamino)ethyl]ethane-1,2-diamine Chemical compound CCCCCCCCCCCCNCCNCCN RRHLGOOTLYHTEW-UHFFFAOYSA-N 0.000 description 2
- DWZJYSSNBXBMLS-UHFFFAOYSA-N n'-[2-[2-(dodecylamino)ethylamino]ethyl]ethane-1,2-diamine Chemical compound CCCCCCCCCCCCNCCNCCNCCN DWZJYSSNBXBMLS-UHFFFAOYSA-N 0.000 description 2
- PQTSAJIDHPKODS-UHFFFAOYSA-N n'-[2-[2-(octadecylamino)ethylamino]ethyl]ethane-1,2-diamine Chemical compound CCCCCCCCCCCCCCCCCCNCCNCCNCCN PQTSAJIDHPKODS-UHFFFAOYSA-N 0.000 description 2
- CAOBWNHRKKGJEA-UHFFFAOYSA-N n'-[2-[2-[2-(benzylamino)ethylamino]ethylamino]ethyl]ethane-1,2-diamine Chemical compound NCCNCCNCCNCCNCC1=CC=CC=C1 CAOBWNHRKKGJEA-UHFFFAOYSA-N 0.000 description 2
- IKGMUURUKOAOQL-UHFFFAOYSA-N n-[2-(2-aminoethylamino)ethyl]dodecanamide Chemical compound CCCCCCCCCCCC(=O)NCCNCCN IKGMUURUKOAOQL-UHFFFAOYSA-N 0.000 description 2
- CFAQSLLBQNAXNY-UHFFFAOYSA-N n-[2-[2-(2-aminoethylamino)ethylamino]ethyl]octadecanamide Chemical compound CCCCCCCCCCCCCCCCCC(=O)NCCNCCNCCN CFAQSLLBQNAXNY-UHFFFAOYSA-N 0.000 description 2
- TVBANASQCOWJTC-UHFFFAOYSA-N n-[2-[2-[2-(dodecanoylamino)ethylamino]ethylamino]ethyl]dodecanamide Chemical compound CCCCCCCCCCCC(=O)NCCNCCNCCNC(=O)CCCCCCCCCCC TVBANASQCOWJTC-UHFFFAOYSA-N 0.000 description 2
- KWLJEKOMAZTKJG-UHFFFAOYSA-N n-[2-[2-[2-(octadecanoylamino)ethylamino]ethylamino]ethyl]octadecanamide Chemical compound CCCCCCCCCCCCCCCCCC(=O)NCCNCCNCCNC(=O)CCCCCCCCCCCCCCCCC KWLJEKOMAZTKJG-UHFFFAOYSA-N 0.000 description 2
- WBAZLMILKDTIQE-UHFFFAOYSA-N n-dodecyl-n'-[2-(dodecylamino)ethyl]ethane-1,2-diamine Chemical compound CCCCCCCCCCCCNCCNCCNCCCCCCCCCCCC WBAZLMILKDTIQE-UHFFFAOYSA-N 0.000 description 2
- 125000005064 octadecenyl group Chemical group C(=CCCCCCCCCCCCCCCCC)* 0.000 description 2
- 125000004365 octenyl group Chemical group C(=CCCCCCC)* 0.000 description 2
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 238000004237 preparative chromatography Methods 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 239000011435 rock Substances 0.000 description 2
- 229910052701 rubidium Inorganic materials 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000004434 sulfur atom Chemical group 0.000 description 2
- LVUQIFNWDIFXFY-KTKRTIGZSA-N (Z)-2-(2-aminoethylamino)icos-11-en-1-ol Chemical compound C(CCCCCCC\C=C/CCCCCCCC)C(CO)NCCN LVUQIFNWDIFXFY-KTKRTIGZSA-N 0.000 description 1
- PSBDWGZCVUAZQS-UHFFFAOYSA-N (dimethylsulfonio)acetate Chemical compound C[S+](C)CC([O-])=O PSBDWGZCVUAZQS-UHFFFAOYSA-N 0.000 description 1
- WSULSMOGMLRGKU-UHFFFAOYSA-N 1-bromooctadecane Chemical compound CCCCCCCCCCCCCCCCCCBr WSULSMOGMLRGKU-UHFFFAOYSA-N 0.000 description 1
- KOFZTCSTGIWCQG-UHFFFAOYSA-N 1-bromotetradecane Chemical compound CCCCCCCCCCCCCCBr KOFZTCSTGIWCQG-UHFFFAOYSA-N 0.000 description 1
- MRMLYDBKPZENMN-UHFFFAOYSA-N 2-(2-aminoethylamino)-1-hydroxyicosan-3-one Chemical compound C(CCCCCCCCCCCCCCCCC)(=O)C(CO)NCCN MRMLYDBKPZENMN-UHFFFAOYSA-N 0.000 description 1
- NWLKFNSTHFEQJJ-UHFFFAOYSA-N 2-(2-aminoethylamino)-3-hydroxy-1-phenylpropan-1-one Chemical compound C(C1=CC=CC=C1)(=O)C(CO)NCCN NWLKFNSTHFEQJJ-UHFFFAOYSA-N 0.000 description 1
- CIPRVLAYVXDBLS-UHFFFAOYSA-N 2-(2-aminoethylamino)hexadecan-1-ol Chemical compound C(CCCCCCCCCCCCC)C(CO)NCCN CIPRVLAYVXDBLS-UHFFFAOYSA-N 0.000 description 1
- JLUUVUUYIXBDCG-UHFFFAOYSA-N 6-[1-benzyl-6-(4-methylpiperazin-1-yl)benzimidazol-2-yl]-n,3-dimethyl-[1,2,4]triazolo[4,3-a]pyrazin-8-amine Chemical compound C=1N2C(C)=NN=C2C(NC)=NC=1C1=NC2=CC=C(N3CCN(C)CC3)C=C2N1CC1=CC=CC=C1 JLUUVUUYIXBDCG-UHFFFAOYSA-N 0.000 description 1
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- JBWRAWTYKJAVIL-UHFFFAOYSA-N N'-[2-(cyclohexylamino)ethyl]-N-[2-[2-(cyclohexylamino)ethylamino]ethyl]ethane-1,2-diamine Chemical compound C1(CCCCC1)NCCNCCNCCNCCNC1CCCCC1 JBWRAWTYKJAVIL-UHFFFAOYSA-N 0.000 description 1
- IAXRGSKHQWAFAI-UHFFFAOYSA-N N'-[2-[2-[2-(cyclohexylamino)ethylamino]ethylamino]ethyl]ethane-1,2-diamine Chemical compound C1(CCCCC1)NCCNCCNCCNCCN IAXRGSKHQWAFAI-UHFFFAOYSA-N 0.000 description 1
- PLBHYLHHENBSNN-UHFFFAOYSA-N N-[2-[2-[2-(2-aminoethylamino)ethylamino]ethylamino]ethyl]benzamide Chemical compound C(C1=CC=CC=C1)(=O)NCCNCCNCCNCCN PLBHYLHHENBSNN-UHFFFAOYSA-N 0.000 description 1
- QEOWFDYSNYCPRK-UHFFFAOYSA-N OCC[Na] Chemical compound OCC[Na] QEOWFDYSNYCPRK-UHFFFAOYSA-N 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 230000004075 alteration Effects 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000003868 ammonium compounds Chemical class 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 239000011260 aqueous acid Substances 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 229940006460 bromide ion Drugs 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 229910000020 calcium bicarbonate Inorganic materials 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 230000002925 chemical effect Effects 0.000 description 1
- 238000004581 coalescence Methods 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000004945 emulsification Methods 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- CAMHHLOGFDZBBG-UHFFFAOYSA-N epoxidized methyl oleate Natural products CCCCCCCCC1OC1CCCCCCCC(=O)OC CAMHHLOGFDZBBG-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-M iodide Chemical compound [I-] XMBWDFGMSWQBCA-UHFFFAOYSA-M 0.000 description 1
- 229940006461 iodide ion Drugs 0.000 description 1
- 125000002346 iodo group Chemical group I* 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229940095102 methyl benzoate Drugs 0.000 description 1
- 239000000693 micelle Substances 0.000 description 1
- IZBVZYNGZBUGAZ-UHFFFAOYSA-N n'-[2-(benzylamino)ethyl]ethane-1,2-diamine Chemical compound NCCNCCNCC1=CC=CC=C1 IZBVZYNGZBUGAZ-UHFFFAOYSA-N 0.000 description 1
- UTDZKADZZPYDNV-UHFFFAOYSA-N n'-[2-(cyclohexylamino)ethyl]ethane-1,2-diamine Chemical compound NCCNCCNC1CCCCC1 UTDZKADZZPYDNV-UHFFFAOYSA-N 0.000 description 1
- UZWLVTABZVASMA-UHFFFAOYSA-N n'-[2-(decylamino)ethyl]ethane-1,2-diamine Chemical compound CCCCCCCCCCNCCNCCN UZWLVTABZVASMA-UHFFFAOYSA-N 0.000 description 1
- MVCXBMAXWHWFSV-UHFFFAOYSA-N n'-[2-(hexadecylamino)ethyl]ethane-1,2-diamine Chemical compound CCCCCCCCCCCCCCCCNCCNCCN MVCXBMAXWHWFSV-UHFFFAOYSA-N 0.000 description 1
- ILKYTZMDSZJWNM-KTKRTIGZSA-N n'-[2-[2-[[(z)-octadec-9-enyl]amino]ethylamino]ethyl]ethane-1,2-diamine Chemical compound CCCCCCCC\C=C/CCCCCCCCNCCNCCNCCN ILKYTZMDSZJWNM-KTKRTIGZSA-N 0.000 description 1
- JEUXZUSUYIHGNL-UHFFFAOYSA-N n,n-diethylethanamine;hydrate Chemical compound O.CCN(CC)CC JEUXZUSUYIHGNL-UHFFFAOYSA-N 0.000 description 1
- BVTFPKVMGFMGFX-UHFFFAOYSA-N n-[2-[2-(2-aminoethylamino)ethylamino]ethyl]dodecanamide Chemical compound CCCCCCCCCCCC(=O)NCCNCCNCCN BVTFPKVMGFMGFX-UHFFFAOYSA-N 0.000 description 1
- 238000001728 nano-filtration Methods 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920002503 polyoxyethylene-polyoxypropylene Polymers 0.000 description 1
- CHKVPAROMQMJNQ-UHFFFAOYSA-M potassium bisulfate Chemical compound [K+].OS([O-])(=O)=O CHKVPAROMQMJNQ-UHFFFAOYSA-M 0.000 description 1
- 229910000343 potassium bisulfate Inorganic materials 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
- 229920005604 random copolymer Polymers 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- UMGBSQBKXZHNHH-UHFFFAOYSA-M sodium 5-chloropentane-1-sulfonate Chemical compound ClCCCCCS(=O)(=O)[O-].[Na+] UMGBSQBKXZHNHH-UHFFFAOYSA-M 0.000 description 1
- WBHQBSYUUJJSRZ-UHFFFAOYSA-M sodium bisulfate Chemical compound [Na+].OS([O-])(=O)=O WBHQBSYUUJJSRZ-UHFFFAOYSA-M 0.000 description 1
- 229910000342 sodium bisulfate Inorganic materials 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 229940117986 sulfobetaine Drugs 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- YMBCJWGVCUEGHA-UHFFFAOYSA-M tetraethylammonium chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC YMBCJWGVCUEGHA-UHFFFAOYSA-M 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
- C09K8/58—Compositions for enhanced recovery methods for obtaining hydrocarbons, i.e. for improving the mobility of the oil, e.g. displacing fluids
- C09K8/584—Compositions for enhanced recovery methods for obtaining hydrocarbons, i.e. for improving the mobility of the oil, e.g. displacing fluids characterised by the use of specific surfactants
Landscapes
- Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Chemistry (AREA)
- Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201310237545.XA CN104232045B (zh) | 2013-06-17 | 2013-06-17 | 复合型表面活性剂组合物、制备方法及应用 |
| PCT/CN2014/000595 WO2014201854A1 (zh) | 2013-06-17 | 2014-06-17 | 一种表面活性剂组合物、其制造方法及其应用 |
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| Publication Number | Publication Date |
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| NO20160047A1 NO20160047A1 (en) | 2016-01-11 |
| NO347784B1 true NO347784B1 (en) | 2024-03-25 |
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| NO20160047A NO347784B1 (en) | 2013-06-17 | 2016-01-11 | A surfactant composition, production and use thereof |
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| CN (1) | CN104232045B (zh) |
| NO (1) | NO347784B1 (zh) |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105199703B (zh) * | 2015-08-24 | 2018-05-22 | 中国石油化工股份有限公司 | 一种耐高温低度交联三元调驱剂及其制备方法 |
| CN106590592B (zh) * | 2015-10-20 | 2019-11-08 | 中国石油化工股份有限公司 | 提高原油采收率的复合表面活性剂 |
| CN106867494B (zh) * | 2015-12-14 | 2020-10-16 | 中国石油化工股份有限公司 | 增溶原油能力强的组合表面活性剂及低成本制备方法 |
| CN106867495B (zh) * | 2015-12-14 | 2020-10-16 | 中国石油化工股份有限公司 | 复合型表面活性剂及其低成本制备方法 |
| EP3652269A1 (en) * | 2017-07-14 | 2020-05-20 | Basf Se | Solubility enhancers on basis of allyl alcohol for aqueous surfactant formulations for enhanced oil recovery |
| CN109679624A (zh) * | 2017-10-19 | 2019-04-26 | 中国石油化工股份有限公司 | 化学驱油用非烷基酚类表面活性剂组合强化采油的方法 |
| CN109679628A (zh) * | 2017-10-19 | 2019-04-26 | 中国石油化工股份有限公司 | 化学驱油用非烷基酚类表面活性剂组合物及其制备方法 |
| CN108276979A (zh) * | 2017-12-20 | 2018-07-13 | 武汉奥克特种化学有限公司 | 一种耐温抗盐型聚醚磺酸盐驱油剂及其制备方法 |
| CN111088013B (zh) * | 2018-10-23 | 2022-07-12 | 中国石油化工股份有限公司 | 阴阳离子复合驱油表面活性剂及其制备方法和驱油方法 |
| CN111088014B (zh) * | 2018-10-23 | 2022-02-01 | 中国石油化工股份有限公司 | 采油用阴阳复合表面活性剂及其制备方法和驱油方法 |
| CN112226225B (zh) * | 2019-07-15 | 2023-04-07 | 中国石油化工股份有限公司 | 低渗透油藏注水井降压增注用耐温抗盐表面活性剂组合物及其制备方法和应用 |
| CN112694877B (zh) * | 2019-10-22 | 2022-12-09 | 中国石油化工股份有限公司 | 含双酚a聚醚二酸盐的复合表面活性剂及其制备方法和应用 |
| CN112795002B (zh) * | 2019-11-14 | 2022-04-01 | 中国石油化工股份有限公司 | 含杂原子的聚醚阴非离子表面活性剂及其制备方法 |
| CN111732946B (zh) * | 2020-06-29 | 2022-11-04 | 中国石油天然气集团有限公司 | 压裂用防膨型助排剂及其制备方法 |
| CN113930227B (zh) * | 2020-07-14 | 2023-05-02 | 中国石油化工股份有限公司 | 含阴-非离子和阳-非离子表面活性剂的组合物及其制备方法和应用 |
| CN113861049B (zh) * | 2021-10-22 | 2024-03-22 | 中国石油化工股份有限公司 | 一种co2增溶降粘剂及其制备方法和应用 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4370243A (en) * | 1981-02-09 | 1983-01-25 | Mobil Oil Corporation | Oil recovery by surfactant-alcohol waterflooding |
| US20120101010A1 (en) * | 2010-08-27 | 2012-04-26 | Board Of Regents, The University Of Texas System | Alkoxy carboxylate surfactants |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101768462B (zh) * | 2008-12-31 | 2013-01-30 | 中国石油化工股份有限公司 | 一种稠油乳化降粘的方法 |
| CN101580705B (zh) * | 2009-06-12 | 2012-03-21 | 中国石油大学(华东) | 一种用于普通稠油油藏的低气液比泡沫起泡剂及其注入方法 |
| CN102575153A (zh) * | 2009-07-30 | 2012-07-11 | 巴斯夫欧洲公司 | 压裂地下岩层的方法 |
| CN102040993B (zh) * | 2010-05-12 | 2013-07-31 | 中国石油天然气股份有限公司 | 一种适合超高温超高盐超钙镁均质油藏驱油剂 |
| CN102485771A (zh) * | 2010-12-03 | 2012-06-06 | 中国石油天然气股份有限公司 | 脂肪醇聚氧丙烯聚氧乙烯醚羧酸盐及其制备和应用 |
-
2013
- 2013-06-17 CN CN201310237545.XA patent/CN104232045B/zh active Active
-
2016
- 2016-01-11 NO NO20160047A patent/NO347784B1/en unknown
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4370243A (en) * | 1981-02-09 | 1983-01-25 | Mobil Oil Corporation | Oil recovery by surfactant-alcohol waterflooding |
| US20120101010A1 (en) * | 2010-08-27 | 2012-04-26 | Board Of Regents, The University Of Texas System | Alkoxy carboxylate surfactants |
Also Published As
| Publication number | Publication date |
|---|---|
| NO20160047A1 (en) | 2016-01-11 |
| CN104232045A (zh) | 2014-12-24 |
| CN104232045B (zh) | 2017-02-15 |
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