US20090057617A1 - Corrosion inhibitors containing anionic surfactants - Google Patents
Corrosion inhibitors containing anionic surfactants Download PDFInfo
- Publication number
- US20090057617A1 US20090057617A1 US12/231,231 US23123108A US2009057617A1 US 20090057617 A1 US20090057617 A1 US 20090057617A1 US 23123108 A US23123108 A US 23123108A US 2009057617 A1 US2009057617 A1 US 2009057617A1
- Authority
- US
- United States
- Prior art keywords
- alkyl
- formula
- anionic surfactant
- cation
- alkenyl
- 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.)
- Abandoned
Links
- 230000007797 corrosion Effects 0.000 title claims abstract description 56
- 238000005260 corrosion Methods 0.000 title claims abstract description 56
- 239000003945 anionic surfactant Substances 0.000 title claims abstract description 25
- 239000003112 inhibitor Substances 0.000 title abstract description 48
- 150000001875 compounds Chemical class 0.000 claims abstract description 13
- 239000000203 mixture Substances 0.000 claims description 49
- 150000003839 salts Chemical class 0.000 claims description 36
- -1 alkali metal salt Chemical class 0.000 claims description 32
- 229910052751 metal Inorganic materials 0.000 claims description 32
- 239000002184 metal Substances 0.000 claims description 32
- 238000000034 method Methods 0.000 claims description 19
- 150000001768 cations Chemical class 0.000 claims description 16
- 229930195733 hydrocarbon Natural products 0.000 claims description 7
- 150000002430 hydrocarbons Chemical class 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 238000012545 processing Methods 0.000 claims description 6
- 229910019142 PO4 Inorganic materials 0.000 claims description 5
- 229910052783 alkali metal Inorganic materials 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 125000005600 alkyl phosphonate group Chemical group 0.000 claims description 3
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 3
- 230000002401 inhibitory effect Effects 0.000 claims description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 3
- 239000010452 phosphate Substances 0.000 claims description 3
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 239000002736 nonionic surfactant Substances 0.000 claims 3
- 239000004215 Carbon black (E152) Substances 0.000 claims 2
- 125000002877 alkyl aryl group Chemical group 0.000 claims 2
- 125000006702 (C1-C18) alkyl group Chemical group 0.000 claims 1
- 150000005215 alkyl ethers Chemical group 0.000 claims 1
- 239000000243 solution Substances 0.000 description 24
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 20
- 229910052708 sodium Inorganic materials 0.000 description 15
- 239000011734 sodium Substances 0.000 description 15
- 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 13
- 239000011575 calcium Substances 0.000 description 11
- 229910052791 calcium Inorganic materials 0.000 description 11
- 239000011777 magnesium Substances 0.000 description 11
- 229910052749 magnesium Inorganic materials 0.000 description 11
- 229910052700 potassium Inorganic materials 0.000 description 11
- UHLNQERYDPVIJE-GMFCBQQYSA-M potassium;4-methylsulfanyl-2-[[(z)-octadec-9-enoyl]amino]butanoate Chemical compound [K+].CCCCCCCC\C=C/CCCCCCCC(=O)NC(C([O-])=O)CCSC UHLNQERYDPVIJE-GMFCBQQYSA-M 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 9
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 9
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 9
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 9
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- 239000011591 potassium Substances 0.000 description 9
- GSEJCLTVZPLZKY-UHFFFAOYSA-O triethanolammonium Chemical compound OCC[NH+](CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-O 0.000 description 9
- 0 CC(*)CCNN=* Chemical compound CC(*)CCNN=* 0.000 description 7
- 235000014113 dietary fatty acids Nutrition 0.000 description 7
- 239000000194 fatty acid Substances 0.000 description 7
- 229930195729 fatty acid Natural products 0.000 description 7
- 230000001988 toxicity Effects 0.000 description 7
- 231100000419 toxicity Toxicity 0.000 description 7
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 6
- 229930182817 methionine Natural products 0.000 description 6
- 235000006109 methionine Nutrition 0.000 description 6
- 239000003921 oil Substances 0.000 description 6
- 239000004470 DL Methionine Substances 0.000 description 5
- 229910002092 carbon dioxide Inorganic materials 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 150000004665 fatty acids Chemical class 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- QSCMVGTXPXZIOH-UHFFFAOYSA-N CSCCC(C)C(=O)O Chemical compound CSCCC(C)C(=O)O QSCMVGTXPXZIOH-UHFFFAOYSA-N 0.000 description 4
- 235000013162 Cocos nucifera Nutrition 0.000 description 4
- 244000060011 Cocos nucifera Species 0.000 description 4
- 239000000470 constituent Substances 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- FFEARJCKVFRZRR-UHFFFAOYSA-N methionine Chemical compound CSCCC(N)C(O)=O FFEARJCKVFRZRR-UHFFFAOYSA-N 0.000 description 4
- 235000021317 phosphate Nutrition 0.000 description 4
- PUAQLLVFLMYYJJ-UHFFFAOYSA-N 2-aminopropiophenone Chemical compound CC(N)C(=O)C1=CC=CC=C1 PUAQLLVFLMYYJJ-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000013543 active substance Substances 0.000 description 3
- 239000001569 carbon dioxide Substances 0.000 description 3
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 3
- 150000002462 imidazolines Chemical class 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- RJSRNVJJDSGOJS-UHFFFAOYSA-M potassium;2-butyl-2-(2,5-dioxopyrrolidin-1-yl)tetradec-3-enoate Chemical compound [K+].CCCCCCCCCCC=CC(CCCC)(C([O-])=O)N1C(=O)CCC1=O RJSRNVJJDSGOJS-UHFFFAOYSA-M 0.000 description 3
- 159000000000 sodium salts Chemical class 0.000 description 3
- ALSTYHKOOCGGFT-KTKRTIGZSA-N (9Z)-octadecen-1-ol Chemical compound CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-N 0.000 description 2
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 2
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 2
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 2
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 2
- OYUOOOMVUYVBGN-CDYZYAPPSA-N CC(=O)[2H]C(=O)O Chemical compound CC(=O)[2H]C(=O)O OYUOOOMVUYVBGN-CDYZYAPPSA-N 0.000 description 2
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical compound CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical class C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 239000005642 Oleic acid Substances 0.000 description 2
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 230000010933 acylation Effects 0.000 description 2
- 238000005917 acylation reaction Methods 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 229940071124 cocoyl glutamate Drugs 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- KBQXYXLZUWULEL-UHFFFAOYSA-L disodium;octyl-dioxido-oxo-$l^{5}-phosphane Chemical compound [Na+].[Na+].CCCCCCCCP([O-])([O-])=O KBQXYXLZUWULEL-UHFFFAOYSA-L 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 150000004679 hydroxides Chemical class 0.000 description 2
- MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical compound C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 2
- 229910000000 metal hydroxide Inorganic materials 0.000 description 2
- 150000004692 metal hydroxides Chemical class 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- 239000002480 mineral oil Substances 0.000 description 2
- 235000010446 mineral oil Nutrition 0.000 description 2
- 239000003345 natural gas Substances 0.000 description 2
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 2
- 229940055577 oleyl alcohol Drugs 0.000 description 2
- XMLQWXUVTXCDDL-UHFFFAOYSA-N oleyl alcohol Natural products CCCCCCC=CCCCCCCCCCCO XMLQWXUVTXCDDL-UHFFFAOYSA-N 0.000 description 2
- YVVZMEOABPIJEW-UHFFFAOYSA-M potassium 3-propan-2-yloxycarbonylundec-4-enoate Chemical compound [K+].CCCCCCC=CC(CC([O-])=O)C(=O)OC(C)C YVVZMEOABPIJEW-UHFFFAOYSA-M 0.000 description 2
- 108700004121 sarkosyl Proteins 0.000 description 2
- KSAVQLQVUXSOCR-UHFFFAOYSA-M sodium lauroyl sarcosinate Chemical compound [Na+].CCCCCCCCCCCC(=O)N(C)CC([O-])=O KSAVQLQVUXSOCR-UHFFFAOYSA-M 0.000 description 2
- 229940045885 sodium lauroyl sarcosinate Drugs 0.000 description 2
- AOBMIXQSBXYCFW-UHFFFAOYSA-M sodium;bis(2-ethylhexyl) phosphate Chemical compound [Na+].CCCCC(CC)COP([O-])(=O)OCC(CC)CCCC AOBMIXQSBXYCFW-UHFFFAOYSA-M 0.000 description 2
- 230000002195 synergetic effect Effects 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 description 1
- IFABLCIRROMTAN-MDZDMXLPSA-N (e)-1-chlorooctadec-9-ene Chemical compound CCCCCCCC\C=C\CCCCCCCCCl IFABLCIRROMTAN-MDZDMXLPSA-N 0.000 description 1
- MLQBTMWHIOYKKC-KTKRTIGZSA-N (z)-octadec-9-enoyl chloride Chemical compound CCCCCCCC\C=C/CCCCCCCC(Cl)=O MLQBTMWHIOYKKC-KTKRTIGZSA-N 0.000 description 1
- OAYXUHPQHDHDDZ-UHFFFAOYSA-N 2-(2-butoxyethoxy)ethanol Chemical compound CCCCOCCOCCO OAYXUHPQHDHDDZ-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- 241000195493 Cryptophyta Species 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- 102000015636 Oligopeptides Human genes 0.000 description 1
- 108010038807 Oligopeptides Proteins 0.000 description 1
- 241000206732 Skeletonema costatum Species 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- ULUAUXLGCMPNKK-UHFFFAOYSA-N Sulfobutanedioic acid Chemical class OC(=O)CC(C(O)=O)S(O)(=O)=O ULUAUXLGCMPNKK-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 125000005210 alkyl ammonium group Chemical group 0.000 description 1
- 150000008051 alkyl sulfates Chemical class 0.000 description 1
- 229940045714 alkyl sulfonate alkylating agent Drugs 0.000 description 1
- 150000008052 alkyl sulfonates Chemical class 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 239000013011 aqueous formulation Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000002599 biostatic effect Effects 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 238000005520 cutting process Methods 0.000 description 1
- IPIVAXLHTVNRBS-UHFFFAOYSA-N decanoyl chloride Chemical compound CCCCCCCCCC(Cl)=O IPIVAXLHTVNRBS-UHFFFAOYSA-N 0.000 description 1
- IQDGSYLLQPDQDV-UHFFFAOYSA-N dimethylazanium;chloride Chemical compound Cl.CNC IQDGSYLLQPDQDV-UHFFFAOYSA-N 0.000 description 1
- NQGIJDNPUZEBRU-UHFFFAOYSA-N dodecanoyl chloride Chemical compound CCCCCCCCCCCC(Cl)=O NQGIJDNPUZEBRU-UHFFFAOYSA-N 0.000 description 1
- 238000005553 drilling Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 239000003630 growth substance Substances 0.000 description 1
- 239000002563 ionic surfactant Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- PYBPYUAKCDQFCS-KVVVOXFISA-N n'-(2-aminoethyl)ethane-1,2-diamine;(z)-octadec-9-enoic acid Chemical compound NCCNCCN.CCCCCCCC\C=C/CCCCCCCC(O)=O PYBPYUAKCDQFCS-KVVVOXFISA-N 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- REEZZSHJLXOIHL-UHFFFAOYSA-N octanoyl chloride Chemical compound CCCCCCCC(Cl)=O REEZZSHJLXOIHL-UHFFFAOYSA-N 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 230000002688 persistence Effects 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- IKGKWKGYFJBGQJ-UHFFFAOYSA-M sodium;2-(dodecanoylamino)acetate Chemical compound [Na+].CCCCCCCCCCCC(=O)NCC([O-])=O IKGKWKGYFJBGQJ-UHFFFAOYSA-M 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C23—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; CHEMICAL SURFACE TREATMENT; DIFFUSION TREATMENT OF METALLIC MATERIAL; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL
- C23F—NON-MECHANICAL REMOVAL OF METALLIC MATERIAL FROM SURFACE; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL; MULTI-STEP PROCESSES FOR SURFACE TREATMENT OF METALLIC MATERIAL INVOLVING AT LEAST ONE PROCESS PROVIDED FOR IN CLASS C23 AND AT LEAST ONE PROCESS COVERED BY SUBCLASS C21D OR C22F OR CLASS C25
- C23F11/00—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent
- C23F11/08—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent in other liquids
- C23F11/10—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent in other liquids using organic inhibitors
- C23F11/14—Nitrogen-containing compounds
- C23F11/145—Amides; N-substituted amides
-
- 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
- C09K8/54—Compositions for in situ inhibition of corrosion in boreholes or wells
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/02—Anionic compounds
- C11D1/04—Carboxylic acids or salts thereof
- C11D1/10—Amino carboxylic acids; Imino carboxylic acids; Fatty acid condensates thereof
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/0005—Other compounding ingredients characterised by their effect
- C11D3/0073—Anticorrosion compositions
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/16—Organic compounds
- C11D3/34—Organic compounds containing sulfur
- C11D3/349—Organic compounds containing sulfur additionally containing nitrogen atoms, e.g. nitro, nitroso, amino, imino, nitrilo, nitrile groups containing compounds or their derivatives or thio urea
-
- C—CHEMISTRY; METALLURGY
- C23—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; CHEMICAL SURFACE TREATMENT; DIFFUSION TREATMENT OF METALLIC MATERIAL; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL
- C23F—NON-MECHANICAL REMOVAL OF METALLIC MATERIAL FROM SURFACE; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL; MULTI-STEP PROCESSES FOR SURFACE TREATMENT OF METALLIC MATERIAL INVOLVING AT LEAST ONE PROCESS PROVIDED FOR IN CLASS C23 AND AT LEAST ONE PROCESS COVERED BY SUBCLASS C21D OR C22F OR CLASS C25
- C23F11/00—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent
- C23F11/08—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent in other liquids
- C23F11/10—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent in other liquids using organic inhibitors
- C23F11/16—Sulfur-containing compounds
-
- C—CHEMISTRY; METALLURGY
- C23—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; CHEMICAL SURFACE TREATMENT; DIFFUSION TREATMENT OF METALLIC MATERIAL; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL
- C23F—NON-MECHANICAL REMOVAL OF METALLIC MATERIAL FROM SURFACE; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL; MULTI-STEP PROCESSES FOR SURFACE TREATMENT OF METALLIC MATERIAL INVOLVING AT LEAST ONE PROCESS PROVIDED FOR IN CLASS C23 AND AT LEAST ONE PROCESS COVERED BY SUBCLASS C21D OR C22F OR CLASS C25
- C23F11/00—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent
- C23F11/08—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent in other liquids
- C23F11/10—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent in other liquids using organic inhibitors
- C23F11/167—Phosphorus-containing compounds
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/16—Organic compounds
- C11D3/34—Organic compounds containing sulfur
- C11D3/3472—Organic compounds containing sulfur additionally containing -COOH groups or derivatives thereof
Definitions
- the present invention relates to a process for corrosion inhibition on and in apparatuses for conveying and transporting hydrocarbons in oil production and processing by adding a metal salt of N-acylmethionine and an ionic surfactant to the corrosive system.
- amides, amidoamines or imidazolines of fatty acids and polyamines have an extremely good oil solubility and, owing to poor partitioning, are therefore present only in low concentration in the corrosive water phase. Accordingly, these products must be used at a high dose in spite of their poor biodegradability.
- Quaternary alkylammonium compounds are alternative corrosion inhibitors of the prior art, which also have biostatic properties in addition to the corrosion-inhibiting properties.
- the quats have a substantially reduced film persistence, for example compared with the imidazolines, and therefore likewise lead to effective corrosion protection only in relatively high doses.
- the strong algae toxicity and the moderate biodegradability are increasingly limiting the use of quats to ecologically insensitive fields of use.
- JP-A-8 337 562 and JP-A-8 337 563 describe N-acylamino acids and their alkali metal salts, which can also be used as corrosion inhibitors.
- JP-A-49 026 145 describes alkali metal salts of N-acylamino acids, which salts can be used as corrosion inhibitors.
- N-Lauroylglycine sodium salt is mentioned as an example.
- metal salts of N-acylmethionine as a mixture with anionic surfactants have an excellent effect as corrosion inhibitors and show good biodegradability and reduced toxicity. Owing to a synergistic effect between the metal salt of N-acylmethionine and anionic surfactant, the dosages can be substantially reduced in comparison with the prior art, with the result that the novel corrosion inhibitor mixtures are also advantageous economically.
- the invention therefore relates to the use of compositions containing metal salts of compounds of the formula (1)
- the invention furthermore relates to a process for inhibiting corrosion on metal surfaces, in particular of iron-containing metals, by adding at least one metal salt of compounds of the formula (1) and an anionic surfactant to a corrosive system which is in contact with the metal surfaces.
- the invention furthermore relates to compositions containing at least one metal salt of a compound of the formula (1) and at least one anionic surfactant.
- the invention furthermore relates to the use of metal salts of compounds of the formula (1) together with anionic surfactants as metal processing compositions.
- the compositions according to the invention also afford very good corrosion protection even under strong mechanical load, such as during grinding, cutting and drilling of metal workpieces.
- Corrosive systems in the context of this invention are preferably liquid/liquid or liquid/gaseous multiphase systems consisting of water and hydrocarbons which contain corrosive constituents, such as salts and acids, in free and/or dissolved form.
- the corrosive constituents may also be gaseous, such as, for example, hydrogen sulfide and carbon dioxide.
- Hydrocarbons in the context of this invention are organic compounds which are constituents of mineral oil/natural gas, and the secondary products thereof. Hydrocarbons in the context of this invention are also readily volatile hydrocarbons, such as, for example, methane, ethane, propane and butane. For the purposes of this invention, these also include the further gaseous constituents of mineral oil/natural gas, such as, for example, hydrogen sulfide and carbon dioxide.
- Preferred surfactants are those which, in a concentration of 0.5% by weight in water, produce a surface tension of this aqueous solution of not more than 55 mN/m, particularly preferably of not more than 50 mN/m and especially not more than 45 mN/m.
- R 1 is C 3 - to C 23 -alkyl, C 3 - to C 23 -alkenyl, C 6 - to C 24 -aryl or C 7 - to C 25 -alkylaryl, in particular an alkyl or alkenyl group having 7 to 17 carbon atoms.
- N-acylmethionine is effected by acylation of methionine by means of carboxylic acid chloride or carboxylic anhydride in the presence of a base (e.g. sodium hydroxide).
- a base e.g. sodium hydroxide
- DL-methionine is preferably used for this purpose, but the pure enantiomeric forms may likewise be used.
- the hydroxides of alkali metals or alkaline earth metals are preferred as the base used for the preparation of the metals salts according to the invention.
- the hydroxides of Na, K, Ca and Mg are particularly preferred.
- the metal salts according to the invention are preferably alkali metal or alkaline earth metal salts, in particular Na, K, Ca or Mg salts, of the compounds of the formula 1.
- the metal salts of N-acylmethionine are present in unneutralized and isolated form and are formulated directly with the anionic surfactants according to the invention to give the corrosion inhibitor mixture according to the invention.
- the preparation process for the corrosion inhibitors according to the invention is substantially more economical.
- the metal salts of N-acylmethionine according to the invention are obtained as a rule as 10-50% strength solutions in water and are formulated directly with one or more anionic surfactants to give the corrosion inhibitor mixture.
- alcoholic solvents such as, for example, methanol, ethanol, propanol, isopropanol, butanol, 2-ethylhexanol, methyl glycol, butyl glycol or butyl diglycol, may be added.
- Suitable anionic surfactants are:
- Suitable alkylphosphates are salts of the formula (RO) n (O ⁇ P)(OM) l , in which R is a C 6 -C 30 -alkyl or a C 7 -C 30 -alkylaryl radical, preferably a C 8 -C 18 -alkyl or a C 10 -C 24 -alkylaryl radical.
- R is a C 6 -C 30 -alkyl or a C 7 -C 30 -alkylaryl radical, preferably a C 8 -C 18 -alkyl or a C 10 -C 24 -alkylaryl radical.
- M is a cation, such as, for example, sodium, potassium, ammonium, mono-, di- or triethanolammonium, calcium or magnesium and mixtures thereof.
- Suitable alkyl ether phosphates are salts of the formula [RO(A) m ] n (O ⁇ P)(OM) l , in which R is a C 6 -C 30 -alkyl or a C 7 -C 30 -alkylaryl radical, preferably a C 8 -C 18 -alkyl or a C 10 -C 24 -alkylaryl radical.
- A is an ethoxy or propoxy unit
- m is a number greater than 0, preferably from 0.5 to 20, particularly preferably from 2 to 12.
- M is a cation, such as, for example, sodium, potassium, ammonium, mono-, di- or triethanolammonium, calcium or magnesium and mixtures thereof.
- Suitable alkylphosphonates are salts of the formula (2)
- Suitable alkylpolyalkylene glycol ether carboxylates or alkylarylpolyalkylene glycol ether carboxylates are salts of the formula RO(A) m CO 2 M, in which R is a C 4 -C 30 -alkyl or a C 7 -C 30 -alkylaryl radical, preferably a C 8 -C 18 -alkyl or a C 10 -C 24 -alkylaryl radical.
- A is an ethoxy or propoxy unit
- m is a number greater than 0, preferably from 0.5 to 20, particularly preferably from 2 to 12
- M is a cation, such as, for example, sodium, potassium, ammonium, mono-, di- or triethanolammonium, calcium or magnesium and mixtures thereof.
- Suitable N-acylmethyltaurates are salts of the formula R(C ⁇ O)(NCH 3 )CH 2 CH 2 SO 3 M, in which R is a C 5 -C 29 -alkyl or a C 5 -C 29 -alkenyl radical, preferably a C 7 -C 17 -alkyl, or a C 7 -C 17 -alkenyl radical.
- M is a cation, such as, for example, sodium, potassium, ammonium, mono-, di- or triethanolammonium, calcium or magnesium and mixtures thereof.
- Suitable N-acylsarcosinates are salts of the formula R(C ⁇ O)(NCH 3 )CH 2 CO 2 M, in which R is a C 5 -C 29 -alkyl or a C 5 -C 29 -alkenyl radical, preferably a C 7 -C 17 -alkyl or an C 7 -C 17 -alkenyl radical.
- M is a cation, such as, for example, sodium, potassium, ammonium, mono-, di- or triethanolammonium, calcium or magnesium and mixtures thereof.
- Suitable N-acylglutamates are salts of the formula (3)
- Suitable alkylsuccinates are salts of the formula (4)
- Suitable alkylsuccinimides are salts of the formula (5)
- compositions according to the invention can be used alone or in combination with other known corrosion inhibitors.
- the composition according to the invention is used in an amount such that sufficient corrosion protection is obtained under the given conditions.
- Preferred concentrations in which the compositions according to the invention are used are from 5 to 5000 ppm, preferably from 10 to 1000 ppm, in particular from 15 to 150 ppm, based on the weight of the phases to be inhibited with respect to the corrosion properties.
- the mixing ratio between metal salt of the compound 1 and anionic surfactant is preferably from 1:9 to 9:1, in particular from 3:7 to 7:3, especially from 1:2 to 2:1.
- compositions according to the invention with other corrosion inhibitors and/or those of the prior art are also particularly suitable as corrosion inhibitors.
- N-cocoyl-DL-methionine sodium salt from example 1 were mixed with 10 g of a 20% strength solution of potassium dodecenylsuccinimidohexanoate, 20 g of butylglycol and 15 g of water.
- the compounds according to the invention were tested as corrosion inhibitors in the Shell wheel test. Coupons of C steel (DIN 1.1203 with 15 cm 2 surface area) were immersed in a salt water/petroleum mixture (9:1,5% strength NaCl solution adjusted to pH 3.5 with acetic acid) and exposed to this medium at a speed of 40 rpm at 70° C. for 24 hours. The inhibitor dose was 50 ppm of a 24% solution of the inhibitor. The protection values were calculated from the decrease in the mass of the coupons, based on a blank value.
- “comparison 1” designates a commercially available residue amine quat based on dicocosalkyl dimethylammonium chloride
- “comparison 2” a commercially available imidazoline salt based on oleic acid diethylenetriamine
- “comparison 3” an example from DE-10 2006 002 784 (morpholinium salt of N-cocoyl-DL-methionine, corrosion inhibitor of the prior art).
- compositions according to the invention have very good corrosion inhibition properties at a very low dose and in some cases even substantially surpass the activity of the inhibitors of the prior art.
- example 39 shows that the synergistic effect of the metal salt of N-acylmethionine in combination with an anionic surfactant decreases at a ratio of >9:1 but is still present.
- the compounds according to the invention exhibit improved biodegradability and lower toxicity compared to the comparative examples from the prior art.
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Abstract
Description
- The present invention is described in the German priority application No. 10 2007 041 204.7 filed Aug. 31, 2007, which is hereby incorporated by reference as is fully disclosed herein.
- The present invention relates to a process for corrosion inhibition on and in apparatuses for conveying and transporting hydrocarbons in oil production and processing by adding a metal salt of N-acylmethionine and an ionic surfactant to the corrosive system.
- In industrial processes in which metals come into contact with water or with oil/water two-phase systems, there is the danger of corrosion. This is particularly pronounced if the aqueous phase has a high salt content, as in oil extraction and processing processors, or is acidic due to dissolved acid gases, such as carbon dioxide or hydrogen sulfide. The exploitation of a deposit and the processing of oil are therefore not possible without special additives for protecting the equipment used.
- Although suitable corrosion inhibitors for oil production and processing have long been known, they are unacceptable in future for offshore applications for reasons relating to environmental protection.
- As typical corrosion inhibitors of the prior art, amides, amidoamines or imidazolines of fatty acids and polyamines have an extremely good oil solubility and, owing to poor partitioning, are therefore present only in low concentration in the corrosive water phase. Accordingly, these products must be used at a high dose in spite of their poor biodegradability.
- Quaternary alkylammonium compounds (quats) are alternative corrosion inhibitors of the prior art, which also have biostatic properties in addition to the corrosion-inhibiting properties. In spite of improved water solubility, the quats have a substantially reduced film persistence, for example compared with the imidazolines, and therefore likewise lead to effective corrosion protection only in relatively high doses. The strong algae toxicity and the moderate biodegradability are increasingly limiting the use of quats to ecologically insensitive fields of use.
- U.S. Pat. No. 4,240,823 describes N-acylmethionine derivatives which are used as growth regulators in the area of crop protection.
- JP-A-8 337 562 and JP-A-8 337 563 describe N-acylamino acids and their alkali metal salts, which can also be used as corrosion inhibitors.
- JP-A-49 026 145 describes alkali metal salts of N-acylamino acids, which salts can be used as corrosion inhibitors. N-Lauroylglycine sodium salt is mentioned as an example.
- A disadvantage of the compounds of the prior art is, however, that their activity at low doses is often not sufficient.
- DE-10 2006 002 784 discloses N-acylmethionine ammonium salts which have an excellent effect as corrosion inhibitors and show good biodegradability and reduced toxicity. A disadvantage of these compounds is, however, their complicated preparation and the associated relatively high production costs.
- It was an object of the present invention to provide novel corrosion inhibitors which, in combination with improved corrosion protection, also afford improved biodegradability and lower toxicity in comparison with the corrosion inhibitors of the prior art in addition to good water solubility. Furthermore, the novel corrosion inhibitors should be capable of being produced at an economically acceptable price.
- It has now surprisingly been found that metal salts of N-acylmethionine as a mixture with anionic surfactants have an excellent effect as corrosion inhibitors and show good biodegradability and reduced toxicity. Owing to a synergistic effect between the metal salt of N-acylmethionine and anionic surfactant, the dosages can be substantially reduced in comparison with the prior art, with the result that the novel corrosion inhibitor mixtures are also advantageous economically.
- The invention therefore relates to the use of compositions containing metal salts of compounds of the formula (1)
-
- in which R1 is C1- to C29-alkyl, C2- to C29-alkenyl, C6- to C30-aryl or C7- to C30-alkylaryl, and anionic surfactants as corrosion inhibitors.
- The invention furthermore relates to a process for inhibiting corrosion on metal surfaces, in particular of iron-containing metals, by adding at least one metal salt of compounds of the formula (1) and an anionic surfactant to a corrosive system which is in contact with the metal surfaces.
- The invention furthermore relates to compositions containing at least one metal salt of a compound of the formula (1) and at least one anionic surfactant.
- The invention furthermore relates to the use of metal salts of compounds of the formula (1) together with anionic surfactants as metal processing compositions. Here, the compositions according to the invention also afford very good corrosion protection even under strong mechanical load, such as during grinding, cutting and drilling of metal workpieces.
- Corrosive systems in the context of this invention are preferably liquid/liquid or liquid/gaseous multiphase systems consisting of water and hydrocarbons which contain corrosive constituents, such as salts and acids, in free and/or dissolved form. The corrosive constituents may also be gaseous, such as, for example, hydrogen sulfide and carbon dioxide.
- Hydrocarbons in the context of this invention are organic compounds which are constituents of mineral oil/natural gas, and the secondary products thereof. Hydrocarbons in the context of this invention are also readily volatile hydrocarbons, such as, for example, methane, ethane, propane and butane. For the purposes of this invention, these also include the further gaseous constituents of mineral oil/natural gas, such as, for example, hydrogen sulfide and carbon dioxide.
- Preferred surfactants are those which, in a concentration of 0.5% by weight in water, produce a surface tension of this aqueous solution of not more than 55 mN/m, particularly preferably of not more than 50 mN/m and especially not more than 45 mN/m.
- In a further preferred embodiment of the invention, R1 is C3- to C23-alkyl, C3- to C23-alkenyl, C6- to C24-aryl or C7- to C25-alkylaryl, in particular an alkyl or alkenyl group having 7 to 17 carbon atoms.
- The preparation of metal salts of N-acylmethionine is effected by acylation of methionine by means of carboxylic acid chloride or carboxylic anhydride in the presence of a base (e.g. sodium hydroxide). For economic reasons, DL-methionine is preferably used for this purpose, but the pure enantiomeric forms may likewise be used. C8-18 alkyl or alkenyl chlorides, such as, for example, octanoyl chloride, decanoyl chloride, dodecanoyl chloride, coconut fatty acid chloride or oleyl chloride, are preferably used for the acylation.
- The hydroxides of alkali metals or alkaline earth metals are preferred as the base used for the preparation of the metals salts according to the invention. The hydroxides of Na, K, Ca and Mg are particularly preferred. Accordingly, the metal salts according to the invention are preferably alkali metal or alkaline earth metal salts, in particular Na, K, Ca or Mg salts, of the compounds of the formula 1.
- In contrast to DE-10 2006 002 784, the metal salts of N-acylmethionine are present in unneutralized and isolated form and are formulated directly with the anionic surfactants according to the invention to give the corrosion inhibitor mixture according to the invention. As a result, the preparation process for the corrosion inhibitors according to the invention is substantially more economical.
- The metal salts of N-acylmethionine according to the invention are obtained as a rule as 10-50% strength solutions in water and are formulated directly with one or more anionic surfactants to give the corrosion inhibitor mixture. For stabilizing the aqueous formulations, alcoholic solvents, such as, for example, methanol, ethanol, propanol, isopropanol, butanol, 2-ethylhexanol, methyl glycol, butyl glycol or butyl diglycol, may be added.
- Suitable anionic surfactants are:
- Alkylsulfonates, olefinsulfonates, alkylsulfates, alkylaryl ether sulfates, alkyl ether sulfates, sulfosuccinates, alkylsuccinates, alkylphosphates, alkyl ether phosphates, alkylphosphonates, alkylpolyalkylene glycol ether carboxylates, alkylarylpolyalkylene glycol ether carboxylates, fatty acid isethionates, N-acylmethyltaurates, N-acylsarcosinates, alkylbenzenesulfonates, alkylnaphthalenesulfonates, N-acylglutamates, amphoacetates, alkylsulfamidocarboxylates, alkyl- and alkenylglycerylsulfates and fatty acid-protein condensates which are obtained by reacting fatty acid chlorides with oligopeptides.
- Preferred anionic surfactants are described in more detail below:
- Suitable alkylphosphates are salts of the formula (RO)n(O═P)(OM)l, in which R is a C6-C30-alkyl or a C7-C30-alkylaryl radical, preferably a C8-C18-alkyl or a C10-C24-alkylaryl radical. For n and l, 0<n<3 and 0<l<3, with the proviso that n+l=3. Preferably, 1≦n≦2 and 1≦l≦2. M is a cation, such as, for example, sodium, potassium, ammonium, mono-, di- or triethanolammonium, calcium or magnesium and mixtures thereof.
- Suitable alkyl ether phosphates are salts of the formula [RO(A)m]n(O═P)(OM)l, in which R is a C6-C30-alkyl or a C7-C30-alkylaryl radical, preferably a C8-C18-alkyl or a C10-C24-alkylaryl radical. A is an ethoxy or propoxy unit, m is a number greater than 0, preferably from 0.5 to 20, particularly preferably from 2 to 12. For n and l, 0<n<3 and 0<l<3, with the proviso that n+l=3. Preferably, 1≦n≦2 and 1≦l≦2. M is a cation, such as, for example, sodium, potassium, ammonium, mono-, di- or triethanolammonium, calcium or magnesium and mixtures thereof.
- Suitable alkylphosphonates are salts of the formula (2)
-
- in which R is a C6-C30-alkyl or a C7-C30-alkylaryl radical, preferably a C8-C18-alkyl or a C10-C24-alkylaryl radical. M is a cation, such as, for example, sodium, potassium, ammonium, mono-, di- or triethanolammonium, calcium or magnesium and mixtures thereof.
- Suitable alkylpolyalkylene glycol ether carboxylates or alkylarylpolyalkylene glycol ether carboxylates are salts of the formula RO(A)mCO2M, in which R is a C4-C30-alkyl or a C7-C30-alkylaryl radical, preferably a C8-C18-alkyl or a C10-C24-alkylaryl radical. A is an ethoxy or propoxy unit, m is a number greater than 0, preferably from 0.5 to 20, particularly preferably from 2 to 12, and M is a cation, such as, for example, sodium, potassium, ammonium, mono-, di- or triethanolammonium, calcium or magnesium and mixtures thereof.
- Suitable N-acylmethyltaurates are salts of the formula R(C═O)(NCH3)CH2CH2SO3M, in which R is a C5-C29-alkyl or a C5-C29-alkenyl radical, preferably a C7-C17-alkyl, or a C7-C17-alkenyl radical. M is a cation, such as, for example, sodium, potassium, ammonium, mono-, di- or triethanolammonium, calcium or magnesium and mixtures thereof.
- Suitable N-acylsarcosinates are salts of the formula R(C═O)(NCH3)CH2CO2M, in which R is a C5-C29-alkyl or a C5-C29-alkenyl radical, preferably a C7-C17-alkyl or an C7-C17-alkenyl radical. M is a cation, such as, for example, sodium, potassium, ammonium, mono-, di- or triethanolammonium, calcium or magnesium and mixtures thereof.
- Suitable N-acylglutamates are salts of the formula (3)
-
- in which R is a C5-C29-alkyl or a C5-C29-alkenyl radical, preferably a C7-C17-alkyl or a C7-C17-alkenyl radical. M+ is a cation, such as, for example, sodium, potassium, ammonium, mono-, di- or triethanolammonium, calcium or magnesium and mixtures thereof.
- Suitable alkylsuccinates are salts of the formula (4)
-
- in which D=CH2CHR and R is a C6-C30-alkyl or a C6-C30-alkenyl radical, preferably a C8-C18-alkyl or a C8-C18-alkenyl radical, R′ is hydrogen or a C1-C8-alkyl or a C3-C18-alkenyl radical. M is a cation, such as, for example, sodium, potassium, ammonium, mono-, di- or triethanolammonium, calcium or magnesium and mixtures thereof.
- Suitable alkylsuccinimides are salts of the formula (5)
-
- in which R is a C6-C30-alkyl or a C6-C30-alkenyl radical, preferably a C8-C18-alkyl or a C8-C18-alkenyl radical. M is a cation, such as, for example, sodium, potassium, ammonium, mono-, di- or triethanolammonium, calcium or magnesium and mixtures thereof.
- The compositions according to the invention can be used alone or in combination with other known corrosion inhibitors. In general, the composition according to the invention is used in an amount such that sufficient corrosion protection is obtained under the given conditions.
- Preferred concentrations in which the compositions according to the invention are used are from 5 to 5000 ppm, preferably from 10 to 1000 ppm, in particular from 15 to 150 ppm, based on the weight of the phases to be inhibited with respect to the corrosion properties. The mixing ratio between metal salt of the compound 1 and anionic surfactant is preferably from 1:9 to 9:1, in particular from 3:7 to 7:3, especially from 1:2 to 2:1.
- Mixtures of the compositions according to the invention with other corrosion inhibitors and/or those of the prior art are also particularly suitable as corrosion inhibitors.
- General Method for the Preparation of Metal Salts of N-acylmethionine
- In a standard stirred apparatus, 1 mol of DL-methionine in 300 ml of water are neutralized with 50% strength aqueous metal hydroxide solution. 1 mol of carboxylic acid chloride is metered into the resulting solution at 15-20° C., the pH being kept at 10-13 by simultaneous metering of 15% strength aqueous metal hydroxide solution. The reaction solution is stirred for a further 3 h at room temperature. The resulting metal salt of N-acylmethionine is characterized by means of the alkali number (AN) and active substance content. Stated percentages are percentages by weight, based on the weight of the salt according to the invention.
- N-Cocoyl-DL-methionine sodium salt having an active substance content of 40% and an AN=65 mg KOH/g was obtained from coconut fatty acid chloride, DL-methionine and sodium hydroxide.
- N-Oleoyl-DL-methionine potassium salt having an active substance content of 40% and an AN=56 mg KOH/g was obtained from oleoyl chloride, DL-methionine and potassium hydroxide.
- 40 g of N-cocoyl-DL-methionine sodium salt from example 1 were mixed with 40 g of a 20% strength solution of sodium di(2-ethylhexyl)phosphate and 20 g of butylglycol.
- 40 g of N-cocoyl-DL-methionine sodium salt from example 1 were mixed with 40 g of a 20% strength solution of sodium bis(lauryltetraethoxy)phosphate and 20 g of butylglycol.
- 40 g of N-cocoyl-DL-methionine sodium salt from example 1 were mixed with 40 g of a 20% strength solution of sodium octylphosphonate and 20 g of butylglycol.
- 40 g of N-cocoyl-DL-methionine sodium salt from example 1 were mixed with 40 g of a 20% strength solution of (oleyl alcohol+10 EO)-ether carboxylic acid sodium salt and 20 g of butylglycol.
- 40 g of N-cocoyl-DL-methionine sodium salt from example 1 were mixed with 40 g of a 20% strength dispersion of coconut fatty acid methyltaurate sodium salt and 20 g of butylglycol.
- 40 g of N-cocoyl-DL-methionine sodium salt from example 1 were mixed with 40 g of a 20% strength solution of sodium lauroyl sarcosinate and 20 g of butylglycol.
- 40 g of N-cocoyl-DL-methionine sodium salt from example 1 were mixed with 40 g of a 20% strength solution of sodium N-cocoylglutamate and 20 g of butylglycol.
- 40 g of N-cocoyl-DL-methionine sodium salt from example 1 were mixed with 40 g of a 20% strength solution of potassium monoisopropyl octenylsuccinate and 20 g of butylglycol.
- 40 g of N-cocoyl-DL-methionine sodium salt from example 1 were mixed with 40 g of a 20% strength solution of potassium dodecenylsuccinimidohexanoate and 20 g of butylglycol.
- 40 g of N-oleoyl-DL-methionine potassium salt from example 2 were mixed with 40 g of a 20% strength solution of sodium di(2-ethylhexyl)phosphate and 20 g of butylglycol.
- 40 g of N-oleoyl-DL-methionine potassium salt from example 2 were mixed with 40 g of a 20% strength solution of sodium bis(lauryltetraethoxy)phosphate and 20 g of butylglycol.
- 40 g of N-oleoyl-DL-methionine potassium salt from example 2 were mixed with 40 g of a 20% strength solution of sodium octylphosphonate and 20 g of butylglycol.
- 40 g of N-oleoyl-DL-methionine potassium salt from example 2 were mixed with 40 g of a 20% strength solution of (oleyl alcohol+10 EO)-ethercarboxylic acid sodium salt and 20 g of butylglycol.
- 40 g of N-oleoyl-DL-methionine potassium salt from example 2 were mixed with 40 g of a 20% strength dispersion of coconut fatty acid methyltaurate sodium salt and 20 g of butylglycol.
- 40 g of N-oleoyl-DL-methionine potassium salt from example 2 were mixed with 40 g of a 20% strength solution of sodium lauroyl sarcosinate and 20 g of butylglycol.
- 40 g of N-oleoyl-DL-methionine potassium salt from example 2 were mixed with 40 g of a 20% strength solution of sodium N-cocoylglutamate and 20 g of butylglycol.
- 40 g of N-oleoyl-DL-methionine potassium salt from example 2 were mixed with 40 g of a 20% strength solution of potassium monoisopropyl octenylsuccinate and 20 g of butylglycol.
- 40 g of N-oleoyl-DL-methionine potassium salt from example 2 were mixed with 40 g of a 20% strength solution of potassium dodecenylsuccinimidohexanoate and 20 g of butylglycol.
- 55 g of N-cocoyl-DL-methionine sodium salt from example 1 were mixed with 10 g of a 20% strength solution of potassium dodecenylsuccinimidohexanoate, 20 g of butylglycol and 15 g of water.
- Activity of the compounds according to the invention as corrosion inhibitors
- The compounds according to the invention were tested as corrosion inhibitors in the Shell wheel test. Coupons of C steel (DIN 1.1203 with 15 cm2 surface area) were immersed in a salt water/petroleum mixture (9:1,5% strength NaCl solution adjusted to pH 3.5 with acetic acid) and exposed to this medium at a speed of 40 rpm at 70° C. for 24 hours. The inhibitor dose was 50 ppm of a 24% solution of the inhibitor. The protection values were calculated from the decrease in the mass of the coupons, based on a blank value.
- In the following tables, “comparison 1” designates a commercially available residue amine quat based on dicocosalkyl dimethylammonium chloride, “comparison 2” a commercially available imidazoline salt based on oleic acid diethylenetriamine and “comparison 3” an example from DE-10 2006 002 784 (morpholinium salt of N-cocoyl-DL-methionine, corrosion inhibitor of the prior art).
-
TABLE 1 (Shell wheel test) Example Corrosion inhibitor ø protection % Comparison 1 Standard quat 28 Comparison 2 Oleic acid DETA imidazoline 70 Comparison 3 Morpholinium salt of N-cocoyl-DL- 75 methionine Comparison 4 from example 1 67 Comparison 5 from example 2 69 21 from example 3 77 22 from example 4 79 23 from example 5 86 24 from example 6 88 25 from example 7 81 26 from example 8 88 27 from example 9 90 28 from example 10 80 29 from example 11 91 30 from example 12 76 31 from example 13 76 32 from example 14 84 33 from example 15 85 34 from example 16 76 35 from example 17 82 36 from example 18 87 37 from example 19 78 38 from example 20 92 39 from example 21 81 - As is evident from table 1, the compositions according to the invention have very good corrosion inhibition properties at a very low dose and in some cases even substantially surpass the activity of the inhibitors of the prior art.
- In comparison with example 29, example 39 shows that the synergistic effect of the metal salt of N-acylmethionine in combination with an anionic surfactant decreases at a ratio of >9:1 but is still present.
-
TABLE 2 Biodegradability (OECD 306) and toxicity (EC50 Skeletonema Costatum) of selected corrosion inhibitors according to the invention Biodegradability Toxicity Example Corrosion inhibitor [%] EC50 [mg/l] Comparison 1 Standard quat 15.2 0.57 Comparison 2 Oleic acid DETA 6.8 0.33 imidazoline 39 from example 6 93.0 80.5 40 from example 9 95.3 65.3 41 from example 10 86.9 120.5 42 from example 15 90.5 105.9 43 from example 18 92.1 91.4 44 from example 19 85.4 150.2 - As can clearly be seen from table 4, the compounds according to the invention exhibit improved biodegradability and lower toxicity compared to the comparative examples from the prior art.
Claims (18)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE102007041204A DE102007041204B3 (en) | 2007-08-31 | 2007-08-31 | Use of composition as corrosion inhibitors containing anionic surfactants and the compositions |
DE102007041204.7 | 2007-08-31 |
Publications (1)
Publication Number | Publication Date |
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US20090057617A1 true US20090057617A1 (en) | 2009-03-05 |
Family
ID=40032614
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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US12/231,231 Abandoned US20090057617A1 (en) | 2007-08-31 | 2008-08-29 | Corrosion inhibitors containing anionic surfactants |
Country Status (4)
Country | Link |
---|---|
US (1) | US20090057617A1 (en) |
EP (1) | EP2031094A3 (en) |
BR (1) | BRPI0803881A2 (en) |
DE (1) | DE102007041204B3 (en) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20120292022A1 (en) * | 2010-11-22 | 2012-11-22 | E. I. Du Pont De Nemours And Company | Composition for improving oil recovery including n-lauroyl amino acid-based compounds and microbes |
US11760920B1 (en) | 2022-04-06 | 2023-09-19 | Halliburton Energy Services, Inc. | Lubricant for monovalent and divalent brines |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN109943312B (en) * | 2019-03-19 | 2021-03-09 | 中国海洋石油集团有限公司 | Oil displacement agent and preparation method thereof |
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2007
- 2007-08-31 DE DE102007041204A patent/DE102007041204B3/en not_active Expired - Fee Related
-
2008
- 2008-08-26 EP EP08015010A patent/EP2031094A3/en not_active Withdrawn
- 2008-08-29 BR BRPI0803881-3A patent/BRPI0803881A2/en not_active Application Discontinuation
- 2008-08-29 US US12/231,231 patent/US20090057617A1/en not_active Abandoned
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US20120292022A1 (en) * | 2010-11-22 | 2012-11-22 | E. I. Du Pont De Nemours And Company | Composition for improving oil recovery including n-lauroyl amino acid-based compounds and microbes |
US11760920B1 (en) | 2022-04-06 | 2023-09-19 | Halliburton Energy Services, Inc. | Lubricant for monovalent and divalent brines |
Also Published As
Publication number | Publication date |
---|---|
EP2031094A3 (en) | 2011-04-20 |
DE102007041204B3 (en) | 2009-04-30 |
EP2031094A2 (en) | 2009-03-04 |
BRPI0803881A2 (en) | 2009-06-30 |
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