US2368606A - Corrosion protection of metals - Google Patents
Corrosion protection of metals Download PDFInfo
- Publication number
- US2368606A US2368606A US475203A US47520343A US2368606A US 2368606 A US2368606 A US 2368606A US 475203 A US475203 A US 475203A US 47520343 A US47520343 A US 47520343A US 2368606 A US2368606 A US 2368606A
- Authority
- US
- United States
- Prior art keywords
- acids
- acid
- corrosion
- alpha
- oil
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 229910052751 metal Inorganic materials 0.000 title description 31
- 239000002184 metal Substances 0.000 title description 31
- 230000007797 corrosion Effects 0.000 title description 19
- 238000005260 corrosion Methods 0.000 title description 19
- 150000002739 metals Chemical class 0.000 title description 9
- -1 carboxyl radicals Chemical class 0.000 description 37
- 239000002253 acid Substances 0.000 description 23
- 239000003981 vehicle Substances 0.000 description 23
- 229930195733 hydrocarbon Natural products 0.000 description 21
- 239000004215 Carbon black (E152) Substances 0.000 description 18
- 239000003921 oil Substances 0.000 description 17
- 235000019198 oils Nutrition 0.000 description 17
- 125000004432 carbon atom Chemical group C* 0.000 description 16
- 150000007513 acids Chemical class 0.000 description 15
- 239000000194 fatty acid Substances 0.000 description 15
- 239000012266 salt solution Substances 0.000 description 13
- 239000007787 solid Substances 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 10
- 235000014113 dietary fatty acids Nutrition 0.000 description 10
- 229930195729 fatty acid Natural products 0.000 description 10
- 239000001257 hydrogen Substances 0.000 description 10
- 229910052739 hydrogen Inorganic materials 0.000 description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- 239000006185 dispersion Substances 0.000 description 9
- 239000003112 inhibitor Substances 0.000 description 9
- 239000008117 stearic acid Substances 0.000 description 9
- 238000011282 treatment Methods 0.000 description 9
- 239000007788 liquid Substances 0.000 description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 7
- 235000021355 Stearic acid Nutrition 0.000 description 7
- 229910000831 Steel Inorganic materials 0.000 description 7
- 150000001875 compounds Chemical class 0.000 description 7
- 239000010687 lubricating oil Substances 0.000 description 7
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 7
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 7
- 239000010959 steel Substances 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- 150000002430 hydrocarbons Chemical class 0.000 description 6
- 229920005989 resin Polymers 0.000 description 6
- 239000011347 resin Substances 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 150000004665 fatty acids Chemical class 0.000 description 5
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 230000007935 neutral effect Effects 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 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 4
- 239000012153 distilled water Substances 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 239000003350 kerosene Substances 0.000 description 4
- 125000005608 naphthenic acid group Chemical group 0.000 description 4
- 230000002265 prevention Effects 0.000 description 4
- 230000003449 preventive effect Effects 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 239000001993 wax Substances 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- 239000004264 Petrolatum Substances 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- 238000001246 colloidal dispersion Methods 0.000 description 3
- 150000001991 dicarboxylic acids Chemical class 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 229910052742 iron Inorganic materials 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 description 3
- 229940066842 petrolatum Drugs 0.000 description 3
- 235000019271 petrolatum Nutrition 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 150000003141 primary amines Chemical class 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 230000001681 protective effect Effects 0.000 description 3
- 239000012260 resinous material Substances 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- 238000003892 spreading Methods 0.000 description 3
- 238000003860 storage Methods 0.000 description 3
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical compound C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 2
- HNNQYHFROJDYHQ-UHFFFAOYSA-N 3-(4-ethylcyclohexyl)propanoic acid 3-(3-ethylcyclopentyl)propanoic acid Chemical class CCC1CCC(CCC(O)=O)C1.CCC1CCC(CCC(O)=O)CC1 HNNQYHFROJDYHQ-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical class CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 2
- 239000000084 colloidal system Substances 0.000 description 2
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 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
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 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
- 238000000605 extraction Methods 0.000 description 2
- 239000000446 fuel Substances 0.000 description 2
- HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 description 2
- 239000003502 gasoline Substances 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 125000001421 myristyl 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])[H] 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- ORTFAQDWJHRMNX-UHFFFAOYSA-M oxidooxomethyl Chemical compound [O-][C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-M 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
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
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- 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
- 125000001424 substituent group Chemical group 0.000 description 2
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- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
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- 235000012343 cottonseed oil Nutrition 0.000 description 1
- 125000000853 cresyl group Chemical group C1(=CC=C(C=C1)C)* 0.000 description 1
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000002939 deleterious effect Effects 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- QTBSBXVTEAMEQO-DYCDLGHISA-N deuterio acetate Chemical compound [2H]OC(C)=O QTBSBXVTEAMEQO-DYCDLGHISA-N 0.000 description 1
- 239000002283 diesel fuel Substances 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- IJDSUFQMYUARCQ-QZTJIDSGSA-N diisophorone Chemical compound C([C@@](C1)(C)C2)C(C)(C)C[C@]1(O)C1=C2CC(C)(C)CC1=O IJDSUFQMYUARCQ-QZTJIDSGSA-N 0.000 description 1
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical class C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 1
- 238000010494 dissociation reaction Methods 0.000 description 1
- 230000005593 dissociations Effects 0.000 description 1
- UKMSUNONTOPOIO-UHFFFAOYSA-N docosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCC(O)=O UKMSUNONTOPOIO-UHFFFAOYSA-N 0.000 description 1
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical class CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003792 electrolyte Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 125000005313 fatty acid group Chemical group 0.000 description 1
- 239000010685 fatty oil Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 235000019382 gum benzoic Nutrition 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- IUJAMGNYPWYUPM-UHFFFAOYSA-N hentriacontane Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCC IUJAMGNYPWYUPM-UHFFFAOYSA-N 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- PQNFLJBBNBOBRQ-UHFFFAOYSA-N indane Chemical compound C1=CC=C2CCCC2=C1 PQNFLJBBNBOBRQ-UHFFFAOYSA-N 0.000 description 1
- 239000012182 japan wax Substances 0.000 description 1
- 229940119170 jojoba wax Drugs 0.000 description 1
- 150000003893 lactate salts Chemical class 0.000 description 1
- 239000010699 lard oil Substances 0.000 description 1
- 230000002045 lasting effect Effects 0.000 description 1
- 239000000944 linseed oil Substances 0.000 description 1
- 235000021388 linseed oil Nutrition 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical class CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- SNMVRZFUUCLYTO-UHFFFAOYSA-N n-propyl chloride Chemical compound CCCCl SNMVRZFUUCLYTO-UHFFFAOYSA-N 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000000025 natural resin Substances 0.000 description 1
- MOFOBJHOKRNACT-UHFFFAOYSA-N nickel silver Chemical compound [Ni].[Ag] MOFOBJHOKRNACT-UHFFFAOYSA-N 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 1
- 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 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid group Chemical group C(CCCCCCC\C=C/CCCCCCCC)(=O)O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 125000001117 oleyl 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])=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 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 150000002942 palmitic acid derivatives Chemical class 0.000 description 1
- IPCSVZSSVZVIGE-UHFFFAOYSA-N palmitic acid group Chemical group C(CCCCCCCCCCCCCCC)(=O)O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 1
- LRTFPLFDLJYEKT-UHFFFAOYSA-N para-isopropylaniline Chemical compound CC(C)C1=CC=C(N)C=C1 LRTFPLFDLJYEKT-UHFFFAOYSA-N 0.000 description 1
- 229920001568 phenolic resin Polymers 0.000 description 1
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 125000005498 phthalate group Chemical class 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000011253 protective coating Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000003248 quinolines Chemical class 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000010802 sludge Substances 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000010736 steam turbine oil Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000003760 tallow Substances 0.000 description 1
- TUNFSRHWOTWDNC-UHFFFAOYSA-N tetradecanoic acid Chemical class CCCCCCCCCCCCCC(O)=O TUNFSRHWOTWDNC-UHFFFAOYSA-N 0.000 description 1
- RSPCKAHMRANGJZ-UHFFFAOYSA-N thiohydroxylamine Chemical compound SN RSPCKAHMRANGJZ-UHFFFAOYSA-N 0.000 description 1
- 150000004992 toluidines Chemical class 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- 239000002383 tung oil Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 150000003738 xylenes Chemical class 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc 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
- C23F11/144—Aminocarboxylic acids
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31678—Of metal
Definitions
- the present invention relates to metals or metal-containing articles of manufacture which are normally subject to corrosion and which have been rendered substantially non-corrodible by treatment with a dispersion of certain free dicarboxylic acids in, a suitable vehicle.
- Metallic surfaces particularly those containing iron, require protection against the hazard of corrosion in the presence of water.
- a protective coating such as a slushing oil
- Diesel engine fuels often corrodes closely fitted parts such as are found in Diesel engine unit type injectors
- water in turbines corrodes turbine lubricant circulatory systems, particularly the governor mechanisms of steam turbines
- water in hydrocarbon oils such as gasoline rusts steel storage tanks and drums
- water in anti-freeze compositions causes corrosion in automobile radiation, etc.
- Corrosion not only has a deleterious effect upon the metal surfaces, but also frequently loosens finely divided metal oxides which may act as oxidation catalysts increasing the rate of deterioration of various organic compounds with which they come in contact or may enter between moving parts of machinery where they act as abrasives.
- the dispersion may be a true or colloidal solution in a suitable vehicle which is capable of flowing under the conditions of the treatment,
- the treating temperature is preferably about atmospheric if the vehicle is normally liquid, although lower or higher temperatures may be employed.
- the lower temperature limit is usually determined by the solidification temperature of the liquid, and temperatures should be below the boiling temperature of the Vehicle and below the decomposition temperatures of both the vehicle and the dicarboxylic acid.
- ferrous metals e. g., soft iron, various steels, cast iron, and to a lesser extent copper, brass, bronze, zinc, aluminum, magnesium alloys, various bearing metals as copper-lead, cadmium-nickel, silver-nickel, etc.
- Corrosion may be due not only to atmospheric exposure, but may be caused or accelerated by contact with acidic materials, for example, by touching with the fingers. It also may occur in closed systems, as in internal combustion engines, steam turbines, pipe lines, etc., due to the corrosive influence of various impurities as water, oxygen, CO2, salts, inorganic or organic acids, I
- the prevention ofcorrosion may consist of a sin-
- the gle contact of the metal to be protected with the dispersion containing the dicarboxylic acid may comprise repeated contacts effected at intervals, or may consist of a continuous treatment lasting as long as the use of the particular dispersion or piece of equipment or both.
- the choice of any particular type of these treatments is usually dictated by circumstances. For example, if newly machined and finished machine parts are to be rust-proofed, they may be dipped or sprayed with a suitable dispersion, and then stored away.
- the circulating lubricating oil it is preferable that the circulating lubricating oil contain the active rust-preventive compound and contact is made as long as this oil is used. Should, after a while, this oil be discarded and otherwise rust protection fails.
- n and m are integers ranging from 1 up to about 8 and preferably are l or 2.
- the unoccupied valences shown are tied with hydrogen or hydrocarbon radicals.
- the latter may be aliphatic, alicyclic, aromatic or mixed and may contain substituents which are preferably not too i strongly polar, such as halogen, carbosulfide sulfur, etc., which should preferably be free from highly polar substituents, such as hydroxyl, carboxyl, carbonyl, amino, hydrosulfide, etc.
- the acid should not contain more than one oleflnic double bond per hydrocarbon radical, and preferably none.
- the acid should have not less than 16 carbon atoms and preferably at least 20 and up to about 60 carbon atoms 'for good anti-corrosive properties. Also the closeness of the nitrogen to the carboxyl radicals has a bearing on this property; in general the closer they are, the greater the protective power. Thus from this angle, homologues in which the nitrogen atom is in alpha position to at least one carboxyl radial nd preferably to both are most desirable.
- Compounds of this type are the N-amino diacetic acids, and more specifically the N-amino alphaalpha di-fatty acids.
- a disadvantage of the N-diacetic acids is their relatively low thermal stability which causes loss of CO2 upon heating to moderately elevated temperatures.
- N-amino alpha-beta di-fatty acids 'or N- amino beta-beta di-fatty acids are very nearly as potent corrosion inhibitors as the corresponding alpha-alpha compounds, and have a somewhat greater thermal stability.
- any one of the following three groups of my acids may be preferred:
- Group I c-coon Group II Group III CQCICOOH In Group I are the N-amino alpha-alpha difatty acids or corresponding naphthenic or'aromatic fatty acids:
- R1 is a hydrogen or a hydrocarbon radical
- R2 and Rs are hydrocarbon radicals, which in the case of ordinary fatty acids are allphatic, in the case of naphthenic acids comprise cycloaliphatic rings, and in the case of aromatic fatty acids are aromatic or alk-aromatic.
- dicarboxylic acids may be produced by reacting a primary amine with an alpha halogenated fatty acid, aromatic fatty acid or naphthenic acid as the case may be.
- Suitable primary amines to be used in this reaction are, for example, ammonia, various alkyl or cycloalkyl amines as methyl, ethyl, propyl, isopropyl, butyl, amyl, hexyl, iso-octyl, cyclopentyl, methyl cyclopentyl, cyclohexyl, dimethyl cyclohexyl, decyl,
- Suitable fatty acids include acetic, propionic, butyric, isobutyric, valeric, caproic, caprylic, decylic, undecylic,.
- Naphthenic acids such as are obtained by caustic alkali extraction of relatively high-boiling straight-run petroleum oils, such as kerosene, gas oil, lubricating oils, etc.
- synthetic naphthenic acids such as cyclohexyl acetic, cyclohexyl propionic, cyclohexyl stearic acids, corresponding alkyl cyclohexyl, tetrallyl, dicyclohexyl fatty acids, or acids derived from naphthenes obtained by hydrogenation of isophorone, diisophorone and homologues, etc.
- the two acids attached to the nitrogen may be different.
- N-amino alpha-beta difatty acids and the N-anthranilic alpha-mono fatty acids.
- the latter have the formula wherein R1 is hydrogen or a hydrocarbon radical, R2 and R3 are hydrocarbon radicals and X is an integer of 0-4.
- These acids may be produced by reacting anthranilic acid or homologues thereof with an alpha halogen fatty acid, naphthenic acid, or aromatic fatty acid of the classes described above.
- Homologues of anthranalic acid are alkyl anthranilic acids, ortho naphthylamine carboxylic acid, alkyl derivatives thereof, etc.
- Compounds of Group III may be prepared, for example, by reacting HBr with crotonic acid and then condensing the resulting brom-butyric acid with a relatively high-molecular weight primary amine, say a Clo-l8 aliphatic amine.
- the resulting compound is, for example:
- Still another type of compound is based on ascacoc alkylated diphenylamine. said phenyl radical having a carboxyl radical.
- colloidal dispersions Inasmuch as the acids are relatively little soluble in most vehicles, at least at ordinary room temperatures, it is usually necessary to produce suitable colloidal dispersions. These may be obtained, for example, by first producing a solution in the vehicle by heating mixtures of the vehicle with the acid to moderately elevated temperatures, and then allowing the solution to cool. This procedure, for instance, is applicable to hydrocarbon oils of sufliclently high boiling temperatures as kerosene, gas oils, Diesel fuels, range fuels, lubricating oils, etc.
- a solution may be formed in a solvent, such as a lower alcohol, benzene, etc., which is then poured into the liquid body of the desired vehicle. In this manner, colloidal dis persions of the acid in oils may be obtained.
- a solvent such as a lower alcohol, benzene, etc.
- the vehicles to which the N-dicarboxylic acids of this invention may be added for the purpose of producing corrosion-protective compositions may be divided into several groups. In the first place, they may be liquids or plastics, the only requirements as to their physical state being (in addition to their being able to act as carrier for the acids under normal atmospheric conditions) that they be spreadable over metal surfaces. Spreading may be accomplished by immersing, flooding, spraying, brushing, troweling, etc.
- the vehicle After being applied, all or part of the vehicle may be evaporated, or it may be more or less permanent. In other words, both volatile carriers may be used, or substances which do not materially volatilize under normal atmospheric conditions. As to chemical requirements, the vehicle must be stable under ordinary conditions of storage and use and be inert to the active inhibitors.
- the vehicle should preferably be substantially neutral, although it may be weakly acidic or. basic, preferably having dissociation constants not above about 10-.
- vehicles of low dielectric constant as hydrocarbon oils, which are not conducive to ionization of dissolved electrolytes, relatively small amounts, i. e., about .1 %-5% of various carboxylic acids, such as fatty or naphthenic acids, may be present, and in many instances this may even be beneficial.
- Both polar and non-polar vehicles may be employed.
- the former are water, alcohols, such as methyl, ethyl, n-propyl, isopropyl, butyl, amyl, hexyl, cyclohexyl, heptyl, methyl cyclohexyl, octyl, decyl, lauryl, myristyl, cetyl, stearyl, benzyl, etc., alcohols; polyhydric alcohols as ethylene glycol, propylene glycol, butylene glycol, glycerol, methyl glycerol, etc.; phenol and various alkyl phenolsr ketones as acetones, methyl ethyl ketone, diethyl ketone.
- keto alcohols as benzoin
- ethers as diethyl ether, diisopropyl ether, diethylene dioxide, beta-beta dichlor diethyl ether.
- diphenyl oxide chlorinated diphenyl oxide, diethylene glycol, triethylene glycol, ethylene glycol mono-methyl ether, corresponding ethyl, propyl, butyl ethers; neutral esters of carboxylic and other acids as ethyl, propyl, butyl, amyl, phenyl, cresyl and higher acetates, propionates, butyrates, lactates, laurates, myristates, palmitates, stearates, oleates,
- ricinoleates phthalates, phosphites, phosphates. thiophosphates, carbonates; natural waves as carnauba wax, candelilla wax, Japan wax, jojoba oil, sperm oil; fats as tallow, lard oil, olive oil, cottonseed oil, Perilla oil, linseed oil, tung oil, soya bean oil, fiaxseed oil, etc.; weak bases as pyridine, alkyl pyrldines, quinolines, petroleum bases, etc.
- Vehicles of little or no polarity comprise hydrocarbons or halogenated hydrocarbons as liquid butanes, pentanes, hexanes, heptanes, octanes, benzene, toluene, xylenes, cumene, indene, hydrindene, alkyl naphthalenes; gasoline distillates, kerosene, gas oil, lubricating oils (which may be soap-thickened to form greases), petrolatum, parafiin wax, albino asphalt; carbon tetrachloride, ethylene dichloride, propyl chloride, butyl chloride, chlor benzol, chlorinated kerosene, chlorinated paramn wax, etc.
- hydrocarbons or halogenated hydrocarbons as liquid butanes, pentanes, hexanes, heptanes, octanes, benzene, toluene, xylenes, cumene
- the amounts of the dicarboxylic acids which must be incorporated in the above vehicles to produce corrosion-protective compositions vary considerably with the type of vehicle used.
- Resinous materials particularly those of a colloidal nature, calls for relatively larger amounts of inhibitors.
- Resinous materials which interfere with the activity of the inhibitors comprise asphaltenes, petroleum resins, various other natural resins, as rosin, resins formed by polymerization of drying fatty oils, phenol-formaldehyde resins, glyptal type resins formed by esterification of polyhydric alcohols with polycarboxylic acids, etc.
- N-amino dicarboxylic acids In the absence of such resinous materials, amounts required of the N-amino dicarboxylic acids vary from about 001% up to about .1%, although larger amounts may be used. However, where the acids are in colloidal dispersion,
- a concentration in excess of about .1% may result in relatively quick loss of part of the inhibitor by precipitation and settling.
- compositions containing these large amounts of colloidally dispersed inhibitors together with resin may be quite resistant to precipitation and settling.
- Suitable refining treatments include, for example, extraction with selective solvent for aromatic hydrocarbons as liquid S02, phenol, furfural, nitrobenzene, aniline, betabeta-dichlorine diethyl ether, antimony trichloride, etc.; treatment with AlCla, sulfuric acid. clay, etc. If the treatment produces a sludge, special care must be taken to remove it very thoroughly and completely.
- Example I The effectiveness of several N-amino dicarboxylic acids in suppressing corrosion was determined by a modified Kuebler test which consists of subjecting a polished steel strip to the action of a vigorously stirred emulsion of an oil under test with 10% by volume of distilled water or of a 2% solution of sodium chloride in distilled water at 75 C. for 48 hours. Results were as follows:
- Example II after 1% of toluidino di-alpha stearic acid had been dissolved therein.
- the two coated strips were then placed in a horizontal position in a glass dish and 30 drops of a 3% salt solution were deposited on the upper surface of the strips.
- a loose fitting cover was placed over the dish and it was allowed to stand at room temperature.
- Th rusting was determined by counting the number of drops that showed signs of rust in any" period of time. Results were as follows:
- Example III Of two polished steel strips, the first was inserted in a lubricating oil containing .01% N- toluidino alpha di-stearic acid. The other was coated in the same lubricating oil not containing a rust-preventive compound. Both steel strips were then touched with the bare fingers and left exposed to the atmosphere. The first strip did not develop fingerprints in many days, while the second one developed fingerprints within a few hours.
- the coated metal of claim 1 the film of which contains an acid having between 20 and 60 carbon atoms.
- An article of manufacture comprising a solid metal corrodible by salt solution treated with a fine dispersion in a substantially neutral vehicle of a free dicarboxylic acid having at least 16 carbon atoms and having the formula ECk-COOH wherein n and m are integers ranging from 1 to 8, and the unoccupied valences are tied to hydrogen or hydrocarbon radicals.
- Method of protecting-a solid metal corrodible by salt solution from corrosion comprising spreading over its surface a fine dispersion in a substantially neutral vehicle of a free diearboxylic acid having at least 16 carbon atoms and having the formula wherein R1 is a radical selected from the group consisting of hydrogen and hydrocarbons, and R: and R3 are hydrocarbon radicals.
- Method of protecting a solid metal corrodi-ble by salt solution from corrosion comprising spreading over its surface a, fine dispersion in a substantially neutral vehicle of a free dicarboxylic acid having at least 16 carbon atoms and having the formula v wherein Rrand R2 are hydrocarbon radicals and a: is an integer of 0-4.
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Mechanical Engineering (AREA)
- Metallurgy (AREA)
- Organic Chemistry (AREA)
- Lubricants (AREA)
- Preventing Corrosion Or Incrustation Of Metals (AREA)
Description
Patented Jan. 30, 1945 coanosron PROTECTION or METALS Ellis R. White, Albany; Calif., as'signor to Shell Development Company, San Francisco, Galif.,-
a corporation of Delaware No Drawing.
Application February 8, 1943,
Serial No. 475,203
. 15 Claims.
This is a continuation-in-part of my copending application Serial No. 439,929, filed April ,21, 1942. The present invention relates to metals or metal-containing articles of manufacture which are normally subject to corrosion and which have been rendered substantially non-corrodible by treatment with a dispersion of certain free dicarboxylic acids in, a suitable vehicle.
Metallic surfaces, particularly those containing iron, require protection against the hazard of corrosion in the presence of water. To illustrate: Moisture readily attacks finished or semi-finished metal objects unless the metal surface is covered during storage or shipment by a protective coating such as a slushing oil; water in Diesel engine fuels often corrodes closely fitted parts such as are found in Diesel engine unit type injectors; water in turbines corrodes turbine lubricant circulatory systems, particularly the governor mechanisms of steam turbines; and water in hydrocarbon oils such as gasoline rusts steel storage tanks and drums; water in anti-freeze compositions causes corrosion in automobile radiation, etc. Corrosion not only has a deleterious effect upon the metal surfaces, but also frequently loosens finely divided metal oxides which may act as oxidation catalysts increasing the rate of deterioration of various organic compounds with which they come in contact or may enter between moving parts of machinery where they act as abrasives.
It is a purpose of this invention to treat metals or articles of manufacture containing metals in a way so that they become resistant to their normal corrosion. It is a specific purpose to treat in a simple manner accurately machined metal parts so that they may be handled without developing corrosion, particularly in places where fingerprints have been left. Another purpose is to protect iron or steel equipment exposed to the atmosphere so that its rusting is prevented or at least retarded. Still another purpose is to protect mechanical equipment from rusting, which equipment stands idle and/ or is shipped over long distances.
It has been discovered that structural metals which are used in the construction of various articles of manufacture and are subject to a normal corrosion can be protected simply and effectively by treating them with a fine dispersion of a dicarboxylic acid having at least 16 carbon atoms and a linkage between the carboxyl radicals comprising a trivalent nitrogen atom.
The dispersion may be a true or colloidal solution in a suitable vehicle which is capable of flowing under the conditions of the treatment,
i. e., is liquid or plastic at the temperature of the treatment.
The treating temperature is preferably about atmospheric if the vehicle is normally liquid, although lower or higher temperatures may be employed. The lower temperature limit is usually determined by the solidification temperature of the liquid, and temperatures should be below the boiling temperature of the Vehicle and below the decomposition temperatures of both the vehicle and the dicarboxylic acid.
Metals capable of being thus protected are in particular the ferrous metals, e. g., soft iron, various steels, cast iron, and to a lesser extent copper, brass, bronze, zinc, aluminum, magnesium alloys, various bearing metals as copper-lead, cadmium-nickel, silver-nickel, etc.
Articles containing these metals are too numerous to recite. However, it may be mentioned that the problem of rust prevention is critical, for example, where accurately machined parts are involved, such as piston rings, engine cylinders, bearing shafts, plungers of pumps, etc. In other instances, rust prevention may perhaps not; be critical, but of vast economic importance as, for example, in the mass production of steel castings which are piled up and often set in the open for months before being finished.
Corrosion may be due not only to atmospheric exposure, but may be caused or accelerated by contact with acidic materials, for example, by touching with the fingers. It also may occur in closed systems, as in internal combustion engines, steam turbines, pipe lines, etc., due to the corrosive influence of various impurities as water, oxygen, CO2, salts, inorganic or organic acids, I
etc.
The treatment, according to this invention, for
the prevention ofcorrosion may consist of a sin-;
gle contact of the metal to be protected with the dispersion containing the dicarboxylic acid, or may comprise repeated contacts effected at intervals, or may consist of a continuous treatment lasting as long as the use of the particular dispersion or piece of equipment or both. The choice of any particular type of these treatments is usually dictated by circumstances. For example, if newly machined and finished machine parts are to be rust-proofed, they may be dipped or sprayed with a suitable dispersion, and then stored away. On the other hand, if rust prevention in a steam turbine is desired, it is preferable that the circulating lubricating oil contain the active rust-preventive compound and contact is made as long as this oil is used. Should, after a while, this oil be discarded and otherwise rust protection fails.
rust-preventive, then corrosion protection usually,
lasts for a long time thereafter, due to the protectlve film left behind. In cases where this film is mechanically destroyed, as in bearings or gears, etc., running under extreme loads, the protective film must be renewed continuously:
The general formula of the corrosion-preventive acids of this invention is:
wherein n and m are integers ranging from 1 up to about 8 and preferably are l or 2. The unoccupied valences shown are tied with hydrogen or hydrocarbon radicals. The latter may be aliphatic, alicyclic, aromatic or mixed and may contain substituents which are preferably not too i strongly polar, such as halogen, carbosulfide sulfur, etc., which should preferably be free from highly polar substituents, such as hydroxyl, carboxyl, carbonyl, amino, hydrosulfide, etc. For maximum stability againstdeterioration by oxidation, the acid should not contain more than one oleflnic double bond per hydrocarbon radical, and preferably none.
As indicated above, the acid should have not less than 16 carbon atoms and preferably at least 20 and up to about 60 carbon atoms 'for good anti-corrosive properties. Also the closeness of the nitrogen to the carboxyl radicals has a bearing on this property; in general the closer they are, the greater the protective power. Thus from this angle, homologues in which the nitrogen atom is in alpha position to at least one carboxyl radial nd preferably to both are most desirable. Compounds of this type are the N-amino diacetic acids, and more specifically the N-amino alphaalpha di-fatty acids. However, a disadvantage of the N-diacetic acids is their relatively low thermal stability which causes loss of CO2 upon heating to moderately elevated temperatures. For; this reason, it is often desirable to have at least one carboxyl radical separated from the nitrogen atom by 2 or even more carbon atoms. In general, N-amino alpha-beta di-fatty acids 'or N- amino beta-beta di-fatty acids are very nearly as potent corrosion inhibitors as the corresponding alpha-alpha compounds, and have a somewhat greater thermal stability.
Accordingly, depending upon the conditions of use, any one of the following three groups of my acids may be preferred:
Group I c-coon Group II Group III CQCICOOH In Group I are the N-amino alpha-alpha difatty acids or corresponding naphthenic or'aromatic fatty acids:
wherein R1 is a hydrogen or a hydrocarbon radical, and R2 and Rs are hydrocarbon radicals, which in the case of ordinary fatty acids are allphatic, in the case of naphthenic acids comprise cycloaliphatic rings, and in the case of aromatic fatty acids are aromatic or alk-aromatic.
These dicarboxylic acids may be produced by reacting a primary amine with an alpha halogenated fatty acid, aromatic fatty acid or naphthenic acid as the case may be. Suitable primary amines to be used in this reaction are, for example, ammonia, various alkyl or cycloalkyl amines as methyl, ethyl, propyl, isopropyl, butyl, amyl, hexyl, iso-octyl, cyclopentyl, methyl cyclopentyl, cyclohexyl, dimethyl cyclohexyl, decyl,
tetrallyl, dodecyl, myristyl, cetyl, stearyl, oleyl, etc., amines; or aromatic amines as aniline, toluidine, xylidines, cumidine, naphthylamine, etc. Suitable fatty acids include acetic, propionic, butyric, isobutyric, valeric, caproic, caprylic, decylic, undecylic,. laurlc, myristic, palmitic, stearic, arachic, behenic, oleic, phenyl acetic, phenyl propionic, phenyl stearic, tolyl stearic, naphthyl acetic, naphthyl stearic, acids, etc. Naphthenic acids, such as are obtained by caustic alkali extraction of relatively high-boiling straight-run petroleum oils, such as kerosene, gas oil, lubricating oils, etc., may be used; or synthetic naphthenic acids, such as cyclohexyl acetic, cyclohexyl propionic, cyclohexyl stearic acids, corresponding alkyl cyclohexyl, tetrallyl, dicyclohexyl fatty acids, or acids derived from naphthenes obtained by hydrogenation of isophorone, diisophorone and homologues, etc. Obviously, the two acids attached to the nitrogen may be different.
In Group II are the N-amino alpha-beta difatty acids and the N-anthranilic alpha-mono fatty acids. The latter have the formula wherein R1 is hydrogen or a hydrocarbon radical, R2 and R3 are hydrocarbon radicals and X is an integer of 0-4. These acids may be produced by reacting anthranilic acid or homologues thereof with an alpha halogen fatty acid, naphthenic acid, or aromatic fatty acid of the classes described above. Homologues of anthranalic acid are alkyl anthranilic acids, ortho naphthylamine carboxylic acid, alkyl derivatives thereof, etc.
Compounds of Group III may be prepared, for example, by reacting HBr with crotonic acid and then condensing the resulting brom-butyric acid with a relatively high-molecular weight primary amine, say a Clo-l8 aliphatic amine. The resulting compound is, for example:
' cnr-cn-cmcoon lan-N cm-cn-cmcoon Still another type of compound is based on ascacoc alkylated diphenylamine. said phenyl radical having a carboxyl radical.
Inasmuch as the acids are relatively little soluble in most vehicles, at least at ordinary room temperatures, it is usually necessary to produce suitable colloidal dispersions. These may be obtained, for example, by first producing a solution in the vehicle by heating mixtures of the vehicle with the acid to moderately elevated temperatures, and then allowing the solution to cool. This procedure, for instance, is applicable to hydrocarbon oils of sufliclently high boiling temperatures as kerosene, gas oils, Diesel fuels, range fuels, lubricating oils, etc.
In other cases, a solution may be formed in a solvent, such as a lower alcohol, benzene, etc., which is then poured into the liquid body of the desired vehicle. In this manner, colloidal dis persions of the acid in oils may be obtained.
The vehicles to which the N-dicarboxylic acids of this invention may be added for the purpose of producing corrosion-protective compositions may be divided into several groups. In the first place, they may be liquids or plastics, the only requirements as to their physical state being (in addition to their being able to act as carrier for the acids under normal atmospheric conditions) that they be spreadable over metal surfaces. Spreading may be accomplished by immersing, flooding, spraying, brushing, troweling, etc.
After being applied, all or part of the vehicle may be evaporated, or it may be more or less permanent. In other words, both volatile carriers may be used, or substances which do not materially volatilize under normal atmospheric conditions. As to chemical requirements, the vehicle must be stable under ordinary conditions of storage and use and be inert to the active inhibitors.
Thus, the vehicle should preferably be substantially neutral, although it may be weakly acidic or. basic, preferably having dissociation constants not above about 10-. In vehicles of low dielectric constant, as hydrocarbon oils, which are not conducive to ionization of dissolved electrolytes, relatively small amounts, i. e., about .1 %-5% of various carboxylic acids, such as fatty or naphthenic acids, may be present, and in many instances this may even be beneficial.
Both polar and non-polar vehicles may be employed. Among the former are water, alcohols, such as methyl, ethyl, n-propyl, isopropyl, butyl, amyl, hexyl, cyclohexyl, heptyl, methyl cyclohexyl, octyl, decyl, lauryl, myristyl, cetyl, stearyl, benzyl, etc., alcohols; polyhydric alcohols as ethylene glycol, propylene glycol, butylene glycol, glycerol, methyl glycerol, etc.; phenol and various alkyl phenolsr ketones as acetones, methyl ethyl ketone, diethyl ketone. methyl propyl, methyl butyl, dipropyl ketones, cyclohexanone and higher ketones; keto alcohols as benzoin; ethers as diethyl ether, diisopropyl ether, diethylene dioxide, beta-beta dichlor diethyl ether. diphenyl oxide, chlorinated diphenyl oxide, diethylene glycol, triethylene glycol, ethylene glycol mono-methyl ether, corresponding ethyl, propyl, butyl ethers; neutral esters of carboxylic and other acids as ethyl, propyl, butyl, amyl, phenyl, cresyl and higher acetates, propionates, butyrates, lactates, laurates, myristates, palmitates, stearates, oleates,
ricinoleates, phthalates, phosphites, phosphates. thiophosphates, carbonates; natural waves as carnauba wax, candelilla wax, Japan wax, jojoba oil, sperm oil; fats as tallow, lard oil, olive oil, cottonseed oil, Perilla oil, linseed oil, tung oil, soya bean oil, fiaxseed oil, etc.; weak bases as pyridine, alkyl pyrldines, quinolines, petroleum bases, etc.
Vehicles of little or no polarity comprise hydrocarbons or halogenated hydrocarbons as liquid butanes, pentanes, hexanes, heptanes, octanes, benzene, toluene, xylenes, cumene, indene, hydrindene, alkyl naphthalenes; gasoline distillates, kerosene, gas oil, lubricating oils (which may be soap-thickened to form greases), petrolatum, parafiin wax, albino asphalt; carbon tetrachloride, ethylene dichloride, propyl chloride, butyl chloride, chlor benzol, chlorinated kerosene, chlorinated paramn wax, etc.
The amounts of the dicarboxylic acids which must be incorporated in the above vehicles to produce corrosion-protective compositions vary considerably with the type of vehicle used. As a general rule, the presence of resinous materials, particularly those of a colloidal nature, calls for relatively larger amounts of inhibitors. Resinous materials which interfere with the activity of the inhibitors comprise asphaltenes, petroleum resins, various other natural resins, as rosin, resins formed by polymerization of drying fatty oils, phenol-formaldehyde resins, glyptal type resins formed by esterification of polyhydric alcohols with polycarboxylic acids, etc.
In the absence of such resinous materials, amounts required of the N-amino dicarboxylic acids vary from about 001% up to about .1%, although larger amounts may be used. However, where the acids are in colloidal dispersion,
rather than in true solution, a concentration in excess of about .1% may result in relatively quick loss of part of the inhibitor by precipitation and settling.
In the presence of resins and other colloids, amounts in excess of .1% and up to 5% may be required. Inasmuch as resins may act as protective colloids, compositions containing these large amounts of colloidally dispersed inhibitors together with resin may be quite resistant to precipitation and settling.
Since resinous and gummy substances in the vehicles do call for greater amounts of inhibitors, it is usually desirable to refine normally liquid vehicles thoroughly and free them from gummy substances, thereby imparting to them maximum inhibitor'susceptibility. This is of particular importance, for example, in lubricating oils, specifically steam turbine oils, which are advantageously highly refined before the inhibitor is introduced. Suitable refining treatments include, for example, extraction with selective solvent for aromatic hydrocarbons as liquid S02, phenol, furfural, nitrobenzene, aniline, betabeta-dichlorine diethyl ether, antimony trichloride, etc.; treatment with AlCla, sulfuric acid. clay, etc. If the treatment produces a sludge, special care must be taken to remove it very thoroughly and completely.
Example I The effectiveness of several N-amino dicarboxylic acids in suppressing corrosion was determined by a modified Kuebler test which consists of subjecting a polished steel strip to the action of a vigorously stirred emulsion of an oil under test with 10% by volume of distilled water or of a 2% solution of sodium chloride in distilled water at 75 C. for 48 hours. Results were as follows:
Oil Additive Conditions Corrosion l b 11, 150 S. U. at 100 F N L Distilled water 100 rusted. fli .oo1% N-toluidino dl-alphastearic acid NaCl i)...
D ...do Distilled water.... rusted. Do .002% N-toluidino di-alpha stearic acid NaCl 1,00% 0 I118 133 .005? N -toluidino di-alpha stearic acid NZ; lg i 0 0. 15311 .003% N-octadecyl amino (ll-815118 stearic acid; no, Do" Less than .01 l N-toluidino phs stearic acetic acid d Do. Do Less than .01 o 1 Nranthranilic alpha stearic acid D Do Less han .01% 1 N-octadecyl amino beta-beta dipropionic Do.
ac Do Less than l N-octadecyl amino alpha propionic beta- Do.
butyric acid. I v
Samples impure, hence amount of active ingredient less than weighed out amount of .01%.
Example II after 1% of toluidino di-alpha stearic acid had been dissolved therein. The two coated strips were then placed in a horizontal position in a glass dish and 30 drops of a 3% salt solution were deposited on the upper surface of the strips. A loose fitting cover was placed over the dish and it was allowed to stand at room temperature.
Th rusting was determined by counting the number of drops that showed signs of rust in any" period of time. Results were as follows:
Per cent rusted Coating 5 days 10 days 507 parafiin wax 507: petrolatum 80 83 49.57 paraifin wax..
49.5% petrolatum 10 5o 1% toluidino (ii-alpha stearic acid Example III Of two polished steel strips, the first was inserted in a lubricating oil containing .01% N- toluidino alpha di-stearic acid. The other was coated in the same lubricating oil not containing a rust-preventive compound. Both steel strips were then touched with the bare fingers and left exposed to the atmosphere. The first strip did not develop fingerprints in many days, while the second one developed fingerprints within a few hours.
I claim as my invention:
1. A solid metal corrodible by salt solution coated with a corrosion-preventive film formed by a dicarboxylic acid having at least 16 carbon atoms and having the formula wherein n and m are integers ranging from 1 to 8, and the unoccupied valences are tied to hydrogen or hydrocarbon radicals.
2. The coated metal of claim 1, the film of which contains an acid having between 20 and 60 carbon atoms.
3. A solid metal corrodible by salt solution coated with a corrosion-preventive film formed by a dicarboxylic acid having at least 16 carbon atoms and having the formula wherein n and m are 1 or 2 and the unoccupied valences are tied to hydrogen or hydrocarbon radicals.
4. A solid metal corrodible by salt solution coated with a corrosion-preventive film formed by a dicarboxylic acid having at least 16 carbon atoms and having the formula m-cn-ooon Rr-N wherein R1 is a, radical selected from the group consisting of hydrogen and hydrocarbons, and R2 and R: are hydrocarbon radicals.
5. A solid metal corrodible by salt solution coated with a corrosion-preventive film formed by a free N-amino alpha-alpha di-fatty acid having at least 16 carbon atoms.
6. A solid metal corrodible by salt solution coated with a corrosion-preventive film formed by N-aromatic amine di-fatty acid containing at least 16 carbon atoms.
7. A solid metal corrodible by salt solution coated with a corrosion preventive film formed by an N-amino alpha-alpha' di-stearic acid.
8. A solid metal corrodible by salt solution.
coated with a corrosion preventive film formed by an N-amino alpha-alpha di-naphthenic acid containing at least 16 carbon atoms.
9. A solid metal corrodible by salt solution coated with a corrosion preventive film formed by a free dicarboxylic acid having at least 16 carbon atoms and having the formula wherein R1 is a hydrogen or hydrocarbon radical and R2 are hydrocarbon radicals and :c is 0-4.
10. A solid metal corrodible by salt solution coated with a corrosion preventive film formed by N-anthranilic alpha 'stearic acid.
11. A ferrous metal coated with a rust-preventive film formed by a dicarboxylic acid having at least 16 carbon atoms and having the formula wherein n and m are integers ranging from 1 to 8, and the unoccupied valences are tied to hydrogen or hydrocarbon radicals.
12. An article of manufacture comprising a solid metal corrodible by salt solution treated with a fine dispersion in a substantially neutral vehicle of a free dicarboxylic acid having at least 16 carbon atoms and having the formula ECk-COOH wherein n and m are integers ranging from 1 to 8, and the unoccupied valences are tied to hydrogen or hydrocarbon radicals.
. 14. Method of protecting-a solid metal corrodible by salt solution from corrosion comprising spreading over its surface a fine dispersion in a substantially neutral vehicle of a free diearboxylic acid having at least 16 carbon atoms and having the formula wherein R1 is a radical selected from the group consisting of hydrogen and hydrocarbons, and R: and R3 are hydrocarbon radicals.
15. Method of protecting a solid metal corrodi-ble by salt solution from corrosion comprising spreading over its surface a, fine dispersion in a substantially neutral vehicle of a free dicarboxylic acid having at least 16 carbon atoms and having the formula v wherein Rrand R2 are hydrocarbon radicals and a: is an integer of 0-4.
ELLIS R. WHITE.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
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US475203A US2368606A (en) | 1943-02-08 | 1943-02-08 | Corrosion protection of metals |
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US475203A US2368606A (en) | 1943-02-08 | 1943-02-08 | Corrosion protection of metals |
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US2368606A true US2368606A (en) | 1945-01-30 |
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Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2496798A (en) * | 1946-05-14 | 1950-02-07 | Texas Co | Rust-inhibiting lubricating composition |
US4225647A (en) * | 1977-12-02 | 1980-09-30 | Parent Richard A | Articles having thin, continuous, impervious coatings |
-
1943
- 1943-02-08 US US475203A patent/US2368606A/en not_active Expired - Lifetime
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2496798A (en) * | 1946-05-14 | 1950-02-07 | Texas Co | Rust-inhibiting lubricating composition |
US4225647A (en) * | 1977-12-02 | 1980-09-30 | Parent Richard A | Articles having thin, continuous, impervious coatings |
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