US2411593A - Corrosion protection of metals - Google Patents

Corrosion protection of metals Download PDF

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Publication number
US2411593A
US2411593A US498434A US49843443A US2411593A US 2411593 A US2411593 A US 2411593A US 498434 A US498434 A US 498434A US 49843443 A US49843443 A US 49843443A US 2411593 A US2411593 A US 2411593A
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United States
Prior art keywords
acids
oil
acid
corrosion
radical
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US498434A
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Willis G Routson
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Shell Development Co
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Shell Development Co
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Priority to US498434A priority Critical patent/US2411593A/en
Priority to NL128A priority patent/NL68160C/xx
Priority to GB13356/45A priority patent/GB600775A/en
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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
    • C23F11/147—Nitrogen-containing compounds containing a nitrogen-to-oxygen bond
    • 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
    • C23F11/146—Nitrogen-containing compounds containing a multiple nitrogen-to-carbon bond

Definitions

  • the present invention relates to metals or metal-containing articles of manufacture which are normall subject to corrosion and which have been rendered substantially non-corrodible by treatment with a dispersion of certain nitrogen containing organic compounds in a. suitable vehicle. It also relates to compositions having anticorrosive, and especially rust-protective properties, and more particularly deals with compositions comprising a substantially neutral vehicle such as normally liquid or normally solid hydrocarb'ons (e. g., fatty oils and natural Waxes) alcohols, ethers, water, etc., containing finely dispersed small amounts of such an organic nitrogen compound.
  • a substantially neutral vehicle such as normally liquid or normally solid hydrocarb'ons (e. g., fatty oils and natural Waxes) alcohols, ethers, water, etc.
  • Metallic surfaces particularly those contain- 2 phere 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.
  • a further object is to provide slushing oils of improved rust-protective properties particularly adapted to withstand the effects of maing iron, require protection against the hazard of a corrosion in the presence of water.
  • This invention is based on the discovery that certain organic nitrogen compounds (as hereafter described) have valuable and unexpected rust protective and otherbeneficial properties. These compounds having, say, upward of about '10 carbon atoms and more preferably '12 or more carbon atoms, which are substantially oil-soluble,
  • the compounds of the invention may advantageously be employed in ailubri'cat-- ing composition or other oily medium.
  • the compounds of the invention may be dispersed in either oily or non-oily media although not with the same efiectiveness.
  • the nitrogen compounds of the present invention are characterized by the presence of a nitrile (CN) nitro (NOa) or nitroso (NO) group. (Since may be found in equilibrium with the isomeric form Y nitroso compounds.)
  • These nitrogen-containing radicals are attached to a carbon atom which is not -more than three atoms removed from an acidic group.
  • the acidic radical may be COOH, CSOH, GOSH, 'CSSH, SOsH, POsH, and the like.
  • this acidic radical is attached to a carbon atom which is alpha or beta to the carbon atom carrying the nltrile, nitro or nitroso group, p.
  • the carboxylic acid radical and the nitrile radical are the preferred radicals of their respective groups.
  • R and R" are hydrogen atoms or hydrocarbon or substituted hydrocarbon radicals
  • Y is a nitrile, nitro or nitroso radical
  • R is a hydrocarbon or substituted hydrocarbon radical and n is 0, 1, 2 or '3, but preferably or 1.
  • Preferable values. for R and R" are hydrogen and/or low molecular weight aliphatic radicals such as methyl, ethyl, propyl, butyl, 'etc.
  • R may also contain an ether type linkage which contains an oxygen, sulfur, selenium or tellurium atom. A preferred group of these latter compounds are those in which this ether linkage is attached to the nitrile, nitro, or nitroso containing carbon atom as represented by the formula in which Z is 0, S, Se, or Te.
  • the several hydrocarbon radicals of the for- Piperidine RzCO+HzC--C OOEt Na r etc. should preferably be free from highly bonyl, amino, hydrosulfide, etc.
  • the acid should not contain more than one olefinic double bond per hydrocarbon radical, and more preferably none.
  • hydrocarbon radicals are methyl, ethyl, propyl, isopropyl, normal butyl, isobutyl, secondary butyl, tertiary butyl, normal pentyl, isopentyl, secondary pentyl, hexyl, normal octyl, iso-octyl, normal decyl, isodecyl, dodecyl, tetradecyl, cetyl, stearyl, trimethyl octodecyl, allyl, methallyl, crotyl, methyl vinyl carbinyl, butenyl, pentenyl, hexenyl, propargyl, geranyl, oleyl, phenyl, naphthyl, anthryl, tolyl, xylyl, secondary butyl-naphthyl, dipropylnaphthyl, benzyl, naphthyl
  • a preferred group of oil-soluble compounds are those in which the organic radical or radicals have a total of not less than about 8 carbon atoms and more preferably at least 10 or 12 and up to about carbon atoms for good anti-corrosive properties.
  • H2O H polar substituents such as hydroxyl,carboxyl,cartained by caustic alkali extraction of relatively high-boiling straight-run petroleum oils.
  • kerosene, gas oil, lubricating'oils, etc. may also be used, as well as 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.
  • carboxylic acids comprises the group of hydroxy acids such as hydroxy benzoic', hydroxy naphthenic, etc., acids and the alkyl homologues thereof, typical representatives being the alkyl salicylic acids.
  • the dispersion of the present anti-rusting compounds may be a true or colloidal solution in a suitable vehicle which is capable of flowing under the conditions of use, i. e., is liquid or plastic at the temperature employed.
  • a suitable vehicle which is capable of flowing under the conditions of use, i. e., is liquid or plastic at the temperature employed.
  • Both true solutions and colloidal dispersion in various vehicles are effective in the matter of corrosion protection.
  • true solutions are preferred for two reasons: first, colloidal solutions may, under many circumstances, coagulate, in which case the active protectiv agent would be eliminated; and second, colloids tend tocause emulsification of oily vehicles with water, emulsification in many instances being very undesirable as in the lubrication of steam turbines.
  • the treating temperature for metals is preferably about room temperature 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 nitrogen compound.
  • Metals capable of being thus protected are in particular the ferrous metals, e. g., softiron,
  • sium' alloys various bearing metals as copperlead,cadmium-nicke1, silver-nickel, etc.
  • 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 be replaced by another one not containing a rust-preventive. then corrosion protection usually lasts for a long time thereafter, due to the protective 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, otherwise rust protection fails.
  • the vehicles to which the compounds 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 stat 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, trowelling, etc. After being applied, all or part of the vehicle may evaporate, 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 besubstan tially neutral, although it may be weakly acidic or basic, preferably having a dissociation con-'- instances this may be beneficial.
  • Both polar and non-polar vehicles may b employed.
  • the former are water; alcohols, such as methyl, ethyl, propyl, isopropyl, butyl,
  • I glycerol, methyl glycerol, etc.; phenol and various Corrosion may be due not only to atmospheric exposure, but; may be caused or accelerated by contact with acidic materials, for example,- by
  • the treatment, according to this invention, for the prevention of corrosion may consist of a single contact of the metal to be protected with the dispersion or piece of equipment or both.
  • the choice usually dictated by circumstances.
  • V V of any particular'type of these treatments is alkyl phenols; ketones as acetone, methyl ethyl ketone, diethyl ketone, methyl propyhmethyl' butyl, dl'propyl ketones, cyclohexanone and higher ketones; keto alcohols as benzoin; ethers'as diethyl ether, diisopropyl ether, diethylene diox ide, beta-beta dichlor diethyl ether, diphenyl methyl ether, corresponding ethyl, propyl, bu'tyl ethers; neutral esters of carboxylic and other 65.
  • oleates oleates, ricinoleates, phthalates, phosphates,
  • phosphites, thiophosphates, carbonates natural waxes as carnauba. wax, candelillia wax, Japan wax, jojoba oil, sperm oil; fats as tallow, lard oil,
  • Vehicles of little or no polarity comprise hydrocarbons or halogenated hydrocarbons as liquid butanes, pentanes, hexanes, heptanes, octanes,
  • dene, hydrindene, alkyl naphthalenes gasoline distillates, kerosene, gas oil, lubricating oils (which may be soap-thickened to form greases), petrolatum, paraflin wax, albino asphalt, carbon tetrachloride, ethylene dichloride, propyl chloride, butyl chloride, chlor-benzol, chlorinated kerosene, chlorinated paraffin wax, etc.
  • 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 esterificatlon of polyhydric alcohols with polycarboxylic acids, etc.
  • compositions containing these larger 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 solvents for aromatic hydrocarbons such as liquid sulfur dioxide, phenol, furfural, nitrobenzene, aniline, beta-beta-dichloro-diethyl ether, antimony trichloride, etc.; treatment with AlCla, sulfuric acid, clay, etc. If the treatments produce a sludge, special care must be taken to remove it very thoroughly and completely.
  • these acids may contain various substitution radicals as hydroxyl, ether, amino, nitro, hydrosulfide, sulfide, halide, etc., radicals, the most important limiting factor being the necessary stability.
  • a saturated aliphatic dicarboxylic acid having the carboxyl radicals as close to each other as possible as is consistent with the requirement for stability.
  • Particularly effective are alkyl succinic acids having at least 16, and preferably 20 to 40 carbon atoms.
  • auxiliary acids to hydrocarbon oils containing the primary anti-corrosives is of greatest importance when dealing with wellrefined hydrocarbon compositions.
  • Conventional refining methods such as acid and alkali treatment, solvent extraction, hydrogenation, etc., remove naphthenic and other monocarboxylic acids which may naturally be contained in the hydrocarbons in small amounts and which may enhance the action of the anti-corrosives.
  • naphthenic and similar acids are naturally present, in general the addition of further amounts of the auxiliary acids of the type described is beneficial.
  • the nitrogen compound in addition to affording rust protection itself, also promotes the formationof a protective film of the dicarboxylic acid on a metallic surface.
  • This combination of nitrogen compound and dicarboxylic acid is particularly important in connection with the rust inhibiting of highly refined lubricating compositions such as turbine oil since the-refining treatment may render the nitrogen compound only sparingly soluble in the finished oil.
  • a refined Mid-Continent 400 vis. at F. turbine raifinate may only dissolve about 0.015% of alpha stearic acid while it will dissolve about 5% alkyl succinic acid obtained by condensation of maleic anhydride with higher molecular weight olefins (Ex C12-C3o) and subsequent hydrolysis to the acid.
  • auxiliary dicarboxylic acids between about 0.001% and 0.1% may be used in petroleum distillate oils; in bright stocks up to about 1% is indicated, while in plastic compositions higher amounts, even up to 5-10%, may be useful.
  • the invention may be further illustrated by reference to the following modified Kuebler or Westinghouse corrosion tests.
  • Steel strips (3"x "x were completely immersed in 460 ml. samples of oil which were continuously agitated with electric motor-driven glass stirrers. Thirty minutes after starting, 10% volume of synthetic sea water was added to each sample.
  • the tests were continued for 48 hours at a controlled temperature of 75 C. and the amount of rusting on the strips .then noted.
  • the synthetic sea water was made up from the following formula: in 1000 ml. water-11.0 g. MgClz'GHsO; 4.0 g. NazSO4 (anhydrous); 1.2 g. CaClz (anhydrous); 25.0 g. NaCl.)
  • bases include metal as well as organic bases.
  • Metal bases include those of the alkali metals, Cu, Mg, Ca, Sr, Ba, Zn, Cd, Al, Sn, Pb, Cr, Mn, Fe, Ni, G0, etc.
  • Organic bases include various nitrogen bases as primary, secondary, tertiary and quaternary amines.
  • detergent forming acids are the various fatty acids of say, 10 to carbon atoms, wool fat acids, parafiin wax acids (produced by oxidation of parafiin wax), chlorinated fatty acids, rosin acids, aromatic carboxylic acids in!
  • composition of claim 1 wherein said cor atoms rerosion retarding acid is an alpha cyano carboxylic acid containing a minimum 013 12 carbon atoms. 3. The composition of claim 1 wherein said vehicle is normally liquid.
  • a lubricating composition comprising a predominant amount of a refined mineral oil and a beneficiating amount of an oil-miscible compound having between about 10 and about 60 carbon such as may be produced by treatment of alkyl aromatic hydrocarbons or high boiling petroleum the calcium and barium salts of diphenol mono and poly sulfides.
  • Non-metallic detergents include compounds such as the phosphatides (e. g., lecithin), certain fatty oils as rapeseed oil, voltolized fatty or mineral oils, etc.
  • Anti-oxidants comprise several types, for example. alkyl phenols such as 2,4,6-trimethyl atoms of the formula comprising hydrogen atoms, hydrocarbon and substituted hydrocarbon radicals, R is an organic radical, X is a radical containing an acidic hydrogen atom, Y represents a radical selected from the group consisting of a nitrile, nitro and nitroso radical and n represents a number selected from the group consisting of 0, 1, 2, and 3.
  • alkyl phenols such as 2,4,6-trimethyl atoms of the formula comprising hydrogen atoms, hydrocarbon and substituted hydrocarbon radicals
  • R is an organic radical
  • X is a radical containing an acidic hydrogen atom
  • Y represents a radical selected from the group consisting of a nitrile, nitro and nitroso radical
  • n represents a number selected from the group consisting of 0, 1, 2, and 3.
  • composition of claim 4 in which said compound is an alpha cyano carboxylic acid.
  • composition of claim 4 in which said com-pound has a, minimum of 12 carbon atoms and is present in the amount of about 0.001% to about 0.1%.
  • composition of claim 4 which also contains a small amount or a corrosion inhibiting iii dicarboxylic acid containing aminimum of 16 carbon atoms.
  • An improved turbine oil comprising a refined mineral lubricating oil in which has been incorporated about (MIDI-0.1% of an oil miscible alpha cyano carboxylic acid having between about 10 and about 60 carbon atoms and about 0.001- 0.i% of an oil soluble alkyl succinic acid possessing a minimum of 16 carbon atoms.
  • a corrosion-preventive composition comprising a predominant amount of a hydrocarbon fraction containing finely dispersed therein a corrosion retarding amount of an organic monobasic acid having between about 10 and about 60 carbon atoms and containing a radical selected from the group consisting of nitrile, nitroso and nitro radicals which is not more than 4 carbon atoms removed from the acid radical, and from about 0.001% to about 0.1% of an alkyl succinic acid having a minimum of about 16 carbon atoms.

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  • 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)
US498434A 1943-08-11 1943-08-11 Corrosion protection of metals Expired - Lifetime US2411593A (en)

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US498434A US2411593A (en) 1943-08-11 1943-08-11 Corrosion protection of metals
NL128A NL68160C (enrdf_load_stackoverflow) 1943-08-11 1945-03-28
GB13356/45A GB600775A (en) 1943-08-11 1945-05-28 Corrosion protective compositions

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Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2532407A (en) * 1945-09-05 1950-12-05 Johansson Sven Christian Corrosion inhibiting compositions
US2577219A (en) * 1946-07-06 1951-12-04 Shell Dev Corrosion inhibition with a mixture of inhibitors of differing volatility
US2581120A (en) * 1948-05-05 1952-01-01 Standard Oil Dev Co Rust inhibiting composition
US2731324A (en) * 1951-09-07 1956-01-17 Sinclair Refining Co Corrosion inhibitor containing alkanoyloxyacetic acid and method of using same
US2863837A (en) * 1955-05-07 1958-12-09 Henkel & Cie Gmbh Corrosion inhibiting bath
US2962356A (en) * 1953-09-09 1960-11-29 Monsanto Chemicals Corrosion inhibition
US3029126A (en) * 1957-05-17 1962-04-10 California Research Corp Method of inhibiting corrosion in steam generating systems
US3127349A (en) * 1964-03-31 Lubricating oil compositions having a
WO2005026106A1 (en) * 2003-09-11 2005-03-24 Invista Technologies S.A R.L. Process of hydrocyanation of unsaturated carboxylic acid derivatives
US20060081381A1 (en) * 2004-09-07 2006-04-20 Kassbohrer All Terrain Vehicles, Inc. Material handling apparatus
US20110092729A1 (en) * 2003-05-13 2011-04-21 Invista North America S.A.R.L. Process of hydrocyanation of unsaturated carboxylic acid derivatives
CN114350428A (zh) * 2022-01-11 2022-04-15 温州市海格阀门有限公司 一种防锈的蝶阀铸件及其加工方法

Cited By (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3127349A (en) * 1964-03-31 Lubricating oil compositions having a
US2532407A (en) * 1945-09-05 1950-12-05 Johansson Sven Christian Corrosion inhibiting compositions
US2577219A (en) * 1946-07-06 1951-12-04 Shell Dev Corrosion inhibition with a mixture of inhibitors of differing volatility
US2581120A (en) * 1948-05-05 1952-01-01 Standard Oil Dev Co Rust inhibiting composition
US2731324A (en) * 1951-09-07 1956-01-17 Sinclair Refining Co Corrosion inhibitor containing alkanoyloxyacetic acid and method of using same
US2962356A (en) * 1953-09-09 1960-11-29 Monsanto Chemicals Corrosion inhibition
US2863837A (en) * 1955-05-07 1958-12-09 Henkel & Cie Gmbh Corrosion inhibiting bath
US3029126A (en) * 1957-05-17 1962-04-10 California Research Corp Method of inhibiting corrosion in steam generating systems
US20110092729A1 (en) * 2003-05-13 2011-04-21 Invista North America S.A.R.L. Process of hydrocyanation of unsaturated carboxylic acid derivatives
WO2005026106A1 (en) * 2003-09-11 2005-03-24 Invista Technologies S.A R.L. Process of hydrocyanation of unsaturated carboxylic acid derivatives
EP2058298A3 (en) * 2003-09-11 2009-08-19 INVISTA Technologies S.à.r.l. Process of hydrocyanation of unsaturated carboxylic acid derivatives
CN1878748B (zh) * 2003-09-11 2010-04-21 因维斯塔技术有限公司 氢氰化不饱和羧酸衍生物的方法
US7737294B2 (en) 2003-09-11 2010-06-15 Invista North America S.A R.L. Process of hydrocyanation of unsaturated carboxylic acid derivatives
US20060081381A1 (en) * 2004-09-07 2006-04-20 Kassbohrer All Terrain Vehicles, Inc. Material handling apparatus
US8119829B2 (en) 2004-09-08 2012-02-21 Invista North America S.A.R.L. Process of hydrocyanation of unsaturated carboxylic acid derivatives
CN114350428A (zh) * 2022-01-11 2022-04-15 温州市海格阀门有限公司 一种防锈的蝶阀铸件及其加工方法

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Publication number Publication date
GB600775A (en) 1948-04-19
NL68160C (enrdf_load_stackoverflow) 1951-07-16

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