US3755176A - Sulfur-containing carboxylic acids as corrosion inhibitors - Google Patents

Sulfur-containing carboxylic acids as corrosion inhibitors Download PDF

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US3755176A
US3755176A US00143660A US3755176DA US3755176A US 3755176 A US3755176 A US 3755176A US 00143660 A US00143660 A US 00143660A US 3755176D A US3755176D A US 3755176DA US 3755176 A US3755176 A US 3755176A
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acid
composition
oil
carbon atoms
percent
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A Williams
R Kinney
V Coty
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ExxonMobil Oil Corp
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Mobil Oil Corp
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    • 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
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    • C10M2219/08—Thiols; Sulfides; Polysulfides; Mercaptals
    • C10M2219/082—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
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    • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
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    • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/12—Inhibition of corrosion, e.g. anti-rust agents or anti-corrosives
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Definitions

  • ABSTRACT Organic compositions comprising a liquid hydrocarbon have improved corrosion inhibiting properties when an alkyl thiohydrocarbyl acid, or amine salt thereof, is present in the composition.
  • U.S. Pat. No. 2,223,129 discloses hydrocarbon oil lubricating compositions containing such compounds as phenylmercapto stearic acid as an extreme pressure agent.
  • U.S. Pat. No. 2,474,604 discloses the use of certain alkylthio carboxylic acids, among them cetylthio acetic acid as a rust inhibiting additive for mineral oils.
  • U.S. Pat. No. 2,477,356 teaches that alkylthio acetic acids, as for example, octadecylthio acetic acid, may be used as anticorrosion agents.
  • an organic composition comprising a hydrocarbon liquid and a corrosion inhibiting amount of 1) an acid of one of the formulas l.RS-R'-COOH and 2.
  • [-R" S R COOH] wherein R is alkyl of from about two to about 16 carbon atoms, R is a straight or branched hydrocarbylene group, such as alkylene, arylene, or an aryl-substituted alkylene, each containing from four to about 22 carbon atoms, R" is alkylene of from about two to about 16 carbon atoms and R' is the same as R, or of (2) an amine salt of such acid.
  • R since R may be branched, R may be such that the whole unit has the number of carbon atoms designated, i.e., from four to about 22 carbon atoms.
  • the sulfurbridged hydrocarbyl or hydrocarbylene must be an alkyl or alkylene group, and according to the discovery herein, such group will contain a minimum of 2 carbon atoms and a maximum of about 16.
  • the other hydrocarbylene group (R' and R" in the formula) may be an alkylene or an arylene group. This will become apparent from the data presented herein.
  • alkylthiohydrocarbyl acids (formula (1) above) of this invention may be synthesized in good yields using known methods.
  • derivatives of acetic and propionic acids may be made by reacting the appropriate thiol salt with the appropriate chloro acid, thus:
  • the dimer acid (the acid of formula (2) above) may be prepared by reacting a dithiol with a lactone in the presence of an alkali metal alkoxide.
  • Example 3 will outline this method in more detail.
  • the additives of this invention are preferably used as the free acid, but may be used in the form of their liquid-soluble amine salts to impart corrosion inhibiting properties.
  • the amines may be primary, secondary or tertiary and will include alkylamines, where the alkyl contains from about four to about 40 carbon atoms, or they may be arylamines, such as aniline and the like, or they may be of a type wherein the nitrogen is part of a ring system, e.g. pyridine.
  • Such salts are prepared by mixing one mole of the amine with one mole of the acid.
  • a synthetic hydrocarbon lubricating oil is one prepared by polymerizing decene-l to the trimer or tetramer. However, any of those liquid polymers containing from about six to about 60 carbon atoms ,may be used.
  • oils mentioned above may be used in a variety of ways. The most obvious of these is as a lubricant, either for applications involving relatively mild conditions, such as in switch contacts, or for applications involving high temperatures. This latter use includes lubrication of an automotive engine. Other areas of use include hydraulic fluids, turbine oils, gear oils and cutting oils.
  • oils used in working metals may or may not be of lubricating viscosity, depending upon the particular application.
  • a metal pre-coat which is applied prior to storage or to rolling operations, from its very nature will require a fairly viscous oil.
  • the oil in coolants which are generally of the oil-in-water type, need not have lubricating viscosities.
  • 4-(ethylthio)dodecanoic acid was soluble by more than 1 percent at 12C in a decene trimer oil, whereas N-(dodecylthio)acetic was not soluble at even 0.05 percent at the same temperature.
  • composition whether containing a hydrocarbon as the major liquid or a large amount of water, will need from about 0.01 percent to about 5 percent by weight, preferably from about 0.01 percent to about 0.2 percent, of the alkyl thiohydrocarbyl acid or its salt to effectively impart anti-corrosion properties thereto.
  • water When used as an aqueous composition, water will comprise from about 50 percent to about 99 percent of the total composition. If it is desirable or necessary to utilize an emulsion, any of the well-known emulsifiers may be used.
  • EXAMPLE 1 A one liter flask was fitted with stirrer, thermometer, dropping funnel, and nitrogen inlet tube. To the flask was added 400 ml. of benzene, 63.7 g. of ethane thiol (1.043 mole). Then 53.5 g. of sodium methoxide (0.991 mole) was added with stirring under nitrogen. The mixture was heated and stirred to distil off methanol and benzene. After cooling the dry salt to room temperature, 152 g. (0.770 mole) of 'y-n-octyl-ybutyro-lactone was added. The mixture was heated and stirred under nitrogen for 16 hours at 150C. Then 400 ml. of 6N.
  • hydrochloric acid was added with stirring and heating.
  • the aqueous layer was separated from the crude product and extracted by two 200 ml. portions of benzene. This extract was combined with the crude product.
  • the benzene was distilled off at atmospheric pressure. Vacuum distillation gave 126 g. of purified 4-(ethylthio) dodecanoic acid distilling at l46-151C at 0.2 mm of mercury.
  • EXAMPLE 2 By the method of Example 1, a product was obtained from the reaction of 10.0 g.- of, sodium methoxide with 34.0 g. of l-decanethiol in 200 ml. of benzene, followed by 60 g. of y-phenyl-y-butyrolactone.
  • the crude sulfide acid (59 g-.)- was purified by dissolving in a solution of 50 g. of sodium carbonate in 1,500 ml. of water, and extracting this with two 250 ml. portions of nhexane.
  • the product was liberated from the aqueous solution by the addition of 6N. hydrochloric acid, and collected in ethyl ether. After evaporation of the ether there remained 50 g. of 4-(n-decylthio)-4- phenylbutyric acid.
  • R may have the requisite number of alkyl carbon atoms, if R is alkyl of less than about 4 carbon atoms or (2) if R is an aromatic hydrocarbyl group, the product fails as a rust inhibitor. This is shown by the following data, found under same conditions and in same oil as above.
  • An organic composition comprising a major proportion of a hydrocarbon liquid and a corrosion inhibiting amount of an acid of one of the formulas R S R COOl-l and [-R" S R COOl-l] wherein R is alkyl of from about two to about 16 carbon atoms, R is arylene of up to about 22 carbon atoms, R" is alkylene of from about two to about 16 carbon atoms and R' is hydrocarbylene of from four to about 22 carbon atoms.
  • composition of claim 1 comprising from about 0.01 to about 5 percent by weight of said acid salt.
  • composition of claim 1 wherein the hydrocarbon liquid is a mineral oil, a synthetic oil or a liquid hydrocarbon fuel.
  • composition of claim 3 wherein the oil is a lubricating oil.
  • composition of claim 3 wherein the oil is a turbine oil.
  • composition of claim 4 wherein the lubricating oil is a polyolefin fluid.
  • An aqueous emulsion comprising the composition of claim 1 and from about 50 to about 99 percent by weight thereof of water.
  • composition of claim 1 wherein the acid is ndecylthio-phenylbutyric acid.
  • composition of claim 1 wherein the acid has the formula [HOOC(CH CH(C H, S CH CH

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  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Mechanical Engineering (AREA)
  • Metallurgy (AREA)
  • Lubricants (AREA)
  • Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
US00143660A 1971-05-14 1971-05-14 Sulfur-containing carboxylic acids as corrosion inhibitors Expired - Lifetime US3755176A (en)

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Cited By (18)

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US4174284A (en) * 1978-08-14 1979-11-13 Phillips Petroleum Company Hydrocarbylpolythiobenzoic acids as anti-oxidation additives
US4297236A (en) * 1977-09-19 1981-10-27 Hoechst Aktiengesellschaft Water miscible corrosion inhibitors
EP0142078A1 (fr) * 1983-10-25 1985-05-22 Phillips Petroleum Company Lubrifiant pour le traitement de métal
US4549974A (en) * 1983-09-23 1985-10-29 Mobil Oil Corporation Lubricants containing sulfurized organic acid diamine salts
US4566879A (en) * 1983-09-23 1986-01-28 Mobil Oil Company Fuels containing sulfurized organic acid diamine salts
US4670163A (en) * 1985-05-29 1987-06-02 Phillips Petroleum Company Inhibiting corrosion
US4744948A (en) * 1987-06-04 1988-05-17 Texaco Inc. Thiol ester corrosion inhibition system
US4786424A (en) * 1985-12-05 1988-11-22 Phillips Petroleum Company Aqueous metal-working composition and process
US4981609A (en) * 1980-06-19 1991-01-01 Petrolite Corporation Compounds containing sulfur and amino groups
US5013482A (en) * 1988-07-21 1991-05-07 Ciba-Geigy Corporation Corrosion inhibition
US5176850A (en) * 1988-07-21 1993-01-05 Ciba-Geigy Corporation Substituted glycerol compounds
US5240625A (en) * 1989-03-23 1993-08-31 Bp Chemicals (Additives) Limited Lubricating oil additives
US5679627A (en) * 1995-12-22 1997-10-21 Exxon Research & Engineering Company High-load carrying turbo oils containing amine phosphate and a sulfur containing carboxylic acid (law348)
US5714441A (en) * 1996-07-12 1998-02-03 Exxon Research And Engineering Company Additive combination to reduce deposit forming tendencies and improve antioxidancy of aviation turbine oils
US5856280A (en) * 1996-07-12 1999-01-05 Exxon Research And Engineering Company Sulfur-containing carboxylic acid derivatives to reduce deposit forming tendencies and improve antioxidancy of aviation turbine oils
US20110034359A1 (en) * 2009-08-07 2011-02-10 Rabbat Philippe Marc Andre Lubricant composition
US8802606B2 (en) 2010-08-06 2014-08-12 Basf Se Lubricant composition having improved antiwear properties
US11168402B2 (en) * 2018-02-16 2021-11-09 Nippon Shokubai Co., Ltd. Metal corrosion inhibitor

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JPS5710695A (en) * 1980-04-18 1982-01-20 Cooper Edwin Inc Lubricant oil containing tertiary amine salt of sulfidized olefinic acid
JP2795890B2 (ja) * 1989-04-12 1998-09-10 出光興産株式会社 水性金属加工油剤
EP0498765A1 (fr) * 1991-02-04 1992-08-12 Ciba-Geigy Ag Procédé pour la préparation d'acides alcoyl-et aroylthiocarboxyliques et de leurs esters
FR2962131B1 (fr) * 2010-06-30 2013-10-18 Centre Nat Rech Scient Procede de fonctionnalisation de corps gras d'origine naturelle
JP7262883B2 (ja) * 2019-05-17 2023-04-24 エルジー・ケム・リミテッド ポリオレフィン－ポリスチレン系多重ブロック共重合体及びこの製造方法
JP7330592B2 (ja) * 2019-05-17 2023-08-22 エルジー・ケム・リミテッド ポリオレフィン－ポリスチレン系多重ブロック共重合体及びその製造方法
WO2020235887A1 (fr) * 2019-05-17 2020-11-26 주식회사 엘지화학 Copolymère multiblocs à base de polyoléfine-polystyrène et procédé de préparation s'y rapportant

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US2216751A (en) * 1935-05-14 1940-10-08 Standard Oil Dev Co Heavy metal salts of thioether carboxylic acids
US2354550A (en) * 1940-10-07 1944-07-25 Standard Oil Dev Co Lubricant
US2423865A (en) * 1944-02-28 1947-07-15 Shell Dev Anticorrosive
US2474604A (en) * 1947-06-11 1949-06-28 Standard Oil Dev Co Rust-preventing compounds
US2683119A (en) * 1949-11-16 1954-07-06 Standard Oil Dev Co Compounded lubricant
US2884379A (en) * 1954-06-30 1959-04-28 Exxon Research Engineering Co Rust inhibitor composition
US2892852A (en) * 1957-05-28 1959-06-30 Nathan H Koenig Alkylthio-, (acetylthio)-and (arylthio)-undecanoic acids

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FR881759A (fr) * 1939-10-21 1943-05-07 Deutsche Hydrierwerke Ag Procédé permettant d'éviter la corrosion du fer par l'eau et les solutions aqueuses et produits servant à l'exécution de ce procédé
US2491066A (en) * 1947-09-15 1949-12-13 Standard Oil Dev Co Rust inhibitor for mineral oils
GB770729A (en) * 1954-06-30 1957-03-20 Exxon Research Engineering Co Rust inhibiting compositions and concentrates containing thioether carboxylic acids
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US2216751A (en) * 1935-05-14 1940-10-08 Standard Oil Dev Co Heavy metal salts of thioether carboxylic acids
US2354550A (en) * 1940-10-07 1944-07-25 Standard Oil Dev Co Lubricant
US2423865A (en) * 1944-02-28 1947-07-15 Shell Dev Anticorrosive
US2474604A (en) * 1947-06-11 1949-06-28 Standard Oil Dev Co Rust-preventing compounds
US2683119A (en) * 1949-11-16 1954-07-06 Standard Oil Dev Co Compounded lubricant
US2884379A (en) * 1954-06-30 1959-04-28 Exxon Research Engineering Co Rust inhibitor composition
US2892852A (en) * 1957-05-28 1959-06-30 Nathan H Koenig Alkylthio-, (acetylthio)-and (arylthio)-undecanoic acids

Cited By (21)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4297236A (en) * 1977-09-19 1981-10-27 Hoechst Aktiengesellschaft Water miscible corrosion inhibitors
US4174284A (en) * 1978-08-14 1979-11-13 Phillips Petroleum Company Hydrocarbylpolythiobenzoic acids as anti-oxidation additives
US4981609A (en) * 1980-06-19 1991-01-01 Petrolite Corporation Compounds containing sulfur and amino groups
US4549974A (en) * 1983-09-23 1985-10-29 Mobil Oil Corporation Lubricants containing sulfurized organic acid diamine salts
US4566879A (en) * 1983-09-23 1986-01-28 Mobil Oil Company Fuels containing sulfurized organic acid diamine salts
EP0142078A1 (fr) * 1983-10-25 1985-05-22 Phillips Petroleum Company Lubrifiant pour le traitement de métal
US4559153A (en) * 1983-10-25 1985-12-17 Phillips Petroleum Company Metal working lubricant
US4670163A (en) * 1985-05-29 1987-06-02 Phillips Petroleum Company Inhibiting corrosion
US4786424A (en) * 1985-12-05 1988-11-22 Phillips Petroleum Company Aqueous metal-working composition and process
US4744948A (en) * 1987-06-04 1988-05-17 Texaco Inc. Thiol ester corrosion inhibition system
US5013482A (en) * 1988-07-21 1991-05-07 Ciba-Geigy Corporation Corrosion inhibition
US5176850A (en) * 1988-07-21 1993-01-05 Ciba-Geigy Corporation Substituted glycerol compounds
US5240625A (en) * 1989-03-23 1993-08-31 Bp Chemicals (Additives) Limited Lubricating oil additives
US5679627A (en) * 1995-12-22 1997-10-21 Exxon Research & Engineering Company High-load carrying turbo oils containing amine phosphate and a sulfur containing carboxylic acid (law348)
US5714441A (en) * 1996-07-12 1998-02-03 Exxon Research And Engineering Company Additive combination to reduce deposit forming tendencies and improve antioxidancy of aviation turbine oils
US5856280A (en) * 1996-07-12 1999-01-05 Exxon Research And Engineering Company Sulfur-containing carboxylic acid derivatives to reduce deposit forming tendencies and improve antioxidancy of aviation turbine oils
US20110034359A1 (en) * 2009-08-07 2011-02-10 Rabbat Philippe Marc Andre Lubricant composition
US8802605B2 (en) 2009-08-07 2014-08-12 Basf Se Lubricant composition
US9340745B2 (en) 2009-08-07 2016-05-17 Basf Se Lubricant composition
US8802606B2 (en) 2010-08-06 2014-08-12 Basf Se Lubricant composition having improved antiwear properties
US11168402B2 (en) * 2018-02-16 2021-11-09 Nippon Shokubai Co., Ltd. Metal corrosion inhibitor

Also Published As

Publication number Publication date
ZA721300B (en) 1973-10-31
FR2137678A1 (fr) 1972-12-29
NL7206483A (fr) 1972-11-16
JPS4847A (fr) 1973-01-05
AU471349B2 (en) 1976-04-15
AU4171372A (en) 1973-11-08
GB1382505A (en) 1975-02-05
FR2137678B1 (fr) 1978-07-07
IT951814B (it) 1973-07-10
JPS5227162B2 (fr) 1977-07-19
DE2223390A1 (de) 1972-11-30

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