DE2530562A1 - Benzotriazole metal surface corrosion inhibitor solns. - in organic solvents, for incorporation in lubricants - Google Patents

Benzotriazole metal surface corrosion inhibitor solns. - in organic solvents, for incorporation in lubricants

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Publication number
DE2530562A1
DE2530562A1 DE19752530562 DE2530562A DE2530562A1 DE 2530562 A1 DE2530562 A1 DE 2530562A1 DE 19752530562 DE19752530562 DE 19752530562 DE 2530562 A DE2530562 A DE 2530562A DE 2530562 A1 DE2530562 A1 DE 2530562A1
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Prior art keywords
amine
solvent
phosphoric acid
corrosion
benzotriazole
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Granted
Application number
DE19752530562
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German (de)
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DE2530562C2 (en
Inventor
Ingo Kreutzer
Klaus Dr Morche
Kurt Schilling
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Rhein Chemie Rheinau GmbH
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Rhein Chemie Rheinau GmbH
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Priority to DE2530562A priority Critical patent/DE2530562C2/en
Publication of DE2530562A1 publication Critical patent/DE2530562A1/en
Application granted granted Critical
Publication of DE2530562C2 publication Critical patent/DE2530562C2/en
Expired legal-status Critical Current

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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
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    • C10M1/00—Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants
    • C10M1/08—Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants with additives
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
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    • C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
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    • C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C10M2215/04—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
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    • C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
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    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/04—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions containing sulfur-to-oxygen bonds, i.e. sulfones, sulfoxides
    • C10M2219/044—Sulfonic acids, Derivatives thereof, e.g. neutral salts
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    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/08—Thiols; Sulfides; Polysulfides; Mercaptals
    • C10M2219/082—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
    • C10M2219/087—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Derivatives thereof, e.g. sulfurised phenols
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  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Organic Chemistry (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Materials Engineering (AREA)
  • Mechanical Engineering (AREA)
  • Metallurgy (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Lubricants (AREA)
  • Preventing Corrosion Or Incrustation Of Metals (AREA)

Abstract

The soln. comprises benzotriazole, methyl benzotriazole and/or tetrahydrobenzotriazole dissolved in an amine salt of a carboxylic or phosphoric acid, a trialkyl phosphate ester, an aminealkyl benzyl sulphonate or mixts. of these. The solns. are added to lubricants to prevent corrosion of machine parts eg. hearings esp. by S-contg. oils. Solubility of the benzotriazole or derivs. in oil is increased around 9 times, and the corrosion-inhibiting action increased, so that a smaller amount can be used. In an example 0.3% of a mixt. of 400 g isohexanic acid, 250 g isodecylamine and 350 g benzotriazole is dissolved in paraffinic spindle oil at 22 degrees C.

Description

Korrosionsinhibierung Metalloberflächen sind häufig chemischen und elektrochemischen Angriffen ausgesetzt, die diese Oberflächen zerstören. Um diese Korrosion zu verhindern, kann man auf der Metalloberfläche mit Benzotriazol, Methylbenzotriazol oder Tetrahydrobenzotriazol eine monomolekulare Chelatkomplexschicht aufbauen, die sehr fest haftet, chemisch inert ist und so die Metalloberfläche korrodierenden Einflüssen entzieht. Corrosion inhibition metal surfaces are often chemical as well exposed to electrochemical attacks that destroy these surfaces. Around To prevent corrosion, one can use benzotriazole, methylbenzotriazole on the metal surface or tetrahydrobenzotriazole build up a monomolecular chelate complex layer which adheres very firmly, is chemically inert and thus corrodes the metal surface Removes influences.

In Ider Praxis steht man meist vor dem Problem,Maschinenteile, die mit Schmiermitteln in Beziehung stehen, z.B. Lagerschalen, gegen die korrodierende Wirkung des Schmiermittels (z.B. aktive Schwefelverbindungen im Schmieröl) zu schützen. Man muß dann das Benzotriazol im Schmiermittel lösen. Dies gelingt aber nur sehr schwer, denn Benzotriazol löst sich in Mineralölen in praktisch vertretbarer Zeit erst bei höheren Temperaturen, und auch dann nur in geringen Mengen. Tetrahydrobenzotriazol hat ebenfalls eine korrosionsinhibierende Wirkung, ist etwas besser löslich, aber auch hier ist das Lösen und Einmischen in ein öl außerordentlich schwierig und zeitraubend.In practice, one is usually faced with the problem of machine parts that are related to lubricants, e.g. bearing shells, against the corrosive To protect the effect of the lubricant (e.g. active sulfur compounds in the lubricating oil). You then have to dissolve the benzotriazole in the lubricant. But this only works very well difficult, because benzotriazole dissolves in mineral oils in a practically acceptable time only at higher temperatures, and then only in small quantities. Tetrahydrobenzotriazole also has a corrosion-inhibiting effect, is somewhat more soluble, but Here too, dissolving and mixing into an oil is extremely difficult and time-consuming.

Ein Teil dieser Schwierigkeiten kann vermieden werden, wenn man Thiodiazole als Korrosionsinhibitoren einsetzt, Diese Produkte sind bei 200C flüssig, lassen sich leicht in Öl einmischen, sind aber erheblich weniger wirksam als Benzotriazol.Some of these difficulties can be avoided by using thiodiazoles used as corrosion inhibitors, these products are liquid at 200C, leave mix easily in oil but are considerably less effective than benzotriazole.

Aufgabe der Erfindung ist daher, ein flüssiges Korrosionsmittel auf Benzotriazolbasis zur Verfügung zu stellen, das sich leicht in Schmiermittel einarbeiten läßt.The object of the invention is therefore to provide a liquid corrosion agent To provide a benzotriazole base that is easy to incorporate into lubricants leaves.

Gegenstand der Erfindung ist demnach ein Korrosionsschutzmittel für Metalloberflächen, bestehend aus einer Lösung von Benzotriazol, Methylbenzotriazol und/oder Tetrahydrobenzotriazol in einem Aminsalz einer Carbonsäure, einem Aminsalz einer Phosphorsäure, einem Phosphorsäuretrialkylester, einem Amin-Alkylbenzolsulfonat oder Mischungen daraus, die zusätzlich noch freie Amine, freie Carbonsäure oder Phosphorsäure-mono- oder Zi-Ester enthalten können.The invention therefore relates to an anti-corrosion agent for Metal surfaces consisting of a solution of benzotriazole, methylbenzotriazole and / or tetrahydrobenzotriazole in an amine salt of a carboxylic acid, an amine salt a phosphoric acid, a phosphoric acid trialkyl ester, an amine-alkylbenzenesulfonate or mixtures thereof, which also contain free amines, free carboxylic acids or Phosphoric acid mono- or Zi-esters may contain.

Diese Lösungen besitzen eine Reihe von unerwarteten Vorteilen.These solutions have a number of unexpected advantages.

So ist Benzotriazol, Methylbenzotriazol bzw. Tetrahydrobenzotriazol in den genannten Lösungsmitteln auch bei Zimmertemperatur (20°C) leicht (bis zu 40 %) löslich. Die Lösungen sind flüssig. Sie können bei Zimmertemperatur in Schmiermittel eingearbeitet werden. Auch dabei wirkt das Lösungsmittel als Lösungsvermittler und erhöht die Löslichkeit des Benzotriazols, Methylbenzotriazols bzw. Tetrahydrobenzotriazols in Öl erheblich (etwa auf das 9-fache). Gleichzeitig wird durch das Lösungsmittel auch die korrosionsinhibierende Wirkung des Benzotriazols gesteigert, so daß für den gleichen Effekt eine erheblich herabgesetzte Menge ausreicht.So is benzotriazole, methylbenzotriazole or tetrahydrobenzotriazole in the solvents mentioned, even at room temperature (20 ° C) easily (up to 40%) soluble. The solutions are liquid. You can put in lubricants at room temperature be incorporated. Here, too, the solvent acts as a solubilizer and increases the solubility of the benzotriazole, methylbenzotriazole or tetrahydrobenzotriazole in oil considerably (about 9 times). At the same time is through the solvent also increased the corrosion-inhibiting effect of benzotriazole, so that for a significantly reduced amount is sufficient for the same effect.

Das Korrosionsschutzmittel der Erfindung wirkt besonders gegen die Korrosion von Buntmetallen, wie Kupfer und Kupferlegierungen durch Schwefelverbindungen, wie aktiven Schwefel enthaltende Schmierölzusätze. Deshalb wird es bevorzugt für diesen Zweck eingesetzt.The anti-corrosion agent of the invention is particularly effective against Corrosion of non-ferrous metals such as copper and copper alloys due to sulfur compounds, such as active sulfur-containing lubricating oil additives. That is why it is preferred for used for this purpose.

Lösungsmittel für Benzotriazol, Methylbenzotriazol bzw. Tetrahydrobenzotriazol im Sinne der Erfindung sind 1) Aminsalze von Carbonsäuren Die den Salzen zugrundeliegenden Carbonsäuren sind insbesondere aliphatische Monocarbonsäuren mit 6 - 18 Kohlenstoffatomen. Besonders bevorzugt sind gesättigte aliphatische Monocarbonsäuren mit 6 - 10 Kohlenstoffatomen und ungesättigte aliphatische Monocarbonsäuren mit 6 - 14 Kohlenstoffatomen.Solvent for benzotriazole, methylbenzotriazole or tetrahydrobenzotriazole are within the meaning of the invention 1) Amine salts of carboxylic acids The den Carboxylic acids on which salts are based are, in particular, aliphatic monocarboxylic acids with 6-18 carbon atoms. Saturated aliphatic monocarboxylic acids are particularly preferred with 6-10 carbon atoms and unsaturated aliphatic monocarboxylic acids with 6-14 carbon atoms.

Die den Salzen zugrundeliegenden Amine sind aliphatische, cycloaliphatische und aromatische Mono-, Di- und Triamine.The amines on which the salts are based are aliphatic and cycloaliphatic and aromatic mono-, di- and triamines.

Besonders bevorzugt sind Mono-, Di- und Trialkylamine, deren Alkylgruppen insgesamt 6 - 18 Kohlenstoffatome enthalten.Mono-, di- and trialkylamines and their alkyl groups are particularly preferred contain a total of 6-18 carbon atoms.

Neben diesen Salzen kann auch ein Uberschuß der Säure vorhanden sein, wobei das Molverhältnis Amin : Säure bevorzugt 1 : 1 nicht übersteigt.In addition to these salts, there may also be an excess of acid, the amine: acid molar ratio preferably not exceeding 1: 1.

Beispiele für geeignete Carbonsäuren sind Capronsäure, Caprinsäure, Isononansäure, Isopalinitinsäure, ölsäure.Examples of suitable carboxylic acids are caproic acid, capric acid, Isononanoic acid, isopalinitic acid, oleic acid.

Beispiele für geeignete Amine sind n-Hexylamin, tert.-Octylamin, tert.-Isotetradecylamin, Oleylamin, Dicyclohexylamin, Anilin.Examples of suitable amines are n-hexylamine, tert-octylamine, tert-isotetradecylamine, Oleylamine, dicyclohexylamine, aniline.

2) Aminsalze von Phosphorsäuren Hier sind die gleichen Amine geeignet, die zur Bildung der Carbonsäuresalze benutzt werden. Phosphorsäuren sind Phosphorsäure selbst oder ihre Mono- und Dialkylester. Bevorzugt wird aus diesen Phosphorsäuren ein neutrales Salz gebildet, d.h.2) Amine salts of phosphoric acids Here the same amines are suitable, which are used to form the carboxylic acid salts. Phosphoric acids are phosphoric acid themselves or their mono- and dialkyl esters. Of these, phosphoric acids are preferred a neutral salt is formed, i.e.

sämtliche vorhandenen aziden Wasserstoffatome werden umgesetzt.all acidic hydrogen atoms present are converted.

Auch hier ist ein Uberschuß der Phosphorsäure möglich.Here too, an excess of phosphoric acid is possible.

Besonders bevorzugt sind Salze aus Alkylaminen und Phosphorsäuren oder deren Mono- oder Dialkylestern. In diesen Salzen ist die Gesamtzahl an Kohlenstoffatomen in allen Alkylgruppen bevorzugt 10 - 40. Beispiele für geeignete Verbindungen sind Mono-butylphosphat, Di-butylphosphat, Di-2-äthylhexylphosphat, Monooctadecenylphosphat.Salts of alkylamines and phosphoric acids are particularly preferred or their mono- or dialkyl esters. In these salts is the total number of carbon atoms in all alkyl groups preferably 10-40. Examples of suitable compounds are Mono-butyl phosphate, di-butyl phosphate, di-2-ethylhexyl phosphate, monooctadecenyl phosphate.

3) Phosphorsäuretrialkylester, gegebenenfalls im Gemisch mit einem der unter (1) genannten Amine. Das Molverhältnis Phosphorsäureester : Amin soll 1 : 1 nicht übersteigen. Phosphorsäuretrialkylester enthalten bevorzugt insgesamt 10 - 40 Kohlenstoffatome in den Alkylgruppen.3) Trialkyl phosphorate, optionally mixed with one the amines mentioned under (1). The molar ratio of phosphoric acid ester: amine should Do not exceed 1: 1. Phosphoric acid trialkyl esters preferably contain in total 10-40 carbon atoms in the alkyl groups.

Beispiele für geeignete Phosphorsäureester sind Tributylphosphat, Tri-2-äthylhexylphosphat, Tridodecylphosphat, Dibutyl-2-äthylhexylphosphat.Examples of suitable phosphoric acid esters are tributyl phosphate, Tri-2-ethylhexyl phosphate, tridodecyl phosphate, dibutyl-2-ethylhexyl phosphate.

4) Amin-Alkylbenzolsulfonate sind bevorzugt Salze der unter (1) genannten Amine mit Alkylbenzolsulfonsäuren, die 1 - 18 Kohlenstoffatome in der Alkylgruppe enthalten.4) Amine-alkylbenzenesulfonates are preferably salts of those mentioned under (1) Amines with alkylbenzenesulfonic acids that have 1-18 carbon atoms in the alkyl group contain.

Beispiele sind p-Toluolsulfonsäure, Isooctadecenylbenzolsulfonsäure.Examples are p-toluenesulfonic acid, isooctadecenylbenzenesulfonic acid.

Es ist möglich, beliebige Kombinationen dieser Lösungsmittel zu verwenden.It is possible to use any combination of these solvents.

Alle diese Lösungsmittel lösen Benzotriazol, Methylbenzotriazol und Tetrahydrobenzotriazol zu sehr konzentrierten Lösungen bei Zimmertemperatur. Diese Lösungen können ohne weiteres ebenfalls bei Zimmertemperatur in das Schmiermittel eingearbeitet werden.All of these solvents dissolve benzotriazole, methylbenzotriazole and Tetrahydrobenzotriazole to very concentrated solutions at room temperature. These Solutions can also be readily incorporated into the lubricant at room temperature be incorporated.

Insbesondere werden sie Mineralschmierölen zugefügt, die korrodierende Bestandteile, z.B. aktive Schwefelverbindungen enthalten. Dabei genügt im Schmieröl i.a. eine Konzentration des Benzotriazols, Methylbenzotriazols bzw. Tetrahydrobenzotriazols von 0,01 bis 0,1 Gew.-0Ä, um die Korrosion von Kupfer oder Kupferverbindungen zu verhindern, die mit dem Öl in Berührung stehen.In particular, they are added to mineral lubricating oils, which are corrosive Contain ingredients, e.g. active sulfur compounds. It is sufficient in the lubricating oil i.a. a concentration of the benzotriazole, methylbenzotriazole or tetrahydrobenzotriazole from 0.01 to 0.1% by weight to prevent corrosion of copper or copper compounds prevent that are in contact with the oil.

Diese Konzentration ist erheblich niedriger als die bei Abwesenheit der Lösungsmittel für denselben Effekt erforderliche. Da dem Öl flüssige Korrosionsinhibitoren zugesetzt werden, deren Lösungsmittel die Löslichkeit der Benzotriazole, Methylbenzotriazole bzw. Tetrahydrobenzotriazole im öl erhöht, besteht auch keine Gefahr der Entmischung.This concentration is considerably lower than that in the absence the solvent required for the same effect. Because the oil is a liquid corrosion inhibitor are added, the solvent of which increases the solubility of the benzotriazoles, methylbenzotriazoles or tetrahydrobenzotriazoles increased in the oil, there is also no risk of segregation.

Grundsätzlich kann jedes Schmiermittel auf diese Weise korrosionshemmend ausgerüstet werden. Beispiele für besonders geeignete Schmiermittel sind Mineralöle auf paraffinischer, naphthenischer, aromatischer oder gemischter Basis mit den üblichen Viskositäten von 1,2 - 200E bei 500C, Syntheseöle, z.B. Esteröle, Alkylbenzole und deren Gemische mit Mineralölen, Schmierfette, z.B. Lithiumfette, Calciumfette.In principle, any lubricant can inhibit corrosion in this way be equipped. Examples of particularly suitable lubricants are mineral oils on a paraffinic, naphthenic, aromatic or mixed basis with the usual Viscosities from 1.2 - 200E at 500C, synthetic oils, e.g. ester oils, alkylbenzenes and Their mixtures with mineral oils, lubricating greases, e.g. lithium greases, calcium greases.

Beispiel 1 1) Benzotriazollösung: 400 g Isoionansäure und 250 g Isododecylamin werden unter Rühren und Kühlen gemischt. In dieser Mischung werden 350 g Benzotriazol langsam aufgelöst und die Lösung filtriert. Es wird eine 35 ziege Benzotriazollösung erhalten. Example 1 1) Benzotriazole solution: 400 g of isoionanoic acid and 250 g of isododecylamine are mixed with stirring and cooling. 350 g of benzotriazole are added to this mixture slowly dissolved and the solution filtered. It becomes a goat benzotriazole solution obtain.

2) Löslichkeit in Mineralöl In je 100 g paraffinbasichem Spindelöl werden bei 22 0c eingeruhrt: (A) 10 mg der Lösung gemäß (1) (B) 30 mg der Lösung gemäß (1) (C) 10 mg Benzotriazol (D) 10 mg Tetrahydrobenzotriazol (E) 10 mg Thiadiazol Die so erhaltenen Schmieröle enthalten: (A) 0.03 Gew.- Benzotriazol (B) 0.1 Gew.- Benzotriazol (C) 0.1 Gew.- Benzotriazol (D) 0.1 Gew.- Tetrahydrobenzotriazol (E) 0.1 Gew.- Thiadiazol Bei der Herstellung waren die Schmieröle A, B und E nach einer Minute vollständig klar während sich bei C und D auch nach einer Stunde der Zusatz noch nicht gelöst hatte. In C löste sich der Zusatz erst beim Erwärmen auf 70°C, in D beim Erwärmen auf 50°C.2) Solubility in mineral oil In 100 g of paraffin-based spindle oil are stirred in at 22 ° C.: (A) 10 mg of the solution according to (1) (B) 30 mg of the solution according to (1) (C) 10 mg benzotriazole (D) 10 mg tetrahydrobenzotriazole (E) 10 mg thiadiazole The lubricating oils obtained in this way contain: (A) 0.03% by weight benzotriazole (B) 0.1% by weight Benzotriazole (C) 0.1% by weight benzotriazole (D) 0.1% by weight tetrahydrobenzotriazole (E) 0.1 wt .- thiadiazole In the production, the lubricating oils A, B and E were after a Minute completely clear while at C and D the addition is even after one hour had not yet resolved. The additive only dissolved in C when heated to 70 ° C, in D when heated to 50 ° C.

In demselben Schmieröl lösten sich bei 220C 0.02 Gew.-% Benzotriazol, aber 0.3 % (entsprechend 0.1 Gew.-% Benzotriazol) der Lösung nach (1). In the same lubricating oil, 0.02% by weight of benzotriazole dissolved at 220C, but 0.3% (corresponding to 0.1% by weight benzotriazole) of the solution according to (1).

3) Korrosionstest: 1.) Cu-Aktivität nach ASTM-D-1 30 Geprüft wurde in einem handelsüblichen paraffinischen Mineralöl mit einer Viskosität von 1,50E bei 500C.3) Corrosion test: 1.) Cu activity according to ASTM-D-1 30 was tested in a commercially available paraffinic mineral oil with a viscosity of 1.50E at 500C.

In diesem öl wurden 0,5 96 Thiononylphenylpolysulfid mit 38 % Gesamtschwefel und 26 % aktivem Schwefel gelöst.In this oil there was 0.5% thiononylphenyl polysulfide with 38% total sulfur and 26% active sulfur dissolved.

Zu je 100 ml dieser Lösung wurden dann a) 30 mg Benzotriazol bei 900c in einer halben Stunde eingerührt.For every 100 ml of this solution, a) 30 mg of benzotriazole were then added at 900c stirred in in half an hour.

b) 30 mg Produkt aus Beispiel 1 bei 250c in 10 Minuten eingerührt.b) 30 mg of product from Example 1 are stirred in at 250c in 10 minutes.

Diese Lösungen wurden dann zusammen mit einer Probe c) = ohne Zusatz von Korrosionsinhibitoren nach ASTM-D-130 im Cu-Streifentest geprüft. Hierbei bedeutet 1a keine, 4c starke Korrosion.These solutions were then used together with a sample c) = no additive of corrosion inhibitors according to ASTM-D-130 in the Cu strip test. Here means 1a no, 4c severe corrosion.

Lösung Cu-Aktivität nach ASTM-D-130 bei 130 0c in 3 Stunden 5 Stunden a 3a 3a b 1a - 1b 1b c 4c 4c 2.) V-W-Ringrillentest gemäß VW-P-1401 Geprüft wurde wieder in einem handelsüblichen paraffinischen Mineralöl mit einer Viskosität von 1,5°E bei nur In. je 100 g dieses Öls wurden 0,9 g Zinkdialkyldithiophosphat, und a) 30 mg Benzotriazol b) 30 mg Produkt aus Beispiel 1 eingerührt und gelöst und 2 g Wasser einemulgiert.Solution Cu activity according to ASTM-D-130 at 130 0c in 3 hours 5 hours a 3a 3a b 1a - 1b 1b c 4c 4c 2.) V-W ring groove test according to VW-P-1401 was tested again in a commercially available paraffinic mineral oil with a viscosity of 1.5 ° E with only In. per 100 g of this oil were 0.9 g of zinc dialkyldithiophosphate, and a) 30 mg of benzotriazole b) 30 mg of product from Example 1 stirred in and dissolved and 2 g of water emulsified.

Diese Emulsionen wurden zusammen mit einer Probe c) = ohne Korrosionsschutz gemäß VW-P-1401 geprüft. Die Bewertung erfolgt durch Cu nach ASTM-D-130, siehe oben, für Eisen, Rostfrei, Rostpunkte, Flächenrost.These emulsions were tested together with a sample c) = without corrosion protection tested according to VW-P-1401. The evaluation is carried out by Cu according to ASTM-D-130, see above, for iron, rustproof, rust spots, surface rust.

Lösung Korrosion nach 48 Stunden/1000C auf Cu Fe a 3b Flächenrost b 3b Rostpunkte c 4a Flächenrost Beispiele 2 - 29: Nach der Methode des Beispiels 1 wurden mit verschiedenen Lösungsmitteln die Löslichkeit des Benzotriazols in diesen Lösungsmitteln, die Löslichkeit der erhaltenen Lösungen in Schmierölen und die Wirkung dieser Schmieröle gegen die Korrosion von Kupfer geprüft. Die Ergebnisse zeigt die Tabelle 1.Solution corrosion after 48 hours / 1000C on Cu Fe a 3b surface rust b 3b grate points c 4a surface grate Examples 2-29: According to the method of the example 1 The solubility of the benzotriazole in these was determined with various solvents Solvents, the solubility of the solutions obtained in lubricating oils and the effect these lubricating oils have been tested against the corrosion of copper. The results shows the Table 1.

Als Schmieröl wurde verwendet: Beispiel 1 - 23 ein paraffinbasisches Spindelöl mit einer 28 - 30 Viskosität von 1,50E bei 500C = 6,O cSt Beispiel 24 - 25 ein paraffinbasisches Getriebeöl mit einer Viskosität von 122,6 cSt bei 500C Beispiel 26 - 27 ein naphthenbasisches Spindelöl mit einer Viskosität von 8,22 cSt bei 500c Beispiel 31 Syntheseöl Alkylbenzol mit einer Viskosität von 17,2 cSt bei 500C Beispiel 32 Syntheseöl, handelsübliches Esteröl auf Sebazinsäurebasis mit einer Viskosität von 12,1 cSt bei 500C Tabelle 1 1 2 3 4 5 6 7 8 Nr. Lösungsmittel Molver- Benzotria- Lösung (4) Benzo- Erhöhung der Lös- Korrosionshältnis zol gelöst in Öl triazol lichkeit gegen- schutzwirkung % % im Öl über reinem Benzo- für Kupfer % triazol um Faktor 2 Octadecylphosphat - 35 0.3 0.105 5.25 + 3 Di-2-äthylhexylphosphat - 35 0.3 0.105 5.25 + 4 Tri-2-butylhexylphosphat - 35 0.35 0.088 4.4 + 5 Tri-n-butylphosphat - 35 0.3 0.105 5.25 + 6 p-Toluolsulfonsäure + i-Tetradecylamin 1:1 40 0.1 0.04 2.0 + 7 i-Octadecenylbenzolsulfonsäure + t-Octylamin 1:1 25 0.15 0.037 1.87 + 8 n-Capronsäure + Dicy ohexylamin 1:0.5 40 0.25 0.1 5 + Tabelle 1 1 2 3 4 5 6 7 8 Nr. Lösungsmittel Molver- Benzotria- Lösung (4) Benzo- Erhöhung der Lös- Korrosionshältnis zol gelöst in Öl triazol lichkeit gegen- schutzwirkung % % im Öl über reinem Benzo- für Kupfer % triazol um Faktor 9 n-Laurinsäure + Dicyclohexalamin 1:0.5 40 0.3 0.12 6 + 10 Capronsäure + t-Isooctylamin 1:0.5 40 0.2 0.08 4 + 11 Laurinsäure + t-Iso-octylamin 1:0.5 30 0.2 0.06 3 + 12 Capronsäure + n-Hexylamin 1:0.5 35 0.3 0.105 5.25 + 13 Valerionsäure + tert.-Isotetradecylamin 1:0.5 40 0.15 0.06 3 + 14 Capronsäure + tert.-Isop-tetradecylamin 1:0.5 40 0.3 0.12 6 + 15 Laurinsäure + tert.-Iso-tetradecylamin 1:0.5 30 0.3 0.09 4.5 + 16 Isononansäure + tert.-Iso-tetradecylamin 1:0.5 35 0.3 0.105 5.25 + Tabelle 1 1 2 3 4 5 6 7 8 Nr. Lösungsmittel Molver- Benzotria- Lösung (4) Benzo- Erhöhung der Lös- Korrosionshältnis zol gelöst in Öl triazol lichkeit gegen- schutzwirkung % % im Öl über reinem Benzo- für Kupfer % triazol um Faktor 17 Isononansäure + t-Iso-tetradecylamin 1:1 30 0.3 0.09 4.5 + 18 mono-n-Butylphosphat + Din-Butylphosphat + tert.-Isotetradecylamin- 0.3:0.3:0.4 40 0.2 0.08 4 + 19 Tributylphosphat + tert.-Iso-tetradecylamin 0.9:0.1 30 0.5 0.15 7.5 + 20 Tributylphosphat + tert.-Iso-tetradecylamin 0.9:0.1 40 - - - -21 Tributylphosphat + tert.-Iso-tetradecylamin 0.7:0.3 30 0.6 0.18 9 + Tabelle 1 1 2 3 4 5 6 7 8 Nr. Lösungsmittel Molver- Benzotria- Lösung (4) Benzo- Erhöhung der Lös- Korrosionshältnis zol gelöst in Öl triazol lichkeit gegen- schutzwirkung % % im Öl über reinem Benzo- für Kupfer % triazol um Faktor 22 Tributylphosphat + tert.-Iso-tetradecylamin 0.7:0.3 40 0.3 0.12 6 + 23 Tributylphosphat + tert.-Iso-tetradecylamin 0.7:0.3 50 0.15 0.075 4 + 24 Tributylphosphat + tert.-Iso-tetradecylamin 0.7:0.3 30 0.8 0.24 5 + 25 Tributylphosphat + tert.-Iso-tetradecylamin 0.7:0.3 40 0.4 0.16 3 + 26 Tributylphosphat + tert.-Iso-tetradecylamin 0.7:0.3 30 0.5 0.15 3 + Tabelle 1 1 2 3 4 5 6 7 8 Nr. Lösungsmittel Molver- Benzotria- Lösung (4) Benzo- Erhöhung der Lös- Korrosionshältnis zol gelöst in Öl triazol lichkeit gegen- schutzwirkung % % im Öl über reinem Benzo- für Kupfer % triazol um Faktor 27 Tributylphosphat + tert.-Iso-tetradecylamin 0.7:0.3 40 0.25 0.10 2 + 28 Tributylphosphat + Isononansäuren 70:30 30 0.4 0.12 6 + 29 Tributylphosphat + tert.-Iso-tetradecylamin + Isononansäure 0.3:0.25:0.6 30 0.4 0.12 6 + 30 Tributylphosphat + tert.-Iso-tetradecylamin + Isononansäure 0.3:0.25:0.45 30 0.3 0.09 4.5 + Tabelle 1 1 2 3 4 5 6 7 8 Nr. Lösungsmittel Molver- Benzotria- Lösung (4) Benzo- Erhöhung der Lös- Korrosionshältnis zol gelöst in Öl triazol lichkeit gegen- schutzwirkung % % im Öl über reinem Benzo- für Kupfer % triazol um Faktor 31 Tributylphosphat + tert.-Iso-tetradecylamin 0.7:0.3 40 0.4 0.16 8 + 32 Tributylphos- in jephat + tert.- dem Iso-tetradecyl- Verhältamin 0.7:0.3 40 nis #40% 20 + mischbarThe lubricating oil used was: Examples 1 - 23, a paraffin-based one Spindle oil with a 28-30 viscosity of 1.50E at 500C = 6, O cSt Example 24 - 25 a paraffin-based gear oil with a viscosity of 122.6 cSt at 500C Examples 26-27 a naphthenic spindle oil having a viscosity of 8.22 cSt at 500c Example 31 Synthetic oil alkylbenzene with a viscosity of 17.2 cSt 500C Example 32 Synthetic oil, commercially available ester oil based on sebacic acid with a Viscosity of 12.1 cSt at 500C Table 1 1 2 3 4 5 6 7 8 No. Solvent Molver- Benzotria- Solution (4) Benzo- Increase the dissolving corrosion ratio zol dissolved in oil triazole Liability counter-protective effect%% in oil over pure benzo- for copper% triazole by a factor of 2 octadecyl phosphate - 35 0.3 0.105 5.25 + 3 di-2-ethylhexyl phosphate - 35 0.3 0.105 5.25 + 4 tri-2-butylhexyl phosphate - 35 0.35 0.088 4.4 + 5 tri-n-butyl phosphate - 35 0.3 0.105 5.25 + 6 p-toluenesulfonic acid + i-tetradecylamine 1: 1 40 0.1 0.04 2.0 + 7 i-octadecenylbenzenesulfonic acid + t-octylamine 1: 1 25 0.15 0.037 1.87 + 8 n-caproic acid + Dicyohexylamine 1: 0.5 40 0.25 0.1 5 + Table 1 1 2 3 4 5 6 7 8 No. Solvent Molver- Benzotria- Solution (4) Benzo- Increase the dissolving corrosion ratio zol dissolved in oil triazole Liability counter-protective effect%% in oil over pure benzo- for copper% triazole by a factor of 9 n-lauric acid + dicyclohexalamine 1: 0.5 40 0.3 0.12 6 + 10 caproic acid + t-isooctylamine 1: 0.5 40 0.2 0.08 4 + 11 lauric acid + t-iso-octylamine 1: 0.5 30 0.2 0.06 3 + 12 caproic acid + n-hexylamine 1: 0.5 35 0.3 0.105 5.25 + 13 Valerionic acid + tert-isotetradecylamine 1: 0.5 40 0.15 0.06 3 + 14 caproic acid + tert-isop-tetradecylamine 1: 0.5 40 0.3 0.12 6 + 15 lauric acid + tert-iso-tetradecylamine 1: 0.5 30 0.3 0.09 4.5 + 16 isononanoic acid + tert-iso-tetradecylamine 1: 0.5 35 0.3 0.105 5.25 + Table 1 1 2 3 4 5 6 7 8 No. Solvent Molar ratio Benzotria solution (4) Benzo increase the dissolving corrosion ratio zol dissolved in oil Triazole Liability counter-protective effect%% in oil over pure benzo- for copper% triazole by a factor of 17 isononanoic acid + t-iso-tetradecylamine 1: 1 30 0.3 0.09 4.5 + 18 mono-n-butyl phosphate + din-butyl phosphate + tert-isotetradecylamine- 0.3: 0.3: 0.4 40 0.2 0.08 4 + 19 tributyl phosphate + tert-iso-tetradecylamine 0.9: 0.1 30 0.5 0.15 7.5 + 20 tributyl phosphate + tert-iso-tetradecylamine 0.9: 0.1 40 - - - -21 tributyl phosphate + tert-iso-tetradecylamine 0.7: 0.3 30 0.6 0.18 9 + Table 1 1 2 3 4 5 6 7 8 No. Solvent Molver- Benzotria- Solution (4) Benzo- Increase the Dissolving Corrosion Ratio Zol Dissolved in Oil Triazole Liability Counter-Protection% % in the oil over pure benzo for copper% triazole by a factor of 22 tributyl phosphate + tert-iso-tetradecylamine 0.7: 0.3 40 0.3 0.12 6 + 23 tributyl phosphate + tert-iso-tetradecylamine 0.7: 0.3 50 0.15 0.075 4 + 24 tributyl phosphate + tert-iso-tetradecylamine 0.7: 0.3 30 0.8 0.24 5 + 25 tributyl phosphate + tert-iso-tetradecylamine 0.7: 0.3 40 0.4 0.16 3 + 26 tributyl phosphate + tert-iso-tetradecylamine 0.7: 0.3 30 0.5 0.15 3 + Tabel 1 1 2 3 4 5 6 7 8 No. Solvent Molver Benzotria Solution (4) Benzo Increase the dissolution corrosion ratio zol dissolved in oil triazole lability counter-protective effect %% in the oil over pure benzo for copper% triazole by a factor of 27 tributyl phosphate + tert-iso-tetradecylamine 0.7: 0.3 40 0.25 0.10 2 + 28 tributyl phosphate + isononanoic acids 70:30 30 0.4 0.12 6 + 29 tributyl phosphate + tert-iso-tetradecylamine + isononanoic acid 0.3: 0.25: 0.6 30 0.4 0.12 6 + 30 tributyl phosphate + tert-iso-tetradecylamine + isononanoic acid 0.3: 0.25: 0.45 30 0.3 0.09 4.5 + Table 1 1 2 3 4 5 6 7 8 No. Solvent Molver- Benzotria- solution (4) Benzo- increase in the dissolving corrosion ratio zol dissolved in oil triazolability counter-protective effect%% in oil over pure benzo- for copper % triazole by a factor of 31 tributyl phosphate + tert-iso-tetradecylamine 0.7: 0.3 40 0.4 0.16 8 + 32 tributylphos- in jephat + tert.- the iso-tetradecyl- ratio amine 0.7: 0.3 40 nis # 40% 20 + miscible

Claims (15)

P a t e n t a n s p r ü c h e: 1. Korrosionsschutzmittel für Metalloberflächen, bestehend aus einer Lösung von Benzotriazol, Methylbenzotriazol und/oder Tetrahydrobenzotriazol in einem Aminsalz einer Carbonsäure, einem Aminsalz einer Phosphorsäure, einem Phosphorsäuretrialkylester, einem Aminalkylbenzolsulfonat oder Mischungen daraus als Lösungsmittel.P a t e n t a n s p r ü c h e: 1. Corrosion protection agent for metal surfaces, consisting of a solution of benzotriazole, methylbenzotriazole and / or tetrahydrobenzotriazole in an amine salt of a carboxylic acid, an amine salt of a phosphoric acid, a phosphoric acid trialkyl ester, an amine alkyl benzene sulfonate or mixtures thereof as a solvent. 2. Korrosionsschutzmittel nach Anspruch 1, dadurch gekennzeichnet, daß als Lösungsmittel ein Aminsalz einer Carbonsäure verwendet wird, das einen Uberschuß an freier Carbonsäure enthält.2. Corrosion protection agent according to claim 1, characterized in that that an amine salt of a carboxylic acid is used as the solvent, which has an excess of free carboxylic acid. 3. Korrosionsschutzmittel nach Anspruch 1, dadurch gekennzeichnet, daß als Lösungsmittel ein Aminsalz einer Phosphorsäure verwendet wird, das einen Uberschuß an Phosphorsäuremono- oder -dialkylester enthält.3. Corrosion protection agent according to claim 1, characterized in that that an amine salt of phosphoric acid is used as a solvent, the one Contains excess of phosphoric acid mono- or dialkyl ester. 4. Korrosionsschutzmittel nach Anspruch 1, dadurch gekennzeichnet, daß als Lösungsmittel ein Phosphorsäuretrialkylester im Gemisch mit einem Amin verwendet wird.4. Corrosion protection agent according to claim 1, characterized in that that a phosphoric acid trialkyl ester is used as a solvent in a mixture with an amine will. 5. Korrosionsschutzmittel nach Anspruch 1, dadurch gekennzeichnet, daß als Lösungsmittel ein Amin-Alkylbenzolsulfonat verwendet wird, das einen Uberschuß an freiem Amin enthält0 5. Corrosion protection agent according to claim 1, characterized in that that an amine-alkylbenzenesulfonate is used as the solvent, which has an excess of free amine contains 0 6. Korrosionshemmendes Schmiermittel, gekennzeichnet durch einen Zusatz einer Lösung von Benzotriazol, Methylbenzotriazol und/oder Tetrahydrobenzotriazol in einem Aminsalz einer Carbonsäure, einem Aminsalz einer Phosphorsäure, einem Phosphorsäuretrialkylester, einem Amin-Alkylbenzolsulfonat oder Mischungen daraus als Lösungsmittel.6. Corrosion-inhibiting lubricant, characterized by an addition of a solution of benzotriazole, methylbenzotriazole and / or tetrahydrobenzotriazole in an amine salt of a carboxylic acid, an amine salt of a phosphoric acid, a phosphoric acid trialkyl ester, an amine-alkylbenzenesulfonate or mixtures thereof as a solvent. 7. Korrosionshemmendes Schmiermittel nach Anspruch 6, dadurch gekennzeichnet, daß als Lösungsmittel ein Aminsalz einer Carbonsäure verwendet wird, das einen Überschuß an freier Carbonsäure enthält.7. Corrosion-inhibiting lubricant according to claim 6, characterized in that that an amine salt of a carboxylic acid is used as the solvent, which is an excess of free carboxylic acid. 8. Korrosionshemmendes Schmiermittel nach Anspruch 6, dadurch gekennzeichnet, daß als Lösungsmittel ein Aminsalz einer Phosphorsäure verwendet wird, das einen Überschuß an Phosphorsäuremono- oder -dialkylester enthält.8. Corrosion-inhibiting lubricant according to claim 6, characterized in that that an amine salt of phosphoric acid is used as a solvent, the one Contains excess of phosphoric acid mono- or dialkyl ester. 9o Korrosionshemmendes Schmiermittel nach Anspruch 6, dadurch gekennzeichnet, daß als Lösungsmittel ein Phosphorsäuretrialkylester im Gemisch mit einem Amin verwendet wird.9o corrosion-inhibiting lubricant according to claim 6, characterized in that that a phosphoric acid trialkyl ester is used as a solvent in a mixture with an amine will. 10. Korrosionshemmendes Schmiermittel nach Anspruch 6, dadurch gekennzeichnet, daß als Lösungsmittel ein Amin-Alkylbenzolsulfonat verwendet wird, das einen Überschuß Amin enthält.10. Corrosion-inhibiting lubricant according to claim 6, characterized in that that an amine-alkylbenzenesulfonate is used as the solvent, which has an excess Contains amine. 11. Verfahren zur Herabsetzung der Korrosion von Metalloberflächen, dadurch gekennzeichnet, daß man Metalloberflächen mit einer Lösung von Benzotriazol, Methylbenzotriazol und/oder Tetrahydrobenzotriazol in einem Aminsalz einer Carbonsäure, einem Aminsalz einer Phosphorsäure, einem Phosphorsäuretrialkylester, einem Amin-Alkylbenzolsulfonat oder Mischungen daraus als Lösungsmittel in Kontakt hält, wobei die Lösung gegebenenfalls einem Schmiermittel zugesetzt ist.11. Processes to reduce the corrosion of metal surfaces, characterized in that metal surfaces with a solution of benzotriazole, Methylbenzotriazole and / or tetrahydrobenzotriazole in an amine salt of a carboxylic acid, an amine salt of a phosphoric acid, a phosphoric acid trialkyl ester, an amine alkylbenzenesulfonate or mixtures thereof as a solvent in contact, the solution optionally is added to a lubricant. 12. Verfahren nach Anspruch 11, dadurch gekennzeichnet, daß als Lösungsmittel ein Aminsalz einer Carbonsäure verwendet wird, das einen Uberschuß an freier Carbonsäure enthält.12. The method according to claim 11, characterized in that the solvent an amine salt of a carboxylic acid is used which has an excess of free carboxylic acid contains. 13. Verfahren nach Anspruch 11, dadurch gekennzeichnet, daß als Lösungsmittel ein Aminsalz einer Phosphorsäure verwendet wird, das einen Uberscnuß an Phosphorsäuremono- oder -dialkylester enthält.13. The method according to claim 11, characterized in that the solvent an amine salt of a phosphoric acid is used, which has an excess of phosphoric acid mono- or dialkyl ester. 14. Verfahren nach Anspruch 11, dadurch gekennzeichnet, daß als Lösungsmittel ein Phosphorsäuretrialkylester im Gemisch mit einem Amin verwendet wird.14. The method according to claim 11, characterized in that the solvent a phosphoric acid trialkyl ester is used in admixture with an amine. 15. Verfahren nach Anspruch 11, dadurch gekennzeichnet, daß als Lösungsmittel ein Amin-Alkylbenzolsulfonat verwendet wird, das einen Uberschuß Amin enthält,15. The method according to claim 11, characterized in that the solvent an amine alkylbenzenesulfonate is used which contains an excess of amine,
DE2530562A 1975-07-09 1975-07-09 Use of a concentrated solution of methyl benzotriazole as a corrosion protection agent Expired DE2530562C2 (en)

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FR2414547A1 (en) * 1978-01-11 1979-08-10 Exxon Research Engineering Co Synthetic ester lubricants - contg. ammonium phosphate ester and ammonium organo-sulphonate, esp. useful as aircraft turbine lubricants
FR2414548A1 (en) * 1978-01-13 1979-08-10 Exxon Research Engineering Co Synthetic ester lubricants for aircraft engines - contg. ammonium organo-sulphonate as EP additive
EP0135981A2 (en) * 1983-08-31 1985-04-03 Mobil Oil Corporation Multifunctional additives
US4683071A (en) * 1982-02-26 1987-07-28 Franz Regenass Benzotriazole mixtures, processes for producing them, and their use as metal passivators
EP1121404A1 (en) * 1998-08-04 2001-08-08 Mobil Oil Corporation High performance lubricating oils
WO2013048763A1 (en) * 2011-09-29 2013-04-04 Dow Global Technologies Llc Method for solubilizing carboxylic acid-containing compound in hydrocarbon solvent
US8968828B2 (en) 2011-01-24 2015-03-03 Dow Global Technologies Llc Composite polyamide membrane
US9051227B2 (en) 2013-03-16 2015-06-09 Dow Global Technologies Llc In-situ method for preparing hydrolyzed acyl halide compound
US9051417B2 (en) 2013-03-16 2015-06-09 Dow Global Technologies Llc Method for solubilizing carboxylic acid-containing compound in hydrocarbon solvent

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US9289729B2 (en) 2013-03-16 2016-03-22 Dow Global Technologies Llc Composite polyamide membrane derived from carboxylic acid containing acyl halide monomer

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FR1538431A (en) * 1965-03-11 1968-09-06 Dow Chemical Co Non-corrosive dry cleaning composition
DE1285835B (en) * 1963-02-06 1968-12-19 Geigy Ag J R Corrosion protection agent for metal surfaces that are in contact with liquid media

Patent Citations (2)

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DE1285835B (en) * 1963-02-06 1968-12-19 Geigy Ag J R Corrosion protection agent for metal surfaces that are in contact with liquid media
FR1538431A (en) * 1965-03-11 1968-09-06 Dow Chemical Co Non-corrosive dry cleaning composition

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2414547A1 (en) * 1978-01-11 1979-08-10 Exxon Research Engineering Co Synthetic ester lubricants - contg. ammonium phosphate ester and ammonium organo-sulphonate, esp. useful as aircraft turbine lubricants
FR2414548A1 (en) * 1978-01-13 1979-08-10 Exxon Research Engineering Co Synthetic ester lubricants for aircraft engines - contg. ammonium organo-sulphonate as EP additive
US4683071A (en) * 1982-02-26 1987-07-28 Franz Regenass Benzotriazole mixtures, processes for producing them, and their use as metal passivators
EP0135981A2 (en) * 1983-08-31 1985-04-03 Mobil Oil Corporation Multifunctional additives
EP0135981A3 (en) * 1983-08-31 1986-04-30 Mobil Oil Corporation Multifunctional additives
EP1121404A1 (en) * 1998-08-04 2001-08-08 Mobil Oil Corporation High performance lubricating oils
EP1121404A4 (en) * 1998-08-04 2003-01-22 Exxonmobil Oil Corp High performance lubricating oils
US8968828B2 (en) 2011-01-24 2015-03-03 Dow Global Technologies Llc Composite polyamide membrane
WO2013048763A1 (en) * 2011-09-29 2013-04-04 Dow Global Technologies Llc Method for solubilizing carboxylic acid-containing compound in hydrocarbon solvent
US9051227B2 (en) 2013-03-16 2015-06-09 Dow Global Technologies Llc In-situ method for preparing hydrolyzed acyl halide compound
US9051417B2 (en) 2013-03-16 2015-06-09 Dow Global Technologies Llc Method for solubilizing carboxylic acid-containing compound in hydrocarbon solvent

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