US2584041A - Process of preparing oil-soluble metal soaps - Google Patents

Process of preparing oil-soluble metal soaps Download PDF

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US2584041A
US2584041A US103316A US10331649A US2584041A US 2584041 A US2584041 A US 2584041A US 103316 A US103316 A US 103316A US 10331649 A US10331649 A US 10331649A US 2584041 A US2584041 A US 2584041A
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Nowak Milton
Fischer Alfred
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Nuodex Products Co Inc
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/41—Preparation of salts of carboxylic acids
    • C07C51/412—Preparation of salts of carboxylic acids by conversion of the acids, their salts, esters or anhydrides with the same carboxylic acid part

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  • the double decomposition reactions have' commonly been referred to as thewet process and the thermal decomposition process is known as the dry process.
  • the object of the present invention is to eliminate the disadvantages of the aforesaid conventional processes and to-permit the production of the desired end products through the use of more simple, highly effi cient and economical process steps.
  • An acid to be suitable within the teachings of this invention must be capable of yielding waterinsoluble, oil-soluble normalmetal soaps.
  • acids are oleic acid, tall oil acids, naphthenic acids, -2-ethylhexoi'c acid, petroleum sulphonate acids, nonanoic acid, linseed oil fatty acids, soya bean oil fatty acids, phenyl stearic acids, and ether acids, such as butoxy butyric acid, etc.
  • naphthenic acid, tall oil acid and z ethylhexoic acid singly. or combination, but
  • the process of this invention employs the metal preferably in powder form, in order that a large surface per weight is exposed to the reaction.
  • the metal together with the selected organic acidand water, is maintained at elevated temperatures while thorough agitation is maintained. Under such conditions, there is a very complete and rapid conversion of the metal into the corresponding metal soap.
  • modifying agents in minor amounts in order to impart certain characteristics to the end products.
  • addition agents in amounts of as little as 1% may reduce the viscosity of the end product, which is desirable for certain applications.
  • certain of these agents serve to prevent oxidation and thus instability of the end product.
  • the agents referred to may also be efiective in improving the com- (1611561381161 an air inlet tube.
  • reaction is complete.
  • the air inlet tube is closed, the reuflx condenser removed, and the water present driven off by heating the reaction mixture to 220 F.
  • Thesolution is then filtered to eliminate siliceous matter, analyzed for percent oil-soluble -cobalt, and diluted with mineral spirits to 6% cobalt.
  • V conversion'of 95% of the metal is obtained.
  • EXAMPLE 1a Cobalt naphthenate A portion of the end product obtained in Ex ample lis stripped ofits volatile solvent by distillation invacuum. The endproduct obtained is thus essentially free ofany solvent and is a solid at room temperature. 7 a
  • modifying agents are added to the end product reaction mass. Specifically 10 grams of triethanolamine lactate and 10 grams of amyl acid phosphate are added to the end products after the reaction is completed and prior to the drivingoff of the water. The addition of these modifying agents results in a cobalt naphthenate end product which is adapted for more universal use. The viscosity of the end product and resist ance to oxidation are considerably improved over that of the straight cobalt naphthenatee'nd prod act of Example 1. 7
  • the end product is a dark violet colored liquid consisting of a solution of cobalt tallate in'toluol, and may be employed as a drying catalyst in paintsand varnishes.
  • EXAMPLE 3 Cobalt Z-ethyl heroate 350 grams of 2-ethyl hexoic acid (acid number i and placed in a 3 liter, 3-neck, round bottom flask, equipped with agitator, reflux condenser, and an air inlet tube. The solution is agitated vigorously, while 100. grams of water are added, together with 64.4 grams of powdered cobalt metal (92% cobalt content). The reaction mix' ture is heated to 175 F. and air passed into'the mixture at the rate of 0.6 liter per minute. After 8 hours, the reaction is complete.
  • the water present is then distilled ofi completely, together with some of the mineral spirits.
  • the water present is then distilled off completely, together with some of the mineral spirits.
  • the material is analyzed and diluted with mineral spirits to exactly 6% manganese metalcontent. iA y'ield'of 984 grams of manganese tallate solution of.6'% metal content is obtained.
  • This product is a dark amber liquid, and is useful as a catalyst in the drying of paints and varnishes'. 1
  • Manganese nonanoate 361- grams of nonanoi'c-acid (acid number 345) are mixed with 130 grams mineral spirits, and placed in a 3 liter, 2-neck, round bottomflask, equipped with agitation, and reflux condenser. 60 grams-of manganese metal powder (particle size; 98% through 300 mesh screen) are added to the solution; together with 60 grams of water. The mixture is agitated rapidly, while heating to 212 F. The reaction is allowed to continue un til all of the manganese metal has dissolved (approximately 2 hours) I H The water present is then distilled ofl complete ly, together with some of the mineral spirits. There is then added grams of nonanoic acid for the.
  • the material is analyzed and diluted with mineral spirits to exactly 6% manganese metal content. A yield of 985 grams of manganese nonanoate solution of 6% metal content is obtained (98.5% yield).
  • This product is a dark amber liquid, and is useful as aa catalyst in the drying of paints and varnishes.
  • EXAMPLE 7 M anganese naphthenate d ill grams rectified naphthenic acid (acid number 230) are mixed with 130 grams mineral spirits, and placed in a 3 liter, 2-neck, round bottom flask, equipped with agitator and reflux condenser. grams of manganese metal powder (particle size: 98% through 300 mesh screen) are. added to the solution, together with 60 grams of water. The mixture is agitated rapidly, while heating to 212 F. The reaction is allowed to continue until all of the manganese metalhas dissolved. (approximately 2 hours).
  • The-water present is then distilled ofl completely, together with some of the mineral spirits.
  • the material is analyzed and diluted with mineral spirits to exactly 6% manganese metal content.- A yield of 986 grams of manganese naphthenate solution of 6% metal content is obtained. (98.6% yield.)
  • This product is a dark amber liquid, and is use-' ful asa catalyst in the drying of paints and varnishesm.
  • EXAMPLE 8 copper oleate"" 785 grams oleic acid (acid number 195) are dissolved in 600 grams mineral spirits, and placed in a 3-liter. round bottom flask, equipped with agitato'nmeflux condenser, and-an air inlet tube. 100 grams-water and grams powdered copper metal (particle size: 98% through 325 mesh screen are .added to the acid solution and the reaction mixture thenagitated. rapidly. Temperature or the mixture is brought to 212 F. and air :bubbled in at the rate of approximately 30:”) liters per hour. 1 1
  • reaction is substantially complete.
  • the water is distilled from the mixture in vacuo, together with some of the mineral spirits.
  • the reaction mixture is then filtered and analyzed for metal content. After analysis, it..is diluted with mineral spirits to yield 900 grams .of a solution of copper oleate containing 8% copper metal.
  • This product is a bright dark green liquid. It is useful as a pesticide in the preservation of celiulosic materials, as canvas, wood, etc.
  • the product is a' bright dark green liquid. It is useful as a pesticide in the preservation of cellulosic materials, as canvas, woods, etc.
  • EXAIVLPLE 10 Copper'tallate 840 grams of .a commercial grade of tall oil (acid number 183, rosin acids content 37%) are dissolved in 600 grams mineral spirits, and placed in a 3-liter, round bottom flask, equipped with agitator, reflux condenser, and an air inlet tube. 100 grams water and 80 grams powdered copper metal (particle size;- 98% through 325 mesh screen) are added to .the acid solution and reaction mixture then agitated rapidly. Temperature ofthe mixture is brought. to 210 F and air bubbled in at the rate 30(l liters per hour.;
  • EXAMPLE 18 Lead naphthenate 244 grams rectified naphthenic acid (acid number 230) are dissolved in 300 grams mineral spirits and solution placed in a 2 liter flask, equipped with reflux condenser, agitator and air inlet tube. 60 grams of water and 103.5 grams of finely powdered lead metal (particle size: 98% passing through 200 mesh screen) are then added to the reaction mixture and the entire mixture agitated rapidly and maintained at temperature of 212 F. Air is blown in at the rate of 90 liters per hour. After 12 hours, reaction is complete. 4
  • This product consists essentially of a solution of neutral lead soap of naphthenic acid, and is an amber liquid. This material may be used as a drying catalyst in paints and varnishes.
  • EXAMPLE 19 Basic lead naphthenate 1'77 grams of rectified naphthenic acid (acid number 230) are dissolved in 150 grams mineral spirits, and placed in a 1 liter flask, equipped with reflux condenser, agitator, and air inlet tube. 60 grams of water, and 103.5 grams finely powdered lead metal (particle size: 98% passing through 200 mesh screen) are added to the reac. tion mixture, which is then rapidly agitated, and heated to a temperature of 212 F.
  • This end product consists of a solution of basic lead tallate in mineral spirits. It is a clear light amber liquid, and is useful as a drying catalys for paints and varnishes.
  • EXAMPLE 21 Lead Z-ethyl hexoate 148 grams Z-ethyl hexoic acid (acid number 380) are dissolved in'300 grams mineral spirits and solution placed in a 2 liter flask, equipped with reflux condenser, agitator, and air inlet tube. 60 grams of water and 103.5 grams of finely powdered lead metal (particle size: 98% passing through 200 mesh screen) are then added to the reaction mixture and the entire mass agitated rapidly and maintained at temperature of 212 F. "Air is blown in at the rate of liters per hour. After 12 hours, reaction is complete.
  • This product consists essentiallyof'a solution of. a neutral lead soap of2-ethy1 hexoic acid, and is an amber liquid. This material maybe used as a drying catalyst in paints and varnishes.
  • the end product is a dark blue-violet liquid consisting of a solutionof-cobalt naphthenate tallate 'in mineral spirits, and containing 6% cobalt.
  • This material is useful as a catalyst in the drying of film-formingoxidizable material, as paints, varnishes, and the. like.
  • the water present is then distilled off completely, together with some of the mineral spirits.
  • the material is analyzed and diluted with mineral spirits-to exactly 6% manganese metal content. A conversion of 99% of manganese metal is obtained.
  • This product is a dark amber liquid, and is useful as a catalyst in the drying of paints and varnishes' EXAIVIPLE 24
  • Lead-(cobalt naphthenate 261grams rectified naphthenic acid (acid numher 230) are dissolved in 300 grams mineral spirits, and placed in a 2 liter flask, equipped with. reflux condenser, agitator, and air inlet tube.
  • To this solution are added '70 cc. water, 11.2 grams finely powdered cobalt metal (cobalt content 92%) (particle size: 98% passing through 325 mesh screen), and 103.5 grams of finely powdered lead metal (particle size: 98% passing through 200 mesh screen).
  • the mixture is agitated rapidly, and maintained at a temperature of 212 R,
  • the water is distilled off in vacuo, and the reaction mixture then filtered and analyzed for per cent soluble lead and cobalt. After analysis, it
  • the end product is a deep violet colored liquid, containing lead and cobalt in the ratio of 10:1; this ratio is one commonly employed where such metal combinations are used as drying catalysts in paints and varnishes.
  • Lead-cobalt salt of z-ethyl disastrous acid as naphthenic acid 177 grams rectified naphthenic acid (acid numher 230) and 51 grams 2-ethyl hexoic acid (acid number 380) are dissolved in 300 grams mineral spirits, and placed in 2,2 liter flask, equipped with reflux condenser, agitator, and air inlet tube. To
  • this solution are added 70 cc. water, 11.2 grams is diluted with mineral spirits to a lead content 01' 16% and a cobalt content of 1.6%. The conversion of each metal is approximately 96%.
  • the end product is a deep violetcolored liquid, containing lead and cobalt in the ratio of 10:1; this ratio is one commonly employed where such metal combinations are used as drying catalysts in paints andv varnishes.
  • the end-products of this invention are suitable for many uses. They are highly satisfactory when used as catalysts for the. drying of oxidizable film-forming materials, such as paints, var
  • nishes and the like are also very effective as drying catalysts for printing inks.
  • the end products may also be employed as coloring agents, e. g., as constituents of plastic compositions, to impart certain desirable color ization.
  • Still another important utility is that of stabilizing certain plastics, such as vinyl plastics against decomposition. It is also quite prac- I tied] to employ the heavy metal soapsthemselves
  • the foregoing examples refer to "naphthenie 7 acid," “tall oil acid” and tall oil.
  • the raw materials so designated are the raw materials of the trade and all of such raw materials so sold on the openmarket will function properly in the ex;
  • hydrous two phase metal-acid fusion-process which comprises: com-'- mingling at least one comminuted polyvalenli metal, at least one organic acid capable of form ing oil-soluble heavy metal soaps, and a quantity of waterto produce a reaction mass, and heating said mass to efi'ect reaction thereof to a temperature above 100 F. under conditions to maintain the water in its liquid phase throughout the reac tion while agitating the mass.
  • the herein described hydrous two-phase metal-acid fusion process which comprises: commingling at least one comminuted polyvalent metal, at least one organic acid capable of forming oil-soluble heavy metal soaps, and a quantity of water to produce a reaction mass, and heating said mass in the presence of air to effect reaction thereof to a temperature above 100 F. under conditions to maintain the water in itsliquid phase throughout the reaction while agitating the mass.

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Description

Patented Jan. 29, 1952 PROCESS OF PREPARING OIL-SOLUBLE METAL SOAPS Milton Nowak, Union, N. J., and Alfred Fischer,
Bronx, N. Y., assignors to Nuodex Products Co Inc., Elizabeth", N. J a corporation of New York No Drawing. Application July Serial No. 103,316
17 Claims. (01. 260-414) This invention is directed to the preparation of oil-soluble metal soaps for use in the various arts.
Heretofore such soaps have generally been produced, either through double decomposition processes employing the respective water-soluble salts of the metals and the water-soluble alkali soaps of the particular organic acids, or, by the reaction of the desired acids with thermally unstable compounds of the desired metals, such as carbonates, oxides andthe like. Both of these conventional processes have recognized disadvantages. In the commercial practice of the double decomposition process, it is impossible to entirely free the end product oil-soluble metal soap from contamination by the lay-product salts of such reactions, e. g., sodium sulphate. Another drawback to said process is the need of employing as an intermediate water-soluble salts of the specific metal. Such salts generally are more costly per metal content than the metal itself. Moreover; the equipment required for the practice of this processis complicated and relatively expensive. The thermal decomposition process can only be practiced-with certain metals, but not all of them, and the economicsare ad.- verse because the cost of the metal content in the oxides and carbonates and the like is generally higher than of the metal itself.
Of the foregoing processes, thedouble decomposition reactions have' commonly been referred to as thewet process and the thermal decomposition process is known as the dry process.
The object of the present invention is to eliminate the disadvantages of the aforesaid conventional processes and to-permit the production of the desired end products through the use of more simple, highly effi cient and economical process steps. We have beenable to accomplish this result by a distinctively novel process which we term a hydrous two-phase acid-metal fusion, wherein the metal in comminuted form is reacted at elevated temperature with free organic acid in the presence of water.
An acid to be suitable within the teachings of this invention, must be capable of yielding waterinsoluble, oil-soluble normalmetal soaps. Examples of such acids are oleic acid, tall oil acids, naphthenic acids, -2-ethylhexoi'c acid, petroleum sulphonate acids, nonanoic acid, linseed oil fatty acids, soya bean oil fatty acids, phenyl stearic acids, and ether acids, such as butoxy butyric acid, etc. For commercial reasons, especially economic reasons and quality considerations, we prefer to use naphthenic acid, tall oil acid and z ethylhexoic acid, singly. or combination, but
we wish it to be understood that the scope of this invention is commensurate with the entire range of those substantially water-insoluble and substantially oil-soluble organic acids capable of forming oil-soluble heavy metal soaps.
While we are particularly concerned with the preparation of heavy metal soaps, we have also obtained satisfactory results with other metals, such as aluminum, strontium and the like. Among the heavy metals which are of especial commercial importance, we have satisfactorily used: lead, cobalt, manganese, iron, copper, zinc, nickel, but we have also carried out preparation with many other members of the group of heavy metals.
Speaking generally, the process of this invention employs the metal preferably in powder form, in order that a large surface per weight is exposed to the reaction. The metal, together with the selected organic acidand water, is maintained at elevated temperatures while thorough agitation is maintained. Under such conditions, there is a very complete and rapid conversion of the metal into the corresponding metal soap. According to this invention, it is necessary to have water present throughout the entire reaction. This can be accomplished in various ways. For example, the process maybe carried out under appropriate refluxing conditions. At the end of the reaction period, which in commercial practice may be a matter of a few hours, it is usually desired to remove the water. This can be accomplished by distilling it off or by mechanical means, e. g., centrifuging. In many instances, we have found it desirable to employ water immiscible solvents for the end product. We have used mineral spirits, xylol and the like which are included within the reaction mass. The presence of such solvents often helps to facilitate the reaction and to reduce the viscosity of the end product, thus improving manipulation. In some cases, the reaction proceeded indifierently to the presence or absence of air, while in other cases the presence or absence of air aifected the velocity of the reaction. p
It is sometimes desirable to employ certain modifying agents in minor amounts in order to impart certain characteristics to the end products. For example, the use of addition agents in amounts of as little as 1% may reduce the viscosity of the end product, which is desirable for certain applications. Moreover, certain of these agents serve to prevent oxidation and thus instability of the end product. The agents referred to may also be efiective in improving the com- (1611561381161 an air inlet tube.
or after the reactions of this invention as they 7 play no part inthe reaction but are useful in modifying the properties of the end preducts.
Having thus generally described the present invention, we will now proceed with specific examples of practical performance.
EXAMPLE 1 Cobalt naphthenate y A solution of 530' grams of crude naphthenic acid (acid number 228) in 720 grams of mineral spirits is charged in a 2 1iter, 3-neck, round bottom flask, equipped with agitator, reflux con- The solution is agitated, and 0 grams of water added, together with 63 grams of-fine y powdered cobalt metal (95% cobalt content). The reaction mixture is heated to 195 F. and air is blown into the mix ture at a rateof 25.liters;per hour.
. After 10 hours, the reaction is complete. The air inlet tube is closed, the reuflx condenser removed, and the water present driven off by heating the reaction mixture to 220 F. Thesolution is then filtered to eliminate siliceous matter, analyzed for percent oil-soluble -cobalt, and diluted with mineral spirits to 6% cobalt. A
V conversion'of 95% of the metal is obtained.
EXAMPLE 1a Cobalt naphthenate A portion of the end product obtained in Ex ample lis stripped ofits volatile solvent by distillation invacuum. The endproduct obtained is thus essentially free ofany solvent and is a solid at room temperature. 7 a
, 1b Cobalt naphthenate with additives V A cobalt naphthenate is prepared in exactly the same manner as described in Example 1, ex
cept that modifying agents are added to the end product reaction mass. Specifically 10 grams of triethanolamine lactate and 10 grams of amyl acid phosphate are added to the end products after the reaction is completed and prior to the drivingoff of the water. The addition of these modifying agents results in a cobalt naphthenate end product which is adapted for more universal use. The viscosity of the end product and resist ance to oxidation are considerably improved over that of the straight cobalt naphthenatee'nd prod act of Example 1. 7
EXAMPLE 2 Cobalt 'tallate A solution of 325grarns of a commercial grade of tall oil (acid number 183, rosin acids content 37%) is dissolved in 310 grams of toluol, and charged in a 2 liter, B-neck, round bottom flask,
- equipped with agitator;refiuxvcondenser, and an air inlet tube. The solution is agitated, and 50 grams of water added with 31.5 grams of finely V powdered cobalt metal cobalt content). The reaction mixture is heated to 195 F. and air is blown into the mixture at a rate of 0.8 liter per minute. 7
After 12 hours, the reaction is complete. The water present is distilled off in-vacuo, the solution filtered, analyzed, and diluted with toluol to 4% cobalt metal content. The yield is 720 grams (a conversion of 96% of the metal).
The end product is a dark violet colored liquid consisting of a solution of cobalt tallate in'toluol, and may be employed as a drying catalyst in paintsand varnishes.
, EXAMPLE 3 Cobalt Z-ethyl heroate 350 grams of 2-ethyl hexoic acid (acid number i and placed in a 3 liter, 3-neck, round bottom flask, equipped with agitator, reflux condenser, and an air inlet tube. The solution is agitated vigorously, while 100. grams of water are added, together with 64.4 grams of powdered cobalt metal (92% cobalt content). The reaction mix' ture is heated to 175 F. and air passed into'the mixture at the rate of 0.6 liter per minute. After 8 hours, the reaction is complete.
The water present is then distilled oii, and t 2 solution filtered to remove siliceous matter originally present in the cobalt metal. The solution is then analyzed, and diluted with mineral spirits to yield 728 grams of a solution of cobalt z-ethyl hexoate containing .8% cobalt (97% conversion EXAMPLE 4 Manganese Z-ethyl hemoate 380 grams of 2-ethyl hexoic acid (acid number 380) are mixed-with grams mineral spirits, and placed in a 3 liter, 2-neck, round-bottom flask, equipped with agitator and reflux condenser. 60 grams of manganese metal flakes of approximately 4 mesh particle size are added to the solution, together with 60 grams water. The mixture is agitated rapidly, while heating to 212 F. The reaction is allowed to continue until all of the manganese metal has dissolved (approximately 10 hours).
The water present is then distilled ofi completely, together with some of the mineral spirits.
685. grams or a commercial grade of tall 011 (acid number 184, rosin acids content 37%), are mixed with 130 grams mineral spirits, and placed in a 3 liter, 2- neck, round bottom flask, equipped with agitator and reflux condenser. 60 grams of manganese metal powder (particle size: 98% through 300 mesh screen) are added to the solution, together with 60 grams of water. The mixture is agitated rapidly, while heating to 212 F. The reaction is-allowed to continue until all of the manganese metal has dissolved (approximately 2 hours).
The water present is then distilled off completely, together with some of the mineral spirits. The material is analyzed and diluted with mineral spirits to exactly 6% manganese metalcontent. iA y'ield'of 984 grams of manganese tallate solution of.6'% metal content is obtained.
f This product is a dark amber liquid, and is useful as a catalyst in the drying of paints and varnishes'. 1
" Manganese nonanoate 361- grams of nonanoi'c-acid (acid number 345) are mixed with 130 grams mineral spirits, and placed in a 3 liter, 2-neck, round bottomflask, equipped with agitation, and reflux condenser. 60 grams-of manganese metal powder (particle size; 98% through 300 mesh screen) are added to the solution; together with 60 grams of water. The mixture is agitated rapidly, while heating to 212 F. The reaction is allowed to continue un til all of the manganese metal has dissolved (approximately 2 hours) I H The water present is then distilled ofl complete ly, together with some of the mineral spirits. There is then added grams of nonanoic acid for the. purpose of adjusting the viscosity and stability characteristics of the end product. The material is analyzed and diluted with mineral spirits to exactly 6% manganese metal content. A yield of 985 grams of manganese nonanoate solution of 6% metal content is obtained (98.5% yield).
This product is a dark amber liquid, and is useful as aa catalyst in the drying of paints and varnishes.
EXAMPLE 7 M anganese naphthenate d ill grams rectified naphthenic acid (acid number 230) are mixed with 130 grams mineral spirits, and placed in a 3 liter, 2-neck, round bottom flask, equipped with agitator and reflux condenser. grams of manganese metal powder (particle size: 98% through 300 mesh screen) are. added to the solution, together with 60 grams of water. The mixture is agitated rapidly, while heating to 212 F. The reaction is allowed to continue until all of the manganese metalhas dissolved. (approximately 2 hours).
The-water present is then distilled ofl completely, together with some of the mineral spirits. The material is analyzed and diluted with mineral spirits to exactly 6% manganese metal content.- A yield of 986 grams of manganese naphthenate solution of 6% metal content is obtained. (98.6% yield.)
This product is a dark amber liquid, and is use-' ful asa catalyst in the drying of paints and varnishesm.
"EXAMPLE7a Manganese naphthenate with additive ?Bll leale y ea i ss s ir nd .i ro salsni 6, of general performance over that of the 'end product of'Example U @Instead of using the particular additive referred to, we have also used as an additive, amyl acid phosphate, triethyl citratatributyl citrate, etc. with satisfactory commercial results.
EXAMPLE 8 copper oleate"" 785 grams oleic acid (acid number 195) are dissolved in 600 grams mineral spirits, and placed in a 3-liter. round bottom flask, equipped with agitato'nmeflux condenser, and-an air inlet tube. 100 grams-water and grams powdered copper metal (particle size: 98% through 325 mesh screen are .added to the acid solution and the reaction mixture thenagitated. rapidly. Temperature or the mixture is brought to 212 F. and air :bubbled in at the rate of approximately 30:") liters per hour. 1 1
After 14 hours, the reaction is substantially complete. The water is distilled from the mixture in vacuo, together with some of the mineral spirits. The reaction mixture is then filtered and analyzed for metal content. After analysis, it..is diluted with mineral spirits to yield 900 grams .of a solution of copper oleate containing 8% copper metal.
- This product is a bright dark green liquid. It is useful as a pesticide in the preservation of celiulosic materials, as canvas, wood, etc.
EXAMPLE!) .Oopper naphthemte 665 grams crude naphthenic acid (acid number 228) are dissolved in 600 grams mineral spirits, and placed in a 3 liter, round bottom flask, equipped with agitator, reflux condenser, and an air inlet tube. 100 grams water and 80 grams powdered copper metal (particle size: 98% through 325 mesh screen) are added to the acid solution; and reaction mixture then agitated rapidly. Temperature of the mixture is brought to 212 F. and air bubbled in at the rate of approximately 300 liters per hour.
"After li hours, the reaction is substantially complete. The water is distilled from the mixture in vacuo, together with some of the mineral spirits. The reaction mixture is then filtered and analyzed for metal content. After analysis, it is diluted with mineral spirits to" yield 930 grams of a solution of coppernaphthenate containing 8% copper metal.
The product is a' bright dark green liquid. It is useful as a pesticide in the preservation of cellulosic materials, as canvas, woods, etc.
EXAIVLPLE 10 Copper'tallate 840 grams of .a commercial grade of tall oil (acid number 183, rosin acids content 37%) are dissolved in 600 grams mineral spirits, and placed in a 3-liter, round bottom flask, equipped with agitator, reflux condenser, and an air inlet tube. 100 grams water and 80 grams powdered copper metal (particle size;- 98% through 325 mesh screen) are added to .the acid solution and reaction mixture then agitated rapidly. Temperature ofthe mixture is brought. to 210 F and air bubbled in at the rate 30(l liters per hour.;
After 14 hours-the reaction is substantially 99 3191 1 The .wa er 1 d st led from. the mixture in vacuo, together with some of the mineral of approximately 9 metal (particle size: 98% passingffthrough 300 mesh screen) are added, and the reaction mixture rapidly agitated. The temperature of the mixture is kept at 212 F. while air is blown mat the mixing of pigments, and as a pesticide and fungicide for the preservation of cellulosic ma terials.
EXAMPLE 18 Lead naphthenate 244 grams rectified naphthenic acid (acid number 230) are dissolved in 300 grams mineral spirits and solution placed in a 2 liter flask, equipped with reflux condenser, agitator and air inlet tube. 60 grams of water and 103.5 grams of finely powdered lead metal (particle size: 98% passing through 200 mesh screen) are then added to the reaction mixture and the entire mixture agitated rapidly and maintained at temperature of 212 F. Air is blown in at the rate of 90 liters per hour. After 12 hours, reaction is complete. 4
Water is distilled from the reaction mixture in vacuo, and the residue filtered and analyzed for lead content. After analysis, the solution is diluted with mineral spirits to exactly 16% lead metal content. A conversion of 97% of the metal is obtained.
This product consists essentially of a solution of neutral lead soap of naphthenic acid, and is an amber liquid. This material may be used as a drying catalyst in paints and varnishes.
EXAMPLE 19 Basic lead naphthenate 1'77 grams of rectified naphthenic acid (acid number 230) are dissolved in 150 grams mineral spirits, and placed in a 1 liter flask, equipped with reflux condenser, agitator, and air inlet tube. 60 grams of water, and 103.5 grams finely powdered lead metal (particle size: 98% passing through 200 mesh screen) are added to the reac. tion mixture, which is then rapidly agitated, and heated to a temperature of 212 F. Air is blown in at the rate of 3 liters per minute for a period of hours, after which time the reaction is EXAMPLE 20 Basic lead tallate 122 grams of a refined grade of tall oil (acid number 183, rosin acids content 37%) are dis:
solved in 150 grams mineral spirits, and placed in a 1 liter flask, equipped with reflux condenser,
agitator, and air inlet tube. 60 grams of water, and 103.5 grams finely powdered lead metal (particle size 98% passing through 200 mesh screen) are added to the reaction mixture, which is then rapidly agitated, and heated to a temperature of 212 F. Air is blown in at the rate of 3 liters perminute for a period of 15 hours, after which time the reactionis found to be substantially complete.
The water present is then distilled irom the reaction mixture in vacuo. The remaining solu-- tion is then filtered and analyzed for lead content. After analysis, it is diluted with mineral spirits to yield 610 grams of a solution containing 16% lead metal:
This end product consists of a solution of basic lead tallate in mineral spirits. It is a clear light amber liquid, and is useful as a drying catalys for paints and varnishes.
EXAMPLE 21 Lead Z-ethyl hexoate 148 grams Z-ethyl hexoic acid (acid number 380) are dissolved in'300 grams mineral spirits and solution placed in a 2 liter flask, equipped with reflux condenser, agitator, and air inlet tube. 60 grams of water and 103.5 grams of finely powdered lead metal (particle size: 98% passing through 200 mesh screen) are then added to the reaction mixture and the entire mass agitated rapidly and maintained at temperature of 212 F. "Air is blown in at the rate of liters per hour. After 12 hours, reaction is complete.
Water is distilled from the reaction mixture in vacuo, and the residuefilteredand analyzed for lead content. After analysis, the solution is diluted with mineral spirits to exactly 24% lead metal content. A- conversion 01' 97% of the metal is obtained.
This product consists essentiallyof'a solution of. a neutral lead soap of2-ethy1 hexoic acid, and is an amber liquid. This material maybe used as a drying catalyst in paints and varnishes.
EXAMPLE 22 Cobalt salt of a combination of tall oilcnd naphthenic acid After 10 hours the reaction is. complete. The
air inlet tube is closed, the reflux, condenser re moved, and the water presentdriven off by heat-, ing the reaction mixture to 220 F. The solution is then filtered toeliminate siliceous mat.-, ter, analyzed for per cent soluble cobalt, and diluted with mineral spirits to 6% cobalt. A conversion of 96% of the metal is obtained. r
The end product is a dark blue-violet liquid consisting of a solutionof-cobalt naphthenate tallate 'in mineral spirits, and containing 6% cobalt. This material is useful as a catalyst in the drying of film-formingoxidizable material, as paints, varnishes, and the. like.
1 1 EXAMPLE 23 Manganese-salt of a combination of z-eth'yl heroic agcid and naphthenic acid solved (approximately hours).
The water present is then distilled off completely, together with some of the mineral spirits. The material is analyzed and diluted with mineral spirits-to exactly 6% manganese metal content. A conversion of 99% of manganese metal is obtained.
This product is a dark amber liquid, and is useful as a catalyst in the drying of paints and varnishes' EXAIVIPLE 24 Lead-(cobalt naphthenate 261grams rectified naphthenic acid (acid numher 230) are dissolved in 300 grams mineral spirits, and placed in a 2 liter flask, equipped with. reflux condenser, agitator, and air inlet tube. To this solution are added '70 cc. water, 11.2 grams finely powdered cobalt metal (cobalt content 92%) (particle size: 98% passing through 325 mesh screen), and 103.5 grams of finely powdered lead metal (particle size: 98% passing through 200 mesh screen). The mixture is agitated rapidly, and maintained at a temperature of 212 R,
. while blowing in air. at the rate of 4 liters per minute. After hours, the reaction is substantially complete. r
The water is distilled off in vacuo, and the reaction mixture then filtered and analyzed for per cent soluble lead and cobalt. After analysis, it
is diluted with mineral spirits to a lead content of 16% and a cobalt content of 1.6%. The conversion of each metal is approximately 93%.
' The end product is a deep violet colored liquid, containing lead and cobalt in the ratio of 10:1; this ratio is one commonly employed where such metal combinations are used as drying catalysts in paints and varnishes.
EXAMPLE.
Lead-cobalt salt of z-ethyl heroic acid as naphthenic acid 177 grams rectified naphthenic acid (acid numher 230) and 51 grams 2-ethyl hexoic acid (acid number 380) are dissolved in 300 grams mineral spirits, and placed in 2,2 liter flask, equipped with reflux condenser, agitator, and air inlet tube. To
' this solution are added 70 cc. water, 11.2 grams is diluted with mineral spirits to a lead content 01' 16% and a cobalt content of 1.6%. The conversion of each metal is approximately 96%..
The end product is a deep violetcolored liquid, containing lead and cobalt in the ratio of 10:1; this ratio is one commonly employed where such metal combinations are used as drying catalysts in paints andv varnishes. I
'It will be apparent from the foregoing examples that a single acid and a single metal may be reacted .in the manner stated or combinations of acids and/or metals may also be satisfactorily carried out. The invention is not limited to the illustrative examples given.
The end-products of this invention are suitable for many uses. They are highly satisfactory when used as catalysts for the. drying of oxidizable film-forming materials, such as paints, var
nishes and the like. They are also very effective as drying catalysts for printing inks. Another important field of application, particularly for the copper soaps, is that of pest control, including the conservation of wood and other cellulosic materials against the ravages of insects, fungi, etc. The end products may also be employed as coloring agents, e. g., as constituents of plastic compositions, to impart certain desirable color ization. Still another important utility is that of stabilizing certain plastics, such as vinyl plastics against decomposition. It is also quite prac- I tied] to employ the heavy metal soapsthemselves The foregoing examples refer to "naphthenie 7 acid," "tall oil acid" and tall oil. The raw materials so designated are the raw materials of the trade and all of such raw materials so sold on the openmarket will function properly in the ex;
amples given for the purpose of carrying out the present invention.
Having thus fully described the invention,
what we: claim as new and desire to secure by Letters Patent is:
l. The herein described hydrous two phase metal-acid fusion-process which comprises: com-'- mingling at least one comminuted polyvalenli metal, at least one organic acid capable of form ing oil-soluble heavy metal soaps, and a quantity of waterto produce a reaction mass, and heating said mass to efi'ect reaction thereof to a temperature above 100 F. under conditions to maintain the water in its liquid phase throughout the reac tion while agitating the mass.
2. Process as claimed in claim 1, which includes the freeing of the oil-solublemetal soap end product from the water at the conclusion of the reaction.
3. The process of claim 1, wherein one metal is a heavy metal.
4 The processof claim 1, wherein one metal is a heavy metal and one acid is naphthenic' acid.
5. The process of claim 1, wherein one metal is cobalt and one acid is naphthenic acid.
I 6. The process of claim 1, wherein one metal is cobalt and one acid is tall 011 acid.
-7. The process of claim 1, wherein one metal is cobalt and one acid is 2-ethylhexoic acid.
8. The process of claim 1, wherein one metal. is manganese and one acid is naphthentic acid.
9. The process of claim 1, wherein one metal is, manganese and one acid is tall oil acid.
10. ..The process of claim 1, wherein one metal is manganese and one acid is 2-ethylhexoic acid...
. .llgjlfhe process- 01' claim 1, wherein one. metalv isiron' andone acid is naphthenic acid. 12. The process of claim 1, wherein the metal is iron and one acid is tall oil acid. I
13. The process or claim 1, wherein the metal is iron and one acid is 2-ethy1hexoic acid.
14. The process of claim 1, wherein the metal is copper and one acid is naphthenic acid.
15. The process of claim 1, wherein the metal is copper and one acid is tall oil acid.
16. The process of claim 1, wherein the metal is copper and one acid is 2-ethylhexoic acid.
17. The herein described hydrous two-phase metal-acid fusion process which comprises: commingling at least one comminuted polyvalent metal, at least one organic acid capable of forming oil-soluble heavy metal soaps, and a quantity of water to produce a reaction mass, and heating said mass in the presence of air to effect reaction thereof to a temperature above 100 F. under conditions to maintain the water in itsliquid phase throughout the reaction while agitating the mass.
MILTON NOWAK. ALFRED FISCHER.
REFERENCES CITED The following references are of record in the file of this patent:
UNITED STATES PATENTS Number Name Date 2,338,128 Minich Jan. 4, 1944 2,397,767 Taylor Apr. 2, 1946 2,409,678 Hamblet Oct. 22, 1946 2,416,074 Weber et a1 Feb. 18, 1947 2,423,619 Roon July 8, 1947 2,445,935 Bondi July 27, 1948 2,472,424 Hoover June 7, 1949 2,527,789 Bondi Oct. 31, 1950 FOREIGN PATENTS Number Country Date 589,242 Great Britain June 16, 1947

Claims (1)

1. THE HEREIN DESCRIBED HYDROUS TWO-PHASE METAL-ACID FUSION PROCESS WHICH COMPRISES: COMMINGLING AT LEAST ONE COMMINUTED POLYVALENT METAL, AT LEAST ONE ORGANIC ACID CAPABLE OF FORMING OIL-SOLUBLE HEAVY METAL SOAPS, AND A QUANTITY OF WATER TO PRODUCE A REACTION MASS, AND HEATING SAID MASS TO EFFECT REACTION THEREOF TO A TEMPERATURE ABOVE 100* F. UNDER CONDITIONS TO MAINTAIN THE WATER IN ITS LIQUID PHASE THROUGHOUT THE REACTION WHILE AGITATING THE MASS.
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Cited By (29)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2739902A (en) * 1952-08-29 1956-03-27 Carlisle Chemical Works Drier compositions
US2739905A (en) * 1952-08-29 1956-03-27 Carlisle Chemical Works Zirconyl 2-ethylhexoate
US2741629A (en) * 1952-11-20 1956-04-10 Cohen Leonard Aluminum soap of iso-octoic acids
US2751361A (en) * 1954-06-14 1956-06-19 Standard Oil Co Liquid hydrocarbon gelling agents
US2751360A (en) * 1953-12-30 1956-06-19 Standard Oil Co Presolvated aluminum soap gelling agents
US2846392A (en) * 1953-10-21 1958-08-05 Exxon Research Engineering Co Metal soap-salt complexes and lubricants containing same
US2892782A (en) * 1955-08-29 1959-06-30 Texaco Inc Mixtures of metal salts of organic hydroxy compounds
US2907799A (en) * 1955-05-31 1959-10-06 Monsanto Chemicals Ullmann reaction
US2985673A (en) * 1957-11-04 1961-05-23 Du Pont Polymerization catalysts
US3133942A (en) * 1960-12-03 1964-05-19 Basf Ag Production of metal salts of organic acids
US3185586A (en) * 1961-02-28 1965-05-25 Pittsburgh Plate Glass Co Coated glass sheets
US3211768A (en) * 1961-01-18 1965-10-12 M & T Chemicals Inc Chemical process for preparing a salt of a metal of groups (iv)a and (v)a and salt
US3260689A (en) * 1960-05-27 1966-07-12 Eastman Kodak Co Polyester and polyamide compositions having improved dyeing properties and processesfor the production of such compositions
US3291738A (en) * 1960-09-02 1966-12-13 Rca Corp Materials for preparing etch resists
US3325429A (en) * 1966-05-31 1967-06-13 Harris James Donald Method of preparing rubber compositions having improved physical properties
US3411936A (en) * 1965-03-01 1968-11-19 Interchem Corp Developing electrostatic images with a liquid developer containing tetraphenyl tin or zirconyl 2-ethylhexoate
US3411937A (en) * 1965-03-01 1968-11-19 Interchem Corp Method of liquid electrostatic developing
US3673229A (en) * 1970-03-05 1972-06-27 Jacobus Rinse Metal oxide acylates and their preparation
US4022725A (en) * 1972-12-04 1977-05-10 Moaco Metal Oxide Acylates Company Condensed oligomeric organo metallic resinous acylates containing ligands of monobasic carboxylic acid of at least 7 carbon atoms and bridging radicals of divalent carboxylic acids of at least 6 carbon atoms and processes for producing such resins
US4257913A (en) * 1979-09-17 1981-03-24 Tenneco Chemicals, Inc. Stable manganese salt solutions and a process for their production
EP0058792A1 (en) * 1981-02-17 1982-09-01 Nuodex Inc. Process for the production of oil-soluble metal salts
US4720352A (en) * 1985-11-01 1988-01-19 Nuodex Inc. Process for the preparation of vanadium-containing mixed metal soap solutions
US5461172A (en) * 1993-08-09 1995-10-24 Mooney Chemicals, Inc. Light-colored manganese carboxylates
US6599472B1 (en) * 2000-11-03 2003-07-29 Surface Chemists Of Florida Inc. Oil soluble scavengers for sulfides and mercaptans
US20090047311A1 (en) * 2005-06-30 2009-02-19 Takeshi Imahashi Antibacterial Agent Composed of Silver-Containing Aluminum Sulfate Hydroxide Particles and Use Thereof
US8889599B1 (en) * 2013-05-20 2014-11-18 Halliburton Energy Services, Inc. Methods for use of oil-soluble weighting agents in subterranean formation treatment fluids
US20150025258A1 (en) * 2013-07-19 2015-01-22 Baker Hughes Incorporation Oil soluble hydrogen sulfide scavenger
US9480946B2 (en) 2013-04-15 2016-11-01 Baker Hughes Incorporated Metal carboxylate salts as H2S scavengers in mixed production or dry gas or wet gas systems
WO2022164532A1 (en) * 2021-01-29 2022-08-04 Koppers Performance Chemicals, Inc. A method for producing copper carboxylate, a wood preservative composition comprising copper carboxylate, and a wood product produced therefrom

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US2338128A (en) * 1944-01-04 Mortar flare shell
US2397767A (en) * 1943-10-04 1946-04-02 Procter & Gamble Process for making copper soaps
US2409678A (en) * 1943-09-18 1946-10-22 Du Pont Preparation of soaps
US2416074A (en) * 1943-09-21 1947-02-18 Du Pont Preparation of heavy metal soaps
GB589242A (en) * 1944-09-25 1947-06-16 Du Pont Improvements in and relating to the preparation of salts of organic acids
US2423619A (en) * 1943-11-10 1947-07-08 Nuodex Products Co Inc Method of preparing copper fungicide solutions
US2445935A (en) * 1945-10-31 1948-07-27 Shell Dev Production of greases
US2472424A (en) * 1946-10-02 1949-06-07 Air Reduction Production of cuprous naphthenate
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US2338128A (en) * 1944-01-04 Mortar flare shell
US2409678A (en) * 1943-09-18 1946-10-22 Du Pont Preparation of soaps
US2416074A (en) * 1943-09-21 1947-02-18 Du Pont Preparation of heavy metal soaps
US2397767A (en) * 1943-10-04 1946-04-02 Procter & Gamble Process for making copper soaps
US2423619A (en) * 1943-11-10 1947-07-08 Nuodex Products Co Inc Method of preparing copper fungicide solutions
GB589242A (en) * 1944-09-25 1947-06-16 Du Pont Improvements in and relating to the preparation of salts of organic acids
US2445935A (en) * 1945-10-31 1948-07-27 Shell Dev Production of greases
US2527789A (en) * 1946-05-02 1950-10-31 Shell Dev Process of and apparatus for cooling a lubricant
US2472424A (en) * 1946-10-02 1949-06-07 Air Reduction Production of cuprous naphthenate

Cited By (36)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2739902A (en) * 1952-08-29 1956-03-27 Carlisle Chemical Works Drier compositions
US2739905A (en) * 1952-08-29 1956-03-27 Carlisle Chemical Works Zirconyl 2-ethylhexoate
US2741629A (en) * 1952-11-20 1956-04-10 Cohen Leonard Aluminum soap of iso-octoic acids
US2846392A (en) * 1953-10-21 1958-08-05 Exxon Research Engineering Co Metal soap-salt complexes and lubricants containing same
US2751360A (en) * 1953-12-30 1956-06-19 Standard Oil Co Presolvated aluminum soap gelling agents
US2751361A (en) * 1954-06-14 1956-06-19 Standard Oil Co Liquid hydrocarbon gelling agents
US2907799A (en) * 1955-05-31 1959-10-06 Monsanto Chemicals Ullmann reaction
US2892782A (en) * 1955-08-29 1959-06-30 Texaco Inc Mixtures of metal salts of organic hydroxy compounds
US2985673A (en) * 1957-11-04 1961-05-23 Du Pont Polymerization catalysts
US3260689A (en) * 1960-05-27 1966-07-12 Eastman Kodak Co Polyester and polyamide compositions having improved dyeing properties and processesfor the production of such compositions
US3291738A (en) * 1960-09-02 1966-12-13 Rca Corp Materials for preparing etch resists
US3133942A (en) * 1960-12-03 1964-05-19 Basf Ag Production of metal salts of organic acids
US3211768A (en) * 1961-01-18 1965-10-12 M & T Chemicals Inc Chemical process for preparing a salt of a metal of groups (iv)a and (v)a and salt
US3185586A (en) * 1961-02-28 1965-05-25 Pittsburgh Plate Glass Co Coated glass sheets
US3411936A (en) * 1965-03-01 1968-11-19 Interchem Corp Developing electrostatic images with a liquid developer containing tetraphenyl tin or zirconyl 2-ethylhexoate
US3411937A (en) * 1965-03-01 1968-11-19 Interchem Corp Method of liquid electrostatic developing
US3325429A (en) * 1966-05-31 1967-06-13 Harris James Donald Method of preparing rubber compositions having improved physical properties
US3673229A (en) * 1970-03-05 1972-06-27 Jacobus Rinse Metal oxide acylates and their preparation
US4022725A (en) * 1972-12-04 1977-05-10 Moaco Metal Oxide Acylates Company Condensed oligomeric organo metallic resinous acylates containing ligands of monobasic carboxylic acid of at least 7 carbon atoms and bridging radicals of divalent carboxylic acids of at least 6 carbon atoms and processes for producing such resins
US4257913A (en) * 1979-09-17 1981-03-24 Tenneco Chemicals, Inc. Stable manganese salt solutions and a process for their production
EP0058792A1 (en) * 1981-02-17 1982-09-01 Nuodex Inc. Process for the production of oil-soluble metal salts
US4720352A (en) * 1985-11-01 1988-01-19 Nuodex Inc. Process for the preparation of vanadium-containing mixed metal soap solutions
AU587294B2 (en) * 1985-11-01 1989-08-10 Huls America Inc. Process for the preparation of vanadium- containing mixed metal soap solutions
US5461172A (en) * 1993-08-09 1995-10-24 Mooney Chemicals, Inc. Light-colored manganese carboxylates
US6599472B1 (en) * 2000-11-03 2003-07-29 Surface Chemists Of Florida Inc. Oil soluble scavengers for sulfides and mercaptans
US20090047311A1 (en) * 2005-06-30 2009-02-19 Takeshi Imahashi Antibacterial Agent Composed of Silver-Containing Aluminum Sulfate Hydroxide Particles and Use Thereof
US8394392B2 (en) * 2005-06-30 2013-03-12 Kyowa Chemical Industry Co., Ltd. Antibacterial agent composed of silver-containing aluminum sulfate hydroxide particles and use thereof
US9480946B2 (en) 2013-04-15 2016-11-01 Baker Hughes Incorporated Metal carboxylate salts as H2S scavengers in mixed production or dry gas or wet gas systems
US20140342950A1 (en) * 2013-05-20 2014-11-20 Halliburton Energy Services, Inc. Methods for Use of Oil-Soluble Weighting Agents in Subterranean Formation Treatment Fluids
US8889599B1 (en) * 2013-05-20 2014-11-18 Halliburton Energy Services, Inc. Methods for use of oil-soluble weighting agents in subterranean formation treatment fluids
US20150025258A1 (en) * 2013-07-19 2015-01-22 Baker Hughes Incorporation Oil soluble hydrogen sulfide scavenger
US9353026B2 (en) * 2013-07-19 2016-05-31 Baker Hughes Incorporated Oil soluble hydrogen sulfide scavenger
WO2022164532A1 (en) * 2021-01-29 2022-08-04 Koppers Performance Chemicals, Inc. A method for producing copper carboxylate, a wood preservative composition comprising copper carboxylate, and a wood product produced therefrom
US20220332008A1 (en) * 2021-01-29 2022-10-20 Koppers Performance Chemicals, Inc. Method for producing copper carboxylate, a wood preservative composition comprising copper carboxylate, and a wood product produced therefrom
US11951649B2 (en) * 2021-01-29 2024-04-09 Koppers Performance Chemicals, Inc. Method for producing copper carboxylate, a wood preservative composition comprising copper carboxylate, and a wood product produced therefrom
US20240278455A1 (en) * 2021-01-29 2024-08-22 Koppers Performance Chemicals, Inc. Method for producing copper carboxylate, a wood preservative composition comprising copper carboxylate, and a wood product produced therefrom

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