US2801973A - Grease process utilizing the alkali fusion of aldehydes - Google Patents

Grease process utilizing the alkali fusion of aldehydes Download PDF

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Publication number
US2801973A
US2801973A US327166A US32716652A US2801973A US 2801973 A US2801973 A US 2801973A US 327166 A US327166 A US 327166A US 32716652 A US32716652 A US 32716652A US 2801973 A US2801973 A US 2801973A
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Prior art keywords
alkali
aldehyde
grease
fusion
aldehydes
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US327166A
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Arnold J Morway
Jeffrey H Bartlett
Louis A Mikeska
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ExxonMobil Technology and Engineering Co
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Exxon Research and Engineering Co
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Priority to US327166A priority Critical patent/US2801973A/en
Priority to GB30946/53A priority patent/GB753339A/en
Priority to FR1092698D priority patent/FR1092698A/fr
Priority to DEST7499A priority patent/DE967837C/de
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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
    • C07C51/16—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation
    • C07C51/295—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with inorganic bases, e.g. by alkali fusion
    • C—CHEMISTRY; METALLURGY
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    • C10M169/00—Lubricating compositions characterised by containing as components a mixture of at least two types of ingredient selected from base-materials, thickeners or additives, covered by the preceding groups, each of these compounds being essential
    • C10M169/02—Mixtures of base-materials and thickeners
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Definitions

  • the present invention relates to an improved method of preparing lubricating greases and to grease compositions produced by this method. More specifically, the invention pertains to improvements in the manufacture of grease thickeners and to greases containing such thickeners.
  • the invention provides for making grease thickenersby fusing aldehydes, particularly branched-chain aldehydes with caustic alkali, producing a metal soap fromthe acid so formed and incorporating this metal soap into a lubricating oil in grease making proportions. In a preferred embodiment of the invention, the fusion is carried out in the presence of lubricating oil.
  • Lubricating greases normally consist of lubricating oils thickened by alkali and alkaline earth metal soaps or other thickeners to a solid or semi-solid consistency.
  • the soaps may be prepared by the neutralization of high molecular weight fatty acids or by the saponification of fats which is usually carried out in a portion of the oil to be thickened.
  • the present invention pertains to highly valuable, stable lubricating greases in which the high molecular weight fatty acids are replaced or at least supplemented by a new grease making material. It has now been found that such greases may be prepared by incorporating into lubricatingloils a 'grease' thickener obtained by fusing suitable aldehydeaparticularly branched-chain aliphatic aldehydes with alkali, particularlycaustic soda or potash at temperatures of about 350-620" R, preferably about 500-560 R, for a time sufiicient to form the alkali metal salt of the acid corresponding to the aldehyde used.
  • the chemical reaction taking place during the fusion process may be illustrated by the following equation? RCl-lO+MOH- H2+RCOOM wherein R maybe a branched-chain aliphatic radical and M is analkali metal such as sodium or potassium.
  • Theme of aldehydes introduces no complication into the grease making procedure. While alkali fusion of 2 the aldehyde may be carried out in a separate preliminary acid-forming stage, the greases are preferably produced essentially in a single process step in which the aldehyde is fused with alkali in the lubricating oil base in grease making proportions and at grease making conditions, although at somewhat higher temperatures. At the conclusion of the fusion process a finished grease is obtained.
  • Aldehydes useful for the purposes :of the present invention have become available in large quantities as intermediate or final products of various synthesis processes and more particularly as products and by-products of the well-known 0x0 synthesis.
  • the last-named process involves the catalytic reaction of olefins with carbon monoxide and hydrogen at elevated temperatures, say about BOW-400 F, and pressures of about 2500 to 4000 p. s. i. g. in the presence of group VIII metal catalysts, particularly cobalt catalysts, to form saturated oldehydes having one carbon atom more than the olefin originally used.
  • aldehydes may be used which, upon alkali fusion, yield acids or salts having about l030 carbon atoms per molecule.
  • aldehydes suitable for the invention straight or branched-chain aldehydes may be used. Oxo-aldehydes having 10 or more carbon atoms are preferred.
  • lower molecular weight aldehydes, such as Cs andCq aldehydes may be used by promoting an aldol condensation in the course containing 10 or more carbon atoms.
  • aldehydes of even lower molecularweight such as C2 or C3 aldehydes
  • aldehydes of higher molecular weight examples include acetaldehyde, propionaldehyde, butyr-aldehyde, etc.
  • aldolization two molecules of aldehyde condense with the elimination of water to yield an unsaturated aldehyde of higher molecular weight.
  • aldolization generally occurs to some extent with all aldehydes that have an alpha hydrogen atom.
  • the alkali-fused product consists of a mixture of soaps of the acid corresponding to the original aldehyde and of the acid corresponding to the aldol product.
  • Particularly desirable starting materials are the 0x0 aldehydes obtained by oxonation of polymerized olefins or olefins from cracked waxes, cracked petrolatums and other high molecular Weight hydrocarbon products, for example Fischer-Tropsch olefins.
  • olefin polymers such as polymers of propylene, butylene, isobutylene, amylene, etc., for example tetrapropylene, triisobutylene, pentapropylene, tetraisobutylene, hexapropylene, pentaisobutylene, etc., as Well as copolymers such as those produced from propylene and butylene, etc.
  • aldehydes are decanal, dodecanal, isododecanal, isotridecanal, tetradecanal, isopentadecanal, isohexadecenal, octadecanal, iso-octadecanal, isooctaclecenal, iso-nonadecanal, iso-pentacosanal, iso-hexacosenal,etc.
  • Oxo-aldehydes are believed to have compositions generallyanalogous to that specified above, chain lengths and degree of branching depending on the type of olefins used. It is noted in this respect that even when pure straight-chain olefins are used as the starting materials, the aldehydes have some branching.
  • This settling tendency of the alkali in the lubricating oil-aldehyde mixture is negligible when a sufficient amount of a solid suspending agent is present in the reaction mixture.
  • Most desirable suspending agents are those which serve simultaneously as grease thickeners, such as soaps of high molecular weight fatty acids, silica gel, carbon black, bentones, Attapulgus clay modifications, etc. Soaps, particularly sodium soaps of high molecular weight fatty acids are preferred for this purpose.
  • the melting points of most of these soaps in lubricating oil is rather low, usually below 400 F. Thus, at the high reaction or fusion temperature of about 500 F.
  • soaps are liquid when used as such and do not entirely counteract the settling tendency of the alkali.
  • This difliculty may be overcome in accordance with a specific embodiment of the invention by using the salt, preferably the alkali metal salt, of a low molecular weight acid in addition to the high molecular weight. fatty acid soap. In this manner, soap-salt complexes are formed 4 which melt well above 500 F. and thus form an excellent suspending agent.
  • soaps or soap-salt complexes are preferably formed in situ by neutralization of the corresponding acids in the aldehyde-oil mixture with alkali added in amounts suflicient for this neutralization and for the subsequent fusion which takes place at considerably higher temperatures.
  • High molecular weight acids useful for this purpose include hydrogenated fish oil acids, Cm-Czz naturally occurring acids of animal or vegetable origin, etc. These acids may be used in amounts ranging from about 2-30 wt. percent based on the finished product.
  • Suitable low molecular weight acids include acetic, furoic, acrylic and similar acids to be used in proportions of about 1-10 wt. percent based on the finished product.
  • Esters of the high and/ or low molecular weight acids may be used in place of the free acids in corresponding proportions. In this case, the alcohol portions of the esters are converted into acids and the corresponding soaps by alkali fusion. If esters of low molecular weight alcohols are used, elevated pressures may be employed to prevent volatilization of the alcohols. Of course, esters of non-volatile low molecular weight alcohols, such as polyhydroxy alcohol esters, e. g. sorbitol acetate, glycol acetate, etc. may be used. Particularly the high molecular weight type of acids or their esters used for this purpose may also be prepared by alakil fusion of 0x0 aldehydes. In this case, a portion of the product of the alkali fusion process in which the principal grease thickener is prepared in accordance with the invention may be returned to the fusion stage to serve as an agent preventing settling of the alkali.
  • Soaps of high molecular weight fatty acids and/or soap-salt complexes of the type specified may be incorporated in the greases of the present invention to improve high temperature or other characteristics even if no suspending agents are required.
  • This is useful when branched-chain aldehydes are employed, since it has been found that the use of soaps of branched chain acids as the sole grease thickeners often tend to form rubbery or cohesive structures which may be undesirable.
  • these branched chain soaps are mixed with straight chain soaps derived from fatty acids, this c-ohesive structure is largely eliminated or modified to an extent that is desirable for certain purposes.
  • the soaps formed by alkali fusion of aldehydes in the presence of other fatty acid soaps consistently yield excellent smooth greases.
  • Other conventional thickeners, anti-oxidants, corrosion inhibitors, tackiness agents, loadcarrying compounds, viscosity index improvers, oiliness agents, and the like may be added prior, during and/or after the fusion process as will be apparent to those skilled in the art.
  • the base oil used as menstruum during the fusion process should be a mineral lubricating oil.
  • synthetic lubricating oils such as a dibasic acid ester (e. g. di-2-ethyl hexyl sebacate, adipate, etc.), polyglycol type synthetic oils, esters of dibasic acids and polyhydric alcohols, etc., as well as alkyl silicates, carbonates, formals, acetals, etc., may be used alone or in addition to mineral lubricating oil to bring the grease to the desired consistency.
  • the oil base preferably comprises about 50 to about of the total weight of the finished grease.
  • the alkali fusion of the invention may be carried out in two stages.
  • the aldehyde to be fused may be added to a molten mixture of alkali and mineral oil, preferably a heavy paraflinic oil maintained at fusion temperatureof, say, about 400- 620 F.
  • the aldehyde and alkali may be used in substantially stoichiometric proportions, When all the aldehyde has been added, heating may be continued at these temperatures until gas evolution substantially ceases.
  • the acid formed may be recovered from the reaction mixture after cooling, by dilution with water followed by extraction of the oil and any unreacted aldehyde with a light hydrocarbon solvent, such as heptane or the like, and acidification of the aqueous rafiinate. If desired, the free acid may be purified by vacuum distillation.
  • the acid so prepared may then be introduced into a lubricating oil base stock, other high and/or low molecular weight fatty acids as well as other grease additives may be added and the mixture may be converted into a grease by the addition of at least sufficient caustic alkali, preferably in aqueous solution, to neutralize the acids present. Conventional grease making conditions including temperatures of about 350-500 F. may be used in this stage.
  • the soap derived from the aldehyde by alkali fusion should form at least 20 wt. percent and preferably about 30-50 wt. percent of the grease thickener or about 2.020 wt. percent of the finished grease.
  • the remainder of the grease thickener is preferably made up by a suitable soapsalt complex of the type described above.
  • the proportion of soap derived from aldehyde to soaps and salts derived from other acids may be about 1:4 to 4:1 and preferably is about 1:1.
  • the grease making procedure may be quite generally as follows.
  • a mineral lubricating oil base is mixed with the aldehyde and the mixture is heated to about 130180 F.
  • the alkali is added preferably in the form of an aqueous solution of about 30-50% concentration.
  • the mass is then dehydrated at temperatures of about 300 400 F. for about 24 hours. Thereafter, the temperature is increased to a fusion temperature of about 400620 F. and maintained Within this range until gas evolution has receded appreciably, which takes place usually after about 1-3 hours.
  • the grease may then be allowed to cool under stirring to about 200-250 F. at which level further additives may be introduced. Finally, the grease may be poured into pans toibe cooled to room temperature.
  • a similar procedure is employed when the aldehyde is subjected to alkali fusion in situ in the presence of suspending agents, such as soaps of high molecular weight fatty acids or complexes of such soaps with low molecular Weight fatty acid salts in accordance with the preferred embodiment of the invention.
  • suspending agents such as soaps of high molecular weight fatty acids or complexes of such soaps with low molecular Weight fatty acid salts in accordance with the preferred embodiment of the invention.
  • the high molecular weight acids are added to the mineral oil together with the aldehyde while the low molecular weight acid may be added after the initial heating stage immediately prior to the alkali addition.
  • suliicient caustic alkali to neutralize the acids and convert the aldehyde to soap is added, preferably in the form of an aqueous solution of about 40-50% and the mixture is heated at a saponification temperature of about 300-400 F. until the acids are converted to soaps and salts and all the Water is volatilized. Alkali fusion is then carried out substantially as described above, except that less violent stirring is required.
  • Example II The grease of Example I was mixed with an equal quantity of a high viscosity index, solvent extracted highly parafiinic lubricating grade mineral oil having a viscosity of 383.9 5. S. U. at F. and of 58.2 S. S. U. at 210 F. with a V. I. of 1032. A grease could not be prepared as described in this oil due to the poor solvency and crystallization of the soap in this non-polar medium, However, as large "a quantity of this oil is desirable in the grease as is compatible with structural stability due to its low volatility, good oxidation stability and excellent viscositytemperatur e relationship.
  • the invention is not limited to the specific figures of the foregoing examples.
  • the relative proportions of the grease constituents may be varied within the limits indicated above to obtain greases of different consistency and varying characteristics.
  • the process of preparing lubricating grease compositions which comprises mixing an aliphatic aldehyde having an alpha hydrogen and from about 10 to 30 carbon atoms per molecule and a high molecular weight carboxylic acid having from about 12 to 22 carbon atoms per molecule with a dispersing proportion of mineral lubricating oil, heating the mixture to about 130 to 180 F., adding a low molecular weight carboxylic acid and alkali sufiicient for neutralization of said acid and for alkali fusion of said aldehyde to said heated mixture, dehydrating the mixture at a temperature of about 300 to 400 F., heatingv the dehydrated mixture at a fusion temperature of about 400 to 620 F. sufficient to cause fusion between said alkali and said aldehyde until gas evolution recedes, and then cooling the grease mixture to obtain said lubricating grease composition.
  • aldehyde is an octadecenyl aldehyde made by aldolization of x0 nonyl aldehyde prepared by reacting a Ca olefin with carbon monoxide and hydrogen at elevated carbonylation temperatures and pressures in the presence of a group VIII catalyst.
  • the process of preparing lubricating greases which comprises admixing a branched chain aliphatic aldehyde containing an alpha hydrogen and having 10 to 30 carbon atoms per molecule with a mineral lubricating oil, heat ing the admixture to a temperature in the range of 120 to 180 F., adding an aqueous solution of an alkali in an amount sufficient foralkali fusion of said aldehyde, dehydrating the mixture at a temperature in the range of 300 to 400 F., then raising the temperature to a fusion temperature in the range of 400 to 620 F., maintaining 1 8 said fusion temperature until gas evolution has appreciably receded and fusion between said alkali and said aldehyde has occurred.
  • the process of preparing lubricating greases which comprises admixing an aldehyde, as defined below, with a mineral lubricating oil, heating the mixture to a temperature in the range of to F., adding an aqueous solution of an alkali sufficient for alkali fusion of said aldehyde, dehydrating the mixture at a temperature in the range of 300 to 400 F., then raising the temperature to a fusion temperature in the range of 400 to 620 F., maintaining said fusion temperature until gas evolution has receded appreciably and alkali fusion has occurred between said alkali and said aldehyde, said aldehyde being a branched chain aliphatic aldehyde containing an alpha hydrogen and 10 to 30 carbon atoms per molecule, and being prepared by reacting an olefin containing one carbon atom less than said aldehyde with carbon monoxide and hydrogen at an elevated carbonylation temperature and pressure in the presence of a group VIII metal catalyst.

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  • Inorganic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
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US327166A 1952-12-20 1952-12-20 Grease process utilizing the alkali fusion of aldehydes Expired - Lifetime US2801973A (en)

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US327166A US2801973A (en) 1952-12-20 1952-12-20 Grease process utilizing the alkali fusion of aldehydes
GB30946/53A GB753339A (en) 1952-12-20 1953-11-09 Preparation of metal carboxylates and lubricating greases containing them
FR1092698D FR1092698A (fr) 1952-12-20 1953-12-09 Graisses lubrifiantes
DEST7499A DE967837C (de) 1952-12-20 1953-12-17 Verfahren zur Herstellung von Schmierfetten

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US2962441A (en) * 1957-05-23 1960-11-29 Exxon Research Engineering Co Alkali fusion products of cyclohexenones in lubricant manufacture
US3000825A (en) * 1958-12-23 1961-09-19 Exxon Research Engineering Co Lubricants containing metal salts of oxonated polymers

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US2449312A (en) * 1947-05-07 1948-09-14 Socony Vacuum Oil Co Inc Block greases
US2454047A (en) * 1947-05-09 1948-11-16 Shell Dev Conversion of alicyclic aldehydes
US2468099A (en) * 1947-10-01 1949-04-26 Standard Oil Dev Co High-temperature grease
US2470859A (en) * 1948-02-25 1949-05-24 Du Pont Nonanoic acid
US2516137A (en) * 1948-10-30 1950-07-25 Standard Oil Dev Co High-temperature lubricating greases
US2537577A (en) * 1948-11-10 1951-01-09 Standard Oil Dev Co Selective oxidation process for producing fatty acids and alcohols
US2575286A (en) * 1949-07-29 1951-11-13 Standard Oil Dev Co Lubricating grease composition
US2576032A (en) * 1949-05-05 1951-11-20 Standard Oil Dev Co Lubricating grease
US2591586A (en) * 1950-09-30 1952-04-01 Standard Oil Dev Co High-temperature lubricating greases
US2594341A (en) * 1949-09-13 1952-04-29 Standard Oil Dev Co Utilization of oxo bottoms
US2606153A (en) * 1951-04-25 1952-08-05 Gen Electric Silicone greases
US2628202A (en) * 1949-09-23 1953-02-10 Leffingwell Chemical Company Soap useful for making lubricating greases
US2628195A (en) * 1949-09-23 1953-02-10 Leffingwell Chemical Company Lubricating grease
US2628938A (en) * 1950-03-17 1953-02-17 Phillips Petroleum Co Production of greases using reaction products of alpha-hydroxy fatty acids
US2648694A (en) * 1950-09-16 1953-08-11 Standard Oil Dev Co Higher fatty acid synthesis from oxo bottoms

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US2318769A (en) * 1941-11-06 1943-05-11 Rockwood Sprinkler Co Method of making nozzles

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US2449312A (en) * 1947-05-07 1948-09-14 Socony Vacuum Oil Co Inc Block greases
US2454047A (en) * 1947-05-09 1948-11-16 Shell Dev Conversion of alicyclic aldehydes
US2468099A (en) * 1947-10-01 1949-04-26 Standard Oil Dev Co High-temperature grease
US2470859A (en) * 1948-02-25 1949-05-24 Du Pont Nonanoic acid
US2516137A (en) * 1948-10-30 1950-07-25 Standard Oil Dev Co High-temperature lubricating greases
US2537577A (en) * 1948-11-10 1951-01-09 Standard Oil Dev Co Selective oxidation process for producing fatty acids and alcohols
US2576032A (en) * 1949-05-05 1951-11-20 Standard Oil Dev Co Lubricating grease
US2575286A (en) * 1949-07-29 1951-11-13 Standard Oil Dev Co Lubricating grease composition
US2594341A (en) * 1949-09-13 1952-04-29 Standard Oil Dev Co Utilization of oxo bottoms
US2628202A (en) * 1949-09-23 1953-02-10 Leffingwell Chemical Company Soap useful for making lubricating greases
US2628195A (en) * 1949-09-23 1953-02-10 Leffingwell Chemical Company Lubricating grease
US2628938A (en) * 1950-03-17 1953-02-17 Phillips Petroleum Co Production of greases using reaction products of alpha-hydroxy fatty acids
US2648694A (en) * 1950-09-16 1953-08-11 Standard Oil Dev Co Higher fatty acid synthesis from oxo bottoms
US2591586A (en) * 1950-09-30 1952-04-01 Standard Oil Dev Co High-temperature lubricating greases
US2606153A (en) * 1951-04-25 1952-08-05 Gen Electric Silicone greases

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2962441A (en) * 1957-05-23 1960-11-29 Exxon Research Engineering Co Alkali fusion products of cyclohexenones in lubricant manufacture
US3000825A (en) * 1958-12-23 1961-09-19 Exxon Research Engineering Co Lubricants containing metal salts of oxonated polymers

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FR1092698A (fr) 1955-04-26
GB753339A (en) 1956-07-25
DE967837C (de) 1957-12-19

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