Lubricating oil additive

Page 1 — bibliographic record

Page 2

of N-carboxyglycine is disclosed in A. C. Farthing, J.

LUBRICATING OL ADDITIVE Chem. Soc. 1950, 3213.

FIELD OF THE INVENTION SUMMARY OF THE INVENTION

This invention relates to a method for preparing lu A process is disclosed for the preparation of a lubri bricating oil additives, particularly overbased lubricat cating oil additive which comprises contacting under ing oil additives, to the additives themselves, and to reaction conditions an amino acid and a basically react lubricating oil compositions containing the additives. ing metal compound, said contacting taking place in the With the increasing severity of operating conditions presence of at least one suspending agent for said basi of the engines caused in part by the deteriorating quality cally reacting metal compound and in the presence of a of fuels for these engines, there is a need for composi hydroxylic promoter.

tions which can lubricate and maintain the cleanliness of the engine while, at the same time, neutralizing large DETAILED DESCRIPTION OF THE quantities of acids which result from the use of fuels INVENTION having an increased sulfur content. Conventional lubri 15 The essential components necessary to produce the cating oil additives used to neutralize base contain ash additive of the present invention are an amino acid, a forming components, generally metallic salts. As in basically reacting metal compound, a suspending agent creasing amounts of the acid-neutralizing components for the basically reacting metal compound, and a reac are used in formulations, the amount of ash in the corn tion-promoting amount of a hydroxylic promoter. position often exceeds the amount of ash for which the 20 engine is designed. The Amino Acid New additives are needed which can maintain the The nitrogen portion of the amino acid serves as a cleanliness of the engine and neutralize the large source of supply of non-ash-forming basic material in amounts of acid being formed from the increased use of the lubricating high-sulfur fuel, while at the same time not exceeding 25 acid' is meant oil any additives of this invention. By “amino organic acid containing at least one the ash requirements of the engines being lubricated. primary, secondary or tertiary amine (-NC) group The preparation of conventional additives which are overbased to obtain additional acid-neutralizing effi and at least one acidic carboxyl (-COOH) group. Mix ciency is taught in U.S. Pat. No. 3,126,340. The additive tures of different amino acids can be used. described in this patent is prepared by treating a lubri 30 Representative amino acids useful in the present in cating oil sulfonate dispersant with an alkaline earth vention include: glycine, alanine, beta-alanine, valine, metal oxide and hydroxide and then introducing carbon leucine, isoleucine, phenylalanine, serine, threonine, tyrosine, methionine, 6-aminohexanoic acid, proline, dioxide and ammonia into the mixture followed by heat hydroxyproline, tryptophan, histidine, lysine, hydroxyl ing the mixture in the presence of water to convert the ysine, arginine, aspartic ammonium carbamate formed from the carbon dioxide 35 acid, asparagine, glutamic acid, and ammonia to an alkaline earth metal carbonate. The glutamine, cysteine, cystine, ethylenediaminetetraacetic alkaline earth metal carbonate is the acid-neutralizing acid and nitrilotriacetic acid and other alpha-amino portion of the composition. acids containing 1 to 5 carboxyl groups. U.S. Pat. No. 3,524,814 teaches the preparation of an Particularly preferred are the amino acids which are overbased alkaline earth metal sulfonate by introducing readily available in commercial duantities such as gly a mixture of carbon dioxide and ammonia, in an amount cine, beta-alanine, nitrilotriacetic acid, etc. Also partic sufficient to form a catalytic amount of ammonium ularly preferred are the alpha- or beta-amino acids such carbamate, into a lubricating oil having in suspension a as alpha- or beta-alanine.

neutral alkaline earth metal sulfonate containing an Numerous processes for the production of amino alkaline earth oxide. After the catalytic amount of an 45 acids are well known in the art and the amino acids of monium carbamate is preformed, carbon dioxide is con the present invention.can be prepared in situ, if desired. tinuously introduced into the reaction mixture until For example, glycine can be prepared from the well substantially all of the alkaline earth oxide is converted known reaction of ammonia, formaldehyde and potas to alkaline earth metal carbonate. The metallic carbon sium cyanide or sodium cyanide. See for example, in ate provides the reserve alkalinity in the sulfonate. As a 50 U.S. Pat. No. 2,663,713, the disclosure of which is in post-treatment step, water is added to the reaction mix corporated herein by reference.

ture. The addition of water decomposes any ammonium The Basically Reacting Metallic Compound carbamate still present in the reaction mixture.

U.S. Pat. No. 4,034,037 teaches the production of The basically reacting metallic compound is any me metal carboxylates or N-organic substituted carbamates 55 tallic compound which reacts under basic conditions, by reaction of a carboxylic acid or carbon dioxide with i.e., at a pH greater than 7.0, to form a salt of an organic an amine in the presence of a soluble metal salt. These acid. Typical of such metallic compounds are calcium salts are disclosed to be useful as lubricating oil addi oxide, hydroxide or methoxide, magnesium oxide, hy tives. droxide or methoxide, barium oxide or hydroxide, alu The production of various alkali and alkaline earth 60 minum hydroxide, sodium hydroxide, lithium hydrox metal salts of N-carboxy amino acids in aqueous and ide, sodium alkoxide, and the like. Useful alkoxides are alcohol systems is well known in the art. See, for exam the lower-molecular-weight alkoxides such as methox ple, the various articles by M. Siegfried (Z. Physiol. ide, ethoxide, t-butoxide, and the like. Preferably the Chem. 44,85 (1905; 46,401 1906; 54,436 (1908) which oxide or hydroxide of a Group II metal or a Group I disclose the production of barium and calcium salts of 65 metal hydroxide is used.

N-carboxy amino acids. The mercury salts of N-car Preferred lubricating oil additives are prepared from boxy amino acids are disclosed in C. Neuberg and J. magnesium, barium and calcium oxides or hydroxides, Kerb, Biochemische Z., 40,498 (1912). The sodium salt although sodium hydroxide is often desirable in certain

Page 3

applications. Most preferred for use in lubricating oil Ordinarily 4 the alkyl or alkenyl group contains from 50 additives are those compositions prepared from a mag to 300 carbon atoms.

nesium or calcium-containing, basically reacting com Alkali metal and alkaline earth metal phenates are pound, especially calcium oxide, calcium hydroxide, well known in the art and are the alkali metal or alkaline and magnesium oxide. earth metal salt of an oil-soluble alkyl-substituted phe The Suspending Agent nol. The composition may be sulfurized. Typical phe nates are prepared by neutralizing a C8-128 alkylphenol

The suspending agent, which must be oil-soluble, is with calcium hydroxide or oxide.

used to keep the basically reacting metallic component Mannich bases are useful suspending agents. Mannich in solution so that it can be an effective portion of the 10 bases are prepared by reacting an oil-soluble phenolic or additive composition. Many of the useful suspending alcoholic material, such as alkylphenol, with an alde agents also have dispersant activity in the final lubricat hyde, such as formaldehyde or acetaldehyde, and a ing oil additive composition. Typical suspending agents nitrogen-containing compound. Typical Mannich bases include alkali metal or alkaline earth metal hydrocarbyl 15 contain from about 8 to 128 or more carbon atoms in the sulfonates or fatty acid carboxylates, hydrocarbyl suc alkyl group. If desired, the alkaline earth metal salt of cinimides, hydrocarbyl succinates, hydrocarbyl suc the phenolic-type Mannich base may be used as a sus cinic anhydrides, alkali metal or alkaline earth metal pending agent.

alkylphenates, alkylphenol-type Mannich bases and alkaline earth metal salts of such Mannich bases. Mix tures of suspending agents are also useful in carrying out 20 Reaction Promoter the process of this invention. A reaction-promoting amount of a hydroxylic pro The alkali metal and alkaline earth metal hydrocarby moter is necessary for the reaction to proceed at an sulfonates useful in the process of this invention are well acceptable rate. Generally from 0.1 to 10 weight per known in the art. The hydrocarby group must have a 25 cent or more of the reaction mixture may be the hydrox sufficient number of carbon atoms to render the sulfo ylic promoter. The promoter is believed to function as nate molecule oil soluble. Ordinarily, the hydrocarbyl a solubilizing agent for the basically reacting metal portion has at least 20 carbon atoms and may be aro compound. The promoter is preferably water or an matic or aliphatic, but is usually alkylaromatic. Certain alkanol of 1 to 6 carbon atoms or an alkanediol of 2 to sulfonates are typically prepared by sulfonating a petro 30 6 carbon atoms such as methanol, ethanol, isopropanol, leum fraction having aromatic groups, usually mono- or butanol, ethylene glycol, 1,4-butanediol and the like. dialkylbenzene groups, and then forming the metal salt Most preferred are water, ethanol and methanol. Mix of the sulfonic acid material. Other feedstocks used for tures of these promoters may also be used, chosen so as preparing these sulfonates include synthetically alkyl to keep water formed during the reaction in solution. ated benzenes and aliphatic hydrocarbons prepared by 35 Chalcogen Reactant polymerizing a mono- or diolefin, for example, a polyisobutenyl group prepared by polymerizing isobu Although not an essential reactant, it is preferred that tene. The metallic salts are formed directly or by me the reaction take place in the presence of a chalcogen tathesis using well-known procedures. compound. Suitable chalcogen compounds include car Succinimide dispersants are also well known in the bon dioxide, carbon disulfide, carbon oxysulfide, sulfur art, and a general method for their preparation is found dioxide or mixtures thereof. While the chalcogen reac in U.S. Pat. Nos. 3,219,666, 3,172,892 and 3,272,746, the tant is ordinarily added in the gaseous form, it may be disclosures of which are hereby incorporated by refer added in liquid or solid form, for example as dry ice or ence. These compositions are prepared by reacting an liquid sulfur dioxide. Carbon dioxide is the preferred oil-soluble alkyl or alkenyl succinic acid or anhydride 45 chalcogen reactant. When a chalcogen reactant is uti with a nitrogen-containing compound. The succinimide lized, the amino acid must contain a primary or second may be of the type commonly known as a mono- or ary amine group. The chalcogen compound is a pre bis-succinimide. Preferred nitrogen compounds used in ferred reactant since it increases the alkalinity value of making the succinimides are those known as the lubricating oil additives by incorporating more of the ethyleneamines, and particularly preferred are trie 50 basically reacting metallic compound. thylenetetraamine and tetraethylenepentamine. The Solvent preferred alkyl or alkenyl groups contain from 50 to 300 carbon atoms, and the most preferred compositions are The reaction is carried out in a suitable solvent. Pref. prepared from polyisobutylene. When this type of sus erably the solvent is a lubricating oil so that no removal pending agent is employed, the amine portion will con 55 of the solvent is necessary before incorporation of the tribute to the alkalinity value. additive into the lubricating oil. Other useful solvents The oil-soluble alkyl or alkenyl succinic anhydrides are lower-boiling hydrocarbon solvents such as hexane used in preparing the succinimides are themselves useful or hydrocarbon thinner. Mixtures of lubricating oil with as suspending agents; however, they are most preferred hexane or hydrocarbon thinner are also useful. After for use as co-suspending agents, particularly in combi preparation is complete, the lower-boiling solvents are nation with a sulfonate suspending agent. Preferably the readily removed by heating, if desired. alkyl or alkenyl portion contains from 50 to 300 carbon Reaction Conditions atOS.

The succinate esters are prepared by reacting an alco The process of this invention may be carried out at hol with an alkenyl or alkyl succinic anhydride as de 65 any temperature from the freezing point of the mixture scribed above, using a procedure such as that described to its boiling point. Ordinarily the reaction is conducted in U.S. Pat. Nos. 3,381,022 and 3,522,179, the disclo at a temperature of from 0 to 75° C., preferably 20' to sures of which are hereby incorporated by reference. 75° C. and most preferably 25 to 50° C. While the

Page 4

reaction proceeds satisfactorily at atmospheric pressure, posed to the decomposition products of sulfur-contain higher or lower pressures may be used if desired. ing diesel fuels. Typical alkalinity values for additive The ratio of the basically reacting metallic compound compositions of this invention range from about 30 to to the chalcogen and the amino acid is such that from 400 or more.

about 1/10 to of the alkalinity value of the final com- 5 Lubricant compositions containing the additives of position is contributed by the ashless amino-containing this invention are prepared by admixing through con material. Preferably it is desirable to have at least one ventional admixing techniques the appropriate amount equivalent of the basically reacting metallic compound of the additive of this invention with a lubricating oil. for each equivalent of the amino compound. The ratio The selection of a particular base oil depends on the will vary depending on the structure of the amino acid O contemplated application of the lubricant and on the used and the amount of alkalinity value desired from the presence of other additives. Generally, the amount of ashless nitrogen portion of the amino acid. For a simple additive of this invention used in the lubricating oil will amino acid (glycine, beta-alanine), generally at least vary from 0.1 to 40% by weight, and preferably from 2 two equivalents of metallic compound per mol of amino to 35% by weight. The resulting lubricating oil will acid are used, whereas for a more complex amino acid 15 usually have an alkalinity value in the range of 1 to 120, (glutamic acid, lysine, nitrilotriacetic acid), generally at preferably 2.5 to 100.

least three equivalents are employed, though fewer The lubricating oil which may be used in this inven equivalents may be used if a higher proportion of ash tion includes a wide variety of hydrocarbon oils such as less alkalinity value is desired. Under typical conditions naphthenic bases, paraffin bases and mixed-base oils. and based on 1 equivalent of the basically reacting me 20 The lubricating oils may be used individually or in com tallic compound, the reaction mixture would contain bination and generally have a viscosity which ranges from 0.1 to 2.0, preferably from 0.3-0.5, equivalents of from 50 to 5000 SUS (Saybolt Universal Seconds) and the amino compound; from 0-1, preferably 0.3-0.5, usually from 100 to 1500' SUS at 38 C.

equivalents of chalcogen compound; and from 2 to 20, In many instances it may be advantageous to form preferably 4 to 10, parts by weight of the suspending 25 concentrates of the additives of this invention within a agent per part of the basically reacting metallic com carrier liquid. These concentrates provide a convenient pound. The hydrocarbon solvent should be present in method of handling and transporting the additives of sufficient amount to enable good mixing of the reactants this invention before their subsequent dilution and use. and is usually present as from 5 to 50 and preferably 10 The concentration of the additives of this invention to 25 milliliters per gram of basically reacting metallic 30 within the concentrates may vary from 90 to 40% by compound. From 0 to 5, preferably 1 to 2, milliliters of weight with the oil comprising from 10 to 60% by the promoter per gram of basically reacting metallic weight. It is preferred to maintain the concentration of compound is also used. the additives between about 50 and 70% by weight. The In a preferred method for carrying out the reaction, a preferred method of obtaining concentrates is to carry sodium, calcium or magnesium alkylbenzene sulfonate 35 out the preparation of the additive in a limited amount is used as the suspending agent. It is also preferred to of lubricating oil, as will be held in making the final use an alkenylsuccinimide or an alkenylsuccinic anhy dilute lubricant composition. Alternatively, the additive dride as a co-suspending agent. If this combination of may be prepared in a low-boiling hydrocarbon which is solubilizing agents is used, an increased alkalinity value removed by distillation after adding a limited amount of for the product is obtained when, prior to addition of 40 lubricating oil.

the amino compound and the basically reacting mate As desired, other additives may be included in the rial, preferably an alkaline earth metal oxide or hydrox lubricating oil compositions of this invention. These ide, the mixture of components and the solvent is pre additives include antioxidants or oxidation inhibitors, treated with a small amount of chalcogen, for example dispersants, rust inhibitors, anticorrosive agents, and so with from 1 to 10%, preferably about 5%, of the total 45 forth. Other types of lubricating oil additives which amount of chalcogen. may be employed include antifoam agents, stabilizers, Compositions antistain agents, tackiness agents, antichatter agents, dropping point improvers, antisquawk agents, extreme

The compositions prepared by this invention provide pressure agents, odor control agents, and the like. a high alkalinity value at a lower ash content than is 50 EXAMPLES present in most conventional dispersants and/or acid neutralizers used as lubricating oil additives. The following examples are presented to illustrate Alkalinity value is one method of specifying the de this invention, and are not in any way to be interpreted gree of overbasing of the lubricating oil composition. It as limiting the scope of the invention. is also a measure of the acid-neutralizing properties of 55 EXAMPLE 1 the composition. The method for determining the alka linity value commonly used for a composition is set To a 1-liter, 3-neck flask were charged 180grams of forth in ASTM Method D-2896. Briefly, the alkalinity a 67% concentrate of a calcium alkylated aromatic value is the total base number given as milligrams of sulfonate in hydrocarbon thinner, 400 ml of a hydrocar potassium hydroxide per gram of sample. It is the quan- 60 bon thinner, 10.3 grams (0.25 mol) magnesium oxide tity of potassium hydroxide required to neutralize the (Maglite A, Merck, 200 m2/g), 18.8 grams (0.25 mol) same amount of perchloric acid that 1 gram of the sam glycine and 10.0 ml water. The mixture was stirred at ple neutralizes. For example, if a composition has the room temperature and warmed to 40 C. and then 3 same acid-neutralizing capacity per gram as 10 mg of grams of carbon dioxide was added over a 25-minute potassium hydroxide, the composition is given an alka- 65 period at a temperature of from 40 to 45 C. Then 10 linity value of 10. The lower limit of alkalinity value is ml of 100% ethanol was added and 2 grams of carbon 0 for a neutral composition. Values of 200 or more are dioxide was added over a period of 20 minutes at tem especially desirable for use in lubricants which are ex peratures ranging from 45 to 55 C. An additional 5 ml

Page 5

of 100% ethanol was added and an additional 8 grams of EXAMPLE 6 carbon dioxide was added over a period of 76 minutes at 55 C. The reaction mixture was then centrifuged for 20 To a 5-liter, 3-neck flask was charged 900 grams of a minutes at 12,000 RPM and then filtered throgh a pad of 67% concentrate of a calcium alkylated aromatic sulfo diatomaceous earth. The filtrate was stripped to 110° C. 5 nate in hydrocarbon thinner, 2300 ml of a hydrocarbon at 20 mm Hg pressure. The mixture yielded 142 grams thinner, 120 ml of methanol, 120 ml of water, 210 grams of product having an alkalinity value of 189.8, and con (2.8 mols) glycine and 153.2 grams (3.8 mols) magne taining 3.22% magnesium, 1.33% calcium, and 1.24% sium oxide. The mixture was stirred for 5 minutes at nitrogen. room temperature and then 126 grams of carbon dioxide 10 and 30 ml of water were added over 8 hours with the

EXAMPLE 2 temperature ranging from 28 to 41 C. The reaction mixture was filtered through a pad of diatomaceous

To a 5-liter, 3-neck flask was charged 670 grams of a earth.

67% concentrate of a calcium alkylated aromatic sulfo pressure. The filtrate was stripped to 115° C. at 20 mm Hg nate in hydrocarbon thinner, 2330 grams of a hydrocar 15 having anThe mixture yielded 1188 grams of product alkalinity value of 332.6, and containing bon thinner, 47 ml water, 75 ml 95% ethanol, 50.5 5.98% magnesium, 1.04% calcium and 2.05% nitrogen. grams magnesium oxide, and 94.0 grams glycine. The mixture was stirred and heated to 40 C. 56 grams of EXAMPLE 7 carbon dioxide was added over 2 hours, 15 minutes To a 1-liter, 3-neck flask was charged 160 grams of a while the temperature ranged from 38 to 47 C. The 20 67% concentrate of a calcium alkylated aromatic sulfo reaction mixture was filtered through a pad of diatoma nate hydrocarbon thinner, 400 ml of a hydrocarbon ceous earth. The filtrate was stripped to 110° C. at 20 thinner, 15 ml methanol, 8.0 grams (0.2 mol) magnesium mm Hg pressure. The mixture yielded 826 grams of oxide, and 7.9 grams ammonium bicarbonate. Then product having an alkalinity value of 203.6 and contain over a 10-minute period 9.8 grams (0.2 mol) of sodium ing 3.08% magnesium, 1.38% calcium, and 1.39% nitro 25 cyanide and 16.2 grams of a 37% formaldehyde solution gen. were slowly added. The mixture was warmed to 40 C.

EXAMPLE 3

and stirred for 3 hours. Then 2 ml of 37% formalde hyde was added and 1 ml of water and the mixture

To a 1-liter, 3-neck flask was charged 150 grams of a stirred for another 95 minutes. Then 11 grams of carbon 67% concentrate of a calcium alkylated aromatic sulfo 30 dioxide was added over a period of 66 minutes at tem nate in hydrocarbon, 450 ml of a hydrocarbon thinner, peratures ranging from 50” to 55 C. The reaction mix 20 ml of methanol, 10 ml of water, 37.5 grams glycine ture was stripped to 130° C. (bottoms), 95 C. (over head). The product was filtered through a pad of diato (0.5 mol) and 20.6 grams magnesium oxide. The mixture maceous was stirred and heated to 45° C. and 25 grams of carbon 35 mm Hg earth. The filtrate was stripped to 110' C. at 20 pressure. The reaction mixture yielded 182 dioxide was added over 5 hours and 13 minutes while the temperature ranged from 33 C. to 48 C. The reac grams of product having an alkalinity value of 120.0 and tion mixture was filtered through a pad of diatomaceous containing 1.41% magnesium, 1.12% calcium, 1.27% earth. The filtrate was stripped to 110° C. at 20 mm Hg nitrogen and 1.60% sodium.

What is claimed is:

pressure. The mixture yielded 184 grams of product 1. A process for the preparation of a lubricating oil having an alkalinity value of 282.4 and containing additive which comprises contacting under reaction 4.94% magnesium, 1.27% calcium, and 1.8% nitrogen. conditions a mixture of an amino acid and a basically EXAMPLE 4 reacting metal compound, said contacting taking place in the presence of a solvent and at least one suspending

To a 500-ml Erlenmeyer flask was charged 4.03 45 agent for said basically reacting metal compound and in grams (0.10 mol) magnesium oxide (Velsicol), 60.0 the presence of a hydroxylic promoter, said reaction grams of a 67% concentrate of a calcium alkylated conditions including a temperature from the freezing aromatic sulfonate in hydrocarbon thinner, 200 ml of a point to the boiling point of the mixture and based on hydrocarbon thinner, 5 ml water and 10 ml of methanol. one equivalent of the basically reacting metallic com The mixture was then stirred and 12.73 grams nitrilotri 50 pound from 0.1 to 2.0 equivalents of the amino acid and acetic acid was added. The mixture was then stirred from 2 to 20 parts by weight of the suspending agent per vigorously at room temperature overight. A small por part of the basically reacting metal compound. tion was then centrifuged for 30 minutes at 11,000 2. The process of claim 1 wherein said amino acid is RPM. The resultant clear supernatant had an alkalinity 55 an alpha-amino acid.

value of 10.84. 3. The process of claim 2 wherein said alpha-amino acid contains 1 to 5 carboxyl groups.

EXAMPLE 5 4. The process of claim 3 wherein said amino acid is To a 500-ml Erlenmeyer flask was charged 4.03 glycine.

grams magnesium oxide (0.1 mol) (Velsicol), 60.0 grams ing5.metal

The process of claim 1 wherein said basically react compound is a Group I metal hydroxide or of a 67% concentrate of a calcium alkylated aromatic Group II metal oxide or hydroxide. sulfonate in hydrocarbon thinner and 200 ml of a hydro 6. The process of claim 1 wherein said suspending carbon thinner. The mixture was then stirred and 14.6 agent is an alkali metal or alkaline earth metal hydrocar grams (0.05 mol) ethylenediaminetetraacetic acid was bylsulfonate, a hydrocarbylsuccinimide, a hyrocarbyl added. The mixture was then stirred at room tempera 65 succinate, a hydrocarbylsuccinic anhydride, an alkali ture overnight and the reaction mixture was filtered metal or alkaline earth metal alkylphenate, a Mannich through a pad of diatomaceous earth. The resultant base or an alkaline earth metal salt of a Mannich base, or clear filtrati had an alkalinity value of 10.07. mixtures thereof.

Page 6

7. The process of claim 6 wherein said suspending one suspending agent for said basically reacting com agent is an alkali metal or alkaline earth metal hydrocar pound, at least one chalcogen compound selected from bylsulfonate, a hydrocarbylsuccinimide or a hydrocar carbon dioxide, carbon disulfide, carbon oxysulfide or bylsuccinic anhydride, or mixtures thereof. sulfur dioxide, and in the presence of a promoting 8. The process of claims 1, 2, 3, 4, 5, 6 or 7 wherein amount of a hydroxylic promoter, said reaction condi said amino group contains a primary or secondary tions including a temperature from the freezing point to amine group and said contacting takes place in the pres the boiling point of the mixture and based on one equiv ence of carbon dioxide, carbon disulfide, carbon oxysul alent of the basically reacting metallic compound from fide or sulfur dioxide.

9. The process of claim 8 wherein said contacting O 0.1 to 2.0 equivalents of the amino acid and from 2 to 20 parts by weight of the suspending agent per part of the takes place in the presence of carbon dioxide. basically reacting metal compound. 10. The process of claim 1 wherein said hydroxylic promoter is water, methanol, ethanol or mixtures is glycine, process 14. The of claim 13 wherein said amino acid said basically reacting metal compound is thereof.

11. The process of claim 1 wherein said amino acid is 15 calcium hydroxide or magnesium oxide, and said chal prepared in situ. cogen is carbon dioxide.

12. The process of claim 11 wherein said amino acid 15. The product prepared by the process of claims 1, is glycine and is prepared in situ from the reaction of 2, 3, 4, 5, 6, 7, 13 or 14.

ammonia, formaldehyde, and sodium or potassium cya 16. A lubricating oil composition comprising an oil of nide. 20 lubricating viscosity and from 0.1 to 40% by weight of 13. A process of the preparation of a lubricating oil a product according to claim 15.

additive which comprises contacting under reaction 17. A lubricating oil concentrate which comprises conditions a mixture of an amino acid selected from from 10 to 60% by weight of an oil of lubricating vis glycine, alpha-or beta-alanine, cystine, methionine or cosity and from 90 to 40% by weight of a product ac lysine and a basically reacting metal compound selected 25 cording to claim 16.

from calcium oxide or hydroxide, magnesium oxide or 18. The product prepared by the process of claim 8. hydroxide, lithium or sodium hydroxide, said contact 19. The product prepared by the process of claim 9. ing taking place in the presence of a solvent and at least sk k k is k