JPH045715B2 - - Google Patents

Description

[Detailed description of the invention]

It is common practice to include lubricant formulation additives to improve antiwear and rust control properties. In the past, sulfurized triglycerides, such as sulfurized lard oil, have been used, especially in combination with lightly refined aromatic perfume oils that provide sufficient solubility for the sulfurized triglycerides. There has been increasing concern about the toxicity of aromatic compounds present in such mineral oils, and lubricating formulations now consist essentially of non-aromatic oils. This change to substantially non-aromatic base oils is due to one main reason: the solubility of sulfurized triglycerides in non-aromatic mineral oils is significantly reduced, resulting in solidification and/or dropout of the sulfurized triglycerides. A problem arose. Although solubility problems have been overcome, it has been found that modified lubricating products either lack the desired lubricating properties or are unable to provide the necessary improvements in these properties. As reported in U.S. Pat. No. 3,455,896,
In a typical approach to this problem, sulfurized low molecular weight polybutenes were reacted with liquid triglycerides susceptible to sulfurization to form additives. In US Pat. No. 3,850,825, another additive was produced by sulfurization of a mixture of primary combustion lard oil and alkyl oleate. US Patent No.
No. 3,740,333, _C10 - _C16 alcohol esters of unsaturated fatty acids having 18-22 carbon atoms were combined with triglycerides and either used "as is" or sulfurized. Modification of such compositions is described in U.S. Pat.
No. 4166796, No. 4166797 and No.
Reported in issue 4188300. Although these prior art efforts have increased the solubility of sulfurized aliphatic oils to an acceptable degree, it has been found that oils with superior solubility and improved lubricity properties, such as better cold flow properties, better There is a significant need for sulfurized additives that have a combination of load-bearing and anti-friction properties with a lack of sludge formation. These improved lubricant properties also make them attractive for use in various fuel systems used for power generation and heating purposes. The present invention provides improved lubricant additive compositions comprising sulfurized aliphatic oils, methods of making the same, and oil products, including both fuels and lubricants, containing such sulfurized aliphatic oils. Regarding the composition. The additive compositions of the present invention exhibit highly desirable solubility when used in either lubricant or fuel formulations. Particularly desirable utilities of these additive compositions are generally improved performance properties,
For example, improved load support, anti-wear and friction properties, reduced levels of deposits and varnish,
and provide improved pour point depression. In particular, according to the present invention, the triglyceride contains a sulfurized, ester-converted triglyceride, and the total acid component of the triglyceride contains about 35 mol% or more of saturated aliphatic acids and about 65 mol% or less of unsaturated fatty acids. , said total acid component further comprises a) greater than about 20 mole percent monounsaturated acids, b) less than about 15 mole percent polyunsaturated fatty acids, and c) saturated aliphatic acids having from 6 to 14 carbon atoms. d) saturated aliphatic acids having 6 to 16 carbon atoms, comprising more than about 10 mole % of acids; and d) saturated fats having 18 or more carbon atoms, having less than about 15 mole %. A sulfurized, fatty oil additive composition is provided, characterized as comprising a group acid. Furthermore, the present invention relates to a process for producing such esterification and sulfurized triglycerides. The present invention further relates to lubricant and combustion compositions containing such sulfurized aliphatic oil additives and having improved performance in common applications. The additives of the present invention may be present in up to about 15% by weight in lubricant formulations and up to about 0.1% in fuel compositions.
Can be used in concentrations up to % by weight. The present invention provides additive compositions of sulfurized aliphatic oils that exhibit the required solubility in non-aromatic base oils without the disadvantages associated with prior art lubricant additive formulations, and The present invention relates to a method for producing a composition. Additionally, the compositions of the present invention exhibit improved performance properties over prior art compositions, such as improved load carrying, anti-wear and friction properties, reduced levels of deposits and varnishes in the oils used, and Shows better pour point depression. The invention likewise relates to lubricant compositions and fuel formulations comprising the additive compositions of the invention. Prior art triglycerides, typically derived from plants and animals, do not offer maximum effectiveness as lubricant additives due to the chain length and/or degree of unsaturation of the acid moieties. Modification of the acid moiety of triglycerides by transesterification results in novel triglycerides. Said triglycerides, when combined via sulfur bonds with solubilizing components such as esters and/or olefins, optimize the properties of the resulting additive. The acid portion of the triglyceride component of the additives of the present invention has less than about 65 mole percent unsaturated acids, primarily at least one ethylenic carbon-carbon double bond;
and an acid mixture having more than 35 mole % of saturated aliphatic acids. Of the total acid moieties, less than about 15 mole percent of the saturated acids have 18 or fewer carbon atoms and more than about 35 mole percent of the saturated acids have less than 18 carbon atoms. Similarly, polyunsaturated acids are less than about 15 mole percent, and monounsaturated acids are about
More than 20 mol%. Transesterification reactions are carried out on blends of (1) triglycerides, (2) triglycerides and organic acids, or (3) esters of triglycerides and organic acids. If an acid is included in the reaction and the amount of free acid present in the transesterified formulation is greater than about 15%, the free acid is preferably treated with a monoalcohol, glycol or glycerol prior to the subsequent sulfurization reaction. Esterification reduces free acid content. Esterification of the free acid can also be carried out when its concentration is less than about 15%, but this is not required. After transesterification or esterification, the reactants are combined by reaction with sulfur, whereupon a solubilizing component, such as an ester, olefin or blend thereof, is added, if desired. Sulfurization is carried out according to known procedures. This known procedure generally consists of heating the mixture with elemental sulfur at a temperature of about 300°C (149°C) to 400°C (204°C) for about 1 to about 8 hours. The sulfur content of the additives of this invention should be within the range of about 4 to about 14% by weight. The additives of the present invention preferably utilize naturally occurring triglycerides as starting compounds.
Such triglyceride compositions are described by Bailey's
Described in detail in Industrial Oil and Fat Products, Vol., 4th edition, John Wiley and Sone. Triglycerides are ester products of glycerol and one or more fatty acids, with the formula where R ₁ , R ₂ and R ₃ are
Represents a hydrocarbon group whose chain lengths can be the same or different and can also be saturated or unsaturated. Triglycerides from fish and animal oils usually contain acids with chain lengths greater than 15 carbon atoms and usually contain large amounts of monounsaturated and polyunsaturated acids. Triglycerides from certain plant species contain amounts of shorter chain acids having 10, 12 or 14 carbon atoms. These shorter chain plant-derived acids tend to be primarily saturated acids. In the method of producing the triglyceride component of the additive of the present invention, commercially available triglycerides that do not have the desired distribution of acids are transesterified with acids, esters or triglycerides that have the desired distribution of acids in higher proportions. do. After transesterification, the resulting mixture has the required average distribution of acids, preferably as triglycerides. The free acid in the transesterification product is then replaced with a monohydric alcohol, from methyl alcohol to a C ₂₀ alcohol, or with a polyhydric alcohol, e.g.
Can be esterified with glycol or glycerol. Esterification is a highly preferred procedure when the free acid content during the transesterification reaction is greater than about 15%, whereas esterification at levels below 15% is optional. Transesterification is preferably carried out in the presence of a strong acid catalyst, at approximately 400
The process is carried out at a temperature within the range of 232° C. to about 450° C. for about 1 to about 8 hours. Prior to sulfurization, the transesterified mixture can be combined with solubilizing components when seeking to further improve solubility. Esterification of such acids can provide a solubilizing factor whenever a sufficient amount of free unsaturated acid is present in the transesterified reaction product. If not,
Prior to sulfurization, additional solubilizing components are added, such as unsaturated esters or olefins. The amount of solubilized components present, prior to sulfurization, is approximately
Although it can be as high as 70% by weight, such solubilizing components, when used, are preferably present in an amount within the range of about 5 to about 55% by weight. It can be used as starting triglyceride for the production of the additives of the invention. Examples of naturally occurring triglycerides include, but are not limited to, lard oil, tallow, palm oil, and peanut oil. After transesterification, the acid part of the triglyceride is
Consisting of less than about 65 mole percent of total monounsaturated and polyunsaturated fatty acids. The acid part is approximately 20
Consisting of greater than mol %, preferably greater than about 35 mol %, monounsaturated fatty acids and less than about 15 mol % polyunsaturated fatty acids, ie, acids having more than one ethylenic carbon-carbon bond. The total saturated aliphatic acids contain greater than about 35 mole percent, preferably greater than about 30 mole percent, of said acid moieties. Of the total acid component, saturated acids having 6 to 14 carbon atoms are present in an amount greater than about 10 mol%, preferably greater than about 15 mol%, and saturated acids having 6 to 14 carbon atoms are present in an amount greater than about 10 mol%; Saturated acids having 6 to 15 carbon atoms, including acids of greater than about 20 mole percent, preferably about
Saturated acids having 18 or more carbon atoms are present in an amount greater than 35 mole % and less than about 15 mole %. The acids used are usually straight chain acids, although some branched chain acids, such as 2-ethylhexanoic acid and 2-methyldecanoic acid, have no adverse effects. Almost any alcohol can be used in any esterification step, such as glycerol, diols and monohydroxy alcohols, especially terminal primary alcohols. Branched chain alcohols, such as 2-ethylhexyl alcohol,
Isodecyl alcohol, iododecyl alcohol and a wide range of alcohols, e.g. 11-22
It is also possible to use mixtures containing alcohols having 5 carbon atoms. When used as a solubilizer, olefins
Usually contains 8 to 20 carbon atoms per molecule. It is also possible to use olefin mixtures. In one embodiment of the invention, transesterification and esterification are carried out in a number of steps by mixing the starting triglyceride, substituted acid, and alcohol together and then heating this mixture in the presence of a transesterification catalyst. Reduce and implement. Transesterification catalysts are commonly used to accelerate the reaction, but the reaction will proceed in the absence of a catalyst. The amount and type of catalyst can vary widely. Known transesterification catalysts include tetrabutyl titanate, zinc acetate, sodium carbonate, sodium hydroxide, potassium hydroxide, sodium methylate,
These include sodium sulfate, stannous oxalate, p-toluenesulfonic acid (PTSA), methanesulfonic acid (MSA), butylchlorotin dihydroxide, sulfuric acid, and phosphoric acid. p-Toluenesulfonic acid and methanesulfonic acid are preferred catalysts. The amount of catalyst used is about 0.01 to about 1% by weight, preferably about
It ranges from 0.03 to 0.5% by weight. Comparative experiments carried out in the presence or absence of transesterification catalyst showed the following degrees of completion: a) Catalyst: 0.15% methanesulfonic acid, 400㎓
(204°C) for 4 hours...approximately 72% completion; b) Catalyst: 0.1% butylchlorotin dihydroxide;
8 hours at 400°C (204°C)...approximately 44% completion; and c) Catalyst: None, 8 hours at 400°C (204°C)...approximately 21% completion. As the above comparative studies show, the transesterification reaction occurs even in the absence of catalyst, and the reaction rate is increased by the addition of catalyst. During the transesterification reaction, the presence of 0.15-1.0% by weight increases the rate of transesterification. However, during the subsequent esterification, any water added or generated during the esterification reaction should be removed as quickly as possible to bring the reaction to completion;
It is desirable to increase yield in this way. The following examples further illustrate the invention as it relates to lubricant additive compositions. In the examples, all parts and percentages are by weight unless otherwise specified. In the examples below, the HOE alcohol is 11
~22, average 16, alkyl alcohols of carbon atoms, primarily branched-chain primary alcohols, Heavy
means commercially available as Oxo Ends. Emery876 acid has approximately 11% _C9 , 2% _C10 ~
C ₁₃ , 16% C ₁₄ , 1% C ₁₅ , 42% C ₁₆ , 1%
_C17 and 12% _C18 monobasic acids and 15% _C6 ~
It is a saturated acid mixture containing _C14 dibasic acids.
Diol concentrate is about 84% diol, mainly
_C13 to _C17 alpha primary, and about 16% monohydric alcohol,
It is a mixture of primarily straight chain alcohols containing primarily _C15 - _C16 alcohols. Example 1 A blend of 67 parts primary lard oil, 28 parts crude coconut oil, and 5 parts oleic acid was prepared in the presence of 0.2% p-toluenesulfonic acid at 400-410
~210°C) for 4 hours. The acid value (AV) of this mixture increased from 16 to 20. Acid value is measured by titration (AOCS method Ca 3a-63),
It is defined as the number of milligrams of potassium hydroxide required to neutralize the free acid in 1 g of sample. To the transesterification mixture was added 8 parts of HOE alcohol and heating was continued for an additional 3 hours. The AV titer decreased to 10 during this process. The resulting product contained approximately 87% transesterified triglycerides and approximately 13% esters, excluding small amounts of free acid and alcohol. This product together with elemental sulfur contains 360-370
(182-188℃) for 3 hours, then 330℃
(166°C), and introduce air into this mixture to approx.
Sulfurization was performed by passing for 1.5 hours to remove H ₂ S or other harmful light ends. The resulting product contained 6.3% bound sulfur. Example 2 60% of the transesterified triglyceride product obtained by the procedure of Example 1 is combined with 40% of an alkyl alcohol (HOE) of an unsaturated fatty acid (tall oil fatty acid) and this mixture was sulfurized to produce a product with 7.3% bound sulfur. Example 3 A blend of 100 parts primary lard oil and 25 parts Emery 621 coconut oil fatty acid is heated to 400-410〓 (204-210°C) for 4 hours in the presence of 0.2% p-toluenesulfonic acid. did. 25 parts of HOE alcohol was added to the mixture and the mixture was heated for an additional 3 hours. The AV of this product was 11. To 150 parts of the reaction product, 20 parts of unsaturated fatty acid (tall oil fatty acid) alkyl alcohol (HOE)
In addition, this mixture was sulfurized to produce a product with 6.7% bound sulfur. Example 4 78 parts of a compound having a melting point of about 100㎓ (37.8°C),
A blend of solid triglycerides and 22 parts of Emery 621 coconut oil fatty acid was heated to 400-410°C (204-210°C) for 4 hours in the presence of 0.2% methanesulfonic acid. 20 parts of HOE alcohol was added and the reaction continued until the AV dropped to 10. 28 parts of HOE alcohol ester of tall oil fatty acids were then added, and the mixture was sulfurized.
A product with 6.5% bound sulfur was produced. This mixture contains approximately 53% transesterified triglycerides and approximately 47% HOE before sulfurization.
Contains ester. Example 5 68 parts of a compound having a melting point of about 100㎓ (37.8°C),
The solid triglycerides were mixed with 19 parts Emery 621 coconut oil fatty acid and 13 parts tall oil fatty acid.
The mixture was heated to 400-410°C (204-210°C) for 4 hours in the presence of 0.15% methanesulfonic acid. Then 30 parts of HOE alcohol was added and heating continued until an AV of 9 was obtained. 6.5
The product was sulfurized using % sulfur to produce the sulfurized product. Example 6 A mixture of 80 parts main combustion lard oil and 20 parts Emery 876 acid was heated to 400-410°C (204-210°C) for 4 hours in the presence of 0.3% p-toluenesulfonic acid. Then add 22 parts HOE alcohol,
Heating was continued until an AV of 10 was obtained. To this mixture was added 30 parts of a diester prepared from 2 moles of tall oil fatty acid and 1 mole of diol concentrate. The resulting mixture was sulfurized to yield a product containing 7.4% bound sulfur. Example 7 12% Chevron C ₁₅ -C ₁₈ α-olefin and 88%
The blend with the product was sulfurized to give a product containing 7.1% sulfurization. Example 8 The procedure of Example 4 was repeated at 6% in the sulfurization step.
was repeated on a larger scale using sulfur. Product XI
contained 5.9% bound sulfur. Example 9 78 parts of a compound having a melting point of about 100㎓ (37.8°C),
A blend of solid triglycerides and 22 parts of Emery 621 coconut oil fatty acid was heated to 400-410°C (204-210°C) for 4 hours in the presence of 0.15% methanesulfonic acid. Then 23 parts of isodecyl alcohol was added and heating continued at 340-380°C (171-193°C) for an additional 4 hours. AV decreased to 8 during this method.
16 parts of isodecyl ester of tall oil fatty acids were then added and the mixture was prepared according to the procedure of Example 1.
By heating with sulfur, product XII containing 6.7% bound sulfur was prepared.
The mixture before sulfurization contained about 56% transesterified triglycerides and about 44% esters. The following products were prepared for comparison purposes. Example A A mixture of 88% main combustion lard oil and 12% methyl oleate was sulfurized to produce product A containing 9.7% bound sulfur. Example B 55% main combustion lard oil and 45% tall oil fatty acid
The mixture with HOE alcohol ester was sulfurized to contain 9.0% bound sulfur and 9%
A sulfurized product B with AV was prepared. Example C A mixture of 50% main combustion oil and 50% isodecyl alcohol esters of tall oil fatty acids was sulfurized to contain 9.1% bound sulfur and an A. of 8.
Product C was prepared with V. Representative products of the sulfurized aliphatic oil additive compositions of the present invention, prepared as described in Examples 1-9 above, were prepared in a conventional manner, along with comparative products A and B. were tested at various concentration levels ranging from 1 to 4% by weight in mineral oil and in three commercially available engine oils to determine the effect of each on flow properties. The results are listed in Tables, and. Mineral oil does not contain pour point depressing additives and has a
It did not flow at temperatures below 17.8℃). The engine oil contains pour point depressing additives, −20〓(−
6.7°C). The solubility of the products of the invention in these oils was excellent. As the table clearly shows, the additive of the present invention has excellent properties as a pour point depressant, and when added to a mineral oil with a pour point of 0〓 (-17.8°C), the oil is heated at a lower temperature. Keep it liquid. However, adding large amounts of additives reduces the ability to flow at low temperatures. As shown in the tables, sulfurized fatty oils (Products A and B) reduce the cold flow properties of pour point depressed engine oils. However, the additives of the present invention can be used in higher concentrations without having a detrimental effect on the flow properties of the same engine oil. The improved load-supporting and friction-reducing properties imparted by the use of the additives of the present invention are demonstrated by the Falex step-up test, as illustrated by the tables and data contained therein.
- test) shows improved load support and friction reduction (torque) as measured by test). The tests listed in the table were conducted using pour point depressed engine oils. The tests described in the table illustrate the performance of the additive using unblended base oils, including mineral oil and synthetic lubricant base stocks. The Farex procedure for evaluating lubricants is
Lubrication Engineering, 24 , No.8349−358
(1968). The procedure used in these tests was as follows: After a 5 minute warmup at 250 lbs., the load was increased in 250 lb. increments, at each increment, welding type, until failure.
Hold for 1 minute. A torque comparison was also made to show the difference in friction. The crankcase oil, formulated in high quality SEGrade 10W40 crankcase oil, was evaluated using a four ball machine in friction and wear tests as described in ASTM-D-2266 method. Crankcase oil alone was compared to crankcase oil with 2% Additive B or 2% Additive XI. The test was carried out at 1800rpm with a load of 40Kg at 350〓
(177°C) for 1 hour. Additive Wear - Scar Diameter Crankcase Oil 0.86mm + 2% Additive B 0.80mm + 2% Additive XI 0.57mm Dissolve some products in Gulf Synlube 4CS with heating or stirring. Specifically, the solubility in synthetic hydrocarbon oils was tested. Then add 45% of the solution
The sample was kept at (7.2°C) for 4 days, and finally, it was observed after being brought to room temperature with salt. The observation results were as follows: 2%A heavy underlayer 2%B slight dropout 2%C 〃 2% very slight dropout 2% slight cloudy 2% cloudy 2%XI slight dropout Cloudiness The sulfurized fatty oil of the present invention contains about 0.05
It is effective when used at concentrations ranging from ~15% by weight. The preferred concentration range is generally about 0.5 to about 5
Weight%. In another embodiment of the invention, the sulfurized fatty oil additive composition improves lubrication, reduces wear on pistons, rings, and cylinders, and reduces deposits in various types of fuels, particularly in fuel pumps. is effective in reducing the formation of Such fuels are broadly classified into gasoline, for use in spark-ignition internal combustion engines; diesel oil, for use in compression-ignition internal combustion engines; and heating (for use in inoil combustion burner assemblies). or furnace) includes oil. Other advantages include lower pour point and concomitant reduction in oil filter clogging when used in fuel oils or diesel fuels.
In such new and improved fuel compositions, the additives of the present invention may be present in an amount of about 0.0005 to about 0.1% by weight;
It is preferably effective in a range of about 0.0015 to about 0.05% by weight.

[Table] It does not flow.

【table】

[Table] (2) Surrounding flow

[Table] (2) Surrounding flow.

It flows in [Table].

【table】

【table】

Claims (1)

[Scope of Claims] 1 Contains a sulfurized transesterified triglyceride, the total acid component of which is about 35 mol% or more saturated aliphatic acid and about 65 mol%
The total acid component further comprises: a) greater than about 20 mole % monounsaturated acids; b) less than about 15 mole % polyunsaturated fatty acids; c) 6 to 14 d) greater than about 20 mole percent saturated aliphatic acids having 6 to 16 carbon atoms, including greater than about 10 mole percent saturated aliphatic acids having carbon atoms, and d) less than about 15 mole percent 18 carbon atoms. A sulfurized triglyceride additive composition characterized as comprising: a saturated aliphatic acid having at least one carbon atom. 2. The sulfurized triglyceride additive composition of claim 1, wherein said monounsaturated fatty acid is present in an amount greater than about 35 mole percent. 3. The sulfurized triglyceride additive composition of claim 1, wherein said polyunsaturated fatty acid is present in an amount less than about 10 mole percent. 4. The sulfurized triglyceride additive composition of claim 1, wherein said total saturated fatty acids are present in an amount greater than about 50 mole percent. 5 The saturated acid having 6 to 14 carbon atoms is about
The sulfurized triglyceride additive composition of claim 1 present in an amount greater than 15 mole percent. 6 The saturated acid having 6 to 16 carbon atoms is about
A sulfurized triglyceride additive composition according to claim 1, wherein the sulfurized triglyceride additive composition is present in an amount greater than 35 mole percent. 7. The sulfurized triglyceride additive composition according to claim 1, further comprising a solubilizer. 8. The sulfurized triglyceride additive composition of claim 7, wherein the solubilizing agent is selected from the group consisting of triglycerides, olefins, esters of unsaturated carboxylic acids, and mixtures thereof. 9. The sulfurized triglyceride additive composition according to claim 8, wherein the solubilizer is a triglyceride. 10. The sulfurized triglyceride additive composition according to claim 8, wherein the solubilizer is an olefin. 11. The sulfurized triglyceride additive composition of claim 10, wherein the olefin contains from about 8 to about 20 carbon atoms, alone or in a mixture. 12. The sulfurized triglyceride additive composition of claim 8, wherein the solubilizer is an ester of an unsaturated carboxylic acid. 13. The sulfurized triglyceride additive composition of claim 7, wherein the solubilizing agent is present in an amount within the range of about 5 to about 70% by weight, based on the transesterified triglyceride. 14. The sulfurized triglyceride additive composition of claim 13, wherein the solubilizing agent is present in an amount within the range of about 5 to about 55 weight percent, based on the transesterified triglyceride. 15. The sulfurized triglyceride additive composition of claim 1, wherein the bound sulfur is present in an amount ranging from about 4% to about 14% by weight, based on the total product. 16 (1) Transesterifying one or more triglycerides with one or more organic acids, or esters thereof, to produce transesterified triglycerides, the total acid content of which triglycerides is about 35 moles. % or more saturated aliphatic acids and up to about 65 mole % unsaturated fatty acids, said total acid component further comprising: a) greater than about 20 mole % monounsaturated acids; b) greater than about 15 mole % less polyunsaturated fatty acids, c) about 20 mol%, including more than about 10 mol% of saturated aliphatic acids having 6 to 14 carbon atoms;
characterized as comprising: a saturated aliphatic acid having more than 6 to 16 carbon atoms, and d) a saturated aliphatic acid having less than about 15 mole % 18 or more carbon atoms, and ( 2) sulfurizing the mixture of transesterified triglyceride products of step (1) with elemental sulfur;
A sulfurized, transesterified triglyceride additive composition incorporating bound sulfur in an amount ranging from about 4% to about 14% by weight, based on the mixture of transesterified triglyceride products. Manufacturing method. 17. The method of claim 16, wherein the monounsaturated fatty acid is present in an amount greater than about 35 mole percent. 18. The method of claim 16, wherein said polyunsaturated fatty acid is present in an amount less than about 10 mole percent. 19. The method of claim 16, wherein said total saturated aliphatic acids are present in an amount greater than about 50 mole percent. 20. The method according to claim 16, further comprising a step of esterifying the free acid in the transesterification reaction product with an alcohol component before the sulfurization step. 21. The method of claim 20, wherein the alcohol component for esterification comprises a branched aliphatic primary alcohol. 22 Before the sulfurization step, the transesterification reaction product, triglyceride, esterified fatty acid,
17. The method of claim 16, further comprising the step of blending with a compound selected from the group consisting of alpha-olefins and mixtures thereof. 23. The method of claim 16, wherein the transesterification step is carried out in the presence of a transesterification catalyst. 24 The transesterification catalyst is a group consisting of tetrabutyl titanate, zinc acetate, sodium carbonate, sodium sulfate, stannous oxalate, p-toluenesulfonic acid, methanesulfonic acid, sulfuric acid, butylchlorotin dihydroxide, and phosphoric acid. 24. The method according to claim 23, selected from: 25. The method of claim 23, wherein the transesterification catalyst is present in an amount ranging from about 0.01 to about 1% by weight based on triglycerides. 26. The method of claim 25, wherein said catalyst is present in an amount ranging from about 0.03 to about 0.5% by weight. 27. The method of claim 24, wherein the catalyst is p-toluenesulfonic acid. 28. The method of claim 24, wherein the catalyst is methanesulfonic acid. 29 (1) Having the viscosity and volatility of a lubricating oil,
a refined base oil, and (2) a small amount of a sulfurized triglyceride additive composition, the additive composition comprising a sulfurized transesterified triglyceride, the total acid content of said triglycerides being about 35 moles. % or more saturated aliphatic acids and up to about 65 mole % unsaturated fatty acids, said total acid component further comprising: a) greater than about 20 mole % monounsaturated acids; b) greater than about 15 mole % less polyunsaturated fatty acids, c) about 20 mol%, including more than about 10 mol% of saturated aliphatic acids having 6 to 14 carbon atoms;
d) a saturated fatty acid having more than 6 to 16 carbon atoms; and d) a saturated aliphatic acid having less than about 15 mole % 18 or more carbon atoms. Lubricating oil composition. 30. The lubricating oil composition of claim 30, wherein the sulfurized triglyceride additive composition is present in an amount within the range of about 0.05 to about 15% by weight of the lubricating oil composition. 31. The lubricating oil composition of claim 30, wherein the sulfurized triglyceride additive composition is present in an amount within the range of about 0.5% to about 5% by weight of the lubricating oil composition. 32 (1) have suitable volatility and flammability;
a blended base fuel; and (2) a small amount of a sulfurized triglyceride additive composition, the additive composition comprising a sulfurized transesterified triglyceride, the total acid content of the triglycerides being about 35 mole percent. or more saturated aliphatic acids and less than about 65 mole % unsaturated fatty acids, the total acid component further comprising: a) greater than about 20 mole % monounsaturated acids; b) less than about 15 mole % polyunsaturated fatty acids, c) about 20 mol%, including more than about 10 mol% of saturated aliphatic acids having 6 to 14 carbon atoms;
d) a saturated aliphatic acid having more than 6 to 16 carbon atoms; and d) a saturated aliphatic acid having less than about 15 mole % 18 or more carbon atoms. fuel composition. 33. Claim 32, wherein the blended basic fuel is gasoline fuel used in a spark-ignition internal combustion engine.
The fuel composition described in Section. 34 The blended basic fuel is a diesel fuel used in a compression ignition internal combustion engine, as claimed in claim 3.
The fuel composition according to item 2. 35. The fuel composition of claim 32, wherein the blended base fuel is a heating oil for use in an oil-fired burner assembly. 36 The sulfurized triglyceride additive composition is
33. The fuel composition of claim 32, wherein the fuel composition is present in an amount ranging from about 0.0005 to about 0.1% by weight of the fuel composition. 37 The sulfurized triglyceride additive composition is
37. The fuel composition of claim 36, wherein the fuel composition is present in an amount ranging from about 0.0015% to about 0.05% by weight of the fuel composition.