US2936320A - Diesters of mixed aromatic dibasic acids - Google Patents

Diesters of mixed aromatic dibasic acids Download PDF

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US2936320A
US2936320A US667716A US66771657A US2936320A US 2936320 A US2936320 A US 2936320A US 667716 A US667716 A US 667716A US 66771657 A US66771657 A US 66771657A US 2936320 A US2936320 A US 2936320A
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isophthalic acid
acid
diesters
terephthalic acid
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Jr George J Benoit
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
    • C07C69/80—Phthalic acid esters
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
    • C07C69/80—Phthalic acid esters
    • C07C69/82—Terephthalic acid esters

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  • This invention relates to novel diesters of mixed aromatic dibasic acids. More particularly, the invention is concerned with a new class of dialkyl diesters of mixtures of isophthalic acid and terephthalic acidwhichare excellent synthetic oils.
  • Synthetic oils are important as lubricants in a variety of applications where there are certain specific requirements not met by the more common lubricating oils such as mineral oils. Applications of this type include the lubrication of instruments, weapons, optical equipment and aircraft gas turbines of the prop and jet types.
  • the most important property of the novel dialkyl diesters of mixtures of isophthalic acid and terephthalic acid of this invention is their thermal stability at high temperatures which make them unusually desirable as base lubricants for aircraft gas turbine lubricating oil compositions.
  • the unusual new synthetic oils, according to the present invention are characterized by a surprisingly low coke formation when subjected to high temperatures for extended periods of time. They are surprisingly superior in this respect to other synthetic oils commonly employed heretofore in high temperature 21,936,329 Patented May 1960 applications such as the lubrication of aircraft gas turbines.
  • dialkyl diesters of mixtures of isophthalic acid and terephthalicacid in accordance with this invention areillustrated by the following general formula:
  • R and R alkyl groups are derived by esterifying the mixture of isophthalic acid and terephthalic acid with a mixture of aliphatic alcohols of from 5 to 13 carbon atoms each. Mixtures of from 10 to 90% by weight of each alcohol and from 2 to 5 different kinds are particularly suitable. Still more preferred are esterifying alcohols and alkyl groups derived therefrom within the foregoing description which are mixed, branched chain alcohols of from 6 to 10 carbon'atoms with an average of 8 carbon atoms each. Isophthalate and terephthalate mixtures derived from such alcohols are characterized by low volatility and at the same time have less tendency to crystallize at low temperatures.
  • the mixtures of isophthalic acid and terephthalic acid from which the dialkyl diesters of this invention are derived preferably contain from 50 to 99% by weight of isophthalic acid and from 1 to 50% by weight of terephthalic acid.
  • Such proportions occur in the usual mixtures of the two acids derived from isomeric xylenes from common sources such as petroleum fractions or coal tar distillates.
  • Particularly suitable mixtures within the aforementioned proportions are those containing about by weight isophthalic acid and 15% by weight terephthalic acid.
  • dialkyl diesters of mixed isophthalic acid and terephthalic acid examples include n-hexyl 2-ethylbutyl isophthalate and terephthalate having an isophthalate to terephthalate weight ratio of 25 to 75, 2-ethylhexyl isooctyl isophthalate and terephthalate derived from a 50-50 mixture of isophthalic acid and terephthalic acid, Z-ethylhexyl isooctyl diester of a mixture of 85 by weight of isophthalic acid and 15% by weight terephthalic acid, 2-ethylhexyl isooctyl n-octyl mixed diester of 85% by weight isophthalic acid and 15% by weight terephthalic acid, di-Z-ethylhexyl diester of a mixture of 85% by weight of isophthalic acid and 15% by weight terephthalic acid,
  • dialkyl diesters of isophthalic acid and terephthalic acid are conveniently prepared by the reaction of the desired aliphatic alcohols of from 5 to 13 carbon atoms each with the mixture of acids under ordinary esterification conditions.
  • Conventional esterification catalysts such as p-toluene sulfonic acid and heating are desirable to accelerate the reaction.
  • dialkyl diesters of three different types results in dialkyl diesters of three different types for the This fact is illus- Mixtures of the dialkyl diesters of the above types in which the R and R alkyl groups are different from one another generally have superior physical properties compared to the diesters in which the alkyl groups are alike.
  • the following examples will serve as further illustraproduct is decolorized with carbon and topped by distilling at 0.1 mm. mercury pressure to a maximum pot temperature of 200 C. It has an average saponification number of 294 and its equivalent weight estimated from analysis is about 188 compared to a theoretical of 195.
  • the product is then distilled at 0.1 mm. of mercury pres sure to a maximum pot temperature of 225 C. The distilled material is clear in appearance and pours slowly at about -55 F.
  • ephthalic acid mixtures according to this invention. Unless otherwise specified, the proportions are given on a weight basis.
  • EXAMPLE I This example shows the preparation of mixed isooctyl, n-octyl, 2-ethylhexyl ester of a mixture of 85% by weight isophthalic acid and 15% by weight terephthalic acid.
  • the combined products obtained above are washed twice with dilute aqueous sodium carbonate solution and then water until neutral.
  • the products are then treated with g. decolorizing carbon and topped by distilling at 0.1 mm. mercury pressure to a maximum pot temperature of 200 C. to remove unreacted materials.
  • 1,428 g. of bottoms product is obtained.
  • This product is filtered through a column filled with 300 g. of clay to give 1,058 g. of mixed isooctyl, n-octyl, 2-ethylhexyl ester of 85: 15 isoand terephthalic acid which has a clear appearance and pours slowly at about -60 F.
  • EXAMPLE II The preparation of mixed isooctyl, Z-ethylhexyl diester of a mixture of 85% by weight isophthalic acid and 15 by weight terephthalic acid is shown in this example.
  • the standard coking test involves maintaining the test oil in a bath at a constant level and splashing it against an overhead inclined plate at the temperature indicated for eight hours.
  • the splashing is effected by steel wires on a wheel rotated at a speed of 1,050 rpm. as it is partially immersed in the oil.
  • the coking value is the weight of the deposit formed on the underside of the plate during the test period.
  • gas turbine oil specifications MIL- L-78 08C and MIL-L-25336 are gas turbine oil specifications.
  • the evaporation characteristics of the compositions are determined by placing them in a bomb through. which air is passed at a given rate over the fluid. The weight losses over the period of time at the temperature indicated are reported in terms of percent by weight. This test is the standard ASTM evaporation test D972-51T.
  • the oxidation and corrosion test involves joining the five metal specimens in the form of a pentagon and immersing them in the oil to be tested. Oxygen is bubbled through the oil at the temperature and for the time indicated and the change in weight of each of the metal specimens is determined.
  • compositions containing base lubricants other than the mixed dialkyl diesters of isophthalic acid and terephthalic acid according to this invention are included as illustrative of one of the more commonly used synthetic oil base lubricants.
  • the separate phthalate isomers are also given for comparative purposes.
  • novel diesters of mixed isophthalic acid and terephthalic acid have other uses in addition to their application as synthetic oils. Such uses include their employment as plasticizers in compositions where low freezing points are desirable.
  • the mixed dialkyl diesters of isophthalic acid andterephthalic acid are outstanding synthetic oil base fluids for aircraft gas turbine lubricating oils. They possess excellent thermal stability at high temperatures as indicated by their low coke formation.
  • the mixed dialkyl diesters of isophthalic acid and terephthalic acid give lubricant compositions which are decidedly superior to similar compositions containing the widely used di(Z-ethylhexyl) sebacate as base lubricant.
  • the coking characteristics of the mixed isophthalates and terephthalates of the invention are also surprisingly superior to the separate isomeric phthalates.
  • the above table also shows that the mixed isophthalate and terephthalate base gas turbine lubricant compositions of the invention possess excellent volatility characteristics which prevent undue consumption of the lubricant compositions at high altitudes and high temperatures.
  • the mixed isophthalates and terephthalates are also fluid at unusually low temperatures and have good viscosity tem perature characteristics which make them suitable as lubricants throughout wide temperature ranges.
  • compositions of the invention are also shown to be unusually resistant to oxidation and formation of corrosive products at high temperatures.
  • the corrosion of all types of metals in the tests is maintained at a satisisophthalic acid and 15% by weight of terephthalic acid in which the alkyl esterifying groups are derived from a mixture of from 2 to 5 aliphatic alcohols of 8 carbon atoms each, said mixture of alcohols containing from 10 to 90% by weight of each alcohol.

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Description

2,936,320 DIESTERS F MIXED AROMATIC DIBASIC ACIDS George J. Benoit, Jr., San Anselmo, Calif., assignor :to California Research Corporation, San Francisco, Calif., a corporation of Delaware No Drawing; Application June 24, 1957 Serial No. 667,716
4 Claims. (Cl. 260-475) This invention relates to novel diesters of mixed aromatic dibasic acids. More particularly, the invention is concerned with a new class of dialkyl diesters of mixtures of isophthalic acid and terephthalic acidwhichare excellent synthetic oils.
Synthetic oils are important as lubricants in a variety of applications where there are certain specific requirements not met by the more common lubricating oils such as mineral oils. Applications of this type include the lubrication of instruments, weapons, optical equipment and aircraft gas turbines of the prop and jet types.
In general, a combination of special properties is desirable in synthetic oils for applications of the above type- Fluidity at low temperatures and low volatility high temperatures are important characteristics. Similarly, good viscosity-temperature characteristics are desirable since properlubrication in most applications requires that the lubricant be adaptable to changes in temperature without extreme variations in viscosity.
The most critical characteristic of synthetic lubricating oils in the important application to aircraft gas turbines is the resistance of the oil to thermal degradation at high temperatures. Aircraft gas turbines are being operated at increasingly higher temperatures where the formation of coke, due to the thermal decomposition and deterioration of the lubricant, is a major problem. The proper functioning of the lubrication system is impeded by the formation of deposits on hearing cages and'housings and the plugging of oil filters.
It has now been found that a superior new class of diesters of mixed aromatic dibasic acids, namely, the dialkyl diesters of mixtures of isophthalic acid and terephthalic acid in which the alkyl esterifying groups are derived from a mixture of aliphatic alcohols of from 5 to 13 carbon atoms each, are excellent synthetic oils having special properties which make them unusually desirable as synthetic lubricants.
The superior new class of dialkyl diesters of mixtures of isophthalic acid and terephthalic acid, according to the present invention as described above, possesses a desirably low volatility at high temperatures and remains fluid at low temperatures. Their viscosity-temperature characteristics are superior to other isomeric forms of diesters of aromatic dibasic acids.
The most important property of the novel dialkyl diesters of mixtures of isophthalic acid and terephthalic acid of this invention is their thermal stability at high temperatures which make them unusually desirable as base lubricants for aircraft gas turbine lubricating oil compositions. The unusual new synthetic oils, according to the present invention, are characterized by a surprisingly low coke formation when subjected to high temperatures for extended periods of time. They are surprisingly superior in this respect to other synthetic oils commonly employed heretofore in high temperature 21,936,329 Patented May 1960 applications such as the lubrication of aircraft gas turbines.
The dialkyl diesters of mixtures of isophthalic acid and terephthalicacid in accordance with this invention, areillustrated by the following general formula:
l-OR:
atoms and R is another alkyl group of from 5 to 13 carbon atoms which may be the same as or different from R Preferably, the R and R alkyl groups are derived by esterifying the mixture of isophthalic acid and terephthalic acid with a mixture of aliphatic alcohols of from 5 to 13 carbon atoms each. Mixtures of from 10 to 90% by weight of each alcohol and from 2 to 5 different kinds are particularly suitable. Still more preferred are esterifying alcohols and alkyl groups derived therefrom within the foregoing description which are mixed, branched chain alcohols of from 6 to 10 carbon'atoms with an average of 8 carbon atoms each. Isophthalate and terephthalate mixtures derived from such alcohols are characterized by low volatility and at the same time have less tendency to crystallize at low temperatures.
The mixtures of isophthalic acid and terephthalic acid from which the dialkyl diesters of this invention are derived preferably contain from 50 to 99% by weight of isophthalic acid and from 1 to 50% by weight of terephthalic acid. Such proportions occur in the usual mixtures of the two acids derived from isomeric xylenes from common sources such as petroleum fractions or coal tar distillates. Particularly suitable mixtures within the aforementioned proportions are those containing about by weight isophthalic acid and 15% by weight terephthalic acid.
Examples of dialkyl diesters of mixed isophthalic acid and terephthalic acid, in accordance with this invention, include n-hexyl 2-ethylbutyl isophthalate and terephthalate having an isophthalate to terephthalate weight ratio of 25 to 75, 2-ethylhexyl isooctyl isophthalate and terephthalate derived from a 50-50 mixture of isophthalic acid and terephthalic acid, Z-ethylhexyl isooctyl diester of a mixture of 85 by weight of isophthalic acid and 15% by weight terephthalic acid, 2-ethylhexyl isooctyl n-octyl mixed diester of 85% by weight isophthalic acid and 15% by weight terephthalic acid, di-Z-ethylhexyl diester of a mixture of 85% by weight of isophthalic acid and 15% by weight terephthalic acid, namyl n-hexyl isooctyl mixed diester of 85:15 isophthalic acid and terephthalic acid, Oxo tridecyl diester of 85:15 isophthalic acid and terephthalic acid, etc.
The dialkyl diesters of isophthalic acid and terephthalic acid are conveniently prepared by the reaction of the desired aliphatic alcohols of from 5 to 13 carbon atoms each with the mixture of acids under ordinary esterification conditions. Conventional esterification catalysts such as p-toluene sulfonic acid and heating are desirable to accelerate the reaction.
The esterification of the isophthalic acid and terephthalic acid with aliphatic alcohols, as described above, results in dialkyl diesters of three different types for the This fact is illus- Mixtures of the dialkyl diesters of the above types in which the R and R alkyl groups are different from one another generally have superior physical properties compared to the diesters in which the alkyl groups are alike.
The following examples will serve as further illustraproduct is decolorized with carbon and topped by distilling at 0.1 mm. mercury pressure to a maximum pot temperature of 200 C. It has an average saponification number of 294 and its equivalent weight estimated from analysis is about 188 compared to a theoretical of 195. The product is then distilled at 0.1 mm. of mercury pres sure to a maximum pot temperature of 225 C. The distilled material is clear in appearance and pours slowly at about -55 F.
The physical characteristics of representative examples of the superior new dialkyl diesters of mixtures of isophthalic acid and terephthalic acid of this invention are given in the following table. Also included, for the purpose of comparison, are esters of phthalic acid which is tions of the dialkyl diesters of isophthalic acid and terthe ortho isomer of isophthalic acid and terephthalic acid.
Table 1 V Viscosity, Centistokes Approximate Acid Alkyl Groups Poug goint,
' -40 F. 100 F 210 F.
'Phthallc 2-Ethylhexyl 100,000 extra--- 29. 6 4. Cloud at 30. Isooetyl 65,000 extr-... 27.2 4. 14 Cloud at --20.
2-Etl1ylhexyl-lsooetyl 77,0 33.5 4.86 -55. 85IPA15TPA 2-Ethylhexyl-Isooctyl-n-Octyl 48,000 extr 28.5 4.55 -so.
ephthalic acid mixtures, according to this invention. Unless otherwise specified, the proportions are given on a weight basis.
EXAMPLE I This example shows the preparation of mixed isooctyl, n-octyl, 2-ethylhexyl ester of a mixture of 85% by weight isophthalic acid and 15% by weight terephthalic acid.
322 g. of 85:15 isophthalic acid and terephthalic acid mixture, 546 g. isooctyl alcohol (75%) 82 g. 2-ethylhexanol (10%) and 109 g. n-octanol (15%) are mixed in a reaction vessel equipped with stirrer, thermometer, water trap and reflux condenser. 5.3 g. sodium bisulfate is added to the mixture. The mixture is heated under reflux conditions for about 16 hours to a maximum pot temperature of about 215 C. under a blanket of nitrogen. 75 ml. water is evolved during this time. This preparation is carried out in duplicate to provide additional product.
The combined products obtained above are washed twice with dilute aqueous sodium carbonate solution and then water until neutral. The products are then treated with g. decolorizing carbon and topped by distilling at 0.1 mm. mercury pressure to a maximum pot temperature of 200 C. to remove unreacted materials. 1,428 g. of bottoms product is obtained. This product is filtered through a column filled with 300 g. of clay to give 1,058 g. of mixed isooctyl, n-octyl, 2-ethylhexyl ester of 85: 15 isoand terephthalic acid which has a clear appearance and pours slowly at about -60 F.
EXAMPLE II The preparation of mixed isooctyl, Z-ethylhexyl diester of a mixture of 85% by weight isophthalic acid and 15 by weight terephthalic acid is shown in this example.
332 g. of 85:15 isophthalic acid and terephthalic acid In the above table the abbreviation extr. indicates that the viscosity was obtained by extrapolation of the viscosity-temperature curve for the fluid.
From the physical properties of the phthalate esters in the above table, it is readily'observed that the mixed dialkyl diesters of isophthalic acid and terephthalic acid are decidedly superior to the corresponding esters of phthalic acid as base lubricants. The viscosity-temperature characteristics are much better, thus'providing more effective lubrication over wide temperature ranges. Another advantage of the mixed dialkyl isophthalates and terephthalates lies in their low pour points.
A further illustration of the superior new dialkyl diesters of isophthalic acid and terephthalic acid mixtures of the invention is obtained in an evaluation of the effectiveness of the phthalic esters as aircraft gas turbine lubricants by a number of standard tests on the phthalic ester base lubricants compounded with conventional additives. In these tests the comparison of the results is facilitated by the employment of identically formulated I compositions as follows:
As mentioned, the tests employed in the evaluations are standard tests known generally to the lubricating art by their descriptions in the table which follows.
The standard coking test involves maintaining the test oil in a bath at a constant level and splashing it against an overhead inclined plate at the temperature indicated for eight hours. The splashing is effected by steel wires on a wheel rotated at a speed of 1,050 rpm. as it is partially immersed in the oil. The coking value is the weight of the deposit formed on the underside of the plate during the test period. The description of this coking test is found in gas turbine oil specifications MIL- L-78 08C and MIL-L-25336.
The evaporation characteristics of the compositions are determined by placing them in a bomb through. which air is passed at a given rate over the fluid. The weight losses over the period of time at the temperature indicated are reported in terms of percent by weight. This test is the standard ASTM evaporation test D972-51T.
The oxidation and corrosion test involves joining the five metal specimens in the form of a pentagon and immersing them in the oil to be tested. Oxygen is bubbled through the oil at the temperature and for the time indicated and the change in weight of each of the metal specimens is determined.
For the purpose of comparison, the following table also gives illustrated test results on compositions containing base lubricants other than the mixed dialkyl diesters of isophthalic acid and terephthalic acid according to this invention. For example, di(Z-ethylhexyl) sebacate is included as illustrative of one of the more commonly used synthetic oil base lubricants. The separate phthalate isomers are also given for comparative purposes.
factorily low level and there is little sludge formed in the compositions.
The novel diesters of mixed isophthalic acid and terephthalic acid have other uses in addition to their application as synthetic oils. Such uses include their employment as plasticizers in compositions where low freezing points are desirable.
I claim:
1. Dialkyl diesters of mixtures of isophthalic acid and terephthalic acid in which the alkyl esterifying groups are derived from a mixture of from 2 to 5 aliphatic alcohols of 8 carbon atoms each said mixture containing from 10 to 90% by weight of each alcohol and the mixtures of acid contain from to 99% by weight of isophthalic acid and from 1 to 50% by weight of terephthalic acid.
2. Dialkyl diesters of a mixture of 85% by weight of Table 2 Ester Type: Di-z-ethyl- Isooctyl Alkyl Group z-Ethylhexyl, Isooetyl hexyl n-octyl 2- ethylhexyl Iso: Ter- Iso: Ter- Acid Group Iso-Phthai- 'Ierephephthalate sebacate ephthalate ate thalate Ratio, (Reference) Ratio,
Properties:
Flash, F 450 Fire, F 610 Viscosity at 210 F., cs 3.38 4. 56 Viscosity at 100 F., cs 32. 74 31. 54 32. 9 13. 1 28. 6 Viscosity at 40 F., cs 135,000 104,000 92, 000 1, 700 64, 500 Neutralization N o 0.31 0. 0. 52 0. 90 0. 40 Oxidation and Corrosion, 72 hours at 347 F.,
Metal Wt. Change, MgJcmJ:
Magnesium +0. 06 Steel +0. 03 +0. ()6 +0.05 +0. 09 Percent change in 100 F. vis +4. 66 Change in Neutralization N o +0.1 Percent pentane insolubles 0. 42 Coking, 8 hours at 600 F., mg Coking, 8 hours at 700 F., mg 904 Used Oil from Sump:
Percent change in 100 F. vis +11. 7 Change in Neutralization No +3.0 Percent pentane insolubles 0. 24 Evaporation, 615 hours at 400 F., Percent 15 1 Coke value equivalent to an 8-hour test. Test terminated beforeS hours.
The above test results show that the mixed dialkyl diesters of isophthalic acid andterephthalic acid are outstanding synthetic oil base fluids for aircraft gas turbine lubricating oils. They possess excellent thermal stability at high temperatures as indicated by their low coke formation. In this very important characteristic for gas turbine lubricants, it can be seen at once from the above results that the mixed dialkyl diesters of isophthalic acid and terephthalic acid give lubricant compositions which are decidedly superior to similar compositions containing the widely used di(Z-ethylhexyl) sebacate as base lubricant. The coking characteristics of the mixed isophthalates and terephthalates of the invention are also surprisingly superior to the separate isomeric phthalates.
The above table also shows that the mixed isophthalate and terephthalate base gas turbine lubricant compositions of the invention possess excellent volatility characteristics which prevent undue consumption of the lubricant compositions at high altitudes and high temperatures. The mixed isophthalates and terephthalates are also fluid at unusually low temperatures and have good viscosity tem perature characteristics which make them suitable as lubricants throughout wide temperature ranges.
The compositions of the invention are also shown to be unusually resistant to oxidation and formation of corrosive products at high temperatures. The corrosion of all types of metals in the tests is maintained at a satisisophthalic acid and 15% by weight of terephthalic acid in which the alkyl esterifying groups are derived from a mixture of from 2 to 5 aliphatic alcohols of 8 carbon atoms each, said mixture of alcohols containing from 10 to 90% by weight of each alcohol.
3. 2-ethylhexyl isooctyl diester of a mixture of by weight isophthalic acid and 15% by weight terephthalic acid in which the 2-ethylhexyl and isooctyl esterifying groups are derived from a mixture consisting of 25% by weight of '2-ethylhexyl alcohol and 75% by weight of isooctyl alcohol.
4. Mixed isooctyl, n-octyl and 2-ethylhexy1 diesters of a mixture of 85% by weight isophthalic acid and 15% by weight terephthalic acid in which the esterifying groups are derived from a mixture consisting of 75 by Weight of isooctyl alcohol, 15% by weight of n-octyl alcohol and 10% by weight of 2-ethylhexyl alcohol.
References Cited in the file of this patent UNITED STATES PATENTS 2,610,205 Trigg et al. Sept. 9, 1952 2,628,207 Smith et al. Feb. 10, 1953 2,650,908 Beears Sept. 1, 1953 2,653,165 Levine Sept. 22, 1953 2,656,377 Pino Oct. 20, 1953 2,802,860 Stack et al. Aug. 13, 1957 2,809,208 Miller Oct. 8. 1957

Claims (1)

1. DIALKYL DIESTERS OF MIXTURES OF ISOPHTHALIC ACID AND TEREPHTHALIC ACID IN WHICH THE ALKYL ESTERIFYING GROUPS ARE DERIVED FROM A MIXTURE OF FROM 2 TO 5 ALIPHATIC ALCOHOLS OF 8 CARBON ATOMS EACH SAID MIXTURE CONTAINING FROM 10 TO 90% BY WEIGHT OF EACH ALCOHOL AND THE MIXTURES OF ACID CONTAIN FROM 50 TO 99% BY WEIGHT OF ISOPHTHALIC ACID AND FROM 1 TO 50% BY WEIGHT OF TEREPHTHALIC ACID.
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Cited By (14)

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US3021357A (en) * 1959-04-15 1962-02-13 Standard Oil Co Dialkyl esters of 5-t-alkylisophthalic acid
US3094503A (en) * 1960-07-25 1963-06-18 Continental Oil Co Phthalates of a mixture of normal 6, 8 and 10 carbon primary alcohols and vinyl chloride polymers plasticized therewith
US3111127A (en) * 1961-06-27 1963-11-19 Brown & Williamson Tobacco Smoking tobacco product and method of making the same
US3155715A (en) * 1959-09-30 1964-11-03 Socony Mobil Oil Co Inc Preparation of dialkyl esters of terephthalic acid
US3912640A (en) * 1972-08-07 1975-10-14 Stauffer Chemical Co Gas turbine lubricants
US4080303A (en) * 1974-07-22 1978-03-21 The Lubrizol Corporation Lubricant compositions containing boron dispersant, VI improver, and aromatic carboxylic acid esters
US4514190A (en) * 1982-10-25 1985-04-30 Standard Oil Company (Indiana) Synthetic fuel composition
US5104751A (en) * 1988-06-06 1992-04-14 Fuji Photo Film Co., Ltd. Magnetic recording medium lubricant comprising a phthalic acid diester and fatty acid ester
US5288432A (en) * 1985-12-20 1994-02-22 Akzo America Inc. High temperature synthetic lubricants and related engine lubricating systems
US5686398A (en) * 1993-06-15 1997-11-11 Idemitsu Kosan Co., Ltd. Additive for lubricant or fuel, lubricating oil composition or fuel composition containing it, and substituted hydroxyaromatic ester derivative
US20100144572A1 (en) * 2008-12-05 2010-06-10 Abhimanyu Onkar Patil Lubricants having alkyl cyclohexyl 1,2-dicarboxylates
US20100216678A1 (en) * 2009-02-24 2010-08-26 Abhimanyu Onkar Patil Lubricant compositions containing glycerol tri-esters
US20150025185A1 (en) * 2012-08-23 2015-01-22 Lg Chem, Ltd. Plasticizer composition
US20160376219A1 (en) * 2014-02-07 2016-12-29 Lg Chem, Ltd. Ester compound, plasticizer composition including the same, preparation method of the plasticizer composition and resin composition including the plasticizer composition

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US2628201A (en) * 1949-07-29 1953-02-10 Rca Corp Zinc-magnesium oxide luminescent materials and methods of making same
US2653165A (en) * 1950-09-27 1953-09-22 California Research Corp Oxidation process
US2656377A (en) * 1951-01-16 1953-10-20 California Research Corp Process for the separation of isophthalic and terephthalic diesters
US2802860A (en) * 1954-08-06 1957-08-13 Sherwin Williams Co Method of manufacture of phthalic esters of anosmic character
US2809208A (en) * 1954-12-13 1957-10-08 Allied Chem & Dye Corp Production of dialkyl esters of isophthalic and terephthalic acids from nitriles

Cited By (18)

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US3021357A (en) * 1959-04-15 1962-02-13 Standard Oil Co Dialkyl esters of 5-t-alkylisophthalic acid
US3155715A (en) * 1959-09-30 1964-11-03 Socony Mobil Oil Co Inc Preparation of dialkyl esters of terephthalic acid
US3094503A (en) * 1960-07-25 1963-06-18 Continental Oil Co Phthalates of a mixture of normal 6, 8 and 10 carbon primary alcohols and vinyl chloride polymers plasticized therewith
US3111127A (en) * 1961-06-27 1963-11-19 Brown & Williamson Tobacco Smoking tobacco product and method of making the same
US3912640A (en) * 1972-08-07 1975-10-14 Stauffer Chemical Co Gas turbine lubricants
US4080303A (en) * 1974-07-22 1978-03-21 The Lubrizol Corporation Lubricant compositions containing boron dispersant, VI improver, and aromatic carboxylic acid esters
US4514190A (en) * 1982-10-25 1985-04-30 Standard Oil Company (Indiana) Synthetic fuel composition
US5288432A (en) * 1985-12-20 1994-02-22 Akzo America Inc. High temperature synthetic lubricants and related engine lubricating systems
US5104751A (en) * 1988-06-06 1992-04-14 Fuji Photo Film Co., Ltd. Magnetic recording medium lubricant comprising a phthalic acid diester and fatty acid ester
US5686398A (en) * 1993-06-15 1997-11-11 Idemitsu Kosan Co., Ltd. Additive for lubricant or fuel, lubricating oil composition or fuel composition containing it, and substituted hydroxyaromatic ester derivative
US20100144572A1 (en) * 2008-12-05 2010-06-10 Abhimanyu Onkar Patil Lubricants having alkyl cyclohexyl 1,2-dicarboxylates
WO2010065129A1 (en) 2008-12-05 2010-06-10 Exxonmobil Research And Engineering Company Lubricants having alkyl cyclohexyl 1,2-dicarboxylates
US8614174B2 (en) 2008-12-05 2013-12-24 Exxonmobil Research And Engineering Company Lubricants having alkyl cyclohexyl 1,2-dicarboxylates
US20100216678A1 (en) * 2009-02-24 2010-08-26 Abhimanyu Onkar Patil Lubricant compositions containing glycerol tri-esters
US20150025185A1 (en) * 2012-08-23 2015-01-22 Lg Chem, Ltd. Plasticizer composition
US9234086B2 (en) * 2012-08-23 2016-01-12 Lg Chem, Ltd. Plasticizer composition
US20160376219A1 (en) * 2014-02-07 2016-12-29 Lg Chem, Ltd. Ester compound, plasticizer composition including the same, preparation method of the plasticizer composition and resin composition including the plasticizer composition
US10150727B2 (en) * 2014-02-07 2018-12-11 Lg Chem, Ltd. Ester compound, plasticizer composition including the same, preparation method of the plasticizer composition and resin composition including the plasticizer composition

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