公开(公告)号：GB683803A

公开(公告)日：1952-12-03

申请号：GB735749

申请日：1949-03-17

Applicant: STANDARD OIL DEV CO

Inventor： MORTON RONALD WILLIAM

IPC: C07C67/03 ,  C07C69/34

Abstract: Complex esters having the general formula R1-OOC-R2-COO-R3-OOC-R4-COOR5 in which R1 and R5 are aliphatic alcohol or ether-alcohol residues, R2 and R4 are the hydrocarbon radicals of aliphatic dicarboxylic acids or are direct carbon-to-carbon linkages and R3 is the hydrocarbon or oxygenated hydrocarbon radical of a glycol or polyglycol, all the R's being saturated, are prepared by heating together in proportions yielding the complex ester, the appropriate diester of the alcohol and dicarboxylic acid with the glycol or polyglycol in the presence of an esterification catalyst and removing the alcohol of esterification formed. The complex esters preferably contain 20-100 carbon atoms per molecule. The esters may be used as lubricants. Suitable starting materials are C4 to C24 polyglycols, C1 to C12 alcohols, especially 2-ethyl hexanol and iso-octanol and C6 to C20 dicarboxylic acids, especially adipic and sebacic acids, though acids down to oxalic may be used. Experiments are described illustrating the production of complex esters from di-2-ethylhexyl sebacate and (1) triethylene glycol and (2) polyglycol 200 (predominantly tetraethylene glycol) by refluxing the reactants in presence of p-toluene sulphonic acid and removing the alcohol of esterification as overhead and comparison is made with the methods of making the same triethylene glycol complex ester by reacting together triethylene glycol, 2-ethylhexyl alcohol and sebacic acid in one stage, by reacting the glycol with the acid to form the glycol half-ester which is then reacted with the alcohol, and by reacting the alcohol with the acid and then reacting the half acid-ester formed with the triethylene glycol. Specifications 666,697 and 680,438 are referred to. The Provisional Specification refers to the use of excess of the dialkyl ester in the reaction whereby there results a blend of complex ester and the excess of dialkyl ester.ALSO:Synthetic lubricants being complex esters of the general formula R1-OOC-R2-COO-R3-OOC-R4-COOR5 in which R1 and R5 are aliphatic alcohol or ether-alcohol residues, R2 and R4 are the hydrocarbon radicals of aliphatic dicarboxylic acids or are direct carbon-to-carbon linkages and R3 is the hydrocarbon or oxygenated hydrocarbon radical of a glycol or polyglycol, all the Rs being saturated, are prepared by heating together in proportions yielding the complex ester the appropriate di-ester of the alcohol and dicarboxylic acid with the glycol or polyglycol in the presence of an esterification catalyst and removing the alcohol of esterification formed. The complex esters preferably contain 20 to 100 carbon atoms per molecule. Suitable starting materials are C4 to C24 polyglycols, C1 to C12 alcohols, especially 2-ethyl hexanol and iso-octanol and C6 to C20 dicarboxylic acids especially adipic and sebacic acids, though acids down to oxalic may be used. Experiments are described illustrating the production of complex esters from di-2-ethylhexyl sebacate and (1) triethylene glycol and (2) polyglycol 200 (predominantly tetraethylene glycol) by refluxing the reactants in the presence of p-toluene sulphonic acid and removing the alcohol of esterification as overhead and comparison is made with the methods of making the same triethylene glycol complex ester by reacting together triethylene glycol, sebacic acid and 2-ethyl hexyl alcohol in one stage, by reacting the glycol with the acid to form the glycol half-ester which is then reacted with the alcohol and by reacting the alcohol with the acid and then reacting the half acid-ester formed with the triethylene glycol. Specifications 666,697 and 680,438 are referred to. The Provisional Specification refers to the use of excess dialkyl ester in the reaction whereby there results a blend of complex ester and the excess of dialkyl ester.

公开(公告)号：GB718179A

公开(公告)日：1954-11-10

申请号：GB626951

申请日：1951-03-15

Applicant: STANDARD OIL DEV CO

Inventor： MORTON RONALD WILLIAM ,  GREENWOOD JOHN

IPC: C10M169/04

Abstract: A hydraulic fluid comprises an ester of an unsubstituted saturated aliphatic monohydric alcohol and a saturated C2-C12 monocarboxylic acid, the ester containing 6-20 carbon atoms, or mixture of such esters, and a polymer of an ester of acrylic or methacrylic acid having a molecular weight of 2,000-20,000. Monomeric esters referred to are isobutyl butyrate, N-octyl acetate iso-octyl acetate, N-heptyl propionate, N-hexyl isobutyrate, N-hexyl n-butyrate, amyl valerate, N-butyl caproate, N-propyl heptanoate, ethyl caprylate, nonyl acetate, N-hexyl valerate, amyl caproate, butyl n-heptanoate, N-propyl iso-octanoate, isopropyl caprylate, ethyl nonanoate, iso-octyl butyrate, amyl heptanoate, butyl iso-octanoate, isopropyl nonanoate, ethylcaproate, nonyl butyrate, ethyl laurate, butyl laurate and esters obtained by esterifying mixtures of alcohols from the Oxo process, for example with acetic or propionic acids. An antioxidant, for example 2, 6-ditertiary-butyl-4-methyl phenol, may be added to the compositions.

公开(公告)号：GB687348A

公开(公告)日：1953-02-11

申请号：GB798349

申请日：1949-03-24

Applicant: STANDARD OIL DEV CO

Inventor： MORTON RONALD WILLIAM

IPC: C07C67/08 ,  C07C69/34 ,  C08G63/20

Abstract: Complex esters having the general formula R1-OOC-R2-COO-R3-OOC-R4-COO -R5, in which R1 and R5 are aliphatic alcohol or ether alcohol residues, R2 and R4 are the hydrocarbon radicals of aliphatic dicarboxylic acids or are direct carbon-to-carbon linkages and R3 is the hydrocarbon or oxygenated hydrocarbon radical of a glycol or polyglycol, all the radicals R1 to R5 being saturated, are prepared by the reaction in one or more stages in the presence of an alkali metal or ammonium bisulphate as esterification catalyst, of appropriate aliphatic alcohols, glycols or polyglycols and dicarboxylic acids in proportions to give said complex ester. Suitable reactants are C4 to C24 polyglycols, or mixtures thereof, C1 to C12 alkanols or mixtures thereof, and C6 to C20 dicarboxylic acids or mixtures thereof, though acids down to oxalic may be used. Esterification may be effected in several ways. Thus, all the ingredients may be reacted together in one stage; the glycol may be reacted with the acid to form a glycol half-ester which is then esterified with the alcohol; the alcohol may be reacted with the acid to form a half-ester which is then esterified with the glycol; the glycol may be reacted in alkyl interchange with the alcohol diester of the acid. The esterifications may be broken down into any number of stages; thus, half the glycol can be esterified with all the acid, half the alcohol is added in a second stage, the remainder of the glycol in a third and the remainder of the alcohol in a fourth stage. The proportions of the reagents may be varied; they may be such as will yield a pure complex ester or a blend of the complex ester with the diester of the alcohol and acid. The products may be used as lubricants (see Group III). In examples: (1) a complex ester is formed from 2-ethyl hexanol, adipic acid and polyglycol 200 (mainly tetraethylene glycol) by the one-stage method; (2) a complex ester is formed from 2-ethyl hexanol, sebacic acid and polyglycol 200 by the glycol half-ester method; (3) blends of complex ester and alcohol diester are formed from sebacic acid, polyglycol 200 and nonyl alcohol, 2-ethylhexanol and C9 Oxo-alcohol respectively by the one-stage and glycol half-ester methods; in all cases, sodium bisulphate is the catalyst. In some of the examples the rate of reaction is compared with the lower rate obtained where p-toluene sulphonic acid is used as catalyst. Iso-octanol, capryl alcohol and triethylene glycol are further examples of specified reactants. Specifications 666,697, 680,438, 683,803, 687,346, [Group III], and 687,347 are referred to.ALSO:Complex esters suitable as lubricants having the general formula R1-OOC-R2-COO-R3-OOC-R4-COO-R5 in which R1 and R5 are aliphatic alcohol or ether alcohol residues, R2 and R4 are hydrocarbon radicals of aliphatic dicarboxylic acids or are direct carbon-to-carbon linkages and R3 is the hydrocarbon or oxygenated hydrocarbon radical of a glycol or polyglycol, all of the radicals R1 to R5 being saturated, are prepared by the reaction in one or more stages in the presence of an alkali metal or ammonium bisulphate as esterification catalyst, of appropriate alcohols, acids and glycols in proportions to give the required complex ester (see Group IV (b)). The reactants may be used in proportions yielding the pure complex ester or a blend of the complex ester and the diester of the alcohol and dicarboxylic acid. Suitable reactants are C4 to C24 polyglycols or mixtures thereof, C1 to C12 alkanols or mixtures thereof and C6 to C20 dicarboxylic acids or mixtures thereof though acids down to oxalic may be used. Complex esters particularly suitable as lubricants contain 20-100 and preferably 30 to 60 carbon atoms. In examples: (1) a complex ester is prepared from 2-ethyl hexanol, adipic acid and polyglycol 200 (mainly tetraethylene glycol); (2) a complex ester is formed from 2-ethyl hexanol, sebacic acid and polyglycol 200; (3) blends of complex ester and alcohol diester are formed from sebacic acid, polyglycol 200 and nonyl alcohol, 2-ethylhexanol and C9 oxoalcohol respectively. Other reactants mentioned are iso-octanol, capryl alcohol and triethylene glycol. Specifications 666,697, 680,438, 683,803, 687,346 and 687,347 are referred to.

公开(公告)号：GB720372A

公开(公告)日：1954-12-15

申请号：GB1739451

申请日：1951-07-23

Applicant: STANDARD OIL DEV CO

Inventor： JONES GWYNETH EUGENIE MARY ,  MORTON RONALD WILLIAM

IPC: C10M169/00

Abstract: A lubricating oil additive is prepared by reacting at an elevated temperature one or more alkaline earth metal oxides, hydrated oxides, hydroxides and alcoholates with one or more nuclear alkylated phenols, heating the reaction product with sulphur and then further reacting the sulphurized product with one or more of the above alkaline earth metal compounds at an elevated temperature, the total amount of the said alkaline earth metal compounds added is such that the molar ratio of alkaline earth metal to the phenol is between 0.55 : 1 and 1.1 to 1, preferably 0.76 : 1 and 0.85 : 1. The reactions with the alkaline earth metal compounds may be carried out at between 90 DEG and 270 DEG C. and preferably between 170 DEG and 190 DEG C., the preferred temperature for the sulphurization reaction being between 90 DEG and 210 DEG C. and preferably between 160 DEG and 190 DEG C. The molar ratio of alkaline earth compound to the phenol in the first stage may be between 0.5 : 1 and 0.8 : 1 and preferably between 0.6 : 1 and 0.75 : 1, and in the final stage the ratio may be between 0.05 : 1 and 0.03 : 1 and preferably between 0.07 : 1 and 0.23 : 1. The sulphur to phenol molar ratio is preferably between 1 : 1 and 2 : 1, e.g. 1.2 : 1 to 1.5 : 1. The reaction can be carried out in an inert solvent, preferably a mineral oil distillate such as a mineral lubricating oil. A minor proportion (preferably between 3 and 15 per cent by weight of the reaction mixture) of a higher aliphatic alcohol having from 8 to 20 carbon atoms used with the mineral oil solvent prevents foaming and acts as an auxiliary solvent. The preferred nuclear alkylated phenols are the p-tert-alkylphenols, e.g. p-tert.-octylphenol. The alkaline earth metal compounds may be calcium or barium compounds or mixtures thereof. The final reaction product may be blown with carbon dioxide and/or volatile materials removed by steam stripping. In the example, an additive is prepared by heating in a mineral oil p-isoctylphenol and barium oxide, the reaction product is then heated with sulphur and the sulphurized product is heated with a further quantity of barium oxide. Specification 586,841 is referred to. The Provisional Specification further discloses the use of thiophenols in place of the alkylated phenols in the above process.ALSO:A lubricating composition comprising a mineral lubricating oil and a minor proportion, preferably between 0.5 and 20 per cent. by weight, of an oil additive obtained by reacting at an elevated temperature one or more alkaline earth metal oxides, hydrated oxides, hydroxides and alcoholates with one or more nuclear alkylated phenols, heating the reaction product with sulphur and then further reacting the sulphurized product at an elevated temperature with one or more of the above alkaline earth metal compounds. The total amount of the said alkaline earth metal compounds added is such that the molar ratio of alkaline earth metal to phenol is between 0.55:1 and 1.1:1 [see Group IV (b)]. The preferred quantity of oil additive is between 1 and 10 per cent. by weight. The composition may contain also a minor proportion of alkaline earth metal mahogany sulphonate-preferably between 0.5 and 20 per cent. by weight, e.g. between 1 and 10 per cent. by weight. A minor proportion, e.g. between 3 and 15 per cent. by weight of the composition, of a higher aliphatic alcohol having from 8 to 20 carbon atoms may be added to the composition, e.g. lauryl, cetyl, stearyl or wool fat alcohol may be present. Antioxidants which are normally used in motor oils may be added to the composition. Specification 586,841 is referred to. The Provisional Specification further discloses the use of an oil additive obtained by using a thiophenol in place of the alkylated phenols referred to above.

公开(公告)号：GB687347A

公开(公告)日：1953-02-11

申请号：GB747349

申请日：1949-03-18

Applicant: STANDARD OIL DEV CO

Inventor： MORTON RONALD WILLIAM

Abstract: Ester blends are prepared by reacting together in one or more stages and in the presence of an esterification catalyst if necessary, an aliphatic dicarboxylic acid or acids or esterifying equivalent, an aliphatic glycol or glycols, polyglycol or polyglycols or esterifying equivalent and an aliphatic alcohol or alcohols or esterifying equivalent in appropriate proportions adapted to yield after the final esterifying stage a mixture of a complex ester of general formula R1-OOC-R2-COO-R3-OOC-R4-COOR5, and the alcohol diester or diesters of the dicarboxylic acid or acids, R1 and R5 representing the alcohol (including ether alcohol) residues, R2 and R4 representing the hydrocarbon radicals of the acid or acids, and R3 representing the hydrocarbon or oxahydrocarbon radical of the glycol or glycols, all the radicals R1 to R5 being saturated and the total number of carbon atoms in the complex ester being from 20 to 100, preferably from 30 to 60. The preferred starting materials are the acids, glycols and alcohols used in presence of an esterification catalyst, but there may also be used alkali metal salts of the acids and halogen derivatives of the alcohol and glycol or the acid chlorides and alkali metal derivatives of the alcohol and glycol. The components may be reacted in several ways; thus all three may be refluxed together; the glycol may be reacted with the acid in a first stage to form a mixture of glycol half-ester and free acid, which mixture is then esterified with the alcohol; the alcohol may be reacted with the acid in a first stage to form a mixture of diester and alcohol half-ester, which mixture is then esterified with the glycol, and in these methods the preferred mol, ratio of the acid, alcohol and glycol starting materials are 2+n : 2+2n : 1 where n : 1 is the desired molar ratio of diester to complex ester in the blend; or the glycol, glycols, polyglycol or polyglycols may be reacted in the presence of an esterification catalyst with more than 2 molar proportions of an alkyl di-ester of a dicarboxylic acid whereby the blend of complex ester and diester is obtained in which connection, Specification 683,803 is referred to. Preferably, the blend contains a minor proportion of the diester. The processes may be artificially broken down to any number of desired stages; for example, half of the glycol may be esterified with all the acid, half the alcohol added in a second stage, the remainder of the glycol in a third and the remainder of the alcohol in a fourth stage. Suitable starting materials are C1 to C12 alkanols or mixtures thereof, e.g. iso-octanol, oxo-nonanol or other oxo-fractions, C6 to C20 acids or mixtures thereof, e.g. polymethylene succinic acids such as adipic or sebacic acid, C4 to C24 polyglycols such as tri- or tetra-ethylene glycol. Ester blends are described obtained by the one stage method or glycol half-ester method, water of esterification being removed by means of toluene as an entrainer, from (1) 2 mols. each of 2-ethyl hexanol and oxo-nonanol, 3 mols sebacic acid and one mol. polyglycol 200; (2) oxo-nonanol, sebacic acid and polyglycol 200, yielding blends containing 64 and 73 per cent complex ester; (3) nonanol, 2-ethyl-hexanol, sebacic acid and polyglycol 200, the resulting blend containing 79 per cent complex ester; (4) nonanol, capryl alcohol, sebacic acid and polyglycol 200, the resulting blend containing 81 per cent complex esters; the blends are compared with similar blends prepared by mixing the complex ester with the diester. Specifications 666,697, 683,803, and 687,346, [Group III], are referred to.ALSO:Lubricant ester blends for use, e.g. in aviation turbines, are prepared by reacting together in one or more stages in the presence of an esterification catalyst if necessary, an aliphatic dicarboxylic acid or acids or esterifying equivalent, an aliphatic glycol or glycols, polyglycol or polyglycols or esterifying equivalent and an aliphatic alcohol or alcohols or esterifying equivalent in appropriate proportions adapted to yield after the final esterifying stage a mixture of complex ester, of the general formula R1-OOOC-R2-COO-R3-OOC-R4-COO R5, and the alcohol diester or diesters of the dicarboxylic acid or acids, R1 and R5 being the alcohol (including ether alcohol) residues, R2 and R4 being the hydrocarbon radicals of the acid or acids, and R3 being the hydrocarbon or oxahydrocarbon radical of the glycol or glycols, all the radicals R1 to R5 being saturated and the total number of carbon atoms in the complex ester being from 20 to 100, preferably from 30 to 60. Several methods of effecting the preparation of the blends are described, (see Group IV(b)). The reactants are preferably used in the mol ratio of acid: alcohol:glycol of 2+n:2+n:1 where n:1 is the desired molar ratio of diester to complex ester in the blend; the diester preferably constitutes a minor proportion of the blend. Suitable starting materials are C1 to C12 alkanols or mixtures thereof, e.g. 2-ethyl hexanol, iso-octanol and oxo-nonanol or other oxo-fractions, C6 to C20 acids or mixtures thereof, e.g. polymethylene succinic acids such as adipic or sebacic, and C4 to C24 polyglycols, e.g. tri-and tetra-ethylene glycols. Blends are described obtained from (1) 2-ethyl-hexanol, oxo-nonanol, polyglycol 200 and sebacic acid, the blend containing 64 per cent complex ester; (2) oxo-nonanol, sebacic acid and polyglycol 200, blends being formed containing 64 and 73 per cent complex ester; (3) nonanol, 2-ethyl-hexanol, sebacic acid and polyglycol 200, the complex ester content being 79 per cent; (4) nonanol, capryl alcohol, sebacic acid and polyglycol 200, the complex ester content being 81 per cent. These blends are compared with those obtained by mixing the complex ester with the diester. Specifications 666,697, 683,803 and 687,346 are referred to.

公开(公告)号：GB711211A

公开(公告)日：1954-06-30

申请号：GB2095950

申请日：1950-08-24

Applicant: STANDARD OIL DEV CO

Inventor： MORTON RONALD WILLIAM ,  PORTER ALAN JAMES ,  GREENWOOD JOHN

IPC: C07C69/34 ,  C10M169/00

Abstract: A lubricating composition (see Group III) comprises a dialkyl ester of a saturated dicarboxylic acid together with a polymer soluble in the dialkyl ester, the viscosity of the composition being greater than that of the dialkyl ester and the acidity of the dialkyl ester being less than 0.3 mg. KOH/gm. In the examples, lubricating compositions are described consisting of (a) dinonyl sebacate (acidity 0.07 mg. KOH/gm.), mineral oil solution of polymethyl methacrylate and phosphosulphurized alpha-pinene and (b) dinonyl sebacate (acidity 0.05 mg. KOH/gm.), polybutyl methacrylate and phenthiazine.ALSO:A lubricating composition (see Group III) comprises a dialkyl ester of a saturated dicarboxylic acid together with a polymer or a complex ester soluble in the dialkyl ester, the viscosity of the composition being greater than that of the dialkyl ester and the acidity of the dialkyl ester being less than 0.3 mg. KOH/gm. Complex esters mentioned are as follows: (1) esters of the formula R1OOC.R2.COOR3.OOCR4.COOR5 (some of which are described in Specifications 666,697, 687,346 and 687,347) where R1 and R5 are aliphatic alcohol or ether alcohol residues, R2 and R4 are the hydrocarbon radicles of aliphatic dicarboxylic acids and R3 is the hydrocarbon or oxygenated hydrocarbon radicle of a glycol or a polyglycol, all the radicles R1-R5 being saturated; (2) esters (including those described in Specification 668,663) formed by fully esterifying a dicarboxylic acid R(COOH)2 (where R is a hydrocarbon radicle containing 0-26 carbon atoms or an organic radicle consisting of a series of saturated aliphatic hydrocarbon radicles linked by at least one non-carbon atom chosen from the elements oxygen and sulphur, the total number of carbon atoms and said non-carbon atoms in the radicle being 3-80, there being at least 2 carbon atoms between each pair of said non-carbon atoms and a total of not more than 2 sulphur atoms) with a hydroxy ester of the formula where R1 is either an aliphatic hydrocarbon radicle containing 1-22 carbon atoms or a radicle containing 2-22 carbon atoms and consisting of two aliphatic hydrocarbon groups interlinked by one atom of oxygen or sulphur, R11 is either an aliphatic hydrocarbon radicle containing 1-20 carbon atoms or a radicle consisting of a series of saturated aliphatic hydrocarbon radicles (each having at least 2 carbon atoms) linked through 1-5 non-carbon atoms chosen from the elements oxygen and sulphur so that the total number of carbon atoms and said non-carbon atoms is 4-20 and the total number of sulphur atoms is not more than 2, R1, R2, R3 and R4 are each chosen from hydrogen, methyl and ethyl, m is an integer from 1 to 20 and n is 1 or 2; (3) esters (including those described in Specification 664,992) of formula where R1 is an aliphatic hydrocarbon group which may contain one or more hydroxyl groups, R is an aliphatic hydrocarbon group, R11 is hydrogen or an alkyl or alkylene group containing not more than 6 carbon atoms, R111 is hydrogen or a methyl group, m is an integer from 1 to 3, n is an integer and x is an integer from 1 to 30; (4) esters (including those described in Specification 662,650) of formula R11OOCRCOOR1OOCR111 and prepared by reacting 1 mol. of a dibasic acid with one mol. of a glycol in such a manner that a half ester is formed and esterifying the terminal OH and COOH groups with a monobasic acid and a monohydric alcohol respectively; and (5) esters (including those described in Specification 659,103) of formula R2COOR1OOCR3COOR11OOCR12 and prepared by reacting, under esterification conditions, 2 mols. of a monobasic aliphatic acid with 2 mols. of a glycol and 1 mol. of a dibasic aliphatic or aromatic acid. The blend of a complex ester with a dialkyl ester of a saturated dicarboxylic acid may be made mechanically, or it may be made chemically as described in Provisional Specification 683,803 and in Specification 687,347. The complex ester may also be of the prescribed low-acidity and the esters may be treated separately to lower their acidity to the prescribed value or the blend may be so treated. Methods described and exemplified for reducing acidity are (a) treatment of the esters with alumina, fuller's earth, attapulgus clay, charcoal or other solid adsorbents; (b) treatment of the esters with aqueous or dry alkali such as sodium carbonate, aqueous sodium carbonate preferably being used in presence of isopropyl alcohol, and optionally being followed by treatment (a); (c) prolongation of the esterification reaction in the preparation of the esters; (d) treatment of the esters with anion exchange resins such as m-phenylene diamine-formaldehyde resins; and (e) treatment with a mixture of solid adsorbent and dry alkali such as sodium carbonate. Specification 600,325 also is referred to.ALSO:A lubricating composition, of sufficiently low corrosivity to permit its use in the lubrication of prop-jet engines, comprises a dialkyl ester of a saturated dicarboxylic acid together with a polymer or a complex ester soluble in the dialkyl ester, the viscosity of the composition being greater than that of the dialkyl ester and the acidity of the dialkyl ester being less than 0.3 mg. KOH/gm. The complex esters referred to are defined as esters containing in the molecule more than 3 monocarboxylic acid, monohydric alcohol, polycarboxylic acid or polyhydric alcohol residues, and in which there is at least one polyhydric alcohol and one polycarboxylic acid residue, each of which has at least two of its functional groups. They are formed by the esterification, in one or more stages, of mixtures of polycarboxylic acids and polyhydric alcohols with or without monocarboxylic acids, monocarboxylic acids and monohydric alcohols, or monohydric alcohols. The various types of suitable complex esters are discussed (see Group IV (b)) and they include the complex esters of Specifications 659,103, 662,650, 664,992, 666,697, 668,663, 687,346, and 687,347. Polymers mentioned are polyolefins, polymerized unsaturated esters, copolymers of olefins and aromatic hydrocarbons with unsaturated side chains, copolymers of two or more unsaturated esters, and mixtures of such polymers. The lubricating composition may contain additional ingredients such as dyes, antioxidants, detergents, mineral and synthetic hydrocarbon oils, and other synthetic lubricating oils such as those of the polyglycol ether type. Methods of reducing the acidity of the dialkyl ester of a saturated dicarboxylic acid to the prescribed value are described (see Group IV (b)) and it is stated that the acidity of the complex ester may similarly be reduced. If desired, the acidity may be reduced only after the formation of the lubricating composition. Although primarily intended for aviation turbine lubricants, the lubricating compositions may also be employed as motor lubricants, as recoil oils and hydraulic fluids, for example in gun control mechanisms, as lubricants and working fluids for precision tools and as electrical oils. In the examples, lubricating compositions are described consisting of (a) dinonyl sebacate of acidity 0.07mg. KOH/gm., mineral oil solution of polymethyl methacrylate and phosphosulphurized alpha-pinene, (b) dinonyl sebacate of acidity 0.05mg. KOH/gm., polybutyl methacrylate and phenthiazine and (c) dinonyl sebacate of acidity 0.07mg. KOH/gm., complex ester of acidity 0.05mg. KOH/gm. and phenthiazine. The complex ester of example (c) is one prepared by esterifying 1 mol. of crude polyethylene glycols, having a mean molecular weight approximating to that of tetraethylene glycol, with 2 mols. of sebacic acid and then esterifying the half ester thus formed with 2 mols. of 2-ethyl-hexanol. Specifications 600,325 and 683,803 also are referred to.

公开(公告)号：GB687346A

公开(公告)日：1953-02-11

申请号：GB747249

申请日：1949-03-18

Applicant: STANDARD OIL DEV CO

Inventor： MORTON RONALD WILLIAM

IPC: C08G59/56 ,  C08G59/62 ,  C09D5/08

Abstract: A complex ester of general formula R1-OOC-R2-COO-R3-OOC-R4-COO-R5 in which R1 and R5 are aliphatic alcohol or ether alcohol residues, R2 and R4 are the hydrocarbon radicals of aliphatic dicarboxylic acids and R3 is the hydrocarbon or oxygenated hydrocarbon radical of a glycol or polyglycol, all the radicals being saturated and the total number of carbon atoms being between 20 and 100, is blended with a liquid aliphatic diester of a saturated aliphatic dicarboxylic acid to give a lubricating composition. Preferably the total number of carbon atoms in the complex ester is about 30-60. The complex esters are preferably prepared by the glycol halfester method described in Specification 666,697 from C4-C24 polyglycols, C1 to C12 alcohols and C6-C20 dicarboxylic acids. The starting compounds may be relatively straight chain compounds, but 2-ethyl hexanol and iso-octanol are preferred as R1 and R5 to give low pour points. The blends may also be prepared by the method described in Specification 687,347. Each radical R may be a blend of materials if desired, e.g. polyglycol fractions, mixtures of dibasic acids and OXO alcohol cuts. The preferred esters are prepared from octyl or nonyl alcohols, adipic or sebacic acids and triethylene or tetraethylene glycols. The preferred diesters are esters of C1-C12 aliphatic alcohols, particularly branched chain alcohols such as 2-ethyl hexanol, iso-octanol, a nonanol or an OXO alcohol, with a C6-C20 aliphatic dicarboxylic acid, particularly of the polymethylene series such as adipic or sebacic acid. Suitable esters are di-(2-ethylhexyl)-sebacate, di-iso-octyl sebacate and dinonyl sebacate. Blends containing up to 70 per cent diester by volume are satisfactory as aviation turbine lubricants, but blends containing a major proportion (60-70 per cent by volume) of the complex ester are preferred. Antioxidants, preferably of the phenolic type such as 2,6-di-tert.-butyl-4-methyl phenol, may be added in amounts up to 1 per cent by weight, preferably 0.1 to 0.5 per cent. The results are given of tests on blends of (1) a complex ester from 2-ethyl hexanol, sebacic acid and polyglycol 200 with dinonyl sebacate and di-iso-octyl sebacate, (2) a complex ester from nonyl alcohol, sebacic acid and polyglycol 200 with di-octyl, dinonyl, di-capryl, and di 2-ethyl-hexyl sebacates, and (3) a complex ester from 2-ethyl hexanol, sebacic acid and polyglycol 200 with di-nonyl sebacate. Specification 687,348 also is referred to.