US2570037A - Esters of aliphatic dibasic acids and ether-alcohols containing a branched chain in the glycol group - Google Patents

Esters of aliphatic dibasic acids and ether-alcohols containing a branched chain in the glycol group Download PDF

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US2570037A
US2570037A US42334A US4233448A US2570037A US 2570037 A US2570037 A US 2570037A US 42334 A US42334 A US 42334A US 4233448 A US4233448 A US 4233448A US 2570037 A US2570037 A US 2570037A
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esters
ether
branched chain
dibasic acids
alcohols containing
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Jr Paul V Smith
Jr Fred Knoth
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Standard Oil Development Co
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    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M3/00—Liquid compositions essentially based on lubricating components other than mineral lubricating oils or fatty oils and their use as lubricants; Use as lubricants of single liquid substances
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/34—Esters of acyclic saturated polycarboxylic acids having an esterified carboxyl group bound to an acyclic carbon atom
    • C07C69/44—Adipic 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
    • C07C69/34—Esters of acyclic saturated polycarboxylic acids having an esterified carboxyl group bound to an acyclic carbon atom
    • C07C69/50—Sebacic acid esters
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/282—Esters of (cyclo)aliphatic oolycarboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/34—Esters having a hydrocarbon substituent of thirty or more carbon atoms, e.g. substituted succinic acid derivatives
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
    • C10M2209/105—Polyethers, i.e. containing di- or higher polyoxyalkylene groups of alkylene oxides containing three carbon atoms only
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
    • C10M2209/106—Polyethers, i.e. containing di- or higher polyoxyalkylene groups of alkylene oxides containing four carbon atoms only
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2020/00—Specified physical or chemical properties or characteristics, i.e. function, of component of lubricating compositions
    • C10N2020/01—Physico-chemical properties
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/08—Resistance to extreme temperature
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/12—Gas-turbines
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/12—Gas-turbines
    • C10N2040/13—Aircraft turbines

Definitions

  • This invention relates to a new class of organic compounds consisting of esters of a type to be specified hereinafter, the same being found to possess properties which indicate that these compounds are particularly suitable for use as synthetic lubricants.
  • Esters represent one class of materials which have attracted unusual interest as synthetic lubricants. In general, they are characterized by higher viscosity indices and lower pour points than mineral oils of corresponding viscosity. The esters described in the present specification have been found to exhibit very low pour points and high viscosity indices. *Lubricants possessing such properties are of special value to the lubrication of engines which are subjected to high temperatures such as combustion turbine engines, particulary those of the prop-jet type.
  • Mineral oil lubricants containing addedviscosity index improvers, thickeners or other highly nonvolatile additives are undesirable for use in such engines because of the tendency to leave a residue which would accumulate and interfere with the operation of the engine.
  • a synthetic lubricant of the type described in the present specification is especially adapted to use under such conditions, since the lubricant contains no additives and thus tends to leave no residue upon volatilization.
  • esters of aliphatic dibasic acids which are distinguished for exhibiting a high viscosity index and very low pour points, are esters of aliphatic dibasic acids, characterized by the presence of at least one oxygen atom and a branched chain hydrocarbon structure in each ester group.
  • Esters of the above typemaybe formed by esterifying the dibasic acids with ether-alcohols obtained by reacting aliphatic monohydric alco- If, then, this product is reacted with a typical dibasic acid such as adipic acid, the resulting product will consist of mixtures of the following three compounds:
  • ether alcohols will be formed having more than one ether linkage in the molecule, and such compounds may be likewise employed in the formation of the 'esters' of the present invention.
  • One series ot ether-alcohols formed in this manner are known to the trade as Dowanols.
  • the alkylene oxide to be employed must contain at least three carbon atoms, a branched chain structure results in the ester group.
  • a mixture of the ether-alcohols is reacted with a dibasic acid, a mixture of esters will be formed, but such mixtures will be suitable for use as synthetic lubricants in the same manner as pure esters.
  • the new class of esters forming the subject matter of the present invention may be defined by the formula a oo (c O)R R5 R1 fishnet I ls is n As can be seen from the formula,
  • bon atoms at least one being an alkyl group
  • R and R each represent an aliphatic hydrocarbon radical, saturated-or unsaturated, straight chain or branched; n and n areintegers; and
  • the present invention may be prepared from any of the paraffin dicarboxylic acids containing from 2 to 28 carbon atoms. Where R of the formula contains no carbon atoms, the acid employed is oxalic acid.
  • acids which may be employed are, for example, oxalic, malonic, succinic, pyrotartaric, dimethylsuccinic, trimethylsuccinic, glutaric, adipic, trimethyladipic, suberic, sebacic, and hexadecane dicarboxylic acids, as well as unsaturated acids such as maleic acid, fumeric acid, and alkenyl succinic acids, the last named being formed by condensing olefins with maleic anhydride. 7
  • the alcohols which may be employed in the esterification of the dicarboxylic acids are of the type which are formed by reacting anyof the monobasie aliphatic alcohols, whether primary, secondary, or tertiary, with propylene oxide, 1,2- or 2,3-butylene oxide, or isobutylene oxide, the chain length of the alcohol and the number of molecular proportions of alkylene oxide for each molecular proportion of alcohol being limited by Acid Propylene- Sebacie.
  • the total vof-carbon and oxygen atoms in each ester group should not exceed 20.
  • the alcohols which are of most particular interest in the preparation of the new esters may be mentioned methyl, ethyl, n-'propyl, isopropyl, n-butyl, isobutyl, sec.-buty1, tert.-butyl, n-amyl, iso-amyl, sec.-amyl, tertamyl, 2-ethylbutyl, n-octyl, tert.-octyl, Z-ethylhexyl, n-decyl, cetyl, lauryl, and oleyl alcohols.
  • the esterification process can be carried out by the usual methods, preferably employing an esterification catalyst such as p-toluenesulfonic acid and a water-entraining agent.
  • an esterification catalyst such as p-toluenesulfonic acid and a water-entraining agent.
  • esters of the present invention may be employed not only as such but also in mixtures with mineral oils to produce lubricants of su'perior properties with respect to viscosity index, pour point, and other desirable characteristics.
  • What is claimed is: 1. A composition of matter having the formula COO(E E O)R IL 1 l1 LOOGLQW where R is an alkylene group containing 4 to S carbon'atoms; where one of the groups R1 and R2 in each esterifying radical is a methyl group and the other is hydrogen; where R is an alkyl groupcontaining 1 to 3 carbon atoms; and where n is an integer from 1 to 3.

Description

Patented Oct. 2, 1 951 OFFICE ESTERS OF ,AL IPHATIC DIBASIC ACIDS AND ETHER-ALCOHOLS CONTAINING A BRANCHED CHAIN IN THE GLYCOL GROUP Paul V. Smith, J 11., Westfield, and Fred Knoth, Jr., Union, N. J. assignors to Standard Oil Development'Company, a corporation of Delaware No Dra wing. Application August 3, 1948,
Serial No. 42,334
-5 Claims. 1 1
This invention relates to a new class of organic compounds consisting of esters of a type to be specified hereinafter, the same being found to possess properties which indicate that these compounds are particularly suitable for use as synthetic lubricants.
In the lubricant art, considerable progress has been realized in recent years in the production of lubricants characterized by one or more speciflc properties and adapted for particular uses. In the main, this progress can be attributed to two developments: the first, new refining procedures, and the second, addition agents capable of imparting particular properties to available lubricants. Thus, viscosity index improvers and pour depressants are added to automotive lubricants to render the lubricants more adaptable to wide changes in temperature conditions, while other agents are added to improve the load carrying properties of a lubricant which is to be employed, for example, under extreme pressure conditions. u
Recently, in an effort to obtain superior lubricants endowed with specific and superior characteristics, a new field has been explored, namely, the synthesis of lubricants from various materials. Esters represent one class of materials which have attracted unusual interest as synthetic lubricants. In general, they are characterized by higher viscosity indices and lower pour points than mineral oils of corresponding viscosity. The esters described in the present specification have been found to exhibit very low pour points and high viscosity indices. *Lubricants possessing such properties are of special value to the lubrication of engines which are subjected to high temperatures such as combustion turbine engines, particulary those of the prop-jet type. Mineral oil lubricants containing addedviscosity index improvers, thickeners or other highly nonvolatile additives are undesirable for use in such engines because of the tendency to leave a residue which would accumulate and interfere with the operation of the engine. A synthetic lubricant of the type described in the present specification is especially adapted to use under such conditions, since the lubricant contains no additives and thus tends to leave no residue upon volatilization.
The new compounds of the present invention,
which are distinguished for exhibiting a high viscosity index and very low pour points, are esters of aliphatic dibasic acids, characterized by the presence of at least one oxygen atom and a branched chain hydrocarbon structure in each ester group.
Esters of the above; typemaybe formed by esterifying the dibasic acids with ether-alcohols obtained by reacting aliphatic monohydric alco- If, then, this product is reacted with a typical dibasic acid such as adipic acid, the resulting product will consist of mixtures of the following three compounds:
and
on, on, I 000 114111200113 o'ooom-tuoon, (0H1); Hi).
CH3 CH3 OO(IJH-CH2OCH3 oocnr-cnocni CHI coodH-omocm on, oocuz-cinoom If more than one mol of alkylene oxide is reacted with the monohydric alcohol, ether alcohols will be formed having more than one ether linkage in the molecule, and such compounds may be likewise employed in the formation of the 'esters' of the present invention. One series ot ether-alcohols formed in this manner are known to the trade as Dowanols.
Since the alkylene oxide to be employed must contain at least three carbon atoms, a branched chain structure results in the ester group. Obviously, when a mixture of the ether-alcohols is reacted with a dibasic acid, a mixture of esters will be formed, but such mixtures will be suitable for use as synthetic lubricants in the same manner as pure esters.
The new class of esters forming the subject matter of the present invention may be defined by the formula a oo (c O)R R5 R1 fishnet I ls is n As can be seen from the formula,
bon atoms, at least one being an alkyl group;
R and R each represent an aliphatic hydrocarbon radical, saturated-or unsaturated, straight chain or branched; n and n areintegers; and
the sum of the carbon and oxygen atoms in each group (Elite 16 8 n and is to 26.
' with Water. After drying over a desiccant, such as anhydrous 02,304, th material is stripped at r "a pressure of 5 mm. to a bath temperature of the esters of Q The data obtained in the tests of properties 6f the esters obtained as described are shown in the table.
Table Mols Oxide per Mol Alcohol Alcohol 'Oxide Isopropyl Do 1 HzooowwmH the present invention may be prepared from any of the paraffin dicarboxylic acids containing from 2 to 28 carbon atoms. Where R of the formula contains no carbon atoms, the acid employed is oxalic acid. Among the acids which may be employed are, for example, oxalic, malonic, succinic, pyrotartaric, dimethylsuccinic, trimethylsuccinic, glutaric, adipic, trimethyladipic, suberic, sebacic, and hexadecane dicarboxylic acids, as well as unsaturated acids such as maleic acid, fumeric acid, and alkenyl succinic acids, the last named being formed by condensing olefins with maleic anhydride. 7
,The alcohols which may be employed in the esterification of the dicarboxylic acids are of the type which are formed by reacting anyof the monobasie aliphatic alcohols, whether primary, secondary, or tertiary, with propylene oxide, 1,2- or 2,3-butylene oxide, or isobutylene oxide, the chain length of the alcohol and the number of molecular proportions of alkylene oxide for each molecular proportion of alcohol being limited by Acid Propylene- Sebacie.
the provision, in accordance with the general formula shown above, that the total vof-carbon and oxygen atoms in each ester group should not exceed 20. Among the alcohols Which are of most particular interest in the preparation of the new esters may be mentioned methyl, ethyl, n-'propyl, isopropyl, n-butyl, isobutyl, sec.-buty1, tert.-butyl, n-amyl, iso-amyl, sec.-amyl, tertamyl, 2-ethylbutyl, n-octyl, tert.-octyl, Z-ethylhexyl, n-decyl, cetyl, lauryl, and oleyl alcohols.
The esterification process can be carried out by the usual methods, preferably employing an esterification catalyst such as p-toluenesulfonic acid and a water-entraining agent.
In the table below will be shown data obtained in tests of the properties of seven typical esters illustratingthe present invention, these esters having been formed by first preparing an ether- 7 alcohol by reacting methyl or isopropyl alcohol with one, two and three molecular proportions, respectively, of propylene oxide, and then preparing di-esters of sebacic or adipic acid by esterifying the acid with the alcohols prepared Flash Kinematic Viscosity Point 0 The above data show that the esters which were tested possess unusually valuable properties with respect to their usefulness as synthetic lubricating oils. j
The esters of the present invention may be employed not only as such but also in mixtures with mineral oils to produce lubricants of su'perior properties with respect to viscosity index, pour point, and other desirable characteristics. What is claimed is: 1. A composition of matter having the formula COO(E E O)R IL 1 l1 LOOGLQW where R is an alkylene group containing 4 to S carbon'atoms; where one of the groups R1 and R2 in each esterifying radical is a methyl group and the other is hydrogen; where R is an alkyl groupcontaining 1 to 3 carbon atoms; and where n is an integer from 1 to 3.
' 2. A composition according to claim 1 in which R is the group --(CHz)a-', and where R is an isopropyl radical.
3. A composition according to claim 2 in which n of the formula is 1.
4. A composition according to claim 2 in which n of the formula is 2.
5. A composition according to claim 1 in which R is the group -(CH2)4-, in which R is a methyl radical, and in which n is 3. I
' PAUL V. SMITH, JR.
FRED KNOTH, JR.
REFERENCES CITED UNITED STATES PATENTS Number D t 1 Name 1,706,639 Van Schaack Mar. 26, 1929 2,118,506 Graves May 24, 1938

Claims (1)

1. A COMPOSITION OF MATTER HAVING THE FORMULA
US42334A 1948-08-03 1948-08-03 Esters of aliphatic dibasic acids and ether-alcohols containing a branched chain in the glycol group Expired - Lifetime US2570037A (en)

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GB6424/49A GB664052A (en) 1948-08-03 1949-03-09 Improvements in or relating to synthetic lubricants

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Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2723957A (en) * 1952-02-27 1955-11-15 Exxon Research Engineering Co Synthetic lubricating oils containing paraffinic resins
US2837562A (en) * 1955-01-04 1958-06-03 Exxon Research Engineering Co Synthetic lubricating oil compositions
US3056745A (en) * 1957-04-30 1962-10-02 Bayer Ag Hydraulic oil compositions
US3278585A (en) * 1962-08-08 1966-10-11 Shell Oil Co Process for esterification of secondary alcohols containing an ether group by reaction in the presence of a cation exchange resin catalyst
US3959187A (en) * 1973-12-28 1976-05-25 Emery Industries, Inc. Mixed synthetic ester lubricants as useful polymeric fiber lubricants
US4339236A (en) * 1978-02-21 1982-07-13 Union Carbide Corporation Low foam scouring agents
US5688750A (en) * 1993-06-02 1997-11-18 Unichema Chemie B. V. Base fluid

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US1706639A (en) * 1927-10-31 1929-03-26 Schaack Bros Chemical Works In Alkoxy esters of polybasic organic acids
US2118506A (en) * 1934-07-07 1938-05-24 Du Pont Long chain alkoxy alkanol esters

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US1706639A (en) * 1927-10-31 1929-03-26 Schaack Bros Chemical Works In Alkoxy esters of polybasic organic acids
US2118506A (en) * 1934-07-07 1938-05-24 Du Pont Long chain alkoxy alkanol esters

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2723957A (en) * 1952-02-27 1955-11-15 Exxon Research Engineering Co Synthetic lubricating oils containing paraffinic resins
US2837562A (en) * 1955-01-04 1958-06-03 Exxon Research Engineering Co Synthetic lubricating oil compositions
US3056745A (en) * 1957-04-30 1962-10-02 Bayer Ag Hydraulic oil compositions
US3278585A (en) * 1962-08-08 1966-10-11 Shell Oil Co Process for esterification of secondary alcohols containing an ether group by reaction in the presence of a cation exchange resin catalyst
US3959187A (en) * 1973-12-28 1976-05-25 Emery Industries, Inc. Mixed synthetic ester lubricants as useful polymeric fiber lubricants
US4339236A (en) * 1978-02-21 1982-07-13 Union Carbide Corporation Low foam scouring agents
US5688750A (en) * 1993-06-02 1997-11-18 Unichema Chemie B. V. Base fluid

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