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 PDFInfo
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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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- Prior art keywords
- esters
- ether
- branched chain
- dibasic acids
- alcohols containing
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- 150000002148 esters Chemical class 0.000 title description 18
- 239000002253 acid Substances 0.000 title description 11
- 150000007513 acids Chemical class 0.000 title description 6
- 125000001931 aliphatic group Chemical group 0.000 title description 3
- 125000003827 glycol group Chemical group 0.000 title 1
- 239000000203 mixture Substances 0.000 claims description 11
- 239000000314 lubricant Substances 0.000 description 16
- -1 ether alcohols Chemical class 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 4
- 125000002947 alkylene group Chemical group 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 125000004185 ester group Chemical group 0.000 description 3
- 230000032050 esterification Effects 0.000 description 3
- 238000005886 esterification reaction Methods 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 239000002480 mineral oil Substances 0.000 description 3
- 125000004430 oxygen atom Chemical group O* 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 235000011037 adipic acid Nutrition 0.000 description 2
- 239000001361 adipic acid Substances 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 230000018109 developmental process Effects 0.000 description 2
- 150000001991 dicarboxylic acids Chemical class 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N methyl alcohol Substances OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- GELKGHVAFRCJNA-UHFFFAOYSA-N 2,2-Dimethyloxirane Chemical compound CC1(C)CO1 GELKGHVAFRCJNA-UHFFFAOYSA-N 0.000 description 1
- PQXKWPLDPFFDJP-UHFFFAOYSA-N 2,3-dimethyloxirane Chemical compound CC1OC1C PQXKWPLDPFFDJP-UHFFFAOYSA-N 0.000 description 1
- 125000006176 2-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 description 1
- MEAHFJBYWLCGDM-UHFFFAOYSA-N 2-pentadecylpropanedioic acid Chemical class CCCCCCCCCCCCCCCC(C(O)=O)C(O)=O MEAHFJBYWLCGDM-UHFFFAOYSA-N 0.000 description 1
- HNUALPPJLMYHDK-UHFFFAOYSA-N C[CH]C Chemical group C[CH]C HNUALPPJLMYHDK-UHFFFAOYSA-N 0.000 description 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical group OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000002485 combustion reaction Methods 0.000 description 1
- 239000002274 desiccant Substances 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 125000001183 hydrocarbyl group Chemical group 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000005461 lubrication Methods 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical group [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 235000011044 succinic acid Nutrition 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000010689 synthetic lubricating oil Substances 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Lubricants (AREA)
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
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US42334A US2570037A (en) | 1948-08-03 | 1948-08-03 | Esters of aliphatic dibasic acids and ether-alcohols containing a branched chain in the glycol group |
| GB6424/49A GB664052A (en) | 1948-08-03 | 1949-03-09 | Improvements in or relating to synthetic lubricants |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US42334A US2570037A (en) | 1948-08-03 | 1948-08-03 | Esters of aliphatic dibasic acids and ether-alcohols containing a branched chain in the glycol group |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2570037A true US2570037A (en) | 1951-10-02 |
Family
ID=21921306
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US42334A Expired - Lifetime US2570037A (en) | 1948-08-03 | 1948-08-03 | Esters of aliphatic dibasic acids and ether-alcohols containing a branched chain in the glycol group |
Country Status (2)
| Country | Link |
|---|---|
| US (1) | US2570037A (en) |
| GB (1) | GB664052A (en) |
Cited By (7)
| 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)
| 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 |
-
1948
- 1948-08-03 US US42334A patent/US2570037A/en not_active Expired - Lifetime
-
1949
- 1949-03-09 GB GB6424/49A patent/GB664052A/en not_active Expired
Patent Citations (2)
| 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)
| 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 |
Also Published As
| Publication number | Publication date |
|---|---|
| GB664052A (en) | 1951-01-02 |
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