US3398165A - Diesters containing adamantane nuclei - Google Patents

Diesters containing adamantane nuclei Download PDF

Info

Publication number
US3398165A
US3398165A US531059A US53105966A US3398165A US 3398165 A US3398165 A US 3398165A US 531059 A US531059 A US 531059A US 53105966 A US53105966 A US 53105966A US 3398165 A US3398165 A US 3398165A
Authority
US
United States
Prior art keywords
diesters
adamantane
diester
acid
carbon atoms
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
Application number
US531059A
Other languages
English (en)
Inventor
Irl N Duling
Schneider Abraham
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Sunoco Inc
Original Assignee
Sun Oil Co
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Sun Oil Co filed Critical Sun Oil Co
Priority to US531059A priority Critical patent/US3398165A/en
Priority to GB58127/66A priority patent/GB1113020A/en
Priority to DE19671594622 priority patent/DE1594622A1/de
Priority to NL6702200A priority patent/NL6702200A/xx
Priority to CH233967A priority patent/CH485639A/de
Priority to BE694786D priority patent/BE694786A/xx
Priority to FR97018A priority patent/FR1517143A/fr
Application granted granted Critical
Publication of US3398165A publication Critical patent/US3398165A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic 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
    • 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
    • C07C2603/00—Systems containing at least three condensed rings
    • 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
    • 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
    • C10M2207/281—Esters of (cyclo)aliphatic monocarboxylic 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
    • C10M2207/282—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
    • C10M2207/283—Esters of polyhydroxy compounds
    • 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
    • C10M2207/286—Esters of polymerised unsaturated 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
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2050/00—Form in which the lubricant is applied to the material being lubricated
    • C10N2050/015—Dispersions of solid lubricants
    • C10N2050/02—Dispersions of solid lubricants dissolved or suspended in a carrier which subsequently evaporates to leave a lubricant coating
    • 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
    • C10N2050/00—Form in which the lubricant is applied to the material being lubricated
    • C10N2050/10—Form in which the lubricant is applied to the material being lubricated semi-solid; greasy

Definitions

  • the diesters of the present invention comprise two types as follows:
  • diesters are represented by structural formulas as hereinafter shown. They are both characterized as being derived from the esterification of the specified monoor di-acids by alcohols in which the hydroxy group or groups are located at bridgehead positions of the adamantane nucleus.
  • the present invention is directed to diesters containing either one or two adamantane nuclei and in which each ester group is the reverse of that in the prior art referred to above.
  • the adamantane nucleus (A) is attached to an oxygen atom of the carboxyl group in tlns fashion,
  • diester products provided by the present invention conform in structure either to Formula I or Formula II as follows:
  • R3-C-O o-c-R H II R o-c-R -c-o R In these formulas the R groups are as follows:
  • R a radical having 0-20 carbon atoms selected from the class of hydrogen, alkyl and cycloalkyl,
  • R an alkylene or cycloalkylene radical having 1-20 carbon atoms.
  • R can be a hydrogen atom. Hence only one tertiary hydrogen atom can be attached to each adamantane nucleus.
  • Embodiments of the invention which may often be preferred for either type of diester will have an alkyl substituent at the R position and hence will contain'no tertiary hydrogen on the adamantane nucleus.
  • ester structure represented by will less readily undergo hydrolysis under non-acidic conditions than the reverse structure Since contamination of the lubricant by water may occur in some lubrication systems, this improved hydrolytic stability provides still another desirable stability feature of the present products.
  • bridgehead mono-, dior tri-alkylated adamantanes corresponding to the desired alkyl or cycloalkyl adamantane moiety of the product can be used.
  • the monoand di-alkylated ada- I! OH ER CCI mantanes can be used, whereas for those of Formula 11 trialkylated adamantanes can also be employed.
  • the number of carbon atoms in each alkyl or cycloalkyl group can vary widely ranging say up to 20, it is usually preferable that the R groups be methyl and/or ethyl since the parent hydrocarbons corresponding thereto are more readily obtainable.
  • l-ethyladamantane, 1,3-dimethyladamantane, l-ethy1-3-methyladamantane, 1,3,5- trimethyladamantane and 1,3-dimethyl-5-ethyladamantane can be prepared by aluminum halide catalyzed isomerization of C C tricyclic perhydroaromatics, as disclosed by Schneider et al., JACS, vol. 86, pp. 5365-5367.
  • alkyl or cycloalkyl groups can be substituted on the adamantane nucleus by a Wurtz snythesis involving reacting bridgehead chloro or bromo adamantanes with alkali metal alkyls or cycloalkyls in the manner disclosed in the aforesaid Spengler et al. reference.
  • the alkylated adamantanes can, for the present purpose, have either nonbranched or branched alkyl groups and can have one or more cycloalkyl radicals in the alkylation moiety with the total number of carbon atoms in each R group ranging up to twenty.
  • the R groups contain no tertiary hydrogen atoms.
  • the starting alkylated adamantane hydrocarbon is first converted to a 1,3-diol if esters according to Formula I are desired, or to a l-monool if Formula II products are the kind to be prepared.
  • One manner of effecting such conversions is by air oxidation of the parent hydrocarbons at, for example, 160 C. in the presence of a metal salt oxidation catalyst, as disclosed in Schneider United States applications Ser. No. 395,557, now U.S. Patent 3,356,740 and Ser. No. 395,580, now US. Patent 3,356,- 741 each filed Sept. 10, 1964.
  • oxidation monools form first and these will subsequently convert to diols if the reaction is allowed to continue sufficiently.
  • Some amounts of ketones are also formed during the oxidation. Production of the monools can be maximized by stopping the oxidation before conversion has been reached, while production of diols can be maximized by oxidizing to higher conversion levels.
  • a preferred procedure for making the diesters is by reacting the hydroxy-containing adamantane compound with aliphatic or cycloaliphatic acid chlorides.
  • the procedure involves the following reaction:
  • This reaction takes place too slowly at room temperature and hence an elevated temperature should be employed, e.g., 100-150 C.
  • a solvent such as pyridine can be used so that the hydrogen chloride will be neutralized as it is formed. While this is not essential, it is advantageous for inhibiting side reaction particularly in cases where R is a hydrogen atom.
  • the preferred esterification procedure for making Type II diesters involves reaction as follows:
  • This esterification reaction takes place more readily than that of the preceding equation and can be carried out at room temperature simply by mixing the two reactants.
  • the reaction is exothermic and hence it is desirable to add the monool slowly to the alkane dioyl chloride while stirring the mixture.
  • a solvent such as pyridine can be used to avoid side reaction and is particularly desirable in case R is a hydrogen rather than an alkyl substituent.
  • the use of a stoichiometric excess of the alcohol helps to insure complete esterification of the alkane dioyl chloride.
  • removal of the excess alcohol is not readily effected, as this requires the use of such separation procedures as chromatography, distillation and/or fractional crystallization.
  • the molar ratio of the dioyl chloride to the monool may be in the range of 0.5 :l to 0.7: 1. Any resulting half-ester can be removed by washing the product with aqueous sodium carbonate.
  • any conventional or suitable procedure can be used for working up the product.
  • the mixture can be diluted with a solvent such as ether, pentane or benzene and then washed with aqueous sodium carbonate solution or other mild alkali to remove any acid chlorides.
  • the diester product can be recovered in relatively pure form by distillation and/ or chromatography. In cases where highly pure product is desired, hydrogenation using Raney nickel catalyst (which does not affect the ester group) and contact with decolorizing adsorbents can be utilized.
  • the diesters of both types when highly pure are colorless, while the less pure products usually have a pale yellow color.
  • acyl chlorides of any alkyl or cycloalkyl monocarboxylic acids having 2-21 carbon atoms are suitable for contributing the moieties to the molecules, and fatty acids are inexpensive sources of this component.
  • Acyl chlorides having 6-12 carbon atoms and a straight chain R group are preferred for making lubricant oils. Specific examples are the chlorides corresponding to the following acids: caproic, nheptylic, caprylic, pelargonic, capric, n-undecylic and lauric.
  • chlorides corresponding to the following carboxylic acids acetic, propionic, butyric, isovaleric, myristic, palmitic, stearic, arachidic and the like.
  • chlorides corresponding to acids containing naphthene rings can be used, for example, corresponding to cyclohexane carboxylic acid or Decalin carboxylic acids.
  • the dioyl chlorides of any alkylene or cycloalkylene dicarboxylic acids having 3-22 carbon atoms can be employed as the source of the o 0 labillinkage.
  • Those corresponding to straight chain diacids having 6-12 atoms are preferred for making lubricant oils namely, the following diterminal diacids: adipic, pimelic, suberic, azelaic, sebacic, undecanedioic and dodecanedioic.
  • dichlorides of diacids having less or more carbon atoms also can be used including those of malonic, succinic and glutaric acids, as also can the dichlorides of diacids containing naphthene rings such as cyclohexane dicarboxylic acids or Decalin dicarboxylic acids.
  • any of the foregoing acid chlorides can be made from the corresponding monoacid or diacid by reacting the same in known manner with suitable chloride reagents such as phosgene, thionyl chloride, oxalyl chloride, PCl or PCl
  • suitable chloride reagents such as phosgene, thionyl chloride, oxalyl chloride, PCl or PCl
  • Oxalyl chloride was used to convert the pelargonic acid to its acyl chloride. Specifically, g. of oxalyl chloride were slowly added to g. of pelargonic acid and the mixture was refluxed for 2 hours. Excess oxalyl chloride was removed under aspirator vacuum at room temperature. The resulting acid chloride was heated to 105-1 10 C. and 70 g.
  • Examples 2-5 For Examples 2, 3, 4 and 5 other Type I diesters were made from 1,3-dihydroxy-5,7-dimethyladamantane in subadamantyl)dodecancdicarboxylate. This oil had prop erties as shown in Table 2 infra.
  • Examples 7-8 In these examples two other Type II diesters were prepared in substantially the same manner as described in TABLE 1.PROPERTIES OF TYPE I DIESTERS Density, R.I., Kv. at Kv. at ASTM Glass Melting Acid Used No. of O g./l. at 20 0. 100 F., 210 F., D-567, Transi- Point,
  • Example 6 Preparation of bis-(3,5-dimethyladamanty l)dodecanedicarboxylate
  • the diacid was first convented to the alkane dioyl chloride by means of oxalyl chloride. Specifically 10 ml. of oxalyl chloride were added dropwise to 5. g. of the diacid in a 100 ml. flask fitted with a reflux condenser and a dropping funnel. Vigorous reaction and evolution of gas occurred.
  • Products of the invention have better low temperature properties than would be predicted from the A.S.T.M. viscosity-temperature slope between F. and 210 F. This is shown, for example, by data listed in Table 3 for the dipelargonate product of Example 1.
  • Table 3 shows measured values of kinematic viscosities at various temperatures compared with values predicted from the A.S.T.M. slope. It also shows flash point, T and pour point values for this product.
  • Example 9' solution (one liter). The mixture was filtered through diatomaceous earth, pentane being used to wash the oil therefrom. The pentane layer was separated from the green aqueous layer and washed three times with water. Most of the pentane was stripped OE and anhydrous sodium carbonate added to the oil to make a thick paste. This was maintained for 2 hours at 70 C. under nitrogen. The sodium carbonate was filtered from the oil and washed with pentane. Alumina (5 g.) was added to the pentane solution and the mixture was stirred two hours at 70 C. under nitrogen. The pentane was stripped oif and the oil was distilled. The first 5% and the last 7% of distillate were discarded.
  • the highly purified dipelargonate product was subjected to two kinds of stability tests.
  • the conventional ester lubricant, di (2 ethylhexyl)sebacate was also tested by this procedure.
  • di 2 ethylhexyl)sebacate was tested in the same manner.
  • both oils contained added inhibitors in conventional amounts.
  • R is a radical having 0-20 carbon atoms selected from the group consisting of hydrogen, alkyl and cycloalkyl, R and R are alkyl or cycloalkyl radicals having 1-20 carbon atoms, and R is an alkylene or cycloalkene radical having 1-20 carbon atoms.
  • R is an alkyl group having 5-41 carbon atoms.
  • a diester according to claim 2 which is a diester Results of the comparative corrosion and oxidation of 1,3-dihydroxy-5,7-dimethyladamantane and an alkanoic stability tests are set forth in Table 5.
  • alkanoic acid is selected from the group consisting of caproic, n-heptylic, caprylic, pelargonic, capric, undecyclic and lauric acids.
  • a diester according to claim 1 corresponding to 13.
  • a diester according to claim 12 wherein said al- Formula II. kanedioic acid is selected from the group consisting of 8.

Landscapes

  • 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)
US531059A 1966-03-02 1966-03-02 Diesters containing adamantane nuclei Expired - Lifetime US3398165A (en)

Priority Applications (7)

Application Number Priority Date Filing Date Title
US531059A US3398165A (en) 1966-03-02 1966-03-02 Diesters containing adamantane nuclei
GB58127/66A GB1113020A (en) 1966-03-02 1966-12-29 Diesters containing adamantane nuclei
DE19671594622 DE1594622A1 (de) 1966-03-02 1967-01-17 Schmiermittel auf der Basis einer Adamantanverbindung
NL6702200A NL6702200A (en:Method) 1966-03-02 1967-02-14
CH233967A CH485639A (de) 1966-03-02 1967-02-17 Verfahren zur Herstellung von Adamantanol-Diestern
BE694786D BE694786A (en:Method) 1966-03-02 1967-02-28
FR97018A FR1517143A (fr) 1966-03-02 1967-03-01 Diesters contenant des noyaux d'adamantane

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US531059A US3398165A (en) 1966-03-02 1966-03-02 Diesters containing adamantane nuclei

Publications (1)

Publication Number Publication Date
US3398165A true US3398165A (en) 1968-08-20

Family

ID=24116074

Family Applications (1)

Application Number Title Priority Date Filing Date
US531059A Expired - Lifetime US3398165A (en) 1966-03-02 1966-03-02 Diesters containing adamantane nuclei

Country Status (6)

Country Link
US (1) US3398165A (en:Method)
BE (1) BE694786A (en:Method)
CH (1) CH485639A (en:Method)
DE (1) DE1594622A1 (en:Method)
GB (1) GB1113020A (en:Method)
NL (1) NL6702200A (en:Method)

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3533947A (en) * 1968-09-12 1970-10-13 Sun Oil Co Use of adamantane polymers as vi improvers
US3648531A (en) * 1969-08-19 1972-03-14 Sun Oil Co Friction or tractive drive fluid
WO1981003657A1 (en) * 1980-06-11 1981-12-24 Battelle Memorial Institute Unsaturated esters of adamantane containing diols and thermo-resistant cross-linked polymers therefrom
US4640884A (en) * 1985-03-29 1987-02-03 Polychrome Corp. Photosensitive compounds and lithographic composition or plate therewith having o-quinone diazide sulfonyl ester group
EP0363866A3 (en) * 1988-10-12 1990-06-20 Idemitsu Kosan Company Limited Higher carboxylic acid triester of adamantane triol and lubricating oil containing the same
EP1717297A1 (en) * 2005-04-28 2006-11-02 Idemitsu Kosan Co., Ltd. Lubricants for power transmission system
JP2006306986A (ja) * 2005-04-28 2006-11-09 New Japan Chem Co Ltd 潤滑油
US20160131566A1 (en) * 2014-11-06 2016-05-12 Caterpillar Inc. System and method of monitoring viscosity of fluid in real-time
RU2696868C1 (ru) * 2018-12-05 2019-08-07 федеральное государственное бюджетное образовательное учреждение высшего образования "Самарский государственный технический университет" Способ получения сложных диэфиров 5,7-диметил-1,3-адамантандиола

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2007094746A1 (fr) * 2006-02-16 2007-08-23 Leonid Vladimirovich Golovko Esters de dialkyle d'acide 5,7-dimethyladamantane-1,3-dicarboxylique, procédés de leur synthèse et procédés de synthèse d'acide 5,7-dimethyladamantane-1,3-dicarboxylique en tant que produit intermédiaire

Cited By (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3533947A (en) * 1968-09-12 1970-10-13 Sun Oil Co Use of adamantane polymers as vi improvers
US3648531A (en) * 1969-08-19 1972-03-14 Sun Oil Co Friction or tractive drive fluid
WO1981003657A1 (en) * 1980-06-11 1981-12-24 Battelle Memorial Institute Unsaturated esters of adamantane containing diols and thermo-resistant cross-linked polymers therefrom
US4640884A (en) * 1985-03-29 1987-02-03 Polychrome Corp. Photosensitive compounds and lithographic composition or plate therewith having o-quinone diazide sulfonyl ester group
EP0363866A3 (en) * 1988-10-12 1990-06-20 Idemitsu Kosan Company Limited Higher carboxylic acid triester of adamantane triol and lubricating oil containing the same
US4990691A (en) * 1988-10-12 1991-02-05 Idemitsu Kosan Company Limited Higher carboxylic acid triester of adamantane triol and lubricating oil containing the same
EP1717297A1 (en) * 2005-04-28 2006-11-02 Idemitsu Kosan Co., Ltd. Lubricants for power transmission system
JP2006306986A (ja) * 2005-04-28 2006-11-09 New Japan Chem Co Ltd 潤滑油
JP2006307064A (ja) * 2005-04-28 2006-11-09 Idemitsu Kosan Co Ltd 動力伝達用潤滑剤
US20070037716A1 (en) * 2005-04-28 2007-02-15 Idemitsu Kosan Co., Ltd. Lubricants for power transmission
US7897551B2 (en) 2005-04-28 2011-03-01 Idemitsu Kosan Co., Ltd. Lubricants for power transmission
US20160131566A1 (en) * 2014-11-06 2016-05-12 Caterpillar Inc. System and method of monitoring viscosity of fluid in real-time
RU2696868C1 (ru) * 2018-12-05 2019-08-07 федеральное государственное бюджетное образовательное учреждение высшего образования "Самарский государственный технический университет" Способ получения сложных диэфиров 5,7-диметил-1,3-адамантандиола

Also Published As

Publication number Publication date
NL6702200A (en:Method) 1967-09-04
BE694786A (en:Method) 1967-08-28
GB1113020A (en) 1968-05-08
CH485639A (de) 1970-02-15
DE1594622A1 (de) 1970-07-23

Similar Documents

Publication Publication Date Title
US3562300A (en) Liquid neoalkylpolyol esters of mixtures of neo-and straight or branched chain alkanoic acids and their preparation
US4144183A (en) Mixed branched and straight chain ester oils
US4053491A (en) Branched-chain aliphatic ester oils
US2889354A (en) Dicarboxylate esters of alcohol containing a quaternary carbon in the beta-position
US3282971A (en) Fatty acid esters of polyhydric alcohols
US3360547A (en) Polyesters of tetraalkylcyclobutanediol
US3048608A (en) Neopentyl glycol esters
US3398165A (en) Diesters containing adamantane nuclei
US2758975A (en) Synthetic lubricants
EP0781265A1 (en) Process for preparing a synthetic ester from a vegetable oil
US2548493A (en) Esters of trimethyladipic acid
US2652411A (en) Alkyl acyloxy stearates
US3341574A (en) Di-(neopentylglycol mononeoheptanoate)azelate
US2798083A (en) Synthetic ester lubricants
US3414618A (en) Mono-p-tertiary alkyl diarylamines
US3462468A (en) Resorcinol esters of alpha,alpha-dimethyl aliphatic acids
US3115519A (en) Stable esters
US3210404A (en) Di-neoalkyl beta, beta, beta1, beta1-tetraloweralkyl-substituted alkylene dicarboxylates
US3681440A (en) Esters of tetrahydroxy dineoalkyl ethers
US3637501A (en) Complex esters
US2588194A (en) Synthetic lubricant
US2844534A (en) High molecular weight branched-chain ethers of lubricating grade
US3125525A (en) Lubricating greases containing borate
US3148147A (en) 2, 2-dialkyl-1, 3-propanediol diesters as functional fluids
US3206401A (en) Lubricating oil compositions containing ester of mercapto acid and a phosphonate