GB882642A - Esters of 2,2,4,4-tetraalkylcyclobutane-1,3-diols - Google Patents

Esters of 2,2,4,4-tetraalkylcyclobutane-1,3-diols

Info

Publication number
GB882642A
GB882642A GB11362/60A GB1136260A GB882642A GB 882642 A GB882642 A GB 882642A GB 11362/60 A GB11362/60 A GB 11362/60A GB 1136260 A GB1136260 A GB 1136260A GB 882642 A GB882642 A GB 882642A
Authority
GB
United Kingdom
Prior art keywords
diol
tetramethylcyclobutane
group
esters
ethyl
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
Application number
GB11362/60A
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.)
Eastman Kodak Co
Original Assignee
Eastman Kodak 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 Eastman Kodak Co filed Critical Eastman Kodak Co
Publication of GB882642A publication Critical patent/GB882642A/en
Expired legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/04—Oxygen-containing compounds
    • C08K5/10—Esters; Ether-esters
    • C08K5/12—Esters; Ether-esters of cyclic polycarboxylic 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
    • 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
    • C10M2201/00—Inorganic compounds or elements as ingredients in lubricant compositions
    • C10M2201/085—Phosphorus oxides, acids or salts
    • 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
    • C10M2207/02—Hydroxy compounds
    • C10M2207/023—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
    • C10M2207/026—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings with tertiary alkyl 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
    • 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
    • C10M2207/34—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
    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/10—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring
    • C10M2219/104—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring containing sulfur and carbon with nitrogen or oxygen in the ring
    • C10M2219/108—Phenothiazine
    • 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
    • C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
    • C10M2223/04—Phosphate esters
    • C10M2223/041—Triaryl phosphates
    • 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
    • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/12—Inhibition of corrosion, e.g. anti-rust agents or anti-corrosives
    • 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
    • C10N2040/08—Hydraulic fluids, e.g. brake-fluids
    • 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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Polyesters Or Polycarbonates (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Esters derived from cyclobutane diol and having the formula <FORM:0882642/III/1> wherein each R is a methyl or ethyl group and R1 is an alkyl group having 1 to 12 carbon atoms, are lubricants of high thermal and hydrolytic stability. A suitable composition comprises 2, 2, 4, 4-tetramethylcyclobutane-1, 3-diol dipelargonate (96%), tricresyl phosphate (3%), and phenothiazine (1%). Another specified composition comprises 2,2,4,4-tetramethylcyclobutane1, 3-diol bis (2-ethyl hexanoate) (98%), phosphorus acid (0,07%), and 2, 6-ditertiarybutyl-p-cresol (1,93%). A third composition comprises bis (2-ethylhexyl) sebacate (50%) and tetramethylcyclobutane-1, 3-diol dipelargonate (50%). For the preparation of the esters (see Group IV(b)). Specification 767,455 is referred to.ALSO:Esters derived from cyclobutane diol and having the formula <FORM:0882642/IV (a)/1> wherein each R is a methyl or ethyl group and R1 is an alkyl group having 1 to 12 carbon atoms, have utility as plasticizers for cellulose esters. In Example 11, cellulose acetate butyrate (80 parts) and 2,2,4,4-tetramethylcyclobutane-1,3-diol bis (2-ethyl hexanoate) are mixed on heated rolls, extruded into sheets, and then granulated and moulded. 2,2,4,4-tetraethylcyclobutane-1,3-diol dipelargonate is also specified as a plasticizer which is compatible with cellulose acetate butyrate. Examples 12 and 13 relate to similar subject-matter. For the preparation of the plasticizers-(see Group IV(b)). Specification 767,455 is referred to.ALSO:Esters of the formula <FORM:0882642/IV (b)/1> wherein each R is a methyl or ethyl group and R1 is an alkyl group having 1 to 12 carbon atoms, are prepared by reacting the appropriate 2,2,4,4-tetra-alkyl-cyclobutane-1,3-diol with an alkanoic acid having 2 to 13 carbon atoms. The esterification can also be carried out using a carboxylic acid chloride or anhydride. In example 1, a solution in toluene of 2,2,4,4-tetramethyl-cyclobutane-1,3-diol and 2-ethylhexanoic acid is refluxed (base temperature about 195 DEG C.) with azeotropic removal of water. The mixture is then washed with sodium bicarbonate solution, dried over sodium sulphate, and stripped of low boilers under vacuum 2,2,4,4-tetramethylcyclobutane - 1, 3 - diol bis (2 - ethyl - hexanoate) is isolated from the product by molecular distillation. In Example 3, the same ester is prepared using 2-ethylhexanoic anhydride, together with zinc chloride as catalyst. Example 2 describes the preparation tetramethylcyclobutane diol diacetate. Example 5 describes the preparation of 2,4-dimethyl-2,4-diethylcyclobutane-1,3-diol dipelargonate by reacting the appropriate diol with pelargonic acid. In Example 14, a solution in pyridine of tetramethylcyclobutane-1,3-diol is reacted with butryl chloride to give tetramethylcyclobutane-1,3-diol monobutyrate. This monoester is then reacted with dodecanoyl chloride to give tetramethylcyclobutane-1,3-diol butyrate dodecanate. These diesters have use as lubricants (Group III) and as plasticisers for cellulose esters (Group IV (a)). Specificatio 767,455 is referred to.
GB11362/60A 1959-04-13 1960-03-31 Esters of 2,2,4,4-tetraalkylcyclobutane-1,3-diols Expired GB882642A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US882642XA 1959-04-13 1959-04-13

Publications (1)

Publication Number Publication Date
GB882642A true GB882642A (en) 1961-11-15

Family

ID=22210356

Family Applications (1)

Application Number Title Priority Date Filing Date
GB11362/60A Expired GB882642A (en) 1959-04-13 1960-03-31 Esters of 2,2,4,4-tetraalkylcyclobutane-1,3-diols

Country Status (1)

Country Link
GB (1) GB882642A (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2006307064A (en) * 2005-04-28 2006-11-09 Idemitsu Kosan Co Ltd Power transmission lubricant
JP2006306986A (en) * 2005-04-28 2006-11-09 New Japan Chem Co Ltd Lubricating oil
JP2020532636A (en) * 2017-09-06 2020-11-12 ビーエーエスエフ ソシエタス・ヨーロピアＢａｓｆ Ｓｅ Esters and ethers of 2,2,4,4-tetramethylcyclobutane-1,3-diol for use as aromatic chemicals

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2006307064A (en) * 2005-04-28 2006-11-09 Idemitsu Kosan Co Ltd Power transmission lubricant
JP2006306986A (en) * 2005-04-28 2006-11-09 New Japan Chem Co Ltd Lubricating oil
JP2020532636A (en) * 2017-09-06 2020-11-12 ビーエーエスエフ ソシエタス・ヨーロピアＢａｓｆ Ｓｅ Esters and ethers of 2,2,4,4-tetramethylcyclobutane-1,3-diol for use as aromatic chemicals

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