DE1252837B - Use of diesters of saturated dicarboxylic acids as lubricants - Google Patents

Use of diesters of saturated dicarboxylic acids as lubricants

Info

Publication number
DE1252837B
DE1252837B DENDAT1252837D DE1252837DA DE1252837B DE 1252837 B DE1252837 B DE 1252837B DE NDAT1252837 D DENDAT1252837 D DE NDAT1252837D DE 1252837D A DE1252837D A DE 1252837DA DE 1252837 B DE1252837 B DE 1252837B
Authority
DE
Germany
Prior art keywords
diesters
bis
lubricants
dicarboxylic acids
saturated dicarboxylic
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.)
Pending
Application number
DENDAT1252837D
Other languages
German (de)
Inventor
Kingsport Tenn. Kent Combs Brannock (V. St. A.)
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.)
Publication date
Publication of DE1252837B publication Critical patent/DE1252837B/en
Pending legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/17—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrogenation of carbon-to-carbon double or triple bonds
    • C07C29/175—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrogenation of carbon-to-carbon double or triple bonds with simultaneous reduction of an oxo group
    • 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
    • C10M105/00—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
    • C10M105/08—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing oxygen
    • C10M105/32—Esters
    • C10M105/36—Esters of 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
    • 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
    • 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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Emergency Medicine (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Description

BUNDESREPUBLIK DEUTSCHLANDFEDERAL REPUBLIC OF GERMANY

DEUTSCHESGERMAN

PATENTAMTPATENT OFFICE

AUSLEGESCHRIFTEDITORIAL

Int. α.:Int. α .:

ClOmClOm

C 1OM 169/80B20C 1OM 169 / 80B20

Deutsche Kl.: 23 c-1/01German class: 23 c-1/01

Nummer:
Aktenzeichen:
Anmeldetag:
Auslegetag:Number:
File number:
Registration date:
Display day:

1252 837
E17688IVC/23C
27. Mai 1959
26. Oktober 19671252 837
E17688IVC / 23C
May 27, 1959
October 26, 1967

Die Erfindung betrifft die Verwendung von Diestern gesättigter Dicarbonsäuren mit 4 bis 7 Kohlenstoffatomen in der Alkylengruppe mit unsubstituierten 2,2,4-Trialkylpentanolen als Schmiermittel.The invention relates to the use of diesters of saturated dicarboxylic acids having 4 to 7 carbon atoms in the alkylene group with unsubstituted 2,2,4-trialkylpentanols as lubricants.

Der Erfindung lag die Erkenntnis zugrunde, daß derartige Diester, insbesondere das Bis(2,2,4-trimethylpentyl)azelat, gegenüber strukturmäßig sehr ähnlichen und als Schmiermittel bekannten Diestern, wie Bis(2 - methylpentyl)adipat, Bis(2 - äthylbutyl)pimelat und Bis(2-äthylhexyl)azelat, unerwartet vorteilhafte Schmiermitteleigenschaften aufweisen.The invention was based on the knowledge that such diesters, in particular bis (2,2,4-trimethylpentyl) azelate, compared to diesters that are structurally very similar and known as lubricants, such as Bis (2-methylpentyl) adipate, bis (2-ethylbutyl) pimelate and bis (2-ethylhexyl) azelate, unexpectedly advantageous Have lubricant properties.

Die erfindungsgemäß verwendeten Diester lassen sich nach üblichen bekannten Veresterungsverfahren herstellen. Die hierzu erforderlichen 2,2,4-Trialkylpentanole lassen sich durch Hydrierung der entsprechenden 2,2,4-Trialkylpentenale herstellen, deren Gewinnung bekannt ist.The diesters used according to the invention can be prepared by conventionally known esterification processes produce. The 2,2,4-trialkylpentanols required for this can be prepared by hydrogenation of the corresponding 2,2,4-trialkyl pentenals, their Extraction is known.

So lassen sich beispielsweise 2,2,4-Trimethyl-4-pentenal und 2,4-Dimethyl-2-äthyl-4-pentenal in methanolischer Lösung bei einer Temperatur von ao 125° C und einem Druck von etwa 140 at in Gegenwart von Raney-Nickel in hervorragenden Ausbeuten zu 2,2,4-Trimethylpentanol mit einem Siedepunkt von 164 bis 166°C, ni° = 1,4300, bzw. 2,4-Dimetb.yl-2-äthyl-4-pentanol mit einem Siedepunkt von 186 «5 bis 188°C, n%° = 1,4383, hydrieren.For example, 2,2,4-trimethyl-4-pentenal and 2,4-dimethyl-2-ethyl-4-pentenal in methanolic solution at a temperature of ao 125 ° C and a pressure of about 140 at in the presence of Raney nickel in excellent yields to 2,2,4-trimethylpentanol with a boiling point of 164 to 166 ° C, ni ° = 1.4300, or 2,4-Dimetb.yl-2-ethyl-4-pentanol with a Hydrogenate boiling point from 186-5 to 188 ° C, n% ° = 1.4383.

Im folgenden wird die Herstellung von Bis(2,2,4-trimethylpentyl)azelat beschrieben.The following describes the preparation of bis (2,2,4-trimethylpentyl) azelate described.

Man erhitzt eine Mischung von 130 g (1 Mol) 2,2,4-Trimethyl-l-pentanol, 94 g (0,5 Mol) Azelainsäure und 50 ml Xylol in einem Kolben mit Rückflußkühler und Wasserfalle auf Rückflußtemperatur, bis sich 18 ml Wasser abgeschieden haben. Die Reaktionsmischung wird anschließend einmal mit 100 ml 5%iger Natriumhydroxydlösung und zweimal mit Wasser gewaschen. Das Xylol wird durch Destillation entfernt. Durch Destillation des Rückstandes wird dann in im wesentlichen quantitativer Ausbeute Verwendung von Diestern gesättigter
Dicarbonsäuren als SchmiermittelA mixture of 130 g (1 mol) of 2,2,4-trimethyl-1-pentanol, 94 g (0.5 mol) of azelaic acid and 50 ml of xylene is heated in a flask with a reflux condenser and water trap to reflux temperature until 18 ml Have separated water. The reaction mixture is then washed once with 100 ml of 5% sodium hydroxide solution and twice with water. The xylene is removed by distillation. By distilling the residue, the use of saturated diesters is then obtained in an essentially quantitative yield
Dicarboxylic acids as lubricants

Anmelder:Applicant:

Eastman Kodak Company,Eastman Kodak Company,

Rochester, N. Y. (V. St. A.)Rochester, N. Y. (V. St. A.)

Vertreter:Representative:

Dr.-Ing. W. WolffDr.-Ing. W. Wolff

und H. Bartels, Patentanwälte,and H. Bartels, patent attorneys,

München 2, Thierschstr. 8Munich 2, Thierschstr. 8th

Als Erfinder benannt:
Kent Combs Brannock,
Kingsport, Tenn. (V. St. A.)Named as inventor:
Kent Combs Brannock,
Kingsport, Tenn. (V. St. A.)

Beanspruchte Priorität:Claimed priority:

V. St. v. Amerika vom 16. Juni 1958 (742 032)V. St. v. America June 16, 1958 (742 032)

Bis(2,2,4-trimethyl-l-pentyl)azelat mit einem Siedepunkt von 98 0C bei einem Druck von 0,065 Torr, „*> = 1,4485, erhalten.Bis (2,2,4-trimethyl-l-pentyl) azelate having a boiling point of 98 0 C at a pressure of 0.065 Torr, "*> = 1.4485, was obtained.

Der Ester besitzt einen Stockpunkt unter —62° C und Viskositäten von 8734, 13,54 und 3,55 cSt bei —54, +38 bzw. +99° C. Beim Erhitzen unter Stickstoff auf etwa 300° C besitzt der Ester eine Zersetzungsgeschwindigkeit von nur 0,02% pro Stunde, und nach 20stündigem Erhitzen auf etwa 3000C ist die Viskosität bei 38° C um nur 4,3% gesunken. Der Ester ist, nachdem er 72 Stunden bei —54°C aufbewahrt wird, immer noch flüssig.The ester has a pour point below -62 ° C and viscosities of 8734, 13.54 and 3.55 cSt at -54, +38 and + 99 ° C. When heated under nitrogen to about 300 ° C, the ester has a decomposition rate of only 0.02% per hour and after 20 hours of heating at about 300 0 C, the viscosity at 38 ° C is decreased by only 4.3%. The ester is still liquid after 72 hours at -54 ° C.

In der folgenden Tabelle sind die physikalischen Eigenschaften von erfindungsgemäß verwendbaren Estern und bekannten, als Schmiermittel verwendeten Estern zusammengestellt.The following table shows the physical properties of those which can be used according to the invention Esters and known esters used as lubricants.

EsterEster

Viskosität
in Centistokes beiviscosity
in centistokes at

-54°C-54 ° C

+990C+99 0 C

ThermischeThermal

Stabilitätstability

°/o Zersetzung° / o decomposition

je Stundeper hour

^()
in D/o nach
20 Stunden*)^ ()
in D / o after
20 hours*)

A. Ester nach der Erfindung:A. Esters according to the invention:

1. Bis(2,2,4-trimethylpentyl)azelat 1. Bis (2,2,4-trimethylpentyl) azelate

2. Bis(2,4-dimethyl-2-äthylpentyl> suberat 2. bis (2,4-dimethyl-2-ethylpentyl> suberate

3. Bis(2,4-dimethyl-2-äthylpentyl)-pimelat 3. Bis (2,4-dimethyl-2-ethylpentyl) pimelate

4. Bis(2,4-dimethyl-2-äthylpentyl)adipat ♦) Fußnote am Ende der Tabelle.4. Bis (2,4-dimethyl-2-ethylpentyl) adipate ♦) footnote at the end of the table.

<-62 <-59<-62 <-59

<-59 <-54 734
867<-59 <-54 734
867

21337
38021337
380

3,55
3,733.55
3.73

3,45
3,243.45
3.24

/0,02 bei 3020C
10,07 bei 315°C/ 0.02 at 302 ° C
10.07 at 315 ° C

0,05 bei 300° C0.05 at 300 ° C

0,04 bei 3000C
0,04 bei 3000C0.04 at 300 ° C
0.04 at 300 ° C

-4,3 -3,0-4.3 -3.0

-2,6
-2,0-2.6
-2.0

709 679/490709 679/490

(Fortsetzung vorstehender Tabelle)(Continuation of the table above)

EsterEster

Viskosität
in Centistokes beiviscosity
in centistokes at

+99° C+ 99 ° C

ThermischeThermal

Stabilitätstability

°/»Zersetzung° / »Decomposition

je Stundeper hour

Δ (η) 38C C Δ (η) 38 C C

in % nachin accordance

20 Stunden ♦)20 hours ♦)

B. Ester nach dem Stand der Technik:B. State-of-the-art esters:

5. Bis(2-methylpentyl)adipat 5. Bis (2-methylpentyl) adipate

6. Bis(2-äthylbutyl)pimelat 6. Bis (2-ethylbutyl) pimelate

7. Bis(2-äthylhexyl)azelat 7. Bis (2-ethylhexyl) azelate

8. Bis(2-äthylhexyl)sebazat 8. Bis (2-ethylhexyl) sebacate

-28,9 -59,4 -59,4-28.9 -59.4 -59.4

1,91
2,08
3,06
3,281.91
2.08
3.06
3.28

1,59 bei 315°C 1,34 bei 315°C 1,34 bei 3150C 0,59 bei 3000C1.59 at 315 ° C 1.34 at 315 ° C 1.34 at 315 0 C 0.59 at 300 0 C

+17,0+17.0

*) Prozentuale Änderung der Viskosität bei 38° C nach 20stündigem Erhitzen auf etwa 3000C.*) Percent change in viscosity at 38 ° C after 20 hours of heating at about 300 0 C.

Wie sich aus der Tabelle ergibt, haben die erfindungsgemäß verwendeten Ester, insbesondere das Bis-(2,2,4-trimethylpentyl)azelat, äußerst günstige Eigenschaften als synthetische Schmiermittel.As can be seen from the table, the esters used according to the invention, in particular bis (2,2,4-trimethylpentyl) azelate, extremely favorable properties as a synthetic lubricant.

Die Stockpunkte liegen sehr tief, die Viskositätswerte, z. B. des letztgenannten Esters, liegen nahe bei denen des bekannten Bis(2-äthylhexyl)sebazats, und die thermischen Stabilitäten sind ausgezeichnet The pour points are very low, the viscosity values, e.g. B. the latter ester, are obvious those of the known bis (2-ethylhexyl) sebazate, and the thermal stabilities are excellent

Claims (1)

Patentanspruch:Claim: Verwendung von Diestern gesättigter Dicarbonsäuren mit 4 bis 7 Kohlenstoffatomen in der Alkylengruppe mit unsubstituierten 2,2,4-Trialkylpentanolen als Schmiermittel.Use of diesters of saturated dicarboxylic acids with 4 to 7 carbon atoms in the alkylene group with unsubstituted 2,2,4-trialkylpentanols as a lubricant. 709 679/490 10.67 © Bundesdruckerei Berlin709 679/490 10.67 © Bundesdruckerei Berlin
DENDAT1252837D 1958-06-16 Use of diesters of saturated dicarboxylic acids as lubricants Pending DE1252837B (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US74203258A 1958-06-16 1958-06-16

Publications (1)

Publication Number Publication Date
DE1252837B true DE1252837B (en) 1967-10-26

Family

ID=24983225

Family Applications (1)

Application Number Title Priority Date Filing Date
DENDAT1252837D Pending DE1252837B (en) 1958-06-16 Use of diesters of saturated dicarboxylic acids as lubricants

Country Status (2)

Country Link
DE (1) DE1252837B (en)
GB (1) GB920122A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1925817A1 (en) * 1969-05-21 1970-12-03 Veba Chemie Ag Fully synthetic lubricant

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1925817A1 (en) * 1969-05-21 1970-12-03 Veba Chemie Ag Fully synthetic lubricant

Also Published As

Publication number Publication date
GB920122A (en) 1963-03-06

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