DE961483C - Synthetic lubricant - Google Patents
Synthetic lubricantInfo
- Publication number
- DE961483C DE961483C DEST7387A DEST007387A DE961483C DE 961483 C DE961483 C DE 961483C DE ST7387 A DEST7387 A DE ST7387A DE ST007387 A DEST007387 A DE ST007387A DE 961483 C DE961483 C DE 961483C
- Authority
- DE
- Germany
- Prior art keywords
- alcohol
- glycol
- formals
- formaldehyde
- viscosity
- 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
Links
Classifications
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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
- C10M1/00—Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants
- C10M1/08—Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants with additives
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- 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
- C10M2201/10—Compounds containing silicon
- C10M2201/105—Silica
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- C10M2201/00—Inorganic compounds or elements as ingredients in lubricant compositions
- C10M2201/14—Inorganic compounds or elements as ingredients in lubricant compositions inorganic compounds surface treated with organic compounds
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- C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
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- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/04—Ethers; Acetals; Ortho-esters; Ortho-carbonates
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- C10M2207/04—Ethers; Acetals; Ortho-esters; Ortho-carbonates
- C10M2207/044—Cyclic ethers having four or more ring atoms, e.g. furans, dioxolanes
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- C10M2207/04—Ethers; Acetals; Ortho-esters; Ortho-carbonates
- C10M2207/046—Hydroxy ethers
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- C10M2207/10—Carboxylix acids; Neutral salts thereof
- C10M2207/12—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
- C10M2207/121—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of seven or less carbon atoms
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- C10M2207/122—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of seven or less carbon atoms monocarboxylic
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- C10M2207/125—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of eight up to twenty-nine carbon atoms, i.e. fatty acids
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- C10M2207/283—Esters of polyhydroxy compounds
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- C10M2207/287—Partial esters
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- C10M2207/30—Complex esters, i.e. compounds containing at leasst three esterified carboxyl groups and derived from the combination of at least three different types of the following five types of compounds: monohydroxyl compounds, polyhydroxy xompounds, monocarboxylic acids, polycarboxylic acids or hydroxy carboxylic acids
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- C10M2207/34—Esters having a hydrocarbon substituent of thirty or more carbon atoms, e.g. substituted succinic acid derivatives
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- C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
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Description
AUSGEGEBEN AM 4. APRIL 1957ISSUED APRIL 4, 1957
St 7387 IVc j 23 cSt 7387 IVc j 23 c
Bei dem Versuch, bessere Spezialschmieröle mit besonderen Eigenschaften zu gewinnen, wurden neuartige synthetische Stoffe mit Schmiereigenschaften entwickelt, die im Vergleich mit Mineralölen gute Viskositäten bei tiefen und hohen Temperaturen aufweisen. Dies macht sie besonders geeignet für die Schmierung von Maschinen, die innerhalb eines großen Temperaturbereiches arbeiten müssen, wie Düsentriebwerke und Verbrennungsmotoren für Flugzeuge u. dgl. Mineralöle sind in Anbetracht ihrer zu niedrigen Viskositätsindizes für diese Zwecke ungeeignet.In an attempt to obtain better specialty lubricating oils with special properties, new types were created Synthetic substances developed with lubricating properties that are good in comparison with mineral oils Have viscosities at low and high temperatures. This makes them particularly suitable for that Lubrication of machines that have to work within a wide temperature range, such as jet engines and internal combustion engines for aircraft and the like, mineral oils are too low in view of theirs Viscosity indices unsuitable for these purposes.
Es wurde ferner festgestellt, daß synthetische Schmieröle auch bei der Schmierung der üblichen Kraftfahrzeugmotoren Vorteile bieten. Verschiedene synthetische Schmieröle besitzen außer der Anpassungsfähigkeit ihrer Viskosität den weiteren Vorzug, insbesondere bei längerer Betriebsdauer sehr wenig Rückstände in der Verbrennungskammer zu hinterlassen. Dies hat eine wirksamere Brennstoffausnutzung, ein geringeres Ansteigen des Octanzahlbedarfs des Motors, eine verringerte Neigung zur Vorzündung und allgemein ein besseres Arbeiten des Motors zur Folge.It was also found that synthetic lubricating oils are also useful in lubricating the usual Automotive engines offer advantages. Various synthetic lubricating oils possess besides the adaptability Their viscosity has a further advantage, especially with very little residue after a long period of operation to be left in the combustion chamber. This has a more efficient fuel economy, one less increase in the octane number requirement of the engine, a reduced tendency to pre-ignition and generally a better working of the engine result.
Diese neuartigen Schmiermittel können außerdem zur Verringerung oder Entfernung bereits vorhandener Verbrennungsrückstände dienen.These novel lubricants can also be used to reduce or remove existing ones Serve combustion residues.
Es wurde nun gefunden, daß die Formale, welche aus einer großen Anzahl verschiedener organischer Verbindungen mit mindestens einer freien.alkoholischen Hydroxylgruppe hergestellt werden können und mindestens drei —-CH2O-Gruppen enthalten, als synthetische Schmieröle oder Bestandteile synthetischerIt has now been found that the formals, which can be prepared from a large number of different organic compounds with at least one free alcoholic hydroxyl group and contain at least three —CH 2 O groups, are used as synthetic lubricating oils or components of synthetic ones
ίο Schmieröle und Schmierfette verwendet werden können, die bei hohen und tiefen Temperaturen hervorragendeSchmierfähigkeit besitzen und in Verbrennungskammern von Kolbenmaschinen praktisch keine Verbrennungsrückstände hinterlassen.ίο lubricating oils and greases can be used, the excellent lubricity at high and low temperatures have and practically none in the combustion chambers of piston engines Leave combustion residues behind.
Es ist allgemein bekannt, daß die meisten Acetale zur Verwendung als Schmiermittel nicht beständig genug sind. Die Formale organischer Oxyverbindungen, welche die GruppeIt is well known that most acetals are not stable for use as lubricants are enough. The formals of organic oxy compounds which make up the group
- O - [CH2 - O- O - [CH 2 - O
CH2 - OCH 2 - O
enthalten, worin χ und η ^ 2 und y S ι sind, besitzen nun eine ausgezeichnete Stabilität und weisen Viskositätseigenschaften auf, die sie zu ausgezeichneten Schmierölgemischen machen.contain, in which χ and η ^ 2 and y S ι, now have excellent stability and have viscosity properties that make them excellent lubricating oil mixtures.
Die Schmiermittel nach der Erfindung haben die allgemeine ZusammensetzungThe lubricants of the invention have the general composition
A-O [CH2 — O (CnH2nO)1,], CH2-O-BAO [CH 2 - O (C n H 2n O) 1], CH 2 -OB
Hierin sind A und B Alkohol- oder Glykolreste, χ und η fe 2 und y § 1. Die Reste können gleich oder verschieden sein" und 1 bis 60 C-Atome enthalten. A und B werden so ausgewählt, daß das Formal insgesamt etwa 20 bis 130, vorzugsweise etwa 25 bis 100 C-Atome enthält. Die zur Einführung der Reste A und B verwendeten organischen Oxyverbindungen werden nachstehend näher beschrieben.Here, A and B are alcohol or glycol residues, χ and η fe 2 and y § 1. The residues can be the same or different "and contain 1 to 60 carbon atoms. A and B are selected so that the formal a total of about 20 contains up to 130, preferably about 25 to 100, C. The organic oxy compounds used to introduce the radicals A and B are described in more detail below.
Zur Schmierung von Kolbenmaschinen, insbesondere von Kraftfahrzeugmotoren, muß das Schmiermittel mehreren Anforderungen genügen. Um einen wirksamen Schmierfihn bilden zu können und diesen bei hohen und tiefen Temperaturen aufrechtzuerhalten, sind gewisse Viskositätseigenschaften erforderlich. Bei tiefen Temperaturen muß das Schmiermittel labil genug sein, um in dem Schmiersystem der Anlage umlaufen zu können und die Bewegung der geschmierten Flächen ohne übermäßigen Kraftaufwand zu erlauben. Ein Schmiermittel von einem ASTM-Fließpunkt unterhalb etwa 1,7° besitzt genügende Labilität bei tiefen Temperaturen. Bei hohen Temperaturen muß ein Schmiermittel genügende Konsistenz haben, um einen ausreichenden Schmierfihn zu bilden und aufrechtzuerhalten. Man hat gefunden, daß ein in dieser Hinsicht befriedigendes Schmiermittel eine Viskosität von etwa 2 bis 60 cSt bei 98,9° haben muß. Um übermäßig hohe Schmierölverluste durch Verflüchtigung und Zerfall zu vermeiden und vor Explosionen, die bei höheren Temperaturen auftreten können, sicher zu sein, soll das Schmieröl einen Flammpunkt von mehr als 150° haben. Diese Forderungen sind in dem Ausdruck »Schmiermittel« eingeschlossen, und die Formale nachder Erfindung sind auf solche beschränkt, die diese Eigenschaften haben. Die vorzugsweise verwendeten Stoffe haben einen ASTM-Fließpunkt unterhalb etwa —260, einen Flammpunkt oberhalb etwa 190° und eine Viskosität von 2,6 bis 13 cSt bei 98,9°.For the lubrication of piston engines, in particular of motor vehicle engines, the lubricant must meet several requirements. In order to be able to form an effective lubricating film and to maintain it at high and low temperatures, certain viscosity properties are required. At low temperatures, the lubricant must be unstable enough to be able to circulate in the system's lubrication system and to allow the lubricated surfaces to move without using excessive force. A lubricant with an ASTM pour point below about 1.7 ° has sufficient instability at low temperatures. At high temperatures, a lubricant must have sufficient consistency to form and maintain a sufficient film of lubricant. It has been found that a lubricant which is satisfactory in this regard must have a viscosity of about 2 to 60 cSt at 98.9 °. In order to avoid excessively high losses of lubricating oil through volatilization and decomposition and to be safe from explosions that can occur at higher temperatures, the lubricating oil should have a flash point of more than 150 °. These requirements are included in the term "lubricant" and the formals of the invention are limited to those having these properties. The substances preferably used have an ASTM pour point below about -26 0, a flash point above about 190 ° and a viscosity from 2.6 to 13 cSt at 98.9 °.
Die obengenannten. Eigenschaften sind Funktionen .der Molekülstruktur und des Molekulargewichts. Daher ist es innerhalb gewisser Grenzen möglich, Schmieröle mit ähnlichen Hoch- und Tieftemperatureigenschaften auf verschiedene Weise herzustellen und sie zur Erfüllung der jeweils gestellten Anforderungen gewissermaßen »nach Maß« anzufertigen; denn die große Zähl organischer, alkoholische Hydroxylgruppen enthaltender Verbindungen gestattet es, die verschiedensten erfindungsgemäßen Schmiermittel herzustellen.The above. Properties are functions of the molecular structure and molecular weight. Therefore it is possible within certain limits to use lubricating oils with similar high and low temperature properties to produce in different ways and to meet the respective requirements to a certain extent To make "to measure"; because the large number of organic, alcoholic containing hydroxyl groups Compounds allow a wide variety of lubricants according to the invention to be prepared.
Die Herstellung der komplexen Formale gemäß der Erfindung, die hier nicht unter Patentschutz gestellt werden soll, erfolgt nach der allgemein üblichen Technik. Es sind hierbei drei allgemeine Wege gangbar.The manufacture of the complex formals according to the invention, which is not patented here is to be carried out according to the generally accepted technique. There are three general ways to do this.
1. Man kann die Reaktionsteilnehmer in der Reaktionszone mischen und in Gegenwart eines Mitnehmers, wie Hexan, Heptan od. dgl., auf Rückflußtemperatur erhitzen. Nach Abtreibung der theoretischen Wassermenge wird das Produkt von sauren Katalysatoren freigewaschen und von nicht in Reaktion getretenen Bestandteilen abgetreift.1. You can put the reactants in the reaction zone Mix and in the presence of a carrier, such as hexane, heptane or the like., To reflux temperature heat. After aborting the theoretical amount of water, the product becomes acidic catalysts Washed free and stripped of unreacted components.
2. Man mischt χ Mol des Glykols mit (x — 1) Mol Formaldehyd, um das Kernstück der Verbindung, nämlich die Gruppe2. Mix χ mol of the glycol with (x - 1) mol of formaldehyde to form the core of the compound, namely the group
HO (CnR2nO)1, [CH2 - O - (QH2nO)L HHO (C n R 2n O) 1 , [CH 2 - O - (QH 2n O) LH
zu erhalten. In einer anderen Reaktionszone erhitzt man gleiche Molanteile eines Alkohols und Formaldehyd auf etwa 60°, um das Halbformal des Alkohols, d. h. R—0-CH2—OH, zu gewinnen. Man vermischt nun beide Produkte, indem man das Glykolformal zu dem Alkoholhalbformal zusetzt, und erhitzt auf Rückflußtemperatur. Nach Abtreibung der theoretischen Wassermenge wird das Produkt wie oben gewaschen und abgestreift.to obtain. In another reaction zone, equal molar proportions of an alcohol and formaldehyde are heated to about 60 ° in order to obtain the semi-formal of the alcohol, ie R — O — CH 2 —OH. The two products are now mixed by adding the glycol formal to the alcohol semi-formal, and the mixture is heated to reflux temperature. After the theoretical amount of water has been aborted, the product is washed and stripped as above.
3. Man stellt zunächst das Halbformal des betreffenden Alkohols dar, indem man gleiche Molanteile Alkohol und Formaldehyd erhitzt. Dann fügt man den gewünschten Molanteil Glykol und Formaldehyd hinzu und erhitzt die Masse auf Rückflußtemperatur, wobei der Oxykomplex3. First, the semi-formal of the alcohol in question is represented by using equal molar proportions Alcohol and formaldehyde heated. Then add the desired molar proportion of glycol and formaldehyde and heated the mass to reflux temperature, whereby the oxy complex
R-O-[CH2-O-(CnH2nO)J05HRO- [CH 2 -O- (C n H 2n O) J 05 H
entsteht. Dann setzt man 2 Mol dieses Produktes mit ι Mol Formaldehyd um und erhält das Endprodukt, welches, wie oben beschrieben, gereinigt wird.arises. Then 2 moles of this product are reacted with ι moles of formaldehyde and the end product is obtained, which is cleaned as described above.
Die zur Herstellung dieser Formale verwendbaren Verbindungen müssen also organische Oxyverbindungen sein, die zumindest eine freie alkoholische Hydroxylgruppe enthalten. Die folgende Aufstellung gibt Beispiele solcher Verbindungen. Es können natürlich auch andere Verbindungen verwendet werden.The compounds that can be used to make these formals must therefore be organic oxy compounds which contain at least one free alcoholic hydroxyl group. The following list give examples of such connections. Other compounds can of course also be used.
I. Nicht substituierte AlkoholeI. Unsubstituted alcohols
A. Einwertige Alkohole i. Aliphatische AlkoholeA. Monohydric alcohols i. Aliphatic alcohols
Methylalkohol A) IsopropylalkOholMethyl alcohol A) isopropyl alcohol
b) Äthylalkoholb) ethyl alcohol
c) Propylalkoholc) propyl alcohol
e) n-Butylalkohole) n-butyl alcohol
f) Isobutylalkoholf) isobutyl alcohol
g) Sekundär-butylalkohol
h) Tertiär-butylalkohol
i) η-Amylalkohol
j) Isoamylalkohol
k) n-Hexylalkohol
1) Isohexylalkohol
m) 2-Äthyl-i-butanol
η) 2-Äthyl-i-hexanol
ο) Octylalkohol
ρ) Isooctylalkoholg) secondary butyl alcohol
h) tertiary butyl alcohol
i) η-amyl alcohol
j) isoamyl alcohol
k) n-hexyl alcohol
1) isohexyl alcohol
m) 2-ethyl-i-butanol
η) 2-ethyl-i-hexanol
ο) octyl alcohol
ρ) isooctyl alcohol
q) 2-Octylalkoholq) 2-octyl alcohol
r) Isononylalkoholr) isononyl alcohol
s) Decylalkohols) decyl alcohol
t) Laurylalkoholt) lauryl alcohol
u) Tetradecylalkoholu) tetradecyl alcohol
v) Pentadecylalkoholv) pentadecyl alcohol
w) Octadecylalkoholw) octadecyl alcohol
x) AUylalkoholx) AUyl alcohol
y) Crotylalkoholy) crotyl alcohol
z) Oleylalkoholz) oleyl alcohol
aa) die Terpineole
bb) die nach bekannten Syntheseverfahren gewonnenen Alkohole oder deren Gemischeaa) the terpineole
bb) the alcohols obtained by known synthesis processes or their mixtures
2. Aromatische Alkohole2. Aromatic alcohols
a) Benzylalkohola) Benzyl alcohol
b) Phenäthylalkoholb) phenethyl alcohol
c) 3-Phenyl-i-propanolc) 3-phenyl-i-propanol
d) a-Naphthylcarbinold) a-naphthylcarbinol
e) Zimtalkohole) cinnamon alcohol
f) Diphenylcarbinolf) diphenylcarbinol
g) Furfurylalkohol h) Cuminalkoholg) furfuryl alcohol h) cumic alcohol
i) Vanillylalkohol j) Piperonylalkoholi) Vanillyl alcohol j) Piperonyl alcohol
ι. Glykoleι. Glycols
B. Mehrwertige AlkoholeB. Polyhydric alcohols
a) Äthylenglykol d) i, 3-Butandiola) Ethylene glycol d) i, 3-butanediol
b) i, 2-Propandiol e) 1, 4-Butandiolb) i, 2-propanediol e) 1,4-butanediol
c) i, 3-Propandiol f) 1, 5-Pentandiol g) die verschiedenen Polyalkylenglykole, z. B.c) i, 3-propanediol f) 1,5-pentanediol g) the various polyalkylene glycols, e.g. B.
i. Polyäthylenglykole 2. Polypropylenglykolei. Polyethylene glycols 2. polypropylene glycols
a) Diäthylenglykol a) Dipropylenglykola) Diethylene glycol a) Dipropylene glycol
b) Triäthylenglykol b) Tripropylenglykolb) triethylene glycol b) tripropylene glycol
c) Tetraäthylenglykol h) i, 2-C3rclohexandiolc) tetraethylene glycol h) i, 2-C3rclohexanediol
i) Decandiol-i, 10i) Decanediol-i, 10
2. Andere mehrwertige Alkohole2. Other polyhydric alcohols
a) Glycerina) glycerin
b) 2-Oxymethyl-2-methyl-propandiol-i, 3b) 2-oxymethyl-2-methyl-propanediol-i, 3
c) Pentaerythritc) pentaerythritol
d) Sorbitd) sorbitol
e) Dipentaerythrite) dipentaerythritol
f) Dulcitf) Dulcit
g) Trimethylolpropang) trimethylol propane
h) Tetramethylolcyclohexanol i) Benzotrimethylolh) tetramethylolcyclohexanol i) benzotrimethylol
II. Substituierte Alkohole A. Einwertige AlkoholeII. Substituted Alcohols A. Monohydric Alcohols
i. Aliphatische Alkoholei. Aliphatic alcohols
a) Halogenierte Alkoholea) Halogenated alcohols
1. Äthylenchlorhydrin1. Ethylene chlorohydrin
2. Trifluoräthanol2. Trifluoroethanol
3. Propylenchlorhydrin3. propylene chlorohydrin
4. die verschiedenen chlorsubstituierten Monoäther von Polyalkylenglykolen4. the various chlorine-substituted monoethers of polyalkylene glycols
b) Äthanolamin, ÄthanohnorphoHnb) Ethanolamine, ÄthanohnorphoHn
c) 2-Aminopropanol e) 2-Nitropropanolc) 2-aminopropanol e) 2-nitropropanol
d) 2-Nitroäthanol f) 2-Nitrobutanold) 2-nitroethanol f) 2-nitrobutanol
2. Aromatische Alkohole2. Aromatic alcohols
a) p-Methoxy-benzylalkohola) p-methoxy-benzyl alcohol
b) die verschiedenen Chlorbenzylalkoholeb) the various chlorobenzyl alcohols
c) die verschiedenen Nitrobenzylalkoholec) the various nitrobenzyl alcohols
d) 2-Anilinäthanold) 2-aniline ethanol
3. Glykohnonoäther3. Glycine ether
a) Äthylenglykol-monomethyläthera) Ethylene glycol monomethyl ether
b) Propylenglykol-monobutylätherb) Propylene glycol monobutyl ether
c) Butylenglykol-monolaurylätherc) butylene glycol monolauryl ether
d) Polyäthylenglyk'ol-monoätherd) Polyethylene glycol monoether
e) Polypropylenglykol-monoäthere) polypropylene glycol monoether
f) Polybutylenglykol-monoätherf) polybutylene glycol monoether
g) Polytrimethylenglykol-monoätherg) polytrimethylene glycol monoether
4. Glykol-mono-formale, z. B. die gemischten Formale von Glykolen und Alkoholen 804. Glycol mono-formal, e.g. B. the mixed formals of glycols and alcohols 80
B. Mehrwertige AlkoholeB. Polyhydric alcohols
1. Glykole1. Glycols
a) Halogenierte Glykole, z. B.a) Halogenated glycols, e.g. B.
1. 3-Chlor-i, 2-propandiol1. 3-chloro-i, 2-propanediol
2. 2-Chlor-i, 3-propandiol2. 2-chloro-i, 3-propanediol
b) Nitroglykole, z. B.b) nitroglycols, e.g. B.
1. 2-Nitro-i, 3-propandiol1. 2-Nitro-i, 3-propanediol
2. 2-Nitro-2-methyl-propandiol-i, 32. 2-Nitro-2-methyl-propanediol-i, 3
3. Trimethylol-nitromethan3. Trimethylol-nitromethane
c) Aminoglykolec) aminoglycols
1. 2-Amino-i, 3-propandiol1. 2-Amino-i, 3-propanediol
2. 2-Amino-2-methyl-i, 3-propandiol2. 2-Amino-2-methyl-1,3-propanediol
3. Diäthanolamin3. Diethanolamine
4. Trimethylol-aminomethan4. Trimethylol aminomethane
2. Glykohnonoester2. Glycol monoesters
a) Äthylenglykol-monoacetata) Ethylene glycol monoacetate
b) Propylenglykol-monobutyratb) propylene glycol monobutyrate
c) Butylenglykol-monolauratc) butylene glycol monolaurate
d) Polyäthylenglykol-monoesterd) Polyethylene glycol monoester
e) Polypropylenglykol-monoestere) polypropylene glycol monoester
f) Polybutylenglykol-monoesterf) polybutylene glycol monoester
C. Andere OxyverbindungenC. Other oxy compounds
1. Ester von Oxysäuren1. Esters of oxyacids
a) Milchsäureestera) lactic acid ester
b) Glykolsäureesterb) glycolic acid ester
c) Oxystearinsäureesterc) oxystearic acid ester
2. Carbonylsubstituierte Alkohole2. Carbonyl-substituted alcohols
a) Oxyketone, ζ. Β.
Oxyacetona) oxyketones, ζ. Β.
Oxyacetone
b) Oxyaldehyde, z. B.b) oxyaldehydes, e.g. B.
1. a-Oxyadipaldehyd1. α-Oxyadipaldehyde
2. /S-Oxypropionaldehyd2. / S-oxypropionaldehyde
3. OxyaJkyl-cyanide3. Oxy-alkyl-cyanide
a) Äthylencyanhydrina) ethylene cyanohydrin
b) a-Oxy-isobutyrnitrilb) a-oxy-isobutyrnitrile
Für das Verfahren gemäß der Erfindung besonders 125 gut verwendbare organische Oxyverbindungen sind dieOrganic oxy compounds which are particularly useful for the process according to the invention are
stark verzweigtkettigen aliphatischen Alkohole, die durch die ;> Oxo «-Synthese erhalten werden.highly branched aliphatic alcohols, the can be obtained by the "oxo" synthesis.
Zur Herstellung der Formale nach der Erfindung besonders gut brauchbare Alkohole lassen sich durch Anwendung der Oxosynthese auf Polymerisate und Mischpolymerisate von C3- und C4-Monoolefinen gewinnen, wie sie in Erdölraffinerieströmen leicht verfügbar sind.Alcohols which are particularly useful for preparing the formals according to the invention can be obtained by applying the oxo synthesis to polymers and copolymers of C 3 and C 4 monoolefins, such as are readily available in petroleum refinery streams.
Bevorzugt werden Oxoalkohole mit 8 bis 20 C-Atomen, die aus Olefincopolymeren mit 7 bis 19 C-Atomen gewonnen sind.Preference is given to oxo alcohols with 8 to 20 carbon atoms, those from olefin copolymers with 7 to 19 carbon atoms are won.
Zur Herstellung der Formale nach der Erfindung werden einwertige Alkohole, Glykole und organische Säuren bevorzugt. Man kann diese Verbindungen vorteilhaft mit Formaldehyd zu Molekülen der nachfolgenden Zusammensetzungen umsetzen, wobei an Stelle der Strukturformeln die einzelnen Bestandteile der komplexen Formale angegeben sind:Monohydric alcohols, glycols and organic are used to prepare the formals according to the invention Acids preferred. These compounds can advantageously be combined with formaldehyde to form molecules of the following Implement compositions, with the individual components instead of the structural formulas of the complex formalities are given:
Alkohol (Formaldehyd-Glykol),,,,
Glykol (Formaldehyd-Glykol)^
Glykolmonoester (Formaldehyd-Glykol) a,
Glykolmonoäther (Formaldehyd-Glykol) x. Alcohol (formaldehyde glycol) ,,,,
Glycol (Formaldehyde Glycol) ^
Glycol monoester (formaldehyde glycol) a ,
Glycol monoether (formaldehyde glycol) x .
Hierin ist λ; in allen Fällen eine ganze Zahl größer als i. Die zur Herstellung der Glykolmonoester verwendeten Säuren können der folgenden beispielhaften Aufzählung entnommen werden: Essigsäure, Propionsäure, Buttersäure, 2-Äthylbuttersäure, Capronsäure, 2-Äthylcapronsäure, Caprylsäure, Pelargonsäure, Caprinsäure, Laurinsäure, Myristinsäure, Oleinsäure, Stearinsäure, Naphthensäuren, Methoxypropionsäure, Äthoxyäthoxyessigsäure, Mono-2-äthylhexyl-adipinsäure, Mono-C8-o^o-sebacinsäure, C3- bis C20-OxO-säuren, einschließlich der Säuren von Bodenfraktionen, Säuren aus der Oxydation von Erdölfraktionen, Säuren aus der alkalischen Schmelze von'Alkoholen und/oder Aldehyden, Glykolsäure, Milchsäure, Oxystearinsäure.Where λ is; in all cases an integer greater than i. The acids used for the preparation of the glycol monoesters can be found in the following list: acetic acid, propionic acid, butyric acid, 2-ethylbutyric acid, caproic acid, 2-ethylcaproic acid, caprylic acid, pelargonic acid, capric acid, lauric acid, myristic acid, oleic acid, stearic acid, methoxyethyleneoxyacid , Mono-2-ethylhexyl-adipic acid, mono-C 8 -o ^ o-sebacic acid, C 3 - to C 20 -oxo acids, including the acids from soil fractions, acids from the oxidation of petroleum fractions, acids from the alkaline melt of 'Alcohols and / or aldehydes, glycolic acid, lactic acid, oxystearic acid.
Zur weiteren Erläuterung der Herstellungsweise der erfindungsgemäß als Schmieröle verwendeten Formale dienen die nachfolgenden Beispiele. Für die Herstellungsverfahren wird jedoch kein Patentschutz beansprucht. To further explain the method of production of the formals used as lubricating oils according to the invention the following examples serve. However, no patent protection is claimed for the manufacturing process.
Herstellung von n-Butyl-carbitol-(CH2-tripropylenglykol)4, d. h.Production of n-butyl-carbitol- (CH 2 -tripropylene glycol) 4 , ie
n—C4H9-(OCH2CH2)2O —(CH2OC3H7OC3H7 OC3H7O)4Hn-C 4 H 9 - (OCH 2 CH 2 ) 2 O - (CH 2 OC 3 H 7 OC 3 H 7 OC 3 H 7 O) 4 H
Man stellte das Halbformal von n-Butyl-carbitol durch halbstündiges Erhitzen von 81,1 g (V2 Mo1) Car" bitol mit 15,1g (V2MoI CH2O) Paraformaldehyd, 200 g Heptan und 2 g NaHSO4 auf 65° her.It presented the half formal of n-butyl carbitol by half-hour heating of 81.1 g (V 2 Mo1) Car "Bitol with 15.1 g of (V 2 MoI CH 2 O) of paraformaldehyde, 200 g of heptane and 2 g of NaHSO 4 to 65 ° her.
Das Polyformal von Tripropylenglykol, alsoThe polyformal of tripropylene glycol, so
TPG-CHaO-TPG-CH2O-TPG-CH2O-TPGTPG-CHaO-TPG-CH 2 O-TPG-CH 2 O-TPG
wurde durch 90 Minuten langes Erhitzen von 384,5 g (2 Mol) Tripropylenglykol, 45,5 g (1,5 MoICH2O) Paraformaldehyd, 200 g Heptan und 3,2 g NaHSO4 auf 89 bis 1040 am Rückflußkühler erhalten. Das Volumen der Wasserschicht betrug 28 ecm (Theorie 27 ecm).long by 90 minutes of heating 384.5 g (2 mol) of tripropylene glycol, 45.5 g (1.5 moich 2 O) of paraformaldehyde, 200 g of heptane and 3.2 g of NaHSO 4 to 89-104 0 was obtained at reflux. The volume of the water layer was 28 ecm (theory 27 ecm).
Zur Verringerung der Bildung des einfachen Formals setzte man das Halbformal von n-Butylcarbitol im Verlaufe von 70 Minuten tropfenweise der unter Rückfluß gehaltenen Lösung des Polyformals von Tripropylenglykol hinzu. Nach beendetem Zusatz des Halbformals setzte man die Rückflußbehandlung weitere 30 Minuten bei 100 bis 102° fort. Das Volumen der Wasserschicht betrug nun 37 ecm (Theorie 36 ecm). Der Katalysator wurde durch Dekantieren entfernt, das Gemisch dreimal mit je 100 ecm 5°/„iger Na2CO3-Lösung und zweimal mit je 100 ecm Wasser gewaschen. Nach Abstreifen des Lösungsmittels und nicht in Reaktion getretenen Materials siedete das Produkt unter 0,2 mm oberhalb 140° (Kesseltemperatur 2310) und hatte folgende Kennwerte:To reduce the formation of the simple formal, the semi-formal of n-butyl carbitol was added dropwise over 70 minutes to the refluxed solution of the polyformal of tripropylene glycol. When the addition of the semi-formal had ended, the reflux treatment was continued for a further 30 minutes at 100 to 102 °. The volume of the water layer was now 37 ecm (theory 36 ecm). The catalyst was removed by decanting, and the mixture was washed three times with 100 ecm 5% Na 2 CO 3 solution each time and twice with 100 ecm water each time. After the solvent had been stripped off and the material had not reacted, the product boiled below 0.2 mm above 140 ° (boiler temperature 231 0 ) and had the following characteristics:
Viskosität in cStViscosity in cSt
bei 98,9° 50,86at 98.9 ° 50.86
bei 37,8° 423,1at 37.8 ° 423.1
bei —17,8° 59 700,0at -17.8 ° 59 700.0
Viskositätsindex 130,0Viscosity index 130.0
Fließpunkt in 0C — 31,7Pour point at 0 C - 31.7
WasserstoffverbrennungsprobeHydrogen combustion test
Kohlenstoff in mg 1,1Carbon in mg 1.1
Beschlag in mg 0,7Fog in mg 0.7
Herstellung von. Polyäthylenglykol-Polyformal HO (CH2CH2O)614 [CH2(OCH2CH2)6)4O].HProduction of. Polyethylene glycol polyformal HO (CH 2 CH 2 O) 614 [CH 2 (OCH 2 CH 2 ) 6) 4 O] .H
Dieses Polyformal wurde durch zweistündiges Erhitzen von 300 g (1 Mol) Polyäthylenglykol von einem Molekulargewicht von etwa 300, 30 g (1 Mol CH2O) Paraformaldehyd, 200 g Heptan und 3,3 g NaHSO4 auf 98° hergestellt. Hierbei gingen 19,2 ecm Wasser über (Theorie 18 ecm). Nach deni Abkühlen trennte man die Heptanschicht ab. Die Polyformalschicht wurde 30 Minuten mit 10 % Tierkohle bei 115° behandelt und dann abgenutscht. Das Polyformal wird nachstehend mit dem ursprünglichen Polyäthylenglykol 300 in Vergleich gesetzt.This polyformal was prepared by heating 300 g (1 mol) of polyethylene glycol with a molecular weight of about 300, 30 g (1 mol CH 2 O) paraformaldehyde, 200 g heptane and 3.3 g NaHSO 4 to 98 ° for two hours. 19.2 ecm of water passed over (theory 18 ecm). After cooling, the heptane layer was separated off. The polyformal layer was treated with 10% animal charcoal at 115 ° for 30 minutes and then suction filtered. The polyformal is compared with the original polyethylene glycol 300 below.
Viskosität in cStViscosity in cSt
bei 98,9° at 98.9 °
bei 37,8° at 37.8 °
Viskositätsindex ..
Fließpunkt in 0C .
Flammpunkt in 0C
Brennpunkt in ° C.Viscosity index ..
Flow point in 0 C.
Flash point in 0 C
Focal point in ° C.
Nach einer anderen Ausführungsform der Erfindung können die durch die oben angegebenen Formeln gekennzeichneten Verbindungen, die eine freie Hydroxylgruppe enthalten, weiter mit Formaldehyd umgesetzt und an eine andere organische Verbindung gekuppelt werden, die ebenfalls eine freie alkoholischeAccording to another embodiment of the invention by the formulas given above labeled compounds which contain a free hydroxyl group, reacted further with formaldehyde and coupled to another organic compound which is also a free alcoholic compound
Hydroxylgruppe enthält. Diese Reihe von Verbindungen, deren jede die Gruppe — (Formaldehyd-Glykol) x — enthält, worin χ größer als ι ist, kann wie folgt gekennzeichnet werden (wobei die gemeinsame Gruppe als »Z« bezeichnet ist):Contains hydroxyl group. This series of compounds, each of which contains the group - (formaldehyde glycol) x -, where χ is greater than ι, can be characterized as follows (the common group being designated as "Z" ):
Alkohol-Z-Formaldehyd-Alkohol Alkohol-Z-Formaldehyd-Glykolmonoester Alkohol-Z-Formaldehyd-Glykolmonoäther Glykolmonoester-Z-Formaldehyd-Glykolmonoester Glykolmonoester-Z-Formaldehyd-Glykolmonoäther Glykohnonoäther-Z-Formaldehyd-GlykohnonoätherAlcohol-Z-formaldehyde alcohol Alcohol-Z-formaldehyde glycol monoester Alcohol-Z-formaldehyde glycol monoether Glycol monoester Z-formaldehyde glycol monoester Glycol monoester Z-formaldehyde glycol monoether Glycine ether-Z-formaldehyde glycine ether
Durch Substitution eines Oxysäuremonoesters, wie der Lactate und Glykolate, kann eine andere Reihe von Verbindungen hergestellt werden, die nachstehend dargestellt ist:By substituting an oxyacid monoester, such as the lactates and glycolates, a different series can be made can be made by compounds shown below:
Oxymonoester-Z-Formaldehyd-Oxymonoester Oxymonoester-Z-Formaldehyd-Alkohol Oxymonoester-Z-Formaldehyd-Glykolmonoäther ao Oxymonoester-Z-Formaldehyd-GlykolmonoesterOxymonoester-Z-formaldehyde-oxymonoester Oxymonoester-Z-formaldehyde-alcohol Oxymonoester-Z-formaldehyde-glycol monoether ao Oxymonoester-Z-formaldehyde-glycol monoester
Alle vorstehend erwähnten komplexen Formale haben die allgemeine ZusammensetzungAll of the complex formals mentioned above have the general composition
as A — (Formaldehyd-Glykol) x — Formaldehyd — B oderas A - (formaldehyde glycol) x - formaldehyde - B or
A-O[CH2-O-(CnH2nO)^CH2-O-BAO [CH 2 -O- (C n H 2n O) ^ CH 2 -OB
worin A und B gleich oder verschieden sein können und aus der Gruppe organischer Reste ausgewählt werden, die 1 bis 60 C-Atome enthalten und von organischen Verbindungen abgeleitet sind, die eine alkoholische Hydroxylgruppe enthalten, und worin χ und η ganze Zahlen größer als 1 sind und y gleich oder größer als 1 ist.where A and B can be the same or different and are selected from the group of organic radicals which contain 1 to 60 carbon atoms and are derived from organic compounds which contain an alcoholic hydroxyl group, and where χ and η are integers greater than 1 and y is equal to or greater than 1.
Herstellung von C13-Oxoalkohol—(CH20-Tripropylenglykol)3CH2O — C13-OxOaIkOhOl, d. h.Preparation of C 13 -Oxoalkohol- (CH 2 0-tripropylene glycol) 3 CH 2 O - C 13 -OxOaIkOhOl, ie
C13H27O-[CH2O(C3H6O)3J3-CH2-OC13H27 C 13 H 27 O- [CH 2 O (C 3 H 6 O) 3 J 3 -CH 2 -OC 13 H 27
Man stellte zuerst das Kernstück dieses Polyformals, d.h.The core of this polyformal was first presented, i.e.
H (OC3H6) OCH2 (OC3HG)3 — OCH2 (OC3H6)3OHH (OC 3 H 6 ) OCH 2 (OC 3 H G ) 3 - OCH 2 (OC 3 H 6 ) 3 OH
her, indem man 288 g (1,5 Mol) Tripropylenglykol, 30 g (1 Mol CH2O) Trioxymethylen, 300 g Heptan und 5,5 g Katalysator (NaHSO4) 40 Minuten lang unter Rückfluß auf 89 bis 100° erhitzte. Hierbei gingen 19 ecm (Theorie 18 ecm) Wasser über. Man kühlte das Reaktionsgemisch auf 700 ab und setzte nun 200 g (1 Mol) C13-Oxoalkohol und 30 g (1 Mol CH2O) Trioxymethylen zu. Dann erhitzte man das Reaktionsgemisch 30 Minuten lang auf Rückflußtemperatur von 90 bis 1030, wobei 19,5 ecm (Theorie 18 ecm) Wasser übergingen. by heating 288 g (1.5 mol) of tripropylene glycol, 30 g (1 mol of CH 2 O) trioxymethylene, 300 g of heptane and 5.5 g of catalyst (NaHSO 4 ) for 40 minutes under reflux at 89 to 100 °. 19 ecm (theory 18 ecm) of water passed over here. The mixture was cooled the reaction mixture to 70 0, and then sat 200 g (1 mole) of C 13 oxo alcohol and 30 g (1 mole of CH 2 O) to trioxymethylene. Then the reaction mixture was heated for 30 minutes at reflux temperature 90-103 0, with 19.5 cc (18 cc theory) passed over water.
Das Reaktionsprodukt wurde vom Katalysator dekantiert und dann mit 150 ecm einer io°/0igen Lösung von Na2CO3 und schließlich zweimal mit je 100 ecm Wasser gewaschen. Dann streifte man das Produkt von Lösungsmittel und leichten Bestandteilen ab. Das Produkt, das bei 0,3 mm über 152° siedete und aus der von 14 bis 100 °/0 übergehenden Fraktion bestand, hatte folgende Eigenschaften:The reaction product was decanted from the catalyst and then with 150 cc of a io ° / 0 solution of Na 2 CO 3, and finally washed twice with 100 cc of water. The product was then stripped of solvent and light components. The product, which boiled above 152 ° at 0.3 mm and consisted of the fraction passing over from 14 to 100 ° / 0 , had the following properties:
Viskosität in cStViscosity in cSt
bei 98,9° 8,91at 98.9 ° 8.91
bei 37,8° -. 56,67at 37.8 ° -. 56.67
bei —17,8° 4657.0at -17.8 ° 4657.0
Viskositätsindex 132,0Viscosity index 132.0
Fließpunkt in °C — 43,0Pour point in ° C - 43.0
Flammpunkt in 0C 216,0Flash point at 0 C 216.0
Brennpunkt in 0C 235,0Focus at 0 C 235.0
WasserstoffverbrennungsprobeHydrogen combustion test
Kohlenstoff in mg 1,3Carbon in mg 1.3
Beschlag in mg 0,2Fog in mg 0.2
Das rückstandsfreie Verbrennen dieses Reaktionsproduktes läßt erkennen, daß es bei Verwendung als Schmieröl für Kurbelwellengehäuse von Kraftfahrzeugmotoren praktisch kein Ansteigen des Octanzahlbedarfs verursachen würde.The residue-free burning of this reaction product shows that it is when used as Lubricating oil for motor vehicle engine crankshaft housings would cause practically no increase in the octane requirement.
Herstellung von C13-Oxoalkohol — (C H2 O-Tripropylenglykol) a-C H2 O — C13-OxOaIkOhOlProduction of C 13 -oxo alcohol - (CH 2 O-tripropylene glycol) a -CH 2 O - C 13 -OxOaIkOhOl
Dieses komplexe Formal, welches dem obigen ähnelt, wurde hergestellt, um ein Produkt von niedrigerer Viskosität zu gewinnen. Man erhitzte 520 g (2,6 Mol) CM-Oxoalkohol, 117 g Paraformaldehyd (3,9 Mol CH2O), 200 g Heptan und 3,1 g (0,25%) NaHSO4-Katalysator 45 Minuten auf 55°. Dann setzte man diesem Halbformal des Cls-Oxoalkohols 500 g (2,6 Mol) Tripropylenglykol zu und erhitzte das Gemisch auf Rückflußtemperatur. Nach 3 Stunden war die Temperatur von 95 auf ii8c gestiegen, und es hatten sich 73 ecm Wasser angesammelt (Theorie 70,2 ecm). Das Produkt war hellbraun gefärbt, was ein Anzeichen dafür ist, daß die geringe Konzentration des Katalysators (0,25 °/0) eine starke Verfärbung verhinderte, wie sie bei Katalysatorkonzentrationen von 1% auftritt. Das Reaktionsprodukt wurde von dem kristallinen Katalysator getrennt, dreimal mit je 100 ecm gesättigter Na2CO3-Lösung und anschließend dreimal mit je 100 ecm Wasser gewaschen und dann von Heptan und der geringen Wassermenge abgestreift. Das Produkt, welches bei 0,2 mm Hg oberhalb 1530 siedete und aus der von 6 bis 100 °/0 übergehenden Fraktion bestand, hatte folgende Eigenschaften:This complex formula, similar to the one above, was made in order to obtain a lower viscosity product. 520 g (2.6 mol) of C M oxoalcohol, 117 g of paraformaldehyde (3.9 mol of CH 2 O), 200 g of heptane and 3.1 g (0.25%) of NaHSO 4 catalyst were heated to 55 minutes for 45 minutes °. 500 g (2.6 mol) of tripropylene glycol were then added to this semi- formal of C ls -oxo alcohol and the mixture was heated to reflux temperature. After 3 hours the temperature had risen from 95 to 18 ° C. and 73 ecm of water had collected (theory 70.2 ecm). The product was colored light brown, which is an indication that the low concentration of the catalyst (0.25 ° / 0 ) prevented severe discoloration, as occurs with catalyst concentrations of 1%. The reaction product was separated from the crystalline catalyst, washed three times with 100 ecm of saturated Na 2 CO 3 solution each time and then three times with 100 ecm of water each time and then stripped of the heptane and the small amount of water. The product, which boiled above 153 0 at 0.2 mm Hg and from 6 to 100 ° / 0 merges fraction consisted of, had the following properties:
Viskosität in cStViscosity in cSt
bei 98,9° 5,82at 98.9 ° 5.82
bei 37,8° 33,82at 37.8 ° 33.82
bei — 17,8° 2 286,0at - 17.8 ° 2 286.0
bei — 40,0° > 80 000,0at - 40.0 °> 80,000.0
Viskositätsindex 125,0 iaoViscosity index 125.0 iao
Fließpunkt in 0C — 46,0Pour point at 0 C - 46.0
Flammpunkt in °C 199,0Flash point in ° C 199.0
Brennpunkt in °C 221,0Fire point in ° C 221.0
WasserstoffverbrennungsprüfungHydrogen combustion test
Kohlenstoff in mg 0,8Carbon in mg 0.8
Beschlag in mg 0,2Fog in mg 0.2
Herstellung von η-Butyl— (OC3H6)2O (CH2O-polypropylenglykol)2 — CH2O — (OC3H6)2n-buty]Production of η-butyl— (OC 3 H 6 ) 2 O (CH 2 O-polypropylene glycol) 2 - CH 2 O - (OC 3 H 6 ) 2 n-buty]
Die Herstellung dieses komplexen Formals erfolgte gemäß Beispiel 4. Das Polypropylenglykol hatte ein mittleres Molekulargewicht von 150.This complex formal was produced according to Example 4. The polypropylene glycol had a average molecular weight of 150.
Das Produkt, welches bei 0,3 mm oberhalb i6i° siedete, hatte folgende Eigenschaften:The product, which at 0.3 mm above i6i ° boiled, had the following properties:
Viskosität in cStViscosity in cSt
bei 98,9° 3,72at 98.9 ° 3.72
bei 37,8° 17,3at 37.8 ° 17.3
bei —17,8° 591,7at -17.8 ° 591.7
bei — 40,0° 12 220,0at - 40.0 ° 12 220.0
Viskositätsindex 116,0Viscosity index 116.0
Fließpunkt in 0C — 57,0Pour point at 0 C - 57.0
Flammpunkt in °C 166,0Flash point in ° C 166.0
Brennpunkt in °C 174.0Fire point in ° C 174.0
Die bei 0,2 mm oberhalb 188° siedende Fraktion des Produktes hatte folgende Eigenschaften:The fraction of the product boiling at 0.2 mm above 188 ° had the following properties:
Viskosität in cStViscosity in cSt
bei 98,9° 5.39at 98.9 ° 5.39
bei 37,8° 29,46at 37.8 ° 29.46
bei —17,8° 1709,0at -17.8 ° 1709.0
bei — 40,0° 55 849,0at - 40.0 ° 55 849.0
Viskositätsihdex 129,0Viscosity dex 129.0
Fließpunkt in 0C — 51,0Pour point at 0 C - 51.0
Flammpunkt in 0C 177,0Flash point at 0 C 177.0
Brennpunkt in 0C 199,0Focus at 0 C 199.0
Herstellung von C13-OxOaIkOhOl-(CH2O-Tnpropylenglykol)2)3 — C H2 O — C13-OxOaIkOhOlProduction of C 13 -OxOaIkOhOl- (CH 2 O-Propylene glycol) 2) 3 - CH 2 O - C 13 -OxOaIkOhOl
2 Mol Cjg-Oxoalkohol, 3,7 Mol Formaldehyd (als Paraformaldehyd) und 2,3 Mol Tripropylenglykol wurden mit 300 g Heptan und 1,5 g Natriumbisulfat gemischt. Das Gemisch wurde auf Rückflußtemperatur erhitzt, bis die theoretische Wassermenge abgetrieben war. Dann wurde das Produkt vom Katalysator dekantiert und dreimal mit je 100 ecm Natriumcarbonatlösung und zweimal mit je 100 ecm Wasser gewaschen und nitriert. Nun wurde die Masse bis auf eine Dampftemperatur von 1760 bei 10 mm abgestreift. Das Produkt hatte folgende Eigenschaften: 2 moles of Cjg-oxo alcohol, 3.7 moles of formaldehyde (as paraformaldehyde) and 2.3 moles of tripropylene glycol were mixed with 300 g of heptane and 1.5 g of sodium bisulfate. The mixture was heated to reflux temperature until the theoretical amount of water was driven off. Then the product was decanted from the catalyst and washed three times with 100 ecm sodium carbonate solution and twice with 100 ecm water and nitrated. The mass was then stripped down to a steam temperature of 176 ° at 10 mm. The product had the following properties:
Viskosität in cStViscosity in cSt
bei 98,9° 8,06at 98.9 ° 8.06
bei 37.8° 47.81at 37.8 ° 47.81
bei—17,8° 3 49i,oat -17.8 ° 3 49i, o
bei — 40,0° > no 000,0at - 40.0 °> no 000.0
Viskositätsindex 136,0Viscosity index 136.0
Fließpunkt in 0C — 46,0Pour point at 0 C - 46.0
Flammpunkt, in 0C 218,0Flash point, at 0 C 218.0
Brennpunkt in 0C 238,0Focus at 0 C 238.0
Herstellung von Cia-Oxoalkohol — CH2O (Triäthylenglykol— CH2O)2— C13-OxOaIkOhOlProduction of C ia -oxo alcohol - CH 2 O (triethylene glycol - CH 2 O) 2 - C 13 -OxOaIkOhOl
400 g C13-Oxoalkohol und 67,2 g Formaldehyd wurden gemischt und mit 2,4 g NaHSO4 in Gegenwart von 240 g Heptan erhitzt. Man erhitzte das Gemisch etwa 25 Minuten auf 550, setzte 300 g Triäthylenglykol zu und erhitzte das Gemisch etwa ι Stunde auf 113°. Nun setzte man dem Reaktionsgemisch 33,6 g weiteren Formaldehyd zu und erhitzte eine weitere Stunde auf 1150. Nach dieser Zeit waren 60 g Wasser (Theorie 54 g) übergegangen.400 g of C 13 oxo alcohol and 67.2 g of formaldehyde were mixed and heated with 2.4 g of NaHSO 4 in the presence of 240 g of heptane. The mixture was heated for about 25 minutes at 55 0, set to 300 g triethyleneglycol and the mixture was heated about ι hour at 113 °. Now you put the reaction mixture 33.6 g further formaldehyde and heated for another hour at 115 0th After this time, 60 g of water (theory 54 g) had passed over.
Das so gewonnene Produkt wurde nach Beispiele gereinigt und bis auf eine Dampftemperatur von 2100 bei 0,9 mm Druck abgestreift.The product obtained in this way was purified according to the examples and stripped down to a steam temperature of 210 ° at 0.9 mm pressure.
Das Produkt hatte folgende Eigenschaften:The product had the following properties:
Viskosität in cStViscosity in cSt
bei 98,9° 6,34at 98.9 ° 6.34
bei 37,8° 33,87at 37.8 ° 33.87
bei —17,8° 16 049,0at -17.8 ° 16,049.0
bei —40,0° 443o6,o·at -40.0 ° 443o6, o ·
Viskositätsindex 142,0Viscosity index 142.0
Fließpunkt in 0C — 51,0Pour point at 0 C - 51.0
Flammpunkt in 0C 221,0Flash point in 0 C 221.0
Brennpunkt in 0C 243,0Focus at 0 C 243.0
Beispiel 8 8s Example 8 8s
Herstellung von C13-Oxoalkohol — O (C H2O-Pentandiol-i, 5)3 CH2 — O — C13-OxoalkoholProduction of C 13 oxo alcohol - O (CH 2 O pentanediol-i, 5) 3 CH 2 - O - C 13 oxo alcohol
Dieses Produkt wurde nach Beispiel hergestellt, jedoch mit der Ausnahme, daß man als Glykol statt Triäthylenglykol Pentandiol-i, 5 verwendete. Das Produkt wurde auf eine Dampftemperatur yon 1820 bei 10 mm Druck abgestreift.This product was prepared according to the example, with the exception that 1.5 pentanediol was used as the glycol instead of triethylene glycol. The product was stripped to a vapor temperature of 182 0 at 10 mm pressure.
Es hatte folgende Eigenschaften:It had the following properties:
Viskosität in cStViscosity in cSt
bei 98,9° 12,28at 98.9 ° 12.28
bei 37,8° 75,56at 37.8 ° 75.56
bei —17,8° 4 035,0at -17.8 ° 4035.0
bei. —40,0° —at. -40.0 ° -
Viskositätsindex 143,0Viscosity index 143.0
Fließpunkt in 0C — 37,0Pour point at 0 C - 37.0
Flammpunkt in 0C 227,0Flash point at 0 C 227.0
Brennpunkt in f C 252,0Focus in f C 252.0
Die hier beschriebenen komplexen Formale können auch als Schmierölgrundlage für Schmierfette dienen.The complex formals described here can also serve as a lubricating oil base for lubricating greases.
Diese neuartigen synthetischen Schmieröle können mit mineralischen oder anderen synthetischen Ölen zu Konzentraten oder fertigen Schmierölen gemischt werden. Sie sind mit den bekannten Schmiermittelzusätzen, wie V.-I.-Verbesserern, Fließpunkterniedrigern, ScMamminhibitoren, Rostschutzmitteln, Antioxydationsmitteln u. dgl., verträglich.These novel synthetic lubricating oils can be mixed with mineral or other synthetic oils be mixed into concentrates or finished lubricating oils. They are with the well-known lubricant additives, such as V.I. improvers, pour point depressants, anti-rust agents, anti-rust agents, antioxidants and the like, compatible.
Claims (9)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US323338A US2796401A (en) | 1952-11-29 | 1952-11-29 | Complex formal lubricating composition |
Publications (1)
Publication Number | Publication Date |
---|---|
DE961483C true DE961483C (en) | 1957-04-04 |
Family
ID=23258784
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DEST7387A Expired DE961483C (en) | 1952-11-29 | 1953-11-28 | Synthetic lubricant |
Country Status (3)
Country | Link |
---|---|
US (1) | US2796401A (en) |
DE (1) | DE961483C (en) |
NL (2) | NL89229C (en) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1059599B (en) * | 1953-05-28 | 1959-06-18 | Exxon Research Engineering Co | Synthetic lubricants |
DE1121759B (en) * | 1954-03-17 | 1962-01-11 | Exxon Research Engineering Co | Synthetic lubricant |
Families Citing this family (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3005774A (en) * | 1957-07-29 | 1961-10-24 | Exxon Research Engineering Co | Lubricants containing cross-linked polymers as thickening agents |
US3205269A (en) * | 1960-05-10 | 1965-09-07 | Union Carbide Corp | Stabilization of ethers with phosphorous compounds |
US3231604A (en) * | 1962-01-23 | 1966-01-25 | Du Pont | Polyethylene oxide and polypropylene oxide perfluoroalkyl substituted oxyalkanoates |
US3249543A (en) * | 1963-04-30 | 1966-05-03 | Monsanto Res Corp | Lubricant composition containing a rhodanine compound |
DE1233842B (en) * | 1965-01-16 | 1967-02-09 | Huels Chemische Werke Ag | Process for making asymmetric formals |
US3392118A (en) * | 1966-06-09 | 1968-07-09 | Sinclair Research Inc | Formal of diene polymer containing terminal hydroxyl groups and mineral oil containing same |
US3875197A (en) * | 1968-07-15 | 1975-04-01 | Hoechst Ag | Amido-methyl-polyglycol formals |
US3900411A (en) * | 1973-11-19 | 1975-08-19 | Mobil Oil Corp | Lubricant compositions containing acetal or ketal detergents |
US4093666A (en) * | 1974-02-06 | 1978-06-06 | Hoechst Aktiengesellschaft | Process for the manufacture of glycol ether formals |
US4189609A (en) * | 1974-08-19 | 1980-02-19 | Basf Wyandotte Corporation | Multi-block coupled polyoxyalkylene copolymer surfactants |
US4408084A (en) * | 1981-01-09 | 1983-10-04 | Basf Wyandotte Corporation | Non-ionic surfactants containing acetal groups |
US5744064A (en) * | 1995-05-12 | 1998-04-28 | Union Carbide Chemicals & Plastics Technology Corporation | Ketone-based surfactant and method for treating industrial, commerical, and institutional waste-water |
US5744065A (en) | 1995-05-12 | 1998-04-28 | Union Carbide Chemicals & Plastics Technology Corporation | Aldehyde-based surfactant and method for treating industrial, commercial, and institutional waste-water |
Family Cites Families (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2350350A (en) * | 1941-05-06 | 1944-06-06 | Du Pont | Glycol formals |
US2397602A (en) * | 1941-11-22 | 1946-04-02 | Du Pont | Preparation of ester polymers |
US2379703A (en) * | 1942-04-24 | 1945-07-03 | Richards Chemical Works Inc | Process for the production of derivatives of polyhydroxy alcohols |
BE461872A (en) * | 1944-12-30 | |||
US2473994A (en) * | 1945-08-04 | 1949-06-21 | Du Pont | 1, 3-dioxolane polymers |
US2594341A (en) * | 1949-09-13 | 1952-04-29 | Standard Oil Dev Co | Utilization of oxo bottoms |
-
0
- NL NLAANVRAGE7807232,A patent/NL181914B/en unknown
- NL NL89229D patent/NL89229C/xx active
-
1952
- 1952-11-29 US US323338A patent/US2796401A/en not_active Expired - Lifetime
-
1953
- 1953-11-28 DE DEST7387A patent/DE961483C/en not_active Expired
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1059599B (en) * | 1953-05-28 | 1959-06-18 | Exxon Research Engineering Co | Synthetic lubricants |
DE1121759B (en) * | 1954-03-17 | 1962-01-11 | Exxon Research Engineering Co | Synthetic lubricant |
Also Published As
Publication number | Publication date |
---|---|
NL89229C (en) | |
NL181914B (en) | |
US2796401A (en) | 1957-06-18 |
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