DE923009C - Process for the production of high molecular weight alcohols - Google Patents

Process for the production of high molecular weight alcohols

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Publication number
DE923009C
DE923009C DER2337D DER0002337D DE923009C DE 923009 C DE923009 C DE 923009C DE R2337 D DER2337 D DE R2337D DE R0002337 D DER0002337 D DE R0002337D DE 923009 C DE923009 C DE 923009C
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Germany
Prior art keywords
molecular weight
high molecular
weight alcohols
production
condensation
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Expired
Application number
DER2337D
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German (de)
Inventor
Otto Dr Roelen
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CHEMISCHE VERWERTUNGSGESELLSCHAFT OBERHAUSEN MBH
Original Assignee
CHEMISCHE VERWERTUNGSGESELLSCHAFT OBERHAUSEN MBH
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Priority to DER2337D priority Critical patent/DE923009C/en
Application granted granted Critical
Publication of DE923009C publication Critical patent/DE923009C/en
Expired legal-status Critical Current

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    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M3/00Liquid 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
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/02Hydroxy compounds
    • C10M2207/021Hydroxy compounds having hydroxy groups bound to acyclic or cycloaliphatic carbon atoms
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10NINDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00Specified use or application for which the lubricating composition is intended
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10NINDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00Specified use or application for which the lubricating composition is intended
    • C10N2040/30Refrigerators lubricants or compressors lubricants
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10NINDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00Specified use or application for which the lubricating composition is intended
    • C10N2040/32Wires, ropes or cables lubricants
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10NINDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00Specified use or application for which the lubricating composition is intended
    • C10N2040/34Lubricating-sealants
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10NINDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00Specified use or application for which the lubricating composition is intended
    • C10N2040/36Release agents or mold release agents
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10NINDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00Specified use or application for which the lubricating composition is intended
    • C10N2040/38Conveyors or chain belts
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10NINDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00Specified use or application for which the lubricating composition is intended
    • C10N2040/40Generators or electric motors in oil or gas winning field
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10NINDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00Specified use or application for which the lubricating composition is intended
    • C10N2040/42Flashing oils or marking oils
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10NINDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00Specified use or application for which the lubricating composition is intended
    • C10N2040/44Super vacuum or supercritical use
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10NINDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00Specified use or application for which the lubricating composition is intended
    • C10N2040/50Medical uses

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

Description

'Verfahren zur Herstellung hochmolekularer Alkohole Die kondensierende Behandlung von Aldehyden und Ketonen ist bereits bekannt. Durch Hydrierung der hierbei erhaltenen Kondensationsprodukte entstehen hochmolekulare Alkohole. Die bisher verarbeiteten Ausgangsstoffe enthielten neben, Aldehyden, Ketonen, Aldolenr, Acetalen und anderen sauerstoffhaltigen Verbindungen keine gesättigten Kohlenwasserstoffe. Auch waren diese Ausgangsstoffe nicht durch katalytische Wassergasanlagerung an olefinische Kohlenstoffbindungen hergestellt.'Process for the production of high molecular weight alcohols The condensing Treatment of aldehydes and ketones is already known. By hydrogenation of this The condensation products obtained form high molecular weight alcohols. The ones processed so far Starting materials contained, besides, aldehydes, ketones, aldolenr, acetals and others oxygen-containing compounds do not contain saturated hydrocarbons. Also were these starting materials are not converted to olefinic ones by catalytic water gas attachment Carbon bonds made.

Es wurde gefunden, daB man besonders wertvolle hochmolekulare Alkohole mit mindestens 6 Kohlenstoffatomen im Molekül durch kondensierende und hydrierende Behandlung von Produkten erhält, die sich bei der katalytischen Anlagerung von Wassergas an ungesättigte, insbesondere olefinische Kohlenwasserstoffgemische ergeben, die größere Mengen von, Paraffinkohlenwasserstoffen enthalten. Die eigentümliche Struktur der Wassergasanlagerungsprodukteerlauht dieHerstellung von neuartigen. Kondensationsprodukten. Durch nachfolgende Hydrierung entstehen hochmolekulare Alkohole mit besonders wertvollen Eigenschaften. Diese Produkte sind sowohl hochviskos als auch tiefstockend und besitzen einen geringen Dampfdruck. Sie eignen sich in; hervorragender Weise; z. B. als Weichmachungsmittel, Schmiermittel, hydraulische Arbeitsflüssigkeiten und als Ausgangsstoffe für die- Herstellung von sulfanierien Wasch- bzw. Netzmittelni.It has been found that particularly valuable high molecular weight alcohols are obtained with at least 6 carbon atoms in the molecule through condensing and hydrogenating Treatment of products obtained from the catalytic attachment of water gas to unsaturated, in particular olefinic hydrocarbon mixtures which contain large amounts of paraffinic hydrocarbons. The peculiar structure the water gas addition products allows the manufacture of novel. Condensation products. The subsequent hydrogenation results in high molecular weight alcohols with particularly valuable Properties. These products are both highly viscous and deeply stocky and possess a low vapor pressure. They are useful in; excellent way; z. B. as a plasticizer, Lubricant, hydraulic working fluids and as raw materials for the production of sulfanated detergents or wetting agentsi.

Zur Kondensation der - Wassergasanlagerungsprodukte sind Alkalien, z. B. Kalilauge oder Natronlauge, geeignet. Die nicht an der Wassergasanlagerun.g teilnehmenden Begleitstoffe, des olefinischen Kohlenwasserstoffgemisches kann man entweder mit in den Kondensationspro.zeß hineinnehmen oder vorher :ganz bzw. teilweise abtrennen.For the condensation of the - water gas addition products are alkalis, z. B. potassium hydroxide solution or sodium hydroxide solution, suitable. Those not connected to the water gas system Participating accompanying substances of the olefinic hydrocarbon mixture can be either take it into the condensation process or beforehand: completely or partially split off.

Besonders vorteilhaft ist es, daß man bei dem neuen Verfahren Struktur und Eigenschaften der erzeugten hochmolekularen Alkohole dem gewünschten Verwendungszweck -weitgehend anpassen kann. Die Umsetzung von Olefi.nen mit Wassergas liefert nämlich .ganz bestimmte Gemische gleicher oder verschiedener Molekülgröße, die sich nunmehr willkürlich in entsprechender Auswahl oder Kombination der Kondensation zuführen lassen. -Man kannbeispielsweise enggeschnitterne olefinische Kahlenwasserstofffräktioneni, welche nur eine. Molekülgröße enthalten, mit Wassergas behandeln und die entstehenden Anlagerungsprodukte mit sich selbst kondensieren. Hierbei ergeben sich Alkohole von einheitlichem Molekülaufbau und entsprechenden Eigenschaften. Man kann aber auch ein breites Band von oleflnischien Kohlenwasserstoffon, das aufeinanderfolgende Molekülgrößen; enthält und z. B. durch Kohlenwasserstoffspaltung oder Kohlemxydhydri,erung leicht zugänglich ist, mit Wassergas umsetzen und das dabei entstehende Gemisch von. Oxoverbindungen der Kondensation unterwerfen. Bei der nachfolgenden Hydrierung ergibt sich sodann ein untrennbares Gemisch hochmolekularer Alkohole- mit Molekülen der verschiedenartigsten Größe und Struktur. Derart verwickelt aufgebaute Gemische sind für bestimmte Verwendungsgebiete, z. B. für SehmierzwedQe, besonders vorteilhaft.It is particularly advantageous that structure is obtained in the new process and properties of the high molecular weight alcohols produced, the desired use -Can adapt to a large extent. The reaction of olefins with water gas delivers . Quite certain mixtures of the same or different molecular size, which are now arbitrarily supply the condensation in the appropriate selection or combination permit. -One can, for example, narrow-cut olefinic hydrocarbon fractionsi, which only one. Contain molecule size, treat with water gas and the resulting Addition products condense with themselves. This results in alcohols of uniform molecular structure and corresponding properties. But you can also a broad band of olefinic hydrocarbons, the successive ones Molecular sizes; contains and z. B. by hydrocarbon splitting or Kohlemxydhydri, erung is easily accessible, react with water gas and the resulting mixture from. Subject oxo compounds to condensation. In the subsequent hydrogenation This then results in an inseparable mixture of high molecular weight alcohols with molecules of the most varied of size and structure. Mixtures built up in such a complex manner are for certain areas of use, e.g. B. for SehmierzwedQe, particularly advantageous.

Es ist aber auch möglich, Oleflne geringerer Molekülgröße und Ole'fine höherer Molekülgröße., und zwar getrennt für sich oder bereits gemeinsam mit Wassergas zu .behandeln, um die dabei entstandenen Aldehydprodukte zu kondensieren und ' zu hydrieren. Auf diese Weise erhält man Alkoholgemische, welche sich in ihrer Zusammensetzung und in ihren physikalischen Eigtenschaften wesentlich von den soeben erwähnten Reaktionisprodu'kten unterscheiden.But it is also possible to use olefins of smaller molecular size and olefins higher molecular size., either separately or together with water gas to .handeln in order to condense the resulting aldehyde products and 'to hydrogenate. In this way, alcohol mixtures are obtained which differ in their composition and in their physical properties essentially from the reaction products just mentioned differentiate.

Die Ausführung des Verfahrens möge an Hand des nachstehenden Ausführungsbeispiels näher erläutert werden. Beispiel Es wurden 5ooo ccm einer zwischen 15o und 230' siedenden Fraktion der Kahlenoxydhydrierung, welche 5oo/o Olefine enthielt, unter Ver-Wendung eines Kobaltmischkatalysators bei z2o° und 18o atü mit Wassergas behandelt. Das entstehende Reaktionsprodukt wurde mit 2ooo ccm Methanol versetzt, dem vorher 511o metallisches Natrium zugemischt waren. Unter starker Temperaturerhöhung trat eine heftige Reaktion ein. Das entstehende Kondensationsprodukt wurde kalt mit einer ausreichenden Menge Wasser gewaschen und vom Kondensationsmittel befreit.The execution of the method will be explained in more detail with reference to the following exemplary embodiment. EXAMPLE 500 cc of a fraction from the Kahlenoxide hydrogenation boiling between 150 and 230 ' and containing 500 per cent olefins were treated with water gas using a cobalt mixed catalyst at 20 ° and 18 ° atm. The resulting reaction product was mixed with 2,000 cc of methanol to which 5110 metallic sodium had previously been admixed. A violent reaction occurred with a sharp increase in temperature. The resulting condensation product was washed cold with a sufficient amount of water and freed from the condensation agent.

Das fertig ausgewaschene Produkt hatte eine Dichte D ü° = o,825 und einen Brechungsindex n D = 1,4462, seine OH-Zahl betrug 87, seine Neutralisationszahl NZ = 3. Es wurde ,bei 140' unter einem Druck von r50 atü. mit einem Kobaltmischkontakthydriert. Nach 2 Stunden war die Wasserstoffaufnahme beendet, so daß der Katalysator ab,-filtriert und das Hydrierprodukt mit verdünnter Salpetersäure von; den aufgenommenen. Metallresten befreit werden konnte. Nach dieser Säurebehandlung wurde mit Wasser neutral gewaschen und eine Endprodukt erzielt, das folgende Eigenschaften besaß Hydroxylzahl .... OHZ = 2o2 Neutralisationszahl NZ = o Dichte . . . . . . . . . . . . Dü° = 0,832 Brechungsindex .... nD = 1,4458.The washed-out product had a density D o = 0.825 and a refractive index n D = 1.4462, its OH number was 87, its neutralization number NZ = 3. It was at 140 ° under a pressure of r50 atm. hydrogenated with a cobalt mixed contact. After 2 hours, the hydrogen uptake was complete, so that the catalyst filtered off, and the hydrogenation product with dilute nitric acid of; the recorded. Metal residues could be freed. After this acid treatment, the product was washed neutral with water and an end product was obtained which had the following properties: hydroxyl number ... OHZ = 2o2 neutralization number NZ = o density . . . . . . . . . . . . Dü ° = 0.832 refractive index .... nD = 1.4458.

Nach Abdestillation der vorhandenen P.araffinkohlenwasserstoffe erhielt man 158o ccm einlos wertvollen hochviskosen Öles mit der OH-Zahl 256, der Neutralisationszahl NZ = o, der Dichte Dz4 = o,868 und dem Brechungsindex n D = 1,q.592. :Die Viskosität bei 3o0 belief sich auf V30 = 9,o 1'°'E und bei 5o0 auf V5, = 3,6o°'E. Die Viskositätspolhöhe wurde zu VPH = 2,34 festgestellt. Der Stockpunkt lag bei -43"# und der Trübungspunkt bei -400.After distilling off the araffin hydrocarbons present, 158o ccm of valuable, highly viscous oil with an OH number of 256, a neutralization number NZ = 0, a density Dz4 = 0.868 and a refractive index n D = 1, 592 was obtained. : The viscosity at 3o0 was V30 = 9, o 1 '°' E and at 5o0 to V5, = 3.6 ° 'E. The viscosity pole height was found to be VPH = 2.34. The pour point was -43 "# and the cloud point was -400.

Das Produkt war beispielsweise als Schmieröl für Kältemaschinen geeignet.The product was suitable, for example, as a lubricating oil for refrigeration machines.

Claims (1)

PATI:NTANSPRU.CI3: Verfahren zur Herstellung hochmolekularer Alkohole mit mindestens 6 Kohlenstoffatomen im Molekül durch Kondensation von Gemischen aliphatischer Oxoverbindungen in Gegenwart basisch wirkender Mittel und nachfolgende Hydrierung der Kondensationserzeugnisse, dadurch gekennzeichnet, daß Ausgangsgemische verarbeitet werden, die durch katalytische Anlagerung von Wassergas an ungesättigte, insbesondere olefinhaltige Kohlenwasserstoffe entstehen, die größere Mengen von, Paraffinkohlenwasserstoffen enthielten. Angezogene Druckschriften: Britische Patentschriften Nr. 309 200, 461 662; französische Patentschrift Nr. 832 O72.PATI: NTANSPRU.CI3: Process for the production of high molecular weight alcohols with at least 6 carbon atoms in the molecule by condensation of mixtures of aliphatic oxo compounds in the presence of basic agents and subsequent hydrogenation of the condensation products, characterized in that starting mixtures are processed which are processed by the catalytic addition of water gas to unsaturated ones , in particular olefin-containing hydrocarbons, which contained large amounts of paraffin hydrocarbons. Cited references: British Patent Nos. 309,200 , 461,662; French patent specification No. 832 O72.
DER2337D 1940-08-21 1940-08-21 Process for the production of high molecular weight alcohols Expired DE923009C (en)

Priority Applications (1)

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DER2337D DE923009C (en) 1940-08-21 1940-08-21 Process for the production of high molecular weight alcohols

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DER2337D DE923009C (en) 1940-08-21 1940-08-21 Process for the production of high molecular weight alcohols

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DE923009C true DE923009C (en) 1955-01-31

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Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB309200A (en) * 1927-09-28 1929-03-28 Ig Farbenindustrie Ag A process for the manufacture and production of mono- and polyhydric alcohols
GB461662A (en) * 1934-12-20 1937-02-22 Carbide & Carbon Chem Corp Improvements in the preparation of oxygenated aliphatic compounds
FR832072A (en) * 1937-02-06 1938-09-20 Ig Farbenindustrie Ag Process for preparing high molecular weight aldehydes, ketones and alcohols

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB309200A (en) * 1927-09-28 1929-03-28 Ig Farbenindustrie Ag A process for the manufacture and production of mono- and polyhydric alcohols
GB461662A (en) * 1934-12-20 1937-02-22 Carbide & Carbon Chem Corp Improvements in the preparation of oxygenated aliphatic compounds
FR832072A (en) * 1937-02-06 1938-09-20 Ig Farbenindustrie Ag Process for preparing high molecular weight aldehydes, ketones and alcohols

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