DE293787C - - Google Patents

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Publication number
DE293787C
DE293787C DENDAT293787D DE293787DA DE293787C DE 293787 C DE293787 C DE 293787C DE NDAT293787 D DENDAT293787 D DE NDAT293787D DE 293787D A DE293787D A DE 293787DA DE 293787 C DE293787 C DE 293787C
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hydrocarbons
hydrogen
compounds
mixtures
carbon
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    • 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
    • C07C29/15—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of oxides of carbon exclusively
    • C07C29/151—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of oxides of carbon exclusively with hydrogen or hydrogen-containing gases
    • C07C29/153—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of oxides of carbon exclusively with hydrogen or hydrogen-containing gases characterised by the catalyst used
    • C07C29/156—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of oxides of carbon exclusively with hydrogen or hydrogen-containing gases characterised by the catalyst used containing iron group metals, platinum group metals or compounds thereof
    • C07C29/157—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of oxides of carbon exclusively with hydrogen or hydrogen-containing gases characterised by the catalyst used containing iron group metals, platinum group metals or compounds thereof containing platinum group metals or compounds thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C1/00—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon
    • C07C1/02—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon from oxides of a carbon
    • 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
    • C07C29/15—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of oxides of carbon exclusively
    • C07C29/151—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of oxides of carbon exclusively with hydrogen or hydrogen-containing gases
    • C07C29/1512—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of oxides of carbon exclusively with hydrogen or hydrogen-containing gases characterised by reaction conditions
    • 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
    • C07C29/15—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of oxides of carbon exclusively
    • C07C29/151—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of oxides of carbon exclusively with hydrogen or hydrogen-containing gases
    • C07C29/153—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of oxides of carbon exclusively with hydrogen or hydrogen-containing gases characterised by the catalyst used
    • 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
    • C07C29/15—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of oxides of carbon exclusively
    • C07C29/151—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of oxides of carbon exclusively with hydrogen or hydrogen-containing gases
    • C07C29/153—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of oxides of carbon exclusively with hydrogen or hydrogen-containing gases characterised by the catalyst used
    • C07C29/156—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of oxides of carbon exclusively with hydrogen or hydrogen-containing gases characterised by the catalyst used containing iron group metals, platinum group metals or compounds thereof

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)

Description

Ι« PATENTAMTΙ «PATENT OFFICE

KAISERLICHES JIMPERIAL J

PATENTSCHRIFTPATENT LETTERING

- M 293787 KLASSE 12 ο. GRUPPE \J[?.(j - M 293787 CLASS 12 ο. GROUP \ J [?. (J

BADISCHE ANILIN- & SODA-FABRIK in LUDWIGSHAFEN a. Rh.BADISCHE ANILINE & SODA FACTORY in LUDWIGSHAFEN a. Rh.

Verfahren zur Darstellung von Kohlenwasserstoffen und deren Derivaten.Process for the preparation of hydrocarbons and their derivatives.

Patentiert im Deutschen Reiche vom 8. März 1913 ab.Patented in the German Empire on March 8, 1913.

Es ist bekannt, daß man aus Kohlenoxyd oder Kohlensäure und Wasserstoff bei erhöhter Temperatur mittels Katalysatoren, insbesondere Nickel, Methan herstellen kann, auch finden sich Angaben, daß man unter veränderten Versuchsbedingungen geringe Mengen Formaldehyd sowie Äthylen erhalte.It is known that one can convert carbon dioxide or carbonic acid and hydrogen at increased Temperature by means of catalysts, in particular nickel, methane can be produced, there are also information that one can find under modified experimental conditions received small amounts of formaldehyde and ethylene.

Es wurde nun gefunden, daß man Kohlenwasserstoffe flüssiger oder leicht zu verflüssigender Natur, und von Kohlenwasserstoffen abgeleitete Verbindungen, namentlich Sauerstoffderivate, leicht aufbauen kann, wenn man die Oxyde des Kohlenstoffs mit Wasserstoff oder wasserstoffreichen Verbindungen, wie z. B.It has now been found that hydrocarbons are more liquid or easy to liquefy Nature, and compounds derived from hydrocarbons, namely oxygen derivatives, can easily build up if you combine the oxides of carbon with hydrogen or hydrogen-rich compounds, such as. B.

Methan, oder mit Gemischen beider untereinander oder mit anderen Gasen in Gegenwart von Katalysatoren unter höheren Drucken, und zwar zweckmäßig von vielen Atmosphären, behandelt. Je nach der Natur des Katalysators und den Arbeitsbedingungen können sehr verschiedene Stoffe bzw. Gemische solcher entstehen, z. B. flüssige Kohlenwasserstoffe gesättigter und ungesättigter Natur, Alkohole, Aldehyde, Ketone, Säuren usw. Für die Erzielung insbesondere größerer Mengen flüssiger Verbindungen kann es vorteilhaft sein, solche Gasgemische zu verwenden, in welchen der Wasserstoffgehalt verhältnismäßig zurücktritt.Methane, or with mixtures of both with each other or with other gases in the presence of catalysts under higher pressures, suitably from many atmospheres, treated. Depending on the nature of the catalyst and the working conditions, very different substances or mixtures of these can be used arise, e.g. B. liquid hydrocarbons of saturated and unsaturated nature, alcohols, Aldehydes, ketones, acids, etc. For achieving particularly large amounts of liquid Compounds, it may be advantageous to use such gas mixtures in which the Hydrogen content decreases proportionally.

Als Katalysatoren kann man die verschiedenartigsten Elemente und Verbindungen verwenden. . Beispielsweise seien Cer, Chrom, Kobalt, Mangan, Molybdän, Osmium, Palladium, Titan, Zink bzw. Oxyde oder sonstige Verbindungen derselben genannt. Man kann auch _Ji5 Gemische anwenden und dem Katalysator andere, z. B. vorteilhaft basischere Stoffe, wie Alkalihydroxyd, beigeben.A wide variety of elements and compounds can be used as catalysts. . For example, cerium, chromium, cobalt, manganese, molybdenum, osmium, palladium, Titanium, zinc or oxides or other compounds of the same are called. One can also _Ji5 apply mixtures and the catalyst others, e.g. B. advantageously more basic substances, such as alkali hydroxide, add.

Verwendet man statt Kohlenoxyd Kohlensäure, so treten im allgemeinen die höheren bzw. flüssigen Kohlenwasserstoffe zurück.If carbonic acid is used instead of carbon dioxide, the higher ones generally occur or liquid hydrocarbons.

Beispiel 1.Example 1.

Über mit reinem Kobaltoxyd oder Osmiumoxyd und etwas Ätznatron imprägnierten "reinen Asbest wird bei 100 Atm. Druck und 300 bis 400 ° eiri Gemisch von etwa zwei oder auch mehr Teilen reinem Kohlenoxyd und einem Teil reinem Wasserstoff übergeleitet. Es entstehen hierbei, meist unter Kohlenstoffabscheidung und Bildung gewisser Mengen von Wasser und Kohlensäure, neben Methan verschiedene höhere Kohlenwasserstoffe sowie Sauerstoffderivate von Kohlenwasserstoffen, die in einer kalten Vorlage verdichtet bzw. absorbiert werden. Hierbei scheidet sich in der Regel eine wässerige Lösung von Aldehyden u. dgl., sowie eine leichtere ölige Flüssigkeit ab, welche in der Hauptsache aus gesättigten und ungesättigten Kohlenwasserstoffen besteht, die bis etwa 250 ° oder noch höher sieden. Man kann die Vorlage zweckmäßig unter gleichem Druck wie den Reaktionsraum halten und die Kondensation durch Tiefkühlung oder auch durch eine fraktionierte Abkühlung mit oder ohne Druckentspannung vornehmen.Over impregnated with pure cobalt oxide or osmium oxide and some caustic soda "Pure asbestos is at 100 atm. pressure and 300 to 400 ° eiri mixture of about two or more parts of pure carbon monoxide and a part of pure hydrogen passed over. It is formed here, mostly with carbon deposition and formation of certain quantities of water and carbonic acid, various besides methane higher hydrocarbons and oxygen derivatives of hydrocarbons, which are compressed or absorbed in a cold receiver will. As a rule, an aqueous solution of aldehydes separates here and the like, as well as a lighter oily liquid, which mainly consists of saturated and unsaturated hydrocarbons that boil up to about 250 ° or even higher. The initial charge can expediently be kept under the same pressure as the reaction space and condensation by freezing or by fractional cooling with or without pressure release.

Ist das angewandte Gasgemisch stickstoff-, ammoniak- oder schwefelhaltig, so können unter Umständen stickstoffhaltige oder schwefelhaltige organische Verbindungen mitentstehen. .If the gas mixture used contains nitrogen, ammonia or sulfur, you can possibly nitrogen-containing or sulfur-containing organic compounds are also formed. .

Analog verfährt man bei Verwendung von Kohlensäure statt oder neben Kohlenoxyd.The procedure is analogous when using carbonic acid instead of or in addition to carbon dioxide.

Beispiel 2.Example 2.

Ein geeigneter Träger, wie gebrannte Magnesia, Schwemmstein, Diatomitstein u. dgl., wird mit Kaliumkarbonatlösung getränkt und getrocknet; hierauf bringt man die Masse in eine konzentrierte Zinknitratlösung, gießt ab, trocknet und erhitzt. Über diese Kontakt-, masse leitet man im Hochdruckapparat beiA suitable carrier such as burnt magnesia, alluvial stone, diatomite stone and the like. is soaked with potassium carbonate solution and dried; then one brings the mass in a concentrated zinc nitrate solution, pour off, dry and heat. About this contact, mass is added to the high-pressure apparatus

■ 120 Atm. und 360 bis 420° ein Gasgemisch, ' bestehend aus z. B. 62 Prozent CO, 28 Prozent H2, 4 Prozent CO2, 2 Prozent CH4, 4 Prozent N2. Es bilden sich in der Hauptsache höhere Kohlenwasserstoffe sowie Kohlenwasserstoffderivate. Kohlenstoff wird in.der Regel nicht oder nur in geringer Menge abgeschieden. Der größte Teil der zu verflüssigenden bzw. absorbierbaren Produkte kann schon bei gewöhnlicher Temperatur abgeschieden werden, wobei das Restgas in der Regel noch einen Gehalt an Olefinen, wie Äthylen, Propylen, unter Umständen auch Äthan usw., aufweist.■ 120 atm. and 360 to 420 ° a gas mixture, 'consisting of z. B. 62 percent CO, 28 percent H 2 , 4 percent CO 2 , 2 percent CH 4 , 4 percent N 2 . Mainly higher hydrocarbons and hydrocarbon derivatives are formed. As a rule, carbon is not deposited or only in a small amount. Most of the liquefied or absorbable products can be separated off at normal temperature, the residual gas usually still containing olefins, such as ethylene, propylene, possibly also ethane, etc.

Die Analyse ergab z. B.:The analysis showed z. B .:

a) in der öligen Schicht hauptsächlich Kohlenwasserstoffe mit Siedepunkten von etwaa) in the oily layer mainly hydrocarbons with boiling points of about

■ 20° bis über 200 °, und zwar etwa ungefähr zu 2/3 gesättigten und zu Y3 olefinischen Charakters, wobei im einzelnen die Verhältnisse stark schwanken können; daneben insbesondere gelöste organische Sauerstoffverbindungen verschiedener Art; durch besondere Reinigungsoperationen kann man hieraus ein Produkt gewinnen, das erdölartigen Charakter hat;■ 20 ° to about 200 °, approximately about 2/3 of saturated and Y 3 of olefinic character, which may vary greatly in detail the conditions; in addition, in particular dissolved organic oxygen compounds of various types; Through special cleaning operations, a product can be obtained from this which has a petroleum-like character;

b) in dem entstandenen bzw. vorgelegten Wasser einen schwankenden Gehalt organischer Verbindungen gesättigter oder auch ungesättigter Natur, bestehend je nach Umständen' aus Alkoholen, Ketonen (wie Aceton), Aidehyden'(wie Formaldehyd), Säuren (wie Essigsäure und höhere Homologe) und Kondensationsprodukten. b) a fluctuating organic content in the water produced or in the water Compounds of a saturated or unsaturated nature, depending on the circumstances' from alcohols, ketones (such as acetone), aidehydes (such as formaldehyde), acids (such as acetic acid and higher homologues) and condensation products.

Im Falle, daß die verwendeten Gasgemische nicht genügend rein sind, sondern Spuren hemmender Stoffe enthalten, ist es zweckmäßig, eine besondere Reinigung vorzunehmen, indem man z. B. der eigentlichen Kontaktmasse einen erwärmten Vorkontakt vorschaltet. Das den Abscheidungsapparat verlassende Restgas kann nach Korrektur seiner Zusammensetzung (z. B. Abscheidung von Kohlensäure, Zuführuug von Wasserstoff usw) von neuem für die Umsetzung verwendet werden.In the event that the gas mixtures used are not sufficiently pure, but rather traces contain inhibiting substances, it is advisable to carry out special cleaning, by z. B. upstream of the actual contact mass a heated pre-contact. The residual gas leaving the separation apparatus can after its composition has been corrected (e.g. separation of carbonic acid, supply of hydrogen, etc.) of new to be used for the implementation.

Claims (1)

Patent-Anspruch:Patent claim: Verfahren zur Darstellung von flüssigen oder leicht zu verflüssigenden Kohlenwasserstoffen bzw. von Kohlenwasserstoffderivaten, dadurch gekennzeichnet, daß man die Oxyde des Kohlenstoffs' mitProcess for the preparation of liquid or easily liquefied hydrocarbons or of hydrocarbon derivatives, characterized in that the oxides of carbon 'with ;.■ Wasserstoff oder wasserstoffreichen Verbindungen oder mit Gemischen beider in;. ■ hydrogen or hydrogen-rich compounds or with mixtures of both in ■ Gegenwart von Katalysatoren unter höheren Drucken behandelt , : ;■ presence of catalysts treated under higher pressures, : ;
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Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE742376C (en) * 1937-10-20 1943-12-14 Metallgesellschaft Ag Process for converting carbon monoxide and hydrogen into hydrocarbon mixtures
DE744078C (en) * 1937-09-26 1944-01-08 Metallgesellschaft Ag Process for the production of hydrocarbons by caroxide hydrogenation
DE761883C (en) * 1936-12-03 1951-08-23 Metallgesellschaft Ag Process for the production of hydrocarbons from carbon monoxide and hydrogen
DE928045C (en) * 1951-03-14 1955-05-23 Basf Ag Process for the production of alcohols, in particular isobutyl alcohol
DE972657C (en) * 1949-07-12 1959-09-03 Ruhrchemie Ag Process for the production of liquid, oxygen-containing products with a high content of esters by carbohydrate hydrogenation
EP0355229A1 (en) * 1988-08-25 1990-02-28 Exxon Research And Engineering Company Production of alcohols and olefins

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE761883C (en) * 1936-12-03 1951-08-23 Metallgesellschaft Ag Process for the production of hydrocarbons from carbon monoxide and hydrogen
DE744078C (en) * 1937-09-26 1944-01-08 Metallgesellschaft Ag Process for the production of hydrocarbons by caroxide hydrogenation
DE742376C (en) * 1937-10-20 1943-12-14 Metallgesellschaft Ag Process for converting carbon monoxide and hydrogen into hydrocarbon mixtures
DE972657C (en) * 1949-07-12 1959-09-03 Ruhrchemie Ag Process for the production of liquid, oxygen-containing products with a high content of esters by carbohydrate hydrogenation
DE928045C (en) * 1951-03-14 1955-05-23 Basf Ag Process for the production of alcohols, in particular isobutyl alcohol
EP0355229A1 (en) * 1988-08-25 1990-02-28 Exxon Research And Engineering Company Production of alcohols and olefins

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