DE767891C - Process for removing sulfur compounds from hydrocarbon mixtures - Google Patents

Process for removing sulfur compounds from hydrocarbon mixtures

Info

Publication number
DE767891C
DE767891C DER109400D DER0109400D DE767891C DE 767891 C DE767891 C DE 767891C DE R109400 D DER109400 D DE R109400D DE R0109400 D DER0109400 D DE R0109400D DE 767891 C DE767891 C DE 767891C
Authority
DE
Germany
Prior art keywords
sulfur compounds
hydrocarbon mixtures
sulfur
removing sulfur
sulfonation
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
DER109400D
Other languages
German (de)
Inventor
Walter Dr Rottig
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.)
Ruhrchemie AG
Original Assignee
Ruhrchemie AG
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Ruhrchemie AG filed Critical Ruhrchemie AG
Priority to DER109400D priority Critical patent/DE767891C/en
Application granted granted Critical
Publication of DE767891C publication Critical patent/DE767891C/en
Expired legal-status Critical Current

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Classifications

    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10GCRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
    • C10G17/00Refining of hydrocarbon oils in the absence of hydrogen, with acids, acid-forming compounds or acid-containing liquids, e.g. acid sludge
    • C10G17/095Refining of hydrocarbon oils in the absence of hydrogen, with acids, acid-forming compounds or acid-containing liquids, e.g. acid sludge with "solid acids", e.g. phosphoric acid deposited on a carrier
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C7/00Purification; Separation; Use of additives
    • C07C7/12Purification; Separation; Use of additives by adsorption, i.e. purification or separation of hydrocarbons with the aid of solids, e.g. with ion-exchangers
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10GCRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
    • C10G29/00Refining of hydrocarbon oils, in the absence of hydrogen, with other chemicals

Landscapes

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

Description

Verfahren zur Entfernung von Schwefelverbindungen aus Kohlenwasserstoffgemischen Bei der Abtrennung von Olefinen aus Kohlenwasserstoffgemischen durch Sulfönierung befinden sich nach Entfernung der durch die Sulfonierung gebildeten Ester in der Paraffinkohlenwasserstoffschicht stets noch Schwefelverbindungen, die hartnäckig an den Kohlenwasserstoffen haften. Diese Schwefelverbindungen können sowohl bei der Sulfonierung niedrigsiedender Olefine im Siedebereich der C3- und C4- Kohlenwasserstoffe als auch hochsiedender Olefine im Siedebereich der C12 bis C2ö und höherer Kohlenwasserstoffe nachgewiesen werden. S ie setzen den Wert der Paraffinkohlenwasserstoffe sehr stark herunter, da sie beim Erhitzen der Paraffinkohlenwasserstoffe ein Schwarzwerden verursachen und diesen auch sonstige unangenehme Eigenschaften erteilen. Sie sind weder durch Behandlung mit konzentrierten Alkalilaugen bzw. mit Bleicherden bei normalen Temperaturen zu entfernen noch mit Säuren zu verseifen.Process for removing sulfur compounds from hydrocarbon mixtures In the separation of olefins from hydrocarbon mixtures by sulfonation are after removal of the esters formed by the sulfonation in the Paraffinic hydrocarbon layer still contains sulfur compounds that are stubborn stick to the hydrocarbons. These sulfur compounds can be used in both the sulfonation of low-boiling olefins in the boiling range of C3 and C4 hydrocarbons as well as high-boiling olefins in the boiling range of C12 to C2ö and higher hydrocarbons be detected. They set the value of paraffinic hydrocarbons very strongly as they turn black when the paraffinic hydrocarbons are heated cause and give them other unpleasant properties. they are neither by treatment with concentrated alkaline solutions or with bleaching earth normal temperatures to remove nor to saponify with acids.

Es wurde nun beobachtet, daß man die Paraffinkohlenwasserstoffe in sehr glatter Weise von diesen Stoffen befreien kann, wenn man sie mit Kontaktmassen, die neben Eisenoxvd Alkali in feiner Verteilung in einer Menge von etwa i bis 2o010 enthalten, bei Temperaturen von etwa 300= behandelt. Beispielsweise hat sich eine Mischung aus etwa 20% Soda und 80% Eisenoxyd gut bewährt. Bei der Behandlung werden die Schwefelverbindungen s0 weit aus den Kohlenwasserstoffen herausgenommen, daß sie analytisch mit normalen :Methoden nicht mehr nachweisbar sind. Eine Anwendung der zu reinigenden Produkte in Gasform ist nicht unbedingt erforderlich. Sie können auch zum Teil in flüssiger Phase mit den Kontakten in Berührung gebracht werden. Die Reinigungswirkung wird sowohl in Gegenwart wie Abwesenheit von Wasserstoff erhalten. Die günstigsten Temperaturen liegen um 30o°, je nach Art der Schwefelverbindungen bei unterhalb oder oberhalb dieser Temperatur.It has now been observed that the paraffin hydrocarbons in very smooth Wise one can get rid of these substances if one can use them with contact masses, which in addition to iron oxide alkali in a fine distribution in a quantity from about 1 to 2o010, treated at temperatures of about 300 =. For example A mixture of about 20% soda and 80% iron oxide has proven itself well. In the Treatment, the sulfur compounds are so far removed from the hydrocarbons, that they can no longer be verified analytically with normal: methods. An application the products to be cleaned in gaseous form is not absolutely necessary. You can can also be brought into contact with the contacts in part in the liquid phase. The cleaning effect is obtained both in the presence and in the absence of hydrogen. The best temperatures are around 30o °, depending on the type of sulfur compounds at below or above this temperature.

Es wurde bereits beschrieben, daß die Nachreinigung von z. B. mit Schwefelsäure gereinigtem Paraffin zwecks Entfernung der noch in ihm enthaltenen Geruchs- und Geschmacksstoffe durch Behandlung des geschmolzenen oder gelösten Stoffes mit Alkalien oder anderen alkalisch reagierenden Substanzen oder Mischungen derselben in fester Form oder in konzentrierter wäßriger Lösung oder Suspension ohne Destillation des Paraffins vorgenommen wird, wobei gleichzeitig der Schwefelgehalt bis auf etwa o,oi % tierabgesetzt wird.It has already been described that the post-purification of z. B. with Sulfuric acid purified paraffin to remove the remaining in it Smells and flavors by treating the melted or solute with alkalis or other alkaline reacting substances or mixtures thereof in solid form or in concentrated aqueous solution or suspension without distillation of the paraffin is made, at the same time the sulfur content up to about o, oi% animal is weaned.

Gegenüber diesem Verfahren ist eine Reihe wesentlicher V orteile gegeben. Zunächst findet sich bei dem älteren Reinigungsverfahren ein großer Verbrauch von Alkalien, die in einer Menge von ; bis ioGlo, berechnet auf die Ausgangsstoffe, verwendet werden. Vor allem erfolgt aber durch das erfindungsgemäße Verfahren eine praktisch vollständige Herausnahme der. schwefelhaltigen Verunreinigungen, während bei der Anwendung des älteren Verfahrens noch nachweisbare Mengen (o,oi 0/0) an Schwefelverbindungen in dem behandelten Produkt zurückbleiben.There are a number of significant advantages over this process. First of all, the older cleaning method has a large consumption of Alkalis in an amount of; up to ioGlo, calculated on the raw materials, be used. Above all, however, the method according to the invention provides a practically complete removal of the. sulphurous impurities while with the application of the older method still detectable quantities (o, oi 0/0) Sulfur compounds remain in the treated product.

Katalytische Verfahren sind zwar schon für die Herausnahme von Schwefelverbindungen aus Rohpetroleum bekanntgeworden. Es wurde hierfür u. a. vorgeschlagen, die Entschwefelung von Petroleum durch Überleiten in der Dampfphase über eine Mischung aus i Teil Calciumhvdroxvd und 3 Teilen Eisenhvdroxyd vorzunehmen (vgl. z. B. die britische Patentschrift .196 779.) sowie die Raffination von Petroleumdestillaten durch Überleiten der Dämpfe über poröses Xlaterial zu bewirken, das aus teilweise liydratisierten Erdalkalihydrotvdeii besteht, deren Oberfläche mitAllzalilivdroxvden aktivierti?t. Schwefelhaltige Verunreinigungen von Rohpetroleum bestehen aus Sulfiden, Disulfiden. llercaptanen, Thioäther n, cylisch gebundenem Schwefel und seinen Derivaten sowie ähnlich konstituierten Verbindungen. Die im vorliegenden Fall zu entfernenden Verunreinigungen sind jedoch Verbindungen von an Sauerstoff gebundenem sechswertigem Schwefel, in denen sich die Radikale SO -, SO.,--und SO.-befinden. Ob überhaupt ein und mit welchen Kontakten katalytisches Verfahren zur Herausnahme dieser Schwefelverbindungen zum Ziele führen würde, ließ sich nicht ohne weiteres voraussehen. Zudem unterscheiden sich die bekannten und die erfindungsgemäß anzuwendenden Kontakte in ihrer Zusammensetzung.Catalytic processes have already become known for the removal of sulfur compounds from crude petroleum. For this purpose, it has been proposed, inter alia, to desulfurize petroleum by passing it over in the vapor phase over a mixture of 1 part calcium hydroxide and 3 parts iron hydroxide (cf., for example, British patent 196 779.) and refining petroleum distillates by passing over the To bring about vapors through porous material, which consists of partially hydrated alkaline earth metal, the surface of which is activated with alkali metal hydroxide. Sulfur-containing impurities in crude petroleum consist of sulfides, disulfides. llercaptans, thioethers, cyclically bound sulfur and its derivatives and similarly constituted compounds. The impurities to be removed in the present case, however, are compounds of oxygen-bound hexavalent sulfur in which the radicals S O -, SO., - and SO.- are located. It could not be foreseen without further ado whether a catalytic process for removing these sulfur compounds and with which contacts would lead to the goal. In addition, the known contacts and those to be used according to the invention differ in their composition.

Claims (1)

PATEXTANSPBUCFI: Verfahren zur praktisch restlosen Entfernung von aus Sulfonierungsverfahren herrührenden schwefelhaltigen Produkten aus den Paraffinanteilen von Kohlenwasserstoffgemischen, aus denen die olefinischen Anteile in Form von Sulfonierungsprodukten entfernt sind. dadurch gekennzeichnet, daß die derart gewonnenen Kohlenwasserstoffe mit Kontaktmassen. die neben Eisenoxyd Alkali in feiner Verteilung in einer Menge von etwa i bis 200."0 enthalten, bei Temperaturen von etwa 300" behandelt werden. Zur Abgrenzung des Erfindungsgegenstands vom Stand der Technik sind im Erteilungsverfahren folgende Druckschriften in Betracht gezogen worden: Deutsche Patentschrift Nr. 517 7.1.1; britische Patentschrift Nr. 496 779; USA.-Patentschrift N r. 2 034 712.PATEXTANSPBUCFI: Process for practically complete removal of Sulfur-containing products from the paraffin fractions resulting from sulfonation processes of hydrocarbon mixtures from which the olefinic fractions in the form of sulfonation products are away. characterized in that the hydrocarbons obtained in this way with contact grounds. which in addition to iron oxide alkali in a fine distribution in an amount from about i to 200. "0, can be treated at temperatures of about 300". To differentiate the subject matter of the invention from the state of the art, the granting procedure the following publications have been considered: German Patent No. 517 7.1.1; British Patent No. 496,779; U.S. Patent No. 2,034,712.
DER109400D 1941-02-19 1941-02-19 Process for removing sulfur compounds from hydrocarbon mixtures Expired DE767891C (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
DER109400D DE767891C (en) 1941-02-19 1941-02-19 Process for removing sulfur compounds from hydrocarbon mixtures

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DER109400D DE767891C (en) 1941-02-19 1941-02-19 Process for removing sulfur compounds from hydrocarbon mixtures

Publications (1)

Publication Number Publication Date
DE767891C true DE767891C (en) 1954-07-05

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2003037835A2 (en) * 2001-11-02 2003-05-08 Solvent Innovation Gmbh Method for eliminating polarizable impurities from hydrocarbons with ionic liquids

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE517744C (en) * 1928-04-05 1931-02-09 Riebeck Sche Montanwerke Akt G Process for post-purification of paraffin
US2034712A (en) * 1933-11-28 1936-03-24 Philip Wiseman Method of refining petroleum distillates
GB496779A (en) * 1937-01-04 1938-12-06 Bataafsche Petroleum A process for removing naphthenic acids from mineral lubricating oils or lubricating oil fractions

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE517744C (en) * 1928-04-05 1931-02-09 Riebeck Sche Montanwerke Akt G Process for post-purification of paraffin
US2034712A (en) * 1933-11-28 1936-03-24 Philip Wiseman Method of refining petroleum distillates
GB496779A (en) * 1937-01-04 1938-12-06 Bataafsche Petroleum A process for removing naphthenic acids from mineral lubricating oils or lubricating oil fractions

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2003037835A2 (en) * 2001-11-02 2003-05-08 Solvent Innovation Gmbh Method for eliminating polarizable impurities from hydrocarbons with ionic liquids
WO2003037835A3 (en) * 2001-11-08 2003-12-24 Solvent Innovation Gmbh Method for eliminating polarizable impurities from hydrocarbons with ionic liquids
US7553406B2 (en) 2001-11-08 2009-06-30 Merck Patent Gmbh Process for removing polar impurities from hydrocarbons and mixtures of hydrocarbons

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