DE875507C - Process for the separation of diacetylene from mixtures containing diacetylene and vinyl acetylene - Google Patents

Process for the separation of diacetylene from mixtures containing diacetylene and vinyl acetylene

Info

Publication number
DE875507C
DE875507C DEC1673D DEC0001673D DE875507C DE 875507 C DE875507 C DE 875507C DE C1673 D DEC1673 D DE C1673D DE C0001673 D DEC0001673 D DE C0001673D DE 875507 C DE875507 C DE 875507C
Authority
DE
Germany
Prior art keywords
diacetylene
vinyl acetylene
separation
mixtures containing
parts
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
DEC1673D
Other languages
German (de)
Inventor
Walter Dr Franke
Karl Heinz Dr Seemann
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.)
Huels AG
Original Assignee
Chemische Werke Huels 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 Chemische Werke Huels AG filed Critical Chemische Werke Huels AG
Priority to DEC1673D priority Critical patent/DE875507C/en
Application granted granted Critical
Publication of DE875507C publication Critical patent/DE875507C/en
Expired legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C7/00Purification; Separation; Use of additives
    • C07C7/148Purification; Separation; Use of additives by treatment giving rise to a chemical modification of at least one compound
    • C07C7/14875Purification; Separation; Use of additives by treatment giving rise to a chemical modification of at least one compound with organic compounds

Description

Verfahren zur Abtrennung von Diacetylen aus Diacetylen und Vinylacetylen enthaltenden Gemischen Es ist bekannt, daß sowohl Diacetvlen als auch @'invlacetyleri in Gegenwart von alkalisch wirken- den Mitteln, wie Alkalialkoholaten, organische Ovverbindungen anlagern. 1s wurde nun gefunden, daß man aus Gemischen von Diacetylen und @'inylacetylen, wie sie beispiels- weise durch Behandeln von Methan oder seinen Homologen im elektrischen Lichtbogen erhalten werden, das Diacett-len abtrennen kann, wenn man die Gemische in Gegenwart basisch wirkender Stoffe mit organischen Otvverbindungeti bei solchen Temperaturen, gegebenenfalls unter Druck, behandelt, daß sich nur das Diacetylen umsetzt.Process for the separation of diacetylene from mixtures containing diacetylene and vinyl acetylene It is known that both diacetvlene and @ 'invlacetyleri act in the presence of alkaline- the agents, such as alkali alcoholates, organic Add ov connections. It has now been found that mixtures of diacetylene and @ 'inylacetylene, as they are for example wisely by treating methane or its Obtained homologues in the electric arc the diacett-len can be cut off if one the mixtures act more basic in the presence Substances with organic compounds are included such temperatures, optionally under pressure, treated that only the diacetylene is converted.

Für das Verfahren besonders geeignete organische Oxvverbindungen sind die niedrigmolekttlaren Alkohole. Die Umsetzungsbedingungen richten sich nach -der Art der verwendeten organischen Oxyverbindung und des basischen Stoffes. Auf Grund der neuen Erkenntnis, daß bei der vorliegenden Umsetzung das Diacetylen anders als Vinvlacetvlen reagiert, wird, die Temperatur stets niedriger gewählt, als sie unter sonst gleichen Umständen bei der Umsetzung von Vinylacetylen mit Alkoholen . üblich ist. Bei Verwendung von niedrigmolekularen Alkoholen arbeitet man beispielsweise bei Temperaturen unter g5°, z@veckmäßig unter 75°. -Als basisch wirkende Stoffe kommen vor allem die Alkaliverbindungen der organischen Oxyverbindungen, wie die Alkalialkoholate oder -pheno-Tate, in Betracht; aber auch Metalloxyde, -hydroxyde, -carbonate oder -cyanilde sind hierfür geeignet. Es können .auch noch andere katalytisch wirkende Stoffe, wie Quecksilbersalze, zugegen sein.Organic oxy compounds particularly suitable for the process are the low molecular weight alcohols. The implementation conditions are based on the Type of organic oxy compound used and the basic substance. Because of the new knowledge that in the present implementation, the diacetylene different than Vinvlacetvlen reacts, the temperature is always chosen lower than below otherwise same Circumstances in the implementation of vinyl acetylene with Alcohols. is common. Works when using low molecular weight alcohols for example, at temperatures below g5 °, z @ veckweise below 75 °. -As basic active substances are mainly the alkali compounds of the organic oxy compounds, such as the alkali metal alcoholates or -pheno-Tate, into consideration; but also metal oxides, hydroxides, Carbonates or cyanilde are suitable for this. Others can also be catalytically active active substances such as mercury salts must be present.

Die Gemische aus Diacetylen und Vinylacetylen können auch noch Propan oder Butan enthalten, und auch die Anwesenheit von Homologen ides Acetylens und anderen Acetylenlcohlen#iva@sserstoffen, wie Methyl- oder Phenylacetylen, öder auch von Estern stört beider Umsetzung nicht. . - . .The mixtures of diacetylene and vinyl acetylene can also contain propane or contain butane, and also the presence of homologues ides acetylene and other acetylenic oils, such as methyl or phenylacetylene, or also of esters does not interfere with the implementation. . -. .

Die im nachstehenden Beispiel angegebenen Volumteile und Gewichtsteile verhalten sich zueinander wie Liter zu Kilogramm.The parts by volume and parts by weight given in the example below relate to one another as liters to kilograms.

Beispiel 170 Volumteile eines flüssigen Gemisches aus Diacetylen, Vinylacetylen und Butan (Verhältnis 30 : 48 :22,) werden im Laufe von 5 Stunden im Kreislauf einer auf 6,5 bis 7d°i erwärmten Lösung von 25 Gewichtsteilen Natrium in 700 Volumteilen Äthanol zugeführt. Aus dem Abgas lassen sich durch I#'-ühl,ung 83 Volwmteile und aus dem Umsetzungsgemisch durch An-destillieren 20 VOlumteile, zusammen also io3 Volumteile, eines Kondensats gewinnen, das frei von Diacetylen ist und die Gesamtmenge :des Vinylacetylens enthält. Das Diacetyleri hat sich mit dem Äthanol zu i-Äthcxybutin-3-en-1 (Äthoxyvinylacetylen) umgesetzt, das aus dem Umsetzungsgemisch durch Destillation gewonnen werden kann. Die Ausbeute beträgt 73 Teile = 75 °/o; der Verlust ist durch Poly merisation verursacht. EXAMPLE 170 parts by volume of a liquid mixture of diacetylene, vinyl acetylene and butane (ratio 30:48:22) are circulated over the course of 5 hours to a solution of 25 parts by weight of sodium in 700 parts by volume of ethanol, heated to 6.5 to 7 ° i. 83 parts by volume of a condensate, which is free of diacetylene and contains the total amount of vinyl acetylene, can be obtained from the exhaust gas by distilling in 83 parts by volume and from the reaction mixture by partial distillation. The diacetyleri has reacted with the ethanol to i-ethoxybutyn-3-en-1 (ethoxyvinylacetylene), which can be obtained from the reaction mixture by distillation. The yield is 73 parts = 75%; the loss is caused by polymerization.

Das Verfahren läßt sich in der gleichen Weise durchführen, wenn man statt 25 g Natrium 2o bis 40 g Ätznatron benutzt.The procedure can be carried out in the same way if one instead of 25 g sodium 20 to 40 g caustic soda used.

Claims (1)

PATENTANSPRUCH: Verfahren zur Abtrennung von Diacetylen aus Diacetylen und Vinylacetylen enthaltenden Gemischen, dadurch gekennzeichnet, daß man die Gemische in Gegenwart von basisch wirkenden Stoffen mit organischen Oxyverbindungen bei solchen Temperaturen, gegebenenfalls unter Druck, behandelt, daß sich nur das Diacetylen umsetzt, während das Vinylacetylen unverändert wiedergewonnen wird.PATENT CLAIM: Process for the separation of diacetylene from diacetylene and mixtures containing vinylacetylene, characterized in that the mixtures in the presence of basic substances with organic oxy compounds in such Temperatures, optionally under pressure, treated that only the diacetylene converts, while the vinyl acetylene is recovered unchanged.
DEC1673D 1943-01-07 1943-01-07 Process for the separation of diacetylene from mixtures containing diacetylene and vinyl acetylene Expired DE875507C (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
DEC1673D DE875507C (en) 1943-01-07 1943-01-07 Process for the separation of diacetylene from mixtures containing diacetylene and vinyl acetylene

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEC1673D DE875507C (en) 1943-01-07 1943-01-07 Process for the separation of diacetylene from mixtures containing diacetylene and vinyl acetylene

Publications (1)

Publication Number Publication Date
DE875507C true DE875507C (en) 1953-05-04

Family

ID=7012682

Family Applications (1)

Application Number Title Priority Date Filing Date
DEC1673D Expired DE875507C (en) 1943-01-07 1943-01-07 Process for the separation of diacetylene from mixtures containing diacetylene and vinyl acetylene

Country Status (1)

Country Link
DE (1) DE875507C (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3325557A (en) * 1965-04-13 1967-06-13 Huels Chemische Werke Ag Process for the production of diacetylene solutions

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3325557A (en) * 1965-04-13 1967-06-13 Huels Chemische Werke Ag Process for the production of diacetylene solutions

Similar Documents

Publication Publication Date Title
Henne et al. Hydrogenation of the triple bond1
US1968601A (en) Preparation of olefine derivatives
DE875507C (en) Process for the separation of diacetylene from mixtures containing diacetylene and vinyl acetylene
US2274057A (en) Process for the oxidation of aliphatic hydrocarbons
Gilman et al. The Reaction of Trityl Methyl Ether with Phenyllithium and with n-Butyllithium
GB576480A (en) Process for producing olefinic hydrocarbons
DE583564C (en) Process for the production of higher molecular olefins
DE865927C (en) Process for the production of lubricants or lubricant additives
DE870856C (en) Process for the production of formamides or amines
Horning et al. The Action of Bases on Organic Halogen Compounds. IV. The Action of the Lithium Salts of Aliphatic Amines on some Organic Halogen Compounds
DE848947C (en) Process for the production of nitriles
DE870845C (en) Process for the preparation of di- or polyacetylene compounds
DE1543086B1 (en) Process for the production of olefins
DE869794C (en) Process for converting unsaturated carbon compounds, in particular olefins, into oxygen-containing compounds
DE805761C (en) Process for the preparation of ª ‰ -mercaptocarboxylic acid esters
US3860667A (en) Method of preparing 1-methyl-3-phenyl-indane
DE565160C (en) Process for the production of unsaturated carbon compounds
Zanetti et al. The formation of butadiene from ethylene
DE965321C (en) Process for the production of pure terephthalic acid
DE1543086C (en) Process for the production of olefins
DE703067C (en) Process for the halogenation of tertiary olefins contained in gas mixtures
DE765521C (en) Process for the preparation of 1,3-diolefins
CH415607A (en) Process for the production of octafluorocyclobutane
Clemo et al. 96. The polymerisation of dideuteroacetylene
DE670420C (en) Process for the preparation of sulfonaethylamines