DE833963C - Process for the production of 3, 4-dioxytetrahydrofurans and higher molecular weight polyoxy compounds - Google Patents

Process for the production of 3, 4-dioxytetrahydrofurans and higher molecular weight polyoxy compounds

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Publication number
DE833963C
DE833963C DEP3036A DEP0003036A DE833963C DE 833963 C DE833963 C DE 833963C DE P3036 A DEP3036 A DE P3036A DE P0003036 A DEP0003036 A DE P0003036A DE 833963 C DE833963 C DE 833963C
Authority
DE
Germany
Prior art keywords
molecular weight
higher molecular
production
dioxytetrahydrofurans
polyoxy compounds
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
DEP3036A
Other languages
German (de)
Inventor
Dr Erwin Bauer
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.)
BASF SE
Original Assignee
BASF SE
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 BASF SE filed Critical BASF SE
Priority to DEP3036A priority Critical patent/DE833963C/en
Application granted granted Critical
Publication of DE833963C publication Critical patent/DE833963C/en
Expired legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C07D307/18—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D307/20—Oxygen atoms

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Description

Verfahren zur Herstellung von 3, 4-Dioxytetrahydrofuranen und höhermolekularen Polyoxyverbindunüen Es wurde gefunden, daß man 3, 4-Dioxytetrahydrofurane neben höhermolekularen PolyoxyverbIndungen erhält, wenn man Butendiole oder ihre llomologen in Gegenwart von Sauerstoff übertragenden Katalysatoren und in saurem Medium mit Wasserstoffperoxyd erwärmt.Process for the production of 3, 4-Dioxytetrahydrofuranen and higher molecular weight Polyoxyverbindunüen It has been found that 3, 4-Dioxytetrahydrofurane besides Higher molecular weight polyoxy compounds are obtained by using butenediols or their homologs in the presence of oxygen-transferring catalysts and in an acidic medium Hydrogen peroxide heated.

Als Buten.diole bzw. deren Homologe seien beispielsweise genannt: Buten-i-diol-3, .4, Buten-2-diol-i, 4 und Hexen-3-diol-2, 5.Examples of butene diols or their homologues are: Butene-i-diol-3, .4, butene-2-diol-i, 4 and hexene-3-diol-2, 5.

Geeignete Sauerstoff ü,hertragende Katalysatoren sind z. B. Persäuren, wie Perschwefel-, Perphosphor- oder Perarsensäure; an Stelle der Persäuren kann man auch Säuren verwenden, die mit Wasserstoffperoxyd Persäuren bilden, z. B. schweflige, phosphorige, Schwefel- oder Phosphorsäure. Auch saure Salze dieser Säuren sind geeignet. Ferner können als Katalysatoren.Salze des Quecksilbers, Arsens, Wismuts oder Zinns oder anderer Metalle verwendet werden, die leicht ihre Oxydationsstufe ändern können.Suitable oxygen transfer catalysts are, for. B. peracids, such as persulfuric, perphosphoric or perarsenic acid; in place of the peracids you can also use acids that form peracids with hydrogen peroxide, e.g. B. sulphurous, phosphorous, sulfuric or phosphoric acid. Acid salts of these acids are also suitable. Furthermore, as catalysts. Salts of mercury, arsenic, bismuth or tin or other metals which can easily change their oxidation state can be used.

Man erhält nach dem vorliegenden Verfahren z. B. aus Buten-2-diol-i, 4 im wesentlichen trans-3, 4-Dioxytetrahydrofuran, aus Buten-i-diol-3, 4 ein Gemisch von cis- und trans-3, 4-DiOxYtetrahydrofuran. Daneben entstehen in mehr oder weniger großen Mengen höhermolekulare Polyoxyverbindungen.According to the present process, for. B. from butene-2-diol-i, 4 essentially trans-3, 4-Dioxytetrahydrofuran, from butene-i-diol-3, 4 a mixture of cis- and trans-3,4-DiOxYtetrahydrofuran. In addition, in more or less large amounts of high molecular weight polyoxy compounds.

Die Verfahrenserzeugnisse sind wertvolle Austauschprodukte für Glycerin; sie sind auch als Zwischenprodukte, insbesondere für dieHerstellung von Kunststoffen und Weichmachern, verwendbar.The products of the process are valuable replacement products for glycerine; they are also used as intermediate products, especially for the manufacture of plastics and plasticizers.

Die in den folgenden Beispielen genannten Teile sind Gewichtsteile.The parts mentioned in the following examples are parts by weight.

Beispiel i Ein Gemisch aus 5oo Teilen Buten-2-diol-i, 4 und 585 Teilen 34%igem Wasserstoffperoxyd wird mit Teilen Quecksilbernitrat und 2 Teilen konzentrierter Salpetersäure versetzt und 20 Stunden in gelindem Sieden gehalten. Dann destilliert man zunächst im W:asserstrahl-, hierauf im Hochvakuum und gewinnt 6o% des insgesamt zu erwartenden trans-3, 4-Dioxytetrahydrofurans als Destillat vom Siedebereich 102 bis 215° bei io bis o.5 mm Druck. Der Rückstand besteht aus höhermolekularen Polyoxyverbindungeii.Example i A mixture of 500 parts of butene-2-diol-i, 4 and 585 parts 34% hydrogen peroxide is concentrated with parts of mercury nitrate and 2 parts Nitric acid was added and the mixture was kept at a gentle boil for 20 hours. Then distilled one first in a water jet, then in a high vacuum and wins 60% of the total expected trans-3, 4-dioxytetrahydrofuran as a distillate with a boiling point of 102 up to 215 ° with io to o.5 mm pressure. The residue consists of higher molecular weight polyoxy compounds.

Beispiel 2 Man löst io Teile Arsentrioxyd in - 585 Teilen 34%igem Wasserstoffperoxyd, fügt zu der sauren Lösung unter Rühren 5oo Teile 13uteii-2-diol-i. 4 hinzu und erwärmt 2o Stunden lang zu gelindem Sieden. Die -Aufarbeitung erfolgt wie im Beispiel i. Man erhält in einer Ausheute von 84% der Theorie hauptsächlich trans-3. 4-Dioxvtetrahydrofuran neben höhersiedendem Rückstand.Example 2 10 parts of arsenic trioxide are dissolved in 585 parts of 34% strength Hydrogen peroxide, add 500 parts of 13uteii-2-diol-i to the acidic solution with stirring. Add 4 and heat to a gentle boil for 20 hours. The processing takes place as in example i. In a day, 84% of theory is mainly obtained trans-3. 4-Dioxvtetrahydrofuran in addition to higher-boiling residue.

Claims (1)

PATENTAxsPEi CH: Verfahren zur Herstellung von 3, 4-Dioxytetrahydrofuranen und höhermolekularen Polyoxyverbindungen, dadurch gekennzeichnet, daß man B.utendiole oder ihre Homologen in saurem Medium und in Gegenwart von Sauerstoff übertragenden Katalysatoren mit Wasserstoffperoxyd erwärmt.PATENTAxsPEi CH: Process for the production of 3, 4-dioxytetrahydrofurans and higher molecular weight polyoxy compounds, characterized in that B.utenediols or their homologues are heated with hydrogen peroxide in an acidic medium and in the presence of oxygen-transferring catalysts.
DEP3036A 1945-03-06 1945-03-06 Process for the production of 3, 4-dioxytetrahydrofurans and higher molecular weight polyoxy compounds Expired DE833963C (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
DEP3036A DE833963C (en) 1945-03-06 1945-03-06 Process for the production of 3, 4-dioxytetrahydrofurans and higher molecular weight polyoxy compounds

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEP3036A DE833963C (en) 1945-03-06 1945-03-06 Process for the production of 3, 4-dioxytetrahydrofurans and higher molecular weight polyoxy compounds

Publications (1)

Publication Number Publication Date
DE833963C true DE833963C (en) 1952-03-13

Family

ID=7358415

Family Applications (1)

Application Number Title Priority Date Filing Date
DEP3036A Expired DE833963C (en) 1945-03-06 1945-03-06 Process for the production of 3, 4-dioxytetrahydrofurans and higher molecular weight polyoxy compounds

Country Status (1)

Country Link
DE (1) DE833963C (en)

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