DE800298C - Process for the production of ring-shaped aether - Google Patents

Process for the production of ring-shaped aether

Info

Publication number
DE800298C
DE800298C DE1948P0003109 DEP0003109D DE800298C DE 800298 C DE800298 C DE 800298C DE 1948P0003109 DE1948P0003109 DE 1948P0003109 DE P0003109 D DEP0003109 D DE P0003109D DE 800298 C DE800298 C DE 800298C
Authority
DE
Germany
Prior art keywords
shaped
ring
production
aether
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
DE1948P0003109
Other languages
German (de)
Inventor
Wilhelm Dr Friedrichsen
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 DE1948P0003109 priority Critical patent/DE800298C/en
Application granted granted Critical
Publication of DE800298C publication Critical patent/DE800298C/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
    • C07D309/16—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D309/18—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member containing only hydrogen and carbon atoms in addition to the ring hetero atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D319/04—1,3-Dioxanes; Hydrogenated 1,3-dioxanes
    • C07D319/06—1,3-Dioxanes; Hydrogenated 1,3-dioxanes not condensed with other rings

Landscapes

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

Description

Verfahren zur Herstellung ringförmiger Äther )?s ist bekannt. (1a13 hui der Einwirkung voti Formaklehvct auf 11(mo()letine in saurem, wäl.irigmn Medium i, 3-l@iotane cntsl>rechen(i der Gleichung gel>ililet wemiett. Es wurdr nun gefunden. Mali inan andersartige i-ingfiii-niige Ather erhält, wenn man i, 3-Dioletine mit Formal#lchyd in w;ilßrigein, saurem Medium zusammenlwingt. Während hei der behamiten Uni- setzung der NIonoolefiiie mit Foi-tnal(lehN-(l aus- schlie()lich cili i.3-Di(#san, als() ein @inrisvstem niit = ITeterosatici-stotiatonien, gebildet wird, ciit- steht aus den I>icilefiiicii und Formal(lehv(1 der I'vranriii@ (l. i. vill System finit cineln Sauerstot- lietero@"tto@tn. vermutlich im Sinne fol@Ten@ler (Wcliung 1 tu in (lein l'vranring noch vorhandene f )()lil>el- hindung kann sich finit zwei weiteren I@ormal<lchvd- m@lehü@en umsetzen. "wobei vermutlich im Sinne der Gleichung "I'riotalierlic(lronal)litlialine entstelicn. Für die 'Unisetzung benutzt inan z\yecl;inäßig verdünnte starke Mineralsäuren, z. B. Schwefel- säure oder Salzsäure, oder auch wä ßrige Lösungen sauer reagierender Salze, z. B. von Zinkchlorid. Durch "Temperaturerhöhung läßt sich der Umsatz verbessern, man arbeitet daher vorteilhaft bei Tenilx raturen über 6o` . Da bei diesen Bedingun- gen die gebräuchlichsten Diolefine gasförmig sind, kann man zur innigeren Vermischung derAusgangs- stoffe erhöhten Druck anwenden, doch gelingt (1i:# L@in:etzung auch drucklos, beispielsweise indem man (las gasförmige Diolefin im Kreislauf durch die forinaldehydhaltige saure Flüssigkeit leitet. Eine solche Arbeitsweise läßt sich leicht kontinuier- lich gestalten. An Stelle von Formaldelivd kann man auch Formal<lehvd abgebende Stoffe ver- wenden. Als Nebenprodukt entsteht bei der Umsetzung entsprechend der Gleichung das nach der Gleichung 1 zu erwartende Alkenyl-1, 3-Dioxan. Die im nachstehenden Beispiel angegebenen Teile sind Gewichtsteile. 1)c isl>iel 760 "feile Butadien, 1400 "l'cile 3o°/oigc wäßrige rormaldehydlösung, 700 'feile Paraforinaldehyd und i.4o Teile Schwefelsäure schüttelt nian in einem Bleiautoklac (> Stunden bei 8o`. Der anfangs 1.4 at betragende Druck gclit auf .2 at zurück. Das Reaktionsprodukt wird mit Natronlauge neutrali- siert. Es bildet zwei Schichten, von denen die obere Schicht abgetrennt und mit Kaliunicarbonat ge- trocknet wird. Bei der Destillation dieser Schicht werden 3 Fraktionen erhalten: Die erste Fraktion besteht aus 122 Teilen und siedet bei etwa hoj. Sie besteht aus Dihydropyran. Als zweite Fraktion erhält nian 6.16 "heile einer zwischen 135 bis i.15" sie(len(ien Flüssigkeit; es handelt sich um 5-Vinvl-I, 3-Dioxan. Als dritte Fraktion erhält inan 662 Teile eines zwischen _>0o und 215 siedenden dicken, gelb- lichen Öls, aus dein sich ciach einiger Geit <lerlic Kristalle eines 'hrioxaperliv(ironaplithalins abschei- den, die aus Hexan umkristallisiert, bei 52° schmel- zen und bei 215° sieden. Process for the production of ring-shaped ethers )? s is well known. (1a13 hui of the action voti Formaklehvct to 11 (mo () letine in sour, wäl.irigmn Medium i, 3-l @ iotane cntsl> rake (i of the equation gel> ililet wemiett. It has now been found. Mali inan different i-ingfiii-niige ethers are obtained when one, 3-dioletins with formaldehyde in aqueous, acidic medium together. While at the behamiten university setting of the nonoolefiiie with Foi-tnal (lehN- (l from- finally cili i.3-Di (#san, as () a @inrisvstem niit = ITeterosatici-stotiatonia, is formed, ciit- comes from the I> icilefiiicii and Formal (lehv (1 der I'vranriii @ (li vill system finit cineln oxygen lietero @ "tto @ tn. probably in the sense of fol @ ten @ ler (Wcliung 1 tu in (lein l'vranring still existing f) () lil> el- binding can finite two further I @ ormal <lchvd- Implement m @ lehü @ en. "being presumably in the sense the equation "Triotalierlic (lronal) litlialine develop. Inan z \ yecl; used for the unisposition diluted strong mineral acids, e.g. B. Sulfur acid or hydrochloric acid, or aqueous solutions acidic salts, e.g. B. of zinc chloride. The conversion can be increased by increasing the temperature improve, it is therefore beneficial to contribute Tenilx ratures over 6o`. Since under these conditions the most common diolefins are gaseous, can be used for a more intimate mixing of the materials apply increased pressure, but succeeds (1i: # L @ in: also pressureless, for example by one (read gaseous diolefin through a cycle the foraldehyde-containing acidic liquid conducts. Such a way of working can easily be design. Instead of Formaldelivd, substances that give off formal substances are also turn around. A by-product arises during the implementation according to the equation that to be expected according to equation 1 Alkenyl-1,3-dioxane. The ones given in the example below Parts are parts by weight. 1) c isl> iel 760 "file butadiene, 1400"l'cile 30% aqueous Formaldehyde solution, 700 'file paraforaldehyde and i.4o parts sulfuric acid shakes nian in a lead autoclave (> hours at 8o`. The initially 1.4 at amount of pressure gclit on .2 at back. That The reaction product is neutralized with sodium hydroxide sated. It forms two layers, the upper one of which Separated layer and treated with potassium carbonate is drying. When distilling this layer 3 fractions are obtained: The first fraction consists of 122 parts and boils at about hoj. It consists of dihydropyran. As the second faction, nian receives 6.16 "heal one between 135 to i.15 "they (len (ien liquid; es is 5-vinyl-1,3-dioxane. The third parliamentary group received 662 parts of one between _> 0o and 215 boiling thick, yellow- lichen oil, from which you can ciach for some time Crystals of a 'hrioxaperliv (ironaplithalins deposit the one, which recrystallizes from hexane, melts at 52 ° zen and boil at 215 °.

Claims (1)

PATENTANSPRLICII: Verfahren zur Herstellung ringförmiger Äther, dadurch gekennzeichnet, <laß man auf 1. 3-Diolefine in wä ßrigem, saurem Medium Formaldehyd oder Forinaldeh_vd abgebende Stoffe einwirken lädt.
PATENT APPLICATION II: Method of making ring-shaped Ether, characterized by <let up 1. 3-Diolefins in an aqueous, acidic medium Formaldehyde or Forinaldeh_vd emitting Substances act invites.
DE1948P0003109 1948-10-02 1948-10-02 Process for the production of ring-shaped aether Expired DE800298C (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
DE1948P0003109 DE800298C (en) 1948-10-02 1948-10-02 Process for the production of ring-shaped aether

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE1948P0003109 DE800298C (en) 1948-10-02 1948-10-02 Process for the production of ring-shaped aether

Publications (1)

Publication Number Publication Date
DE800298C true DE800298C (en) 1950-01-30

Family

ID=577553

Family Applications (1)

Application Number Title Priority Date Filing Date
DE1948P0003109 Expired DE800298C (en) 1948-10-02 1948-10-02 Process for the production of ring-shaped aether

Country Status (1)

Country Link
DE (1) DE800298C (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1056621B (en) * 1955-11-03 1959-05-06 Basf Ag Process for the preparation of substituted 1,3-dioxanes

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1056621B (en) * 1955-11-03 1959-05-06 Basf Ag Process for the preparation of substituted 1,3-dioxanes

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