DE715815C - Process for the production of tetrahydrofurans - Google Patents

Process for the production of tetrahydrofurans

Info

Publication number
DE715815C
DE715815C DEI59547D DEI0059547D DE715815C DE 715815 C DE715815 C DE 715815C DE I59547 D DEI59547 D DE I59547D DE I0059547 D DEI0059547 D DE I0059547D DE 715815 C DE715815 C DE 715815C
Authority
DE
Germany
Prior art keywords
tetrahydrofurans
production
temperatures
those
vaporous
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
DEI59547D
Other languages
German (de)
Inventor
Dr Otto Hecht
Dr Walter Reppe
Dr Adolf Steinhofer
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.)
IG Farbenindustrie AG
Original Assignee
IG Farbenindustrie 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 IG Farbenindustrie AG filed Critical IG Farbenindustrie AG
Priority to DEI59547D priority Critical patent/DE715815C/en
Application granted granted Critical
Publication of DE715815C publication Critical patent/DE715815C/en
Expired legal-status Critical Current

Links

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
    • C07D307/06—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 only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring carbon atoms
    • C07D307/08—Preparation of tetrahydrofuran

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Description

Verfahren zur Herstellung von - Tetrahydrofuranen Eis wurde gefunden, daß man Tetrahydrofurane erhält, wenn -inan i, 4-But5,lenglylkole in der Gasphase ,über wasserabspaltende Katalysatoren bei solchen zwischen etwa 250 und 350° liegenden Temperaturen leitet, bei .denen Diolefine noch nicht in nennenswerter Menge gebildet werden. Es eignen sich außer dem c, 4-Butylen:glykol selbst auch dessen Alkyl-, Aryl- öder Aralkylsubstitutionsprodukte.Process for the production of - Tetrahydrofurans ice was found that tetrahydrofurans are obtained when -inan i, 4-but5, lenglylkole in the gas phase , over dehydrating catalysts in those between about 250 and 350 ° Temperatures conducts where diolefins have not yet been formed in any appreciable amount will. In addition to the c, 4-butylene: glycol itself, its alkyl, Aryl or aralkyl substitution products.

Es ist zwar bereits bekannt, dampfförmige Butylenglykole der verschiedensten Art der Wasserabspaltung zu unterwerfen, doch wurde hierbei entweder nur die Abspaltung von z Mol Wasser unter Diolefinbildung (vgl. österreichische Patentschrift 82 804 und britische Patentschrift 21 173/191a) .oder. :die. Abspaltung eines Mols - Wasser unter Bildung -ungesättigter Alkohole beobachtet. überraschenderweise kann nman aus dampfförmigen r, 4-Butylenglykolen bei. etwa 25o bis 35o° durch Abspalten nur eines Mols Wasser Tetrahydrofurane erhalten, die chemisch von Diolefinen und ungesättigten Alkoholen völlig verschieden sind. .Although it is already known to subject vaporous butylene glycols of various types of dehydration, either only z moles of water were split off with diolefin formation (cf. Austrian patent specification 82 804 and British patent specification 21 173 / 191a) .or. :the. Splitting of a mole of water with formation of unsaturated alcohols observed. Surprisingly, it is possible to obtain from vaporous r, 4-butylene glycols. about 25o to 35o ° by splitting off only one mole of water tetrahydrofurans are obtained, which are chemically completely different from diolefins and unsaturated alcohols. .

Besonders nichtsaure, osydische Katalysatoren eignen sich für die Herstellung von Tetrahydrofuranen bei Temperaturen von etwa 250 bis 350°, während bei höheren Temperaturur in der Hauptsache Propylen und Formaldehyd neben öligen und teerartigen Stoffen entstehen und die Katalysatoren bald unwirk--. sam-:werden-: Beispiel ÜLxr j25 ccm ,gefälltes, bei erhöhter Tem- peratur erhitztes und geformtes Chromoxyd werden stündlich 25 g dampfförmiges i, 4.-Bu- tylenglykol bei 3oo bis 350° geleitet. Bei fast rooo/oi,gem Umsatz entsteht @praktisch reines Tetrahydrofuran. Nimmt man statt Chromoxyd sekundäres Calciumphosphat, so wird bei Temperaturen unterhalb 3oo° ebenfalls fast reines Tetra- hydrofuran erhalten. Particularly non-acidic, oily catalysts are suitable for the production of tetrahydrofurans at temperatures of about 250 to 350 °, while at higher temperatures mainly propylene and formaldehyde are formed in addition to oily and tar-like substances and the catalysts soon become ineffective. sam-: will-: example ÜLxr j25 ccm, felled, at elevated temperatures temperature heated and formed chromium oxide 25 g of vaporous i, 4.-Bu- tylene glycol passed at 3oo to 350 °. at almost rooo / oi, according to sales, @practical results pure tetrahydrofuran. If one takes secondary instead of chromium oxide Calcium phosphate, so will at temperatures below 300 ° also almost pure tetra- obtained hydrofuran.

Claims (1)

.hATLN'rA\SPICUCH: ' Verfahren zur Herstellung von Tetra- liydrofuranen, dadurch gekennzeichnet, dafl man. i,¢-Butylenglykole in der Gas- phase über wasserabspaltende Kataly- satoren bei solchen zwischen 25o und 35o° liegenden Temperaturen leitet, bei, denen Diolefrne noch nicht in nennenswerter Menge gebildet werden.
.hATLN'rA \ SPICUCH: ' Process for the production of tetra- liydrofurans, characterized that one. i, ¢ -Butylene glycols in the gas phase via water-releasing catalysis with those between 25o and 35o ° lying temperatures, at, those Diolefrne not yet in any appreciable way Amount to be formed.
DEI59547D 1937-11-09 1937-11-09 Process for the production of tetrahydrofurans Expired DE715815C (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
DEI59547D DE715815C (en) 1937-11-09 1937-11-09 Process for the production of tetrahydrofurans

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEI59547D DE715815C (en) 1937-11-09 1937-11-09 Process for the production of tetrahydrofurans

Publications (1)

Publication Number Publication Date
DE715815C true DE715815C (en) 1942-01-07

Family

ID=7195033

Family Applications (1)

Application Number Title Priority Date Filing Date
DEI59547D Expired DE715815C (en) 1937-11-09 1937-11-09 Process for the production of tetrahydrofurans

Country Status (1)

Country Link
DE (1) DE715815C (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1031772B (en) * 1951-12-19 1958-06-12 Ici Ltd Process for the production of p-xylene by catalytic aromatization of 2,5-dimethylhexadienes
EP0041790A2 (en) * 1980-06-11 1981-12-16 E.I. Du Pont De Nemours And Company Purification of tetrahydrofuran

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1031772B (en) * 1951-12-19 1958-06-12 Ici Ltd Process for the production of p-xylene by catalytic aromatization of 2,5-dimethylhexadienes
EP0041790A2 (en) * 1980-06-11 1981-12-16 E.I. Du Pont De Nemours And Company Purification of tetrahydrofuran
EP0041790A3 (en) * 1980-06-11 1982-03-10 E.I. Du Pont De Nemours And Company Purification of tetrahydrofuran, apparatus therefor and derivatives of the purified product

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