DE330358C - Process for the preparation of furfurakrolein - Google Patents
Process for the preparation of furfurakroleinInfo
- Publication number
- DE330358C DE330358C DE1919330358D DE330358DD DE330358C DE 330358 C DE330358 C DE 330358C DE 1919330358 D DE1919330358 D DE 1919330358D DE 330358D D DE330358D D DE 330358DD DE 330358 C DE330358 C DE 330358C
- Authority
- DE
- Germany
- Prior art keywords
- furfurakrolein
- acetaldehyde
- preparation
- percent
- furfural
- 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
Links
- 238000000034 method Methods 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title claims description 3
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 claims description 10
- HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 claims description 10
- 239000000126 substance Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- SQYNKIJPMDEDEG-UHFFFAOYSA-N paraldehyde Chemical compound CC1OC(C)OC(C)O1 SQYNKIJPMDEDEG-UHFFFAOYSA-N 0.000 description 3
- 229960003868 paraldehyde Drugs 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 238000000605 extraction Methods 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000005292 vacuum distillation Methods 0.000 description 2
- 101150095408 CNMD gene Proteins 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 235000011194 food seasoning agent Nutrition 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- XPFVYQJUAUNWIW-UHFFFAOYSA-N furfuryl alcohol Chemical compound OCC1=CC=CO1 XPFVYQJUAUNWIW-UHFFFAOYSA-N 0.000 description 1
- 238000011081 inoculation Methods 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
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
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/40—Radicals substituted by oxygen atoms
- C07D307/46—Doubly bound oxygen atoms, or two oxygen atoms singly bound to the same carbon atom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Description
Verfahren zur Darstellung von Furfurakrolein. Das bereits ;imi Jahre i88o von G. S chmi dt erstmalig dargestellte, als Würz- und Riechstoff verwendbare Furfurak'rolein konnte nach den in den Berichten der Deutschen Chemischen Gesellschaft Bd. 13, S. 2345 niedergelegten Angaben des Entdeckers nur in einer Ausbeute von 5 Prozent erhalten werden. Nach dem Verfahren von R ö h m e r (Ber. a. a. 0. Bd. 31, S. 283) soll die Ausbeute erhöht werden. Es setzt -sich dabei ein schweres orangefarbenes Öl ab, daß auch beim Impfen mit Furfurakrolein nicht zum Erstarren zu bringen ist, da es große Mengen, höherer Kondensationsprodukte des Acetaldehyds (Aldehydharze) und des Furfurols enthält. Durch eine umständliche Reinigung (Extraktion und Vakuumdestillation) können daraus etwa 25 Prozent Furfurakrolein, bezogen auf das angewandte Furfurol, erhalten werden.Process for the preparation of furfurakrolein. That already; imi years In 1880 by G. S chmi dt for the first time, usable as a seasoning and fragrance substance Furfurak'rolein could according to the reports of the German Chemical Society Bd. 13, p. 2345 recorded information of the discoverer only in a yield of 5 percent can be obtained. According to the method of Rö h m e r (Ber. A. A. 0. Vol. 31, p. 283) the yield should be increased. A heavy orange-colored one sets itself Oil off, so that even when vaccinated with furfurakrolein it cannot be made to solidify, as there are large amounts of higher condensation products of acetaldehyde (aldehyde resins) and containing furfural. Through cumbersome cleaning (extraction and vacuum distillation) about 25 percent furfurakrolein, based on the applied furfurol, can be obtained.
Es wurde nun die bemerkenswerte Beobachtung gemacht, daß man das Furfurakrolein unmittelbar kristallinisch in einer Mindestausbeute von 4o Prozent an chemisch: reinem Produkt dadurch erhalten kann, daß man. die Reaktionstemperatur während der Umsetzungsdauer niedrig, zweckmäßig auf etwa o° hält, die Alkalimenge gegenüber der nach Röhmer zu verwendenden wesentlich herabsetzt und dafür sorgt, daß das Furfurol möglichst lange im Überiscüuß vorhanden bleibt, was sich dadurch erreichen läßt, daß man den Acetaldehyd, nur langsam unter gutem Rühren hinzugibt. Unter diesen Umständen scheidet sich das Furfurakrolein allmählich als gut filtr, ierbarer, schwach gelber Kristallbrei in reiner Form ab, Nach Übertreiben mit Dampf und Umkristallisieren- aus Ligroin zeigt .es den Schmelzpunkt von 54°.The remarkable observation has now been made that one furfurakrolein immediately crystalline with a minimum yield of 40 percent of chemical: pure product can be obtained by. the reaction temperature during the Keeps the reaction time low, expediently at about 0 °, compared to the amount of alkali which according to Röhmer to be used significantly reduces and ensures that the furfural remains in excess as long as possible, which can be achieved by that the acetaldehyde is added slowly with thorough stirring. Under these Under certain circumstances, the furfurakrolein gradually separates itself as easily filtrable, manageable, weak yellow crystal pulp in pure form, after exaggerating with steam and recrystallization- from ligroin shows .es the melting point of 54 °.
An: Stelle von reinem Acetaldehyd läßt sich mit gleichem Erfolg technischer, d. h. wasser-und paraldehydhaltiger Acetaldehyd in entsprechender Menge verwenden. Der Paraldehyd setzt sich hierbei fast gar nicht um; er findet sich im Filtrat vom auskristallisierten Furfurakrolein und kann daraus neben einer weiteren geringen Menge des letztgenannten Stoffes durch Extrahieren und Vakuumdestillation, gewonnen werden.Instead of pure acetaldehyde, technical, d. H. Use acetaldehyde containing water and paraldehyde in the appropriate amount. The paraldehyde is hardly converted at all; it is found in the filtrate from crystallized Furfurakrolein and can from it in addition to another low Amount of the latter substance obtained by extraction and vacuum distillation will.
Beispiel. In 2 ooo Gewichtsteilen auf o° abgekühltes Wasser werden zunächst io Gewichtsteile Ätznatron und dann innerhalb einer Viertelstunde ioo Gewichtsteile Furfurol unter gutem Rühren in Lösung gebracht. Dann läßt man wiederum bei o° im Laufe von 31[, Stunden 2oö Gewichtsteile technischen Acetaldehvd (enthaltend 30 Prozent reinen Acetaldehyd. ebensoviel Paraldehyd und 40 Prozent Wasser) zutropfen und rührt bei derselbenTemperatur noch i?l,Stunden weiter. Schon bald nach Beginn des AcetaldeUydzusatzes tritt rheistens spontan, andernfalls nach Animpfen mit einer Spur Furfurakrolein eine kristallinische Fällung auf, welche sich stetig vermehrt. Sie wird nach fünfstündiger Versuchsdauer abfiltriert und die schwachgelbe Kristallmasse mit kaltem Wasser gewaschen. Zur völligen Reinigung wird. sie mit mäßig überhitztem Dampf übergetrieben. Aus dem stark abgekühlten Destillat scheiden Sich nur noch' ganz schwach gefärbte Kristalle aus, die im Vakuum bei niedriger Temperatur gt:troclcnet und einmal aus wenig Ligroin (Siedepunkt etwa 9o°) umkristallisiert werden. NI.an erhält #so-unbegrenzt haltbares Furfurakrolein vorn Schmelzpunkt 3q.°. Die Ausbeuten @bäräÜ-tr,4aufr" Furfurol berechnet, etwa 41 Prozent.Example. First 10 parts by weight of caustic soda and then 100 parts by weight of furfural are dissolved in 2,000 parts by weight of water cooled to 0 ° with thorough stirring. Then 2o0 parts by weight of technical acetaldehyde (containing 30 percent pure acetaldehyde, just as much paraldehyde and 40 percent water) are added dropwise at 0 ° in the course of 31.1 hours and stirring is continued at the same temperature for a further 1.5 hours. Soon after the addition of acetaldehyde, rheistically spontaneous, otherwise after inoculation with a trace of furfurakrolein, a crystalline precipitation occurs, which increases steadily. After a test duration of five hours, it is filtered off and the pale yellow crystal mass is washed with cold water. For complete purification becomes. overdriven them with moderately superheated steam. From the strongly cooled distillate, only very weakly colored crystals separate out, which are recrystallized in vacuo at low temperature and dry once from a little ligroin (boiling point about 90 °). NI.an receives # so-unlimited shelf life furfurakrolein with a melting point of 3q. °. The yields @ bäräÜ-tr.4 calculated on "furfural" are about 41 percent.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE330358T | 1919-11-12 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE330358C true DE330358C (en) | 1920-12-10 |
Family
ID=6189898
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1919330358D Expired DE330358C (en) | 1919-11-12 | 1919-11-12 | Process for the preparation of furfurakrolein |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE330358C (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE962614C (en) * | 1955-04-20 | 1957-04-25 | Dr Otto Moldenhauer | Process for the manufacture of furylacrolein |
| DE1063180B (en) * | 1953-06-23 | 1959-08-13 | Lepeti S P A | Process for the preparation of thiophene derivatives |
-
1919
- 1919-11-12 DE DE1919330358D patent/DE330358C/en not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1063180B (en) * | 1953-06-23 | 1959-08-13 | Lepeti S P A | Process for the preparation of thiophene derivatives |
| DE962614C (en) * | 1955-04-20 | 1957-04-25 | Dr Otto Moldenhauer | Process for the manufacture of furylacrolein |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE541362C (en) | Process for the hydrogenation of polyoxy compounds | |
| DE330358C (en) | Process for the preparation of furfurakrolein | |
| DE859461C (en) | Process for the preparation of aromatic sulfonic acid halides | |
| DE839799C (en) | Process for the preparation of morphine-6-glycosides | |
| DE503031C (en) | Process for the preparation of the N-oxyethyl derivatives of core substitution products of -amino-1-oxybenzene | |
| DE638830C (en) | Process for the production of water-soluble azo dyes | |
| DE750398C (en) | Process for the preparation of 3- and 4-oxypyridine-4- and -3-carboxylic acids | |
| DE737495C (en) | Process for the production of alkaline earth lactates from monosaccharides | |
| DE1011411B (en) | Process for obtaining pure tert. Butylbenzoic acids | |
| DE634036C (en) | Process for the production of colored condensation products of oxalylurea | |
| DE634285C (en) | Process for the preparation of Abkoemmlingen des 2,4-Dioxotetrahydropyridins | |
| DE436524C (en) | Process for the preparation of 2-oxynaphthalene-6-carboxylic acid | |
| DE1153029B (en) | Process for the preparation of o-aminophenol-ª ‰ -hydroxyaethylsulfon-sulfuric acid esters | |
| DE226220C (en) | ||
| CH134847A (en) | Process for the preparation of an arylcarboxamide-o-thioglycolic acid. | |
| DE512821C (en) | Process for the preparation of 1, 1-dianthraquinonyl-2, 2-diurethane, its derivatives and, if appropriate, condensation products | |
| DE447539C (en) | Process for the preparation of O, 0-diacetyldiphenolisatin | |
| DE728410C (en) | Process for the preparation of N-substituted aliphatic and aromatic aminosulfonic or aminosulfonic acids | |
| DE764488C (en) | Process for purifying adipic acid and its homologues | |
| DE492509C (en) | Process for the production of borneol from nopinen | |
| DE516676C (en) | Process for the preparation of reduction products of indoxylene | |
| DE724162C (en) | Process for the preparation of 1-cyclohexyl-3-methyl-5-pyrazolone | |
| DE719271C (en) | Process for the production of aldehyde compounds of the quinoline series | |
| DE512820C (en) | Process for the preparation of oxyanthraquinone derivatives, in particular alizarin and its derivatives | |
| DE565799C (en) | Process for the preparation of 1-pheny1-3-methy1-4-alkyl- and -4-aralkylpyrazolones |