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DE685143C - Process for the preparation of organic acids from solutions containing pentoses and hexoses - Google Patents

Process for the preparation of organic acids from solutions containing pentoses and hexoses

Info

Publication number
DE685143C
DE685143C DEH148932D DEH0148932D DE685143C DE 685143 C DE685143 C DE 685143C DE H148932 D DEH148932 D DE H148932D DE H0148932 D DEH0148932 D DE H0148932D DE 685143 C DE685143 C DE 685143C
Authority
DE
Germany
Prior art keywords
hexoses
organic acids
solutions containing
furfural
preparation
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
DEH148932D
Other languages
German (de)
Inventor
Dr Eduard Faerber
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.)
HOLZHYDROLYSE AG
Original Assignee
HOLZHYDROLYSE 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 HOLZHYDROLYSE AG filed Critical HOLZHYDROLYSE AG
Priority to DEH148932D priority Critical patent/DE685143C/en
Application granted granted Critical
Publication of DE685143C publication Critical patent/DE685143C/en
Expired legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D307/00Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34Heterocyclic 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
    • C07D307/38Heterocyclic 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
    • C07D307/40Radicals substituted by oxygen atoms
    • C07D307/46Doubly bound oxygen atoms, or two oxygen atoms singly bound to the same carbon atom
    • C07D307/48Furfural
    • C07D307/50Preparation from natural products
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00Preparation of carboxylic acids or their salts, halides or anhydrides
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/16Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation
    • C07C51/295Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with inorganic bases, e.g. by alkali fusion

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Inorganic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Description

Verfahren zur Herstellung organischer Säuren aus Pentosen und Hex_ osen enthaltenden Lösungen Durch das Aufschließen cellulosehaltiger Pflanzenstoffe entstehen Lösungen, die Pentosen und Hexosen enthalten. Diese sollen entweder unmittelbar oder nach .dem Abtrennen eines Teiles der' Kohlenhydrate verarbeitet werden.Process for the production of organic acids from pentoses and hex_ osen-containing solutions By breaking down cellulose-containing plant substances solutions are created that contain pentoses and hexoses. These should either be immediate or after some of the carbohydrates have been separated off.

Wenn man die Pentosen in bekannter Weise durch Erhitzen mit Mineralsäure in Furfuröl umwandelt, dann werden gleichzeitig Hexosen, teilweise unter Bildung unlöslicher Ausscheidungen, zersetzt. Der Rest der Hexosenblieb bisher ohne Verwertbarkeit zurück. Die unlöslichen Stoffe machen es praktisch unmöglich, die Gewinnung von Furfurol ununterbrochen durchzuführen; sie sind ein, unerwünschter Ballast und verringern dieAusbeute sowohl an Furfurol als auch an den aus den Hexosen gebildeten organischen Säuren.If the pentoses are made in a known manner by heating with mineral acid converted into furfural oil, then hexoses are formed at the same time, sometimes with formation insoluble waste, decomposed. The rest of the hexoses have so far remained useless return. The insoluble substances make it practically impossible to obtain To carry out furfural continuously; they are an unwanted ballast and reduce the yield of both furfural and the organic formed from the hexoses Acids.

flach der Erfindung werden diese Nachteile vermieden. Im Anschluß an die Gewinnung von Furfurol durch Erhitzen mit Säure macht man die Flüssigkeit alkalisch, erhitzt sie dann weiter und trennt die entstandenen organischen Säuren .ab. Es ist bekannt, daß Hexosen beim Erhitzen mit Alkalien zum Teil in organische Säuren übergehen. Neu ist jedoch die Erkenntnis, daß jene unlöslichen Ausscheidungen durch Kocheninalkalischer Flüssigkeit in Lösung gehen und dabei aufgeschlossen werden. Sie gehen in ähnliche Produkte über, wie sie durch Alkalien aus den Hexosen gebildet werden. Außerdem wird der noch verbliebene Rest von Hexosen bei der alkalischen Kochung völlig umgewandelt.According to the invention, these disadvantages are avoided. In connection The liquid is used to obtain furfural by heating it with acid alkaline, it then heats it further and separates the organic acids formed .away. It is known that when heated with alkalis, some of the hexoses are converted into organic Acids pass over. What is new, however, is the knowledge that these insoluble excretions go into solution by boiling alkaline liquid and are digested in the process. They pass over into products similar to those formed from the hexoses by alkalis will. In addition, the remainder of the hexoses becomes alkaline Cooking completely transformed.

Aus den in Wasser unlöslichen Stoffen und den Hexosen entstehen dabei hauptsächlich Milchsäure und Lävulinsäure neben geringen Mengen von Essig- und Ameisensäure. Man trennt diese Stoffe in an sich bekannter Weise voneinander, indem man z. B. ansäuert, die flüchtigen Säuren abtreibt und die nichtflüchtigen extrahiert.The water-insoluble substances and the hexoses result from this mainly lactic acid and levulinic acid, along with small amounts of acetic and formic acid. These substances are separated from one another in a manner known per se by z. B. acidifies, drives off the volatile acids and extracts the non-volatile ones.

Beispielsweise sei eine wäßrige Lösung mit 30/0 Pentosen und 2,50/0 Hexosen zu verarbeiten. Man stellt ihre Acidität .auf o,8 bis i,5o,'o Mineralsäure, als Salzsäure -gerechnet, ein und erhitzt unter. Druck. Das dahei,-sex@t_ stehende Furfurol wird abdestilliert;: D J bringt man, vorzugsweise ohne den lf@rf@`y verringern, Natronlauge oder eine alkalisch reagierende Lösung in solch-eren:°@' in das Druckgefäß, daß die Flüssigkeit eine Alkalität 4entsprechend o,5%iger Natronlauge erhält. Man erhitzt kurze Zeit, z. B. 20 Minuten bei i 5o', bis die Lösung wieder homogen oder nahezu homogen geworden ist. Beim Abdrücken der Lösung setzt man ihr wieder Säure zu und kondensiert die die flüchtigen Säuren enthaltenden Dämpfe zwecks Gewinnung von Ameisen- und Essigsäure. Bei der nunmehr folgenden Extraktion der gegebenenfalls weitereingeengten Lösung gewinnt man Milchsäure und Lävulinsäure. Die Ausbeuten an diesen beiden Säuren sindungefährdoppelt so hoch als sonst; aus ioo 1 der ohenerwähnten Ausgangslösung kann man nach dem Abdestillieren des Furfurols birher ungefähr 3oo g Lävulinsäure und q.o g Milchsäure gewinnen; wenn man jedoch die alkalische Kochung einschaltet, so gewinnt man ungefähr 7O0 g Lävulinsäure'und fast ioog Milchsäure.For example, an aqueous solution with 30/0 pentoses and 2.50/0 hexoses is to be processed. Its acidity is set at 0.8 to 1.5o, mineral acid, calculated as hydrochloric acid, one and heated under. Pressure. Das dahei, -sex @ t_ standing furfural is distilled off ;: DJ bring it, preferably without the lf @ rf @ `y decrease, caustic soda or a alkaline reacting solution in such-eren: ° @ ' into the pressure vessel so that the liquid has an alkalinity of 4.5% sodium hydroxide solution. It is heated for a short time, e.g. B. 20 minutes at i 50 'until the solution has become homogeneous or almost homogeneous again. When the solution is squeezed out, acid is added again and the vapors containing the volatile acids are condensed to obtain formic and acetic acid. In the extraction of the optionally further concentrated solution that now follows, lactic acid and levulinic acid are obtained. The yields of these two acids are about twice as high as usual; From 100 liters of the above-mentioned starting solution, after the furfural has been distilled off, about 300 g of levulinic acid and qo g of lactic acid can be obtained; but if the alkaline cooking is switched on, about 700 g of levulinic acid and almost 100 g of lactic acid are obtained.

Alle diese Operationen lassen sich konti-#huierlich durchführen. Die Ausgangslösung ann z. B. eine Batterie von Druckgefäßen erchströmen, in der nacheinander .die saure ''und die alkalische Kochung geschehen, die Destillationsprodukte getrennt abgezogen werden und die kontinuierliche Extraktion angeschlossen wird.All of these operations can be performed continuously. the Starting solution ann z. B. erchström a battery of pressure vessels in which one after the other The acidic and the alkaline boiling are done, the distillation products are separated withdrawn and the continuous extraction is connected.

Claims (2)

PATENTANSPRÜCHE: i. Verfahren zur Herstellung organischer Säuren neben Furfurol durch Behandlung von Pentosen und Hexosen enthaltenden Lösungen in der Hitze unter Druck in Gegenwart von Mineralsäure,und Entfernung des Furfurols durch Destillation, dadurch gekennzeichnet, daß man nach der Entfernung des Furfurols alkalisch macht, weiter erhitzt und darauf die ,entstandenen Säuren nach an sich bekannten Arbeitsweisen entfernt. PATENT CLAIMS: i. Process for the production of organic acids besides Furfurol by treating solutions containing pentoses and hexoses in the Heat under pressure in the presence of mineral acid, and remove the furfural through Distillation, characterized in that after the removal of the furfural makes it alkaline, heated further and then the acids that have formed after themselves known working methods removed. 2. Verfahren nach Anspruch i, dadurch gekennzeichnet, daß man es fortlaufend ausführt.2. The method according to claim i, characterized in that that it is carried out continuously.
DEH148932D 1936-09-23 1936-09-23 Process for the preparation of organic acids from solutions containing pentoses and hexoses Expired DE685143C (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
DEH148932D DE685143C (en) 1936-09-23 1936-09-23 Process for the preparation of organic acids from solutions containing pentoses and hexoses

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEH148932D DE685143C (en) 1936-09-23 1936-09-23 Process for the preparation of organic acids from solutions containing pentoses and hexoses

Publications (1)

Publication Number Publication Date
DE685143C true DE685143C (en) 1939-12-21

Family

ID=7180563

Family Applications (1)

Application Number Title Priority Date Filing Date
DEH148932D Expired DE685143C (en) 1936-09-23 1936-09-23 Process for the preparation of organic acids from solutions containing pentoses and hexoses

Country Status (1)

Country Link
DE (1) DE685143C (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0373082A1 (en) * 1988-12-09 1990-06-13 Societe Francaise D'organo-Synthese Process for preparing levulinic acid

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0373082A1 (en) * 1988-12-09 1990-06-13 Societe Francaise D'organo-Synthese Process for preparing levulinic acid
FR2640263A1 (en) * 1988-12-09 1990-06-15 Organo Synthese Ste Fse PREPARATION OF LEVULINIC ACID
US5175358A (en) * 1988-12-09 1992-12-29 Societe Francaise D'organo-Synthese Preparation of laevulinic acid

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