DE943886C - Process for purifying m-cresol - Google Patents
Process for purifying m-cresolInfo
- Publication number
- DE943886C DE943886C DEL9110A DEL0009110A DE943886C DE 943886 C DE943886 C DE 943886C DE L9110 A DEL9110 A DE L9110A DE L0009110 A DEL0009110 A DE L0009110A DE 943886 C DE943886 C DE 943886C
- Authority
- DE
- Germany
- Prior art keywords
- cresol
- urea
- addition compound
- purifying
- cleavage
- 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/68—Purification; separation; Use of additives, e.g. for stabilisation
- C07C37/70—Purification; separation; Use of additives, e.g. for stabilisation by physical treatment
- C07C37/84—Purification; separation; Use of additives, e.g. for stabilisation by physical treatment by crystallisation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/68—Purification; separation; Use of additives, e.g. for stabilisation
- C07C37/685—Processes comprising at least two steps in series
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/68—Purification; separation; Use of additives, e.g. for stabilisation
- C07C37/70—Purification; separation; Use of additives, e.g. for stabilisation by physical treatment
- C07C37/72—Purification; separation; Use of additives, e.g. for stabilisation by physical treatment by liquid-liquid treatment
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/68—Purification; separation; Use of additives, e.g. for stabilisation
- C07C37/70—Purification; separation; Use of additives, e.g. for stabilisation by physical treatment
- C07C37/74—Purification; separation; Use of additives, e.g. for stabilisation by physical treatment by distillation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/68—Purification; separation; Use of additives, e.g. for stabilisation
- C07C37/86—Purification; separation; Use of additives, e.g. for stabilisation by treatment giving rise to a chemical modification
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Crystallography & Structural Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Reinigung von m-Kresol Es ist bekannt, m-Kresol, das noch andere Phenols enthält, durch Behandeln mit Harnstoff in eine Additionsverbindung überzuführen, diese von anhaftenden Phenolen durch Abschleudern zu befreien und die Additionsverbindung entweder durch Behandeln mit Wasser oder Säure bzw. durch Vakuum- oder Wasserdampfdestillation in ihreKomponenten zu zerlegen. Es ist auch nicht mehr neu, die Abtrennung der Phenols, die der m-Kreso@l-Harnstoff-Additionsverbindung noch anhaften, durch Waschen mit Lösungsmitteln, wie Tetrachlorkohlenstoff, vorzunehmen.Methods for Purifying m-Cresol It is known that m-cresol still contains other phenols by treating with urea to form an addition compound to free them from adhering phenols by centrifuging them and the addition compound either by treatment with water or acid or by Vacuum or steam distillation into its components. It is also no longer new, the separation of the phenol, that of the m-Kreso @ l-urea addition compound still adhere by washing with solvents such as carbon tetrachloride.
Diese Verfahren haben beträchtliche Nachteile. So führt z. B. die Zerlegung der Additionsverbindung durch Vakuumdestillation unter beträchtlicher Zersetzung des Harnstoffes zu einem ammoniakhaltigen m-Kresol. Noch ungünstiger wirkt sich eine Wasserdampfdestillation aus, da dann das m-Kresol wasserhaltig anfällt und der Harnstoff nur urnständhch und mit Verlusten aus der wäßri.gen Lösung wiederzugewinnen ist. Ähnlich verhält es sich bei der Spaltung der Harnstoffadditionsverbindung mit Säuren; man erhält eine kresolhaltige saure wäßrige Harnstofflös.ung einerseits und andererseits eine wasserhaltige saure Kresolschicht.These methods have significant disadvantages. So z. B. the Decomposition of the addition compound by vacuum distillation under considerable pressure Decomposition of the urea to an ammonia-containing m-cresol. Even worse a steam distillation has an effect, since the m-cresol is then obtained as a water-containing product and the urea can only be recovered from the aqueous solution inconveniently and with losses is. The situation is similar with the cleavage of the urea addition compound Acids; On the one hand, an acidic aqueous urea solution containing cresol is obtained and on the other hand a hydrous acidic cresol layer.
Es wurde nun gefunden, daß man m-Kresol in vorzügliche- Weise reinigen kann, wenn man das bekannte Verfahren zur Reinigung, bei dem m-Kresol zunächst in seine Harnstoffadditionsverbindung übergeführt wird, von dieser die noch anhaftenden Phenols durch Waschen mit Lösungsmitteln abgetrennt werden und die verbleibende Harnstoffa4ditionsverbindung bei erhöhter Temperatur gespalten wird, in der Weise ausführt; daß man die Spaltung durch Behandeln mit Halogenkoh .lenwasserstoffen vornimmt, deren Siedepunkte unter dem des m-Kresols liegen.It has now been found that m-cresol can be cleaned in an excellent manner can, if one uses the known method of cleaning, in which m-cresol initially in its urea addition compound is converted, from this the still adhering Separated phenol by washing with solvents will and the remaining urea addition compound is cleaved at elevated temperature is carried out in the manner; that the cleavage by treatment with halocarbon .Open hydrogen with a boiling point below that of m-cresol.
Vorteilhaift werden solche Chlorkohlenwasserstoffe gewählt, die bei niedriger Temperatur nur die anhaftenden Phenole lösen und die m-Kresol-Harnsteff-Ad'ditionsverbindung noch nicht zerlegen.Those chlorinated hydrocarbons are advantageously chosen that are used in low temperature only dissolve the adhering phenols and the m-cresol-Harnsteff addition compound do not disassemble yet.
Zweckmäßigerweise arbeitet man beim Zerlegen der m-Kresal-Harnstoff-Additionsverbindung bei einer Temperatur, bei der der Harnstoff noch beständig ist.. Die- Chlorkohlenwasserstoff-m-Kresol-Lösung wird vom abgeschiedenen Harnstoff abfiltriert. Nach dem Abtreiben des Chlorkohlenwasserstoffes über eine kurze Kolonne hinterb:leibt ein m-Kresol vom Erstarrungspunkt 1o,9 bis 11,q.°. Der Harnstoff ist nach -dieser Arbeitsweise leicht wiederzugewinnen und von neuem zu verwenden.It is expedient to work with the decomposition of the m-cresal-urea addition compound at a temperature at which the urea is still stable .. The chlorinated hydrocarbon m-cresol solution is filtered off from the separated urea. After driving off the chlorinated hydrocarbon behind a short column: an m-cresol remains from the solidification point 1o, 9 to 11, q. °. The urea is easy to recover and after this procedure to use again.
Als Chlorkohlenwasserstoffe seien unter anderem genannt: Methylenchlorid, Methylchlorid, Chloroform, Tetrachlorkohlenstoff, Äthylchlorid, Trichloräthylen, Propyl- und Isopropylchlo.rid, Butylchlorid, Isoamylchlorid.The following may be mentioned as chlorinated hydrocarbons: methylene chloride, Methyl chloride, chloroform, carbon tetrachloride, ethyl chloride, trichlorethylene, Propyl and isopropyl chloride, butyl chloride, isoamyl chloride.
Folgendes Beispiel möge die Arbeitsweise erläutern: 5oo Gewichtssteile eines 82o/oigen m-Kresol enthaltenden m-Kresols werden mit 333 Teilen Harnstoff unter Rühren auf Zoo bis 12o° erhitzt, bis alles gelöst ist. Nach dem Abkühlen wird die kalte Masse mit 2 Gewichtsteilen eines Halogenkohlenwasserstoffes, z. B. Tetrachlorkohlenstoff; Methylenchlorid oder Chloroform, zerrieben, etwa 2 Stunden gerührt und abfiltriert. Das Filtrat enthält 135 Gewichtsteile Kresole (o-, p-Kresol neben Xylenolen) und etwa 6 Gewichtsteilen Harnstoff, während 668 Gewichtsteile der reinen m-Kresol-Hairnstoff-Additionsverbindung erhalten werden.The following example explains how it works: 500 parts by weight of a m-cresol containing 820% m-cresol are mixed with 333 parts of urea heated to 120 ° while stirring on zoo until everything is dissolved. After cooling it will the cold mass with 2 parts by weight of a halogenated hydrocarbon, e.g. B. carbon tetrachloride; Methylene chloride or chloroform, triturated, stirred for about 2 hours and filtered off. The filtrate contains 135 parts by weight of cresols (o-, p-cresol in addition to xylenols) and about 6 parts by weight of urea, while 668 parts by weight of the pure m-cresol-hairnea addition compound can be obtained.
Zur Zersetzung der Harnstoffadditionsverbindung wird 1 Gewichtsteil mit 2,5 Gewichtsteilen Methylenchlorid unter Rühren 21/2 Stunden kräftig gekocht. Nach dem Abkühlen wird vom zurückgebliebenen Harnstoff abfiltriert und das Lösungsmittel zur Entfernung des darin enthaltenen Harnstoffs - etwa 9 0/0 - mit 300 CCM 2 n-Schwefelsäure ausgeschüttelt, getrocknet und abdestilliert. Es hinterb:leiben 3oo Gewichtsteile eines reinen m-Kresols vom Erstarrungspunkt 1o,5°. Durch Destillation kann das m-Kresol weitergereinigt werden und zeigt dann einen Erstärrungspunkt von 11,q.°. Die Ausbeute an destilliertem m-Kresol beträgt etwa 6o °/o; an reinem Harnstoff werden etwa 82 °/o der eingesetzten Menge direkt zurückgewonnen.To decompose the urea addition compound, 1 part by weight is required boiled vigorously with 2.5 parts by weight of methylene chloride with stirring for 21/2 hours. After cooling, the remaining urea is filtered off and the solvent to remove the urea contained in it - about 9 0/0 - with 300 CCM 2 n-sulfuric acid shaken out, dried and distilled off. It leaves 300 parts by weight of a pure m-cresol with a solidification point of 10.5 °. The m-cresol be cleaned further and then shows a solidification point of 11, q. °. The yield of distilled m-cresol is about 60%; of pure urea are about 82 ° / o of the amount used recovered directly.
Statt Methylenchlorid kann mit ebensolchem Erfolg Chloroform angewendet werden, während die Behandlung mit Trichloräthylen eine erhöhte Kochzeit und die Anwendung größerer' Mengen Lösungsmittel erfordert. Die Zerlegung mit Tetrachlorkohlenstoff verläuft am vorteilhaftesten nach der Extraktionsmethode. Mit Amylchlorid benötigt die Aufspaltung ebenfalls längere Zeit.Instead of methylene chloride, chloroform can be used with just as success while treatment with trichlorethylene increases the cooking time and the Use of larger 'amounts of solvent required. The decomposition with carbon tetrachloride proceeds most advantageously according to the extraction method. Needed with amyl chloride the split also takes a longer time.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEL9110A DE943886C (en) | 1951-05-26 | 1951-05-26 | Process for purifying m-cresol |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEL9110A DE943886C (en) | 1951-05-26 | 1951-05-26 | Process for purifying m-cresol |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE943886C true DE943886C (en) | 1956-06-01 |
Family
ID=7257854
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEL9110A Expired DE943886C (en) | 1951-05-26 | 1951-05-26 | Process for purifying m-cresol |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE943886C (en) |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR660091A (en) * | 1927-09-14 | 1929-07-06 | Schering Kahlbaum Ag | Process for the preparation of pure m- and p- cresols |
| GB297083A (en) * | 1927-09-14 | 1929-09-05 | Schering Kahlbaum Ag | Improvements in or relating to the manufacture of pure m- and p-cresols |
| DE541037C (en) * | 1927-09-15 | 1932-01-07 | Schering Kahlbaum Ag | Process for the production of pure m- and p-cresol |
-
1951
- 1951-05-26 DE DEL9110A patent/DE943886C/en not_active Expired
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR660091A (en) * | 1927-09-14 | 1929-07-06 | Schering Kahlbaum Ag | Process for the preparation of pure m- and p- cresols |
| GB297083A (en) * | 1927-09-14 | 1929-09-05 | Schering Kahlbaum Ag | Improvements in or relating to the manufacture of pure m- and p-cresols |
| DE541037C (en) * | 1927-09-15 | 1932-01-07 | Schering Kahlbaum Ag | Process for the production of pure m- and p-cresol |
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