DE2839565C2 - Process for the extraction of pure beech wood tar creosote - Google Patents
Process for the extraction of pure beech wood tar creosoteInfo
- Publication number
- DE2839565C2 DE2839565C2 DE19782839565 DE2839565A DE2839565C2 DE 2839565 C2 DE2839565 C2 DE 2839565C2 DE 19782839565 DE19782839565 DE 19782839565 DE 2839565 A DE2839565 A DE 2839565A DE 2839565 C2 DE2839565 C2 DE 2839565C2
- Authority
- DE
- Germany
- Prior art keywords
- creosote
- beech wood
- wood tar
- extraction
- pure
- 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
- WHRZCXAVMTUTDD-UHFFFAOYSA-N 1h-furo[2,3-d]pyrimidin-2-one Chemical compound N1C(=O)N=C2OC=CC2=C1 WHRZCXAVMTUTDD-UHFFFAOYSA-N 0.000 title claims description 20
- 235000006173 Larrea tridentata Nutrition 0.000 title claims description 20
- 244000073231 Larrea tridentata Species 0.000 title claims description 20
- 229960002126 creosote Drugs 0.000 title claims description 20
- 238000000034 method Methods 0.000 title claims description 8
- 235000010099 Fagus sylvatica Nutrition 0.000 title claims description 7
- 239000011276 wood tar Substances 0.000 title claims description 5
- 240000000731 Fagus sylvatica Species 0.000 title claims 2
- 238000000605 extraction Methods 0.000 title 1
- 238000004821 distillation Methods 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 238000003756 stirring Methods 0.000 claims description 5
- 239000008346 aqueous phase Substances 0.000 claims description 4
- 239000012074 organic phase Substances 0.000 claims description 4
- NVIFVTYDZMXWGX-UHFFFAOYSA-N sodium metaborate Chemical compound [Na+].[O-]B=O NVIFVTYDZMXWGX-UHFFFAOYSA-N 0.000 claims description 4
- 239000007864 aqueous solution Substances 0.000 claims description 3
- 230000035484 reaction time Effects 0.000 claims description 3
- 239000011734 sodium Substances 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 241001070947 Fagus Species 0.000 description 5
- AVAYCNNAMOJZHO-UHFFFAOYSA-N [Na+].[Na+].[O-]B[O-] Chemical compound [Na+].[Na+].[O-]B[O-] AVAYCNNAMOJZHO-UHFFFAOYSA-N 0.000 description 5
- 239000000243 solution Substances 0.000 description 4
- 238000009835 boiling Methods 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 235000011121 sodium hydroxide Nutrition 0.000 description 3
- PETRWTHZSKVLRE-UHFFFAOYSA-N 2-Methoxy-4-methylphenol Chemical compound COC1=CC(C)=CC=C1O PETRWTHZSKVLRE-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- LHGVFZTZFXWLCP-UHFFFAOYSA-N guaiacol Chemical compound COC1=CC=CC=C1O LHGVFZTZFXWLCP-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 238000001256 steam distillation Methods 0.000 description 2
- 239000011269 tar Substances 0.000 description 2
- 239000002641 tar oil Substances 0.000 description 2
- 238000006887 Ullmann reaction Methods 0.000 description 1
- 230000002421 anti-septic effect Effects 0.000 description 1
- 239000003434 antitussive agent Substances 0.000 description 1
- 229940124584 antitussives Drugs 0.000 description 1
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 1
- 229910052601 baryte Inorganic materials 0.000 description 1
- 239000010428 baryte Substances 0.000 description 1
- 229910021538 borax Inorganic materials 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000006103 coloring component Substances 0.000 description 1
- 238000005188 flotation Methods 0.000 description 1
- 229960001867 guaiacol Drugs 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 150000008379 phenol ethers Chemical class 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 235000010339 sodium tetraborate Nutrition 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10C—WORKING-UP PITCH, ASPHALT, BITUMEN, TAR; PYROLIGNEOUS ACID
- C10C1/00—Working-up tar
- C10C1/04—Working-up tar by distillation
- C10C1/08—Winning of aromatic fractions
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Materials Engineering (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
1515th
Die Erfindung betrifft ein Verfahren zur Gewinnung von reinem Buchenholzteer-Kreosot.The invention relates to a method for obtaining pure beech wood tar creosote.
Kreosot (Buchenholzteer-Kreosot) ist eine schwach gelbliche Flüssigkeit von spezifischem Geruch. Es weist einen Siedebereich von 200 bis 2200C sowie ein spezifisches Gewicht von 1,08 bis 1,09 auf. Die wichtigsten Bestandteile des Kreosotes sind Kreosol, Guajakol, p-Kiesol und andere Phenole und Phenoläther. Es hat antiseptische Eigenschaften und wird zur' Herstellung pharmazeutischer Präparate verwendet, z. B. für Hustenmittel. Für diesen Anwendungszweck werden in der deutschen Pharmakopoe gemäß DAB VI bestimmte Eigenschaften verlangtCreosote (beech wood tar creosote) is a pale yellowish liquid with a specific odor. It has a boiling range from 200 to 220 ° C. and a specific weight from 1.08 to 1.09. The main components of creosote are creosol, guaiacol, p-kiesol and other phenols and phenol ethers. It has antiseptic properties and is used in the 'manufacture of pharmaceutical preparations, e.g. B. for cough suppressants. In accordance with DAB VI, the German Pharmacopoeia requires certain properties for this purpose
Ausgangsprodukt für die Erzeugung von Kreosot ist das sogenannte schwere Teeröl, welches bei der Verkohlung von Buchenholz anfällt Man behandelt im allgemeinen das Teeröl zunächst mit Natronlauge, wobei sich die sogenannten indifferenten öle abscheiden. Diese werden z. B. zur Herstellung von Flotationsölen verwendet Die von den indifferenten ölen befreite Lauge wird mit Schwefelsäure versetzt, wobei iich das sogenannte Rohkreosot abscheidet Aus diesem Rohkreosot wird durch mehrfache Rektifikation das Kreosot in pharmazeutischer Qualität gewonnen (vgl. Ullmanns Enzyklopädie der technischen Chemie, 3. Auflage, 8. Band, Seite 590 (1957), Verlag Urban und Schwarzenberg, München-Berlin).The starting product for the production of creosote is the so-called heavy tar oil, which is used in the Charring of beech wood occurs. In general, the tar oil is first treated with caustic soda, whereby the so-called indifferent oils separate out. These are z. B. used for the production of flotation oils The freed from the indifferent oils Lye is mixed with sulfuric acid, whereby the so-called raw creosote is separated from this raw creosote the creosote is obtained in pharmaceutical quality by repeated rectification (cf. Ullmanns Enzyklopädie der technischen Chemie, 3rd edition, 8th volume, page 590 (1957), Verlag Urban and Schwarzenberg, Munich-Berlin).
Das bekannte Verfahren zur Erzeugung von Buchenholzteer-Kreosot weist den Nachteil auf, daß man das Rohkreosot für die Entfernung der stark färbenden Bestandteile durch mehrfache (bis zu 4- bis 5fache) arbeits- und energieaufwendige Destillation führen muß.The known method for the production of beech tar creosote has the disadvantage that it is Raw creosote for the removal of the strongly coloring components by multiples (up to 4 to 5 times) must lead labor and energy consuming distillation.
Gegenstand der Erfindung ist ein Verfahren zur Gewinnung von reinem Buchenholzteer-Kreosot durch mehrfache Destillation von Rohkreosot, welches dadurch gekennzeichnet ist, daß man zu dem bei der ersten Destillation erhaltenen Destillat eine wäßrige Lösung von Natriumboranat (Na BH4) unter Rühren zutropft, nach einer Reaktionszeit von 1 bis 60 Minuten die wäßrige Phase abtrennt und die organische Phase im Vakuum destilliert oder einer Wasserdampfdestillation unterwirftThe invention relates to a process for obtaining pure beech wood tar creosote by multiple distillation of raw creosote, which is characterized in that an aqueous solution of sodium boranate (Na BH 4 ) is added dropwise with stirring to the distillate obtained in the first distillation, after a The aqueous phase is separated off for a reaction time of 1 to 60 minutes and the organic phase is distilled in vacuo or subjected to steam distillation
Die wäßrige Lösung von Natriumboranat (Na BH4) kann eine Konzentration von 0,5 bis 10 g NaBH4 in 150 ml Wasser aufweisen, dies entspricht einer Konzentration von 30 bis 70 g/l.The aqueous solution of sodium boronate (Na BH 4 ) can have a concentration of 0.5 to 10 g of NaBH 4 in 150 ml of water, which corresponds to a concentration of 30 to 70 g / l.
Die zu dem Erstdestillat zugetropfte Menge an wäßriger Natriumboranat-Lösung kann zu der Menge des Erstdestillates im Verhältnis von vorzugsweise 155 zu 500 (=31:100) betragen. Das Verhältnis kann aber auch 10 bis 200 zu 50 bis 500 betragen.The amount of aqueous sodium boronate solution added dropwise to the primary distillate can add to the amount of the first distillate in a ratio of preferably 155 to 500 (= 31: 100). But the relationship can also be 10 to 200 to 50 to 500.
Bezogen auf die Menge des Erstdestillates kann die Menge des pulverförmiger! Natriumboranates 0,1 bis 3 Gew.-%, vorzugsweise 1 bis 2 Gew.-% betragen.In relation to the amount of the first distillate, the amount of the powdery! Sodium Boranates 0.1 to 3 % By weight, preferably 1 to 2% by weight.
Das Zutropfen der wäßrigen Natriumboranat-Lösung kann bei beliebigen Temperaturen erfolgen. Vorzugsweise tropft man die wäßrige Natriumboranat-Lösung unter Rühren langsam bei Raumtemperatur zu, da eine exotherme Reaktion eintritt Vorteilhafterweise läßt man nach Zugabe der gesamten wäßrigen Natriumboranat-Lösung das erhaltene Gemisch unter Rühren einige Zeit, vorzugsweise 10 bis 30 Minuten, reagieren.The aqueous sodium boronate solution can be added dropwise at any temperature. Preferably the aqueous sodium boronate solution is slowly added dropwise with stirring at room temperature, since a exothermic reaction occurs. Advantageously, all of the aqueous sodium boronate solution is left in the resulting mixture react with stirring for some time, preferably 10 to 30 minutes.
Nach der Abtrennung der wäßrigen Phase kann die Destillation der organischen Phase vorteilhafterweise im Wasserstrahlvakuum durchgeführt werden. Auch eine Wasserdampfdestillation ist möglich.After the aqueous phase has been separated off, the organic phase can advantageously be distilled be carried out in a water jet vacuum. Steam distillation is also possible.
Das mittels dem erfindungsgemäßen Verfahren erhaltene Reinkreosot ist fast wasserklar und dunkelt innerhalb eines Zeitraumes von 60 Tagen nicht nach. Es entspricht den Anforderungen der deutschen Pharmakopoe gemäß DAB VI.The pure creosote obtained by means of the method according to the invention is almost water-clear and dark within a period of 60 days. It meets the requirements of the German Pharmacopoeia according to DAB VI.
Aufgrund des erfindungsgemäßen Verfahrens ist es möglich, aus dem Buchenholzteer-Rohkreosot in zwei Destillationsstufen das Reinkreosot zu erzeugen.Due to the method according to the invention, it is possible from the beechwood tar raw creosote in two Distillation stages to produce the pure creosote.
Das erfindungsgemäße Verfahren wird an Hand des folgenden Beispiels näher erläutert und beschrieben.The method according to the invention is explained and described in more detail using the following example.
SeispielExample
5 g Natriumboranat (Na BH4) werden in 150 ml Wasser gelöst und innerhalb 15 Minuten unter Rühren zu 500 g Erstdestillat getropft. Nach einer Reaktionszeit von weiteren 30 Minuten wird die wäßrige Phase abgetrennt und die organische Phase im Wasserstrahlvakuum an einer 25 cm Vigreux-Kolonne destilliert Die Ausbeute beträgt 431,4 g (86,3 Gew.-% berechnet auf das eingesetzte Erstdestillat).5 g of sodium borate (Na BH 4 ) are dissolved in 150 ml of water and added dropwise to 500 g of primary distillate over a period of 15 minutes with stirring. After a reaction time of a further 30 minutes, the aqueous phase is separated off and the organic phase is distilled in a water jet vacuum on a 25 cm Vigreux column. The yield is 431.4 g (86.3% by weight, calculated on the initial distillate used).
Das erhaltene Reinkreosot zeigt im Vergleich zu den Anforderungen gemäß der deutschen Pharmakopoe DAB VI die folgenden Eigenschaften:The pure creosote obtained shows a comparison with the requirements of the German Pharmacopoeia DAB VI has the following properties:
DABVIDABVI
Produktproduct
Klare, schwach gelbe Flüssigkeit entspricht
Dichte l,075/20°C 1,084Clear, pale yellow liquid corresponds
Density 1.075 / 20 ° C 1.084
Siedebereich größtenteils Siedebeginn:Boiling range mostly onset of boiling:
200-2200C 197,90/760 mm HG200-220 0 C 197.90 / 760 mm HG
199,6°C = 5%
200,40C = 10%
• 201,90C = 15%
202,90C = 20%
204,30C = 30%
205,80C = 40%
207,50C = 50%
209,50C = 60%
211,9°C =70%
215,7°C = 80%
221,3°C = 90%
227,4°C = 95%199.6 ° C = 5%
200.4 0 C = 10%
• 201.9 0 C = 15%
202.9 0 C = 20%
204.3 0 C = 30%
205.8 0 C = 40%
207.5 0 C = 50%
209.5 0 C = 60%
211.9 ° C = 70%
215.7 ° C = 80%
221.3 ° C = 90%
227.4 ° C = 95%
Fortsetzungcontinuation
DABVIDABVI
Produktproduct
1 Tropfen Kreosot darf Lackmus höchstens schwach röten
Löslichkeit in Äther
Löslichkeit in heißem Wasser Trübung bei Abkühlung
FeCl3-Teste
NaOH-Test1 drop of creosote is allowed to redden litmus at most. Solubility in ether
Solubility in hot water. Cloudy on cooling
FeCl 3 tests
NaOH test
DABVIDABVI
entsprichtis equivalent to
entspricht entspricht entspricht nicht entsprechen entsprichtcorresponds to corresponds to does not correspond to corresponds to
1010
Produktproduct
Löslichkeit in Glycerin- entsprichtSolubility in glycerine- corresponds
Wasser-GemischWater mixture
Prüfung mit Petrolbenzin entsprichtTest with petrol
und Barytwasserand barite water
Wertbestimmung entsprichtValue determination corresponds
Der Test »Trübung bei Abkühlung« entspricht nicht, weil das erfindungsgemäß erhaltene Produkt eine höhere Reinheit aufweistThe "turbidity on cooling" test does not correspond because the product obtained according to the invention is a has higher purity
Claims (1)
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19782839565 DE2839565C2 (en) | 1978-09-12 | 1978-09-12 | Process for the extraction of pure beech wood tar creosote |
| FR7921520A FR2436174A1 (en) | 1978-09-12 | 1979-08-28 | Two=stage distillative purificn. of beech tar creosote - by mixing the first distillate obtd. by conventional distn. with sodium boranate and then distilling the organic phase |
| SE7907543A SE7907543L (en) | 1978-09-12 | 1979-09-11 | PROCEDURE FOR RENE STILLATION OF BOOK RECORDS |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19782839565 DE2839565C2 (en) | 1978-09-12 | 1978-09-12 | Process for the extraction of pure beech wood tar creosote |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2839565A1 DE2839565A1 (en) | 1980-03-27 |
| DE2839565C2 true DE2839565C2 (en) | 1982-07-29 |
Family
ID=6049211
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19782839565 Expired DE2839565C2 (en) | 1978-09-12 | 1978-09-12 | Process for the extraction of pure beech wood tar creosote |
Country Status (3)
| Country | Link |
|---|---|
| DE (1) | DE2839565C2 (en) |
| FR (1) | FR2436174A1 (en) |
| SE (1) | SE7907543L (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1056363C (en) * | 1995-10-04 | 2000-09-13 | 朱昌朋 | Extraction of 4-methyl guaiacol and 4-ethyl guaiacol from creasote |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR602866A (en) * | 1925-05-20 | 1926-04-02 | Process for the refining of beech tar oils and for the manufacture of high-value pure preparations | |
| US2573990A (en) * | 1948-03-08 | 1951-11-06 | Crossett Lumber Company | Recovery of medicinal creosote |
| US3150191A (en) * | 1960-02-29 | 1964-09-22 | California Research Corp | Phenol color reduction |
-
1978
- 1978-09-12 DE DE19782839565 patent/DE2839565C2/en not_active Expired
-
1979
- 1979-08-28 FR FR7921520A patent/FR2436174A1/en active Granted
- 1979-09-11 SE SE7907543A patent/SE7907543L/en not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| DE2839565A1 (en) | 1980-03-27 |
| SE7907543L (en) | 1980-03-13 |
| FR2436174A1 (en) | 1980-04-11 |
| FR2436174B1 (en) | 1984-02-24 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OD | Request for examination | ||
| OGA | New person/name/address of the applicant | ||
| D2 | Grant after examination | ||
| 8339 | Ceased/non-payment of the annual fee |