DE63027C - Process for the preparation of vanillin from vanilloyl carboxylic acid and for the separation of these two compounds - Google Patents
Process for the preparation of vanillin from vanilloyl carboxylic acid and for the separation of these two compoundsInfo
- Publication number
- DE63027C DE63027C DENDAT63027D DE63027DA DE63027C DE 63027 C DE63027 C DE 63027C DE NDAT63027 D DENDAT63027 D DE NDAT63027D DE 63027D A DE63027D A DE 63027DA DE 63027 C DE63027 C DE 63027C
- Authority
- DE
- Germany
- Prior art keywords
- vanillin
- vanilloyl
- carboxylic acid
- acid
- compounds
- 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 - Lifetime
Links
- MWOOGOJBHIARFG-UHFFFAOYSA-N Vanillin Chemical compound COC1=CC(C=O)=CC=C1O MWOOGOJBHIARFG-UHFFFAOYSA-N 0.000 title claims description 26
- 229940117960 vanillin Drugs 0.000 title claims description 13
- 235000012141 vanillin Nutrition 0.000 title claims description 13
- -1 vanilloyl carboxylic acid Chemical class 0.000 title claims description 9
- 150000001875 compounds Chemical class 0.000 title claims description 8
- 238000000034 method Methods 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title claims 2
- 238000000926 separation method Methods 0.000 title claims 2
- 239000002253 acid Substances 0.000 claims description 10
- 239000000243 solution Substances 0.000 claims description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 4
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 claims description 4
- 229940001607 sodium bisulfite Drugs 0.000 claims description 4
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 claims description 4
- IUSBVFZKQJGVEP-SNAWJCMRSA-N isoeugenol acetate Chemical compound COC1=CC(\C=C\C)=CC=C1OC(C)=O IUSBVFZKQJGVEP-SNAWJCMRSA-N 0.000 claims description 3
- 238000002844 melting Methods 0.000 claims description 3
- 230000003647 oxidation Effects 0.000 claims description 3
- 238000007254 oxidation reaction Methods 0.000 claims description 3
- SCCDQYPEOIRVGX-UHFFFAOYSA-N Acetyleugenol Chemical compound COC1=CC(CC=C)=CC=C1OC(C)=O SCCDQYPEOIRVGX-UHFFFAOYSA-N 0.000 claims description 2
- 239000007864 aqueous solution Substances 0.000 claims description 2
- 238000010438 heat treatment Methods 0.000 claims description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 claims 1
- 229910052783 alkali metal Inorganic materials 0.000 claims 1
- 150000001340 alkali metals Chemical class 0.000 claims 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims 1
- 150000001342 alkaline earth metals Chemical class 0.000 claims 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims 1
- 229910052749 magnesium Inorganic materials 0.000 claims 1
- 239000011777 magnesium Substances 0.000 claims 1
- 238000001556 precipitation Methods 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- HEDRZPFGACZZDS-UHFFFAOYSA-N chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate dianion Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N Carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L Magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M Potassium bicarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- UKTDQTGMXUHPIF-UHFFFAOYSA-N [Na].S(O)(O)=O Chemical compound [Na].S(O)(O)=O UKTDQTGMXUHPIF-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000011776 magnesium carbonate Substances 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- 229940094025 potassium bicarbonate Drugs 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
- C07C45/54—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition of compounds containing doubly bound oxygen atoms, e.g. esters
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
KAISERLICHESIMPERIAL
PATENTAMT:PATENT OFFICE:
KLASSE 12:CLASS 12:
Gemische Apparate und Processe.Mixtures of apparatus and processes.
beiden Verbindungen.both connections.
Bei der Oxydation von Aceteugenol,· wie von Acetisoeugenol und Isolirung des dabei gebildeten Vanillins durch Natriumbisulfit wird ein Vanillin gewonnen, das zuweilen gröfsere Mengen von Vanilloylcarbonsäure:In the oxidation of Aceteugenol, as of Acetisoeugenol and isolation of it Vanillin formed by sodium bisulfite produces a vanillin, which is sometimes larger Amounts of vanilloyl carboxylic acid:
/COCOOH
C6 Hs - OCH, / COCOOH
C 6 H s - OCH,
\ OH
enthält.\ OH
contains.
Beide Verbindungen werden von wässeriger Natriumbisulfitlösung leicht aufgenommen und dadurch ätherischen. Lösungen gleichzeitig entzogen. Both compounds are easily absorbed by aqueous sodium bisulfite solution and thereby ethereal. Solutions withdrawn at the same time.
Das Vanillin läfst sich von der Vanilloylcarbonsäure trennen:The vanillin can be removed from the vanilloyl carboxylic acid separate:
1. indem man die ätherische Lösung beider Verbindungen mit Wasser schüttelt, in welchem man Magnesiumcarbonat oder ein Erdalkalicarbonat suspendirt oder Natrium-, besser Kaliumbicarbonat aufgelöst hat, wobei die Vanilloylcarbonsäure als Salz in die wässerige Lösung übergeht, oder1. by shaking the ethereal solution of both compounds with water in which one suspends magnesium carbonate or an alkaline earth carbonate, or sodium, better Potassium bicarbonate has dissolved, with the vanilloyl carboxylic acid as a salt in the aqueous Solution skips, or
2. indem man eine concentrirte wässerige . Lösung der , Poppelverbindungen von saurem schwefligsaurem Natron mit Vanillin und Vanilloylcarbonsäure fractionirt mit Alkohol fällt. Die '. Poppelverbindung der Vanilloylcarbonsäure wird dabei zuerst gefällt.2. by making a concentrated aqueous. Solution of the, Poppel connections of acid Sodium sulphurous acid with vanillin and vanilloylcarboxylic acid fractionated with alcohol falls. The '. Poppel's compound of vanilloylcarboxylic acid is precipitated first.
Die aus ihrer Salzlösung oder der Natriumbisulfit-Doppelverbindungin Freiheit gesetzte Vanilloylcarbonsäure wird in Aether aufgenommen und kann aus Benzol umkrystallisirt werden, wenn man den beim Verdampfen des Aethers bleibenden Rückstand zur Verjagung von Wasser, Alkohol, Aether etc. einige Zeit im luftverdünnten Raum bei ca. 500C erhitzt.The vanilloylcarboxylic acid released from its salt solution or the sodium bisulfite double compound is taken up in ether and can be recrystallized from benzene if the residue left after evaporation of the ether is used to drive away water, alcohol, ether, etc. for some time in an air-diluted room at approx. 50 0 C heated.
Die so behandelte Verbindung wird durch Umkrystallisiren aus Benzol in wasserhellen Prismen gewonnen, welche Krystallbenzol enthalten. The compound thus treated becomes water-white by recrystallization from benzene Obtained prisms which contain crystal benzene.
Die Prismen verwittern schnell beim Liegen an der Luft, indem das Benzol sich daraus verflüchtigt.The prisms weather quickly when lying in the air, as the benzene dissolves out of them evaporated.
Die bei 10O0C. getrocknete Vanilloylcarbonsäure schmilzt bei 133 bis 1340C.The vanilloylcarboxylic acid dried at 10O 0 C. melts at 133 to 134 0 C.
Sie löst sich unschwer, und zwar mit gelber Farbe in Wasser," leicht auch in Alkohol, Aether, Benzol und Chloroform, schwer in Ligro'in.It dissolves easily, with a yellow color in water, "easily also in alcohol, Ether, benzene and chloroform, heavy in ligro'in.
Sie ist als a-Ketonsäure gegen Wasser, Alkalien und Säuren ziemlich beständig, zerfällt aber bei dem Erhitzen über ihren Schmelzpunkt glatt in Kohlensäure und Vanillin.As a-ketonic acid, it is fairly resistant to water, alkalis and acids, and it disintegrates but when heated above their melting point smoothly in carbonic acid and vanillin.
Das Vanillin wird dementsprechend aus der Vanilloylcarbonsäure erhalten durch Erhitzen der letzteren über ihren Schmelzpunkt oder von Gemischen aus Vanillin und Vanilloylcarbonsäure auf die gleiche Temperatur.The vanillin is accordingly obtained from the vanilloyl carboxylic acid by heating the latter via their melting point or mixtures of vanillin and vanilloyl carboxylic acid at the same temperature.
Da indessen im letzteren Falle secündäre Zersetzungen nicht ganz auszuschliefsen sind, ist es im allgemeinen vortheilhafter, die beiden Verbindungen vorher auf den beschriebenen Wegen von einander zu trennen.Since, however, in the latter case it is secondary If decompositions cannot be completely ruled out, it is generally more advantageous to use both Separate connections beforehand using the methods described.
Claims (1)
behufs Umwandlung der auf diese Weise isolirten Vanilloylcarbonsäure in Vanillin nach Anspruch ι.b) by fractionated precipitation of aqueous solutions of the sodium bisulfite double compounds of vanillin and vanilloylcorbonic acid by alcohol
for the conversion of the vanilloylcarboxylic acid isolated in this way into vanillin according to claim ι.
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE63027C true DE63027C (en) |
Family
ID=336980
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT63027D Expired - Lifetime DE63027C (en) | Process for the preparation of vanillin from vanilloyl carboxylic acid and for the separation of these two compounds |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE63027C (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6310129B1 (en) | 1997-10-02 | 2001-10-30 | Rebaseproducts Inc. | Processing and use of carbide lime |
-
0
- DE DENDAT63027D patent/DE63027C/en not_active Expired - Lifetime
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6310129B1 (en) | 1997-10-02 | 2001-10-30 | Rebaseproducts Inc. | Processing and use of carbide lime |
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