DE72600C - Method for the preparation of vanillin - Google Patents
Method for the preparation of vanillinInfo
- Publication number
- DE72600C DE72600C DENDAT72600D DE72600DA DE72600C DE 72600 C DE72600 C DE 72600C DE NDAT72600 D DENDAT72600 D DE NDAT72600D DE 72600D A DE72600D A DE 72600DA DE 72600 C DE72600 C DE 72600C
- Authority
- DE
- Germany
- Prior art keywords
- vanillin
- preparation
- acid
- water
- aldehydoguajacolcarboxylic
- 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 8
- 229940117960 vanillin Drugs 0.000 title claims description 4
- 235000012141 vanillin Nutrition 0.000 title claims description 4
- 239000002253 acid Substances 0.000 claims description 5
- BVKZGUZCCUSVTD-UHFFFAOYSA-N Carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 2
- -1 As the silver salt Chemical class 0.000 description 1
- GGCZERPQGJTIQP-UHFFFAOYSA-M Sodium 2-anthraquinonesulfonate Chemical compound [Na+].C1=CC=C2C(=O)C3=CC(S(=O)(=O)[O-])=CC=C3C(=O)C2=C1 GGCZERPQGJTIQP-UHFFFAOYSA-M 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 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
- 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
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/673—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by change of size of the carbon skeleton
- C07C45/676—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by change of size of the carbon skeleton by elimination of carboxyl groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
Wird Aldehydoguajacolcarbonsäure erhitzt, so spaltet sich Kohlensäure ab und es bleibt Aldehydoguajacol, das ist Vanillin, zurück:If aldehydoguajacolcarboxylic acid is heated, carbonic acid is split off and it remains Aldehydoguajacol, that is vanillin, back:
,COOH, COOH
= CO. = CO.
/OH \COHS / OH \ COH S
Diese Abspaltung der Kohlensäure geschieht am besten durch Erhitzen der freien Säure oder eines ihrer Salze, z. B. des Silbersalzes, über 1800C. Man kann auch Wasser, verdünnte Säure, Salzlösungen oder irgend eine andere nicht direct reagirende Flüssigkeit hinzusetzen und führt dann die Kohlensäureabspaltung zweckmäfsig im Druckapparat aus.This splitting off of the carbonic acid is best done by heating the free acid or one of its salts, e.g. As the silver salt, over 180 0 C. One can also add water, dilute acid, salt solutions, or any other non-direct reagirende liquid and the carbon dioxide elimination leads zweckmäfsig from the printing apparatus.
Statt der Aldehydoguajacolcarbonsäure kann man auch Abkömmlinge derselben, wie Amid, Ester u. s. w., anwenden, welche während des Erhitzens durch das Wasser zunächst verseift werden.Instead of the aldehydoguajacolcarboxylic acid, one can also use its derivatives, such as amide, Use esters and the like, which are initially saponified during heating by the water will.
Man erhitzt Aldehydoguajacolcarbonsäure mit ungefähr der doppelten Menge Wasser im geschlossenen Gefäfs auf ca. 200° C. Beim Oeffnen des Gefäfses nach dem Erkalten entweicht Kohlensäure. Das darin befindliche rohe Vanillin ist meist noch ölförmig und wird durch Umkrystallisiren aus Wasser oder Ligroin gereinigt.Aldehydoguajacolcarbonsäure is heated with about twice the amount of water in the closed vessel to approx. 200 ° C. When the vessel is opened, it escapes after it has cooled down Carbonic acid. The raw vanillin in it is mostly still in the form of an oil and becomes purified by recrystallization from water or ligroin.
Claims (1)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE72600C true DE72600C (en) |
Family
ID=345810
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT72600D Expired - Lifetime DE72600C (en) | Method for the preparation of vanillin |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE72600C (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2730730A1 (en) * | 1995-02-20 | 1996-08-23 | Rhone Poulenc Chimie | PROCESS FOR THE PREPARATION OF SUBSTITUTED 4-HYDROXYBENZALDEHYDE |
| WO1996037454A1 (en) * | 1995-05-24 | 1996-11-28 | Rhone-Poulenc Chimie | Method for preparing 3-carboxy-4-hydroxybenzaldehydes and derivatives thereof |
| WO1998022419A1 (en) * | 1996-11-22 | 1998-05-28 | Rhodia Chimie | Method for preparing a 4-hydroxybenzaldehyde and derivatives |
-
0
- DE DENDAT72600D patent/DE72600C/en not_active Expired - Lifetime
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2730730A1 (en) * | 1995-02-20 | 1996-08-23 | Rhone Poulenc Chimie | PROCESS FOR THE PREPARATION OF SUBSTITUTED 4-HYDROXYBENZALDEHYDE |
| WO1996026175A1 (en) * | 1995-02-20 | 1996-08-29 | Rhone-Poulenc Chimie | Method for preparing a substituted 4-hydroxybenzaldehyde |
| US5756853A (en) * | 1995-02-20 | 1998-05-26 | Rhone-Poulenc Chimie | Process for the preparation of a substituted 4-hydroxybenzaldehyde |
| WO1996037454A1 (en) * | 1995-05-24 | 1996-11-28 | Rhone-Poulenc Chimie | Method for preparing 3-carboxy-4-hydroxybenzaldehydes and derivatives thereof |
| FR2734565A1 (en) * | 1995-05-24 | 1996-11-29 | Rhone Poulenc Chimie | PROCESS FOR THE PREPARATION OF 3-CARBOXY-4-HYDROXYBENZALDEHYDES AND DERIVATIVES |
| CN1082942C (en) * | 1995-05-24 | 2002-04-17 | 罗纳·布朗克化学公司 | Method for preparing 3-carboxy-4-hydroxybenzaldehydes and derivatives thereof |
| WO1998022419A1 (en) * | 1996-11-22 | 1998-05-28 | Rhodia Chimie | Method for preparing a 4-hydroxybenzaldehyde and derivatives |
| FR2756278A1 (en) * | 1996-11-22 | 1998-05-29 | Rhodia Chimie Sa | PROCESS FOR THE PREPARATION OF A 4-HYDROXYBENZALDEHYDE AND DERIVATIVES |
| US6184421B1 (en) * | 1996-11-22 | 2001-02-06 | Rhodia Chimie | Method for preparing a 4-hydroxybenzaldehyde and derivatives |
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