DE20909C - Innovations in the process for the preparation of benzaldehyde - Google Patents
Innovations in the process for the preparation of benzaldehydeInfo
- Publication number
- DE20909C DE20909C DENDAT20909D DE20909DA DE20909C DE 20909 C DE20909 C DE 20909C DE NDAT20909 D DENDAT20909 D DE NDAT20909D DE 20909D A DE20909D A DE 20909DA DE 20909 C DE20909 C DE 20909C
- Authority
- DE
- Germany
- Prior art keywords
- benzaldehyde
- chloride
- preparation
- molecules
- innovations
- 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.)
- Active
Links
- HUMNYLRZRPPJDN-UHFFFAOYSA-N Benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 title claims description 9
- 229940095076 benzaldehyde Drugs 0.000 title claims description 4
- 238000000034 method Methods 0.000 title description 3
- NUJOXMJBOLGQSY-UHFFFAOYSA-N Manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 claims description 6
- 229940073608 benzyl chloride Drugs 0.000 claims description 6
- KCXMKQUNVWSEMD-UHFFFAOYSA-N Benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 claims description 5
- 239000000203 mixture Substances 0.000 claims description 5
- CAHQGWAXKLQREW-UHFFFAOYSA-N Benzal chloride Chemical compound ClC(Cl)C1=CC=CC=C1 CAHQGWAXKLQREW-UHFFFAOYSA-N 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- AGEZXYOZHKGVCM-UHFFFAOYSA-N Benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 claims description 2
- VCJZTATVUDMNLU-UHFFFAOYSA-N dibromomethylbenzene Chemical compound BrC(Br)C1=CC=CC=C1 VCJZTATVUDMNLU-UHFFFAOYSA-N 0.000 claims description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- 230000000875 corresponding Effects 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 2
- SNLOCRBUBDQVOC-UHFFFAOYSA-N (1,1-dichloro-2-phenylethyl)benzene Chemical class C=1C=CC=CC=1C(Cl)(Cl)CC1=CC=CC=C1 SNLOCRBUBDQVOC-UHFFFAOYSA-N 0.000 description 1
- 229910018663 Mn O Inorganic materials 0.000 description 1
- 150000003935 benzaldehydes Chemical class 0.000 description 1
- 150000005524 benzylchlorides Chemical class 0.000 description 1
- 150000001649 bromium compounds Chemical class 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 230000005484 gravity Effects 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 229910000464 lead oxide Inorganic materials 0.000 description 1
- 239000011572 manganese Substances 0.000 description 1
- 238000010992 reflux Methods 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
- C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
KAISERLICHESIMPERIAL
PATENTAMTPATENT OFFICE
Dieses Verfahren bezweckt die Darstellung von Benzaldehyd, dessen Homologen' und Substitutionsproducten durch Einwirkung von in Wasser vertheiltem Mangandioxyd auf ein Gemenge von wesentlich 2 Molecülen Benzylchlorid und ι Molecül Benzalchlorid oder 2 Molecülen Benzylbromid und 1 Molecül Benzalbromid oder auf entsprechende Gemenge ihrer Homologen und Substitutionsproducte. Der Procefs vollzieht sich in glatter Weise nach folgender Gleichung:The purpose of this process is to prepare benzaldehyde, its homologues and substitution products by the action of manganese dioxide dispersed in water on a mixture of essentially 2 molecules of benzyl chloride and ι Molecül Benzalchlorid or 2 Molecül benzyl bromide and 1 Molecül benzal bromide or to a corresponding mixture of their homologues and substitution products. The Procefs perform in a smooth manner according to the following equation:
2 C6Jy5. CIP Cl-\-Cs H*. CHCP + 2 Mn O2 = 3 C6 Hb. CBO-+- 2 Mn CP -+■ H2 O. 2 C 6 Jy 5 . CIP Cl - \ - C s H * . CHCP + 2 Mn O 2 = 3 C 6 H b . CBO - + - 2 Mn CP - + ■ H 2 O.
Durch Weiterchloriren des aus dem Toluol dargestellten Benzylchlorids bis annähernd zum specifischen Gewicht 1,17s erhält man das erforderliche Gemisch von wesentlich 2 Molecülen Benzylchlorid und 1 Molecül Benzalchlorid.By further chlorination of the benzyl chloride prepared from the toluene up to approximately specific gravity 1.17s one obtains the required Mixture of essentially 2 molecules of benzyl chloride and 1 molecule of benzal chloride.
Specielles Verfahren.Special procedure.
Ein Gemisch von 2 Molecülen Benzylchlorid und ι Molecül Benzalchlorid wird mit der sechsfachen Menge Wasser versetzt, worauf 2 Molecule Mangandioxyd oder die entsprechende Menge fein pulverisirten Braunsteins zugefügt werden. Man kocht am Rückfiufskühler so lange, bis alles Chlorid in Aldehyd übergeführt ist. Der Aldehyd wird mit Wasserdampf abdestillirt und in bekannter Weise gereinigt.A mixture of 2 molecules of benzyl chloride and ι Molecül benzal chloride is sixfold Amount of water added, whereupon 2 molecules of manganese dioxide or the corresponding amount finely powdered brown stones are added. You cook on the reflux cooler until everything Chloride is converted into aldehyde. The aldehyde is distilled off with steam and in a known manner Way cleaned.
Von substituirtem Benzyl-Benzalchlorid ausgehend, können in derselben Weise substituirte Benzaldehyde gewonnen werden. Die Chloride können durch die Bromide ersetzt werden. Die Operation kann auch unter Druck ausgeführt werden. Bei Anwendung der Oxyde des Bleies und Eisens wird in derselben Weise Benzaldehyd erhalten. Statt Wasser kann beispielsweise Alkohol zugesetzt werden.Starting from substituted benzyl benzal chloride, substituted benzyl chloride can be used in the same way Benzaldehydes are obtained. The chlorides can be replaced by the bromides. the Operation can also be performed under pressure. When using lead oxides and iron, benzaldehyde is obtained in the same way. Instead of water, for example, alcohol can be added.
Claims (1)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE20909C true DE20909C (en) |
Family
ID=297622
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT20909D Active DE20909C (en) | Innovations in the process for the preparation of benzaldehyde |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE20909C (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4317934A (en) * | 1980-08-15 | 1982-03-02 | Ethyl Corporation | Preparation of carbonyl compounds |
-
0
- DE DENDAT20909D patent/DE20909C/en active Active
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4317934A (en) * | 1980-08-15 | 1982-03-02 | Ethyl Corporation | Preparation of carbonyl compounds |
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