GB812064A - Improvements in or relating to the production of aromatic aldehydes - Google Patents
Improvements in or relating to the production of aromatic aldehydesInfo
- Publication number
- GB812064A GB812064A GB21933/55A GB2193355A GB812064A GB 812064 A GB812064 A GB 812064A GB 21933/55 A GB21933/55 A GB 21933/55A GB 2193355 A GB2193355 A GB 2193355A GB 812064 A GB812064 A GB 812064A
- Authority
- GB
- United Kingdom
- Prior art keywords
- hydrofluoric acid
- boron trifluoride
- fluoborate
- synthesis
- fluoride
- 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
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/49—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with carbon monoxide
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- B01J27/06—Halogens; Compounds thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
<PICT:0812064/III/1> A reaction mixture containing an aldehydeboron trifluoride-hydrofluoric acid complex and obtained from a continuous aromatic aldehyde synthesis using an aromatic hydrocarbon, carbon monoxide and a boron trifluoride-hydrofluoric acid catalyst, is treated with at least the stoichiometrically correct quantity of barium fluoride or strontium fluoride which is required to combine the boron trifluoride to form the metal fluoborate and at the same time to liberate hydrofluoric acid from the complex in an anhydrous state. The liberated hydrofluoric acid may be removed from the mixture by distillation or evaporation before or after the metal fluoborate is removed, and condensed and recycled to the synthesis. The fluoborate may be heated in a revolving drum to liberate the metal fluoride and boron trifluoride both of which may be used again. In a preferred embodiment, complex from aldehyde synthesis reactor 1 is depressurized in 2 and continuously run into each of the stirrer vessels 3 or 3a in turn. In 3 or 3a barium fluoride in toluene from 4 is run in to combine with the boron trifluoride only. Liberated hydrofluoric acid is drawn off by vacuum and condensed in cooler 7 and recycled to the synthesis at 1. The fluorborate slurry is run out of 3 or 3a, centrifuged in 10 and the filtrate processed to recover aldehyde. The fluoborate is heated in drum 12 to liberate boron trifluoride which may be recycled to the synthesis and barium fluoride which may be recycled to the decomposition. An example is given.ALSO:In a continuous process for making aromatic aldehydes from aromatic hydrocarbons and carbon monoxide in the presence of boron trifluoride and hydrofluoric acid as catalysts, the reaction mixture comprising an organic aldehyde-boron trifluoride-hydrofluoric acid complex, excess hydrofluoric acid and aromatic hydrocarbon and discharged from the reaction zone is treated with at least the stoichiometrically correct quantity of barium fluoride or strontium fluoride which is required to combine with the boron trifluoride to form a metal fluoborate and at the same time to liberate hydrofluoric acid from the complex in an anhydrous state. The liberated hydrofluoric acid may be removed from the mixture by distillation or by a vacuum pump either before or after the metal fluoborate is removed by centrifuging or filtration. The recovered fluoborate may be heated in a revolving drum to liberate the metal fluoride and boron trifluoride both of which may be used in the process again. The hydrofluoric acid may be condensed and recycled to the synthesis. The metal fluoride may be added to the reaction mixture in an inert vehicle such as toluene or benzene. In a preferred embodiment, the reaction mixture from the aldehyde synthesis is run continuously into each of at least two vessels in turn. One of these vessels is always in operation decomposing the complex, the reaction mixture being discharged continuously into one or other of the vessels. The calculated amount of barium or strontium fluoride is added to the reaction mixture in the vessel with stirring, free hydrofluoric acid is removed under vacuum and with slight heating and the mixture is run out of the vessel. The metal fluoborate is removed and the aldehyde obtained from the filtrate by distillation. An example illustrating the preparation of p-tolualdehyde from toluene is given. The aldehyde synthesis is conducted by continuously injecting the aromatic hydrocarbon, anhydrous hydrofluoric acid, gaseous boron trifluoride and carbon monoxide into a reactor vessel under 50-150 atmospheres pressure, the reaction mixture being continuously pumped through a condenser connected across the reaction vessel and maintained at -30 DEG to +20 DEG C.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE812064X | 1954-08-02 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB812064A true GB812064A (en) | 1959-04-15 |
Family
ID=6729397
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB21933/55A Expired GB812064A (en) | 1954-08-02 | 1955-07-29 | Improvements in or relating to the production of aromatic aldehydes |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB812064A (en) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP1044990A1 (en) * | 1998-10-29 | 2000-10-18 | Nippon Petrochemicals Company, Limited | Method of removing and recovering boron trifluoride with metal fluoride and process for polyolefin production using the same |
CN111167198A (en) * | 2019-03-29 | 2020-05-19 | 江西粤磁稀土新材料科技有限公司 | Filtration recovery unit of tombarthite |
-
1955
- 1955-07-29 GB GB21933/55A patent/GB812064A/en not_active Expired
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP1044990A1 (en) * | 1998-10-29 | 2000-10-18 | Nippon Petrochemicals Company, Limited | Method of removing and recovering boron trifluoride with metal fluoride and process for polyolefin production using the same |
EP1044990A4 (en) * | 1998-10-29 | 2001-10-31 | Nippon Petrochemicals Co Ltd | Method of removing and recovering boron trifluoride with metal fluoride and process for polyolefin production using the same |
CN111167198A (en) * | 2019-03-29 | 2020-05-19 | 江西粤磁稀土新材料科技有限公司 | Filtration recovery unit of tombarthite |
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