GB816253A - Improvements relating to the production of benzaldehyde from toluene - Google Patents
Improvements relating to the production of benzaldehyde from tolueneInfo
- Publication number
- GB816253A GB816253A GB154757A GB154757A GB816253A GB 816253 A GB816253 A GB 816253A GB 154757 A GB154757 A GB 154757A GB 154757 A GB154757 A GB 154757A GB 816253 A GB816253 A GB 816253A
- Authority
- GB
- United Kingdom
- Prior art keywords
- toluene
- chlorination
- benzaldehyde
- chloride
- benzal
- 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
- YXFVVABEGXRONW-UHFFFAOYSA-N toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 title abstract 16
- HUMNYLRZRPPJDN-UHFFFAOYSA-N Benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 title abstract 9
- 229940095076 benzaldehyde Drugs 0.000 title abstract 4
- 238000004519 manufacturing process Methods 0.000 title abstract 2
- CAHQGWAXKLQREW-UHFFFAOYSA-N Benzal chloride Chemical compound ClC(Cl)C1=CC=CC=C1 CAHQGWAXKLQREW-UHFFFAOYSA-N 0.000 abstract 5
- 238000005660 chlorination reaction Methods 0.000 abstract 4
- 239000000460 chlorine Substances 0.000 abstract 3
- 229910052801 chlorine Inorganic materials 0.000 abstract 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 3
- 238000000034 method Methods 0.000 abstract 3
- KCXMKQUNVWSEMD-UHFFFAOYSA-N Benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 abstract 2
- 229940073608 benzyl chloride Drugs 0.000 abstract 2
- 238000006243 chemical reaction Methods 0.000 abstract 2
- 230000005484 gravity Effects 0.000 abstract 2
- 238000010992 reflux Methods 0.000 abstract 2
- FAIAAWCVCHQXDN-UHFFFAOYSA-N Phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 abstract 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 1
- 230000005587 bubbling Effects 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 239000011521 glass Substances 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- 230000003301 hydrolyzing Effects 0.000 abstract 1
- 239000007791 liquid phase Substances 0.000 abstract 1
- 239000002184 metal Substances 0.000 abstract 1
- 229910052751 metal Inorganic materials 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 238000006396 nitration reaction Methods 0.000 abstract 1
- 235000011149 sulphuric acid Nutrition 0.000 abstract 1
- 239000001117 sulphuric acid Substances 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 abstract 1
- 239000011701 zinc Substances 0.000 abstract 1
- 229910052725 zinc Inorganic materials 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
- C07C17/10—Preparation of halogenated hydrocarbons by replacement by halogens of hydrogen atoms
- C07C17/14—Preparation of halogenated hydrocarbons by replacement by halogens of hydrogen atoms in the side-chain of aromatic compounds
-
- 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
- C07C45/42—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by hydrolysis
- C07C45/43—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by hydrolysis of >CX2 groups, X being halogen
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
A process for the production of benzaldehyde comprises reacting toluene at elevated temperatures in the liquid phase with chlorine until no more than about 35 per cent of the toluene has been converted to benzal chloride, distilling the reaction mass to separate the benzal chloride and hydrolysing the benzal chloride to benzaldehyde. The toluene should be dry and substantially pure, e.g. nitration grade toluene. The chlorination may be effected by bubbling chlorine into toluene or refluxing toluene in the presence of gaseous chlorine. The chlorination may take place in the presence of ultra-violet light or phosphorus trichloride. Plastic or glass reaction vessels should be used; the use of metal-containing catalysts or equipment being avoided. The hydrolysis may be effected with aqueous sulphuric acid, steam and compounds of zinc or water. In examples: toluene is chlorinated under reflux whilst exposed to ultra-violet light, until the specific gravity rises to 1-16 at room temperature. The chlorinated product is fractionated and the benzal chloride fraction is hydrolysed with steam to obtain benzaldehyde (1), and in a similar process the chlorination is discontinued when the specific gravity rises to 1.02 at room temperature (2). Other fractions obtained contain benzyl chloride and mixtures of benzyl and benzal chlorides. The benzyl chloride may be returned to the chlorination process.
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB816253A true GB816253A (en) | 1959-07-08 |
Family
ID=1626879
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB154757A Expired GB816253A (en) | 1957-01-15 | Improvements relating to the production of benzaldehyde from toluene |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB816253A (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3089908A (en) * | 1960-09-06 | 1963-05-14 | Pittsburgh Chemical Company | Preparation of terephthalaldehyde from xylene dichloride |
| EP0011281A2 (en) * | 1978-11-16 | 1980-05-28 | Hoechst Aktiengesellschaft | Process for the preparation of p-tert.-butyl benzaldehyde and the derivatives thereof substituted in the nucleus by halogen. |
| EP0045429A2 (en) * | 1980-08-01 | 1982-02-10 | Bayer Ag | Process for the preparation of 4-tert. butylbenzaldehydes |
| US4450298A (en) * | 1981-07-21 | 1984-05-22 | Central Glass Company, Limited | Vapor phase catalytic hydrolysis of benzal chloride or its halogen- or trifluoromethyl-substitute to form benzaldehyde or substitute |
| CN114456049A (en) * | 2022-01-24 | 2022-05-10 | 连云港市工投集团利海化工有限公司 | Preparation method and device of benzaldehyde |
-
1957
- 1957-01-15 GB GB154757A patent/GB816253A/en not_active Expired
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3089908A (en) * | 1960-09-06 | 1963-05-14 | Pittsburgh Chemical Company | Preparation of terephthalaldehyde from xylene dichloride |
| EP0011281A2 (en) * | 1978-11-16 | 1980-05-28 | Hoechst Aktiengesellschaft | Process for the preparation of p-tert.-butyl benzaldehyde and the derivatives thereof substituted in the nucleus by halogen. |
| EP0011281A3 (en) * | 1978-11-16 | 1980-09-03 | Hoechst Aktiengesellschaft | Process for the preparation of p-tert.-butyl benzaldehyde and the derivatives thereof substituted in the nucleus by halogen, p.-tert. butylbenzal bromide formed thereby as intermediate and the derivatives thereof substituted in the nucleus by halogen |
| US4277421A (en) * | 1978-11-16 | 1981-07-07 | Hoechst Aktiengesellschaft | Process for the manufacture of para-tert.butylbenzaldehyde and its derivatives which are halogen-substituted at the nucleus |
| EP0045429A2 (en) * | 1980-08-01 | 1982-02-10 | Bayer Ag | Process for the preparation of 4-tert. butylbenzaldehydes |
| EP0045429A3 (en) * | 1980-08-01 | 1982-03-17 | Bayer Ag | Process for the preparation of 4-tert. butylbenzaldehydes |
| US4450298A (en) * | 1981-07-21 | 1984-05-22 | Central Glass Company, Limited | Vapor phase catalytic hydrolysis of benzal chloride or its halogen- or trifluoromethyl-substitute to form benzaldehyde or substitute |
| CN114456049A (en) * | 2022-01-24 | 2022-05-10 | 连云港市工投集团利海化工有限公司 | Preparation method and device of benzaldehyde |
| CN114456049B (en) * | 2022-01-24 | 2023-02-17 | 连云港市工投集团利海化工有限公司 | Preparation device of benzaldehyde |
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