CN102030624B - Preparation method of 2,3,5,6-tetrachloro-terephthalaldehyde - Google Patents
Preparation method of 2,3,5,6-tetrachloro-terephthalaldehyde Download PDFInfo
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- CN102030624B CN102030624B CN 201010285257 CN201010285257A CN102030624B CN 102030624 B CN102030624 B CN 102030624B CN 201010285257 CN201010285257 CN 201010285257 CN 201010285257 A CN201010285257 A CN 201010285257A CN 102030624 B CN102030624 B CN 102030624B
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- phenylene
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Abstract
The invention discloses a preparation method of 2,3,5,6-tetrachloro-terephthalaldehyde, comprising the following steps: carrying out an oxidation reaction on 2,3,5,6-tetrachloro-p-dibenzyl chloride, nitric acid and vanadium pentoxide, and then collecting the target product from the reaction products. The method provided by the invention has high yield above 88%, is simple in operation, almost has no waste acid, has low production cost, and is easy for industrialization.
Description
Technical field
The present invention relates to the preparation method of 2,3,5,6-tetrachloro-p-phenylene dicarbaldehyde.
Background technology
2,3,5,6-tetrachloro-p-phenylene dicarbaldehyde is a kind of medicine, chemistry of pesticide intermediate, has in fields such as medicine, agricultural chemicals very widely to use.Mainly contain at present following several preparation method:
Document Ger360414, Neth6408879, Us3146086, Russian chemicalBulletin, 46 (1), 101, mention with a, a, à, à, 2,3,5,6-eight chlorine are that raw material is hydrolyzed in the vitriol oil and obtains target product 2,3,5 to dimethyl benzene, 6-tetrachloro-p-phenylene dicarbaldehyde, productive rate approximately 60% can produce a large amount of spent acid simultaneously.
Document J.O.C, 48 (5), 727,1983 to mention with 2,3,5,6-tetrachloro-p-phenylene dimethanol be that raw material prepares 2,3,5,6-tetrachloro-p-phenylene dicarbaldehyde, productive rate: 40.4% by oxidation.
Also have document DE2201251 to represent to be raw material with 2,3,5,6-tetrachloro-p-phenylene benzyl dichloride, hydrolysis obtains 2,3,5,6-tetrachloro-p-phenylene dicarbaldehyde in frozen water after reacting with SO3, but yield is not high, produces equally a large amount of spent acid.
To sum up, described above method or raw material is more expensive, or have very large shortcoming, so must seek other preparation method.
Summary of the invention
The technical issues that need to address of the present invention be disclose a kind of new 2,3,5, the synthetic method of 6-tetrachloro-p-phenylene dicarbaldehyde, the defects that exists to overcome prior art.
Method of the present invention comprises the steps:
Described method comprises the following steps: with 2,3,5,6-tetrachloro-p-phenylene benzyl dichloride, weight concentration are the rare nitric acid of 5-10% and Vanadium Pentoxide in FLAKES under 120-150 ℃, 0.25-1Mpa pressure, oxidizing reaction 15-20 hour, then collect target product from reaction product;
Reaction formula is as follows:
Wherein, nitric acid is oxygenant, and Vanadium Pentoxide in FLAKES is catalyzer;
Described method of collecting target product from reaction product comprises the steps:
Reaction product is cooling, filter, then use acetone and water recrystallization, mother liquor is removed after HCL can be by adding recycle after nitric acid.
Weight concentration is that the nitric acid of 5-10% and the weight ratio of 2,3,5,6-tetrachloro-p-phenylene benzyl dichloride are 5～20: 1;
The weight ratio of Vanadium Pentoxide in FLAKES and 2,3,5,6-tetrachloro-p-phenylene benzyl dichloride is 0.03～0.1: 1;
Method of the present invention, productive rate can reach more than 88%, and be easy and simple to handle, almost low without spent acid, production cost, is convenient to industrialization.
Embodiment
Embodiment 1
With 31.3 grams 2,3,5,6-tetrachloro-p-phenylene benzyl dichloride, 600 gram weight concentration are that 5% rare nitric acid and 1.5 gram Vanadium Pentoxide in FLAKESs add in autoclave pressure, then oxidizing reaction 20 hours under 150 ℃, 0.8MPa pressure.Then cooling, filtration heavily tie with acetone and water.Dry 23 grams 2,3,5,6-tetrachloro-p-phenylene dicarbaldehyde, productive rate approximately 85%.Mother liquor is removed after HCL can be by adding recycle after nitric acid.
Embodiment 2
With 31.3 grams 2,3,5,6-tetrachloro-p-phenylene benzyl dichloride, 400 gram weight concentration are that 10% rare nitric acid and 1 gram Vanadium Pentoxide in FLAKES add in autoclave pressure, then oxidation 20 hours under 120 ℃, 0.25MPa pressure.Then cooling, filtration heavily tie with acetone and water.Dry 20.5 grams 2,3,5,6-tetrachloro-p-phenylene dicarbaldehyde, productive rate approximately 75%.Mother liquor is removed after HCL can be by adding recycle after nitric acid.
Embodiment 3
With 31.3 grams 2,3,5,6-tetrachloro-p-phenylene benzyl dichloride, the 600 rare nitric acid of gram weight concentration 8% and 1.5 gram Vanadium Pentoxide in FLAKESs add in autoclave pressure, then oxidation 20 hours under 150 ℃, 0.5MPa pressure.Then cooling, filtration heavily tie with acetone and water.Dry 24 grams 2,3,5,6-tetrachloro-p-phenylene dicarbaldehyde, productive rate approximately 88%.Mother liquor is removed after HCL can be by adding recycle after nitric acid.
Embodiment 4
With 31.3 grams 2,3,5,6-tetrachloro-p-phenylene benzyl dichloride, the 600 rare nitric acid of gram weight concentration 8% and 3 gram Vanadium Pentoxide in FLAKESs add in autoclave pressure, then oxidation 15 hours under 150 ℃, 0.5MPa pressure.Then cooling, filtration heavily tie with acetone and water.Dry 22.5 grams 2,3,5,6-tetrachloro-p-phenylene dicarbaldehyde, productive rate approximately 82%.Mother liquor is removed after HCL can be by adding recycle after nitric acid.
Claims (2)
1. one kind 2,3,5, the preparation method of 6-tetrachloro-p-phenylene dicarbaldehyde is characterized in that, comprises the steps: 2,3,5,6-tetrachloro-p-phenylene benzyl dichloride, nitric acid and Vanadium Pentoxide in FLAKES are carried out oxidizing reaction, then collects target product from reaction product;
The weight concentration of acid is 5-10%;
Temperature of reaction is 120-150 ℃;
Reaction pressure is 0.25-1Mpa;
Reaction times is 15-20 hour;
Weight concentration is that the nitric acid of 5-10% and the weight ratio of 2,3,5,6-tetrachloro-p-phenylene benzyl dichloride are 5～20: 1;
The weight ratio of Vanadium Pentoxide in FLAKES and 2,3,5,6-tetrachloro-p-phenylene benzyl dichloride is 0.03～0.1: 1.
2. method according to claim 1, is characterized in that, described method of collecting target product from reaction product, comprise the steps: reaction product is cooling, filtration, then use acetone and water recrystallization, after mother liquor is removed HCl, add recycle after nitric acid.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 201010285257 CN102030624B (en) | 2010-09-17 | 2010-09-17 | Preparation method of 2,3,5,6-tetrachloro-terephthalaldehyde |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 201010285257 CN102030624B (en) | 2010-09-17 | 2010-09-17 | Preparation method of 2,3,5,6-tetrachloro-terephthalaldehyde |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN102030624A CN102030624A (en) | 2011-04-27 |
| CN102030624B true CN102030624B (en) | 2013-06-05 |
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| Application Number | Title | Priority Date | Filing Date |
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| CN 201010285257 Active CN102030624B (en) | 2010-09-17 | 2010-09-17 | Preparation method of 2,3,5,6-tetrachloro-terephthalaldehyde |
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| CN (1) | CN102030624B (en) |
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2010
- 2010-09-17 CN CN 201010285257 patent/CN102030624B/en active Active
Non-Patent Citations (2)
| Title |
|---|
| 催化水解氧化法制备苯甲醛的研究;李金志;《化工时刊》;20001031;第26页右栏 * |
| 李金志.催化水解氧化法制备苯甲醛的研究.《化工时刊》.2000,第26页右栏. |
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| CN102030624A (en) | 2011-04-27 |
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