CN107778152B - Preparation method of 4-tert-butyl phthalaldehyde - Google Patents
Preparation method of 4-tert-butyl phthalaldehyde Download PDFInfo
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- CN107778152B CN107778152B CN201710936156.4A CN201710936156A CN107778152B CN 107778152 B CN107778152 B CN 107778152B CN 201710936156 A CN201710936156 A CN 201710936156A CN 107778152 B CN107778152 B CN 107778152B
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- 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
- C07C45/32—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen
- C07C45/33—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen of CHx-moieties
- C07C45/34—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen of CHx-moieties in unsaturated compounds
- C07C45/36—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen of CHx-moieties in unsaturated compounds in compounds containing six-membered aromatic rings
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Abstract
The invention discloses a preparation method of 4-tert-butyl phthalic aldehyde, belonging to the technical field of organic synthesis. The technical scheme provided by the invention has the key points that: a preparation method of 4-tert-butyl phthalic aldehyde comprises the following specific steps: the 4-tert-butyl ortho-xylene is used as an initial raw material, a mixture of silver carbonate, copper acetylacetonate, manganese acetate, cobalt acetate, nickel acetate, ammonium molybdate and selenium dioxide is used as a mixed catalyst, air is used as an oxidant, and the mixture is reacted at the temperature of 150 ℃ and 200 ℃ to prepare the 4-tert-butyl ortho-phthalaldehyde. The method has the advantages of mild reaction conditions, high yield and low cost, is suitable for industrial production, and is a synthetic method with industrial production value.
Description
Technical Field
The invention belongs to the technical field of organic synthesis, and particularly relates to a preparation method of 4-tert-butyl phthalic aldehyde.
Background
The aldehyde group is an important functional group in organic chemistry, and can be subjected to a plurality of transformations, such as aldehyde group reduction to obtain alcohol, oxidation to obtain acid, and amination and dehydration to obtain cyano. In modern chemical industry, catalytic oxidation is one of the main technologies in organic synthesis production and is also a key technology for promoting economic development of China. However, the currently used techniques have some drawbacks and deficiencies, which limit the application of these techniques in industrial production. The method for preparing aldehyde groups is the most difficult and promising method for selectively oxidizing hydrocarbon compounds to generate aldehyde, and one of the difficulties lies in the preparation control of the catalyst, and different substrates have different requirements on the performance of the catalyst, which is almost equivalent to the requirement that one substrate needs to establish a catalytic system.
4-tert-butyl o-phthalaldehyde is an important organic chemical raw material, can be further used for preparing 4-tert-butyl phthalonitrile and is applied to the preparation of phthalocyanine. The prior publication reports that 4-tert-butyl-o-phthalaldehyde is obtained by brominating and hydrolyzing 4-tert-butyl-o-xylene (1996, JP 08245478). although 4-tert-butyl-o-xylene is used as a raw material for the reaction and the two-step reaction is carried out, bromine is needed, the cost is high, and the yield is only 78%. The similar structure is the preparation of phthalic aldehyde, and the preparation method has a few reports in documents, but the direct oxidation of o-xylene is rare. Patent publication No. CN 106552622A discloses that O-xylene is used as a raw material to prepare O-phthalaldehyde, and the prepared V-Ag-Si-O catalyst is used for catalyzing and oxidizing O-xylene to prepare O-phthalaldehyde, wherein the yield is 73 percent. Therefore, the establishment of the synthesis method of the 4-tert-butyl o-phthalaldehyde with mild reaction conditions has practical significance.
Disclosure of Invention
The technical problem to be solved by the invention is to provide a preparation method of 4-tert-butyl phthalic aldehyde, which has the advantages of mild reaction conditions, higher yield and low cost and is suitable for industrial production.
The invention adopts the following technical scheme for solving the technical problems, and the preparation method of the 4-tert-butyl phthalic aldehyde is characterized by comprising the following specific processes: the method comprises the steps of taking 4-tert-butyl ortho-xylene as an initial raw material, taking a mixture of silver carbonate, copper acetylacetonate, manganese acetate, cobalt acetate, nickel acetate, ammonium molybdate and selenium dioxide as a mixed catalyst, taking air as an oxidant, and reacting at the temperature of 150 ℃ and 200 ℃ to prepare the 4-tert-butyl ortho-phthalaldehyde, wherein the molar ratio of the silver carbonate to the copper acetylacetonate to the manganese acetate to the cobalt acetate to the nickel acetate to the ammonium molybdate to the selenium dioxide is 0.5-1:1:1:1:1: 1-2.
Further preferably, the feeding weight ratio of the 4-tert-butyl-o-xylene to the mixed catalyst is 1: 0.2-0.5.
Further preferably, the preparation method of the 4-tert-butyl phthalic aldehyde is characterized by comprising the following specific steps: adding 162 g of 4-tert-butyl o-xylene and 45g of mixed catalyst into a high-pressure reaction kettle, wherein the molar ratio of silver carbonate to copper acetylacetonate to manganese acetate to cobalt acetate to nickel acetate to ammonium molybdate to selenium dioxide is 0.8:1:1:1:1: 1.5, heating to 180 ℃ for reaction, adding a dichloromethane solvent after the reaction is finished, filtering out insoluble substances, distilling and recovering dichloromethane to obtain 165 g of 4-tert-butyl o-phthalaldehyde, wherein the yield is 87%, and the purity is 99.0%.
Compared with the prior art, the invention has the following advantages: mild reaction conditions, high yield, low cost and suitability for industrial application.
Detailed Description
The present invention is described in further detail below with reference to examples, but it should not be construed that the scope of the above subject matter of the present invention is limited to the following examples, and that all the technologies realized based on the above subject matter of the present invention belong to the scope of the present invention.
Example 1
Adding 162 g (1.0 mol) of 4-tert-butyl o-xylene and 32.4g of mixed catalyst (silver carbonate: copper acetylacetonate: manganese acetate: cobalt acetate: nickel acetate: ammonium molybdate: selenium dioxide =0.5:1:1:1:1:1:1, molar ratio) into a high-pressure reaction kettle, heating to 150 ℃ for reaction, adding a dichloromethane solvent after the reaction is finished, filtering to remove insoluble substances, distilling and recovering dichloromethane to obtain 162 g of 4-tert-butyl o-phthalaldehyde, wherein the yield is 85%, and the purity is 98.5%.
Example 2
Adding 162 g (1.0 mol) of 4-tert-butyl o-xylene and 81 g of mixed catalyst (silver carbonate: copper acetylacetonate: manganese acetate: cobalt acetate: nickel acetate: ammonium molybdate: selenium dioxide =1:1:1:1:1: 2, molar ratio) into a high-pressure reaction kettle, heating to 200 ℃ for reaction, adding a dichloromethane solvent after the reaction is finished, filtering to remove insoluble substances, distilling and recovering dichloromethane to obtain 152 g of 4-tert-butyl o-phthalaldehyde, wherein the yield is 80%, and the purity is 98.0%.
Example 3
162 g (1.0 mol) of 4-tert-butyl o-xylene and 45g of mixed catalyst (silver carbonate: copper acetylacetonate: manganese acetate: cobalt acetate: nickel acetate: ammonium molybdate: selenium dioxide =0.8:1:1:1:1:1:1.5, molar ratio) are added into a high-pressure reaction kettle, the mixture is heated to 180 ℃ for reaction, a dichloromethane solvent is added after the reaction is finished, insoluble substances are filtered out, dichloromethane is distilled and recovered to obtain 165 g of 4-tert-butyl o-phthalaldehyde, the yield is 87%, and the purity is 99.0%.
Example 4
162 g (1.0 mol) of o-xylene and 32.4g of mixed catalyst (silver carbonate: copper acetylacetonate: manganese acetate: cobalt acetate: nickel acetate: ammonium molybdate: selenium dioxide =0.5:1:1:1:1:1, molar ratio) are added into a high-pressure reaction kettle, the mixture is heated to 150 ℃ for reaction, a dichloromethane solvent is added after the reaction is finished, insoluble substances are filtered out, dichloromethane is distilled and recovered to obtain 114 g of phthalaldehyde, the yield is 85%, and the purity is 99.5%.
The foregoing embodiments illustrate the principles, principal features and advantages of the invention, and it will be understood by those skilled in the art that the invention is not limited to the foregoing embodiments, which are merely illustrative of the principles of the invention, and that various changes and modifications may be made therein without departing from the scope of the principles of the invention.
Claims (1)
1. A preparation method of 4-tert-butyl phthalaldehyde is characterized by comprising the following specific steps: adding 162 g of 4-tert-butyl o-xylene and 45g of mixed catalyst into a high-pressure reaction kettle, wherein the molar ratio of silver carbonate to copper acetylacetonate to manganese acetate to cobalt acetate to nickel acetate to ammonium molybdate to selenium dioxide is 0.8:1:1:1:1: 1.5, heating to 180 ℃ for reaction, adding a dichloromethane solvent after the reaction is finished, filtering out insoluble substances, distilling and recovering dichloromethane to obtain 165 g of 4-tert-butyl o-phthalaldehyde, wherein the yield is 87%, and the purity is 99.0%.
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| CN201710936156.4A CN107778152B (en) | 2017-10-10 | 2017-10-10 | Preparation method of 4-tert-butyl phthalaldehyde |
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| CN201710936156.4A CN107778152B (en) | 2017-10-10 | 2017-10-10 | Preparation method of 4-tert-butyl phthalaldehyde |
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| CN107778152B true CN107778152B (en) | 2020-10-27 |
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| CN114524718B (en) * | 2022-01-25 | 2023-09-22 | 上海巽田科技股份有限公司 | Method for preparing high-purity phthalic dicarboxaldehyde from phthalic diester |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0925261A (en) * | 1995-07-13 | 1997-01-28 | Wako Pure Chem Ind Ltd | New production of phthalonitrile derivative |
| CN1663941A (en) * | 2004-03-01 | 2005-09-07 | 中国科学院大连化学物理研究所 | Process for synthesizing benzaldehyde by selective oxidation of toluene |
| CN102070382A (en) * | 2011-01-19 | 2011-05-25 | 山东瀛洋香精香料有限公司 | Method for preparing benzaldehyde or substituted benzaldehyde by catalytically oxidizing methylbenzene or substituted methylbenzene |
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2017
- 2017-10-10 CN CN201710936156.4A patent/CN107778152B/en active Active
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0925261A (en) * | 1995-07-13 | 1997-01-28 | Wako Pure Chem Ind Ltd | New production of phthalonitrile derivative |
| CN1663941A (en) * | 2004-03-01 | 2005-09-07 | 中国科学院大连化学物理研究所 | Process for synthesizing benzaldehyde by selective oxidation of toluene |
| CN102070382A (en) * | 2011-01-19 | 2011-05-25 | 山东瀛洋香精香料有限公司 | Method for preparing benzaldehyde or substituted benzaldehyde by catalytically oxidizing methylbenzene or substituted methylbenzene |
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