CN107778152A - A kind of preparation method of 4 tert-butyl o phthalaldehyde - Google Patents
A kind of preparation method of 4 tert-butyl o phthalaldehyde Download PDFInfo
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- CN107778152A CN107778152A CN201710936156.4A CN201710936156A CN107778152A CN 107778152 A CN107778152 A CN 107778152A CN 201710936156 A CN201710936156 A CN 201710936156A CN 107778152 A CN107778152 A CN 107778152A
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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 kind of preparation method of 4 tert-butyl o phthalaldehyde, belong to technical field of organic synthesis.Technical scheme main points are：A kind of preparation method of 4 tert-butyl o phthalaldehyde, detailed process are：Using 4 terting butyl-o-xylenes as initiation material, using the mixture of silver carbonate, acetylacetone copper, manganese acetate, cobalt acetate, nickel acetate, ammonium molybdate and selenium dioxide as mixed catalyst, using air as oxidant, 4 tert-butyl o phthalaldehydes are made in 150 200 DEG C of reactions.Reaction condition of the present invention is gentle, yield is higher, cost is cheap and suitable industrialized production, is a kind of synthetic method with industrial production value.
Description
Technical field
The invention belongs to technical field of organic synthesis, and in particular to a kind of preparation method of 4- tert-butyl os phthalaldehyde.
Background technology
Aldehyde radical is functional group important in organic chemistry, and aldehyde radical can be converted a lot, for example aldehyde radical reduction can obtain
Alcohol, oxidation can obtain acid, and cyano group can be converted into by being dehydrated after hydroxylamination.In modern chemical industry, catalysis oxidation is organic
One of major technique in synthetically produced, and promote the key technique of China's economic development.But the technology used at present
Also there is some shortcomings and deficiencies, so as to limit the application of these technologies in the industrial production.The method for preparing aldehyde radical has
A lot, wherein selective oxidation hydro carbons compound produces the method difficulty maximum of aldehyde, and also most one of prospect, its difficulty is
In the preparation control of catalyst, different substrates is different to the performance requirement of catalyst, and being almost equivalent to a substrate just needs
Want the foundation of a catalyst system and catalyzing.
4- tert-butyl o phthalaldehydes are important Organic Chemicals, can further prepare 4- tert-butyl group O-phthalics
Nitrile, the preparation applied to phthalocyanine.Open source literature report 4- tert-butyl o phthalaldehydes are by 4- terting butyl-o-xylenes at present
Bromination, hydrolysis obtain（1996, JP 08245478）Although reaction is that raw material passes through two-step reaction with 4- terting butyl-o-xylenes,
But need to use bromine, cost is higher, and yield only has 78%.Similar structure is the preparation of OPA therewith, preparation side
Method document report is although more, but directly passes through the seldom of o xylene oxidation.Publication No. CN 106552622A patent
Disclose and prepare OPA by raw material of ortho-xylene, adjacent diformazan is aoxidized by the V-Ag-Si-O catalysts of preparation
OPA, yield 73% is made in benzene, and shortcoming is that reaction temperature is too high, and catalyst preparation is complex.Therefore establish a kind of
The synthetic method of the gentle 4- tert-butyl o phthalaldehydes of reaction condition has practical significance.
The content of the invention
Present invention solves the technical problem that there is provided, a kind of reaction condition is gentle, yield is higher, cost is cheap and suitable
The preparation method of the 4- tert-butyl o phthalaldehydes of industrialized production.
The present invention is to solve above-mentioned technical problem to adopt the following technical scheme that, a kind of preparation of 4- tert-butyl os phthalaldehyde
Method, it is characterised in that detailed process is：Using 4- terting butyl-o-xylenes as initiation material, with silver carbonate, acetylacetone copper, vinegar
Sour manganese, cobalt acetate, nickel acetate, the mixture of ammonium molybdate and selenium dioxide are mixed catalyst, using air as oxidant, in 150-
200 DEG C of reactions are made 4- tert-butyl o phthalaldehydes, silver carbonate, acetylacetone copper, manganese acetate, acetic acid in the mixed catalyst
Cobalt, nickel acetate, the mol ratio of ammonium molybdate and selenium dioxide are 0.5-1:1:1:1:1:1:1-2.
Further preferably, the charged material weight ratio of the 4- terting butyl-o-xylenes and mixed catalyst is 1:0.2-0.5.
Further preferably, the preparation method of the 4- tert-butyl os phthalaldehyde, it is characterised in that concretely comprise the following steps：In height
Press and the g and g of mixed catalyst 45 of 4- terting butyl-o-xylenes 162 is added in reactor, silver carbonate, acetyl in the mixed catalyst
Acetone copper, manganese acetate, cobalt acetate, nickel acetate, the mol ratio of ammonium molybdate and selenium dioxide are 0.8:1:1:1:1:1:1.5, heating
To 180 DEG C of reactions, reaction adds dichloromethane solvent after terminating, and filters out insoluble matter, is distilled to recover dichloromethane and obtains 4-
The g of tert-butyl o phthalaldehyde 165, yield 87%, purity 99.0%.
The present invention has advantages below compared with prior art：Reaction condition is gentle, yield is higher, cost is cheap and is suitable to
Commercial application.
Embodiment
The above of the present invention is described in further details by the following examples, but this should not be interpreted as to this
The scope for inventing above-mentioned theme is only limitted to following embodiment, and all technologies realized based on the above of the present invention belong to this hair
Bright scope.
Embodiment 1
The g of 4- terting butyl-o-xylenes 162 is added in autoclave（1.0 mol）And mixed catalyst（Silver carbonate：Acetyl
Acetone copper：Manganese acetate：Cobalt acetate：Nickel acetate：Ammonium molybdate：Selenium dioxide=0.5:1:1:1:1:1:1, mol ratio）32.4 g, add
Heat to 150 DEG C of reactions, reaction adds dichloromethane solvent after terminating, and filters out insoluble matter, is distilled to recover dichloromethane and obtains
The g of 4- tert-butyl os phthalaldehyde 162, yield 85%, purity 98.5%.
Embodiment 2
The g of 4- terting butyl-o-xylenes 162 is added in autoclave（1.0 mol）And mixed catalyst（Silver carbonate：Acetyl
Acetone copper：Manganese acetate：Cobalt acetate：Nickel acetate：Ammonium molybdate：Selenium dioxide=1:1:1:1:1:1:2, mol ratio）81 g, are heated to
200 DEG C of reactions, reaction add dichloromethane solvent after terminating, and filter out insoluble matter, are distilled to recover dichloromethane and obtain uncle 4-
The g of butyl OPA 152, yield 80%, purity 98.0%.
Embodiment 3
The g of 4- terting butyl-o-xylenes 162 is added in autoclave（1.0 mol）And mixed catalyst（Silver carbonate：Acetyl
Acetone copper：Manganese acetate：Cobalt acetate：Nickel acetate：Ammonium molybdate：Selenium dioxide=0.8:1:1:1:1:1:1.5, mol ratio）45 g, add
Heat to 180 DEG C of reactions, reaction adds dichloromethane solvent after terminating, and filters out insoluble matter, is distilled to recover dichloromethane and obtains
The g of 4- tert-butyl os phthalaldehyde 165, yield 87%, purity 99.0%.
Embodiment 4
The g of ortho-xylene 162 is added in autoclave（1.0 mol）And mixed catalyst（Silver carbonate：Acetylacetone copper：Vinegar
Sour manganese：Cobalt acetate：Nickel acetate：Ammonium molybdate：Selenium dioxide=0.5:1:1:1:1:1:1, mol ratio）32.4 g, it is heated to 150 DEG C
Reaction, reaction add dichloromethane solvent after terminating, and filter out insoluble matter, are distilled to recover dichloromethane and obtain OPA
114 g, yield 85%, purity 99.5%.
Embodiment above describes the general principle of the present invention, main features and advantages, the technical staff of the industry should
Understand, the present invention is not limited to the above embodiments, the original for simply illustrating the present invention described in above-described embodiment and specification
Reason, under the scope for not departing from the principle of the invention, various changes and modifications of the present invention are possible, and these changes and improvements are each fallen within
In the scope of protection of the invention.
Claims (3)
1. a kind of preparation method of 4- tert-butyl os phthalaldehyde, it is characterised in that detailed process is：With 4- tert-butyl o diformazans
Benzene is initiation material, with the mixing of silver carbonate, acetylacetone copper, manganese acetate, cobalt acetate, nickel acetate, ammonium molybdate and selenium dioxide
Thing is mixed catalyst, and using air as oxidant, 4- tert-butyl o phthalaldehydes, the mixing is made in 150-200 DEG C of reaction
Silver carbonate in catalyst, acetylacetone copper, manganese acetate, cobalt acetate, nickel acetate, the mol ratio of ammonium molybdate and selenium dioxide are 0.5-
1:1:1:1:1:1:1-2。
2. the preparation method of 4- tert-butyl os phthalaldehyde according to claim 1, it is characterised in that：The 4- tert-butyl groups
The charged material weight of ortho-xylene and mixed catalyst ratio is 1:0.2-0.5.
3. the preparation method of 4- tert-butyl os phthalaldehyde according to claim 1, it is characterised in that concretely comprise the following steps：
Add the g and g of mixed catalyst 45 of 4- terting butyl-o-xylenes 162 in autoclave, silver carbonate, second in the mixed catalyst
Acyl acetone copper, manganese acetate, cobalt acetate, nickel acetate, the mol ratio of ammonium molybdate and selenium dioxide are 0.8:1:1:1:1:1:1.5, add
Heat to 180 DEG C of reactions, reaction adds dichloromethane solvent after terminating, and filters out insoluble matter, is distilled to recover dichloromethane and obtains
The g of 4- tert-butyl os phthalaldehyde 165, yield 87%, purity 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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| CN107778152A true CN107778152A (en) | 2018-03-09 |
| CN107778152B CN107778152B (en) | 2020-10-27 |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114524718A (en) * | 2022-01-25 | 2022-05-24 | 上海巽田科技股份有限公司 | Method for preparing high-purity o-phthalaldehyde from diester phthalate |
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 |
-
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 |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114524718A (en) * | 2022-01-25 | 2022-05-24 | 上海巽田科技股份有限公司 | Method for preparing high-purity o-phthalaldehyde from diester phthalate |
| 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 |
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| CN107778152B (en) | 2020-10-27 |
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