CN106749304B - A kind of method of superacid catalysis hydrolysis 3,4,9,10- tetracarboxylic acid dianhydrides of preparation - Google Patents
A kind of method of superacid catalysis hydrolysis 3,4,9,10- tetracarboxylic acid dianhydrides of preparation Download PDFInfo
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- CN106749304B CN106749304B CN201611113961.9A CN201611113961A CN106749304B CN 106749304 B CN106749304 B CN 106749304B CN 201611113961 A CN201611113961 A CN 201611113961A CN 106749304 B CN106749304 B CN 106749304B
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- Prior art keywords
- tetracarboxylic acid
- sulfuric acid
- superacid
- acid dianhydrides
- acid
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/0001—Post-treatment of organic pigments or dyes
- C09B67/0017—Influencing the physical properties by treatment with an acid, H2SO4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/06—Peri-condensed systems
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B3/00—Dyes with an anthracene nucleus condensed with one or more carbocyclic rings
- C09B3/14—Perylene derivatives
- C09B3/18—Preparation from starting materials already containing the perylene nucleus
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
Abstract
The present invention relates to a kind of methods for preparing 3,4,9,10- tetracarboxylic acid dianhydrides more particularly to a kind of superacid catalysis hydrolysis 3,4,9,10- tetracarboxylic acid dianhydrides of preparation.By 300 part 3,4,9,10- 4 formyl-2-imides are added in 2000 part of 90%~100% concentrated sulfuric acid, are warming up to 60~120 DEG C of heat preservations and are all dissolved to material；Then 80 DEG C are cooled to, it is slowly added to 4.5 parts of Superacid Catalysts thereto, it is warming up to 125 DEG C and keeps the temperature 8 hours, be cooled to 60 DEG C of filterings, wash filter cake with 1500 part 85% of the concentrated sulfuric acid, then filter cake is transferred in 3000 parts of water, it filters after mixing evenly, is washed with water to neutrality and obtains 3,4,9,10- tetracarboxylic acid dianhydrides.The dosage of sulfuric acid can be reduced, the amount for the sulfur dioxide for generating and discharging in hydrolysis reaction is reduced.
Description
Technical field
3,4,9,10- tetracarboxylic acid dianhydrides more particularly to a kind of superacid catalysis hydrolysis system are prepared the present invention relates to a kind of
The method of standby 3,4,9,10- tetracarboxylic acid dianhydrides.
Background technique
3,4,9,10- tetracarboxylic acid dianhydrides are the important intermediates for being dye (face) material, and there are many product in downstream.Red colour system
Have：C.I. pigment red 123, C.I. pigment red 149, C.I. paratonere 178, C.I. pigment red179, C.I. paratonere 190,
C.I. paratonere 224, C.I. vat red 23, C.I. Vat Red 29, C.I. vat red 32 and red dye Lumogen Red
F300；Green system has：C.I. solvent green 5；Violet has：C.I. pigment violet 29；Brown system has：C.I. pigment brown 26；
Black system has：C.I. pigment black 32.The technique of tradition 3,4,9,10- tetracarboxylic acid dianhydrides of preparation is existed with a large amount of concentrated sulfuric acid
3,4,9,10- 4 formyl-2-imides are hydrolyzed and are made by 200 DEG C or more of temperature.Since temperature is too high, a large amount of substrate is by oxygen
Change or sulfonation cause to receive it is low very low, and pollute it is very serious.
Summary of the invention
The present invention mainly solve the deficiencies in the prior art, provide it is a kind of using super acids as the catalyst to urging
Change hydrolysis 3,4,9,10- tetracarboxylic acid dianhydrides of preparation, can reduce the dosage of sulfuric acid, reduces reaction temperature to improve 3,4,9,
The yield of 10- tetracarboxylic acid dianhydride can also reduce one kind of the amount for the sulfur dioxide for generating and discharging in hydrolysis reaction
The method of superacid catalysis hydrolysis 3,4,9,10- tetracarboxylic acid dianhydrides of preparation.
Above-mentioned technical problem of the invention is mainly to be addressed by following technical proposals：
A kind of method of superacid catalysis hydrolysis 3,4,9,10- tetracarboxylic acid dianhydrides of preparation, carries out according to the following steps：
By 300 part 3,4,9,10- 4 formyl-2-imides are added in 2000 part of 90%~100% concentrated sulfuric acid, are warming up to 60
~120 DEG C of heat preservations are all dissolved to material；Then 80 DEG C are cooled to, 4.5 parts of Superacid Catalysts is slowly added to thereto, is warming up to
125 DEG C keep the temperature 8 hours, are cooled to 60 DEG C of filterings, wash filter cake with 1500 part 85% of the concentrated sulfuric acid, be then transferred to filter cake
It in 3000 parts of water, filters after mixing evenly, is washed with water to neutrality and obtains 3,4,9,10- tetracarboxylic acid dianhydrides.
Preferably, it is described in claim 1 dissolution 3,4,9,10- 4 formyl-2-imides sulfuric acid concentration be 93%~
96%.
Preferably, the sulfuric acid dosage is 5~20 times of 3,4,9,10- 4 formyl-2-imide weight.
Preferably, the Superacid Catalyst is one of fluorine metaantimmonic acid, evil spirit acid and charcoal borine acid.
Preferably, the additional amount of the Superacid Catalyst be 3,4,9,10- 4 formyl-2-imide weight 0.2~
10%.
Preferably, the hydrolysis temperature is 90~220 DEG C.
Super acids are also known as " super acid ", are that the acidity of 100% concentrated sulfuric acid of an analogy is also eager to excel millions of times even tens times
Acid.This kind of acid has application value in pole on chemistry and chemical industry, it is inorganic and organic protonating agent, and is activity
High catalyst.Past, some chemical reactions that is difficult to realize or cannot achieve under household condition at all were with super acids
When catalyst, but can smoothly it complete.
The present invention can reduce the dosage of sulfuric acid, reduce the amount for the sulfur dioxide for generating and discharging in hydrolysis reaction.
Specific embodiment
Below by embodiment, the technical solutions of the present invention will be further described.
Embodiment 1:A kind of method of superacid catalysis hydrolysis 3,4,9,10- tetracarboxylic acid dianhydrides of preparation, according to the following steps
It carries out：
By 300 part 3,4,9,10- 4 formyl-2-imides are added in 2000 part of 90% concentrated sulfuric acid, are warming up to 60 DEG C of heat preservations extremely
Material all dissolves；Then 80 DEG C are cooled to, is slowly added to 4.5 parts of Superacid Catalysts thereto, it is small to be warming up to 125 DEG C of heat preservations 8
When, 60 DEG C of filterings are cooled to, wash filter cake with 1500 part 85% of the concentrated sulfuric acid, then filter cake is transferred in 3000 parts of water, is stirred
Filtering, is washed with water to neutrality and obtains 3,4,9,10- tetracarboxylic acid dianhydrides after mixing uniformly.
The sulfuric acid dosage is 5 times of 3,4,9,10- 4 formyl-2-imide weight.
The Superacid Catalyst is fluorine metaantimmonic acid.
The additional amount of the Superacid Catalyst is the 0.2% of 3,4,9,10- 4 formyl-2-imide weight.
The hydrolysis temperature is 90 DEG C.
Embodiment 2:A kind of method of superacid catalysis hydrolysis 3,4,9,10- tetracarboxylic acid dianhydrides of preparation, according to the following steps
It carries out：
By 300 part 3,4,9,10- 4 formyl-2-imides are added in 2000 part of 95% concentrated sulfuric acid, are warming up to 80 DEG C of heat preservations extremely
Material all dissolves；Then 80 DEG C are cooled to, is slowly added to 4.5 parts of Superacid Catalysts thereto, it is small to be warming up to 125 DEG C of heat preservations 8
When, 60 DEG C of filterings are cooled to, wash filter cake with 1500 part 85% of the concentrated sulfuric acid, then filter cake is transferred in 3000 parts of water, is stirred
Filtering, is washed with water to neutrality and obtains 3,4,9,10- tetracarboxylic acid dianhydrides after mixing uniformly.
The sulfuric acid dosage is 10 times of 3,4,9,10- 4 formyl-2-imide weight.
The Superacid Catalyst is evil spirit acid.
The additional amount of the Superacid Catalyst is the 5% of 3,4,9,10- 4 formyl-2-imide weight.
The hydrolysis temperature is 120 DEG C.
Embodiment 3:A kind of method of superacid catalysis hydrolysis 3,4,9,10- tetracarboxylic acid dianhydrides of preparation, according to the following steps
It carries out：
By 300 part 3,4,9,10- 4 formyl-2-imides are added in 2000 part of 100% concentrated sulfuric acid, are warming up to 120 DEG C of heat preservations
It is all dissolved to material；Then 80 DEG C are cooled to, is slowly added to 4.5 parts of Superacid Catalysts thereto, is warming up to 125 DEG C of heat preservations 8
Hour, 60 DEG C of filterings are cooled to, wash filter cake with 1500 part 85% of the concentrated sulfuric acid, then filter cake is transferred in 3000 parts of water,
It filters after mixing evenly, is washed with water to neutrality and obtains 3,4,9,10- tetracarboxylic acid dianhydrides.
The sulfuric acid dosage is 20 times of 3,4,9,10- 4 formyl-2-imide weight.
The Superacid Catalyst is charcoal borine acid.
The additional amount of the Superacid Catalyst is the 10% of 3,4,9,10- 4 formyl-2-imide weight.
The hydrolysis temperature is 220 DEG C.
Claims (3)
1. a kind of method of superacid catalysis hydrolysis 3,4,9,10- tetracarboxylic acid dianhydrides of preparation, it is characterised in that according to the following steps
It carries out：
By 300 part 3,4,9,10- 4 formyl-2-imides are added in 2000 part of 90%~100% concentrated sulfuric acid, are warming up to 60~120
DEG C heat preservation to material all dissolve；Then 80 DEG C are cooled to, 4.5 parts of super acidic catalysts is slowly added to thereto, is warming up to 125
DEG C heat preservation 8 hours, be cooled to 60 DEG C of filterings, wash filter cake with 1500 part 85% of the concentrated sulfuric acid, filter cake is then transferred to 3000
In part water, filters after mixing evenly, be washed with water to neutrality and obtain 3,4,9,10- tetracarboxylic acid dianhydrides.
2. a kind of method of superacid catalysis hydrolysis 3,4,9,10- tetracarboxylic acid dianhydrides of preparation according to claim 1,
It is characterized in that：The sulfuric acid concentration for dissolving 3,4,9,10- 4 formyl-2-imides is 93%~96%.
3. a kind of method of superacid catalysis hydrolysis 3,4,9,10- tetracarboxylic acid dianhydrides of preparation according to claim 1,
It is characterized in that：The super acidic catalyst is one of fluorine metaantimmonic acid, evil spirit acid and charcoal borine acid.
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| CN201611113961.9A CN106749304B (en) | 2016-12-06 | 2016-12-06 | A kind of method of superacid catalysis hydrolysis 3,4,9,10- tetracarboxylic acid dianhydrides of preparation |
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| CN201611113961.9A CN106749304B (en) | 2016-12-06 | 2016-12-06 | A kind of method of superacid catalysis hydrolysis 3,4,9,10- tetracarboxylic acid dianhydrides of preparation |
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| CN106749304B true CN106749304B (en) | 2018-11-23 |
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| DE10218618A1 (en) * | 2002-04-25 | 2003-11-06 | Basf Ag | Process for the preparation of perylene-3,4: 9,10-tetracarboximide and perylene-3,4: 9,10-tetracarboximide and of naphthalene-1,8-dicarboximides |
| JP5619729B2 (en) * | 2008-05-28 | 2014-11-05 | ビーエーエスエフ ソシエタス・ヨーロピアＢａｓｆ Ｓｅ | Improved red filter composition |
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