CN105777525A - Separating and purifying method for 2-(4-ethyl benzene formyl) benzoic acid - Google Patents
Separating and purifying method for 2-(4-ethyl benzene formyl) benzoic acid Download PDFInfo
- Publication number
- CN105777525A CN105777525A CN201610218730.8A CN201610218730A CN105777525A CN 105777525 A CN105777525 A CN 105777525A CN 201610218730 A CN201610218730 A CN 201610218730A CN 105777525 A CN105777525 A CN 105777525A
- Authority
- CN
- China
- Prior art keywords
- benzoic
- acyl group
- ethylamino benzonitrile
- benzonitrile acyl
- acid
- 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.)
- Pending
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/083—Preparation of carboxylic acids or their salts, halides or anhydrides from carboxylic acid anhydrides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
- C07C51/43—Separation; Purification; Stabilisation; Use of additives by change of the physical state, e.g. crystallisation
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Crystallography & Structural Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a separating and purifying method for 2-(4-ethyl benzene formyl) benzoic acid (BE acid for short).An aqueous hydrochloric acid solution is adopted as a stripping agent, a reaction system with chlorobenzene as solvent for synthesizing the BE acid is washed at certain temperature, separated liquid stands after washing, organic phases obtained through separation are put at the low temperature to be cooled and crystallized, and by means of centrifugation and drying, BE acid crystals with high purity are obtained.The method is simple, operation is easy, alchlor in chlorobenzene can be completely removed, selectivity precipitation of the BE acid is achieved, the method can replace a traditional evaporation technology, the product yield and purity are high, the energy consumption is low, and the method is an ideal technology for separating and purifying the BE acid.
Description
Technical field
The present invention relates to the technical field of a kind of compound separating-purifying, especially relate to a kind of 2-(4-second
Base benzoyl) benzoic separation method.
Background technology
2-ethyl-anthraquinone (2-EAQ) is a kind of important organic synthesis intermediate, is anthraquinone production dioxygen
The carrier of water, is the most also to produce Photoactive compounds, dyestuff and the important source material of degradative resin, extensively should
For manufacturing hydrogen peroxide, reducing dye, disperse dyes, reactive dye etc..
Current domestic and international large-scale Hydrogen Peroxide Production producer all uses anthraquinone manufacture hydrogen peroxide, 2-ethyl-anthraquinone
Yield and quality affect the development of hydrogen peroxide manufacture and related industry largely.Hydrogen peroxide is in North America
The year growth rate of demand of paper industry is 18%, and the year growth rate of demand of Europe hydrogen peroxide is 10%.Along with
The development of Asian-Pacific area paper pulp industry, demand is sharply increasing, and some major companies arrive this area one after another and invest and build
Factory, developing target market.In the long term, having very promising prospects of development hydrogen peroxide, but 2-ethyl must be first developed
The production of anthraquinone, hydrogen dioxide solution production by anthraquinone process greatly reduces production cost, and power consumption is only electrolysis
1/10th, it is the main method producing hydrogen peroxide at present, along with the quick growth of hydrogen peroxide industry, 2-
The demand of EAQ also can increase substantially therewith.
Industrial main use Phthalic Anhydride produces 2-ethyl-anthraquinone, first with ethylbenzene and phthalic anhydride as raw material, and chlorine
Benzene is solvent, and condensation reaction occurs under the catalytic action of aluminum chloride, generates BE acid, then BE acid
Under the effect of oleum, dehydration closed-loop generates 2-ethyl-anthraquinone.Wherein, sour for BE yield and purity
Yield and purity on product 2-ethyl-anthraquinone have conclusive impact.Therefore, suitable BE acid separates
Method of purification is significant for the production of 2-ethyl-anthraquinone.
The technique of current industrial commonly used separating-purifying BE acid is will be anti-after condensation reaction terminates
Answer system to join in a large amount of water, wash away the aluminum chloride in organic facies, separate organic facies, use decompression
Solvent chlorobenzene is evaporated by the modes such as distillation, obtains BE acid solid.The method has a following open defect:
1, aluminum chloride dissolubility in water is limited, it is impossible to by complete for aluminum chloride back extraction to aqueous phase, cause
The BE acid finally given still contains a certain amount of aluminium salt, causes BE acid purity the highest, affects subsequent reactions
The yield of middle 2-ethyl-anthraquinone and purity, and need to consume substantial amounts of water in washing process;
2, higher due to solvent chlorobenzene boiling point, use the mode of evaporation of solvent to need high-temperature heating, energy
Consumption is relatively big, does not meets the requirement of energy-saving and emission-reduction.
Summary of the invention
In view of this, it is an object of the invention to provide that a kind of method is simple, energy consumption is low, product yield and
2-(4-ethylamino benzonitrile acyl group) the benzoic process for separation and purification that purity is higher.
In order to realize foregoing invention purpose, the present invention provides techniques below scheme:
The invention provides a kind of 2-(4-ethylamino benzonitrile acyl group) benzoic process for separation and purification, including
Following steps:
2-(4-ethylamino benzonitrile acyl group) benzoic reaction solution, described 2-(4-ethylamino benzonitrile acyl group) are provided
Benzoic acid with ethylbenzene and phthalic anhydride as raw material, chlorobenzene as solvent, aluminum chloride obtains for catalyst synthesis;
Using aqueous hydrochloric acid solution is that back washing agent washs described 2-(4-ethylamino benzonitrile acyl group) benzoic reaction
Solution;
Feed liquid after washing is stood separatory, obtains organic facies;
By organic facies crystallisation by cooling, obtain 2-(4-ethylamino benzonitrile acyl group) Benzoic Acid Crystal;
Preferably washing process is: by described 2-(4-ethylamino benzonitrile acyl group) benzoic reaction solution with
Combined, stirs 30~60 minutes under the conditions of 40~90 DEG C;
Preferably the molar concentration of aqueous hydrochloric acid solution is 0.1~0.5mol/L;
Preferably aqueous hydrochloric acid solution is 0.8~1.2:1 with the volume ratio of reaction solution;
The time preferably standing separatory is 5~10 minutes;
The preferably temperature of crystallisation by cooling is-20~-5 DEG C;
Preferably the time of crystallisation by cooling is 20~120min;
Preferably also include after crystallisation by cooling being centrifuged, being dried;
The temperature being preferably dried is 60~90 DEG C;
The time being preferably dried is 60~90 minutes.
The invention provides a kind of 2-(4-ethylamino benzonitrile acyl group) benzoic process for separation and purification, including
Following steps: 2-(4-ethylamino benzonitrile acyl group) benzoic reaction solution, described 2-(4-ethylo benzene are provided
Formoxyl) benzoic acid with ethylbenzene and phthalic anhydride as raw material, chlorobenzene as solvent, aluminum chloride synthesizes for catalyst
Obtain;Using aqueous hydrochloric acid solution is that the back washing agent described 2-of washing (4-ethylamino benzonitrile acyl group) is benzoic instead
Answer solution;Feed liquid after described washing is stood separatory, obtains organic facies;By described organic facies cooling knot
Crystalline substance, obtains 2-(4-ethylamino benzonitrile acyl group) Benzoic Acid Crystal.The present invention uses aqueous hydrochloric acid solution as instead
Extraction agent, increases aluminum chloride dissolubility in aqueous phase, can completely remove three remained in chlorobenzene
Aluminum chloride, it is to avoid the aluminium salt residual in end product BE acid crystal, improves BE acid significantly
The purity of crystal;The organic facies crystallisation by cooling that separatory is obtained by the present invention, BE acid in chlorobenzene dissolubility with
Temperature drastically changes, and organic acid molecule is selectivity deposition on lattice, it is achieved that the Selective separation-out of BE acid,
Thus improve the purity of BE acid further.Test result indicate that, the BE that the method that the present invention provides obtains
Acid crystal purity can reach more than 98%.
And, the method that the present invention provides instead of traditional evaporation technology, it is not necessary to high-temperature heating is with big
The washing of amount water, and inorganic phase can be pollution-free directly by enterprise's recycling of production aluminium polychlorid,
Reduce energy consumption, economize on resources, meet the requirement of energy-saving and emission-reduction.
Detailed description of the invention
The invention provides a kind of 2-(4-ethylamino benzonitrile acyl group) benzoic process for separation and purification, including
Following steps:
2-(4-ethylamino benzonitrile acyl group) benzoic reaction solution, described 2-(4-ethylamino benzonitrile acyl group) are provided
Benzoic acid with ethylbenzene and phthalic anhydride as raw material, chlorobenzene as solvent, aluminum chloride obtains for catalyst synthesis;
Using aqueous hydrochloric acid solution is that back washing agent washs described 2-(4-ethylamino benzonitrile acyl group) benzoic reaction
Solution;
Feed liquid after described washing is stood separatory, obtains organic facies;By described organic facies crystallisation by cooling,
Obtain 2-(4-ethylamino benzonitrile acyl group) Benzoic Acid Crystal.
The present invention as raw material with 2-(4-ethylamino benzonitrile acyl group) benzoic reaction solution, carries out separation and carries
Pure, obtain 2-(4-ethylamino benzonitrile acyl group) Benzoic Acid Crystal.In the present invention, described 2-(4-ethylo benzene
Formoxyl) benzoic reaction solution be ethylbenzene and phthalic anhydride be raw material, chlorobenzene be that solvent, aluminum chloride are
Catalyst synthesis obtains.In the present invention, the detailed process of described synthesis preferably includes following steps:
Chlorobenzene is mixed with phthalic anhydride and aluminum trichloride (anhydrous), obtains mixed solution;
In described mixed solution, add ethylbenzene, obtain reaction raw materials liquid;
The heating of described reaction raw materials liquid is reacted, obtains 2-(4-ethylamino benzonitrile acyl group) benzoic
Reaction solution.
In an embodiment of the present invention, in chlorobenzene, phthalic anhydride and aluminum trichloride (anhydrous) are added successively.At this
In bright, the mol ratio of described chlorobenzene, phthalic anhydride and aluminum trichloride (anhydrous) is preferably 4.0~4.5:0.9~1.0:2.0~2.2,
More preferably 4.2~4.3:0.95~1.0:2.1~2.2.
After obtaining mixed solution, the present invention is to described mixed solution and dripping ethylbenzene.The present invention is preferably stirring
Under conditions of mixing, in described mixed solution, add ethylbenzene.Stir speed (S.S.) is preferably 150~200r/min,
More preferably 180~190r/min.In the present invention, described ethylbenzene is preferably under 20~30 DEG C of temperature conditionss
Add, more preferably 25~28 DEG C.The addition speed of ethylbenzene is preferably 1~10ml/min, more preferably
4~6ml/min.In the present invention, the mol ratio of described phthalic anhydride and ethylbenzene is preferably 0.8~1.0:1.0, more excellent
Elect 0.9:1.0 as.
After obtaining reaction raw materials liquid, the heating of described reaction raw materials liquid is reacted by the present invention.In the present invention
In, the temperature of described heating is preferably 40~60 DEG C, more preferably 45~55 DEG C;The time of described reaction is excellent
Elect 1.5~3h as, more preferably 2.0~2.5h.
After obtaining 2-(4-ethylamino benzonitrile acyl group) benzoic reaction solution, the present invention uses hydrochloric acid water-soluble
Liquid is that back washing agent washs described 2-(4-ethylamino benzonitrile acyl group) benzoic reaction solution.In the present invention,
The process of described washing is preferably:
By 2-(4-ethylamino benzonitrile acyl group) benzoic reaction solution and combined, at 40~90 DEG C
Under the conditions of stir 30~60 minutes.
In the present invention, the molar concentration of described aqueous hydrochloric acid solution is preferably 0.1~0.5mol/L, more preferably
0.1~0.2mol/L;The volume ratio of described aqueous hydrochloric acid solution and described reaction solution is preferably 0.8~1.2:1, more
It is preferably 1.05:1;
In the present invention, in described washing process, the speed of described stirring is preferably 150~200r/min,
More preferably 160~180r/min;The temperature of described washing is preferably 40~90 DEG C, more preferably 50~80 DEG C,
Most preferably 60~75 DEG C;The time of described washing is preferably 30~60min, more preferably 40~55min.
After described washing completes, the feed liquid after described washing is stood separatory by the present invention, obtains organic facies.
In the present invention, the time of described standing is preferably 5~10min, more preferably 6~8min.The present invention couple
The method of described separatory does not has special restriction, uses separatory funnel well known to those skilled in the art to carry out
Separatory.
After obtaining organic facies, the present invention, by described organic facies crystallisation by cooling, obtains 2-(4-ethylbenzoyl
Base) Benzoic Acid Crystal.In the present invention, the temperature of described crystallisation by cooling preferably-20~-5 DEG C, more preferably
For-15~-10 DEG C;The time of described crystallisation by cooling is preferably 20~120min, more preferably 50~100min,
Most preferably 60~80min.
After described crystallisation by cooling, the product of described crystallisation by cooling is preferably centrifuged and is dried by the present invention,
Obtain 2-(4-ethylamino benzonitrile acyl group) Benzoic Acid Crystal.Method that is described centrifugal and that be dried is not had by the present invention
There is special restriction, use technical scheme that is well known to those skilled in the art centrifugal and that be dried;?
In the present invention, described centrifugal condition is preferably centrifugal rotational speed 5000~10000r/min, centrifugation time
1~10min, more preferably centrifugal rotational speed 8000~9000r/min, centrifugation time 3~4min;Described dry
Temperature is preferably 60~90 DEG C, more preferably 70~80 DEG C;The described dry time is preferably 60~90min,
More preferably 70~80min.
2-(4-ethylamino benzonitrile acyl group) the benzoic separation provided the present invention below in conjunction with embodiment carries
Pure method is described in detail, but they can not be interpreted as limiting the scope of the present invention.
Embodiment 1
In the four-hole bottle with agitator, add chlorobenzene 500g (about 4.6mol), then put into phthalic anhydride successively
148g (about 1.0mol) and aluminum trichloride (anhydrous) 270g (about 2.03mol), opens stirring, controls stirring
Speed is 180r/min, keeps the temperature at 25 DEG C, puts into ethylbenzene 117g (about 1.1mol) the most equably,
Adding speed is 5ml/min, after adding ethylbenzene, material liquid temperature rises to 60 DEG C, and reaction starts i.e. to have salt
Acid vapor escapes, and with the hydrogen chloride gas of Alkali absorption effusion, the response time is 3h, to without hydrogen chloride gas
After effusion, reaction stops, and obtains the reaction solution containing BE acid.
Embodiment 2
The reactant liquor 100ml that Example 1 obtains, reaction system joins 110ml molar concentration is
In the aqueous hydrochloric acid solution of 0.1mol/L, stand layering in 10 minutes after stirring 30min at 60 DEG C, after layering
Aqueous phase water white transparency, organic facies is rufous, uses separatory funnel to carry out separatory, by isolated afterwards
Organic facies be placed in-15 DEG C in the environment of freezing 1 hour, the graininess separating out a large amount of white yellowish is brilliant
Body, the BE acid crystal that centrifugation separates out, and be dried 1 hour at 80 DEG C, it is dried, pure
BE acid crystal.Reclaim upper strata chlorobenzene clear liquid and continue on for synthesizing the reaction of BE acid.
The present invention uses Yi Lite E3100 high performance liquid chromatograph to detect product purity, and calculated yield,
Obtaining product purity is 98.5%, BE acid yield 95%.
Embodiment 3
The reactant liquor 100ml that Example 1 obtains, reaction system joins 80ml molar concentration is
In the aqueous hydrochloric acid solution of 0.3mol/L, stand 5 minutes after stirring 45min at 90 DEG C, aqueous phase after layering
Water white transparency, organic facies is rufous, uses separatory funnel to carry out separatory, having isolated afterwards
Machine in the environment of being placed in-5 DEG C mutually freezing 2 hours, separates out the granular crystals of a large amount of white yellowish, from
The heart divides isolated BE acid crystal, and is dried 1.5 hours at 80 DEG C, is dried, pure BE
Acid crystal.Reclaim upper strata chlorobenzene clear liquid and continue on for synthesizing the reaction of BE acid.
Use Yi Lite E3100 high performance liquid chromatograph detection product purity, and calculated yield, produced
Thing purity is 98%, BE acid yield 96%.
Embodiment 4
The reactant liquor 100ml that Example 1 obtains, reaction system joins 100ml molar concentration is
In the aqueous hydrochloric acid solution of 0.5mol/L, stand 10 minutes after stirring 60min at 40 DEG C, aqueous phase after layering
Water white transparency, organic facies is rufous, uses separatory funnel to carry out separatory, having isolated afterwards
Machine in the environment of being placed in-20 DEG C mutually freezing 2 hours, separates out the granular crystals of a large amount of white yellowish,
The BE acid crystal that centrifugation separates out, and be dried 1.5 hours at 80 DEG C, it is dried, pure
BE acid crystal.Reclaim upper strata chlorobenzene clear liquid and continue on for synthesizing the reaction of BE acid.
Use Yi Lite E3100 high performance liquid chromatograph detection product purity, and calculated yield, produced
Thing purity is 97%, BE acid yield 95%.
As seen from the above embodiment, use process for separation and purification of the present invention to BE acid condensation reaction body
System carries out separating-purifying, and method is simple, energy consumption is low, and product yield is high, and the BE acid crystal purity obtained is high,
And upper strata chlorobenzene clear liquid can reclaim the reaction continuing on for synthesizing BE acid, scheme of the present invention is a kind of
Environmental protection, efficient BE acid process for separation and purification.
The above is only the preferred embodiment of the present invention, it is noted that general for the art
For logical technical staff, under the premise without departing from the principles of the invention, it is also possible to make some improvement and profit
Decorations, these improvements and modifications also should be regarded as protection scope of the present invention.
Claims (9)
1. 2-(4-ethylamino benzonitrile acyl group) benzoic process for separation and purification, comprises the following steps:
2-(4-ethylamino benzonitrile acyl group) benzoic reaction solution, described 2-(4-ethylamino benzonitrile acyl group) are provided
Benzoic acid with ethylbenzene and phthalic anhydride as raw material, chlorobenzene as solvent, aluminum chloride obtains for catalyst synthesis;
Using aqueous hydrochloric acid solution is that back washing agent washs described 2-(4-ethylamino benzonitrile acyl group) benzoic reaction
Solution;
Feed liquid after described washing is stood separatory, obtains organic facies;
By described organic facies crystallisation by cooling, obtain 2-(4-ethylamino benzonitrile acyl group) Benzoic Acid Crystal.
Process for separation and purification the most according to claim 1, it is characterised in that: the process of described washing
For: by described 2-(4-ethylamino benzonitrile acyl group) benzoic reaction solution and combined,
Stir 30~60 minutes under the conditions of 40~90 DEG C.
A kind of 2-(4-ethylamino benzonitrile acyl group) benzoic separation the most according to claim 1 and 2
Method of purification, it is characterised in that: the molar concentration of described aqueous hydrochloric acid solution is 0.1~0.5mol/L.
A kind of 2-(4-ethylamino benzonitrile acyl group) benzoic separating-purifying the most according to claim 1
Method, it is characterised in that: described aqueous hydrochloric acid solution is 0.8~1.2:1 with the volume ratio of reaction solution.
A kind of 2-(4-ethylamino benzonitrile acyl group) benzoic separating-purifying the most according to claim 1
Method, it is characterised in that: the time of described standing is 5~10 minutes.
A kind of 2-(4-ethylamino benzonitrile acyl group) benzoic separating-purifying the most according to claim 1
Method, it is characterised in that: the temperature of described crystallisation by cooling is-20~-5 DEG C.
7. according to a kind of 2-(4-ethylamino benzonitrile acyl group) the benzoic separation described in claim 1 or 6
Method of purification, it is characterised in that: the time of described crystallisation by cooling is 20~120min.
A kind of 2-(4-ethylamino benzonitrile acyl group) benzoic separating-purifying the most according to claim 1
Method, it is characterised in that: also include after described crystallisation by cooling being centrifuged, being dried;
Described dry temperature is 60~90 DEG C.
A kind of 2-(4-ethylamino benzonitrile acyl group) benzoic separating-purifying side the most according to claim 8
Method, it is characterised in that: the described dry time is 60~90 minutes.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201610218730.8A CN105777525A (en) | 2016-04-11 | 2016-04-11 | Separating and purifying method for 2-(4-ethyl benzene formyl) benzoic acid |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201610218730.8A CN105777525A (en) | 2016-04-11 | 2016-04-11 | Separating and purifying method for 2-(4-ethyl benzene formyl) benzoic acid |
Publications (1)
Publication Number | Publication Date |
---|---|
CN105777525A true CN105777525A (en) | 2016-07-20 |
Family
ID=56395132
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN201610218730.8A Pending CN105777525A (en) | 2016-04-11 | 2016-04-11 | Separating and purifying method for 2-(4-ethyl benzene formyl) benzoic acid |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN105777525A (en) |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN110790655A (en) * | 2018-08-03 | 2020-02-14 | 广西田东兴鹏精细化学品有限公司 | Closed-loop reaction process for producing 2-ethyl anthraquinone |
CN111747839A (en) * | 2020-06-24 | 2020-10-09 | 潍坊门捷化工有限公司 | Synthetic method of 2- (4' -ethylbenzoyl) benzoic acid |
CN113956146A (en) * | 2021-11-22 | 2022-01-21 | 浙江金科日化原料有限公司 | Environment-friendly 2-ethyl anthraquinone production process |
CN115521199A (en) * | 2021-12-31 | 2022-12-27 | 山东华夏神舟新材料有限公司 | Method and device for purifying benzophenone tetracarboxylic acid |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS4739059B1 (en) * | 1966-09-28 | 1972-10-03 | Ford Motor Co | Battery |
US3764664A (en) * | 1970-06-19 | 1973-10-09 | Sumitomo Chemical Co | Process for the production of active anhydrous aluminum chloride |
US4379092A (en) * | 1980-12-16 | 1983-04-05 | P C U K Produits Chimiques Ugine Kuhlmann | Process for the preparation of anthraquinone and its substituted derivatives |
-
2016
- 2016-04-11 CN CN201610218730.8A patent/CN105777525A/en active Pending
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS4739059B1 (en) * | 1966-09-28 | 1972-10-03 | Ford Motor Co | Battery |
US3764664A (en) * | 1970-06-19 | 1973-10-09 | Sumitomo Chemical Co | Process for the production of active anhydrous aluminum chloride |
US4379092A (en) * | 1980-12-16 | 1983-04-05 | P C U K Produits Chimiques Ugine Kuhlmann | Process for the preparation of anthraquinone and its substituted derivatives |
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN110790655A (en) * | 2018-08-03 | 2020-02-14 | 广西田东兴鹏精细化学品有限公司 | Closed-loop reaction process for producing 2-ethyl anthraquinone |
CN110790655B (en) * | 2018-08-03 | 2022-09-20 | 百色世裕科技股份有限公司 | Closed-loop reaction process for producing 2-ethyl anthraquinone |
CN111747839A (en) * | 2020-06-24 | 2020-10-09 | 潍坊门捷化工有限公司 | Synthetic method of 2- (4' -ethylbenzoyl) benzoic acid |
CN113956146A (en) * | 2021-11-22 | 2022-01-21 | 浙江金科日化原料有限公司 | Environment-friendly 2-ethyl anthraquinone production process |
CN113956146B (en) * | 2021-11-22 | 2023-11-24 | 浙江金科日化新材料股份有限公司 | 2-ethyl anthraquinone production process |
CN115521199A (en) * | 2021-12-31 | 2022-12-27 | 山东华夏神舟新材料有限公司 | Method and device for purifying benzophenone tetracarboxylic acid |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN105777525A (en) | Separating and purifying method for 2-(4-ethyl benzene formyl) benzoic acid | |
PT2220021E (en) | Process for the preparation of terephthalic acid | |
CN109928872B (en) | Method for high-purity synthesis of anthraquinone and co-production of magnesium sulfate | |
CN106588709A (en) | Preparation method for sodium fatty acyl methyl taurate | |
CN117986162B (en) | Preparation method of ethyl sulfonyl chloride | |
CN107540581A (en) | The preparation method of 4,4 ' dichloro diphenyl sulfones | |
CN101143841B (en) | Method for producing 4-aminotoluene-3-sulfonic acid | |
CN101302176A (en) | Method for preparing p-toluenesulfonic acid by gas-phase sulphonation of toluol with sulfur trioxide | |
CN108586296B (en) | Continuous synthesis method of p-nitrotoluene-o-sulfonic acid | |
CN103694151B (en) | The method of p-acetaminobenzenesulfonyl chloride dry product is directly synthesized in a kind of solvent extraction | |
CN109336789A (en) | A kind of preparation method of 3- hydroxy-propanesulfonic acid | |
CN102838562A (en) | Method for synthesizing rubber vulcanization accelerator NS (N-tertiary butyl-2-benzothiazole sulfenamide) through two-step method by taking hydrogen peroxide as oxidant | |
CN102815737A (en) | New method for producing potassium alum | |
CN104016890B (en) | Method for preparing 1-amino-4-sodium naphthalene sulfonate through solid-phase continuous reaction | |
CN108947870B (en) | Preparation method of bromosartanbiphenyl | |
CN108752181A (en) | The method that direct chlorination prepares high-purity 1- chloroanthraquinones | |
CN105198697B (en) | Synthetic method for 2-bromofluorene derivatives | |
CN102417525A (en) | Preparation method of synthesized D-glucosamine sulfate sodium | |
CN105622481A (en) | Process for efficient synthesis of 5-bromoindole | |
CN113956147A (en) | Decolorizing process of 2-ethyl anthraquinone crude product | |
CN110483530B (en) | Production method of urotropine for co-producing organic phosphine corrosion inhibitor | |
CN106810476A (en) | Synthesize the method and its system of N-acetylsulfanilyl chloride as sulfonating agent with sulfur trioxide | |
CN106518687A (en) | Efficient preparation method of high-purity tetraethyl ammonium chloride | |
CN110746293A (en) | Process for preparing p-toluic acid by continuous catalytic oxidation | |
CN205856358U (en) | The continuous production device of 1 LOMAR PWA EINECS 246-676-2 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
C06 | Publication | ||
PB01 | Publication | ||
C10 | Entry into substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
AD01 | Patent right deemed abandoned | ||
AD01 | Patent right deemed abandoned |
Effective date of abandoning: 20180713 |