CN104402840A - Synthesis process of isatoic anhydride - Google Patents
Synthesis process of isatoic anhydride Download PDFInfo
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- CN104402840A CN104402840A CN201410635513.XA CN201410635513A CN104402840A CN 104402840 A CN104402840 A CN 104402840A CN 201410635513 A CN201410635513 A CN 201410635513A CN 104402840 A CN104402840 A CN 104402840A
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- isatoic anhydride
- anhydride
- hypochlorite
- hydrochloric acid
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- VYFOAVADNIHPTR-UHFFFAOYSA-N isatoic anhydride Chemical compound NC1=CC=CC=C1CO VYFOAVADNIHPTR-UHFFFAOYSA-N 0.000 title claims abstract description 53
- 238000000034 method Methods 0.000 title claims abstract description 38
- 230000015572 biosynthetic process Effects 0.000 title claims abstract description 31
- 238000003786 synthesis reaction Methods 0.000 title claims abstract description 31
- 230000008569 process Effects 0.000 title abstract description 19
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims abstract description 46
- 238000006243 chemical reaction Methods 0.000 claims abstract description 42
- 239000007788 liquid Substances 0.000 claims abstract description 31
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 claims abstract description 25
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 claims abstract description 25
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims abstract description 21
- 239000004202 carbamide Substances 0.000 claims abstract description 21
- 238000001816 cooling Methods 0.000 claims abstract description 12
- 239000007795 chemical reaction product Substances 0.000 claims abstract description 10
- 238000002156 mixing Methods 0.000 claims abstract description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 72
- WQYVRQLZKVEZGA-UHFFFAOYSA-N hypochlorite Chemical compound Cl[O-] WQYVRQLZKVEZGA-UHFFFAOYSA-N 0.000 claims description 54
- 235000011121 sodium hydroxide Nutrition 0.000 claims description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 12
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical group [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 claims description 10
- 239000002351 wastewater Substances 0.000 claims description 8
- 238000007599 discharging Methods 0.000 abstract description 4
- 239000006227 byproduct Substances 0.000 abstract description 3
- 238000010438 heat treatment Methods 0.000 abstract description 2
- 239000003513 alkali Substances 0.000 abstract 1
- 238000005904 alkaline hydrolysis reaction Methods 0.000 description 7
- 239000013078 crystal Substances 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 238000005352 clarification Methods 0.000 description 5
- 238000001035 drying Methods 0.000 description 5
- 230000007423 decrease Effects 0.000 description 4
- 238000006386 neutralization reaction Methods 0.000 description 4
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 3
- 235000011089 carbon dioxide Nutrition 0.000 description 3
- 230000008859 change Effects 0.000 description 3
- -1 formamido group Chemical group 0.000 description 3
- 150000003949 imides Chemical class 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 3
- 235000010234 sodium benzoate Nutrition 0.000 description 3
- 239000004299 sodium benzoate Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 238000000967 suction filtration Methods 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 238000005576 amination reaction Methods 0.000 description 2
- 239000007844 bleaching agent Substances 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 238000006731 degradation reaction Methods 0.000 description 2
- 238000005580 one pot reaction Methods 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 238000006105 Hofmann reaction Methods 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000012847 fine chemical Substances 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000012434 nucleophilic reagent Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 235000013599 spices Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D265/04—1,3-Oxazines; Hydrogenated 1,3-oxazines
- C07D265/12—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems
- C07D265/14—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D265/24—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring with hetero atoms directly attached in positions 2 and 4
- C07D265/26—Two oxygen atoms, e.g. isatoic anhydride
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Indole Compounds (AREA)
Abstract
The invention provides a synthesis process of isatoic anhydride. The synthesis process comprises the following steps: a) heating phthalic anhydride until phthalic anhydride is molten and mixing the molten phthalic anhydride with urea, and cooling to 10-20 DEG C after a reaction; b) mixing reaction products obtained after cooling with liquid alkali, cooling to minus 5- 0 DEG C to carry out a first reaction, mixing reaction products with pypocholoride, mixing reaction products with hydrochloric acid after a second reaction, and carrying out a third reaction to obtain isatoic anhydride. During the synthesis process of isatoic anhydride, reaction temperature is controlled strictly. Thus, generation of by-products is avoided, and yield of isatoic anhydride is raised. Meanwhile, by one kettle way for synthesis of isatoic anhydride, industrial operations are minimized, the discharging link is reduced, and yield is raised. It shows through experimental results that yield of isatoic anhydride reaches more than 94% and purity reaches more than 99%.
Description
Technical field
The present invention relates to fine chemistry industry technical field of producing, particularly relate to a kind of synthesis technique of isatoic anhydride.
Background technology
Isatoic anhydride (C
8h
5nO
3) be a kind of important chemical intermediate, it can react with electrophilic reagent, also can react with nucleophilic reagent.Isatoic anhydride and homologue thereof, derivative are widely used in synthesizing agrochemicals, dyestuff, pigment, spices, essence, medicine, UV light absorber, whipping agent, fire retardant, sanitas, SYNTHETIC OPTICAL WHITNER, sterilant and sanitizer etc. fine chemical product.
The synthesis technique of traditional isatoic anhydride is with phthalic anhydride and urea raw material, phthalic imidine discharging post-drying prepared by phthalic anhydride and urea reaction, then with the phthalic imidine of drying for raw material, it adopts hypochlorite oxidation namely to obtain isatoic anhydride after dissolving.In the process of phthalic anhydride synthesis phthalic imidine, the yield of phthalic imidine is only 92% ~ 93%, and phthalic imidine is in the process of synthesis isatoic anhydride, the yield of isatoic anhydride is 91% ~ 92%, the purity of isatoic anhydride reaches as high as 96%, therefore the yield of isatoic anhydride and purity lower, this synthesis technique creates a large amount of trade effluents simultaneously, adds production cost.
Summary of the invention
The technical problem that the present invention solves is the synthesis technique providing a kind of isatoic anhydride, and the synthesis technique of the application's isatoic anhydride can reduce costs, and the yield of isatoic anhydride and purity are very high.
This application provides a kind of synthesis technique of isatoic anhydride, comprise the following steps:
A) mix after phthalic anhydride heat fused with urea, after reaction, be cooled to 10 DEG C ~ 20 DEG C;
B) reaction product after cooling mixed with liquid caustic soda, be cooled to-5 DEG C ~ 0 DEG C and carry out the first reaction, then mix with hypochlorite, second reacts rear and mixed in hydrochloric acid, obtains isatoic anhydride after the 3rd reaction.
Preferably, step b) in also comprised before mixing with liquid caustic soda:
Reaction product after cooling is mixed with water, is cooled to 5 DEG C ~ 10 DEG C.
Preferably, described hypochlorite is clorox.
Preferably, the mol ratio of described phthalic anhydride, urea, liquid caustic soda, hypochlorite and hydrochloric acid is 1.0:(1.0 ~ 1.3): (1.0 ~ 1.1): (0.9 ~ 1.0): (1.0 ~ 1.4); Described liquid paper mill wastewater is 32wt%, and the concentration of described hypochlorite is 10wt% ~ 13wt%, and the concentration of described hydrochloric acid is 31wt%.
Preferably, the mol ratio of described phthalic anhydride, urea, liquid caustic soda, hypochlorite and hydrochloric acid is 1.0:(1.05 ~ 1.2): (1.0 ~ 1.05): (0.95 ~ 1.0): (1.0 ~ 1.3); Described liquid paper mill wastewater is 32wt%, and the concentration of described hypochlorite is 10wt% ~ 13wt%, and the concentration of described hydrochloric acid is 31wt%.
Preferably, step b) described in reduce temperature to-5 DEG C ~ 5 DEG C after the first reaction.
This application provides a kind of synthesis technique of isatoic anhydride, comprise the following steps: a) mix after phthalic anhydride heat fused with urea, after reaction, be cooled to 10 DEG C ~ 20 DEG C; B) reaction product after cooling mixed with liquid caustic soda, be cooled to-5 DEG C ~ 0 DEG C and carry out the first reaction, then mix with hypochlorite, second reacts rear and mixed in hydrochloric acid, obtains isatoic anhydride after the 3rd reaction.The application is in the process of synthesis isatoic anhydride, first phthalic anhydride fusing is made itself and urea reaction, the carbonic acid gas of phthalic imidine and gaseous state, water is obtained after reaction, again adjacent benzene divalence imide is carried out alkaline hydrolysis, obtain adjacent formamido group Sodium Benzoate, then through hypochlorite decomposition's reaction and acid neutralization, isatoic anhydride is obtained.In the process of synthesis isatoic anhydride, before liquid caustic soda mixes with phthalic imidine, need the temperature reducing phthalic imidine, the same control also needed after phthalic imidine alkaline hydrolysis temperature, affects the yield of isatoic anhydride to prevent by-product in the process of phthalic imidine alkaline hydrolysis from producing; The application adopts one pot process isatoic anhydride simultaneously, decreases industrial operation amount, reduces discharging link, is also conducive to the yield and the purity that improve isatoic anhydride; Water in reaction process exists in a gaseous form, decreases the quantity discharged of waste water, reduces production cost.Experimental result shows, the yield of the isatoic anhydride of the present invention's synthesis is more than 94%, and purity is more than 99%.
Embodiment
In order to understand the present invention further, below in conjunction with embodiment, the preferred embodiment of the invention is described, but should be appreciated that these describe just for further illustrating the features and advantages of the present invention, instead of limiting to the claimed invention.
The embodiment of the invention discloses a kind of synthesis technique of isatoic anhydride, comprise the following steps:
A) mix after phthalic anhydride heat fused with urea, after reaction, be cooled to 10 DEG C ~ 20 DEG C;
B) reaction product after cooling mixed with liquid caustic soda, be cooled to-5 DEG C ~ 0 DEG C and carry out the first reaction, then mix with hypochlorite, second reacts rear and mixed in hydrochloric acid, obtains isatoic anhydride after the 3rd reaction.
This application provides a kind of synthesis technique of isatoic anhydride, first phthalic anhydride is heated up after melting with urea generation amination reaction, obtain phthalic imidine, add liquid caustic soda at low temperatures again and carry out alkaline hydrolysis at low temperatures, then Hofmann reaction is carried out with hypochlorite solutions, last and hydrochloric acid carries out neutralization reaction, obtains isatoic anhydride.
In the process of synthesis isatoic anhydride, first make it melt phthalic anhydride heating, the phthalic anhydride after fusing and urea are carried out amination reaction, obtains phthalic imidine, generate carbonic acid gas and the water of gaseous state, the chemical reaction that this process occurs is such as formula shown in (1) simultaneously:
According to the present invention, after generation phthalic imidine, reaction system is cooled to 10 DEG C ~ 20 DEG C, lower to ensure the temperature that liquid caustic soda adds in reaction system, continue to be cooled to-5 DEG C ~ 0 DEG C after liquid caustic soda adds, make phthalic imidine and liquid caustic soda generation Basic fluxing raction, obtain adjacent formamido group Sodium Benzoate, by the control to temperature before Basic fluxing raction and after Basic fluxing raction in this process, make the reaction of generation only such as formula shown in (2), and the reaction of non-generating polynomial (3).In order to reduce the temperature of the rear system of phthalic imidine reaction, water and liquid caustic soda can be added simultaneously, also first can add water, making temperature be reduced to 5 DEG C ~ 10 DEG C, then add liquid caustic soda, be cooled to-5 DEG C ~ 0 DEG C.
After phthalic imidine carries out Basic fluxing raction, then add hypochlorite carry out hoffman degradation reaction.In order to avoid the side reaction shown in generating polynomial (3) in the process of hypochlorite at hoffman degradation reaction, the beginning temperature controlling to drip hypochlorite is-5 DEG C ~ 5 DEG C, more preferably 0 DEG C.Described hypochlorite is preferably clorox.The reaction that said process carries out is such as formula shown in (4):
The application finally adds hydrochloric acid, carries out sour neutralization reaction, obtains isatoic anhydride.The reaction that said process carries out is such as formula shown in (5):
The application is in the process preparing isatoic anhydride, as preferably, the mol ratio of described phthalic anhydride, urea, liquid caustic soda, hypochlorite, hydrochloric acid is preferably 1.0:(1.0 ~ 1.3): (1.0 ~ 1.1): (0.9 ~ 1.0): (1.0 ~ 1.4); Described liquid paper mill wastewater is 32wt%, and the concentration of described hypochlorite is 10wt% ~ 13wt%, and the concentration of described hydrochloric acid is 31wt%; In certain embodiments, the mol ratio of described phthalic anhydride, urea, liquid caustic soda, hypochlorite and hydrochloric acid is 1.0:(1.05 ~ 1.2): (1.0 ~ 1.05): (0.95 ~ 1.0): (1.0 ~ 1.3); Described liquid paper mill wastewater is 32wt%, and the concentration of described hypochlorite is 10wt% ~ 13wt%, and the concentration of described hydrochloric acid is 31wt%.
This application provides a kind of synthesis technique of isatoic anhydride, comprise the following steps: a) mix after phthalic anhydride heat fused with urea, after reaction, be cooled to 10 DEG C ~ 20 DEG C; B) reaction product after cooling mixed with liquid caustic soda, be cooled to-5 DEG C ~ 0 DEG C and carry out the first reaction, then mix with hypochlorite, second reacts rear and mixed in hydrochloric acid, obtains isatoic anhydride after the 3rd reaction.The application is in the process of synthesis isatoic anhydride, first phthalic anhydride fusing is made itself and urea reaction, the carbonic acid gas of phthalic imidine and gaseous state, water is obtained after reaction, again adjacent benzene divalence imide is carried out alkaline hydrolysis, obtain adjacent formamido group Sodium Benzoate, then through hypochlorite decomposition's reaction and acid neutralization, isatoic anhydride is obtained.In the process of synthesis isatoic anhydride, before liquid caustic soda mixes with phthalic imidine, need the temperature reducing phthalic imidine, the same control also needed after adjacent benzene divalence imide alkaline hydrolysis temperature, affects the yield of isatoic anhydride to prevent by-product in the process of phthalic imidine alkaline hydrolysis from producing; The application adopts one pot process isatoic anhydride simultaneously, decreases industrial operation amount, reduces discharging link, is also conducive to the yield and the purity that improve isatoic anhydride; Water in reaction process exists in a gaseous form, decreases the discharge of waste water, reduces production cost.Experimental result shows, the yield of isatoic anhydride of the present invention is more than 94%, and purity is more than 99%.
In order to understand the present invention further, be described in detail below in conjunction with the synthesis technique of embodiment to isatoic anhydride provided by the invention, protection scope of the present invention is not limited by the following examples.
Embodiment 1
1) get phthalic anhydride 100g and be placed in 2000mL flask, heated and stirred fusing 5 ~ 10min;
2) add 21.5g urea until completely melted, be fully cooled to 10 DEG C after reaction;
3) add the liquid caustic soda 84g that 500mL water and concentration are 32wt%, continue stirring and dissolving and be cooled to 1 DEG C, when system becomes clarification, phthalic imidine dissolves completely;
4) in flask, add chlorine bleach liquor, system becomes clarification again by clarifying change muddiness, and KI test paper color development is obvious, stops adding clorox, adds the chlorine bleach liquor 424.7g that concentration is 10wt%;
5) slowly dripping concentration is 31wt% hydrochloric acid 77.2g, regulates pH=6.4, has crystal to separate out;
6) suction filtration, the crystal drawn puts into oven for drying.
Embodiment 2
1) get phthalic anhydride 100g and be placed in 2000mL flask, heated and stirred fusing 5 ~ 10min;
2) add 21.5g urea until completely melted, be fully cooled to 15 DEG C after reaction;
3) add 500mL water and continue stirring and dissolving cooling, treat that temperature is down to about 10 DEG C, add the liquid caustic soda 85g that concentration is 32wt%, continue cooling and be dissolved to 1 DEG C, system becomes phthalic imidine when clarifying and dissolves completely;
4) in flask, add clorox, system becomes clarification again by clarifying change muddiness, and KI test paper color development is obvious, stops adding clorox, adds the clorox 427.4g that concentration is 13wt%;
5) slowly drip the hydrochloric acid 77g that concentration is 31wt%, regulate pH=6.4, have crystal to separate out;
6) suction filtration, the crystal drawn puts into oven for drying.
Embodiment 3
1) get phthalic anhydride 100g and be placed in 2000mL flask, heated and stirred fusing 5 ~ 10min;
2) add 21.5g urea until completely melted, be fully cooled to 20 DEG C after reaction;
3) add the liquid caustic soda 85g that 400mL water and concentration are 32wt%, continue stirring and dissolving and be cooled to 1 DEG C, when system becomes clarification, phthalic imidine dissolves completely;
4) in flask, add clorox, system becomes clarification again by clarifying change muddiness, and KI test paper color development is obvious, stops adding clorox, and adding concentration is 12wt% clorox 439.3g;
5) slowly drip the hydrochloric acid 78g that concentration is 31wt%, regulate pH=6.4, have crystal to separate out;
6) suction filtration, the crystal drawn puts into oven for drying.
The yield data table of table 1 embodiment 1 ~ embodiment 3 isatoic anhydride
| Group | Isatoic anhydride quality/g | Isatoic anhydride purity/% | Yield % |
| Embodiment 1 | 103.66 | 99.4 | 94.5 |
| Embodiment 2 | 103.53 | 99.1 | 94.1 |
| Embodiment 3 | 103.20 | 99.0 | 93.7 |
The explanation of above embodiment just understands method of the present invention and core concept thereof for helping.It should be pointed out that for those skilled in the art, under the premise without departing from the principles of the invention, can also carry out some improvement and modification to the present invention, these improve and modify and also fall in the protection domain of the claims in the present invention.
To the above-mentioned explanation of the disclosed embodiments, professional and technical personnel in the field are realized or uses the present invention.To be apparent for those skilled in the art to the multiple amendment of these embodiments, General Principle as defined herein can without departing from the spirit or scope of the present invention, realize in other embodiments.Therefore, the present invention can not be restricted to these embodiments shown in this article, but will meet the widest scope consistent with principle disclosed herein and features of novelty.
Claims (6)
1. a synthesis technique for isatoic anhydride, comprises the following steps:
A) mix after phthalic anhydride heat fused with urea, after reaction, be cooled to 10 DEG C ~ 20 DEG C;
B) reaction product after cooling mixed with liquid caustic soda, be cooled to-5 DEG C ~ 0 DEG C and carry out the first reaction, then mix with hypochlorite, second reacts rear and mixed in hydrochloric acid, obtains isatoic anhydride after the 3rd reaction.
2. synthesis technique according to claim 1, is characterized in that, step b) in also comprised before mixing with liquid caustic soda:
Reaction product after cooling is mixed with water, is cooled to 5 DEG C ~ 10 DEG C.
3. synthesis technique according to claim 1, is characterized in that, described hypochlorite is clorox.
4. synthesis technique according to claim 1, it is characterized in that, the mol ratio of described phthalic anhydride, urea, liquid caustic soda, hypochlorite and hydrochloric acid is 1.0:(1.0 ~ 1.3): (1.0 ~ 1.1): (0.9 ~ 1.0): (1.0 ~ 1.4); Described liquid paper mill wastewater is 32wt%, and the concentration of described hypochlorite is 10wt% ~ 13wt%, and the concentration of described hydrochloric acid is 31wt%.
5. synthesis technique according to claim 1, it is characterized in that, the mol ratio of described phthalic anhydride, urea, liquid caustic soda, hypochlorite and hydrochloric acid is 1.0:(1.05 ~ 1.2): (1.0 ~ 1.05): (0.95 ~ 1.0): (1.0 ~ 1.3); Described liquid paper mill wastewater is 32wt%, and the concentration of described hypochlorite is 10wt% ~ 13wt%, and the concentration of described hydrochloric acid is 31wt%.
6. synthesis technique according to claim 1, is characterized in that, step b) described in reduce temperature to-5 DEG C ~ 5 DEG C after the first reaction.
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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105037291A (en) * | 2015-06-11 | 2015-11-11 | 武汉大学 | Preparation method of isatoic anhydride derivative |
| CN108101800A (en) * | 2018-01-12 | 2018-06-01 | 山东聚强化学有限公司 | A kind of synthetic method of ortho-aminobenzoic acid |
| CN111978269A (en) * | 2020-09-23 | 2020-11-24 | 青岛科技大学 | Continuous production process and device for isatoic anhydride |
| CN112079793A (en) * | 2020-09-23 | 2020-12-15 | 江苏剑牌农化股份有限公司 | Refining process and equipment for batch production of bentazon |
| JP2022081532A (en) * | 2017-10-05 | 2022-05-31 | ノボマー， インコーポレイテッド | Isocyanate, derivative and its manufacturing method |
| CN115140788A (en) * | 2022-08-02 | 2022-10-04 | 王兵雷 | Processing method of water pollution control agent |
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| JP2022081532A (en) * | 2017-10-05 | 2022-05-31 | ノボマー， インコーポレイテッド | Isocyanate, derivative and its manufacturing method |
| JP7357394B2 (en) | 2017-10-05 | 2023-10-06 | ノボマー， インコーポレイテッド | Isocyanates, derivatives and their production methods |
| CN108101800A (en) * | 2018-01-12 | 2018-06-01 | 山东聚强化学有限公司 | A kind of synthetic method of ortho-aminobenzoic acid |
| CN108101800B (en) * | 2018-01-12 | 2019-02-19 | 山东聚强化学有限公司 | A kind of synthetic method of ortho-aminobenzoic acid |
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| CN111978269B (en) * | 2020-09-23 | 2022-08-02 | 青岛科技大学 | Continuous production process and device for isatoic anhydride |
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