CN101973955A - Method for synthesizing isatoic anhydride - Google Patents
Method for synthesizing isatoic anhydride Download PDFInfo
- Publication number
- CN101973955A CN101973955A CN 201010278025 CN201010278025A CN101973955A CN 101973955 A CN101973955 A CN 101973955A CN 201010278025 CN201010278025 CN 201010278025 CN 201010278025 A CN201010278025 A CN 201010278025A CN 101973955 A CN101973955 A CN 101973955A
- Authority
- CN
- China
- Prior art keywords
- isatoic anhydride
- reaction
- synthesizing
- isatoic
- anhydride
- 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.)
- Granted
Links
Abstract
The invention discloses a method for synthesizing isatoic anhydride, which comprises the following steps: (1) adding phthalimide to a reaction solvent; (2) controlling the temperature to be within the range of 40-45 DEG C, introducing chlorine gas, and reacting for 1.5-2 hours; (3) controlling the temperature to be below 45 DEG C, adding solid caustic soda, and then continuing to react for 0.5-1.5 hours; and (4) filtering and collecting salts to obtain an isatoic anhydride filtrate, cooling, crystallizing, filtering, and drying to obtain solid isatoic anhydride. The method for synthesizing the isatoic anhydride avoids the use of a large amount of virulent and dangerous chemical substances and has moderate anhydrous reaction conditions, and hydrogen chloride and sodium chloride as reaction byproducts can be treated to produce high-quality hydrochloric acid and industrial sodium chloride byproducts, thereby reducing the generation and the discharge of harmful impurities and a large amount of waste water difficult to treat. The yield can be up to 92% or above. Thus, the invention is suitable for industrial application.
Description
Technical field
The present invention relates to a kind of method of synthetic isatoic anhydride, belong to field of fine chemical.
Background technology
Isatoic anhydride has another name called the support acid anhydrides, and English name Isatoic anhydride is very useful chemical intermediate, and it can react with electrophilic reagent, can react with nucleophilic reagent again.It and it homologue and derivative are widely used in synthetic agrochemicals, dyestuff, pigment, spices, essence, medicine, UV light absorber, whipping agent, fire retardant, sanitas, SYNTHETIC OPTICAL WHITNER, sterilant and sanitizer etc. fine chemical product.Its chemical structure is as follows:
Existing Isatoic acid anhydride synthesis method has a lot:
(1) is that reactions such as raw material and phosgene or Vinyl chloroformate are synthetic with the anthranilic acid, also can obtain isatoic anhydride by methyl o-aminobenzoate and phosgene reaction, but this method will be used the phosgene of severe toxicity;
(2) the isatin oxidation style is promptly with chromic acid oxidation isatin, and the used chromium trioxide of this method belongs to the heavy metal compound that restriction is used;
(3) Tetra hydro Phthalic anhydride and triazo-compound react under vitriol oil effect, and this reaction process heat release is violent, have generated the mixture of isatoic anhydride and benzimidazolone simultaneously, handle also difficulty;
(4) by the synthetic isatoic anhydride of phthalic imidine, as phthalic imidine is dissolved in the aqueous solution of sodium hydroxide, low temperature adds hypochlorite oxidation, adds acid and transfers pH to weakly alkaline, can obtain isatoic anhydride.Though this method yield is high temperature of reaction, time, pH are required very highly, if when departing from top condition, productive rate obviously reduces, and produces a large amount of reluctant contaminated wastewaters in the reaction.
The processing method of the synthetic isatoic anhydride of traditional production has many drawbacks in the production, such as not being the phosgene that has severe toxicity dangerous, raw materials such as chromium trioxide are exactly that reaction conditions is higher or produce a large amount of trade effluents, pollute problems such as big.
Summary of the invention
The object of the present invention is to provide a kind of method of synthetic isatoic anhydride, this method has avoided using a large amount of dangerous chemical substances of severe toxicity, the reaction conditions gentleness, treated high-quality hydrochloric acid and the industrial sodium-chlor byproduct produced of byproduct of reaction hydrogenchloride and sodium-chlor reduced the detrimental impurity generation.
The method of synthetic isatoic anhydride of the present invention comprises the steps:
(1) phthalic imidine is added in the reaction solvent;
(2) controlled temperature 40-45 ℃, logical chlorine reacted 1.5-2 hour;
(3) controlled temperature adds solid caustic soda below 45 ℃, finishes to continue reaction 0.5-1.5 hour;
(4) filter collection salt, get isatoic anhydride filtrate, cooling, crystallization, filtration drying get the solid isatoic anhydride.
Described reaction solvent is the halogenated alkane kind solvent, as methylene dichloride, ethylene dichloride or trichloromethane.
Described reaction solvent volume (ml): phthalic imidine quality (g)=6～3: 1.
The mol ratio of described reaction raw materials phthalic imidine, chlorine and solid caustic soda is 1: 0.9～1.25: 1～1.2.
The method of synthetic isatoic anhydride of the present invention has avoided using a large amount of dangerous chemical substances of severe toxicity, the anhydrous response mild condition, treated high-quality hydrochloric acid and the industrial sodium-chlor byproduct produced of byproduct of reaction hydrogenchloride and sodium-chlor, reduced the generation discharging of detrimental impurity and a large amount of unmanageable waste water, yield is up to more than 92%.Suitable industrial application.
Embodiment
Embodiment 1
In 250 milliliters of four-hole bottles that agitator, protractor, reflux, logical chlorine device and hydrogen chloride tail gas absorption unit are housed, add 150 milliliters of ethylene dichloride.(content 99% 0.168mol), is heated to 60～65 ℃ of stirring and dissolving to open stirring back adding 25.0 gram phthalic imidines; Cool to 40～45 ℃, feed 12.1 gram chlorine (content 99% then, 0.169mol), stirred 1.5 hours, slowly add 6.9 gram solid caustic soda sodium hydroxide (content 98%, 0.169mol) go in the bottle and controlled temperature at 40～45 ℃, add the back and continue to stir 1 hour, filtered while hot sodium chloride salt, filtrate are isatoic anhydride solution.This solution is cooled to 15～20 ℃, and isatoic anhydride is separated out in the solution, filter the solid isatoic anhydride, dry back 25.6 grams, recording content is 99.2%, calculating the isatoic anhydride product yield is 92.7%.The sodium-chlor of filtered and recycled can reach national Exposure to Sunlight Industrial Salt primary standard (GB1T5462-2003), and every index is to such as table 1.
Embodiment 2
In 250 milliliters of four-hole bottles that agitator, protractor, reflux, logical chlorine device and hydrogen chloride tail gas absorption unit are housed, add 120 milliliters of trichloromethanes.(content 99% 0.168mol), is heated to reflux state, stirring and dissolving to open stirring back adding 25.0 gram phthalic imidines; Cool to 40～45 ℃, feed 12.6 gram chlorine (content 99% then, 0.176mol), stirred 2 hours, slowly add 7.2 gram solid caustic soda sodium hydroxide (content 98%, 0.176mol) go in the bottle and controlled temperature below 45 ℃, add the back and continue to stir 1 hour, the filtered while hot sodium chloride salt, filtrate is isatoic anhydride solution.This solution is cooled to 15～20 ℃ separate out isatoic anhydride, 25.5 grams behind the filtration drying, recording content is 99.0%.By analytical calculation isatoic anhydride product yield is 92.4%.The sodium-chlor of filtered and recycled can reach national Exposure to Sunlight Industrial Salt primary standard (GB1T5462-2003), every index correlation data such as table 1.
Embodiment 3
In 250 milliliters of four-hole bottles that agitator, protractor, reflux, logical chlorine device and hydrogen chloride tail gas absorption unit are housed, add 150 milliliters of methylene dichloride.(content 99% 0.168mol), is heated to 60～65 ℃ of stirring and dissolving to open stirring back adding 25.0 gram phthalic imidines; Cool to 40～45 ℃, feed 12.1 gram chlorine (content 99% then, 0.169mol), stirred 2 hours, slowly add 7 gram solid caustic soda sodium hydroxide (content 98%, 0.172mol) go in the bottle and controlled temperature at 40～45 ℃, add the back and continue to stir 1 hour, filtered while hot sodium chloride salt, filtrate are isatoic anhydride solution.This solution is cooled to 15～20 ℃, and isatoic anhydride is separated out in the solution, filter the solid isatoic anhydride, dry back 25.4 grams, recording content is 99.1%, calculating the isatoic anhydride product yield is 92.1%.The sodium-chlor of filtered and recycled can reach national Exposure to Sunlight Industrial Salt primary standard (GB1T5462-2003), and every index is to such as table 1.
Table 1
Claims (5)
1. the method for a synthetic isatoic anhydride comprises the steps:
(1) phthalic imidine is added in the reaction solvent;
(2) controlled temperature 40-45 ℃, logical chlorine reacted 1.5-2 hour;
(3) controlled temperature adds solid caustic soda below 45 ℃, finishes to continue reaction 0.5-1.5 hour;
(4) filter collection salt, get isatoic anhydride filtrate, cooling, crystallization, filtration drying get the solid isatoic anhydride.
2. the method for the described synthetic isatoic anhydride of claim 1, reaction solvent is the halogenated alkane kind solvent.
3. the method for the described synthetic isatoic anhydride of claim 2, the halogenated alkane kind solvent is methylene dichloride, ethylene dichloride or trichloromethane.
4. the method for the described synthetic isatoic anhydride of claim 1, reaction solvent volume (ml): phthalic imidine quality (g)=6～3: 1.
5. the method for the described synthetic isatoic anhydride of claim 1, the mol ratio of phthalic imidine, chlorine and solid caustic soda is 1: 0.9～1.25: 1～1.2.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201010278025XA CN101973955B (en) | 2010-09-07 | 2010-09-07 | Method for synthesizing isatoic anhydride |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201010278025XA CN101973955B (en) | 2010-09-07 | 2010-09-07 | Method for synthesizing isatoic anhydride |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN101973955A true CN101973955A (en) | 2011-02-16 |
| CN101973955B CN101973955B (en) | 2012-03-07 |
Family
ID=43573872
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201010278025XA Active CN101973955B (en) | 2010-09-07 | 2010-09-07 | Method for synthesizing isatoic anhydride |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN101973955B (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103159694A (en) * | 2011-12-08 | 2013-06-19 | 中国中化股份有限公司 | Continuous isatoic anhydride production method |
| CN103450107A (en) * | 2013-09-13 | 2013-12-18 | 陕西嘉禾植物化工有限责任公司 | Method for preparing N-methyl isatoic anhydride |
| CN104402840A (en) * | 2014-11-12 | 2015-03-11 | 合肥星宇化学有限责任公司 | Synthesis process of isatoic anhydride |
| CN115768815A (en) * | 2020-07-07 | 2023-03-07 | 科思创德国股份有限公司 | Method for producing poly (anthranilamides), poly (anthranilamides) and use thereof |
-
2010
- 2010-09-07 CN CN201010278025XA patent/CN101973955B/en active Active
Non-Patent Citations (2)
| Title |
|---|
| 《化工科技市场》 20031231 徐金峰等 靛红酸酐的合成与应用 6-9 1-5 第26卷, 第1期 2 * |
| 《药物化学》 20071231 张士英，卢冠忠 从邻苯二甲酰亚胺合成依托酸酐 473-474 1-5 第24卷, 第6期 2 * |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103159694A (en) * | 2011-12-08 | 2013-06-19 | 中国中化股份有限公司 | Continuous isatoic anhydride production method |
| CN103159694B (en) * | 2011-12-08 | 2015-03-18 | 中国中化股份有限公司 | Continuous isatoic anhydride production method |
| CN103450107A (en) * | 2013-09-13 | 2013-12-18 | 陕西嘉禾植物化工有限责任公司 | Method for preparing N-methyl isatoic anhydride |
| CN103450107B (en) * | 2013-09-13 | 2016-05-25 | 陕西嘉禾生物科技股份有限公司 | A kind of preparation method of N-methyl-isatin acid anhydrides |
| CN104402840A (en) * | 2014-11-12 | 2015-03-11 | 合肥星宇化学有限责任公司 | Synthesis process of isatoic anhydride |
| CN104402840B (en) * | 2014-11-12 | 2017-02-15 | 合肥星宇化学有限责任公司 | Synthesis process of isatoic anhydride |
| CN115768815A (en) * | 2020-07-07 | 2023-03-07 | 科思创德国股份有限公司 | Method for producing poly (anthranilamides), poly (anthranilamides) and use thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| CN101973955B (en) | 2012-03-07 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN101973955B (en) | Method for synthesizing isatoic anhydride | |
| US10858337B2 (en) | Method for preparing 1,1′-ethylene-2,2′-bipyridinium dichloride | |
| US20200369612A1 (en) | Method for Safely Preparing Pimavanserin and Tartrate Thereof by Using Triphosgene | |
| CN106083543B (en) | A method of preparing sun-screening agent intermediate 2,4-DihydroxyBenzophenone | |
| CN104628545B (en) | A kind of preparation method of P-methoxybenzal-dehyde | |
| CN103664912B (en) | A kind of synthesis technique of prucalopride | |
| CN108341776A (en) | The technique for synthesizing Chlorquinaldol | |
| CN105254575B (en) | A kind of synthetic method of sulphadiazine | |
| CN104370791A (en) | Purifying method of levetiracetam | |
| CN101624366B (en) | Industrialized cleaning production process of captan | |
| CN104230821B (en) | The synthetic method of Fluoxastrobin | |
| JP4629322B2 (en) | Production method of cilostazol | |
| WO2017205622A1 (en) | Method of making benznidazole | |
| CN102532010B (en) | Preparation method of 2-chloro-3-aminopyridine | |
| CN108997209A (en) | A kind of preparation method of Rui Gefeini | |
| CN106518729A (en) | Lurasidone hydrochloride intermediate preparation method | |
| JP4801661B2 (en) | Method for acetylating 5-amino-2,4,6-triiodoisophthalic acid derivative | |
| CN108947919A (en) | A kind of novel processing step and its key intermediate of gout suppressant Lesinurad | |
| CN109897075B (en) | Green synthesis method of sucralose-6-acetate | |
| CN106167471A (en) | A kind of preparation method of chlorzoxazone | |
| CN113773235B (en) | Synthesis method of clorsulon | |
| CN104557604B (en) | Synthetic method for 5-acetylsalicylamide | |
| CN108383720A (en) | A kind of neighbour's substituted benzoic acid meta position chlorination | |
| CN108929206A (en) | A method of the activation bromo- 1,1- dimethoxy-ethane of 2- | |
| JP4035287B2 (en) | Method for producing isatin bis (o-cresol) |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C14 | Grant of patent or utility model | ||
| GR01 | Patent grant | ||
| PE01 | Entry into force of the registration of the contract for pledge of patent right |
Denomination of invention: Method for synthesizing isatoic anhydride Effective date of registration: 20161104 Granted publication date: 20120307 Pledgee: Hefei SME financing Company limited by guarantee Pledgor: Hefei Xingyu Chemical Co., Ltd. Registration number: 2016990000941 |
|
| PLDC | Enforcement, change and cancellation of contracts on pledge of patent right or utility model | ||
| PC01 | Cancellation of the registration of the contract for pledge of patent right |
Date of cancellation: 20171109 Granted publication date: 20120307 Pledgee: Hefei SME financing Company limited by guarantee Pledgor: Hefei Xingyu Chemical Co., Ltd. Registration number: 2016990000941 |
|
| PC01 | Cancellation of the registration of the contract for pledge of patent right |