CN101973955B - Method for synthesizing isatoic anhydride - Google Patents
Method for synthesizing isatoic anhydride Download PDFInfo
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- CN101973955B CN101973955B CN201010278025XA CN201010278025A CN101973955B CN 101973955 B CN101973955 B CN 101973955B CN 201010278025X A CN201010278025X A CN 201010278025XA CN 201010278025 A CN201010278025 A CN 201010278025A CN 101973955 B CN101973955 B CN 101973955B
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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 verivate 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 process 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; Reaction conditions is gentle; Treated high-quality hydrochloric acid and the industrial sodium-chlor sub product 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 filtrating, cooling, crystallization, filtration drying get the solid isatoic anhydride.
Said reaction solvent is the halogenated alkane kind solvent, like methylene dichloride, ethylene dichloride or trichloromethane.
Said reaction solvent volume (ml): phthalic imidine quality (g)=6～3: 1.
The mol ratio of said 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 sub product 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 whisking appliance, 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 then 12.1 the gram chlorine (content 99%, 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 continued and stirred 1 hour; The filtered while hot sodium chloride salt, filtrating is isatoic anhydride solution.This solution is cooled to 15～20 ℃, and isatoic anhydride is separated out in the solution, crosses to filter the solid isatoic anhydride, dry back 25.6 grams, and 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 each item index is to such as table 1.
Embodiment 2
In 250 milliliters of four-hole bottles that whisking appliance, 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 continued and stirred 1 hour, the filtered while hot sodium chloride salt, filtrating 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%.Through 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), each item index correlation data such as table 1.
Embodiment 3
In 250 milliliters of four-hole bottles that whisking appliance, 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 then 12.1 the gram chlorine (content 99%, 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 continued and stirred 1 hour; The filtered while hot sodium chloride salt, filtrating is isatoic anhydride solution.This solution is cooled to 15～20 ℃, and isatoic anhydride is separated out in the solution, crosses to filter the solid isatoic anhydride, dry back 25.4 grams, and 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 each item 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 filtrating, 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.
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| CN201010278025XA CN101973955B (en) | 2010-09-07 | 2010-09-07 | Method for synthesizing isatoic anhydride |
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| CN201010278025XA CN101973955B (en) | 2010-09-07 | 2010-09-07 | Method for synthesizing isatoic anhydride |
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| CN101973955A CN101973955A (en) | 2011-02-16 |
| CN101973955B true CN101973955B (en) | 2012-03-07 |
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| CN103159694B (en) * | 2011-12-08 | 2015-03-18 | 中国中化股份有限公司 | Continuous isatoic anhydride production method |
| 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 |
| 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 |
| US20230257523A1 (en) * | 2020-07-07 | 2023-08-17 | Covestro Deutschland Ag | Method for producing a poly(anthranilamide), poly(anthranilamide) and use thereof |
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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 |
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