CN103012205B - Preparation method of salicylonitrile - Google Patents
Preparation method of salicylonitrile Download PDFInfo
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- CN103012205B CN103012205B CN201210572630.7A CN201210572630A CN103012205B CN 103012205 B CN103012205 B CN 103012205B CN 201210572630 A CN201210572630 A CN 201210572630A CN 103012205 B CN103012205 B CN 103012205B
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Abstract
The invention discloses a method for synthesizing salicylonitrile by using ortho-hydroxybenzamide as a raw material, dioxane or tetrahydropyrane and tetrahydrofuran as catalysts, and dimethylbenzene or benzene, methylbenzene and chlorobenzene as solvents through introducing phosgene at a refluxing temperature. The reaction formula is described in the specification. The invention relates to a method for preparing the salicylonitrile without generating waste water and waste slag. Compared with the prior art, the method has the advantages of less reaction byproducts, high quality, high yield, simplicity and safety in operation, low price and easily available raw material, the content of the salicylonitrile is not less than 98 percent (liquid chromatogram, external standard method), and the yield of the salicylonitrile is not less than 95 percent (in the terms of o-hydroxybenzamide).
Description
Technical field
The present invention relates to a kind of intermediate salicylonitrile preparation method of sterilant Azoxystrobin.
Background technology
Salicylonitrile is the important intermediate of synthesizing new high-efficiency broad spectrum methoxy acrylic bactericide Azoxystrobin, structural formula:
Its synthetic method has multiple, and through phosgene dehydration, Acket directly generates the method for salicylonitrile, and the method produces waste water, and product content and yield are on the low side.With the adjacent hydroxyl aldoxime of salicylaldhyde and oxammonium hydrochloride synthetic intermediate, then under acidic conditions the method for synthesizing o-hydroxy formonitrile HCN, yield is less than 90%, content is less than 95%, operational condition is gentle but this synthetic method produces a large amount of unmanageable waste water.Take ortho-methyl phenol as raw material, pass through into ether, methyl cyano group, last under alkaline condition the method for synthesizing o-hydroxy formonitrile HCN, this synthetic method craft is complicated, yield is low, is not suitable for scale production.Acket dehydration generates the method for salicylonitrile, and this synthetic method produces phosphorus-containing wastewater, and in product, phosphorous major impurity is difficult to remove.Acket dehydration generates the method for salicylonitrile, and this synthetic method is usingd nitrogenous class alkaline organic as catalyzer, produces processing wastewater.
Summary of the invention
The preparation method who the object of this invention is to provide a kind of salicylonitrile is characterized in that take that Acket is as raw material, take dioxane, tetrahydropyrans or tetrahydrofuran (THF) as catalyzer, take dimethylbenzene, benzene, toluene or chlorobenzene as solvent, under reflux temperature, pass into phosgene synthesizing o-hydroxy formonitrile HCN, reaction solution obtains the salicylonitrile solid that content is greater than 98% after precipitation, crystallization.
Reaction formula:
The quality consumption of described solvent is 3～8 times of Acket quality, the mol ratio of phosgene and Acket is 1.2:1, the quality consumption of catalyzer is 0.1%～0.5% of Acket quality, and the reaction times is 2～4hr, and temperature of reaction is reflux temperature.During reaction solution precipitation, remove approximately half solvent, crystallize out in ice-water bath, filters, dry, can obtain solid salicylonitrile.
The invention provides a class and promote reaction process, suppress the catalyzer that by product generates, is a kind of salicylonitrile preparation method who does not produce waste water and waste residue, compared with prior art has the following advantages:
1. byproduct of reaction is few, and quality is high, and yield is high, product content >=98%(liquid chromatography, external standard method), product yield >=95%(is in Acket);
2. do not produce waste water and waste residue;
3. safety simple to operate, the raw material of use is cheaply easy to get.
Embodiment
Embodiment 1
13.7g(0.1mol) Acket, 41.1g(0.39mol) dimethylbenzene, 0.014g(1.6 * 10
-4mol) dioxane adds to the 100mL there-necked flask with stirring and return line, is heated to reflux, and passes into 11.9g(0.12mol in 2hr) phosgene.
After insulation 0.5hr, reaction solution is evaporated to 21g dimethylbenzene, concentrated solution is stirring and crystallizing in ice-water bath, filters to obtain 11.8g salicylonitrile, and content 98.3%(liquid chromatography external standard method is lower same), yield 97.5%.
Embodiment 2
13.7g(0.1mol) Acket, 68.5g(0.65mol) dimethylbenzene, 0.041g(4.7 * 10
-4mol) dioxane adds to the 100mL there-necked flask with stirring and return line, is heated to reflux, and passes into 11.9g(0.12mol in 3hr) phosgene.
After insulation 0.5hr, reaction solution is evaporated to 34g dimethylbenzene, concentrated solution is stirring and crystallizing in ice-water bath, filters to obtain 11.6g salicylonitrile, content 98.9%, yield 96.4%.
Embodiment 3
13.7g(0.1mol) Acket, 108g(1.02mol) dimethylbenzene, 0.068g(7.7 * 10
-4mol) dioxane adds to the 100mL there-necked flask with stirring and return line, is heated to reflux, and passes into 11.9g(0.12mol in 4hr) phosgene.
After insulation 0.5hr, reaction solution is evaporated to 55g dimethylbenzene, concentrated solution is stirring and crystallizing in ice-water bath, filters to obtain 11.5g salicylonitrile, content 99.2%, yield 95.9%.
Embodiment 4
13.7g(0.1mol) Acket, 41.3g(0.53mol) benzene, 0.014g(1.6 * 10
-4mol) dioxane adds to the 100mL there-necked flask with stirring and return line, is heated to reflux, and passes into 12g(0.12mol in 2hr) phosgene.
After insulation 0.5hr, reaction solution is evaporated to 21g benzene, concentrated solution is stirring and crystallizing in ice-water bath, filters to obtain 11.7g salicylonitrile, content 98.1%, yield 96.5%.
Embodiment 5
13.7g(0.1mol) Acket, 68.6g(0.88mol) benzene, 0.041g(4.7 * 10
-4mol) dioxane adds to the 100mL there-necked flask with stirring and return line, is heated to reflux, and passes into 11.9g(0.12mol in 3hr) phosgene.
After insulation 0.5hr, reaction solution is evaporated to 34.8g benzene, concentrated solution is stirring and crystallizing in ice-water bath, filters to obtain 11.6g salicylonitrile, content 98.9%, yield 96.4%.
Embodiment 6
13.7g(0.1mol) Acket, 109g(1.4mol) benzene, 0.068g(7.7 * 10
-4mol) dioxane adds to the 100mL there-necked flask with stirring and return line, is heated to reflux, and passes into 11.9g(0.12mol in 4hr) phosgene.
After insulation 0.5hr, reaction solution is evaporated to 54g benzene, concentrated solution is stirring and crystallizing in ice-water bath, filters to obtain 11.4g salicylonitrile, content 99.3%, yield 95.1%.
Embodiment 7
13.7g(0.1mol) Acket, 41.4g(0.45mol) toluene, 0.014g(1.6 * 10
-4mol) dioxane adds to the 100mL there-necked flask with stirring and return line, is heated to reflux, and passes into 11.9g(0.12mol in 2hr) phosgene.
After insulation 0.5hr, reaction solution is evaporated to 22g toluene, concentrated solution is stirring and crystallizing in ice-water bath, filters to obtain 11.9g salicylonitrile, content 98.0%, yield 98.0%.
Embodiment 8
13.7g(0.1mol) Acket, 69g(0.75mol) toluene, 0.041g(4.7 * 10
-4mol) dioxane adds to the 100mL there-necked flask with stirring and return line, is heated to reflux, and passes into 12g(0.12mol in 3hr) phosgene.
After insulation 0.5hr, reaction solution is evaporated to 35.3g toluene, concentrated solution is stirring and crystallizing in ice-water bath, filters to obtain 11.6g salicylonitrile, content 98.2%, yield 95.7%.
Embodiment 9
13.7g(0.1mol) Acket, 109g(1.18mol) toluene, 0.068g(7.7 * 10
-4mol) dioxane adds to the 100mL there-necked flask with stirring and return line, is heated to reflux, and passes into 11.9g(0.12mol in 4hr) phosgene.
After insulation 0.5hr, reaction solution is evaporated to 55g toluene, concentrated solution is stirring and crystallizing in ice-water bath, filters to obtain 11.5g salicylonitrile, content 98.9%, yield 95.6%.
Embodiment 10
13.7g(0.1mol) Acket, 41.5g(0.37mol) chlorobenzene, 0.014g(1.6 * 10
-4mol) dioxane adds to the 100mL there-necked flask with stirring and return line, is heated to reflux, and passes into 12g(0.12mol in 2hr) phosgene.
After insulation 0.5hr, reaction solution is evaporated to 21.1g chlorobenzene, concentrated solution is stirring and crystallizing in ice-water bath, filters to obtain 11.8g salicylonitrile, content 98.3%, yield 97.5%.
Embodiment 11
13.7g(0.1mol) Acket, 67.5g(0.6mol) chlorobenzene, 0.041g(4.7 * 10
-4mol) dioxane adds to the 100mL there-necked flask with stirring and return line, is heated to reflux, and passes into 12g(0.12mol in 3hr) phosgene.
After insulation 0.5hr, reaction solution is evaporated to 33.8g chlorobenzene, concentrated solution is stirring and crystallizing in ice-water bath, filters to obtain 11.7g salicylonitrile, content 98.5%, yield 96.8%.
Embodiment 12
13.7g(0.1mol) Acket, 108g(0.96mol) chlorobenzene, 0.068g(7.7 * 10
-4mol) dioxane adds to the 100mL there-necked flask with stirring and return line, is heated to reflux, and passes into 12g(0.12mol in 4hr) phosgene.
After insulation 0.5hr, reaction solution is evaporated to 55.8g chlorobenzene, concentrated solution is stirring and crystallizing in ice-water bath, filters to obtain 11.5g salicylonitrile, content 98.5%, yield 95.2%.
Embodiment 13
13.7g(0.1mol) Acket, 42g(0.4mol) dimethylbenzene, 0.014g(1.6 * 10
-4mol) tetrahydropyrans adds to the 100mL there-necked flask with stirring and return line, is heated to reflux, and passes into 12g(0.12mol in 2hr) phosgene.
After insulation 0.5hr, reaction solution is evaporated to 21.3g dimethylbenzene, concentrated solution is stirring and crystallizing in ice-water bath, filters to obtain 11.5g salicylonitrile, content 98.5%, yield 95.2%.
Embodiment 14
13.7g(0.1mol) Acket, 68.4g(0.65mol) dimethylbenzene, 0.041g(4.8 * 10
-4mol) tetrahydropyrans adds to the 100mL there-necked flask with stirring and return line, is heated to reflux, and passes into 12g(0.12mol in 3hr) phosgene.
After insulation 0.5hrr, reaction solution is evaporated to 34g dimethylbenzene, concentrated solution is stirring and crystallizing in ice-water bath, filters to obtain 11.6g salicylonitrile, content 98.5%, yield 96.0%.
Embodiment 15
13.7g(0.1mol) Acket, 108g(1.02mol) dimethylbenzene, 0.068g(7.9 * 10
-4mol) tetrahydropyrans adds to the 100mL there-necked flask with stirring and return line, is heated to reflux, and passes into 11.9g(0.12mol in 4hr) phosgene.
After insulation 0.5hrr, reaction solution is evaporated to 55g dimethylbenzene, concentrated solution is stirring and crystallizing in ice-water bath, filters to obtain 11.5g salicylonitrile, content 98.9%, yield 95.6%.
Embodiment 16
13.7g(0.1mol) Acket, 42g(0.54mol) benzene, 0.014g(1.6 * 10
-4mol) tetrahydropyrans adds to the 100mL there-necked flask with stirring and return line, is heated to reflux, and passes into 12g(0.12mol in 2hr) phosgene.
After insulation 0.5hr, reaction solution is evaporated to 21g benzene, concentrated solution is stirring and crystallizing in ice-water bath, filters to obtain 11.7g salicylonitrile, content 98.1%, yield 96.5%.
Embodiment 17
13.7g(0.1mol) Acket, 67.9g(0.87mol) benzene, 0.041g(4.8 * 10
-4mol) tetrahydropyrans adds to the 100mL there-necked flask with stirring and return line, is heated to reflux, and passes into 11.9g(0.12mol in 3hr) phosgene.
After insulation 0.5hr, reaction solution is evaporated to 34g benzene, concentrated solution is stirring and crystallizing in ice-water bath, filters to obtain 11.6g salicylonitrile, content 98.3%, yield 95.8%.
Embodiment 18
13.7g(0.1mol) Acket, 109g(1.4mol) benzene, 0.068g(7.9 * 10
-4mol) tetrahydropyrans adds to the 100mL there-necked flask with stirring and return line, is heated to reflux, and passes into 11.9g(0.12mol in 4hr) phosgene.
After insulation 0.5hr, reaction solution is evaporated to 50.4g benzene, concentrated solution is stirring and crystallizing in ice-water bath, filters to obtain 11.5g salicylonitrile, content 98.4%, yield 95.1%.
Embodiment 19
13.7g(0.1mol) Acket, 41.5g(0.45mol) toluene, 0.014g(1.6 * 10
-4mol) tetrahydropyrans adds to the 100mL there-necked flask with stirring and return line, is heated to reflux, and passes into 12.1g(0.12mol in 2hr) phosgene.
After insulation 0.5hr, reaction solution is evaporated to 22g toluene, concentrated solution is stirring and crystallizing in ice-water bath, filters to obtain 11.8g salicylonitrile, content 98.0%, yield 97.2%.
Embodiment 20
13.7g(0.1mol) Acket, 70g(0.76mol) toluene, 0.041g(4.8 * 10
-4mol) tetrahydropyrans adds to the 100mL there-necked flask with stirring and return line, is heated to reflux, and passes into 12g(0.12mol in 3hr) phosgene.
After insulation 0.5hr, reaction solution is evaporated to 35g toluene, concentrated solution is stirring and crystallizing in ice-water bath, filters to obtain 11.7g salicylonitrile, content 98.2%, yield 96.5%.
Embodiment 21
13.7g(0.1mol) Acket, 108g(1.17mol) toluene, 0.068g(7.9 * 10
-4mol) tetrahydropyrans adds to the 100mL there-necked flask with stirring and return line, is heated to reflux, and passes into 11.9g(0.12mol in 4hr) phosgene.
After insulation 0.5hr, reaction solution is evaporated to 55g toluene, concentrated solution is stirring and crystallizing in ice-water bath, filters to obtain 11.7g salicylonitrile, content 98.4%, yield 96.7%.
Embodiment 22
13.7g(0.1mol) Acket, 43g(0.38mol) chlorobenzene, 0.014g(1.6 * 10
-4mol) tetrahydropyrans adds to the 100mL there-necked flask with stirring and return line, is heated to reflux, and passes into 12g(0.12mol in 2hr) phosgene.
After insulation 0.5hr, reaction solution is evaporated to 21g chlorobenzene, concentrated solution is stirring and crystallizing in ice-water bath, filters to obtain 11.4g salicylonitrile, content 99.3%, yield 95.1%.
Embodiment 23
13.7g(0.1mol) Acket, 67.5g(0.6mol) chlorobenzene, 0.041g(4.8 * 10
-4mol) tetrahydropyrans adds to the 100mL there-necked flask with stirring and return line, is heated to reflux, and passes into 12g(0.12mol in 3hr) phosgene.
After insulation 0.5hr, reaction solution is evaporated to 34.1g chlorobenzene, concentrated solution is stirring and crystallizing in ice-water bath, filters to obtain 11.4g salicylonitrile, content 99.5%, yield 95.3%.
Embodiment 24
13.7g(0.1mol) Acket, 108g(0.96mol) chlorobenzene, 0.068g(7.9 * 10
-4mol) tetrahydropyrans adds to the 100mL there-necked flask with stirring and return line, is heated to reflux, and passes into 12.1g(0.12mol in 4hr) phosgene.
After insulation 0.5hr, reaction solution is evaporated to 55.3g chlorobenzene, concentrated solution is stirring and crystallizing in ice-water bath, filters to obtain 11.4g salicylonitrile, content 99.5%, yield 95.3%.
Embodiment 25
13.7g(0.1mol) Acket, 42g(0.4mol) dimethylbenzene, 0.014g(1.9 * 10
-4mol) tetrahydrofuran (THF) adds to the 100mL there-necked flask with stirring and return line, is heated to reflux, and passes into 11.9g(0.12mol in 2hr) phosgene.
After insulation 0.5hr, reaction solution is evaporated to 20.5g dimethylbenzene, concentrated solution is stirring and crystallizing in ice-water bath, filters to obtain 11.7g salicylonitrile, content 98.3%, yield 96.6%.
Embodiment 26
13.7g(0.1mol) Acket, 68.5g(0.65mol) dimethylbenzene, 0.041g(5.7 * 10
-4mol) tetrahydrofuran (THF) adds to the 100mL there-necked flask with stirring and return line, is heated to reflux, and passes into 11.9g(0.12mol in 3hr) phosgene.
After insulation 0.5hr, reaction solution is evaporated to 33.3g dimethylbenzene, concentrated solution is stirring and crystallizing in ice-water bath, filters to obtain 11.7g salicylonitrile, content 98.5%, yield 96.8%.
Embodiment 27
13.7g(0.1mol) Acket, 108g(1.02mol) dimethylbenzene, 0.068g(9.4 * 10
-4mol) tetrahydrofuran (THF) adds to the 100mL there-necked flask with stirring and return line, is heated to reflux, and passes into 11.9g(0.12mol in 4hr) phosgene.
After insulation 0.5hr, reaction solution is evaporated to 52g dimethylbenzene, concentrated solution is stirring and crystallizing in ice-water bath, filters to obtain 11.6g salicylonitrile, content 98.6%, yield 96.1%.
Embodiment 28
13.7g(0.1mol) Acket, 42g(0.54mol) benzene, 0.014g(1.9 * 10
-4mol) tetrahydrofuran (THF) adds to the 100mL there-necked flask with stirring and return line, is heated to reflux, and passes into 12.2g(0.12mol in 2hr) phosgene.
After insulation 0.5hr, reaction solution is evaporated to 20g benzene, concentrated solution is stirring and crystallizing in ice-water bath, filters to obtain 11.5g salicylonitrile, content 98.3%, yield 95.0%.
Embodiment 29
13.7g(0.1mol) Acket, 69g(0.88mol) benzene, 0.041g(5.7 * 10
-4mol) tetrahydrofuran (THF) adds to the 100mL there-necked flask with stirring and return line, is heated to reflux, and passes into 11.9g(0.12mol in 3hr) phosgene.
After insulation 0.5hr, reaction solution is evaporated to 35.8g benzene, concentrated solution is stirring and crystallizing in ice-water bath, filters to obtain 11.5g salicylonitrile, content 98.5%, yield 95.2%.
Embodiment 30
13.7g(0.1mol) Acket, 109g(1.4mol) benzene, 0.068g(9.4 * 10
-4mol) tetrahydrofuran (THF) adds to the 100mL there-necked flask with stirring and return line, is heated to reflux, and passes into 11.9g(0.12mol in 4hr) phosgene.
After insulation 0.5hr, reaction solution is evaporated to 56g benzene, concentrated solution is stirring and crystallizing in ice-water bath, filters to obtain 11.4g salicylonitrile, content 99.2%, yield 95.0%.
Embodiment 31
13.7g(0.1mol) Acket, 41.7g(0.45mol) toluene, 0.014g(1.9 * 10
-4mol) tetrahydrofuran (THF) adds to the 100mL there-necked flask with stirring and return line, is heated to reflux, and passes into 11.8g(0.12mol in 2hr) phosgene.
After insulation 0.5hr, reaction solution is evaporated to 22.7g toluene, concentrated solution is stirring and crystallizing in ice-water bath, filters to obtain 11.8g salicylonitrile, content 98.3%, yield 97.5%.
Embodiment 32
13.7g(0.1mol) Acket, 69g(0.75mol) toluene, 0.041g(5.7 * 10
-4mol) tetrahydrofuran (THF) adds to the 100mL there-necked flask with stirring and return line, is heated to reflux, and passes into 12g(0.12mol in 3hr) phosgene.
After insulation 0.5hr, reaction solution is evaporated to 35.3g toluene, concentrated solution is stirring and crystallizing in ice-water bath, filters to obtain 11.6g salicylonitrile, content 98.8%, yield 96.3%.
Embodiment 33
13.7g(0.1mol) Acket, 109g(1.18mol) toluene, 0.068g(9.4 * 10
-4mol) tetrahydrofuran (THF) adds to the 100mL there-necked flask with stirring and return line, is heated to reflux, and passes into 12g(0.12mol in 4hr) phosgene.
After insulation 0.5hr, reaction solution is evaporated to 55g toluene, concentrated solution is stirring and crystallizing in ice-water bath, filters to obtain 11.5g salicylonitrile, content 98.9%, yield 95.6%.
Embodiment 34
13.7g(0.1mol) Acket, 42g(0.37mol) chlorobenzene, 0.014g(1.9 * 10
-4mol) tetrahydrofuran (THF) adds to the 100mL there-necked flask with stirring and return line, is heated to reflux, and passes into 12g(0.12mol in 2hr) phosgene.
After insulation 0.5hr, reaction solution is evaporated to 21.9g chlorobenzene, concentrated solution is stirring and crystallizing in ice-water bath, filters to obtain 11.5g salicylonitrile, content 98.8%, yield 95.6%.
Embodiment 35
13.7g(0.1mol) Acket, 67.5g(0.6mol) chlorobenzene, 0.041g(5.7 * 10
-4mol) tetrahydrofuran (THF) adds to the 100mL there-necked flask with stirring and return line, is heated to reflux, and passes into 12.1g(0.12mol in 3hr) phosgene.
After insulation 0.5hr, reaction solution is evaporated to 33g chlorobenzene, concentrated solution is stirring and crystallizing in ice-water bath, filters to obtain 11.5g salicylonitrile, content 98.9%, yield 95.6%.
Embodiment 36
13.7g(0.1mol) Acket, 108g(0.96mol) chlorobenzene, 0.068g(9.4 * 10
-4mol) tetrahydrofuran (THF) adds to the 100mL there-necked flask with stirring and return line, is heated to reflux, and passes into 11.9g(0.12mol in 4hr) phosgene.
After insulation 0.5hr, reaction solution is evaporated to 55g chlorobenzene, concentrated solution is stirring and crystallizing in ice-water bath, filters to obtain 11.4g salicylonitrile, content 99.4%, yield 95.2%.
Claims (2)
1. the preparation method of a salicylonitrile, it is characterized in that take that Acket is as raw material, take dioxane, tetrahydropyrans or tetrahydrofuran (THF) as catalyzer, take dimethylbenzene, benzene, toluene or chlorobenzene as solvent, under reflux temperature, pass into phosgene synthesizing o-hydroxy formonitrile HCN
Reaction formula:
Reaction solution obtains the salicylonitrile solid of content >=98% after precipitation, crystallization.
2. the preparation method of a kind of salicylonitrile according to claim 1, the quality consumption that it is characterized in that described solvent is 3～8 times of Acket quality, the mol ratio of phosgene and Acket is 1.2 ︰ 1, the quality consumption of catalyzer is 0.1%～0.5% of Acket quality, reaction times is 2～4hr, and temperature of reaction is reflux temperature.
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN103664698B (en) * | 2013-12-18 | 2015-12-09 | 湖南化工研究院 | The preparation method of o-hydroxy nitrile |
| CN103739518B (en) * | 2013-12-26 | 2016-03-30 | 安徽广信农化股份有限公司 | A kind of synthesis technique of salicylonitrile |
| CN104610095B (en) * | 2015-01-04 | 2016-09-28 | 尹山红 | A kind of preparation method of salicylonitrile |
| CN106496066A (en) * | 2016-09-27 | 2017-03-15 | 江苏嘉隆化工有限公司 | A kind of preparation method of salicylonitrile |
| CN109336781A (en) * | 2018-12-12 | 2019-02-15 | 湖南海利常德农药化工有限公司 | A kind of purification process of salicylonitrile |
| CN110003052A (en) * | 2019-05-17 | 2019-07-12 | 常州工程职业技术学院 | A method of using micro passage reaction synthesizing o-hydroxy formonitrile HCN |
| CN110041229A (en) * | 2019-05-17 | 2019-07-23 | 常州工程职业技术学院 | A kind of high-efficient synthesis method of salicylonitrile |
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Application publication date: 20130403 Assignee: Ningxia Haili Technology Co.,Ltd. Assignor: HUNAN HAILI CHANGDE PESTICIDE & CHEMICAL INDUSTRY CO.,LTD. Contract record no.: X2023980037360 Denomination of invention: Preparation of o-hydroxy Benzonitrile Granted publication date: 20141008 License type: Common License Record date: 20230703 |