CN110041229A - A kind of high-efficient synthesis method of salicylonitrile - Google Patents
A kind of high-efficient synthesis method of salicylonitrile Download PDFInfo
- Publication number
- CN110041229A CN110041229A CN201910412205.3A CN201910412205A CN110041229A CN 110041229 A CN110041229 A CN 110041229A CN 201910412205 A CN201910412205 A CN 201910412205A CN 110041229 A CN110041229 A CN 110041229A
- Authority
- CN
- China
- Prior art keywords
- reaction
- acket
- salicylonitrile
- phosgene
- micro passage
- 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
- C07C253/00—Preparation of carboxylic acid nitriles
- C07C253/20—Preparation of carboxylic acid nitriles by dehydration of carboxylic acid amides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a kind of high-efficient synthesis methods of salicylonitrile, including reactant pre-treatment, the setting of micro passage reaction reaction condition, four processes of synthesis and post-processing of salicylonitrile, this method be in micro passage reaction in a manner of continuous flow synthesizing o-hydroxy formonitrile HCN product, compared with the technique of existing synthesizing o-hydroxy formonitrile HCN, the method of the present invention has reaction condition controllable precise, production method serialization, highly-safe and short reaction time feature, and Acket reaction raw materials conversion ratio is up to 100%, byproduct of reaction is few, quality is high, product content >=98 (liquid chromatogram, external standard method), salicylonitrile product yield is up to 90~95% (in terms of Ackets).
Description
Technical field
The invention belongs to organic synthesis applied technical fields, and in particular to Acket solution and phosgene be original
Material carries out reaction synthesizing o-hydroxy formonitrile HCN product in micro passage reaction.It in particular is answered in bold and generous microchannel plate
In device, the technique of Acket solution and optical self-encoding salicylonitrile is utilized.
Background technique
Salicylonitrile (also known as salicylonitrile) belongs to important fine-chemical intermediate, and one side p-HBN can
For producing medical, for example, Betriol (Boehringer,Ing.), Betriol (Boehringer,Ing.) belongs to beta-receptor blocking agent, is mainly used for the heart
The treatment of the arrhythmia cordis, angina pectoris and hypertension such as the dynamic, supraventricular tachycardia of atrial fibrillation；Another aspect p-HBN is available
In the benzene cyano pesticide such as production " cynock ", " Surecide ", " Brominal ", " chloroxynil ", " white bacterium is clear "；Meanwhile to hydroxyl
Benzonitrile can also be used for liquid crystal material and field of perfumery.
Micro passage reaction than conventional tubular reactor much smaller size, because with large specific surface area and laminar mass transfer
Etc. characteristics, so that it is possessed the incomparable mass transfer of conventional reactor, heat transfer and mixed characteristic, and reactant dosage is few, energy
Expensive, toxic, adverse reaction object dosage is reduced, is a kind of environmentally friendly, safety new platform of organic synthesis.
Chinese invention patent 201610932350.0,201610931483.6 and 201610965286.6 discloses several mountains
Micro passage reaction designed by the bold and generous Chemical Engineering Technology Co., Ltd in east, which describes in detail the knots of several micro passage reactions
Structure, size and the arrangement in channel etc., it is indicated that the reactor increases reinforcing reaction process by high-specific surface area, holds liquid
Amount and treating capacity are further increased, and conversion rate of products and yield, while the coefficient of heat conduction and heat transfer effect can be effectively improved
It is significantly improved, to be conducive to the accurate control and reduction energy consumption to reaction.
So far, there is not yet carrying out Acket solution and phosgene reaction conjunction in a manner of the continuous flow of microchannel
At the research of the method for salicylonitrile.The present invention provide it is a kind of in bold and generous micro passage reaction in a manner of continuous flow,
Using Acket solution and phosgene as the process route of reactant synthesizing o-hydroxy formonitrile HCN, reaction equation is as follows:
The advantages of route, is, accurately controls condition, raw material additional amount and the residence time of reaction of reaction etc.,
Target product salicylonitrile is obtained to higher yields in a few minutes clock time within tens seconds.
Summary of the invention
It is an object of the present invention to overcome defect existing in the prior art, a kind of the efficient of salicylonitrile is provided
Synthetic method, this method be in micro passage reaction in a manner of continuous flow synthesizing o-hydroxy formonitrile HCN product, with existing synthesis
The technique of salicylonitrile compares, which has reaction condition controllable precise, production method serialization, safety
Property height and reaction time short feature, and Acket reaction raw materials conversion ratio, up to 100%, byproduct of reaction is few, product
Matter is high, and product content >=98 (liquid chromatogram, external standard method), salicylonitrile product yield is up to 90~95% (with o-hydroxy
Formamide meter).
To achieve the above object, the technical scheme is to design a kind of high-efficient synthesis method of salicylonitrile, packets
Include following steps:
S1: Acket is dissolved in atent solvent and is configured to certain density adjacent hydroxyl by reactant pre-treatment
Benzamide solution；
S2: the setting of micro passage reaction reaction condition is changed what is integrated in micro passage reaction with reaction plate
Backing is connect with external heating cooling cycle device, and the heat transferring medium in heat exchanger fin is conduction oil, by heating cooling cycle device
Set the reaction temperature of micro passage reaction；
S3: the synthesis of salicylonitrile, using Acket solution and phosgene as raw material, in micro passage reaction
It inside carries out reaction synthesizing o-hydroxy formonitrile HCN product: different flow pumps is respectively adopted by Acket solution and phosgene
The feed inlet of micro passage reaction is passed through with certain feed flow rate, Acket solution and phosgene are answered in microchannel plate
Successively preheated in device, flowing mixing and reaction, obtains reaction product mixed liquor, wherein adjusts o-hydroxy first by flow pump
The inlet amount molar ratio of amide molecule and phosgene molecule is 1: 1~4, and Acket solution feed flow velocity is 5~10mL/
Min, phosgene feed flow rate are 2~10mL/min；The reaction process in micro passage reaction reaction time be 60s~
120s, reaction temperature are 100~150 DEG C, and pressure is 0.5~1.5Mpa；
S4: the step S3 reaction product mixed liquor synthesized is isolated gas phase through gas-liquid cooling separator by post-processing
And liquid phase, wherein gas phase is recycled through gas collection tank and is post-processed, and liquid phase obtains salicylonitrile product through crystallisation by cooling, suction filtration
And filtrate, Acket total conversion are 100%, selectivity is 90~95%, and salicylonitrile product yield is
90~95%.
Preferred technical solution is that the Solute mass concentration range of Acket solution is 10 in the step S1
~30%, phosgene purity is 90~98%.
Further preferred technical solution in addition, in the step S3 Acket molecule and phosgene molecule into
Doses molar ratio is 1: 2~3, in the step S3 Acket solution feed flow velocity be 6~8mL/min, phosgene into
Stream speed is 5~10mL/min, in the step S3 reaction process reaction time in micro passage reaction be 70s~
85s, reaction temperature are 100~120 DEG C, and pressure is 0.6~1.0Mpa.
Further preferred technical solution is in addition, atent solvent used in the step S1 is toluene, dimethylbenzene or chlorine
One of benzene.
Further preferred technical solution is in addition, the filtrate in the step S4 is molten through being evaporated under reduced pressure the inertia that precipitation is sloughed
Agent recovery is to step S1.
Further preferred technical solution is in addition, the phosgene can be with surpalite or triphosgene solution substitution, neighbour's hydroxyl
The inlet amount molar ratio of yl-benzamide molecule and surpalite molecule is 1: 0.5~2, Acket molecule and triphosgene
The inlet amount molar ratio of molecule is 1: 0.33~1.33.
The advantages and beneficial effects of the present invention are:
1, the method for the present invention be in micro passage reaction in a manner of continuous flow synthesizing o-hydroxy formonitrile HCN product, and it is existing
There is the technique of synthesizing o-hydroxy formonitrile HCN to compare, which has reaction condition controllable precise, and production method is continuous
Change, highly-safe and reaction time short feature, wherein reaction time from traditional a few hours shorten to tens seconds to a few minutes,
Significantly improve reaction efficiency.
2, due to reaction mass, mixed effect is splendid in microchannel, temperature controllable precise, hence it is evident that improve reactant
Conversion ratio and the selection unicity for generating target product, wherein Acket reaction raw materials conversion ratio is reacted up to 100%
By-product is few, and selectivity of product is 90~95%, product content >=98 (liquid chromatogram, external standard method), salicylonitrile product
Yield is up to 90~95% (in terms of Ackets).
3, in micro passage reaction, reaction raw materials are successively preheated, flow mixing and reaction, which is continuous
Stream reaction avoids the leakage for needing occur in Conventional batch reaction in additional configuration device and transfer, improves entire reaction
The safety and the feature of environmental protection of process, ensure that the high efficiency of production.
Detailed description of the invention
Fig. 1 is the flow chart of the method for synthesizing o-hydroxy formonitrile HCN of the present invention.
Specific embodiment
With reference to the accompanying drawings and examples, further description of the specific embodiments of the present invention.Following embodiment is only
For clearly illustrating technical solution of the present invention, and not intended to limit the protection scope of the present invention.
Micro passage reaction used in Examples 1 to 4 is the microchannel plate of the bold and generous Chemical Engineering Technology Co., Ltd production in Shandong
It answers device (model C S1005, liquid holdup 10.4mL), which is assembled by multiple groups reaction plate serial or parallel connection, reaction plate
It fits closely and is integrated in one with heat exchanger fin.It is furnished with temperature sensor in heat exchanger fin, can be used in the real time measure heat exchanger fin
The temperature of heat transferring medium.The material of the reaction plate can be metal material, such as 304 stainless steels, Hastelloy, titanium or non-gold
Belong to material, such as SiC, quartz, different materials can be applicable in different reaction conditions, if metal material is more resistant to high pressure, SiC material
Matter is more resistant to acid and alkali corrosion；The material and quantity of heat exchanger fin and reaction plate are consistent；The particular number of reaction plate is stopped by reacting
The time is stayed to determine, agents useful for same is commercially available chemical reagent in Examples 1 to 4 and comparative example 1~4.
Embodiment 1
Using the method for micro passage reaction synthesizing o-hydroxy formonitrile HCN of the present invention, it is with Acket and phosgene
Reactant feed synthesizing o-hydroxy formonitrile HCN, includes the following steps:
S1: Acket 50g (0.36mol) is dissolved in toluene and is configured to mass concentration by reactant pre-treatment
For 30% Acket solution 167g；
S2: the setting of micro passage reaction reaction condition is changed what is integrated in micro passage reaction with reaction plate
Backing is connect with external heating cooling cycle device, and the heat transferring medium in heat exchanger fin is conduction oil, by heating cooling cycle device
Set the reaction temperature of micro passage reaction；
S3: the Acket solution and purity that the synthesis of salicylonitrile is 30% with mass concentration is
98% phosgene is raw material, and reaction synthesizing o-hydroxy formonitrile HCN product is carried out in micro passage reaction: being respectively adopted different
Acket solution and phosgene are passed through the feed inlet of micro passage reaction, adjacent hydroxyl by flow pump with certain feed flow rate
Yl-benzamide solution and phosgene are successively preheated in micro passage reaction, flow mixing and reaction, obtain reaction product mixing
Liquid, wherein the inlet amount molar ratio that Acket molecule and phosgene molecule are adjusted by flow pump is 1: 1.4, adjacent hydroxyl
Yl-benzamide solution feed flow velocity is 6mL/min, phosgene feed flow rate is 3mL/min；The reaction process is answered in microchannel plate
Reaction time is 80s in device, and reaction temperature is 100 DEG C, pressure 0.8Mpa；
S4: the step S3 reaction product mixed liquor synthesized is isolated gas phase through gas-liquid cooling separator by post-processing
And liquid phase, wherein gas phase is recycled through gas collection tank and is post-processed, and liquid phase obtains salicylonitrile product through crystallisation by cooling, suction filtration
40g and filtrate, Acket total conversion are 100%, and salicylonitrile content 98.5%, selectivity is 92%,
Yield is 92% (in terms of Acket).
Embodiment 2
Using the method for micro passage reaction synthesizing o-hydroxy formonitrile HCN of the present invention, it is with Acket and phosgene
Reactant feed synthesizing o-hydroxy formonitrile HCN, includes the following steps:
S1: Acket 50g (0.36mol) is dissolved in dimethylbenzene that be configured to quality dense by reactant pre-treatment
The Acket solution 250g that degree is 20%；
S2: the setting of micro passage reaction reaction condition is changed what is integrated in micro passage reaction with reaction plate
Backing is connect with external heating cooling cycle device, and the heat transferring medium in heat exchanger fin is conduction oil, by heating cooling cycle device
Set the reaction temperature of micro passage reaction；
S3: the Acket solution and purity that the synthesis of salicylonitrile is 40% with mass concentration is
95% phosgene is raw material, and reaction synthesizing o-hydroxy formonitrile HCN product is carried out in micro passage reaction: being respectively adopted different
Acket solution and phosgene are passed through the feed inlet of micro passage reaction, adjacent hydroxyl by flow pump with certain feed flow rate
Yl-benzamide solution and phosgene are successively preheated in micro passage reaction, flow mixing and reaction, obtain reaction product mixing
Liquid, wherein the inlet amount molar ratio that Acket molecule and phosgene molecule are adjusted by flow pump is 1: 1.8, adjacent hydroxyl
Yl-benzamide solution feed flow velocity is 8mL/min, phosgene feed flow rate is 6mL/min；The reaction process is answered in microchannel plate
Reaction time is 70s in device, and reaction temperature is 110 DEG C, pressure 0.5Mpa；
S4: the step S3 reaction product mixed liquor synthesized is isolated gas phase through gas-liquid cooling separator by post-processing
And liquid phase, wherein gas phase is recycled through gas collection tank and is post-processed, and liquid phase obtains salicylonitrile product through crystallisation by cooling, suction filtration
40.7g and filtrate, Acket total conversion are 100%, and salicylonitrile content 99%, selectivity is 94%,
Yield is 94% (in terms of Acket).
Embodiment 3
Using the method for micro passage reaction synthesizing o-hydroxy formonitrile HCN of the present invention, with Acket and surpalite
For reactant feed synthesizing o-hydroxy formonitrile HCN, include the following steps:
S1: Acket 50g (0.36mol) is dissolved in dimethylbenzene that be configured to quality dense by reactant pre-treatment
The Acket solution 500g that degree is 10%；
S2: the setting of micro passage reaction reaction condition is changed what is integrated in micro passage reaction with reaction plate
Backing is connect with external heating cooling cycle device, and the heat transferring medium in heat exchanger fin is conduction oil, by heating cooling cycle device
Set the reaction temperature of micro passage reaction；
S3: the Acket solution and purity that the synthesis of salicylonitrile is 10% with mass concentration is
98% surpalite is raw material, and reaction synthesizing o-hydroxy formonitrile HCN product is carried out in micro passage reaction: difference is respectively adopted
Flow pump Acket solution and surpalite are passed through to the feed inlet of micro passage reaction with certain feed flow rate,
Acket solution and phosgene are successively preheated in micro passage reaction, flow mixing and reaction, obtain reaction product
Mixed liquor, wherein the inlet amount molar ratio that Acket molecule and surpalite molecule are adjusted by flow pump is 1:
0.5, Acket solution feed flow velocity is 5mL/min, surpalite feed flow rate is 2mL/min；The reaction process exists
Reaction time is 100s in micro passage reaction, and reaction temperature is 150 DEG C, pressure 1.2Mpa；
S4: the step S3 reaction product mixed liquor synthesized is isolated gas phase through gas-liquid cooling separator by post-processing
And liquid phase, wherein gas phase is recycled through gas collection tank and is post-processed, and liquid phase obtains salicylonitrile product through crystallisation by cooling, suction filtration
40.7g and filtrate, Acket total conversion are 100%, and salicylonitrile content 98%, selectivity is 93%,
Yield is 93% (in terms of Acket).
Embodiment 4
Using the method for micro passage reaction synthesizing o-hydroxy formonitrile HCN of the present invention, with Acket and triphosgene
For reactant feed synthesizing o-hydroxy formonitrile HCN, include the following steps:
S1: reactant pre-treatment, respectively by Acket 50g (0.36mol) and triphosgene 160g (0.54mol)
It is dissolved in and is configured to Acket solution 200g and triphosgene solution 641g that mass concentration is 25% in dimethylbenzene；
S2: the setting of micro passage reaction reaction condition is changed what is integrated in micro passage reaction with reaction plate
Backing is connect with external heating cooling cycle device, and the heat transferring medium in heat exchanger fin is conduction oil, by heating cooling cycle device
Set the reaction temperature of micro passage reaction；
S3: the synthesis of salicylonitrile, it is molten for 25% Acket solution and triphosgene with mass concentration
Liquid is raw material, and reaction synthesizing o-hydroxy formonitrile HCN product is carried out in micro passage reaction: different flow pumps is respectively adopted will
Acket solution and triphosgene are passed through the feed inlet of micro passage reaction, o-hydroxy first with certain feed flow rate
Amide solution and triphosgene are successively preheated in micro passage reaction, flow mixing and reaction, obtain reaction product mixed liquor,
In, the inlet amount molar ratio that Acket molecule and triphosgene molecule are adjusted by flow pump is 1: 1.5, o-hydroxy
Formamide solution feed flow rate is 10mL/min, triphosgene feed flow rate is 10mL/min；The reaction process is answered in microchannel plate
Reaction time is 60s in device, and reaction temperature is 140 DEG C, pressure 1.0Mpa；
S4: the step S3 reaction product mixed liquor synthesized is isolated gas phase through gas-liquid cooling separator by post-processing
And liquid phase, wherein gas phase is recycled through gas collection tank and is post-processed, and liquid phase obtains salicylonitrile product through crystallisation by cooling, suction filtration
41.1g and filtrate, Acket total conversion are 100%, and salicylonitrile content 99%, selectivity is 95%,
Yield is 95% (in terms of Acket).
Comparative example 1
Comparative example 1 the difference from embodiment 1 is that, using o-hydroxy first disclosed in Chinese patent 20121057263.7
The preparation method of nitrile carrys out synthesizing o-hydroxy formonitrile HCN product, by 50g (0.36mol) Acket, toluene 116g,
0.05g(5.76×10-4Mol) dioxane is added in the 1000mL three-necked flask with stirring and return pipe, is heated to flowing back,
It is 51g (0.5mol) that the phosgene quality that purity is 98% is passed through in 2h, and the molar ratio of Acket and phosgene is 1:
1.4；Reaction solution evaporated into 58g toluene after heat preservation 0.5h, and by concentrate in ice-water bath stirred crystallization, filter 40g is solid
Body product, wherein Acket content is 13%, and salicylonitrile content is 81.0%, and Acket turns
Rate is about 89.6%, and salicylonitrile yield is 74.6% (in terms of Acket).
Comparative example 2
Comparative example 2 the difference from example 2 is that, using o-hydroxy first disclosed in Chinese patent 20121057263.7
The preparation method of nitrile carrys out synthesizing o-hydroxy formonitrile HCN product, by 50g (0.36mol) Acket, dimethylbenzene 75g,
0.05g(5.76×10-4Mol) dioxane is added in the 1000mL three-necked flask with stirring and return pipe, is heated to flowing back,
Purity is passed through in 2h as 98% phosgene 66g (0.65mol), the molar ratio of Acket and phosgene is 1: 1.8；Heat preservation
Reaction solution is evaporated into 38g dimethylbenzene after 1h, and by concentrate in ice-water bath stirred crystallization, filter to obtain 44g solid product,
Middle Acket content is 7.5%, and salicylonitrile content is 83.0%, and Acket conversion ratio is about
93.4%, salicylonitrile yield is 84.0% (in terms of Acket).
Comparative example 3
Comparative example 3 and the difference of embodiment 3 are, using o-hydroxy first disclosed in Chinese patent 20121057263.7
The preparation method of nitrile carrys out synthesizing o-hydroxy formonitrile HCN product, by 50g (0.36mol) Acket, toluene 116g,
0.05g(5.76×10-4Mol) dioxane is added in the 1000mL three-necked flask with stirring and return pipe, is heated to flowing back,
Concentration is passed through in 2h as 98% surpalite 36.4g (0.18mol), the molar ratio of Acket and surpalite is 1:
0.5；Reaction solution evaporated into 58g toluene after heat preservation 0.5h, and by concentrate in ice-water bath stirred crystallization, filter 47g is solid
Body product, wherein Acket content is 15.1%, and salicylonitrile content is 63.0%, Acket
Conversion ratio is about 85.8%, and salicylonitrile yield is 68.2% (in terms of Acket).
Comparative example 4
Comparative example 4 and the difference of embodiment 4 are, using o-hydroxy first disclosed in Chinese patent 20121057263.7
The preparation method of nitrile carrys out synthesizing o-hydroxy formonitrile HCN product, by 50g (0.36mol) Acket, chlorobenzene 75g, 0.05g
(5.76×10-4Mol) dioxane is added in the 1000mL three-necked flask with stirring and return pipe, is heated to flowing back, in 2h
The triphosgene chlorobenzene solution 400g (triphosgene 0.54mol) that concentration is 40% is slowly introducing into three-necked flask；It will after heat preservation 1h
Reaction solution evaporates 38g chlorobenzene, and by concentrate in ice-water bath stirred crystallization, 44g solid product is filtered to obtain, wherein adjacent hydroxyl
Benzamide content is 10.5%, and salicylonitrile content is 74.1%, and Acket conversion ratio is about 90.8%,
Salicylonitrile yield is 75.1% (in terms of Acket).
1~4 experimental data of 1 Examples 1 to 4 of table and comparative example
The results showed that Examples 1 to 4 uses the method for the present invention synthesizing o-hydroxy formonitrile HCN, wherein o-hydroxy first
The conversion ratio of amide is up to 100%, and for salicylonitrile content 98% or more, yield 90% or more, illustrates this hair
Hydroxybenzamide generates the selectivity height of target molecule in bright synthetic method, reduces the generation of by-product, ensure that reaction
Transformation efficiency, the product quality of Examples 1 to 4 be apparently higher than comparative example 1~4 use Chinese patent 201110301805.6
The quality of the salicylonitrile of the preparation method synthesis of disclosed neighbour's (to) hydroxy-phenylformonitrile, and Examples 1 to 4 is compared with comparative example
1~4 reaction time is obviously shortened, and illustrates synthetic method of the invention combined coefficient with higher, the present invention provides one
Kind efficiently synthesizes the new method of salicylonitrile.
The above is only a preferred embodiment of the present invention, it is noted that for the ordinary skill people of the art
For member, without departing from the technical principles of the invention, several improvements and modifications can also be made, these improvements and modifications
Also it should be regarded as protection scope of the present invention.
Claims (6)
1. a kind of high-efficient synthesis method of salicylonitrile, which comprises the steps of:
S1: Acket is dissolved in atent solvent and is configured to certain density o-hydroxy first by reactant pre-treatment
Amide solution；
S2: the setting of micro passage reaction reaction condition, the heat exchanger fin that will be integrated in micro passage reaction with reaction plate
It is connect with external heating cooling cycle device, the heat transferring medium in heat exchanger fin is conduction oil, passes through heating cooling cycle device setting
The reaction temperature of good micro passage reaction；
S3: the synthesis of salicylonitrile, using Acket solution and phosgene as raw material, in micro passage reaction into
Row reaction synthesizing o-hydroxy formonitrile HCN product: different flow pumps is respectively adopted by Acket solution and phosgene with one
Fixed feed flow rate is passed through the feed inlet of micro passage reaction, and Acket solution and phosgene are in micro passage reaction
Successively preheated, flowing mixing and reaction, obtains reaction product mixed liquor, wherein adjust Acket by flow pump
The inlet amount molar ratio of molecule and phosgene molecule be 1: 1~4, Acket solution feed flow velocity be 5~10mL/min,
Phosgene feed flow rate is 2~10mL/min；Reaction process reaction time in micro passage reaction is 60s~120s,
Reaction temperature is 100~150 DEG C, and pressure is 0.5~1.5Mpa；
S4: the step S3 reaction product mixed liquor synthesized is isolated gas phase and liquid through gas-liquid cooling separator by post-processing
Phase, wherein gas phase is recycled through gas collection tank and is post-processed, and liquid phase obtains salicylonitrile product and filter through crystallisation by cooling, suction filtration
Liquid, Acket total conversion be 100%, selectivity be 90~95%, salicylonitrile product yield be 90~
95%.
2. the high-efficient synthesis method of salicylonitrile as described in claim 1, which is characterized in that adjacent hydroxyl in the step S1
The Solute mass concentration range of benzamide solution is 10~30%, and phosgene purity is 90~98%.
3. the high-efficient synthesis method of salicylonitrile as claimed in claim 2, which is characterized in that adjacent hydroxyl in the step S3
The inlet amount molar ratio of benzamide molecule and phosgene molecule is 1: 2~3, in the step S3 Acket solution into
Stream speed is 6~8mL/min, phosgene feed flow rate is 5~10mL/min, and the reaction process is in microchannel plate in the step S3
Answering reaction time in device is 70s~85s, and reaction temperature is 100~120 DEG C, and pressure is 0.6~1.0Mpa.
4. the high-efficient synthesis method of salicylonitrile as claimed in claim 3, which is characterized in that used in the step S1
Atent solvent is one of toluene, dimethylbenzene or chlorobenzene.
5. the high-efficient synthesis method of salicylonitrile as claimed in claim 4, which is characterized in that the filtrate in the step S4
The atent solvent recovery sloughed of precipitation is evaporated under reduced pressure to step S1.
6. the high-efficient synthesis method of salicylonitrile as claimed in claim 5, which is characterized in that the phosgene can be with surpalite
Or triphosgene solution substitution, the inlet amount molar ratio of the Acket molecule and surpalite molecule is 1: 0.5~2,
The inlet amount molar ratio of Acket molecule and triphosgene molecule is 1: 0.33~1.33.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201910412205.3A CN110041229A (en) | 2019-05-17 | 2019-05-17 | A kind of high-efficient synthesis method of salicylonitrile |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201910412205.3A CN110041229A (en) | 2019-05-17 | 2019-05-17 | A kind of high-efficient synthesis method of salicylonitrile |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN110041229A true CN110041229A (en) | 2019-07-23 |
Family
ID=67282430
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201910412205.3A Pending CN110041229A (en) | 2019-05-17 | 2019-05-17 | A kind of high-efficient synthesis method of salicylonitrile |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN110041229A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111704538A (en) * | 2020-06-15 | 2020-09-25 | 杭州迈科瑞科技有限公司 | Method for preparing p-hydroxyphenylacetic acid by using microreactor |
| CN113248402A (en) * | 2021-05-26 | 2021-08-13 | 南京先进生物材料与过程装备研究院有限公司 | Method for preparing salicylaldehyde by adopting micro-flow field technology |
| CN115636769A (en) * | 2021-07-20 | 2023-01-24 | 联化科技股份有限公司 | Preparation process of 4-carbamoylbenzoyl chloride and process for preparing 4-cyanobenzoyl chloride by using same |
| CN115636763A (en) * | 2021-07-20 | 2023-01-24 | 联化科技股份有限公司 | Continuous preparation process of 4-carbamoylbenzoyl chloride and process for preparing 4-cyanobenzoyl chloride by using same |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103012205A (en) * | 2012-12-26 | 2013-04-03 | 湖南海利常德农药化工有限公司 | Preparation method of salicylonitrile |
| CN105017076A (en) * | 2015-06-29 | 2015-11-04 | 安徽广信农化股份有限公司 | 2-cyanophenol solvent recovery pretreatment method |
| CN106083655A (en) * | 2016-05-28 | 2016-11-09 | 安徽广信农化股份有限公司 | A kind of novel method for synthesizing of salicylonitrile |
-
2019
- 2019-05-17 CN CN201910412205.3A patent/CN110041229A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103012205A (en) * | 2012-12-26 | 2013-04-03 | 湖南海利常德农药化工有限公司 | Preparation method of salicylonitrile |
| CN105017076A (en) * | 2015-06-29 | 2015-11-04 | 安徽广信农化股份有限公司 | 2-cyanophenol solvent recovery pretreatment method |
| CN106083655A (en) * | 2016-05-28 | 2016-11-09 | 安徽广信农化股份有限公司 | A kind of novel method for synthesizing of salicylonitrile |
Non-Patent Citations (2)
| Title |
|---|
| 何伟明，等: "光气法合成邻羟基苯甲腈研究", 《上海化工》 * |
| 赵忠奎，等: "《高效反应技术与绿色化学》", 31 July 2012 * |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111704538A (en) * | 2020-06-15 | 2020-09-25 | 杭州迈科瑞科技有限公司 | Method for preparing p-hydroxyphenylacetic acid by using microreactor |
| CN113248402A (en) * | 2021-05-26 | 2021-08-13 | 南京先进生物材料与过程装备研究院有限公司 | Method for preparing salicylaldehyde by adopting micro-flow field technology |
| CN113248402B (en) * | 2021-05-26 | 2023-08-25 | 南京先进生物材料与过程装备研究院有限公司 | Method for preparing salicylonitrile by adopting micro-flow field technology |
| CN115636769A (en) * | 2021-07-20 | 2023-01-24 | 联化科技股份有限公司 | Preparation process of 4-carbamoylbenzoyl chloride and process for preparing 4-cyanobenzoyl chloride by using same |
| CN115636763A (en) * | 2021-07-20 | 2023-01-24 | 联化科技股份有限公司 | Continuous preparation process of 4-carbamoylbenzoyl chloride and process for preparing 4-cyanobenzoyl chloride by using same |
| CN115636763B (en) * | 2021-07-20 | 2024-03-08 | 联化科技股份有限公司 | Continuous preparation process of 4-carbamoyl benzoyl chloride and process for preparing 4-cyano benzoyl chloride by using same |
| CN115636769B (en) * | 2021-07-20 | 2024-04-16 | 联化科技股份有限公司 | Preparation process of 4-carbamoyl benzoyl chloride and process for preparing 4-cyano benzoyl chloride by using same |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN110041229A (en) | A kind of high-efficient synthesis method of salicylonitrile | |
| CN110003052A (en) | A method of using micro passage reaction synthesizing o-hydroxy formonitrile HCN | |
| JP2002038043A (en) | Preparation of disazo condensation pigment in microreactor | |
| CN108409516A (en) | A kind of method of continuous current micro-reactor synthesis benzophenone derivates | |
| CN107473949A (en) | A kind of synthesis technique of the pentanone of 3,5 dichloro 2 | |
| CN108586389A (en) | A kind of new method of synthesis Cariliprazine | |
| CN106380375A (en) | A method of continuously synthesizing hexanedioic acid through a microchannel reactor | |
| CN113277942B (en) | Method for rapidly preparing 5-chloro-2-fluoro-4- (trifluoromethyl) benzoic acid based on microchannel reaction technology | |
| CN108654549A (en) | A kind of venturi injection mixing reactor, a kind of oleamide are continuously synthesizing to device and its application method | |
| CN113181850A (en) | Microchannel preparation method of indole compound | |
| CN106892840B (en) | A method of purification para-Phthalonitrile | |
| CN101659626B (en) | Method for preparing mint-based carboxylic acid in process of synthesizing N-Ethyl-p-menthane-3-carboxamide | |
| CN107216256A (en) | A kind of synthetic method of N, N diisopropyl ethylenediamine | |
| CN103896858A (en) | Technology for preparing cytosine | |
| CN110746326A (en) | Method for continuously producing hydroxyethyl sulfonic acid | |
| CN101391943B (en) | Method for preparing 4-chlorophenylcyclopropyl methyl ketone | |
| CN106563438A (en) | Catalyst for synthesizing amide and method for synthesizing N,N-dimethylpropionamide | |
| JP2010024187A (en) | Method for producing aromatic nitrile | |
| CN105646513B (en) | The method for continuously preparing pyrans and indolizine is reacted using micro flow field | |
| CN113234030B (en) | Preparation method of 6-bromo-3-hydroxy-2-pyrazinecarboxamide | |
| CN112778146B (en) | Method for preparing p-hydroxyphenylglycine in pulse tubular reactor | |
| CN104592003A (en) | Decoloring method of crude stearyl chloride | |
| CN107867979B (en) | Method for continuously preparing 4- (6-hydroxyhexyloxy) phenol | |
| CN107353229B (en) | A kind of preparation method of agomelatine intermediate body | |
| CN114602453B (en) | Method for preparing amide |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| RJ01 | Rejection of invention patent application after publication | ||
| RJ01 | Rejection of invention patent application after publication |
Application publication date: 20190723 |