CN106883154A - A kind of method of continuous synthesis sulphones - Google Patents
A kind of method of continuous synthesis sulphones Download PDFInfo
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- CN106883154A CN106883154A CN201710013937.6A CN201710013937A CN106883154A CN 106883154 A CN106883154 A CN 106883154A CN 201710013937 A CN201710013937 A CN 201710013937A CN 106883154 A CN106883154 A CN 106883154A
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- quenched
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C315/00—Preparation of sulfones; Preparation of sulfoxides
- C07C315/02—Preparation of sulfones; Preparation of sulfoxides by formation of sulfone or sulfoxide groups by oxidation of sulfides, or by formation of sulfone groups by oxidation of sulfoxides
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Abstract
The invention discloses a kind of method of continuous synthesis sulphones.The method is comprised the following steps：Using water as solvent, using sodium tungstate and/or potassium tungstate as catalyst, under 55~80 DEG C of temperature conditionss, sulfide oxidation is synthesized by sulphones using hydrogen peroxide in flow reactor, wherein, the structural formula of thioether isN=1,3,4.Apply the technical scheme of the present invention, it is easy to operate, the product polluted to environment will not be produced, it is very friendly to environment；With safe, economic, environmentally friendly, operability it is high, reaction effect is good, hold facility rate is low the characteristics of.
Description
Technical field
The present invention relates to chemosynthesis technical field, in particular to a kind of method of continuous synthesis sulphones.
Background technology
Sulfone compound is not only important intermediate in organic synthesis, and because biology of the majority with spectrum is living
Property, shown in the medicine such as desinsection, sterilization, weeding, antitumor, antiviral, human body HIV 1, waterlogging-resistant
Good effect, is widely used to agricultural chemicals and medicine and other fields.
Sulfone is generally obtained by thioether, and various oxidants can realize this transformation, including H2O2, NaClO, H5IO6,
PhICl2, CrO3, KMnO4, KHSO5, CH3CO3H etc..Although thioether can be direct oxidation into sulfone by above-mentioned oxidant, from
Atom economy, environment are nuisanceless, safe operation and simplicity are angularly set out, H2O2Undoubtedly a kind of most popular oxidant.
With H2O2It is oxidant, the oxidation system oxidation system oxidizing sulfur ether such as co-catalyst into sulfone on sulfide oxidation it has been reported that but exist
Application in terms of continuous reaction, post processing is little.
Existing pharmacy, chemical production field, intermittent reaction is readily adapted to accommodate different operating condition and product variety due to it
The characteristics of still as main reaction formation, but with the continuous expansion of range of application, intermittent reaction can only go into operation in batches, need
The shortcomings of having the auxiliary operations such as charging and discharging, unstable product quality determines to be increasingly difficult to meet fine chemistry industry and pharmacy
The demand in field, further, since batch tank reactor Existential Space takes greatly, position fixes limited, and reaction time is long, mass transfer
Heat transfer efficiency is poor, and local reaction is uneven, the shortcomings of side reaction is more, and can not the continuously large batch of production that feeds intake, cause it to make
With being very limited, it is increasingly difficult to meet the growth requirement of fine chemistry industry.
In the synthesis of critical medication intermediate, the influence that successive reaction technology has a wide range of applications with abyss.It is continuous anti-
It should be the direction of current chemical reaction development.Successive reaction possesses that equipment volume is small, and the operating time is adjustable, product quality stabilization,
Easily operated control, the advantages of flow is adjustable, was widely deployed and was applied to field of medicine and chemical technology in the last few years, had saved a large amount of
Manpower and materials, and reduce very big producing cost.
The content of the invention
The present invention is intended to provide a kind of method of continuous synthesis sulphones, is synthesized with solving intermittent reaction in the prior art
Sulphones are reaction time long, the unstable technical problem of quality.
To achieve these goals, according to an aspect of the invention, there is provided a kind of side of continuous synthesis sulphones
Method.The method is comprised the following steps：Using water as solvent, using sodium tungstate and/or potassium tungstate as catalyst, in 55~80 DEG C of temperature
Under the conditions of degree, sulfide oxidation is synthesized by sulphones using hydrogen peroxide in flow reactor, wherein, the structural formula of thioether isN=1,3,4.
Further, the molar ratio of thioether, hydrogen peroxide, sodium tungstate and/or potassium tungstate is 1：2~3.5：0.01.
Further, the B component that the component A and hydrogen peroxide of thioether, water and sodium tungstate and/or potassium tungstate composition are constituted is simultaneously
Flow reactor is flowed into, the first product is obtained after hybrid reaction in flow reactor.
Further, also include：First product be quenched reagent flow into simultaneously it is continuous reactor be quenched be quenched,
Obtain the second product.
Further, also include：Second product is extracted into continuous extraction apparatus, obtains water phase and organic
Phase, wherein, extractant is ethyl acetate, methyl tertiary butyl ether(MTBE) or isopropyl acetate.
Further, organic phase is directly concentrated under reduced pressure or removes solvent into film apparatus concentration, obtains sulphones.
Further, component A and the B component residence time in flow reactor are 5~20min, and reaction continuously is being quenched
The residence time is 2~10min in device, and the residence time is 0.5~5min in continuous extraction apparatus.
Further, flow reactor uses stainless steel tube, Hastelloy pipe or the polytetrafluoroethylene (PTFE) of external diameter 3mm~10mm
Pipe makes.
Further, flow reactor temperature control is continuously quenched reactor temperature control at 5~10 DEG C at 55~80 DEG C.
Further, flow reactor, the continuous charging that reactor and continuous extraction apparatus is quenched passes through to automate and feeds
System is controlled.
Apply the technical scheme of the present invention, it is easy to operate, the product polluted to environment will not be produced, to environment very
It is friendly；With safe, economic, environmentally friendly, operability it is high, reaction effect is good, hold facility rate is low the characteristics of.
Brief description of the drawings
The Figure of description for constituting the part of the application is used for providing a further understanding of the present invention, of the invention to show
Meaning property and its illustrates, for explaining the present invention, not constitute inappropriate limitation of the present invention embodiment.In the accompanying drawings：
Fig. 1 shows the schematic flow sheet of according to embodiments of the present invention 1 continuous synthesis sulphones.
Specific embodiment
It should be noted that in the case where not conflicting, the feature in embodiment and embodiment in the application can phase
Mutually combination.Describe the present invention in detail below with reference to the accompanying drawings and in conjunction with the embodiments.
According to a kind of typical implementation method of the present invention, there is provided a kind of method of continuous synthesis sulphones.The method bag
Include following steps：Using water as solvent, using sodium tungstate and/or potassium tungstate as catalyst, under 55~80 DEG C of temperature conditionss,
Sulfide oxidation is synthesized by sulphones using hydrogen peroxide in flow reactor, wherein, the structural formula of thioether isn
=1,3,4.
Apply the technical scheme of the present invention, it is easy to operate, the product polluted to environment will not be produced, to environment very
It is friendly；With safe, economic, environmentally friendly, operability it is high, reaction effect is good, hold facility rate is low the characteristics of.
Preferably, the molar ratio of thioether, hydrogen peroxide, sodium tungstate and/or potassium tungstate is 1：2~3.5：0.01.Herein
The carrying out of reaction is not only improved in proportion, is unlikely to waste hydrogen peroxide again.According to a kind of typical implementation method of the present invention,
The B component of the component A and hydrogen peroxide composition of thioether, water and sodium tungstate and/or potassium tungstate composition flows into flow reactor simultaneously,
The first product is obtained in flow reactor after hybrid reaction.Material mixed stability in component A is good, but anti-with B component
Should, it is divided into two groups, be conducive to the manipulation of industrialized production.According to a kind of typical implementation method of the present invention, the method is further
Including：First product be quenched reagent flow into simultaneously it is continuous reactor be quenched be quenched, obtain the second product.This
Planting and mode benefit is quenched can be terminated in time after the first product is produced, it is to avoid possible rotten, and when having saved post processing
Between, improve production efficiency.
According to a kind of typical implementation method of the present invention, the method is further included：Second product enters continuous extraction
Take device to be extracted, obtain water phase and organic phase, wherein, extractant is ethyl acetate, methyl tertiary butyl ether(MTBE) or acetic acid
Isopropyl ester.
According to a kind of typical implementation method of the present invention, organic phase is directly concentrated under reduced pressure or is concentrated into film apparatus and removes
Solvent, obtains sulphones.
Preferably, according to reaction speed, component A and the B component residence time in flow reactor are 5~20min, even
It is continuous reactor is quenched in the residence time be 2~10min, the residence time is 0.5~5min in continuous extraction apparatus.When this is stopped
Between can both ensure reaction effect, production efficiency can be ensured again, it may be said that be reaction effect and production efficiency preferably put down
Weighing apparatus point.
According to a kind of typical implementation method of the present invention, stainless steel tube, Kazakhstan of the flow reactor using external diameter 3mm~10mm
Family name's compo pipe or polyfluortetraethylene pipe make.The selection such less external diameters of 3~10mm can ensure that reaction mixed effect is good, adopt
With stainless steel tube, Hastelloy pipe or polyfluortetraethylene pipe reactor can be made to corrosion materials more resistant to corrosion.
Preferably, the temperature according to needed for reaction, at 55~80 DEG C, this temperature can make material continuous to flow reactor temperature control
Fully reacted in reactor, reactor temperature control is continuously quenched at 5~10 DEG C.According to a kind of typical implementation method of the present invention, connect
Continue reactor, the charging of reactor and continuous extraction apparatus continuously is quenched by automating feed system control.Controlled by it
Program can realize a closed-loop control system of computer-feed pump-electronic scale, only need to set each mass flow, so that it may automatic
The stable state of each raw material is kept to feed, if system failure or flow error can be automatically stopped the charging of pump when exceeding setting value,
And alarm.
The method of the present invention, beneficial to the commodity production for realizing scale, automation, application prospect is good.
Beneficial effects of the present invention are further illustrated below in conjunction with embodiment.
The structural formula of thioether is in the present inventionPreparing sulfone structural formula isWherein n=1,
3,4.
Embodiment 1
Prepare 3- (methyl sulphonyl) acetic acid
As shown in figure 1, adding 100g 3- methyl thios acetic acid (thioether), 3.1g bis- to be hydrated in the conical flasks of 500ml first
Sodium tungstate, 500ml water.First conical flask is placed on corresponding first balance of the first pump 11, by automatic feed software set
The setting charging rate of one pump 11 21g/min.225g hydrogen peroxide (3.5% concentration) is added in the conical flasks of 500ml second.Second cone
Shape bottle is placed on corresponding second balance of the second pump 12, and charging rate is set by the second pump of automatic feed software set 12
7.8g/min。
58.0g sodium thiosulfate is added in 1000ml triconics bottle, the 745ml aqueous solution is used as being quenched reagent.Taper
Bottle is placed on corresponding 3rd balance of the 3rd pump 13, and charging rate 27.8g/ is set by the 3rd pump of automatic feed software set 13
min。
450g ethyl acetate is added in the conical flasks of 1000ml the 4th as extractant.Conical flask is placed in the 4th pump 14 pairs
On the 4th balance answered, charging rate 15.6g/min is set by the 4th pump of automatic feed software set 14.
By continuous 60~70 DEG C of (tubular type) the reactor temperature controls of 200ml, 0~10 DEG C of reactor temperature control is continuously quenched, continuous extraction
Take post and keep room temperature.
First pump 11, the second pump 12, respectively by the first conical flask, the second conical flask are run by automatic feed system simultaneously
Middle material is pumped into flow reactor 20, after 5min, runs the 3rd pump 13, is continuously quenched reagent being quenched and pumping into triconic bottle
Go out in reactor 30, run the 4th pump 14, ethyl acetate in the 4th conical flask is pumped into churned mechanically continuous extraction post
In 40.System from reactor 30 is continuously quenched out carries out continuous extraction point liquid and obtains light component into continuous extraction post 40
Organic phase and heavy constituent water phase.Organic phase is collected, and concentration removes the grease that solvent obtains 98%HPLC purity.
The data of resulting product are as follows：
HNMR：(500MHz,CDCl3) δ=2.83 (s, 3H), 4.54 (s, 2H), 11.0 (s, H)
Above-mentioned as shown by data product is 3- (methyl sulphonyl) acetic acid, detects quantitative with nuclear-magnetism internal standard, 3- (sulfonyloxy methyls
Base) yield of acetic acid is 82%, its structural formula is
Embodiment 2
Prepare 3- (methyl sulphonyl) acetic acid
100g 3- methylpropanethioates, 3.1g Disodium tungstate (Na2WO4) dihydrates, 500ml water are added in the conical flasks of 500ml first.
First conical flask is placed on corresponding first balance of the first pump, by the pump of automatic feed software set first set charging rate as
21g/min.282.9g hydrogen peroxide (35% concentration) is added in the conical flasks of 500ml second, the second conical flask is placed in the second pump pair
On the second balance answered, charging rate as 9.9g/min is set by the pump of automatic feed software set second.
52.2g sodium thiosulfate, the 670ml aqueous solution are added in 1000ml triconics bottle 3.Triconic bottle is placed in the
On corresponding 3rd balance of three pumps, charging rate as 25g/min is set by the pump of automatic feed software set the 3rd.
450g ethyl acetate is added in the conical flasks of 1000ml the 4th.It is corresponding 4th day that 4th conical flask is placed in the 4th pump
On flat, charging rate 15.6g/min is set by the pump of automatic feed software set the 4th.
By 55~60 DEG C of 200ml continuous tubular reactors temperature control, 5~10 DEG C of reactor temperature control, continuous extraction is continuously quenched
Post keeps room temperature.
First pump, the second pump are run by automatic feed system simultaneously, respectively by the first conical flask and the second conical flask
Material is pumped into flow reactor (coil reactor retention time 5min), after 5min, runs the 3rd pump, by triconic bottle
Reagent is quenched pumps into and be continuously quenched in reactor, quenching time 2min runs the 4th pump, by ethyl acetate pump in the 4th conical flask
Enter with churned mechanically continuous extraction post.System from reactor continuously is quenched out is connected into continuous extraction post
Continuous extraction point liquid, extracts residence time 0.5min, and organic phase is collected, and concentration removes the oily that solvent obtains 98%HPLC purity
Thing.Detect quantitative with nuclear-magnetism internal standard, the yield of 3- (methyl sulphonyl) propionic acid is 90%.
Embodiment 3
All of operation after 20min, runs the 3rd pump with embodiment 1, coil reactor retention time 20min.Produced
Product HPLC purity 98%, nuclear-magnetism internal standard yield 91%.
Embodiment 4
All of operation is with embodiment 1, quenching time 10min.Obtain product HPLC purity 98%, nuclear-magnetism internal standard yield
89%.
Embodiment 5
All of operation extracts residence time 5min with embodiment 1.Product HPLC purity 98% is obtained, nuclear-magnetism internal standard is received
Rate 90%.
Embodiment 6
All of operation is with embodiment 1,75~80 DEG C of reactor temperature control.Obtain product HPLC purity 98%, nuclear-magnetism internal standard
Yield 90%.
Embodiment 7
Prepare 3- (methyl sulphonyl) butyric acid
100g 3- methyl-thiobutanoic acids, 2.5g Disodium tungstate (Na2WO4) dihydrates, 500ml water are added in the conical flasks of 500ml first.
First conical flask is placed on corresponding first balance of the first pump, and charging rate is set by the pump of automatic feed software set first
21g/min.173.7g hydrogen peroxide (3.5% concentration) is added in the conical flasks of 500ml second.Second conical flask is placed in the second pump pair
On the second balance answered, charging rate 6g/min is set by the pump of automatic feed software set second.
44.8g sodium thiosulfate, the 575ml aqueous solution are added in 1000ml triconics bottle.Conical flask is placed in the 3rd pump
On corresponding 3rd balance, charging rate 21.5g/min is set by the pump of automatic feed software set the 3rd.
450g ethyl acetate is added in the conical flasks of 1000ml the 4th.Conical flask is placed in corresponding 4th balance of the 4th pump
On, charging rate 15.6g/min is set by the pump of automatic feed software set the 4th.
By 65~75 DEG C of 200ml continuous tubular reactors temperature control, 0~10 DEG C of reactor temperature control, continuous extraction is continuously quenched
Post keeps room temperature.
First pump, the second pump, respectively by the first conical flask, the second taper vial are run by automatic feed system simultaneously
During material pumps into flow reactor, after 5min, the 3rd pump is run, reagent will be quenched in triconic bottle and pump into reactor continuously is quenched
In, the 4th pump is run, ethyl acetate in the 4th conical flask is pumped into in churned mechanically continuous extraction post.From being continuously quenched
System in reactor out carries out continuous extraction point liquid into continuous extraction post.Organic phase is collected, and concentration removes solvent and obtains
The grease of 98%HPLC purity.
The data of resulting product are as follows：
1H-NMR(CDC13):δ 3.20 (t, 2H, J=7.6Hz), 2.98 (s, 3H), 2.52 (t, 2H, J=7.2Hz),
2.09(m,2H)
Above-mentioned as shown by data product is 3- (methyl sulphonyl) butyric acid, detects quantitative with nuclear-magnetism internal standard, 3- (sulfonyloxy methyls
Base) yield of butyric acid is 81%, its structural formula is
Embodiment 8
Prepare 3- (methyl sulphonyl) valeric acid
100g 3- methyl thios valeric acid, 2.2g Disodium tungstate (Na2WO4) dihydrates, 500ml water are added in the conical flasks of 500ml first.
First conical flask is placed on corresponding first balance of the first pump, and charging rate is set by the pump of automatic feed software set first
21g/min.225g hydrogen peroxide (3.5% concentration) is added in the conical flasks of 500ml second.Second conical flask is placed in the second pump correspondence
The second balance on, charging rate 7.8g/min is set by the pump of automatic feed software set second.
58.0g sodium thiosulfate, the 745ml aqueous solution are added in 1000ml triconics bottle.Conical flask is placed in the 3rd pump
On corresponding 3rd balance, charging rate 27.8g/min is set by the pump of automatic feed software set the 3rd.
450g ethyl acetate is added in the conical flasks of 1000ml the 4th.Conical flask is placed in corresponding 4th balance of the 4th pump
On, charging rate 15.6g/min is set by the pump of automatic feed software set the 4th.
By 60~70 DEG C of 200ml continuous tubular reactors temperature control, 0~10 DEG C of reactor temperature control, continuous extraction is continuously quenched
Post keeps room temperature.
First pump, the second pump, respectively by the first conical flask, the second taper vial are run by automatic feed system simultaneously
During material pumps into flow reactor, after 5min, the 3rd pump is run, reagent will be quenched in triconic bottle and pump into reactor continuously is quenched
In, the 4th pump is run, ethyl acetate in the 4th conical flask is pumped into in churned mechanically continuous extraction post.From being continuously quenched
System in reactor out carries out continuous extraction point liquid into continuous extraction post.Organic phase is collected, and concentration removes solvent and obtains
The grease of 98%HPLC purity.
The data of resulting product are as follows：
HNMR：(500MHz,CDCl3) δ=1.5~1.6 (m, 4H), 2.3 (m, 2H), 2.83 (s, 3H), 3.41 (m, 2H)
Above-mentioned as shown by data product is 3- (methyl sulphonyl) valeric acid, detects quantitative with nuclear-magnetism internal standard, 3- (sulfonyloxy methyls
Base) yield of valeric acid is 90%, its structural formula is
Embodiment 9
With embodiment 1, catalyst replaces sodium tungstate using 3.1g potassium tungstates for all of operation.Obtain product HPLC purity
98%, nuclear-magnetism internal standard yield 88%.
Embodiment 10
With embodiment 1, extractant replaces ethyl acetate using 450g methyl tertiary butyl ether(MTBE)s for all of operation.Obtain product
HPLC purity 98%, nuclear-magnetism internal standard yield 90%.
Embodiment 11
All of operation takes solvent and replaces ethyl acetate using 450g isopropyl acetates with embodiment 1.Obtain product HPLC
Purity 98%, nuclear-magnetism internal standard yield 90%.
As can be seen from the above description, the above embodiments of the present invention realize following technique effect：
The present invention is a kind of continuous oxidation thioether into the method for sulfone and continuously is quenched, continuous extraction answering in post processing
With.Its innovative point is, for the reaction of current system, can with continuous feed, discharge, be quenched, extract, reactor liquid holdup
Few, mass-transfer efficiency is high, and precisely, the operating time is adjustable for temperature control, and precisely, package unit floor space is small, security for inlet amount
Height, it is simple to operate.Amplification that is high to the screening efficiency of reaction condition and being conducive to continuous processing.
The preferred embodiments of the present invention are the foregoing is only, is not intended to limit the invention, for the skill of this area
For art personnel, the present invention can have various modifications and variations.It is all within the spirit and principles in the present invention, made any repair
Change, equivalent, improvement etc., should be included within the scope of the present invention.
Claims (10)
1. it is a kind of it is continuous synthesis sulphones method, it is characterised in that comprise the following steps：Using water as solvent, with wolframic acid
Sodium and/or potassium tungstate under 55~80 DEG C of temperature conditionss, use hydrogen peroxide by thioether oxygen as catalyst in flow reactor
Sulphones are combined to, wherein, the structural formula of the thioether isN=1,3,4.
2. method according to claim 1, it is characterised in that the thioether, the hydrogen peroxide, the sodium tungstate and/or
The molar ratio of potassium tungstate is 1：2~3.5：0.01.
3. method according to claim 1, it is characterised in that the thioether, the water and the sodium tungstate and/or wolframic acid
The component A of potassium composition flows into the flow reactor simultaneously with the B component of hydrogen peroxide composition, mixes in the flow reactor
The first product is obtained after reaction.
4. method according to claim 3, it is characterised in that further include：First product with examination is quenched
Agent inflow simultaneously is continuously quenched reactor and is quenched, and obtains the second product.
5. method according to claim 4, it is characterised in that further include：Second product enters continuous
Extraction equipment is extracted, and obtains water phase and organic phase, wherein, extractant is ethyl acetate, methyl tertiary butyl ether(MTBE) or second
Isopropyl propionate.
6. method according to claim 5, it is characterised in that the organic phase is directly concentrated under reduced pressure or enters film apparatus
Concentration removes solvent, obtains sulphones.
7. method according to claim 6, it is characterised in that the component A and the B component are in the flow reactor
The middle residence time is 5~20min, it is described it is continuous reactor is quenched in the residence time be 2~10min, in the continuous extraction
The residence time is 0.5~5min in device.
8. method according to claim 6, it is characterised in that the flow reactor using external diameter 3mm~10mm not
Rust steel pipe, Hastelloy pipe or polyfluortetraethylene pipe make.
9. method according to claim 6, it is characterised in that described that reactor temperature control continuously is quenched at 0~10 DEG C.
10. method according to claim 6, it is characterised in that the flow reactor, it is described it is continuous be quenched reactor and
The charging of the continuous extraction apparatus is by automating feed system control.
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN107421306A (en) * | 2017-08-02 | 2017-12-01 | 凯莱英医药集团（天津）股份有限公司 | Pyrrolidones oxidation reaction apparatus and method |
| CN108129267A (en) * | 2018-01-11 | 2018-06-08 | 吉林凯莱英医药化学有限公司 | Low temperature Total continuity reaction system and application |
| CN108329241A (en) * | 2018-04-12 | 2018-07-27 | 重庆华邦胜凯制药有限公司 | A kind of preparation method of dapsone |
| CN114292216A (en) * | 2021-12-27 | 2022-04-08 | 宁波南大光电材料有限公司 | Process for producing diphenylsulfoxide compound |
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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107421306A (en) * | 2017-08-02 | 2017-12-01 | 凯莱英医药集团（天津）股份有限公司 | Pyrrolidones oxidation reaction apparatus and method |
| CN107421306B (en) * | 2017-08-02 | 2023-05-05 | 凯莱英医药集团（天津）股份有限公司 | Pyrrolidone oxidation reaction device and method |
| CN108129267A (en) * | 2018-01-11 | 2018-06-08 | 吉林凯莱英医药化学有限公司 | Low temperature Total continuity reaction system and application |
| CN108129267B (en) * | 2018-01-11 | 2024-04-19 | 吉林凯莱英医药化学有限公司 | Low-temperature full-continuous reaction system and application |
| CN108329241A (en) * | 2018-04-12 | 2018-07-27 | 重庆华邦胜凯制药有限公司 | A kind of preparation method of dapsone |
| CN114292216A (en) * | 2021-12-27 | 2022-04-08 | 宁波南大光电材料有限公司 | Process for producing diphenylsulfoxide compound |
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