CN107473992A - A kind of utilize produces the method that discarded object caused by dimethyl sulfone prepares mesyl chloride - Google Patents
A kind of utilize produces the method that discarded object caused by dimethyl sulfone prepares mesyl chloride Download PDFInfo
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- CN107473992A CN107473992A CN201710745419.3A CN201710745419A CN107473992A CN 107473992 A CN107473992 A CN 107473992A CN 201710745419 A CN201710745419 A CN 201710745419A CN 107473992 A CN107473992 A CN 107473992A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/02—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/42—Separation; Purification; Stabilisation; Use of additives
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Abstract
The invention discloses a kind of method for preparing mesyl chloride using discarded object caused by dimethyl sulfone is produced, comprise the following steps：A, solid waste will be mixed caused by production dimethyl sulfone with acetone, condensing reflux removes the organic sulphur components in solid waste；B, the solid waste for removing organic sulphur components is mixed with water, separates methanesulfonic sodium and sodium nitrate using storng-acid cation exchange resin, by isolated methanesulfonic sodium aqueous solution rotary evaporation, obtain methanesulfonic sodium solid；C, obtained methanesulfonic sodium solid is dissolved in chloroform, adds appropriate DMF, be then slowly added into thionyl chloride, then reacted mixed liquor oil bath heating, after the completion of reaction, reaction solution cooled down, vacuum filter, mesyl chloride is produced after filtrate rotary evaporation.Present invention utilization produces solid waste caused by dimethyl sulfone and prepares mesyl chloride, takes full advantage of waste resource, not only reduces cost, it is thus also avoided that waste pollution environment.
Description
Technical field
The invention belongs to chemical field, and in particular to one kind utilization produces discarded object caused by dimethyl sulfone and prepares methylsulfonyl
The method of chlorine.
Background technology
Dimethyl sulfone has the ability that insulin is produced in enhancing human body, to the generation of carbohydrate as a kind of organic sulfur compound
Thank and play a driving role, and the necessary material of human collagen albumen synthesis, while wound healing can also be promoted, also can be to new old generation
Thank and worked with the vitamin B needed for neurological health, vitamin C, the synthesis of biotin and activation, be referred to as " beautifying carbon naturally
Material ".
At present, the industrial process of domestic dimethyl sulfone is mainly obtained by dimethyl sulfoxide (DMSO) through nitric acid oxidation, the party
Not the problems such as method does not only exist reaction temperature height, high energy consumption, technological process is long, accessory substance is more, and can generate containing a large amount of nitric acid
The waste materials such as sodium, natrium nitrosum, methanesulfonic sodium, these waste utilization rates are low, largely make waste treatment, not only pollute environment, and
And to it is therein using material be also a kind of waste.
Mesyl chloride has very high reactivity, be important organic synthesis intermediate, can be used as esterification, polymerisation
Catalyst；On chemical industry, as woolen dyed auxiliary agent, the color development conditioning agent of photochrome, drying oil oil film, the speed of coating are consolidated
Agent, also serve as the raw material of medicine and agricultural chemicals.Industrially conventional methanesulfonic acid is with thionyl chloride and with methyl mercaptan oxychloride, both sides
The raw material of method is more expensive, with methyl mercaptan, dimethyl disulphide, methyl-rhodanide etc. for substrate, with chlorine direct oxidation or electrolysis
Mesyl chloride is produced, side reaction is more, low yield, and product is not readily separated.
The content of the invention
The present invention produces the problem of waste utilization rate caused by dimethyl sulfone is low for existing method, there is provided one kind utilizes
The method that discarded object caused by production dimethyl sulfone prepares mesyl chloride.
To achieve the above object, the present invention adopts the following technical scheme that：
A kind of utilize produces the method that discarded object caused by dimethyl sulfone prepares mesyl chloride, comprises the following steps：
A, solid waste will be mixed caused by production dimethyl sulfone with acetone, condensing reflux removes organic in solid waste
Sulphur composition；
B, the solid waste for removing organic sulphur components is mixed with water, first sulphur is separated using storng-acid cation exchange resin
Sour sodium and sodium nitrate, by isolated methanesulfonic sodium aqueous solution rotary evaporation, obtain methanesulfonic sodium solid；
C, obtained methanesulfonic sodium solid is dissolved in chloroform, adds appropriate DMF, then add thionyl chloride, then will
Mixed liquor oil bath heating is reacted, and after the completion of reaction, reaction solution is cooled down, vacuum filter, and first is produced after filtrate rotary evaporation
Sulfonic acid chloride.In this step, thionyl chloride and methanesulfonic sodium are exothermic reaction, and thionyl chloride need to be slowly added to, and DMF is catalyst；
Filter residue after filtering is dried after being washed with ethanol, obtains sodium chloride.
Preferably, the step a specifically includes following steps：
A1, solid waste and acetone it will press mass volume ratio 1g caused by production dimethyl sulfone:1.2~1.8mL is mixed,
Stirring and 1~1.5h of condensing reflux, are subsequently cooled to 20~25 DEG C under 65~70 DEG C of water-baths；
A2, by the mixture vacuum filter after cooling, filter residue is in 60 DEG C of drying.
Step a is mainly to remove the organic sulphur components in solid waste, wherein, the filter residue after being filtered in step a2 can basis
It is 1g to need to add with solid waste mass volume ratio:0.6~0.7mL acetone mixes 30min, further to remove
Organic sulphur components, obtained filter residue mainly contain methanesulfonic sodium and sodium nitrate；Obtained filtrate is collected by filtration, rotary evaporation can be passed through
Acetone is removed, obtains dimethyl sulfone and dimethyl sulfoxide (DMSO).
Preferably, the step b specifically includes following steps：
B1, the quality such as filter residue and water after being dried in step a2 are mixed, with dust technology regulation pH to 5~6, be warming up to 55
1.5~3h is stirred after~65 DEG C, is subsequently cooled to 20~25 DEG C；Contain a small amount of natrium nitrosum in filter residue after drying, pass through addition
A small amount of dust technology, and coordinate heating stirring, the dust technology of addition can react generation nitrous acid, the nitrous of generation with natrium nitrosum
Acid can be further broken into nitrogen dioxide, so as to remove natrium nitrosum；
B2, by the reaction solution after being cooled down in step b1 and strong acidic ion resin by volume 1:3.5~4.5 add extremely
In separatory funnel, after standing 1~2h, the aqueous solution of separatory funnel bottom is collected；In this step, the water of control separatory funnel bottom
Solution flow rate discharges 4~4.5h of the aqueous solution, can add appropriate amount of deionized water as needed and rinse cationic ion-exchange resin number
It is secondary, wherein, control that the flow velocity of the aqueous solution is particularly critical, and flow velocity is too fast, sodium ion in liquor may be adsorbed not exclusively, so as to make
Nitric acid sodium content is excessive into final product, and flow velocity is excessively slow, then may have methanesulfonic sodium and rinse incomplete problem；
B3, the aqueous solution rotary evaporation that will be collected in step b2, obtain white-yellowish solid, by the white-yellowish solid and nothing
Water-ethanol is mixed, 5~6h of stirring in water bath, and mixed liquor vacuum filter, filter residue then are obtained into methanesulfonic sodium solid in 90 DEG C of drying.
In this step, rotary evaporation concentration goes to remove water to drips without any water from condenser, removes most of nitric acid with the evaporation of dampening
Fall；Absolute ethyl alcohol can have exothermic phenomenon with nitric acid reaction remaining in solid, generate acetaldehyde, bubble of emerging.
Preferably, the oil bath heating reactions steps described in step c are as follows：
Oil temperature first rises to 35 DEG C, 30~35min of stirring reaction, then is warming up to 60 DEG C, reacts 50~60min, then be warming up to
80 DEG C, 10~15min is reacted, then is warming up to 100 DEG C, 6~7h is reacted, is then cooled to 60 DEG C, and adds chloroform, wherein described
Methanesulfonic sodium and the chloroform mass volume ratio added are 1g:2~3mL, 20~25 DEG C are cooled to after stirring evenly.Reacted in this step
The influence of heating and temperature-fall period to mesyl chloride yield is particularly critical, need to strictly control.
Preferably, when methanesulfonic sodium solid is dissolved in chloroform in step c, the mass volume ratio of methanesulfonic sodium and chloroform is
1g:0.4~0.5mL.
Preferably, the mol ratio of methanesulfonic sodium and thionyl chloride is 1 in step c:1.1~1.5.
Compared with prior art, the present invention has the advantages that：
1. present invention utilization produces discarded object caused by dimethyl sulfone and prepares mesyl chloride, discarded money is taken full advantage of
Source, not only reduce cost, it is thus also avoided that waste pollution environment, improve the value of industrial by-products.
2. the present invention uses chloroform as solvent, using DMF as catalyst, thionyl chloride is chlorinating agent, and association reaction process
In control to heating, cooling, substantially increase the yield of reaction product, wherein, heating and temperature-fall period are to first sulphur in reaction
The influence of acyl chlorides yield is particularly critical, need to strictly control.
Embodiment
The present invention is described in further detail with reference to specific embodiment.
Embodiment 1
1st, the organic sulphur components in solid waste are extracted
A, taking the permanent outstanding chemical spent material 300g samples taken back from Dianjiang in March, 2014, (pH value is not more than 8, and main component is
The waste materials such as sodium nitrate, natrium nitrosum, methanesulfonic sodium), add in 1L single-necked flasks, measure 450mL acetone with graduated cylinder and be added to burning
In bottle, stirring seed is added.Flask is placed in magnetic agitation water-bath, installs the spherical condensation tube with cooling water, opens magnetic
Power stirs.To 65 DEG C, acetone gradually starts to flow back warming-in-water, after the stable backflow of acetone, is stirred at reflux 1 hour, Ran Houleng
To room temperature.
B, gained mixture glass sand hourglass vacuumizing filtration after cooling down, solid return to flask after draining and add 200ml
Acetone room temperature magnetic agitation 30 minutes, then vacuumizing filtration, finally washs solid with 50ml acetone, and solid is drained.Gained is consolidated
Body is placed in drying box 60 DEG C of dryings 3 hours, obtains 224g solids, the solid mainly contains methanesulfonic sodium, sodium nitrate.
C, all acetone filtered fluids are collected to merge, vacuumizes decompression and remove acetone using Rotary Evaporators concentration, finally
Yellow oil 68.8g, the grease solidification of room temperature part is cooled to, separates out solid, predominantly dimethyl sulfone and dimethyl sulfoxide (DMSO).
2nd, methanesulfonic sodium and sodium nitrate are separated using storng-acid cation exchange resin
A, the dried solid 200g of above-mentioned steps B are taken in 1L beakers, add 200ml deionized waters (with it is dried
The quality such as solid), stirring seed is put into, beaker is placed in magnetic agitation water-bath, opens stirring, after being well mixed, with a small amount of
Dust technology adjusts pH value to have natrium nitrosum and the nitrous acid of nitric acid reaction generation to decompose and produce nitrogen dioxide to 5-6.Then by water-bath
It is warming up to 60 DEG C of stirrings and eliminates nitrous acid in 2 hours, reaction solution is cooled to room temperature, it is methanesulfonic sodium and sodium nitrate to obtain main component
Mixed aqueous solution, volume 330ml.
B, the strong acidic ion resin for taking 1.2L to regenerate is added in separatory funnel, by water therein be discarded to
Resin flushes, and the mixed aqueous solution 330ml after cooling is added in separatory funnel, stood close to 7 by the water pH value now released
1 hour.
C, open separatory funnel lower switches, release the aqueous solution, now pH value of water solution 1,4 hours used times discharge, flow velocity
About 100ml/ hours.After the mixed aqueous solution of addition discharges, it is initially added into deionized water and continues to rinse ion exchange resin, often
Secondary addition 100ml (half for the deionized water that step A is added) deionized water, adds 800ml, flow velocity about 114ml/ is small altogether
When, 7 hours used times discharged.Whole process there are the 1100ml aqueous solution, 11 hours used times.
The judgement of terminal：With the thin wire of cleaning in alcolhol burner calcination a moment, the water that mouth under separatory funnel is released is stained with, in wine
Smart lamp calcination, if containing methanesulfonic sodium in water sample, with the evaporation of dampening, gradually there is carbonization material generation, and flame is in yellow
(flame reaction)；If without methanesulfonic sodium, then Non-carbonized material produces for calcination, and now pH value of water solution is about 4 or so.
D, obtained methanesulfonic sodium will be collected, aqueous solution of nitric acid is added in 1L single-necked flasks, is vacuumized decompression and is used rotation
Turn evaporimeter concentration and remove water to being dripped without any water from condenser, remove most of nitric acid with the evaporation of dampening, finally
White-yellowish solid.
E, obtained yellow-white methanesulfonic sodium crude product is placed in 1L single-necked flasks, addition 200ml absolute ethyl alcohols, in solid
Remaining nitric acid reacts with absolute ethyl alcohol, has exothermic phenomenon, there is acetaldehyde generation, bubble of emerging.Flask is placed in magnetic agitation water
In bath, add magnetic agitation seed and stir 5 hours.
F, by methanesulfonic sodium, absolute ethyl alcohol mixture glass sand hourglass vacuumizing filtration, gained methanesulfonic sodium with 50ml without
Water-ethanol washs, and drains, and collects methanesulfonic sodium 90 DEG C of dryings of baking oven, obtains methanesulfonic sodium 138.1g, yield 69%, through infrared detection
Without sodium nitrate characteristic peak.Filtering gained ethanol is distilled to recover ethanol, raffinate naoh treatment through normal pressure.
G, the regeneration of strong acidic ion resin：
Sodium ion in about 62g sodium nitrate is on resin, 62 ÷ 85=0.729mol sodium ions, in requisition for 0.729mol
Hydrogen ion is replaced.
Resin is taken out from separatory funnel and is added in 2L beakers.Aqueous about 0.3L in resin, add 0.3L go from
Sub- water, take concentrated hydrochloric acid (12mol/L) 0.06L × 12=0.72mol to be added in beaker, hydrogen ion concentration about 1.1mol/L, stir
Resin is mixed, and is soaked 24 hours.Soaked resin is added in separatory funnel, wherein acid solution will be released, then use 1mol/
L hydrochloric acid solutions 240ml rinses resin, flow velocity 120ml/ hours.
Tested with deionized water rinsing resin to pH test paper close to 7, share deionized water 1200ml, 7.6 hours used times, stream
Fast 157ml/ hours.Now resin regeneration is completed, and can be reused.
Removing regenerating resin must use beyond deionized water, the pretreatment of other samples, resin separation methanesulfonic sodium, nitre
Sour sodium process can use the running water of soft replace deionized water, and the cation in running water can take a part of resin friendship
Capacity is changed, the close effect using deionized water of the methanesulfonic sodium quality finally obtained.
3rd, mesyl chloride is prepared using methanesulfonic sodium
The chloroform used in this step must be without alcohols materials such as methanol, ethanol, and if alcohols material, chloroform must be used
Water washing, liquid separation 5 times, alcohol is removed, with sodium sulphate drying for standby.The glass apparatus used used must dry anhydrous, glass instrument
Each interface of device must have good sealing.
Reaction equation is：
CH3SO3Na+SOCl2→CH3SO2Cl+NaCl+SO2
A, methanesulfonic sodium 50g (0.49mol) and DMF1.2g that above-mentioned steps F is obtained, chloroform 20ml are added to
In 500ml three-necked flasks, flask is placed in magnetic force oil bath pan, installs thermometer, spherical condensation tube, and condenser pipe is suitable for reading to connect tail gas
Absorption plant, tail gas are absorbed with sodium hydrate aqueous solution.Thionyl chloride 75.6g (0.64mol) is then slowly added into, has heat release to show
As reacting liquid temperature rises to 35 DEG C, is slowly stirred reaction 30min, and reaction raw materials gradually become yellow.
B, heat stage by stage, oil temperature rises to 60 DEG C, opens condensed water, has liquid backflow, have bubble to emerge, anti-in this temperature
Answer 50 minutes.
C, oil temperature continues to raise, and rises to 80 DEG C, and reaction bubble, which is emerged, to be increased, and is reacted 10 minutes, then is warming up to 100 DEG C, instead
Answering liquid temperature degree, reactant gradually becomes white by yellow, is reacted at 100 DEG C because the generation of mesyl chloride is gradually increased to 87 DEG C
Time is 6 hours.
D, reaction finishes, and stops heating, cools to 60 DEG C of addition 130ml chloroforms, stirs.
E, reaction solution is cooled to room temperature and vacuumizes fast filtering with glass sand hourglass, and solid is drained with 100ml chloroforms, collects
Solid is placed in 250ml single-necked flasks addition 100ml ethanol agitator treatings, filtered through glass sand hourglass, and 80 DEG C of baking oven is dry
25g.Infrared test, no methanesulfonic sodium peak, this solid is mainly sodium chloride.
G, the chloroformic solution being filtrated to get, vacuumize decompression and remove chloroform using Rotary Evaporators concentration, obtain mesyl chloride
44.7g.It is 98.1% through vapor detection (normalization method) main content.
It is evaporated under reduced pressure purifying mesyl chloride：
Mesyl chloride 44.7g obtained above is added in 250ml single-necked flasks, flask is placed in magnetic agitation oil bath pan
In, still head, thermometer, straight cold finger, dovetail pipe, receiving flask are installed, each interface smears a small amount of vacuum grease sealing.Water circulation
Vacuum pump pressure, magnetic agitation to be opened, be stepped up oil temperature, oil temperature finally rises to 110 DEG C, and stable cut temperature is 90 DEG C,
41.8g mesyl chlorides are collected into altogether, and this time overall yield of reaction is 83.6%.
Embodiment 2~3
Embodiment 2 is identical with the method for embodiment 1, and difference is, the mol ratio of methanesulfonic sodium and thionyl chloride in embodiment 2
For 1:1.5, reaction result is shown in Table 1.
Embodiment 3 is identical with the method for embodiment 1, and difference is, the mol ratio of methanesulfonic sodium and thionyl chloride in embodiment 3
For 1:1.1, reaction result is shown in Table 1.
The reaction product test result of 1 embodiment of table 1~3
| Embodiment | Methanesulfonic sodium inventory | Yield | Yield | Purity after distillation |
| 1 | 50g | 41.8g | 83.6% | 99.7% |
| 2 | 75.8g | 63.7g | 84.0% | 99.7% |
| 3 | 50g | 41.3g | 82.6% | 99.7% |
Finally illustrate, the above embodiments are merely illustrative of the technical solutions of the present invention and it is unrestricted, although with reference to compared with
The present invention is described in detail good embodiment, it will be understood by those within the art that, can be to the skill of the present invention
Art scheme is modified or equivalent substitution, and without departing from the objective and scope of technical solution of the present invention, it all should cover at this
Among the right of invention.
Claims (6)
1. a kind of utilize produces the method that discarded object caused by dimethyl sulfone prepares mesyl chloride, it is characterised in that including as follows
Step：
A, solid waste and acetone caused by production dimethyl sulfone are mixed, condensing reflux remove organic sulfur in solid waste into
Point；
B, the solid waste for removing organic sulphur components is mixed with water, methanesulfonic sodium is separated using storng-acid cation exchange resin
And sodium nitrate, by isolated methanesulfonic sodium aqueous solution rotary evaporation, obtain methanesulfonic sodium solid；
C, obtained methanesulfonic sodium solid is dissolved in chloroform, adds appropriate DMF, be then slowly added into thionyl chloride, then will
Mixed liquor oil bath heating is reacted, and after the completion of reaction, reaction solution is cooled down, vacuum filter, and first is produced after filtrate rotary evaporation
Sulfonic acid chloride.
2. according to the method for claim 1, it is characterised in that the step a specifically includes following steps：
A1, solid waste and acetone it will press mass volume ratio 1g caused by production dimethyl sulfone:1.2 ~ 1.8mL is mixed, 65 ~ 70
Stirring and 1 ~ 1.5h of condensing reflux, are subsequently cooled to 20 ~ 25 DEG C under DEG C water-bath；
A2, by the mixture vacuum filter after cooling, filter residue is in 60 DEG C of drying.
3. according to the method for claim 2, it is characterised in that the step b specifically includes following steps：
B1, the quality such as filter residue and water after being dried in step a2 are mixed, with dust technology regulation pH to 5 ~ 6, be warming up to 55 ~ 65 DEG C
1.5 ~ 3h is stirred afterwards, is subsequently cooled to 20 ~ 25 DEG C；
B2, by the reaction solution after being cooled down in step b1 and strong acidic ion resin by volume 1:3.5 ~ 4.5 add to liquid separation
In funnel, after standing 1 ~ 2h, the aqueous solution of separatory funnel bottom is collected；
B3, the aqueous solution rotary evaporation that will be collected in step b2, obtain white-yellowish solid, by the white-yellowish solid and anhydrous second
Alcohol is mixed, 5 ~ 6h of stirring in water bath, and mixed liquor vacuum filter, filter residue then are obtained into methanesulfonic sodium solid in 90 DEG C of drying.
4. according to the method for claim 3, it is characterised in that the oil bath heating reactions steps described in step c are as follows：
Oil temperature first rises to 35 DEG C, 30 ~ 35min of stirring reaction, then is warming up to 60 DEG C, reacts 50 ~ 60min, then is warming up to 80 DEG C, instead
10 ~ 15min is answered, then is warming up to 100 DEG C, 6 ~ 7h is reacted, is then cooled to 60 DEG C, and adds chloroform, wherein the methanesulfonic sodium
It is 1g with the chloroform mass volume ratio added:2 ~ 3mL, 20 ~ 25 DEG C are cooled to after stirring evenly.
5. according to the method for claim 4, it is characterised in that when methanesulfonic sodium solid is dissolved in chloroform in step c, methanesulfonic acid
The mass volume ratio of sodium and chloroform is 1g:0.4~0.5mL.
6. according to the method for claim 4, it is characterised in that the mol ratio of methanesulfonic sodium and thionyl chloride is in step c
1:1.1~1.5。
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| CN201710745419.3A CN107473992B (en) | 2017-08-26 | 2017-08-26 | Method for preparing methanesulfonyl chloride by using waste generated in dimethyl sulfone production |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN111138841A (en) * | 2019-12-30 | 2020-05-12 | 江苏利宏科技发展有限公司 | Environment-friendly polyurethane grouting material and preparation method thereof |
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| CN104311460A (en) * | 2014-09-15 | 2015-01-28 | 夏瑜 | Waste dimethyl sulfoxide recovery and treatment method |
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| CN104311460A (en) * | 2014-09-15 | 2015-01-28 | 夏瑜 | Waste dimethyl sulfoxide recovery and treatment method |
| CN104592067A (en) * | 2015-01-30 | 2015-05-06 | 湖北大学 | Method for recycling dimethyl sulfoxide waste residue through multi-stage extraction |
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| CN111138841A (en) * | 2019-12-30 | 2020-05-12 | 江苏利宏科技发展有限公司 | Environment-friendly polyurethane grouting material and preparation method thereof |
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