CN109232518A - A kind of preparation method of three sulfuric acid vinyl ester of ring - Google Patents
A kind of preparation method of three sulfuric acid vinyl ester of ring Download PDFInfo
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- CN109232518A CN109232518A CN201811074499.5A CN201811074499A CN109232518A CN 109232518 A CN109232518 A CN 109232518A CN 201811074499 A CN201811074499 A CN 201811074499A CN 109232518 A CN109232518 A CN 109232518A
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D327/00—Heterocyclic compounds containing rings having oxygen and sulfur atoms as the only ring hetero atoms
- C07D327/10—Heterocyclic compounds containing rings having oxygen and sulfur atoms as the only ring hetero atoms two oxygen atoms and one sulfur atom, e.g. cyclic sulfates
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Abstract
The invention discloses a kind of preparation methods of three sulfuric acid vinyl ester of ring, steps are as follows: a certain amount of inositol being added in nonaqueous solvents A, and then thionyl chloride is added dropwise thereto, it is reacted, decompression removes solvent after complete reaction, white solid is obtained, is then washed with distilled water, three sulfuric acid vinylene of ring is obtained after vacuum drying.It disperses three sulfuric acid vinylene of gained ring and a certain amount of catalyst in nonaqueous solvent B, then oxidant is slowly added dropwise thereto, it is reacted, liquid separation is stood after complete reaction, supernatant liquor is taken, then decompression removes solvent, obtains white solid, it is washed with distilled water again, three sulfuric acid vinyl ester of ring is obtained after vacuum drying.The structure novel of three sulfuric acid vinyl ester of ring provided by the invention, preparation method simple process, reaction condition be mild, the easily separated purifying of product, high production efficiency, the compound has higher stability compared to DTD, is expected to that the high temperature performance of battery is used and improved as lithium-ion battery electrolytes additive.
Description
[technical field]
The present invention relates to the preparation methods for nonaqueous lithium ion battery electrolyte with three sulfuric acid vinyl ester of additive ring.
[background technique]
Lithium ion battery has high-energy-density density, length compared to traditional lead-acid battery, nickel-metal hydride battery, nickel-cadmium cell etc.
The features such as cycle life, but its low temperature charge-discharge performance is poor.The new-energy automobile of lithium ion battery driving is in northern China
In use, often there is the problems such as short low temperature cruise duration, low temperature charging analysis lithium, battery can be sent out when serious in area especially winter
Raw short circuit, flatulence and spontaneous combustion problems, hinder the large-scale promotion application of electric car.
The DC internal resistance (DCR) of battery directly determines the low temperature charge-discharge performance of battery, the smaller lithium ion battery of DCR it is low
Warm nature can be better.Relative to the exploitation and battery design of positive and negative pole material, electrolyte has the characteristics that formula is flexible and changeable.Therefore
Scientific research and enterprise field improve often through to electrolyte, the DCR of battery are reduced, to improve the low temperature properties of battery
Energy.Wherein sulfuric acid ester compound can be used as the use of lithium-ion battery electrolytes SEI film film for additive, by suitable sulfuric acid
After electrolyte is added in vinylene, the DCR of battery can be substantially reduced and improve the low-temperature circulating performance of electrolyte；In addition, sulphur
Vinyl acetate can also inhibit battery initial capacity to decline, and increase initial discharge capacity, reduce the cell expansion after high temperature is placed,
Improve the charge-discharge performance and cycle-index of battery；Kuk Young Cho is in Journal of Power Sources., and 2018,
Reported in 378:112 3,3- union II sulfuric acid vinylene (BDTD) can be improved aluminium oxide package NCM532 positive electrode exist
Cyclical stability under 3.0-4.6V；In patent CN106905291A, 3, the 3- union II sulfuric acid vinyl ester is negative in battery
Pole film forming, can effectively protect cathode, not only prevents the reduction of battery capacity under high temperature, can also effectively improve battery under low temperature condition
Performance.But the stability of DTD and BDTD combound itself is poor, electrolyte acidity and coloration in room temperature and high temperature storage
It is unstable, low-temperature transport and storage are needed, its large-scale use is affected.Different from aforementioned report, the present invention is using inositol the bottom of as
Object designs and synthesizes cyclic annular three sulfuric acid vinyl esters, which has higher stability compared to DTD, be expected to as lithium from
Sub- battery electrolyte additive uses and improves the high temperature performance of battery.
[summary of the invention]
The purpose of the present invention is to provide a kind of simple processes, and reaction condition is mild, the easily separated purifying of product, production efficiency
The high method for preparing three sulfuric acid vinyl ester of ring.
To achieve the goals above, the present invention adopts the following technical scheme:
A kind of preparation method of three sulfuric acid vinyl ester (structural formula I) of ring, comprising the following steps:
Inositol is added into the reaction vessel for filling nonaqueous solvents A, and then thionyl chloride is added dropwise thereto by step a, control
Reaction temperature is simultaneously stirred to react；
Step b, is removed under reduced pressure solvent after complete reaction, obtains white solid, is then washed with distilled water 4 times, vacuum
It is dry, obtain three sulfuric acid vinylene of ring；
Step c disperses three sulfuric acid vinylene of gained ring and catalyst in nonaqueous solvent B；
Oxidant is slowly added into the reaction solution of step c by step d, is controlled reaction temperature and is stirred to react；
Step e, stratification, takes supernatant liquor, solvent is then removed under reduced pressure, obtain white solid after complete reaction,
It is washed with distilled water again 4 times, is dried in vacuo, obtains three sulfuric acid vinyl ester of ring.
The structural formula (structural formula I) of obtained three sulfuric acid vinyl ester of ring of the present invention is as follows:
Further, the preparation method of three sulfuric acid vinyl ester of ring above-mentioned, in which: the nonaqueous solvents A is selected from ring-type
One of ether, chain ether, chloralkane, chain carboxylate, cyclic carboxylic esters, linear carbonate, cyclic carbonate are a variety of
Mixing.
Further, the preparation method of three sulfuric acid vinyl ester of ring above-mentioned, in which: the nonaqueous solvent B be selected from nitrile,
One of alkyl chloride hydro carbons, chain ether, cyclic ether or a variety of mixing.
Further, the preparation method of three sulfuric acid vinyl ester of ring above-mentioned, in which: mole of the inositol and thionyl chloride
Than for 1:3~1:3.6.
Further, the preparation method of three sulfuric acid vinyl ester of ring above-mentioned, in which: the inositol is reacted with thionyl chloride
Temperature range is 0~80 DEG C, preferably 45~65 DEG C.
Further, the preparation method of three sulfuric acid vinyl ester of ring above-mentioned, in which: the inositol and thionyl chloride are completely anti-
Time required for answering is 4h~10h.
Further, the preparation method of three sulfuric acid vinyl ester of ring above-mentioned, in which: the catalyst is ruthenium trichloride, oxygen
Change one of ruthenium, tetrakis triphenylphosphine palladium, radium chloride or ferric sulfate or a variety of mixing.
Further, the preparation method of three sulfuric acid vinyl ester of ring above-mentioned, in which: the dosage of the catalyst is substrate
0.01%-1%.
Further, the preparation method of three sulfuric acid vinyl ester of ring above-mentioned, in which: oxidant can be selected from: hydrogen peroxide, smelly
One of oxygen, metachloroperbenzoic acid, sodium tungstate, sodium hypochlorite, SODIUM PERCARBONATE, potassium permanganate are a variety of；Three sulfuric acid of ring is sub-
Vinyl acetate and the molar ratio of oxidant are 1:3.6~1:6.
Further, the preparation method of three sulfuric acid vinyl ester of ring above-mentioned, in which: the oxygen of the three sulfuric acid vinylene of ring
The temperature range for changing reaction is 0~60 DEG C, preferably 10~30 DEG C.
Further, the preparation method of three sulfuric acid vinyl ester of ring above-mentioned, in which: the oxygen of the three sulfuric acid vinylene of ring
Changing the time required for reacting is 4h~8h.
Present invention process is simple, and reaction condition is mild, the easily separated purifying of product, high production efficiency.
[specific embodiment]
The present invention is described further below with reference to embodiment, but protection scope of the present invention is not limited only to embodiment.
Embodiment 1
400g tetrahydrofuran is put into 1000mL two mouth flask, is then put into 40.00g inositol thereto, is put into stirring
Two mouth flask is immersed in 55 DEG C of oil baths and opens magnetic stirring apparatus, is sufficiently stirred by son, then using constant pressure separatory funnel to
83.21g thionyl chloride, time for adding 1h are added dropwise in above-mentioned mixed liquor.HCl is constantly generated in solution during dropwise addition
Gas is absorbed by calcium oxide.As the additional amount of thionyl chloride is gradually increased, reaction severe degree is increased, and reaction is not
It is disconnected to carry out.After completion of dropwise addition, stop reaction after the reaction was continued 3h.
It is depressurized to liquid is produced, removes by-product HCl, solvent and unreacted thionyl chloride, obtain white solid, then
It is washed with distilled water 4 times, is dried in vacuo, obtains three sulfuric acid vinylene of 61.20g ring, yield 86.6%.
Two mouthfuls of burnings by three sulfuric acid vinylene of 61.20g ring and 0.05g catalyst ruthenium trichloride investment equipped with 400g acetonitrile
In bottle, it is put into stirrer, two mouth flask is immersed in 20 DEG C of water-baths and opens magnetic stirring apparatus, is sufficiently stirred.Then it uses
The liquor natrii hypochloritis of 515.24g10% concentration, time for adding 1h are added dropwise into above-mentioned mixed liquor for constant pressure separatory funnel.
After completion of dropwise addition, stop reaction after the reaction was continued 4h.
Liquid standing will be produced after reaction, layering, upper layer is acetonitrile solution, and there are a large amount of white solids to suspend wherein, and lower layer is
Water layer.Liquid separation, takes upper organic phase, and decompression removes solvent, obtains white solid, be then washed with distilled water 4 times, obtain 58.70g
Three sulfuric acid vinyl ester of ring identifies that purity is 99.69% through nuclear-magnetism, and the yield of product is 72.18%.
Embodiment 2
239.52g tetrahydrofuran and 160.48g methylene chloride are put into 1000mL two mouth flask, are then put into thereto
40.00g inositol, is put into stirrer, and two mouth flask is immersed in 55 DEG C of oil baths and opens magnetic stirring apparatus, is sufficiently stirred, so
87.16g thionyl chloride, time for adding 1h are added dropwise into above-mentioned mixed liquor using constant pressure separatory funnel afterwards.It had been added dropwise
HCl gas is constantly generated in journey in solution, is absorbed by calcium oxide.As the additional amount of thionyl chloride is gradually increased, instead
It answers severe degree to increase, reacts and constantly carry out.After completion of dropwise addition, stop reaction after the reaction was continued 3h.
It is depressurized to liquid is produced, removes by-product HCl, solvent and unreacted thionyl chloride, obtain white solid, then
It is washed with distilled water 4 times, is dried in vacuo, obtains three sulfuric acid vinylene of 62.40g ring, yield 88.3%.
Three sulfuric acid vinylene of 62.40g ring and 0.10g catalyst ruthenium-oxide investment are equipped with to the two mouth flask of 400g acetonitrile
In, it is put into stirrer, two mouth flask is immersed in 20 DEG C of water-baths and opens magnetic stirring apparatus, is sufficiently stirred.Then using perseverance
The hydrogen peroxide of 80.07g30% mass concentration, time for adding 1h are added dropwise into above-mentioned mixed liquor for pressure separatory funnel.It is added dropwise
After, stop reaction after the reaction was continued 4h.
Liquid standing will be produced after reaction, layering, upper layer is acetonitrile solution, and there are a large amount of white solids to suspend wherein, and lower layer is
Water layer.Liquid separation, takes upper organic phase, and decompression removes solvent, obtains white solid, be then washed with distilled water 4 times, obtain 61.50g
Three sulfuric acid vinyl ester of ring identifies that purity is 99.57% through nuclear-magnetism, and the yield of product is 75.62%.
Embodiment 3
400g tetrahydrofuran is put into 1000mL two mouth flask, is then put into 40.00g inositol thereto, is put into stirring
Two mouth flask is immersed in 55 DEG C of oil baths and opens magnetic stirring apparatus, is sufficiently stirred by son, then using constant pressure separatory funnel to
87.16g thionyl chloride, time for adding 1h are added dropwise in above-mentioned mixed liquor.HCl is constantly generated in solution during dropwise addition
Gas is absorbed by calcium oxide.As the additional amount of thionyl chloride is gradually increased, reaction severe degree is increased, and reaction is not
It is disconnected to carry out.After completion of dropwise addition, stop reaction after the reaction was continued 3h.
It is depressurized to liquid is produced, removes by-product HCl, solvent and unreacted thionyl chloride, obtain white solid, then
It is washed with distilled water 4 times, is dried in vacuo, obtains three sulfuric acid vinylene of 61.55g ring, yield 87.1% is identified pure through nuclear-magnetism
Degree is 99.25%.
Three sulfuric acid vinylene of 61.55g ring and 0.05g catalyst sulfuric acid iron investment are equipped with to the two mouth flask of 400g acetonitrile
In, it is put into stirrer, two mouth flask is immersed in 20 DEG C of water-baths and opens magnetic stirring apparatus, is sufficiently stirred.Then using perseverance
The SODIUM PERCARBONATE aqueous solution of 364.53g30% concentration, time for adding 1h are added dropwise into above-mentioned mixed liquor for pressure separatory funnel.
After completion of dropwise addition, stop reaction after the reaction was continued 4h.
Liquid standing will be produced after reaction, layering, upper layer is acetonitrile solution, and there are a large amount of white solids to suspend wherein, and lower layer is
Water layer.Liquid separation, takes upper organic phase, and decompression removes solvent, obtains white solid, be then washed with distilled water 4 times, obtain 46.17g
Three sulfuric acid vinyl ester of ring identifies that purity is 99.36% through nuclear-magnetism, and the yield of product is 56.77%.
Embodiment 4
400g tetrahydrofuran is put into 1000mL two mouth flask, is then put into 40.00g inositol thereto, is put into stirring
Two mouth flask is immersed in 0 DEG C of oil bath and opens magnetic stirring apparatus, is sufficiently stirred by son, then using constant pressure separatory funnel to
83.21g thionyl chloride, time for adding 1h are added dropwise in above-mentioned mixed liquor.HCl is constantly generated in solution during dropwise addition
Gas is absorbed by calcium oxide.As the additional amount of thionyl chloride is gradually increased, reaction severe degree is increased, and reaction is not
It is disconnected to carry out.After completion of dropwise addition, stop reaction after the reaction was continued 9h.
It is depressurized to liquid is produced, removes by-product HCl, solvent and unreacted thionyl chloride, obtain white solid, then
It is washed with distilled water 4 times, is dried in vacuo, obtains three sulfuric acid vinylene of 61.69g ring, yield 87.3%.
By three sulfuric acid vinylene of 61.69g ring and 0.05g catalyst tetrakis triphenylphosphine palladium investment equipped with 400g acetonitrile
In two mouth flask, it is put into stirrer, two mouth flask is immersed in 60 DEG C of water-baths and opens magnetic stirring apparatus, is sufficiently stirred.So
The metachloroperbenzoic acid solution of 160.66g75% concentration is added dropwise into above-mentioned mixed liquor using constant pressure separatory funnel afterwards,
Time for adding is 1h.After completion of dropwise addition, stop reaction after the reaction was continued 4h.
Liquid standing will be produced after reaction, layering, upper layer is acetonitrile solution, and there are a large amount of white solids to suspend wherein, and lower layer is
Water layer.Liquid separation, takes upper organic phase, and decompression removes solvent, obtains white solid, be then washed with distilled water 4 times, obtain 52.31g
Three sulfuric acid vinyl ester of ring identifies that purity is 99.33% through nuclear-magnetism, and the yield of product is 64.32%.
Embodiment 5
400g tetrahydrofuran is put into 1000mL two mouth flask, is then put into 40.00g inositol thereto, is put into stirring
Two mouth flask is immersed in 55 DEG C of oil baths and opens magnetic stirring apparatus, is sufficiently stirred by son, then using constant pressure separatory funnel to
83.21g thionyl chloride, time for adding 1h are added dropwise in above-mentioned mixed liquor.HCl is constantly generated in solution during dropwise addition
Gas is absorbed by calcium oxide.As the additional amount of thionyl chloride is gradually increased, reaction severe degree is increased, and reaction is not
It is disconnected to carry out.After completion of dropwise addition, stop reaction after the reaction was continued 9h.
It is depressurized to liquid is produced, removes by-product HCl, solvent and unreacted thionyl chloride, obtain white solid, then
It is washed with distilled water 4 times, is dried in vacuo, obtains three sulfuric acid vinylene of 60.64g ring, yield 85.8%.
Two mouthfuls of burnings by three sulfuric acid vinylene of 60.64g ring and 0.05g catalyst ruthenium trichloride investment equipped with 400g acetonitrile
In bottle, it is put into stirrer, two mouth flask is immersed in 20 DEG C of water-baths and opens magnetic stirring apparatus, is sufficiently stirred.Then it uses
The liquor natrii hypochloritis of 515.24g10% concentration, time for adding 1h are added dropwise into above-mentioned mixed liquor for constant pressure separatory funnel.
After completion of dropwise addition, stop reaction after the reaction was continued 7h.
Liquid standing will be produced after reaction, layering, upper layer is acetonitrile solution, and there are a large amount of white solids to suspend wherein, and lower layer is
Water layer.Liquid separation, takes upper organic phase, and decompression removes solvent, obtains white solid, be then washed with distilled water 4 times, obtain 57.90g
Three sulfuric acid vinyl ester of ring identifies that purity is 99.58% through nuclear-magnetism, and the yield of product is 71.19%.
Embodiment 6
400g tetrahydrofuran is put into 1000mL two mouth flask, is then put into 40.00g inositol thereto, is put into stirring
Two mouth flask is immersed in 80 DEG C of oil baths and opens magnetic stirring apparatus, is sufficiently stirred by son, then using constant pressure separatory funnel to
83.21g thionyl chloride, time for adding 1h are added dropwise in above-mentioned mixed liquor.HCl is constantly generated in solution during dropwise addition
Gas is absorbed by calcium oxide.As the additional amount of thionyl chloride is gradually increased, reaction severe degree is increased, and reaction is not
It is disconnected to carry out.After completion of dropwise addition, stop reaction after the reaction was continued 3h.
It is depressurized to liquid is produced, removes by-product HCl, solvent and unreacted thionyl chloride, obtain white solid, then
It is washed with distilled water 4 times, is dried in vacuo, obtains three sulfuric acid vinylene of 61.00g ring, yield 86.3%.
Two mouthfuls of burnings by three sulfuric acid vinylene of 61.00g ring and 0.05g catalyst ruthenium trichloride investment equipped with 400g acetonitrile
In bottle, it is put into stirrer, two mouth flask is immersed in 0 DEG C of water-bath and opens magnetic stirring apparatus, is sufficiently stirred.Then using perseverance
The liquor natrii hypochloritis of 515.24g10% concentration, time for adding 1h are added dropwise into above-mentioned mixed liquor for pressure separatory funnel.Drop
After adding, stop reaction after the reaction was continued 7h.
Liquid standing will be produced after reaction, layering, upper layer is acetonitrile solution, and there are a large amount of white solids to suspend wherein, and lower layer is
Water layer.Liquid separation, takes upper organic phase, and decompression removes solvent, obtains white solid, be then washed with distilled water 4 times, obtain 57.53g
Three sulfuric acid vinyl ester of ring identifies that purity is 99.44% through nuclear-magnetism, and the yield of product is 70.74%.
Present invention process is simple, and reaction condition is mild, the easily separated purifying of product, high production efficiency.
The above description is only an embodiment of the present invention, not limits the technical scheme described by the invention, all according to this
The modification or equivalence replacement that description of the invention content is made, should all be included within the scope of protection of the present invention.
Claims (10)
1. a kind of preparation method of three sulfuric acid vinyl ester of ring, which comprises the following steps:
Inositol is added into the reaction vessel for filling nonaqueous solvents A, and then thionyl chloride is added dropwise thereto by step a, control reaction
Temperature is simultaneously stirred to react；
Step b, is removed under reduced pressure solvent after complete reaction, obtains white solid, is then washed with distilled water 4 times, vacuum drying
After obtain three sulfuric acid vinylene of ring；
Step c disperses three sulfuric acid vinylene of gained ring and catalyst in nonaqueous solvent B；
Oxidant is slowly added into the reaction solution of step c by step d, is controlled reaction temperature and is stirred to react；
Step e, stratification, takes supernatant liquor, solvent is then removed under reduced pressure after complete reaction, obtains white solid, then use
Distillation water washing 4 times, obtains three sulfuric acid vinyl ester of ring after vacuum drying.
2. the preparation method of three sulfuric acid vinyl ester of ring according to claim 1, it is characterised in that: the nonaqueous solvents A is
One in cyclic ether, chain ether, chloralkane, chain carboxylate, cyclic carboxylic esters, linear carbonate, cyclic carbonate
Kind or a variety of mixing.
3. the preparation method of three sulfuric acid vinyl ester of ring according to claim 1, it is characterised in that: the nonaqueous solvent B is
Selected from one of nitrile, alkyl chloride hydro carbons, chain ether, cyclic ether or a variety of mixing.
4. the preparation method of three sulfuric acid vinyl ester of ring according to claim 1, it is characterised in that: the inositol and thionyl
The molar ratio of chlorine is 1:3~1:3.6.
5. the preparation method of three sulfuric acid vinyl ester of ring according to claim 1, it is characterised in that: the inositol and thionyl
The range of reaction temperature of chlorine is 0~80 DEG C, preferably 45~65 DEG C.
6. the preparation method of three sulfuric acid vinyl ester of ring according to claim 1, it is characterised in that: the inositol and thionyl
Time required for chlorine reacts completely is 4h~10h.
7. the preparation method of three sulfuric acid vinyl ester of ring according to claim 1, it is characterised in that: the catalyst is trichlorine
Change one of ruthenium, ruthenium-oxide, tetrakis triphenylphosphine palladium, radium chloride or ferric sulfate or a variety of mixing, dosage is substrate
0.01%-1%.
8. the preparation method of three sulfuric acid vinyl ester of ring according to claim 1, it is characterised in that: the oxidant can select
From: one of hydrogen peroxide, ozone, metachloroperbenzoic acid, sodium tungstate, sodium hypochlorite, SODIUM PERCARBONATE, potassium permanganate are more
Kind；The molar ratio of three sulfuric acid vinylene of ring and oxidant is 1:3.6~1:6.
9. the preparation method of three sulfuric acid vinyl ester of ring according to claim 1, it is characterised in that: the three sulfuric acid Asia second of ring
Temperature range when enester and oxidant reaction is 0~60 DEG C, preferably 10~30 DEG C.
10. the preparation method of three sulfuric acid vinyl ester of ring according to claim 1, it is characterised in that: three sulfuric acid of ring is sub-
Time required for vinyl acetate is reacted completely with oxidant is 4h~8h.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN116351413A (en) * | 2023-02-24 | 2023-06-30 | 无锡威孚环保催化剂有限公司 | Catalyst for synthesizing vinyl sulfate and preparation method of vinyl sulfate |
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| JP2003238556A (en) * | 2002-02-19 | 2003-08-27 | Daicel Chem Ind Ltd | Method for producing cyclic sulfate |
| CN101253183A (en) * | 2005-07-29 | 2008-08-27 | 巴斯夫欧洲公司 | Process for preparing optically active diphosphanes |
| CN102603705A (en) * | 2012-03-27 | 2012-07-25 | 武汉大学 | Preparation method of chiral five-membered ring sulfite with active functional groups on alpha-carbon in substituent |
| CN105481826A (en) * | 2016-01-11 | 2016-04-13 | 烟台海川化学制品有限公司 | Preparation method of ethylene sulfate |
| CN106905291A (en) * | 2015-12-22 | 2017-06-30 | 天津鑫源广泰新材料科技有限公司 | A kind of 3, the production method of 3-di- sulfuric acid vinyl ester |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6180799B1 (en) * | 2000-05-01 | 2001-01-30 | The United States Of America As Represented By The Secretary Of The Air Force | Sulfalation of tetraol |
| JP2003238556A (en) * | 2002-02-19 | 2003-08-27 | Daicel Chem Ind Ltd | Method for producing cyclic sulfate |
| CN101253183A (en) * | 2005-07-29 | 2008-08-27 | 巴斯夫欧洲公司 | Process for preparing optically active diphosphanes |
| CN102603705A (en) * | 2012-03-27 | 2012-07-25 | 武汉大学 | Preparation method of chiral five-membered ring sulfite with active functional groups on alpha-carbon in substituent |
| CN106905291A (en) * | 2015-12-22 | 2017-06-30 | 天津鑫源广泰新材料科技有限公司 | A kind of 3, the production method of 3-di- sulfuric acid vinyl ester |
| CN105481826A (en) * | 2016-01-11 | 2016-04-13 | 烟台海川化学制品有限公司 | Preparation method of ethylene sulfate |
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| CN116351413A (en) * | 2023-02-24 | 2023-06-30 | 无锡威孚环保催化剂有限公司 | Catalyst for synthesizing vinyl sulfate and preparation method of vinyl sulfate |
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Application publication date: 20190118 |