CN107857752A - A kind of preparation method of the sultones of acrylic 1,3 - Google Patents
A kind of preparation method of the sultones of acrylic 1,3 Download PDFInfo
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- CN107857752A CN107857752A CN201711205128.1A CN201711205128A CN107857752A CN 107857752 A CN107857752 A CN 107857752A CN 201711205128 A CN201711205128 A CN 201711205128A CN 107857752 A CN107857752 A CN 107857752A
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- dichloroethanes
- sulfonic acid
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D327/00—Heterocyclic compounds containing rings having oxygen and sulfur atoms as the only ring hetero atoms
- C07D327/02—Heterocyclic compounds containing rings having oxygen and sulfur atoms as the only ring hetero atoms one oxygen atom and one sulfur atom
- C07D327/04—Five-membered rings
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Abstract
The invention discloses a kind of preparation method of the sultones of acrylic 1,3, pass through 1 first, the sulfonation addition reaction of 1 dichloroethylene is prepared 1,1 dichloroethanes sulfonic acid, 1,1 dichloroethanes sulfonic acid and methanol esterification are obtained 1,1 dichloroethanes methylmesylate, 1,1 dichloroethanes methylmesylate is further obtained into the sultones of 2 chloropropyl 1,3 through catalytic cyclization, last triethylamine catalysis elimination reaction obtains the sultones of acrylic 1,3.Raw material economics of the present invention is easy to get, and toxicity is low, and reaction is gentle, and product separation is simple, high income, is adapted to industrialized production.
Description
Technical field
The invention belongs to technical field prepared by compound, more particularly to a kind of preparation of propenyl-1,3-sulfonic acid lactone
Method.
Background technology
Propenyl-1,3-sulfonic acid lactone, English name Prop-1-ene-1,3-sultone or 5H-1,2-Oxathiole
2,2-dioxide, abbreviation PST, CAS 21806-61-1, it can be used as lithium battery electrolytes additive, pharmaceutical intermediate, polysaccharide
The multiple fields such as modification.
In terms of prior art, PST preparation at present mainly has four kinds of routes, propilolic alcohol route, α propylene halides route, ring
Propylene sulfone route and ring closing metathesis (RCM) route.
Propilolic alcohol route is first to propilolic alcohol addition sulfonic acid group（Böhme Fettchemie G.m.b.H., Dü
sseldorf.Verfahren zur Herstellung von Propensulton: Germany, DBP1146870[P]
.1963-12-11）, then intramolecular esterification cyclization, as follows：
, following two problems be present in the route：First, first step raw material is severe poisonous chemicals, and yield is relatively low（1,3- insatiable hungers
Synthesis and reactivity worth research with sultones, 2004, Tian Li, Nankai University Ph.D. Dissertation）, " three wastes ", which are handled, to be compared
It is complicated；Second, intramolecular esterification easily forms polymer when reacting, technological requirement is high.
α propylene halides route forms α sulfonic acid propylene by the sulfonic acid substitution reaction of halogen first, and further halogen addition is anti-
The α sulfonic acid propane of two halogens substitution should be formed, then PST is formed by two step elimination reactions（La Sheng Jiang et al.
Synthesis and Diels-Alder Reactions of Prop-1-ene-1,3-sultone, and Chemical
Transformations of the Diels-Alder Adducts, Tetrahedron, 1999, 2245-2262）,
Although the raw materials used toxicity of the route is small compared with propilolic alcohol, the physical characteristic of product and side reaction product approaches, separation
Difficulty, and reaction scheme is longer.
Cyclobufene sultone route is that propylene sulfite is formed to cyclobufene sultone pyroreaction, and further oxidation forms PST
（Lee Albert W. M. et al. Synthesis and Diels-Alder Reactions of α,β-
unsaturated γ-sultone. Chemical Communication, 1997, 611-612）,
Although the route step is less, raw material is not easy to obtain, and expensive, and side reaction is more, is unfavorable for industrialized production.
RCM routes are reacted using the sulfonic acid chloride with double bond and enol generates sulphonic acid ester, and two double bonds in sulphonic acid ester occur
RCM reacts to form PST（Sandra Karsch et al. Synthesis of Sultones by Ring Closing
Metathesis, Synlett, 2002, 2019-2022）.The raw materials used sulfonic acid chloride toxicity of the route is larger, and technique will
Ask strict, be unfavorable for industrialized production.
It is relatively low to there is yield for technology of preparing at present, and " three wastes " processing is more complicated, and raw material is not easy to obtain, and expensive, secondary
Reaction is more, and raw material sulphur toxicity is larger, and technological requirement is strict, is unfavorable for industrialized production.Therefore, it is necessary to design a kind of propylene
The preparation method of base -1,3- sultones.
The content of the invention
The defects of in order to overcome in the prior art, invent a kind of preparation method of propenyl-1,3-sulfonic acid lactone.
The present invention is realized by following proposal：
A kind of preparation method of propenyl-1,3-sulfonic acid lactone, it is characterised in that:The preparation method includes following four step：（1）1,
1- dichloroethylene sulfonation additions；（2）1,1- dichloroethanes is esterified；（3）1,1- dichloroethanes methylmesylate is cyclized；（4）2- chlorine third
Base -1,3- sultones elimination reactions obtain the sultones of acrylic -1,3.
The 1,1- dichloroethylene sulfonation addition includes step in detail below：By the deionized water of 10~200 mass parts, 50
1,1- dichloroethylene, the Na of 0.5 mass parts of mass parts2S2O8, 3.0 mass parts Na2SO4Add in reactor, be slowly added to
The sulfonated reagent of 10-100 mass parts, reaction temperature -5~130 DEG C, 2~12h of stirring reaction, reaction adjust the temperature to after terminating
45 DEG C of emptying, tail gas are absorbed with 2 mol/L NaOH solutions.
The 1,1- dichloroethanes esterification comprises the following steps：By the absolute methanol of 10 mass parts and 0.1~0.3 mass parts
NaOH or KOH add into reactor, 4 h are reacted at a temperature of 50~60 DEG C, add the 1,1- of 1.5~3.0 mass parts
Dichloroethanes sulfonic acid, 90 DEG C are progressively warming up to after the h of stirring reaction 3 at a temperature of 60 DEG C, continue to stop after reacting 5 h, by 1,1-
The reaction system of dichloroethanes esterification uses petroleum ether extraction after 90 DEG C of concentrations, and steaming petroleum ether obtains 1,1- dichloroethanes sulfonic acid
Methyl esters.
The 1,1- dichloroethanes methylmesylate cyclisation comprises the following steps：By the 1,1- dichloroethanes sulfonic acid of 1 mass parts
Methyl esters is dissolved in the toluene of 5 mass parts, adds the CaH of 0.3 mass parts2Or 0.15 mass parts Na, in temperature is 0 DEG C of environment
Be warming up to 90 DEG C after the h of stirring reaction 2, continue react 4h after stop, being slowly added to 0.15 mass parts methanol be quenched it is unreacted
CaH2Or Na, it is evaporated under reduced pressure and removes toluene and methanol, uses CH2Cl2Filtered after dilution, be evaporated CH2Cl2Obtain 2- chloropropyls -1,3-
Sultones.
The elimination reaction of the 2- chloropropyls -1,3- sultones press include can following steps：By the 2- chlorine third of 1 mass parts
Base -1,3 sultones is added into the toluene of 15 mass parts, adds the triethylamine of 1 mass parts, in the ring that temperature is 20~30 DEG C
5h is reacted in border, is filtered, is evaporated under reduced pressure and removes solvent, obtain propenyl-1,3-sulfonic acid lactone.
The sulfonated reagent includes NaHSO3And SO3；Sulfonated reagent is NaHSO3When, with 1 mol/L hydrochloric acid solutions by 1,1-
The pH value of dichloroethylene sulfonation addition reaction system is adjusted to 3~4, is extracted after concentration using organic solvent, by organic phase rectifying
After obtain 1,1- dichloroethanes sulfonic acid；Sulfonated reagent is SO3When, it is not necessary to adjust vinylidene chloride sulfonation addition reaction system
PH value, 1,1- dichloroethanes sulfonic acid is obtained after direct rectifying.
The organic solvent includes petroleum ether, CH2Cl2。
The solution have the advantages that：The present invention uses low toxicity, low boiling, is easy to get and the cheap chloroethenes of 1,1- bis-
Alkene is raw material, and 1,1- dichloroethanes methylmesylates are obtained through addition, esterification, and yield is high, and separation is simple, and " three wastes " amount is few；1,1-
Dichloroethanes sulphonic acid ester is further cyclized, eliminates and obtains PST, and reaction is gentle, and separation is simple, and comprehensive PST yields are fitted up to 20%
Close industrialized production.
Embodiment
With reference to specific embodiment, the present invention is further described：
A kind of preparation method of propenyl-1,3-sulfonic acid lactone, it is characterised in that:The preparation method includes following four step：（1）1,
1- dichloroethylene sulfonation additions；（2）1,1- dichloroethanes is esterified；（3）1,1- dichloroethanes methylmesylate is cyclized；（4）2- chlorine third
Base -1,3- sultones elimination reactions obtain the sultones of acrylic -1,3.
The 1,1- dichloroethylene sulfonation addition includes step in detail below：By the deionized water of 10~200 mass parts, 50
1,1- dichloroethylene, the Na of 0.5 mass parts of mass parts2S2O8, 3.0 mass parts Na2SO4Add in reactor, be slowly added to
The sulfonated reagent of 10-100 mass parts, reaction temperature -5~130 DEG C, 2~12h of stirring reaction, reaction adjust the temperature to after terminating
45 DEG C of emptying, tail gas are absorbed with 2 mol/L NaOH solutions.The sulfonated reagent includes NaHSO3And SO3；Sulfonated reagent is
NaHSO3When, the pH value of vinylidene chloride sulfonation addition reaction system is adjusted to 3~4 with 1 mol/L hydrochloric acid solutions, concentrated
Extracted afterwards using organic solvent, 1,1- dichloroethanes sulfonic acid will be obtained after organic phase rectifying；Sulfonated reagent is SO3When, it is not necessary to
The pH value of vinylidene chloride sulfonation addition reaction system is adjusted, 1,1- dichloroethanes sulfonic acid is obtained after direct rectifying.It is described to have
Solvent includes petroleum ether, CH2Cl2。
The 1,1- dichloroethanes esterification comprises the following steps：By the absolute methanol of 10 mass parts and 0.1~0.3 mass parts
NaOH or KOH add into reactor, 4 h are reacted at a temperature of 50~60 DEG C, add the 1,1- of 1.5~3.0 mass parts
Dichloroethanes sulfonic acid, 90 DEG C are progressively warming up to after the h of stirring reaction 3 at a temperature of 60 DEG C, continue to stop after reacting 5 h, by 1,1-
The reaction system of dichloroethanes esterification uses petroleum ether extraction after 90 DEG C of concentrations, and steaming petroleum ether obtains 1,1- dichloroethanes sulfonic acid
Methyl esters.In the present invention, it is catalyzed in the esterification of 1,1- dichloroethanes sulfonic acid with NaOH or KOH, methanol is excessive so that 1,1- bis-
Chloroethene alkyl sulfonic acid reacts completely, and 1, the 1- dichloroethanes methylmesylates of generation dissolve in petroleum ether, can pass through extract and separate.
The 1,1- dichloroethanes methylmesylate cyclisation comprises the following steps：By the 1,1- dichloroethanes sulfonic acid of 1 mass parts
Methyl esters is dissolved in the toluene of 5 mass parts, adds the CaH of 0.3 mass parts2Or 0.15 mass parts Na, in temperature is 0 DEG C of environment
Be warming up to 90 DEG C after the h of stirring reaction 2, continue react 4h after stop, being slowly added to 0.15 mass parts methanol be quenched it is unreacted
CaH2Or Na, it is evaporated under reduced pressure and removes toluene and methanol, uses CH2Cl2Filtered after dilution, be evaporated CH2Cl2Obtain 2- chloropropyls -1,3-
Sultones.In the present invention, the cyclisation Na or CaH of 1,1- dichloroethanes methylmesylate2As catalyst, cyclisation product is obtained
Yield is high, is easy to separate.
The elimination reaction of the 2- chloropropyls -1,3- sultones press include can following steps：By the 2- chlorine third of 1 mass parts
Base -1,3 sultones is added into the toluene of 15 mass parts, adds the triethylamine of 1 mass parts, in the ring that temperature is 20~30 DEG C
5h is reacted in border, is filtered, is evaporated under reduced pressure and removes solvent, obtain propenyl-1,3-sulfonic acid lactone.In the present invention, 2- chloropropyl -1,
The elimination reaction of 3- sultones is taken to be carried out at room temperature, triethylamine catalysis, yield 93%.
In order to confirm PST structures and purity that the technical scheme of the present patent application obtains, with reference to three specific implementations
Example further illustrates that the result of three embodiments uses liquid chromatogram Agilent1200 HPLC liquid chromatograies, and methanol is flowing
Phase, 1 mL/min measurement of rate of flow purity；PST structures, CDCl are determined using Bruker 400M NMR3For solvent.
Embodiment 1
At room temperature, in 1L stainless steel cauldrons, 200 g deionized waters, 0.5 g Na are added2S2O8With 3.0 gNa2SO4, stir
Mix dissolving.50 g vinylidene chloride is added, by 100 g NaHSO3 It is slowly added to after the dissolving of 300 g water to reactor, drop
130 DEG C, the h of stirring reaction 8 are warming up to after adding, reaction adjusts the temperature to 45 DEG C of emptying, 2 mol/L of tail gas after terminating
NaOH solution absorbs.System pH is adjusted to 3 ~ 4 with 1 mol/L hydrochloric acid solutions, be concentrated under reduced pressure into after about 150 mL with 3 ×
300 mL CH2Cl2Extraction, it is also possible to 4 × 300 mL petroleum ether extractions.1,1- dichloroethanes sulphurs will be obtained after organic phase rectifying
Acid.
100 g absolute methanols and 1 g NaOH are added in 500 mL glass reaction kettles, 60 DEG C of h of stirring reaction 4, added
15 g 1,1- dichloroethanes sulfonic acid, 90 DEG C are progressively warming up to after 60 DEG C of h of stirring reaction 3, continue to stop after reacting 5 h.By body
Lie in after 90 DEG C of concentrations with 3 × 200 mL petroleum ether extractions, 1,1- dichloroethanes methylmesylates are obtained after steaming petroleum ether.
The toluene of 10 g 1,1- dichloroethanes methylmesylate and 50 g is added into 200 mL glass reaction kettles, stirred
Dissolving, continuously adds 3 g CaH2, 90 DEG C are warming up to after 0 DEG C of h of stirring reaction 2, continues to stop after reacting 4h, is slowly added to
Unreacted CaH is quenched in 1.5 g methanol2, it is evaporated under reduced pressure and removes toluene and methanol, with 50 mL CH2Cl2Filtered after dilution,
It is evaporated CH2Cl2Obtain 2- chloropropyl -1,3- sultones.
The toluene of 10 g 2- chloropropyls -1,3 sultones and 150 g is added into 200 mL glass reaction kettles, delayed
The slow triethylamine for adding 10 g, controlling reaction temperature are 20 ~ 30 DEG C, react 5h, filtering, are evaporated under reduced pressure and remove solvent, obtain
PST。
Embodiment 2
At room temperature, in 1L stainless steel cauldrons, 150 g deionized waters, 0.5 g Na are added2S2O8With 3.0 gNa2SO4, stir
Mix dissolving.50 g vinylidene chloride is added, by 40 g NaHSO3 It is slowly added to reactor, is added dropwise after the dissolving of 200 g water
After be warming up to 130 DEG C, the h of stirring reaction 12, reaction adjusts the temperature to 45 DEG C of emptying, 2 mol/L of tail gas after terminating
NaOH solution absorbs.System pH is adjusted to 3 ~ 4 with 1 mol/L hydrochloric acid solutions, be concentrated under reduced pressure into after about 150 mL with 3 ×
300 mL CH2Cl2Extraction, it is also possible to 4 × 300 mL petroleum ether extractions.1,1- dichloroethanes sulphurs will be obtained after organic phase rectifying
Acid.
100 g absolute methanols and 3 g KOH are added in 500 mL glass reaction kettles, 50 DEG C of h of stirring reaction 4, add 15
G 1,1- dichloroethanes sulfonic acid, 90 DEG C are progressively warming up to after 60 DEG C of h of stirring reaction 3, continue to stop after reacting 5 h.By system
With 3 × 200 mL petroleum ether extractions after 90 DEG C of concentrations, 1,1- dichloroethanes methylmesylates are obtained after steaming petroleum ether.
The toluene of 10 g 1,1- dichloroethanes methylmesylate and 50 g is added into 200 mL glass reaction kettles, stirred
Dissolving, continuously adds 1.5 g Na, 90 DEG C are warming up to after 0 DEG C of h of stirring reaction 2, continues to stop after reacting 4h, is slowly added to
Unreacted CaH is quenched in 1.5 g methanol2, it is evaporated under reduced pressure and removes toluene and methanol, with 50 mL CH2Cl2Filtered after dilution,
It is evaporated CH2Cl2Obtain 2- chloropropyl -1,3- sultones.
The toluene of 10 g 2- chloropropyls -1,3 sultones and 150 g is added into 200 mL glass reaction kettles, delayed
The slow triethylamine for adding 10 g, controlling reaction temperature are 20 ~ 30 DEG C, react 5h, filtering, are evaporated under reduced pressure and remove solvent, obtain
PST。
Embodiment 3
In 200 mL stainless steel cauldrons, 10 g water, 0.5 g Na are sequentially added2S2O8With 3.0 gNa2SO4, stir molten
Solution, is cooled to -5 DEG C.50 g vinylidene chloride is added, by 10 g SO3It is slowly added into kettle, the h of stirring reaction 12, instead
45 DEG C of emptying are adjusted the temperature to after should terminating, tail gas is absorbed with 2 mol/L NaOH solutions, will obtain 1,1- after organic phase rectifying
Dichloroethanes sulfonic acid.
100 g absolute methanols and 3 g KOH are added in 500 mL glass reaction kettles, 50 DEG C of h of stirring reaction 4, add 15
G 1,1- dichloroethanes sulfonic acid, 90 DEG C are progressively warming up to after 60 DEG C of h of stirring reaction 3, continue to stop after reacting 5 h.By system
With 3 × 200 mL petroleum ether extractions after 90 DEG C of concentrations, 1,1- dichloroethanes methylmesylates are obtained after steaming petroleum ether.
The toluene of 10 g 1,1- dichloroethanes methylmesylate and 50 g is added into 200 mL glass reaction kettles, stirred
Dissolving, continuously adds 2.5 g CaH2, 90 DEG C are warming up to after 0 DEG C of h of stirring reaction 2, continues to stop after reacting 4h, slowly adds
Unreacted CaH is quenched in the methanol for entering 1.5 g2, it is evaporated under reduced pressure and removes toluene and methanol, with 50 mL CH2Cl2Mistake after dilution
Filter, is evaporated CH2Cl2Obtain 2- chloropropyl -1,3- sultones.
The toluene of 10 g 2- chloropropyls -1,3 sultones and 150 g is added into 200 mL glass reaction kettles, delayed
The slow triethylamine for adding 10 g, controlling reaction temperature are 20 ~ 30 DEG C, react 5h, filtering, are evaporated under reduced pressure and remove solvent, obtain
PST。
The gained PST of embodiment 1,2,3 purity is all higher than 99.5%, and overall conversion is respectively 16.3%, 13.6% and
21.5%。
The present invention uses low toxicity, low boiling, is easy to get and cheap vinylidene chloride is raw material, through addition, ester
Change obtains 1,1- dichloroethanes methylmesylates, and yield is high, and separation is simple, and " three wastes " amount is few；1,1- dichloroethanes sulphonic acid esters enter one
Step cyclisation, cancellation obtain PST, and reaction is gentle, and separation is simple, and synthesis PST yields are adapted to industrialized production up to 20%.
Although more detailed elaboration is done to technical scheme and has been enumerated, it will be appreciated that for ability
For field technique personnel, modification is made to above-described embodiment or uses equivalent alternative solution, this is to those skilled in the art
It is it is clear that these modifications or improvements without departing from theon the basis of the spirit of the present invention, belong to the present invention for member
Claimed scope.
Claims (7)
- A kind of 1. preparation method of propenyl-1,3-sulfonic acid lactone, it is characterised in that:The preparation method includes following four step：（1） 1,1- dichloroethylene sulfonation additions；（2）1,1- dichloroethanes is esterified；（3）1,1- dichloroethanes methylmesylate is cyclized；（4）2- chlorine Propyl group -1,3- sultones elimination reactions obtain the sultones of acrylic -1,3.
- A kind of 2. preparation method of propenyl-1,3-sulfonic acid lactone according to right 1, it is characterised in that 1, the 1- bis- Vinyl chloride sulfonation addition includes step in detail below：By the chloroethenes of 1,1- bis- of the deionized water of 10~200 mass parts, 50 mass parts The Na of alkene, 0.5 mass parts2S2O8, 3.0 mass parts Na2SO4Add in reactor, be slowly added to the sulfonation of 10-100 mass parts Reagent, reaction temperature -5~130 DEG C, 2~12h of stirring reaction, reaction adjust the temperature to 45 DEG C of emptying after terminating, and tail gas is with 2 Mol/L NaOH solutions absorb.
- A kind of 3. preparation method of propenyl-1,3-sulfonic acid lactone according to right 1, it is characterised in that 1, the 1- bis- Chloroethanes esterification comprises the following steps：By the NaOH or KOH of the absolute methanol of 10 mass parts and 0.1~0.3 mass parts add to In reactor, 4 h are reacted at a temperature of 50~60 DEG C, 1, the 1- dichloroethanes sulfonic acid of 1.5~3.0 mass parts are added, 60 90 DEG C are progressively warming up to after the h of stirring reaction 3 at a temperature of DEG C, continues to stop after reacting 5 h, by the anti-of 1,1- dichloroethanes esterification System is answered to use petroleum ether extraction after 90 DEG C of concentrations, steaming petroleum ether obtains 1,1- dichloroethanes methylmesylates.
- A kind of 4. preparation method of propenyl-1,3-sulfonic acid lactone according to right 1, it is characterised in that 1, the 1- bis- The cyclisation of chloroethanes methylmesylate comprises the following steps：The 1,1- dichloroethanes methylmesylates of 1 mass parts are dissolved in the first of 5 mass parts In benzene, the CaH of 0.3 mass parts is added2Or 0.15 mass parts Na, be warming up to after the h of stirring reaction 2 during temperature is 0 DEG C of environment 90 DEG C, continue to stop after reacting 4h, unreacted CaH is quenched in the methanol for being slowly added to 0.15 mass parts2Or Na, vacuum distillation remove Toluene and methanol are removed, uses CH2Cl2Filtered after dilution, be evaporated CH2Cl2Obtain 2- chloropropyl -1,3- sultones.
- A kind of 5. preparation method of propenyl-1,3-sulfonic acid lactone according to right 1, it is characterised in that the 2- chlorine third The elimination reaction of base -1,3- sultones press include can following steps：The sultones of 2- chloropropyls -1,3 of 1 mass parts is added Into the toluene of 15 mass parts, the triethylamine of 1 mass parts is added, reacts 5h in the environment that temperature is 20~30 DEG C, filters, subtracts Solvent is distilled off in pressure, obtains propenyl-1,3-sulfonic acid lactone.
- A kind of 6. preparation method of propenyl-1,3-sulfonic acid lactone according to right 2, it is characterised in that：The sulfonation examination Agent includes NaHSO3And SO3；Sulfonated reagent is NaHSO3When, it is with 1 mol/L hydrochloric acid solutions that vinylidene chloride sulfonation addition is anti- Answer the pH value of system to adjust to 3~4, extracted after concentration using organic solvent, 1,1- dichloroethanes will be obtained after organic phase rectifying Sulfonic acid；Sulfonated reagent is SO3When, it is not necessary to the pH value of vinylidene chloride sulfonation addition reaction system is adjusted, after direct rectifying Obtain 1,1- dichloroethanes sulfonic acid.
- A kind of 7. preparation method of propenyl-1,3-sulfonic acid lactone according to right 6, it is characterised in that：It is described organic molten Agent includes petroleum ether, CH2Cl2。
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20090108934A (en) * | 2008-04-14 | 2009-10-19 | 주식회사 엘지화학 | Process for preparing 1,3-propenesultone |
| WO2011016440A1 (en) * | 2009-08-04 | 2011-02-10 | 和光純薬工業株式会社 | Method for producing cyclic sulfonic acid ester and intermediate thereof |
| CN104610221A (en) * | 2015-01-19 | 2015-05-13 | 烟台海川化学制品有限公司 | Preparation method of 1-propenyl-1,3-sultone |
-
2017
- 2017-11-27 CN CN201711205128.1A patent/CN107857752A/en active Pending
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20090108934A (en) * | 2008-04-14 | 2009-10-19 | 주식회사 엘지화학 | Process for preparing 1,3-propenesultone |
| WO2011016440A1 (en) * | 2009-08-04 | 2011-02-10 | 和光純薬工業株式会社 | Method for producing cyclic sulfonic acid ester and intermediate thereof |
| CN104610221A (en) * | 2015-01-19 | 2015-05-13 | 烟台海川化学制品有限公司 | Preparation method of 1-propenyl-1,3-sultone |
Non-Patent Citations (3)
| Title |
|---|
| COOTE, SUSANNAH C.等: ""Enantioselective Template-Directed [2+2] Photocycloadditions of Isoquinolones: Scope, Mechanism and Synthetic Applications"", 《CHEMISTRY - A EUROPEAN JOURNAL》 * |
| CORBU,ANDREI 等: ""Prop-2-ene-1-sulfonyl chloride"", 《E-EROS ENCYCLOPEDIA OF REAGENTS FOR ORGANIC SYNTHESIS》 * |
| T. DURST等: ""A new route to 5- and 6-membered ring sultones"", 《CANADIAN JOURNAL OF CHEMISTRY》 * |
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Application publication date: 20180330 |