CN117534648A - Preparation method of sulfite compound - Google Patents
Preparation method of sulfite compound Download PDFInfo
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- CN117534648A CN117534648A CN202210913860.9A CN202210913860A CN117534648A CN 117534648 A CN117534648 A CN 117534648A CN 202210913860 A CN202210913860 A CN 202210913860A CN 117534648 A CN117534648 A CN 117534648A
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- preparation
- sulfite
- reaction
- olefin
- sulfite compound
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- 238000002360 preparation method Methods 0.000 title claims abstract description 14
- -1 sulfite compound Chemical class 0.000 title claims abstract description 14
- 238000006243 chemical reaction Methods 0.000 claims abstract description 40
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 claims abstract description 30
- 238000000034 method Methods 0.000 claims abstract description 16
- 150000001336 alkenes Chemical class 0.000 claims abstract description 12
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims abstract description 12
- 239000003054 catalyst Substances 0.000 claims abstract description 11
- 239000002638 heterogeneous catalyst Substances 0.000 claims abstract description 5
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical class OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 claims description 15
- 230000002378 acidificating effect Effects 0.000 claims description 10
- 241000282326 Felis catus Species 0.000 claims description 8
- 150000002500 ions Chemical class 0.000 claims description 6
- 239000011347 resin Substances 0.000 claims description 6
- 229920005989 resin Polymers 0.000 claims description 6
- 239000007787 solid Substances 0.000 claims description 6
- 239000003930 superacid Substances 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 239000002994 raw material Substances 0.000 claims description 5
- 239000012264 purified product Substances 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims 1
- 238000005194 fractionation Methods 0.000 claims 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 claims 1
- 238000010924 continuous production Methods 0.000 abstract description 3
- 230000003321 amplification Effects 0.000 abstract description 2
- 238000003199 nucleic acid amplification method Methods 0.000 abstract description 2
- 239000011949 solid catalyst Substances 0.000 abstract description 2
- 239000000047 product Substances 0.000 description 14
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 description 10
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 7
- 238000005481 NMR spectroscopy Methods 0.000 description 7
- 238000004821 distillation Methods 0.000 description 7
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 6
- 239000005977 Ethylene Substances 0.000 description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 239000001257 hydrogen Substances 0.000 description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- 238000002156 mixing Methods 0.000 description 5
- WDXYVJKNSMILOQ-UHFFFAOYSA-N 1,3,2-dioxathiolane 2-oxide Chemical compound O=S1OCCO1 WDXYVJKNSMILOQ-UHFFFAOYSA-N 0.000 description 4
- 238000004817 gas chromatography Methods 0.000 description 4
- 239000003456 ion exchange resin Substances 0.000 description 4
- 229920003303 ion-exchange polymer Polymers 0.000 description 4
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 4
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 4
- 238000001228 spectrum Methods 0.000 description 4
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 3
- 239000002699 waste material Substances 0.000 description 3
- BKOOMYPCSUNDGP-UHFFFAOYSA-N 2-methylbut-2-ene Chemical compound CC=C(C)C BKOOMYPCSUNDGP-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 2
- 238000007792 addition Methods 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 238000011097 chromatography purification Methods 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 229920001567 vinyl ester resin Polymers 0.000 description 2
- MHNNAWXXUZQSNM-UHFFFAOYSA-N 2-methylbut-1-ene Chemical compound CCC(C)=C MHNNAWXXUZQSNM-UHFFFAOYSA-N 0.000 description 1
- YHQXBTXEYZIYOV-UHFFFAOYSA-N 3-methylbut-1-ene Chemical compound CC(C)C=C YHQXBTXEYZIYOV-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 1
- HBBGRARXTFLTSG-UHFFFAOYSA-N Lithium ion Chemical compound [Li+] HBBGRARXTFLTSG-UHFFFAOYSA-N 0.000 description 1
- 240000001949 Taraxacum officinale Species 0.000 description 1
- 235000005187 Taraxacum officinale ssp. officinale Nutrition 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 229910001508 alkali metal halide Inorganic materials 0.000 description 1
- 150000008045 alkali metal halides Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000012159 carrier gas Substances 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003792 electrolyte Substances 0.000 description 1
- RBBXSUBZFUWCAV-UHFFFAOYSA-N ethenyl hydrogen sulfite Chemical compound OS(=O)OC=C RBBXSUBZFUWCAV-UHFFFAOYSA-N 0.000 description 1
- 231100000086 high toxicity Toxicity 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 229910001416 lithium ion Inorganic materials 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000011973 solid acid Substances 0.000 description 1
- 238000009834 vaporization Methods 0.000 description 1
- 230000008016 vaporization Effects 0.000 description 1
Classifications
-
- 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
- C07D327/10—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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a preparation method of a sulfite compound, which specifically comprises the step of reacting olefin with sulfur trioxide in the presence of a heterogeneous catalyst to generate the sulfite compound. The catalyst of the reaction system is a solid catalyst, can realize continuous production, and is suitable for industrial amplification; and the reaction condition is mild, and the sulfite compound can be prepared with high conversion rate and high selectivity under the conditions of low cost and low process difficulty.
Description
Technical Field
The invention relates to a preparation method, in particular to a preparation method of a sulfite compound.
Background
Sulfite compounds are important chemical intermediates and have wide application in the fields of chemical industry and pharmacy. In recent years, with the development of lithium ion battery materials, sulfite compounds have also been found to be useful as additives for improving the performance of electrolytes, and the market demand is increasing.
Currently, the reaction of ethylene glycol with thionyl chloride is the predominant production process for obtaining sulfite. However, the process is an intermittent reaction and cannot be used for continuous production, the raw material sulfoxide chloride adopted by the process is unstable and has high toxicity, meanwhile, the production cost is high, a large amount of HCl can be generated in the production process, three wastes are difficult to treat and the like, and the release of the future yield of the sulfite is greatly limited.
Patent report (CN 101210008A) uses ethylene oxide and sulfur dioxide as raw materials, uses alkali metal halide, alkaline earth metal or iron, cobalt and nickel halide as catalyst, and makes them react under the harsher condition (220-300 deg.C, > 10 MPa) to obtain ethylene sulfite. The method has the limitations of harsh reaction conditions, high requirements on reaction equipment and low product yield.
In view of the foregoing, there is a need to develop a novel process for producing sulfite compounds with atomic economy, while reducing the process difficulty and reducing the production cost of three wastes.
Disclosure of Invention
In order to solve the technical problems, the invention provides a preparation method of a sulfite compound.
In order to achieve the above purpose, the technical scheme adopted by the invention is as follows:
a preparation method of sulfite compounds specifically comprises the following steps: reacting an olefin with sulfur trioxide in the presence of a heterogeneous catalyst to form a sulfite.
Taking ethylene as an example, the reaction mechanism and the chemical equation expression are as follows:
under the catalysis of an acid catalyst, pi bonds of sulfur trioxide molecules interact with pi bonds in ethylene molecules to form a five-membered ring intermediate state, and finally ethylene sulfite is formed.
In a preferred embodiment of the invention, the heterogeneous catalyst is selected from the group consisting of acidic ion resins and solid superacids, preferably acidic ion resins DNW-II, acidic ion resins DA-330, SO 4 -ZrO 2 One or more of solid superacids. The catalyst adopted by the invention is a solid acid catalyst, is easy to separate, and has higher activity on the reaction of the olefin and sulfur trioxide through experimentsCan synthesize sulfite compounds with high selectivity.
In a preferred embodiment of the invention, the molar ratio of olefin to sulfur trioxide is in the range of 0.1 to 10, preferably 0.2 to 2, such as 0.1, 0.5, 1, 3, 6, 8, 10, etc.
In a preferred embodiment of the invention, the olefin is fed in an amount of 3 to 8 g/(mL) of space velocity by mass relative to the catalyst cat H), preferably 4-7 g/(mL) cat H), e.g. 3 g/(mL) cat .h)、4g/(mL cat .h)、5g/(mL cat .h)、6g/(mL cat .h)、7g/(mL cat .h)、8g/(mL cat H) and the like.
In a preferred embodiment of the present invention, the reaction temperature is 10 to 200 ℃, preferably 50 to 150 ℃, such as 50 ℃, 70 ℃, 90 ℃, 100 ℃, 120 ℃, 150 ℃, etc.
In a preferred embodiment of the present invention, the reaction pressure is 0.5-2MPa, preferably 0.5-1.5MPa, for example 0.5MPa, 0.8MPa, 1.0MPa, 1.2MPa, 1.3MPa, 1.5MPa, etc.
In a preferred embodiment of the present invention, the olefin is a C2-C5 linear or linear olefin such as ethylene, propylene, 1-butene, isobutylene, 1-pentene, 2-methyl-1-butene, 3-methyl-1-butene, 2-methyl-2-butene, and the like.
In a preferred embodiment of the invention, after the reaction is completed, the purified product sulfite is obtained by rectification separation; the separated unreacted raw materials are recycled.
The invention has the following beneficial effects:
1) The catalyst of the reaction system is a solid catalyst, can realize continuous production, and is suitable for industrial amplification;
2) The reaction condition is mild, and the sulfite compound can be prepared with high conversion rate and high selectivity under the conditions of low cost and low process difficulty;
3) The reaction process basically generates no byproducts, the atom economy is good, and the three-waste treatment pressure is low.
Detailed Description
The invention will now be further illustrated by means of specific examples which are given solely by way of illustration of the invention and do not limit the scope thereof.
The sources of the raw materials in the following examples and comparative examples of the present invention are obtained from commercial sources unless otherwise specified. Wherein the acidic ion exchange resins DNW-II and DA-330 are available from Dandelion, SO 4 -ZrO 2 Solid superacids are available from south big synthetic chemistry.
The components involved in each reaction of the process are analyzed by gas chromatography, an analytical instrument is a Shimadzu GC-2010 gas chromatograph, and chromatographic analysis conditions are shown in table 1:
TABLE 1 gas chromatography conditions
| Carrier gas | High purity nitrogen |
| Hydrogen flow rate | 40mL/min |
| Air flow rate | 400mL/min |
| Supplementary air flow | 30mL/min |
| Sample injection mode | Constant current |
| Vaporization chamber temperature | 280℃ |
| Split ratio | 50/1 |
| Sample injection amount | 0.2μL |
| Column flow rate | 1mL/min |
| Detector temperature | 300℃ |
Column temperature: second-order programmed heating, wherein the initial temperature is 50 ℃, the temperature is kept for 2 minutes, and then the temperature is increased to 80 ℃ at the speed of 5 ℃/min; then the temperature is raised to 280 ℃ at the speed of 15 ℃/min and the temperature is kept for 10 minutes.
[ example 1 ]
Ethylene and sulfur trioxide were thoroughly mixed in a molar ratio of 0.5 by a mixer, preheated to 50 ℃ after mixing and fed into a tubular reactor packed with 20mL of an acidic ion exchange resin DNW-II catalyst. The ethylene feed rate was 120g/h and the space velocity of the feed (in terms of ethylene) was 6 g/(mL) cat H), controlling the reaction temperature to be 50 ℃ and the reaction pressure to be 0.5MPa. After the reaction is finished, the conversion rate of the reaction is detected to reach 85%, and the selectivity of the target product vinyl sulfite is 96.7%. Under the condition of heating in an oil bath at 150 ℃, carrying out reduced pressure distillation, firstly removing a small amount of unreacted ethylene and sulfur trioxide under the absolute pressure of 20kPa, then distilling under reduced pressure to 10kPa to obtain a ethylene sulfite product, and carrying out gas chromatographic analysis to purify the product, wherein the purity of the product is more than 99.95 percent.
Nuclear magnetic resonance hydrogen spectrum:
1 HNMR(CDCl 3 ,400MHz,TMS):δ＝4.276(s,4H)
[ example 2 ]
Propylene and sulfur trioxide were thoroughly mixed by a mixer in a molar ratio of 0.2, preheated to 50 ℃ after mixing and fed into a tubular reactor packed with 50mL of an acidic ion exchange resin DA-330 catalyst. The propylene feed rate was 350g/h and the space velocity of the feed (in terms of propylene) was 7 g/(mL) cat H), controlling the reaction temperature to be 80 ℃ and the reaction pressure to be 1MPa. After the reaction is finished, the conversion rate of the reaction is detected to reach 88%, and the selectivity of the target product 4-methyl ethylene sulfite is 97%. Under the condition of heating in an oil bath at 150 ℃, the reduced pressure distillation is carried out, a small amount of unreacted propylene and sulfur trioxide are removed under the absolute pressure of 20kPa, then the reduced pressure is reduced to 10kPa for distillation to obtain a 4-methyl ethylene sulfite product, and the purity of the product after gas chromatographic analysis and purification is more than 99.97 percent.
Nuclear magnetic resonance hydrogen spectrum:
1 H NMR(CDCl 3 ,400MHz,TMS):δ＝5.08-5.12(m,1H),3.80(dd,1H,J＝18Hz,7Hz),3.54(dd,1H,J＝18Hz,7Hz),1.34(d,3H,J＝7Hz).
[ example 3 ]
Fully mixing 1-butene and sulfur trioxide according to the mol ratio of 1 by a mixer, preheating to 50 ℃ after mixing and feeding into a mixer filled with 25mL SO 4 -ZrO 2 In a tubular reactor of a solid superacid catalyst. The 1-butene feed rate was 350g/h and the space velocity of the feed (based on 1-butene) was 5 g/(mL) cat H), controlling the reaction temperature to be 150 ℃ and the reaction pressure to be 1.5MPa. After the reaction is finished, the conversion rate of the reaction is detected to reach 61%, and the selectivity of the target product 4-ethylsulfinate vinyl ester is 96%. Under 160 ℃ oil bath heating condition, reduced pressure distillation is carried out, firstly, unreacted small amount of butene and sulfur trioxide are removed under 20kPa absolute pressure, and then reduced pressure is reduced to 5kPa for distillation to obtain 4-ethylThe purity of the product of the ethylene sulfite product after being purified by gas chromatography analysis is more than 99.95 percent.
Nuclear magnetic resonance hydrogen spectrum:
1 H NMR(CDCl 3 ,400MHz,TMS):δ＝4.88-4.94(m,1H),3.81(dd,1H,J＝18Hz,7Hz),3.58(dd,1H,J＝18Hz,7Hz),1.49-1.52(m,2H),0.89(t,3H,J＝7Hz).
[ example 4 ]
The 1-pentene and sulfur trioxide were thoroughly mixed in a molar ratio of 2 by a mixer, preheated to 50℃after mixing and fed into a tubular reactor packed with 80mL of an acidic ion exchange resin DNW-II catalyst. The 1-pentene feed rate was 320g/h and the space velocity of the feed (in 1-pentene) was 4 g/(mL) cat H), controlling the reaction temperature to 120 ℃ and the reaction pressure to 0.8MPa. After the reaction is finished, the conversion rate of the reaction is detected to reach 45%, and the selectivity of the target product 4-propylsulfinate vinyl ester is 98%. Under 160 ℃ oil bath heating condition, reduced pressure distillation is carried out, firstly, unreacted small amount of 1-pentene and sulfur trioxide are removed under 20kPa absolute pressure, then, the reduced pressure is reduced to 5kPa for distillation to obtain a 4-propylvinylene sulfite product, and the purity of the product is more than 99.96% after gas chromatography analysis and purification.
Nuclear magnetic resonance hydrogen spectrum:
1 H NMR(CDCl 3 ,400MHz,TMS):δ＝4.88-4.95(m,1H),3.78(dd,1H,J＝18Hz,7Hz),3.52(dd,1H,J＝18Hz,7Hz),1.30-1.40(m,4H),0.87(t,3H,J＝7Hz).
the foregoing is merely a preferred embodiment of the present invention, and it should be noted that modifications and additions may be made to those skilled in the art without departing from the method of the present invention, which modifications and additions are also to be considered as within the scope of the present invention.
Claims (8)
1. A process for preparing sulfite compounds, characterized in that in the presence of heterogeneous catalyst, olefin and sulfur trioxide are reacted to generate sulfite compounds.
2. The process for the preparation of sulphites according to claim 1, wherein the heterogeneous catalyst is selected from the group consisting of acidic ion resins and solid superacids, preferably acidic ion resins DNW-II, acidic ion resins DA-330, SO 4 -ZrO 2 One or more of solid superacids.
3. The process for the preparation of sulphites according to claim 2, wherein the molar ratio of olefin to sulphur trioxide is between 0.1 and 10, preferably between 0.2 and 2.
4. A process for the preparation of a sulfite compound as claimed in any of claims 1 to 3, wherein the olefin is fed in an amount of 3 to 8 g/(mL) of space velocity by mass relative to the catalyst cat H), preferably 4-7 g/(mL) cat .h)。
5. A process for the preparation of a sulphite-based compound according to any one of claims 1 to 3, wherein the reaction temperature is 10 to 200 ℃, preferably 50 to 150 ℃.
6. The process for the preparation of sulphites according to claim 5, wherein the reaction pressure is 0.5-2MPa, preferably 0.5-1.5MPa.
7. A process for the preparation of a sulfite compound according to any of claims 1 to 3, wherein the olefin is a C2 to C5 linear or linear olefin.
8. A process for the preparation of a sulfite compound according to any of claims 1 to 3, characterized in that after the end of the reaction, the purified product sulfite compound is obtained by fractionation; the separated unreacted raw materials are recycled.
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| CN202210913860.9A CN117534648A (en) | 2022-08-01 | 2022-08-01 | Preparation method of sulfite compound |
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| Application Number | Priority Date | Filing Date | Title |
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| CN202210913860.9A CN117534648A (en) | 2022-08-01 | 2022-08-01 | Preparation method of sulfite compound |
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| CN202210913860.9A Pending CN117534648A (en) | 2022-08-01 | 2022-08-01 | Preparation method of sulfite compound |
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