CN114478203A - Preparation method of vinyl low-carbon alcohol for polyether initiator - Google Patents
Preparation method of vinyl low-carbon alcohol for polyether initiator Download PDFInfo
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- CN114478203A CN114478203A CN202210104542.8A CN202210104542A CN114478203A CN 114478203 A CN114478203 A CN 114478203A CN 202210104542 A CN202210104542 A CN 202210104542A CN 114478203 A CN114478203 A CN 114478203A
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- Prior art keywords
- reaction
- diethylene glycol
- lower alcohol
- catalyst
- polyether
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- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 title claims abstract description 14
- 239000004721 Polyphenylene oxide Substances 0.000 title claims abstract description 13
- 229920000570 polyether Polymers 0.000 title claims abstract description 13
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 title claims abstract description 13
- 229920002554 vinyl polymer Polymers 0.000 title claims abstract description 13
- 238000002360 preparation method Methods 0.000 title claims abstract description 12
- 239000003999 initiator Substances 0.000 title claims abstract description 10
- 229910052799 carbon Inorganic materials 0.000 title description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims abstract description 63
- 238000006243 chemical reaction Methods 0.000 claims abstract description 51
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 27
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims abstract description 21
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims abstract description 21
- 238000000034 method Methods 0.000 claims abstract description 17
- 239000003054 catalyst Substances 0.000 claims abstract description 16
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims abstract description 14
- 239000012295 chemical reaction liquid Substances 0.000 claims abstract description 13
- 238000010992 reflux Methods 0.000 claims abstract description 11
- 238000010438 heat treatment Methods 0.000 claims abstract description 10
- 239000007787 solid Substances 0.000 claims abstract description 9
- 238000003756 stirring Methods 0.000 claims abstract description 6
- 230000008569 process Effects 0.000 claims abstract description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 30
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 26
- WULAHPYSGCVQHM-UHFFFAOYSA-N 2-(2-ethenoxyethoxy)ethanol Chemical compound OCCOCCOC=C WULAHPYSGCVQHM-UHFFFAOYSA-N 0.000 claims description 19
- 229910052757 nitrogen Inorganic materials 0.000 claims description 13
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 12
- 239000007789 gas Substances 0.000 claims description 10
- 239000012043 crude product Substances 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 238000001704 evaporation Methods 0.000 claims description 2
- 239000011261 inert gas Substances 0.000 claims description 2
- 239000007858 starting material Substances 0.000 claims 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 11
- 239000007788 liquid Substances 0.000 description 10
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 8
- 239000000203 mixture Substances 0.000 description 6
- 239000000126 substance Substances 0.000 description 5
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical compound C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 4
- 229910052786 argon Inorganic materials 0.000 description 4
- 239000010410 layer Substances 0.000 description 4
- 238000005070 sampling Methods 0.000 description 4
- 238000004809 thin layer chromatography Methods 0.000 description 4
- 238000001816 cooling Methods 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- 230000020477 pH reduction Effects 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- JFMADMRWGIJWGL-UHFFFAOYSA-N 2-(2-hydroxyethoxy)ethanol;potassium Chemical compound [K].OCCOCCO JFMADMRWGIJWGL-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 150000004703 alkoxides Chemical class 0.000 description 2
- 238000011835 investigation Methods 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- 229910000510 noble metal Inorganic materials 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 230000002194 synthesizing effect Effects 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 238000007259 addition reaction Methods 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000006704 dehydrohalogenation reaction Methods 0.000 description 1
- 150000002148 esters Chemical group 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- XLYOFNOQVPJJNP-ZSJDYOACSA-N heavy water Substances [2H]O[2H] XLYOFNOQVPJJNP-ZSJDYOACSA-N 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 238000006317 isomerization reaction Methods 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- 239000012038 nucleophile Substances 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 238000011172 small scale experimental method Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/18—Preparation of ethers by reactions not forming ether-oxygen bonds
- C07C41/26—Preparation of ethers by reactions not forming ether-oxygen bonds by introduction of hydroxy or O-metal groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F1/00—Compounds containing elements of Groups 1 or 11 of the Periodic Table
- C07F1/04—Sodium compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention relates to a preparation method of vinyl lower alcohol used for a polyether initiator, which comprises the following steps: (1) stirring the catalyst and the diglycol and heating to dissolve the catalyst solid completely; (2) adding cyclohexane, removing water at reflux temperature, and distilling out cyclohexane and unreacted diglycol to obtain pre-reaction liquid; (3) adding the pre-reaction liquid into a reaction bottle, heating to 90-105 ℃, starting to introduce acetylene gas for reaction, controlling the reaction temperature at 160-. The method has the advantages of simple process, low equipment requirement, high product purity, high yield and low cost.
Description
Technical Field
The invention relates to the technical field of chemical industry, in particular to a preparation method of vinyl low carbon alcohol for a polyether initiator.
Background
As a method for synthesizing vinyl ether, there are acetylene method, thermal acetal decomposition method, dehydrohalogenation method, olefin oxidation method, ester exchange method, allyl isomerization reaction and the like. Acetylene is a cheap and easily available raw material, and is generally industrially prepared by an acetylene method, i.e. generally by reacting alcohol with acetylene under the action of a basic catalyst at a certain pressure and a certain temperature.
The prior preparation method of diethylene glycol monovinyl ether comprises the steps of taking acetylene and diethylene glycol as raw materials, taking potassium diethylene glycol as a catalyst, and adopting a tubular reactor to carry out liquid phase circulation reaction to generate the diethylene glycol monovinyl ether. The reaction conditions are preferably that the amount of the catalyst of the diethylene glycol potassium is 4% of the mass of the diethylene glycol, the reaction temperature is 175 ℃, the reaction pressure is 6MPa, and the retention time is 175 s. When the liquid phase continuous circulation reaction was carried out under these conditions and the reaction reached a steady state, the conversion of diethylene glycol was 76.03%, the yield of diethylene glycol monovinyl ether was 59.03%, the yield of diethylene glycol monovinyl ether was 15.10%, and the total yield of diethylene glycol vinyl ether was 74.13%. The preparation method has high requirements on reaction equipment in the preparation process, and has the disadvantages of complicated preparation process and high cost.
US6037482 mentions that noble metal compounds such as rhodium, ruthenium, palladium, platinum and gold as catalysts for addition reaction of nucleophiles such as alcohols and acetylenic substances such as acetylene have good catalytic activity, but vinyl ether selectivity is low and noble metals are expensive, and chinese patent CN102173982B provides a method for synthesizing glycol monovinyl ether and bis vinyl ether, but the yield of diethylene glycol vinyl ether is low.
Disclosure of Invention
The invention aims to provide a preparation method of vinyl lower alcohol used for a polyether initiator.
The technical scheme of the invention is as follows:
a preparation method of vinyl lower alcohol used for polyether initiator comprises the following steps:
(1) adding a catalyst and diethylene glycol into a reactor, wherein the ratio of the catalyst to the diethylene glycol is 1.0-1.1mol/100mL, stirring, heating to 80 ℃ for reaction for 0.5 hour, and then heating to 85 ℃ for reaction for 0.5 hour to completely dissolve catalyst solids;
(2) adding cyclohexane and removing water at reflux temperature, wherein the volume ratio of the cyclohexane to the diglycol is 1.5:1-1.2, and when the water layer quality in the water separator reaches the theoretical water generation amount, evaporating the cyclohexane and unreacted diglycol to obtain a pre-reaction liquid;
(3) the air in the reaction bottle is replaced by gas;
(4) adding the pre-reaction liquid into a reaction bottle, heating to 90-105 ℃, starting to introduce acetylene gas for reaction, controlling the reaction temperature at 160-180 ℃, controlling the reaction pressure to be more than 0.3MPa, sampling every half an hour, determining whether the reaction is complete by using a thin layer chromatography, and obtaining a crude product of diethylene glycol monovinyl ether after the reaction is finished;
(5) rectifying the crude product of the diethylene glycol monovinyl ether to obtain the diethylene glycol monovinyl ether.
Preferably, the catalyst in step (1) is potassium hydroxide or sodium hydroxide.
Preferably, the reflux temperature in step (2) is 80-85 ℃.
Preferably, the theoretical amount of water produced in step (2) is 18g of water per 1moL of catalyst.
Preferably, the temperature for distilling cyclohexane and unreacted diethylene glycol in the step (2) is 245 ℃ until no more cyclohexane is distilled out.
Preferably, the gas used in step (3) is an inert gas or nitrogen.
Preferably, the molar ratio of the acetylene introduced in the step (4) to the pre-reaction liquid is 6:1-9: 1.
Preferably, the acetylene is introduced in step (4) at a rate of 30 ml/min.
The invention has the beneficial effects that:
the method has the advantages of simple process, low equipment requirement, high product purity, high yield and low cost.
Detailed Description
Example 1
The reaction mechanism is as follows: first, sodium hydroxide is reacted with diethylene glycol to form an alkoxide
HOCH2CH2OCH2CH2OH+2NaOH→NaOCH2CH2OCH2CH2ONa+2H2O
Second, reacting the alkoxide with acetylene to form a metal substituent of diethylene glycol vinyl ether
NaOCH2CH2OCH2CH2ONa+CH≡CH→CHNa＝CHOCH2CH2OCH2CH2OCH＝NaCH
+CHNa＝CHOCH2CH2OCH2CH2ONa
Thirdly, acidifying to obtain diethylene glycol monovinyl ether
CHNa＝CHOCH2CH2OCH2CH2ONa+CH3COOH→
CHNa＝CHOCH2CH2OCH2CH2OH+CH3COONa
100ml of diethylene glycol and 1mol of sodium hydroxide solid and 40g of sodium hydroxide solid are added into a 500ml dry anhydrous round-bottom flask provided with a condenser and a water separator, the mixture is stirred and heated to 80 ℃ for reaction for 0.5 hour, then the temperature is raised to 85 ℃ for reaction for 0.5 hour, 150ml of cyclohexane is added after the sodium hydroxide and the diethylene glycol completely react, the reflux temperature is maintained at 80-85 ℃ to remove water generated by the reaction, 17.5g of water is obtained when the liquid level of a water layer in the water separator does not change any more, the temperature is continuously raised, the reflux temperature is maintained at 245 ℃ to remove unreacted diethylene glycol, and the reaction is stopped until no more substances are evaporated, so that 107ml of pre-reaction liquid is obtained.
Adding the pre-reaction solution into a four-neck flask with a thermometer, a nitrogen protection interface and a stirrer, starting stirring, connecting nitrogen, introducing the nitrogen at a speed of 5ml/min, completely replacing air in the flask, when the temperature is heated to 95 ℃, the nitrogen flow is reduced, acetylene gas is introduced, the introduction rate of acetylene is 30ml/min, the acetylene gas is continuously introduced for 20min, the reaction temperature is controlled at 175 ℃, the reaction pressure is 0.35MPa, a glass capillary tube is used for sampling every 30min, and (3) confirming whether the reaction is complete through thin-layer chromatography, stopping the reaction until the reaction is complete, continuously introducing nitrogen for cooling, adding dilute acetic acid for acidification after the liquid in the flask is cooled to room temperature, separating the liquid of the mixture to obtain an organic layer which is a crude product of the diethylene glycol monovinyl ether, and rectifying to obtain 85.8g of pure diethylene glycol monovinyl ether liquid with the yield of 65%.
Example 2
50ml of diethylene glycol and 0.5mol of potassium hydroxide solid and 28g of potassium hydroxide solid are added into a 250ml dry anhydrous round-bottom flask provided with a condenser and a water separator, the mixture is stirred and heated to 80 ℃ for reaction for 0.5 hour, then the temperature is raised to 85 ℃ for reaction for 0.5 hour, 80ml of cyclohexane is added after the sodium hydroxide and the diethylene glycol completely react, the reflux temperature is maintained at 80-85 ℃ to remove water generated by the reaction, when the liquid level of an aqueous layer in the water separator is not changed any more, 8.8g of water is obtained, the temperature is continuously raised, the reflux temperature is maintained at 245 ℃ to remove unreacted diethylene glycol, and the reaction is stopped until no more substances are evaporated, so that 53ml of pre-reaction liquid is obtained.
Adding the pre-reaction liquid into a four-neck flask with a thermometer, a nitrogen protection interface and a stirrer, starting stirring, connecting argon, controlling the argon introduction rate to be 5ml/min, completely replacing air in the flask, starting heating to 95 ℃, reducing the argon flow, starting introducing acetylene gas, controlling the acetylene introduction rate to be 35ml/min, continuously introducing for 20min, controlling the reaction temperature to be 170 plus 175 ℃, controlling the reaction pressure to be 0.35MPa, sampling by using a glass capillary tube every 30min, confirming whether the reaction is complete through thin-layer chromatography, continuously introducing argon for cooling, adding dilute acetic acid for acidification after the liquid in the flask is cooled to room temperature, obtaining an organic layer which is a crude product of diethylene glycol monovinyl ether after the mixture is separated, and obtaining 45.5g of pure diethylene glycol monovinyl ether liquid through rectification, wherein the yield is 69%.
Example 3
200ml of diethylene glycol and 2mol of sodium hydroxide solid and 80g of sodium hydroxide solid are added into a 1L anhydrous round bottom flask provided with a condenser and a water separator, the mixture is stirred and heated to 80 ℃ for reaction for 0.5 hour, then the temperature is raised to 85 ℃ for reaction for 0.5 hour, 300ml of cyclohexane is added after the sodium hydroxide and the diethylene glycol completely react, the reflux temperature is maintained at 80-85 ℃ to remove water generated by the reaction, 35.4g of water is obtained when the liquid level of a water layer in the water separator is not changed any more, the temperature is continuously raised, the reflux temperature is maintained at 245 ℃ to remove unreacted diethylene glycol, and the reaction is stopped until no more substances are evaporated, so that 213ml of pre-reaction liquid is obtained.
Adding the pre-reaction liquid into a four-neck flask with a thermometer, a nitrogen protection interface and a stirrer, starting stirring, connecting nitrogen, wherein the nitrogen introduction rate is 5ml/min, completely replacing air in the flask, heating to 95 ℃, reducing the nitrogen flow, introducing acetylene gas, wherein the acetylene introduction rate is 38ml/min, continuously introducing for 20min, controlling the reaction temperature at 170-175 ℃, the reaction pressure at 0.35MPa, sampling every 30min by using a glass capillary tube, confirming whether the reaction is complete through thin-layer chromatography, continuously introducing nitrogen for cooling, adding dilute acetic acid for acidification after the liquid in the flask is cooled to room temperature, obtaining an organic layer which is a crude product of diethylene glycol monovinyl ether after the mixture is separated, and obtaining 179g of pure diethylene glycol monovinyl ether liquid through rectification, wherein the yield is 68%.
At present, the technical scheme of the application has been subjected to pilot plant test, namely small-scale experiment before large-scale mass production of products; after the pilot test is finished, the investigation for the use of the user is carried out in a small range, and the investigation result shows that the satisfaction degree of the user is higher; the preparation of products for formal production for industrialization (including intellectual property risk early warning research) has been started.
Claims (8)
1. A preparation method of vinyl lower alcohol used for polyether initiator is characterized by comprising the following steps:
(1) adding a catalyst and diethylene glycol into a reactor, wherein the ratio of the catalyst to the diethylene glycol is 1.0-1.1mol/100ml, stirring, heating to 80 ℃ for reaction for 0.5 hour, and then heating to 85 ℃ for reaction for 0.5 hour to completely dissolve catalyst solids;
(2) adding cyclohexane and removing water at reflux temperature, wherein the volume ratio of the cyclohexane to the diglycol is 1.2:1-1.5:1, and when the water layer mass in the water separator reaches the theoretical water generation amount, evaporating the cyclohexane and the unreacted diglycol to obtain a pre-reaction liquid;
(3) the air in the reaction bottle is replaced completely by gas;
(4) adding the pre-reaction liquid into a reaction bottle, heating to 90-105 ℃, starting to introduce acetylene gas for reaction, controlling the reaction temperature at 160-;
(5) rectifying the crude product of the diethylene glycol monovinyl ether to obtain the diethylene glycol monovinyl ether.
2. The method for preparing vinyl lower alcohol used for polyether initiator according to claim 1, wherein the catalyst in step (1) is potassium hydroxide or sodium hydroxide.
3. The method for preparing vinyl lower alcohol for polyether initiator as claimed in claim 1, wherein the reflux temperature in step (2) is 80-85 ℃.
4. The method of claim 1, wherein the theoretical amount of water generated in step (2) is 18g of water per 1moL of catalyst.
5. The process for preparing a vinyl lower alcohol for a polyether starter as claimed in claim 1, wherein the temperature at which cyclohexane and unreacted diethylene glycol are distilled off in step (2) is 245 ℃ until they are not distilled off any more.
6. The process for preparing a vinyl lower alcohol for a polyether starter as claimed in claim 1, wherein the gas used in the step (3) is an inert gas or nitrogen.
7. The method for preparing vinyl lower alcohol for polyether initiator as claimed in claim 1, wherein the molar ratio of the acetylene introduced in step (4) to the pre-reaction liquid is 6:1-9: 1.
8. The process for producing a vinyl lower alcohol for polyether starter as claimed in claim 1, wherein the feed rate of acetylene in the step (4) is 30 ml/min.
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| Application Number | Priority Date | Filing Date | Title |
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| CN202210104542.8A CN114478203B (en) | 2022-01-28 | 2022-01-28 | Preparation method of vinyl low-carbon alcohol for polyether initiator |
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|---|---|---|---|
| CN202210104542.8A CN114478203B (en) | 2022-01-28 | 2022-01-28 | Preparation method of vinyl low-carbon alcohol for polyether initiator |
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| CN114478203B CN114478203B (en) | 2023-04-07 |
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|---|---|---|---|---|
| GB580748A (en) * | 1943-11-25 | 1946-09-18 | William John Roy Evans | Improvements in the manufacture of vinyl ethers |
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Denomination of invention: A Preparation Method for Vinyl Low Carbon Alcohols Used as Polyether Initiating Agents Effective date of registration: 20230912 Granted publication date: 20230407 Pledgee: Bank of China Limited by Share Ltd. Cangzhou branch Pledgor: Cangzhou Zhongrun chemical additives Co.,Ltd. Registration number: Y2023980056408 |