CN118373799A - Preparation method of paraldehyde - Google Patents
Preparation method of paraldehyde Download PDFInfo
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- CN118373799A CN118373799A CN202410460621.1A CN202410460621A CN118373799A CN 118373799 A CN118373799 A CN 118373799A CN 202410460621 A CN202410460621 A CN 202410460621A CN 118373799 A CN118373799 A CN 118373799A
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- Prior art keywords
- ionic liquid
- acetaldehyde
- paraldehyde
- reaction
- preparation
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- SQYNKIJPMDEDEG-UHFFFAOYSA-N paraldehyde Chemical compound CC1OC(C)OC(C)O1 SQYNKIJPMDEDEG-UHFFFAOYSA-N 0.000 title claims abstract description 32
- 229960003868 paraldehyde Drugs 0.000 title claims abstract description 32
- 238000002360 preparation method Methods 0.000 title claims abstract description 13
- 238000006243 chemical reaction Methods 0.000 claims abstract description 49
- 239000002608 ionic liquid Substances 0.000 claims abstract description 36
- 238000000034 method Methods 0.000 claims abstract description 21
- -1 1-ethyl-3-butyl sulfonic acid imidazole p-toluenesulfonate Chemical compound 0.000 claims abstract description 13
- 239000002994 raw material Substances 0.000 claims abstract description 12
- 238000004821 distillation Methods 0.000 claims abstract description 4
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 claims description 68
- 238000006116 polymerization reaction Methods 0.000 claims description 11
- 238000006555 catalytic reaction Methods 0.000 claims description 4
- 238000004064 recycling Methods 0.000 claims description 2
- 238000003756 stirring Methods 0.000 claims description 2
- 239000003054 catalyst Substances 0.000 abstract description 20
- 239000002904 solvent Substances 0.000 abstract description 6
- IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 abstract description 5
- 239000000047 product Substances 0.000 description 15
- 239000002253 acid Substances 0.000 description 7
- 239000000203 mixture Substances 0.000 description 6
- 229910001220 stainless steel Inorganic materials 0.000 description 6
- 239000010935 stainless steel Substances 0.000 description 6
- VKFOCPKVTXIIOD-UHFFFAOYSA-N 1h-imidazol-1-ium;4-methylbenzenesulfonate Chemical compound [NH2+]1C=CN=C1.CC1=CC=C(S([O-])(=O)=O)C=C1 VKFOCPKVTXIIOD-UHFFFAOYSA-N 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 5
- WAASCVGPJBHARY-UHFFFAOYSA-N hexane-2-sulfonic acid Chemical compound CCCCC(C)S(O)(=O)=O WAASCVGPJBHARY-UHFFFAOYSA-N 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 4
- 239000012295 chemical reaction liquid Substances 0.000 description 4
- 238000004817 gas chromatography Methods 0.000 description 4
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 125000002091 cationic group Chemical group 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 239000005956 Metaldehyde Substances 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 2
- 238000009776 industrial production Methods 0.000 description 2
- GKKDCARASOJPNG-UHFFFAOYSA-N metaldehyde Chemical compound CC1OC(C)OC(C)OC(C)O1 GKKDCARASOJPNG-UHFFFAOYSA-N 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- BGJSXRVXTHVRSN-UHFFFAOYSA-N 1,3,5-trioxane Chemical group C1OCOCO1 BGJSXRVXTHVRSN-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- 229920000877 Melamine resin Polymers 0.000 description 1
- 229910006213 ZrOCl2 Inorganic materials 0.000 description 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 208000012839 conversion disease Diseases 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 239000011964 heteropoly acid Substances 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 239000011829 room temperature ionic liquid solvent Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000011973 solid acid Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- IPCAPQRVQMIMAN-UHFFFAOYSA-L zirconyl chloride Chemical compound Cl[Zr](Cl)=O IPCAPQRVQMIMAN-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/584—Recycling of catalysts
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention relates to a preparation method of paraldehyde, which takes ionic liquid 1-ethyl-3-butyl sulfonic acid imidazole p-toluenesulfonate as a catalyst, does not need other solvents in the reaction process, saves cost and is more environment-friendly. In addition, the method of the invention not only greatly improves the conversion rate of acetaldehyde, but also has good reaction selectivity, improves the utilization rate of raw materials and has more atom economy. In addition, the invention has simple post-treatment, can separate the product through simple reduced pressure distillation operation, and the ionic liquid catalyst can be recycled, thereby being more environment-friendly.
Description
Technical Field
The invention relates to the field of organic synthesis, in particular to a preparation method of paraldehyde.
Background
Paraffin is also named as secondary (ethyl) aldehyde, melamine aldehyde and paraaldehyde, and has a molecular formula of C 6H12O3, colorless oily liquid and aromatic smell; the melting point is 12.6 ℃, the boiling point is 128 ℃, the relative density is 0.994 (20/4 ℃), and the water-insoluble and miscible organic solvent is the most organic solvent; can be decomposed into acetaldehyde again in the presence of a small amount of acid, can be used as a stable form of acetaldehyde, and is convenient for storage and transportation of acetaldehyde. Used as solvent, organic synthesis, rubber accelerator and antioxidant. Is used in the fields of pesticides, incense, medicine and paint industry.
The prior method for preparing the paraldehyde generally takes the acetaldehyde as a raw material and generates the trioxymethylene through polymerization reaction under the acidic condition. CN102250054a discloses that aldehyde is used as raw material, strong acid cationic resin with sulfonic acid group on styrene-divinylbenzene copolymer is used as catalyst, and the conversion rate of aldehyde can reach more than 90%. CN 105367542a discloses that first ethanol is dehydrogenated to produce acetaldehyde, then calcium chloride is used as a catalyst to produce paraldehyde, and the patent does not report on specific reaction yields. CN 113173907A discloses the preparation of paraldehyde by a fixed bed reactor in the presence of acetaldehyde, a solvent selected from methanol, ethanol and a catalyst selected from a strong acid cationic resin or a solid acid. The patent states that the conversion of acetaldehyde and the selectivity to paraldehyde are both greater than 99%. JP2002145877A discloses the preparation of paraldehyde with acetaldehyde as starting material and ZrOCl2 as catalyst, wherein the conversion of acetaldehyde is 76%.
Liu Ruijiang et al (university of Nanjing Industrial journal, 2004, 26 (6), 29) studied the reaction law of acetaldehyde synthesis to paraldehyde and examined the effect of catalyst on acetaldehyde polymerization with different acids (hydrochloric acid, sulfuric acid, formic acid, oxalic acid, ferric chloride, palladium chloride). Zuolin Zhu et al (Synthesis, 1998, (4), 417) disclose the preparation of acetaldehyde as paraldehyde with MTO as catalyst, with conversions of 80-99%.
CN101544628a discloses a method for preparing acetal compounds by room temperature ionic liquid catalysis, wherein the adopted ionic liquid is imidazolyl and pyridyl functionalized ionic liquid. However, the conversion of the process is not high, and the amount of paraldehyde after 4 hours of reaction is only 14% when aqueous acetic acid is used as the starting material.
A method for preparing trimeric aldehydes by polymerizing aldehydes under the catalysis of ionic liquids is reported in Xinyu et al (Chinese Journal of Chemistry,2006,24,1066). The influence of different ionic liquids on the reaction is examined, and the selectivity of the reaction can reach 100% and the conversion rate is 90.2% by the [ Et 3NH]Cl/FeCl3 effect is optimal.
In summary, in the existing method for preparing the paraldehyde, most of the method uses acid (such as inorganic acid, organic acid, lewis acid, heteropolyacid, acid cationic resin and the like) as a catalyst, and when the acid is used as the catalyst, the problems of difficult separation of products, low conversion rate and the like exist, the catalyst is difficult to recycle, the production cost is greatly increased, and the industrial production is not facilitated. CN101544628a discloses that ionic liquid is used as a catalyst, however, the reaction conversion rate is low, which causes raw material waste and is difficult to industrialize. The conversion rate of the reaction can be improved to a certain extent by using FeCl3 and ionic liquid as catalysts in the presence of the jades, but the conversion rate is only 90.2%, and a large amount of raw materials still have incomplete reaction. Therefore, it is highly desirable to provide a method for preparing paraldehyde which is environment-friendly and suitable for industrial production.
Disclosure of Invention
In order to solve the technical problems in the prior art, the invention provides a preparation method of paraldehyde. The method has mild reaction conditions, can recycle the catalyst, accords with the green chemical concept, is more environment-friendly, and greatly improves the conversion rate and selectivity of raw materials.
The invention provides a preparation method of paraldehyde, which is characterized by comprising the following steps:
Taking acetaldehyde as a raw material, and carrying out polymerization reaction under the catalysis of ionic liquid to prepare paraldehyde; the ionic liquid is 1-ethyl-3-butyl sulfonic acid imidazole p-toluenesulfonate.
Preferably, the temperature of the polymerization reaction is from 0 to 60 ℃, more preferably from 20 to 40 ℃, most preferably room temperature.
Preferably, the polymerization time is from 0.4 to 4 hours, more preferably from 0.5 to 2 hours, most preferably from 0.5 to 1 hour.
Preferably, the mass ratio of the ionic liquid to the acetaldehyde is 1 (5-100), more preferably 1 (10-20).
Preferably, the preparation method of the paraldehyde comprises the following steps:
Adding acetaldehyde and ionic liquid into a reaction kettle, stirring at room temperature for reaction for 0.5-1 hour, recovering acetaldehyde and collecting product paraldehyde by reduced pressure distillation after the reaction is finished, wherein the remainder is the ionic liquid, and the ionic liquid can be recovered for recycling.
Takes acetaldehyde as raw material, and when polymerization reaction is carried out under acidic condition, the generated products comprise paraldehyde, metaldehyde and the like. When the activity of the catalyst is low, the conversion rate of acetaldehyde may be low, the utilization rate of raw materials is reduced, and finally the yield is reduced; when the activity of the catalyst is high, acetaldehyde may be excessively polymerized, so that a large amount of metaldehyde byproducts are generated, the purity of the product is reduced, and the yield of the product is affected.
Based on the report of the prior literature, the inventor researches and researches various ionic liquids, and finally screens out the ionic liquid catalyst 1-ethyl-3-butyl sulfonic acid imidazole p-toluenesulfonate. Compared with [ Et 3NH]Cl/FeCl3 ] reported by Yu Xinyu and the like, the method has the advantages that the conversion rate is over 95.0 percent, the method has great improvement, and unexpected technical effects are obtained.
Compared with the prior art, the invention has the beneficial effects that:
The method takes the ionic liquid as the catalyst, does not need other solvents in the reaction process, saves the cost and is more environment-friendly. In addition, the method of the invention adopts specific ionic liquid as the catalyst, thus not only greatly improving the conversion rate of acetaldehyde, but also having good reaction selectivity, improving the utilization rate of raw materials and having more atomic economy. In addition, the post-treatment of the invention is simple, and the boiling point of the raw material acetaldehyde is low, the boiling point of the product paraldehyde is only 128 ℃, the product can be separated through simple reduced pressure distillation operation, and the ionic liquid catalyst can be recycled, thus being more environment-friendly.
Detailed Description
The following is a detailed description of the present invention by way of examples. In the present invention, the following examples are provided for better illustration of the present invention and are not intended to limit the scope of the present invention. Materials, reagents and the like used in the examples described below are commercially available unless otherwise specified.
Thus, before describing the present invention in detail, it is to be understood that this invention is not limited to the particular illustrated system or process parameters, which may, of course, vary. It is also to be understood that the terminology used herein is for the purpose of describing particular embodiments of the invention only, and is not intended to limit the scope of the invention in any way. The examples used anywhere in this specification (including examples of any terms discussed herein) are illustrative only, and in no way limit the scope and meaning of the invention or any illustrated terms. Also, the present invention is not limited to the various embodiments presented in this specification. Unless defined otherwise, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this invention belongs. In case of conflict, the present document, including definitions, will control.
Example 1
44.0G of acetaldehyde and 3.5g of 1-ethyl-3-butylsulfonic acid imidazole p-toluenesulfonate ionic liquid are added into a stainless steel reaction kettle, and the mixture is stirred at room temperature for reaction for 0.5h.
Then, the reaction liquid is distilled under reduced pressure, unreacted acetaldehyde is recovered, and the product paraldehyde is collected; the remainder is the 1-ethyl-3-butyl sulfonic acid imidazole p-toluenesulfonate ionic liquid, and can be recycled. 41.8g of the product paraldehyde was obtained in a yield of 95.0% and a purity of 99.5% by GC analysis.
Example 2
44.0G of acetaldehyde and 3.5g of 1-ethyl-3-butylsulfonic acid imidazole p-toluenesulfonate ionic liquid are added into a stainless steel reaction kettle, and the mixture is stirred at room temperature for reaction for 1h.
Then, the reaction liquid is distilled under reduced pressure, unreacted acetaldehyde is recovered, and the product paraldehyde is collected; the remainder is the 1-ethyl-3-butyl sulfonic acid imidazole p-toluenesulfonate ionic liquid, and can be recycled. 41.6g of the product paraldehyde was obtained in a yield of 94.5% and a purity of 99.2% by GC analysis.
Example 3
440G of acetaldehyde and 50g of 1-ethyl-3-butyl sulfoimidazole p-toluenesulfonate ionic liquid are added into a stainless steel reaction kettle, and the mixture is stirred and reacted for 0.5h at room temperature.
Then, the reaction liquid is distilled under reduced pressure, unreacted acetaldehyde is recovered, and the product paraldehyde is collected; the remainder is the 1-ethyl-3-butyl sulfonic acid imidazole p-toluenesulfonate ionic liquid, and can be recycled. 421g of the product paraldehyde are obtained in a yield of 95.7% and a purity of 99.5% by GC analysis.
Example 4
220G of acetaldehyde and 15g of 1-ethyl-3-butylsulfonic acid imidazole p-toluenesulfonate ionic liquid are added into a stainless steel reaction kettle, and the mixture is stirred and reacted for 1h at room temperature.
Then, the reaction liquid is distilled under reduced pressure, unreacted acetaldehyde is recovered, and the product paraldehyde is collected; the remainder is the 1-ethyl-3-butyl sulfonic acid imidazole p-toluenesulfonate ionic liquid, and can be recycled. 211g of the product paraldehyde was obtained in a yield of 95.9% and a purity of 99.5% by GC analysis.
Example 5
44.0G of acetaldehyde and 3.5g of 1-ethyl-3-butylsulfonic acid imidazole p-toluenesulfonate ionic liquid are added into a stainless steel reaction kettle, and the mixture is stirred at room temperature for reaction for 0.5h.
After the reaction was completed, n-hexane (50 mL) was added to the reaction vessel, stirred uniformly, the solvent phase was decanted, and analyzed by GC-MS, and as a result, it was shown that the conversion of acetaldehyde was 96.1%.
Example 6
44.0G of acetaldehyde and 3.5g of 1-ethyl-3-butylsulfonic acid imidazole p-toluenesulfonate ionic liquid are added into a stainless steel reaction kettle, and the mixture is stirred at room temperature for reaction for 1h.
After the reaction was completed, n-hexane (50 mL) was added to the reaction vessel, stirred uniformly, the solvent phase was decanted, and analyzed by GC-MS, and as a result, the conversion of acetaldehyde was shown to be 95.7%.
Claims (8)
1. A process for the preparation of paraldehyde comprising the steps of:
Taking acetaldehyde as a raw material, and carrying out polymerization reaction under the catalysis of ionic liquid to prepare paraldehyde; the ionic liquid is 1-ethyl-3-butyl sulfonic acid imidazole p-toluenesulfonate.
2. The process according to claim 1, wherein the polymerization reaction temperature is 20 to 40 ℃.
3. The method according to claim 2, wherein the reaction temperature of the polymerization reaction is room temperature.
4. A process according to any one of claims 1 to 3, wherein the polymerization is carried out for a period of time of from 0.5 to 2 hours.
5. The process according to claim 4, wherein the polymerization time is 0.5 to 1 hour.
6. A method according to any one of claims 1 to 3, wherein the mass ratio of ionic liquid to acetaldehyde is 1 (5-100).
7. The preparation method according to claim 6, wherein the mass ratio of the ionic liquid to the acetaldehyde is 1 (10-20).
8. A method of preparation according to any one of claims 1 to 3, comprising the steps of: adding acetaldehyde and ionic liquid into a reaction kettle, stirring at room temperature for reaction for 0.5-1 hour, recovering acetaldehyde and collecting product paraldehyde by reduced pressure distillation after the reaction is finished, wherein the remainder is the ionic liquid, and the ionic liquid can be recovered for recycling.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202410460621.1A CN118373799A (en) | 2024-04-17 | 2024-04-17 | Preparation method of paraldehyde |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202410460621.1A CN118373799A (en) | 2024-04-17 | 2024-04-17 | Preparation method of paraldehyde |
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| CN118373799A true CN118373799A (en) | 2024-07-23 |
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| CN202410460621.1A Pending CN118373799A (en) | 2024-04-17 | 2024-04-17 | Preparation method of paraldehyde |
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| Country | Link |
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| CN (1) | CN118373799A (en) |
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- 2024-04-17 CN CN202410460621.1A patent/CN118373799A/en active Pending
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