CN104327038A - Method for preparing acetal (ketone) by catalyzing acidic magnetic material containing -SO3H - Google Patents
Method for preparing acetal (ketone) by catalyzing acidic magnetic material containing -SO3H Download PDFInfo
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- CN104327038A CN104327038A CN201410545674.XA CN201410545674A CN104327038A CN 104327038 A CN104327038 A CN 104327038A CN 201410545674 A CN201410545674 A CN 201410545674A CN 104327038 A CN104327038 A CN 104327038A
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- ketone
- acetal
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- 150000002576 ketones Chemical class 0.000 title claims abstract description 35
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 title claims abstract description 32
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 title claims abstract description 30
- 238000000034 method Methods 0.000 title claims abstract description 22
- 230000002378 acidificating effect Effects 0.000 title abstract description 7
- 229910006069 SO3H Inorganic materials 0.000 title abstract 3
- 239000000696 magnetic material Substances 0.000 title abstract 3
- 238000006243 chemical reaction Methods 0.000 claims abstract description 40
- 239000003054 catalyst Substances 0.000 claims abstract description 17
- 238000002360 preparation method Methods 0.000 claims abstract description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 6
- 239000002994 raw material Substances 0.000 claims abstract description 4
- 230000035484 reaction time Effects 0.000 claims abstract description 3
- 239000002253 acid Substances 0.000 claims description 20
- 238000006555 catalytic reaction Methods 0.000 claims description 14
- 230000009466 transformation Effects 0.000 claims description 9
- 150000001299 aldehydes Chemical class 0.000 claims description 8
- 230000008569 process Effects 0.000 claims description 8
- 238000001514 detection method Methods 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 238000004587 chromatography analysis Methods 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 230000008901 benefit Effects 0.000 abstract description 4
- 239000000126 substance Substances 0.000 abstract description 3
- 239000000463 material Substances 0.000 abstract description 2
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 abstract 2
- 238000001816 cooling Methods 0.000 abstract 1
- 238000011031 large-scale manufacturing process Methods 0.000 abstract 1
- 238000000926 separation method Methods 0.000 abstract 1
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 6
- 239000007789 gas Substances 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 4
- 150000002500 ions Chemical class 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 239000012621 metal-organic framework Substances 0.000 description 4
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 230000003197 catalytic effect Effects 0.000 description 3
- TVEOIQKGZSIMNG-UHFFFAOYSA-N hydron;1-methyl-1h-imidazol-1-ium;sulfate Chemical compound OS([O-])(=O)=O.C[NH+]1C=CN=C1 TVEOIQKGZSIMNG-UHFFFAOYSA-N 0.000 description 3
- 239000002608 ionic liquid Substances 0.000 description 3
- -1 phenyl aldehyde Chemical class 0.000 description 3
- 238000004064 recycling Methods 0.000 description 3
- QPYKYDBKQYZEKG-UHFFFAOYSA-N 2,2-dimethylpropane-1,1-diol Chemical compound CC(C)(C)C(O)O QPYKYDBKQYZEKG-UHFFFAOYSA-N 0.000 description 2
- 125000004825 2,2-dimethylpropylene group Chemical group [H]C([H])([H])C(C([H])([H])[H])(C([H])([H])[*:1])C([H])([H])[*:2] 0.000 description 2
- BXRFQSNOROATLV-UHFFFAOYSA-N 4-nitrobenzaldehyde Chemical compound [O-][N+](=O)C1=CC=C(C=O)C=C1 BXRFQSNOROATLV-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000011831 acidic ionic liquid Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- JARKCYVAAOWBJS-UHFFFAOYSA-N hexanal Chemical compound CCCCCC=O JARKCYVAAOWBJS-UHFFFAOYSA-N 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 238000005935 nucleophilic addition reaction Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000000523 sample Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- KJUGUADJHNHALS-UHFFFAOYSA-N 1H-tetrazole Chemical class C=1N=NNN=1 KJUGUADJHNHALS-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- 239000007848 Bronsted acid Substances 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 239000002638 heterogeneous catalyst Substances 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 239000002122 magnetic nanoparticle Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 238000012805 post-processing Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D319/04—1,3-Dioxanes; Hydrogenated 1,3-dioxanes
- C07D319/06—1,3-Dioxanes; Hydrogenated 1,3-dioxanes not condensed with other rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/48—Preparation of compounds having groups
- C07C41/50—Preparation of compounds having groups by reactions producing groups
- C07C41/56—Preparation of compounds having groups by reactions producing groups by condensation of aldehydes, paraformaldehyde, or ketones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/30—Compounds having groups
- C07C43/303—Compounds having groups having acetal carbon atoms bound to acyclic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
- C07D317/14—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D317/16—Radicals substituted by halogen atoms or nitro radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D319/04—1,3-Dioxanes; Hydrogenated 1,3-dioxanes
- C07D319/08—1,3-Dioxanes; Hydrogenated 1,3-dioxanes condensed with carbocyclic rings or ring systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
The invention discloses a method for preparing acetal (ketone) by catalyzing an acidic magnetic material containing -SO3H, which belongs to the technical field of chemical material and preparation thereof. According to the invention, mol ratio of aldehyde or ketone to alcohol used in the preparation method is 1: (1-5), mole of the acidic magnetic material catalyst accounts for 8-10% of that of the used aldehyde or ketone by calculating -SO3H, reaction temperature is 110 DEG C, the reaction time is 0.5-3 hours, the reaction pressure is one atmospheric pressure, a cooling step is carried out to room temperature after reaction is completed, the catalyst is sucked by a magnet, and the conversion rate, selectivity and acetal(ketone) yield of the reaction raw material are detected by a reaction solution through a gas chromatograph. Compared with the preparation method of other catalysts, the method has the advantages of high reaction selectivity, simple separation of the catalyst and the product, the catalyst enables cycle usage without any treatment, the operation of whole preparation process is simple, the economic benefit is high, and the method is convenient for industrial large scale production.
Description
Technical field
The invention belongs to chemical material and preparing technical field thereof, be specifically related to a kind of containing-SO
3the method of acetal (ketone) is prepared in the acid magneticsubstance catalysis of H.
Background technology
Acetal (ketone) is the important intermediate in chemical industry, is usually used in the protection of aldehydes or ketones, is even used as special reaction solvent.The method that tradition prepares acetal (ketone) is carried out under mineral acid (sulfuric acid, hydrochloric acid, phosphoric acid etc.) catalysis, but this method to there is side reaction many, equipment corrosion is serious, and product purity is not high, and aftertreatment is more loaded down with trivial details, and produces three-waste pollution.Therefore, develop acetal (ketone) green, efficiently, can be recycled and cause the great interest of chemists with the segregative new catalyst of product.
In recent years, acidic ion liquid, particularly bronsted acid ionic liquid owing to having green non-pollution, to organicly there is good solubility, the acidic site be evenly distributed with mineral compound, be easy to product and be separated and can be recycled etc. advantage and being used in the preparation of acetal (ketone).Such as applicant uses the salt acidic ionic liquid of N-methylimidazolium hydrogen sulphate as catalyzer, can nucleophilic addition occur between catalysis aldehydes or ketones and alcohol effectively and then prepare acetal (ketone) under condition of no solvent.Due to catalyzer and acetal (ketone) mutual solubility poor, only need just can realize being separated of product and catalyzer by simple separatory, and the catalyzer after dewatering can recycle.Acidity but due to the salt acidic ionic liquid of N-methylimidazolium hydrogen sulphate is more weak, in preparation process, (method [P] of acetal or ketal is prepared in the catalysis of a kind of N-methylimidazolium hydrogen sulphate ionic liquid to its large usage quantity, Yue Caibo, Yi Tingfeng. application number: 200810243309.8).In order to improve the acidity of acidic ion liquid and then reduce its consumption, old waiting quietly uses containing-SO
3the sulfonic acid funtionalized ionic liquid of H is as catalyzer, preparation process (the research [J] of functionalized ion liquid catalytic performance in acetal (ketone) reaction of acetal (ketone) can be realized when its consumption is only 1%, dragon Venus, Zhao Yingwei, Liu Jianhua, Li Zhen, Chen Jing. Journal of Molecular Catalysis, 2008,22 (3): 199-204).
In addition, in order to reduce the separating difficulty between acetal (ketone) and catalyzer further, thus simplify post-processing operation, simultaneously also in order to reduce the number of dropouts of catalyzer in recycling.Applicant employs a kind of containing-SO
3the metal organic framework compound of H is as heterogeneous catalyst, (method [P] of acetal or ketal is prepared in a kind of metal organic framework compound catalysis to achieve the reaction preparing acetal (ketone) under condition of no solvent, Yue Caibo, Yi Tingfeng. application number: 201310042438.1).
Although above-mentioned metal organic framework compound catalyzer catalysis efficiently can prepare acetal (ketone), because its thermostability is poor, structure is easily caved in the reaction, thus affects its catalytic effect and recycle performance.In addition, prepare the raw material of acidic ion liquid and metal organic framework compound costly, be difficult to be used on a large scale in suitability for industrialized production.
Summary of the invention
The object of the invention is to overcome existing catalysis, to prepare catalyzer usage quantity in acetal (ketone) technology large and recycle that middle number of dropouts is large, catalyst preparing price is higher and the shortcoming such as last handling process is complicated, and provide a kind of acidity higher, inexpensive and preparation is simple containing-SO
3the method of acetal (ketone) is prepared in the acid magneticsubstance catalysis of H.
The skeleton symbol of acid magnetic catalyst used in the present invention is:
One of the present invention contains-SO
3the method particular content that acetal (ketone) is prepared in the acid magneticsubstance catalysis of H is as follows: the mol ratio preparing aldehydes or ketones used and alcohol in acetal (ketone) reaction is 1:(1 ~ 5), with-SO
3the molar weight that H calculates acid magnetic catalyst used is 8 ~ 10% of aldehydes or ketones used, temperature of reaction is 110 DEG C, reaction times is 0.5 ~ 3h, reaction pressure is a normal atmosphere, room temperature is cooled to after reaction, with magnet sucking-off catalyzer, reaction solution is by the productive rate of the transformation efficiency of gas chromatographic analysis detection reaction raw material, selectivity and acetal (ketone).The catalyzer of sucking-off is directly used in without the need to any process and reacts next time, and can reuse at least 7 times, its products collection efficiency does not have obvious reduction.
Described aldehydes or ketones is selected from
In one; Wherein: a is the integer between 0 ~ 6, R is the one in alkyl, alkoxyl group, halogen, hydroxyl.
Described alcohol is selected from
In one; Wherein: b is the integer between 1 ~ 5, c is the integer between 0 ~ 4.
The preparation method of acid magnetic catalyst used in the present invention, see pertinent literature (Sulfonic acid-functionalized silica-coated magnetic nanoparticles as an efficient reusable catalyst for the synthesis of 1-substituted 1H-tetrazoles under solvent-free conditions [J], Hossein Naeimi and Samaneh Mohamadabadi.Dalton Transactions, 2014,43:12967 ~ 12973).
The present invention, compared with the preparation method of other catalyzer, has the following advantages:
1, catalyst activity is good, and reaction preference is high and environmentally friendly;
2, catalyzer does not need to carry out any process recycling in process;
3, catalyzer and product mutual solubility poor, simple, the convenient and easy handling of sepn process;
4, whole building-up process economy, efficient, is convenient to industrialization scale operation.
Embodiment
Substantive features of the present invention and unusual effect can be embodied from following embodiment; but they do not impose any restrictions the present invention; those skilled in the art's content according to the present invention makes some nonessential improvement and adjustment, all belongs to protection scope of the present invention.
Embodiment 1: acid to 10mmol butyraldehyde-n, 10mmol 1,3-PD and 2.72g magneticsubstance is joined in the 25ml single port bottle with stirrer and prolong.At 110 DEG C, vigorous stirring reaction 0.75h, is cooled to room temperature after reaction, with magnet sucking-off catalyzer.The transformation efficiency that reaction solution gas chromatographic detection obtains butyraldehyde-n is 97%, and the selectivity of product butyraldehyde-n 1,3-PD acetal is 100%, and calculating its productive rate is 97%, and catalyzer uses without cycle for the treatment of.
Embodiment 2: acid to 10mmol phenyl aldehyde, 15mmol 1,3-PD and 3.04g magneticsubstance is joined in the 50ml single port bottle with stirrer and prolong.At 110 DEG C, vigorous stirring reaction 1.5h, is cooled to room temperature after reaction, with magnet sucking-off catalyzer.The transformation efficiency that reaction solution gas chromatographic detection obtains phenyl aldehyde is 93%, and the selectivity of product phenyl aldehyde 1,3-PD acetal is 100%, and calculating its productive rate is 93%, and catalyzer uses without cycle for the treatment of.
Embodiment 3: acid to 10mmol paranitrobenzaldehyde, 25mmol ethylene glycol and 2.41g magneticsubstance is joined in the 50ml single port bottle with stirrer and prolong.At 110 DEG C, vigorous stirring reaction 2h, is cooled to room temperature after reaction, with magnet sucking-off catalyzer.The transformation efficiency that reaction solution gas chromatographic detection obtains paranitrobenzaldehyde is 96%, and the selectivity of product paranitrobenzaldehyde-Glycol Acetal is 100%, and calculating its productive rate is 96%, and catalyzer uses without cycle for the treatment of.
Embodiment 4: acid to 10mmol pimelinketone, 15mmol 2,2-dimethyl propylene glycol and 2.72g magneticsubstance is joined in the 50ml single port bottle with stirrer and prolong.At 110 DEG C, vigorous stirring reaction 2h, is cooled to room temperature after reaction, with magnet sucking-off catalyzer.The transformation efficiency that reaction solution gas chromatographic detection obtains pimelinketone is 90%, and the selectivity of product pimelinketone 2,2-dimethyl propanediol Ketal is 100%, and calculating its productive rate is 90%, and catalyzer uses without cycle for the treatment of.
Embodiment 5: acid to 10mmol n-hexyl aldehyde, 50mmol methyl alcohol and 3.04g magneticsubstance is joined in the 100ml single port bottle with stirrer and prolong.At 110 DEG C, vigorous stirring reaction 3h, is cooled to room temperature after reaction, with magnet sucking-off catalyzer.The transformation efficiency that reaction solution gas chromatographic detection obtains n-hexyl aldehyde is 88%, and the selectivity of product n-hexyl aldehyde-methyl alcohol acetal is 100%, and calculating its productive rate is 88%, and catalyzer uses without cycle for the treatment of.
Embodiment 6: with embodiment 1 for probe reaction, make the active replica test of the acid magneticsubstance of catalysts, catalyzer reuses 7 times, and the transformation efficiency of butyraldehyde-n and the selectivity of product butyraldehyde-n 1,3-PD acetal, yield data are in table 1.
The active revision test result of table 1. catalyzer in butyraldehyde-n and 1,3-PD aldolization
Embodiment 7: with embodiment 4 for probe reaction, make the active replica test of the acid magneticsubstance of catalysts, catalyzer reuses 7 times, and the transformation efficiency of pimelinketone and the selectivity of product pimelinketone 2,2-dimethyl propanediol Ketal, yield data are in table 2.
The active revision test result of table 2. catalyzer in pimelinketone and 2,2-dimethyl propylene glycol ketal reaction
As can be seen from table 1 and 2: in the present invention, this acid magnetic catalyst is recycling in process, and its catalytic capability almost remains unchanged.Can prove that it is prepared in the nucleophilic addition of acetal (ketone) can be reused at least 7 times in catalysis thus.
Claims (2)
1. one kind contains-SO
3the method of acetal (ketone) is prepared in the acid magneticsubstance catalysis of H, it is characterized in that, in described preparation method, the mol ratio of aldehydes or ketones used and alcohol is 1:1 ~ 5, with-SO
3the molar weight that H calculates acid magnetic catalyst used is 8 ~ 10% of aldehydes or ketones used, temperature of reaction is 110 DEG C, reaction times is 0.5 ~ 3h, reaction pressure is a normal atmosphere, room temperature is cooled to after reaction, with magnet sucking-off catalyzer, reaction solution is by the productive rate of the transformation efficiency of gas chromatographic analysis detection reaction raw material, selectivity and acetal (ketone);
Described aldehydes or ketones is selected from
In one; Wherein: a is the integer between 0 ~ 6, R is the one in alkyl, alkoxyl group, halogen, hydroxyl;
Described alcohol is selected from
In one; Wherein: b is the integer between 1 ~ 5, c is the integer between 0 ~ 4;
The skeleton symbol of described acid magnetic catalyst is:
2. as claimed in claim 1 a kind of containing-SO
3the method of acetal (ketone) is prepared in the acid magneticsubstance catalysis of H, it is characterized in that, the catalyzer after described sucking-off is directly used in without the need to any process and reacts next time, can reuse at least 7 times.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201410545674.XA CN104327038B (en) | 2014-10-15 | 2014-10-15 | A kind of containing-SO 3the method of acetal (ketone) is prepared in the acid magneticsubstance catalysis of H |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201410545674.XA CN104327038B (en) | 2014-10-15 | 2014-10-15 | A kind of containing-SO 3the method of acetal (ketone) is prepared in the acid magneticsubstance catalysis of H |
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| Publication Number | Publication Date |
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| CN104327038A true CN104327038A (en) | 2015-02-04 |
| CN104327038B CN104327038B (en) | 2016-04-27 |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105859496A (en) * | 2016-04-19 | 2016-08-17 | 合肥工业大学 | Green synthesis method of acetal-type or ketal-type compound |
| CN112138717A (en) * | 2020-09-25 | 2020-12-29 | 常州大学 | Preparation method and application of vinyl pyrrolidone salt magnetic nanoparticles |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103113347A (en) * | 2013-02-04 | 2013-05-22 | 安徽工业大学 | Method for preparing acetal or ketal under catalytic action of metal-organic frameworks |
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2014
- 2014-10-15 CN CN201410545674.XA patent/CN104327038B/en not_active Expired - Fee Related
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103113347A (en) * | 2013-02-04 | 2013-05-22 | 安徽工业大学 | Method for preparing acetal or ketal under catalytic action of metal-organic frameworks |
Non-Patent Citations (1)
| Title |
|---|
| HOSSEIN NAEIMI，ET AL.，: "Sulfonic acid-functionalized silica-coated magnetic nanoparicles as an efficient reusable catalyst for the synthesis of 1-substituted 1H-tetrazoles under solvent-free conditions", 《DALTON TRANSACTIONS》 * |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105859496A (en) * | 2016-04-19 | 2016-08-17 | 合肥工业大学 | Green synthesis method of acetal-type or ketal-type compound |
| CN112138717A (en) * | 2020-09-25 | 2020-12-29 | 常州大学 | Preparation method and application of vinyl pyrrolidone salt magnetic nanoparticles |
| CN112138717B (en) * | 2020-09-25 | 2023-09-22 | 常州大学 | Preparation method and application of vinyl pyrrolidone salt magnetic nanoparticles |
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