CN103910652A - Method for aqueous-phase synthesizing cyan-substituted styrene compounds - Google Patents
Method for aqueous-phase synthesizing cyan-substituted styrene compounds Download PDFInfo
- Publication number
- CN103910652A CN103910652A CN201410163874.9A CN201410163874A CN103910652A CN 103910652 A CN103910652 A CN 103910652A CN 201410163874 A CN201410163874 A CN 201410163874A CN 103910652 A CN103910652 A CN 103910652A
- Authority
- CN
- China
- Prior art keywords
- water
- substituted styrene
- reaction
- aromatic aldehyde
- cyan
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 238000000034 method Methods 0.000 title claims abstract description 14
- 125000003011 styrenyl group Chemical class [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 title abstract 3
- 239000008346 aqueous phase Substances 0.000 title abstract 2
- 230000002194 synthesizing effect Effects 0.000 title abstract 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 32
- 238000006243 chemical reaction Methods 0.000 claims abstract description 19
- SUSQOBVLVYHIEX-UHFFFAOYSA-N phenylacetonitrile Chemical compound N#CCC1=CC=CC=C1 SUSQOBVLVYHIEX-UHFFFAOYSA-N 0.000 claims abstract description 12
- 150000003934 aromatic aldehydes Chemical class 0.000 claims abstract description 11
- 239000002904 solvent Substances 0.000 claims abstract description 8
- 238000006482 condensation reaction Methods 0.000 claims abstract description 5
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 27
- -1 styrene compound Chemical class 0.000 claims description 19
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Natural products C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 18
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 14
- 239000007787 solid Substances 0.000 claims description 6
- 239000002994 raw material Substances 0.000 claims description 3
- 238000001914 filtration Methods 0.000 claims description 2
- 239000013049 sediment Substances 0.000 claims description 2
- 238000003756 stirring Methods 0.000 claims description 2
- 239000000047 product Substances 0.000 abstract description 11
- 229910052799 carbon Inorganic materials 0.000 abstract description 6
- 230000009286 beneficial effect Effects 0.000 abstract description 2
- 230000018044 dehydration Effects 0.000 abstract description 2
- 238000006297 dehydration reaction Methods 0.000 abstract description 2
- 239000000463 material Substances 0.000 abstract description 2
- 239000002244 precipitate Substances 0.000 abstract 2
- 230000007935 neutral effect Effects 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 description 8
- 238000001556 precipitation Methods 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 238000000967 suction filtration Methods 0.000 description 4
- 239000000126 substance Substances 0.000 description 3
- CSDSSGBPEUDDEE-UHFFFAOYSA-N 2-formylpyridine Chemical compound O=CC1=CC=CC=N1 CSDSSGBPEUDDEE-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000007810 chemical reaction solvent Substances 0.000 description 2
- 230000002209 hydrophobic effect Effects 0.000 description 2
- 231100000252 nontoxic Toxicity 0.000 description 2
- 230000003000 nontoxic effect Effects 0.000 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
- 238000006053 organic reaction Methods 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- BGUWFUQJCDRPTL-UHFFFAOYSA-N pyridine-4-carbaldehyde Chemical compound O=CC1=CC=NC=C1 BGUWFUQJCDRPTL-UHFFFAOYSA-N 0.000 description 2
- 239000012429 reaction media Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 230000009466 transformation Effects 0.000 description 2
- BKUSTPSDMHTLDC-UHFFFAOYSA-N O=Cc1cc(C2[O]=C2)c[s]1 Chemical compound O=Cc1cc(C2[O]=C2)c[s]1 BKUSTPSDMHTLDC-UHFFFAOYSA-N 0.000 description 1
- HUMNYLRZRPPJDN-UHFFFAOYSA-N O=Cc1ccccc1 Chemical compound O=Cc1ccccc1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 1
- 239000000809 air pollutant Substances 0.000 description 1
- 231100001243 air pollutant Toxicity 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 125000000058 cyclopentadienyl group Chemical group C1(=CC=CC1)* 0.000 description 1
- 125000004663 dialkyl amino group Chemical group 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- ZSWFCLXCOIISFI-UHFFFAOYSA-N endo-cyclopentadiene Natural products C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000003344 environmental pollutant Substances 0.000 description 1
- CNUDBTRUORMMPA-UHFFFAOYSA-N formylthiophene Chemical compound O=CC1=CC=CS1 CNUDBTRUORMMPA-UHFFFAOYSA-N 0.000 description 1
- 230000007773 growth pattern Effects 0.000 description 1
- 238000013332 literature search Methods 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 231100000719 pollutant Toxicity 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- YAYGSLOSTXKUBW-UHFFFAOYSA-N ruthenium(2+) Chemical compound [Ru+2] YAYGSLOSTXKUBW-UHFFFAOYSA-N 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Abstract
The invention discloses a method for aqueous-phase synthesizing cyan-substituted styrene compounds. The cyan-substituted styrene compounds are synthesized by taking water as a solvent and taking benzyl cyanide and aromatic aldehyde as materials through noevenagel condensation reaction, wherein the aromatic aldehyde is selected from formula shown in the specification. According to the invention, the reaction is carried out at a room temperature; relative to other high-temperature reactions in the prior art, not only is yield improved, but also energy resources are saved, and therefore, the method is beneficial to low-carbon harmless green engineering. White spherical precipitates are generated after reaction and dehydration, and the white spherical precipitates are washed in water to neutral, and dried to obtain a target product; and besides, the method is simple in synthetic steps, easy for treatment and high in yield.
Description
One, technical field
The present invention relates to a kind of water phase synthesis method, specifically a kind of method that the water of high yield synthesizes cyano group substituted styrene compound under room temperature environment.
Two, background technology
21 century, the problem of the Sustainable development of society and related ecology thereof, environment, resource, economic dispatch aspect more and more becomes the focus of international concern, the height of referred development strategy.Country constantly puts into effect the regulation of protection of the environment, impels chemical circles attention to be focused on to the generation aspect of stopping or reduce waste from origin, i.e. the prevention of original pollution, and be not the vicious cycle process for the treatment of after pollution.The Eleventh Five-Year Plan period energy consumption per unit reduces by 20% left and right, total emissions of major pollutants reduces 10%.The major action that this is implement scientific view of development, build a harmonious socialist society; It is the inevitable choice of building a resource-conserving and environment-friendly society; Be to promote economic restructuring, change the only way of growth pattern; It is the inevitable requirement of safeguarding Chinese nation's long-term interest.
Comply with this new development trend, a new chemical subdiscipline-Green Chemistry is arisen at the historic moment.The green synthetic target of pursuing is to realize highly selective, chemical reaction efficiently, and few by product, zero release, reaches the reaction of Atom economy then.Obviously relatively stoichiometric reaction, highly selective, efficient water react more meet green synthetic basic demand.
In traditional organic reaction, organic solvent is the most frequently used reaction medium, and this is mainly because they can be dissolved with organic compounds well, but the toxicity of organic solvent makes it again to become environmentally harmful factor with being difficult to reclaim.Nowadays, the some areas such as China northeast, North China and south China meet with haze weather continuously.It is that social fossil energy expenditure increases the Air Pollutant Emission causing and increases year by year that haze weather increases topmost reason.In the face of the haze shade of can't get rid of, the discharge of taking measures to reduce atmospheric polluting material is extremely urgent.Therefore the organic reaction of, carrying out under solvent-free existence and by water as reaction medium become development Clean synthesis important channel.Although poorly soluble in water of most of organic compound, and much reagent can decompose in water, and water has its unique superiority as reaction solvent.Because water is natural abundance the highest " solvent " on the earth, inexpensive, nontoxic, do not endanger environment.In addition, the distinctive hydrophobic effect of water solvent is very useful to some important organic transformation, sometimes can improve speed of reaction and selectivity, and the chemical reaction in life entity carries out mostly in water still more.
Applicant has carried out following literature search to the application's theme:
1, www.google.com net result for retrieval: (2014/4/15)
2, CNKI result for retrieval: (2014/4/15)
Retrieval mode one:
Section name-cyano group substituted styrene compound: without pertinent literature.
The synthetic cyano group substituted styrene compound of section name-water: without document.
Retrieval mode two:
In full-cyano group substituted styrene compound: without pertinent literature.
In full-water synthesizes cyano group substituted styrene compound: without pertinent literature.
Retrieval mode three:
Theme-cyano group substituted styrene compound: without pertinent literature.
Theme-water synthesizes cyano group substituted styrene compound: without document.
Retrieval mode four:
Keyword-cyano group substituted styrene compound: without document.
Keyword-water synthesizes cyano group substituted styrene compound: without document.
Three, summary of the invention
The present invention aims to provide a kind of method that water high yield is synthesized cyano group substituted styrene compound under room temperature environment, taking water as solvent, taking benzyl cyanide and aromatic aldehyde as raw material, by the synthetic cyano group substituted styrene compound of Knoevnagel condensation reaction (Ke Laowengaier condensation reaction), reaction yield is all higher than 90%.
Technical solution problem of the present invention adopts following technical scheme:
The method of the synthetic cyano group substituted styrene compound of water of the present invention, is taking water as solvent, taking benzyl cyanide and aromatic aldehyde as raw material, by the synthetic cyano group substituted styrene compound of Ke Laowengaier condensation reaction;
Described aromatic aldehyde is selected from
The step of the method for the synthetic cyano group substituted styrene compound of water of the present invention is as follows:
Aromatic aldehyde and benzyl cyanide are scattered in water, and stirring at room temperature is even, then drips the NaOH solution of mass concentration 5%, under room temperature, reacts 10-12 hour, generates solid sediment, and reaction finishes rear filtration, is washed to neutrality, after being dried, obtains target product; The mol ratio of aromatic aldehyde, benzyl cyanide and NaOH is 1:1:1.5.
The structural formula of cyano group substituted styrene compound prepared by the present invention is:
Concrete synthetic route is as follows:
Compared with the prior art, beneficial effect of the present invention is embodied in:
1, the present invention is using water as reaction solvent, inexpensive, nontoxic, do not endanger environment.
2, the present invention's reaction is at room temperature carried out, with respect to the pyroreaction of other prior arts
[1-2], both improved productive rate, save again the energy, be conducive to the innoxious green engineering of low-carbon (LC).
3, after reaction dehydration, generate white nodular precipitation, be washed to neutrality, dry, obtain target product, synthesis step is simple, is easy to process, and productive rate is high.
4, the distinctive hydrophobic effect of water solvent is very useful to some important organic transformation, has effectively improved speed of reaction and reaction preference.
[1]M.Judith?Percino,Víctor?M.Chapela,Ling-Fa?Montiel,Enrique?Pérez-Gutiérrez,José?Luis?Maldonado,Spectroscopic?characterization?of?halogen-and?cyano-substituted?pyridinevinylenes?synthesized?without?catalyst?or?solvent,Chemical?Papers,2010；64(3),360-367.
[2]Hung?Wai?Cheung,Juan?Li,Wenxu?Zheng,Zhongyuan?Zhou,Yu?Hin?Chiu,Zhenyang?Lin,Chak?Po?Lau,Dialkylamino?cyclopentadienyl?ruthenium(ii)complex-catalyzedα-alkylation?of?arylaceto-nitriles?with?primary?alcohols,Dalton?Transactions,2010；39(1),265-274.
Four, brief description of the drawings
Fig. 1 is the hydrogen spectrogram of target product Y1.
Fig. 2 is the carbon spectrogram of target product Y1.
Fig. 3 is the hydrogen spectrogram of target product Y2.
Fig. 4 is the carbon spectrogram of target product Y2.
Fig. 5 is the hydrogen spectrogram of target product Y3.
Fig. 6 is the carbon spectrogram of target product Y3.
Fig. 7 is the hydrogen spectrogram of target product Y4.
Fig. 8 is the carbon spectrogram of target product Y4.
Five, embodiment
1, the preparation of compound Y1:
Phenyl aldehyde 0.530g (5mmol), benzyl cyanide 0.585g (5mmol) and 30mL water are placed in to 100mL round-bottomed flask, under whipped state, dropwise add the aqueous sodium hydroxide solution of 6mL mass concentration 5%, dropwise room temperature reaction 12h, obtain white solid precipitation, suction filtration, is washed to neutrality, dry, obtain target compound 0.965g, productive rate 94.146%.
1H?NMR(DMSO-d
6,400MHz,ppm)δ:7.45-7.57(m,6H),7.78(d,J＝7.2Hz,2H),7.95(d,J＝7.6Hz,2H),8.07(s,1H).
13C?NMR(DMSO-d
6,100MHz,ppm)δ:110.33,117.86,125.77,128.91,129.10,129.15,129.25,130.57,133.70,133.74,142.91。
2, the preparation of compound Y2:
4-pyridylaldehyde 0.535g (5mmol), benzyl cyanide 0.585g (5mmol) and 30mL water are placed in to 100mL round-bottomed flask, under whipped state, dropwise add the aqueous sodium hydroxide solution of 6mL mass concentration 5%, dropwise room temperature reaction 12h, obtain white solid precipitation, suction filtration, is washed to neutrality, dry, obtain target compound 0.978g, productive rate 94.951%.
1H?NMR(DMSO-d
6,400MHz,ppm)δ:7.50-7.58(m,3H),7.82(d,J＝6.4Hz,4H),8.11(s,1H),8.76(d,J＝5.6Hz,2H).
13C?NMR(DMSO-d
6,100MHz,ppm)δ:114.70,116.97,122.62,126.13,129.27,130.07,132.93,140.20,140.74,150.43。
3, the preparation of compound Y3:
2-pyridylaldehyde 0.535g (5mmol), benzyl cyanide 0.585g (5mmol) and 30mL water are placed in to 100mL round-bottomed flask, under whipped state, dropwise add the aqueous sodium hydroxide solution of 6mL mass concentration 5%, dropwise room temperature reaction 12h, obtain white solid precipitation, suction filtration, is washed to neutrality, dry, obtain target compound 0.970g, productive rate 94.174%.
1H?NMR(DMSO-d
6,400MHz,ppm)δ:7.47-7.57(m,4H),7.78(d,J＝7.6Hz,1H),7.84(d,J＝7.6Hz,2H),7.95-7.99(m,1H),8.05(s,1H),8.75(d,J＝4.4Hz,1H).
13C?NMR(DMSO-d
6,100MHz,ppm)δ:112.99,117.31,124.81,125.96,126.17,129.16,129.66,133.86,137.21,140.83,149.58,151.56。
4, the preparation of compound Y4:
2 thiophene carboxaldehyde 0.559g (5mmol), benzyl cyanide 0.585g (5mmol) and 30mL water are placed in to 100mL round-bottomed flask, under whipped state, drip the aqueous sodium hydroxide solution of 6mL mass concentration 5%, dropwise rear room temperature reaction 12h, obtain yellow solid precipitation, suction filtration, is washed to neutrality, dry, obtain target compound 0.975g, productive rate 92.417%.
1H?NMR(DMSO-d
6,400MHz,ppm)δ:7.26-7.28(m,1H),7.41-7.44(m,1H),7.49-7.53(m,2H),7.73(d,J＝7.6Hz,2H),7.77(d,J＝3.6Hz,1H),7.92(d,J＝4.8Hz,1H),8.31(s,1H).
13C?NMR(DMSO-d
6,100MHz,ppm)δ:106.20,117.99,125.41,127.98,128.87,129.16,131.50,133.35,134.52,135.59,137.52。
Claims (3)
1. a method for the synthetic cyano group substituted styrene compound of water, is characterized in that:
Taking water as solvent, taking benzyl cyanide and aromatic aldehyde as raw material, by the synthetic cyano group substituted styrene compound of Ke Laowengaier condensation reaction;
Described aromatic aldehyde is selected from
2. method according to claim 1, is characterized in that operating according to the following steps:
Aromatic aldehyde and benzyl cyanide are scattered in water, and stirring at room temperature is even, then drips NaOH solution, under room temperature, reacts 10-12 hour, generates solid sediment, and reaction finishes rear filtration, is washed to neutrality, after being dried, obtains target product; The mol ratio of aromatic aldehyde, benzyl cyanide and NaOH is 1:1:1.5.
3. method according to claim 2, is characterized in that:
The mass concentration of NaOH solution is 5%.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201410163874.9A CN103910652B (en) | 2014-04-22 | 2014-04-22 | A kind of method of synthesis in water cyano group substituted styrene compound |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201410163874.9A CN103910652B (en) | 2014-04-22 | 2014-04-22 | A kind of method of synthesis in water cyano group substituted styrene compound |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN103910652A true CN103910652A (en) | 2014-07-09 |
| CN103910652B CN103910652B (en) | 2016-04-27 |
Family
ID=51036703
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201410163874.9A Expired - Fee Related CN103910652B (en) | 2014-04-22 | 2014-04-22 | A kind of method of synthesis in water cyano group substituted styrene compound |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN103910652B (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104360512A (en) * | 2014-12-01 | 2015-02-18 | 合肥鑫晟光电科技有限公司 | Electric control fluorescent liquid crystal light valve and display equipment thereof |
| CN105111102A (en) * | 2015-07-20 | 2015-12-02 | 浙江工业大学 | Cyanostilbene derivative, preparation method and application thereof |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2006206548A (en) * | 2005-01-31 | 2006-08-10 | Kyoto Univ | Method for producing nitrile compound |
| CN103710030A (en) * | 2013-11-27 | 2014-04-09 | 合肥工业大学 | Cyano group-substituted stilbene-type liquid crystal material and its preparation technology and use |
-
2014
- 2014-04-22 CN CN201410163874.9A patent/CN103910652B/en not_active Expired - Fee Related
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2006206548A (en) * | 2005-01-31 | 2006-08-10 | Kyoto Univ | Method for producing nitrile compound |
| CN103710030A (en) * | 2013-11-27 | 2014-04-09 | 合肥工业大学 | Cyano group-substituted stilbene-type liquid crystal material and its preparation technology and use |
Non-Patent Citations (2)
| Title |
|---|
| ILKER ESEN等: ""Long chain dicationic phase transfer catalystss in the condensation reactions of aromatic aldehydes in water under ultrasonic effect"", 《BULL.KOREAN CHEM.SOC.》, vol. 31, no. 8, 31 December 2010 (2010-12-31), pages 2289 - 2292 * |
| 姜恒等: "室温水介质中氟化钾催化的Knoevenagel反应", 《化学研究》, vol. 18, no. 3, 30 September 2007 (2007-09-30), pages 27 * |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104360512A (en) * | 2014-12-01 | 2015-02-18 | 合肥鑫晟光电科技有限公司 | Electric control fluorescent liquid crystal light valve and display equipment thereof |
| CN104360512B (en) * | 2014-12-01 | 2017-03-22 | 合肥鑫晟光电科技有限公司 | Electric control fluorescent liquid crystal light valve and display equipment thereof |
| CN105111102A (en) * | 2015-07-20 | 2015-12-02 | 浙江工业大学 | Cyanostilbene derivative, preparation method and application thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| CN103910652B (en) | 2016-04-27 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| RekhaáBoruah et al. | Pd (OAc) 2 in WERSA: a novel green catalytic system for Suzuki–Miyaura cross-coupling reactions at room temperature | |
| CN101830920B (en) | Prolinol derivative induced chiral MOFs material with asymmetric catalysis | |
| CN102558572B (en) | Method for preparing xylogen acetylated derivative in ionic liquid solvent | |
| CN104326909A (en) | Methods for preparation of alpha, alpha-dimethyl-4-(2-haloethyl) phenyl acetate and synthesis of bilastine | |
| CN107790178B (en) | Based on three (2,4,6- trimethoxyphenyl) phosphine ionic-liquid catalysts and preparation method thereof | |
| CN103910652A (en) | Method for aqueous-phase synthesizing cyan-substituted styrene compounds | |
| CN102731333B (en) | Method for preparing tetracaine | |
| CN102190683B (en) | A kind of phosphorous anion ionic liquid and preparation method thereof | |
| CN105503677B (en) | A kind of environmental protection, high performance vulcanization crosslinking agent 1,6 2（The sulphur of N, N dibenzyl amino formyl two）The preparation method of hexane | |
| CN102276608A (en) | Method for synthesizing tetrahydro-beta-carboline diketopiperazine compound | |
| CN105348037A (en) | Synthetic method of directly coupling aryl halide by aromatic hydrocarbon Grignard reagent in the presence of recycled modified palladium-charcoal | |
| CN105218560B (en) | The synthesis technique of the chlorothiophene of 7 bromine 4 simultaneously [3,2 D] pyrimidine | |
| CN104624242A (en) | Synthetic biodiesel acidic ionic liquid immobilized catalyst and preparation method thereof | |
| CN104262127A (en) | Brush-type difluoro monomer and synthetic method thereof | |
| CN103961978B (en) | A kind of method containing tertiary amine groups and itrile group pyridines functionalized ion liquid capture sulfur dioxide | |
| CN101143862B (en) | Ionic compound containing chiral amine-thiourea (urea) and its preparation method and application | |
| CN102822161A (en) | Method for producing optically active n-monoalkyl-3-hydroxy-3-arylpropylamine compound | |
| CN109574938B (en) | Method for synthesizing rosuvastatin sodium | |
| CN105498451A (en) | Ether-based bis-imidazole ionic liquid binary system used for absorbing SO2, and preparation method and application method thereof | |
| CN110283149A (en) | Biomass diamines, its salt and its preparation based on furylamine and levulic acid | |
| CN103396347B (en) | Method for synthesizing p-hydroxyl thiobenzamide | |
| CN109081817A (en) | CuI/ ionic liquid normal temperature and pressure catalysis converts CO2The method for synthesizing 1,3- oxazolidine -2- ketone compounds | |
| CN103772269A (en) | Controllable preparation method of carbazole bromo-compound | |
| CN101643450B (en) | Synthesis method for multi substituted 2, 3-dihydro-4(1H)-pyrimidin thionone | |
| CN203790917U (en) | Feeding device for hydrolyzed polyacrylonitrile ammonium salt production |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C14 | Grant of patent or utility model | ||
| GR01 | Patent grant | ||
| CF01 | Termination of patent right due to non-payment of annual fee |
Granted publication date: 20160427 |