CN114029092B - Synthesis method of metal catalyst - Google Patents
Synthesis method of metal catalyst Download PDFInfo
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- CN114029092B CN114029092B CN202111626739.XA CN202111626739A CN114029092B CN 114029092 B CN114029092 B CN 114029092B CN 202111626739 A CN202111626739 A CN 202111626739A CN 114029092 B CN114029092 B CN 114029092B
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- 239000003054 catalyst Substances 0.000 title claims abstract description 28
- 229910052751 metal Inorganic materials 0.000 title claims abstract description 22
- 239000002184 metal Substances 0.000 title claims abstract description 22
- 238000001308 synthesis method Methods 0.000 title claims description 10
- 239000003960 organic solvent Substances 0.000 claims abstract description 56
- 239000012046 mixed solvent Substances 0.000 claims abstract description 26
- 238000006243 chemical reaction Methods 0.000 claims abstract description 25
- 239000000706 filtrate Substances 0.000 claims abstract description 23
- 238000001914 filtration Methods 0.000 claims abstract description 15
- 238000010992 reflux Methods 0.000 claims abstract description 14
- HFPZCAJZSCWRBC-UHFFFAOYSA-N p-cymene Chemical compound CC(C)C1=CC=C(C)C=C1 HFPZCAJZSCWRBC-UHFFFAOYSA-N 0.000 claims abstract description 12
- 238000000034 method Methods 0.000 claims abstract description 11
- YILMOQBPBZHHFY-UHFFFAOYSA-L C(C)(C)[Ru](C1=CC=CC=C1)(Cl)Cl Chemical compound C(C)(C)[Ru](C1=CC=CC=C1)(Cl)Cl YILMOQBPBZHHFY-UHFFFAOYSA-L 0.000 claims abstract description 10
- 230000002194 synthesizing effect Effects 0.000 claims abstract description 9
- 238000001816 cooling Methods 0.000 claims abstract description 8
- GPAYUJZHTULNBE-UHFFFAOYSA-N diphenylphosphine Chemical compound C=1C=CC=CC=1PC1=CC=CC=C1 GPAYUJZHTULNBE-UHFFFAOYSA-N 0.000 claims abstract description 8
- 239000012065 filter cake Substances 0.000 claims abstract description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 24
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 21
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 16
- 239000000047 product Substances 0.000 claims description 16
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 12
- 238000003756 stirring Methods 0.000 claims description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- 238000005406 washing Methods 0.000 claims description 6
- 239000012295 chemical reaction liquid Substances 0.000 claims description 5
- 239000003208 petroleum Substances 0.000 claims description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 4
- 238000010438 heat treatment Methods 0.000 claims description 4
- 239000003446 ligand Substances 0.000 claims description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 4
- 238000004321 preservation Methods 0.000 claims description 4
- YKYONYBAUNKHLG-UHFFFAOYSA-N propyl acetate Chemical compound CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 claims description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 2
- JWUJQDFVADABEY-UHFFFAOYSA-N 2-methyltetrahydrofuran Chemical compound CC1CCCO1 JWUJQDFVADABEY-UHFFFAOYSA-N 0.000 claims description 2
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 claims description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 2
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 claims description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims description 2
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 claims description 2
- 229940011051 isopropyl acetate Drugs 0.000 claims description 2
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 claims description 2
- 239000007858 starting material Substances 0.000 claims description 2
- 238000001291 vacuum drying Methods 0.000 claims description 2
- 239000012043 crude product Substances 0.000 claims 1
- 239000002904 solvent Substances 0.000 abstract description 13
- UCXDWSTYBSBFFB-UHFFFAOYSA-L 1-methyl-4-propan-2-ylbenzene;ruthenium(2+);dichloride Chemical compound Cl[Ru]Cl.CC(C)C1=CC=C(C)C=C1 UCXDWSTYBSBFFB-UHFFFAOYSA-L 0.000 abstract description 7
- 239000000203 mixture Substances 0.000 abstract description 3
- 239000007787 solid Substances 0.000 description 5
- 239000013078 crystal Substances 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 238000010586 diagram Methods 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 206010058467 Lung neoplasm malignant Diseases 0.000 description 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
- -1 biology Substances 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- DHCWLIOIJZJFJE-UHFFFAOYSA-L dichlororuthenium Chemical compound Cl[Ru]Cl DHCWLIOIJZJFJE-UHFFFAOYSA-L 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 201000005202 lung cancer Diseases 0.000 description 1
- 208000020816 lung neoplasm Diseases 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- YAYGSLOSTXKUBW-UHFFFAOYSA-N ruthenium(2+) Chemical compound [Ru+2] YAYGSLOSTXKUBW-UHFFFAOYSA-N 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 230000008685 targeting Effects 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/24—Phosphines, i.e. phosphorus bonded to only carbon atoms, or to both carbon and hydrogen atoms, including e.g. sp2-hybridised phosphorus compounds such as phosphabenzene, phosphole or anionic phospholide ligands
- B01J31/2404—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring
- B01J31/2409—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring with more than one complexing phosphine-P atom
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/80—Complexes comprising metals of Group VIII as the central metal
- B01J2531/82—Metals of the platinum group
- B01J2531/821—Ruthenium
Abstract
The invention relates to a method for synthesizing a metal catalyst, wherein the catalyst is [ (S) -BINAPRuCl2 (p-cymene ]/[ (S) - (-) -2,2 '-bis (diphenylphosphine) -1,1' -binaphthyl ] (p-isopropyl toluene) ruthenium dichloride, isopropyl phenyl ruthenium dichloride, (S) -BINAP and a first organic solvent are heated to reflux and react at a constant temperature, the reaction is carried out, cooling and filtering are carried out, the filter cake is washed by the first organic solvent, the filtrate is combined and concentrated under reduced pressure, then the mixed solvent with equal volume is added and concentrated again, then the mixed solvent with equal volume is added and concentrated continuously, and the mixture is cooled to room temperature, and is stirred and filtered, the mixed solvent is washed and dried to obtain the catalyst, and the mixed solvent is a second solvent and a third solvent.
Description
Technical Field
The invention belongs to the technical field of metal organic catalysis, and particularly relates to a synthesis method of a metal catalyst.
Background
The transition metal ruthenium (II) complex is usually hexacoordinated octahedral configuration complex with ligand, the complex is triplet state luminophor, has good optical performance, can excite and emit wavelength adjustable, long emission wavelength, long fluorescence lifetime, large Stokes shift and the like, thus obtaining close attention of people and achieving rapid development in application research in aspects of materials, biology, medicaments and the like.
The fourth generation lung cancer targeting drug eai045 is synthesized by adopting a metal ruthenium catalyst generally: [ (S) -BINAP RuCl 2 (p-cymene],/[ (S) - (-) -2,2 '-bis (diphenylphosphine) -1,1' -binaphthyl]The synthesis method of (p-isopropyl toluene) ruthenium dichloride at present is generally that isopropylphenyl ruthenium dichloride and (S) -BINAP are subjected to ligand exchange reaction under the reflux state of an organic solvent to obtain a catalyst product, and the catalyst product is filtered, concentrated and then subjected to n-heptane crystallization to obtain the product, but the purity of the product obtained by sequentially filtering, concentrating and n-heptane crystallization of the catalyst product is not high, the crystallization crystal form is not stable, and the product stability is not good.
Disclosure of Invention
The invention aims to provide a synthesis method of a metal catalyst, which has the advantages of easily obtained reaction raw materials, simple operation of the reaction process, low requirements on reaction equipment, relatively mild reaction conditions, stable quality, high yield and high content of catalyst products, and the content of the finally obtained metal catalyst is more than 99%.
The invention solves the problems by adopting the following technical scheme: a method for synthesizing a metal catalyst, wherein the metal catalyst is [ (S) -BINAP RuCl 2 (p-cymene],/[ (S) - (-) -2,2 '-bis (diphenylphosphine) -1,1' -binaphthyl]The synthesis method of (p-isopropyl toluene) ruthenium dichloride takes isopropyl phenyl ruthenium dichloride as a starting material, and the synthetic method is prepared through ligand exchange reaction and comprises the following steps:
(1) Under the condition of nitrogen, adding isopropylphenyl ruthenium dichloride, (S) -BINAP and a first organic solvent in sequence, heating to reflux, carrying out heat preservation reflux reaction, and cooling the reaction liquid after the reaction;
(2) Filtering the reaction liquid cooled in the step (1), washing a filter cake with a first organic solvent, and combining the filtrates;
(3) Concentrating the combined filtrate in the step (2) under reduced pressure until the volume of the combined filtrate is 1/5-1/2 of the total volume of the filtrate to obtain a first concentrated solution, adding the mixed solvent of the second organic solvent and the third organic solvent with equal volume, concentrating the mixed solvent to 1/5-1/2 of the total volume to obtain a second concentrated solution, and adding the mixed solvent of the second organic solvent and the third organic solvent with equal volume, and continuously concentrating the mixed solvent to 1/2-4/5 of the total volume of the filtrate to obtain a third concentrated solution;
(4) Cooling the concentrated solution obtained in the step (3) to room temperature, stirring at room temperature, filtering, washing the mixed solvent of the second organic solvent and the third organic solvent to obtain pale yellow to pale brown crystalline solid, and vacuum drying to obtain pale yellow crystalline solid powder;
wherein the first organic solvent is one of methanol, ethanol, isopropanol, tetrahydrofuran and 2-methyltetrahydrofuran;
the second organic solvent is one of ethyl acetate, isopropyl ether, diethyl ether, isopropyl acetate, n-propyl acetate, butyl acetate and 1, 4-dioxane.
The third organic solvent is one of n-heptane, n-hexane, cyclohexane and petroleum ether.
The reaction formula of the synthesis method is shown as follows:
preferably, the volume ratio of the second organic solvent to the third organic solvent in the mixed solvent is 1:1.
Preferably, the molar ratio of (S) -BINAP to isopropylphenyl ruthenium dichloride in step (1) is 1:2 to 2.9.
Preferably, the heat preservation reflux time in the step (1) is 2-5 hours.
Preferably, the reaction solution in step (1) is cooled to 20.+ -. 5 ℃.
Preferably, the filtration in step (2) is a diatomite-assisted filtration.
Preferably, in the step (4), the stirring time at room temperature is 5-10 hours.
Compared with the prior art, the invention has the advantages that:
(1) The synthesis method of the metal catalyst has the advantages of easily obtained reaction raw materials, simple operation of the reaction process, low requirements on reaction equipment, relatively mild reaction conditions, high yield and content, suitability for industrial production and capability of finally obtaining the metal catalyst with the content of more than 99 percent.
(2) Compared with the defect that the purity of the concentrated product is not high by using the same solvent in the post-treatment in the prior art, the synthesis method of the invention has the advantages that the reaction liquid is cooled and filtered, the filter cake is washed by the first organic solvent, the filtrate is combined, the combined filtrate is concentrated under reduced pressure, then the mixed solvent of the second organic solvent and the third organic solvent with the same volume is added for re-concentration, and then the mixed solvent of the second organic solvent and the third organic solvent with the same volume is added for continued concentration; the first organic solvent is a benign solvent with high solubility, the second organic solvent is a general benign solvent with medium solubility, the third organic solvent is a poor solvent with low solubility, the benign solvent is firstly utilized to dissolve and concentrate the product to a smaller volume in the post-treatment, then the general benign solvent is added to take the benign solvent out of the system through distillation, then the poor solvent is added to separate out the product, and the difference of distribution coefficients of the product and impurity components in the mixture in the two solvents is utilized to maximize the separation product and dissolve impurities, thereby increasing the post-treatment yield and improving the product purity.
Drawings
FIG. 1 shows the structure of [ (S) -BINAP RuCl ] of the present invention 2 (p-cymene],/[ (S) - (-) -2,2 '-bis (diphenylphosphine) -1,1' -binaphthyl]Process flow diagram of (p-isopropyltoluene) ruthenium dichloride.
Detailed Description
The invention is described in further detail below with reference to the embodiments of the drawings.
As shown in FIG. 1, the process flow diagram of [ (S) -BINAP RuCl2 (p-cymene ]/[ (S) - (-) -2,2 '-bis (diphenylphosphine) -1,1' -binaphthyl ] (p-isopropyltoluene) ruthenium dichloride according to the present invention.
Example 1
12Kg of isopropylphenyl ruthenium dichloride, 26Kg (S) -BINAP and 120Kg of first organic solvent tetrahydrofuran are sequentially added into a reaction device provided with a thermometer, a reflux condenser and stirring under the condition of nitrogen at room temperature, and the system is replaced by nitrogen three times; stirring, heating to 64 ℃ for reflux, keeping the temperature for reflux reaction for 5 hours, cooling the reaction to 23-25 ℃, filtering under the assistance of diatomite, washing a filter cake by using a first organic solvent tetrahydrofuran, combining filtrate, concentrating the filtrate under reduced pressure to 1/2 volume of the total volume of the filtrate, adding an equal volume of a mixed solvent of a second organic solvent (ethyl acetate)/a third organic solvent (petroleum ether) (1:1, v/v) for concentrating to 1/2 volume, adding an equal volume of a mixed solvent of a second organic solvent (ethyl acetate)/a third organic solvent (petroleum ether) (1:1, v/v), continuing concentrating to 4/5 of the total volume of the filtrate, cooling to room temperature, stirring at room temperature for 8 hours, filtering, washing the mixed solvent of the second organic solvent (ethyl acetate)/the third organic solvent (petroleum ether) (1:1, v/v) to obtain a pale yellow crystalline solid, and drying in vacuum to obtain pale yellow crystalline solid powder.
The final product [ (S) - (-) -2,2 '-bis (diphenylphosphine) -1,1' -binaphthyl ] (p-isopropyl toluene) ruthenium dichloride content is 99.2%, and the molar yield of the product is 90.65%.
Example 2
Under room temperature nitrogen, 19Kg of isopropylphenyl ruthenium dichloride, 45Kg (S) -BINAP and 190Kg of first organic solvent methanol are sequentially added into a reaction device provided with a thermometer, a reflux condenser and a stirrer, the system is replaced by nitrogen three times, stirring is started, heating is carried out to 65 ℃ for reflux, the reflux reaction is kept for 5 hours, the reaction is cooled to 23-25 ℃, diatomite is filtered under a filtration assisting mode, a filter cake is washed by the first organic methanol solvent, the filtrates are combined, the filtrate is concentrated to 1/2 volume of the total volume of the filtrate under reduced pressure, an equal volume of a second organic solvent (ethyl acetate)/a third organic solvent (n-heptane) (1:1, v/v) mixed solvent is added to 1/2 volume, an equal volume of a second organic solvent (ethyl acetate)/third organic solvent (n-heptane) (1:1, v/v) mixed solvent is further added, the mixture solvent is concentrated to 4/5 of the total volume of the filtrate, cooling is carried out to room temperature, stirring is carried out for 10 hours, and the filtration is carried out, the second organic solvent (ethyl acetate)/third organic solvent (n-heptane) (1:1, v/v) mixed solvent is dried to obtain light yellow crystal solid, and the light yellow crystal powder is obtained.
The final product [ (S) - (-) -2,2 '-bis (diphenylphosphine) -1,1' -binaphthyl ] (p-isopropyl toluene) ruthenium dichloride content was 99.3%, and the molar yield was 92.82%.
In addition to the above embodiments, the present invention also includes other embodiments, and all technical solutions that are formed by equivalent transformation or equivalent substitution should fall within the protection scope of the claims of the present invention.
Claims (7)
1. A method for synthesizing a metal catalyst is characterized in that: the metal catalyst is [ (S) -BINAP RuCl 2 (p-cymene],/[ (S) - (-) -2,2 '-bis (diphenylphosphine) -1,1' -binaphthyl]The synthesis method takes isopropyl phenyl ruthenium dichloride as a starting material, and a catalyst product is prepared through ligand exchange reaction, and comprises the following steps:
(1) Under the condition of nitrogen, adding isopropylphenyl ruthenium dichloride, (S) -BINAP and a first organic solvent in sequence, heating to reflux, carrying out heat preservation reflux reaction, and cooling the reaction liquid after the reaction;
(2) Filtering the reaction liquid cooled in the step (1), washing a filter cake with a first organic solvent, and combining the filtrates;
(3) Concentrating the combined filtrate in the step (2) under reduced pressure to obtain a first concentrated solution, adding a mixed solvent of a second organic solvent and a third organic solvent with equal volume, concentrating to obtain a second concentrated solution, adding a mixed solvent of the second organic solvent and the third organic solvent with equal volume, and continuously concentrating to obtain a third concentrated solution;
(4) Cooling the third concentrated solution obtained in the step (3) to room temperature, stirring at room temperature, filtering, washing the mixed solvent of the second organic solvent and the third organic solvent to obtain a crude product of the metal catalyst, and vacuum drying to obtain a finished product of the metal catalyst;
wherein the first organic solvent is one of methanol, ethanol, isopropanol, tetrahydrofuran and 2-methyltetrahydrofuran;
the second organic solvent is one of ethyl acetate, isopropyl ether, diethyl ether, isopropyl acetate, n-propyl acetate, butyl acetate and 1, 4-dioxane;
the third organic solvent is one of n-heptane, n-hexane, cyclohexane and petroleum ether;
the volume ratio of the second organic solvent to the third organic solvent in the mixed solvent is 1:1.
2. The method for synthesizing a metal catalyst according to claim 1, wherein: the molar ratio of the isopropyl phenyl ruthenium dichloride to the (S) -BINAP in the step (1) is 1:2 to 2.9.
3. The method for synthesizing a metal catalyst according to claim 1, wherein: and (3) the heat preservation reflux time in the step (1) is 2-5 hours.
4. The method for synthesizing a metal catalyst according to claim 1, wherein: the reaction solution in the step (1) is cooled to 20+/-5 ℃.
5. The method for synthesizing a metal catalyst according to claim 1, wherein: the filtration in the step (2) is diatomite filtration-assisted filtration.
6. The method for synthesizing a metal catalyst according to claim 1, wherein: the step (3) is specifically as follows: and (3) merging the filtrates in the step (2), concentrating under reduced pressure until the volume of the filtrate is 1/5-1/2 of the total volume of the filtrate to obtain a first concentrated solution, adding the mixed solvent of the second organic solvent and the third organic solvent with equal volume, concentrating again until the volume of the mixed solvent is 1/5-1/2 of the total volume of the filtrate to obtain a second concentrated solution, and adding the mixed solvent of the second organic solvent and the third organic solvent with equal volume, and continuously concentrating until the volume of the mixed solvent is 1/2-4/5 of the total volume of the filtrate to obtain a third concentrated solution.
7. The method for synthesizing a metal catalyst according to claim 1, wherein: and (3) stirring at room temperature for 5-10 hours in the step (4).
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Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5223632A (en) * | 1990-03-01 | 1993-06-29 | Takasago International Corporation | 2,2'-bis(di-(3,5-dialkylphenyl)phosphino)-1,1'-binaphthyl and transition metal complex containing the samd ligand |
| CN102858788A (en) * | 2010-04-28 | 2013-01-02 | 高砂香料工业株式会社 | Ruthenium complex and method for preparing optically active alcohol compound |
| WO2014056421A1 (en) * | 2012-10-09 | 2014-04-17 | 江西同和药业有限责任公司 | 1-cyan-1-(7-methoxyl-1-naphtyl) methanol ester compound and preparation method and use thereof |
| CN112194685A (en) * | 2020-10-27 | 2021-01-08 | 西安凯立新材料股份有限公司 | Preparation method of [ (S) - (-) -2,2 '-bis (diphenylphosphino) -1,1' -binaphthyl ] palladium dichloride |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6620955B1 (en) * | 2001-11-15 | 2003-09-16 | Richard L. Pederson | Chelating carbene ligand precursors and their use in the synthesis of metathesis catalysts |
| GB0822064D0 (en) * | 2008-12-03 | 2009-01-07 | Johnson Matthey Plc | Process for preparing cationic ruthenium complexes |
| CN105669642B (en) * | 2014-11-19 | 2020-06-09 | 江苏天士力帝益药业有限公司 | Preparation method of loflupridine hydrochloride |
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Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5223632A (en) * | 1990-03-01 | 1993-06-29 | Takasago International Corporation | 2,2'-bis(di-(3,5-dialkylphenyl)phosphino)-1,1'-binaphthyl and transition metal complex containing the samd ligand |
| CN102858788A (en) * | 2010-04-28 | 2013-01-02 | 高砂香料工业株式会社 | Ruthenium complex and method for preparing optically active alcohol compound |
| WO2014056421A1 (en) * | 2012-10-09 | 2014-04-17 | 江西同和药业有限责任公司 | 1-cyan-1-(7-methoxyl-1-naphtyl) methanol ester compound and preparation method and use thereof |
| CN112194685A (en) * | 2020-10-27 | 2021-01-08 | 西安凯立新材料股份有限公司 | Preparation method of [ (S) - (-) -2,2 '-bis (diphenylphosphino) -1,1' -binaphthyl ] palladium dichloride |
Non-Patent Citations (2)
| Title |
|---|
| Chemistry of Ruthenium(II) Alkyl Binap Complexes: Novel Bonding, Cyclometalation, and P-C Bond Splitting;Tilmann J. Geldbach等;《Organometallics》;第第22卷卷;第1443-1451页 * |
| 祁晓津.《基础化学实验（有机化学）》.黄河出版传媒集团,2011,第097页倒数第一段. * |
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