CN116282240A - Purification method of triruthenium laurcarbonyl - Google Patents
Purification method of triruthenium laurcarbonyl Download PDFInfo
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- CN116282240A CN116282240A CN202310535590.7A CN202310535590A CN116282240A CN 116282240 A CN116282240 A CN 116282240A CN 202310535590 A CN202310535590 A CN 202310535590A CN 116282240 A CN116282240 A CN 116282240A
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- triruthenium
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- dodecacarbonyl
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- 238000000034 method Methods 0.000 title claims abstract description 26
- 238000000746 purification Methods 0.000 title description 9
- 239000012043 crude product Substances 0.000 claims abstract description 31
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims abstract description 20
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 claims abstract description 18
- 239000003729 cation exchange resin Substances 0.000 claims abstract description 18
- 239000003960 organic solvent Substances 0.000 claims abstract description 12
- 238000004440 column chromatography Methods 0.000 claims abstract description 10
- 239000011259 mixed solution Substances 0.000 claims abstract description 10
- 239000000377 silicon dioxide Substances 0.000 claims abstract description 10
- VMDTXBZDEOAFQF-UHFFFAOYSA-N formaldehyde;ruthenium Chemical compound [Ru].O=C VMDTXBZDEOAFQF-UHFFFAOYSA-N 0.000 claims abstract description 9
- 230000002829 reductive effect Effects 0.000 claims abstract description 8
- 239000007791 liquid phase Substances 0.000 claims abstract description 6
- 239000007788 liquid Substances 0.000 claims abstract description 3
- 238000000926 separation method Methods 0.000 claims abstract description 3
- NQZFAUXPNWSLBI-UHFFFAOYSA-N carbon monoxide;ruthenium Chemical group [Ru].[Ru].[Ru].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-] NQZFAUXPNWSLBI-UHFFFAOYSA-N 0.000 claims description 36
- 238000006243 chemical reaction Methods 0.000 claims description 23
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims description 13
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 13
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical group ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical group CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 12
- 239000000243 solution Substances 0.000 claims description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 9
- 238000010438 heat treatment Methods 0.000 claims description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 8
- 238000001914 filtration Methods 0.000 claims description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 6
- 238000001816 cooling Methods 0.000 claims description 6
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 claims description 6
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 4
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 4
- 150000001412 amines Chemical class 0.000 claims description 4
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 claims description 4
- YBCAZPLXEGKKFM-UHFFFAOYSA-K ruthenium(iii) chloride Chemical compound [Cl-].[Cl-].[Cl-].[Ru+3] YBCAZPLXEGKKFM-UHFFFAOYSA-K 0.000 claims description 4
- 229910001220 stainless steel Inorganic materials 0.000 claims description 4
- 239000010935 stainless steel Substances 0.000 claims description 4
- 238000000859 sublimation Methods 0.000 claims description 4
- 230000008022 sublimation Effects 0.000 claims description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 4
- 230000002378 acidificating effect Effects 0.000 claims description 2
- 239000013078 crystal Substances 0.000 claims description 2
- 229940043279 diisopropylamine Drugs 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 1
- 239000000047 product Substances 0.000 abstract description 12
- 239000012535 impurity Substances 0.000 abstract description 11
- 238000002506 high-vacuum sublimation Methods 0.000 abstract description 5
- 125000002091 cationic group Chemical group 0.000 abstract description 4
- 238000007796 conventional method Methods 0.000 abstract description 3
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 5
- 229910052707 ruthenium Inorganic materials 0.000 description 5
- 238000004458 analytical method Methods 0.000 description 4
- 238000001095 inductively coupled plasma mass spectrometry Methods 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 238000001179 sorption measurement Methods 0.000 description 2
- LRCMWDSWXDKYJS-UHFFFAOYSA-N [Fe].[Na].[K] Chemical compound [Fe].[Na].[K] LRCMWDSWXDKYJS-UHFFFAOYSA-N 0.000 description 1
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 230000006315 carbonylation Effects 0.000 description 1
- 238000005810 carbonylation reaction Methods 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 238000003889 chemical engineering Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 239000012847 fine chemical Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01G—COMPOUNDS CONTAINING METALS NOT COVERED BY SUBCLASSES C01D OR C01F
- C01G55/00—Compounds of ruthenium, rhodium, palladium, osmium, iridium, or platinum
- C01G55/007—Compounds containing at least one carbonyl group
- C01G55/008—Carbonyls
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01G—COMPOUNDS CONTAINING METALS NOT COVERED BY SUBCLASSES C01D OR C01F
- C01G55/00—Compounds of ruthenium, rhodium, palladium, osmium, iridium, or platinum
- C01G55/001—Preparation involving a liquid-liquid extraction, an adsorption or an ion-exchange
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01P—INDEXING SCHEME RELATING TO STRUCTURAL AND PHYSICAL ASPECTS OF SOLID INORGANIC COMPOUNDS
- C01P2006/00—Physical properties of inorganic compounds
- C01P2006/80—Compositional purity
-
- 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
- Y02P10/00—Technologies related to metal processing
- Y02P10/20—Recycling
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The embodiment of the invention discloses a method for purifying dodecacarbonyl triruthenium. The method comprises the following steps: (1) Dissolving a crude product of the triruthenium laurcarbonyl in an organic solvent to form a mixed solution; (2) Contacting the mixed solution with cation exchange resin, performing solid-liquid separation, and collecting a liquid phase; (3) Purifying the liquid phase by silica column chromatography, concentrating under reduced pressure, and sublimating to obtain high-purity dodecacarbonyl triruthenium. According to the invention, the crude product of the dodecacarbonyl triruthenium synthesized by the conventional method is sequentially subjected to cation exchange resin contact, silica column chromatography and high vacuum sublimation treatment, so that the contained cationic impurity elements can be effectively removed, and the purity of the product is ensured to be more than 6N (99.9999%).
Description
Technical Field
The embodiment of the invention relates to the technical field of fine chemical engineering, in particular to a method for purifying triruthenium dodecacarbonyl.
Background
Triruthenium dodecacarbonyl (CAS number: 15243-33-1) as a precursor to carbonyl groups and an H-transfer catalyst for the reductive carbonylation of aromatic nitro complexes to carbamates. With the development of the semiconductor preparation process, the product is applied to the preparation process of a 3nm chip, the purity of the current commercial ruthenium dodecacarbonyl is 98%, and the commercial ruthenium dodecacarbonyl is taken as a raw material, so that a large amount of black substances appear in the formed ruthenium film, and the normal function of the film is influenced. Therefore, purification of triruthenium dodecacarbonyl is highly desired.
CN 106458637a discloses a purification method of triruthenium dodecacarbonyl, which adopts recrystallization to purify, and the method can remove impurities insoluble in organic solvents, but cannot completely remove trace amounts of soluble cationic impurities.
CN 105683410a discloses a process for producing DCR, which comprises a step of separating impurity elements from crude DCR by sublimation to purify DCR, wherein the crude DCR is heated in an atmosphere having a carbon monoxide concentration of 3 to 100% to sublimate, and then cooled to precipitate DCR. The purification method needs to adopt special equipment, and the vacuum degree is adjusted by controlling the adding speed of CO, so that the sublimation purification of the product can be ensured under higher heating temperature.
Disclosure of Invention
The applicant found that the synthesized dodecacarbonyl triruthenium contains a large amount of cations such as iron potassium sodium and other impurity elements due to experimental equipment, experimental raw materials and other reasons. Therefore, the embodiment of the invention provides a method for purifying the dodecacarbonyl triruthenium, which can effectively remove trace soluble cationic impurities, and has simple process and strong operability.
In order to achieve the above object, the embodiment of the present invention provides the following technical solutions:
a method for purifying triruthenium dodecacarbonyl, comprising the following steps:
(1) Dissolving a crude product of the triruthenium laurcarbonyl in an organic solvent to form a mixed solution;
(2) Contacting the mixed solution with cation exchange resin, performing solid-liquid separation, and collecting a liquid phase;
(3) Purifying the liquid phase by silica column chromatography, concentrating under reduced pressure, and sublimating to obtain high-purity dodecacarbonyl triruthenium.
Further, the cation exchange resin is a strongly acidic cation exchange resin.
Further, the cation exchange resin includes AMBERSEP 252H,AMBERJE 1000H or AMBERLIT 1600H.
Further, the contact temperature of the mixed solution and the cation exchange resin is-20-40 ℃ and the time is 1-60 minutes.
Further, the organic solvent is dichloromethane, tetrahydrofuran or diethyl ether; the mass volume ratio of the crude product of the triruthenium dodecacarbonyl to the organic solvent is 1:3-20.
Further, the volume-mass ratio of the mixed solution to the cation exchange resin is 10-100:1.
Further, the sublimation is 5.0X10 -5 -10.0×10 -5 The heating is carried out under high vacuum of Pa, and the heating temperature is 55-70 ℃.
The preparation method of the crude product of the dodecacarbonyl triruthenium is a conventional method in the field. Preferably, the preparation method of the crude product of the triruthenium dodecacarbonyl comprises the following steps:
dissolving ruthenium chloride in an organic solvent, transferring the obtained reaction solution into a stainless steel high-pressure reaction kettle, adding organic amine, simultaneously introducing carbon monoxide, starting the reaction when the pressure of the carbon monoxide reaches 4-10MPa, continuously introducing carbon monoxide gas during the reaction, keeping the pressure in the kettle basically unchanged, cooling to room temperature after the reaction is finished, and filtering to obtain orange crystals, namely the crude product of the tri-ruthenium dodecacarbonyl.
Further, the temperature of the reaction is 60-130 ℃ and the time is 8-16 hours.
Further, the organic solvent is methanol, isopropanol or ethanol; the organic amine is triethylamine, diisopropylamine, cyclohexylamine, morpholine or piperazine.
The embodiment of the invention has the following advantages:
according to the invention, the crude product of the dodecacarbonyl triruthenium synthesized by the conventional method is sequentially subjected to cation exchange resin contact, silica column chromatography and high vacuum sublimation treatment, so that the contained cationic impurity elements can be effectively removed, and the purity of the product is ensured to be more than 6N (99.9999%).
Detailed Description
Other advantages and advantages of the present invention will become apparent to those skilled in the art from the following detailed description, which, by way of illustration, is to be read in connection with certain specific embodiments, but not all embodiments. All other embodiments, which can be made by those skilled in the art based on the embodiments of the invention without making any inventive effort, are intended to be within the scope of the invention.
High purity silica column chromatography: the purity is 99.5 percent, and the grain diameter is 200-300 meshes.
Example 1
The present example provides a purification method of triruthenium dodecacarbonyl:
step 1: 50g of ruthenium chloride is dissolved in 1000mL of methanol, transferred into a stainless steel high-pressure reaction kettle with the capacity of 3L, 90g of triethylamine is added into the reaction kettle, then carbon monoxide is introduced, the reaction is carried out for 12 hours at 60 ℃ when the pressure of the carbon monoxide in the reaction kettle reaches 5MPa, carbon monoxide gas is continuously introduced during the reaction, the pressure in the kettle is kept basically unchanged, after the reaction is finished, the reaction kettle is cooled to room temperature, and 41g of orange crude product of the tricarbonyl ruthenium is obtained by filtering.
Step 2: 41g of the crude product of the triruthenium dodecacarbonyl obtained in the step 1 is dissolved in 200ml of anhydrous dichloromethane, 20g of AMBERSEP 252H cation exchange resin is added, the adsorption is carried out for 20min at the temperature of 0 ℃, the filtration is carried out, the obtained solution is subjected to high-purity silica column chromatography, and the obtained solution is concentrated under reduced pressure to obtain 38g of the intermediate crude product of the triruthenium dodecacarbonyl.
Step 3: subjecting 20g of the above intermediate crude product to high vacuum sublimation with vacuum degree of 5.0X10 -5 Pa, heating temperature is 55 ℃, cooling temperature is 10-20 ℃, and 19.7g of product is obtained. The total yield of the three steps is 72.7 percent.
And (3) respectively carrying out ICP-MS analysis on the crude product obtained in the step (1), the intermediate crude product obtained in the step (2) and the product obtained in the step (3), wherein the test result of impurity content is shown in Table 1.
TABLE 1
Example 2
The present example provides a purification method of triruthenium dodecacarbonyl:
step 1: 160g of ruthenium chloride and 10L of isopropanol were mixed and stirred and transferred to a 30L capacity stainless steel autoclave. Adding 300 g triethylamine into a reaction kettle, then introducing carbon monoxide gas, reacting for 10 hours at 70 ℃ when the pressure of carbon monoxide in the reaction kettle reaches 4MPa, continuously introducing the carbon monoxide gas during the reaction, keeping the pressure in the kettle basically unchanged, cooling to room temperature after the reaction is finished, and filtering to obtain 117g of orange crude product of the tricarbonyl ruthenium.
Step 2: dissolving 117g of the crude product of the triruthenium dodecacarbonyl obtained in the step 1 in 1000ml of dichloromethane, adding 90g of AMBERSEP 252H cation exchange resin, adsorbing for 30min at 0 ℃, filtering, subjecting the obtained solution to high-purity silica column chromatography to obtain the solution of the triruthenium dodecacarbonyl, and concentrating under reduced pressure to obtain 109g of the intermediate crude product of the triruthenium dodecacarbonyl.
Step 3: taking 40g of the intermediate crude product, performing high vacuum sublimation, and vacuum degree is 5.0X10 -5 Pa, heating temperature to 65 ℃, cooling temperature to 10-20 ℃, and collecting 39.0g of product. The total yield of the three steps is 64.5%.
And (3) respectively carrying out ICP-MS analysis on the crude product obtained in the step (1), the intermediate crude product obtained in the step (2) and the product obtained in the step (3), wherein the test result of impurity content is shown in Table 2.
TABLE 2
Example 3
The present example provides a purification method of triruthenium dodecacarbonyl:
step 1: as in example 2.
Step 2: 117g of the crude product of triruthenium dodecacarbonyl obtained in the step 1 of example 2 was dissolved in 1000ml of tetrahydrofuran, 80g of amberrje 1000H cation exchange resin was added, adsorption was performed at 0 ℃ for 30min, filtration was performed, the obtained solution was subjected to high purity silica column chromatography to obtain a solution of triruthenium dodecacarbonyl, and concentration was performed under reduced pressure to obtain 111g of the intermediate crude product of triruthenium dodecacarbonyl.
Step 3: 40g of the Chinese medicinal composition is takenThe intermediate crude product is sublimated under high vacuum with the vacuum degree of 5.0 multiplied by 10 -5 Pa, heating temperature to 65 ℃, cooling temperature to 10-20 ℃, and collecting 38.5g of product. The total yield of the three steps is 64.9%.
ICP-MS analysis is carried out on the intermediate crude product obtained in the step 2 and the product obtained in the step 3 respectively, and the test results of impurity content are shown in Table 3.
TABLE 3 Table 3
Comparative example 1
This comparative example provides a method for purifying triruthenium dodecacarbonyl:
step 1: as in example 2.
Step 2: 117g of the crude product of triruthenium dodecacarbonyl obtained in the step 1 of the example 2 is dissolved in 1000ml of tetrahydrofuran, the obtained solution is subjected to high-purity silica column chromatography to obtain a triruthenium dodecacarbonyl solution, and the solution is concentrated under reduced pressure to obtain 102g of the intermediate crude product of triruthenium dodecacarbonyl.
Step 3: taking 40g of the intermediate crude product, performing high vacuum sublimation, and vacuum degree is 5.0X10 -5 Pa, heating temperature 65 ℃, collecting 37g of product.
ICP-MS analysis is carried out on the intermediate crude product obtained in the step 2 and the product obtained in the step 3 respectively, and the test results of impurity content are shown in Table 4.
TABLE 4 Table 4
While the invention has been described in detail in the foregoing general description and specific examples, it will be apparent to those skilled in the art that modifications and improvements can be made thereto. Accordingly, such modifications or improvements may be made without departing from the spirit of the invention and are intended to be within the scope of the invention as claimed.
Claims (10)
1. A method for purifying triruthenium dodecacarbonyl, which is characterized by comprising the following steps:
(1) Dissolving a crude product of the triruthenium laurcarbonyl in an organic solvent to form a mixed solution;
(2) Contacting the mixed solution with cation exchange resin, performing solid-liquid separation, and collecting a liquid phase;
(3) Purifying the liquid phase by silica column chromatography, concentrating under reduced pressure, and sublimating to obtain high-purity dodecacarbonyl triruthenium.
2. The method for purifying triruthenium dodecacarbonyl according to claim 1, wherein the cation exchange resin is a strongly acidic cation exchange resin.
3. The method for purifying triruthenium dodecacarbonyl according to claim 1, wherein the cation exchange resin comprises AMBERSEP 252H,AMBERJE 1000H or AMBERLIT 1600H.
4. The method for purifying triruthenium dodecacarbonyl according to claim 1, wherein the contact temperature of the mixed solution and the cation exchange resin is-20 ℃ to 40 ℃ for 1 to 60 minutes.
5. The method for purifying triruthenium dodecacarbonyl according to claim 1, wherein the organic solvent is dichloromethane, tetrahydrofuran, or diethyl ether; the mass volume ratio of the crude product of the triruthenium dodecacarbonyl to the organic solvent is 1:3-20.
6. The method for purifying triruthenium dodecacarbonyl according to claim 1, wherein the volume to mass ratio of the mixed solution to the cation exchange resin is 10-100:1.
7. The method for purifying triruthenium dodecacarbonyl according to claim 1, wherein the sublimation is performed at 5.0X10: -5 -10.0×10 -5 the heating is carried out under high vacuum of Pa, and the heating temperature is 55-70 ℃.
8. The method for purifying triruthenium dodecacarbonyl according to any one of claims 1 to 7, wherein the method for producing the crude triruthenium dodecacarbonyl comprises:
dissolving ruthenium chloride in an organic solvent, transferring the obtained reaction solution into a stainless steel high-pressure reaction kettle, adding organic amine, simultaneously introducing carbon monoxide, starting the reaction when the pressure of the carbon monoxide reaches 4-10MPa, continuously introducing carbon monoxide gas during the reaction, keeping the pressure in the kettle basically unchanged, cooling to room temperature after the reaction is finished, and filtering to obtain orange crystals, namely the crude product of the tri-ruthenium dodecacarbonyl.
9. The method for purifying triruthenium dodecacarbonyl according to claim 8, wherein the reaction is carried out at a temperature of 60 to 130 ℃ for 8 to 16 hours.
10. The method for purifying triruthenium dodecacarbonyl according to claim 8, wherein the organic solvent is methanol, isopropanol, or ethanol; the organic amine is triethylamine, diisopropylamine, cyclohexylamine, morpholine or piperazine.
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| CN111808071A (en) * | 2020-08-13 | 2020-10-23 | 中国科学院兰州化学物理研究所 | Method for synthesizing polysubstituted aminoisoquinoline compound by cyclization of pyridine and alkyne under catalysis of rhodium |
| CN112062769A (en) * | 2020-09-03 | 2020-12-11 | 中国科学院兰州化学物理研究所 | Process for preparing penta-and hepta-homopiperazinone derivatives by catalytic carbonylation of aminoalkyleneamine oxides |
| CN112473662A (en) * | 2020-11-18 | 2021-03-12 | 铜陵欣诺科新材料有限公司 | Ruthenium-carbon catalyst and preparation method thereof |
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