NL2032470B1 - Preparation method for benzene-d6 - Google Patents
Preparation method for benzene-d6 Download PDFInfo
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- NL2032470B1 NL2032470B1 NL2032470A NL2032470A NL2032470B1 NL 2032470 B1 NL2032470 B1 NL 2032470B1 NL 2032470 A NL2032470 A NL 2032470A NL 2032470 A NL2032470 A NL 2032470A NL 2032470 B1 NL2032470 B1 NL 2032470B1
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- benzene
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- UHOVQNZJYSORNB-MZWXYZOWSA-N benzene-d6 Chemical compound [2H]C1=C([2H])C([2H])=C([2H])C([2H])=C1[2H] UHOVQNZJYSORNB-MZWXYZOWSA-N 0.000 title claims abstract description 22
- 238000002360 preparation method Methods 0.000 title abstract description 9
- 239000000243 solution Substances 0.000 claims abstract description 54
- 239000007789 gas Substances 0.000 claims abstract description 23
- 238000000034 method Methods 0.000 claims abstract description 23
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims abstract description 18
- 229910052805 deuterium Inorganic materials 0.000 claims abstract description 18
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 16
- 238000006243 chemical reaction Methods 0.000 claims abstract description 16
- 239000011259 mixed solution Substances 0.000 claims abstract description 12
- 150000001555 benzenes Chemical class 0.000 claims abstract description 10
- 239000003153 chemical reaction reagent Substances 0.000 claims abstract description 9
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 8
- 239000003054 catalyst Substances 0.000 claims description 18
- 239000000706 filtrate Substances 0.000 claims description 14
- -1 lithium aluminum deuteride Chemical compound 0.000 claims description 13
- 238000003756 stirring Methods 0.000 claims description 13
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 8
- 230000008569 process Effects 0.000 claims description 8
- 239000008367 deionised water Substances 0.000 claims description 7
- 229910021641 deionized water Inorganic materials 0.000 claims description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
- 239000010457 zeolite Substances 0.000 claims description 7
- ZQBFAOFFOQMSGJ-UHFFFAOYSA-N hexafluorobenzene Chemical compound FC1=C(F)C(F)=C(F)C(F)=C1F ZQBFAOFFOQMSGJ-UHFFFAOYSA-N 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 6
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 claims description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 4
- DSVGQVZAZSZEEX-UHFFFAOYSA-N [C].[Pt] Chemical compound [C].[Pt] DSVGQVZAZSZEEX-UHFFFAOYSA-N 0.000 claims description 4
- 238000001035 drying Methods 0.000 claims description 4
- CAYGQBVSOZLICD-UHFFFAOYSA-N hexabromobenzene Chemical compound BrC1=C(Br)C(Br)=C(Br)C(Br)=C1Br CAYGQBVSOZLICD-UHFFFAOYSA-N 0.000 claims description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 4
- 239000012354 sodium borodeuteride Substances 0.000 claims description 4
- CKAPSXZOOQJIBF-UHFFFAOYSA-N hexachlorobenzene Chemical compound ClC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl CKAPSXZOOQJIBF-UHFFFAOYSA-N 0.000 claims description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 2
- 238000011049 filling Methods 0.000 claims description 2
- 238000001914 filtration Methods 0.000 claims description 2
- QNMKKFHJKJJOMZ-UHFFFAOYSA-N hexaiodobenzene Chemical compound IC1=C(I)C(I)=C(I)C(I)=C1I QNMKKFHJKJJOMZ-UHFFFAOYSA-N 0.000 claims description 2
- 229910052763 palladium Inorganic materials 0.000 claims description 2
- 229910052697 platinum Inorganic materials 0.000 claims description 2
- 239000000376 reactant Substances 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 abstract description 5
- 230000015572 biosynthetic process Effects 0.000 abstract description 2
- 150000001875 compounds Chemical class 0.000 abstract description 2
- 230000000694 effects Effects 0.000 abstract description 2
- 238000005516 engineering process Methods 0.000 abstract description 2
- 238000013341 scale-up Methods 0.000 abstract description 2
- 238000003786 synthesis reaction Methods 0.000 abstract description 2
- RXXCIBALSKQCAE-UHFFFAOYSA-N 3-methylbutoxymethylbenzene Chemical compound CC(C)CCOCC1=CC=CC=C1 RXXCIBALSKQCAE-UHFFFAOYSA-N 0.000 abstract 1
- XLYOFNOQVPJJNP-ZSJDYOACSA-N Heavy water Chemical group [2H]O[2H] XLYOFNOQVPJJNP-ZSJDYOACSA-N 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 238000010438 heat treatment Methods 0.000 description 5
- 230000009286 beneficial effect Effects 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- 230000009471 action Effects 0.000 description 2
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 2
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 2
- 230000006870 function Effects 0.000 description 2
- 230000008676 import Effects 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 229960001701 chloroform Drugs 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 230000036267 drug metabolism Effects 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 239000003344 environmental pollutant Substances 0.000 description 1
- 238000003384 imaging method Methods 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 238000011031 large-scale manufacturing process Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 239000002207 metabolite Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- 239000000447 pesticide residue Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 230000036647 reaction Effects 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 238000004454 trace mineral analysis Methods 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B59/00—Introduction of isotopes of elements into organic compounds ; Labelled organic compounds per se
- C07B59/001—Acyclic or carbocyclic compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/05—Isotopically modified compounds, e.g. labelled
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The present invention relates to a preparation method for a benzene—d6, and, belongs to synthesis technologies of deuterated compounds. In the method, a hexahalogenated benzene is prepared to obtain clear solution A; the clear solution A is transferred to a 5 high—pressure kettle, a deuterated reagent B is slowly added to the solution A under a condition of nitrogen protection, and mixed solution C is prepared; and after the mixed solution C is treated, a fraction at 78.8°C is taken to obtain the benzene—d6. The reaction achieves the effect of simultaneous deuteration of six 10 reaction sites, it does not need to be repeatedly operated, the production cycle is short, and it is suitable for industrial scale—up production; the obtained benzene—d6 is high in purity, and the yield may reach up to 90.6%; and a high—pressure deuterium gas atmosphere promotes the forward progress of the reaction. 15
Description
P1461 /NLpd
PREPARATION METHOD FOR BENZENE-D6
The present invention relates to a preparation method for a benzene-d6, and belongs to synthesis technologies of deuterated compounds.
Benzene-d6 is an organic material with special functions, and it has a wide range of applications in explaining reaction mecha- nisms, elucidating synthetic pathways, enhancing drug metabolism stability, biomedical imaging, gene detection, trace analysis of metabolites, pesticide residues, environmental pollutants and oth- er aspects.
At present, there are two common synthetic methods for the benzene-d6. 1. H/D exchange method: the traditional H/D exchange method includes acid, base, or transition metal-catalyzed H/D ex- changes, the disadvantages of these methods include carbon frame- work rearrangement, incompatibility with specific functions, the need for large amounts of deuterium sources and expensive cata- lysts, and slow or incomplete exchange of deuterium, and an H/D exchange operation needs to be repeated for many times; super- critical deuterium oxide exchange is a method developed in recent years for preparation of deuterides, and much attention is paid to it due to the low cost, the short reaction time, the high possi- bility of selective deuteration or hyperdeuteration of different organic compounds, and the high yield. An application of the su- percritical deuterium oxide exchange may adjust the physicochemi- cal properties of a supercritical deuterium oxide by adjusting the temperature and pressure, thereby the reaction efficiency, reac- tion rate and selectivity are further controlled. However, this method also has the apparent shortcomings, such as the high oper- ating pressure and the high temperature, and it is not suitable for large-scale development and utilization under existing condi- tions. 2. Acetylene polymerization method: in this method, deuter-
ated acetylene is polymerized under the action of a catalyst to generate the benzene-d6. This method has a high isotope utiliza- tion rate, but a product contains impurities and is difficult to purify, it is not beneficial to large-scale production. At pre- sent, the source of the benzene-d6 in China is mainly dependent on import, and has the disadvantage of being expensive. Therefore, it is necessary to develop a method for preparing the benzene-d6 with high isotope utilization rate, high product purity and simple op- eration.
A purpose of the present invention is to provide a prepara- tion method of a benzene-dé. The method is relatively simple in operation, high in isotope utilization rate, relatively high in yield and high in product purity, achieves the preparation of the benzene-d6, and provides a reference for industrial production of the benzene-dé.
The purpose of the present invention is achieved by the fol- lowing technical schemes.
A preparation method for a benzene-d6, including the follow- ing steps:
Step 1, slowly adding a hexahalogenated benzene to a solvent in a dry room temperature environment, wherein the mass ratio of the hexahalogenated benzene to the solvent is 1:(80~100), stirring at a speed of 200-300 rpm, and stirring for 0.5~1 hour, to obtain clear solution A;
Step 2, transferring the clear solution A obtained in the
Step 1 to a high-pressure kettle, slowly adding a deuterated rea- gent B to the solution A under a condition of nitrogen protection, wherein the molar ratio of the deuterated reagent B to the hexa- halogenated benzene is (2~12):1, maintaining the solution tempera- ture not to be higher than 25°C in the adding process, and after adding the deuterated reagent B, adding a catalyst to mixed solu- tion, wherein the mass ratio of the hexahalogenated benzene to the catalyst is (10~15):1, and after no bubbles emerge in the solu- tion, sealing a reaction system, checking the air tightness of a device, then replacing a gas in the high-pressure kettle with a deuterium gas, filling the high-pressure kettle with the deuterium gas after replacing for 3~5 times, and while the pressure in the kettle reaches 1~3 MPa, closing an air inlet valve, stirring at a rate of 400-600 rpm and raising the temperature to 35~70°C, keep- ing the temperature for 12~24 hours, stopping the stirring and naturally cooling to a room temperature, to obtain mixed solution
C; and
Step 3, filtering the mixed solution C obtained in the Step 2, transferring a filtrate to a container and placing in a high- precision medium-temperature circulating bath of -5~0°C, and slow- ly adding deionized water of which the temperature is not higher than 5°C dropwise to the filtrate at a rate of 3~9 mL/min by a constant-pressure dropping funnel, stopping the dropwise adding while no bubbles are generated, adding 3-5 grains of zeolites to the solution, fractionating the solution, and taking a fraction at 78.8°C, to obtain the benzene-d6.
In the Step 1, the hexahalogenated benzene is one of hex- afluorobenzene, hexzachlorobenzene, hexabromobenzene and hexaiodo- benzene.
In the Step 1, the solvent is one of anhydrous ether, anhy- drous tetrahydrofuran, anhydrous dichloromethane, anhydrous chlo- roform and anhydrous acetone.
In the Step 2, the deuterated reagent B is one of lithium aluminum deuteride, lithium deuteride and sodium borodeuteride.
The catalyst in the Step 2 is a palladium-carbon catalyst (the palladium content is 10%) or a platinum-carbon catalyst (the platinum content is 10%).
All steps are performed in a drying room, and the relative humidity of air in the drying room is 5%~15%.
Beneficial effect (1) The present invention provides a preparation method for a benzene-d6, and compared with the supercritical deuterium oxide exchange, this method is relatively mild in reaction conditions; and the reaction achieves the effect of simultaneous deuteration of six reaction sites, it does not need to be repeatedly operated, the production cycle is short, and it is suitable for industrial scale-up production;
(2) the obtained benzene-d6 is high in purity, and the yield may reach up to 80.6%; and (3) a high-pressure deuterium gas atmosphere promotes the forward progress of the reaction, and the use of the catalyst re- duces the amount of the deuterated reagent, so the production cost is reduced, and the dependence of domestic markets on imports may be effectively broken.
The content of the present invention is further described be- low in combination with embodiments.
Embodiment 1
In a dry room temperature environment, 14.2 g of a hexachlo- robenzene is slowly added to 1200 g of anhydrous ether, it is stirred at a rate of 200 rpm, and after being stirred for 0.5 hours, clear solution A is obtained; the clear solution A is transferred to a high-pressure kettle with a volume of 3000 mL, 8.4 g of a lithium aluminum deuteride is slowly added to the clear solution A under a condition of nitrogen protection, the solution temperature is maintained not to be higher than 25°C in the adding process, and after the lithium aluminum deuteride is completely added, 1.4 g of a palladium-carbon catalyst is added to mixed so- lution, and after no bubbles emerge in the solution, a reaction system is sealed, the air tightness of a device is checked, then a gas in the kettle is replaced with a deuterium gas, and after be- ing replaced for 3 times, the high-pressure kettle is filled with the deuterium gas, an air inlet valve is closed while the pressure in the kettle reaches 1.5 MPa, and it is stirred at a rate of 600 rpm and the temperature is raised to 45°C, after the temperature is kept for 24 hours, the stirring is stopped and it is naturally cooled to a room temperature; and it is filtered, a filtrate is transferred to a three-port pressure-resistant device with a vol- ume of 3000 mL and placed in a high-precision medium-temperature circulating bath at -5°C, 5°C of deionized water is slowly added dropwise to the filtrate at a rate of 3 mL/min by a constant- pressure dropping funnel, the dropwise adding is stopped while no bubbles are generated, 3 grains of zeolites are added to the solu-
tion, the solution is fractionated, and the solution is heated at a heating rate of 5°C/min, and 78.8°C of a fraction is taken to obtain 3.1 g of the benzene-d6, wherein the product yield is 73.6%, and the purity is 99.1%. 5 Embodiment 2
In a dry room temperature environment, 31.3 g of a hexachlo- robenzene is slowly added to 2800 g of anhydrous ether, it is stirred at a rate of 250 rpm, and after being stirred for 0.6 hours, clear solution A is obtained; the clear solution A is transferred to a high-pressure kettle with a volume of 6000 mL, 11.8 g of a lithium aluminum deuteride is slowly added to the clear solution A under a condition of nitrogen protection, the so- lution temperature is maintained not to be higher than 25°C in the adding process, and after the lithium aluminum deuteride is com- pletely added, 3.1 g of a palladium-carbon catalyst is added to mixed solution, and after no bubbles emerge in the solution, a re- action system is sealed, the air tightness of a device is checked, then a gas in the kettle is replaced with a deuterium gas, and af- ter being replaced for 3 times, the high-pressure kettle is filled with the deuterium gas, an air inlet valve is closed while the pressure in the kettle reaches 3 MPa, and it is stirred at a rate of 600 rpm and the temperature is raised to 50°C, after the tem- perature is kept for 24 hours, the stirring is stopped and it is naturally cooled to a room temperature; and it is filtered, a fil- trate is transferred to a three-port pressure-resistant device with a volume of 6000 mL and placed in a high-precision medium- temperature circulating bath at -5°C, 5°C of deionized water is slowly added dropwise to the filtrate at a rate of 4 mL/min by a constant-pressure dropping funnel, the dropwise adding is stopped while no bubbles are generated, 5 grains of zeolites are added to the solution, the solution is fractionated, and the solution is heated at a heating rate of 5°C/min, and 78.8°C of a fraction is taken to obtain 7.7 g of the benzene-d6, wherein the product yield is 83.7%, and the purity is 99.3%.
Embodiment 3
In a dry room temperature environment, 49.6 g of a hexabromo- benzene is slowly added to 4000 g of anhydrous tetrahydrofuran, it is stirred at a rate of 250 rpm, and after being stirred for 1 hours, clear solution A is obtained; the clear solution A is transferred to a high-pressure kettle with a volume of 10 L, 18.8 g of a sodium borodeuteride is slowly added to the clear solution
A under a condition of nitrogen protection, the solution tempera- ture is maintained not to be higher than 25°C in the adding pro- cess, and after the sodium borodeuteride is completely added, 5.0 g of a palladium-carbon catalyst is added to mixed solution, and after no bubbles emerge in the solution, a reaction system is sealed, the air tightness of a device is checked, then a gas in the kettle is replaced with a deuterium gas, and after being re- placed for 3 times, the high-pressure kettle is filled with the deuterium gas, an air inlet valve is closed while the pressure in the kettle reaches 3 MPa, and it is stirred at a rate of 550 rpm and the temperature is raised to 65°C, after the temperature is kept for 24 hours, the stirring is stopped and it is naturally cooled to a room temperature; and it is filtered, a filtrate is transferred to a three-port pressure-resistant device with a vol- ume of 10 L and placed in a high-precision medium-temperature cir- culating bath at -5°C, 5°C of deionized water is slowly added dropwise to the filtrate at a rate of 6 mL/min by a constant- pressure dropping funnel, the dropwise adding is stopped while no bubbles are generated, 5 grains of zeolites are added to the solu- tion, the solution is fractionated, and the solution is heated at a heating rate of 8°C/min, and 78.8°C of a fraction is taken to obtain 6.5 g of the benzene-d6, wherein the product yield is 86.3%, and the purity is 99.3%.
Embodiment 4
In a dry room temperature environment, 66.2 g of a hexabromo- benzene is slowly added to 6000 g of anhydrous tetrahydrofuran, it is stirred at a rate of 250 rpm, and after being stirred for 1 hours, clear solution A is obtained; the clear solution A is transferred to a high-pressure kettle with a volume of 12 L, 25.4 g of a lithium aluminum deuteride is slowly added to the clear so- lution A under a condition of nitrogen protection, the solution temperature is maintained not to be higher than 25°C in the adding process, and after the lithium aluminum deuteride is completely added, 6.6 g of a platinum-carbon catalyst is added to mixed solu- tion, and after no bubbles emerge in the solution, a reaction sys- tem is sealed, the air tightness of a device is checked, then a gas in the kettle is replaced with a deuterium gas, and after be- ing replaced for 3 times, the high-pressure kettle is filled with the deuterium gas, an air inlet valve is closed while the pressure in the kettle reaches 3 MPa, and it is stirred at a rate of 600 rpm and the temperature is raised to 65°C, after the temperature is kept for 24 hours, the stirring is stopped and it is naturally cooled to a room temperature; and it is filtered, a filtrate is transferred to a three-port pressure-resistant device with a vol- ume of 12 L and placed in a high-precision medium-temperature cir- culating bath at -5°C, 5°C of deionized water is slowly added dropwise to the filtrate at a rate of 9 mL/min by a constant- pressure dropping funnel, the dropwise adding is stopped while no bubbles are generated, 5 grains of zeolites are added to the solu- tion, the solution is fractionated, and the solution is heated at a heating rate of 5°C/min, and 78.8°C of a fraction is taken to obtain 9.1 g of the benzene-d6, wherein the product yield is 90.6%, and the purity is 99.6%.
Embodiment 5
In a dry room temperature environment, 27.9 g of a hex- afluorobenzene is slowly added to 2500 g of anhydrous tetrahydro- furan, it is stirred at a rate of 250 rpm, and after being stirred for 1 hours, clear solution A is obtained; the clear solution A is transferred to a high-pressure kettle with a volume of 6 L, 75.6 g of a lithium aluminum deuteride is slowly added to the clear solu- tion A under a condition of nitrogen protection, the solution tem- perature is maintained not to be higher than 25°C in the adding process, and after the lithium aluminum deuteride is completely added, 2.8 g of a platinum-carbon catalyst is added to mixed solu- tion, and after no bubbles emerge in the solution, a reaction sys- tem is sealed, the air tightness of a device is checked, then a gas in the kettle is replaced with a deuterium gas, and after be- ing replaced for 3 times, the high-pressure kettle is filled with the deuterium gas, an air inlet valve is closed while the pressure in the kettle reaches 2 MPa, and it is stirred at a rate of 500 rpm and the temperature is raised to 70°C, after the temperature is kept for 24 hours, the stirring is stopped and it is naturally cooled to a room temperature; and it is filtered, a filtrate is transferred to a three-port pressure-resistant device with a vol- ume of 6 L and placed in a high-precision medium-temperature cir- culating bath at -5°C, 5°C of deionized water is slowly added dropwise to the filtrate at a rate of 5 mL/min by a constant- pressure dropping funnel, the dropwise adding is stopped while no bubbles are generated, 3 grains of zeolites are added to the solu- tion, the solution is fractionated, and the solution is heated at a heating rate of 5°C/min, and 78.8°C of a fraction is taken to obtain 9.0 g of the benzene-d6, wherein the product yield is 88.9%, and the purity is 99.5%.
The above specific descriptions further describe the purpos- es, technical schemes and beneficial effects of the present inven- tion in detail. It should be understood that the above are only specific embodiments of the present invention, and are not intend- ed to limit a scope of protection of the present invention. Any modifications, equivalent replacements, improvements and the like made within the spirit and principle of the present invention shall be included within the scope of protection of the present invention.
Claims (3)
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|---|---|---|---|
| NL2032470A NL2032470B1 (en) | 2022-07-12 | 2022-07-12 | Preparation method for benzene-d6 |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL2032470A NL2032470B1 (en) | 2022-07-12 | 2022-07-12 | Preparation method for benzene-d6 |
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| NL2032470B1 true NL2032470B1 (en) | 2024-01-25 |
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