CN116496310B - Preparation method and preparation device of precursor N, N' -trimethyl borane triamine - Google Patents
Preparation method and preparation device of precursor N, N' -trimethyl borane triamine Download PDFInfo
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- CN116496310B CN116496310B CN202310584097.4A CN202310584097A CN116496310B CN 116496310 B CN116496310 B CN 116496310B CN 202310584097 A CN202310584097 A CN 202310584097A CN 116496310 B CN116496310 B CN 116496310B
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- 229910052757 nitrogen Inorganic materials 0.000 title claims abstract description 72
- 238000002360 preparation method Methods 0.000 title claims abstract description 31
- 239000002243 precursor Substances 0.000 title claims description 13
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims abstract description 50
- 238000006243 chemical reaction Methods 0.000 claims abstract description 50
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 28
- 239000007789 gas Substances 0.000 claims abstract description 27
- FAQYAMRNWDIXMY-UHFFFAOYSA-N trichloroborane Chemical compound ClB(Cl)Cl FAQYAMRNWDIXMY-UHFFFAOYSA-N 0.000 claims abstract description 25
- 238000003756 stirring Methods 0.000 claims abstract description 21
- 239000007788 liquid Substances 0.000 claims abstract description 20
- 230000015572 biosynthetic process Effects 0.000 claims abstract description 19
- 238000003786 synthesis reaction Methods 0.000 claims abstract description 19
- 239000003960 organic solvent Substances 0.000 claims abstract description 10
- 239000012429 reaction media Substances 0.000 claims abstract description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 6
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 5
- 239000000203 mixture Substances 0.000 abstract description 15
- 239000002904 solvent Substances 0.000 abstract description 9
- 238000000926 separation method Methods 0.000 abstract description 8
- 239000012452 mother liquor Substances 0.000 abstract description 5
- UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 abstract description 4
- 229910000085 borane Inorganic materials 0.000 abstract description 2
- 229910000831 Steel Inorganic materials 0.000 description 17
- 239000010959 steel Substances 0.000 description 17
- 239000012071 phase Substances 0.000 description 7
- 238000003860 storage Methods 0.000 description 5
- 238000009776 industrial production Methods 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000007791 liquid phase Substances 0.000 description 3
- 238000007789 sealing Methods 0.000 description 3
- 150000003384 small molecules Chemical class 0.000 description 3
- PLDAEAHODDBZCL-UHFFFAOYSA-N toluene;trichloroborane Chemical compound ClB(Cl)Cl.CC1=CC=CC=C1 PLDAEAHODDBZCL-UHFFFAOYSA-N 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- NQMRYBIKMRVZLB-UHFFFAOYSA-N methylamine hydrochloride Chemical compound [Cl-].[NH3+]C NQMRYBIKMRVZLB-UHFFFAOYSA-N 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- VXEGSRKPIUDPQT-UHFFFAOYSA-N 4-[4-(4-methoxyphenyl)piperazin-1-yl]aniline Chemical compound C1=CC(OC)=CC=C1N1CCN(C=2C=CC(N)=CC=2)CC1 VXEGSRKPIUDPQT-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 229910003902 SiCl 4 Inorganic materials 0.000 description 1
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- BGECDVWSWDRFSP-UHFFFAOYSA-N borazine Chemical class B1NBNBN1 BGECDVWSWDRFSP-UHFFFAOYSA-N 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- 239000012700 ceramic precursor Substances 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000005049 silicon tetrachloride Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000008096 xylene Substances 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
- B01J19/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J19/18—Stationary reactors having moving elements inside
-
- 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
- B01J4/00—Feed or outlet devices; Feed or outlet control devices
- B01J4/001—Feed or outlet devices as such, e.g. feeding tubes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
- C07F5/022—Boron compounds without C-boron linkages
-
- 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
- B01J2204/00—Aspects relating to feed or outlet devices; Regulating devices for feed or outlet devices
- B01J2204/002—Aspects relating to feed or outlet devices; Regulating devices for feed or outlet devices the feeding side being of particular interest
-
- 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
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E60/00—Enabling technologies; Technologies with a potential or indirect contribution to GHG emissions mitigation
- Y02E60/10—Energy storage using batteries
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
Abstract
The invention belongs to the technical field of borane preparation, and particularly relates to a preparation method and a preparation device of N, N' -trimethyl borane triamine. Organic solvent is taken as a reaction medium, the organic solvent is put into a dry synthesis device, after air is replaced by nitrogen, the synthesis device is sealed, cooled and stirred, stirring is continued until the reaction is completed, when the temperature is reduced to-20-0 ℃, liquid boron trichloride is put into the synthesis device, the reaction temperature and the reaction pressure are controlled, the reaction temperature is-20-0 ℃, and monomethylamine gas is introduced for reaction to prepare a solid-liquid mixture; and under the protection of nitrogen, recovering the obtained solid-liquid mixture to room temperature, transferring the mixture into centrifugal separation equipment, and removing the solvent from the obtained mother liquor to obtain N, N' -trimethyl borane triamine. The preparation method and the device adopted by the invention greatly improve the yield of the product.
Description
Technical Field
The invention belongs to the technical field of borane preparation, and particularly relates to a preparation method and a preparation device of a precursor N, N' -trimethyl borane triamine.
Background
N, N' -trimethyl borane triamine is a key intermediate of ceramic precursor borazine series products, the preparation is prepared by reacting boron trichloride gas and monomethylamine gas, the gas and the gas react with each other at great risk, and the gas escapes and other problems are caused, so that raw materials are wasted, environmental pollution is caused, the reaction is insufficient, the yield is low and other problems are caused.
Patent CN101913877a, publication time 2010.12.15. Discloses a preparation method of a silazane ceramic fiber precursor, which comprises the following steps: the method comprises the steps of firstly using boron trichloride (BCl) 3 ) And methylamine (CH) 3 NH 2 ) Reacting for 12-18 h at-80 ℃ and reacting for 12-18 h at-40 ℃ to synthesize B (NHCH) 3 ) 3 Small molecules, silicon tetrachloride (SiCl 4 ) And methylamine (CH) 3 NH 2 ) Synthesis of Si (NHCH) 3 ) 4 A small molecule; the two small molecules are mixed after excessive methylamine is removed and filtered, and the precursor with good filament picking effect is obtained through polycondensation reaction at 135-165 ℃. However, the preparation method has lower temperature, is unfavorable for the reaction of boron trichloride and monomethylamine, greatly reduces the product yield once the amount of single-batch reactants is increased, and cannot be used for the industrial production of the product with high yield.
In conclusion, the prior art can prepare N, N' -trimethyl borane triamine, but the preparation method has the problems of harsh reaction conditions, difficult industrial production, insufficient reaction, low yield and the like.
Disclosure of Invention
Aiming at the defects of the prior art, the invention aims to provide a preparation method of a precursor N, N' -trimethyl borane triamine, which adopts a method of introducing monomethylamine gas into boron trichloride liquid for reaction, so that the reaction can be carried out under milder conditions, industrial production is realized, raw material reaction is more complete, and the yield is higher.
The invention also aims to provide a preparation device used in the preparation method of the precursor N, N' -trimethylborane triamine, and the escape of monomethylamine and boron trichloride is reduced by sealing the reaction kettle, so that the product yield is improved.
The technical scheme adopted by the invention is as follows:
the preparation method of the precursor N, N' -trimethyl borane triamine comprises the steps of taking an organic solvent as a reaction medium, putting the organic solvent into a dry synthesis device, replacing air by nitrogen, sealing the synthesis device, cooling and starting stirring until the reaction is completed, putting liquid boron trichloride into the synthesis device when the temperature is reduced to-20-0 ℃, controlling the reaction temperature and the reaction pressure, and introducing monomethylamine gas for reaction to obtain a solid-liquid mixture; and under the protection of nitrogen, recovering the obtained solid-liquid mixture to room temperature, transferring the mixture into centrifugal separation equipment, and removing the solvent from the obtained mother liquor to obtain N, N' -trimethyl borane triamine.
The reaction equation is as follows:
the organic solvent is one of toluene, xylene, cyclohexane and n-hexane.
The molar ratio of the boron trichloride to the monomethylamine is 1: (3-3.55).
The reaction temperature is-20-0 ℃.
The mass ratio of the organic solvent to the boron trichloride is as follows: (15-25): 1.
the stirring rotation speed is 100-150 r/min, and the reaction pressure is 0-1.5 MPa.
The preparation device used in the preparation method of the N, N' -trimethyl borane triamine comprises a monomethylamine steel bottle, a solvent storage tank, a closed reaction kettle and a boron trichloride steel bottle, wherein the monomethylamine steel bottle is connected with the closed reaction kettle through a gas phase feeding pipeline, the solvent storage tank is connected with the closed reaction kettle through a diaphragm pump, the boron trichloride steel bottle is connected with the closed reaction kettle through a liquid phase feeding pipeline, and the nitrogen steel bottle is connected with the boron trichloride steel bottle through a gas phase pipeline.
The closed reaction kettle is internally provided with a gas distributor, and the gas distributor is connected with a monomethylamine steel bottle through a gas phase feeding pipeline.
Compared with the prior art, the invention has the following beneficial effects:
(1) The method adopts the monomethylamine gas to introduce the boron trichloride liquid for reaction, so that the reaction can be carried out at the initial reaction temperature of-20 ℃, industrial production is realized, the raw material reaction is more complete, and the yield is higher.
(2) The invention adopts closed reaction, solves the escape problem of boron trichloride and monomethylamine, improves the utilization rate of raw materials, greatly improves the contact area of gas phase and liquid phase in the reaction process by adding the gas distributor, and improves the reaction rate.
Drawings
FIG. 1 is a schematic structural diagram of a preparation device of a precursor N, N' -trimethylborane triamine;
FIG. 2 is a liquid mass spectrum of N, N' -trimethylborane triamine synthesized in example 1 of the present invention;
FIG. 3 is a nuclear magnetic resonance hydrogen spectrum of N, N' -trimethylborane triamine synthesized in example 1 of the present invention;
in the figure: 1. a methylamine steel cylinder; 2. a diaphragm pump; 3. a solvent storage tank; 4. sealing the reaction kettle; 5. boron trichloride steel cylinder; 6. a nitrogen steel cylinder; 7. a gas distributor.
Detailed Description
The invention is further illustrated below with reference to examples, which are not intended to limit the practice of the invention.
As shown in figure 1, the preparation device used in the preparation method of N, N' -trimethylborane triamine comprises a monomethylamine steel bottle 1, a solvent storage tank 3, a closed reaction kettle 4 and a boron trichloride steel bottle 5, wherein the monomethylamine steel bottle 1 is connected with the closed reaction kettle 4 through a gas phase feeding pipeline, the solvent storage tank 3 is connected with the closed reaction kettle 4 through a diaphragm pump 2, the boron trichloride steel bottle 5 is connected with the closed reaction kettle 4 through a liquid phase feeding pipeline, and a nitrogen steel bottle 6 is connected with the boron trichloride steel bottle 5 through a gas phase pipeline. The gas distributor 7 is arranged in the closed reaction kettle 4, and the gas distributor 7 is connected with the monomethylamine steel bottle 1 through a gas phase feeding pipeline.
The following examples were prepared using the preparation apparatus used in the above-described preparation method of N, N' -trimethylborane triamine.
Example 1
The preparation method of the N, N' -trimethylborane triamine comprises the following steps:
(1) Firstly, using high-purity nitrogen to replace air and water vapor in a synthesis device and a solid-liquid separation device, putting 1100L of toluene into the synthesis device, starting stirring (stirring rotation speed is 120 r/min), and keeping the temperature in a kettle at-20 ℃;
(2) Accurately metering 65kg of boron trichloride into a synthesis device by a metering device, and fully stirring for 1h (stirring rotation speed 120 r/min);
(3) Introducing dried 50kg of monomethylamine gas into a continuously stirred boron trichloride toluene solution, keeping the reaction temperature at-20 ℃, keeping the container closed, keeping the reaction pressure at 0.7MPa, continuously stirring for 20 hours, and controlling the stirring rotating speed at 150r/min to obtain a solid-liquid mixture;
(4) Under the protection of nitrogen, transferring the solid-liquid mixture obtained in the step three into centrifugal separation equipment after the solid-liquid mixture is restored to room temperature, controlling the rotating speed to 1800r/min, and removing the solvent from the obtained mother liquor to obtain 53.31kg of N, N' -trimethylborane triamine, wherein the yield is 95%; LC-MS, m/z:102.1; 1 H NMR (400 MHz, Chloroform-d) δ 2.69 (s, 9H, -CH 3 ), 1.46 (s, 3H, -NH)。
example 2
The preparation method of the N, N' -trimethylborane triamine comprises the following steps:
(1) Firstly, air and steam in a synthesis device and a solid-liquid separation device are replaced by high-purity nitrogen, 1080L of dimethylbenzene is put into the synthesis device, stirring is started (stirring rotation speed is 120 r/min), and the temperature in a kettle is kept at 0 ℃.
(2) 60kg of boron trichloride is accurately metered into the synthesis device by the metering device, and is fully stirred for 1h (stirring rotation speed is 120 r/min).
(3) Introducing dry 55kg of monomethylamine gas into a continuously stirred boron trichloride toluene solution, keeping the reaction temperature at 0 ℃, keeping the container closed, keeping the reaction pressure at 1.2MPa, continuously stirring for 20h, and controlling the stirring rotating speed at 120r/min to obtain a solid-liquid mixture.
(4) Under the protection of nitrogen, after the solid-liquid mixture obtained in the step III is restored to room temperature, transferring the mixture into centrifugal separation equipment, controlling the rotating speed to 1800r/min, and removing the solvent from the obtained mother liquor to obtain 46.15kg of N, N' -trimethylborane triamine, wherein the yield is 89.1%.
Comparative example 1
The preparation method of the N, N' -trimethylborane triamine comprises the following steps:
(1) Firstly, air and water vapor in a synthesis device and a solid-liquid separation device are replaced by high-purity nitrogen, 1100L of n-pentane is taken as a reaction solvent to be put into the synthesis device, stirring is started (stirring rotation speed is 120 r/min), and the temperature in a kettle is kept at minus 20 ℃.
(2) 65kg of boron trichloride is accurately metered into the synthesis device by the metering device, and is fully stirred for 1h (stirring rotation speed 120 r/min).
(3) Adding monomethylamine hydrochloride into a sodium hydroxide solution to obtain 50kg of monomethylamine gas, drying, introducing the monomethylamine gas into a continuously stirred boron trichloride toluene solution, keeping the reaction temperature at-20 ℃, keeping the container closed, keeping the reaction pressure at 0.7MPa, continuously stirring for 20h, and controlling the stirring rotating speed at 150r/min to obtain a solid-liquid mixture.
(4) Under the protection of nitrogen, after the solid-liquid mixture obtained in the step III is restored to room temperature, transferring the mixture into centrifugal separation equipment, controlling the rotating speed to 1800r/min, and carrying out reduced pressure distillation on the obtained mother liquor to obtain 38.72kg of N, N' -trimethylborane triamine, wherein the yield is 69.0%.
The above results show that the yield of the obtained N, N '-and N' -trimethyl borane triamine is high and can reach about 90% by adopting the preparation method and the device of the invention; the comparative example uses monomethylamine hydrochloride to react, and the yield is only 69%.
Claims (4)
1. The preparation method of the precursor N, N '-trimethyl borane triamine is characterized in that an organic solvent is taken as a reaction medium, the organic solvent is put into a dry synthesis device, air is replaced by nitrogen, the synthesis device is sealed, the temperature is reduced, stirring is started until the reaction is completed, when the temperature is reduced to-20-0 ℃, liquid boron trichloride is put into the synthesis device, the reaction temperature and the reaction pressure are controlled, the reaction temperature is-20-0 ℃, and monomethylamine gas is introduced for reaction to prepare N, N' -trimethyl borane triamine;
the organic solvent is one of toluene and dimethylbenzene.
2. The method for preparing the precursor N, N' -trimethylborane triamine according to claim 1, wherein the molar ratio of the boron trichloride to the monomethylamine is 1: (3-3.55).
3. The method for preparing precursor N, N' -trimethylborane triamine according to claim 1, wherein the mass ratio of the organic solvent to boron trichloride is (15-25): 1.
4. the method for preparing the precursor N, N' -trimethylborane triamine according to claim 1, wherein the stirring speed is 100-150 r/min, and the reaction pressure is 0-1.5 MPa.
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