CN104402918B - A kind of preparation method of the double tetraethyl ammonium of decahydro ten boric acid - Google Patents
A kind of preparation method of the double tetraethyl ammonium of decahydro ten boric acid Download PDFInfo
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- CN104402918B CN104402918B CN201410738891.0A CN201410738891A CN104402918B CN 104402918 B CN104402918 B CN 104402918B CN 201410738891 A CN201410738891 A CN 201410738891A CN 104402918 B CN104402918 B CN 104402918B
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- decahydro
- double
- boric acid
- catalyst
- tetraethyl ammonium
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- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 title claims abstract description 20
- 239000004327 boric acid Substances 0.000 title claims abstract description 20
- CBXCPBUEXACCNR-UHFFFAOYSA-N tetraethylammonium Chemical compound CC[N+](CC)(CC)CC CBXCPBUEXACCNR-UHFFFAOYSA-N 0.000 title claims abstract description 20
- 238000002360 preparation method Methods 0.000 title description 6
- 239000003054 catalyst Substances 0.000 claims abstract description 21
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims abstract description 18
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 18
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract description 12
- 238000006243 chemical reaction Methods 0.000 claims abstract description 10
- 239000000706 filtrate Substances 0.000 claims abstract description 10
- 238000000034 method Methods 0.000 claims abstract description 9
- YMBCJWGVCUEGHA-UHFFFAOYSA-M tetraethylammonium chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC YMBCJWGVCUEGHA-UHFFFAOYSA-M 0.000 claims abstract description 9
- 239000005662 Paraffin oil Substances 0.000 claims abstract description 8
- 239000002131 composite material Substances 0.000 claims abstract description 8
- 238000001914 filtration Methods 0.000 claims abstract description 8
- 229910000033 sodium borohydride Inorganic materials 0.000 claims abstract description 8
- 239000012279 sodium borohydride Substances 0.000 claims abstract description 8
- 239000008367 deionised water Substances 0.000 claims abstract description 7
- 229910021641 deionized water Inorganic materials 0.000 claims abstract description 7
- 239000000047 product Substances 0.000 claims abstract description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 7
- 239000003208 petroleum Substances 0.000 claims abstract description 6
- 239000012065 filter cake Substances 0.000 claims abstract description 5
- 239000000203 mixture Substances 0.000 claims abstract description 5
- 238000003756 stirring Methods 0.000 claims abstract description 5
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 10
- 238000010992 reflux Methods 0.000 claims description 8
- PNEYBMLMFCGWSK-UHFFFAOYSA-N Alumina Chemical compound [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 6
- 239000010949 copper Substances 0.000 claims description 5
- 229910052782 aluminium Inorganic materials 0.000 claims description 4
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 4
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 claims description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 claims description 3
- 239000000395 magnesium oxide Substances 0.000 claims description 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 229910052802 copper Inorganic materials 0.000 claims description 2
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 claims description 2
- 229910044991 metal oxide Inorganic materials 0.000 claims description 2
- 150000004706 metal oxides Chemical group 0.000 claims description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims 1
- DZUYMRNKBBRIEO-UHFFFAOYSA-N C(C)Cl(CC)(CC)CC Chemical compound C(C)Cl(CC)(CC)CC DZUYMRNKBBRIEO-UHFFFAOYSA-N 0.000 claims 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 claims 1
- YOBAEOGBNPPUQV-UHFFFAOYSA-N iron;trihydrate Chemical compound O.O.O.[Fe].[Fe] YOBAEOGBNPPUQV-UHFFFAOYSA-N 0.000 claims 1
- 239000011787 zinc oxide Substances 0.000 claims 1
- 239000007789 gas Substances 0.000 abstract description 4
- 238000001816 cooling Methods 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 6
- 229910052796 boron Inorganic materials 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 3
- 230000005311 nuclear magnetism Effects 0.000 description 3
- 239000003380 propellant Substances 0.000 description 3
- 238000001228 spectrum Methods 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 238000005336 cracking Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 229910052759 nickel Inorganic materials 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- -1 Filtering Substances 0.000 description 1
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 1
- 239000012752 auxiliary agent Substances 0.000 description 1
- 229910000085 borane Inorganic materials 0.000 description 1
- 150000001639 boron compounds Chemical class 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000007233 catalytic pyrolysis Methods 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 238000002485 combustion reaction Methods 0.000 description 1
- 230000009089 cytolysis Effects 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 238000000197 pyrolysis Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- UORVGPXVDQYIDP-UHFFFAOYSA-N trihydridoboron Substances B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a kind of method preparing the double tetraethyl ammonium of decahydro ten boric acid, it comprises the steps: to be sequentially added into tetraethylammonium chloride in the microwave reactor with device for absorbing tail gas, sodium borohydride, composite catalyst, deionized water, paraffin oil, after stirring at 25 DEG C ~ 30 DEG C 300W microwave irradiation 50 ~ 80s, 800W microwave irradiation 40min ~ 1h at 175 ~ 180 DEG C the most again, mixture reaction obtained takes out and filters with petroleum ether, the backflow of acetonitrile post-heating is added in filter cake, cooling, filter, the methanol that volume fraction is 85% is added after filtrate being evaporated, heated backflow, heat filter, filtrate cools down, the double tetraethyl ammonium product of white crystalline decahydro ten boric acid is obtained after filtration.The present invention has easy and simple to handle, and the response time is short, product yield advantages of higher.
Description
Technical field
The invention belongs to the field of chemical synthesis, be specifically related to the preparation method of the double tetraethyl ammonium of a kind of decahydro ten boric acid.
Background technology
Ion-type boron hydracid salt superelevation burning ratemodifier has the advantages such as fuel value height, low, the good stability of toxicity, with carbon
Borine is compared has synthesis conveniently, lower-cost feature.The U.S. starts this compounds in nineteen seventies
Preparation and research, wherein, it is equal for composite propellant and double base propellant that United States Patent (USP) US4138282 discloses this compounds
It is remarkably improved the combustion speed of propellant.Wherein the double tetraethyl ammonium of decahydro ten boric acid is the ion-type boron hydrogen that a kind of using value is higher
Hydrochlorate, reports that " the research I. of boron compound synthesizes ten boron decahydro (B " journal chemistry " the 4th phase in 197810H10 2-) new side
Method, it uses method double tetraethyl ammonium of synthesis decahydro ten boric acid that oil bath is pyrolyzed, and the response time is long, product yield low (40% with
Under), therefore, it is badly in need of at present its preparation method is improved.
Summary of the invention
It is an object of the invention to overcome the deficiencies in the prior art, it is provided that a kind of reactions steps is few, yield is high, easy and simple to handle
The preparation method of the double tetraethyl ammonium of decahydro ten boric acid.
For achieving the above object, the present invention, with sodium borohydride, tetraethylammonium chloride as raw material, uses microwave cracking to be prepared into
To the double tetraethyl ammonium of decahydro ten boric acid.Specifically adopt the following technical scheme that
A kind of method preparing the double tetraethyl ammonium of decahydro ten boric acid, is realized by following steps:
In the microwave reactor with device for absorbing tail gas, it is sequentially added into sodium borohydride, tetraethylammonium chloride, is combined and urges
Agent, deionized water, paraffin oil, after stirring at 25 ~ 30 DEG C 300W microwave irradiation 50 ~ 80s；Again at 175 ~ 180 DEG C
800W microwave irradiation 40min ~ 1h, the mixture then reaction obtained takes out, and filters, filter after filtration after adding petroleum ether
Cake adds acetonitrile, cold filtration after being heated to reflux 50 ~ 60min at 80 ~ 85 DEG C, after filtrate being evaporated, adds volume integral
Number is the methanol of 85%, is heated to reflux 20 ~ 40min after heat filter at 65 ~ 70 DEG C, and filtrate cools down, obtains ten after filtered at room temperature
The double tetraethyl ammonium product of hydrogen ten boric acid.Reaction equation is as follows:
In above-mentioned steps, composite catalyst is composited by catalyst A and catalyst promoter B, and wherein catalyst A is metal
One in nickel (Ni) or copper (Cu), preferably nickel (Ni)；Catalyst promoter B is metal oxide magnesium (MgO), aluminium oxide
(Al2O3), ferrum oxide (Fe2O3), any one in zinc oxide (ZnO) etc., preferential oxidation aluminum (Al2O3)；Catalyst A and catalyst
The mass ratio of auxiliary agent B is: 1:1 ~ 3, and total consumption is the 0.1 ~ 0.3% of tetraethylammonium chloride quality.
In above-mentioned steps, tetraethylammonium chloride, sodium borohydride, deionized water, the mass ratio of paraffin oil are 1:0.1 ~ 0.4:
0.2 ~ 0.6:2 ~ 3.
In above-mentioned steps, petroleum ether consumption is 2 times of paraffin oil quality；Filter cake is 1:10 ~ 20 with the mass ratio of acetonitrile；Filter
The mass ratio going out the methanol that thing and volume fraction are 85% is 1:2 ~ 5.
The synthesis technique of present invention tetraethyl ammonium double to decahydro ten boric acid is significantly improved, and has following useful effect
Really: (1) uses microwave cracking to enormously simplify reactions steps, shortens the response time, reaction is made to be more convenient for operating；(2) compound
The electromagnetic energy of microwave can be converted into heat energy by catalyst effectively, it is provided that energy necessary to pyrolysis and catalytic pyrolysis, significantly carries
High lysis efficiency, and wherein the addition of catalyst aid can further enhance the interaction between component, promotes catalysis activity, significantly
Shorten the response time.(3) reaction yield reaches more than 90%.
Accompanying drawing explanation
Fig. 1 is decahydro ten boric acid double tetraethyl ammonium nuclear-magnetism boron spectrogram spectrum that the present invention prepares.
Detailed description of the invention
Below by way of several preferred embodiments, synthetic method of the present invention is described in further detail, but the protection of the present invention
Scope is not limited thereto.
Embodiment 1
It is sequentially added into sodium borohydride 34g, tetraethylammonium chloride 166g, Ni and oxygen in the microwave reactor that hot tail gas absorbs
Change aluminum composite catalyst 0.2g, deionized water 50g, paraffin oil 332g, after stirring, 300W microwave irradiation 50s at 25 DEG C,
Then 800W microwave irradiation 1 hour at 175 ~ 180 DEG C, the mixture then reaction obtained takes out, and disperses with 664g petroleum ether,
Filtering, filter cake adds acetonitrile 500g, is heated to reflux cold filtration after 1 hour, adds body after filtrate being evaporated at 80 ~ 85 DEG C
Long-pending percentage ratio 85% methanol 100g, is heated to reflux after heat filter half an hour at 65 ~ 70 DEG C, filtrate cools down, and filtered at room temperature obtains white
The double tetraethyl ammonium product 34.6g(yield 91.5% of color crystalloid decahydro ten boric acid).(nuclear-magnetism boron spectrogram spectrum is shown in Fig. 1).Ni and oxidation
The mass ratio of aluminum is 1:1.
Embodiment 2
It is sequentially added into sodium borohydride 24g, tetraethylammonium chloride 83g, Cu and oxygen in the microwave reactor that hot tail gas absorbs
Change magnesium composite catalyst 0.2g, deionized water 33g, paraffin oil 240g, after stirring, 300W microwave irradiation 60s at 25 DEG C,
Then 800W microwave irradiation 50min at 175 ~ 180 DEG C, the mixture then reaction obtained takes out, and filters with 480g petroleum ether,
Filter cake adds acetonitrile 400g, is heated to reflux cold filtration after 1 hour, adds 85% methanol after filtrate being evaporated at 80 ~ 85 DEG C
100g, is heated to reflux after heat filter half an hour at 65 ~ 70 DEG C, filtrate cools down, and filtered at room temperature obtains white crystalline decahydro ten
The double tetraethyl ammonium product 17.1g(yield 90.5% of boric acid).The mass ratio of Cu and magnesium oxide is 1:2.(nuclear-magnetism boron spectrogram spectrum is shown in figure
1).
Claims (4)
1. the method preparing the double tetraethyl ammonium of decahydro ten boric acid, it is characterised in that: it is through the following steps that realize:
Microwave reactor with device for absorbing tail gas is sequentially added into sodium borohydride, tetraethylammonium chloride, composite catalyst,
Deionized water, paraffin oil, after stirring at 25 ~ 30 DEG C 300W microwave irradiation 50 ~ 80s；At 175 ~ 180 DEG C, 800W is micro-again
Ripple irradiates 40min ~ 1h, and the mixture then reaction obtained takes out, and filters, add in filter cake after filtration after adding petroleum ether
Entering acetonitrile, cold filtration after being heated to reflux 50 ~ 60min at 80 ~ 85 DEG C, adding volume fraction after filtrate being evaporated is 85%
Methanol, be heated to reflux at 65 ~ 70 DEG C 20 ~ 40min after heat filter, filtrate cool down, obtain decahydro ten boric acid after filtered at room temperature
Double tetraethyl ammonium products；Wherein, described composite catalyst is composited by catalyst A and catalyst promoter B, wherein catalyst
A is the one in metallic nickel or copper；Catalyst promoter B is metal oxide aluminum, magnesium oxide, iron sesquioxide, zinc oxide
In any one；The mass ratio of catalyst A and catalyst promoter B is: 1:1 ~ 3.
The method preparing the double tetraethyl ammonium of decahydro ten boric acid the most as claimed in claim 1, it is characterised in that: described composite catalyzing
The preferred metallic nickel of agent and aluminium oxide.
The method preparing the double tetraethyl ammonium of decahydro ten boric acid the most as claimed in claim 1 or 2, it is characterised in that: described is compound
Catalyst amount is the 0.1 ~ 0.3% of tetraethylammonium chloride quality.
The method preparing the double tetraethyl ammonium of decahydro ten boric acid the most as claimed in claim 1, it is characterised in that: described tetraethyl chlorine
Change ammonium, sodium borohydride, deionized water, the mass ratio of paraffin oil are 1:0.1 ~ 0.4:0.2 ~ 0.6:2 ~ 3.
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| CN201410738891.0A CN104402918B (en) | 2014-12-08 | 2014-12-08 | A kind of preparation method of the double tetraethyl ammonium of decahydro ten boric acid |
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|---|---|---|---|
| CN201410738891.0A CN104402918B (en) | 2014-12-08 | 2014-12-08 | A kind of preparation method of the double tetraethyl ammonium of decahydro ten boric acid |
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| CN104402918A CN104402918A (en) | 2015-03-11 |
| CN104402918B true CN104402918B (en) | 2016-08-24 |
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| EP3125253A1 (en) * | 2015-07-30 | 2017-02-01 | Great South Group Limited | A method and composition for absorbing ionizing radiation |
| CN111573624B (en) * | 2020-06-28 | 2021-10-15 | 郑州原理生物科技有限公司 | Method for preparing dodecahydrododecaboron disodium salt by using byproduct of decahydrododecaboron bistetraethylammonium salt |
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Non-Patent Citations (4)
| Title |
|---|
| 硼化合物的研究 Ⅰ.合成十硼十氢阴离子(B10 H10 2-)的新方法;张国敏等;《化学学报》;19781130;第36卷(第4期);1-4 * |
| 硼氢化合物作为固体推进剂高燃速调节剂的最新进展;唐松青等;《推进技术》;19830531;第35-53页 * |
| 薛云娜等.高燃速调节剂十氢十硼酸双四乙基铵的合成及热性能.《中国化学会第五届全国化学推进剂学术会议• * |
| 论文集》.2010,第382-384页. * |
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Inventor after: Hu Xiaolun Inventor after: Li Yibo Inventor after: Wang Jianli Inventor after: Yang Yong Inventor after: Wang Yajuan Inventor before: Hu Xiaolun Inventor before: Li Yibo Inventor before: Wang Jianli Inventor before: Yang Yong Inventor before: Wang Yajuan |
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Address after: No. 6, No. 4, No. 52, No. 4, Huang Yang Street, high tech Industrial Development Zone, Zhengzhou City, Henan Province, 41 Patentee after: Zhengzhou principle Biological Technology Co., Ltd. Address before: No. 41, No. 4, No. 4, phase 2, long Ding enterprise center of electronic and electrical appliances Industrial Park, Henan Province Patentee before: Zhengzhou Sigma Chemical Co., Ltd. |
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