CN109438526A - Benzoates burningrate catalyst of the group containing biferrocene and preparation method thereof - Google Patents
Benzoates burningrate catalyst of the group containing biferrocene and preparation method thereof Download PDFInfo
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- CN109438526A CN109438526A CN201811497626.2A CN201811497626A CN109438526A CN 109438526 A CN109438526 A CN 109438526A CN 201811497626 A CN201811497626 A CN 201811497626A CN 109438526 A CN109438526 A CN 109438526A
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- burningrate
- burningrate catalyst
- biferrocene
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- 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
- C07F17/00—Metallocenes
- C07F17/02—Metallocenes of metals of Groups 8, 9 or 10 of the Periodic System
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- C—CHEMISTRY; METALLURGY
- C06—EXPLOSIVES; MATCHES
- C06B—EXPLOSIVES OR THERMIC COMPOSITIONS; MANUFACTURE THEREOF; USE OF SINGLE SUBSTANCES AS EXPLOSIVES
- C06B23/00—Compositions characterised by non-explosive or non-thermic constituents
- C06B23/007—Ballistic modifiers, burning rate catalysts, burning rate depressing agents, e.g. for gas generating
Abstract
The invention discloses benzoates burningrate catalysts of a kind of group containing biferrocene and preparation method thereof, and the structural formula of the burningrate catalyst isBurningrate catalyst of the present invention is not easy to migrate under field conditions (factors) and volatilizees, thermal stability is good, due to introducing rich nitrogen groups, itself generation heat with higher and the combustion heat, for in solid propellant, the energy level of solid propellant can be improved in combustion process, and there is preferable combustion catalysis to solid propellant major constituent ammonium perchlorate and hexogen.The preparation method of burningrate catalyst of the present invention is easy to operate, synthesis cost is low, overcomes the disadvantages of existing Ferrocene and its derivative synthesis technology is complicated, expensive, at high cost.
Description
Technical field
The invention belongs to solid propellant technical fields, and in particular to the benzoates of a kind of group containing biferrocene
The preparation method of burningrate catalyst and the burningrate catalyst.
Background technique
Solid propellant (solid gunpowder) gradually develops as a kind of compound energetic material for the purpose of promoting
Come, it is mainly rocket, shell, firearms, guided missile offer driving force, is played in guided missile and aerospace industry development very heavy
The effect wanted, its performance quality play decisive role to the fight capability of weapon guided missile, account in science and techniques of defence cause
According to important position.In order to guarantee that solid propellant rocket ballistic performance and engine operation are stablized, most of strategy and war
Art wishes that the burning rate pressure exponent of solid propellant is lower.And burningrate catalyst can play reduction Propellants With Lower Pressure Exponent
Effect, it is a kind of additive that propellant burning rate is adjusted by physically or chemically acting on, by changing the structure of combustion wave,
To increase or decrease the burn rate of propellant, influence of the pressure index to burn rate is reduced significantly, and the amount of being usually added into is quality point
Between number 1%~5%.As indispensable ingredient a kind of in solid propellant propulsion agent prescription, the research of burningrate catalyst is solid
Biggish development at home and abroad has been obtained in recent decades in one important content of propellant research.
Ferrocene and its derivative is the advantages that its good combustibility, dispersibility, uniformity, compatibility and by extensive
Concern, as normal-butyl ferrocene, tert-butyl ferrocene and Kato it is pungent be to be commercialized at present and be widely used in compound propulsion
Burningrate catalyst is used as in agent.But there are the problems such as easy to migrate, volatile for the ferrocene class burningrate catalyst applied at present, sternly
Storage life, use reliability and the environmental suitability of all kinds of missile propellant powder charges in China are affected again, also virtually substantially
Degree increases the funds expenditure of national defence basis deposit.So researcher has done a large amount of research work and has been attempted to out mechanics
Performance is more preferable, processing performance is simpler and the higher ferrocene class burningrate catalyst of combustibility, to improve ferrocene and its derivative
Object there are the problem of.
It proposes for allyl alcohol structure to be introduced into the United States Patent (USP) that Huskins in 1972 is delivered to be prepared for containing in ferrocene
There is the monokaryon ferrocene of diene propyl alcohol, the introducing of hydroxyl significantly reduces migration and volatility.Then in 1974,
Huskins is attempted to roll into a ball in isopropyl cyano again and is introduced into ferrocene butadiene, by the introducing for increasing carbochain and active group cyanic acid
Migration and volatility are reduced, and obtains preferable catalytic activity.1989 Nian Wuyan clocks et al. have also synthesized double-(methyl
Ferrocenyl)-methane, 2,2- be bis--(methyl ferrocenyl)-propane and bis- (methyl the ferrocenyl)-butane of 2,2-.Nineteen ninety-five moral
The Bu Luduo factory of national strength and prestige bar Oil Co., Ltd has carried out two kinds of efficient burningrate catalysts of modified synthesis to Catocene, i.e., and 2,
2- is bis--(butyl ferrocene) propane (BBFPr) and 1,1- it is bis--(butyl ferrocene) pentane (BBFPe).2001 peaks Nian Yuanyao et al.
It designs and is prepared for three kinds of high azepine derivatives of di-ferrocene, and test the stability and burn rate catalysis effect of synthesized compound
Fruit finds that such compound has preferable combustion catalysis effect to ammonium perchlorate, while having excellent thermal stability, has
Potential application value.Bian Zhanxi in 2004 et al. synthesized 2,2- it is bis--(monoalkyl ferrocenyl)-propane and the bis- (alkane of 2,2-
Base ferrocenyl) two series compounds of-propane.Lee in 2009 accounts in the patent that male and Tang Xiaoming is published and is prepared for one kind
Novel sub- ethylene ferrocene derivatives, the product synthesis cost is lower, and preparation flow is relatively easy, and catalytic action is good.
2011, Zhang Yan et al. was by ferrocenecarboxylic acid and high performance adhesive epoxidation end hydroxy butadiene (EHTPB) situ-formed graft
It is prepared for a kind of epoxidation end hydroxy butadiene ferrocenecarboxylic acid (EHTPB) burningrate catalyst.2012 Nian Yuanyao cutting edges of a knife or a sword et al. with
Ferrocene is that raw material obtains propyl bridging double focusing ferrocene formonitrile HCN by processes such as formylated, condensation, dehydrations and propyl bridging is double
Poly-ferrocene tetrazolium, and combustion catalysis performance when compound is added in ammonium perchlorate is tested, perchloric acid after display addition
Decomposition peak's temperature of ammonium is advanced by 50 DEG C or so, but its synthesis technology is complicated.2016, Gao Xiaoni et al. was with ferrocene tetrazole
For anion, rich nitrogen groups and ferrocene class quaternary ammonium salt are cation, have synthesized two class of high nitrogen-containing type and high Fe content type
Close object.By test, two class compounds have good combustion catalysis effect to propellant major constituent ammonium perchlorate, and migrate
Property and volatility are lower.
Summary of the invention
It is volatile easy to migrate existing for ferrocene burningrate catalyst the purpose of the present invention is overcoming the problems, such as to be commercialized, it mentions simultaneously
The energy level of high solid propellant, provides a kind of not easy to migrate under field conditions (factors) and volatilization, thermal stability it is good contain double-core
The benzoates burningrate catalyst of ferrocene group, and provide for the burningrate catalyst a kind of easy to operate, lower-cost
Preparation method.
For above-mentioned purpose, the knot of the benzoates burningrate catalyst of the group of the present invention containing biferrocene
Structure formula is as follows:
The benzoates burningrate catalyst of the above-mentioned group containing biferrocene the preparation method comprises the following steps: in N2It, will under atmosphere
Azido-methyl ferrocene shown in the -2- alkynyl propyl ester of phthalic acid two shown in Formulas I and Formula II is added in methanol, stirs evenly, then
Salzburg vitriol and sodium ascorbate is added, is stirred at room temperature 20~for 24 hours, filters to obtain crude product, by crude product column chromatography for separation,
Obtain the benzoates burningrate catalyst of the group containing biferrocene；
In above-mentioned preparation method, the two -2- alkynyl propyl ester of phthalic acid, cupric sulfate pentahydrate, resists azido-methyl ferrocene
The molar ratio of bad hematic acid sodium is 1:1.5~2.5:0.2~0.4:0.2~0.4.
Beneficial effects of the present invention are as follows:
The Phthalates compound containing biferrocene group that the present invention chooses be one by ferrocene group,
The molecule of 1,2,3- triazole group and carboxylic group composition, it is not only containing ferrocenyl required by ferrocene class catalyst
Group, and contains 1, this high nitrogen heterocycle perssad with the positive enthalpy of formation of 2,3- triazoles, the combustion heat with higher and generation
Heat can improve the energy level of propellant when decomposing.This kind of compound iron content increases, and has more excellent than monokaryon ferrocene
Burn rate catalytic activity.Another advantage of this kind of compound is nitrogen and oxygen original in 1,2,3- triazole group and carboxylic acid group
Son is easily formed hydrogen bond, and thermal stability, resistance to migration and the volatility of ferrocene class compound are improved by hydrogen bond action, is
A kind of not easy to migrate under field conditions (factors) and volatilization, thermal stability is good and the Phthalates biferrocene derivative of rich nitrogen
Object, for energy can be contributed to solid propellant in solid propellant.And the preparation method of such compound it is easy to operate, at
This is lower.
Detailed description of the invention
Fig. 1 is the differential scanning calorimetric analysis curve that 5% embodiment 1,2 burningrate catalysts are added in ammonium perchlorate.
Fig. 2 is the differential scanning calorimetric analysis curve that 5% embodiment 1,2 burningrate catalysts are added in hexogen.
Fig. 3 is the thermogravimetric curve of embodiment 1,2 burningrate catalysts.
Specific embodiment
The present invention is described in more detail with reference to the accompanying drawings and examples, but protection scope of the present invention is not limited only to
These embodiments.
Terephthalic acid (TPA) -2- alkynyl propyl ester used is prepared according to following methods in following example:
2g (12.03mmol) para Toluic Acid is dissolved in 20mL DMF, 4.16g (30mmol) K is then added2CO3, and
30min is persistently stirred at 60 DEG C, 2.36mL (30mmol) propargyl bromide is then added dropwise dropwise, continues to stir 8h at 60 DEG C,
After the reaction was completed, reaction mixture is cooled to room temperature, filters, filtrate is boiled off into solvent by Rotary Evaporators, is slightly produced
Object obtains two -2- alkynes of terephthalic acid (TPA) then by column chromatography for separation (eluant, eluent is petroleum ether: ethyl acetate=5:1, V/V)
Base propyl ester, yield 80%, reaction equation is as follows:
The structural characterization data of two -2- alkynyl propyl ester of gained terephthalic acid (TPA) are as follows:1H NMR(400MHz,CDCl3):δ8.15
(s,4H),4.96(s,4H),2.55(s,2H).
By the terephthalic acid (TPA) equimolar O-phthalic in the preparation method of above-mentioned two -2- alkynyl propyl ester of terephthalic acid (TPA)
Acid replacement, obtains two -2- alkynyl propyl ester of phthalic acid, yield 80%, reaction equation is as follows:
The structural characterization data of two -2- alkynyl propyl ester of gained phthalic acid are as follows:1H NMR(400MHz,CDCl3):δ7.77
(s,2H),7.57(s,2H),4.92(vs,4H),2.53(s,2H).
Embodiment 1
Preparation structure formula following terephthalic acid (TPA) pair-(ferrocenyl methyl-1,2,3- triazol radical methyl) ester
Two -2- alkynyl propyl ester of 0.2230g (1mmol) terephthalic acid (TPA) and 0.4931g are added into 250mL round-bottomed flask
(2.05mmol) azido-methyl ferrocene, in N230mL methanol is added under atmosphere, stirs evenly, 15mL is then added dropwise and contains 0.077g
The aqueous solution and 15mL of (0.3mmol) Salzburg vitriol contain the aqueous solution of 0.0604g (0.3mmol) sodium ascorbate, room temperature
Stirring for 24 hours, filters to obtain crude product, by crude product by column chromatography for separation, obtain terephthalic acid (TPA) it is double-(ferrocenyl methyl-1,
2,3- triazol radical methyl) ester, yield 82%, structural characterization data are as follows: FT-IR (cm-1):3431m,3155m,2955w,
1715vs,1626m,1383m,1335m,1265vs,1106vs,1044m,933m,801s,718m,490s；1H NMR
(400MHz,CDCl3):δ8.04(s,4H),7.59(s,2H),5.43(s,4H),5.30(s,4H),4.29(s,4H),4.23
(s,4H),4.18(vs,10H).
Embodiment 2
Preparation structure formula following phthalic acid pair-(ferrocenyl methyl-1 23- triazol radical methyl) ester
In the present embodiment, with the terephthalic acid (TPA) in two -2- alkynyl propyl ester alternative embodiment 1 of equimolar phthalic acid
Two -2- alkynyl propyl ester, other steps are same as Example 1, phthalic acid pair-(ferrocenyl methyl-1,2,3- triazol radicals
Methyl) ester, yield 79%, structural characterization data are as follows: FT-IR (cm-1):3427m,3094m,2955w,1723vs,
1626w,1445m,1383m,1272vs,1120vs,1058s,940m,822s,753m,635w,490s；1H NMR(400MHz,
CDCl3):δ7.68(s,2H),7.62(s,2H),7.51(s,2H),5.30(s,8H),4.31(s,4H),4.19(s,14H).
In order to prove beneficial effects of the present invention, inventor is right respectively by taking ammonium perchlorate (AP) and hexogen (RDX) as an example
The catalytic performance of the burningrate catalyst of Examples 1 and 2 preparation is tested, and specific experiment situation is as follows:
Burningrate catalyst 5mg, powdered ammonium perchlorate 95mg are taken, ground and mixed is uniform；Take burningrate catalyst 5mg, powder
The hexogen 95mg of last shape, grinding uniformly, are tested its catalytic performance using differential scanning calorimeter, and the result is shown in Figure 1~
2.Burningrate catalyst 3mg is taken, its thermal stability is tested using thermogravimetric analyzer, as a result sees Fig. 3.
As seen from Figure 1, the thermal decomposition of AP can be divided into three phases: the decalescence process that first process is AP, peak value
Temperature is 237.9 DEG C, and it is the low-temperature decomposition process of AP, the peak value temperature of phase III that the peak temperature of second stage, which is 284.4 DEG C,
Degree is 415.3 DEG C, referred to as the pyrolytic stage, downward endothermic peak is shown as from the low temperature pyrogenation stage to the pyrolytic stage,
This is because stage AP is decomposed thermally to form gas (HCl, NH3) heat that is absorbed is greater than itself and decomposes discharged heat
Amount is not obvious so the thermal decomposition process of AP itself releases heat.It is catalyzed when adding 5% Examples 1 and 2 burn rate in AP respectively
After agent, the crystal transfer temperature of AP has moved backward 10 DEG C or so by original 237.5 DEG C.Meanwhile the pyrolytic stage of AP
20 DEG C or so have been moved backward by original 284.4 DEG C.Changing maximum is endothermic peak of the original AP at the pyrolytic stage
It disappears, i.e. peak in figure at 415.3 DEG C, new exothermic peak occurs at 346.4 DEG C, 347.9 DEG C again respectively, and compared with AP
Endothermic peak at 415.3 DEG C, which has, largely to move forward, and the heat released is up to 1005.26~1012.94J/g, so,
Can analyze out Examples 1 and 2 burningrate catalyst has significant catalytic action to the thermal decomposition of AP.It can be seen that with pure AP phase
Than, the pyrolytic stage presentation concentration exothermic phenomenon of system after burningrate catalyst of the present invention is added, exothermic peak temperature shifts to an earlier date, and
The heat of releasing obviously increases, and illustrates that burningrate catalyst of the present invention has good combustion catalysis to the thermal decomposition of AP.
From Figure 2 it can be seen that the fusing point of RDX, at 202 DEG C, decomposition caused heat release peak temperature is in 231.2 DEG C, the heat of releasing
827.9J/g；After adding 5% Examples 1 and 2 burningrate catalyst in RDX respectively, occur one respectively before RDX melts
A peak temperature is the exothermic peak of 198.6 DEG C, 199.2 DEG C, illustrates that RDX has had already appeared decomposed phenomenon before not melting, separately
Outside, the thermal discharge of mixed system is respectively 1084.9J/g and 1236.9J/g, illustrates the addition of Examples 1 and 2 burningrate catalyst
Increase the thermal discharge of RDX, wherein 2 burningrate catalyst of embodiment keeps RDX thermal discharge increasing degree most significant, increases 49%
Left and right, thermal discharge reach 1236.9J/g.Illustrate that Examples 1 and 2 burningrate catalyst has catalytic action to RDX thermal decomposition, wherein real
It is most obvious to apply the catalytic effect that 2 burningrate catalyst of example thermally decomposes RDX.
As seen from Figure 3, the weightless initial temperature of burningrate catalyst of the present invention is at 200 DEG C or more, hence it is evident that it is pungent to be higher than Kato
Weightless initial temperature, show good thermal stability.
Claims (3)
1. a kind of benzoates burningrate catalyst of group containing biferrocene, it is characterised in that the structure of the burningrate catalyst
Formula is as follows:
2. a kind of preparation method of the benzoates burningrate catalyst of the group described in claim 1 containing biferrocene,
It is characterized in that: in N2Under atmosphere, azido-methyl ferrocene shown in the -2- alkynyl propyl ester of phthalic acid two shown in Formulas I and Formula II is added
Enter in methanol, stir evenly, Salzburg vitriol and sodium ascorbate is then added, it is stirred at room temperature 20~for 24 hours, it filters slightly to produce
Crude product column chromatography for separation is obtained the benzoates burningrate catalyst of the group containing biferrocene by object；
3. the preparation method of the benzoates burningrate catalyst of the group according to claim 2 containing biferrocene,
Be characterized in that: the two -2- alkynyl propyl ester of phthalic acid, azido-methyl ferrocene, cupric sulfate pentahydrate, sodium ascorbate mole
Than for 1:1.5~2.5:0.2~0.4:0.2~0.4.
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Cited By (6)
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| CN110294780A (en) * | 2019-07-09 | 2019-10-01 | 陕西师范大学 | The aromatic amine burningrate catalyst and preparation method thereof of the triazole group of -1,2,3- containing ferrocenylmethyl |
| CN110385144A (en) * | 2019-07-09 | 2019-10-29 | 陕西师范大学 | The fatty ethers burningrate catalyst and preparation method thereof of the triazole group of -1,2,3- containing ferrocenylmethyl |
| CN112778377A (en) * | 2021-01-14 | 2021-05-11 | 陕西师范大学 | Ferrocene burning-rate catalyst containing bis (imidazole or pyrazole-1, 2, 3-triazole) group and preparation method thereof |
| CN112939708A (en) * | 2021-02-08 | 2021-06-11 | 陕西师范大学 | Imidazole and pyrazole combustion rate catalyst containing ferrocenyl methyl-1, 2, 3-triazolyl group and preparation method thereof |
| CN113896748A (en) * | 2021-11-05 | 2022-01-07 | 西北大学 | Binuclear ferrocenyl energetic compound and synthesis method and application thereof |
| CN116041720A (en) * | 2023-01-04 | 2023-05-02 | 浙江大学 | Anti-migration ferrocenyl dendritic polymer burning rate catalyst, and preparation method and application thereof |
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| CN110294780A (en) * | 2019-07-09 | 2019-10-01 | 陕西师范大学 | The aromatic amine burningrate catalyst and preparation method thereof of the triazole group of -1,2,3- containing ferrocenylmethyl |
| CN110385144A (en) * | 2019-07-09 | 2019-10-29 | 陕西师范大学 | The fatty ethers burningrate catalyst and preparation method thereof of the triazole group of -1,2,3- containing ferrocenylmethyl |
| CN110294780B (en) * | 2019-07-09 | 2021-09-28 | 陕西师范大学 | Aromatic amine burning rate catalyst containing ferrocenyl methyl-1, 2, 3-triazole group and preparation method thereof |
| CN110385144B (en) * | 2019-07-09 | 2022-04-05 | 陕西师范大学 | Aliphatic ether burning rate catalyst containing ferrocenyl methyl-1, 2, 3-triazole group and preparation method thereof |
| CN112778377A (en) * | 2021-01-14 | 2021-05-11 | 陕西师范大学 | Ferrocene burning-rate catalyst containing bis (imidazole or pyrazole-1, 2, 3-triazole) group and preparation method thereof |
| CN112778377B (en) * | 2021-01-14 | 2021-12-24 | 陕西师范大学 | Ferrocene burning-rate catalyst containing bis (imidazole or pyrazole-1, 2, 3-triazole) group and preparation method thereof |
| CN112939708A (en) * | 2021-02-08 | 2021-06-11 | 陕西师范大学 | Imidazole and pyrazole combustion rate catalyst containing ferrocenyl methyl-1, 2, 3-triazolyl group and preparation method thereof |
| CN112939708B (en) * | 2021-02-08 | 2021-11-30 | 陕西师范大学 | Imidazole and pyrazole combustion rate catalyst containing ferrocenyl methyl-1, 2, 3-triazolyl group and preparation method thereof |
| CN113896748A (en) * | 2021-11-05 | 2022-01-07 | 西北大学 | Binuclear ferrocenyl energetic compound and synthesis method and application thereof |
| CN113896748B (en) * | 2021-11-05 | 2022-07-19 | 西北大学 | Binuclear ferrocenyl energetic compound and synthesis method and application thereof |
| CN116041720A (en) * | 2023-01-04 | 2023-05-02 | 浙江大学 | Anti-migration ferrocenyl dendritic polymer burning rate catalyst, and preparation method and application thereof |
| CN116041720B (en) * | 2023-01-04 | 2024-02-27 | 浙江大学 | Anti-migration ferrocenyl dendritic polymer burning rate catalyst, and preparation method and application thereof |
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