CN101417980B - Metal complex and synthesis and use thereof - Google Patents
Metal complex and synthesis and use thereof Download PDFInfo
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- CN101417980B CN101417980B CN2008102437811A CN200810243781A CN101417980B CN 101417980 B CN101417980 B CN 101417980B CN 2008102437811 A CN2008102437811 A CN 2008102437811A CN 200810243781 A CN200810243781 A CN 200810243781A CN 101417980 B CN101417980 B CN 101417980B
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Abstract
The invention discloses a metal complex, synthesis and application thereof, wherein the product can be used as a catalyst for the thermal decomposition of ammonium perchlorate. The invention belongs to the technical field of chemical synthesis and propellant application. The technical proposal of the invention is to use 5 (Z)-amino-2-substituted-phenyl-1H-imidazole-5(2H)-ketoxime-3-oxygen and metal salts as raw materials to synthesize a kind of metal complexes which have remarkable catalytic effect on the thermal decomposition of the ammonium perchlorate, the product can be used as the catalyst for accelerating the burning rate of the propellant and has the advantages that raw materials are available, the preparation process is easy to realize, and the product is advantageous to popularization and application.
Description
Technical field
The present invention relates to a kind of structure, compound method and application thereof of metal complex, product can be used as the The Thermal Decomposition of Ammonium Perchlorate catalyzer, belongs to chemosynthesis, propelling agent applied technical field.
Background technology
Ammoniumper chlorate (AP) is component oxygenant and a high energy component commonly used in the solid rocket propellant; Its characteristic has material impact to the overall performance of solid rocket propellant; The combustionproperty of SP is the important factor that directly influences the thrust chamber ballisticperformances; The height of combustion speed has determined the working hour of mover, and the combustionproperty of control and adjusting propelling agent is very important to thrust chamber.Especially the combustioncharacteristics of the thermal decomposition characteristic of AP and propelling agent (combustion speed) is closely related.
Except physical aspect (like granularity, crystal formation) of AP etc. influences the thermal decomposition performance of AP, the decomposition of AP can accelerated or slow down to additive (like the ammonium salt NH of fluo anion complex compound
4PF
6, NH
4BF
4, NH
4TiF
6Deng Performance for Decomposition of Ammonium Perchlorate is also had retarding effect), to realize the control of combustion processes.Adding catalyzer can make the composition of ammoniumper chlorate degradation production change.Generally speaking, the catalyzer that improves decomposition rate can both suppress Cl
2And N
2The generation of O.The Nomenclature Composition and Structure of Complexes by catalyzer divides, and effectively catalyzer is concluded and had four types basically: (1) metal and alloy catalyst thereof (Cu, Ni and Al etc.); (2) MOX and O composite metallic oxide catalyst thereof (catalyst of transition metal oxide, like NiO, MnO
2, CuO, Cr
2O
3, Fe
2O
3, Co
2O
3Deng, O composite metallic oxide catalyst LaCoO
3); (3) saline catalyst such as LiF, C
2CuO
4, KMnO
4, CuNO
3(4) metal complex catalyzer.
Summary of the invention
The object of the invention provides a kind ofly has remarkable catalytic effect to Performance for Decomposition of Ammonium Perchlorate, and the product starting material are easy to get, the new type of metal complex compound that preparation technology is prone to realize and synthetic and application.
For achieving the above object, the technical scheme that the present invention adopts is: a kind of metal complex has following structure:
Wherein, M is metallic copper, nickel, chromium, iron or lead; R
1, R
2, R
3And R
4Be selected from-H ,-CH
3,-CH
2CH
3,-OCH
3,-OCH
2CH
3,-NO
2,-Cl ,-Br or-OH.
The compound method of above-mentioned metal complex is, is part with 5 (Z)-amino-2-substituted-phenyl-1H-imidazoles-5 (2H)-ketoxime-3-oxygen, carries out obtaining metal complex after the metal ion exchanged reaction with metal-salt.
Wherein, the substituting group on the described substituted-phenyl is hydrogen, methyl, ethyl, methoxyl group, oxyethyl group, nitro, halogen or hydroxyl.
Described metal-salt is acetate, nitrate salt or the hydrochloride of copper, nickel, chromium, iron or lead metal.
Above-mentioned metal complex can be applied to the Performance for Decomposition of Ammonium Perchlorate catalyst for reaction.
Synthetic metal complex reaction formula of the present invention is following:
Wherein, MX is a metal-salt, and like metallic copper, nickel, chromium, iron or plumbous acetate, nitrate salt or hydrochloride, then M is metallic copper, nickel, chromium, iron or lead; R
1, R
2, R
3And R
4For-H ,-CH
3,-CH
2CH
3,-OCH
3,-OCH
2CH
3,-NO
2,-Cl ,-Br or-OH, they are identical or inequality.
Principle of the present invention is: metal complex itself is the same with some metal salt compound catalyzer, is the presoma of catalysis Performance for Decomposition of Ammonium Perchlorate reaction, and its degradation production is only the Performance for Decomposition of Ammonium Perchlorate catalyst for reaction.Therefore, the thermal decomposition behavior of metal complex itself has decisive influence to its catalytic performance.
Because the technique scheme utilization, the present invention compared with prior art has advantage:
The present invention is a raw material with 5 (Z)-amino-2-substituted-phenyl-1H-imidazoles-5 (2H)-ketoxime-3-oxygen and metal-salt; Synthesized a metalloid complex compound; Performance for Decomposition of Ammonium Perchlorate is had remarkable catalytic effect, and product is expected to be used as the propellant burning rate catalyzer, and has starting material and be easy to get; Preparation technology is prone to realize the advantage that helps applying.
Description of drawings
Fig. 1 be weightless (TG-DTG) graphic representation of the thermal weight loss-differential of ammoniumper chlorate (temperature rise rate be 20 ℃/min);
Fig. 2 is the TG-DTG graphic representation that is heated and decomposes fast by the hydroxyl-substituted polymerization of olefin using catalyst Compound C uL-OH metal complex that the embodiment of the invention 1 technical scheme prepares;
Fig. 3 is the TG-DTG graphic representation by the hydroxyl-substituted polymerization of olefin using catalyst Compound C uL-OH catalysis AP of the embodiment of the invention 1 technical scheme preparation;
Fig. 4 is the TG-DTG graphic representation by the phenyl coordination compound NiL-Ph catalysis AP of the embodiment of the invention 5 technical schemes preparation;
Fig. 5 is the TG-DTG graphic representation by the methyl substituted phenyl coordination compound PbL-Me catalysis AP of the embodiment of the invention 9 technical schemes preparation.
Embodiment
Below in conjunction with accompanying drawing and embodiment the present invention is further described:
Hydroxyl-substituted polymerization of olefin using catalyst Compound C uL-OH's is synthetic:
In the 500mL three-necked bottle, add 0.82g 5 (Z)-amino-2-phenylor-1H-imidazoles-5 (2H)-ketoxime-3-oxygen, 240mL methyl alcohol; Be warming up to 50～60 ℃ of dissolvings, add 0.40g one hydration neutralized verdigris, it is coffee-like muddy that reaction solution is immediately; Behind the reaction 24h, filter, for several times with methanol wash; Obtain the hydroxyl-substituted polymerization of olefin using catalyst Compound C of the coffee-like powder blocks of solid of 0.71g uL-OH, productive rate 58%.IR?v
max(KBr)：3320(NH，OH)，1670(C＝N)，1570，1460，1340(N＝O)，1230(C-N)，935(N-O)，700cm
-1。
Hydroxyl-substituted polymerization of olefin using catalyst compound N iL-OH's is synthetic:
In the 500mL three-necked bottle, add 0.82g 5 (Z)-amino-2-phenylor-1H-imidazoles-5 (2H)-ketoxime-3-oxygen, 240mL ethanol; Be warming up to 50～60 ℃ of dissolvings, add the 0.36g nickel acetate, reaction solution is the reddish-brown muddiness immediately; Behind the reaction 24h, filter, for several times with methanol wash; Obtain the hydroxyl-substituted polymerization of olefin using catalyst compound N of 0.70g reddish-brown pulverulent solids iL-OH, productive rate 60%.IR?v
max(KBr)：3320(NH，OH)，1640(C＝N)，1560，1450，1340(N＝O)，1110(C-N)，993(N-O)，692cm
-1。
Hydroxyl-substituted polymerization of olefin using catalyst compound Pb L-OH's is synthetic:
In the 500mL three-necked bottle, add 0.82g 5 (Z)-amino-2-phenylor-1H-imidazoles-5 (2H)-ketoxime-3-oxygen, the water of 240mL; Be warming up to 50～60 ℃ of dissolvings, add the 0.56g plumbic acetate, it is muddy that reaction solution is the khaki color look immediately; Behind the reaction 24h, filter, for several times with methanol wash; Obtain the hydroxyl-substituted polymerization of olefin using catalyst Compound C of 0.80g khaki color powder blocks of solid uL-OH, productive rate 60%.IR?v
max(KBr)：3320(NH，OH)，1640(C＝N)，1560，1450，1340(N＝O)，1110(C-N)，993(N-O)，692cm
-1。IR?v
max(KBr)：3420(NH，OH)，1618(C＝N)，1560，1400，1335(N＝O)，1230(C-N)，1010(N-O)，889，714cm
-1。
Phenyl coordination compound CuL-Ph's is synthetic:
In the 500mL three-necked bottle, add 0.85g 5 (Z)-amino-2-phenyl-1H-imidazoles-5 (2H)-ketoxime-3-oxygen, 240mL methyl alcohol; Be warming up to 47 ℃ of dissolvings, add 0.40g one hydration neutralized verdigris, reaction solution is the yellow-green colour muddiness immediately and fades to coffee-like muddy again; Behind the reaction 50h, filter, for several times with methanol wash; Obtain 0.50g brown ceramic powder fritter shape solid product, productive rate 40%.IR?v
max(KBr)：3430，3330(NH)，3243，3157(OH)，1643，1617(C＝N)，1580，，1530，1440，1320(N＝O)，1150(C-N)，1020(N-O)cm
-1。
Phenyl coordination compound NiL-Ph's is synthetic:
In the 500mL three-necked bottle, add 0.85g 5 (Z)-amino-2-phenyl-1H-imidazoles-5 (2H)-ketoxime-3-oxygen, 240mL ethanol; Be warming up to 47 ℃ of dissolvings, add the 0.36g nickel acetate, reaction solution is the yellow-green colour muddiness immediately and fades to dark-brown again; Behind the reaction 50h, filter, for several times with methanol wash; Obtain 0.33g dark-brown pulverulent solids, productive rate 24%.IR?v
max(KBr)：3410，3353(NH)，3259，3120(OH)，1668，1640(C＝N)，1608，1470，1318(N＝O)，1164(C-N)，1060(N-O)cm
-1。
Embodiment 6
Phenyl coordination compound PbL-Ph's is synthetic:
In the 500mL three-necked bottle, add 0.85g 5 (Z)-amino-2-phenyl-1H-imidazoles-5 (2H)-ketoxime-3-oxygen, 240mL water; Be warming up to 47 ℃ of dissolvings, add the 0.56g plumbic acetate, reaction solution is light brown red immediately; Behind the reaction 50h, filter, for several times with methanol wash; Obtain 0.36g red-brown pulverulent solids, productive rate 22%.IR?v
max(KBr)：3470(NH)，3360，3328(OH)，1677，1610(C＝N)，1557，1470，1330(N＝O)，1240(C-N)，1020(N-O)cm
-1。
Embodiment 7
Methyl substituted phenyl coordination compound CuL-Me's is synthetic:
In the 500mL three-necked bottle, add 0.89g5 (Z)-amino-2-tolyl-1H-imidazoles-5 (2H)-ketoxime-3-oxygen, 275mL methyl alcohol; Be warming up to 57 ℃ of dissolvings, add 0.40g one hydration neutralized verdigris, reaction solution is the greyish-green muddiness immediately and slowly fades to weak coffee look muddiness again; Behind reaction 17h under 44 ℃; Filter, with methanol wash for several times, obtain light khaki color powder blocks of solid CuL
4, 0.60g, productive rate 47%, IRv
Max(KBr): 3388 (NH), 3320,3230 (OH), 1720,1670 (C=N), 1660,1450,1360 (N=O), 1230 (C-N), 933 (N-O), 827,729cm
-1Anal.Calcd?forC
20H
24N
8O
4Cu：C?47.66；H?4.80；N?22.23.Found：C?47.48；H?4.60；N?22.03。
Methyl substituted phenyl coordination compound NiL-Me's is synthetic:
In the 500mL three-necked bottle, add 0.89g5 (Z)-amino-2-tolyl-1H-imidazoles-5 (2H)-ketoxime-3-oxygen, 275mL ethanol; Be warming up to 57 ℃ of dissolvings, add the 0.36g nickel acetate, it is brick-red that reaction solution is immediately; Behind reaction 17h under 44 ℃, filter, for several times with methanol wash; Obtain the brick-red powder of 0.28g, productive rate 20%.IR?v
max(KBr)：3450，3396(NH)，3330(OH)，1720，1609(C＝N)，1585，1540，1430，1250(N＝O)，1140(C-N)，1052(N-O)，858，816cm
-1。
Embodiment 9
Methyl substituted phenyl coordination compound PbL-Me's is synthetic:
In the 500mL three-necked bottle, add 0.89g5 (Z)-amino-2-tolyl-1H-imidazoles-5 (2H)-ketoxime-3-oxygen, 275mL water; Be warming up to 57 ℃ of dissolvings, add the 0.56g plumbic acetate, it is brick-red that reaction solution is immediately; Behind reaction 17h under 44 ℃, filter, for several times with methanol wash; Obtain 0.15g reddish-brown powder bulk solid, productive rate 9%.IR v
Max(KBr): 3360 (NH), 3260,3190 (OH), 1720,1643 (C=N), 1608,1560,1410,1335 (N=O), 1230 (C-N), 928 (N-O), 825,742 (δ
N-HFace is outer) cm
-1
Methoxyl group substituted-phenyl coordination compound CuL-OMe's is synthetic:
In the 500mL three-necked bottle, add 0.94g5 (Z)-amino-2-methoxyphenyl-1H-imidazoles-5 (2H)-ketoxime-3-oxygen, 200mL methyl alcohol; Be warming up to 40 ℃ of dissolvings, add 0.40g one hydration neutralized verdigris, reaction solution is the greyish-green muddiness immediately and slowly fades to the dark-brown muddiness again; Behind reaction 46h under 50 ℃, filter, for several times with methanol wash; Obtain the shinny powder of 0.18g black, productive rate 13%, IR v
Max(KBr): 3379 (NH), 3310 (OH), 2832 (CH
3), 1702 (C=N), 1600,1566,1514,1340 (N=O), 1250 (C-N), 1112 (Ar-O-C), 1020 (N-O), 756cm
-1
Embodiment 11
Methoxyl group substituted-phenyl coordination compound NiL-OMe's is synthetic:
In the 500mL three-necked bottle, add 0.94g5 (Z)-amino-2-methoxyphenyl-1H-imidazoles-5 (2H)-ketoxime-3-oxygen, 200mL methyl alcohol; Be warming up to 40 ℃ of dissolvings, add the 0.36g nickel acetate, reaction solution is the large red muddiness immediately; Behind reaction 46h under 50 ℃, filter, for several times with methanol wash; Obtain 0.91g large red powder, productive rate 63%.IR?v
max(KBr)：3470，3413(NH)，3340(OH)，2830(CH
3)，1617，1608(C＝N)，1591，1550，1460，1309(N＝O)，1260(C-N)，1130(Ar-O-C)，1030(N-O)，858，750cm
-1。
Embodiment 12
Methoxyl group substituted-phenyl coordination compound PbL-OMe's is synthetic:
In the 500mL three-necked bottle, add 0.94g5 (Z)-amino-2-methoxyphenyl-1H-imidazoles-5 (2H)-ketoxime-3-oxygen, 200mL methyl alcohol; Be warming up to 40 ℃ of dissolvings, add the 0.56g plumbic acetate, reaction solution is the yellow-green colour muddiness immediately; Behind reaction 46h under 50 ℃, filter, for several times with methanol wash; Obtain 0.19g yellow-green colour powder, productive rate 11.IR?v
max(KBr)：3388，3234(NH)，3050(OH)，2832(CH
3)，1690，1608(C＝N)，1560，1489，1410，1330(N＝O)，1240(C-N)，1190(Ar-O-C)，1050(N-O)，951，754cm
-1。
Embodiment 13
Nitro substituted-phenyl coordination compound CuL-NO
2Synthetic:
In the 1000mL three-necked bottle, add 1.00g 5 (Z)-amino-2-nitrophenyl-1H-imidazoles-5 (2H)-ketoxime-3-oxygen, 790mL methyl alcohol; Be warming up to 60 ℃ of dissolvings, add 0.4g one hydration neutralized verdigris, reaction solution is the greyish-green muddiness immediately and slowly fades to weak coffee look muddiness again; Behind reaction 23h under 50 ℃; Filter, with methanol wash for several times, obtain weak coffee toner end blocks of solid CuL
6, 0.7248g, productive rate 52%, IRv
Max(KBr): 3430,3290 (NH), 3130 (OH), 1711,1670 (C=N), 1530,1340 (N=O), 1326 (NO
2), 1190 (C-N), 947,791,708cm
-1
Embodiment 14
Nitro substituted-phenyl coordination compound NiL-NO
2Synthetic:
In the 1000mL three-necked bottle, add 1.00g 5 (Z)-amino-2-nitrophenyl-1H-imidazoles-5 (2H)-ketoxime-3-oxygen, 790mL methyl alcohol; Be warming up to 60 ℃ of dissolvings, add the 0.36g nickel acetate, it is coffee-like muddy that reaction solution is immediately; Behind reaction 23h under 50 ℃, filter, for several times with methanol wash; Obtain coffee-like powder blocks of solid 0.06g, productive rate 4%.IR?v
max(KBr)：3422(NH)，3330(OH)，1630(C＝N)，1574，1530，1350(N＝O)，1326(NO
2)，1147(C-N)，1080(N-O)，787cm
-1。
Metal complex as catalyst applications in The Thermal Decomposition of Ammonium Perchlorate reaction:
Use respectively by embodiment 1, embodiment 5 and 9 hydroxyl-substituted polymerization of olefin using catalyst Compound C of synthetic of embodiment uL-OH, phenyl coordination compound NiL-Ph and three kinds of metal complexs of methyl substituted phenyl coordination compound PbL-Me; Is 50: 50 by quality than metal complex and ammoniumper chlorate; In ammoniumper chlorate, add metal complex respectively; Fully grind 5min with agate mortar, obtain the mixture of ammoniumper chlorate and metal complex.
Utilize Diamond TG/DTA thermal analyzer respectively sample to be carried out hot analytical test, judge that according to the variation of thermolysis summit temperature metal complex is to the The Thermal Decomposition of Ammonium Perchlorate catalytic effect.Sample size is about 5mg during test, and heat-up rate is 10 ℃/min, and atmosphere is high purity nitrogen, gas flow 100ml/min, and Range of measuring temp is 40～500 ℃, sample disc is an alumina crucible.
Referring to accompanying drawing 1; It is ammoniumper chlorate (AP) weightless (TG-DTG) graphic representation of thermal weight loss-differential (temperature rise rate be 20 ℃/min); Visible by Fig. 1, ammoniumper chlorate is heated and shows as two sections decomposition, and first section is decomposed summit temperature and appear at 316.4 ℃; Second section is decomposed summit temperature and appears at 453.0 ℃, 270 ℃ of temperature for being about to begin to decompose.
Referring to accompanying drawing 2; It is the TG-DTG graphic representation that is heated and is decomposed fast by the hydroxyl-substituted polymerization of olefin using catalyst Compound C uL-OH metal complex that the embodiment of the invention 1 technical scheme prepares; The DTG curve display, maximum rate of decomposition even reach 656.0%/min belongs to the material that moment decomposes fast.Thermal weight loss situation analysis test result by metal complex provided by the invention shows; They are in the time of 270 ℃; Part is decomposed or is decomposed the new compound of generation fully, can know that to the thermal decomposition process and the product analysis comparison thereof of these metal complexs the thermal decomposition process of these complex compounds only has a decomposition peak; Its degradation production is more stable, does not find to have tangible weightlessness in the temperature-rise period afterwards.
Referring to accompanying drawing 3, it is the TG-DTG graphic representation by the hydroxyl-substituted polymerization of olefin using catalyst Compound C uL-OH catalysis AP of the embodiment of the invention 1 technical scheme preparation; Can know after CuL-OH adds AP as the copper-containing metal complex compound, to have only a decomposition peak (346.03 ℃) on the DTG curve of mixture by Fig. 3, just corresponding the sharp-pointed exothermic peak that has 350.55 ℃ on the DTA curve, the decomposition peak has shifted to an earlier date 105.47 ℃.
Referring to accompanying drawing 4, it is the TG-DTG graphic representation by the phenyl coordination compound NiL-Ph catalysis AP of the embodiment of the invention 5 technical schemes preparation; Can be known after phenyl coordination compound NiL-Ph adds AP as nickeliferous metal complex, also to have only a decomposition peak (387.68 ℃) on the DTG curve of mixture by Fig. 4, the decomposition peak has shifted to an earlier date 66.27 ℃.
Referring to accompanying drawing 5, it is the TG-DTG graphic representation by the methyl substituted phenyl coordination compound PbL-Me catalysis AP of the embodiment of the invention 9 technical schemes preparation; Can be known that by Fig. 5 after methyl substituted phenyl coordination compound PbL-Me added AP as leaded metal complex, the thermolysis low-temperature decomposition peak of mixture moved 21.31 ℃ to low-temperature end, the pyrolytic decomposition peak has also moved 32.52 ℃ to low-temperature end simultaneously.
This shows that metal complex provided by the present invention is a quick decompose material of moment, it has significant catalytic effect to Performance for Decomposition of Ammonium Perchlorate.
The present invention is through doing heat analysis with the mixture of metal complex and ammoniumper chlorate, and the thermal decomposition behavior that the research ammoniumper chlorate adds before and after the metal complex changes,
Relatively different metal element such as copper, nickel and lead metal complex compound and the different organic ligand metal complexs of same metal element are to the influence of Performance for Decomposition of Ammonium Perchlorate; Use heat analytical procedure (TG and DTG) is studied Catalyzed Decomposition of Ammonium Perchlorate; Filter out thus to Performance for Decomposition of Ammonium Perchlorate have remarkable catalytic effect metal complex, the result shows that the catalytic activity of copper-containing metal complex compound is the highest in the different metal complex compound; Nickel complex takes second place, and lead complex is poor slightly; Several kinds of copper-containing metal complex compound and the nickeliferous metal complexs with high catalytic activity provided by the invention can be used as the propellant burning rate catalyst applications.
Claims (3)
1. metal complex is characterized in that it has following structure:
Wherein, M is metallic copper, nickel, iron or lead; R
1, R
2, R
3And R
4Be selected from-H ,-CH
3,-CH
2CH
3,-OCH
3,-OCH
2CH
3,-NO
2,-Cl ,-Br or-OH.
2. the compound method of the said metal complex of claim 1; It is characterized in that: it is a part with (5Z)-4-amino-2-(substituted-phenyl)-1H-imidazoles-5 (2H)-ketoxime-3-oxygen; Carry out obtaining metal complex after the metal ion exchanged reaction with metal-salt, reaction formula is following:
Acetate, nitrate salt or hydrochloride that described metal-salt MX is copper, nickel, iron or lead metal; R
1, R
2, R
3And R
4Be selected from-H ,-CH
3,-CH
2CH
3,-OCH
3,-OCH
2CH
3,-NO
2,-Cl ,-Br or-OH.
3. the said metal complex of claim 1 is as the application of Performance for Decomposition of Ammonium Perchlorate catalyst for reaction.
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| CN104402916A (en) * | 2014-11-19 | 2015-03-11 | 西南科技大学 | Cerium trimesic acid complex for catalyzing thermal decomposition of AP (ammonium perchlorate) and preparation method of cerium trimesic acid complex |
| CN106083504B (en) * | 2016-06-01 | 2018-11-09 | 中国工程物理研究院化工材料研究所 | One kind being based on energetic compound [Mn (BTO) (H2O)2]nEfficient catalytic decompose ammonium perchlorate method |
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