CN105820178A - Amino pyrrole metal lithium compound as well as preparation method and application thereof - Google Patents
Amino pyrrole metal lithium compound as well as preparation method and application thereof Download PDFInfo
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- CN105820178A CN105820178A CN201610255247.7A CN201610255247A CN105820178A CN 105820178 A CN105820178 A CN 105820178A CN 201610255247 A CN201610255247 A CN 201610255247A CN 105820178 A CN105820178 A CN 105820178A
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- pyrroles
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- lithium metal
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- QLSWIGRIBOSFMV-UHFFFAOYSA-N 1h-pyrrol-2-amine Chemical compound NC1=CC=CN1 QLSWIGRIBOSFMV-UHFFFAOYSA-N 0.000 title claims abstract description 23
- 238000002360 preparation method Methods 0.000 title claims abstract description 10
- 229910052751 metal Inorganic materials 0.000 title abstract description 8
- 239000002184 metal Substances 0.000 title abstract description 6
- 150000002642 lithium compounds Chemical class 0.000 title abstract 3
- 229910052744 lithium Inorganic materials 0.000 claims abstract description 20
- 238000006243 chemical reaction Methods 0.000 claims abstract description 18
- 239000012948 isocyanate Substances 0.000 claims abstract description 14
- 238000005829 trimerization reaction Methods 0.000 claims abstract description 9
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 claims abstract description 6
- 239000013078 crystal Substances 0.000 claims abstract description 6
- 239000000706 filtrate Substances 0.000 claims abstract description 4
- 239000005457 ice water Substances 0.000 claims abstract description 4
- 239000011261 inert gas Substances 0.000 claims abstract description 4
- 238000006555 catalytic reaction Methods 0.000 claims description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 9
- 150000002736 metal compounds Chemical class 0.000 claims description 9
- 238000010992 reflux Methods 0.000 claims description 3
- DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 claims description 2
- -1 isocyanate compounds Chemical class 0.000 abstract description 17
- 239000003054 catalyst Substances 0.000 abstract description 15
- 125000004122 cyclic group Chemical group 0.000 abstract description 7
- 239000003446 ligand Substances 0.000 abstract description 7
- 230000003197 catalytic effect Effects 0.000 abstract description 5
- 239000002994 raw material Substances 0.000 abstract description 2
- 238000001914 filtration Methods 0.000 abstract 1
- 238000006138 lithiation reaction Methods 0.000 abstract 1
- IRLSMTNXLYCUDR-UHFFFAOYSA-N n-tert-butyl-1h-pyrrol-2-amine Chemical compound CC(C)(C)NC1=CC=CN1 IRLSMTNXLYCUDR-UHFFFAOYSA-N 0.000 abstract 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- 239000003863 metallic catalyst Substances 0.000 description 9
- 230000000694 effects Effects 0.000 description 8
- 150000002513 isocyanates Chemical class 0.000 description 7
- 150000003233 pyrroles Chemical class 0.000 description 6
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Natural products OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 5
- KAESVJOAVNADME-UHFFFAOYSA-N 1H-pyrrole Natural products C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 4
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 3
- 238000001514 detection method Methods 0.000 description 2
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 2
- 239000010931 gold Substances 0.000 description 2
- 229910052737 gold Inorganic materials 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 229910052761 rare earth metal Inorganic materials 0.000 description 2
- 238000007363 ring formation reaction Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- YNABZXVRMXPLDX-UHFFFAOYSA-N 2-methyl-1h-pyrrol-3-amine Chemical compound CC=1NC=CC=1N YNABZXVRMXPLDX-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 229910000765 intermetallic Inorganic materials 0.000 description 1
- JJTUDXZGHPGLLC-UHFFFAOYSA-N lactide Chemical group CC1OC(=O)C(C)OC1=O JJTUDXZGHPGLLC-UHFFFAOYSA-N 0.000 description 1
- 229910052747 lanthanoid Inorganic materials 0.000 description 1
- 150000002641 lithium Chemical group 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000013110 organic ligand Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 150000002910 rare earth metals Chemical class 0.000 description 1
- 238000007151 ring opening polymerisation reaction Methods 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- QVTVDJWJGGEOGX-UHFFFAOYSA-N urea;cyanide Chemical compound N#[C-].NC(N)=O QVTVDJWJGGEOGX-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
- C07F1/00—Compounds containing elements of Groups 1 or 11 of the Periodic Table
- C07F1/02—Lithium compounds
-
- 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
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/18—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms
- B01J31/1805—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms the ligands containing nitrogen
- B01J31/181—Cyclic ligands, including e.g. non-condensed polycyclic ligands, comprising at least one complexing nitrogen atom as ring member, e.g. pyridine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
- C07D251/30—Only oxygen atoms
-
- 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
- B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
- B01J2231/10—Polymerisation reactions involving at least dual use catalysts, e.g. for both oligomerisation and polymerisation
- B01J2231/14—Other (co) polymerisation, e.g. of lactides, epoxides
-
- 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
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/02—Compositional aspects of complexes used, e.g. polynuclearity
- B01J2531/0202—Polynuclearity
- B01J2531/0205—Bi- or polynuclear complexes, i.e. comprising two or more metal coordination centres, without metal-metal bonds, e.g. Cp(Lx)Zr-imidazole-Zr(Lx)Cp
-
- 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
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/10—Complexes comprising metals of Group I (IA or IB) as the central metal
- B01J2531/11—Lithium
-
- 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
- C07B2200/13—Crystalline forms, e.g. polymorphs
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Inorganic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Catalysts (AREA)
Abstract
The invention provides an amino pyrrole metal lithium compound as well as a preparation method and application thereof, relates to cyclic trimerization reaction of isocyanate compounds, and in particular to a lithium metal catalyst which takes 2-tert-butylamino pyrrole as ligand. The preparation method comprises the following steps: under the condition of inert gas protection and ice water bath, performing lithiation on amino pyrrole ligand by using an equal amount of n-butyllithium, after the reaction is completed, filtering, and concentrating the filtrate in vacuum till colorless transparent crystal is separated, thereby obtaining the amino pyrrole metal lithium compound. The lithium metal catalyst is simple and convenient in preparation method, easily available in raw material, gentle in reaction condition, and very high in catalytic activity on cyclic trimerization of the isocyanate compounds.
Description
Technical field
The present invention relates to isocyanates cyclic trimerization catalysts, in particular to a kind of lithium containing amino-pyrroles part gold
Metal catalyst and its preparation method and application.
Background technology
The compound that organic ligand with pyrroles as precursor skeleton and metal are formed has stronger metal-ligand key, flexible
Sterically hindered and be easy to compensate for participating in the electronic property at unsatuated metal center of coordination, enjoy the concern of vast chemist,
Especially they have coordination mode (N-η flexibly1(σ),η2,η3,η4η5(π), or two kinds, multiple simultaneous coordination mould
Formula).Experimental results demonstrate, can be with metallic atom with η containing the substituted pyrrole ligand of supplied for electronic1Or η5Pattern is bonded, but very
Rare example report pyrrole structure and metallic atom are with η1,η5Both of which is coordinated simultaneously, and with N-η1(σ),η2,η3Three models
The compound being simultaneously coordinated is the most rare.
Particular, it is important that in many cases, in this metal compound, catalysis activity is had by the bonding pattern of pyrrole ligand
The biggest directly affects.Such as, Hou Zhaomin professor seminar reports containing pyrroles η5The aminophenyl rare earth metal chemical combination of coordination
Thing has higher catalysis activity and Stereo control to cinnamic polymerization, and containing pyrroles η1The aminophenyl rare earth gold of coordination
Belong to compound and be not the most catalyzed activity.Meanwhile, Cui Dongmei professor seminar reports and contains η simultaneously5/η1Mixed ligand pattern double
It is active that tooth pyrroles's amino lanthanide metal compound is respectively provided with higher catalysis to lactide ring-opening polymerisation and isoprene, but for
Catalytic polymerization isoprene controllability is the lowest.Therefore, research metal center with the coordination mode of pyrrole radicals part with bonding pattern is
Improve one of this metal compound important method of catalysis activity in catalytic reaction.
Isocyanuric acid ester, owing to having industry and commercial application value widely, has attracted many chemists to go in for the study exploitation
The cyclisation of significantly more efficient catalysis isocyanates generates the catalyst of isocyanuric acid ester, and period substantial amounts of catalyst includes inorganic, organic
And orgnometallic catalyst is in the news.But, improve catalysis ring by changing the coordination mode of metal and part in catalyst
The research changing isocyanuric acid ester activity is seldom concerned.The invention provides one and contain N-η simultaneously1(σ),η2,η3Three kinds of coordinations
The amino-pyrroles lithium metal compounds of pattern bonding, this metallic compound, as catalyst, can be catalyzed isocyanates efficiently
The cyclic trimerization reaction of compound.
Summary of the invention
It is an object of the invention to provide a kind of amino-pyrroles lithium metallic catalyst, this catalyst is convieniently synthesized, and reaction condition is gentle,
The cyclic trimerization reaction and display of isocyanate ester compound is gone out fabulous catalysis activity.
A kind of amino-pyrroles lithium metallic catalyst that the present invention provides, its structural formula is:
In formula: amino-pyrroles lithium compound is six dimeric structure, wherein four lithium atoms are common four-coordination pattern, other two
Individual lithium atom is η1: η2: η3Coordination mode.
The preparation method of a kind of amino-pyrroles lithium metallic catalyst that the present invention provides, reaction equation is as follows:
Reactions steps is:
Under the conditions of inert gas shielding and ice-water bath, with toluene as reaction dissolvent, with the n-BuLi of equivalent to amino-pyrroles
Part carries out lithiumation, after question response solution clear-cutting forestland to room temperature, is heated to reflux 1-2 hour, is cooled to room temperature, filters, very
Empty concentrated filtrate, places refrigerator 2 days (-25 DEG C), separates out colourless transparent crystal, is amino-pyrroles lithium metallic catalyst, produces
Rate is up to 86%.
Above-mentioned amino-pyrroles lithium metallic catalyst can be applied in the cyclic trimerization of isocyanate ester compound reacts.
Compared with prior art advantages of the present invention and effect: the catalyst preparation process of present invention synthesis is simple, and raw material is easy to get,
Yield is higher, has the highest catalysis activity, have preferably application in the cyclic trimerization reaction of catalysis isocyanate ester compound
Prospect.
Accompanying drawing explanation
Fig. 1 is the Single Crystal X-ray structure chart of amino-pyrroles lithium metallic catalyst of the present invention
Detailed description of the invention:
Hereinafter being only the specific embodiment describing the present invention in detail and provide, these embodiments are not intended to limit the guarantor of the present invention
Protect scope.
The preparation of embodiment 1 amino-pyrroles lithium metallic catalyst and sign
Under the conditions of inert gas shielding and ice-water bath, to the toluene of 2-tertiary fourth amino methyl pyrrole ligand (0.457g, 3mmol)
Solution is slowly added dropwise n-butyllithium solution (1.36mL, 2.2M), drips complete, after clear-cutting forestland to room temperature, be heated to reflux
2 hours, it is cooled to room temperature, filters, filtrate is concentrated in vacuo, place refrigerator 2 days, separate out colourless transparent crystal, be amino
Pyrroles's lithium metallic catalyst (hereinafter referred to as catalyst), productivity 86%.
Crystal parameter: chemical formula C27H45Li3N6, monoclinic system (Monoclinic), space group P-1, cell parameter α=103.295 (2) °, β=95.956 (2), γ=104.913 (2) °, V=
1776.82 (17), Z=22.Mono-crystalline structures figure is shown in Fig. 1.
Part bond distanceLi1-N1 2.083(7),Li1-N3 2.099(7),Li1-N6 2.116(7),Li1-N5 2.135(7),Li1-Li2
2.538(8),Li1-C22 2.649(7),Li1-C1 2.747(7),Li1-Li3 2.913(9),Li2-N2 2.007(7),Li2-N3 2.075(7),
Li2-N4 2.083(7),Li2-N1 2.100(7),Li2-C5 2.629(7),Li2-C4 2.638(7),Li2-C14 2.728(7),Li2-C13
2.747(7),Li3-N5 2.009(7),Li3-C11 2.347(8),Li3-C10 2.495(8),Li3-C12 2.509(8),Li3-C20
2.511(8),Li3-C22 2.644(8),Li3-C13 2.743(8),N1-C1 1.371(5),N1-C4 1.386(4),N2-C5 1.298(5),
N2-C6 1.471(5),N3-C13 1.369(5),N3-C10 1.390(5),N4-C14 1.483(5),N4-C15 1.506(5),N5-C22
1.376(5),N5-C19 1.388(5),N6-C23 1.470(5),N6-C24 1.498(5),C1-C2 1.387(6),C2-C3 1.412(6),
C3-C4 1.394(5),C4-C5 1.437(5),C6-C9 1.512(8),C6-C7 1.510(7),C6-C8 1.515(7)；Part bond angle (°):
N1-Li1-N3 103.8(3),N1-Li1-N6 107.1(3),N3-Li1-N6 136.1(3),N1-Li1-N5 121.1(3),N3-Li1-N5
102.2(3),N6-Li1-N5 87.8(2),N2-Li2-N3 129.9(4),N2-Li2-N4 132.4(3),N3-Li2-N4 86.3(3),
N2-Li2-N1 89.0(3),N3-Li2-N1 104.1(3),N4-Li2-N1 113.7(3),C5-N2-C6 122.2(3),C5-N2-Li2
103.3(3).
Embodiment 2 phenyl isocyanate reaction condition screening experiment
With the pyrroles's lithium metal compounds in embodiment 1 as catalyst, phenyl isocyanate is reaction substrate, carries out cyclic trimerization
Reaction condition screens.Reaction general step is: in 100mL Schlenk reaction bulb, adds 30mL amino-pyrroles lithiumation and closes
The solution of thing, under room temperature condition, is added dropwise over isocyanates (30mmol) by syringe, and solution becomes cloudy immediately, generates white
Color precipitates, and after reaction 30min, TLC detection reaction is complete.Standing, filter, precipitation ether washs 3 times, and vacuum is drained,
Obtain isocyanuric acid ester.Concrete outcome is shown in Table 1.
Table 1 amino-pyrroles lithium compound catalytic cyclization trimeric benzene based isocyanate condition optimizing a
aReaction condition: phenyl isocyanate (30mmol), room temperature, 30 minutes,
bSeparate productivity
The catalytic reaction that embodiment 3 is carried out with different isocyanates for substrate
In 100mL Schlenk reaction bulb, add the diethyl ether solution of 30mL amino-pyrroles lithium compound (0.02mol%), room
Under the conditions of temperature, being added dropwise over corresponding isocyanates (30mmol) by syringe, solution becomes cloudy immediately, generates white precipitate,
After reaction 30min, TLC detection reaction is complete.Standing, filter, precipitation ether washs 3 times, and vacuum is drained, and obtains isocyanide
Urea acid esters.Concrete outcome is shown in Table 2.
Table 2 amino-pyrroles lithium compound catalytic cyclization isocyanuric acid estera
aReaction condition: catalyst amount (0.02%mol), isocyanates (30mmol), ether (30mL), 30 minutes, room
Temperature；
bSeparate productivity
In a word, the amino-pyrroles lithium metallic catalyst that the present invention provides, its metallic lithium atoms coordination mode is various, compares single joining
The similar catalyst (Inorg.Chem.Commun.2013,33,68-72) of bit pattern, catalytic efficiency improves an order of magnitude, tool
There is certain application prospect.
Claims (3)
1. an amino-pyrroles lithium metal compounds, it is characterised in that structural formula is:
The preparation method of a kind of amino-pyrroles lithium metal compounds the most as claimed in claim 1, it is characterised in that include as follows
Step: under the conditions of inert gas shielding and ice-water bath, toluene is reaction dissolvent, with the n-BuLi of equivalent to amino-pyrroles
Part carries out lithiumation, after question response solution slowly returns to room temperature, is heated to reflux 1-2 hour, is cooled to room temperature, filters, vacuum
Concentrated filtrate, places refrigerator, separates out colourless transparent crystal, is amino-pyrroles lithium metal compounds.
3. amino-pyrroles lithium metal compounds as claimed in claim 1 is in catalysis isocyanate ester compound cyclic trimerization reaction
Application.
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| CN106902882A (en) * | 2017-03-03 | 2017-06-30 | 山西大学 | Two-dimentional amino-pyrroles potassium Al bimetal catalyst and its preparation method and application |
| CN110327977A (en) * | 2019-06-21 | 2019-10-15 | 山西大学 | A kind of aluminium Li metal catalyst and its preparation method and application |
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Cited By (3)
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| CN106902882A (en) * | 2017-03-03 | 2017-06-30 | 山西大学 | Two-dimentional amino-pyrroles potassium Al bimetal catalyst and its preparation method and application |
| CN110327977A (en) * | 2019-06-21 | 2019-10-15 | 山西大学 | A kind of aluminium Li metal catalyst and its preparation method and application |
| CN110327977B (en) * | 2019-06-21 | 2021-05-14 | 山西大学 | Aluminum-lithium bimetallic catalyst and preparation method and application thereof |
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