CN107915759A - A kind of three phosphonitrile of efficient flame-retarding agent siloxy fluoro ring and its synthetic method - Google Patents
A kind of three phosphonitrile of efficient flame-retarding agent siloxy fluoro ring and its synthetic method Download PDFInfo
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- CN107915759A CN107915759A CN201711088948.7A CN201711088948A CN107915759A CN 107915759 A CN107915759 A CN 107915759A CN 201711088948 A CN201711088948 A CN 201711088948A CN 107915759 A CN107915759 A CN 107915759A
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- China
- Prior art keywords
- phosphonitrile
- siloxy
- ring
- synthetic method
- fluoro
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- ZSTLPJLUQNQBDQ-UHFFFAOYSA-N azanylidyne(dihydroxy)-$l^{5}-phosphane Chemical compound OP(O)#N ZSTLPJLUQNQBDQ-UHFFFAOYSA-N 0.000 title claims abstract description 59
- 125000001153 fluoro group Chemical group F* 0.000 title claims abstract description 36
- 125000004469 siloxy group Chemical group [SiH3]O* 0.000 title claims abstract description 30
- 238000010189 synthetic method Methods 0.000 title claims abstract description 14
- 239000003340 retarding agent Substances 0.000 title abstract description 4
- -1 silicane sodium alkoxide Chemical class 0.000 claims abstract description 24
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims abstract description 16
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims abstract description 12
- 239000011591 potassium Substances 0.000 claims abstract description 12
- 229910052700 potassium Inorganic materials 0.000 claims abstract description 12
- 239000003960 organic solvent Substances 0.000 claims abstract description 11
- 150000001875 compounds Chemical class 0.000 claims abstract description 10
- 238000006243 chemical reaction Methods 0.000 claims abstract description 8
- 239000000377 silicon dioxide Substances 0.000 claims abstract description 8
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 7
- 238000003682 fluorination reaction Methods 0.000 claims abstract description 6
- OXOZHAWWRPCVGL-UHFFFAOYSA-N lithium;trimethyl(oxido)silane Chemical compound [Li+].C[Si](C)(C)[O-] OXOZHAWWRPCVGL-UHFFFAOYSA-N 0.000 claims abstract description 6
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims abstract 2
- 239000003063 flame retardant Substances 0.000 claims description 28
- 239000003792 electrolyte Substances 0.000 claims description 23
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 11
- HBBGRARXTFLTSG-UHFFFAOYSA-N Lithium ion Chemical compound [Li+] HBBGRARXTFLTSG-UHFFFAOYSA-N 0.000 claims description 11
- 229910001416 lithium ion Inorganic materials 0.000 claims description 11
- 229910052698 phosphorus Inorganic materials 0.000 claims description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 9
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 9
- 239000011574 phosphorus Substances 0.000 claims description 8
- HHVIBTZHLRERCL-UHFFFAOYSA-N sulfonyldimethane Chemical compound CS(C)(=O)=O HHVIBTZHLRERCL-UHFFFAOYSA-N 0.000 claims description 8
- QGHDLJAZIIFENW-UHFFFAOYSA-N 4-[1,1,1,3,3,3-hexafluoro-2-(4-hydroxy-3-prop-2-enylphenyl)propan-2-yl]-2-prop-2-enylphenol Chemical group C1=C(CC=C)C(O)=CC=C1C(C(F)(F)F)(C(F)(F)F)C1=CC=C(O)C(CC=C)=C1 QGHDLJAZIIFENW-UHFFFAOYSA-N 0.000 claims description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 6
- 239000000463 material Substances 0.000 claims description 5
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 5
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 4
- 239000007788 liquid Substances 0.000 claims description 4
- 239000003208 petroleum Substances 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 3
- MVPPADPHJFYWMZ-IDEBNGHGSA-N chlorobenzene Chemical group Cl[13C]1=[13CH][13CH]=[13CH][13CH]=[13CH]1 MVPPADPHJFYWMZ-IDEBNGHGSA-N 0.000 claims description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Substances ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 2
- NTSNXSJENBZFSF-UHFFFAOYSA-N [Na+].[SiH3][O-] Chemical compound [Na+].[SiH3][O-] NTSNXSJENBZFSF-UHFFFAOYSA-N 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 238000000034 method Methods 0.000 abstract description 6
- 239000011734 sodium Substances 0.000 abstract description 5
- 229910052708 sodium Inorganic materials 0.000 abstract description 5
- 238000004519 manufacturing process Methods 0.000 abstract description 2
- 230000008569 process Effects 0.000 abstract description 2
- 239000000376 reactant Substances 0.000 abstract description 2
- 239000002904 solvent Substances 0.000 abstract description 2
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 description 25
- 239000000654 additive Substances 0.000 description 25
- 230000000996 additive effect Effects 0.000 description 22
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 19
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 12
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 11
- 230000000694 effects Effects 0.000 description 11
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 7
- 229910052744 lithium Inorganic materials 0.000 description 7
- GKTNLYAAZKKMTQ-UHFFFAOYSA-N n-[bis(dimethylamino)phosphinimyl]-n-methylmethanamine Chemical class CN(C)P(=N)(N(C)C)N(C)C GKTNLYAAZKKMTQ-UHFFFAOYSA-N 0.000 description 7
- 239000000243 solution Substances 0.000 description 6
- KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 description 4
- 230000014759 maintenance of location Effects 0.000 description 4
- 229910052710 silicon Inorganic materials 0.000 description 4
- VAYTZRYEBVHVLE-UHFFFAOYSA-N 1,3-dioxol-2-one Chemical compound O=C1OC=CO1 VAYTZRYEBVHVLE-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- 125000001309 chloro group Chemical group Cl* 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 238000004090 dissolution Methods 0.000 description 3
- 239000013538 functional additive Substances 0.000 description 3
- 239000010703 silicon Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
- BJWMSGRKJIOCNR-UHFFFAOYSA-N 4-ethenyl-1,3-dioxolan-2-one Chemical compound C=CC1COC(=O)O1 BJWMSGRKJIOCNR-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
- 229910002097 Lithium manganese(III,IV) oxide Inorganic materials 0.000 description 2
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 2
- QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical group CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 2
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 238000005868 electrolysis reaction Methods 0.000 description 2
- 239000008151 electrolyte solution Substances 0.000 description 2
- 229910002804 graphite Inorganic materials 0.000 description 2
- 239000010439 graphite Substances 0.000 description 2
- 229910003002 lithium salt Inorganic materials 0.000 description 2
- 159000000002 lithium salts Chemical class 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 231100000989 no adverse effect Toxicity 0.000 description 2
- JMANVNJQNLATNU-UHFFFAOYSA-N oxalonitrile Chemical compound N#CC#N JMANVNJQNLATNU-UHFFFAOYSA-N 0.000 description 2
- YTZKOQUCBOVLHL-UHFFFAOYSA-N tert-butylbenzene Chemical compound CC(C)(C)C1=CC=CC=C1 YTZKOQUCBOVLHL-UHFFFAOYSA-N 0.000 description 2
- 238000005292 vacuum distillation Methods 0.000 description 2
- ZZXUZKXVROWEIF-UHFFFAOYSA-N 1,2-butylene carbonate Chemical compound CCC1COC(=O)O1 ZZXUZKXVROWEIF-UHFFFAOYSA-N 0.000 description 1
- XJYDIOOQMIRSSY-UHFFFAOYSA-N 1,3,2-dioxathiepane 2-oxide Chemical compound O=S1OCCCCO1 XJYDIOOQMIRSSY-UHFFFAOYSA-N 0.000 description 1
- WDXYVJKNSMILOQ-UHFFFAOYSA-N 1,3,2-dioxathiolane 2-oxide Chemical compound O=S1OCCO1 WDXYVJKNSMILOQ-UHFFFAOYSA-N 0.000 description 1
- DZKXDEWNLDOXQH-UHFFFAOYSA-N 1,3,5,2,4,6-triazatriphosphinine Chemical compound N1=PN=PN=P1 DZKXDEWNLDOXQH-UHFFFAOYSA-N 0.000 description 1
- 125000006091 1,3-dioxolane group Chemical class 0.000 description 1
- QHTJSSMHBLGUHV-UHFFFAOYSA-N 2-methylbutan-2-ylbenzene Chemical compound CCC(C)(C)C1=CC=CC=C1 QHTJSSMHBLGUHV-UHFFFAOYSA-N 0.000 description 1
- JWUJQDFVADABEY-UHFFFAOYSA-N 2-methyltetrahydrofuran Chemical class CC1CCCO1 JWUJQDFVADABEY-UHFFFAOYSA-N 0.000 description 1
- SJHAYVFVKRXMKG-UHFFFAOYSA-N 4-methyl-1,3,2-dioxathiolane 2-oxide Chemical compound CC1COS(=O)O1 SJHAYVFVKRXMKG-UHFFFAOYSA-N 0.000 description 1
- NLOAOXIUYAGBGO-UHFFFAOYSA-N C.[O] Chemical compound C.[O] NLOAOXIUYAGBGO-UHFFFAOYSA-N 0.000 description 1
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 1
- 229910013188 LiBOB Inorganic materials 0.000 description 1
- 229910000552 LiCF3SO3 Inorganic materials 0.000 description 1
- 229910001290 LiPF6 Inorganic materials 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000011149 active material Substances 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- RTZKMGZSJBRJFI-UHFFFAOYSA-N boric acid;lithium Chemical compound [Li].OB(O)O RTZKMGZSJBRJFI-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- SIXOAUAWLZKQKX-UHFFFAOYSA-N carbonic acid;prop-1-ene Chemical compound CC=C.OC(O)=O SIXOAUAWLZKQKX-UHFFFAOYSA-N 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 150000008422 chlorobenzenes Chemical class 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000002485 combustion reaction Methods 0.000 description 1
- 150000005676 cyclic carbonates Chemical group 0.000 description 1
- HHNHBFLGXIUXCM-GFCCVEGCSA-N cyclohexylbenzene Chemical compound [CH]1CCCC[C@@H]1C1=CC=CC=C1 HHNHBFLGXIUXCM-GFCCVEGCSA-N 0.000 description 1
- 230000006837 decompression Effects 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical group COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 description 1
- VUPKGFBOKBGHFZ-UHFFFAOYSA-N dipropyl carbonate Chemical compound CCCOC(=O)OCCC VUPKGFBOKBGHFZ-UHFFFAOYSA-N 0.000 description 1
- 230000005611 electricity Effects 0.000 description 1
- 239000002001 electrolyte material Substances 0.000 description 1
- 229940021013 electrolyte solution Drugs 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000000686 essence Substances 0.000 description 1
- VEWLDLAARDMXSB-UHFFFAOYSA-N ethenyl sulfate;hydron Chemical compound OS(=O)(=O)OC=C VEWLDLAARDMXSB-UHFFFAOYSA-N 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 1
- 229910001540 lithium hexafluoroarsenate(V) Inorganic materials 0.000 description 1
- MHCFAGZWMAWTNR-UHFFFAOYSA-M lithium perchlorate Chemical compound [Li+].[O-]Cl(=O)(=O)=O MHCFAGZWMAWTNR-UHFFFAOYSA-M 0.000 description 1
- 229910001486 lithium perchlorate Inorganic materials 0.000 description 1
- 229910001496 lithium tetrafluoroborate Inorganic materials 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 238000005554 pickling Methods 0.000 description 1
- 238000012805 post-processing Methods 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000000979 retarding effect Effects 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 150000008053 sultones Chemical class 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000005406 washing Methods 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
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6564—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms
- C07F9/6581—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and nitrogen atoms with or without oxygen or sulfur atoms, as ring hetero atoms
- C07F9/65812—Cyclic phosphazenes [P=N-]n, n>=3
- C07F9/65815—Cyclic phosphazenes [P=N-]n, n>=3 n = 3
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
- H01M10/00—Secondary cells; Manufacture thereof
- H01M10/05—Accumulators with non-aqueous electrolyte
- H01M10/056—Accumulators with non-aqueous electrolyte characterised by the materials used as electrolytes, e.g. mixed inorganic/organic electrolytes
- H01M10/0564—Accumulators with non-aqueous electrolyte characterised by the materials used as electrolytes, e.g. mixed inorganic/organic electrolytes the electrolyte being constituted of organic materials only
- H01M10/0566—Liquid materials
- H01M10/0567—Liquid materials characterised by the additives
-
- 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)
- Electrochemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Inorganic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Manufacturing & Machinery (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Condensed Matter Physics & Semiconductors (AREA)
- Secondary Cells (AREA)
Abstract
The invention discloses a kind of three phosphonitrile of efficient flame-retarding agent siloxy fluoro ring and its synthetic method, fluorination three phosphonitrile of ring is dissolved in organic solvent, adds silica based compound, reacts 0.5 72h, substitute a fluorine atom with a siloxy, obtain three phosphonitrile of siloxy fluoro ring.The silica based compound is trimethyl silicane potassium alcoholate or trimethyl silicane sodium alkoxide or lithium trimethylsilanolate.The synthesising method reacting condition that the present invention uses is gentle, and reaction controllability is good, easy to industrialized production；And technological process is simple, reactant and solvent are recyclable, and product purity and yield are also higher.
Description
Technical field
The present invention relates to a kind of three phosphonitrile of efficient flame-retarding agent siloxy fluoro ring and its synthetic method.
Background technology
Phosphazene compound is the hybrid inorganic-organic compound that a kind of skeleton is alternately arranged by nitrogen and phosphorus, can be divided into poly- phosphorus
Nitrile and ring phosphonitrile.Wherein, three phosphonitrile of chloro ring is most representative compound in cyclic phosphazene compound, since chlorine atom has
Very strong reactivity, is easily substituted by various nucleopilic reagents.Therefore, using three phosphonitrile of chloro ring as intermediate, can synthesize
Phosphazene derivative with various organo-functional groups.
At present, studying more phosphazene derivative has：Hexaaniline cyclotriphosphazene, six ethamine basic rings, three phosphonitrile, hexafluoro ring
Three phosphonitriles, six isopropoxy rings, three phosphonitrile, three phosphonitrile of hexakis-methoxy basic ring, six ethoxy basic rings, three phosphonitrile, six positive propoxy rings, three phosphorus
Nitrile.Phosphazene derivative is mainly used as fire retardant.
But there is the shortcomings that notable as the flame-retardant additive of lithium-ion battery electrolytes, above-mentioned phosphazene derivative.Through grinding
Study carefully discovery, hexaphenoxycyclotriphosphazene, three phosphonitrile of hexakis-methoxy basic ring, six propoxyl group rings, three phosphonitrile, 1- ethyoxyls -1,3,3,5,5-
Five fluorine rings, three phosphonitrile cannot significantly improve the flash-point of lithium-ion battery electrolytes, and resistance combustion temperature section is small, fire resistance with
Range of temperature is big, therefore cannot thoroughly prevent what battery from occurring in the case of abuse catch fire, burn and even explode
The problem of Deng some securities.In addition, after addition flame-retardant additive, larger negative shadow is had to the battery performance of lithium battery
Ring.
The content of the invention
For above technical problem, the present invention provides a kind of synthetic method of three phosphonitrile of siloxy fluoro ring, is prepared
Three phosphonitrile of siloxy fluoro ring be applied to high performance lithium ion battery electrolysis additive in.
Three phosphorus nitrile compounds of siloxy fluoro ring, have following structural formula：
The present invention also provides a kind of synthetic method of three phosphonitrile of siloxy fluoro ring, comprise the following steps：
Fluorination three phosphonitrile of ring is dissolved in organic solvent, adds silica based compound, 0.5-72h is reacted, with a silicon
Epoxide substitutes a fluorine atom, obtains three phosphonitrile of siloxy fluoro ring.
Preferably, the silica based compound is trimethyl silicane potassium alcoholate or trimethyl silicane sodium alkoxide or lithium trimethylsilanolate.Through
Overtesting verifies that the siloxy effect of these three silica based compounds is more preferable.
In order to improve the conversion ratio of three phosphonitrile of fluoro ring, it is preferred that three phosphonitrile of fluoro ring and siloxy chemical combination
The ratio between amount of material of thing is 1:2-4:1.
Preferably, the reaction temperature is -30-120 DEG C.
It is further preferred that the reaction temperature is 10~40 DEG C.
Preferably, three phosphonitrile of fluoro ring is three phosphonitrile of hexafluoro ring.Different fluoro rings can be prepared according to the difference of raw material
Three phosphonitrile products.
In order to improve reaction efficiency, it is preferred that the organic solvent is chlorobenzene, petroleum ether, pyridine, tetrahydrochysene furan
Mutter, in n-hexane, acetonitrile, benzonitrile, toluene, N,N-dimethylformamide (DMF), dimethylbenzene or dimethyl sulfone (DMSO2)
One or more mixtures.
Application of the three phosphorus nitrile compounds of siloxy fluoro ring in lithium-ion battery electrolytes are prepared, specifically, described
Fire retardant of three phosphonitrile of siloxy fluoro ring as lithium-ion battery electrolytes.
Wherein, the lithium-ion battery electrolytes are made of four class components：Lithium salts, carbonates and/or ethers are organic molten
Agent, phosphazene derivative class flame-retardant additive and other functional additives, the phosphazene derivative class flame-retardant additive are siloxy
Five fluorine rings, three phosphonitrile.
Wherein, lithium salts is LiPF6、LiClO4、LiAsF6、LiBF4、LiCH3SO3、LiCF3SO3, LiBOB (dioxalic acid boric acid
Lithium) and LiN (CF3SO2)2In one kind or its mixture.
The carbonate based organic solvent is cyclic carbonates and/or linear carbonate class compound.
The cyclic carbonates compound is ethylene carbonate (EC), propene carbonate (PC), gamma-butyrolacton (GBL)
With the one or more in butylene carbonate.The linear carbonate class compound preferably is selected from dimethyl carbonate (DMC), carbonic acid two
Ethyl ester (DEC), dipropyl carbonate, methyl ethyl ester (EMC) and carbon number be 3-8 straight or branched aliphatic monool with
One or more in the carbonic acid ester derivative of carbonic acid synthesis.
The ether organic solvent is selected from tetrahydrofuran (THF), 2- methyltetrahydrofurans, 1,3- dioxolanes, diformazan
One or more in oxygen methane, 1,2- dimethoxies and diethylene glycol dimethyl ether.
Other functional additives are that the one or more in following compounds coexist：Biphenyl (BP), vinylene carbonate
(VC), vinylethylene carbonate (VEC), fluorinated ethylene carbonate (FEC), propylene sulfite, butylene sulfite, 1,3-
(1- propylene) sultone, ethylene sulfite (ES), sulfuric acid vinyl ester, cyclohexyl benzene, tert-butyl benzene, tert-amyl benzene and fourth two
Cyanogen.
The present invention is substituted a fluorine atom with a siloxy, is obtained siloxy fluoro ring three using fluorination three phosphonitrile of ring
Phosphonitrile.Wherein, two kinds of ignition-proof elements of P and F are connected directly in five fluorine ring of siloxy, three phosphonitrile, can increase by five fluorine ring three of siloxy
Combination power between phosphonitrile and carbonates and/or ether organic solvent, reduces the volatility of carbonate based organic solvent, from
And further improve the security of battery；P is connected with Si elements by an oxygen atom, not only effectively reduces inflammable gas
Release, and enable to the flash-point of the additive to improve, so as to improve the flash-point of electrolyte.And the phosphonitrile fluorination ring used
Four kinds of ignition-proof elements are effectively connected to together by shape structure, not only to being had no adverse effect to the battery performance of lithium battery, on the contrary
The cyclical stability and battery capacity conservation rate of battery can be improved.Found through experiment, the present invention is using phosphonitrile fluorination ring ring
Shape structure links together four kinds of ignition-proof elements, and ignition-proof element is compact, not only reduces the usage amount of flame-retardant additive so that
Flame retardant effect is excellent, moreover, improving the cyclical stability and battery capacity conservation rate of battery, this is those skilled in the art institute
The technique effect that cannot be expected.
Above-mentioned technical proposal has the advantages that：
(1) viscosity of three phosphonitrile of siloxy fluoro ring is relatively low, ensures the high conductivity of electrolyte；It is with N, P, F and Si
Four kinds of ignition-proof elements, have synergistic effect, can reduce additive amount, can improve flame retarding efficiency；The presence of F elements contributes to electricity
Pole interface forms excellent SEI films, improves the compatibility between electrolyte and active material, F elements can also weaken intermolecular
Viscous force so that molecule, the migration resistance of ion reduce, and then reduce viscosity, improve electrolytic conductivity.Si elements, have
Temperature-resistance characteristic, heat endurance are high so that electrolyte not only can be and low temperature resistant with high temperature resistant, can be in a very wide temperature
Used in the range of degree.Either chemical property or physical mechanical property, variation with temperature all very littles.With weatherability, no
Easily decomposed by ultraviolet light and ozone.Si elements have heat endurance more more preferable than other materials and resistance to irradiation and weather-proof ability.
Service life of the silicon in natural environment is up to decades.
(2) compared with prior art, the synthesising method reacting condition that the present invention uses is gentle, and reaction controllability is good, just
In industrialized production；The post processing of synthetic method need to only be filtered to having reacted material, and the simple operations such as concentration are i.e. available
The product of better quality and yield, it is not necessary to through multiple pickling, alkali cleaning, so as to avoid because multiple washing and caused by it is unnecessary
Loss, improves yield.Present invention process flow is simple, and energy consumption is low, and reactant and solvent are recyclable, product purity and yield
It is higher.
Brief description of the drawings
The Figure of description for forming the part of the present invention is used for providing a further understanding of the present invention, and of the invention shows
Meaning property embodiment and its explanation are used to explain the present invention, do not form inappropriate limitation of the present invention.
Fig. 1 is the infrared spectrogram of three phosphorus nitrile compounds of siloxy fluoro ring.
Embodiment
It is noted that described further below be all exemplary, it is intended to provides further instruction to the present invention.It is unless another
Indicate, all technical and scientific terms used herein has usual with general technical staff of the technical field of the invention
The identical meanings of understanding.
It should be noted that term used herein above is merely to describe embodiment, and be not intended to restricted root
According to the illustrative embodiments of the present invention.As used herein, unless the context clearly indicates otherwise, otherwise singulative
It is also intended to include plural form, additionally, it should be understood that, when in the present specification using term "comprising" and/or " bag
Include " when, it indicates existing characteristics, step, operation and/or combinations thereof.
In order to enable those skilled in the art can clearly understand technical scheme, below with reference to tool
The embodiment of the body technical solution that the present invention will be described in detail.
Embodiment 1：
Three phosphonitrile dissolution of crystals of 49.8g hexafluoros ring is formed into three phosphonitrile solution of hexafluoro ring, Xiang Rong in 200ml tetrahydrofurans
12.9g trimethyl silicane potassium alcoholates are added in liquid, are stirred until homogeneous, and 20h is reacted under 10 DEG C of temperature conditionss, filtered, decompression is steamed
Three phosphonitrile of phosphazene derivative siloxy fluoro ring is obtained after evaporating, there is following structural formula,
Yield 95%, and determine its structure with infrared, such as Fig. 1 institutes
Show.
Embodiment 2：
Three phosphonitrile dissolution of crystals of 49.8g hexafluoros ring forms three phosphonitrile solution of hexafluoro ring in 300ml n-hexanes, into solution
12.9g trimethyl silicane potassium alcoholates are added, are stirred until homogeneous, and 10h is reacted under 40 DEG C of temperature conditionss, after filtered, vacuum distillation
Obtain three phosphonitrile of phosphazene derivative siloxy fluoro ring, yield 96%.
Embodiment 3：
Three phosphonitrile dissolution of crystals of 49.8g hexafluoros ring forms three phosphonitrile solution of hexafluoro ring in 200ml chlorobenzenes, into solution
12.9g trimethyl silicane potassium alcoholates are added, are stirred until homogeneous, and 15h is reacted under 30 DEG C of temperature conditionss, after filtered, vacuum distillation
Obtain three phosphonitrile of phosphazene derivative siloxy fluoro ring, yield 95%.
Embodiment 4：
The present embodiment is same as Example 1, and difference is tetrahydrofuran being changed to petroleum ether, by trimethyl silicane potassium alcoholate
Trimethyl silicane sodium alkoxide is changed to, obtains three phosphonitrile of phosphazene derivative siloxy fluoro ring, yield 97%.
Embodiment 5：
The present embodiment is same as Example 1, and difference is tetrahydrofuran being changed to pyridine, and trimethyl silicane potassium alcoholate is changed
For trimethyl silicane sodium alkoxide, three phosphonitrile of phosphazene derivative siloxy fluoro ring, yield 96% are obtained.
Embodiment 6：
The present embodiment is same as Example 1, and difference is tetrahydrofuran being changed to DMF, and trimethyl silicane potassium alcoholate is changed
For trimethyl silicane sodium alkoxide, three phosphonitrile of phosphazene derivative siloxy fluoro ring, yield 97% are obtained.
Embodiment 7：
The present embodiment is same as Example 1, and difference is tetrahydrofuran being changed to acetonitrile, and trimethyl silicane potassium alcoholate is changed
For lithium trimethylsilanolate, three phosphonitrile of phosphazene derivative siloxy fluoro ring, yield 96% are obtained.
Embodiment 8：
The present embodiment is same as Example 1, and difference is tetrahydrofuran being changed to benzonitrile, by trimethyl silicane potassium alcoholate
Lithium trimethylsilanolate is changed to, obtains three phosphonitrile of phosphazene derivative siloxy fluoro ring, yield 97%.
Embodiment 9：
The present embodiment is same as Example 1, and difference is tetrahydrofuran being changed to the mixed of tetrahydrofuran and petroleum ether
Compound, lithium trimethylsilanolate is changed to by trimethyl silicane potassium alcoholate, obtains three phosphonitrile of phosphazene derivative siloxy fluoro ring, and yield is
95%.
1~32 flame retardant effect of experimental example
The present invention is used as phosphazene derivative based flame retardant, and compared with the based flame retardant before, difference lies in siloxy fluorine
Contain elements Si in Dai Huansan phosphonitriles.Elements Si, has temperature-resistance characteristic, and heat endurance is high so that electrolyte not only can be with resistance to height
Temperature, and it is low temperature resistant, it can be used within the scope of a very wide temperature.Either chemical property or Physical Mechanical
Can, variation with temperature all very littles.With weatherability, it is not easy to be decomposed by ultraviolet light and ozone.Si elements have than other materials
Expect more preferable heat endurance and resistance to irradiation and weather-proof ability.Service life of the silicon in natural environment is up to decades.
The component of the invention for using form to list 32 kinds of flame-retardant electrolyte solutions forms and each electrolyte is molten
The test data of liquid self-extinguishing time, specific data such as table 1 below.
Component, the self-extinguishing time of 1 various electrolyte of table
It can be obtained by table 1, the electrolyte in the present invention adds five fluorine ring of siloxy, three phosphonitrile flame-retardant additive, can significantly improve
The fire resistance of electrolyte, such as the electrolyte in experimental example 18, its organic solvent is that volume ratio is 1：1：1 EC/DEC/EMC,
LiClO containing 0.3mol/L4, 0.2mol/L VC and 6% five fluorine ring of siloxy, three phosphonitrile flame-retardant additive, can reach
Complete non-flammable effect (self-extinguishing time 0s), the mass fraction of flame-retardant additive of the prior art in the electrolytic solution are general
A preferable non-flammable effect could be had by reaching 10~40%, but the electrolysis that the flame-retardant additive of better quality fraction can make
The viscosity rise of liquid, influences the electric conductivity of electrolyte, and then influences the battery performance of lithium battery.
This table 1 is it can also be seen that different organic solvents and other functional additives has not the fire resistance of electrolyte
Same influence, by screening and optimizing, the formula for obtaining the optimal electrolyte of the present invention is experimental example 18 and experimental example 14, when fire-retardant
When the content of additive is less, complete non-flammable effect can be played.
The battery capacity effect of 33 lithium ion battery of experimental example
Electrolyte described in experimental example 18 is injected into commodity LiMn2O4Charge-discharge test is carried out in/graphite lithium ion battery.
Draw, after circulating battery 20 weeks, the capacity retention ratio for being not added with the battery of flame-retardant additive is 90%, contains flame-retardant additive
Battery capacity retention ratio be 94%.
Electrolyte described in experimental example 24 is injected into commodity LiMn2O4Charge-discharge test is carried out in/graphite lithium ion battery.
Draw, after circulating battery 20 weeks, the capacity retention ratio for being not added with the battery of flame-retardant additive is 89%, contains flame-retardant additive
Battery capacity retention ratio be 93%.
Flame-retardant additive of the prior art can reduce the combustibility of electrolyte, but most of flame-retardant additives are to lithium
Battery performance has larger negative effect, and a small number of flame-retardant additives also can cause the battery performance of lithium battery to decline.
And after the flame-retardant additive in the application adds, on the premise of excellent flame effect is ensured, a small amount of flame-retardant additive is added,
Not only the battery performance of lithium battery is had no adverse effect, the cyclical stability and battery capacity that can improve battery on the contrary are protected
Holdup, can apply as safety additives in actual battery, this is lithium battery electrolytes resistance conventional in the prior art
Fire the inaccessiable technique effect of additive institute.When the content of flame-retardant additive is higher, can influence the electric conductivity of electrolyte with
And the cyclical stability and battery capacity conservation rate of battery.
Above-described embodiment is the preferable embodiment of the present invention, but embodiments of the present invention and from above-described embodiment
Limitation, other any Spirit Essences without departing from the present invention with made under principle change, modification, replacement, combine, simplification,
Equivalent substitute mode is should be, is included within protection scope of the present invention.
Claims (10)
1. three phosphorus nitrile compounds of siloxy fluoro ring, have following structural formula：
2. a kind of synthetic method of three phosphonitrile of siloxy fluoro ring, it is characterized in that, comprise the following steps：
Fluorination three phosphonitrile of ring is dissolved in organic solvent, adds silica based compound, 0.5-72h is reacted, with a siloxy
Substitute a fluorine atom, obtain three phosphonitrile of siloxy fluoro ring.
3. synthetic method as claimed in claim 2, it is characterized in that：The silica based compound is trimethyl silicane potassium alcoholate or front three
Base sodium silanolate or lithium trimethylsilanolate.
4. synthetic method as claimed in claim 2, it is characterized in that：The material of three phosphonitrile of fluoro ring and silica based compound
The ratio between amount be 1:2-4:1.
5. synthetic method as claimed in claim 2, it is characterized in that：The reaction temperature is -30-120 DEG C.
6. synthetic method as claimed in claim 5, it is characterized in that：The reaction temperature is 10~40 DEG C.
7. synthetic method as claimed in claim 2, it is characterized in that：Three phosphonitrile of fluoro ring is three phosphonitrile of hexafluoro ring.
8. synthetic method as claimed in claim 2, it is characterized in that：The organic solvent is chlorobenzene, petroleum ether, pyridine, four
Hydrogen furans, n-hexane, acetonitrile, benzonitrile, toluene, N,N-dimethylformamide (DMF), dimethylbenzene or dimethyl sulfone (DMSO2)
In one or more mixtures.
9. the answering in lithium-ion battery electrolytes are prepared of the three phosphorus nitrile compounds of siloxy fluoro ring described in claim 1
With.
10. application as claimed in claim 9, it is characterized in that：Three phosphonitrile of siloxy fluoro ring is as lithium ion battery battery
Solve the fire retardant of liquid.
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| CN111193068A (en) * | 2020-02-16 | 2020-05-22 | 成都市水泷头化工科技有限公司 | Polyphosphazene composite flame retardant additive for lithium battery electrolyte and preparation method thereof |
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| CN113871716A (en) * | 2020-06-30 | 2021-12-31 | 东营市海科新源化工有限责任公司 | Multifunctional electrolyte for high-nickel lithium ion battery and lithium ion battery |
| CN114573637A (en) * | 2020-12-02 | 2022-06-03 | 张家港市国泰华荣化工新材料有限公司 | Preparation method of trimethylsiloxy pentafluorocyclotriphosphazene |
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| CN110724160A (en) * | 2019-11-12 | 2020-01-24 | 成都硅宝科技股份有限公司 | Organic silicon flame-retardant additive and flame-retardant lithium ion battery electrolyte |
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| CN114573637A (en) * | 2020-12-02 | 2022-06-03 | 张家港市国泰华荣化工新材料有限公司 | Preparation method of trimethylsiloxy pentafluorocyclotriphosphazene |
| CN114573637B (en) * | 2020-12-02 | 2023-11-17 | 张家港市国泰华荣化工新材料有限公司 | Preparation method of trimethylsiloxy pentafluoroethyl triphosphazene |
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