JP5702393B2 - ホスホリルクロライド及びグリコール又はポリグリコールのモノアルキルエーテルからリン酸エステルを製造する方法 - Google Patents
ホスホリルクロライド及びグリコール又はポリグリコールのモノアルキルエーテルからリン酸エステルを製造する方法 Download PDFInfo
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- JP5702393B2 JP5702393B2 JP2012533201A JP2012533201A JP5702393B2 JP 5702393 B2 JP5702393 B2 JP 5702393B2 JP 2012533201 A JP2012533201 A JP 2012533201A JP 2012533201 A JP2012533201 A JP 2012533201A JP 5702393 B2 JP5702393 B2 JP 5702393B2
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- Japan
- Prior art keywords
- glycol
- phosphoryl chloride
- monoether
- reaction
- lithium
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- -1 phosphate ester Chemical class 0.000 title claims description 79
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 title claims description 72
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 title description 62
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 title description 41
- 229910019142 PO4 Inorganic materials 0.000 title description 21
- 239000010452 phosphate Substances 0.000 title description 19
- 150000001346 alkyl aryl ethers Chemical class 0.000 title description 7
- 229920000151 polyglycol Polymers 0.000 title description 2
- 239000010695 polyglycol Substances 0.000 title description 2
- 238000004519 manufacturing process Methods 0.000 title 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 18
- 238000000034 method Methods 0.000 claims description 15
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 10
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 9
- SBASXUCJHJRPEV-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethanol Chemical compound COCCOCCO SBASXUCJHJRPEV-UHFFFAOYSA-N 0.000 claims description 7
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 claims description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 5
- 125000004076 pyridyl group Chemical group 0.000 claims description 4
- JLGLQAWTXXGVEM-UHFFFAOYSA-N triethylene glycol monomethyl ether Chemical compound COCCOCCOCCO JLGLQAWTXXGVEM-UHFFFAOYSA-N 0.000 claims description 4
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-N phosphoric acid Substances OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims 1
- 239000000203 mixture Substances 0.000 description 37
- 238000006243 chemical reaction Methods 0.000 description 31
- 239000000047 product Substances 0.000 description 27
- 239000003792 electrolyte Substances 0.000 description 21
- 235000021317 phosphate Nutrition 0.000 description 20
- 239000002904 solvent Substances 0.000 description 19
- 229910052744 lithium Inorganic materials 0.000 description 17
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 16
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- 150000001875 compounds Chemical class 0.000 description 12
- 125000000217 alkyl group Chemical group 0.000 description 11
- 239000011541 reaction mixture Substances 0.000 description 11
- 229920001515 polyalkylene glycol Polymers 0.000 description 10
- 229910003002 lithium salt Inorganic materials 0.000 description 9
- 159000000002 lithium salts Chemical class 0.000 description 9
- 239000000463 material Substances 0.000 description 8
- HBBGRARXTFLTSG-UHFFFAOYSA-N Lithium ion Chemical compound [Li+] HBBGRARXTFLTSG-UHFFFAOYSA-N 0.000 description 7
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 7
- 239000008151 electrolyte solution Substances 0.000 description 7
- 150000002148 esters Chemical class 0.000 description 7
- 238000004811 liquid chromatography Methods 0.000 description 7
- 229910001416 lithium ion Inorganic materials 0.000 description 7
- 238000004949 mass spectrometry Methods 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 125000005910 alkyl carbonate group Chemical group 0.000 description 6
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 6
- 150000005676 cyclic carbonates Chemical class 0.000 description 6
- 150000003840 hydrochlorides Chemical class 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 5
- 239000000654 additive Substances 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 239000002131 composite material Substances 0.000 description 5
- 239000001257 hydrogen Substances 0.000 description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 5
- YPFDHNVEDLHUCE-UHFFFAOYSA-N propane-1,3-diol Chemical compound OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 5
- 150000003457 sulfones Chemical class 0.000 description 5
- 229910052723 transition metal Inorganic materials 0.000 description 5
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 4
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- KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical compound COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 description 4
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 4
- 229910052759 nickel Inorganic materials 0.000 description 4
- 239000002798 polar solvent Substances 0.000 description 4
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 4
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- 229910013870 LiPF 6 Inorganic materials 0.000 description 3
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- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 3
- 239000012535 impurity Substances 0.000 description 3
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- 229910052698 phosphorus Inorganic materials 0.000 description 3
- 239000011574 phosphorus Substances 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 239000007784 solid electrolyte Substances 0.000 description 3
- 230000004580 weight loss Effects 0.000 description 3
- DHKHKXVYLBGOIT-UHFFFAOYSA-N 1,1-Diethoxyethane Chemical compound CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 2
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- 229910015015 LiAsF 6 Inorganic materials 0.000 description 2
- 229910013063 LiBF 4 Inorganic materials 0.000 description 2
- 229910013684 LiClO 4 Inorganic materials 0.000 description 2
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- 239000004698 Polyethylene Substances 0.000 description 2
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 2
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- 125000002947 alkylene group Chemical group 0.000 description 2
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- 150000001412 amines Chemical class 0.000 description 2
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- 238000004587 chromatography analysis Methods 0.000 description 2
- 229910017052 cobalt Inorganic materials 0.000 description 2
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- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 2
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- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 2
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- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 2
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- AIRPCZTWEOZWNF-UHFFFAOYSA-N lithium hydroxy(trioxido)silane iron(2+) Chemical group [Li+].[Fe+2].O[Si]([O-])([O-])[O-] AIRPCZTWEOZWNF-UHFFFAOYSA-N 0.000 description 1
- GELKBWJHTRAYNV-UHFFFAOYSA-K lithium iron phosphate Chemical compound [Li+].[Fe+2].[O-]P([O-])([O-])=O GELKBWJHTRAYNV-UHFFFAOYSA-K 0.000 description 1
- SBWRUMICILYTAT-UHFFFAOYSA-K lithium;cobalt(2+);phosphate Chemical compound [Li+].[Co+2].[O-]P([O-])([O-])=O SBWRUMICILYTAT-UHFFFAOYSA-K 0.000 description 1
- DVATZODUVBMYHN-UHFFFAOYSA-K lithium;iron(2+);manganese(2+);phosphate Chemical compound [Li+].[Mn+2].[Fe+2].[O-]P([O-])([O-])=O DVATZODUVBMYHN-UHFFFAOYSA-K 0.000 description 1
- ILXAVRFGLBYNEJ-UHFFFAOYSA-K lithium;manganese(2+);phosphate Chemical compound [Li+].[Mn+2].[O-]P([O-])([O-])=O ILXAVRFGLBYNEJ-UHFFFAOYSA-K 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 239000011572 manganese Substances 0.000 description 1
- 229910001092 metal group alloy Inorganic materials 0.000 description 1
- 229910052914 metal silicate Inorganic materials 0.000 description 1
- 229910021382 natural graphite Inorganic materials 0.000 description 1
- 229920001220 nitrocellulos Polymers 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 239000012811 non-conductive material Substances 0.000 description 1
- 239000012454 non-polar solvent Substances 0.000 description 1
- 239000011255 nonaqueous electrolyte Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 239000010702 perfluoropolyether Substances 0.000 description 1
- RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 description 1
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 1
- 229920001483 poly(ethyl methacrylate) polymer Polymers 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920001748 polybutylene Polymers 0.000 description 1
- 229920001690 polydopamine Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 239000005077 polysulfide Substances 0.000 description 1
- 229920001021 polysulfide Polymers 0.000 description 1
- 150000008117 polysulfides Polymers 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 229920002981 polyvinylidene fluoride Polymers 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000002516 radical scavenger Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 229920003048 styrene butadiene rubber Polymers 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 150000003464 sulfur compounds Chemical class 0.000 description 1
- 150000008053 sultones Chemical class 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 229910052715 tantalum Inorganic materials 0.000 description 1
- GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical compound [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 0.000 description 1
- 125000005207 tetraalkylammonium group Chemical group 0.000 description 1
- CBXCPBUEXACCNR-UHFFFAOYSA-N tetraethylammonium Chemical class CC[N+](CC)(CC)CC CBXCPBUEXACCNR-UHFFFAOYSA-N 0.000 description 1
- 229910000326 transition metal silicate Inorganic materials 0.000 description 1
- 150000005691 triesters Chemical class 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- CBIQXUBDNNXYJM-UHFFFAOYSA-N tris(2,2,2-trifluoroethyl) phosphite Chemical compound FC(F)(F)COP(OCC(F)(F)F)OCC(F)(F)F CBIQXUBDNNXYJM-UHFFFAOYSA-N 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 230000037303 wrinkles Effects 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
Images
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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
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/141—Esters of phosphorous acids
- C07F9/142—Esters of phosphorous acids with hydroxyalkyl compounds without further substituents on alkyl
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
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- H01M10/052—Li-accumulators
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- C—CHEMISTRY; METALLURGY
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- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
- C07F9/091—Esters of phosphoric acids with hydroxyalkyl compounds with further substituents on alkyl
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- C—CHEMISTRY; METALLURGY
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- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/22—Amides of acids of phosphorus
- C07F9/24—Esteramides
- C07F9/2404—Esteramides the ester moiety containing a substituent or a structure which is considered as characteristic
- C07F9/2408—Esteramides the ester moiety containing a substituent or a structure which is considered as characteristic of hydroxyalkyl compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/40—Esters thereof
- C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4006—Esters of acyclic acids which can have further substituents on alkyl
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- 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
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Description
を有するホスフェート化合物は、電池用電解液中の添加剤としての使用が提案されている。例えば、米国特許第6,642,294号、欧州特許第906641号及びSolid State Electronics 133, 2000, 171-177参照。これらのホスフェート化合物は、電解液に及び電解液を含む電池にいくつかの望ましい機械的、熱的及び電気的特性を付与することができる。それらは難燃性をもたらすことができ、これは、特にリチウム電池に関して、大いに有意である。これらの電池は、非水性電解質を含むからであり、高いエネルギー及び出力密度を有するからでもある。高いエネルギー密度及び出力密度と相まって、電解質の有機性により、リチウム電池は、熱暴走事象、例えば暴走発熱反応及びさらに燃焼を非常に被りやすくなる。このため、難燃剤がリチウム電池用電解質に常例的に添合されている。
を有する少なくとも1つの部分を含有し、この式中、R基は、独立して、水素、アルキル、アリール、アリール置換アルキルなどである。2つ又はそれ以上のR基が、それらが付いている炭素原子(及び、もしあれば、この芳香族環の任意の介在炭素原子)と一緒に、縮合環構造を形成することがある。前記縮合環は、芳香族であることがあり、又は脂肪族であることがある。いずれの置換基にも脂肪族質素原子がないべきであるが、芳香族環構造の一部を形成する追加の窒素原子(単数又は複数)が存在することがある。すべてのR基が水素であることが好ましく、この場合、そのピリジニル化合物はピリジンである。
(I)
によって表すことができ、この式中の各xは、独立して1又はそれ以上であり、各Rは、水素又はアルキルであり、及び各R1は、アルキル又は
(II)
である。アルキレングリコール又はポリアルキレングリコールが反応混合物中に存在するとき、R1基のうちのいくつかは構造(II)を有するであろう。そうでなければ、R1基は、アルキルであり、モノエーテル化合物上の末端アルキル基に対応するだろう。R1基のうちの少なくともいくつかは、アルキル基である。
各xは1から5であることが好ましく、各xは1から3であることがさらに好ましい。各Rは、好ましくは、水素又はC1−2アルキルである。Rは、さらに好ましくは、いずれの場合も水素である。1つより多くのR1基が構造IIを有さず、残りのものがC1−4アルキル、特にメチル、であることが好ましい。各R1基はC1−4アルキルであることがさらに好ましく、各R1基はメチルであることがさらにいっそう好ましい。
攪拌棒及び添加漏斗を装備したアルゴンフラッシュ済み丸底フラスコにテトラヒドロフランを添加する。ジエチレングリコールモノメチルエーテル及びピリジンをそのフラスコに添加し、氷浴で0℃に冷却する。その後、ホスホリルクロライドを攪拌しながら一滴ずつ添加する。配合材料の比率は、得られるホスホリルクロライド出発濃度(すなわち、ホスホリルクロライドの添加が完了した後)が約0.5Mであり、6当量のモノエーテルが1モルのホスホリルクロライドに対して供給され、及び5モルのピリジンが1モルのホスホリルクロライドに対して供給されるような比率である。ホスホリルクロライド添加が開始するやいなや、ピリジン:HClが沈殿し始める。ホスホリルクロライド添加が完了した後、反応混合物を放置して室温(25℃)に温め、約24時間攪拌する。
を有する化合物に対応する。
実施例1を繰り返すが、今回はピリジンの代わりにトリエチルアミンを用いる。反応は、実施例1よりゆっくりと進行し、完了するまでに室温で約48時間を要する。反応中に形成するトリエチルアミン:HCl塩を濾過によって粗反応混合物から分離する;残存液相は非常に着色されている。実施例1において説明したように溶剤、過剰なモノエーテル及びアミンを除去した後、再び実施例1におけるように、生成物をアセトニトリルに再溶解し、アルミナカラムに通す。その後、実施例1におけるように生成物を脱溶剤し、乾燥させる。
及び
を有すると考えられる。点Fによって確認される化合物は、点Eの化合物の異性体であると考えられる。
実施例1を繰り返すが、今回は、モノエチレングリコールモノメチルエーテルを、実施例1において使用したジエチレングリコールモノメチルエーテルの代わりに用いる。液体クロマトグラフィー/質量分析は、ホスホリルクロライドのトリス(モノエチレングリコールモノメチルエーテル)エステルである生成物と一致する。本質的に他のリン化合物は検出されない。この実験をニートで及び1,2−ジクロロエタン中で繰り返した場合にも同様の結果が得られる。
実施例1を再び繰り返すが、今回は、トリエチレングリコールモノメチルエーテルを、実施例1において使用したジエチレングリコールモノメチルエーテルの代わりに用いる。液体クロマトグラフィー/質量分析は、ホスホリルクロライドのトリス(トリエチレングリコールモノメチルエーテル)エステルである生成物と一致する。本質的に他のリン化合物は検出されない。この生成物は、25℃で25cPsの粘度を有する。この実験をニートで及び1,2−ジクロロエタン中で繰り返した場合にも同様の結果が得られる。
以下に、本願の当初の特許請求の範囲に記載された発明を付記する。
[1]
ホスホリルクロライドと、少なくとも1つのモノ(アルキレングリコール)モノエーテル若しくはポリ(アルキレングリコール)モノエーテルとを、又は少なくとも1つのモノ(アルキレングリコール)モノエーテル若しくはポリ(アルキレングリコール)モノエーテルと少なくとも1つのアルキレングリコール若しくはポリアルキレングリコールの混合物とを、1モルのホスホリルクロライドにつき少なくとも3モルの、脂肪族窒素原子がない、ピリジニル化合物の存在下で反応させることを含む、リン酸エステル化合物を形成するための方法。
[2]
前記ピリジニル化合物が、ピリジンである、[1]に記載の方法。
[3]
ホスホリルクロライドをジエチレングリコールモノメチルエーテル又はトリエチレングリコールモノメチルエーテルと反応させる、[1]又は[2]に記載の方法。
[4]
溶剤中で行う、[1]から[3]のいずれかに記載の方法。
[5]
前記溶剤が、極性溶剤である、[4]に記載の方法。
[6]
[1]から[5]のいずれかに記載の方法で生成されたリン酸エステルを含有する電池用電解液。
[7]
[6]に記載の電池用電解液を含む電池。
Claims (2)
- ホスホリルクロライドと、ジエチレングリコールモノメチルエーテル又はトリエチレングリコールモノメチルエーテルとを、1モルのホスホリルクロライドにつき少なくとも3モルの、脂肪族窒素原子がない、ピリジニル化合物の存在下、溶剤であるテトラヒドロフラン又は1,2−ジクロロエタン中で反応させることを含む、リン酸トリエステル化合物を形成するための方法。
- 前記ピリジニル化合物が、ピリジンである、請求項1に記載の方法。
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US24883109P | 2009-10-05 | 2009-10-05 | |
US61/248,831 | 2009-10-05 | ||
PCT/US2010/050100 WO2011043934A2 (en) | 2009-10-05 | 2010-09-24 | Process for manufacturing phosphate esters from phosphoryl chloride and monoalkyl ethers of glycols or polyglycols |
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KR101852521B1 (ko) * | 2016-10-14 | 2018-06-07 | 에스디코리아(주) | 비할로겐 인계 난연제 제조방법 |
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CN110931862B (zh) * | 2019-10-31 | 2022-03-11 | 合肥国轩高科动力能源有限公司 | 一种双功能电解液添加剂及含有该添加剂的锂离子电池电解液 |
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US5302758A (en) * | 1993-05-10 | 1994-04-12 | General Electric Company | Deuterated dibutyl and monobutyl phosphates |
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WO2002056408A1 (fr) | 2001-01-04 | 2002-07-18 | Mitsubishi Chemical Corporation | Liquides electrolytiques non aqueux et pile au lithium secondaire faisant intervenir ces liquides |
US6727343B2 (en) | 2001-04-17 | 2004-04-27 | Phoenix Innovation, Inc. | Heteroatomic polymer for more efficient solid polymer electrolytes for lithium batteries |
EP1555711B1 (en) | 2002-10-22 | 2011-12-21 | Mitsubishi Chemical Corporation | Nonaqueous electrolytic solution and nonaqueous electrolyte secondary battery containing the same |
CN101148457A (zh) * | 2007-11-02 | 2008-03-26 | 湖南大学 | 一种含磷三官能团液体脂环族环氧化合物及制备方法 |
WO2009086170A1 (en) * | 2007-12-21 | 2009-07-09 | Joyant Pharmaceuticals, Inc. | Diazonamide analogs with improved solubility |
-
2010
- 2010-09-24 KR KR1020127011632A patent/KR20120093262A/ko not_active Application Discontinuation
- 2010-09-24 JP JP2012533201A patent/JP5702393B2/ja not_active Expired - Fee Related
- 2010-09-24 CN CN201080044722.7A patent/CN102639544B/zh not_active Expired - Fee Related
- 2010-09-24 WO PCT/US2010/050100 patent/WO2011043934A2/en active Application Filing
- 2010-09-24 US US13/395,913 patent/US9130239B2/en not_active Expired - Fee Related
- 2010-09-24 EP EP10760874A patent/EP2519531A2/en not_active Withdrawn
Also Published As
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WO2011043934A3 (en) | 2011-06-16 |
JP2013506711A (ja) | 2013-02-28 |
US9130239B2 (en) | 2015-09-08 |
CN102639544B (zh) | 2015-04-29 |
WO2011043934A2 (en) | 2011-04-14 |
KR20120093262A (ko) | 2012-08-22 |
US20120172613A1 (en) | 2012-07-05 |
CN102639544A (zh) | 2012-08-15 |
EP2519531A2 (en) | 2012-11-07 |
WO2011043934A9 (en) | 2012-04-12 |
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