JP5946361B2 - Method for producing 1,3-difluorodisiloxane compound - Google Patents
Method for producing 1,3-difluorodisiloxane compound Download PDFInfo
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- JP5946361B2 JP5946361B2 JP2012175922A JP2012175922A JP5946361B2 JP 5946361 B2 JP5946361 B2 JP 5946361B2 JP 2012175922 A JP2012175922 A JP 2012175922A JP 2012175922 A JP2012175922 A JP 2012175922A JP 5946361 B2 JP5946361 B2 JP 5946361B2
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- JP
- Japan
- Prior art keywords
- group
- compound
- general formula
- difluorodisiloxane
- compound represented
- 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.)
- Expired - Fee Related
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- -1 1,3-difluorodisiloxane compound Chemical class 0.000 title claims description 42
- 238000004519 manufacturing process Methods 0.000 title claims description 18
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 claims description 44
- 150000001875 compounds Chemical class 0.000 claims description 26
- 229910000040 hydrogen fluoride Inorganic materials 0.000 claims description 14
- 239000011255 nonaqueous electrolyte Substances 0.000 claims description 5
- 239000000463 material Substances 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 description 19
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 125000004432 carbon atom Chemical group C* 0.000 description 15
- 239000012044 organic layer Substances 0.000 description 10
- 238000000034 method Methods 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- 125000000217 alkyl group Chemical group 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 5
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- HTJCZBQEAWWKRZ-UHFFFAOYSA-N fluoro-[fluoro(dimethyl)silyl]oxy-dimethylsilane Chemical compound C[Si](C)(F)O[Si](C)(C)F HTJCZBQEAWWKRZ-UHFFFAOYSA-N 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 239000010408 film Substances 0.000 description 4
- 239000010410 layer Substances 0.000 description 4
- 229910001512 metal fluoride Inorganic materials 0.000 description 4
- 239000012299 nitrogen atmosphere Substances 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- 230000009257 reactivity Effects 0.000 description 4
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 239000002000 Electrolyte additive Substances 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- YQJZJFISVSODIX-UHFFFAOYSA-N F[SiH2]O[SiH2]F Chemical class F[SiH2]O[SiH2]F YQJZJFISVSODIX-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- JJQZDUKDJDQPMQ-UHFFFAOYSA-N dimethoxy(dimethyl)silane Chemical compound CO[Si](C)(C)OC JJQZDUKDJDQPMQ-UHFFFAOYSA-N 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- ODNBVEIAQAZNNM-UHFFFAOYSA-N 1-(6-chloroimidazo[1,2-b]pyridazin-3-yl)ethanone Chemical compound C1=CC(Cl)=NN2C(C(=O)C)=CN=C21 ODNBVEIAQAZNNM-UHFFFAOYSA-N 0.000 description 2
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 2
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 2
- HWFNGQWTXGVRAE-UHFFFAOYSA-N 3-chloropropyl-(3-chloropropyl-fluoro-methylsilyl)oxy-fluoro-methylsilane Chemical compound ClCCC[Si](O[Si](C)(F)CCCCl)(C)F HWFNGQWTXGVRAE-UHFFFAOYSA-N 0.000 description 2
- KNTKCYKJRSMRMZ-UHFFFAOYSA-N 3-chloropropyl-dimethoxy-methylsilane Chemical compound CO[Si](C)(OC)CCCCl KNTKCYKJRSMRMZ-UHFFFAOYSA-N 0.000 description 2
- GUNJVIDCYZYFGV-UHFFFAOYSA-K Antimony trifluoride Inorganic materials F[Sb](F)F GUNJVIDCYZYFGV-UHFFFAOYSA-K 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical group CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical class [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- MTNMPCMHZLVLJY-UHFFFAOYSA-N chloro(chlorosilyloxy)silane Chemical class Cl[SiH2]O[SiH2]Cl MTNMPCMHZLVLJY-UHFFFAOYSA-N 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- SJJCABYOVIHNPZ-UHFFFAOYSA-N cyclohexyl-dimethoxy-methylsilane Chemical compound CO[Si](C)(OC)C1CCCCC1 SJJCABYOVIHNPZ-UHFFFAOYSA-N 0.000 description 2
- ZMAPKOCENOWQRE-UHFFFAOYSA-N diethoxy(diethyl)silane Chemical compound CCO[Si](CC)(CC)OCC ZMAPKOCENOWQRE-UHFFFAOYSA-N 0.000 description 2
- VSYLGGHSEIWGJV-UHFFFAOYSA-N diethyl(dimethoxy)silane Chemical compound CC[Si](CC)(OC)OC VSYLGGHSEIWGJV-UHFFFAOYSA-N 0.000 description 2
- AHUXYBVKTIBBJW-UHFFFAOYSA-N dimethoxy(diphenyl)silane Chemical compound C=1C=CC=CC=1[Si](OC)(OC)C1=CC=CC=C1 AHUXYBVKTIBBJW-UHFFFAOYSA-N 0.000 description 2
- CVQVSVBUMVSJES-UHFFFAOYSA-N dimethoxy-methyl-phenylsilane Chemical compound CO[Si](C)(OC)C1=CC=CC=C1 CVQVSVBUMVSJES-UHFFFAOYSA-N 0.000 description 2
- YYLGKUPAFFKGRQ-UHFFFAOYSA-N dimethyldiethoxysilane Chemical compound CCO[Si](C)(C)OCC YYLGKUPAFFKGRQ-UHFFFAOYSA-N 0.000 description 2
- ODKQFCVJHYCUIZ-UHFFFAOYSA-N fluoro-(fluoro-methyl-phenylsilyl)oxy-methyl-phenylsilane Chemical compound C=1C=CC=CC=1[Si](F)(C)O[Si](C)(F)C1=CC=CC=C1 ODKQFCVJHYCUIZ-UHFFFAOYSA-N 0.000 description 2
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 2
- BHHYHSUAOQUXJK-UHFFFAOYSA-L zinc fluoride Chemical compound F[Zn]F BHHYHSUAOQUXJK-UHFFFAOYSA-L 0.000 description 2
- RTEKUJFDNWKQGL-UHFFFAOYSA-N 1,1,2,2,3,3,3-heptafluoropropyl-dimethoxy-methylsilane Chemical compound CO[Si](C)(OC)C(F)(F)C(F)(F)C(F)(F)F RTEKUJFDNWKQGL-UHFFFAOYSA-N 0.000 description 1
- SRGPIPMMOXKWHH-UHFFFAOYSA-N 1,1,2,2,3,3,3-heptafluoropropyl-methyl-dipropoxysilane Chemical compound FC(C(F)(F)[Si](OCCC)(OCCC)C)(C(F)(F)F)F SRGPIPMMOXKWHH-UHFFFAOYSA-N 0.000 description 1
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- 229940093475 2-ethoxyethanol Drugs 0.000 description 1
- 125000005916 2-methylpentyl group Chemical group 0.000 description 1
- SLXXRVCYKMHKQM-UHFFFAOYSA-N 2-phenylethyl(dipropoxy)silane Chemical compound C1(=CC=CC=C1)CC[SiH](OCCC)OCCC SLXXRVCYKMHKQM-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- KEZMLECYELSZDC-UHFFFAOYSA-N 3-chloropropyl-diethoxy-methylsilane Chemical compound CCO[Si](C)(OCC)CCCCl KEZMLECYELSZDC-UHFFFAOYSA-N 0.000 description 1
- HFGAQFWWMOBWDV-UHFFFAOYSA-N 3-chloropropyl-methyl-dipropoxysilane Chemical compound CCCO[Si](C)(CCCCl)OCCC HFGAQFWWMOBWDV-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- FSQCHFZJIHPGQG-UHFFFAOYSA-N C(CCCC)[Si](OCCCC)(OCCCC)C Chemical compound C(CCCC)[Si](OCCCC)(OCCCC)C FSQCHFZJIHPGQG-UHFFFAOYSA-N 0.000 description 1
- QEYSYISXNYNKDT-UHFFFAOYSA-N C1(=CC=CC=C1)CC[SiH](OCCCC)OCCCC Chemical compound C1(=CC=CC=C1)CC[SiH](OCCCC)OCCCC QEYSYISXNYNKDT-UHFFFAOYSA-N 0.000 description 1
- UCHWOTBMOQVNOB-UHFFFAOYSA-N C1(CCCCC1)C[SiH](OCCCC)OCCCC Chemical compound C1(CCCCC1)C[SiH](OCCCC)OCCCC UCHWOTBMOQVNOB-UHFFFAOYSA-N 0.000 description 1
- LMMSMCYKELWOBW-UHFFFAOYSA-N CC=C[SiH](OCCC)OCCC Chemical compound CC=C[SiH](OCCC)OCCC LMMSMCYKELWOBW-UHFFFAOYSA-N 0.000 description 1
- ICKLOFVFFMQIJP-UHFFFAOYSA-N CCO[SiH](C(F)(F)F)OCC Chemical compound CCO[SiH](C(F)(F)F)OCC ICKLOFVFFMQIJP-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 229910021594 Copper(II) fluoride Inorganic materials 0.000 description 1
- BLHYAOKGDVRQOG-UHFFFAOYSA-N FC(F)(F)[Si](OCCC)(OCCC)C Chemical compound FC(F)(F)[Si](OCCC)(OCCC)C BLHYAOKGDVRQOG-UHFFFAOYSA-N 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- WZPSLYBTZUWDLG-UHFFFAOYSA-N [SiH4].C1(=CC=CC=C1)CC[Si](OCCC)(OCCC)C Chemical compound [SiH4].C1(=CC=CC=C1)CC[Si](OCCC)(OCCC)C WZPSLYBTZUWDLG-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- XSVRIICVXZBSCH-UHFFFAOYSA-N benzyl(dipropoxy)silane Chemical compound CCCO[SiH](OCCC)CC1=CC=CC=C1 XSVRIICVXZBSCH-UHFFFAOYSA-N 0.000 description 1
- VLKGHSKMEBJFAK-UHFFFAOYSA-N benzyl-diethoxy-methylsilane Chemical compound CCO[Si](C)(OCC)CC1=CC=CC=C1 VLKGHSKMEBJFAK-UHFFFAOYSA-N 0.000 description 1
- GSKAIYAPIGRGRZ-UHFFFAOYSA-N benzyl-dimethoxy-methylsilane Chemical compound CO[Si](C)(OC)CC1=CC=CC=C1 GSKAIYAPIGRGRZ-UHFFFAOYSA-N 0.000 description 1
- CSXPRVTYIFRYPR-UHFFFAOYSA-N bis(ethenyl)-diethoxysilane Chemical compound CCO[Si](C=C)(C=C)OCC CSXPRVTYIFRYPR-UHFFFAOYSA-N 0.000 description 1
- ZPECUSGQPIKHLT-UHFFFAOYSA-N bis(ethenyl)-dimethoxysilane Chemical compound CO[Si](OC)(C=C)C=C ZPECUSGQPIKHLT-UHFFFAOYSA-N 0.000 description 1
- SNAFCWIFMFKILC-UHFFFAOYSA-N bis(ethenyl)-dipropoxysilane Chemical compound CCCO[Si](C=C)(C=C)OCCC SNAFCWIFMFKILC-UHFFFAOYSA-N 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 1
- XIDIFQCMMOCJGX-UHFFFAOYSA-N butoxy-(3-chloropropyl)-methylsilane Chemical compound ClCCC[SiH](OCCCC)C XIDIFQCMMOCJGX-UHFFFAOYSA-N 0.000 description 1
- ZZHNUBIHHLQNHX-UHFFFAOYSA-N butoxysilane Chemical compound CCCCO[SiH3] ZZHNUBIHHLQNHX-UHFFFAOYSA-N 0.000 description 1
- AFNPFLDWLMEASV-UHFFFAOYSA-N butyl-diethoxy-methylsilane Chemical compound CCCC[Si](C)(OCC)OCC AFNPFLDWLMEASV-UHFFFAOYSA-N 0.000 description 1
- OOSZILWKTQCRSZ-UHFFFAOYSA-N butyl-dimethoxy-methylsilane Chemical compound CCCC[Si](C)(OC)OC OOSZILWKTQCRSZ-UHFFFAOYSA-N 0.000 description 1
- WHFVJENFZHIOKB-UHFFFAOYSA-N butyl-methyl-dipropoxysilane Chemical compound CCCC[Si](C)(OCCC)OCCC WHFVJENFZHIOKB-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- GWFAVIIMQDUCRA-UHFFFAOYSA-L copper(ii) fluoride Chemical compound [F-].[F-].[Cu+2] GWFAVIIMQDUCRA-UHFFFAOYSA-L 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- PRHSMZXKVQBUOW-UHFFFAOYSA-N cyclohexyl-methyl-dipropoxysilane Chemical compound CCCO[Si](C)(OCCC)C1CCCCC1 PRHSMZXKVQBUOW-UHFFFAOYSA-N 0.000 description 1
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- RTYZQVDVGVAXSW-UHFFFAOYSA-N cyclohexylmethyl(diethoxy)silane Chemical compound CCO[SiH](OCC)CC1CCCCC1 RTYZQVDVGVAXSW-UHFFFAOYSA-N 0.000 description 1
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 description 1
- MGQFVQQCNPBJKC-UHFFFAOYSA-N dibutoxy(diethyl)silane Chemical compound CCCCO[Si](CC)(CC)OCCCC MGQFVQQCNPBJKC-UHFFFAOYSA-N 0.000 description 1
- GQNWJCQWBFHQAO-UHFFFAOYSA-N dibutoxy(dimethyl)silane Chemical compound CCCCO[Si](C)(C)OCCCC GQNWJCQWBFHQAO-UHFFFAOYSA-N 0.000 description 1
- OSMIWEAIYFILPL-UHFFFAOYSA-N dibutoxy(diphenyl)silane Chemical compound C=1C=CC=CC=1[Si](OCCCC)(OCCCC)C1=CC=CC=C1 OSMIWEAIYFILPL-UHFFFAOYSA-N 0.000 description 1
- BKGSSPASYNBWRR-UHFFFAOYSA-N dibutoxy(dipropyl)silane Chemical compound CCCCO[Si](CCC)(CCC)OCCCC BKGSSPASYNBWRR-UHFFFAOYSA-N 0.000 description 1
- XUOXGXLCJPCUAW-UHFFFAOYSA-N dibutoxy(prop-1-enyl)silane Chemical compound CC=C[SiH](OCCCC)OCCCC XUOXGXLCJPCUAW-UHFFFAOYSA-N 0.000 description 1
- DALSUKORAFZPLR-UHFFFAOYSA-N dibutoxy-(1,1,2,2,3,3,3-heptafluoropropyl)-methylsilane Chemical compound FC(C(F)(F)[Si](OCCCC)(OCCCC)C)(C(F)(F)F)F DALSUKORAFZPLR-UHFFFAOYSA-N 0.000 description 1
- PBBAHPAMIQGMEE-UHFFFAOYSA-N dibutoxy-bis(ethenyl)silane Chemical compound CCCCO[Si](C=C)(C=C)OCCCC PBBAHPAMIQGMEE-UHFFFAOYSA-N 0.000 description 1
- XLQRVKOZXDPYNI-UHFFFAOYSA-N dibutoxy-butyl-methylsilane Chemical compound C(CCC)[Si](OCCCC)(OCCCC)C XLQRVKOZXDPYNI-UHFFFAOYSA-N 0.000 description 1
- VULDKXCHNPRZCS-UHFFFAOYSA-N dibutoxy-ethyl-methylsilane Chemical compound CCCCO[Si](C)(CC)OCCCC VULDKXCHNPRZCS-UHFFFAOYSA-N 0.000 description 1
- YBYAENBQXGEWTI-UHFFFAOYSA-N dibutoxy-hexyl-methylsilane Chemical compound C(CCCCC)[Si](OCCCC)(OCCCC)C YBYAENBQXGEWTI-UHFFFAOYSA-N 0.000 description 1
- RVIGSDJUDDLMJU-UHFFFAOYSA-N dibutoxy-methyl-(2-phenylethyl)silane Chemical compound C(CC1=CC=CC=C1)[Si](OCCCC)(OCCCC)C RVIGSDJUDDLMJU-UHFFFAOYSA-N 0.000 description 1
- IWOBRMKIOJMQRL-UHFFFAOYSA-N dibutoxy-methyl-propylsilane Chemical compound CCCCO[Si](C)(CCC)OCCCC IWOBRMKIOJMQRL-UHFFFAOYSA-N 0.000 description 1
- DGPFXVBYDAVXLX-UHFFFAOYSA-N dibutyl(diethoxy)silane Chemical compound CCCC[Si](OCC)(OCC)CCCC DGPFXVBYDAVXLX-UHFFFAOYSA-N 0.000 description 1
- YPENMAABQGWRBR-UHFFFAOYSA-N dibutyl(dimethoxy)silane Chemical compound CCCC[Si](OC)(OC)CCCC YPENMAABQGWRBR-UHFFFAOYSA-N 0.000 description 1
- ZZNQQQWFKKTOSD-UHFFFAOYSA-N diethoxy(diphenyl)silane Chemical compound C=1C=CC=CC=1[Si](OCC)(OCC)C1=CC=CC=C1 ZZNQQQWFKKTOSD-UHFFFAOYSA-N 0.000 description 1
- HZLIIKNXMLEWPA-UHFFFAOYSA-N diethoxy(dipropyl)silane Chemical compound CCC[Si](CCC)(OCC)OCC HZLIIKNXMLEWPA-UHFFFAOYSA-N 0.000 description 1
- KMLXBWCNYKONBY-UHFFFAOYSA-N diethoxy-(1,1,2,2,3,3,3-heptafluoropropyl)-methylsilane Chemical compound FC(C([Si](OCC)(OCC)C)(F)F)(C(F)(F)F)F KMLXBWCNYKONBY-UHFFFAOYSA-N 0.000 description 1
- NWQIWFOQNHTTIA-UHFFFAOYSA-N diethoxy-bis(prop-2-enyl)silane Chemical compound CCO[Si](CC=C)(CC=C)OCC NWQIWFOQNHTTIA-UHFFFAOYSA-N 0.000 description 1
- UWGJCHRFALXDAR-UHFFFAOYSA-N diethoxy-ethyl-methylsilane Chemical compound CCO[Si](C)(CC)OCC UWGJCHRFALXDAR-UHFFFAOYSA-N 0.000 description 1
- YTDDWYQXURUACY-UHFFFAOYSA-N diethoxy-hexyl-methylsilane Chemical compound CCCCCC[Si](C)(OCC)OCC YTDDWYQXURUACY-UHFFFAOYSA-N 0.000 description 1
- PDMSWKOWFWHYQF-UHFFFAOYSA-N diethoxy-methyl-pentylsilane Chemical compound CCCCC[Si](C)(OCC)OCC PDMSWKOWFWHYQF-UHFFFAOYSA-N 0.000 description 1
- MNFGEHQPOWJJBH-UHFFFAOYSA-N diethoxy-methyl-phenylsilane Chemical compound CCO[Si](C)(OCC)C1=CC=CC=C1 MNFGEHQPOWJJBH-UHFFFAOYSA-N 0.000 description 1
- UJTGYJODGVUOGO-UHFFFAOYSA-N diethoxy-methyl-propylsilane Chemical compound CCC[Si](C)(OCC)OCC UJTGYJODGVUOGO-UHFFFAOYSA-N 0.000 description 1
- BZCJJERBERAQKQ-UHFFFAOYSA-N diethyl(dipropoxy)silane Chemical compound CCCO[Si](CC)(CC)OCCC BZCJJERBERAQKQ-UHFFFAOYSA-N 0.000 description 1
- CYICXDQJFWXGTC-UHFFFAOYSA-N dihexyl(dimethoxy)silane Chemical compound CCCCCC[Si](OC)(OC)CCCCCC CYICXDQJFWXGTC-UHFFFAOYSA-N 0.000 description 1
- JVUVKQDVTIIMOD-UHFFFAOYSA-N dimethoxy(dipropyl)silane Chemical compound CCC[Si](OC)(OC)CCC JVUVKQDVTIIMOD-UHFFFAOYSA-N 0.000 description 1
- PKTOVQRKCNPVKY-UHFFFAOYSA-N dimethoxy(methyl)silicon Chemical compound CO[Si](C)OC PKTOVQRKCNPVKY-UHFFFAOYSA-N 0.000 description 1
- YSLPJPIFWBBCKF-UHFFFAOYSA-N dimethoxy(trifluoromethyl)silane Chemical compound CO[SiH](OC)C(F)(F)F YSLPJPIFWBBCKF-UHFFFAOYSA-N 0.000 description 1
- WERMRYHPOOABQT-UHFFFAOYSA-N dimethoxy-bis(prop-2-enyl)silane Chemical compound C=CC[Si](OC)(CC=C)OC WERMRYHPOOABQT-UHFFFAOYSA-N 0.000 description 1
- FXXLLMOVBDFOKK-UHFFFAOYSA-N dimethoxy-methyl-(2-phenylethyl)silane Chemical compound CO[Si](C)(OC)CCC1=CC=CC=C1 FXXLLMOVBDFOKK-UHFFFAOYSA-N 0.000 description 1
- UNDUWLPONQBXSZ-UHFFFAOYSA-N dimethoxy-methyl-pentylsilane Chemical compound CCCCC[Si](C)(OC)OC UNDUWLPONQBXSZ-UHFFFAOYSA-N 0.000 description 1
- WQTNGCZMPUCIEX-UHFFFAOYSA-N dimethoxy-methyl-prop-2-enylsilane Chemical compound CO[Si](C)(OC)CC=C WQTNGCZMPUCIEX-UHFFFAOYSA-N 0.000 description 1
- XKRPWHZLROBLDI-UHFFFAOYSA-N dimethoxy-methyl-propylsilane Chemical compound CCC[Si](C)(OC)OC XKRPWHZLROBLDI-UHFFFAOYSA-N 0.000 description 1
- YQGOWXYZDLJBFL-UHFFFAOYSA-N dimethoxysilane Chemical compound CO[SiH2]OC YQGOWXYZDLJBFL-UHFFFAOYSA-N 0.000 description 1
- ZIDTUTFKRRXWTK-UHFFFAOYSA-N dimethyl(dipropoxy)silane Chemical compound CCCO[Si](C)(C)OCCC ZIDTUTFKRRXWTK-UHFFFAOYSA-N 0.000 description 1
- SLAYMDSSGGBWQB-UHFFFAOYSA-N diphenyl(dipropoxy)silane Chemical compound C=1C=CC=CC=1[Si](OCCC)(OCCC)C1=CC=CC=C1 SLAYMDSSGGBWQB-UHFFFAOYSA-N 0.000 description 1
- AVBCBOQFOQZNFK-UHFFFAOYSA-N dipropoxy(dipropyl)silane Chemical compound CCCO[Si](CCC)(CCC)OCCC AVBCBOQFOQZNFK-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- MBGQQKKTDDNCSG-UHFFFAOYSA-N ethenyl-diethoxy-methylsilane Chemical compound CCO[Si](C)(C=C)OCC MBGQQKKTDDNCSG-UHFFFAOYSA-N 0.000 description 1
- NOTNKQGHVOKIJS-UHFFFAOYSA-N ethyl-dimethoxy-(2-phenylethyl)silane Chemical compound CC[Si](OC)(OC)CCC1=CC=CC=C1 NOTNKQGHVOKIJS-UHFFFAOYSA-N 0.000 description 1
- GXAOCGRUWCYNML-UHFFFAOYSA-N ethyl-methyl-dipropoxysilane Chemical compound CCCO[Si](C)(CC)OCCC GXAOCGRUWCYNML-UHFFFAOYSA-N 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 125000006038 hexenyl group Chemical group 0.000 description 1
- APQKDJQPCPXLQL-UHFFFAOYSA-N hexyl-dimethoxy-methylsilane Chemical compound CCCCCC[Si](C)(OC)OC APQKDJQPCPXLQL-UHFFFAOYSA-N 0.000 description 1
- UTGITLYUYJSKFK-UHFFFAOYSA-N hexyl-methyl-dipropoxysilane Chemical compound CCCCCC[Si](C)(OCCC)OCCC UTGITLYUYJSKFK-UHFFFAOYSA-N 0.000 description 1
- 239000011229 interlayer Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- QERMJAIQFKCHCE-UHFFFAOYSA-N methyl-dipropoxy-propylsilane Chemical compound CCCO[Si](C)(CCC)OCCC QERMJAIQFKCHCE-UHFFFAOYSA-N 0.000 description 1
- IAONSFOILDBNHB-UHFFFAOYSA-N methyl-pentyl-dipropoxysilane Chemical compound C(CCCC)[Si](OCCC)(OCCC)C IAONSFOILDBNHB-UHFFFAOYSA-N 0.000 description 1
- 229940078552 o-xylene Drugs 0.000 description 1
- 125000004365 octenyl group Chemical group C(=CCCCCCC)* 0.000 description 1
- 238000002161 passivation Methods 0.000 description 1
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000005268 plasma chemical vapour deposition Methods 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 150000003109 potassium Chemical class 0.000 description 1
- FWZMWMSAGOVWEZ-UHFFFAOYSA-N potassium;hydrofluoride Chemical compound F.[K] FWZMWMSAGOVWEZ-UHFFFAOYSA-N 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000005070 ripening Effects 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
Landscapes
- Formation Of Insulating Films (AREA)
- Secondary Cells (AREA)
- Chemical Vapour Deposition (AREA)
Description
本発明は、１，３−ジフルオロジシロキサン化合物の製造方法に関する。 The present invention relates to a method for producing a 1,3-difluorodisiloxane compound.
１，３−ジフルオロジシロキサン化合物は、適度な反応性を有しながら、安定性に優れ、また金属の腐食の原因となる塩素や臭素を含まないことからケイ素系高分子薄膜製造の原料（例えば、特許文献１、２を参照）、非水電解液二次電池用電解液添加剤（例えば、特許文献３を参照）等として有用である。１，３−ジフルオロジシロキサン化合物の製造方法としては、１，３−ジクロロジシロキサン化合物に、三フッ化アンチモン、フッ化銅、フッ化亜鉛等の金属フッ化物とを反応させる方法（例えば、特許文献１、３を参照）や、フッ化水素酸カリウム類（例えば、特許文献１を参照）を反応させる方法が知られているが、金属フッ化物は価格や毒性に問題があり、フッ化水素酸カリウム類を反応させる方法は、アルキルクロロシラン化合物に対して収率が低いという問題がある。従来知られた１，３−ジフルオロジシロキサン化合物の製造方法は、何れも１，３−ジクロロジシロキサン化合物を原料としているが、１，３−ジクロロジシロキサン化合物はモノシラン化合物から製造する必要があり、モノシラン化合物から１段階で１，３−ジフルオロジシロキサン化合物を得る製造方法は知られていない。 A 1,3-difluorodisiloxane compound has an appropriate reactivity, is excellent in stability, and does not contain chlorine or bromine that causes metal corrosion. , See Patent Documents 1 and 2), electrolyte additives for non-aqueous electrolyte secondary batteries (for example, see Patent Document 3), and the like. As a method for producing a 1,3-difluorodisiloxane compound, a method in which a 1,3-dichlorodisiloxane compound is reacted with a metal fluoride such as antimony trifluoride, copper fluoride, or zinc fluoride (for example, a patent) References 1 and 3) and methods of reacting potassium hydrofluoride (see, for example, Patent Document 1) are known, but metal fluorides have problems in price and toxicity, and hydrogen fluoride. The method of reacting potassium acids has a problem that the yield is low with respect to the alkylchlorosilane compound. All known methods for producing 1,3-difluorodisiloxane compounds use 1,3-dichlorodisiloxane compounds as raw materials, but 1,3-dichlorodisiloxane compounds must be produced from monosilane compounds. A production method for obtaining a 1,3-difluorodisiloxane compound from a monosilane compound in one step is not known.
本発明の目的は、モノシラン化合物を使用して、安価な原料から簡便な工程により１，３−ジフルオロジシロキサン化合物を製造することにある。 An object of the present invention is to produce a 1,3-difluorodisiloxane compound from an inexpensive raw material by a simple process using a monosilane compound.
本発明者らは、鋭意検討を行なった結果、ジアルコキシシラン化合物にフッ化水素酸を反応させることにより上記目的を達成することを見出し、本発明を完成させた。すなわち、本発明は、下記一般式（１）で表されるジアルコキシシラン化合物にフッ化水素酸を反応させることを特徴とする下記一般式（２）で表される１，３−ジフルオロジシロキサン化合物の製造方法である。 As a result of intensive studies, the present inventors have found that the above object can be achieved by reacting a dialkoxysilane compound with hydrofluoric acid, thereby completing the present invention. That is, the present invention is a 1,3-difluorodisiloxane represented by the following general formula (2), characterized in that hydroalkanoic acid is reacted with a dialkoxysilane compound represented by the following general formula (1). It is a manufacturing method of a compound.
本発明によれば、ケイ素系高分子薄膜製造の原料や非水電解液二次電池用電解液添加剤等に有用な１，３−ジフルオロジシロキサン化合物を安価な原料から簡便な工程で製造することが可能になる。 According to the present invention, a 1,3-difluorodisiloxane compound useful as a raw material for producing a silicon-based polymer thin film or an electrolyte additive for a non-aqueous electrolyte secondary battery is produced from an inexpensive raw material in a simple process. It becomes possible.
まず、本発明の製造方法に用いられる前記一般式（１）で表されるジアルコキシシラン化合物について説明する。 First, the dialkoxysilane compound represented by the general formula (1) used in the production method of the present invention will be described.
前記一般式（１）においてＲ1及びＲ2はそれぞれ独立に、炭素原子数１〜８のアルキル基、炭素原子数２〜８のアルケニル基、炭素原子数５〜８のシクロアルキル基、炭素原子数６〜８のアリール基、炭素原子数７〜８のアラルキル基、炭素原子数１〜８のハロゲン化アルキル基を表す。 In the general formula (1), R 1 and R 2 are each independently an alkyl group having 1 to 8 carbon atoms, an alkenyl group having 2 to 8 carbon atoms, a cycloalkyl group having 5 to 8 carbon atoms, or a carbon atom. An aryl group having 6 to 8 carbon atoms, an aralkyl group having 7 to 8 carbon atoms, and a halogenated alkyl group having 1 to 8 carbon atoms are represented.
炭素原子数１〜８のアルキル基としては、メチル基、エチル基、プロピル基、イソプロピル基、ブチル基、イソブチル基、２級ブチル基、ｔ−ブチル基、ペンチル基、イソペンチル基、２級ペンチル基、ｔ−ペンチル基、ヘキシル基、２級ヘキシル基、ヘプチル基、２級ヘプチル基、オクチル基、２級オクチル基、２−メチルペンチル基、２−エチルヘキシル基等が挙げられる。炭素原子数２〜８のアルケニル基としては、ビニル基、アリル基、プロペニル基、ブテニル基、イソブテニル基、ペンテニル基、イソペンテニル基、ヘキセニル基、ヘプテニル基、オクテニル基等が挙げられる。炭素原子数５〜８のシクロアルキル基としては、シクロペンチル基、シクロヘキシル基、シクロヘプチル基、シクロオクチル基、シクロペンチルメチル基、シクロヘキシルメチル基、シクロヘキシルエチル基、メチルシクロヘキシル基、ジメチルシクロヘキシル基、エチルシクロヘキシル基等が挙げられる。炭素原子数６〜８のアリール基としては、フェニル基、メチルフェニル基、ジメチルフェニル基、エチルフェニル基等が挙げられる。炭素原子数７〜８のアラルキル基としては、ベンジル基、フェニルエチル基等が挙げられる。炭素原子数１〜８のハロゲン化アルキル基としては、２−クロロエチル基、３−クロロプロピル基、４−クロロブチル基、トリフルオロメチル基、３−フルオロプロピル基、３，３，３−トリフルオロプロピル基、３，３，４，４，５，５，６，６，６−ノナフルオロヘキシル基が挙げられる。Ｒ1及びＲ2としては、目的物が収率良く得られることから、メチル基、エチル基、プロピル基、ブチル基、フェニル基、シクロヘキシル基、２−クロロエチル基、３−クロロプロピル基が好ましく、メチル基、エチル基、フェニル基、３−クロロプロピル基が更に好ましく、メチル基が最も好ましい。 Examples of the alkyl group having 1 to 8 carbon atoms include methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, secondary butyl group, t-butyl group, pentyl group, isopentyl group, and secondary pentyl group. , T-pentyl group, hexyl group, secondary hexyl group, heptyl group, secondary heptyl group, octyl group, secondary octyl group, 2-methylpentyl group, 2-ethylhexyl group and the like. Examples of the alkenyl group having 2 to 8 carbon atoms include vinyl group, allyl group, propenyl group, butenyl group, isobutenyl group, pentenyl group, isopentenyl group, hexenyl group, heptenyl group, octenyl group and the like. Examples of the cycloalkyl group having 5 to 8 carbon atoms include cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, cyclopentylmethyl group, cyclohexylmethyl group, cyclohexylethyl group, methylcyclohexyl group, dimethylcyclohexyl group, and ethylcyclohexyl group. Etc. Examples of the aryl group having 6 to 8 carbon atoms include phenyl group, methylphenyl group, dimethylphenyl group, and ethylphenyl group. Examples of the aralkyl group having 7 to 8 carbon atoms include a benzyl group and a phenylethyl group. Examples of the halogenated alkyl group having 1 to 8 carbon atoms include 2-chloroethyl group, 3-chloropropyl group, 4-chlorobutyl group, trifluoromethyl group, 3-fluoropropyl group, 3,3,3-trifluoropropyl. Group, 3,3,4,4,5,5,6,6,6-nonafluorohexyl group. R 1 and R 2 are preferably a methyl group, an ethyl group, a propyl group, a butyl group, a phenyl group, a cyclohexyl group, a 2-chloroethyl group, and a 3-chloropropyl group, because the target product can be obtained with good yield. A methyl group, an ethyl group, a phenyl group and a 3-chloropropyl group are more preferable, and a methyl group is most preferable.
前記一般式（１）においてＲ3は炭素原子数１〜４のアルキル基を表す。炭素原子数１〜４のアルキル基としては、例えば、メチル基、エチル基、プロピル基、イソプロピル基、ブチル基、イソプロピル基、２級ブチル基等が挙げられる。Ｒ3としては、反応性が良好であることから、メチル基、エチル基が好ましい。 In the general formula (1), R 3 represents an alkyl group having 1 to 4 carbon atoms. Examples of the alkyl group having 1 to 4 carbon atoms include methyl group, ethyl group, propyl group, isopropyl group, butyl group, isopropyl group, and secondary butyl group. R 3 is preferably a methyl group or an ethyl group because of good reactivity.
前記一般式（１）で表されるジアルコキシシラン化合物として、好ましい化合物としては、例えば、ジメチルジメトキシシラン、ジエチルジメトキシシラン、ジプロピルジメトキシシラン、ジブチルジメトキシシラン、ジペンチルジメトキシシラン、ジヘキシルジメトキシシラン、エチルメチルジメトキシシラン、メチルプロピルジメトキシシラン、ブチルメチルジメトキシシラン、ペンチルメチルジメトキシシラン、ヘキシルメチルジメトキシシラン、３−クロロプロピルメチルジメトキシシラン、トリフルオロメチルジメトキシシラン、ヘプタフルオロプロピルメチルジメトキシシラン、シクロヘキシルメチルジメトキシシラン、ジアリルジメトキシシラン、アリルメチルジメトキシシラン、ジビニルジメトキシシラン、メチルビニルジメトキシシラン、ジフェニルジメトキシシラン、フェニルメチルジメトキシシラン、ベンジルメチルジメトキシシラン、フェネチルメチルジメトキシシラン、ジメチルジエトキシシラン、ジエチルジエトキシシラン、ジプロピルジエトキシシラン、ジブチルジエトキシシラン、ジペンチルジエトキシシラン、ジヘキシルジエトキシシラン、エチルメチルジエトキシシラン、メチルプロピルジエトキシシラン、ブチルメチルジエトキシシラン、ペンチルメチルジエトキシシラン、ヘキシルメチルジエトキシシラン、３−クロロプロピルメチルジエトキシシラン、トリフルオロメチルジエトキシシラン、ヘプタフルオロプロピルメチルジエトキシシラン、シクロヘキシルメチルジエトキシシラン、ジアリルジエトキシシラン、アリルメチルジエトキシシラン、ジビニルジエトキシシラン、メチルビニルジエトキシシラン、ジフェニルジエトキシシラン、フェニルメチルジエトキシシラン、ベンジルメチルジエトキシシラン、フェネチルエチルジメトキシシラン、ジメチルジプロポキシシラン、ジエチルジプロポキシシラン、ジプロピルジプロポキシシラン、ジブチルジプロポキシシラン、ジペンチルジプロポキシシラン、ジヘキシルジプロポキシシラン、エチルメチルジプロポキシシラン、メチルプロピルジプロポキシシラン、ブチルメチルジプロポキシシラン、ペンチルメチルジプロポキシシラン、ヘキシルメチルジプロポキシシラン、３−クロロプロピルメチルジプロポキシシラン、トリフルオロメチルメチルジプロポキシシラン、ヘプタフルオロプロピルメチルジプロポキシシラン、シクロヘキシルメチルジプロポキシシラン、ジアリルジプロポキシシラン、アリルメチルジプロポキシシラン、ジビニルジプロポキシシラン、メチルビニルジプロポキシシラン、ジフェニルジプロポキシシラン、フェニルメチルジプロポキシシラン、ベンジルメチルジプロポキシシラン、フェネチルメチルジプロポキシシラン、ジメチルジブトキシシラン、ジエチルジブトキシシラン、ジプロピルジブトキシシラン、ジブチルジブトキシシラン、ジペンチルジブトキシシラン、ジヘキシルジブトキシシラン、エチルメチルジブトキシシラン、メチルプロピルジブトキシシラン、ブチルメチルジブトキシシラン、ペンチルメチルジブトキシシラン、ヘキシルメチルジブトキシシラン、３−クロロプロピルメチルブトキシシラン、トリフルオロメチルメチルジブトキシシラン、ヘプタフルオロプロピルメチルジブトキシシラン、シクロヘキシルメチルジブトキシシラン、ジアリルジブトキシシラン、アリルメチルジブトキシシラン、ジビニルジブトキシシラン、メチルビニルジブトキシシラン、ジフェニルジブトキシシラン、フェニルメチルジブトキシシラン、ベンジルメチルジブトキシシラン、フェネチルメチルジブトキシシラン等が挙げられる。 Preferred dialkoxysilane compounds represented by the general formula (1) include, for example, dimethyldimethoxysilane, diethyldimethoxysilane, dipropyldimethoxysilane, dibutyldimethoxysilane, dipentyldimethoxysilane, dihexyldimethoxysilane, and ethylmethyl. Dimethoxysilane, methylpropyldimethoxysilane, butylmethyldimethoxysilane, pentylmethyldimethoxysilane, hexylmethyldimethoxysilane, 3-chloropropylmethyldimethoxysilane, trifluoromethyldimethoxysilane, heptafluoropropylmethyldimethoxysilane, cyclohexylmethyldimethoxysilane, diallyl Dimethoxysilane, allylmethyldimethoxysilane, divinyldimethoxysilane, methylvinyldi Toxisilane, diphenyldimethoxysilane, phenylmethyldimethoxysilane, benzylmethyldimethoxysilane, phenethylmethyldimethoxysilane, dimethyldiethoxysilane, diethyldiethoxysilane, dipropyldiethoxysilane, dibutyldiethoxysilane, dipentyldiethoxysilane, dihexyldiethoxy Silane, ethylmethyldiethoxysilane, methylpropyldiethoxysilane, butylmethyldiethoxysilane, pentylmethyldiethoxysilane, hexylmethyldiethoxysilane, 3-chloropropylmethyldiethoxysilane, trifluoromethyldiethoxysilane, heptafluoro Propylmethyldiethoxysilane, cyclohexylmethyldiethoxysilane, diallyldiethoxysilane, allylmethyldiet Sisilane, divinyldiethoxysilane, methylvinyldiethoxysilane, diphenyldiethoxysilane, phenylmethyldiethoxysilane, benzylmethyldiethoxysilane, phenethylethyldimethoxysilane, dimethyldipropoxysilane, diethyldipropoxysilane, dipropyldipropoxysilane , Dibutyldipropoxysilane, dipentyldipropoxysilane, dihexyldipropoxysilane, ethylmethyldipropoxysilane, methylpropyldipropoxysilane, butylmethyldipropoxysilane, pentylmethyldipropoxysilane, hexylmethyldipropoxysilane, 3-chloropropyl Methyldipropoxysilane, trifluoromethylmethyldipropoxysilane, heptafluoropropylmethyldipropoxysilane , Cyclohexylmethyldipropoxysilane, diallyldipropoxysilane, allylmethyldipropoxysilane, divinyldipropoxysilane, methylvinyldipropoxysilane, diphenyldipropoxysilane, phenylmethyldipropoxysilane, benzylmethyldipropoxysilane, phenethylmethyldipropoxysilane Silane, dimethyldibutoxysilane, diethyldibutoxysilane, dipropyldibutoxysilane, dibutyldibutoxysilane, dipentyldibutoxysilane, dihexyldibutoxysilane, ethylmethyldibutoxysilane, methylpropyldibutoxysilane, butylmethyldibutoxysilane , Pentylmethyldibutoxysilane, hexylmethyldibutoxysilane, 3-chloropropylmethylbutoxysilane, trifluoro Tylmethyldibutoxysilane, heptafluoropropylmethyldibutoxysilane, cyclohexylmethyldibutoxysilane, diallyldibutoxysilane, allylmethyldibutoxysilane, divinyldibutoxysilane, methylvinyldibutoxysilane, diphenyldibutoxysilane, phenylmethyldi Examples include butoxysilane, benzylmethyldibutoxysilane, and phenethylmethyldibutoxysilane.
前記一般式（１）で表されるジアルコキシシラン化合物としては、反応性及び入手の容易さの点から、ジメチルジメトキシシラン、ジメチルジエトキシシラン、ジエチルジメトキシシラン、ジエチルジエトキシシラン、３−クロロプロピルメチルジメトキシシラン、シクロヘキシルメチルジメトキシシラン、ジフェニルジメトキシシラン、フェニルメチルジメトキシランが好ましい。 The dialkoxysilane compound represented by the general formula (1) includes dimethyldimethoxysilane, dimethyldiethoxysilane, diethyldimethoxysilane, diethyldiethoxysilane, and 3-chloropropyl from the viewpoints of reactivity and availability. Methyldimethoxysilane, cyclohexylmethyldimethoxysilane, diphenyldimethoxysilane, and phenylmethyldimethoxylane are preferred.
次に、フッ化水素酸について説明する。本発明においてフッ化水素酸とは、フッ化水素の水溶液をいう。フッ化水素酸中のフッ化水素の濃度は、１〜５０質量％が好ましく、１０〜５０質量％が更に好ましい。 Next, hydrofluoric acid will be described. In the present invention, hydrofluoric acid refers to an aqueous solution of hydrogen fluoride. The concentration of hydrogen fluoride in hydrofluoric acid is preferably 1 to 50% by mass, and more preferably 10 to 50% by mass.
次に本発明の製造方法について説明する。
本発明の製造方法において、ジアルコキシシラン化合物に対してフッ化水素があまりに少ない場合には、反応が十分進行せず、またあまりに多い場合には、副生物のジフルオロシラン化合物が増えて、１，３−ジフルオロジシロキサン化合物の収量が減少してしまう。このため、ジアルコキシシラン化合物とフッ化水素酸の使用量は、ジアルコキシシラン化合物１モルに対して、フッ化水素が０．９〜２モルであることが好ましく、１．０〜１．５モルであることが更に好ましく、１．０５〜１．３モルであることが最も好ましい。
Next, the manufacturing method of this invention is demonstrated.
In the production method of the present invention, when the hydrogen fluoride is too small relative to the dialkoxysilane compound, the reaction does not proceed sufficiently, and when it is too much, the by-product difluorosilane compound increases, The yield of 3-difluorodisiloxane compound is reduced. For this reason, it is preferable that the usage-amounts of a dialkoxysilane compound and hydrofluoric acid are 0.9-2 mol of hydrogen fluoride with respect to 1 mol of dialkoxysilane compounds, and 1.0-1.5 More preferably, it is mol, and most preferably 1.05-1.3 mol.
ジアルコキシシラン化合物とフッ化水素の反応は、あまりに低い温度では反応があまり進行せず、また、あまり高い温度では副反応が起こり易くなることから、反応温度は−１５〜３０℃が好ましく、０〜３０℃が更に好ましい。ジアルコキシシラン化合物とフッ化水素は、一括して仕込んで反応させてもよいし、分割して仕込んでもよいが、ジアルコキシシラン化合物とフッ化水素の反応が発熱反応であり、反応の制御が容易であり副生物の生成量も少なくなることから、ジアルコキシシラン化合物にフッ化水素酸を滴下または分割添加することが好ましい。前記反応温度におけるフッ化水素酸とジアルコキシシラン化合物との反応時間は、フッ化水素酸をジアルコキシシラン化合物に一括、滴下または分割の何れの方法で添加するかにもよるが、好ましくは、１〜６０分である。フッ化水素酸の滴下終了後、発熱がおさまったら、反応を完結させるために４０℃〜６０℃に昇温し３０〜１２０分程度追加熟成することが好ましい。 The reaction between the dialkoxysilane compound and hydrogen fluoride does not proceed much at a too low temperature, and a side reaction tends to occur at a too high temperature. Therefore, the reaction temperature is preferably −15 to 30 ° C., 0 More preferably, -30 ° C. The dialkoxysilane compound and hydrogen fluoride may be charged and reacted in a lump or may be charged separately, but the reaction of the dialkoxysilane compound and hydrogen fluoride is an exothermic reaction, and the reaction is controlled. Since it is easy and the amount of by-products generated is small, it is preferable to add hydrofluoric acid dropwise or dividedly to the dialkoxysilane compound. The reaction time between hydrofluoric acid and the dialkoxysilane compound at the reaction temperature depends on whether hydrofluoric acid is added to the dialkoxysilane compound all at once, dropwise, or divided, but preferably, 1-60 minutes. After completion of the dropwise addition of hydrofluoric acid, it is preferable to raise the temperature to 40 ° C. to 60 ° C. and additional ripening for about 30 to 120 minutes in order to complete the reaction.
本発明の製造方法では、ジアルコキシシラン化合物とフッ化水素との反応性が上がることから、アルコール溶媒を使用することが好ましい。アルコール溶媒としては、例えば、メタノール、エタノール、プロパノール、イソプロパノール、ブタノール、イソブタノール、エチレングリコール、プロピレングリコール、２−メトキシエタノール、２−エトキシエタノール、１−メトキシ−２−プロパノール等が挙げられ、反応性の向上効果が高く、反応終了後に容易に除去できることから、メタノール、エタノールが好ましく、メタノールが更に好ましい。アルコール溶媒の使用量は、ジアルコキシシラン化合物１００質量部に対して、５〜１０００質量部が好ましく、２０〜１０００質量部が更に好ましく、４０〜２００質量部が最も好ましい。 In the production method of the present invention, an alcohol solvent is preferably used because the reactivity between the dialkoxysilane compound and hydrogen fluoride increases. Examples of the alcohol solvent include methanol, ethanol, propanol, isopropanol, butanol, isobutanol, ethylene glycol, propylene glycol, 2-methoxyethanol, 2-ethoxyethanol, 1-methoxy-2-propanol, and the like. Methanol and ethanol are preferable, and methanol is more preferable because it can be easily removed after completion of the reaction. The amount of the alcohol solvent used is preferably 5 to 1000 parts by mass, more preferably 20 to 1000 parts by mass, and most preferably 40 to 200 parts by mass with respect to 100 parts by mass of the dialkoxysilane compound.
ジアルコキシシラン化合物とフッ化水素とを反応させた後、過剰のフッ化水素酸を水洗等により除去し、蒸留等の方法により精製することにより、純度よく１，３−ジフルオロジシロキサン化合物を得ることができる。 After reacting the dialkoxysilane compound with hydrogen fluoride, the excess hydrofluoric acid is removed by washing with water, etc., and purified by a method such as distillation to obtain a 1,3-difluorodisiloxane compound with high purity. be able to.
本発明の製造方法により得られる前記一般式（２）で表される１，３−ジフルオロジシロキサン化合物は、各種添加剤、合成中間体等として有用であり、中でも、プラズマＣＶＤ等の方法により形成される、層間絶縁膜、パッシベーション膜、ゲート絶縁膜等の絶縁膜の材料；非水電解液二次電池用の電解液添加剤として有用である。 The 1,3-difluorodisiloxane compound represented by the general formula (2) obtained by the production method of the present invention is useful as various additives, synthetic intermediates, etc., among others, formed by a method such as plasma CVD. Materials for insulating films such as interlayer insulating films, passivation films, gate insulating films, etc .; useful as an electrolyte additive for non-aqueous electrolyte secondary batteries.
以下に、実施例及び比較例等により本発明を更に詳細に説明する。ただし、以下の実施例等により本発明はなんら制限されるものではない。尚、実施例中の「部」や「％」は、特に断らない限り質量によるものである。また、実施例及び比較例等により製造された化合物の同定は1Ｈ−ＮＭＲのスペクトルチャートを用いて行い、純度はガスクロマトグラフィーのチャートにおいて、目的物の純度が９９％以上であることを確認した。 Hereinafter, the present invention will be described in more detail with reference to Examples and Comparative Examples. However, the present invention is not limited by the following examples. In the examples, “parts” and “%” are based on mass unless otherwise specified. In addition, identification of the compounds produced in Examples and Comparative Examples is performed using a spectrum chart of 1 H-NMR, and the purity is confirmed to be 99% or more in the gas chromatography chart. did.
実施例１
＜１，３−ジフルオロ−１，１，３，３−テトラメチルジシロキサンの合成＞
撹拌機、温度計、還流器を備えた反応容器に窒素雰囲気下で、ジメチルジメトキシシラン２９３ｇ（２モル）を仕込み、０℃で撹拌しながら、１５％フッ化水素酸２６７ｇ（フッ化水素として２．２モル）を１時間かけて滴下し、滴下後、更に０℃で３０分間攪拌を続けた。その後、３０分かけて６０℃まで昇温し、更に６０℃で６０分間撹拌を行った。反応容器にジブチルエーテル４８ｇを仕込み、撹拌、静置後、水層を除去し、残った有機層を分液ロートに移して飽和食塩水６０ｍｌで洗浄した後、有機層を無水硫酸ナトリウムで乾燥させた。有機層を蒸留することによって、１，３−ジフルオロ−１，１，３，３−テトラメチルジシロキサン１１９ｇを得た（収率７０％）。
Example 1
<Synthesis of 1,3-difluoro-1,1,3,3-tetramethyldisiloxane>
In a reaction vessel equipped with a stirrer, thermometer, and refluxer, 293 g (2 mol) of dimethyldimethoxysilane was charged in a nitrogen atmosphere and stirred at 0 ° C., and 267 g of 15% hydrofluoric acid (2 as hydrogen fluoride). 2 mol) was added dropwise over 1 hour, and after the addition, stirring was further continued at 0 ° C. for 30 minutes. Then, it heated up to 60 degreeC over 30 minutes, and also stirred at 60 degreeC for 60 minutes. The reaction vessel was charged with 48 g of dibutyl ether, stirred and allowed to stand, the aqueous layer was removed, the remaining organic layer was transferred to a separatory funnel and washed with 60 ml of saturated brine, and then the organic layer was dried over anhydrous sodium sulfate. It was. The organic layer was distilled to obtain 119 g of 1,3-difluoro-1,1,3,3-tetramethyldisiloxane (yield 70%).
実施例２
＜１，３−ビス（３−クロロプロピル）−１，３−ジフルオロ−１，３−ジメチルジシロキサンの合成＞
実施例１と同様の反応容器に、窒素雰囲気下で、３−クロロプロピルメチルジメトキシシラン１８２．５ｇ（１モル）とメタノール１２０ｇを仕込み、０℃で撹拌しながら、４６％フッ化水素酸６５ｇ（フッ化水素として１．２モル）を１時間かけて滴下し、滴下後、更に０℃で３０分間攪拌を続けた。その後、３０分かけて６０℃まで昇温し、更に６０℃で６０分間撹拌を行った。反応容器にヘキサン１５０ｇと飽和食塩水１５０ｇを仕込み、撹拌、静置後、水層を除去し、残った有機層を分液ロートに移して飽和炭酸水素ナトリウム水溶液６０ｇで洗浄した後、有機層を無水硫酸ナトリウムで乾燥させた。有機層を蒸留することによって、１，３−ビス（３−クロロプロピル）−１，３−ジフルオロ−１，３−ジメチルジシロキサン１２１ｇを得た（収率８２％）。
Example 2
<Synthesis of 1,3-bis (3-chloropropyl) -1,3-difluoro-1,3-dimethyldisiloxane>
In a reaction vessel similar to that in Example 1, 182.5 g (1 mol) of 3-chloropropylmethyldimethoxysilane and 120 g of methanol were charged in a nitrogen atmosphere and stirred at 0 ° C. with 65 g of 46% hydrofluoric acid ( 1.2 mol of hydrogen fluoride) was added dropwise over 1 hour, and after the addition, stirring was further continued at 0 ° C. for 30 minutes. Then, it heated up to 60 degreeC over 30 minutes, and also stirred at 60 degreeC for 60 minutes. The reaction vessel was charged with 150 g of hexane and 150 g of saturated brine, stirred and allowed to stand. The aqueous layer was removed, and the remaining organic layer was transferred to a separatory funnel and washed with 60 g of a saturated aqueous sodium hydrogen carbonate solution. Dry over anhydrous sodium sulfate. The organic layer was distilled to obtain 121 g of 1,3-bis (3-chloropropyl) -1,3-difluoro-1,3-dimethyldisiloxane (yield 82%).
実施例３
＜１，３−ジフルオロ−１，３−ジフェニル−１，３−ジメチルジシロキサンの合成＞
実施例１と同様の反応容器に、窒素雰囲気下で、フェニルメチルジメトキシシラン１８２．５ｇ（１モル）とメタノール１２０ｇを仕込み、０℃で撹拌しながら、２３％フッ化水素酸１３０ｇ（フッ化水素として１．２モル）を１時間かけて滴下し、滴下後、更に０℃で３０分間攪拌を続けた。その後、３０分かけて６０℃まで昇温し、更に６０℃で６０分間撹拌を行った。反応容器にヘキサン１５０ｇと飽和食塩水１５０ｇを仕込み、撹拌、静置後、水層を除去し、残った有機層を分液ロートに移して飽和炭酸水素ナトリウム水溶液６０ｇで洗浄した後、有機層を無水硫酸ナトリウムで乾燥させた。有機層を蒸留することによって、１，３−ジフルオロ−１，３−ジフェニル−１，３−ジメチルジシロキサン１０６ｇを得た（収率７２％）。
Example 3
<Synthesis of 1,3-difluoro-1,3-diphenyl-1,3-dimethyldisiloxane>
In a reaction vessel similar to that in Example 1, 182.5 g (1 mol) of phenylmethyldimethoxysilane and 120 g of methanol were charged in a nitrogen atmosphere, and 130 g of 23% hydrofluoric acid (hydrogen fluoride) was stirred at 0 ° C. 1.2 mol) was added dropwise over 1 hour, and after the addition, stirring was further continued at 0 ° C. for 30 minutes. Then, it heated up to 60 degreeC over 30 minutes, and also stirred at 60 degreeC for 60 minutes. The reaction vessel was charged with 150 g of hexane and 150 g of saturated brine, stirred and allowed to stand. The aqueous layer was removed, and the remaining organic layer was transferred to a separatory funnel and washed with 60 g of a saturated aqueous sodium hydrogen carbonate solution. Dry over anhydrous sodium sulfate. The organic layer was distilled to obtain 106 g of 1,3-difluoro-1,3-diphenyl-1,3-dimethyldisiloxane (yield 72%).
比較例１
＜１，３−ジフルオロ−１，１，３，３−テトラメチルジシロキサンの合成＞
特開２０１０−２７２３７６号公報の合成例１に準じ、１，３−ジフルオロ−１，１，３，３−テトラメチルジシロキサンを合成した。
実施例１と同様の反応容器に、三フッ化アンチモン７５ｇ（０．４モル）及びｏ−キシレン１５０ｇを仕込み、窒素雰囲気下で、０℃で攪拌し、１，３−ジクロロ−１，１，３，３−テトラメチルジシロキサン１２２ｇ（０．６モル）を１時間かけて滴下した。滴下後、２５℃で、更に２時間撹拌し反応を完結させた。反応容器に飽和食塩水１５０ｇを仕込み、撹拌、静置後、水層を除去し、残った有機層を分液ロートに移して飽和炭酸水素ナトリウム水溶液６０ｇで洗浄した後、有機層を無水硫酸ナトリウムで乾燥させた。有機層を蒸留することによって、１，３−ジフルオロ−１，１，３，３−テトラメチルジシロキサン１１６ｇを得た（収率６８％）。
Comparative Example 1
<Synthesis of 1,3-difluoro-1,1,3,3-tetramethyldisiloxane>
1,3-difluoro-1,1,3,3-tetramethyldisiloxane was synthesized according to Synthesis Example 1 of JP 2010-272376 A.
In a reaction vessel similar to that of Example 1, 75 g (0.4 mol) of antimony trifluoride and 150 g of o-xylene were charged and stirred at 0 ° C. in a nitrogen atmosphere to obtain 1,3-dichloro-1,1, 122 g (0.6 mol) of 3,3-tetramethyldisiloxane was added dropwise over 1 hour. After the dropwise addition, the reaction was completed by further stirring at 25 ° C. for 2 hours. A reaction vessel was charged with 150 g of saturated brine, stirred and allowed to stand, the aqueous layer was removed, the remaining organic layer was transferred to a separatory funnel and washed with 60 g of a saturated aqueous sodium bicarbonate solution, and then the organic layer was anhydrous sodium sulfate. And dried. The organic layer was distilled to obtain 116 g of 1,3-difluoro-1,1,3,3-tetramethyldisiloxane (yield 68%).
実施例１と比較例１を比較すれば明らかなように、本発明の製造法によれば、従来の１，３−ジクロロジシロキサン化合物と金属フッ化物との反応と同程度の収率で、１，３−ジフルオロジシロキサン化合物を得ることができ、毒性の高い金属フッ化物を使用することもない。また、１，３−ジクロロジシロキサン化合物はモノシラン化合物から製造する必要があるのに対し、本発明の製造法では、工業的に一般なジアルコキシシラン化合物から１段階で１，３−ジフルオロジシロキサン化合物を得ることができ、本発明の製造方法は、化学産業的価値が高いといえる。 As is clear from comparison between Example 1 and Comparative Example 1, according to the production method of the present invention, the yield is similar to the reaction of the conventional 1,3-dichlorodisiloxane compound and metal fluoride. A 1,3-difluorodisiloxane compound can be obtained, and a highly toxic metal fluoride is not used. Further, while the 1,3-dichlorodisiloxane compound needs to be produced from a monosilane compound, in the production method of the present invention, 1,3-difluorodisiloxane is produced in one step from an industrially common dialkoxysilane compound. A compound can be obtained, and it can be said that the production method of the present invention has high chemical industrial value.
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