JP6681284B2 - 糖アルコール化合物の金属低減方法 - Google Patents
糖アルコール化合物の金属低減方法 Download PDFInfo
- Publication number
- JP6681284B2 JP6681284B2 JP2016124209A JP2016124209A JP6681284B2 JP 6681284 B2 JP6681284 B2 JP 6681284B2 JP 2016124209 A JP2016124209 A JP 2016124209A JP 2016124209 A JP2016124209 A JP 2016124209A JP 6681284 B2 JP6681284 B2 JP 6681284B2
- Authority
- JP
- Japan
- Prior art keywords
- metal
- sugar alcohol
- alcohol compound
- reaction
- group
- 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.)
- Active
Links
- 229910052751 metal Inorganic materials 0.000 title claims description 89
- 239000002184 metal Substances 0.000 title claims description 89
- -1 sugar alcohol compound Chemical class 0.000 title claims description 86
- 238000000034 method Methods 0.000 title claims description 38
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 claims description 31
- 239000000600 sorbitol Substances 0.000 claims description 31
- 125000006239 protecting group Chemical group 0.000 claims description 25
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 24
- 239000012535 impurity Substances 0.000 claims description 23
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 20
- QWOJMRHUQHTCJG-UHFFFAOYSA-N CC([CH2-])=O Chemical compound CC([CH2-])=O QWOJMRHUQHTCJG-UHFFFAOYSA-N 0.000 claims description 19
- 238000004519 manufacturing process Methods 0.000 claims description 14
- 239000004065 semiconductor Substances 0.000 claims description 14
- 238000010511 deprotection reaction Methods 0.000 claims description 12
- 238000004821 distillation Methods 0.000 claims description 12
- 238000005406 washing Methods 0.000 claims description 12
- 239000008367 deionised water Substances 0.000 claims description 11
- 229910021641 deionized water Inorganic materials 0.000 claims description 11
- 238000000926 separation method Methods 0.000 claims description 11
- 239000007788 liquid Substances 0.000 claims description 9
- 238000000354 decomposition reaction Methods 0.000 claims 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 36
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 36
- 235000010356 sorbitol Nutrition 0.000 description 31
- 238000006243 chemical reaction Methods 0.000 description 30
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- HEBKCHPVOIAQTA-UHFFFAOYSA-N meso ribitol Natural products OCC(O)C(O)C(O)CO HEBKCHPVOIAQTA-UHFFFAOYSA-N 0.000 description 21
- 239000002904 solvent Substances 0.000 description 17
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 16
- 239000011734 sodium Substances 0.000 description 16
- 229910052708 sodium Inorganic materials 0.000 description 16
- TVXBFESIOXBWNM-UHFFFAOYSA-N Xylitol Natural products OCCC(O)C(O)C(O)CCO TVXBFESIOXBWNM-UHFFFAOYSA-N 0.000 description 15
- 239000000203 mixture Substances 0.000 description 15
- 239000000811 xylitol Substances 0.000 description 15
- 235000010447 xylitol Nutrition 0.000 description 15
- HEBKCHPVOIAQTA-SCDXWVJYSA-N xylitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)CO HEBKCHPVOIAQTA-SCDXWVJYSA-N 0.000 description 15
- 229960002675 xylitol Drugs 0.000 description 15
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 239000007787 solid Substances 0.000 description 12
- 239000003377 acid catalyst Substances 0.000 description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 230000000052 comparative effect Effects 0.000 description 9
- 238000001914 filtration Methods 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- 238000001095 inductively coupled plasma mass spectrometry Methods 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- UNXHWFMMPAWVPI-UHFFFAOYSA-N Erythritol Natural products OCC(O)C(O)CO UNXHWFMMPAWVPI-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 6
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 238000004811 liquid chromatography Methods 0.000 description 6
- 238000001953 recrystallisation Methods 0.000 description 6
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 6
- OXQKEKGBFMQTML-UHFFFAOYSA-N alpha-Glucoheptitol Chemical compound OCC(O)C(O)C(O)C(O)C(O)CO OXQKEKGBFMQTML-UHFFFAOYSA-N 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 238000006136 alcoholysis reaction Methods 0.000 description 4
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 4
- 150000002148 esters Chemical group 0.000 description 4
- 238000004817 gas chromatography Methods 0.000 description 4
- 238000006460 hydrolysis reaction Methods 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 239000011347 resin Substances 0.000 description 4
- 229920005989 resin Polymers 0.000 description 4
- 238000004809 thin layer chromatography Methods 0.000 description 4
- IMPKVMRTXBRHRB-MBMOQRBOSA-N (+)-quercitol Chemical compound O[C@@H]1C[C@@H](O)[C@H](O)C(O)[C@H]1O IMPKVMRTXBRHRB-MBMOQRBOSA-N 0.000 description 3
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 3
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 3
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- DRDSDQVQSRICML-UHFFFAOYSA-N D-Erythro-D-galacto-octitol Chemical compound OCC(O)C(O)C(O)C(O)C(O)C(O)CO DRDSDQVQSRICML-UHFFFAOYSA-N 0.000 description 3
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 3
- HEBKCHPVOIAQTA-QWWZWVQMSA-N D-arabinitol Chemical compound OC[C@@H](O)C(O)[C@H](O)CO HEBKCHPVOIAQTA-QWWZWVQMSA-N 0.000 description 3
- FBPFZTCFMRRESA-ZXXMMSQZSA-N D-iditol Chemical compound OC[C@@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-ZXXMMSQZSA-N 0.000 description 3
- UNXHWFMMPAWVPI-QWWZWVQMSA-N D-threitol Chemical compound OC[C@@H](O)[C@H](O)CO UNXHWFMMPAWVPI-QWWZWVQMSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 239000004386 Erythritol Substances 0.000 description 3
- SQUHHTBVTRBESD-UHFFFAOYSA-N Hexa-Ac-myo-Inositol Natural products CC(=O)OC1C(OC(C)=O)C(OC(C)=O)C(OC(C)=O)C(OC(C)=O)C1OC(C)=O SQUHHTBVTRBESD-UHFFFAOYSA-N 0.000 description 3
- 229930195725 Mannitol Natural products 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- JVWLUVNSQYXYBE-UHFFFAOYSA-N Ribitol Natural products OCC(C)C(O)C(O)CO JVWLUVNSQYXYBE-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 239000003729 cation exchange resin Substances 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 235000019414 erythritol Nutrition 0.000 description 3
- UNXHWFMMPAWVPI-ZXZARUISSA-N erythritol Chemical compound OC[C@H](O)[C@H](O)CO UNXHWFMMPAWVPI-ZXZARUISSA-N 0.000 description 3
- 229940009714 erythritol Drugs 0.000 description 3
- 150000002170 ethers Chemical class 0.000 description 3
- FBPFZTCFMRRESA-GUCUJZIJSA-N galactitol Chemical compound OC[C@H](O)[C@@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-GUCUJZIJSA-N 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- 150000002430 hydrocarbons Chemical class 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 229910052500 inorganic mineral Inorganic materials 0.000 description 3
- CDAISMWEOUEBRE-GPIVLXJGSA-N inositol Chemical compound O[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@H](O)[C@@H]1O CDAISMWEOUEBRE-GPIVLXJGSA-N 0.000 description 3
- 229960000367 inositol Drugs 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- 239000000594 mannitol Substances 0.000 description 3
- 235000010355 mannitol Nutrition 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000011707 mineral Substances 0.000 description 3
- 235000010755 mineral Nutrition 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- HEBKCHPVOIAQTA-ZXFHETKHSA-N ribitol Chemical compound OC[C@H](O)[C@H](O)[C@H](O)CO HEBKCHPVOIAQTA-ZXFHETKHSA-N 0.000 description 3
- CDAISMWEOUEBRE-UHFFFAOYSA-N scyllo-inosotol Natural products OC1C(O)C(O)C(O)C(O)C1O CDAISMWEOUEBRE-UHFFFAOYSA-N 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- HEWZVZIVELJPQZ-UHFFFAOYSA-N 2,2-dimethoxypropane Chemical compound COC(C)(C)OC HEWZVZIVELJPQZ-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
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 229910015900 BF3 Inorganic materials 0.000 description 2
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 239000002841 Lewis acid Substances 0.000 description 2
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 2
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- WLFQVYGQQKKEMR-UHFFFAOYSA-M [Cl+].[Cl-] Chemical compound [Cl+].[Cl-] WLFQVYGQQKKEMR-UHFFFAOYSA-M 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 239000007810 chemical reaction solvent Substances 0.000 description 2
- 238000011109 contamination Methods 0.000 description 2
- RYPWQHONZWFXBN-UHFFFAOYSA-N dichloromethyl(methylidene)-$l^{3}-chlorane Chemical compound ClC(Cl)Cl=C RYPWQHONZWFXBN-UHFFFAOYSA-N 0.000 description 2
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- 150000007517 lewis acids Chemical class 0.000 description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
- 239000011976 maleic acid Substances 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- 229940098779 methanesulfonic acid Drugs 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 229910017604 nitric acid Inorganic materials 0.000 description 2
- 150000002825 nitriles Chemical class 0.000 description 2
- 235000006408 oxalic acid Nutrition 0.000 description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
- 239000002798 polar solvent Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- ZDYVRSLAEXCVBX-UHFFFAOYSA-N pyridinium p-toluenesulfonate Chemical compound C1=CC=[NH+]C=C1.CC1=CC=C(S([O-])(=O)=O)C=C1 ZDYVRSLAEXCVBX-UHFFFAOYSA-N 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 150000005846 sugar alcohols Chemical class 0.000 description 2
- 150000003460 sulfonic acids Chemical class 0.000 description 2
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- KPZGRMZPZLOPBS-UHFFFAOYSA-N 1,3-dichloro-2,2-bis(chloromethyl)propane Chemical compound ClCC(CCl)(CCl)CCl KPZGRMZPZLOPBS-UHFFFAOYSA-N 0.000 description 1
- FGQLGYBGTRHODR-UHFFFAOYSA-N 2,2-diethoxypropane Chemical compound CCOC(C)(C)OCC FGQLGYBGTRHODR-UHFFFAOYSA-N 0.000 description 1
- YQTCQNIPQMJNTI-UHFFFAOYSA-N 2,2-dimethylpropan-1-one Chemical group CC(C)(C)[C]=O YQTCQNIPQMJNTI-UHFFFAOYSA-N 0.000 description 1
- FSGHEPDRMHVUCQ-UHFFFAOYSA-N 2-ethoxyprop-1-ene Chemical compound CCOC(C)=C FSGHEPDRMHVUCQ-UHFFFAOYSA-N 0.000 description 1
- YOWQWFMSQCOSBA-UHFFFAOYSA-N 2-methoxypropene Chemical compound COC(C)=C YOWQWFMSQCOSBA-UHFFFAOYSA-N 0.000 description 1
- YLZOPXRUQYQQID-UHFFFAOYSA-N 3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-1-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]propan-1-one Chemical compound N1N=NC=2CN(CCC=21)CCC(=O)N1CCN(CC1)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F YLZOPXRUQYQQID-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- OXQKEKGBFMQTML-WAHCGKIUSA-N Perseitol Natural products OC[C@H](O)[C@H](O)C(O)[C@H](O)[C@H](O)CO OXQKEKGBFMQTML-WAHCGKIUSA-N 0.000 description 1
- PDBOLQCPEKXSBW-UHFFFAOYSA-M [Ti]Cl Chemical compound [Ti]Cl PDBOLQCPEKXSBW-UHFFFAOYSA-M 0.000 description 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
- 150000001241 acetals Chemical group 0.000 description 1
- 235000011054 acetic acid Nutrition 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 239000003957 anion exchange resin Substances 0.000 description 1
- 238000000998 batch distillation Methods 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 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
- 125000000649 benzylidene group Chemical group [H]C(=[*])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 1
- 229910000024 caesium carbonate Inorganic materials 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 125000005587 carbonate group Chemical group 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 229940023913 cation exchange resins Drugs 0.000 description 1
- 229920001429 chelating resin Polymers 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000001944 continuous distillation Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 150000005676 cyclic carbonates Chemical group 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- JGFBRKRYDCGYKD-UHFFFAOYSA-N dibutyl(oxo)tin Chemical compound CCCC[Sn](=O)CCCC JGFBRKRYDCGYKD-UHFFFAOYSA-N 0.000 description 1
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical group [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 1
- 239000012776 electronic material Substances 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 125000000219 ethylidene group Chemical group [H]C(=[*])C([H])([H])[H] 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 125000000654 isopropylidene group Chemical group C(C)(C)=* 0.000 description 1
- 229910001629 magnesium chloride Inorganic materials 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 238000001465 metallisation Methods 0.000 description 1
- ZEIWWVGGEOHESL-UHFFFAOYSA-N methanol;titanium Chemical compound [Ti].OC.OC.OC.OC ZEIWWVGGEOHESL-UHFFFAOYSA-N 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- OXQKEKGBFMQTML-BIVRFLNRSA-N perseitol Chemical compound OC[C@H](O)[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO OXQKEKGBFMQTML-BIVRFLNRSA-N 0.000 description 1
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Chemical group O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
- CHKVPAROMQMJNQ-UHFFFAOYSA-M potassium bisulfate Chemical compound [K+].OS([O-])(=O)=O CHKVPAROMQMJNQ-UHFFFAOYSA-M 0.000 description 1
- 229910000343 potassium bisulfate Inorganic materials 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 239000013076 target 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
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
- 125000000025 triisopropylsilyl group Chemical group C(C)(C)[Si](C(C)C)(C(C)C)* 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/74—Separation; Purification; Use of additives, e.g. for stabilisation
- C07C29/88—Separation; Purification; Use of additives, e.g. for stabilisation by treatment giving rise to a chemical modification of at least one compound
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/74—Separation; Purification; Use of additives, e.g. for stabilisation
- C07C29/88—Separation; Purification; Use of additives, e.g. for stabilisation by treatment giving rise to a chemical modification of at least one compound
- C07C29/92—Separation; Purification; Use of additives, e.g. for stabilisation by treatment giving rise to a chemical modification of at least one compound by a consecutive conversion and reconstruction
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B51/00—Introduction of protecting groups or activating groups, not provided for in the preceding groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/09—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/128—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by alcoholysis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/74—Separation; Purification; Use of additives, e.g. for stabilisation
- C07C29/76—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment
- C07C29/80—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment by distillation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C31/00—Saturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C31/18—Polyhydroxylic acyclic alcohols
- C07C31/24—Tetrahydroxylic alcohols, e.g. pentaerythritol
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C31/00—Saturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C31/18—Polyhydroxylic acyclic alcohols
- C07C31/26—Hexahydroxylic alcohols
-
- 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
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
また、本発明の糖アルコール化合物であれば、金属低減されたものであるため、半導体装置製造工程に好適に用いることができるものとなる。
本発明の糖アルコール化合物は、不純物として含有されるナトリウムの含有量が100ppb以下のものであり、好ましくは50ppb以下のものである。特に、本発明の糖アルコール化合物としては、ナトリウムを始め各金属不純物の含有量が固形分あたり100ppb以下のものであることが好ましい。
本発明の糖アルコール化合物の金属除去方法は、(A)金属を不純物として含有する糖アルコール化合物の水酸基を保護基で保護する保護化工程、(B)前記水酸基が保護基で保護された糖アルコール化合物から不純物である金属を除去する金属除去工程、及び(C)前記金属除去された糖アルコール化合物の保護基を脱保護する脱保護工程、を含む。
まず、本発明では、金属を不純物として含有する糖アルコール化合物(以下、金属低減対象の糖アルコール化合物とも言う)の水酸基を保護基で保護する保護化工程を行う(工程(A))。
次に、工程(A)で水酸基が保護基で保護された糖アルコール化合物から不純物である金属を除去する金属除去工程を行う(工程(B))。工程(B)における金属除去の方法としては、特に限定されないが、(B1)分液水洗及び(B2)蒸留のいずれかを行うこと、もしくは両者を組合せて行うことが好ましい。
工程(B)の後、金属除去された糖アルコール化合物の保護基を脱保護する脱保護工程を行う(工程(C))。工程(C)における脱保護の方法としては、特に限定されず、用いた保護基に応じて適切な方法を選択することが望ましいが、工程(C)を加水分解反応又は加アルコール分解反応で行うことが、金属不純物汚染を防止するという観点から特に好ましい。
本発明の糖アルコール化合物の金属低減方法を用いて、キシリトールの金属低減を行った。まず、キシリトール152g、2,2−ジメトキシプロパン312g、p−トルエンスルホン酸1.9g、トルエン450gの混合物を、反応により生成するメタノールを徐々に留去しながら、16時間加熱還流した(工程(A))。室温に冷却後、28%アンモニア水1.2gを加えて反応を停止した。その後、脱イオン水150gを用いて4回分液水洗を行い(工程(B))、減圧濃縮して、アセトニド保護されたキシリトールを生成物として得た。
東京化成工業製のキシリトールについて、ICP−MSにより測定したナトリウム含有量は、3,500ppbであった。
本発明の糖アルコール化合物の金属低減方法を用いて、ソルビトールの金属低減を行った。まず、ソルビトール1,000g、アセトン9L、陽イオン交換樹脂アンバーリスト(登録商標)15 23gの混合物を50℃で6時間撹拌した(工程(A))。室温に冷却後、トリエチルアミン17gを加えて反応を停止した。固形分をろ別後、減圧濃縮し、粗生成物1,532gを得た。減圧蒸留を行い(工程(B))、アセトニド保護されたソルビトール1,180gを得た。
東京化成工業製のソルビトールについて、ICP−MSにより測定したナトリウム含有量は、4,000ppbであった。
ソルビトール303g、メタノール1,860gの混合物を70℃で撹拌し溶かした。室温に冷却後、氷浴で冷却し、ソルビトールの固体を得た。固形分をろ別後、これにメタノール800gを加え、1時間撹拌した。再度ろ別後、60℃で減圧乾燥し、ソルビトールの固体を191g、収率63%で得た。ICP−MSにより測定したナトリウム含有量は、4,000ppbであった。
ソルビトール300g、メタノール1,200g、脱イオン水150gの混合物を80℃で撹拌し溶かした。室温に冷却後、氷浴で冷却し、ソルビトールの固体を得た。固形分をろ別後、これにメタノール600gを加え、1時間撹拌した。再度ろ別後、60℃で減圧乾燥し、ソルビトールの固体を136g、収率45%で得た。ICP−MSにより測定したナトリウム含有量は、3,500ppbであった。
ソルビトール103g、メタノール500g、脱イオン水10g、24質量%のマレイン酸水溶液0.05gの混合物を75℃で撹拌し溶かした。室温に冷却後、氷浴で冷却し、ソルビトールの固体を得た。固形分をろ別後、これにメタノール350gを加え、1時間撹拌した。再度ろ別後、脱イオン水を加え、ソルビトール水溶液500gを得た。得られたソルビトール水溶液について、加熱残分法(160℃、1時間)により求めた濃度は10.9質量%であり、収率は90%であった。ICP−MSにより測定したナトリウム含有量は、510ppbであった。
Claims (3)
- (A)金属を不純物として含有する糖アルコール化合物の水酸基を保護基で保護する保護化工程、
(B)前記水酸基が保護基で保護された糖アルコール化合物から不純物である金属を除去する金属除去工程、及び
(C)前記金属除去された糖アルコール化合物の保護基を脱イオン水を用いた加水分解反応で脱保護する脱保護工程、
を含み、かつ、
前記金属を不純物として含有する糖アルコール化合物を、半導体装置製造工程に用いるものであり、かつ、ソルビトールを含むものとすることを特徴とする糖アルコール化合物の金属低減方法。 - 前記工程(B)において、(B1)分液水洗及び(B2)蒸留のいずれかを行うことを特徴とする請求項1に記載の糖アルコール化合物の金属低減方法。
- 前記保護基を、アセトニドとすることを特徴とする請求項1又は請求項2に記載の糖アルコール化合物の金属低減方法。
Priority Applications (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2016124209A JP6681284B2 (ja) | 2016-06-23 | 2016-06-23 | 糖アルコール化合物の金属低減方法 |
US15/585,720 US10131603B2 (en) | 2016-06-23 | 2017-05-03 | Method for reducing metal of sugar-alcohol compound and sugar-alcohol compound |
CN201710387797.9A CN107540491B (zh) | 2016-06-23 | 2017-05-27 | 糖醇化合物的金属低减法以及糖醇化合物 |
KR1020170075663A KR20180000680A (ko) | 2016-06-23 | 2017-06-15 | 당알코올 화합물의 금속 저감 방법 및 당알코올 화합물 |
TW106120468A TWI651296B (zh) | 2016-06-23 | 2017-06-20 | 糖醇化合物之金屬雜質降低方法及糖醇化合物 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2016124209A JP6681284B2 (ja) | 2016-06-23 | 2016-06-23 | 糖アルコール化合物の金属低減方法 |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2017226625A JP2017226625A (ja) | 2017-12-28 |
JP6681284B2 true JP6681284B2 (ja) | 2020-04-15 |
Family
ID=60675869
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2016124209A Active JP6681284B2 (ja) | 2016-06-23 | 2016-06-23 | 糖アルコール化合物の金属低減方法 |
Country Status (5)
Country | Link |
---|---|
US (1) | US10131603B2 (ja) |
JP (1) | JP6681284B2 (ja) |
KR (1) | KR20180000680A (ja) |
CN (1) | CN107540491B (ja) |
TW (1) | TWI651296B (ja) |
Family Cites Families (15)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
AT342080B (de) * | 1976-03-25 | 1978-03-10 | Studiengesellschaft Kohle Mbh | Verfahren zur trennung und/oder reinigung von oligo- und polyhydroxyverbindungen |
JP2807460B2 (ja) * | 1987-12-09 | 1998-10-08 | クローダ ジャパン株式会社 | 糖アルコール又はショ糖の脂肪酸エステルの精製方法 |
JP2815859B2 (ja) * | 1987-12-09 | 1998-10-27 | クローダ ジャパン株式会社 | 糖アルコール又はショ糖の脂肪酸エステルの精製法 |
US5126268A (en) * | 1990-03-30 | 1992-06-30 | Eastman Kodak Company | Alcohol-ester sparation by reaction with acetate |
JP3302120B2 (ja) | 1993-07-08 | 2002-07-15 | 関東化学株式会社 | レジスト用剥離液 |
US6083903A (en) * | 1994-10-28 | 2000-07-04 | Leukosite, Inc. | Boronic ester and acid compounds, synthesis and uses |
JP4853601B2 (ja) * | 2000-03-15 | 2012-01-11 | 日油株式会社 | グリセリン誘導体の製造方法 |
KR100360985B1 (ko) * | 2000-04-26 | 2002-11-18 | 주식회사 동진쎄미켐 | 레지스트 스트리퍼 조성물 |
JP4832955B2 (ja) | 2005-06-07 | 2011-12-07 | 信越化学工業株式会社 | レジスト下層膜材料並びにそれを用いたパターン形成方法 |
JP5288153B2 (ja) * | 2007-03-30 | 2013-09-11 | 日油株式会社 | 糖アルコール誘導体およびアルケニル基含有糖アルコール誘導体の製造方法 |
DE102007048937A1 (de) * | 2007-10-12 | 2009-04-16 | Evonik Degussa Gmbh | Entfernung von polaren organischen Verbindungen und Fremdmetallen aus Organosilanen |
JP2013032445A (ja) * | 2011-08-02 | 2013-02-14 | Nof Corp | 金属粉末スラリー |
JP6215777B2 (ja) | 2013-06-27 | 2017-10-18 | 信越化学工業株式会社 | 塗布型bpsg膜形成用組成物、該組成物で膜を形成した基板、及び前記組成物を用いたパターン形成方法 |
JP2015145353A (ja) * | 2014-02-04 | 2015-08-13 | 第一工業製薬株式会社 | 無水糖アルコールの精製方法、無水糖アルコール及び樹脂 |
JP6657642B2 (ja) | 2014-10-09 | 2020-03-04 | 三菱ケミカル株式会社 | 糖アルコールの製造方法および糖液 |
-
2016
- 2016-06-23 JP JP2016124209A patent/JP6681284B2/ja active Active
-
2017
- 2017-05-03 US US15/585,720 patent/US10131603B2/en active Active
- 2017-05-27 CN CN201710387797.9A patent/CN107540491B/zh active Active
- 2017-06-15 KR KR1020170075663A patent/KR20180000680A/ko active Search and Examination
- 2017-06-20 TW TW106120468A patent/TWI651296B/zh active
Also Published As
Publication number | Publication date |
---|---|
KR20180000680A (ko) | 2018-01-03 |
TW201811722A (zh) | 2018-04-01 |
JP2017226625A (ja) | 2017-12-28 |
CN107540491A (zh) | 2018-01-05 |
TWI651296B (zh) | 2019-02-21 |
CN107540491B (zh) | 2020-09-08 |
US10131603B2 (en) | 2018-11-20 |
US20170369407A1 (en) | 2017-12-28 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP4866237B2 (ja) | アダマンタン誘導体、その製造方法及びフォトレジスト用感光材料 | |
US20090156854A1 (en) | Adamantane derivatives and process for producing the same | |
JP2010265193A (ja) | アルキルクロルヒドリンエーテルの製造方法及びアルキルグリシジルエーテルの製造方法 | |
US8168809B2 (en) | 2-methyl-3-(3,4-methylenedioxyphenyl)propanal, and method for production thereof | |
JPWO2012033055A1 (ja) | ジトリメチロールプロパンの製造方法 | |
JP5092209B2 (ja) | 3,5−ジヒドロキシ−1−アダマンチルアクリレート類の製造方法 | |
JP6681284B2 (ja) | 糖アルコール化合物の金属低減方法 | |
CA2951930C (en) | Process for producing low voc coalescing aids | |
JP2005029563A (ja) | スピログリコールの製造方法 | |
CN113286802A (zh) | 高产率的血管渗漏阻断剂的制备方法 | |
JP2015030700A (ja) | エステル系溶剤の製造方法 | |
JP2005314383A (ja) | アダマンタン誘導体及びその製造方法 | |
JP4790290B2 (ja) | アダマンタン誘導体及びその製造方法 | |
TWI619705B (zh) | 烷二醇單縮水甘油醚(甲基)丙烯酸酯的製造方法 | |
TWI525084B (zh) | (甲基)丙烯酸縮水甘油酯及其製造方法 | |
WO2014034628A1 (ja) | 脂環式エポキシ化合物及びその製造方法 | |
JP2008297242A (ja) | 高純度アルキルアダマンチル(メタ)アクリレートの製造方法 | |
JPH04187682A (ja) | グリシジルアクリレート又はグリシジルメタクリレートの精製法 | |
CN104837803A (zh) | 碳酸酯化合物的制造方法 | |
JP5008311B2 (ja) | 六員環ラクトン(メタ)アクリル酸エステルの製造方法 | |
JP2004143087A (ja) | 光学活性2−アルコキシ−1−(トリフルオロメチル置換フェニル)エタノール誘導体の製造方法 | |
CN112592270A (zh) | 一种2-卤代-2,2-二氟乙酸烯酯的制备方法 | |
JP2018104379A (ja) | 2−メチル−2−ヒドロキシ−1−プロピル(メタ)アクリレートおよび/または3−メチル−3−ヒドロキシ−1−ブチル(メタ)アクリレートの製造方法ならびに組成物 | |
JP2010053057A (ja) | N,n−ジメチルカルバミン酸アルキルの製造方法 | |
JP2008143791A (ja) | ヒドロキシビニルナフタレン化合物の製造方法 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20180628 |
|
A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20190612 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20190702 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20190726 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20191224 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20200213 |
|
TRDD | Decision of grant or rejection written | ||
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20200303 |
|
A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20200323 |
|
R150 | Certificate of patent or registration of utility model |
Ref document number: 6681284 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 |