CN108026011A - The purification process of compound - Google Patents
The purification process of compound Download PDFInfo
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- CN108026011A CN108026011A CN201680051083.4A CN201680051083A CN108026011A CN 108026011 A CN108026011 A CN 108026011A CN 201680051083 A CN201680051083 A CN 201680051083A CN 108026011 A CN108026011 A CN 108026011A
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 79
- 238000000746 purification Methods 0.000 title claims abstract description 45
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 66
- 150000001491 aromatic compounds Chemical class 0.000 claims abstract description 47
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 42
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 42
- 125000003118 aryl group Chemical group 0.000 claims abstract description 25
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 22
- 238000000034 method Methods 0.000 claims abstract description 21
- 239000000203 mixture Substances 0.000 claims abstract description 21
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 20
- 239000002904 solvent Chemical class 0.000 claims abstract description 20
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims abstract description 14
- 125000001424 substituent group Chemical group 0.000 claims abstract description 13
- 239000004305 biphenyl Chemical group 0.000 claims abstract description 7
- 235000010290 biphenyl Nutrition 0.000 claims abstract description 7
- 125000001624 naphthyl group Chemical group 0.000 claims abstract description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 4
- 239000000463 material Substances 0.000 claims description 26
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 claims description 19
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 13
- 239000001301 oxygen Substances 0.000 claims description 13
- 229910052760 oxygen Inorganic materials 0.000 claims description 13
- 239000012528 membrane Substances 0.000 claims description 12
- 229920001721 polyimide Polymers 0.000 claims description 12
- 239000011651 chromium Substances 0.000 claims description 10
- 239000012510 hollow fiber Substances 0.000 claims description 10
- 239000004642 Polyimide Substances 0.000 claims description 9
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 claims description 8
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 claims description 8
- 238000001914 filtration Methods 0.000 claims description 8
- 229940043265 methyl isobutyl ketone Drugs 0.000 claims description 8
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 6
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 claims description 6
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 claims description 6
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims description 5
- 229910052804 chromium Inorganic materials 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 claims description 4
- 239000012298 atmosphere Substances 0.000 claims description 4
- QQZOPKMRPOGIEB-UHFFFAOYSA-N 2-Oxohexane Chemical compound CCCCC(C)=O QQZOPKMRPOGIEB-UHFFFAOYSA-N 0.000 claims description 3
- DFQICHCWIIJABH-UHFFFAOYSA-N naphthalene-2,7-diol Chemical compound C1=CC(O)=CC2=CC(O)=CC=C21 DFQICHCWIIJABH-UHFFFAOYSA-N 0.000 claims description 3
- 150000002576 ketones Chemical class 0.000 claims description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims 1
- 239000000243 solution Substances 0.000 description 54
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 29
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 23
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 16
- -1 dihydroxy naphthlene Chemical class 0.000 description 16
- 239000011148 porous material Substances 0.000 description 16
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- WURBVZBTWMNKQT-UHFFFAOYSA-N 1-(4-chlorophenoxy)-3,3-dimethyl-1-(1,2,4-triazol-1-yl)butan-2-one Chemical compound C1=NC=NN1C(C(=O)C(C)(C)C)OC1=CC=C(Cl)C=C1 WURBVZBTWMNKQT-UHFFFAOYSA-N 0.000 description 10
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- 239000004615 ingredient Substances 0.000 description 7
- 239000002994 raw material Substances 0.000 description 7
- 238000009835 boiling Methods 0.000 description 6
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 239000004677 Nylon Substances 0.000 description 5
- 229920006169 Perfluoroelastomer Polymers 0.000 description 5
- 239000004698 Polyethylene Substances 0.000 description 5
- 229920001778 nylon Polymers 0.000 description 5
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- 238000003756 stirring Methods 0.000 description 5
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- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 3
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- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 3
- 239000000284 extract Substances 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 239000011737 fluorine Substances 0.000 description 3
- 238000005342 ion exchange Methods 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
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- 238000000926 separation method Methods 0.000 description 3
- 238000006467 substitution reaction Methods 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 2
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- BPIUIOXAFBGMNB-UHFFFAOYSA-N 1-hexoxyhexane Chemical compound CCCCCCOCCCCCC BPIUIOXAFBGMNB-UHFFFAOYSA-N 0.000 description 2
- OJVAMHKKJGICOG-UHFFFAOYSA-N 2,5-hexanedione Chemical compound CC(=O)CCC(C)=O OJVAMHKKJGICOG-UHFFFAOYSA-N 0.000 description 2
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 2
- MSXVEPNJUHWQHW-UHFFFAOYSA-N 2-methylbutan-2-ol Chemical compound CCC(C)(C)O MSXVEPNJUHWQHW-UHFFFAOYSA-N 0.000 description 2
- ZPVFWPFBNIEHGJ-UHFFFAOYSA-N 2-octanone Chemical compound CCCCCCC(C)=O ZPVFWPFBNIEHGJ-UHFFFAOYSA-N 0.000 description 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 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
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
- ATHHXGZTWNVVOU-UHFFFAOYSA-N N-methylformamide Chemical compound CNC=O ATHHXGZTWNVVOU-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- JKRZOJADNVOXPM-UHFFFAOYSA-N Oxalic acid dibutyl ester Chemical compound CCCCOC(=O)C(=O)OCCCC JKRZOJADNVOXPM-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical group OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 2
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- 239000002253 acid Substances 0.000 description 2
- 150000001336 alkenes Chemical class 0.000 description 2
- QUKGYYKBILRGFE-UHFFFAOYSA-N benzyl acetate Chemical compound CC(=O)OCC1=CC=CC=C1 QUKGYYKBILRGFE-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical group OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 2
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 2
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- 238000006073 displacement reaction Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 2
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- VGVHNLRUAMRIEW-UHFFFAOYSA-N 4-methylcyclohexan-1-one Chemical compound CC1CCC(=O)CC1 VGVHNLRUAMRIEW-UHFFFAOYSA-N 0.000 description 1
- LPEKGGXMPWTOCB-UHFFFAOYSA-N 8beta-(2,3-epoxy-2-methylbutyryloxy)-14-acetoxytithifolin Natural products COC(=O)C(C)O LPEKGGXMPWTOCB-UHFFFAOYSA-N 0.000 description 1
- MRABAEUHTLLEML-UHFFFAOYSA-N Butyl lactate Chemical compound CCCCOC(=O)C(C)O MRABAEUHTLLEML-UHFFFAOYSA-N 0.000 description 1
- YYLLIJHXUHJATK-UHFFFAOYSA-N Cyclohexyl acetate Chemical compound CC(=O)OC1CCCCC1 YYLLIJHXUHJATK-UHFFFAOYSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- SUAKHGWARZSWIH-UHFFFAOYSA-N N,N‐diethylformamide Chemical class CCN(CC)C=O SUAKHGWARZSWIH-UHFFFAOYSA-N 0.000 description 1
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 1
- OHLUUHNLEMFGTQ-UHFFFAOYSA-N N-methylacetamide Chemical class CNC(C)=O OHLUUHNLEMFGTQ-UHFFFAOYSA-N 0.000 description 1
- 229920002302 Nylon 6,6 Polymers 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- YENIOYBTCIZCBJ-UHFFFAOYSA-N acetic acid;1-methoxypropan-2-ol Chemical compound CC(O)=O.COCC(C)O YENIOYBTCIZCBJ-UHFFFAOYSA-N 0.000 description 1
- FUECIDVNGAUMGJ-UHFFFAOYSA-N acetic acid;2-(2-butoxyethoxy)ethanol Chemical compound CC(O)=O.CCCCOCCOCCO FUECIDVNGAUMGJ-UHFFFAOYSA-N 0.000 description 1
- GTYLEVMOSBBKCQ-UHFFFAOYSA-N acetic acid;2-(2-ethoxyethoxy)ethanol Chemical compound CC(O)=O.CCOCCOCCO GTYLEVMOSBBKCQ-UHFFFAOYSA-N 0.000 description 1
- BGYBTGDDOPTJSB-UHFFFAOYSA-N acetic acid;ethane-1,2-diol Chemical compound CC(O)=O.OCCO BGYBTGDDOPTJSB-UHFFFAOYSA-N 0.000 description 1
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical class CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- HUFIRBOBXZUFPV-UHFFFAOYSA-N benzene-1,3-diol Chemical compound OC1=CC=CC(O)=C1.OC1=CC=CC(O)=C1 HUFIRBOBXZUFPV-UHFFFAOYSA-N 0.000 description 1
- 229940007550 benzyl acetate Drugs 0.000 description 1
- BTMVHUNTONAYDX-UHFFFAOYSA-N butyl propionate Chemical compound CCCCOC(=O)CC BTMVHUNTONAYDX-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 239000003729 cation exchange resin Substances 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 230000000295 complement effect Effects 0.000 description 1
- 230000003750 conditioning effect Effects 0.000 description 1
- 238000012790 confirmation Methods 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 150000001896 cresols Chemical class 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- FUGIIBWTNARRSF-UHFFFAOYSA-N decane-5,6-diol Chemical compound CCCCC(O)C(O)CCCC FUGIIBWTNARRSF-UHFFFAOYSA-N 0.000 description 1
- 229940019778 diethylene glycol diethyl ether Drugs 0.000 description 1
- 229940028356 diethylene glycol monobutyl ether Drugs 0.000 description 1
- XXJWXESWEXIICW-UHFFFAOYSA-N diethylene glycol monoethyl ether Chemical compound CCOCCOCCO XXJWXESWEXIICW-UHFFFAOYSA-N 0.000 description 1
- 229940075557 diethylene glycol monoethyl ether Drugs 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 150000004862 dioxolanes Chemical class 0.000 description 1
- POLCUAVZOMRGSN-UHFFFAOYSA-N dipropyl ether Chemical compound CCCOCCC POLCUAVZOMRGSN-UHFFFAOYSA-N 0.000 description 1
- ODQWQRRAPPTVAG-GZTJUZNOSA-N doxepin Chemical compound C1OC2=CC=CC=C2C(=C/CCN(C)C)/C2=CC=CC=C21 ODQWQRRAPPTVAG-GZTJUZNOSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 229940093858 ethyl acetoacetate Drugs 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 229940116333 ethyl lactate Drugs 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 229940074391 gallic acid Drugs 0.000 description 1
- 235000004515 gallic acid Nutrition 0.000 description 1
- 239000003292 glue Substances 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- NGAZZOYFWWSOGK-UHFFFAOYSA-N heptan-3-one Chemical compound CCCCC(=O)CC NGAZZOYFWWSOGK-UHFFFAOYSA-N 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 150000003949 imides Chemical class 0.000 description 1
- 230000008676 import Effects 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000001095 inductively coupled plasma mass spectrometry Methods 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 229910000765 intermetallic Inorganic materials 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- GJRQTCIYDGXPES-UHFFFAOYSA-N iso-butyl acetate Natural products CC(C)COC(C)=O GJRQTCIYDGXPES-UHFFFAOYSA-N 0.000 description 1
- WFKAJVHLWXSISD-UHFFFAOYSA-N isobutyramide Chemical class CC(C)C(N)=O WFKAJVHLWXSISD-UHFFFAOYSA-N 0.000 description 1
- FGKJLKRYENPLQH-UHFFFAOYSA-M isocaproate Chemical compound CC(C)CCC([O-])=O FGKJLKRYENPLQH-UHFFFAOYSA-M 0.000 description 1
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 1
- 229940011051 isopropyl acetate Drugs 0.000 description 1
- GWYFCOCPABKNJV-UHFFFAOYSA-M isovalerate Chemical compound CC(C)CC([O-])=O GWYFCOCPABKNJV-UHFFFAOYSA-M 0.000 description 1
- OQAGVSWESNCJJT-UHFFFAOYSA-N isovaleric acid methyl ester Natural products COC(=O)CC(C)C OQAGVSWESNCJJT-UHFFFAOYSA-N 0.000 description 1
- 238000005374 membrane filtration Methods 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- DKJCSMHIPYRALV-UHFFFAOYSA-N methoxymethyl propanoate Chemical compound CCC(=O)OCOC DKJCSMHIPYRALV-UHFFFAOYSA-N 0.000 description 1
- OJURWUUOVGOHJZ-UHFFFAOYSA-N methyl 2-[(2-acetyloxyphenyl)methyl-[2-[(2-acetyloxyphenyl)methyl-(2-methoxy-2-oxoethyl)amino]ethyl]amino]acetate Chemical compound C=1C=CC=C(OC(C)=O)C=1CN(CC(=O)OC)CCN(CC(=O)OC)CC1=CC=CC=C1OC(C)=O OJURWUUOVGOHJZ-UHFFFAOYSA-N 0.000 description 1
- 229940057867 methyl lactate Drugs 0.000 description 1
- 125000001421 myristyl 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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229940017144 n-butyl lactate Drugs 0.000 description 1
- QJQAMHYHNCADNR-UHFFFAOYSA-N n-methylpropanamide Chemical class CCC(=O)NC QJQAMHYHNCADNR-UHFFFAOYSA-N 0.000 description 1
- 229910017464 nitrogen compound Inorganic materials 0.000 description 1
- 150000002830 nitrogen compounds Chemical class 0.000 description 1
- 239000004745 nonwoven fabric Substances 0.000 description 1
- SJWFXCIHNDVPSH-UHFFFAOYSA-N octan-2-ol Chemical compound CCCCCCC(C)O SJWFXCIHNDVPSH-UHFFFAOYSA-N 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- JCGNDDUYTRNOFT-UHFFFAOYSA-N oxolane-2,4-dione Chemical compound O=C1COC(=O)C1 JCGNDDUYTRNOFT-UHFFFAOYSA-N 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- GXOHBWLPQHTYPF-UHFFFAOYSA-N pentyl 2-hydroxypropanoate Chemical compound CCCCCOC(=O)C(C)O GXOHBWLPQHTYPF-UHFFFAOYSA-N 0.000 description 1
- 229960005323 phenoxyethanol Drugs 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229920002239 polyacrylonitrile Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- CIBMHJPPKCXONB-UHFFFAOYSA-N propane-2,2-diol Chemical compound CC(C)(O)O CIBMHJPPKCXONB-UHFFFAOYSA-N 0.000 description 1
- 238000013094 purity test Methods 0.000 description 1
- 238000001226 reprecipitation Methods 0.000 description 1
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- 229940057402 undecyl alcohol Drugs 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D63/00—Apparatus in general for separation processes using semi-permeable membranes
- B01D63/02—Hollow fibre modules
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D63/00—Apparatus in general for separation processes using semi-permeable membranes
- B01D63/14—Pleat-type membrane modules
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D69/00—Semi-permeable membranes for separation processes or apparatus characterised by their form, structure or properties; Manufacturing processes specially adapted therefor
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D71/00—Semi-permeable membranes for separation processes or apparatus characterised by the material; Manufacturing processes specially adapted therefor
- B01D71/06—Organic material
- B01D71/26—Polyalkenes
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D71/00—Semi-permeable membranes for separation processes or apparatus characterised by the material; Manufacturing processes specially adapted therefor
- B01D71/06—Organic material
- B01D71/26—Polyalkenes
- B01D71/261—Polyethylene
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D71/00—Semi-permeable membranes for separation processes or apparatus characterised by the material; Manufacturing processes specially adapted therefor
- B01D71/06—Organic material
- B01D71/30—Polyalkenyl halides
- B01D71/32—Polyalkenyl halides containing fluorine atoms
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D71/00—Semi-permeable membranes for separation processes or apparatus characterised by the material; Manufacturing processes specially adapted therefor
- B01D71/06—Organic material
- B01D71/56—Polyamides, e.g. polyester-amides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/68—Purification; separation; Use of additives, e.g. for stabilisation
- C07C37/70—Purification; separation; Use of additives, e.g. for stabilisation by physical treatment
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C39/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
- C07C39/12—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic with no unsaturation outside the aromatic rings
- C07C39/14—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic with no unsaturation outside the aromatic rings with at least one hydroxy group on a condensed ring system containing two rings
Abstract
The purification process of the compound of the present invention includes making following formula (A0) and/or (B0) shown in hydroxyl substituted aromatic compound and solvent the process that circulates in the filter of solution.(previously described formula (A0) in, n0For 0~9 integer, m0For 0~2 integer, p0For 0~9 integer, herein, m0For 1 when, represent previously described formula (A0) there is naphthalene skeleton or biphenyl backbone, Ra is each independently the group selected in free hydroxyl, halogeno-group, the straight-chain of carbon number 1~40, branched or cricoid alkyl, the optionally group of the alkenyl and combinations thereof of the aryl of the carbon number 6~40 with substituent or carbon number 2~40 composition, and the alkyl, the aryl or the alkenyl optionally include ehter bond, ketonic bond or ester bond.Previously described formula (B0) in, n1For 0~9 integer, p1For 0~9 integer, Rb is each independently the group in the group being made of hydrogen atom, hydroxyl, halogeno-group, the straight-chain of carbon number 1~40, branched or cricoid alkyl, the aryl of carbon number 6~40 optionally with substituent or the alkenyl and combinations thereof of carbon number 2~40, and the alkyl, the aryl or the alkenyl optionally include ehter bond, ketonic bond or ester bond.)
Description
Technical field
The present invention relates to the purification process of compound (such as hydroxyl substituted aromatic compound).
Background technology
The hydroxyl such as dihydroxy naphthlene substituted aromatic compound is as the encapsulating material of semiconductor, smears, against corrosion
Agent with the raw material of material, the compound of semiconductor lower floor film formation material or resin be it is useful (referring for example to patent document 1~
2).In addition, the purification process as the hydroxyl substituted aromatic compound such as dihydroxy naphthlene, it is known to specific method (such as join
According to patent document 3).
Prior art literature
Patent document
Patent document 1:International Publication No. 2013/024778
Patent document 2:International Publication No. 2013/024779
Patent document 3:Chinese patent application discloses No. 103467249
The content of the invention
Problems to be solved by the invention
In such use, especially tenor is in order to which yield rate improves and becomes important performance evaluation project.That is, will
It is remaining in semiconductor hydroxyl substituted aromatic compound is as a large amount of metals are included in compound obtained from raw material or resin when
Metal and reduce the electrical characteristics of semiconductor, therefore it is required that reducing tenor as impurity.
Purifying as the tenor for reducing the compound obtained by hydroxyl substituted aromatic compound or resin
Method, considers following methods:Ion exchange water or pure is added in the mixture comprising the compound or resin and organic solvent
Water and the method that separation of solid and liquid is carried out after being recrystallized;Make the compound or resin in organic solvent arbitrarily not miscible with water
Middle dissolving, makes the solution be contacted with aqueous solution and carries out extraction process, metal ingredient is transferred to water phase, then by organic phase
The method that tenor is reduced with the liquid separation of water phase.
However, in the above-mentioned methods, when the high hydroxyl substituted aromatic compound of tenor is used as raw material, exist pair
The problem of removal effect of specific metal species is insufficient such.
Therefore, it is desirable to the hydroxyl substituted aromatic compound for establishing the high-purity that tenor reduces is industrially favourable
Purification process.
In addition, when the purity of hydroxyl substituted aromatic compound is low, exists and obtained by the hydroxyl substituted aromatic compound
Compound or resin yield reduce or occur deviation it is such the problem of.
And then do not studied on reducing tenor, the reduction of tenor is not in disclosed purification process in the past
Fully.
It is an object of the present invention to provide for industrially advantageously being purified to hydroxyl substituted aromatic compound
Method.
The solution used to solve the problem
The inventors of the present invention have made intensive studies in order to solve the above problems, it turns out that by making comprising hydroxyl substitution virtue
The solution of fragrant compounds of group and solvent circulates in the filter, can significantly reduce the content of the metal ingredient in the solution, so that
Complete the present invention.
That is, the present invention is as described below.
[1]
A kind of purification process of compound, it includes making to include following formula (A0) and/or (B0) shown in hydroxyl substituted aroma
The process that the solution of compounds of group and solvent circulates in the filter.
(previously described formula (A0) in, n0For 0~9 integer, m0For 0~2 integer, p0For 0~9 integer, herein, m0For 1
When, represent previously described formula (A0) there is naphthalene skeleton or biphenyl backbone, Ra be each independently select free hydroxyl, halogeno-group, carbon number 1~
40 straight-chain, branched or cricoid alkyl, the aryl of carbon number 6~40 or the alkene of carbon number 2~40 optionally with substituent
Group in the group of base and combinations thereof composition, the alkyl, the aryl or the alkenyl optionally include ehter bond, ketonic bond or ester
Key.Previously described formula (B0) in, n1For 0~9 integer, p1For 0~9 integer, Rb be each independently selected from by hydrogen atom, hydroxyl,
Halogeno-group, the straight-chain of carbon number 1~40, branched or cricoid alkyl, the optionally aryl of the carbon number 6~40 with substituent,
Or the group in the group of alkenyl and the combinations thereof composition of carbon number 2~40, the alkyl, the aryl or the alkenyl optionally include
Ehter bond, ketonic bond or ester bond.)
[2]
The purification process of compound according to claim 1, wherein, under foregoing hydroxy substituted aromatic compound is
State formula (A) and/or the compound shown in (B).
(in previously described formula (A), n0For 0~9 integer, m0For 0~2 integer, p0For 0~9 integer, herein, m0For 1
When, represent that previously described formula (A) has naphthalene skeleton or biphenyl backbone, R0Be each independently the straight-chain of carbon number 1~30, branched or
Cricoid alkyl, the aryl of carbon number 6~15 or the alkenyl of carbon number 2~15 optionally with substituent, in previously described formula (B), n1For
0~9 integer, p1For 0~9 integer, R1Be each independently carbon number 1~30 straight-chain, branched or cricoid alkyl,
Optionally there is the aryl of carbon number 6~15 or the alkenyl of carbon number 2~15 of substituent.)
[3]
The purification process of compound according to [1], wherein, foregoing hydroxy substituted aromatic compound is selected from following
The compound shown in compound, following formula (A-2) shown in formula (A-1), the compound shown in following formula (A-3), following formula (A-
4) more than a kind in the group of the compound composition shown in the compound and following formula (B-1) shown in.
(in previously described formula (A-1), n0For 0~5 integer, in previously described formula (A-2), n0For 0~7 integer, previously described formula (A-3)
In~(A-4), n0For 0~9 integer, in previously described formula (B-1), n1For 0~9 integer.)
[4]
The purification process of compound according to [1], wherein, foregoing hydroxy substituted aromatic compound is following formula
(1) compound shown in.
[5]
The purification process of compound according to [1], wherein, foregoing hydroxy substituted aromatic compound be selected from by 2,
More than a kind in the group of 6- dihydroxy naphthlenes and 2,7 dihydroxy naphthalene composition.
[6]
The purification process of compound according to any one of [1]~[5], wherein, the nominal pore of aforementioned filter
Footpath is less than 1.0 μm.
[7]
The purification process of compound according to any one of [1]~[6], wherein, aforementioned filter be selected from by
More than a kind in the group of hollow fiber membrane filter, molecular filter and fold film filter composition.
[8]
The purification process of compound according to any one of [1]~[7], wherein, the filter material of aforementioned filter
Expect for more than a kind in the group being made of polyimides system, vistanex system and fluororesin system.
[9]
The purification process of compound according to any one of [1]~[8], wherein, aforementioned filter includes ion
Permutoid.
[10]
The purification process of compound according to any one of [1]~[9], wherein, aforementioned filter, which includes, to be had
The material of Zeta potential.
[11]
The purification process of compound according to any one of [1]~[10], wherein, aforementioned solvents are selected from by vinegar
Acetoacetic ester, butyl acetate, methyl iso-butyl ketone (MIBK), propylene glycol monomethyl ether, propylene glycol monomethyl ether acetate, cyclopentanone and cyclohexanone
More than a kind in the group of composition.
[12]
The purification process of compound according to any one of [1]~[11], wherein, the preparation of previous solu and stream
Lead in atmosphere of the oxygen concentration less than 20% and carry out.
[13]
The purification process of compound according to any one of [1]~[12], wherein, substitute relative to foregoing hydroxy
The quality of aromatic compound, the content of contained chromium is reduced for below 50ppb in previous solu.
The effect of invention
According to the present invention it is possible to industrially advantageously hydroxyl substituted aromatic compound is purified.
Embodiment
Hereinafter, embodiments of the present invention (are also denoted as " present embodiment " below.) be described in detail.Need to illustrate
, implementation below is the illustration for illustrating the present invention, and the present invention is not limited to these embodiments.
The purification process of the compound of present embodiment includes making to include following formula (A0) and/or (B0) shown in hydroxyl take
The process to circulate in the filter for the solution of aromatic compound and solvent.Due to forming as described above, pass through this
The purification process of the compound of embodiment, industrially advantageously can purify hydroxyl substituted aromatic compound.
Especially, as be described hereinafter shown in embodiment, on the content of chromium (Cr) contained in dihydroxy naphthlene solution, relative to the dihydroxy naphthlene
Quality can be reduced to below 50ppb.
It can be total to as described above, " purifying " in present embodiment refers to fully reduce with hydroxyl substituted aromatic compound
The operation for the metal ingredient deposited, specifically, obtain Na amounts be below 50ppb, Fe amounts are below 60ppb, Cr amounts be 70ppb with
Under and Sn amounts be below 50ppb hydroxyl substituted aromatic compound.In present embodiment, preferably after purification can be with
The Na amounts that hydroxyl substituted aromatic compound coexists are below 50ppb, Fe amounts are below 50ppb, Cr amounts be below 50ppb, with
And Sn amounts are below 50ppb.The method that these metal ingredient amounts can be recorded with aftermentioned embodiment measures.
It should be noted that " circulation " in present embodiment refers to above-mentioned solution outside filter by the filter
It is internal and again to moving outside filter, for example, make state that above-mentioned solution is only in contact in filter surfaces, make it is above-mentioned
Solution is in contact state (that is, the shape being only in contact while being moved outside ion exchange resin on a surface on one side
State) be except.
(previously described formula (A0) in, n0For 0~9 integer, m0For 0~2 integer, p0For 0~9 integer, herein, m0For 1
When, represent previously described formula (A0) there is naphthalene skeleton or biphenyl backbone, Ra be each independently select free hydroxyl, halogeno-group, carbon number 1~
40 straight-chain, branched or cricoid alkyl, the aryl of carbon number 6~40 or the alkene of carbon number 2~40 optionally with substituent
Group in the group of base and combinations thereof composition, the alkyl, the aryl or the alkenyl optionally include ehter bond, ketonic bond or ester
Key.Previously described formula (B0) in, n1For 0~9 integer, p1For 0~9 integer, Rb be each independently selected from by hydrogen atom, hydroxyl,
Halogeno-group, the straight-chain of carbon number 1~40, branched or cricoid alkyl, the optionally aryl of the carbon number 6~40 with substituent,
Or the group in the group of alkenyl and the combinations thereof composition of carbon number 2~40, the alkyl, the aryl or the alkenyl optionally include
Ehter bond, ketonic bond or ester bond.)
In the purification process of the compound of present embodiment, from the viewpoint of the supply of raw material, foregoing hydroxy substitution
Aromatic compound is more preferably following formula (A) and/or the compound shown in (B).
(in previously described formula (A), n0For 0~9 integer, m0For 0~2 integer, p0For 0~9 integer, herein, m0For 1
When, represent that previously described formula (A) has naphthalene skeleton or biphenyl backbone, R0Be each independently the straight-chain of carbon number 1~30, branched or
Cricoid alkyl, the aryl of carbon number 6~15 or the alkenyl of carbon number 2~15 optionally with substituent, in previously described formula (B), n1For
0~9 integer, p1For 0~9 integer, R1 be each independently carbon number 1~30 straight-chain, branched or cricoid alkyl,
Optionally there is the aryl of carbon number 6~15 or the alkenyl of carbon number 2~15 of substituent.)
In the purification process of the compound of present embodiment, from the viewpoint of the dissolubility to organic solvent, foregoing hydroxyl
Base substituted aromatic compound is more preferably selected from as shown in the compound shown in following formula (A-1), following formula (A-2)
The change shown in the compound and following formula (B-1) shown in compound, following formula (A-4) shown in compound, following formula (A-3)
More than a kind in the group of compound composition.
(in previously described formula (A-1), n0For 0~5 integer, in previously described formula (A-2), n0For 0~7 integer, previously described formula (A-3)
In~(A-4), n0For 0~9 integer, in previously described formula (B-1), n1For 0~9 integer.)
In the purification process of the compound of present embodiment, from the sight of the dissolubility to organic solvent and the kettle efficiency of purifying
From the point of view of point, foregoing hydroxy substituted aromatic compound is particularly preferably the compound shown in following formula (1).
Herein, to the compound shown in above-mentioned formula (1), there is no particular limitation, from the viewpoint of the supply of raw material,
Be preferably selected from by 1,2- dihydroxy naphthlenes, 1,3- dihydroxy naphthlenes, 1,4- dihydroxy naphthlenes, 1,5- dihydroxy naphthlenes, 1,6- dihydroxy naphthlenes,
In the group that 1,7- dihydroxy naphthlenes, 1,8- dihydroxy naphthlenes, 2,3- dihydroxy naphthlenes, 2,6- dihydroxy naphthlenes and 2,7 dihydroxy naphthalene form
More than a kind.
In addition, had no particular limits to the compound shown in above-mentioned formula (1), from using the compound shown in formula (1) as
From the viewpoint of compound obtained from raw material or the heat resistance of resin, more preferably it is selected from by 2,6- dihydroxy naphthlenes and 2,7- bis-
More than a kind in the group of hydroxyl naphthalene composition.
Compound shown in above-mentioned formula (1) is had no particular limits, from using the compound shown in formula (1) as raw material and
It is more preferably 2,6- dihydroxy naphthlenes from the viewpoint of obtained compound or the further heat resistance of resin.
The hydroxyl substituted aromatic compound used in present embodiment can be by known to manufacturer and reagent business etc.
Means are readily available.Furthermore it is possible to suitably be synthesized using known gimmick, synthesizing gimmick to it is not particularly limited.
The hydroxyl substituted aromatic compound used in present embodiment can also individually mix two or more.In addition,
Hydroxyl substituted aromatic compound can contain various surfactants, various crosslinking agents, various acid agents, various stabilizers
Deng.
As the solvent used in present embodiment, there is no particular limitation, preferably can be with safety applications in semiconductor system
Make the organic solvent of technique.From the viewpoint of the easy degree of solid recycling from deliquescent raising and after purification, preferably make
The amount of solvent is usually 1~100 mass times relative to the compound shown in the formula (1) used.More preferably 5~50 mass
Times, more preferably 10~50 mass are again.
As the specific example of the solvent used in present embodiment, it is not limited to following, can includes:It is ether, different
Propyl ether, n-butyl ether, hexyl ether, 2- ethylhexyls ether, ethylene oxide, 1,2 epoxy prapane, dioxolanes, 4- methyl dioxolanes,
Dioxane, dimethyl dioxane, glycol monoethyl ether, ethylene glycol monoethyl ether, ethylene glycol diethyl ether, ethylene glycol monobutyl ether,
Ethylene glycol list n-hexyl ether, ethyleneglycol monophenylether, ethylene glycol list -2- ethyl-butyls ether, butyl cellosolve, diethylene glycol list first
Ether, diethylene glycol monoethyl ether, diethylene glycol diethyl ether, diethylene glycol monobutyl ether, dibutyl ethylene glycol ether, diethylene glycol list just oneself
Ether, ethoxytriglycol, tetraethylene glycol butyl oxide, propylene glycol monomethyl ether (PGME), dipropylene glycol methyl ether, tripropylene glycol first
The ethers such as ether, propylene glycol monopropyl ether, tetrahydrofuran, 2- methyltetrahydrofurans, methanol, ethanol, normal propyl alcohol, isopropanol, n-butanol,
Isobutanol, sec-butyl alcohol, the tert-butyl alcohol, n-amyl alcohol, isoamyl alcohol, 2- methyl butanols, sec-amyl alcohol, tert-pentyl alcohol, 3- methoxybutanols, just oneself
Alcohol, 2- methyl anyl alcohols, secondary hexyl alcohol, 2- ethyl butanols, secondary enanthol, 3- enanthol, n-octyl alcohol, 2-Ethylhexyl Alcohol, sec-octyl alcohol, nonyl alcohol,
2,6- 2,6-dimethyl-4-heptanols, Decanol, secondary undecyl alcohol, Exxal 12, secondary tetradecyl alchohol, secondary heptadecanol, phenol, cyclohexanol, first
The unary alcohol such as cyclohexanol, 3,3,5- cyclonols, benzylalcohol, phenyl methyl carbitol, diacetone alcohol, cresols, carbonic acid
The positive fourth of diethylester, methyl acetate, ethyl acetate, gamma-butyrolacton, gamma-valerolactone, n-propyl acetate, isopropyl acetate, acetic acid
The secondary pentyl ester of ester, isobutyl acetate, sec-Butyl Acetate, n-Amyl acetate, acetic acid, acetic acid 3- methoxybutyls, acetic acid methyl pentyl ester,
Acetic acid 2- ethyls butyl ester, acetic acid 2- ethylhexyls, benzyl acetate, cyclohexyl acetate, methyl cyclohexanol acetate, acetic acid nonyl ester, second
Acyl methyl acetate, ethyl acetoacetate, acetic acid glycol monoethyl ether, acetic acid ethylene glycol monoethyl ether, acetic acid propylene glycol monomethyl ether, vinegar
Acid diethylene glycol monomethyl ether, acetic acid diethylene glycol monoethyl ether, acetic acid diethylene glycol monobutyl ether, two acetic acid ethylene glycol, acetic acid methoxy
Base triethylene glycol, ethyl propionate, n-butyl propionate, isoamyl propionate, methoxy methyl propionate, ethoxyl ethyl propionate, oxalic acid two
Ethyl ester, dibutyl oxalate, methyl lactate, ethyl lactate, n-butyl lactate, N_amyl lactate, diethyl malonate, adjacent benzene two
The esters such as formic acid dimethyl ester, diethyl phthalate, acetone, methyl ethyl ketone, methyl n-propyl ketone, methyl n-butyl ketone, diethyl
Ketone, methyl iso-butyl ketone (MIBK), Methylpentanone, ethyl butyl ketone, methyl hexyl ketone, diisobutyl ketone, trimethyl nonanone, cyclohexanone,
The ketones such as methyl cyclohexanone, 2,4- pentanediones, acetonyl acetone, acetophenone, 1-methyl-2-pyrrolidinone, ethylene glycol monoethyl ether acetic acid
The glycol ethers vinegar such as ester, ethylene glycol monomethyl ether acetate, propylene glycol monomethyl ether acetate (PGMEA), dihydroxypropane single-ether acetate
Esters of gallic acid, N-METHYLFORMAMIDE, n,N-Dimethylformamide, N, N- diethylformamides, acetamide, N- methylacetamides, N,
The fat such as nitrogen compound series solvent, n-hexane, normal heptane such as N- dimethylacetylamides, N- methyl propanamides, 1-methyl-2-pyrrolidinone
Halogenated hydrocarbons such as aromatic hydrocarbon, dichloromethane, the chloroforms such as fat race hydro carbons, toluene, dimethylbenzene etc..
Above-mentioned solvent can be used individually, can also mix two or more use.
Among above-mentioned, from the viewpoint of operability, the management easy degree of inventory, it is preferably selected from by acetic acid second
Ester, butyl acetate, methyl iso-butyl ketone (MIBK), propylene glycol monomethyl ether (PGME), propylene glycol monomethyl ether acetate (PGMEA), cyclopentanone
With more than a kind in the group of cyclohexanone composition.
During circulation in the present embodiment, for removing in the solution comprising hydroxyl substituted aromatic compound and solvent
Metal ingredient filter can usually use as liquid filtering use and commercially available filter.To the filtering accuracy of filter
There is no particular limitation, and the normal pore size of filter is preferably smaller than 1.0 μm, more preferably less than 0.2 μm, more preferably
Less than 0.05 μm.In addition, to the lower limit of the normal pore size of filter, there is no particular limitation, is usually 0.005 μm.This place
The normal pore size said refers to represent the aperture on the item of the separating property of filter, for example, passes through bubble point test, mercury injection method
The apertures definite by the test method(s) that the manufacturer of filter determines such as experiment, standard particle complementary testing.During using commercially available product,
For the value described in the catalogue data of manufacturer.By the way that normal pore size is set smaller than 1.0 μm, existing more effectively to drop
The low solution for making hydroxyl substituted aromatic compound circulate in the filter 1 time after metal ingredient content tendency.Especially,
In the presence of can make the content of chromium (Cr) relative to the quality of hydroxyl substituted aromatic compound be reduced to preferably below 50ppb,
The tendency of more preferably below 20ppb, more preferably below 5ppb.In present embodiment, in order to further reduce hydroxyl
The content of each metal ingredient of the solution of substituted aromatic compound, can carry out circulating for more than 2 times.
As the form of filter, it is not limited to following, such as can uses using hollow fiber membrane filter, membrane filtration
Device, fold film filter and it is filled with filter of the filtering materials such as non-woven fabrics, cellulose and diatomite etc..Especially from height
Fine filtering accuracy and other forms compare the high degree of filter area and set out, and filter is preferably selected from by hollow-fibre membrane
More than a kind in the group of filter, molecular filter and fold film filter composition, more preferably using hollow fiber membrane filter.
The material of above-mentioned filter is not limited to following, such as can include:The vistanexes such as polyethylene, polypropylene
The fluorine-containing trees such as the resin-mades of the polar functionalities such as system, polyimide resin system, polyester, polyacrylonitrile, fluorinated polyethylene (PTFE)
Fat system.In present embodiment, from the viewpoint of heat resistance and solvent resistance, the filtering material of filter is preferably selected from by gathering
More than a kind in the group of imide resin system, vistanex system and fluororesin system composition, more preferably polyimide resin
System.
As polyimides system filter, (being below trade mark) is not limited to following, such as can include:KITZ
The Polyfix nylon series of MICRO FILTER CORPORATION manufactures, NIHON PALL LTD. are manufactured
Ultipleat P-nylon66, Ultipore N66, the Life ASSURE PSN series of 3M Company manufactures, Life
ASSURE EF series etc..
As polyolefin filter, it is not limited to following, such as can includes:NIHON PALL LTD. manufactures
Ultipleat PEclean, Microgard Plus HC10, the Optimizer of Entegris Japan Co., Ltd. manufactures
D etc..
As fluororesin system filter, it is not limited to following, such as NIHON PALL LTD. manufactures can be included
Life ASSURE FA series of Emflon HTPFR, 3M Company manufacture etc..
These filters can be used individually, can also combine two or more use.
In addition, in above-mentioned filter can include cation exchange resin plasma permutoid, make to be filtered it is organic molten
Agent solution produces cationic charge conditioning agent of Zeta potential etc..Such as:As including polyimides polyamine epichlorohydrin cation
Resin etc. has the filter (being below trade mark) of the material of positive Zeta potential, is not limited to following, such as can include
Zeta plus40QSH, the Zeta plus020GN of 3M Company manufactures or Life ASSURE EF series etc..
Especially for the material as effective filter for reducing the heavy metals such as chromium (Cr), tin (Sn) it is preferred that polyamides is sub-
The reasons why polyimide resin, can include:The absorption property of metal is excellent.On the absorption property of the metal of filter material, Ke Yitong
Cross the sheet material (hereinafter referred to as " base material " of measure and filter phase same material.) with make foregoing hydroxy substituted compound dissolving form it is molten
The contact angle of liquid simultaneously compares the reduction behavior of the metal and confirms.Specifically, it is smaller with the contact angle of base material, solution and filtering
Device wettability of the surface becomes higher,, also can be into even if the filtering accuracy of filter is identical compared with the big base material of contact angle
One step reduces the metal.
As comprising the hydroxyl substituted aromatic compound in present embodiment and the solution of solvent and the contact angle of base material,
Preferably 1 °~40 ° of scope, more preferably 1 °~30 °, more preferably 1 °~20 °.Contact angle is 1 °~40 ° of scope
When, it is abundant to the wetability of base material, exist to obtain the tendency of good adsorption properties.
In addition, at least one of the seal member such as O-ring that the jointing of filter, shell are included is by perfluor rubber
Glue, Perfluoroelastomer form, preferably these member of formation all by selected from fluorine resin, perfluoroelastomer, Perfluoroelastomer material
Material is formed.Further, above-mentioned seal member is particularly preferably made of the material selected from perfluoroelastomer, Perfluoroelastomer.It is only sharp
The containing ratio of the metallic compound in hydroxyl substituted aromatic compound cannot be reduced to ppb sometimes with the component beyond these
It is horizontal.
When temperature when the preparation and circulation of the solution of hydroxyl substituted aromatic compound is excessive, there is the kind according to solvent
Class and the tendency for producing hydrolysis, volatile acid is free state sometimes, therefore not preferably, when too low, there are hydroxyl substitution virtue
The tendency that the solubility of fragrant compounds of group diminishes.In this way, from the viewpoint for preventing volatile sour free viewpoint and efficiency
From the point of view of, temperature is preferably adjusted, usually can be set as 0~40 DEG C, is preferably 5~30 DEG C, more preferably 10~25 DEG C.
It should be noted that in present embodiment, purified hydroxyl substituted aromatic is obtained except through above-mentioned circulation
Beyond the process of compound, further purification procedures can also be included.
Mixed moisture can pass through in the so obtained solution for including hydroxyl substituted aromatic compound and solvent
Implement the operation such as vacuum distillation and be readily removable.Furthermore it is possible to add solvent as needed and by hydroxyl substituted aromatic
The concentration of compound is adjusted to any concentration.
To only obtaining hydroxyl substituted aromatic compound from the solution comprising hydroxyl substituted aromatic compound and solvent
There is no particular limitation for method, such as can utilize known in decompression removal, the separation based on reprecipitation and combinations thereof etc.
Method carry out.Concentration operation, filter operation can be carried out as needed, centrifuged known to operation, drying process etc.
Processing.
The preparation and circulation of the solution comprising hydroxyl substituted aromatic compound and solvent in present embodiment preferably exist
Oxygen concentration carries out under the atmosphere less than 20%.Oxygen concentration is more preferably less than 10%, is further preferably no larger than 5%, particularly preferably small
In 1%.By making oxygen concentration be less than 20%, there is the rotten tendency for further suppressing hydroxyl substituted aromatic compound, deposit
In the tendency for the hydroxyl substituted aromatic compound for obtaining higher purity.
Allow oxygen concentration reduce method implemented with known method, there is no particular limitation, for example, can by
Nitrogen or decompression are blown into the column or kettle that are purified and imports nitrogen afterwards to carry out gas displacement.To the column or kettle purified
It is preferable that nitrogen is imported after decompression at easy and reliable aspect.
The confirmation of oxygen concentration can be implemented with known method, and there is no particular limitation, such as:It can purified
Nitrogen is blown into kettle, the oxygen concentration for the gas discharged with oxymeter measure by venthole.Alternatively, it is also possible to purified
Oxymeter is set in kettle.
Embodiment
Hereinafter, enumerate embodiment and further illustrate present embodiment.But present embodiment is not limited to these realities
Apply example.
(embodiment 1)
In the clean space of rank 1000, in the four-hole boiling flask (bottom detachable type) of 1000mL capacity, addition makes
The 2,6- dihydroxy naphthlenes of organic purity 99.3% (are also referred to as 2,6-DHN below.) it is dissolved in what propylene glycol monomethyl ether (PGME) formed
Solution (2.5 mass % of concentration) 500g, then decompression remove kettle inner air, are then introduced into nitrogen until recovering to atmospheric pressure,
Under the nitrogen ventilation of every point of 100mL, internal oxygen concentration is adjusted to after less than 1%, is stirred while being heated to 30 DEG C.
Removed with vacuum pump pressure from bottom valve opening underface up to the air of the terminal of filter liquid flow line, then from bottom valve opening
Extract 2,6-DHN solution out, via the pressure pipe of fluororesin, using diaphragm pump using the flow of every point of 100mL normal pore size as
0.01 μm of polyimides hollow fiber membrane filter (KITZ MICRO FILTER CORPORATION manufactures, trade name:
Polyfix nylon series) in circulation.Obtained 2,6-DHN solution is analyzed under the following conditions.Need what is illustrated
It is that oxygen concentration is measured (below similarly using the oxymeter " OM-25MF10 " of ASONE manufactures.).
(embodiment 2)
Use polyethylene hollow fiber membrane filter (the KITZ MICRO FILTER that normal pore size is 0.01 μm
CORPORATION manufactures, trade name:Polyfix), in addition, circulate similarly to Example 1,2 obtained, 6-DHN is molten
Liquid is analyzed under the following conditions.
(embodiment 3)
Use polyimides hollow fiber membrane filter (the KITZ MICRO FILTER that normal pore size is 0.05 μm
CORPORATION manufactures, trade name:Polyfix), in addition, circulate similarly to Example 1,2 obtained, 6-DHN is molten
Liquid is analyzed under the following conditions.
(embodiment 4)
Filter (NIHON PALL LTD. manufactures, trade name are film-made using the polyethylene that normal pore size is 0.05 μm:
Ultipleat PEclean), in addition, circulate similarly to Example 1, by obtained 2,6-DHN solution under the following conditions
Analyzed.
(embodiment 5)
Filter (Millipore (strain) systems, trade name are film-made using the PTFE that normal pore size is 0.05 μm:Omnipore),
In addition, circulate similarly to Example 1, obtained 2,6-DHN solution is analyzed under the following conditions.
(embodiment 6)
Using the Zeta plus filter 40QSH that normal pore size is 0.2 μm, (3M Company manufactures, have ion exchange
Ability), in addition, circulate similarly to Example 1, obtained 2,6-DHN solution is analyzed under the following conditions.
(embodiment 7)
Using the Zeta plus filter 020GN that normal pore size is 0.2 μm, (3M Company manufactures, have ion exchange
Ability), in addition, circulate similarly to Example 1, obtained 2,6-DHN solution is analyzed under the following conditions.
(embodiment 8) is without nitrogen gas displacement
In the clean space of rank 1000, being added in the four-hole boiling flask (bottom detachable type) of 1000mL capacity makes to have
2,6-DHN of machine purity 99.3% is dissolved in solution (2.5 mass % of concentration) 500g that PGME is formed, and stirs while heating
To 30 DEG C.2,6-DHN solution is extracted out from bottom valve opening, via the pressure pipe of fluororesin, using diaphragm pump with the stream of every point of 100mL
Measure polyimides hollow fiber membrane filter (the KITZ MICRO FILTER for being 0.01 μm in normal pore size
CORPORATION manufactures, trade name:Polyfix nylon series) in circulation.By obtained 2,6-DHN solution in following conditions
Under analyzed.
(embodiment 9)
In the clean space of rank 1000, in the four-hole boiling flask (bottom detachable type) of 1000mL capacity, addition makes
2,6-DHN of organic purity 99.3% is dissolved in solution (2.5 mass % of concentration) 500g that PGME is formed, and then decompression removes kettle
Inner air, is then introduced into nitrogen and recovers to atmospheric pressure, and under the nitrogen ventilation of every point of 100mL, internal oxygen concentration is adjusted
To after being less than 1%, stir while being heated to 30 DEG C.2,6-DHN solution is extracted out from bottom valve opening, via the pressure-resistant of fluororesin
Pipe, filter (NIHON PALL are film-made using diaphragm pump in normal pore size using the flow of every point of 100mL as 1.0 μm of polyethylene
LTD. manufacture, trade name:Ultipleat PEclean) in circulation.By obtained 2,6-DHN solution under the following conditions into
Row analysis.
(embodiment 10)
In the clean space of rank 1000, in the four-hole boiling flask (bottom detachable type) of 1000mL capacity, addition makes
2,6-DHN of organic purity 99.3% is dissolved in solution (2.5 mass % of concentration) 500g that PGME is formed, and then decompression removes kettle
Inner air, is then introduced into nitrogen and recovers to atmospheric pressure, and under the nitrogen ventilation of every point of 100mL, internal oxygen concentration is adjusted
To after 5.0%, stir while being heated to 30 DEG C.Removed with vacuum pump pressure immediately below the valve opening of bottom up to filter liquid
The air of the terminal of flow line, then extracts 2,6-DHN solution out from bottom valve opening, via the pressure pipe of fluororesin, using every
Membrane pump using the flow of every point of 100mL in normal pore size as 0.01 μm of polyimides hollow fiber membrane filter (KITZ
MICRO FILTER CORPORATION manufactures, trade name:Polyfix nylon series) in circulation.The 2,6-DHN that will be obtained
Solution is analyzed under the following conditions.
(embodiment 11)
In the clean space of rank 1000, in the four-hole boiling flask (bottom detachable type) of 1000mL capacity, addition makes
2,6-DHN of organic purity 99.3% is dissolved in solution (2.5 mass % of concentration) 500g that PGME is formed, and then decompression removes kettle
Inner air, is then introduced into nitrogen and recovers to atmospheric pressure, and under the nitrogen ventilation of every point of 100mL, internal oxygen concentration is adjusted
To after 10.0%, stir while being heated to 30 DEG C.Removed with vacuum pump pressure immediately below the valve opening of bottom up to filter liquid
The air of the terminal of body flow line, then extracts 2,6-DHN solution out from bottom valve opening, via the pressure pipe of fluororesin, utilizes
Diaphragm pump using the flow of every point of 100mL in normal pore size as 0.01 μm of polyimides hollow fiber membrane filter (KITZ
MICRO FILTER CORPORATION manufactures, trade name:Polyfix nylon series) in circulation.The 2,6-DHN that will be obtained
Solution is analyzed under the following conditions.
(comparative example 1) circulates without filter
In the clean space of rank 1000, in the four-hole boiling flask (bottom detachable type) of 1000mL capacity, addition makes
2,6-DHN of organic purity 99.3% is dissolved in solution (2.5 mass % of concentration) 500g that PGME is formed, and then decompression removes kettle
Internal air, is then introduced into nitrogen and recovers to atmospheric pressure, under the nitrogen ventilation of every point of 100mL, stirs while heating
To 30 DEG C.2,6-DHN solution is extracted out from bottom valve opening, via the pressure pipe of fluororesin, using diaphragm pump with the stream of every point of 100mL
Amount is recycled in fluorine resin container.The 2,6-DHN solution of recycling is analyzed under the following conditions.
(embodiment 12)
Change 2,6-DHN, using 4, the 4- xenols of purity 99.2%, in addition, circulate similarly to Example 1, will
Obtained purification solution is analyzed under the following conditions.
(embodiment 13)
Change 2,6-DHN, it is in addition, same with embodiment 1 using the resorcinol (Resorcinol) of purity 99.1%
Sample circulates, and obtained solution is analyzed under the following conditions.
(embodiment 14)
Change 2,6-DHN, using 9, the 10- dihydroxy-anthracenes of purity 98.7%, in addition, circulate similarly to Example 1,
Obtained solution is analyzed under the following conditions.
(embodiment 15)
Change 2,6-DHN, using the 1- hydroxyl pyrenes of purity 98.8%, in addition, circulate similarly to Example 1, will
To solution analyzed under the following conditions.
2,6-DHN's to the PGME solution of 2,6-DHN that is obtained in embodiment 1~11 and comparative example 1 and before purification
PGME solution (2.5 mass % of concentration), measures various tenors and organic purity.In addition, in embodiment 1~5, prepare by
The sheet test film (2cm × 5cm) for 100 μ m-thicks that the material identical with filter is formed, carries out the sheet test film and purifying
The contact angle determination of the PGME solution (2.5 mass % of concentration) of preceding 2,6-DHN.Measurement result is shown in table 1.
Further, to obtained in embodiment 12~15 before purification after various hydroxyl substituted compounds PGME solution,
Measure various tenors and organic purity.In addition, prepare the sheet examination of 100 μ m-thicks being made of the material identical with filter
Piece (2cm × 5cm) is tested, carries out the PGME solution (concentration 2.5 of the sheet test film and various hydroxyl substituted compounds before purification
Quality %) contact angle determination.Measurement result is shown in table 2.
It should be noted that in an example in office, as " purifying before the solution of preparation will be circulated to filter
Before ", by the solution at the time point for said determination.
Each measure carries out under following device and determination condition.
[various tenor measure]
Using ICP-MS, the various tenors of 2,6-DHN are measured under following determination condition.
Device:ELAN DRCII (PerkinElmer Co., Ltd manufacture)
Temperature:25℃
Environment:100 toilet of rank
[organic purity testing]
Organic purity of 2,6-DHN is measured under following determination condition using high performance liquid chromatography.
Device:GL-7400 types (Hitachi's system)
Column:X-BRIDE C18
Eluent:Acetonitrile/water
Temperature:40℃
[contact angle determination]
Measured using contact angle meter under following determination condition the PGME solution of 2,6-DHN and each hydroxyl substituted compound with
The contact angle of each sheet material.
Device:The CA-Smicro2 types of Kyowa Interface Science Co., LTD manufactures
Measure gimmick:Sessile drop method
Atmosphere:In air
Determination of the environment:23 DEG C/50%RH
[table 1]
[table 2]
The application is based on Japanese patent application (Japanese Patent Application 2015-174635) filed in September in 2015 4 days, in it
Hold and be incorporated herein as reference.
Industrial applicability
According to the present invention it is possible to industrially advantageously be purified to hydroxyl substituted aromatic compound, can be made
The hydroxyl substituted aromatic compound that tenor reduces.
Claims (13)
1. a kind of purification process of compound, it includes making to include following formula (A0) and/or (B0) shown in hydroxyl substituted aromatic
The process that the solution of compound and solvent circulates in the filter,
Formula (the A0) in, n0For 0~9 integer, m0For 0~2 integer, p0For 0~9 integer, herein, m0For 1 when, represent
Formula (the A0) there is naphthalene skeleton or biphenyl backbone, Ra be each independently select free hydroxyl, halogeno-group, carbon number 1~40 it is straight
Chain, branched or cricoid alkyl, optionally with substituent the aryl of carbon number 6~40 or the alkenyl of carbon number 2~40 and
Group in the group of combinations thereof composition, the alkyl, the aryl or the alkenyl optionally include ehter bond, ketonic bond or ester bond;It is described
Formula (B0) in, n1For 0~9 integer, p1For 0~9 integer, Rb be each independently selected from by hydrogen atom, hydroxyl, halogeno-group,
The aryl or carbon number 2 of straight-chain, branched or the cricoid alkyl of carbon number 1~40, the optionally carbon number 6~40 with substituent
Group in the group of~40 alkenyl and combinations thereof composition, the alkyl, the aryl or the alkenyl are optionally comprising ehter bond, ketone
Key or ester bond.
2. the purification process of compound according to claim 1, wherein, the hydroxyl substituted aromatic compound is following
Formula (A) and/or the compound shown in (B),
In the formula (A), n0For 0~9 integer, m0For 0~2 integer, p0For 0~9 integer, herein, m0For 1 when, represent
The formula (A) has naphthalene skeleton or biphenyl backbone, R0It is each independently straight-chain, the branched or cricoid of carbon number 1~30
Alkyl, the aryl of carbon number 6~15 or the alkenyl of carbon number 2~15 optionally with substituent, in the formula (B), n1For 0~9
Integer, p1For 0~9 integer, R1It is each independently straight-chain, branched or the cricoid alkyl of carbon number 1~30, optionally has
The aryl of the carbon number 6~15 of substituted base or the alkenyl of carbon number 2~15.
3. the purification process of compound according to claim 1, wherein, the hydroxyl substituted aromatic compound be selected from
It is the compound shown in compound, following formula (A-2) shown in following formula (A-1), the compound shown in following formula (A-3), following
More than a kind in the group of compound composition shown in compound and following formula (B-1) shown in formula (A-4),
In the formula (A-1), n0For 0~5 integer, in the formula (A-2), n0For 0~7 integer, formula (A-3)~(A-
4) in, n0For 0~9 integer, in the formula (B-1), n1For 0~9 integer.
4. the purification process of compound according to claim 1, wherein, the hydroxyl substituted aromatic compound is following
Compound shown in formula (1),
5. the purification process of compound according to claim 1, wherein, the hydroxyl substituted aromatic compound be selected from
More than a kind in the group be made of 2,6- dihydroxy naphthlenes and 2,7 dihydroxy naphthalene.
6. the purification process of the compound according to any one of Claims 1 to 5, wherein, the filter it is nominal
Aperture is less than 1.0 μm.
7. the purification process of the compound according to any one of claim 1~6, wherein, the filter be selected from
More than a kind in the group be made of hollow fiber membrane filter, molecular filter and fold film filter.
8. the purification process of the compound according to any one of claim 1~7, wherein, the filtering of the filter
Material is more than a kind in the group being made of polyimides system, vistanex system and fluororesin system.
9. the purification process of the compound according to any one of claim 1~8, wherein, the filter include from
Sub- permutoid.
10. the purification process of the compound according to any one of claim 1~9, wherein, the filter includes tool
There is the material of Zeta potential.
11. the purification process of the compound according to any one of claim 1~10, wherein, the solvent be selected from
By ethyl acetate, butyl acetate, methyl iso-butyl ketone (MIBK), propylene glycol monomethyl ether, propylene glycol monomethyl ether acetate, cyclopentanone and ring
More than a kind in the group of hexanone composition.
12. the purification process of the compound according to any one of claim 1~11, wherein, the preparation of the solution
Carried out with circulation in atmosphere of the oxygen concentration less than 20%.
13. the purification process of the compound according to any one of claim 1~12, wherein, relative to the hydroxyl
The quality of substituted aromatic compound, the content of contained chromium is reduced for below 50ppb in the solution.
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JP7306790B2 (en) | 2023-07-11 |
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