TWI831913B - 由廢物流製造鹽之方法 - Google Patents
由廢物流製造鹽之方法 Download PDFInfo
- Publication number
- TWI831913B TWI831913B TW109103105A TW109103105A TWI831913B TW I831913 B TWI831913 B TW I831913B TW 109103105 A TW109103105 A TW 109103105A TW 109103105 A TW109103105 A TW 109103105A TW I831913 B TWI831913 B TW I831913B
- Authority
- TW
- Taiwan
- Prior art keywords
- salt
- organic
- aqueous
- layer
- peroxide
- Prior art date
Links
- 150000003839 salts Chemical class 0.000 title claims abstract description 68
- 238000000034 method Methods 0.000 title claims abstract description 36
- 230000008569 process Effects 0.000 title claims abstract description 18
- 239000002699 waste material Substances 0.000 title description 8
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims abstract description 35
- 239000012044 organic layer Substances 0.000 claims abstract description 26
- 239000010410 layer Substances 0.000 claims abstract description 25
- 239000007788 liquid Substances 0.000 claims abstract description 23
- 239000011780 sodium chloride Substances 0.000 claims abstract description 18
- 238000004519 manufacturing process Methods 0.000 claims abstract description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 34
- -1 peroxyester Chemical compound 0.000 claims description 15
- 239000008346 aqueous phase Substances 0.000 claims description 14
- 239000002002 slurry Substances 0.000 claims description 13
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 9
- 230000020477 pH reduction Effects 0.000 claims description 9
- 239000003960 organic solvent Substances 0.000 claims description 8
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 claims description 7
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 4
- KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 claims description 4
- BEQKKZICTDFVMG-UHFFFAOYSA-N 1,2,3,4,6-pentaoxepane-5,7-dione Chemical compound O=C1OOOOC(=O)O1 BEQKKZICTDFVMG-UHFFFAOYSA-N 0.000 claims description 3
- FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 claims description 3
- 238000001704 evaporation Methods 0.000 claims description 3
- 230000008020 evaporation Effects 0.000 claims description 3
- 150000002432 hydroperoxides Chemical class 0.000 claims description 3
- MMCOUVMKNAHQOY-UHFFFAOYSA-L oxido carbonate Chemical compound [O-]OC([O-])=O MMCOUVMKNAHQOY-UHFFFAOYSA-L 0.000 claims description 3
- 239000012855 volatile organic compound Substances 0.000 claims description 3
- XRXANEMIFVRKLN-UHFFFAOYSA-N 2-hydroperoxy-2-methylbutane Chemical compound CCC(C)(C)OO XRXANEMIFVRKLN-UHFFFAOYSA-N 0.000 claims description 2
- 239000007864 aqueous solution Substances 0.000 claims description 2
- IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 claims description 2
- RSPISYXLHRIGJD-UHFFFAOYSA-N OOOO Chemical compound OOOO RSPISYXLHRIGJD-UHFFFAOYSA-N 0.000 claims 1
- 150000001451 organic peroxides Chemical class 0.000 abstract description 12
- 239000000203 mixture Substances 0.000 description 35
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
- 238000002425 crystallisation Methods 0.000 description 18
- 230000008025 crystallization Effects 0.000 description 18
- NIQCNGHVCWTJSM-UHFFFAOYSA-N Dimethyl phthalate Chemical compound COC(=O)C1=CC=CC=C1C(=O)OC NIQCNGHVCWTJSM-UHFFFAOYSA-N 0.000 description 14
- 239000000243 solution Substances 0.000 description 13
- 238000011020 pilot scale process Methods 0.000 description 12
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 11
- 239000013078 crystal Substances 0.000 description 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- 238000005119 centrifugation Methods 0.000 description 6
- FBSAITBEAPNWJG-UHFFFAOYSA-N dimethyl phthalate Natural products CC(=O)OC1=CC=CC=C1OC(C)=O FBSAITBEAPNWJG-UHFFFAOYSA-N 0.000 description 6
- 229960001826 dimethylphthalate Drugs 0.000 description 6
- 238000000926 separation method Methods 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 238000005406 washing Methods 0.000 description 6
- 239000005711 Benzoic acid Substances 0.000 description 5
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 5
- 235000010233 benzoic acid Nutrition 0.000 description 5
- 235000019400 benzoyl peroxide Nutrition 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 5
- 239000005416 organic matter Substances 0.000 description 5
- 239000012074 organic phase Substances 0.000 description 5
- 150000002978 peroxides Chemical group 0.000 description 5
- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 5
- 239000004299 sodium benzoate Substances 0.000 description 5
- 235000010234 sodium benzoate Nutrition 0.000 description 5
- 150000001735 carboxylic acids Chemical class 0.000 description 4
- 238000000605 extraction Methods 0.000 description 4
- 239000012535 impurity Substances 0.000 description 4
- LPNBBFKOUUSUDB-UHFFFAOYSA-N p-toluic acid Chemical compound CC1=CC=C(C(O)=O)C=C1 LPNBBFKOUUSUDB-UHFFFAOYSA-N 0.000 description 4
- 238000001556 precipitation Methods 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- XKXIQBVKMABYQJ-UHFFFAOYSA-M tert-butyl carbonate Chemical compound CC(C)(C)OC([O-])=O XKXIQBVKMABYQJ-UHFFFAOYSA-M 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- 239000004808 2-ethylhexylester Substances 0.000 description 3
- MSXVEPNJUHWQHW-UHFFFAOYSA-N 2-methylbutan-2-ol Chemical compound CCC(C)(C)O MSXVEPNJUHWQHW-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 3
- 239000001692 EU approved anti-caking agent Substances 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 238000004065 wastewater treatment Methods 0.000 description 3
- LGJCFVYMIJLQJO-UHFFFAOYSA-N 1-dodecylperoxydodecane Chemical compound CCCCCCCCCCCCOOCCCCCCCCCCCC LGJCFVYMIJLQJO-UHFFFAOYSA-N 0.000 description 2
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 2
- ZACVGCNKGYYQHA-UHFFFAOYSA-N 2-ethylhexoxycarbonyloxy 2-ethylhexyl carbonate Chemical compound CCCCC(CC)COC(=O)OOC(=O)OCC(CC)CCCC ZACVGCNKGYYQHA-UHFFFAOYSA-N 0.000 description 2
- RIQSLGAADRJNSG-UHFFFAOYSA-N 2-ethylhexoxycarbonyloxyperoxy 2-ethylhexyl carbonate Chemical compound CCCCC(CC)COC(=O)OOOOC(=O)OCC(CC)CCCC RIQSLGAADRJNSG-UHFFFAOYSA-N 0.000 description 2
- TVWBTVJBDFTVOW-UHFFFAOYSA-N 2-methyl-1-(2-methylpropylperoxy)propane Chemical compound CC(C)COOCC(C)C TVWBTVJBDFTVOW-UHFFFAOYSA-N 0.000 description 2
- DZRUNSUYJCQUIG-UHFFFAOYSA-N 2-methylbutan-2-yl hydrogen carbonate Chemical compound CCC(C)(C)OC(O)=O DZRUNSUYJCQUIG-UHFFFAOYSA-N 0.000 description 2
- HIIFQZPOXXTXGY-UHFFFAOYSA-N 2-methylpropyl ethaneperoxoate Chemical compound CC(C)COOC(C)=O HIIFQZPOXXTXGY-UHFFFAOYSA-N 0.000 description 2
- GTJOHISYCKPIMT-UHFFFAOYSA-N 2-methylundecane Chemical compound CCCCCCCCCC(C)C GTJOHISYCKPIMT-UHFFFAOYSA-N 0.000 description 2
- QPIRYFWCAHUZTB-UHFFFAOYSA-N 3,5,5-trimethyl-1-(3,5,5-trimethylhexylperoxy)hexane Chemical compound CC(C)(C)CC(C)CCOOCCC(C)CC(C)(C)C QPIRYFWCAHUZTB-UHFFFAOYSA-N 0.000 description 2
- CARSMBZECAABMO-UHFFFAOYSA-N 3-chloro-2,6-dimethylbenzoic acid Chemical compound CC1=CC=C(Cl)C(C)=C1C(O)=O CARSMBZECAABMO-UHFFFAOYSA-N 0.000 description 2
- SGVYKUFIHHTIFL-UHFFFAOYSA-N Isobutylhexyl Natural products CCCCCCCC(C)C SGVYKUFIHHTIFL-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 2
- 239000012267 brine Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000005260 corrosion Methods 0.000 description 2
- 230000007797 corrosion Effects 0.000 description 2
- 125000002592 cumenyl group Chemical group C1(=C(C=CC=C1)*)C(C)C 0.000 description 2
- 239000012933 diacyl peroxide Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 230000005484 gravity Effects 0.000 description 2
- VKPSKYDESGTTFR-UHFFFAOYSA-N isododecane Natural products CC(C)(C)CC(C)CC(C)(C)C VKPSKYDESGTTFR-UHFFFAOYSA-N 0.000 description 2
- 239000010985 leather Substances 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 235000005985 organic acids Nutrition 0.000 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
- 125000005634 peroxydicarbonate group Chemical group 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000010926 purge Methods 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 235000012247 sodium ferrocyanide Nutrition 0.000 description 2
- VYPDUQYOLCLEGS-UHFFFAOYSA-M sodium;2-ethylhexanoate Chemical compound [Na+].CCCCC(CC)C([O-])=O VYPDUQYOLCLEGS-UHFFFAOYSA-M 0.000 description 2
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- NMOALOSNPWTWRH-UHFFFAOYSA-N tert-butyl 7,7-dimethyloctaneperoxoate Chemical compound CC(C)(C)CCCCCC(=O)OOC(C)(C)C NMOALOSNPWTWRH-UHFFFAOYSA-N 0.000 description 2
- 239000004753 textile Substances 0.000 description 2
- ZICNIEOYWVIEQJ-UHFFFAOYSA-N (2-methylbenzoyl) 2-methylbenzenecarboperoxoate Chemical compound CC1=CC=CC=C1C(=O)OOC(=O)C1=CC=CC=C1C ZICNIEOYWVIEQJ-UHFFFAOYSA-N 0.000 description 1
- AGKBXKFWMQLFGZ-UHFFFAOYSA-N (4-methylbenzoyl) 4-methylbenzenecarboperoxoate Chemical compound C1=CC(C)=CC=C1C(=O)OOC(=O)C1=CC=C(C)C=C1 AGKBXKFWMQLFGZ-UHFFFAOYSA-N 0.000 description 1
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- PAOHAQSLJSMLAT-UHFFFAOYSA-N 1-butylperoxybutane Chemical compound CCCCOOCCCC PAOHAQSLJSMLAT-UHFFFAOYSA-N 0.000 description 1
- OMMGZSUKFYZRCV-UHFFFAOYSA-N 1-decylperoxydecane Chemical compound CCCCCCCCCCOOCCCCCCCCCC OMMGZSUKFYZRCV-UHFFFAOYSA-N 0.000 description 1
- ZHKBLALOBMBJLL-UHFFFAOYSA-N 1-hexylperoxyhexane Chemical compound CCCCCCOOCCCCCC ZHKBLALOBMBJLL-UHFFFAOYSA-N 0.000 description 1
- FFHGJCBXRQUCED-UHFFFAOYSA-N 1-methyl-2-(2-methylphenyl)peroxybenzene Chemical compound CC1=CC=CC=C1OOC1=CC=CC=C1C FFHGJCBXRQUCED-UHFFFAOYSA-N 0.000 description 1
- KEFKGTYAXAQBCF-UHFFFAOYSA-N 1-methyl-4-[(4-methylphenyl)methylperoxymethyl]benzene Chemical compound C1=CC(C)=CC=C1COOCC1=CC=C(C)C=C1 KEFKGTYAXAQBCF-UHFFFAOYSA-N 0.000 description 1
- LWRXNMLZNDYFAW-UHFFFAOYSA-N 1-octylperoxyoctane Chemical compound CCCCCCCCOOCCCCCCCC LWRXNMLZNDYFAW-UHFFFAOYSA-N 0.000 description 1
- ZKEUVTROUPQVTM-UHFFFAOYSA-N 1-pentylperoxypentane Chemical compound CCCCCOOCCCCC ZKEUVTROUPQVTM-UHFFFAOYSA-N 0.000 description 1
- MUOYRBYBTJDAOT-UHFFFAOYSA-N 2,4,4-trimethylpentan-2-yl 2,2-dimethylpropaneperoxoate Chemical compound CC(C)(C)CC(C)(C)OOC(=O)C(C)(C)C MUOYRBYBTJDAOT-UHFFFAOYSA-N 0.000 description 1
- MSIJNEPFXZFULB-UHFFFAOYSA-N 2,4,4-trimethylpentan-2-yl 2-methylpropaneperoxoate Chemical compound CC(C)C(=O)OOC(C)(C)CC(C)(C)C MSIJNEPFXZFULB-UHFFFAOYSA-N 0.000 description 1
- XTJYGTVCDMNODS-UHFFFAOYSA-N 2,4,4-trimethylpentan-2-yl 7,7-dimethyloctaneperoxoate Chemical compound CC(C)(C)CCCCCC(=O)OOC(C)(C)CC(C)(C)C XTJYGTVCDMNODS-UHFFFAOYSA-N 0.000 description 1
- KFKWOVMTRULHKC-UHFFFAOYSA-N 2,4,4-trimethylpentan-2-yl hydrogen carbonate Chemical compound CC(C)(C)CC(C)(C)OC(O)=O KFKWOVMTRULHKC-UHFFFAOYSA-N 0.000 description 1
- DPGYCJUCJYUHTM-UHFFFAOYSA-N 2,4,4-trimethylpentan-2-yloxy 2-ethylhexaneperoxoate Chemical compound CCCCC(CC)C(=O)OOOC(C)(C)CC(C)(C)C DPGYCJUCJYUHTM-UHFFFAOYSA-N 0.000 description 1
- AQKYLAIZOGOPAW-UHFFFAOYSA-N 2-methylbutan-2-yl 2,2-dimethylpropaneperoxoate Chemical compound CCC(C)(C)OOC(=O)C(C)(C)C AQKYLAIZOGOPAW-UHFFFAOYSA-N 0.000 description 1
- KLILDKXSRNDFKB-UHFFFAOYSA-N 2-methylbutan-2-yl 2-methylpropaneperoxoate Chemical compound CCC(C)(C)OOC(=O)C(C)C KLILDKXSRNDFKB-UHFFFAOYSA-N 0.000 description 1
- RFSCGDQQLKVJEJ-UHFFFAOYSA-N 2-methylbutan-2-yl benzenecarboperoxoate Chemical compound CCC(C)(C)OOC(=O)C1=CC=CC=C1 RFSCGDQQLKVJEJ-UHFFFAOYSA-N 0.000 description 1
- FSGAMPVWQZPGJF-UHFFFAOYSA-N 2-methylbutan-2-yl ethaneperoxoate Chemical compound CCC(C)(C)OOC(C)=O FSGAMPVWQZPGJF-UHFFFAOYSA-N 0.000 description 1
- WGNABEIXVJEKIE-UHFFFAOYSA-N 2-propylheptoxycarbonyloxy 2-propylheptyl carbonate Chemical compound CCCCCC(CCC)COC(OOC(OCC(CCC)CCCCC)=O)=O WGNABEIXVJEKIE-UHFFFAOYSA-N 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- XYFRHHAYSXIKGH-UHFFFAOYSA-N 3-(5-methoxy-2-methoxycarbonyl-1h-indol-3-yl)prop-2-enoic acid Chemical compound C1=C(OC)C=C2C(C=CC(O)=O)=C(C(=O)OC)NC2=C1 XYFRHHAYSXIKGH-UHFFFAOYSA-N 0.000 description 1
- KIXBHBIAUACDNJ-UHFFFAOYSA-N 3-chloro-2-methylhexane Chemical compound CCCC(Cl)C(C)C KIXBHBIAUACDNJ-UHFFFAOYSA-N 0.000 description 1
- DLKXCEVTKBSHKK-UHFFFAOYSA-N 3-methyl-1-(3-methylbutylperoxy)butane Chemical compound CC(C)CCOOCCC(C)C DLKXCEVTKBSHKK-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
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- 239000004342 Benzoyl peroxide Substances 0.000 description 1
- FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 description 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
- PYGXAGIECVVIOZ-UHFFFAOYSA-N Dibutyl decanedioate Chemical compound CCCCOC(=O)CCCCCCCCC(=O)OCCCC PYGXAGIECVVIOZ-UHFFFAOYSA-N 0.000 description 1
- VIZORQUEIQEFRT-UHFFFAOYSA-N Diethyl adipate Chemical class CCOC(=O)CCCCC(=O)OCC VIZORQUEIQEFRT-UHFFFAOYSA-N 0.000 description 1
- UDSFAEKRVUSQDD-UHFFFAOYSA-N Dimethyl adipate Chemical compound COC(=O)CCCCC(=O)OC UDSFAEKRVUSQDD-UHFFFAOYSA-N 0.000 description 1
- 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 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- OXHZXVHTGNBKTG-UHFFFAOYSA-N acetyl cyclohexanecarboperoxoate Chemical compound CC(=O)OOC(=O)C1CCCCC1 OXHZXVHTGNBKTG-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- MTZQAGJQAFMTAQ-UHFFFAOYSA-N benzoic acid ethyl ester Natural products CCOC(=O)C1=CC=CC=C1 MTZQAGJQAFMTAQ-UHFFFAOYSA-N 0.000 description 1
- ZFMQKOWCDKKBIF-UHFFFAOYSA-N bis(3,5-difluorophenyl)phosphane Chemical compound FC1=CC(F)=CC(PC=2C=C(F)C=C(F)C=2)=C1 ZFMQKOWCDKKBIF-UHFFFAOYSA-N 0.000 description 1
- FBQZJBMRDNLFQO-UWVGGRQHSA-N bis[(3S)-3-methoxybutyl] ethanediperoxoate Chemical compound CO[C@@H](C)CCOOC(=O)C(=O)OOCC[C@H](C)OC FBQZJBMRDNLFQO-UWVGGRQHSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- DTGWMJJKPLJKQD-UHFFFAOYSA-N butyl 2,2-dimethylpropaneperoxoate Chemical compound CCCCOOC(=O)C(C)(C)C DTGWMJJKPLJKQD-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000012824 chemical production Methods 0.000 description 1
- 238000003843 chloralkali process Methods 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- YQHLDYVWEZKEOX-UHFFFAOYSA-N cumene hydroperoxide Chemical compound OOC(C)(C)C1=CC=CC=C1 YQHLDYVWEZKEOX-UHFFFAOYSA-N 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- JBSLOWBPDRZSMB-FPLPWBNLSA-N dibutyl (z)-but-2-enedioate Chemical compound CCCCOC(=O)\C=C/C(=O)OCCCC JBSLOWBPDRZSMB-FPLPWBNLSA-N 0.000 description 1
- 239000002283 diesel fuel Substances 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- WIGIXKBUJWOGQR-UHFFFAOYSA-N dodecyl ethaneperoxoate Chemical compound C(CCCCCCCCCCC)OOC(C)=O WIGIXKBUJWOGQR-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 230000004720 fertilization Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000005188 flotation Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- QWVBGCWRHHXMRM-UHFFFAOYSA-N hexadecoxycarbonyloxy hexadecyl carbonate Chemical compound CCCCCCCCCCCCCCCCOC(=O)OOC(=O)OCCCCCCCCCCCCCCCC QWVBGCWRHHXMRM-UHFFFAOYSA-N 0.000 description 1
- QDYCXRGMMICPCC-UHFFFAOYSA-N hexyl ethaneperoxoate Chemical compound CCCCCCOOC(C)=O QDYCXRGMMICPCC-UHFFFAOYSA-N 0.000 description 1
- 125000001145 hydrido group Chemical group *[H] 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- UETZVSHORCDDTH-UHFFFAOYSA-N iron(2+);hexacyanide Chemical compound [Fe+2].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-] UETZVSHORCDDTH-UHFFFAOYSA-N 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 239000010808 liquid waste Substances 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 230000009965 odorless effect Effects 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- WPPLKRDOKPISSC-UHFFFAOYSA-N pentyl 2,2-dimethylpropaneperoxoate Chemical compound CCCCCOOC(=O)C(C)(C)C WPPLKRDOKPISSC-UHFFFAOYSA-N 0.000 description 1
- ZLAJWQIJAVXCAT-UHFFFAOYSA-N pentyl 7,7-dimethyloctaneperoxoate Chemical compound CCCCCOOC(=O)CCCCCC(C)(C)C ZLAJWQIJAVXCAT-UHFFFAOYSA-N 0.000 description 1
- 125000000864 peroxy group Chemical group O(O*)* 0.000 description 1
- 150000004978 peroxycarbonates Chemical class 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 125000005498 phthalate group Chemical class 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- IWZKICVEHNUQTL-UHFFFAOYSA-M potassium hydrogen phthalate Chemical compound [K+].OC(=O)C1=CC=CC=C1C([O-])=O IWZKICVEHNUQTL-UHFFFAOYSA-M 0.000 description 1
- BWJUFXUULUEGMA-UHFFFAOYSA-N propan-2-yl propan-2-yloxycarbonyloxy carbonate Chemical compound CC(C)OC(=O)OOC(=O)OC(C)C BWJUFXUULUEGMA-UHFFFAOYSA-N 0.000 description 1
- KNNLWVUFUIAFJW-UHFFFAOYSA-N propyl benzenecarboperoxoate Chemical compound CCCOOC(=O)C1=CC=CC=C1 KNNLWVUFUIAFJW-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000011833 salt mixture Substances 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 238000004062 sedimentation Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- WBHQBSYUUJJSRZ-UHFFFAOYSA-M sodium bisulfate Chemical compound [Na+].OS([O-])(=O)=O WBHQBSYUUJJSRZ-UHFFFAOYSA-M 0.000 description 1
- 229910000342 sodium bisulfate Inorganic materials 0.000 description 1
- GTSHREYGKSITGK-UHFFFAOYSA-N sodium ferrocyanide Chemical compound [Na+].[Na+].[Na+].[Na+].[Fe+2].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-] GTSHREYGKSITGK-UHFFFAOYSA-N 0.000 description 1
- CASCCINXYVTVRI-UHFFFAOYSA-M sodium;7,7-dimethyloctanoate Chemical compound [Na+].CC(C)(C)CCCCCC([O-])=O CASCCINXYVTVRI-UHFFFAOYSA-M 0.000 description 1
- FOTNEEVHXTXVFX-UHFFFAOYSA-M sodium;benzenecarboperoxoate Chemical compound [Na+].[O-]OC(=O)C1=CC=CC=C1 FOTNEEVHXTXVFX-UHFFFAOYSA-M 0.000 description 1
- 235000015096 spirit Nutrition 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- WYKYCHHWIJXDAO-UHFFFAOYSA-N tert-butyl 2-ethylhexaneperoxoate Chemical compound CCCCC(CC)C(=O)OOC(C)(C)C WYKYCHHWIJXDAO-UHFFFAOYSA-N 0.000 description 1
- PFBLRDXPNUJYJM-UHFFFAOYSA-N tert-butyl 2-methylpropaneperoxoate Chemical compound CC(C)C(=O)OOC(C)(C)C PFBLRDXPNUJYJM-UHFFFAOYSA-N 0.000 description 1
- GJBRNHKUVLOCEB-UHFFFAOYSA-N tert-butyl benzenecarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1 GJBRNHKUVLOCEB-UHFFFAOYSA-N 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F9/00—Multistage treatment of water, waste water or sewage
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01D—COMPOUNDS OF ALKALI METALS, i.e. LITHIUM, SODIUM, POTASSIUM, RUBIDIUM, CAESIUM, OR FRANCIUM
- C01D3/00—Halides of sodium, potassium or alkali metals in general
- C01D3/04—Chlorides
- C01D3/06—Preparation by working up brines; seawater or spent lyes
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D11/00—Solvent extraction
- B01D11/04—Solvent extraction of solutions which are liquid
- B01D11/0446—Juxtaposition of mixers-settlers
- B01D11/0461—Juxtaposition of mixers-settlers mixing by counter-current streams provoked by centrifugal force
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D11/00—Solvent extraction
- B01D11/04—Solvent extraction of solutions which are liquid
- B01D11/0492—Applications, solvents used
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D9/00—Crystallisation
- B01D9/0004—Crystallisation cooling by heat exchange
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D9/00—Crystallisation
- B01D9/0018—Evaporation of components of the mixture to be separated
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D17/00—Separation of liquids, not provided for elsewhere, e.g. by thermal diffusion
- B01D17/02—Separation of non-miscible liquids
- B01D17/0205—Separation of non-miscible liquids by gas bubbles or moving solids
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D17/00—Separation of liquids, not provided for elsewhere, e.g. by thermal diffusion
- B01D17/02—Separation of non-miscible liquids
- B01D17/0208—Separation of non-miscible liquids by sedimentation
- B01D17/0214—Separation of non-miscible liquids by sedimentation with removal of one of the phases
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D17/00—Separation of liquids, not provided for elsewhere, e.g. by thermal diffusion
- B01D17/02—Separation of non-miscible liquids
- B01D17/04—Breaking emulsions
- B01D17/047—Breaking emulsions with separation aids
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D2257/00—Components to be removed
- B01D2257/70—Organic compounds not provided for in groups B01D2257/00 - B01D2257/602
- B01D2257/708—Volatile organic compounds V.O.C.'s
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D3/00—Distillation or related exchange processes in which liquids are contacted with gaseous media, e.g. stripping
- B01D3/34—Distillation or related exchange processes in which liquids are contacted with gaseous media, e.g. stripping with one or more auxiliary substances
- B01D3/38—Steam distillation
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01P—INDEXING SCHEME RELATING TO STRUCTURAL AND PHYSICAL ASPECTS OF SOLID INORGANIC COMPOUNDS
- C01P2006/00—Physical properties of inorganic compounds
- C01P2006/80—Compositional purity
- C01P2006/82—Compositional purity water content
-
- C—CHEMISTRY; METALLURGY
- C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F1/00—Treatment of water, waste water, or sewage
- C02F1/02—Treatment of water, waste water, or sewage by heating
- C02F1/04—Treatment of water, waste water, or sewage by heating by distillation or evaporation
- C02F1/041—Treatment of water, waste water, or sewage by heating by distillation or evaporation by means of vapour compression
-
- C—CHEMISTRY; METALLURGY
- C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F1/00—Treatment of water, waste water, or sewage
- C02F1/02—Treatment of water, waste water, or sewage by heating
- C02F1/04—Treatment of water, waste water, or sewage by heating by distillation or evaporation
- C02F1/048—Purification of waste water by evaporation
-
- C—CHEMISTRY; METALLURGY
- C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F1/00—Treatment of water, waste water, or sewage
- C02F1/20—Treatment of water, waste water, or sewage by degassing, i.e. liberation of dissolved gases
-
- C—CHEMISTRY; METALLURGY
- C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F1/00—Treatment of water, waste water, or sewage
- C02F1/24—Treatment of water, waste water, or sewage by flotation
-
- C—CHEMISTRY; METALLURGY
- C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F1/00—Treatment of water, waste water, or sewage
- C02F1/26—Treatment of water, waste water, or sewage by extraction
-
- C—CHEMISTRY; METALLURGY
- C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F1/00—Treatment of water, waste water, or sewage
- C02F1/40—Devices for separating or removing fatty or oily substances or similar floating material
-
- C—CHEMISTRY; METALLURGY
- C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F1/00—Treatment of water, waste water, or sewage
- C02F1/66—Treatment of water, waste water, or sewage by neutralisation; pH adjustment
-
- C—CHEMISTRY; METALLURGY
- C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F1/00—Treatment of water, waste water, or sewage
- C02F1/52—Treatment of water, waste water, or sewage by flocculation or precipitation of suspended impurities
- C02F2001/5218—Crystallization
-
- C—CHEMISTRY; METALLURGY
- C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F2101/00—Nature of the contaminant
- C02F2101/10—Inorganic compounds
- C02F2101/12—Halogens or halogen-containing compounds
-
- C—CHEMISTRY; METALLURGY
- C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F2101/00—Nature of the contaminant
- C02F2101/30—Organic compounds
- C02F2101/34—Organic compounds containing oxygen
-
- C—CHEMISTRY; METALLURGY
- C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F2103/00—Nature of the water, waste water, sewage or sludge to be treated
- C02F2103/34—Nature of the water, waste water, sewage or sludge to be treated from industrial activities not provided for in groups C02F2103/12 - C02F2103/32
- C02F2103/36—Nature of the water, waste water, sewage or sludge to be treated from industrial activities not provided for in groups C02F2103/12 - C02F2103/32 from the manufacture of organic compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Crystallography & Structural Chemistry (AREA)
- Materials Engineering (AREA)
- Inorganic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Environmental & Geological Engineering (AREA)
- Water Supply & Treatment (AREA)
- Hydrology & Water Resources (AREA)
- Physics & Mathematics (AREA)
- Thermal Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Removal Of Floating Material (AREA)
Abstract
本發明係關於由來自一或多個有機過氧化物製造方法之水性流出物製造包含NaCl及/或KCl之鹽的方法,該方法包含以下步驟:(a) 確保該等水性流出物之pH在範圍1-5中,(b) 將該等流出物分成液體有機層及水層,(c) 去除該有機層,(d)使該水層之pH升高至在範圍6-14中之值,及(e) 使該鹽自pH在範圍6-14中之該水層結晶。
Description
本發明係關於由化學製造方法流出物、更具體而言有機過氧化物製造流出物製造鹽、更具體而言含NaCl及/或KCl之鹽之方法。
各種有機過氧化物(例如二醯基過氧化物、過氧酯及過氧二碳酸酯)之製造涉及醯氯或氯甲酸酯與有機氫過氧化物或H2
O2
在鹼性條件下之反應。端視特定方法而定,鹼性條件係藉由添加NaOH、KOH或其組合獲得。
作為副產物,形成大量鹽(KCl及/或NaCl)。亦可存在其他鹽,例如Na2
SO4
。高鹽濃度通常使得不允許水性含鹽流出物直接處理至生物廢水處理單元。
代之以稀釋流出物,自環境及經濟角度來看,更具吸引力的係將鹽以可在其他方法(例如紡織品製造、皮革鞣製或氯鹼方法)中使用之形式分離。
鹽可藉由習用蒸發結晶回收。然而,在此一系統中直接處理流出物導致安全及操作問題。首先,在結晶器中可形成危險的濃有機過氧化物殘餘物相。此外,所得鹽可含有過氧化物殘餘物及/或高有機雜質含量,此使其無法重複使用或在重複使用鹽時可導致健康及安全問題。另外,在來自使用苯甲醯氯作為反應物之方法的流出物中存在之苯甲酸殘餘物之沉降可引起結垢及吹掃問題。且最後,在來自使用高級醯氯作為反應物之方法的流出物中存在的高級羧酸(≥8個碳原子)或其鹽可最終存於水層中且可導致起泡沫,由此降低結晶器之容量。
為了使該鹽適於重複使用,基於乾鹽之重量,其應不含超過1000 ppm、較佳不超過500 ppm、甚至更佳不超過300 ppm且最佳不超過200 ppm之有機雜質。此有機雜質之含量定義為不可吹掃有機化合物(non-purgeable organic compound, NPOC)含量,其可如以下實例中所述測定。
現已發現,為減輕該等問題並獲得適於重複使用之鹽,首先將流出物酸化至在範圍1-5中之pH,隨後分離有機液體層,且然後使流出物之pH值再次升高至在範圍6-14中之值。
酸化使得在製造有機過氧化物時方法流中通常存在之苯甲酸及高級羧酸進入有機層中,此允許其在結晶前與水層分離。隨後的高pH用於防止不銹鋼結晶設備腐蝕及/或防止有機酸沈澱。
因此,本發明係關於由來自一或多個有機過氧化物製造方法之水性流出物製造包含NaCl及/或KCl之鹽的方法,該方法包含以下步驟:
a) 確保水性流出物之pH在範圍1-5中,
b) 將流出物分成液體有機層及水層,
c) 去除液體有機層,
d) 使水層之pH升高至在範圍6-14中之值,
e) 使鹽自pH在範圍6-14中之水層結晶。
應注意,CN 108423908揭示其中處理來自有機過氧化物方法之流出物的方法,該方法包含以下步驟:酸化流出物,藉由沈澱分離呈固體形式之4-甲基苯甲酸並將剩餘流體之pH增加至介於5與7之間之值,且然後藉由沈澱步驟分離NaCl。CN 108423908中所揭示方法之目的主要係分離並回收未反應之4-甲基苯甲酸,而非主要地以高純度回收鹽。已驚訝地發現,當在步驟b)中該分離係液-液分離時(其中分離有機相及水性液相),如此分離之鹽的純度明顯改良,該鹽所含(不可吹掃)有機物之量顯著低於CN 108423908中所揭示方法。換言之,在CN 108423908之方法中,希望獲得具有增加之低有機物量之鹽,則將需要其他純化步驟,此將使該方法不具吸引力並導致分離出較少的該鹽,此乃因任何純化步驟均將損失一些產量。
水性流出物
水性流出物係藉由醯氯或氯甲酸酯與有機氫過氧化物或H2
O2
在鹼性條件下反應製造二醯基過氧化物、過氧酯、過氧碳酸酯或過氧二碳酸酯而產生。
過氧酯之實例係過氧苯甲酸第三丁基酯、過氧苯甲酸第三戊基酯、過氧苯甲酸異丙苯基酯、過氧苯甲酸1,1,3,3-四甲基丁基酯、過氧異丁酸第三丁基酯、過氧異丁酸第三戊基酯、過氧異丁酸1,1,3,3-四甲基丁基酯、過氧異丁酸異丙苯基酯、過氧新癸酸異丙苯基酯、過氧新癸酸1,1,3,3-四甲基丁基酯、過氧新癸酸第三戊基酯、過氧新癸酸第三丁基酯、過氧新戊酸1,1,3,3-四甲基丁基酯、過氧新戊酸第三戊基酯、過氧新戊酸第三丁基酯、過氧新戊酸異丙苯基酯、過氧-2-乙基己酸1,1,3,3-四甲基丁基酯、過氧-2-乙基己酸第三戊基酯、過氧-2-乙基己酸第三丁基酯、過氧-2-乙基己酸異丙苯基酯、過氧乙酸第三戊基酯、過氧乙酸第三丁基酯、過氧乙酸異丙苯基酯、過氧-3,5,5-三甲基己酸第三丁基酯、過氧-3,5,5-三甲基己酸第三戊基酯及過氧-3,5,5-三甲基己酸異丙苯基酯。
較佳過氧酯係過氧新戊酸第三戊基酯、過氧新戊酸第三丁基酯、過氧-2-乙基己酸第三戊基酯、過氧-2-乙基己酸第三丁基酯、過氧-3,5,5-三甲基己酸第三丁基酯、過氧新癸酸異丙苯基酯及過氧新癸酸第三丁基酯。
過氧碳酸酯之實例係碳酸第三丁基酯過氧-2-乙基己基酯、碳酸第三戊基酯過氧-2-乙基己基酯、碳酸異丙苯基酯過氧-2-乙基己基酯、碳酸第三丁基酯過氧-2-乙基己基酯、碳酸1,1,3,3-四甲基丁基酯過氧-2-乙基己基酯、碳酸第三丁基酯過氧異丙基酯、碳酸第三戊基酯過氧異丙基酯、碳酸異丙苯基酯過氧異丙基酯、碳酸第三丁基酯過氧異丙基酯及碳酸1,1,3,3-四甲基丁基酯過氧異丙基酯。
較佳過氧碳酸酯係碳酸第三丁基酯過氧-2-乙基己基酯。
二醯基過氧化物之實例係二-異丁醯基過氧化物、二-正丁醯基過氧化物、二-異戊醯基過氧化物、二-正戊醯基過氧化物、二-2-甲基丁醯基過氧化物、二-己醯基過氧化物、二-辛醯基過氧化物、過氧化二苯甲醯、乙醯基異丁醯基過氧化物、環己基羰基乙醯基過氧化物、乙醯基過氧化苯甲醯、月桂醯基乙醯基過氧化物、己醯基乙醯基過氧化物、丙醯基異丁醯氯、丙醯基過氧化苯甲醯、二(對-甲基苯甲醯基)過氧化物、二(鄰-甲基苯甲醯基)過氧化物、二月桂醯基過氧化物、二(3,5,5-三甲基己醯基)過氧化物及二癸醯基過氧化物。
較佳二醯基過氧化物係二-異丁醯基過氧化物、乙醯基異丁醯基過氧化物、過氧化二苯甲醯、二(對-甲基苯甲醯基)過氧化物、二(鄰-甲基苯甲醯基)過氧化物、二月桂醯基過氧化物及二(3,5,5-三甲基己醯基)過氧化物。
過氧二碳酸酯之實例係二(3-甲氧基丁基)過氧二碳酸酯、過氧二碳酸二(2-乙基己基)酯、過氧二碳酸二-第二丁基酯、過氧二碳酸二異丙基酯、過氧二碳酸二(十六烷基)酯、過氧二碳二-(4-第三丁基環己基)酸酯、過氧二碳酸二肉豆蔻基酯及過氧二碳酸二(2-丙基庚基)酯。
較佳過氧二碳酸酯係過氧二碳酸二(2-乙基己基)酯。
本發明方法中可使用來自一個個別過氧化物製造方法之水性流出物,但其亦可使用來自兩個或以上過氧化物製造方法之水性流出物的混合物。
使用此一混合物之優點在於所形成並在步驟b)中去除之(組合)液體有機相可作為用於來自該混合物水層之水溶性有機雜質之萃取溶劑。
欲用於本發明方法中之水性流出物通常含有大於3 wt%、更佳大於7 wt%、甚至更佳大於12 wt%之包含NaCl及/或KCl之鹽。
流出物中有機物質之濃度通常等於0.1-10 wt%、更佳0.3-7 wt%、最佳0.5-4 wt%。該等有機物之部分係由有機(氫)過氧化物殘餘物組成。該等殘餘物通常以0.01至4 wt%、較佳0.05至3 wt%、最佳0.1至2.5 wt%之濃度存在於流出物中。
可存在於該等流出物中之其他有機物質係過氧化物分解產物(例如丙酮、甲醇、甲基乙基酮、乙醇、第三丁醇或第三戊醇)及溶劑(例如鄰苯二甲酸二甲酯、異十二烷、無臭礦油精、乙酸乙酯或甲苯)。
欲用於該方法中之流出物的pH較佳為至少8、甚至更佳至少10、最佳至少11。
步驟 a)
步驟a)要求確保水性流出物之pH在範圍1-5中、較佳在範圍2-4中。此意味著若pH已在彼範圍中,則不需要任何動作。
然而,由於流出物係由在鹼性條件下實施之方法產生,故其通常將需要藉由添加酸以降低pH。
儘管可使用許多酸,但對於含氯離子之流出物而言較佳使用HCl。倘若流出物亦含有硫酸根陰離子,則可適宜地使用H2
SO4
或NaHSO4
。
步驟 b)
步驟a)之酸化通常將導致形成液體有機相。在酸化步驟a)之前或期間,可視情況添加有機溶劑。若沒有或幾乎沒有任何液體有機相形成,則期望在酸化步驟a)之前或期間添加有機溶劑,以自流出物中萃取有機物,由此減少結垢並改良相分離及有機層之安全特性。在其中形成之液體有機相太少以致於無法實施良好的液-液分離之實施例中,添加有機溶劑。
此有機溶劑較佳係在水中僅具有有限溶解度之極性溶劑。適宜溶劑之實例係低級鄰苯二甲酸酯、C6-18
羧酸、C6-18
醇、具有多於5個碳原子之酯、具有多於5個碳原子之醚、具有多於5個碳原子之烷烴、具有多於6個碳之芳香族化合物及該等溶劑之混合物。特定實例係2-乙基己醇、鄰苯二甲酸二甲酯、油酸、柴油、異構C12
-混合物(例如異十二烷)、含有己二酸二甲酯或己二酸二乙酯、己二酸二辛酯、癸二酸二丁酯、馬來酸二丁酯、苯甲酸乙酯之酯混合物、甲苯、二甲苯及其混合物。
液體有機層將含有流出物中存在之大多數有機組分,包括有機過氧化物殘餘物、苯甲酸、醇及高級羧酸。
步驟 c)
將在步驟b)中形成之液體有機層自水層去除。此可以各種方式實施。例如,其可藉由重力沉降、隨後傾析上部層來實施。其亦可利用撇油器實施,即,含有旋轉皮帶或緩慢移動之刮刀的裝置,其浸入有機層中並將有機層去除。液體有機層亦可藉由液-液分離器、藉由施加離心力、藉由板分離器、藉由浮選或藉由萃取去除。
去除之液體有機層可轉移至生物廢水處理單元;按原樣或分散於(鹼性)水中。有機層亦可作為有機液體廢物進行處置,或在洗滌及/或中和後用作燃料。若在步驟b期間添加有機溶劑,則較佳實施例中之有機層視情況藉由例如用鹼性水溶液洗滌來純化,在步驟b)中重複用作萃取溶劑。
若期望,可藉由蒸汽汽提去除揮發性有機化合物,例如丙酮、甲醇、乙酸、甲酸、異丁酸、正丁酸、特戊酸、氫過氧化第三戊基及氫過氧化第三丁基。此可在酸化步驟a)之後及去除液體有機層之前或之後實施。
蒸汽汽提通常在90-120℃之溫度範圍內及0.1-0.2 Mpa之壓力下實施。
所得蒸氣流可經冷凝並發送至生物廢水處理單元。
步驟 d)
在分離出液體有機層之後,使水層之pH增加至範圍6-14、較佳7-13、更佳8-13、甚至更佳9-13且最佳11-13中之值,以防止步驟e)中所用結晶設備腐蝕及/或以防止有機酸沈澱。
pH較佳藉由添加KOH或NaOH來升高。
步驟 e)
鹽可以各種方式結晶。該等途徑中之一者係蒸發結晶。結晶溫度及壓力取決於鹽溶液之沸騰溫度及結晶器構形。溫度通常將介於50與150℃之間;壓力介於50毫巴(mbar)與4巴之間。
結晶器可為任何習用類型,例如由機械蒸汽再壓縮(MVR)驅動之強制循環結晶器或由蒸汽驅動之單效或多效結晶器,視情況與熱蒸汽再壓縮(TVR)組合;或簡單地噴霧乾燥器。
對於KCl結晶,冷卻結晶亦係可能的。
對於NaCl結晶,雙效或三效蒸汽驅動之結晶器或MVR係較佳的。
結晶導致形成鹽漿液。若出於品質原因需要,可使用例如(推料式)離心機、淘析腿、洗滌塔或洗滌容器洗滌此漿液。洗滌可利用清潔水或鹽水(例如,來自前一洗滌循環之鹽水)來實施。鹽係藉由重力沉降、離心、過濾或任何其他適宜固液分離技術自漿液中作為「濕鹽」收集。濾液可經處置或(部分地)再循環至步驟a)或步驟e)。
在實施例中,在將濕鹽與黏附液體分離之後,亦可在過濾器或另一適宜設備上洗滌濕鹽。
若期望,所得(經洗滌或未經洗滌)「濕」鹽可經乾燥。乾燥可在任何習用乾燥器中實施,例如流化床乾燥器或帶式乾燥器。
所得鹽較佳具有小於10 wt%、更佳小於5%且在乾燥後較佳小於0.5 wt%之水分含量。
基於乾燥鹽重量,其較佳含有小於1000 ppm、更佳小於500 ppm、甚至更佳不超過300 ppm且最佳不超過200 ppm之不可吹掃有機化合物(NPOC),因此其適於重複使用。
若期望,可將抗結塊劑添加至鹽。抗結塊劑之實例係六氰鐵酸鈉(黃血鹽鈉(yellow prussiate of soda), YPS)或二氧化矽。
抗結塊劑通常以5-100 ppm之量添加。
所獲得鹽可作為廢物處置,但較佳重複使用。其可重複用於各種應用中,例如紡織品製造、皮革鞣製、施肥或氯鹼方法。
實例
在所有實例中,使用Shimadzu TOC (總有機碳)分析器量測NPOC。首先,將鹽溶解於水中並藉由添加HCl使其為酸性,之後利用N2
進行吹掃。此後,將試樣在680℃下在試管中在Pt-觸媒之存在下燃燒。利用非分散式紅外(NDIR)檢測器測定所形成之CO2
並相對於外部標準品(鄰苯二甲酸氫鉀)計算碳量。
實例 1
將30 l來自有機過氧化物製造方法之若干水性廢物流之混合物添加至實驗性規模反應器。混合物具有10.5之pH及以下大致組成:
NaCl | 15 wt% |
苯甲酸鈉 | 1 wt% |
2-乙基己酸鈉 | 2 wt% |
氫過氧化第三丁基 | 2 wt% |
水 | 剩餘部分 |
藉由添加30 wt% HCl溶液將混合物酸化至pH 2.5,隨後添加0.5 wt%鄰苯二甲酸二甲酯(基於混合物之總重量)。獲得澄清有機層,其可容易地與水相分離。
將30 wt% NaOH溶液添加至所得水相,直至pH為10.5。然後將混合物轉移至實驗性規模間歇式結晶器,在1巴之壓力下加熱至約110℃。結晶期間,自頂部去除水蒸氣。一段時間之後,開始形成NaCl晶體。將所得鹽漿液轉移至離心機。離心期間,將鹽用200 ml/kg鹽之總洗滌水流量洗滌。所得NaCl具有4 wt%之水含量及233 ppm之不可吹掃有機碳(NPOC)含量。
實例 2
將30 l來自有機過氧化物製造方法之若干水性廢物流之混合物添加至實驗性規模反應器。混合物具有約11之pH及以下大致組成:
KCl | 15 wt% |
新癸酸鈉 | 2 wt% |
異丙苯基氫過氧化物 | 1.5 wt% |
水 | 剩餘部分 |
藉由添加30 wt% HCl溶液將混合物酸化至pH 2.5。在水相之頂部上形成澄清液體有機層。此有機層藉由使用小規模撇油器(ex-Abanaki)分離與水相。
將30 wt% KOH溶液添加至所得水相,直至pH為10.5。然後將混合物轉移至實驗性規模間歇式結晶器,在60毫巴之壓力下加熱至約50℃。結晶期間,自頂部去除水蒸氣。一段時間之後,開始形成KCl晶體。將所得鹽漿液轉移至離心機。離心期間,將鹽用300 ml/kg鹽之總洗滌水流量洗滌。所得KCl具有4 wt%之水含量及215 ppm之NPOC含量。將KCl轉移至實驗性規模流化床乾燥器。所得乾燥鹽具有0.2 wt%之水含量。
實例 3
將30 l來自有機過氧化物製造方法之若干水性廢物流之混合物添加至實驗性規模反應器。混合物具有以下大致組成:
NaCl | 15 wt% |
苯甲酸鈉 | 0.3 wt% |
2-乙基己酸鈉 | 2 wt% |
氫過氧化第三丁基 | 2 wt% |
水 | 剩餘部分 |
藉由添加30 wt% HCl溶液將混合物酸化至pH 2.5並添加實例2中所獲得之有機層。獲得澄清有機層,其可容易地與水相分離。
將30 wt% NaOH溶液添加至所得水相,直至pH為10.5。然後將混合物轉移至實驗性規模間歇式結晶器,在1巴之壓力下加熱至約110℃。結晶期間,自頂部去除水蒸氣。一段時間之後,開始形成NaCl晶體。將所得鹽漿液轉移至離心機。離心期間,將鹽用400 ml/kg鹽之總洗滌水流量洗滌。所得NaCl具有4 wt%之水含量及177 ppm之NPOC含量。
實例 4
將30 l來自有機過氧化物製造方法之若干水性廢物流之混合物添加至實驗性規模反應器。混合物具有以下大致組成:
NaCl | 15 wt% |
KCl | 3 wt% |
Na2 SO4 | 2 wt% |
混合有機物 | 4 wt% |
水 | 剩餘部分 |
藉由添加30 wt% HCl溶液將混合物酸化至pH 2.5。在水相之頂部上形成澄清液體有機層。將有機層與水相分離。
將30 wt% NaOH溶液添加至所得水相,直至pH為10.5。然後將混合物轉移至實驗性規模間歇式結晶器,在1巴之壓力下加熱至約110℃。結晶期間,自頂部去除水蒸氣。一段時間之後,開始形成鹽晶體。將所得鹽漿液轉移至離心機。所得鹽混合物具有6 wt%之水含量及760 ppm之NPOC含量。
比較實例 5
將30 l實例1中使用之廢物流混合物轉移至實驗性規模間歇式結晶器,在1巴之壓力下加熱至約110℃。一段時間之後,開始形成NaCl晶體。大約在同一時間,開始形成苯甲酸鈉沈澱。其試圖繼續結晶,直至形成合理的漿液密度,但苯甲酸鈉及其他沈澱堵塞設備。由於鹽/有機混合物不能充分脫水,故漿液不能離心至水含量<10%。
此試驗說明,實例1中所實施之酸化步驟對於鹽之適當分離係必需的。
比較實例 6
將30 l實例2中所用之廢物流混合物轉移至實驗性規模間歇式結晶器,在60毫巴之壓力下加熱至約50℃。結晶期間,自頂部去除水蒸氣。一段時間之後,開始形成KCl晶體。將所得鹽漿液轉移至離心機。在離心中,觀察到形成泡沫,此導致緩慢且不完全離心。嘗試用300 ml/kg鹽之總洗滌水流量洗滌鹽。將鹽轉移至實驗性規模流化床乾燥器。所得乾燥鹽具有2600 ppm之NPOC含量。
此試驗說明,實例2中所實施之酸化步驟對於獲得具有足夠低有機物含量之鹽係必需的。
實例 7
過氧化二苯甲醯係利用苯甲醯氯、H2O2-30%、NaOH-25%及表面活性劑製得。將反應混合物過濾以分離產物及水層。水層具有以下組成:
NaCl | 7 wt% |
苯甲酸鈉 | 0.6 wt% |
過苯甲酸鈉 | 0.03 wt% |
水 | 剩餘部分 |
向利用Knick pH計及Mettler Toledo Inlab pH電極量測之pH > 6之100.4 g水層添加8.04 g鄰苯二甲酸二甲酯(DMP)。藉由添加0.84 g 18 wt% HCl溶液將合併之混合物在攪拌下於20-25℃下酸化至pH 2.3。繼續攪拌5分鐘後,將各層分開。將下部DMP層與水層分離。將所獲得苯甲酸含量為0.07%之水相用30 wt% NaOH溶液中和至pH > 7。然後將混合物轉移至間歇式結晶器,在1巴之壓力下加熱至約110℃。結晶期間,自頂部去除水蒸氣。一段時間之後,開始形成鹽晶體。將所得鹽漿液轉移至離心機。所獲得鹽具有6 wt%之水含量及620 ppm之NPOC含量。將DMP層用3% NaOH溶液洗滌直至pH > 7並在苯甲酸之萃取中重複使用。
比較實例 8
將77.3 g如實例7中一樣之過氧化苯甲醯方法之水層藉由添加0.64 g 18 wt% HCl溶液在攪拌下於20-25℃下酸化至pH 2.3。在水相中形成白色沈澱。繼續攪拌5分鐘後,濾出固體。將所獲得苯甲酸含量為0,17%之澄清水相用30 wt% NaOH溶液中和至pH > 7。然後將混合物轉移至間歇式結晶器,在1巴之壓力下加熱至約110℃。結晶期間,自頂部去除水蒸氣。一段時間之後,開始形成鹽晶體。將所得鹽漿液轉移至離心機。所獲得鹽具有6 wt%之水含量及1490 ppm之NPOC含量。
此試驗說明,在實例7中所實施之酸化步驟中添加溶劑及隨後液液分離係獲得具有足夠低有機物含量之鹽所必需的。
Claims (11)
- 一種由水性流出物製造包含NaCl及/或KCl之鹽的方法,該水性流出物係來自藉由醯氯或氯甲酸酯與有機氫過氧化物或H2O2在鹼性條件下反應以製造二醯基過氧化物、過氧酯、過氧碳酸酯或過氧二碳酸酯之製程,該方法包含以下步驟:a)確保該等水性流出物之pH在範圍1-5中,b)將該等流出物分成液體有機層及水層,c)去除該有機層,d)使該水層之pH升高至在範圍6-14中之值,e)使該鹽自pH在範圍6-14中之該水層結晶。
- 如請求項1之方法,其中步驟a)涉及將該等流出物酸化至在範圍1-4中之pH。
- 如請求項2之方法,其中HCl用於該酸化。
- 如請求項1至3中任一項之方法,其中在步驟d)之前,該水層經受蒸汽汽提以去除揮發性有機化合物。
- 如請求項4之方法,其中該等揮發性有機化合物包含異丁酸、正丁酸、特戊酸、氫過氧化第三戊基及/或氫過氧化第三丁基。
- 如請求項1至3中任一項之方法,其中在步驟b)之前或期間添加有機溶劑。
- 如請求項6之方法,其中在步驟c)中所收集之該有機層經循環並作為該有機溶劑重複使用。
- 如請求項6之方法,其中在步驟c)中所收集之該有機層經循環並在其用鹼性水溶液洗滌之後作為該有機溶劑重複使用。
- 如請求項1至3中任一項之方法,其中步驟c)涉及使用撇油器。
- 如請求項1至3中任一項之方法,其中步驟e)涉及使該水相經歷蒸發,藉此使該鹽結晶以形成鹽漿液。
- 如請求項1至3中任一項之方法,其中將步驟e)中所獲得之該鹽乾燥至水分含量低於0.5wt%。
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP19154884 | 2019-01-31 | ||
EP19154884.1 | 2019-01-31 |
Publications (2)
Publication Number | Publication Date |
---|---|
TW202035290A TW202035290A (zh) | 2020-10-01 |
TWI831913B true TWI831913B (zh) | 2024-02-11 |
Family
ID=65496690
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
TW109103105A TWI831913B (zh) | 2019-01-31 | 2020-01-31 | 由廢物流製造鹽之方法 |
Country Status (6)
Country | Link |
---|---|
US (1) | US20220081307A1 (zh) |
EP (1) | EP3917885A1 (zh) |
JP (1) | JP7328340B2 (zh) |
BR (1) | BR112021014934A2 (zh) |
TW (1) | TWI831913B (zh) |
WO (1) | WO2020157061A1 (zh) |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
ES2963382T3 (es) | 2019-06-12 | 2024-03-26 | Nouryon Chemicals Int Bv | Proceso para la producción de peróxidos de diacilo |
ES2963357T3 (es) | 2019-06-12 | 2024-03-26 | Nouryon Chemicals Int Bv | Proceso para la producción de peróxidos de diacilo |
JP2023548614A (ja) * | 2020-12-01 | 2023-11-17 | ヌーリオン ケミカルズ インターナショナル ベスローテン フェノーツハップ | アルカリ金属塩の共生成を用いて水性副流からカルボン酸を単離するための方法 |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102963971A (zh) * | 2012-11-20 | 2013-03-13 | 乌鲁木齐市华泰隆化学助剂有限公司 | 从引发剂生产废液中回收氯化钾及有机物的方法 |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20130313199A1 (en) * | 2012-05-23 | 2013-11-28 | High Sierra Energy, LP | System and method for treatment of produced waters |
CN103787442A (zh) * | 2012-10-31 | 2014-05-14 | 中国石油化工集团公司 | 过氧化二异丙苯缩合废水的处理方法 |
CN108423908A (zh) | 2018-04-11 | 2018-08-21 | 常熟市滨江化工有限公司 | 一种过氧化双(4-甲基苯甲酰)废水的处理方法 |
-
2020
- 2020-01-28 US US17/310,327 patent/US20220081307A1/en active Pending
- 2020-01-28 BR BR112021014934-1A patent/BR112021014934A2/pt unknown
- 2020-01-28 JP JP2021544503A patent/JP7328340B2/ja active Active
- 2020-01-28 EP EP20701363.2A patent/EP3917885A1/en active Pending
- 2020-01-28 WO PCT/EP2020/052039 patent/WO2020157061A1/en unknown
- 2020-01-31 TW TW109103105A patent/TWI831913B/zh active
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102963971A (zh) * | 2012-11-20 | 2013-03-13 | 乌鲁木齐市华泰隆化学助剂有限公司 | 从引发剂生产废液中回收氯化钾及有机物的方法 |
Also Published As
Publication number | Publication date |
---|---|
WO2020157061A1 (en) | 2020-08-06 |
US20220081307A1 (en) | 2022-03-17 |
JP7328340B2 (ja) | 2023-08-16 |
BR112021014934A2 (pt) | 2021-09-28 |
TW202035290A (zh) | 2020-10-01 |
EP3917885A1 (en) | 2021-12-08 |
JP2022518845A (ja) | 2022-03-16 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
TWI831913B (zh) | 由廢物流製造鹽之方法 | |
KR101650694B1 (ko) | 락트산 추출 | |
US3452088A (en) | Terephthalic acid recovery | |
JP4954873B2 (ja) | 乳酸マグネシウム含有媒質からの乳酸または乳酸塩の調製方法 | |
RU2395486C2 (ru) | Очистка карбоновых кислот путем комплексообразования с селективными растворителями | |
JP3976832B2 (ja) | 2−ケト−l−グロン酸の単離方法 | |
CA2933129A1 (en) | Process for lignin purification and isolation | |
EP3820841B1 (en) | Process for producing 4,4'-dichlorodiphenyl sulfone | |
CN113382968A (zh) | 从有机过氧化物生产的含水废物流生产盐的方法 | |
CA3024780C (en) | Method for separating biomass from solid fermentation product | |
US3726917A (en) | Process for preparing adipic acid | |
JP7336541B2 (ja) | 過酸化ジアシルを生成するためのプロセス | |
JPH02102703A (ja) | 有機化合物で汚染された無機塩の処理方法 | |
JP7355858B2 (ja) | 水性側流からカルボン酸を単離するための方法 | |
US3875222A (en) | Process for the production of malic acid | |
JPS6360965A (ja) | 無水ペルオキシカルボン酸を不動化する方法 | |
JP7462761B2 (ja) | 塩化マグネシウム溶液を精製する方法 | |
CN113924282B (zh) | 用于从含水侧流中分离羧酸的方法 | |
CN113993844B (zh) | 用于生产过氧化二酰的方法 | |
JP7335362B2 (ja) | 過酸化ジアシルを生成するためのプロセス | |
WO2022117439A1 (en) | Method for isolating carboxylic acid from an aqueous side stream with co-production of alkali metal salt | |
JP2022535948A (ja) | 過酸化ジアシルを生成するためのプロセス | |
WO2013140752A1 (ja) | 5-オキソ-4-オキサ-5-ホモアダマンタン-2-オールの製造方法 | |
JPH03290303A (ja) | 二酸化塩素の製造方法 | |
JPH0142890B2 (zh) |