JPS5978136A - 水性溶液からのフエノ−ル類の抽出 - Google Patents
水性溶液からのフエノ−ル類の抽出Info
- Publication number
- JPS5978136A JPS5978136A JP58177172A JP17717283A JPS5978136A JP S5978136 A JPS5978136 A JP S5978136A JP 58177172 A JP58177172 A JP 58177172A JP 17717283 A JP17717283 A JP 17717283A JP S5978136 A JPS5978136 A JP S5978136A
- Authority
- JP
- Japan
- Prior art keywords
- phenol
- aqueous
- oxide
- phase
- organic phase
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 150000002989 phenols Chemical class 0.000 title claims description 18
- 239000007864 aqueous solution Substances 0.000 title claims description 13
- 238000000605 extraction Methods 0.000 title claims description 8
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 31
- 238000000034 method Methods 0.000 claims description 24
- 239000012074 organic phase Substances 0.000 claims description 14
- 150000004996 alkyl benzenes Chemical class 0.000 claims description 10
- 239000008346 aqueous phase Substances 0.000 claims description 10
- -1 phosphine oxide compound Chemical group 0.000 claims description 9
- 238000009835 boiling Methods 0.000 claims description 8
- 238000004821 distillation Methods 0.000 claims description 7
- AUONHKJOIZSQGR-UHFFFAOYSA-N oxophosphane Chemical compound P=O AUONHKJOIZSQGR-UHFFFAOYSA-N 0.000 claims description 7
- 239000012071 phase Substances 0.000 claims description 5
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- PMPBFICDXLLSRM-UHFFFAOYSA-N 1-propan-2-ylnaphthalene Chemical compound C1=CC=C2C(C(C)C)=CC=CC2=C1 PMPBFICDXLLSRM-UHFFFAOYSA-N 0.000 claims description 3
- IAUKWGFWINVWKS-UHFFFAOYSA-N 1,2-di(propan-2-yl)naphthalene Chemical compound C1=CC=CC2=C(C(C)C)C(C(C)C)=CC=C21 IAUKWGFWINVWKS-UHFFFAOYSA-N 0.000 claims description 2
- ZMBHCYHQLYEYDV-UHFFFAOYSA-N trioctylphosphine oxide Chemical group CCCCCCCCP(=O)(CCCCCCCC)CCCCCCCC ZMBHCYHQLYEYDV-UHFFFAOYSA-N 0.000 claims description 2
- 150000008442 polyphenolic compounds Chemical class 0.000 claims 1
- 239000002904 solvent Substances 0.000 description 19
- 239000000243 solution Substances 0.000 description 15
- 239000002699 waste material Substances 0.000 description 8
- 238000011084 recovery Methods 0.000 description 5
- 238000000638 solvent extraction Methods 0.000 description 5
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 4
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 229930195733 hydrocarbon Natural products 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 102220049405 rs147669920 Human genes 0.000 description 4
- PTTPXKJBFFKCEK-UHFFFAOYSA-N 2-Methyl-4-heptanone Chemical compound CC(C)CC(=O)CC(C)C PTTPXKJBFFKCEK-UHFFFAOYSA-N 0.000 description 3
- 239000004215 Carbon black (E152) Substances 0.000 description 3
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 3
- 150000002430 hydrocarbons Chemical class 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallol Chemical class OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- HXDOZKJGKXYMEW-UHFFFAOYSA-N 4-ethylphenol Chemical compound CCC1=CC=C(O)C=C1 HXDOZKJGKXYMEW-UHFFFAOYSA-N 0.000 description 2
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- JPYHHZQJCSQRJY-UHFFFAOYSA-N Phloroglucinol Natural products CCC=CCC=CCC=CCC=CCCCCC(=O)C1=C(O)C=C(O)C=C1O JPYHHZQJCSQRJY-UHFFFAOYSA-N 0.000 description 2
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000003245 coal Substances 0.000 description 2
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 2
- QCDYQQDYXPDABM-UHFFFAOYSA-N phloroglucinol Chemical compound OC1=CC(O)=CC(O)=C1 QCDYQQDYXPDABM-UHFFFAOYSA-N 0.000 description 2
- 229960001553 phloroglucinol Drugs 0.000 description 2
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
- 239000002689 soil Substances 0.000 description 2
- XFRVVPUIAFSTFO-UHFFFAOYSA-N 1-Tridecanol Chemical compound CCCCCCCCCCCCCO XFRVVPUIAFSTFO-UHFFFAOYSA-N 0.000 description 1
- CWFAZNDDFUSZFH-UHFFFAOYSA-N 1-[2-methylpropyl(octyl)phosphoryl]octane Chemical compound CCCCCCCCP(=O)(CC(C)C)CCCCCCCC CWFAZNDDFUSZFH-UHFFFAOYSA-N 0.000 description 1
- WWYUQXYAGXKBNE-UHFFFAOYSA-N 1-[bis(2,4,4-trimethylpentyl)phosphoryl]-2,4,4-trimethylpentane Chemical compound CC(C)(C)CC(C)CP(=O)(CC(C)CC(C)(C)C)CC(C)CC(C)(C)C WWYUQXYAGXKBNE-UHFFFAOYSA-N 0.000 description 1
- XPHJACAQAZXEIZ-UHFFFAOYSA-N 1-[bis(6-methylheptyl)phosphoryl]-6-methylheptane Chemical compound CC(C)CCCCCP(=O)(CCCCCC(C)C)CCCCCC(C)C XPHJACAQAZXEIZ-UHFFFAOYSA-N 0.000 description 1
- SXSPHZYWRUCEOB-UHFFFAOYSA-N 1-[hexyl(methyl)phosphoryl]hexane Chemical compound CCCCCCP(C)(=O)CCCCCC SXSPHZYWRUCEOB-UHFFFAOYSA-N 0.000 description 1
- PPDZLUVUQQGIOJ-UHFFFAOYSA-N 1-dihexylphosphorylhexane Chemical compound CCCCCCP(=O)(CCCCCC)CCCCCC PPDZLUVUQQGIOJ-UHFFFAOYSA-N 0.000 description 1
- XHOHEJRYAPSRPZ-UHFFFAOYSA-N 1-dioctadecylphosphoryloctadecane Chemical compound CCCCCCCCCCCCCCCCCCP(=O)(CCCCCCCCCCCCCCCCCC)CCCCCCCCCCCCCCCCCC XHOHEJRYAPSRPZ-UHFFFAOYSA-N 0.000 description 1
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 1
- LAIZULYZLIEMOR-UHFFFAOYSA-N 1-phosphorosooctane Chemical compound CCCCCCCCP=O LAIZULYZLIEMOR-UHFFFAOYSA-N 0.000 description 1
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 1
- 235000017166 Bambusa arundinacea Nutrition 0.000 description 1
- 235000017491 Bambusa tulda Nutrition 0.000 description 1
- 241000694440 Colpidium aqueous Species 0.000 description 1
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 description 1
- 235000011511 Diospyros Nutrition 0.000 description 1
- 244000236655 Diospyros kaki Species 0.000 description 1
- JYGLAHSAISAEAL-UHFFFAOYSA-N Diphenadione Chemical compound O=C1C2=CC=CC=C2C(=O)C1C(=O)C(C=1C=CC=CC=1)C1=CC=CC=C1 JYGLAHSAISAEAL-UHFFFAOYSA-N 0.000 description 1
- 101100427344 Mus musculus Usp10 gene Proteins 0.000 description 1
- 244000082204 Phyllostachys viridis Species 0.000 description 1
- 235000015334 Phyllostachys viridis Nutrition 0.000 description 1
- MOGGWQKHCKZRIZ-UHFFFAOYSA-N [cyclohexyl(octyl)phosphoryl]cyclohexane Chemical compound C1CCCCC1P(=O)(CCCCCCCC)C1CCCCC1 MOGGWQKHCKZRIZ-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000011425 bamboo Substances 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 210000001124 body fluid Anatomy 0.000 description 1
- 239000010839 body fluid Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000010543 cumene process Methods 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 150000002085 enols Chemical class 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 238000002309 gasification Methods 0.000 description 1
- LHGVFZTZFXWLCP-UHFFFAOYSA-N guaiacol Chemical compound COC1=CC=CC=C1O LHGVFZTZFXWLCP-UHFFFAOYSA-N 0.000 description 1
- 238000000622 liquid--liquid extraction Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000005192 partition Methods 0.000 description 1
- 238000005504 petroleum refining Methods 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-M phenolate Chemical compound [O-]C1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-M 0.000 description 1
- 229940031826 phenolate Drugs 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000005086 pumping Methods 0.000 description 1
- 229940079877 pyrogallol Drugs 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 238000001256 steam distillation Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- MDDUHVRJJAFRAU-YZNNVMRBSA-N tert-butyl-[(1r,3s,5z)-3-[tert-butyl(dimethyl)silyl]oxy-5-(2-diphenylphosphorylethylidene)-4-methylidenecyclohexyl]oxy-dimethylsilane Chemical compound C1[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)C(=C)\C1=C/CP(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 MDDUHVRJJAFRAU-YZNNVMRBSA-N 0.000 description 1
- 150000001461 trihydroxyphenols Chemical class 0.000 description 1
- RMZAYIKUYWXQPB-UHFFFAOYSA-N trioctylphosphane Chemical group CCCCCCCCP(CCCCCCCC)CCCCCCCC RMZAYIKUYWXQPB-UHFFFAOYSA-N 0.000 description 1
- 125000002256 xylenyl group Chemical class C1(C(C=CC=C1)C)(C)* 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
- C02F1/00—Treatment of water, waste water, or sewage
- C02F1/26—Treatment of water, waste water, or sewage by extraction
-
- 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
- C07C37/72—Purification; separation; Use of additives, e.g. for stabilisation by physical treatment by liquid-liquid treatment
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Hydrology & Water Resources (AREA)
- Engineering & Computer Science (AREA)
- Environmental & Geological Engineering (AREA)
- Water Supply & Treatment (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Extraction Or Liquid Replacement (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US429907 | 1982-09-30 | ||
| US06/429,907 US4420643A (en) | 1982-09-30 | 1982-09-30 | Extraction of phenols from aqueous solutions |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5978136A true JPS5978136A (ja) | 1984-05-04 |
| JPH0333142B2 JPH0333142B2 (enExample) | 1991-05-16 |
Family
ID=23705210
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP58177172A Granted JPS5978136A (ja) | 1982-09-30 | 1983-09-27 | 水性溶液からのフエノ−ル類の抽出 |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US4420643A (enExample) |
| EP (1) | EP0105161A1 (enExample) |
| JP (1) | JPS5978136A (enExample) |
| CA (1) | CA1182839A (enExample) |
| ES (1) | ES8504099A1 (enExample) |
| ZA (1) | ZA837306B (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2013540863A (ja) * | 2010-09-30 | 2013-11-07 | エーエスケー ケミカルズ ゲゼルシャフト ミット ベシュレンクテル ハフツング | 鋳造用中子及び鋳型製造のための置換ベンゼン及びナフタレンを含有するバインダー、モールド材混合物及び方法 |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4547596A (en) * | 1983-03-30 | 1985-10-15 | General Electric Company | Separation and recovery of alkylated phenols |
| DE3626968A1 (de) * | 1986-08-08 | 1988-02-11 | Hoechst Ag | Kontinuierliches verfahren zur extraktion von carbonsaeuren, aldehyden, ketonen, alkoholen und phenolen aus verduennten waessrigen loesungen |
| US5340483A (en) * | 1993-06-11 | 1994-08-23 | University Of Maryland At College Park | Two step process for conversion of a weakly adsorbable compound to a strongly adsorbable compound and selective removal thereof |
| WO2006096891A1 (en) * | 2005-03-11 | 2006-09-14 | Jelenka Savkovic-Stevanovic | Process for removing phenol from water |
| JP5064690B2 (ja) * | 2006-01-27 | 2012-10-31 | 出光興産株式会社 | フェノール含有水の処理方法及び処理設備 |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1135485B (de) * | 1960-06-18 | 1962-08-30 | Koppers Gmbh Heinrich | Verfahren zur Gewinnung von Phenolen aus phenolhaltigen waessrigen Gemischen |
| FR1377213A (fr) * | 1963-01-02 | 1964-10-31 | Otto & Co Gmbh Dr C | Procédé pour déphénoler des eaux résiduelles |
| US3968171A (en) * | 1970-03-05 | 1976-07-06 | The Goodyear Tire & Rubber Company | Process for the continuous isolation of dihydric phenols |
| NL7410872A (nl) * | 1974-08-14 | 1976-02-17 | Shell Int Research | Werkwijze voor het zuiveren van in polyhydroxy- verbindingen aanwezige ruwe bishydroxyarylver- bindingen. |
| DE2501376A1 (de) * | 1975-01-15 | 1976-07-22 | Metallgesellschaft Ag | Verfahren zur entfernung von mono- und diphenolen und dergleichen aus abwaessern |
| JPS527930A (en) * | 1975-07-07 | 1977-01-21 | Jo Eguchi | Process for purification of hydroquinone |
| US4026791A (en) * | 1975-10-02 | 1977-05-31 | Pullman Incorporated | Treatment of aqueous waste |
| GB1538212A (en) * | 1976-05-07 | 1979-01-10 | Bp Chem Int Ltd | Recovery of phenols from the aqueous effluent from a phenol/aldehyde resin plant |
| US4113974A (en) * | 1976-12-30 | 1978-09-12 | General Electric Company | Process for purifying impure diphenols |
| US4152528A (en) * | 1977-04-15 | 1979-05-01 | Chevron Research Company | Process for extracting phenol from phenol-water mixtures |
| DE2904831A1 (de) * | 1979-02-08 | 1980-08-14 | Bayer Ag | Verfahren zur abtrennung von phenol aus einem kresolgemisch |
| US4324926A (en) * | 1980-03-06 | 1982-04-13 | Buffalo Color Corporation | Process for the purification of 4,4' dihydroxydiphenyl |
| US4294993A (en) * | 1980-04-14 | 1981-10-13 | General Electric Company | Purification of bisphenol-A |
| US4374283A (en) * | 1981-06-25 | 1983-02-15 | General Electric Company | Purification of aqueous effluent streams containing BPA and phenol |
-
1982
- 1982-09-30 US US06/429,907 patent/US4420643A/en not_active Expired - Lifetime
-
1983
- 1983-08-19 EP EP83108193A patent/EP0105161A1/en not_active Ceased
- 1983-09-27 JP JP58177172A patent/JPS5978136A/ja active Granted
- 1983-09-28 CA CA000437796A patent/CA1182839A/en not_active Expired
- 1983-09-29 ZA ZA837306A patent/ZA837306B/xx unknown
- 1983-09-29 ES ES526112A patent/ES8504099A1/es not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2013540863A (ja) * | 2010-09-30 | 2013-11-07 | エーエスケー ケミカルズ ゲゼルシャフト ミット ベシュレンクテル ハフツング | 鋳造用中子及び鋳型製造のための置換ベンゼン及びナフタレンを含有するバインダー、モールド材混合物及び方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0333142B2 (enExample) | 1991-05-16 |
| ES526112A0 (es) | 1985-04-01 |
| US4420643A (en) | 1983-12-13 |
| ZA837306B (en) | 1984-05-30 |
| ES8504099A1 (es) | 1985-04-01 |
| CA1182839A (en) | 1985-02-19 |
| EP0105161A1 (en) | 1984-04-11 |
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