CA1182839A - Extraction of phenols from aqueous solutions - Google Patents
Extraction of phenols from aqueous solutionsInfo
- Publication number
- CA1182839A CA1182839A CA000437796A CA437796A CA1182839A CA 1182839 A CA1182839 A CA 1182839A CA 000437796 A CA000437796 A CA 000437796A CA 437796 A CA437796 A CA 437796A CA 1182839 A CA1182839 A CA 1182839A
- Authority
- CA
- Canada
- Prior art keywords
- phenol
- extraction
- aqueous
- solution
- oxide
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 150000002989 phenols Chemical class 0.000 title claims abstract description 27
- 238000000605 extraction Methods 0.000 title claims abstract description 18
- 239000007864 aqueous solution Substances 0.000 title claims abstract description 16
- 238000000034 method Methods 0.000 claims abstract description 22
- 239000000243 solution Substances 0.000 claims abstract description 22
- 230000008569 process Effects 0.000 claims abstract description 21
- 238000009835 boiling Methods 0.000 claims abstract description 12
- AUONHKJOIZSQGR-UHFFFAOYSA-N oxophosphane Chemical group P=O AUONHKJOIZSQGR-UHFFFAOYSA-N 0.000 claims abstract description 6
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 30
- ZMBHCYHQLYEYDV-UHFFFAOYSA-N trioctylphosphine oxide Chemical group CCCCCCCCP(=O)(CCCCCCCC)CCCCCCCC ZMBHCYHQLYEYDV-UHFFFAOYSA-N 0.000 claims description 18
- 150000004996 alkyl benzenes Chemical class 0.000 claims description 13
- 239000012074 organic phase Substances 0.000 claims description 11
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 8
- 239000008346 aqueous phase Substances 0.000 claims description 7
- 238000004821 distillation Methods 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- -1 phosphine oxide compound Chemical class 0.000 claims description 4
- 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 3
- 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
- 238000000926 separation method Methods 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 abstract description 7
- 239000002904 solvent Substances 0.000 description 14
- 238000000638 solvent extraction Methods 0.000 description 9
- 239000002699 waste material Substances 0.000 description 8
- PTTPXKJBFFKCEK-UHFFFAOYSA-N 2-Methyl-4-heptanone Chemical compound CC(C)CC(=O)CC(C)C PTTPXKJBFFKCEK-UHFFFAOYSA-N 0.000 description 7
- 238000009826 distribution Methods 0.000 description 5
- 238000011084 recovery Methods 0.000 description 5
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 3
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical class [PH3]=O MPQXHAGKBWFSNV-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
- 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
- 239000003245 coal Substances 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- XEYYARMGRQZDGJ-UHFFFAOYSA-N dicyclohexyl(octyl)phosphane Chemical compound C1CCCCC1P(CCCCCCCC)C1CCCCC1 XEYYARMGRQZDGJ-UHFFFAOYSA-N 0.000 description 2
- 229960004337 hydroquinone Drugs 0.000 description 2
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 2
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 2
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 2
- 239000012071 phase Substances 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
- WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallol Chemical compound OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 description 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
- 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
- MSKVTMZQUUEALA-UHFFFAOYSA-N 1-[hexyl(2-methylpropyl)phosphoryl]hexane Chemical compound CCCCCCP(=O)(CC(C)C)CCCCCC MSKVTMZQUUEALA-UHFFFAOYSA-N 0.000 description 1
- GYGISEPATDGSPS-UHFFFAOYSA-N 1-didecylphosphoryldecane Chemical compound CCCCCCCCCCP(=O)(CCCCCCCCCC)CCCCCCCCCC GYGISEPATDGSPS-UHFFFAOYSA-N 0.000 description 1
- BRLCBJSJAACAFG-UHFFFAOYSA-N 1-didodecylphosphoryldodecane Chemical compound CCCCCCCCCCCCP(=O)(CCCCCCCCCCCC)CCCCCCCCCCCC BRLCBJSJAACAFG-UHFFFAOYSA-N 0.000 description 1
- KNFWHHCXXKWASF-UHFFFAOYSA-N 1-diheptylphosphorylheptane Chemical compound CCCCCCCP(=O)(CCCCCCC)CCCCCCC KNFWHHCXXKWASF-UHFFFAOYSA-N 0.000 description 1
- GBPPJPKBRDHVOJ-UHFFFAOYSA-N 1-dihexadecylphosphorylhexadecane Chemical compound CCCCCCCCCCCCCCCCP(=O)(CCCCCCCCCCCCCCCC)CCCCCCCCCCCCCCCC GBPPJPKBRDHVOJ-UHFFFAOYSA-N 0.000 description 1
- YFBDFZUHISABHK-UHFFFAOYSA-N 1-dihexylphosphoryldodecane Chemical compound CCCCCCCCCCCCP(=O)(CCCCCC)CCCCCC YFBDFZUHISABHK-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
- YUOASWSSAJRLPI-UHFFFAOYSA-N C1(CCCCCCC1)C(C[PH2]=O)C1CCCCCCC1 Chemical compound C1(CCCCCCC1)C(C[PH2]=O)C1CCCCCCC1 YUOASWSSAJRLPI-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000000470 constituent 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
- 108010037444 diisopropylglutathione ester Proteins 0.000 description 1
- 238000002474 experimental method Methods 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
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 238000000622 liquid--liquid extraction Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 150000004780 naphthols Chemical class 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 150000004707 phenolate Chemical class 0.000 description 1
- 229940079877 pyrogallol Drugs 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- CMXPERZAMAQXSF-UHFFFAOYSA-M sodium;1,4-bis(2-ethylhexoxy)-1,4-dioxobutane-2-sulfonate;1,8-dihydroxyanthracene-9,10-dione Chemical compound [Na+].O=C1C2=CC=CC(O)=C2C(=O)C2=C1C=CC=C2O.CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC CMXPERZAMAQXSF-UHFFFAOYSA-M 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 238000001256 steam distillation Methods 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 group 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
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 150000003739 xylenols Chemical class 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 |
|---|---|---|---|
| US429,907 | 1982-09-30 | ||
| US06/429,907 US4420643A (en) | 1982-09-30 | 1982-09-30 | Extraction of phenols from aqueous solutions |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1182839A true CA1182839A (en) | 1985-02-19 |
Family
ID=23705210
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000437796A Expired CA1182839A (en) | 1982-09-30 | 1983-09-28 | Extraction of phenols from aqueous solutions |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US4420643A (https=) |
| EP (1) | EP0105161A1 (https=) |
| JP (1) | JPS5978136A (https=) |
| CA (1) | CA1182839A (https=) |
| ES (1) | ES526112A0 (https=) |
| ZA (1) | ZA837306B (https=) |
Families Citing this family (6)
| 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 |
| DE102010046981A1 (de) * | 2010-09-30 | 2012-04-05 | Ashland-Südchemie-Kernfest GmbH | Bindemittel enthaltend substituierte Benzole und Napthaline zur Herstellung von Kernen und Formen für den Metallguss, Formstoffmischung und Verfahren |
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 ES ES526112A patent/ES526112A0/es active Granted
- 1983-09-29 ZA ZA837306A patent/ZA837306B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0333142B2 (https=) | 1991-05-16 |
| ZA837306B (en) | 1984-05-30 |
| ES8504099A1 (es) | 1985-04-01 |
| ES526112A0 (es) | 1985-04-01 |
| EP0105161A1 (en) | 1984-04-11 |
| JPS5978136A (ja) | 1984-05-04 |
| US4420643A (en) | 1983-12-13 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEC | Expiry (correction) | ||
| MKEX | Expiry |