CA2176277A1 - Aldehyde-based surfactant and method for treating industrial, commercial, and institutional waste-water - Google Patents
Aldehyde-based surfactant and method for treating industrial, commercial, and institutional waste-waterInfo
- Publication number
- CA2176277A1 CA2176277A1 CA002176277A CA2176277A CA2176277A1 CA 2176277 A1 CA2176277 A1 CA 2176277A1 CA 002176277 A CA002176277 A CA 002176277A CA 2176277 A CA2176277 A CA 2176277A CA 2176277 A1 CA2176277 A1 CA 2176277A1
- Authority
- CA
- Canada
- Prior art keywords
- hydrogen
- aldehyde
- dioxolane
- hydrophobic
- residue
- 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
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 title abstract 3
- 239000004094 surface-active agent Substances 0.000 title abstract 3
- 239000002351 wastewater Substances 0.000 title 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 5
- 239000001257 hydrogen Substances 0.000 abstract 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 5
- 230000002209 hydrophobic effect Effects 0.000 abstract 4
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 abstract 2
- 125000004122 cyclic group Chemical group 0.000 abstract 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 2
- 239000002736 nonionic surfactant Substances 0.000 abstract 2
- 150000002894 organic compounds Chemical class 0.000 abstract 2
- VDFVNEFVBPFDSB-UHFFFAOYSA-N 1,3-dioxane Chemical compound C1COCOC1 VDFVNEFVBPFDSB-UHFFFAOYSA-N 0.000 abstract 1
- 125000006091 1,3-dioxolane group Chemical group 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 239000007864 aqueous solution Substances 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 239000000356 contaminant Substances 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- 239000000203 mixture Chemical group 0.000 abstract 1
- 229920005862 polyol Polymers 0.000 abstract 1
- 150000003077 polyols Chemical class 0.000 abstract 1
Classifications
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
- C09K23/017—Mixtures of compounds
- C09K23/018—Mixtures of two or more different organic oxygen-containing compounds
-
- 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
- C02F1/54—Treatment of water, waste water, or sewage by flocculation or precipitation of suspended impurities using organic material
- C02F1/547—Tensides
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/26—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds
- C08G65/2603—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing oxygen
- C08G65/2606—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing oxygen containing hydroxyl groups
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
- C09K23/42—Ethers, e.g. polyglycol ethers of alcohols or phenols
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/66—Non-ionic compounds
- C11D1/72—Ethers of polyoxyalkylene glycols
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/66—Non-ionic compounds
- C11D1/825—Mixtures of compounds all of which are non-ionic
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2650/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G2650/28—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule characterised by the polymer type
- C08G2650/38—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule characterised by the polymer type containing oxygen in addition to the ether group
- C08G2650/44—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule characterised by the polymer type containing oxygen in addition to the ether group containing acetal or formal groups
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/66—Non-ionic compounds
- C11D1/72—Ethers of polyoxyalkylene glycols
- C11D1/721—End blocked ethers
-
- C11D2111/12—
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S210/00—Liquid purification or separation
- Y10S210/902—Materials removed
- Y10S210/908—Organic
Abstract
A nonionic surfactant having cyclic 1,3-dioxane and/or 1,3-dioxolane functionality is irreversibly splittable by lowering the pH of its aqueous solution. The cyclic 1,3-dioxolane has the formula:
(see figure I) The 1,3-dioxolane has the formula:
(see figure II) of which R is hydrogen and R' has no alkoxy linkage and is the residue of an organic compound (substituted or unsubstituted) derived from an aldehyde of the formula (see figure III) wherein R is hydrogen and R' is the residue of an organic compound (substituted or unsubstituted) which contains a total of 8 to 20 carbon atoms and which contains no moieties or linkages which significantly interfere with the performance of the surfactant for its intended purpose; X is hydrogen or the residue of a hydrophobic end-cap; Y is hydrogen, methyl, ethyl, or mixtures thereof; Z is hydrogen, methyl, or ethyl; m is 0 or 1; and n is an integer of 1 to 40. After splitting of the surfactant into its components aldehyde and polyol, the hydrophobic components phase-separate and can be removed from the aqueous stream by routine means. The nonionic surfactant is useful in various processes requiring the removal of emulsified hydrophobic contaminants or other hydrophobic materials from an aqueous stream.
(see figure I) The 1,3-dioxolane has the formula:
(see figure II) of which R is hydrogen and R' has no alkoxy linkage and is the residue of an organic compound (substituted or unsubstituted) derived from an aldehyde of the formula (see figure III) wherein R is hydrogen and R' is the residue of an organic compound (substituted or unsubstituted) which contains a total of 8 to 20 carbon atoms and which contains no moieties or linkages which significantly interfere with the performance of the surfactant for its intended purpose; X is hydrogen or the residue of a hydrophobic end-cap; Y is hydrogen, methyl, ethyl, or mixtures thereof; Z is hydrogen, methyl, or ethyl; m is 0 or 1; and n is an integer of 1 to 40. After splitting of the surfactant into its components aldehyde and polyol, the hydrophobic components phase-separate and can be removed from the aqueous stream by routine means. The nonionic surfactant is useful in various processes requiring the removal of emulsified hydrophobic contaminants or other hydrophobic materials from an aqueous stream.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US08/439,964 | 1995-05-12 | ||
US08/439,964 US5744065A (en) | 1995-05-12 | 1995-05-12 | Aldehyde-based surfactant and method for treating industrial, commercial, and institutional waste-water |
Publications (2)
Publication Number | Publication Date |
---|---|
CA2176277A1 true CA2176277A1 (en) | 1996-11-13 |
CA2176277C CA2176277C (en) | 2001-07-03 |
Family
ID=23746857
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CA002176277A Expired - Fee Related CA2176277C (en) | 1995-05-12 | 1996-05-10 | Aldehyde-based surfactant and method for treating industrial, commercial, and institutional waste-water |
Country Status (9)
Country | Link |
---|---|
US (4) | US5744065A (en) |
EP (1) | EP0742177B1 (en) |
KR (1) | KR100329452B1 (en) |
CN (2) | CN1143536A (en) |
AU (1) | AU708763B2 (en) |
CA (1) | CA2176277C (en) |
DE (1) | DE69612421T2 (en) |
DK (1) | DK0742177T3 (en) |
MY (1) | MY132307A (en) |
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US5744064A (en) * | 1995-05-12 | 1998-04-28 | Union Carbide Chemicals & Plastics Technology Corporation | Ketone-based surfactant and method for treating industrial, commerical, and institutional waste-water |
US5744065A (en) * | 1995-05-12 | 1998-04-28 | Union Carbide Chemicals & Plastics Technology Corporation | Aldehyde-based surfactant and method for treating industrial, commercial, and institutional waste-water |
US6013185A (en) * | 1997-09-25 | 2000-01-11 | Rhodia Inc. | Recovery and reuse of nonionic surfactants from aqueous solutions |
DE19757904C1 (en) * | 1997-12-24 | 1999-07-22 | Celanese Gmbh | Process for the purification of waste water from an aldolization reaction with subsequent hydrogenation |
US6110231A (en) * | 1998-06-01 | 2000-08-29 | Boehme Filatex, Inc. | Method of processing textile products utilizing decomposable emulsifiers |
WO2002097393A2 (en) | 2001-05-29 | 2002-12-05 | Vanderbilt University | Cleavable surfactants and methods of use thereof |
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US20040118540A1 (en) * | 2002-12-20 | 2004-06-24 | Kimberly-Clark Worlwide, Inc. | Bicomponent strengtheninig system for paper |
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US7201227B2 (en) * | 2004-12-20 | 2007-04-10 | Bj Services Company | Method and composition for treating a subterranean formation with splittable foams |
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CA2665579C (en) | 2006-10-06 | 2015-06-30 | Robert C. Yeggy | Separating compositions and methods of use |
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US8062512B2 (en) * | 2006-10-06 | 2011-11-22 | Vary Petrochem, Llc | Processes for bitumen separation |
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JP5364319B2 (en) * | 2007-09-14 | 2013-12-11 | 花王株式会社 | Alkali-type nonionic surfactant composition |
US7816305B2 (en) * | 2008-05-15 | 2010-10-19 | Halliburton Energy Services, Inc. | Reversible surfactants and methods of use in subterranean formations |
EP2135989B1 (en) * | 2008-06-19 | 2015-03-04 | Electrolux Home Products Corporation N.V. | Washing method and washing machine implementing this method |
CA2736636A1 (en) * | 2008-09-25 | 2010-04-01 | Segetis, Inc. | Ketal ester derivatives |
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CN101962531B (en) * | 2009-07-22 | 2013-07-24 | 李英范 | Multi-functional poly-inorganic salt flooding synergist for tertiary oil recovery and production method thereof |
ES2400266T3 (en) | 2009-10-02 | 2013-04-08 | Cognis Ip Management Gmbh | Alkoxylated glycerol acetals and their derivatives |
WO2011143242A2 (en) | 2010-05-10 | 2011-11-17 | Segetis, Inc. | Fragrant formulations, methods of manufacture thereof and articles comprising the same |
US8828917B2 (en) | 2010-08-12 | 2014-09-09 | Segetis, Inc. | Carboxy ester ketal removal compositions, methods of manufacture, and uses thereof |
US9074065B2 (en) | 2010-08-12 | 2015-07-07 | Segetis, Inc. | Latex coating compositions including carboxy ester ketal coalescents, methods of manufacture, and uses thereof |
US8632612B2 (en) | 2010-09-07 | 2014-01-21 | Segetis, Inc. | Compositions for dyeing keratin fibers |
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US8349777B2 (en) * | 2010-11-22 | 2013-01-08 | Chevron Oronite Company Llc | Lubricating composition containing 1,3-dioxolane-4-methanol compounds as antiwear additives |
US10633579B2 (en) | 2011-08-01 | 2020-04-28 | Rhodia Operations | Use of environmentally friendly solvents to replace glycol-based solvents |
CN103930619B (en) | 2011-08-25 | 2016-12-07 | 索理思科技开曼公司 | The method increasing strength aid advantage in manufacturing paper and cardboard |
KR101904824B1 (en) * | 2011-09-06 | 2018-11-29 | 리쿠아비스타 비.브이. | Surfactant and method of manufacturing electrowetting display devices uisng the same |
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US9777434B2 (en) | 2011-12-22 | 2017-10-03 | Kemira Dyj | Compositions and methods of making paper products |
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US10624986B2 (en) | 2012-09-26 | 2020-04-21 | Kemira Oyj | Absorbent materials, products including absorbent materials, compositions, and methods of making absorbent materials |
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US5744065A (en) * | 1995-05-12 | 1998-04-28 | Union Carbide Chemicals & Plastics Technology Corporation | Aldehyde-based surfactant and method for treating industrial, commercial, and institutional waste-water |
US5744064A (en) * | 1995-05-12 | 1998-04-28 | Union Carbide Chemicals & Plastics Technology Corporation | Ketone-based surfactant and method for treating industrial, commerical, and institutional waste-water |
-
1995
- 1995-05-12 US US08/439,964 patent/US5744065A/en not_active Expired - Lifetime
-
1996
- 1996-05-10 CA CA002176277A patent/CA2176277C/en not_active Expired - Fee Related
- 1996-05-10 DE DE69612421T patent/DE69612421T2/en not_active Expired - Fee Related
- 1996-05-10 AU AU52223/96A patent/AU708763B2/en not_active Ceased
- 1996-05-10 KR KR1019960015340A patent/KR100329452B1/en not_active IP Right Cessation
- 1996-05-10 MY MYPI96001781A patent/MY132307A/en unknown
- 1996-05-10 DK DK96303260T patent/DK0742177T3/en active
- 1996-05-10 EP EP96303260A patent/EP0742177B1/en not_active Expired - Lifetime
- 1996-05-11 CN CN96108406A patent/CN1143536A/en active Pending
-
1997
- 1997-12-04 US US08/985,006 patent/US5919372A/en not_active Expired - Fee Related
-
1999
- 1999-03-03 US US09/261,371 patent/US6051035A/en not_active Expired - Fee Related
-
2000
- 2000-02-24 US US09/511,838 patent/US6306249B1/en not_active Expired - Fee Related
-
2001
- 2001-07-17 CN CN01123062A patent/CN1385509A/en active Pending
Also Published As
Publication number | Publication date |
---|---|
DK0742177T3 (en) | 2001-07-23 |
DE69612421T2 (en) | 2001-11-22 |
KR960041066A (en) | 1996-12-17 |
CA2176277C (en) | 2001-07-03 |
US5744065A (en) | 1998-04-28 |
MY132307A (en) | 2007-10-31 |
KR100329452B1 (en) | 2002-10-11 |
CN1385509A (en) | 2002-12-18 |
CN1143536A (en) | 1997-02-26 |
US6051035A (en) | 2000-04-18 |
AU5222396A (en) | 1996-11-21 |
US6306249B1 (en) | 2001-10-23 |
EP0742177A1 (en) | 1996-11-13 |
EP0742177B1 (en) | 2001-04-11 |
AU708763B2 (en) | 1999-08-12 |
US5919372A (en) | 1999-07-06 |
DE69612421D1 (en) | 2001-05-17 |
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