CA1206118A - Process for the separation of a glycol from an electrolite-containing aqueous solution - Google Patents
Process for the separation of a glycol from an electrolite-containing aqueous solutionInfo
- Publication number
- CA1206118A CA1206118A CA000423204A CA423204A CA1206118A CA 1206118 A CA1206118 A CA 1206118A CA 000423204 A CA000423204 A CA 000423204A CA 423204 A CA423204 A CA 423204A CA 1206118 A CA1206118 A CA 1206118A
- Authority
- CA
- Canada
- Prior art keywords
- glycol
- compartment
- solution
- water
- salt
- 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
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 title claims abstract description 110
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 title claims abstract description 51
- 238000000034 method Methods 0.000 title claims abstract description 35
- 239000007864 aqueous solution Substances 0.000 title abstract description 8
- 238000000926 separation method Methods 0.000 title abstract description 6
- 239000012528 membrane Substances 0.000 claims abstract description 33
- 239000000243 solution Substances 0.000 claims abstract description 16
- 239000003792 electrolyte Substances 0.000 claims abstract description 12
- 238000000909 electrodialysis Methods 0.000 claims abstract description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 26
- 150000003839 salts Chemical class 0.000 claims description 12
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 11
- 230000004907 flux Effects 0.000 claims description 11
- 150000002334 glycols Chemical class 0.000 claims description 11
- 238000002360 preparation method Methods 0.000 claims description 8
- 150000001450 anions Chemical class 0.000 claims description 7
- 150000001768 cations Chemical class 0.000 claims description 7
- 239000002351 wastewater Substances 0.000 claims description 7
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims description 6
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 4
- -1 alkoxy alcohol Chemical compound 0.000 claims description 4
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical class CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 claims description 4
- 230000003647 oxidation Effects 0.000 claims description 4
- 238000007254 oxidation reaction Methods 0.000 claims description 4
- 239000011780 sodium chloride Substances 0.000 claims description 4
- 239000003054 catalyst Substances 0.000 claims description 3
- 230000007062 hydrolysis Effects 0.000 claims description 3
- 238000006460 hydrolysis reaction Methods 0.000 claims description 3
- 239000003345 natural gas Substances 0.000 claims description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 2
- 238000010521 absorption reaction Methods 0.000 claims description 2
- 238000001035 drying Methods 0.000 claims description 2
- 239000008151 electrolyte solution Substances 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 230000008929 regeneration Effects 0.000 claims description 2
- 238000011069 regeneration method Methods 0.000 claims description 2
- 239000004711 α-olefin Substances 0.000 claims description 2
- 238000006384 oligomerization reaction Methods 0.000 claims 2
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 9
- 239000011148 porous material Substances 0.000 description 9
- 210000004027 cell Anatomy 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- 238000012546 transfer Methods 0.000 description 5
- 239000000463 material Substances 0.000 description 4
- 238000001223 reverse osmosis Methods 0.000 description 4
- 239000012266 salt solution Substances 0.000 description 4
- 239000012141 concentrate Substances 0.000 description 3
- 235000008504 concentrate Nutrition 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 150000002500 ions Chemical class 0.000 description 3
- YPFDHNVEDLHUCE-UHFFFAOYSA-N propane-1,3-diol Chemical compound OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 3
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 235000019254 sodium formate Nutrition 0.000 description 2
- HLBBKKJFGFRGMU-UHFFFAOYSA-M sodium formate Chemical compound [Na+].[O-]C=O HLBBKKJFGFRGMU-UHFFFAOYSA-M 0.000 description 2
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 2
- 239000002699 waste material Substances 0.000 description 2
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-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
- 108010053481 Antifreeze Proteins Proteins 0.000 description 1
- 101000837192 Drosophila melanogaster Teneurin-m Proteins 0.000 description 1
- 239000005977 Ethylene Substances 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
- 239000004280 Sodium formate Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 230000002528 anti-freeze Effects 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 235000012206 bottled water Nutrition 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- MYSWGUAQZAJSOK-UHFFFAOYSA-N ciprofloxacin Chemical compound C12=CC(N3CCNCC3)=C(F)C=C2C(=O)C(C(=O)O)=CN1C1CC1 MYSWGUAQZAJSOK-UHFFFAOYSA-N 0.000 description 1
- 230000002328 demineralizing effect Effects 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 238000000502 dialysis Methods 0.000 description 1
- 239000003651 drinking water Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- CAPAZTWTGPAFQE-UHFFFAOYSA-N ethane-1,2-diol Chemical compound OCCO.OCCO CAPAZTWTGPAFQE-UHFFFAOYSA-N 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 238000012994 industrial processing Methods 0.000 description 1
- VUZPPFZMUPKLLV-UHFFFAOYSA-N methane;hydrate Chemical compound C.O VUZPPFZMUPKLLV-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000005416 organic matter Substances 0.000 description 1
- 230000003204 osmotic effect Effects 0.000 description 1
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 1
- 210000003429 pore cell Anatomy 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- QHGVXILFMXYDRS-UHFFFAOYSA-N pyraclofos Chemical compound C1=C(OP(=O)(OCC)SCCC)C=NN1C1=CC=C(Cl)C=C1 QHGVXILFMXYDRS-UHFFFAOYSA-N 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D61/00—Processes of separation using semi-permeable membranes, e.g. dialysis, osmosis or ultrafiltration; Apparatus, accessories or auxiliary operations specially adapted therefor
- B01D61/42—Electrodialysis; Electro-osmosis ; Electro-ultrafiltration; Membrane capacitive deionization
- B01D61/44—Ion-selective electrodialysis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2/00—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms
- C07C2/02—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons
- C07C2/04—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons by oligomerisation of well-defined unsaturated hydrocarbons without ring formation
- C07C2/06—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons by oligomerisation of well-defined unsaturated hydrocarbons without ring formation of alkenes, i.e. acyclic hydrocarbons having only one carbon-to-carbon double bond
- C07C2/08—Catalytic processes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/74—Separation; Purification; Use of additives, e.g. for stabilisation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/74—Separation; Purification; Use of additives, e.g. for stabilisation
- C07C29/76—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C31/00—Saturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C31/18—Polyhydroxylic acyclic alcohols
- C07C31/20—Dihydroxylic alcohols
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C7/00—Purification; Separation; Use of additives
- C07C7/11—Purification; Separation; Use of additives by absorption, i.e. purification or separation of gaseous hydrocarbons with the aid of liquids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Water Supply & Treatment (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Analytical Chemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Health & Medical Sciences (AREA)
- Urology & Nephrology (AREA)
- Separation Using Semi-Permeable Membranes (AREA)
- Water Treatment By Electricity Or Magnetism (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL8201174 | 1982-03-22 | ||
| NL8201174 | 1982-03-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1206118A true CA1206118A (en) | 1986-06-17 |
Family
ID=19839452
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000423204A Expired CA1206118A (en) | 1982-03-22 | 1983-03-09 | Process for the separation of a glycol from an electrolite-containing aqueous solution |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US4427507A (https=) |
| EP (1) | EP0089704B1 (https=) |
| JP (1) | JPS58170505A (https=) |
| CA (1) | CA1206118A (https=) |
| DE (1) | DE3381559D1 (https=) |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4810340A (en) * | 1986-11-13 | 1989-03-07 | Shell Oil Company | Process for recovering organic values from aqueous solutions containing both organic values and scale-forming ions |
| DE3721474A1 (de) * | 1987-06-30 | 1989-01-12 | Huels Chemische Werke Ag | Verfahren zur herstellung von hexadiin(2,4)-diol-1,6 |
| US4822926A (en) * | 1988-02-29 | 1989-04-18 | Shell Oil Company | Ethylene oxide/glycols recovery process |
| FR2637510B1 (fr) * | 1988-10-07 | 1991-01-11 | Meridional Oenologie Centre | Procedes et dispositifs pour secher de l'air a basse temperature |
| US5102549A (en) | 1989-12-27 | 1992-04-07 | Union Carbide Chemicals & Plastics Technology Corporation | Treatment of lower glycol-containing operative fluids |
| US5194159A (en) * | 1989-12-27 | 1993-03-16 | Union Carbide Chemicals & Plastics Technology Corporation | Treatment of lower glycol-containing operative fluids |
| US5034134A (en) * | 1989-12-27 | 1991-07-23 | Union Carbide Chemicals And Plastics Technology Corporation | Treatment of impurity-containing liquid streams in ethylene oxide/glycol processes with semi-permeable membranes |
| FR2711650B1 (fr) * | 1993-10-29 | 1995-12-01 | Elf Aquitaine | Procédé de purification d'une solution glycolique à base d'un ou plusieurs glycols et renfermant, en outre, de l'eau et, à titre d'impuretés, des sels et des hydrocarbures. |
| US6023003A (en) * | 1998-01-13 | 2000-02-08 | Reading & Bates Development Co. | Process and system for recovering glycol from glycol/brine streams |
| DE19803675A1 (de) * | 1998-01-30 | 1999-08-05 | Basf Ag | Verfahren zur Herstellung von Alkylenglykol |
| DE19838425A1 (de) * | 1998-08-24 | 2000-03-02 | Degussa | Verfahren zur Abtrennung mehrfunktioneller Alkohole von wasserlöslichen Salzen aus wäßrigen Systemen |
| US6187197B1 (en) * | 1998-10-28 | 2001-02-13 | Marvin Haddock | Multi-stage engine coolant recycling process |
| US6274020B1 (en) * | 2000-04-28 | 2001-08-14 | Ernst Schmidt | Electrodialysis membrane and gasket stack system |
| JP3671917B2 (ja) * | 2002-02-08 | 2005-07-13 | 日産自動車株式会社 | 燃料電池システム |
| US20030155243A1 (en) * | 2002-02-21 | 2003-08-21 | Eet Corporation | Multi-path split cell spacer and electrodialysis stack design |
| FR2846323B1 (fr) * | 2002-10-28 | 2004-12-10 | Inst Francais Du Petrole | Procede de regeneration d'une solution aqueuse de glycol contenant des sels |
| AR067384A1 (es) * | 2007-06-29 | 2009-10-07 | Archer Daniels Midland Co | Proceso para desalar soluciones de glicerol y recuperacion de sustancias quimicas |
| PL217778B1 (pl) * | 2011-06-20 | 2014-08-29 | Piotr Medoń | Sposób osuszania glikolu i układ do osuszania glikolu |
| JP5305309B2 (ja) * | 2011-11-28 | 2013-10-02 | 株式会社Ｍｏｒｅｓｃｏ | グリコールまたはグリコール水溶液の回収方法 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2860091A (en) * | 1955-09-22 | 1958-11-11 | Ionics | Treatment of polyhydric solutions |
| US2865822A (en) | 1956-04-30 | 1958-12-23 | Warren Petroleum Corp Inc | Method for deionizing aqueous pentaerythritol solutions |
| US3030287A (en) * | 1957-10-26 | 1962-04-17 | Benckiser Gmbh Joh A | Method for the removal of small quantities of strong electrolytes from solutions of weak electrolytes |
| US3192143A (en) | 1962-06-28 | 1965-06-29 | Shell Oil Co | Electrodialytic demineralization of water |
| US3779883A (en) | 1972-11-03 | 1973-12-18 | Sybron Corp | Pentaerythritol purification process |
| DE2350567A1 (de) | 1973-10-09 | 1975-04-10 | Hoechst Ag | Wiedergewinnung von glykol aus salzhaltigem abwasser |
| JPS561049A (en) * | 1979-06-15 | 1981-01-08 | Fuji Photo Film Co Ltd | Regenerating method for waste photographic processing solution |
-
1982
- 1982-10-06 US US06/433,065 patent/US4427507A/en not_active Expired - Lifetime
-
1983
- 1983-02-25 DE DE8383200284T patent/DE3381559D1/de not_active Expired - Lifetime
- 1983-02-25 EP EP19830200284 patent/EP0089704B1/en not_active Expired - Lifetime
- 1983-03-09 CA CA000423204A patent/CA1206118A/en not_active Expired
- 1983-03-22 JP JP58046125A patent/JPS58170505A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| EP0089704A2 (en) | 1983-09-28 |
| EP0089704A3 (en) | 1987-02-04 |
| JPS58170505A (ja) | 1983-10-07 |
| DE3381559D1 (de) | 1990-06-21 |
| EP0089704B1 (en) | 1990-05-16 |
| US4427507A (en) | 1984-01-24 |
| JPH042290B2 (https=) | 1992-01-17 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |