CA1311236C - Procede de separation supercritique pour des melanges organiques complexes - Google Patents
Procede de separation supercritique pour des melanges organiques complexesInfo
- Publication number
- CA1311236C CA1311236C CA000590134A CA590134A CA1311236C CA 1311236 C CA1311236 C CA 1311236C CA 000590134 A CA000590134 A CA 000590134A CA 590134 A CA590134 A CA 590134A CA 1311236 C CA1311236 C CA 1311236C
- Authority
- CA
- Canada
- Prior art keywords
- entrainer
- solution
- molecular weight
- low molecular
- carbon dioxide
- 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 - Fee Related
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 75
- 238000000926 separation method Methods 0.000 title claims abstract description 45
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims abstract description 117
- 238000000034 method Methods 0.000 claims abstract description 75
- 239000001569 carbon dioxide Substances 0.000 claims abstract description 58
- 229910002092 carbon dioxide Inorganic materials 0.000 claims abstract description 58
- 238000007614 solvation Methods 0.000 claims abstract description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 75
- 239000000243 solution Substances 0.000 claims description 73
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 37
- 229920005610 lignin Polymers 0.000 claims description 30
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 28
- 150000001875 compounds Chemical class 0.000 claims description 23
- 238000000605 extraction Methods 0.000 claims description 22
- 239000012634 fragment Substances 0.000 claims description 19
- 239000002253 acid Substances 0.000 claims description 17
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 16
- 150000007513 acids Chemical class 0.000 claims description 14
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 12
- 238000012545 processing Methods 0.000 claims description 12
- 239000002028 Biomass Substances 0.000 claims description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 9
- 150000001261 hydroxy acids Chemical class 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 8
- 150000002989 phenols Chemical class 0.000 claims description 8
- 150000001735 carboxylic acids Chemical class 0.000 claims description 7
- 239000002699 waste material Substances 0.000 claims description 7
- 150000001413 amino acids Chemical class 0.000 claims description 6
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 claims description 6
- 235000013824 polyphenols Nutrition 0.000 claims description 6
- 238000009835 boiling Methods 0.000 claims description 5
- 239000001913 cellulose Substances 0.000 claims description 5
- 229920002678 cellulose Polymers 0.000 claims description 5
- 238000004537 pulping Methods 0.000 claims description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 5
- 238000002955 isolation Methods 0.000 claims description 4
- 150000001720 carbohydrates Chemical class 0.000 claims description 3
- 235000014633 carbohydrates Nutrition 0.000 claims description 3
- -1 carboxylic acid compounds Chemical class 0.000 claims description 3
- 235000013351 cheese Nutrition 0.000 claims description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 238000001914 filtration Methods 0.000 claims description 2
- 239000000725 suspension Substances 0.000 claims description 2
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims 3
- 239000002023 wood Substances 0.000 claims 2
- 229920001273 Polyhydroxy acid Polymers 0.000 claims 1
- 239000012224 working solution Substances 0.000 claims 1
- DFYRUELUNQRZTB-UHFFFAOYSA-N apocynin Chemical compound COC1=CC(C(C)=O)=CC=C1O DFYRUELUNQRZTB-UHFFFAOYSA-N 0.000 description 10
- 239000012530 fluid Substances 0.000 description 9
- 238000002474 experimental method Methods 0.000 description 8
- 150000002500 ions Chemical class 0.000 description 7
- 239000002655 kraft paper Substances 0.000 description 7
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 239000002904 solvent Substances 0.000 description 5
- 229940024606 amino acid Drugs 0.000 description 4
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- 235000010323 ascorbic acid Nutrition 0.000 description 3
- 229960005070 ascorbic acid Drugs 0.000 description 3
- 239000011668 ascorbic acid Substances 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 239000000470 constituent Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 150000002894 organic compounds Chemical class 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- RGHNJXZEOKUKBD-SQOUGZDYSA-N D-gluconic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 229920002488 Hemicellulose Polymers 0.000 description 2
- 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 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 241000183024 Populus tremula Species 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 238000010420 art technique Methods 0.000 description 2
- 208000037516 chromosome inversion disease Diseases 0.000 description 2
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 2
- 239000004310 lactic acid Substances 0.000 description 2
- 235000014655 lactic acid Nutrition 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 239000000123 paper Substances 0.000 description 2
- 238000005504 petroleum refining Methods 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- WYUYEJNGHIOFOC-VVTVMFAVSA-N 2-[(z)-1-(4-methylphenyl)-3-pyrrolidin-1-ylprop-1-enyl]pyridine;hydrochloride Chemical compound Cl.C1=CC(C)=CC=C1C(\C=1N=CC=CC=1)=C\CN1CCCC1 WYUYEJNGHIOFOC-VVTVMFAVSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- QNAYBMKLOCPYGJ-UHFFFAOYSA-N D-alpha-Ala Natural products CC([NH3+])C([O-])=O QNAYBMKLOCPYGJ-UHFFFAOYSA-N 0.000 description 1
- RGHNJXZEOKUKBD-UHFFFAOYSA-N D-gluconic acid Natural products OCC(O)C(O)C(O)C(O)C(O)=O RGHNJXZEOKUKBD-UHFFFAOYSA-N 0.000 description 1
- QNAYBMKLOCPYGJ-UWTATZPHSA-N L-Alanine Natural products C[C@@H](N)C(O)=O QNAYBMKLOCPYGJ-UWTATZPHSA-N 0.000 description 1
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 description 1
- 235000008331 Pinus X rigitaeda Nutrition 0.000 description 1
- 241000018646 Pinus brutia Species 0.000 description 1
- 235000011613 Pinus brutia Nutrition 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- 239000005862 Whey Substances 0.000 description 1
- 102000007544 Whey Proteins Human genes 0.000 description 1
- 108010046377 Whey Proteins Proteins 0.000 description 1
- 229960003767 alanine Drugs 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000003965 capillary gas chromatography Methods 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 238000001311 chemical methods and process Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- MCWXGJITAZMZEV-UHFFFAOYSA-N dimethoate Chemical compound CNC(=O)CSP(=S)(OC)OC MCWXGJITAZMZEV-UHFFFAOYSA-N 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 239000000174 gluconic acid Substances 0.000 description 1
- 235000012208 gluconic acid Nutrition 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 239000012978 lignocellulosic material Substances 0.000 description 1
- HYVVJDQGXFXBRZ-UHFFFAOYSA-N metam Chemical compound CNC(S)=S HYVVJDQGXFXBRZ-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- HCTVWSOKIJULET-LQDWTQKMSA-M phenoxymethylpenicillin potassium Chemical compound [K+].N([C@H]1[C@H]2SC([C@@H](N2C1=O)C([O-])=O)(C)C)C(=O)COC1=CC=CC=C1 HCTVWSOKIJULET-LQDWTQKMSA-M 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000011403 purification operation Methods 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 238000000194 supercritical-fluid extraction Methods 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
Classifications
-
- D—TEXTILES; PAPER
- D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
- D21C—PRODUCTION OF CELLULOSE BY REMOVING NON-CELLULOSE SUBSTANCES FROM CELLULOSE-CONTAINING MATERIALS; REGENERATION OF PULPING LIQUORS; APPARATUS THEREFOR
- D21C11/00—Regeneration of pulp liquors or effluent waste waters
- D21C11/0007—Recovery of by-products, i.e. compounds other than those necessary for pulping, for multiple uses or not otherwise provided for
-
- 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
- B01D11/0403—Solvent extraction of solutions which are liquid with a supercritical fluid
- B01D11/0407—Solvent extraction of solutions which are liquid with a supercritical fluid the supercritical fluid acting as solvent for the solute
-
- 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
- C02F11/00—Treatment of sludge; Devices therefor
- C02F11/002—Sludge treatment using liquids immiscible with water
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Hydrology & Water Resources (AREA)
- Engineering & Computer Science (AREA)
- Environmental & Geological Engineering (AREA)
- Water Supply & Treatment (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Extraction Or Liquid Replacement (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US15421088A | 1988-02-10 | 1988-02-10 | |
| US154,210 | 1988-02-10 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1311236C true CA1311236C (fr) | 1992-12-08 |
Family
ID=22550449
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000590134A Expired - Fee Related CA1311236C (fr) | 1988-02-10 | 1989-02-03 | Procede de separation supercritique pour des melanges organiques complexes |
Country Status (3)
| Country | Link |
|---|---|
| AU (1) | AU3064189A (fr) |
| CA (1) | CA1311236C (fr) |
| WO (1) | WO1989007480A1 (fr) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5240603A (en) * | 1990-03-02 | 1993-08-31 | Hewlett-Packard Company | Decoupled flow and pressure setpoints in an extraction instrument using compressible fluids |
| DE19634111A1 (de) * | 1996-08-23 | 1998-02-26 | Eisenmann Ernst Dipl Ing Fh | Biomasseumsetzung zu Kraftstoffen mittels überkritischer Kohlensäure |
| US8048304B2 (en) | 2007-12-27 | 2011-11-01 | Dynasep Llc | Solvent extraction and recovery |
| CN111040880A (zh) * | 2020-01-08 | 2020-04-21 | 湖北中烟工业有限责任公司 | 一种高纯度芸香草精油的制备方法 |
| CN116065243B (zh) * | 2021-10-29 | 2025-06-10 | 中国石油化工股份有限公司 | 提高聚丙烯腈纺丝溶液固含量的方法 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2772965A (en) * | 1953-06-02 | 1956-12-04 | Rayonier Inc | Recovery of chemicals in wood pulp preparation |
| US3478109A (en) * | 1967-07-28 | 1969-11-11 | Eastman Kodak Co | Solvent extraction of polymeric glycols using methanol |
| US4349415A (en) * | 1979-09-28 | 1982-09-14 | Critical Fluid Systems, Inc. | Process for separating organic liquid solutes from their solvent mixtures |
| US4474994A (en) * | 1982-09-13 | 1984-10-02 | Monsanto Company | Purification of vanillin |
| US4770780A (en) * | 1984-04-25 | 1988-09-13 | Cf Systems Corporation | Liquid CO2 /cosolvent extraction |
| US4617090A (en) * | 1984-12-20 | 1986-10-14 | The United States Of America As Represented By The United States Department Of Energy | Process for producing peracids from aliphatic hydroxy carboxylic acids |
| US4584057A (en) * | 1985-04-22 | 1986-04-22 | The United States Of America As Represented By The Secretary Of Agriculture | Membrane processes for separation of organic acids from kraft black liquors |
| US4568447A (en) * | 1985-07-29 | 1986-02-04 | Uop Inc. | Process for the removal of trace quantities of hydrocarbonaceous compounds from an aqueous stream |
-
1989
- 1989-02-03 CA CA000590134A patent/CA1311236C/fr not_active Expired - Fee Related
- 1989-02-08 WO PCT/US1989/000494 patent/WO1989007480A1/fr not_active Ceased
- 1989-02-08 AU AU30641/89A patent/AU3064189A/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| WO1989007480A1 (fr) | 1989-08-24 |
| AU3064189A (en) | 1989-09-06 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US4964995A (en) | Supercritical separation process for complex organic mixtures | |
| AU2010278595B2 (en) | Method for extracting lignite wax | |
| US20160002358A1 (en) | Biomass processing using ionic liquids | |
| de França Serpa et al. | Extraction and characterization of lignins from cashew apple bagasse obtained by different treatments | |
| FI73962C (fi) | Foerfarande foer framstaellning av vanillin. | |
| CA1311236C (fr) | Procede de separation supercritique pour des melanges organiques complexes | |
| Dias et al. | Uncovering the potentialities of protic ionic liquids based on alkanolammonium and carboxylate ions and their aqueous solutions as non-derivatizing solvents of Kraft lignin | |
| JPH11292799A (ja) | 超臨界水処理による芳香族化合物の製造方法 | |
| WO2020013752A1 (fr) | Purification de lignine | |
| US20180030554A1 (en) | Biomass processing using ionic liquids | |
| Klett | Purification, fractionation, and characterization of lignin from Kraft black liquor for use as a renewable biomaterial | |
| EP3921386A1 (fr) | Procédé de production d'une bio-huile | |
| EP3502118A1 (fr) | Procédé de dépolymérisation de lignine ultra-rapide | |
| US3442753A (en) | Pulping or ligno-cellulosic material with a reaction product of triethyleneglycol and organic acid | |
| CA2842372A1 (fr) | Procede et systeme pour l'elimination de composes organiques dissous dans de l'eau de procede | |
| Gomes | Development of a continuous process for the production of vanillin and syringaldehyde from kraft black liquor | |
| Akim et al. | 13C NMR studies on lignins depolymerized with dry hydrogen iodide | |
| RU2134148C1 (ru) | Способ очистки пирогаза от сероводорода и двуокиси углерода | |
| FI127777B (en) | Extracted lignocellulosic material as adsorbent | |
| WO2020161313A1 (fr) | Procédé de production d'une bio-huile à l'aide d'une huile contenant de la rosin | |
| JP2003071204A (ja) | 被処理水からの水可溶性有機物の分離回収方法 | |
| FI98835B (fi) | Menetelmä kemiallisten komponenttien uuttamiseksi höyryräjähdysprosessilla hajotetusta lignoselluloosamateriaalista | |
| Zhou et al. | Sustainable hierarchical extraction of lignin with simultaneous recovery of acidic deep eutectic solvent | |
| Lê | Wood biorefinery concept based on γ-valerolactone/water fractionation | |
| US3453253A (en) | Method of selectively extracting the alkali metal salts of tall oil fatty and resin acids from alkaline black liquor |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKLA | Lapsed |