CA2911456C - Procede de valorisation de produits derives d'une biomasse, par utilisation d'une extraction liquide-liquide - Google Patents
Procede de valorisation de produits derives d'une biomasse, par utilisation d'une extraction liquide-liquide Download PDFInfo
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- CA2911456C CA2911456C CA2911456A CA2911456A CA2911456C CA 2911456 C CA2911456 C CA 2911456C CA 2911456 A CA2911456 A CA 2911456A CA 2911456 A CA2911456 A CA 2911456A CA 2911456 C CA2911456 C CA 2911456C
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- Prior art keywords
- mixture
- extraction
- water
- oil
- organics
- Prior art date
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- 238000000034 method Methods 0.000 title claims abstract description 86
- 230000008569 process Effects 0.000 title claims abstract description 47
- 239000002028 Biomass Substances 0.000 title claims abstract description 44
- 238000000638 solvent extraction Methods 0.000 title abstract description 9
- 238000000622 liquid--liquid extraction Methods 0.000 title abstract description 7
- 239000000203 mixture Substances 0.000 claims abstract description 205
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- 239000000047 product Substances 0.000 claims abstract description 89
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- 229910052799 carbon Inorganic materials 0.000 claims abstract description 57
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 46
- 239000007787 solid Substances 0.000 claims abstract description 45
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- 239000003921 oil Substances 0.000 claims description 114
- 238000000605 extraction Methods 0.000 claims description 111
- 239000012075 bio-oil Substances 0.000 claims description 97
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 claims description 77
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 claims description 77
- 239000008346 aqueous phase Substances 0.000 claims description 75
- 239000002904 solvent Substances 0.000 claims description 55
- 125000004432 carbon atom Chemical group C* 0.000 claims description 21
- 239000007795 chemical reaction product Substances 0.000 claims description 13
- 239000013067 intermediate product Substances 0.000 claims description 13
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- 238000009835 boiling Methods 0.000 claims description 6
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- YCOXTKKNXUZSKD-UHFFFAOYSA-N 3,4-xylenol Chemical compound CC1=CC=C(O)C=C1C YCOXTKKNXUZSKD-UHFFFAOYSA-N 0.000 description 4
- HMNKTRSOROOSPP-UHFFFAOYSA-N 3-Ethylphenol Chemical compound CCC1=CC=CC(O)=C1 HMNKTRSOROOSPP-UHFFFAOYSA-N 0.000 description 4
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- LHGVFZTZFXWLCP-UHFFFAOYSA-N guaiacol Chemical compound COC1=CC=CC=C1O LHGVFZTZFXWLCP-UHFFFAOYSA-N 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 229960004337 hydroquinone Drugs 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- 238000001095 inductively coupled plasma mass spectrometry Methods 0.000 description 2
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 2
- BTFQKIATRPGRBS-UHFFFAOYSA-N o-tolualdehyde Chemical compound CC1=CC=CC=C1C=O BTFQKIATRPGRBS-UHFFFAOYSA-N 0.000 description 2
- XNLICIUVMPYHGG-UHFFFAOYSA-N pentan-2-one Chemical compound CCCC(C)=O XNLICIUVMPYHGG-UHFFFAOYSA-N 0.000 description 2
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 2
- TZMFJUDUGYTVRY-UHFFFAOYSA-N pentane-2,3-dione Chemical compound CCC(=O)C(C)=O TZMFJUDUGYTVRY-UHFFFAOYSA-N 0.000 description 2
- 150000002978 peroxides Chemical class 0.000 description 2
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 2
- 239000010734 process oil Substances 0.000 description 2
- ODLMAHJVESYWTB-UHFFFAOYSA-N propylbenzene Chemical compound CCCC1=CC=CC=C1 ODLMAHJVESYWTB-UHFFFAOYSA-N 0.000 description 2
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 2
- NXLOLUFNDSBYTP-UHFFFAOYSA-N retene Chemical compound C1=CC=C2C3=CC=C(C(C)C)C=C3C=CC2=C1C NXLOLUFNDSBYTP-UHFFFAOYSA-N 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000002699 waste material Substances 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- LABTWGUMFABVFG-ONEGZZNKSA-N (3E)-pent-3-en-2-one Chemical compound C\C=C\C(C)=O LABTWGUMFABVFG-ONEGZZNKSA-N 0.000 description 1
- FTNJQNQLEGKTGD-UHFFFAOYSA-N 1,3-benzodioxole Chemical compound C1=CC=C2OCOC2=C1 FTNJQNQLEGKTGD-UHFFFAOYSA-N 0.000 description 1
- DZTYCPNBSJZKSS-UHFFFAOYSA-N 1,3-dimethyl-1h-indene Chemical compound C1=CC=C2C(C)C=C(C)C2=C1 DZTYCPNBSJZKSS-UHFFFAOYSA-N 0.000 description 1
- LRTOHSLOFCWHRF-UHFFFAOYSA-N 1-methyl-1h-indene Chemical compound C1=CC=C2C(C)C=CC2=C1 LRTOHSLOFCWHRF-UHFFFAOYSA-N 0.000 description 1
- QDXQAOGNBCOEQX-UHFFFAOYSA-N 1-methylcyclohexa-1,4-diene Chemical compound CC1=CCC=CC1 QDXQAOGNBCOEQX-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
- JLIDVCMBCGBIEY-UHFFFAOYSA-N 1-penten-3-one Chemical compound CCC(=O)C=C JLIDVCMBCGBIEY-UHFFFAOYSA-N 0.000 description 1
- UDHZFLBMZZVHRA-UHFFFAOYSA-N 2-(furan-2-yl)furan Chemical compound C1=COC(C=2OC=CC=2)=C1 UDHZFLBMZZVHRA-UHFFFAOYSA-N 0.000 description 1
- 239000001431 2-methylbenzaldehyde Substances 0.000 description 1
- SRJCJJKWVSSELL-UHFFFAOYSA-N 2-methylnaphthalen-1-ol Chemical compound C1=CC=CC2=C(O)C(C)=CC=C21 SRJCJJKWVSSELL-UHFFFAOYSA-N 0.000 description 1
- NOEGNKMFWQHSLB-UHFFFAOYSA-N 5-hydroxymethylfurfural Chemical compound OCC1=CC=C(C=O)O1 NOEGNKMFWQHSLB-UHFFFAOYSA-N 0.000 description 1
- 241000609240 Ambelania acida Species 0.000 description 1
- TXVHTIQJNYSSKO-UHFFFAOYSA-N BeP Natural products C1=CC=C2C3=CC=CC=C3C3=CC=CC4=CC=C1C2=C34 TXVHTIQJNYSSKO-UHFFFAOYSA-N 0.000 description 1
- 101100336279 Caenorhabditis elegans icl-1 gene Proteins 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical class NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 1
- NPBVQXIMTZKSBA-UHFFFAOYSA-N Chavibetol Natural products COC1=CC=C(CC=C)C=C1O NPBVQXIMTZKSBA-UHFFFAOYSA-N 0.000 description 1
- 241000195493 Cryptophyta Species 0.000 description 1
- 244000166124 Eucalyptus globulus Species 0.000 description 1
- 239000005770 Eugenol Substances 0.000 description 1
- 229920002488 Hemicellulose Polymers 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- SXQBHARYMNFBPS-UHFFFAOYSA-N Indeno[1,2,3-cd]pyrene Chemical compound C=1C(C2=CC=CC=C22)=C3C2=CC=C(C=C2)C3=C3C2=CC=CC3=1 SXQBHARYMNFBPS-UHFFFAOYSA-N 0.000 description 1
- 238000003109 Karl Fischer titration Methods 0.000 description 1
- STNJBCKSHOAVAJ-UHFFFAOYSA-N Methacrolein Chemical compound CC(=C)C=O STNJBCKSHOAVAJ-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 241001520808 Panicum virgatum Species 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- UVMRYBDEERADNV-UHFFFAOYSA-N Pseudoeugenol Natural products COC1=CC(C(C)=C)=CC=C1O UVMRYBDEERADNV-UHFFFAOYSA-N 0.000 description 1
- 240000000111 Saccharum officinarum Species 0.000 description 1
- 235000007201 Saccharum officinarum Nutrition 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- 229910021536 Zeolite Inorganic materials 0.000 description 1
- ZEEBGORNQSEQBE-UHFFFAOYSA-N [2-(3-phenylphenoxy)-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound C1(=CC(=CC=C1)OC1=NC(=CC(=C1)CN)C(F)(F)F)C1=CC=CC=C1 ZEEBGORNQSEQBE-UHFFFAOYSA-N 0.000 description 1
- 125000004054 acenaphthylenyl group Chemical group C1(=CC2=CC=CC3=CC=CC1=C23)* 0.000 description 1
- 150000001243 acetic acids Chemical class 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000002154 agricultural waste Substances 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 150000004996 alkyl benzenes Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 239000012223 aqueous fraction Substances 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 239000010905 bagasse Substances 0.000 description 1
- RFRXIWQYSOIBDI-UHFFFAOYSA-N benzarone Chemical compound CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC=C(O)C=C1 RFRXIWQYSOIBDI-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 239000011111 cardboard Substances 0.000 description 1
- 239000012876 carrier material Substances 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 239000010779 crude oil Substances 0.000 description 1
- UBKHHFOBCZFFKL-UHFFFAOYSA-N cyclopenta[c]pyran Chemical compound C1=COC=C2C=CC=C21 UBKHHFOBCZFFKL-UHFFFAOYSA-N 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 230000005611 electricity Effects 0.000 description 1
- SRCZQMGIVIYBBJ-UHFFFAOYSA-N ethoxyethane;ethyl acetate Chemical compound CCOCC.CCOC(C)=O SRCZQMGIVIYBBJ-UHFFFAOYSA-N 0.000 description 1
- 229960002217 eugenol Drugs 0.000 description 1
- 238000001722 flash pyrolysis Methods 0.000 description 1
- 229960001867 guaiacol Drugs 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- RJGBSYZFOCAGQY-UHFFFAOYSA-N hydroxymethylfurfural Natural products COC1=CC=C(C=O)O1 RJGBSYZFOCAGQY-UHFFFAOYSA-N 0.000 description 1
- RKZJFAONHOYOKU-UHFFFAOYSA-N indeno[1,2,3-cd]pyrene Natural products C1Cc2ccc3ccc4c5ccccc5c6cc(=C1)c2c3c46 RKZJFAONHOYOKU-UHFFFAOYSA-N 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- KXUHSQYYJYAXGZ-UHFFFAOYSA-N isobutylbenzene Chemical compound CC(C)CC1=CC=CC=C1 KXUHSQYYJYAXGZ-UHFFFAOYSA-N 0.000 description 1
- TWNIBLMWSKIRAT-VFUOTHLCSA-N levoglucosan Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@H]2CO[C@@H]1O2 TWNIBLMWSKIRAT-VFUOTHLCSA-N 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- 239000012978 lignocellulosic material Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 229940078552 o-xylene Drugs 0.000 description 1
- 239000011087 paperboard Substances 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 150000004672 propanoic acids Chemical class 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000013049 sediment Substances 0.000 description 1
- 239000011949 solid catalyst Substances 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 238000009987 spinning Methods 0.000 description 1
- 238000013112 stability test Methods 0.000 description 1
- 239000010907 stover Substances 0.000 description 1
- 239000010902 straw Substances 0.000 description 1
- 230000008646 thermal stress Effects 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 238000003809 water extraction Methods 0.000 description 1
- 239000010925 yard waste Substances 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B1/00—Production of fats or fatty oils from raw materials
-
- 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
- B01D11/0492—Applications, solvents used
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
- Extraction Or Liquid Replacement (AREA)
Abstract
L'invention porte sur un procédé pour altérer le rapport entre les densités de la phase huileuse et de la phase aqueuse résultant de la conversion d'une biomasse en produits liquides, la réduction de la conductivité et de métaux du mélange produit, dont chacune peut aider à l'enlèvement des matières solides contenues dans la phase huileuse ; et un procédé d'extraction liquide-liquide pour partager les composés contenant du carbone souhaitable dans la phase huileuse et les composés contenant du carbone indésirable dans la phase aqueuse.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US13/889,105 | 2013-05-07 | ||
| US13/889,105 US9387415B2 (en) | 2011-08-18 | 2013-05-07 | Process for upgrading biomass derived products using liquid-liquid extraction |
| PCT/US2014/035804 WO2014182499A1 (fr) | 2013-05-07 | 2014-04-29 | Procédé de valorisation de produits dérivés d'une biomasse, par utilisation d'une extraction liquide-liquide |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2911456A1 CA2911456A1 (fr) | 2014-11-13 |
| CA2911456C true CA2911456C (fr) | 2021-04-27 |
Family
ID=51867643
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2911456A Expired - Fee Related CA2911456C (fr) | 2013-05-07 | 2014-04-29 | Procede de valorisation de produits derives d'une biomasse, par utilisation d'une extraction liquide-liquide |
Country Status (3)
| Country | Link |
|---|---|
| EP (1) | EP2994209A4 (fr) |
| CA (1) | CA2911456C (fr) |
| WO (1) | WO2014182499A1 (fr) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US10427069B2 (en) | 2011-08-18 | 2019-10-01 | Inaeris Technologies, Llc | Process for upgrading biomass derived products using liquid-liquid extraction |
| CA3031344A1 (fr) * | 2016-07-11 | 2018-01-18 | Inaeris Technologies, Llc | Procede de valorisation de produits derives d'une biomasse par extraction liquide-liquide |
| FI128345B (en) | 2016-08-05 | 2020-03-31 | Neste Oyj | Method for cleaning the feed |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4405448A (en) * | 1982-03-31 | 1983-09-20 | Googin John M | Process for removing halogenated aliphatic and aromatic compounds from petroleum products |
| US4960507A (en) * | 1989-03-20 | 1990-10-02 | Shell Oil Company | Two-step heterocyclic nitrogen extraction from petroleum oils |
| EE04818B1 (et) * | 1999-05-24 | 2007-04-16 | James W. Bunger And Associates, Inc. | Protsess süsivesinikuliste looduslike ressurssideväärtuse suurendamiseks |
| US6416655B1 (en) * | 1999-07-23 | 2002-07-09 | Exxonmobil Research And Engineering Company | Selective extraction using mixed solvent system |
| DE102004020113A1 (de) * | 2004-04-24 | 2005-11-17 | Bayer Materialscience Ag | Extraktion phenolhaltiger Abwasserströme |
| US8076504B2 (en) * | 2007-12-31 | 2011-12-13 | The University Of North Dakota | Method for production of short chain carboxylic acids and esters from biomass and product of same |
| US8211308B2 (en) * | 2010-04-06 | 2012-07-03 | Heliae Development, Llc | Extraction of polar lipids by a two solvent method |
| US9028696B2 (en) * | 2010-07-26 | 2015-05-12 | Sapphire Energy, Inc. | Process for the recovery of oleaginous compounds from biomass |
-
2014
- 2014-04-29 EP EP14794254.4A patent/EP2994209A4/fr not_active Withdrawn
- 2014-04-29 CA CA2911456A patent/CA2911456C/fr not_active Expired - Fee Related
- 2014-04-29 WO PCT/US2014/035804 patent/WO2014182499A1/fr active Application Filing
Also Published As
| Publication number | Publication date |
|---|---|
| EP2994209A1 (fr) | 2016-03-16 |
| EP2994209A4 (fr) | 2017-01-25 |
| WO2014182499A1 (fr) | 2014-11-13 |
| CA2911456A1 (fr) | 2014-11-13 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request |
Effective date: 20190118 |
|
| MKLA | Lapsed |
Effective date: 20220429 |