EP3215247A1 - Procédé d'obtention de produits de valeur aromatiques à partir de compositions contenant de la lignine - Google Patents
Procédé d'obtention de produits de valeur aromatiques à partir de compositions contenant de la lignineInfo
- Publication number
- EP3215247A1 EP3215247A1 EP15790940.9A EP15790940A EP3215247A1 EP 3215247 A1 EP3215247 A1 EP 3215247A1 EP 15790940 A EP15790940 A EP 15790940A EP 3215247 A1 EP3215247 A1 EP 3215247A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- activated carbon
- aqueous
- lignin
- aromatic
- aromatic compounds
- 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.)
- Withdrawn
Links
- 229920005610 lignin Polymers 0.000 title claims abstract description 88
- 239000000203 mixture Substances 0.000 title claims abstract description 88
- 238000000034 method Methods 0.000 title claims abstract description 71
- 125000003118 aryl group Chemical group 0.000 title description 38
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 248
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 49
- 238000003795 desorption Methods 0.000 claims abstract description 45
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims abstract description 31
- 239000003960 organic solvent Substances 0.000 claims abstract description 25
- 150000001491 aromatic compounds Chemical class 0.000 claims abstract description 24
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 24
- 239000002253 acid Substances 0.000 claims description 22
- 238000000926 separation method Methods 0.000 claims description 18
- 238000001179 sorption measurement Methods 0.000 claims description 16
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 6
- 239000011707 mineral Substances 0.000 claims description 6
- 239000002245 particle Substances 0.000 claims description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
- 239000008096 xylene Substances 0.000 claims description 4
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- 229960000907 methylthioninium chloride Drugs 0.000 claims description 3
- 238000004438 BET method Methods 0.000 claims description 2
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- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
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- RBTBFTRPCNLSDE-UHFFFAOYSA-N 3,7-bis(dimethylamino)phenothiazin-5-ium Chemical compound C1=CC(N(C)C)=CC2=[S+]C3=CC(N(C)C)=CC=C3N=C21 RBTBFTRPCNLSDE-UHFFFAOYSA-N 0.000 claims 1
- 239000007857 degradation product Substances 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 abstract description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 39
- MWOOGOJBHIARFG-UHFFFAOYSA-N vanillin Chemical compound COC1=CC(C=O)=CC=C1O MWOOGOJBHIARFG-UHFFFAOYSA-N 0.000 description 32
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- 235000012141 vanillin Nutrition 0.000 description 31
- 239000000126 substance Substances 0.000 description 30
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 22
- LHGVFZTZFXWLCP-UHFFFAOYSA-N guaiacol Chemical compound COC1=CC=CC=C1O LHGVFZTZFXWLCP-UHFFFAOYSA-N 0.000 description 20
- 238000005406 washing Methods 0.000 description 17
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
- 239000003463 adsorbent Substances 0.000 description 16
- 238000011068 loading method Methods 0.000 description 14
- 239000000243 solution Substances 0.000 description 14
- KQPXJFAYGYIGRU-UHFFFAOYSA-N 3,3'-dimethoxystilbene-4,4'-diol Chemical compound C1=C(O)C(OC)=CC(C=CC=2C=C(OC)C(O)=CC=2)=C1 KQPXJFAYGYIGRU-UHFFFAOYSA-N 0.000 description 11
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 10
- 229960001867 guaiacol Drugs 0.000 description 10
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- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
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- 239000002699 waste material Substances 0.000 description 5
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- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 4
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 239000003513 alkali Substances 0.000 description 4
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- KSEBMYQBYZTDHS-HWKANZROSA-N ferulic acid Chemical compound COC1=CC(\C=C\C(O)=O)=CC=C1O KSEBMYQBYZTDHS-HWKANZROSA-N 0.000 description 4
- HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 description 4
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- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 241000196324 Embryophyta Species 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 3
- 239000007900 aqueous suspension Substances 0.000 description 3
- 230000036983 biotransformation Effects 0.000 description 3
- KSEBMYQBYZTDHS-UHFFFAOYSA-N ferulic acid Natural products COC1=CC(C=CC(O)=O)=CC=C1O KSEBMYQBYZTDHS-UHFFFAOYSA-N 0.000 description 3
- 229940114124 ferulic acid Drugs 0.000 description 3
- 235000001785 ferulic acid Nutrition 0.000 description 3
- 238000011049 filling Methods 0.000 description 3
- LNTHITQWFMADLM-UHFFFAOYSA-N gallic acid Chemical compound OC(=O)C1=CC(O)=C(O)C(O)=C1 LNTHITQWFMADLM-UHFFFAOYSA-N 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
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- QURCVMIEKCOAJU-UHFFFAOYSA-N trans-isoferulic acid Natural products COC1=CC=C(C=CC(O)=O)C=C1O QURCVMIEKCOAJU-UHFFFAOYSA-N 0.000 description 3
- 239000002023 wood Substances 0.000 description 3
- 238000010626 work up procedure Methods 0.000 description 3
- IBKQQKPQRYUGBJ-UHFFFAOYSA-N 1-(3,4,5-trihydroxyphenyl)ethanone Chemical compound CC(=O)C1=CC(O)=C(O)C(O)=C1 IBKQQKPQRYUGBJ-UHFFFAOYSA-N 0.000 description 2
- XXQGYGJZNMSSFD-UHFFFAOYSA-N 2-[2-(dimethylcarbamoyl)phenoxy]acetic acid Chemical compound CN(C)C(=O)C1=CC=CC=C1OCC(O)=O XXQGYGJZNMSSFD-UHFFFAOYSA-N 0.000 description 2
- 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 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- 102100022443 CXADR-like membrane protein Human genes 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
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- 230000004913 activation Effects 0.000 description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- 239000003957 anion exchange resin Substances 0.000 description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- JXLHNMVSKXFWAO-UHFFFAOYSA-N azane;7-fluoro-2,1,3-benzoxadiazole-4-sulfonic acid Chemical compound N.OS(=O)(=O)C1=CC=C(F)C2=NON=C12 JXLHNMVSKXFWAO-UHFFFAOYSA-N 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
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- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
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- JMFRWRFFLBVWSI-NSCUHMNNSA-N coniferol Chemical compound COC1=CC(\C=C\CO)=CC=C1O JMFRWRFFLBVWSI-NSCUHMNNSA-N 0.000 description 2
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- 229920005611 kraft lignin Polymers 0.000 description 2
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- CXKWCBBOMKCUKX-UHFFFAOYSA-M methylene blue Chemical compound [Cl-].C1=CC(N(C)C)=CC2=[S+]C3=CC(N(C)C)=CC=C3N=C21 CXKWCBBOMKCUKX-UHFFFAOYSA-M 0.000 description 2
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- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- YIBXWXOYFGZLRU-UHFFFAOYSA-N syringic aldehyde Natural products CC12CCC(C3(CCC(=O)C(C)(C)C3CC=3)C)C=3C1(C)CCC2C1COC(C)(C)C(O)C(O)C1 YIBXWXOYFGZLRU-UHFFFAOYSA-N 0.000 description 1
- PTNLHDGQWUGONS-UHFFFAOYSA-N trans-p-coumaric alcohol Natural products OCC=CC1=CC=C(O)C=C1 PTNLHDGQWUGONS-UHFFFAOYSA-N 0.000 description 1
- PTNLHDGQWUGONS-OWOJBTEDSA-N trans-p-coumaryl alcohol Chemical compound OC\C=C\C1=CC=C(O)C=C1 PTNLHDGQWUGONS-OWOJBTEDSA-N 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 239000002912 waste gas Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/78—Separation; Purification; Stabilisation; Use of additives
- C07C45/79—Separation; Purification; Stabilisation; Use of additives by solid-liquid treatment; by chemisorption
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D15/00—Separating processes involving the treatment of liquids with solid sorbents; Apparatus therefor
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C47/00—Compounds having —CHO groups
- C07C47/52—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings
- C07C47/575—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings containing ether groups, groups, groups, or groups
- C07C47/58—Vanillin
Definitions
- Another disadvantage of obtaining aromatic products of value with the aid of ion-exchange resins is that it is a chemical process and that the products thus obtained can no longer be classified as "natural".
- the ion exchangers have no sufficient selectivity and effectiveness in the adsorption of aromatic components, since the inorganic substances present in the alkaline, lignin-containing solutions are also bound and thus a large part of the adsorption capacity of the ion exchangers is lost.
- the aqueous dilute acid if appropriate after a washing step, will be passed through the adsorbent arrangement in ascending or descending order to protonate at most any bound anionic aromatic valuable substances.
- the amount of aqueous dilute acid is usually 0.1 to 10 times the bed volume, more preferably 0.5 to 5 times the bed volume.
- the passage of the aqueous dilute acid takes place in usually with a specific flow rate (specific load) in the range of 0.5 to 10 BV / h, in particular in the range of 1 to 8 BV / h.
- the organic solvent used for desorption is at least 80
- the eluate obtained in the elution is worked up to obtain the aromatic valuable substances in the usual way. If the eluate contains acid you will find it in the First remove rule, for example, by an aqueous-extractive workup, or neutralize by adding base and separate the resulting salts. Optionally, one may previously concentrate the eluate, for example by removing the solvent in a conventional evaporator arrangement. The resulting condensate can be reused, for example, in a subsequent elution.
- Example II.2 Adsorption and desorption of aromatic valuable substances such as vanillin, acetovanillon, guaiacol and 3,3'-dimethoxy-4,4'-dihydroxystilbene on activated charcoal
- black liquor from pulp production was used.
- HPLC analysis of the filtered black liquor yielded the following concentrations of the organic components: 457 mg / kg vanillin, 349 mg / kg acetovanillon, 506 mg / kg guaiacol, and 308 mg / kg 3,3'-dimethoxy-4,4'-dihydroxystilbene ,
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Analytical Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Solid-Sorbent Or Filter-Aiding Compositions (AREA)
- Compounds Of Unknown Constitution (AREA)
Abstract
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP14192283 | 2014-11-07 | ||
| PCT/EP2015/075869 WO2016071476A1 (fr) | 2014-11-07 | 2015-11-06 | Procédé d'obtention de produits de valeur aromatiques à partir de compositions contenant de la lignine |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| EP3215247A1 true EP3215247A1 (fr) | 2017-09-13 |
Family
ID=51900177
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP15790940.9A Withdrawn EP3215247A1 (fr) | 2014-11-07 | 2015-11-06 | Procédé d'obtention de produits de valeur aromatiques à partir de compositions contenant de la lignine |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US20170334824A1 (fr) |
| EP (1) | EP3215247A1 (fr) |
| JP (1) | JP2017533236A (fr) |
| CN (1) | CN107074710A (fr) |
| MX (1) | MX2017005876A (fr) |
| WO (1) | WO2016071476A1 (fr) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP6741687B2 (ja) | 2015-05-04 | 2020-08-19 | ビーエーエスエフ ソシエタス・ヨーロピアBasf Se | メロナールの調製方法 |
| CN107848929A (zh) | 2015-07-15 | 2018-03-27 | 巴斯夫欧洲公司 | 制备芳基丙烯的方法 |
| US10202323B2 (en) | 2015-07-15 | 2019-02-12 | Basf Se | Process for preparing an arylpropene |
| PL3370540T3 (pl) | 2015-11-06 | 2025-11-12 | Flavologic Gmbh | Układ adsorpcji i sposób obsługi układu adsorpcji |
| DE102016105997A1 (de) * | 2016-04-01 | 2017-10-05 | Flavologic Gmbh | Adsorptionssystem und Verfahren zum Betreiben eines Adsorptionssystems |
| ES2899827T3 (es) | 2015-12-08 | 2022-03-14 | Basf Se | Material zeolítico que contiene estaño y que tiene una estructura de marco BEA |
| US10981885B2 (en) | 2016-05-31 | 2021-04-20 | Basf Se | Tetrahydropyranyl lower alkyl esters and the production of same using a ketene compound |
| CN114514218A (zh) * | 2019-07-16 | 2022-05-17 | 斯佩罗可再生能源有限责任公司 | 从生物质中提取和纯化天然阿魏酸盐和香豆酸盐 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NO792311L (no) * | 1978-07-27 | 1980-01-29 | Erich Hayek | Fremgangsmaate for utnyttelse av sulfittavlut fra industriell cellulosefremstilling |
| US5068184A (en) * | 1987-07-28 | 1991-11-26 | Escagenetics, Inc. | Flavor composition and method |
| EP2157184B1 (fr) * | 2007-04-19 | 2020-11-18 | Laboratorios Minkab, S.A. de C.V. | Procédé de production de vanilline à partir de micro-organismes immobilisés par culture de surface |
-
2015
- 2015-11-06 WO PCT/EP2015/075869 patent/WO2016071476A1/fr not_active Ceased
- 2015-11-06 CN CN201580060238.6A patent/CN107074710A/zh active Pending
- 2015-11-06 US US15/522,550 patent/US20170334824A1/en not_active Abandoned
- 2015-11-06 JP JP2017523885A patent/JP2017533236A/ja active Pending
- 2015-11-06 EP EP15790940.9A patent/EP3215247A1/fr not_active Withdrawn
- 2015-11-06 MX MX2017005876A patent/MX2017005876A/es unknown
Non-Patent Citations (2)
| Title |
|---|
| None * |
| See also references of WO2016071476A1 * |
Also Published As
| Publication number | Publication date |
|---|---|
| MX2017005876A (es) | 2017-06-26 |
| CN107074710A (zh) | 2017-08-18 |
| WO2016071476A1 (fr) | 2016-05-12 |
| JP2017533236A (ja) | 2017-11-09 |
| US20170334824A1 (en) | 2017-11-23 |
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