CA2551418A1 - Novel lignin derivatives, molded products using the same and processes for making the same - Google Patents
Novel lignin derivatives, molded products using the same and processes for making the same Download PDFInfo
- Publication number
- CA2551418A1 CA2551418A1 CA002551418A CA2551418A CA2551418A1 CA 2551418 A1 CA2551418 A1 CA 2551418A1 CA 002551418 A CA002551418 A CA 002551418A CA 2551418 A CA2551418 A CA 2551418A CA 2551418 A1 CA2551418 A1 CA 2551418A1
- Authority
- CA
- Canada
- Prior art keywords
- derivative
- lignin
- phenol derivative
- unit
- phenol
- 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
- 229920005610 lignin Polymers 0.000 title claims abstract 26
- 238000000034 method Methods 0.000 title claims abstract 19
- 150000002989 phenols Chemical class 0.000 claims abstract 22
- ODLMAHJVESYWTB-UHFFFAOYSA-N propylbenzene Chemical compound CCCC1=CC=CC=C1 ODLMAHJVESYWTB-UHFFFAOYSA-N 0.000 claims abstract 14
- 229910052799 carbon Inorganic materials 0.000 claims abstract 9
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract 9
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims abstract 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract 8
- MILSYCKGLDDVLM-UHFFFAOYSA-N 2-phenylpropan-2-ylbenzene Chemical group C=1C=CC=CC=1C(C)(C)C1=CC=CC=C1 MILSYCKGLDDVLM-UHFFFAOYSA-N 0.000 claims abstract 6
- HBEDSQVIWPRPAY-UHFFFAOYSA-N 2,3-dihydrobenzofuran Chemical group C1=CC=C2OCCC2=C1 HBEDSQVIWPRPAY-UHFFFAOYSA-N 0.000 claims abstract 3
- 125000003118 aryl group Chemical group 0.000 claims abstract 3
- 239000003513 alkali Substances 0.000 claims abstract 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims abstract 2
- 239000000463 material Substances 0.000 claims 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 6
- 239000002904 solvent Substances 0.000 claims 6
- 239000000758 substrate Substances 0.000 claims 6
- 238000000465 moulding Methods 0.000 claims 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 4
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 claims 4
- WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallol Chemical compound OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 claims 4
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 claims 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims 2
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 claims 2
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 claims 2
- 239000002253 acid Substances 0.000 claims 2
- 229920002678 cellulose Polymers 0.000 claims 2
- 239000001913 cellulose Substances 0.000 claims 2
- 229930003836 cresol Natural products 0.000 claims 2
- LHGVFZTZFXWLCP-UHFFFAOYSA-N guaiacol Chemical compound COC1=CC=CC=C1O LHGVFZTZFXWLCP-UHFFFAOYSA-N 0.000 claims 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 239000000203 mixture Substances 0.000 claims 2
- 229940079877 pyrogallol Drugs 0.000 claims 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 2
- 238000001704 evaporation Methods 0.000 claims 1
- 239000002657 fibrous material Substances 0.000 claims 1
- 238000002791 soaking Methods 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07G—COMPOUNDS OF UNKNOWN CONSTITUTION
- C07G1/00—Lignin; Lignin derivatives
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08H—DERIVATIVES OF NATURAL MACROMOLECULAR COMPOUNDS
- C08H6/00—Macromolecular compounds derived from lignin, e.g. tannins, humic acids
-
- D—TEXTILES; PAPER
- D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
- D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
- D21H13/00—Pulp or paper, comprising synthetic cellulose or non-cellulose fibres or web-forming material
- D21H13/36—Inorganic fibres or flakes
-
- D—TEXTILES; PAPER
- D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
- D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
- D21H27/00—Special paper not otherwise provided for, e.g. made by multi-step processes
- D21H27/30—Multi-ply
-
- 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
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/582—Recycling of unreacted starting or intermediate materials
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Materials Engineering (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Manufacture Of Macromolecular Shaped Articles (AREA)
- Compounds Of Unknown Constitution (AREA)
Abstract
The present invention provides a process for producing novel lignin derivatives, which comprises using a lignophenol derivative containing a diphenylpropane unit formed by binding a carbon atom at an ortho-position relative to a phenolic hydroxyl group of a phenol derivative to a carbon atom at a benzyl-position of a phenylpropane fundamental unit of lignin, and binding an oxygen atom of the hydroxyl group and a .beta.
-positional carbon atom under alkali conditions under which the hydroxyl group can dissociate, to obtain an arylcoumaran derivative containing an arylcoumaran unit in which a coumaran skeleton is bound to an aromatic ring of lignin.
-positional carbon atom under alkali conditions under which the hydroxyl group can dissociate, to obtain an arylcoumaran derivative containing an arylcoumaran unit in which a coumaran skeleton is bound to an aromatic ring of lignin.
Claims (23)
1. A method for producing a lignin derivative, said method comprising the step of:
binding an oxygen atom of the hydroxyl group and a .beta.-positional carbon atom of a diphenylpropane unit contained in a lignophenol derivative, where the diphenylpropane unit is formed by binding a carbon atom at an ortho-position relative to a phenolic hydroxyl group of a phenol derivative to a carbon atom at a benzyl-position of a phenylpropane unit of lignin, to obtain an arylcoumaran derivative containing an arylcoumaran unit in which a coumaran skeleton is bound to an aromatic ring of the phenylpropane unit of lignin.
binding an oxygen atom of the hydroxyl group and a .beta.-positional carbon atom of a diphenylpropane unit contained in a lignophenol derivative, where the diphenylpropane unit is formed by binding a carbon atom at an ortho-position relative to a phenolic hydroxyl group of a phenol derivative to a carbon atom at a benzyl-position of a phenylpropane unit of lignin, to obtain an arylcoumaran derivative containing an arylcoumaran unit in which a coumaran skeleton is bound to an aromatic ring of the phenylpropane unit of lignin.
2. The method according to claim 1, said method further comprising the step of adding an acid to a lignin solvated with phenol derivative to convert a phenylpropane unit of lignin into a diphenylpropane unit by grafting the phenol derivative to the phenylpropane unit.
3. The method according to claim 1, said method further comprising the step of adding an acid to a lignin solvated with phenol derivative to convert a phenylpropane into a diphenylpropane unit by grafting the phenol derivative to the phenylpropane unit, where a carbon atom at an para-position relative to a phenolic hydroxyl group of the phenol derivative is bound to a carbon atom at a benzyl-position of the phenylpropane unit of lignin, to obtain a lignophenol derivative.
4. The method according to claim 1, 2 or 3, wherein said binding step heats the lignophenol derivative under alkali conditions such that the phenolic hydroxyl group of the phenol derivative can dissociate.
5. The method according to any one of claims 1 to 4, wherein the phenol derivative comprises monovalent phenol derivative, divalent phenol derivative, or trivalent phenol derivative, or any combination thereof, and wherein the phenolic hydrogen group of the phenol derivative comprises at least one unsubstituted ortho-position.
6. The method according to claim 5, wherein the phenol derivative comprising a phenol, a cresol, methoxyphenol, a naphthol, a catechol, a resorcinol, or a pyrogallol, or any combination thereof.
7. The method according to any one of claims 1 to 6, wherein the lignin derivative further comprises an additional phenylpropane unit of lignin.
8. A lignin derivative comprising:
an arylcoumaran unit in which a coumaran skeleton is bound to an aromatic ring of a phenylpropane unit of lignin; and a diphenylpropane unit formed by binding a carbon atom at an ortho-position and/or a para-position relative to a phenolic hydroxyl group of a phenol derivative and grafting the phenol derivative to a benzyl-position of a phenylpropane unit of lignin.
an arylcoumaran unit in which a coumaran skeleton is bound to an aromatic ring of a phenylpropane unit of lignin; and a diphenylpropane unit formed by binding a carbon atom at an ortho-position and/or a para-position relative to a phenolic hydroxyl group of a phenol derivative and grafting the phenol derivative to a benzyl-position of a phenylpropane unit of lignin.
9. The lignin derivative according to claim 8, wherein the phenol derivative comprises monovalent phenol derivative, divalent phenol derivative, or trivalent phenol derivative, or any combination thereof, and a phenolic hydrogen group of the phenol derivative comprising at least one unsubstituted ortho position.
10. The lignin derivative according to claim 9, wherein the phenol derivative comprises a phenol, a cresol, methoxyphenol, a naphthol, a catechol, a resorcinol, or a pyrogallol, or any combination thereof.
11. The lignin derivative according to claim 8, 9 or 10, further comprising a phenylpropane unit.
12. The lignin derivative according to any one of claims 8 to 11, having a weight-average molecular weight of about 500 to 2000.
13. A molded product comprising the lignin derivative as defined in any one of claims 8 to 12.
14. The molded product according to claim 13, wherein a molding substrate material is molded to obtain said molded product, said molded substrate material comprising a chip-like material, fibrous material, or powdery material, or any combination thereof.
15. The molded material according to claim 14, wherein the molding substrate material comprises cellulose.
16. A method for producing a molded product comprising the step of:
using the lignin derivative as defined in any one of claims 8 to 12 to obtain a molding substrate material.
using the lignin derivative as defined in any one of claims 8 to 12 to obtain a molding substrate material.
17. The method according to claim 16, further comprising the step of:
dissolving the lignin derivative in a solvent to form the molding substrate material and evaporating the solvent.
dissolving the lignin derivative in a solvent to form the molding substrate material and evaporating the solvent.
18. The method according to claim 17, wherein the solvent comprises acetone, ethanol, methanol, dioxane, or tetrahydrofuran, or a mixture of any one of them with water.
19. A method for treating a molded product, said method comprising the steps of:
(a) adding a solvent having affinity for the lignin derivative as defined in any one of claims 8 to 12 to a molded product containing the lignin derivative; and (b) recovering the lignin derivative.
(a) adding a solvent having affinity for the lignin derivative as defined in any one of claims 8 to 12 to a molded product containing the lignin derivative; and (b) recovering the lignin derivative.
20. The method according to claim 19, wherein the molded product comprises cellulose.
21. The method according to claim 19 or 20, wherein the solvent comprises acetone, ethanol, methanol, dioxane, or tetrahydrofuran, or a mixture of any one of them with water.
22. The method according to claim 19, 20 or 21, wherein said step (b) comprises soaking the molded product into the solvent.
23. The method according to any one of claims 19 to 22, wherein said step (b) further comprises recovering molding substrate material of the molded product.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA2551418A CA2551418C (en) | 1997-09-12 | 1997-09-12 | Novel lignin derivatives, molded products using the same and processes for making the same |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA002303122A CA2303122C (en) | 1997-09-12 | 1997-09-12 | Novel lignin derivatives, molded products using the same and processes for making the same |
| CA2551418A CA2551418C (en) | 1997-09-12 | 1997-09-12 | Novel lignin derivatives, molded products using the same and processes for making the same |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002303122A Division CA2303122C (en) | 1997-09-12 | 1997-09-12 | Novel lignin derivatives, molded products using the same and processes for making the same |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2551418A1 true CA2551418A1 (en) | 1999-03-25 |
| CA2551418C CA2551418C (en) | 2010-09-28 |
Family
ID=36998218
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2551418A Expired - Fee Related CA2551418C (en) | 1997-09-12 | 1997-09-12 | Novel lignin derivatives, molded products using the same and processes for making the same |
Country Status (1)
| Country | Link |
|---|---|
| CA (1) | CA2551418C (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US10301437B2 (en) | 2013-11-26 | 2019-05-28 | Upm-Kymmene Corporation | Method for treating lignin and for producing a binder composition |
| CN112442924A (en) * | 2019-09-03 | 2021-03-05 | 中国科学院大连化学物理研究所 | Method for preparing high-hardness environment-friendly material by using protogenic plant biomass as raw material |
-
1997
- 1997-09-12 CA CA2551418A patent/CA2551418C/en not_active Expired - Fee Related
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US10301437B2 (en) | 2013-11-26 | 2019-05-28 | Upm-Kymmene Corporation | Method for treating lignin and for producing a binder composition |
| CN112442924A (en) * | 2019-09-03 | 2021-03-05 | 中国科学院大连化学物理研究所 | Method for preparing high-hardness environment-friendly material by using protogenic plant biomass as raw material |
| CN112442924B (en) * | 2019-09-03 | 2022-06-14 | 中国科学院大连化学物理研究所 | Method for preparing high-hardness environment-friendly material by using protogenic plant biomass as raw material |
Also Published As
| Publication number | Publication date |
|---|---|
| CA2551418C (en) | 2010-09-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |
Effective date: 20130912 |