US4250088A
Expired / Lapsed
US
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Demethylated lignin and process
Assignee: REED LIGNIN Inc 100 HWY 51 SOUTH ROTHSCHILD WI 54474-1198 A CORP OF
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Filing: 1979-08-20
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Granted: 1981-02-10
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Expires: 1999-08-20
Abstract
Abstract Lignin compounds are demethylated without degradation of the lignin polymer backbone to provide a highly reactive lignin and methyl chloride as products. The reaction is applicable to Kraft lignin or lignosulfonates derived from spent sulfite liquor. Demethylation is accomplished by reacting the lignin material at an elevated temperature with an amine hydrohalide salt.
Inventors
- 👤 Lau S. Yang
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-07 20:58
CPC Classifications
C; C08; C08H; C08H6/00
Claims Analysis
Total Claims: 19
Claim 1
Independent Claim
153 words
A method for demethylation of lignin materials to produce a lignin material of improved reactivity and a methyl halide which comprises reacting (1) a lignin material selected from the group consisting of (a) Kraft lignin derived by acid precipitation of black liguor and (b) purified lignosulfonates derived from spent sulfite liquor, said lignosulfonates being substantially free of reducing suguars and having a sulfonic sulfur content of less than about 5 weight percent with an amine hydrochloride or hydrobromide salt at a temperature between about 180° to 250° C.; the amine component of said salt being an aliphatic amine having a boiling point below about 100° C., said amine functioning as a hydrochloride or hydrobromide carrier in the reaction; (2) continuing said reaction for a period sufficient to permit demethylation; (3) recovering aliphatic amine and methyl halide as a distillate fraction produced during the reaction; and (4) recovering demethylated lignin from the reaction mixture.
Claim 2
Independent Claim
153 words
A method for demethylation of lignin materials to produce a lignin material of improved reactivity and a methyl halide which comprises reacting (1) a lignin material selected from the group consisting of (a) Kraft lignin derived by acid precipitation of black liguor and (b) purified lignosulfonates derived from spent sulfite liquor, said lignosulfonates being substantially free of reducing suguars and having a sulfonic sulfur content of less than about 5 weight percent with an amine hydrochloride or hydrobromide salt at a temperature between about 180° to 250° C.; the amine component of said salt being an aliphatic amine having a boiling point below about 100° C., said amine functioning as a hydrochloride or hydrobromide carrier in the reaction; (2) continuing said reaction for a period sufficient to permit demethylation; (3) recovering aliphatic amine and methyl halide as a distillate fraction produced during the reaction; and (4) recovering demethylated lignin from the reaction mixture.
Claim 3
Dependent Claim
23 words
A method as claimed in claim 1 wherein said lignin material is alkali soluble Kraft lignin derived from spent liquor of alkaline pulping.
Claim 4
Dependent Claim
23 words
A method as claimed in claim 1 wherein said amine salt is a primary aliphatic amine hydrochloride having 1 to 4 carbon atoms.
Claim 5
Dependent Claim
15 words
A method as claimed in claim 1 wherein said amine salt is n-butyl amine hydrochloride.
Claim 6
Dependent Claim
19 words
A method as claimed in claim 1 wherein said lignin material is a lignosulfonate derived from spent sulfite liquor.
Claim 7
Dependent Claim
23 words
A method as claimed in claim 5 wherein said amine salt is a primary aliphatic amine hydrochloride having 1 to 4 carbon atoms.
Claim 8
Dependent Claim
40 words
A method as claimed in claim 2 wherein said Kraft lignin is water-insoluble and soluble in aqueous alkaline solution, has a phenolic hydroxyl content of at least 5 weight percent and a methoxy content of at least 13.5 weight percent.
Claim 9
Dependent Claim
45 words
A method as claimed in claim 7 wherein said demethylation results in a lignin material having a phenolic hydroxyl content of about 10 weight percent and a methoxy content of less than 5 weight percent, said material being water-insoluble and soluble in aqueous alkaline solution.
Claim 10
Independent Claim
162 words
A method for the demethylation of water-insoluble Kraft lignin material, derived by acid precipitation of black liquor, having a phenolic hydroxyl content of about 5 weight percent and a methoxy content of about 13.5 weight percent to produce a water-insoluble demethylated lignin having increased reactive sites, a phenolic content of about 10 weight percent and a methoxy content of less than 1 weight percent; methyl chloride; and an amine; said method comprising the steps of: (a) reacting said Kraft lignin material with an aliphatic amine hydrochloride salt at a temperature between about 180° C. and 250° C., the amine component of said salt being an aliphatic amine having 1 to 4 carbon atoms and functioning as a hydrochloride carrier in the reaction; (b) continuing said reaction for a period sufficient to permit demethylation; (c) recovering amine and methyl chloride as a distillate fraction produced during the reaction; and (d) admixing the reaction mixture with water and recovering the precipitated demethylated lignin therefrom.
Claim 11
Independent Claim
162 words
A method for the demethylation of water-insoluble Kraft lignin material, derived by acid precipitation of black liquor, having a phenolic hydroxyl content of about 5 weight percent and a methoxy content of about 13.5 weight percent to produce a water-insoluble demethylated lignin having increased reactive sites, a phenolic content of about 10 weight percent and a methoxy content of less than 1 weight percent; methyl chloride; and an amine; said method comprising the steps of: (a) reacting said Kraft lignin material with an aliphatic amine hydrochloride salt at a temperature between about 180° C. and 250° C., the amine component of said salt being an aliphatic amine having 1 to 4 carbon atoms and functioning as a hydrochloride carrier in the reaction; (b) continuing said reaction for a period sufficient to permit demethylation; (c) recovering amine and methyl chloride as a distillate fraction produced during the reaction; and (d) admixing the reaction mixture with water and recovering the precipitated demethylated lignin therefrom.
Claim 12
Dependent Claim
15 words
A method as claimed in claim 9 wherein said amine salt is n-butyl amine hydrochloride.
Claim 13
Dependent Claim
24 words
A water-insoluble demethylated Kraft lignin or lignosulfonate material having increased reactivity relative to said material before demethylation obtained by the method of claim 1.
Claim 14
Dependent Claim
22 words
A water-insoluble demethylated Kraft lignin material having increased reactivity relative to said material before demethylation obtained by the method of claim 9.
Claim 15
Dependent Claim
24 words
A demethylated, substantially desulfonated lignosulfonate material having increased phenolic hydroxyl content relative to said material before demethylation obtained by the method of claim 1.
Claim 16
Dependent Claim
24 words
A demethylated, substantially desulfonated lignosulfonate material having increased phenolic hydroxyl content relative to said material before demethylation obtained by the method of claim 5.
Claim 17
Independent Claim
109 words
A method for demethylation of purified lignosulfonate derived from spent sulfite liquor, said lignosulfonate being substantially free of reducing sugars and having a sulfonic sulfur content of less than about 5 weight percent (1) reacting said ligno sulfonate with an aliphatic amine hydrochloride or hydrobromide salt having 1 to 4 carbon atoms at a temperature between about 180° to 250° C.; said amine functioning as a hydrochloride or hydrobromide carrier in the reaction; (2) continuing said reaction for a period sufficient to permit demethylation; (3) recovering an amine and methyl halide as a distillate fraction during the reaction; and (4) recovering demethylated, substantially desulfonated lignin from the reaction mixture.
Claim 18
Independent Claim
109 words
A method for demethylation of purified lignosulfonate derived from spent sulfite liquor, said lignosulfonate being substantially free of reducing sugars and having a sulfonic sulfur content of less than about 5 weight percent (1) reacting said ligno sulfonate with an aliphatic amine hydrochloride or hydrobromide salt having 1 to 4 carbon atoms at a temperature between about 180° to 250° C.; said amine functioning as a hydrochloride or hydrobromide carrier in the reaction; (2) continuing said reaction for a period sufficient to permit demethylation; (3) recovering an amine and methyl halide as a distillate fraction during the reaction; and (4) recovering demethylated, substantially desulfonated lignin from the reaction mixture.
Claim 19
Dependent Claim
14 words
A method as claimed in claim 15 wherein the amine salt is n-butylamine hydrochloride.
References Cited (Backward Citations)
No citation records indexed.
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1984-02-10 | 1984-08-11 | 1985-02-10 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1988-02-10 | 1988-08-11 | 1989-02-10 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1992-02-10 | 1992-08-11 | 1993-02-10 | $7700.00 | Window Closed / Lapsed |