CA1040216A - Production de syringealdehyde ou de vanilline a partir des liqueurs de pulpe de bois franc - Google Patents

Production de syringealdehyde ou de vanilline a partir des liqueurs de pulpe de bois franc

Info

Publication number: CA1040216A
Authority: CA; Canada
Prior art keywords: liquor; syringealdehyde; vanillin; lignin; organic solvent
Prior art date: 1975-09-11
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

Application number

CA235,220A

Other languages

English (en)

Other versions

CA235220S (en

Inventor

Harry B. Marshall

Donald L. Vincent

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Domtar Inc

Original Assignee

Domtar Inc

Priority date (The priority date 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 date listed.)

1975-09-11

Filing date

1975-09-11

Publication date

1978-10-10

1975-09-11 Application filed by Domtar Inc filed Critical Domtar Inc

1975-09-11 Priority to CA235,220A priority Critical patent/CA1040216A/fr

1978-10-10 Application granted granted Critical

1978-10-10 Publication of CA1040216A publication Critical patent/CA1040216A/fr

Status Expired legal-status Critical Current

Links

KCDXJAYRVLXPFO-UHFFFAOYSA-N syringaldehyde Chemical compound COC1=CC(C=O)=CC(OC)=C1O KCDXJAYRVLXPFO-UHFFFAOYSA-N 0.000 title claims abstract description 36
239000002699 waste material Substances 0.000 title claims abstract description 23
MWOOGOJBHIARFG-UHFFFAOYSA-N vanillin Chemical compound COC1=CC(C=O)=CC=C1O MWOOGOJBHIARFG-UHFFFAOYSA-N 0.000 title claims description 30
FGQOOHJZONJGDT-UHFFFAOYSA-N vanillin Natural products COC1=CC(O)=CC(C=O)=C1 FGQOOHJZONJGDT-UHFFFAOYSA-N 0.000 title claims description 30
235000012141 vanillin Nutrition 0.000 title claims description 30
238000004519 manufacturing process Methods 0.000 title claims description 9
239000011121 hardwood Substances 0.000 title claims description 8
239000003265 pulping liquor Substances 0.000 title description 4
150000001299 aldehydes Chemical class 0.000 claims abstract description 14
230000007935 neutral effect Effects 0.000 claims abstract description 8
229920005610 lignin Polymers 0.000 claims description 42
238000000034 method Methods 0.000 claims description 31
239000000203 mixture Substances 0.000 claims description 21
239000003513 alkali Substances 0.000 claims description 19
239000002655 kraft paper Substances 0.000 claims description 17
239000007864 aqueous solution Substances 0.000 claims description 16
239000003960 organic solvent Substances 0.000 claims description 16
238000004537 pulping Methods 0.000 claims description 11
LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 claims description 10
239000003054 catalyst Substances 0.000 claims description 9
230000003647 oxidation Effects 0.000 claims description 9
238000007254 oxidation reaction Methods 0.000 claims description 9
239000000126 substance Substances 0.000 claims description 9
DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 claims description 8
235000010267 sodium hydrogen sulphite Nutrition 0.000 claims description 8
238000011084 recovery Methods 0.000 claims description 7
239000000243 solution Substances 0.000 claims description 6
239000012223 aqueous fraction Substances 0.000 claims description 5
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 4
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 4
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
238000004508 fractional distillation Methods 0.000 claims description 4
239000007789 gas Substances 0.000 claims description 4
239000001301 oxygen Substances 0.000 claims description 4
229910052760 oxygen Inorganic materials 0.000 claims description 4
150000003839 salts Chemical class 0.000 claims description 4
230000003472 neutralizing effect Effects 0.000 claims description 3
238000005406 washing Methods 0.000 claims description 3
DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims description 2
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical class [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 2
AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 claims description 2
229910017052 cobalt Inorganic materials 0.000 claims description 2
239000010941 cobalt Substances 0.000 claims description 2
GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 2
229910052802 copper Inorganic materials 0.000 claims description 2
239000010949 copper Substances 0.000 claims description 2
229910052742 iron Inorganic materials 0.000 claims description 2
WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical class [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 claims description 2
229910052759 nickel Inorganic materials 0.000 claims description 2
229910052723 transition metal Inorganic materials 0.000 claims description 2
150000003624 transition metals Chemical class 0.000 claims 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 claims 1
238000004064 recycling Methods 0.000 claims 1
229910052708 sodium Inorganic materials 0.000 claims 1
239000011734 sodium Substances 0.000 claims 1
238000011282 treatment Methods 0.000 abstract description 4
230000001590 oxidative effect Effects 0.000 abstract description 3
238000002955 isolation Methods 0.000 abstract 1
238000000746 purification Methods 0.000 abstract 1
LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 abstract 1
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
229910052721 tungsten Inorganic materials 0.000 description 11
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 7
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
238000006243 chemical reaction Methods 0.000 description 4
239000000543 intermediate Substances 0.000 description 4
235000011121 sodium hydroxide Nutrition 0.000 description 4
239000007787 solid Substances 0.000 description 4
229910000366 copper(II) sulfate Inorganic materials 0.000 description 3
238000000605 extraction Methods 0.000 description 3
238000001030 gas--liquid chromatography Methods 0.000 description 3
239000012535 impurity Substances 0.000 description 3
229940099596 manganese sulfate Drugs 0.000 description 3
235000007079 manganese sulphate Nutrition 0.000 description 3
239000011702 manganese sulphate Substances 0.000 description 3
SQQMAOCOWKFBNP-UHFFFAOYSA-L manganese(II) sulfate Chemical compound [Mn+2].[O-]S([O-])(=O)=O SQQMAOCOWKFBNP-UHFFFAOYSA-L 0.000 description 3
239000000047 product Substances 0.000 description 3
OPHQOIGEOHXOGX-UHFFFAOYSA-N 3,4,5-trimethoxybenzaldehyde Chemical compound COC1=CC(C=O)=CC(OC)=C1OC OPHQOIGEOHXOGX-UHFFFAOYSA-N 0.000 description 2
239000002253 acid Substances 0.000 description 2
239000008346 aqueous phase Substances 0.000 description 2
239000000470 constituent Substances 0.000 description 2
ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 2
238000004821 distillation Methods 0.000 description 2
230000000694 effects Effects 0.000 description 2
239000000284 extract Substances 0.000 description 2
239000000295 fuel oil Substances 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
239000003921 oil Substances 0.000 description 2
239000012071 phase Substances 0.000 description 2
WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallol Chemical compound OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 description 2
238000000926 separation method Methods 0.000 description 2
239000002904 solvent Substances 0.000 description 2
238000003860 storage Methods 0.000 description 2
239000002023 wood Substances 0.000 description 2
RRKMWVISRMWBAL-UHFFFAOYSA-N 3,4-dihydroxy-5-methoxybenzaldehyde Chemical class COC1=CC(C=O)=CC(O)=C1O RRKMWVISRMWBAL-UHFFFAOYSA-N 0.000 description 1
241000532370 Atla Species 0.000 description 1
UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
229920001732 Lignosulfonate Polymers 0.000 description 1
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
241001062472 Stokellia anisodon Species 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
239000012670 alkaline solution Substances 0.000 description 1
239000006286 aqueous extract Substances 0.000 description 1
230000015556 catabolic process Effects 0.000 description 1
238000009993 causticizing Methods 0.000 description 1
239000003518 caustics Substances 0.000 description 1
238000002485 combustion reaction Methods 0.000 description 1
238000010960 commercial process Methods 0.000 description 1
150000001875 compounds Chemical class 0.000 description 1
238000010411 cooking Methods 0.000 description 1
239000012043 crude product Substances 0.000 description 1
230000007423 decrease Effects 0.000 description 1
239000013530 defoamer Substances 0.000 description 1
230000029087 digestion Effects 0.000 description 1
239000003814 drug Substances 0.000 description 1
229940079593 drug Drugs 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
239000003546 flue gas Substances 0.000 description 1
238000005259 measurement Methods 0.000 description 1
238000002156 mixing Methods 0.000 description 1
238000006386 neutralization reaction Methods 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
230000020477 pH reduction Effects 0.000 description 1
229920001021 polysulfide Polymers 0.000 description 1
239000005077 polysulfide Substances 0.000 description 1
150000008117 polysulfides Polymers 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
229940079877 pyrogallol Drugs 0.000 description 1
238000011935 selective methylation Methods 0.000 description 1
238000000638 solvent extraction Methods 0.000 description 1
241000894007 species Species 0.000 description 1
239000007858 starting material Substances 0.000 description 1
238000010025 steaming Methods 0.000 description 1
239000001117 sulphuric acid Substances 0.000 description 1
235000011149 sulphuric acid Nutrition 0.000 description 1

Landscapes

Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CA235,220A 1975-09-11 1975-09-11 Production de syringealdehyde ou de vanilline a partir des liqueurs de pulpe de bois franc Expired CA1040216A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA235,220A CA1040216A (fr)	1975-09-11	1975-09-11	Production de syringealdehyde ou de vanilline a partir des liqueurs de pulpe de bois franc

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CA235,220A CA1040216A (fr)	1975-09-11	1975-09-11	Production de syringealdehyde ou de vanilline a partir des liqueurs de pulpe de bois franc

Publications (1)

Publication Number	Publication Date
CA1040216A true CA1040216A (fr)	1978-10-10

Family

ID=4104018

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA235,220A Expired CA1040216A (fr)	1975-09-11	1975-09-11	Production de syringealdehyde ou de vanilline a partir des liqueurs de pulpe de bois franc

Country Status (1)

Country	Link
CA (1)	CA1040216A (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN1060464C (zh) *	1998-05-29	2001-01-10	中国科学院广州化学研究所	蔗渣碱木质素催化氧化制紫丁香醛和香兰素的方法
EP2334625A1 (fr) *	2008-09-08	2011-06-22	Basf Se	Procédé de production intégrée de cellulose et de matière réutilisable de faible poids moléculaire

1975
- 1975-09-11 CA CA235,220A patent/CA1040216A/fr not_active Expired

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN1060464C (zh) *	1998-05-29	2001-01-10	中国科学院广州化学研究所	蔗渣碱木质素催化氧化制紫丁香醛和香兰素的方法
EP2334625A1 (fr) *	2008-09-08	2011-06-22	Basf Se	Procédé de production intégrée de cellulose et de matière réutilisable de faible poids moléculaire

Publication	Publication Date	Title
US4075248A (en)	1978-02-21	Production of syringealdehyde from hardwood waste pulping liquors
US2057117A (en)	1936-10-13	Process of making vanillin
EP0038317A1 (fr)	1981-10-21	Procédé de production de substances chimiques à partir d'hydrolysats acides de matières végétales
US4847422A (en)	1989-07-11	Method for the production of vanillin
NO153140B (no)	1985-10-14	Fremgangsmaate for separering av lignosulfonsyrer og lignosulfater fra sulfittavlut
US2296952A (en)	1942-09-29	Chemical treatment of black liquor and tall oil
US2813900A (en)	1957-11-19	Process for producing levulinic acid
US4135967A (en)	1979-01-23	Process for producing cellulose pulp by solid phase digestion
US3887426A (en)	1975-06-03	Process for producing cellulose pulp by digestion with a diol or triol solvent and an aniline or phenol salt
US2187366A (en)	1940-01-16	Manufacture of vanillin
US2078963A (en)	1937-05-04	Process for refining crude naphthalene
CA1121384A (fr)	1982-04-06	Methode de preparation de la vanilline
US4208350A (en)	1980-06-17	Separating phenols from alkaline pulping spent liquors
US2436804A (en)	1948-03-02	Process of recovering organic compounds
US2964449A (en)	1960-12-13	Method of processing lignified cellulose
US1754207A (en)	1930-04-08	Treatment of residual liquors
US2433227A (en)	1947-12-23	Treatment of lignin substances
EP0593744A1 (fr)	1994-04-27	Procede de recuperation de produits chimiques de cuisson a partir de la liqueur noire dans la fabrication de la cellulose selon le procede organosolver
US2382572A (en)	1945-08-14	Manufacture of levulinic acid
US3054825A (en)	1962-09-18	Method of producing vanillin and other useful products
US1944681A (en)	1934-01-23	Production of tar acids
US4450291A (en)	1984-05-22	Decontamination of KA oil refinement waste stream
US2913309A (en)	1959-11-17	Chemical recovery process
DE2036937C3 (de)	1978-10-05	Verfahren zur Gewinnung von p-Diisopropylbenzoldihydroperoxid
US2642458A (en)	1953-06-16	Process of preparing 2-sulfobenzoic acid

CA1040216A - Production de syringealdehyde ou de vanilline a partir des liqueurs de pulpe de bois franc - Google Patents

Info

Links

Landscapes

Priority Applications (1)

Applications Claiming Priority (1)

Publications (1)

Family

ID=4104018

Family Applications (1)

Country Status (1)

Cited By (2)

Cited By (2)

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