CA1096111A - Delignification of lignocellulosic material with a soda pulping liquor containing a diels alder adduct of naphthoquinone in admixture with a nitro aromatic compound - Google Patents
Delignification of lignocellulosic material with a soda pulping liquor containing a diels alder adduct of naphthoquinone in admixture with a nitro aromatic compoundInfo
- Publication number
- CA1096111A CA1096111A CA291,186A CA291186A CA1096111A CA 1096111 A CA1096111 A CA 1096111A CA 291186 A CA291186 A CA 291186A CA 1096111 A CA1096111 A CA 1096111A
- Authority
- CA
- Canada
- Prior art keywords
- diketo
- lignocellulosic material
- anthracene
- weight
- aromatic compound
- 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.)
- Expired
Links
- 239000012978 lignocellulosic material Substances 0.000 title claims abstract description 37
- -1 nitro aromatic compound Chemical class 0.000 title claims abstract description 23
- 239000003265 pulping liquor Substances 0.000 title claims abstract description 21
- 238000005698 Diels-Alder reaction Methods 0.000 title claims abstract description 10
- 229930192627 Naphthoquinone Natural products 0.000 title claims abstract description 8
- 150000002791 naphthoquinones Chemical class 0.000 title claims abstract description 8
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 title abstract description 28
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 claims abstract description 41
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 claims abstract description 26
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 claims abstract description 8
- 238000000034 method Methods 0.000 claims description 56
- 238000011282 treatment Methods 0.000 claims description 25
- 239000001301 oxygen Substances 0.000 claims description 22
- 229910052760 oxygen Inorganic materials 0.000 claims description 22
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 20
- 239000000654 additive Substances 0.000 claims description 18
- 239000000463 material Substances 0.000 claims description 12
- 239000002585 base Substances 0.000 claims description 10
- 229910052783 alkali metal Inorganic materials 0.000 claims description 9
- 150000001340 alkali metals Chemical class 0.000 claims description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 9
- AWKYKXCWTDDILL-UHFFFAOYSA-N 1,4,4a,5,8,8a,9a,10a-octahydroanthracene-9,10-dione Chemical compound O=C1C2CC=CCC2C(=O)C2C1CC=CC2 AWKYKXCWTDDILL-UHFFFAOYSA-N 0.000 claims description 5
- IZUKQUVSCNEFMJ-UHFFFAOYSA-N 1,2-dinitrobenzene Chemical class [O-][N+](=O)C1=CC=CC=C1[N+]([O-])=O IZUKQUVSCNEFMJ-UHFFFAOYSA-N 0.000 claims description 4
- 239000003513 alkali Substances 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 238000004061 bleaching Methods 0.000 claims description 4
- 239000007789 gas Substances 0.000 claims description 4
- YFXCHAUHDMOLPI-UHFFFAOYSA-N 2,3-dimethyl-1,4,4a,9a-tetrahydroanthracene-9,10-dione Chemical compound C1=CC=C2C(=O)C3CC(C)=C(C)CC3C(=O)C2=C1 YFXCHAUHDMOLPI-UHFFFAOYSA-N 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 239000000203 mixture Substances 0.000 claims description 3
- 150000005181 nitrobenzenes Chemical class 0.000 claims description 3
- WDCYWAQPCXBPJA-UHFFFAOYSA-N 1,3-dinitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC([N+]([O-])=O)=C1 WDCYWAQPCXBPJA-UHFFFAOYSA-N 0.000 claims description 2
- FYFDQJRXFWGIBS-UHFFFAOYSA-N 1,4-dinitrobenzene Chemical compound [O-][N+](=O)C1=CC=C([N+]([O-])=O)C=C1 FYFDQJRXFWGIBS-UHFFFAOYSA-N 0.000 claims description 2
- YFZHODLXYNDBSM-UHFFFAOYSA-N 1-ethenyl-4-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(C=C)C=C1 YFZHODLXYNDBSM-UHFFFAOYSA-N 0.000 claims description 2
- XGVLKZBDQXJEBB-UHFFFAOYSA-N 2,3,6,7-tetramethyl-1,4,4a,5,8,8a,9a,10a-octahydroanthracene-9,10-dione Chemical compound C1C(C)=C(C)CC2C(=O)C3CC(C)=C(C)CC3C(=O)C21 XGVLKZBDQXJEBB-UHFFFAOYSA-N 0.000 claims description 2
- LQCKFXAPVKCRRU-UHFFFAOYSA-N 2,4-dinitrobenzene-1,3-diol Chemical compound OC1=CC=C([N+]([O-])=O)C(O)=C1[N+]([O-])=O LQCKFXAPVKCRRU-UHFFFAOYSA-N 0.000 claims description 2
- RMBFBMJGBANMMK-UHFFFAOYSA-N 2,4-dinitrotoluene Chemical compound CC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O RMBFBMJGBANMMK-UHFFFAOYSA-N 0.000 claims description 2
- DPJCXCZTLWNFOH-UHFFFAOYSA-N 2-nitroaniline Chemical compound NC1=CC=CC=C1[N+]([O-])=O DPJCXCZTLWNFOH-UHFFFAOYSA-N 0.000 claims description 2
- ZLCPKMIJYMHZMJ-UHFFFAOYSA-N 2-nitrobenzene-1,3-diol Chemical compound OC1=CC=CC(O)=C1[N+]([O-])=O ZLCPKMIJYMHZMJ-UHFFFAOYSA-N 0.000 claims description 2
- PLAZTCDQAHEYBI-UHFFFAOYSA-N 2-nitrotoluene Chemical compound CC1=CC=CC=C1[N+]([O-])=O PLAZTCDQAHEYBI-UHFFFAOYSA-N 0.000 claims description 2
- VYWYYJYRVSBHJQ-UHFFFAOYSA-N 3,5-dinitrobenzoic acid Chemical compound OC(=O)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1 VYWYYJYRVSBHJQ-UHFFFAOYSA-N 0.000 claims description 2
- ZXVONLUNISGICL-UHFFFAOYSA-N 4,6-dinitro-o-cresol Chemical compound CC1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1O ZXVONLUNISGICL-UHFFFAOYSA-N 0.000 claims description 2
- TYMLOMAKGOJONV-UHFFFAOYSA-N 4-nitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1 TYMLOMAKGOJONV-UHFFFAOYSA-N 0.000 claims description 2
- BXRFQSNOROATLV-UHFFFAOYSA-N 4-nitrobenzaldehyde Chemical compound [O-][N+](=O)C1=CC=C(C=O)C=C1 BXRFQSNOROATLV-UHFFFAOYSA-N 0.000 claims description 2
- OTLNPYWUJOZPPA-UHFFFAOYSA-N 4-nitrobenzoic acid Chemical compound OC(=O)C1=CC=C([N+]([O-])=O)C=C1 OTLNPYWUJOZPPA-UHFFFAOYSA-N 0.000 claims description 2
- ZPTVNYMJQHSSEA-UHFFFAOYSA-N 4-nitrotoluene Chemical compound CC1=CC=C([N+]([O-])=O)C=C1 ZPTVNYMJQHSSEA-UHFFFAOYSA-N 0.000 claims description 2
- 239000012736 aqueous medium Substances 0.000 claims description 2
- 239000007900 aqueous suspension Substances 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- LIIJAADTGFEECC-UHFFFAOYSA-N 2,7-diethyl-1,4,4a,5,8,8a,9a,10a-octahydroanthracene-9,10-dione Chemical compound C1C(CC)=CCC2C(=O)C3CC=C(CC)CC3C(=O)C21 LIIJAADTGFEECC-UHFFFAOYSA-N 0.000 claims 1
- DLIVBMRBFQRLKC-UHFFFAOYSA-N 2-ethyl-1,4,4a,9a-tetrahydroanthracene-9,10-dione Chemical compound C1=CC=C2C(=O)C3CC=C(CC)CC3C(=O)C2=C1 DLIVBMRBFQRLKC-UHFFFAOYSA-N 0.000 claims 1
- 239000002023 wood Substances 0.000 abstract description 9
- 241000609240 Ambelania acida Species 0.000 abstract description 2
- 239000010905 bagasse Substances 0.000 abstract description 2
- 239000010902 straw Substances 0.000 abstract description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
- 238000004537 pulping Methods 0.000 description 24
- 238000010411 cooking Methods 0.000 description 13
- 230000000996 additive effect Effects 0.000 description 8
- 239000002655 kraft paper Substances 0.000 description 8
- 230000029087 digestion Effects 0.000 description 6
- OSVXSBDYLRYLIG-UHFFFAOYSA-N dioxidochlorine(.) Chemical compound O=Cl=O OSVXSBDYLRYLIG-UHFFFAOYSA-N 0.000 description 6
- 150000001454 anthracenes Chemical class 0.000 description 5
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 4
- 230000008901 benefit Effects 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 229920005610 lignin Polymers 0.000 description 4
- 239000000123 paper Substances 0.000 description 4
- 241000894007 species Species 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 239000004155 Chlorine dioxide Substances 0.000 description 3
- 240000009002 Picea mariana Species 0.000 description 3
- 235000017997 Picea mariana var. mariana Nutrition 0.000 description 3
- 235000018000 Picea mariana var. semiprostrata Nutrition 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
- 239000005864 Sulphur Substances 0.000 description 3
- 239000001913 cellulose Substances 0.000 description 3
- 229920002678 cellulose Polymers 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 235000019398 chlorine dioxide Nutrition 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 150000004053 quinones Chemical class 0.000 description 3
- 235000018185 Betula X alpestris Nutrition 0.000 description 2
- 235000018212 Betula X uliginosa Nutrition 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- 229930194542 Keto Natural products 0.000 description 2
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 2
- JLVVSXFLKOJNIY-UHFFFAOYSA-N Magnesium ion Chemical compound [Mg+2] JLVVSXFLKOJNIY-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
- 238000005660 chlorination reaction Methods 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000011121 hardwood Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 159000000003 magnesium salts Chemical class 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 239000002609 medium Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 238000007670 refining Methods 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 239000011122 softwood Substances 0.000 description 2
- 229910021653 sulphate ion Inorganic materials 0.000 description 2
- UBZAFMFVKZCUHC-UHFFFAOYSA-N 1,3-dimethyl-1,4,4a,9a-tetrahydroanthracene-9,10-dione Chemical compound C1=CC=C2C(=O)C3CC(C)=CC(C)C3C(=O)C2=C1 UBZAFMFVKZCUHC-UHFFFAOYSA-N 0.000 description 1
- XPCZSIPRUSOJFO-UHFFFAOYSA-N 1,4,4a,9a-tetrahydroanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2C1CC=CC2 XPCZSIPRUSOJFO-UHFFFAOYSA-N 0.000 description 1
- IJJWOSAXNHWBPR-HUBLWGQQSA-N 5-[(3as,4s,6ar)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]-n-(6-hydrazinyl-6-oxohexyl)pentanamide Chemical compound N1C(=O)N[C@@H]2[C@H](CCCCC(=O)NCCCCCC(=O)NN)SC[C@@H]21 IJJWOSAXNHWBPR-HUBLWGQQSA-N 0.000 description 1
- RZVHIXYEVGDQDX-UHFFFAOYSA-N 9,10-anthraquinone Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3C(=O)C2=C1 RZVHIXYEVGDQDX-UHFFFAOYSA-N 0.000 description 1
- YYVYAPXYZVYDHN-UHFFFAOYSA-N 9,10-phenanthroquinone Chemical compound C1=CC=C2C(=O)C(=O)C3=CC=CC=C3C2=C1 YYVYAPXYZVYDHN-UHFFFAOYSA-N 0.000 description 1
- 244000283070 Abies balsamea Species 0.000 description 1
- 235000007173 Abies balsamea Nutrition 0.000 description 1
- 235000004710 Abies lasiocarpa Nutrition 0.000 description 1
- 241000208140 Acer Species 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 240000000731 Fagus sylvatica Species 0.000 description 1
- 235000010099 Fagus sylvatica Nutrition 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 241000218657 Picea Species 0.000 description 1
- 235000008331 Pinus X rigitaeda Nutrition 0.000 description 1
- 241000018646 Pinus brutia Species 0.000 description 1
- 235000011613 Pinus brutia Nutrition 0.000 description 1
- 241000218978 Populus deltoides Species 0.000 description 1
- 241000183024 Populus tremula Species 0.000 description 1
- 244000305267 Quercus macrolepis Species 0.000 description 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 238000003915 air pollution Methods 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 1
- 150000004056 anthraquinones Chemical class 0.000 description 1
- RJGDLRCDCYRQOQ-UHFFFAOYSA-N anthrone Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3CC2=C1 RJGDLRCDCYRQOQ-UHFFFAOYSA-N 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 229940000425 combination drug Drugs 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 150000005182 dinitrobenzenes Chemical class 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000013505 freshwater Substances 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 229910001629 magnesium chloride Inorganic materials 0.000 description 1
- 229910001425 magnesium ion Inorganic materials 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
Classifications
-
- D—TEXTILES; PAPER
- D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
- D21C—PRODUCTION OF CELLULOSE BY REMOVING NON-CELLULOSE SUBSTANCES FROM CELLULOSE-CONTAINING MATERIALS; REGENERATION OF PULPING LIQUORS; APPARATUS THEREFOR
- D21C3/00—Pulping cellulose-containing materials
- D21C3/003—Pulping cellulose-containing materials with organic compounds
Landscapes
- Paper (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/750,442 US4036680A (en) | 1976-12-14 | 1976-12-14 | Delignification of lignocellulosic material with a soda pulping liquor containing a Diels Alder adduct of benzoquinone or naphthoquinone in admixture with a nitro aromatic compound |
| US750,442 | 1976-12-14 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1096111A true CA1096111A (en) | 1981-02-24 |
Family
ID=25017892
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA291,186A Expired CA1096111A (en) | 1976-12-14 | 1977-11-18 | Delignification of lignocellulosic material with a soda pulping liquor containing a diels alder adduct of naphthoquinone in admixture with a nitro aromatic compound |
Country Status (13)
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2442912A1 (fr) * | 1978-07-27 | 1980-06-27 | Ugine Kuhlmann | Procede de cuisson de materiaux lignocellulosiques en vue de la production de pate a papier |
| CA1132763A (en) * | 1978-10-25 | 1982-10-05 | Harry H. Holton | Use of cyclic keto compounds as additives in vapor phase pulping process |
| DE2925544A1 (de) * | 1979-06-25 | 1981-01-22 | Bayer Ag | Verfahren zur delignifizierung von lignocellulose-materialien |
| DE2950693A1 (de) * | 1979-12-17 | 1981-06-25 | Bayer Ag, 5090 Leverkusen | Dispersionen von dinitroanthrachinonen, verfahren zu deren herstellung und ihre verwendung |
| JP6134445B2 (ja) | 2015-01-26 | 2017-05-24 | 日本製紙株式会社 | キシラン含有物の製造方法 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2538457A (en) * | 1946-11-02 | 1951-01-16 | Monie S Hudson | Treating wood |
| JPS51112903A (en) * | 1975-03-26 | 1976-10-05 | Honshu Paper Co Ltd | Process for digesting lignocellulose material with sulphites |
| JPS5143403A (en) * | 1974-10-09 | 1976-04-14 | Honshu Paper Co Ltd | Arukariparupuno seizohoho |
| FI51833C (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1975-03-18 | 1978-01-24 | Ahlstroem Oy | |
| CA1073161A (en) * | 1975-09-05 | 1980-03-11 | Canadian Industries Limited | Delignification process |
| JPS5374101A (en) * | 1976-12-10 | 1978-07-01 | Honshu Paper Co Ltd | Pulp making method |
-
1976
- 1976-12-14 US US05/750,442 patent/US4036680A/en not_active Expired - Lifetime
-
1977
- 1977-11-18 CA CA291,186A patent/CA1096111A/en not_active Expired
- 1977-11-22 NZ NZ185751A patent/NZ185751A/xx unknown
- 1977-11-23 ZA ZA00776988A patent/ZA776988B/xx unknown
- 1977-11-24 AU AU30921/77A patent/AU504215B2/en not_active Expired
- 1977-12-09 NO NO774234A patent/NO774234L/no unknown
- 1977-12-12 BR BR7708250A patent/BR7708250A/pt unknown
- 1977-12-13 JP JP14894177A patent/JPS5374103A/ja active Granted
- 1977-12-13 FI FI773772A patent/FI773772A7/fi not_active Application Discontinuation
- 1977-12-13 SE SE7714130A patent/SE434856B/xx unknown
- 1977-12-14 ES ES465040A patent/ES465040A1/es not_active Expired
- 1977-12-14 FR FR7737645A patent/FR2374465A1/fr active Granted
- 1977-12-14 DE DE19772755767 patent/DE2755767A1/de not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5374103A (en) | 1978-07-01 |
| FR2374465A1 (fr) | 1978-07-13 |
| DE2755767A1 (de) | 1978-06-15 |
| BR7708250A (pt) | 1978-09-05 |
| NZ185751A (en) | 1980-09-12 |
| SE7714130L (sv) | 1978-06-15 |
| JPS5345403B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1978-12-06 |
| AU504215B2 (en) | 1979-10-04 |
| FI773772A7 (fi) | 1978-06-15 |
| AU3092177A (en) | 1979-06-28 |
| FR2374465B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1981-03-06 |
| SE434856B (sv) | 1984-08-20 |
| ZA776988B (en) | 1978-09-27 |
| US4036680A (en) | 1977-07-19 |
| ES465040A1 (es) | 1978-12-01 |
| NO774234L (no) | 1978-06-15 |
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