CH653054A5 - Procede pour delignifier le bois et autres produits lignocellulosiques. - Google Patents

Procede pour delignifier le bois et autres produits lignocellulosiques. Download PDF

Info

Publication number: CH653054A5
Authority: CH; Switzerland
Prior art keywords: phenol; aqueous; lignin; liquid; acid
Prior art date: 1981-12-10

Application number

CH7108/82A

Other languages

English (en)

French (fr)

Inventor

Herve Tournier

Jean-Pierre Sachetto

Jean-Pierre Michel

Alain Roman

Allan Johansson

Jean-Michel Armanet

Original Assignee

Battelle Memorial Institute

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.)

1981-12-10

Filing date

1982-12-07

Publication date

1985-12-13

1982-12-07 Application filed by Battelle Memorial Institute filed Critical Battelle Memorial Institute

1985-12-13 Publication of CH653054A5 publication Critical patent/CH653054A5/fr

Links

238000000034 method Methods 0.000 title claims abstract description 49
230000008569 process Effects 0.000 title claims description 24
239000002023 wood Substances 0.000 title description 30
229920005610 lignin Polymers 0.000 claims abstract description 79
239000007788 liquid Substances 0.000 claims abstract description 63
239000001913 cellulose Substances 0.000 claims abstract description 55
229920002678 cellulose Polymers 0.000 claims abstract description 55
150000002989 phenols Chemical class 0.000 claims abstract description 54
239000007787 solid Substances 0.000 claims abstract description 52
150000002972 pentoses Chemical class 0.000 claims abstract description 47
239000012978 lignocellulosic material Substances 0.000 claims abstract description 23
238000006243 chemical reaction Methods 0.000 claims abstract description 20
239000000463 material Substances 0.000 claims abstract description 18
238000004821 distillation Methods 0.000 claims abstract description 12
239000007791 liquid phase Substances 0.000 claims abstract description 12
238000001914 filtration Methods 0.000 claims abstract description 5
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 216
229960003742 phenol Drugs 0.000 claims description 105
239000008346 aqueous phase Substances 0.000 claims description 43
239000002253 acid Substances 0.000 claims description 39
239000000203 mixture Substances 0.000 claims description 39
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 37
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 37
239000012074 organic phase Substances 0.000 claims description 25
HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 claims description 18
230000007062 hydrolysis Effects 0.000 claims description 17
238000006460 hydrolysis reaction Methods 0.000 claims description 17
239000012071 phase Substances 0.000 claims description 17
238000010438 heat treatment Methods 0.000 claims description 16
229920002488 Hemicellulose Polymers 0.000 claims description 15
238000010992 reflux Methods 0.000 claims description 15
238000000926 separation method Methods 0.000 claims description 15
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 12
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 9
239000007864 aqueous solution Substances 0.000 claims description 9
150000007513 acids Chemical class 0.000 claims description 8
-1 aryl sulfonic acids Chemical class 0.000 claims description 7
239000000706 filtrate Substances 0.000 claims description 6
235000011149 sulphuric acid Nutrition 0.000 claims description 5
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
239000003153 chemical reaction reagent Substances 0.000 claims description 4
150000001875 compounds Chemical class 0.000 claims description 4
239000007789 gas Substances 0.000 claims description 4
235000006408 oxalic acid Nutrition 0.000 claims description 4
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 3
150000007524 organic acids Chemical class 0.000 claims description 3
235000005985 organic acids Nutrition 0.000 claims description 3
235000011007 phosphoric acid Nutrition 0.000 claims description 3
238000009987 spinning Methods 0.000 claims description 3
239000007858 starting material Substances 0.000 claims description 3
235000011167 hydrochloric acid Nutrition 0.000 claims description 2
230000003301 hydrolyzing effect Effects 0.000 claims description 2
238000002955 isolation Methods 0.000 claims description 2
229920006395 saturated elastomer Polymers 0.000 claims description 2
YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 claims description 2
125000000217 alkyl group Chemical group 0.000 claims 1
SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 claims 1
238000002425 crystallisation Methods 0.000 claims 1
230000008025 crystallization Effects 0.000 claims 1
239000000376 reactant Substances 0.000 claims 1
239000010410 layer Substances 0.000 abstract description 11
239000011260 aqueous acid Substances 0.000 abstract description 9
238000000197 pyrolysis Methods 0.000 abstract description 9
239000012044 organic layer Substances 0.000 abstract description 7
239000000470 constituent Substances 0.000 abstract description 6
238000004537 pulping Methods 0.000 abstract 1
239000000835 fiber Substances 0.000 description 35
235000000346 sugar Nutrition 0.000 description 28
239000000243 solution Substances 0.000 description 24
241000609240 Ambelania acida Species 0.000 description 21
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
239000010905 bagasse Substances 0.000 description 21
150000008163 sugars Chemical class 0.000 description 21
238000004458 analytical method Methods 0.000 description 18
239000000047 product Substances 0.000 description 17
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
230000008901 benefit Effects 0.000 description 11
239000002904 solvent Substances 0.000 description 10
238000009835 boiling Methods 0.000 description 9
150000002402 hexoses Chemical class 0.000 description 9
238000001816 cooling Methods 0.000 description 8
230000000694 effects Effects 0.000 description 8
238000005406 washing Methods 0.000 description 8
241000196324 Embryophyta Species 0.000 description 7
235000011121 sodium hydroxide Nutrition 0.000 description 7
239000000126 substance Substances 0.000 description 7
YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 6
238000000354 decomposition reaction Methods 0.000 description 6
LHGVFZTZFXWLCP-UHFFFAOYSA-N guaiacol Chemical compound COC1=CC=CC=C1O LHGVFZTZFXWLCP-UHFFFAOYSA-N 0.000 description 6
238000004519 manufacturing process Methods 0.000 description 6
238000011084 recovery Methods 0.000 description 6
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 5
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 5
238000010908 decantation Methods 0.000 description 5
238000000605 extraction Methods 0.000 description 5
239000008103 glucose Substances 0.000 description 5
239000003960 organic solvent Substances 0.000 description 5
230000002829 reductive effect Effects 0.000 description 5
238000011282 treatment Methods 0.000 description 5
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
235000018185 Betula X alpestris Nutrition 0.000 description 4
235000018212 Betula X uliginosa Nutrition 0.000 description 4
230000015572 biosynthetic process Effects 0.000 description 4
238000004090 dissolution Methods 0.000 description 4
235000011837 pasties Nutrition 0.000 description 4
229920005989 resin Polymers 0.000 description 4
239000011347 resin Substances 0.000 description 4
239000010902 straw Substances 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
239000003054 catalyst Substances 0.000 description 3
238000001704 evaporation Methods 0.000 description 3
230000008020 evaporation Effects 0.000 description 3
239000000446 fuel Substances 0.000 description 3
229960001867 guaiacol Drugs 0.000 description 3
230000006872 improvement Effects 0.000 description 3
229910052500 inorganic mineral Inorganic materials 0.000 description 3
238000004898 kneading Methods 0.000 description 3
239000002609 medium Substances 0.000 description 3
239000011707 mineral Substances 0.000 description 3
235000010755 mineral Nutrition 0.000 description 3
230000035484 reaction time Effects 0.000 description 3
238000004064 recycling Methods 0.000 description 3
MWOOGOJBHIARFG-UHFFFAOYSA-N vanillin Chemical compound COC1=CC(C=O)=CC=C1O MWOOGOJBHIARFG-UHFFFAOYSA-N 0.000 description 3
235000012141 vanillin Nutrition 0.000 description 3
FGQOOHJZONJGDT-UHFFFAOYSA-N vanillin Natural products COC1=CC(O)=CC(C=O)=C1 FGQOOHJZONJGDT-UHFFFAOYSA-N 0.000 description 3
PETRWTHZSKVLRE-UHFFFAOYSA-N 2-Methoxy-4-methylphenol Chemical compound COC1=CC(C)=CC=C1O PETRWTHZSKVLRE-UHFFFAOYSA-N 0.000 description 2
JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 2
CHWNEIVBYREQRF-UHFFFAOYSA-N 4-Ethyl-2-methoxyphenol Chemical compound CCC1=CC=C(O)C(OC)=C1 CHWNEIVBYREQRF-UHFFFAOYSA-N 0.000 description 2
HXDOZKJGKXYMEW-UHFFFAOYSA-N 4-ethylphenol Chemical compound CCC1=CC=C(O)C=C1 HXDOZKJGKXYMEW-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
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
PXIKRTCSSLJURC-UHFFFAOYSA-N Dihydroeugenol Chemical compound CCCC1=CC=C(O)C(OC)=C1 PXIKRTCSSLJURC-UHFFFAOYSA-N 0.000 description 2
240000000731 Fagus sylvatica Species 0.000 description 2
235000010099 Fagus sylvatica Nutrition 0.000 description 2
QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
240000000111 Saccharum officinarum Species 0.000 description 2
235000007201 Saccharum officinarum Nutrition 0.000 description 2
LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 2
241000209140 Triticum Species 0.000 description 2
235000021307 Triticum Nutrition 0.000 description 2
239000012223 aqueous fraction Substances 0.000 description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
229910052794 bromium Inorganic materials 0.000 description 2
230000015556 catabolic process Effects 0.000 description 2
239000007795 chemical reaction product Substances 0.000 description 2
150000001896 cresols Chemical class 0.000 description 2
238000006731 degradation reaction Methods 0.000 description 2
RRAFCDWBNXTKKO-UHFFFAOYSA-N eugenol Chemical compound COC1=CC(CC=C)=CC=C1O RRAFCDWBNXTKKO-UHFFFAOYSA-N 0.000 description 2
239000011521 glass Substances 0.000 description 2
238000004128 high performance liquid chromatography Methods 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 2
RNVCVTLRINQCPJ-UHFFFAOYSA-N o-toluidine Chemical compound CC1=CC=CC=C1N RNVCVTLRINQCPJ-UHFFFAOYSA-N 0.000 description 2
IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 2
239000000123 paper Substances 0.000 description 2
230000036961 partial effect Effects 0.000 description 2
239000002245 particle Substances 0.000 description 2
238000000746 purification Methods 0.000 description 2
239000002994 raw material Substances 0.000 description 2
GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
230000000717 retained effect Effects 0.000 description 2
238000003756 stirring Methods 0.000 description 2
LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 2
239000000725 suspension Substances 0.000 description 2
229920003002 synthetic resin Polymers 0.000 description 2
239000002699 waste material Substances 0.000 description 2
239000003643 water by type Substances 0.000 description 2
RNHDAKUGFHSZEV-UHFFFAOYSA-N 1,4-dioxane;hydrate Chemical compound O.C1COCCO1 RNHDAKUGFHSZEV-UHFFFAOYSA-N 0.000 description 1
JERRISPMQOTPKR-UHFFFAOYSA-N 1-ethyl-6-methoxycyclohexa-2,4-dien-1-ol Chemical compound CCC1(O)C=CC=CC1OC JERRISPMQOTPKR-UHFFFAOYSA-N 0.000 description 1
BSWWXRFVMJHFBN-UHFFFAOYSA-N 2,4,6-tribromophenol Chemical compound OC1=C(Br)C=C(Br)C=C1Br BSWWXRFVMJHFBN-UHFFFAOYSA-N 0.000 description 1
KUFFULVDNCHOFZ-UHFFFAOYSA-N 2,4-xylenol Chemical compound CC1=CC=C(O)C(C)=C1 KUFFULVDNCHOFZ-UHFFFAOYSA-N 0.000 description 1
KLIDCXVFHGNTTM-UHFFFAOYSA-N 2,6-dimethoxyphenol Chemical compound COC1=CC=CC(OC)=C1O KLIDCXVFHGNTTM-UHFFFAOYSA-N 0.000 description 1
ISPYQTSUDJAMAB-UHFFFAOYSA-N 2-chlorophenol Chemical compound OC1=CC=CC=C1Cl ISPYQTSUDJAMAB-UHFFFAOYSA-N 0.000 description 1
RSZPVOABCKCPKY-UHFFFAOYSA-N 2-ethyl-6-methoxyphenol Chemical class CCC1=CC=CC(OC)=C1O RSZPVOABCKCPKY-UHFFFAOYSA-N 0.000 description 1
IQUPABOKLQSFBK-UHFFFAOYSA-N 2-nitrophenol Chemical compound OC1=CC=CC=C1[N+]([O-])=O IQUPABOKLQSFBK-UHFFFAOYSA-N 0.000 description 1
ZBCATMYQYDCTIZ-UHFFFAOYSA-N 4-methylcatechol Chemical compound CC1=CC=C(O)C(O)=C1 ZBCATMYQYDCTIZ-UHFFFAOYSA-N 0.000 description 1
RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
NPBVQXIMTZKSBA-UHFFFAOYSA-N Chavibetol Natural products COC1=CC=C(CC=C)C=C1O NPBVQXIMTZKSBA-UHFFFAOYSA-N 0.000 description 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
239000005770 Eugenol Substances 0.000 description 1
238000005481 NMR spectroscopy Methods 0.000 description 1
240000007594 Oryza sativa Species 0.000 description 1
235000007164 Oryza sativa Nutrition 0.000 description 1
JPYHHZQJCSQRJY-UHFFFAOYSA-N Phloroglucinol Natural products CCC=CCC=CCC=CCC=CCCCCC(=O)C1=C(O)C=C(O)C=C1O JPYHHZQJCSQRJY-UHFFFAOYSA-N 0.000 description 1
235000008331 Pinus X rigitaeda Nutrition 0.000 description 1
235000011613 Pinus brutia Nutrition 0.000 description 1
241000018646 Pinus brutia Species 0.000 description 1
UVMRYBDEERADNV-UHFFFAOYSA-N Pseudoeugenol Natural products COC1=CC(C(C)=C)=CC=C1O UVMRYBDEERADNV-UHFFFAOYSA-N 0.000 description 1
240000004885 Quercus rubra Species 0.000 description 1
235000009135 Quercus rubra Nutrition 0.000 description 1
229910008433 SnCU Inorganic materials 0.000 description 1
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
239000004809 Teflon Substances 0.000 description 1
229920006362 Teflon® Polymers 0.000 description 1
240000008042 Zea mays Species 0.000 description 1
235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
235000002017 Zea mays subsp mays Nutrition 0.000 description 1
239000003377 acid catalyst Substances 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
239000000853 adhesive Substances 0.000 description 1
230000001070 adhesive effect Effects 0.000 description 1
239000003463 adsorbent Substances 0.000 description 1
239000003513 alkali Substances 0.000 description 1
239000012736 aqueous medium Substances 0.000 description 1
239000003125 aqueous solvent Substances 0.000 description 1
239000007900 aqueous suspension Substances 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
239000012159 carrier gas Substances 0.000 description 1
238000006555 catalytic reaction Methods 0.000 description 1
238000005119 centrifugation Methods 0.000 description 1
235000013339 cereals Nutrition 0.000 description 1
230000008859 change Effects 0.000 description 1
QVFWZNCVPCJQOP-UHFFFAOYSA-N chloralodol Chemical compound CC(O)(C)CC(C)OC(O)C(Cl)(Cl)Cl QVFWZNCVPCJQOP-UHFFFAOYSA-N 0.000 description 1
230000000052 comparative effect Effects 0.000 description 1
239000000356 contaminant Substances 0.000 description 1
238000011109 contamination Methods 0.000 description 1
238000010924 continuous production Methods 0.000 description 1
230000008602 contraction Effects 0.000 description 1
235000005822 corn Nutrition 0.000 description 1
239000012043 crude product Substances 0.000 description 1
230000009089 cytolysis Effects 0.000 description 1
230000003247 decreasing effect Effects 0.000 description 1
239000007857 degradation product Substances 0.000 description 1
238000001514 detection method Methods 0.000 description 1
230000029087 digestion Effects 0.000 description 1
238000006073 displacement reaction Methods 0.000 description 1
238000009826 distribution Methods 0.000 description 1
238000001035 drying Methods 0.000 description 1
230000009977 dual effect Effects 0.000 description 1
210000005069 ears Anatomy 0.000 description 1
230000008030 elimination Effects 0.000 description 1
238000003379 elimination reaction Methods 0.000 description 1
238000011067 equilibration Methods 0.000 description 1
239000000686 essence Substances 0.000 description 1
229960002217 eugenol Drugs 0.000 description 1
239000000284 extract Substances 0.000 description 1
238000000855 fermentation Methods 0.000 description 1
230000004151 fermentation Effects 0.000 description 1
239000012530 fluid Substances 0.000 description 1
238000005243 fluidization Methods 0.000 description 1
150000002240 furans Chemical class 0.000 description 1
238000004817 gas chromatography Methods 0.000 description 1
230000005484 gravity Effects 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
239000012535 impurity Substances 0.000 description 1
239000011872 intimate mixture Substances 0.000 description 1
239000002655 kraft paper Substances 0.000 description 1
238000002386 leaching Methods 0.000 description 1
150000002672 m-cresols Chemical class 0.000 description 1
229940057952 methanol Drugs 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
238000002156 mixing Methods 0.000 description 1
238000012986 modification Methods 0.000 description 1
230000004048 modification Effects 0.000 description 1
NXPPAOGUKPJVDI-UHFFFAOYSA-N naphthalene-1,2-diol Chemical class C1=CC=CC2=C(O)C(O)=CC=C21 NXPPAOGUKPJVDI-UHFFFAOYSA-N 0.000 description 1
150000004780 naphthols Chemical class 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
150000002883 o-cresols Chemical class 0.000 description 1
150000002931 p-cresols Chemical class 0.000 description 1
230000020477 pH reduction Effects 0.000 description 1
238000010422 painting Methods 0.000 description 1
230000000149 penetrating effect Effects 0.000 description 1
238000005325 percolation Methods 0.000 description 1
KSSNXJHPEFVKHY-UHFFFAOYSA-N phenol;hydrate Chemical compound O.OC1=CC=CC=C1 KSSNXJHPEFVKHY-UHFFFAOYSA-N 0.000 description 1
ISWSIDIOOBJBQZ-UHFFFAOYSA-M phenolate Chemical compound [O-]C1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-M 0.000 description 1
229940031826 phenolate Drugs 0.000 description 1
QCDYQQDYXPDABM-UHFFFAOYSA-N phloroglucinol Chemical compound OC1=CC(O)=CC(O)=C1 QCDYQQDYXPDABM-UHFFFAOYSA-N 0.000 description 1
229960001553 phloroglucinol Drugs 0.000 description 1
239000010908 plant waste Substances 0.000 description 1
229920000642 polymer Polymers 0.000 description 1
239000002952 polymeric resin Substances 0.000 description 1
238000006116 polymerization reaction Methods 0.000 description 1
239000000843 powder Substances 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
238000003825 pressing Methods 0.000 description 1
230000002035 prolonged effect Effects 0.000 description 1
239000005297 pyrex Substances 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
239000003507 refrigerant Substances 0.000 description 1
229920003987 resole Polymers 0.000 description 1
230000002441 reversible effect Effects 0.000 description 1
235000009566 rice Nutrition 0.000 description 1
238000004904 shortening Methods 0.000 description 1
229910052814 silicon oxide Inorganic materials 0.000 description 1
229920002545 silicone oil Polymers 0.000 description 1
239000011343 solid material Substances 0.000 description 1
239000008247 solid mixture Substances 0.000 description 1
229910001220 stainless steel Inorganic materials 0.000 description 1
239000010935 stainless steel Substances 0.000 description 1
238000001256 steam distillation Methods 0.000 description 1
239000011593 sulfur Substances 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
150000003464 sulfur compounds Chemical class 0.000 description 1
DHCDFWKWKRSZHF-UHFFFAOYSA-N sulfurothioic S-acid Chemical compound OS(O)(=O)=S DHCDFWKWKRSZHF-UHFFFAOYSA-N 0.000 description 1
239000000057 synthetic resin Substances 0.000 description 1
238000005979 thermal decomposition reaction Methods 0.000 description 1
229920001187 thermosetting polymer Polymers 0.000 description 1
238000004448 titration Methods 0.000 description 1
239000010875 treated wood Substances 0.000 description 1
238000003828 vacuum filtration Methods 0.000 description 1
239000002966 varnish Substances 0.000 description 1
235000013311 vegetables Nutrition 0.000 description 1
239000003039 volatile agent Substances 0.000 description 1
238000005303 weighing Methods 0.000 description 1
150000003739 xylenols Chemical class 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

Compounds Of Unknown Constitution (AREA)
Chemical And Physical Treatments For Wood And The Like (AREA)
Paper (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Polysaccharides And Polysaccharide Derivatives (AREA)
Stringed Musical Instruments (AREA)
Saccharide Compounds (AREA)

CH7108/82A 1981-12-10 1982-12-07 Procede pour delignifier le bois et autres produits lignocellulosiques. CH653054A5 (fr)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US32936081A	1981-12-10	1981-12-10

Publications (1)

Publication Number	Publication Date
CH653054A5 true CH653054A5 (fr)	1985-12-13

Family

ID=23285029

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH7108/82A CH653054A5 (fr)	1981-12-10	1982-12-07	Procede pour delignifier le bois et autres produits lignocellulosiques.

Country Status (12)

Country	Link
EP (2)	EP0097188A1 (de)
AT (1)	ATE16206T1 (de)
BE (1)	BE895299A (de)
BR (1)	BR8208011A (de)
CA (1)	CA1210209A (de)
CH (1)	CH653054A5 (de)
DE (1)	DE3267062D1 (de)
ES (1)	ES8404725A1 (de)
FI (1)	FI70938C (de)
FR (1)	FR2518141B1 (de)
NO (1)	NO832783L (de)
WO (1)	WO1983002125A1 (de)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
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FI77062C (fi) *	1986-12-31	1989-01-10	Neste Oy	Foerfarande foer cirkulering av fenol vid en fenolkokningsprocess av lignocellulosamaterial.
FI77061C (fi) *	1986-12-31	1989-01-10	Neste Oy	Foerfarande foer separering av lignin och fenol fraon fenolloesningar.
DE19856582C1 (de) *	1998-12-08	2001-03-15	Rhodia Acetow Ag	Verfahren zur Gewinnung von Chemiezellstoff aus Hackschnitzeln
CN102186871B (zh) *	2008-10-23	2014-03-19	独立行政法人科学技术振兴机构	浓酸处理部、浓酸处理方法、植物资源相分离系统转换装置和转换方法
CA3110389A1 (en) *	2021-02-25	2022-08-25	Sixring Inc.	Modified sulfuric acid and uses thereof
CN113307983B (zh) *	2021-05-21	2022-08-05	北京林业大学	一种绿色溶剂快速、高得率分离木质素的方法
CN116770613A (zh) *	2023-08-01	2023-09-19	贵州大学	热致液液相分离溶剂和纤维素预处理及组分分离的方法
CN119570060A (zh) *	2024-12-02	2025-03-07	齐鲁工业大学(山东省科学院)	一种提取浅色酚化木质素的方法

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Publication number	Priority date	Publication date	Assignee	Title
BE457089A (de) *	1943-02-27
FR989191A (fr) *	1944-09-07	1951-09-05	Traitement Chimique Des Vegeta	Procédé de traitement des matières fibreuses, plus particulièrement des végétaux en vue de l'obtention de la cellulose
US3215588A (en) *	1963-08-15	1965-11-02	Lummus Co	Continuous impregnation, cooking, and washing of fibrous material
AT336992B (de) *	1975-02-18	1977-06-10	Visch Khim T I Nis	Verfahren und vorrichtung zum herstellen von fasermaterial aus pflanzenrohstoffen
DE3161585D1 (en) *	1980-06-20	1984-01-12	Battelle Memorial Institute	A method for the delignification of wood and other ligno-cellulosic products
DE3168397D1 (en) *	1980-11-20	1985-02-28	Simmering Graz Pauker Ag	Process and apparatus for producing cellulose

1982
- 1982-12-07 CH CH7108/82A patent/CH653054A5/fr not_active IP Right Cessation
- 1982-12-07 BR BR8208011A patent/BR8208011A/pt unknown
- 1982-12-07 CA CA000417171A patent/CA1210209A/fr not_active Expired
- 1982-12-07 EP EP83900024A patent/EP0097188A1/de not_active Withdrawn
- 1982-12-07 ES ES518003A patent/ES8404725A1/es not_active Expired
- 1982-12-07 WO PCT/EP1982/000255 patent/WO1983002125A1/en not_active Ceased
- 1982-12-08 FR FR8220587A patent/FR2518141B1/fr not_active Expired
- 1982-12-09 BE BE0/209694A patent/BE895299A/fr not_active IP Right Cessation
- 1982-12-09 DE DE8282810536T patent/DE3267062D1/de not_active Expired
- 1982-12-09 EP EP82810536A patent/EP0082116B1/de not_active Expired
- 1982-12-09 AT AT82810536T patent/ATE16206T1/de not_active IP Right Cessation
- 1982-12-10 FI FI824244A patent/FI70938C/fi not_active IP Right Cessation
1983
- 1983-08-01 NO NO832783A patent/NO832783L/no unknown

Also Published As

Publication number	Publication date
ATE16206T1 (de)	1985-11-15
FI70938C (fi)	1986-10-27
FI824244A0 (fi)	1982-12-10
FR2518141A1 (fr)	1983-06-17
BE895299A (fr)	1983-06-09
BR8208011A (pt)	1983-11-08
FI824244L (fi)	1983-06-11
WO1983002125A1 (en)	1983-06-23
EP0082116A1 (de)	1983-06-22
NO832783L (no)	1983-08-01
EP0097188A1 (de)	1984-01-04
CA1210209A (fr)	1986-08-26
FR2518141B1 (fr)	1986-08-14
ES518003A0 (es)	1984-05-01
EP0082116B1 (de)	1985-10-23
DE3267062D1 (en)	1985-11-28
ES8404725A1 (es)	1984-05-01
FI70938B (fi)	1986-07-18

Legal Events

Date	Code	Title	Description
1988-08-31	PL	Patent ceased
2024-10-31	PL	Patent ceased

Publication	Publication Date	Title
US4511433A (en)	1985-04-16	Method for the simultaneous delignification of wood and other ligno-cellulosic materials and hydrolysis of the hemicellulose component thereof
US8901325B2 (en)	2014-12-02	Method for producing furfural from lignocellulosic biomass material
SU1194282A3 (ru)	1985-11-23	Способ разложени лигноцеллюлозного материала
EP1180171B1 (de)	2003-10-08	Verfahren zur herstellung von zellstoff, lignin, zucker und essigsäure durch fraktionierung des lignocellulosematerials mittels ameisensäure und essigsäure
WO2011114058A1 (fr)	2011-09-22	Procede de depolymerisation de biomasse lignocellulosique
US9382283B2 (en)	2016-07-05	Oxygen assisted organosolv process, system and method for delignification of lignocellulosic materials and lignin recovery
JPH06511043A (ja)	1994-12-08	リグノセルロース原料のパルプ化及び生成する副生物の回収
US11535582B2 (en)	2022-12-27	Levulinic acid purification
US20160145398A1 (en)	2016-05-26	Method for manufacturing lignin degradation product
CN108358770A (zh)	2018-08-03	由木质纤维素生物物质生产乙酰丙酸的方法
FI20195401A1 (en)	2020-11-16	Process for fractionating lignocellulosic materials and products obtained by said process
EP0082116B1 (de)	1985-10-23	Verfahren zur Delignifizierung von Holz und anderen Lignozelluloseprodukten
US20250075427A1 (en)	2025-03-06	Catalyst free organosolv process, system, and method for fractionation of lignocellulosic materials and bioproducts recovery
KR20150091155A (ko)	2015-08-07	레불린산 및 폼산의 단리 방법
JPS58502155A (ja)	1983-12-15	木材その他のリグノセルロ−ス製品の脱リグニン方法
WO2014087013A1 (en)	2014-06-12	Process for the isolation of levulinic acid
FR3048247B1 (fr)	2019-10-04	Procede de preparation d'un melange de monosaccharides et/ou d'oligosaccharides et/ou de polysaccharides par purification d'un hydrolysat de matieres lignocellulosiques
JPS58500431A (ja)	1983-03-24	高能率オルガノソルブ糖化法
WO2014087017A1 (en)	2014-06-12	Process for the preparation of levulinic acid esters
Kuruppu Arachchige Dona	2024	Recovery of caustic soda and side-products from the washing filtrates of the novel dissolving pulp process “StExCell”(steam-exploded cellulose pulp)
WO2015134352A1 (en)	2015-09-11	Method for removing mineral acid from levulinic acid
CA3106488C (en)	2024-11-12	Levulinic acid purification
FR3046790A1 (fr)	2017-07-21	Procede de transformation en milieu aqueux des glucides presents dans une biomasse en des levulinates d’alkyles