WO1982000483A1 - Pulping of lignocellulose with aqueous alcohol and alkaline earth metal salt catalyst - Google Patents
Pulping of lignocellulose with aqueous alcohol and alkaline earth metal salt catalyst Download PDFInfo
- Publication number
- WO1982000483A1 WO1982000483A1 PCT/EP1981/000105 EP8100105W WO8200483A1 WO 1982000483 A1 WO1982000483 A1 WO 1982000483A1 EP 8100105 W EP8100105 W EP 8100105W WO 8200483 A1 WO8200483 A1 WO 8200483A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- acid
- cooking
- cooking liquor
- alcohol
- zero
- Prior art date
Links
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 title claims abstract description 48
- 229910052784 alkaline earth metal Inorganic materials 0.000 title claims abstract description 16
- -1 alkaline earth metal salt Chemical class 0.000 title claims abstract description 11
- 239000003054 catalyst Substances 0.000 title description 9
- 238000004537 pulping Methods 0.000 title description 6
- 238000010411 cooking Methods 0.000 claims abstract description 51
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 23
- 239000002253 acid Substances 0.000 claims abstract description 20
- 229920005610 lignin Polymers 0.000 claims abstract description 16
- 239000000463 material Substances 0.000 claims abstract description 12
- 239000000203 mixture Substances 0.000 claims abstract description 10
- 150000003839 salts Chemical class 0.000 claims abstract description 10
- 150000007524 organic acids Chemical class 0.000 claims abstract description 4
- 229910052500 inorganic mineral Inorganic materials 0.000 claims abstract 6
- 239000011707 mineral Substances 0.000 claims abstract 6
- 235000019441 ethanol Nutrition 0.000 claims description 30
- 238000000034 method Methods 0.000 claims description 18
- 239000000126 substance Substances 0.000 claims description 9
- 235000000346 sugar Nutrition 0.000 claims description 9
- 230000029087 digestion Effects 0.000 claims description 8
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- 150000008163 sugars Chemical class 0.000 claims description 3
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 2
- 229910002651 NO3 Inorganic materials 0.000 claims description 2
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 claims description 2
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 claims description 2
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Inorganic materials [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 claims description 2
- 229910052791 calcium Inorganic materials 0.000 claims description 2
- 239000011575 calcium Substances 0.000 claims description 2
- 229910052749 magnesium Inorganic materials 0.000 claims description 2
- 239000011777 magnesium Substances 0.000 claims description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 claims description 2
- 235000019341 magnesium sulphate Nutrition 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 235000010755 mineral Nutrition 0.000 claims 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 claims 2
- HFVMEOPYDLEHBR-UHFFFAOYSA-N (2-fluorophenyl)-phenylmethanol Chemical compound C=1C=CC=C(F)C=1C(O)C1=CC=CC=C1 HFVMEOPYDLEHBR-UHFFFAOYSA-N 0.000 claims 1
- 239000005711 Benzoic acid Substances 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 1
- 229910021577 Iron(II) chloride Inorganic materials 0.000 claims 1
- 229910021578 Iron(III) chloride Inorganic materials 0.000 claims 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 claims 1
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 claims 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims 1
- 235000010233 benzoic acid Nutrition 0.000 claims 1
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 claims 1
- 239000004327 boric acid Substances 0.000 claims 1
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 claims 1
- NMCUIPGRVMDVDB-UHFFFAOYSA-L iron dichloride Chemical compound Cl[Fe]Cl NMCUIPGRVMDVDB-UHFFFAOYSA-L 0.000 claims 1
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 claims 1
- 229910017604 nitric acid Inorganic materials 0.000 claims 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 16
- 150000001720 carbohydrates Chemical class 0.000 abstract description 11
- 230000015556 catabolic process Effects 0.000 abstract description 7
- 238000006731 degradation reaction Methods 0.000 abstract description 7
- 239000000843 powder Substances 0.000 abstract description 3
- 239000011877 solvent mixture Substances 0.000 abstract description 2
- 230000008020 evaporation Effects 0.000 abstract 1
- 238000001704 evaporation Methods 0.000 abstract 1
- 229910052751 metal Inorganic materials 0.000 abstract 1
- 239000002184 metal Substances 0.000 abstract 1
- 239000002023 wood Substances 0.000 description 12
- 239000000835 fiber Substances 0.000 description 11
- 241000218657 Picea Species 0.000 description 10
- 235000014633 carbohydrates Nutrition 0.000 description 10
- 230000000694 effects Effects 0.000 description 9
- 241000894007 species Species 0.000 description 6
- 229920002678 cellulose Polymers 0.000 description 5
- 238000000926 separation method Methods 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 241000183024 Populus tremula Species 0.000 description 4
- 239000001913 cellulose Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 229920002488 Hemicellulose Polymers 0.000 description 3
- 239000003377 acid catalyst Substances 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 238000011084 recovery Methods 0.000 description 3
- SRBFZHDQGSBBOR-IOVATXLUSA-N D-xylopyranose Chemical compound O[C@@H]1COC(O)[C@H](O)[C@H]1O SRBFZHDQGSBBOR-IOVATXLUSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- 229920001131 Pulp (paper) Polymers 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 229910001413 alkali metal ion Inorganic materials 0.000 description 2
- 230000003139 buffering effect Effects 0.000 description 2
- 238000000855 fermentation Methods 0.000 description 2
- 230000004151 fermentation Effects 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 230000035515 penetration Effects 0.000 description 2
- 230000002035 prolonged effect Effects 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 235000018185 Betula X alpestris Nutrition 0.000 description 1
- 235000018212 Betula X uliginosa Nutrition 0.000 description 1
- 241000283690 Bos taurus Species 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- 235000014466 Douglas bleu Nutrition 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 244000166124 Eucalyptus globulus Species 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 229920000057 Mannan Polymers 0.000 description 1
- 235000008565 Pinus banksiana Nutrition 0.000 description 1
- 241000218680 Pinus banksiana Species 0.000 description 1
- 244000019397 Pinus jeffreyi Species 0.000 description 1
- 235000013267 Pinus ponderosa Nutrition 0.000 description 1
- 235000013269 Pinus ponderosa var ponderosa Nutrition 0.000 description 1
- 235000013268 Pinus ponderosa var scopulorum Nutrition 0.000 description 1
- 240000001416 Pseudotsuga menziesii Species 0.000 description 1
- 235000005386 Pseudotsuga menziesii var menziesii Nutrition 0.000 description 1
- 240000000111 Saccharum officinarum Species 0.000 description 1
- 235000007201 Saccharum officinarum Nutrition 0.000 description 1
- 241000209140 Triticum Species 0.000 description 1
- 235000021307 Triticum Nutrition 0.000 description 1
- 240000003021 Tsuga heterophylla Species 0.000 description 1
- 235000008554 Tsuga heterophylla Nutrition 0.000 description 1
- 235000011054 acetic acid Nutrition 0.000 description 1
- 150000001243 acetic acids Chemical class 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- PYMYPHUHKUWMLA-UHFFFAOYSA-N arabinose Natural products OCC(O)C(O)C(O)C=O PYMYPHUHKUWMLA-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- SRBFZHDQGSBBOR-UHFFFAOYSA-N beta-D-Pyranose-Lyxose Natural products OC1COC(O)C(O)C1O SRBFZHDQGSBBOR-UHFFFAOYSA-N 0.000 description 1
- 235000019846 buffering salt Nutrition 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000001143 conditioned effect Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 150000004674 formic acids Chemical class 0.000 description 1
- 239000012634 fragment Substances 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000003265 pulping liquor Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 239000011122 softwood Substances 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000010902 straw Substances 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 238000007669 thermal treatment Methods 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 229920001221 xylan Polymers 0.000 description 1
- 150000004823 xylans 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
- D21C3/20—Pulping cellulose-containing materials with organic solvents or in solvent environment
Definitions
- the invention relates to a method for the digestion of lignocellulose material which comprises cooking the fragmented lignocellulose material with an aqueous methyl or ethyl alcohol containing dissolved therein an alkaline earth metal salt, namely a chloride or nitrate of magnesium, calcium or barium or magnesium sulfate or a soluble mixture thereof in a concentration of less than 1.0 molar and, optionally, an acid reacting substance in a concentration of Less than 0.008 normal for not more than two hours at a temperature above 130°C, the amount of cooking liquor being at least 4 parts by weight per part by weight of the lignocellulose material, recovering the fibres liberated thereby from the cooking liquor, and separating the remaining spent cooking liquor into solvent, lignin and sugars.
- an alkaline earth metal salt namely a chloride or nitrate of magnesium, calcium or barium or magnesium sulfate or a soluble mixture thereof in a concentration of less than 1.0 molar and, optional
- the problem to be solved by the invention is to improve deligniflcation specificity for all lignocellulose species and thereby to increase the yield of cellulose pulp, to reduce viscosity losses in cellulose due to carbohydrate degradation, improve the quality and stability of dissolved lignin in solution and increase the uniformity of digestion at reduced cooking times of air-dry softwood chips and increase temperature stability of lignocellulose materials during high temperature digestion.
- Great Britain patent No. 357 821 (Kleinert) describes a process for the decomposition of vegetable fibrous matter for the purpose of obtaining the cellulose and the incrusting materials which uses as the decomposing agent mixtures of alcohol and water with a water content of 20 to 75 percent by weight and states on page 1, lines 74 to 77, that with 96 percent alcohol a dark brown residue amounting to 92 percent of the raw material is obtained.
- angewandte Chemie 44 (1931), pages 788 to 791, states on page 789 that absolute alcohol solves only little lignin and nearly no carbohydrates, and on same page, lines 4 to 2 from the bottom with reference to figure 1 that maximum digestion results with an alcohol content of 45 to 50 percent, and United States patent No. 3 585 104 (Kleinert) states in lines 42 to 44 of c.2 that methanol or ethanol in the medium concentration range between about 20 per cent and 75 percent by weight alcohol content have a stronger delignifying effect upon fibrous plant materials than the water-free alcohols.
- methanol is the preferred alcohol, bute where methanol is not available in sufficient amount ethanol can be used as well.
- the preferred alcohol content of the cooking liquor is 80 to 98 pe rc e n t by volume, but the higher percentages within this range are relatively difficult to achieve because of the moisture contained in the lignocellulose starting material.
- the preferred ratio of lignocellulose material to cooking liquor is 1:6 to 1:20.
- Wood chips in both air-dry and green conditions were conditioned to a uniform moisture content before the pulping trials.
- Batch quantities of commercial size chips were charged into the digester with ten times their weight of cooking liquor containing predetermined quantities of the salt catalysts.
- the volume ratio of methanol to water ranged between 90:10.
- the sealed stationary vessel was quickly brought to cooking temperature in a thermostatically controlled glycerine bath and the temperature held constant for the cooking interval required.
- the reported cooks are those which at the end of the stated period produced a free pulp when slurried in a disintegrator at slow stirred speed.
- the process also appeals to be quite tolerant to extended cooking times wherein the parameter most affected is residual lignin content.
- the pulping liquor when subjected to vacuum distillation at low temperature yields a flocculated lignin precipitate.
- a sugar solution having a solids concentration up to 25 percent is obtained.
- Charcoal filtration removes most of the yellow color due to the water soluble lignin depolymerisation products.
- the molecular weight distribution of the lignin shows one major and 2 to 3 minor peaks with the maximum being under 3800. Purification of the crude lingin is most effectively done by redissolution in acetone and spray drying in vacuum at low temperature to avoid melting and resinification. A dried solid filter cake is easily broken up into a free flowing tan-colored powder.
Landscapes
- Paper (AREA)
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE8181902305T DE3177195D1 (de) | 1980-07-25 | 1981-07-24 | Pulpen von lignocellulose mit waessrigem alkohol und einem alkali-erdmetallsalz-katalysator. |
| BR8108706A BR8108706A (pt) | 1980-07-25 | 1981-07-24 | Polpacao de lignocelulose com alcool aquoso e catalisador de sal de metal alcalino terroso |
| AT81902305T ATE54190T1 (de) | 1980-07-25 | 1981-07-24 | Pulpen von lignocellulose mit waessrigem alkohol und einem alkali-erdmetallsalz-katalysator. |
| FI820927A FI71781C (fi) | 1980-07-25 | 1982-03-17 | Kokning av lignocellulosa med vattenhaltig alkohol och jordalkalimetallsaltkatalysator. |
| SU823411783A RU1830091C (ru) | 1980-07-25 | 1982-03-24 | Способ варки лигноцеллюлозного материала |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA359443800725 | 1980-07-25 | ||
| CA000359443A CA1150012A (en) | 1980-07-25 | 1980-07-25 | Aqueous catalysed solvent pulping of lignocellulose |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO1982000483A1 true WO1982000483A1 (en) | 1982-02-18 |
Family
ID=4117790
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/EP1981/000105 WO1982000483A1 (en) | 1980-07-25 | 1981-07-24 | Pulping of lignocellulose with aqueous alcohol and alkaline earth metal salt catalyst |
Country Status (8)
| Country | Link |
|---|---|
| EP (1) | EP0056409B1 (enrdf_load_stackoverflow) |
| JP (1) | JPH0329917B2 (enrdf_load_stackoverflow) |
| BR (1) | BR8108706A (enrdf_load_stackoverflow) |
| CA (1) | CA1150012A (enrdf_load_stackoverflow) |
| DE (1) | DE3177195D1 (enrdf_load_stackoverflow) |
| FI (1) | FI71781C (enrdf_load_stackoverflow) |
| RU (1) | RU1830091C (enrdf_load_stackoverflow) |
| WO (1) | WO1982000483A1 (enrdf_load_stackoverflow) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1982003409A1 (en) * | 1981-03-26 | 1982-10-14 | Bau Forschung Thermoform | High efficiency organosolv saccharification process |
| WO1993020279A1 (en) * | 1992-04-06 | 1993-10-14 | A. Ahlstrom Corporation | Method of producing pulp |
| WO2006134126A1 (en) * | 2005-06-15 | 2006-12-21 | Shell Internationale Research Maatschappij B.V. | A process for organosolv pulping and use of a gamma lactone in a solvent for organosolv pulping |
| US8003818B2 (en) | 2004-12-23 | 2011-08-23 | Shell Oil Company | Process for the hydrogenation of a lactone or of a carboxylic acid or an ester having a gamma-carbonyl group |
| US8580978B2 (en) | 2009-08-07 | 2013-11-12 | Shell Oil Company | Process for preparing a hydroxyacid or hydroxyester |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4699124A (en) * | 1985-06-28 | 1987-10-13 | Power Alcohol, Inc. | Process for converting cellulose to glucose and other saccharides |
| JP5136984B2 (ja) * | 2007-04-04 | 2013-02-06 | 独立行政法人産業技術総合研究所 | 糖の製造方法 |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2022654A (en) * | 1933-03-07 | 1935-12-03 | Dreyfus Henry | Treatment of cellulosic materials |
| US2560638A (en) * | 1942-03-11 | 1951-07-17 | Celanese Corp | Manufacture of cellulose |
| CH386823A (de) * | 1959-02-06 | 1965-01-15 | Ceskoslovenska Akademie Ved | Verfahren zur Gewinnung von nativem Lignin und Hemizellulose |
| DE2920731A1 (de) * | 1978-11-27 | 1980-05-29 | Thermoform Bau Forschung | Verfahren zur chemischen umwandlung von lignocellulose unter abtrennung von fasern davon |
-
1980
- 1980-07-25 CA CA000359443A patent/CA1150012A/en not_active Expired
-
1981
- 1981-07-24 BR BR8108706A patent/BR8108706A/pt unknown
- 1981-07-24 DE DE8181902305T patent/DE3177195D1/de not_active Expired - Lifetime
- 1981-07-24 WO PCT/EP1981/000105 patent/WO1982000483A1/en active IP Right Grant
- 1981-07-24 JP JP56502589A patent/JPH0329917B2/ja not_active Expired
- 1981-07-24 EP EP19810902305 patent/EP0056409B1/en not_active Expired
-
1982
- 1982-03-17 FI FI820927A patent/FI71781C/fi not_active IP Right Cessation
- 1982-03-24 RU SU823411783A patent/RU1830091C/ru active
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2022654A (en) * | 1933-03-07 | 1935-12-03 | Dreyfus Henry | Treatment of cellulosic materials |
| US2560638A (en) * | 1942-03-11 | 1951-07-17 | Celanese Corp | Manufacture of cellulose |
| CH386823A (de) * | 1959-02-06 | 1965-01-15 | Ceskoslovenska Akademie Ved | Verfahren zur Gewinnung von nativem Lignin und Hemizellulose |
| DE2920731A1 (de) * | 1978-11-27 | 1980-05-29 | Thermoform Bau Forschung | Verfahren zur chemischen umwandlung von lignocellulose unter abtrennung von fasern davon |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1982003409A1 (en) * | 1981-03-26 | 1982-10-14 | Bau Forschung Thermoform | High efficiency organosolv saccharification process |
| WO1993020279A1 (en) * | 1992-04-06 | 1993-10-14 | A. Ahlstrom Corporation | Method of producing pulp |
| US8003818B2 (en) | 2004-12-23 | 2011-08-23 | Shell Oil Company | Process for the hydrogenation of a lactone or of a carboxylic acid or an ester having a gamma-carbonyl group |
| WO2006134126A1 (en) * | 2005-06-15 | 2006-12-21 | Shell Internationale Research Maatschappij B.V. | A process for organosolv pulping and use of a gamma lactone in a solvent for organosolv pulping |
| US8580978B2 (en) | 2009-08-07 | 2013-11-12 | Shell Oil Company | Process for preparing a hydroxyacid or hydroxyester |
Also Published As
| Publication number | Publication date |
|---|---|
| FI71781B (fi) | 1986-10-31 |
| RU1830091C (ru) | 1993-07-23 |
| JPS57501239A (enrdf_load_stackoverflow) | 1982-07-15 |
| JPH0329917B2 (enrdf_load_stackoverflow) | 1991-04-25 |
| DE3177195D1 (de) | 1990-08-02 |
| CA1150012A (en) | 1983-07-19 |
| EP0056409A1 (en) | 1982-07-28 |
| EP0056409B1 (en) | 1990-06-27 |
| BR8108706A (pt) | 1982-06-01 |
| FI71781C (fi) | 1987-02-09 |
| FI820927L (fi) | 1982-03-17 |
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