EP0021264B1 - Verfahren zur Delignifizierung von Lignocellulose-Materialien - Google Patents
Verfahren zur Delignifizierung von Lignocellulose-Materialien Download PDFInfo
- Publication number
- EP0021264B1 EP0021264B1 EP80103278A EP80103278A EP0021264B1 EP 0021264 B1 EP0021264 B1 EP 0021264B1 EP 80103278 A EP80103278 A EP 80103278A EP 80103278 A EP80103278 A EP 80103278A EP 0021264 B1 EP0021264 B1 EP 0021264B1
- Authority
- EP
- European Patent Office
- Prior art keywords
- nitro
- dinitroanthraquinone
- anthraquinone
- weight
- nitroanthraquinone
- 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
- 238000000034 method Methods 0.000 title claims abstract description 47
- 239000012978 lignocellulosic material Substances 0.000 title abstract description 7
- YCANAXVBJKNANM-UHFFFAOYSA-N 1-nitroanthracene-9,10-dione Chemical class O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2[N+](=O)[O-] YCANAXVBJKNANM-UHFFFAOYSA-N 0.000 claims abstract description 25
- 230000029087 digestion Effects 0.000 claims abstract description 20
- NMNSBFYYVHREEE-UHFFFAOYSA-N 1,2-dinitroanthracene-9,10-dione Chemical class C1=CC=C2C(=O)C3=C([N+]([O-])=O)C([N+](=O)[O-])=CC=C3C(=O)C2=C1 NMNSBFYYVHREEE-UHFFFAOYSA-N 0.000 claims abstract description 10
- 238000006243 chemical reaction Methods 0.000 claims abstract description 4
- 239000000463 material Substances 0.000 claims description 20
- 239000000203 mixture Substances 0.000 claims description 16
- 239000007788 liquid Substances 0.000 claims description 13
- -1 aromatic nitro-compounds Chemical class 0.000 claims description 11
- XFLONXIGNOXKCG-UHFFFAOYSA-N 2,7-dinitroanthracene-9,10-dione Chemical compound C1=C([N+]([O-])=O)C=C2C(=O)C3=CC([N+](=O)[O-])=CC=C3C(=O)C2=C1 XFLONXIGNOXKCG-UHFFFAOYSA-N 0.000 claims description 6
- XVMVHWDCRFNPQR-UHFFFAOYSA-N 1,5-dinitroanthracene-9,10-dione Chemical compound O=C1C=2C([N+](=O)[O-])=CC=CC=2C(=O)C2=C1C=CC=C2[N+]([O-])=O XVMVHWDCRFNPQR-UHFFFAOYSA-N 0.000 claims description 3
- UQKJUEALIQRECQ-UHFFFAOYSA-N 1,6-dinitroanthracene-9,10-dione Chemical compound O=C1C2=CC([N+](=O)[O-])=CC=C2C(=O)C2=C1C=CC=C2[N+]([O-])=O UQKJUEALIQRECQ-UHFFFAOYSA-N 0.000 claims description 3
- FAVDZWIRBSMLOV-UHFFFAOYSA-N 1,7-dinitroanthracene-9,10-dione Chemical compound C1=CC([N+]([O-])=O)=C2C(=O)C3=CC([N+](=O)[O-])=CC=C3C(=O)C2=C1 FAVDZWIRBSMLOV-UHFFFAOYSA-N 0.000 claims description 3
- MBIJFIUDKPXMAV-UHFFFAOYSA-N 1,8-dinitroanthracene-9,10-dione Chemical compound O=C1C2=CC=CC([N+]([O-])=O)=C2C(=O)C2=C1C=CC=C2[N+](=O)[O-] MBIJFIUDKPXMAV-UHFFFAOYSA-N 0.000 claims description 3
- KXMLYSJUXIUOHI-UHFFFAOYSA-N 1-amino-4-nitroanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C([N+]([O-])=O)=CC=C2N KXMLYSJUXIUOHI-UHFFFAOYSA-N 0.000 claims description 3
- HNKYUEBEJOEAJG-UHFFFAOYSA-N 1-ethoxy-5-nitroanthracene-9,10-dione Chemical compound O=C1C=2C(OCC)=CC=CC=2C(=O)C2=C1C=CC=C2[N+]([O-])=O HNKYUEBEJOEAJG-UHFFFAOYSA-N 0.000 claims description 3
- XXUOKOYLVBHBCG-UHFFFAOYSA-N 1-hydroxy-4-nitroanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C([N+]([O-])=O)=CC=C2O XXUOKOYLVBHBCG-UHFFFAOYSA-N 0.000 claims description 3
- OPXXCGAYBFDPHY-UHFFFAOYSA-N 2,6-dinitroanthracene-9,10-dione Chemical compound [O-][N+](=O)C1=CC=C2C(=O)C3=CC([N+](=O)[O-])=CC=C3C(=O)C2=C1 OPXXCGAYBFDPHY-UHFFFAOYSA-N 0.000 claims description 3
- QCVMOSGPTRRUQZ-UHFFFAOYSA-N 2-nitroanthracene-9,10-dione Chemical compound C1=CC=C2C(=O)C3=CC([N+](=O)[O-])=CC=C3C(=O)C2=C1 QCVMOSGPTRRUQZ-UHFFFAOYSA-N 0.000 claims description 3
- VGIVZECXTZAEHI-UHFFFAOYSA-N 8-nitro-9,10-dioxoanthracene-1-sulfonic acid Chemical compound O=C1C2=CC=CC([N+]([O-])=O)=C2C(=O)C2=C1C=CC=C2S(=O)(=O)O VGIVZECXTZAEHI-UHFFFAOYSA-N 0.000 claims description 3
- VOZLLWQPJJSWPR-UHFFFAOYSA-N 1-chloro-5-nitroanthracene-9,10-dione Chemical compound O=C1C2=C(Cl)C=CC=C2C(=O)C2=C1C=CC=C2[N+](=O)[O-] VOZLLWQPJJSWPR-UHFFFAOYSA-N 0.000 claims description 2
- PMOCDYOEOUEPAN-UHFFFAOYSA-N 1-nitro-9,10-dioxoanthracene-2-carboxylic acid Chemical compound C1=CC=C2C(=O)C3=C([N+]([O-])=O)C(C(=O)O)=CC=C3C(=O)C2=C1 PMOCDYOEOUEPAN-UHFFFAOYSA-N 0.000 claims description 2
- 238000010411 cooking Methods 0.000 description 30
- 239000002023 wood Substances 0.000 description 19
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 8
- 241000218657 Picea Species 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 5
- 239000003513 alkali Substances 0.000 description 4
- 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 4
- 150000004056 anthraquinones Chemical class 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 3
- 238000007792 addition Methods 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 239000001913 cellulose Substances 0.000 description 3
- 229920002678 cellulose Polymers 0.000 description 3
- 238000006396 nitration reaction Methods 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 239000005077 polysulfide Substances 0.000 description 3
- 229920001021 polysulfide Polymers 0.000 description 3
- 150000008117 polysulfides Polymers 0.000 description 3
- 235000018185 Betula X alpestris Nutrition 0.000 description 2
- 235000018212 Betula X uliginosa Nutrition 0.000 description 2
- 240000000731 Fagus sylvatica Species 0.000 description 2
- 235000010099 Fagus sylvatica Nutrition 0.000 description 2
- 235000008331 Pinus X rigitaeda Nutrition 0.000 description 2
- 241000018646 Pinus brutia Species 0.000 description 2
- 235000011613 Pinus brutia Nutrition 0.000 description 2
- 230000001133 acceleration Effects 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000004904 shortening Methods 0.000 description 2
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 2
- CKDYLXCYEQVJHE-UHFFFAOYSA-N 1,2,6-trihydroxy-3-nitroanthracene-9,10-dione Chemical compound OC1=C([N+]([O-])=O)C=C2C(=O)C3=CC(O)=CC=C3C(=O)C2=C1O CKDYLXCYEQVJHE-UHFFFAOYSA-N 0.000 description 1
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 1
- SDICTISQCKLMEB-UHFFFAOYSA-N 1,4-diamino-5-nitroanthracene-9,10-dione Chemical compound O=C1C=2C(N)=CC=C(N)C=2C(=O)C2=C1C=CC=C2[N+]([O-])=O SDICTISQCKLMEB-UHFFFAOYSA-N 0.000 description 1
- OPZUWDAYFQMSMY-UHFFFAOYSA-N 1,5-dihydroxy-4,8-dinitro-9,10-dioxoanthracene-2,6-disulfonic acid Chemical compound C1=C(S(O)(=O)=O)C(O)=C2C(=O)C3=C([N+]([O-])=O)C=C(S(O)(=O)=O)C(O)=C3C(=O)C2=C1[N+]([O-])=O OPZUWDAYFQMSMY-UHFFFAOYSA-N 0.000 description 1
- CUIHODIOWPLCMG-UHFFFAOYSA-N 1,5-dihydroxy-4,8-dinitroanthracene-9,10-dione Chemical compound O=C1C2=C(O)C=CC([N+]([O-])=O)=C2C(=O)C2=C1C([N+]([O-])=O)=CC=C2O CUIHODIOWPLCMG-UHFFFAOYSA-N 0.000 description 1
- JHVMTWUDBADLCI-UHFFFAOYSA-N 1,8-dichloro-3-nitroanthracene-9,10-dione Chemical compound C1=CC=C2C(=O)C3=CC([N+](=O)[O-])=CC(Cl)=C3C(=O)C2=C1Cl JHVMTWUDBADLCI-UHFFFAOYSA-N 0.000 description 1
- GJCHQJDEYFYWER-UHFFFAOYSA-N 1,8-dihydroxy-4,5-dinitroanthracene-9,10-dione Chemical compound O=C1C2=C([N+]([O-])=O)C=CC(O)=C2C(=O)C2=C1C([N+]([O-])=O)=CC=C2O GJCHQJDEYFYWER-UHFFFAOYSA-N 0.000 description 1
- MKBOTTRSSNRPPF-UHFFFAOYSA-N 1-amino-2,4-dinitroanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C([N+]([O-])=O)=CC([N+]([O-])=O)=C2N MKBOTTRSSNRPPF-UHFFFAOYSA-N 0.000 description 1
- SSLUBNFUCQBYTP-UHFFFAOYSA-N 1-amino-4-nitro-9,10-dioxoanthracene-2-carboxylic acid Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C([N+]([O-])=O)=CC(C(O)=O)=C2N SSLUBNFUCQBYTP-UHFFFAOYSA-N 0.000 description 1
- QQBJRPSLIUWNTI-UHFFFAOYSA-N 1-bromo-4-nitro-9,10-dioxoanthracene-2-sulfonic acid Chemical compound C1=CC=C2C(=O)C3=C(Br)C(S(=O)(=O)O)=CC([N+]([O-])=O)=C3C(=O)C2=C1 QQBJRPSLIUWNTI-UHFFFAOYSA-N 0.000 description 1
- AOCQSZUIFJHWNF-UHFFFAOYSA-N 1-bromo-4-nitroanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(Br)=CC=C2[N+](=O)[O-] AOCQSZUIFJHWNF-UHFFFAOYSA-N 0.000 description 1
- NGQRAAQPTFAOQG-UHFFFAOYSA-N 1-chloro-2-nitroanthracene-9,10-dione Chemical compound C1=CC=C2C(=O)C3=C(Cl)C([N+](=O)[O-])=CC=C3C(=O)C2=C1 NGQRAAQPTFAOQG-UHFFFAOYSA-N 0.000 description 1
- FHJIMXQVBSTKAF-UHFFFAOYSA-N 1-ethoxy-4-nitroanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C([N+]([O-])=O)=CC=C2OCC FHJIMXQVBSTKAF-UHFFFAOYSA-N 0.000 description 1
- CYXGLGFQKSCUSV-UHFFFAOYSA-N 1-methyl-2-nitroanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC([N+]([O-])=O)=C2C CYXGLGFQKSCUSV-UHFFFAOYSA-N 0.000 description 1
- FYXKXZFTZBYYNP-UHFFFAOYSA-N 2-Methyl-1-nitroanthraquinone Chemical compound C1=CC=C2C(=O)C3=C([N+]([O-])=O)C(C)=CC=C3C(=O)C2=C1 FYXKXZFTZBYYNP-UHFFFAOYSA-N 0.000 description 1
- FECNOIODIVNEKI-UHFFFAOYSA-N 2-[(2-aminobenzoyl)amino]benzoic acid Chemical class NC1=CC=CC=C1C(=O)NC1=CC=CC=C1C(O)=O FECNOIODIVNEKI-UHFFFAOYSA-N 0.000 description 1
- QBBPBRYGFOXJOB-UHFFFAOYSA-N 3,7-dihydroxy-4,8-dinitro-9,10-dioxoanthracene-2,6-disulfonic acid Chemical compound O=C1C2=CC(S(O)(=O)=O)=C(O)C([N+]([O-])=O)=C2C(=O)C2=C1C([N+]([O-])=O)=C(O)C(S(O)(=O)=O)=C2 QBBPBRYGFOXJOB-UHFFFAOYSA-N 0.000 description 1
- JTJMVZPSIKNOLB-UHFFFAOYSA-N 3-nitro-9,10-dioxoanthracene-2-carboxylic acid Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=C(C(=O)O)C([N+]([O-])=O)=C2 JTJMVZPSIKNOLB-UHFFFAOYSA-N 0.000 description 1
- ZXVONLUNISGICL-UHFFFAOYSA-N 4,6-dinitro-o-cresol Chemical group CC1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1O ZXVONLUNISGICL-UHFFFAOYSA-N 0.000 description 1
- CZZFIABCNJUYFY-UHFFFAOYSA-N 8-chloro-5-nitro-9,10-dioxoanthracene-1-sulfonic acid Chemical compound O=C1C(C(=CC=C2Cl)[N+]([O-])=O)=C2C(=O)C2=C1C=CC=C2S(=O)(=O)O CZZFIABCNJUYFY-UHFFFAOYSA-N 0.000 description 1
- 241000208140 Acer Species 0.000 description 1
- 241000609240 Ambelania acida Species 0.000 description 1
- 241000219495 Betulaceae Species 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- 241000726768 Carpinus Species 0.000 description 1
- 241000218631 Coniferophyta Species 0.000 description 1
- 238000005698 Diels-Alder reaction Methods 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 244000166124 Eucalyptus globulus Species 0.000 description 1
- 229930192627 Naphthoquinone Natural products 0.000 description 1
- 241000219000 Populus Species 0.000 description 1
- 241000183024 Populus tremula Species 0.000 description 1
- 244000305267 Quercus macrolepis Species 0.000 description 1
- 241000124033 Salix Species 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000010905 bagasse Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000004061 bleaching Methods 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000009089 cytolysis Effects 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 239000011121 hardwood Substances 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 238000005470 impregnation Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 239000002655 kraft paper Substances 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- 150000002791 naphthoquinones Chemical class 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 150000005338 nitrobenzoic acids Chemical class 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 239000010902 straw Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- D21C3/22—Other features of pulping processes
- D21C3/222—Use of compounds accelerating the pulping processes
Definitions
- the invention relates to a method for delignifying lignocellulose materials with the addition of nitroanthraquinone compounds.
- nitroanthraquinone compounds have now been found as auxiliaries for the digestion of lignocellulose materials which do not have the disadvantages of aromatic nitro compounds, such as nitrobenzene, which have been investigated as wood digesters, but which are more potent than the previous ones by one or two powers of ten Aromatic nitro compounds used as digestion aids.
- the invention therefore relates to a process for delignifying lignocellulose materials by disintegrating lignocellulose materials with conventional cooking liquids under conventional cooking conditions in the presence of aromatic nitro compounds, which is characterized in that one or more nitroanthraquinone compounds are used as aromatic nitro compounds.
- lignocellulose materials can be delignified using the method according to the invention.
- conifers such as spruce, pine and fir, hardwoods such as beech, birch, eucalyptus, aspen, poplar, willow, hornbeam, alder, oak and maple, and straw and bagasse from annual plants are suitable.
- Spruce, pine, fir, birch and beech are preferably delignified by the method according to the invention.
- one or more nitroanthraquinone compounds are added to the cooking liquid.
- One of the usual cooking liquids for alkaline cooking processes or sulfite processes or similar processes can be used as the cooking liquid.
- the term "alkaline cooking method” encompasses various methods, for example the soda method, the sulfate method, the polysulfide method and the like, and the term “sulfite method” used here includes various methods, for example the alkaline, neutral and acidic sulfite method , the bisulfite process and the like (see P. Lengyel, S. Morvay, Chemistry and Technology of Pulp Production, Güntter-Staib Verlag, Biberach / Riss, 1973, pages 62 ff).
- the additives according to the invention are preferably added to alkaline cooking liquids, as are used, for example, in the processes known as the soda process, sulfate process and polysulfide process.
- the additives according to the invention are very particularly preferably added to alkaline cooking liquids, such as are used in the process known as the soda process.
- the process according to the invention can be carried out in a closed reaction vessel in which the lignocellulose material with the cooking liquid at maximum temperatures in the range from 150 to 200 ° C., preferably from 160 to 180 ° C., over a period of 0.5 to 480 minutes , preferably from 15 to 200 minutes.
- the delignified material can be worked up in a conventional manner, for example by displacing the cooking liquid from the lignocellulose material (pulp) by adding water or an aqueous liquid which is inert to the lignocellulose material (pulp).
- the lignocellulosic material (pulp) processed in this way and optionally mechanically shredded can be used without further treatment or subjected to conventional bleaching processes.
- the delignified lignocellulosic material (pulp) can be further treated in the following way:
- the material is in an aqueous suspension, the content of lignocellulosic material (pulp) is 2 to 40% by weight, for 0.5 to 60 minutes at 20 to 90 ° C with 2 to 20 wt .-% of an alkali metal base and optionally subsequently with oxygen or an oxygen-containing gas for 0.5 to 120 minutes at a temperature of 80 to 150 ° C and treated with an oxygen partial pressure of 1.4 to 14 kg / cm 2 .
- the lignocellulose material used is made of wood, it is advantageous to convert it into chips first.
- nitroanthraquinone compounds can also be added to the lignocellulose material during the impregnation.
- nitroanthraquinone compounds can also be advantageous to allow nitroanthraquinone compounds to act on the lignocellulose material in a pretreatment phase together with the digestion chemicals in the temperature range from about 90 ° -1500 ° C. in such a way that the lignin content is not significant, i. H. is brought to less than 20% in solution and that, if necessary, the proportion of nitroanthraquinone compounds which has not penetrated into the lignocellulose material can be recovered.
- one or more nitroanthraquinone compounds are added to the digestion process.
- mono- and / or dinitroanthraquinones are suitable, which may optionally have one or more further substituents in addition to the nitro groups.
- further substituents are alkyl, alkoxy, halogen, amino, hydroxyl, carboxy and / or sulfo groups and / or fused iso- or heterocyclic rings.
- Preferred further substituents are alkyl and alkoxy groups each having 1 to 4 carbon atoms and chloro and / or sulfo groups.
- the number of further substituents can be, for example, 1 to 6, preferably 1 to 4.
- nitroanthraquinone compounds to be added are: 1- and 2-nitroanthraquinone; 1,5-, 1,6-, 1,7-, 1,8-, 2,6- and 2,7-dinitroanthraquinone; 1-nitro-5-, 1-nitro-7-, 1-nitro-8-sulfo-anthraquinone; 1-nitro-4-chloro-5-sulfo-anthraquinone; 1-nitro-5-, 1-nitro-6-, 1-nitro-8-, 2-nitro-1-chloro-anthraquinone; 2-nitro-4,5-dichloro-anthraquinone; 2-nitro-1,4-, 1-nitro-5,8-diamino-anthraquinone; 1-nitro-4-amino-anthraquinone; 1,3-dinitro-4-amino-anthraquinone; 1-nitro-4-hydroxyanthraquinone; 1-nitro-3,4-, 1-nitro-5,8-, 1,5-dinitro
- 1- and 2-nitroanthraquinone 1,5-, 1,6-, 1,7-, 1,8-, 2,6- and 2,7-dinitroanthraquinone, 1-nitro-5-chloro-anthraquinone are preferred, 1-nitro-8-sulfo-anthraquinone, 1-nitro-4-amino-anthraquinone, 1-nitro-4-hydroxy-anthraquinone, 1-nitro-2-carboxy-anthraquinone, 1-nitro-5-ethoxy-anthraquinone and / or 2-methyl-1-nitro-anthraquinone, in particular the aforementioned dinitro compounds.
- the aforementioned compounds can be added individually or in any mixtures with one another.
- mixtures which contain unsubstituted mono- and / or dinitroanthraquinones is particularly preferred. Such mixtures can be obtained, for example, in the industrial nitration of anthraquinone and / or mononitroanthraquinone.
- mixtures of mono- and / or dinitroanthraquinones can be used in the process according to the invention, which are obtained when anthraquinone is mono- or dinitrated on an industrial scale and / or nitronated with mononitroanthraquinone mixtures and, for example, the isomers important as dye intermediates from the resulting products, e.g. B.
- Particularly preferred mixtures contain, for example, 0 to 3% by weight of 1-nitroanthraquinone, 5 to 12% by weight of 1,5-dinitroanthraquinone, 15 to 35% by weight of 1,6-dinitroanthraquinone, 15 to 35% by weight of 1 , 7-dinitroanthraquinone, 15 to 50% by weight 1,8-dinitroanthraquinone, 0.5 to 3% by weight 2,6-dinitroanthraquinone and 0.5 to 3% by weight 2,7-dinitroanthraquinone.
- nitroanthraquinone compounds according to the invention can take place, for example, in amounts of 0.001 to 10% by weight, based on the lignocellulose material used. 0.01 to 1.0% by weight of the additives, based on lignocellulose material, are preferably used.
- the method according to the invention has the advantage that it leads to a substantial acceleration of delignification in the soda process. A significant acceleration is also observed in the sulfate process and polysulfide process.
- the process according to the invention has the further advantage that substances and mixtures of substances which have hitherto been undesirable by-products in the nitration of anthraquinone can be recycled in a technically advantageous manner.
- the increase in the delignification speed can be used in different ways depending on the circumstances.
- a given Kappa number can e.g. B. achieved in a shorter time, ie, the capacity of an already installed pulp cooker can be expanded. However, it can also be digested at a lower maximum cooking temperature. Energy is saved in both cases.
- Instead of shortening the cooking time and / or lowering the maximum cooking temperature can also be used with a reduced use of chemicals, which has a known effect (see TAPPI, 50 (8), p. 400 [1967]) which has a favorable effect on the reduced formation of strongly smelling by-products.
- TAPPI, 50 (8), p. 400 [1967] which has a favorable effect on the reduced formation of strongly smelling by-products.
- the way in which these advantages can be optimally used in individual cases depends on the circumstances of the pulp production process used.
- the process according to the invention also has a stabilizing effect on the cellulose, so that the cellulose can be obtained in a higher yield for a given kappa number.
- Spruce wood chips were digested in a laboratory cooker with a soda liquor containing 22% active alkali (based on the weight of the wood).
- the ratio of liquid to wood was 4: 1, the heating time was 60 minutes, the cooking time at 175 ° C was 80 minutes (digestion A).
- a further digestion was carried out in the same way (digestion B), in which, however, 0.1% by weight (based on oven-dry wood) of a mixture of dinitroanthraquinone of the following composition was added to the mixture of wood and cooking liquor:
Landscapes
- Paper (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Bakery Products And Manufacturing Methods Therefor (AREA)
- External Artificial Organs (AREA)
- General Preparation And Processing Of Foods (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AT80103278T ATE2279T1 (de) | 1979-06-25 | 1980-06-12 | Verfahren zur delignifizierung von lignocellulose-materialien. |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19792925544 DE2925544A1 (de) | 1979-06-25 | 1979-06-25 | Verfahren zur delignifizierung von lignocellulose-materialien |
| DE2925544 | 1979-06-25 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| EP0021264A1 EP0021264A1 (de) | 1981-01-07 |
| EP0021264B1 true EP0021264B1 (de) | 1983-01-19 |
Family
ID=6074073
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP80103278A Expired EP0021264B1 (de) | 1979-06-25 | 1980-06-12 | Verfahren zur Delignifizierung von Lignocellulose-Materialien |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US4350566A (no) |
| EP (1) | EP0021264B1 (no) |
| JP (1) | JPS568403A (no) |
| AT (1) | ATE2279T1 (no) |
| AU (1) | AU5932980A (no) |
| BR (1) | BR8003938A (no) |
| CA (1) | CA1154208A (no) |
| DE (2) | DE2925544A1 (no) |
| ES (1) | ES8103227A1 (no) |
| FI (1) | FI72541C (no) |
| NO (1) | NO155585C (no) |
| NZ (1) | NZ194113A (no) |
| ZA (1) | ZA803766B (no) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5728265A (en) * | 1995-06-12 | 1998-03-17 | Henkel Corporation | Process for enhancing white liquor penetration into wood chips by contacting the chips with a mixture of the white liquor and a polymethylalkyl siloxane |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4036080A (en) * | 1974-11-29 | 1977-07-19 | The Garrett Corporation | Multi-rim flywheel |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1449828A (en) * | 1973-04-26 | 1976-09-15 | Canadian Ind | Oxygen pulping process |
| JPS5143403A (en) * | 1974-10-09 | 1976-04-14 | Honshu Paper Co Ltd | Arukariparupuno seizohoho |
| CA1073161A (en) * | 1975-09-05 | 1980-03-11 | Canadian Industries Limited | Delignification process |
| JPS5845562B2 (ja) * | 1976-07-21 | 1983-10-11 | 株式会社日立製作所 | タ−ビン等の振動状態表示制御方法 |
| CA1097463A (en) * | 1976-12-13 | 1981-03-17 | Naphtali N. Vanderhoek | Pulping processes |
| CA1094264A (en) * | 1976-12-14 | 1981-01-27 | Canadian Industries Limited | Delignification of lignocellulosic material with a soda liquor containing a cyclic keto compound and a nitro aromatic compound |
| US4036680A (en) * | 1976-12-14 | 1977-07-19 | Canadian Industries, Ltd. | 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 |
| JPS54100332A (en) * | 1978-01-20 | 1979-08-08 | Nippon Steel Chem Co Ltd | Quinone compound composition and its preparation |
-
1979
- 1979-06-25 DE DE19792925544 patent/DE2925544A1/de not_active Withdrawn
-
1980
- 1980-06-11 NO NO801742A patent/NO155585C/no unknown
- 1980-06-12 AT AT80103278T patent/ATE2279T1/de active
- 1980-06-12 DE DE8080103278T patent/DE3061673D1/de not_active Expired
- 1980-06-12 EP EP80103278A patent/EP0021264B1/de not_active Expired
- 1980-06-17 AU AU59329/80A patent/AU5932980A/en not_active Abandoned
- 1980-06-23 CA CA000354580A patent/CA1154208A/en not_active Expired
- 1980-06-23 FI FI802001A patent/FI72541C/fi not_active IP Right Cessation
- 1980-06-23 NZ NZ194113A patent/NZ194113A/xx unknown
- 1980-06-23 JP JP8413180A patent/JPS568403A/ja active Granted
- 1980-06-24 BR BR8003938A patent/BR8003938A/pt unknown
- 1980-06-24 ZA ZA00803766A patent/ZA803766B/xx unknown
- 1980-06-25 ES ES492781A patent/ES8103227A1/es not_active Expired
-
1981
- 1981-04-27 US US06/257,842 patent/US4350566A/en not_active Expired - Fee Related
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4036080A (en) * | 1974-11-29 | 1977-07-19 | The Garrett Corporation | Multi-rim flywheel |
Also Published As
| Publication number | Publication date |
|---|---|
| EP0021264A1 (de) | 1981-01-07 |
| NO155585C (no) | 1987-04-22 |
| ES492781A0 (es) | 1981-02-16 |
| JPS568403A (en) | 1981-01-28 |
| US4350566A (en) | 1982-09-21 |
| DE3061673D1 (en) | 1983-02-24 |
| NZ194113A (en) | 1982-06-29 |
| CA1154208A (en) | 1983-09-27 |
| JPS6258362B2 (no) | 1987-12-05 |
| AU5932980A (en) | 1981-01-08 |
| ZA803766B (en) | 1981-07-29 |
| FI72541B (fi) | 1987-02-27 |
| ES8103227A1 (es) | 1981-02-16 |
| NO155585B (no) | 1987-01-12 |
| BR8003938A (pt) | 1981-01-27 |
| NO801742L (no) | 1980-12-29 |
| FI72541C (fi) | 1987-06-08 |
| FI802001A (fi) | 1980-12-26 |
| ATE2279T1 (de) | 1983-02-15 |
| DE2925544A1 (de) | 1981-01-22 |
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