EP0006790B1 - Hexahydro-1,2,3,4,4a,9a anthracène-dione-9,10, sa préparation et son application à la délignification des matériaux lignocellulosiques - Google Patents

Hexahydro-1,2,3,4,4a,9a anthracène-dione-9,10, sa préparation et son application à la délignification des matériaux lignocellulosiques Download PDF

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Publication number
EP0006790B1
EP0006790B1 EP79400378A EP79400378A EP0006790B1 EP 0006790 B1 EP0006790 B1 EP 0006790B1 EP 79400378 A EP79400378 A EP 79400378A EP 79400378 A EP79400378 A EP 79400378A EP 0006790 B1 EP0006790 B1 EP 0006790B1
Authority
EP
European Patent Office
Prior art keywords
anthracene
dione
hexahydro
cooking
tetrahydro
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
Application number
EP79400378A
Other languages
German (de)
English (en)
French (fr)
Other versions
EP0006790A1 (fr
Inventor
Lucien Bourson
Serge Delavarenne
Pierre Tellier
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Produits Chimiques Ugine Kuhlmann
Original Assignee
Produits Chimiques Ugine Kuhlmann
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.)
Filing date
Publication date
Application filed by Produits Chimiques Ugine Kuhlmann filed Critical Produits Chimiques Ugine Kuhlmann
Priority to AT79400378T priority Critical patent/ATE179T1/de
Publication of EP0006790A1 publication Critical patent/EP0006790A1/fr
Application granted granted Critical
Publication of EP0006790B1 publication Critical patent/EP0006790B1/fr
Expired legal-status Critical Current

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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 present invention relates, as a new industrial product, to hexahydro-1,2,3,4,4a, 9a anthracene-dione-9,10, a compound which can be considered as a hydrogenated anthraquinone: hexahydro-1, 2,3,4,4a, 9a anthraquinone. It also relates to a process for the preparation of hexahydro-1,2,3,4,4a, 9a anthracene-dione-9,10 by hydrogenation of tetrahydro-1,4,4a, 9a anthraquinone. It also relates to the use of hexahydro-1,2,3,4,4a, 9a anthracene-dione-9,10 in the delignification of lignocellulosic materials.
  • the hydrogenated compounds of anthraquinone have, to date, been obtained by hydrogenation of anthraquinone or by addition of a diene on benzoquinone or naphthoquinone. These methods make it possible to synthesize different compounds but none of them corresponds to hexahydro-1,2,3,4,4a, 9a anthracene-dione-9,10.
  • solvents examples include aliphatic, cycloaliphatic or aromatic hydrocarbons, ethers, tetrahydrofuran, dioxane, alcohols. Generally, all solvents which do not contain a functional group which can be hydrogenated under the reaction conditions can be used.
  • the catalyst is chosen from those usually used in hydrogenation. Mention may be made, for example, of those based on nickel, such as Raney nickel, those based on precious metals such as palladium or platinum.
  • the hydrogenation reaction can be carried out over a wide temperature range from 20 to 200 ° C. It is preferred to operate between 60 and 130 ° C.
  • the hydrogenation can be carried out at atmospheric pressure but it is then slow. It is therefore preferable to operate under pressure. There is no upper limit of the hydrogenation pressure which is preferably chosen between 10 and 50 bars.
  • the hydrogenation is continued until the theoretical amount of hydrogen corresponding to the formation of hexahydroanthracene-dione has been absorbed.
  • the concentration of 1,4,4a-tetrahydro, 9a anthraquinone in the reaction medium can also vary within wide limits. There is no lower limit of this concentration but for reasons of productivity it is preferably greater than 10% by weight. For practical reasons it is less than 50% by weight. The preferred concentration is between 15 and 40%.
  • the present invention also relates to the application of hexahydro-1,2,3,4,4a, 9a anthracene-dione-9,10 to the delignification of lignocellulosic materials such as wood, straw, linen, alfa, bagasse, etc. .... for the production of pulp.
  • the preparation of paper pulps from lignocellulosic plant materials generally includes a cooking stage with alkaline detergents intended to dissolve non-cellulosic impurities, in particular the lignin present in greater or lesser proportion depending on the plant species. Proteins, gums, hemicelluloses can also be eliminated by the alkaline cooking treatment. Depending on the conditions under which this treatment is carried out, the cellulose may or may not undergo a certain chemical degradation which modifies its qualities and alters its mechanical properties, which is detrimental to its paper use.
  • soda baking process which consists in acting a caustic soda lye (Na OH) sand another additive at high temperature and pressure on wood shavings, generally leads to paper pulp of weak characteristics with a poor yield .
  • the amount of hexahydro-1,2,3,4,4a, 9a antracene-dione-9,1 0 to be used can be between 0.01 and 10% preferably between 0.05 and 2% by weight relative dry vegetable.
  • the level of active alkali can be between 10 and 30% by weight of soda relative to the dry vegetable and the sulfidity between 15 and 35% relative to the active alkali.
  • the cooking temperature can be between 130 and 200 ° C and the level of adjuvant between 0.01 and 10%, preferably between 0.05 and 2% by weight relative to the dry vegetable.
  • Example 2 The procedure is as in Example 1, but with 63.6 g of 1,4,4a tetrahydro, 9a anthraquinone, 150 cc of touene and 0.4 g of palladium catalyst. After 3 hours of reaction at 80 ° C. at 100 bars, 7 g of tetrahydro-1,2,3,4 anthracene-diol-9,10 and 56 g of hexahydro-1,2,3,4,4a are collected. , 9a anthracene-dione-9,10.
  • Example 2 The procedure is as in Example 1 but with 424 g of 1,4,4a tetrahydro, 9a anthraquinone, 2 liters of toluene and 4 g of catalyst. After 2 hours of reaction there is no longer absorption of hydrogen. 28.5 g of tetrahydro-1,2,3,4 anthracene-diol-9,10 containing the catalyst are collected by filtration and, after concentration of the solution, 402 g of hexahydro-1,2,3,4, 4a, 9a anthracene-dione-9,10.
  • the reference unbleached pasta and those obtained with 0.5% adjuvant in cooking, are refined in the Jokro mill.
  • the sheets for physical tests are made with the Rapid Kothen form. Their grammage is approximately 70 g per m2.
  • Example 9 After cooking, the same operations as those described in Example 9 are carried out on the pasta and the cooking liquors.

Landscapes

  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Paper (AREA)
  • Luminescent Compositions (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Photoreceptors In Electrophotography (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Polysaccharides And Polysaccharide Derivatives (AREA)
  • Graft Or Block Polymers (AREA)
  • Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
  • Polymerisation Methods In General (AREA)
  • Dental Preparations (AREA)
  • Compounds Of Unknown Constitution (AREA)
EP79400378A 1978-06-29 1979-06-12 Hexahydro-1,2,3,4,4a,9a anthracène-dione-9,10, sa préparation et son application à la délignification des matériaux lignocellulosiques Expired EP0006790B1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AT79400378T ATE179T1 (de) 1978-06-29 1979-06-12 1,2,3,4,4a,9a-hexahydroanthrazen-9,10-dion, seine herstellung und seine verwendung beim delignifizieren von ligninhaltigem cellulosematerial.

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FR7819466 1978-06-29
FR7819466A FR2435457A1 (fr) 1978-06-29 1978-06-29 Hexahydro-1,2,3,4,4a, 9a anthracene-dione-9,10, sa preparation et son application a la delignification des materiaux lignocellulosiques

Publications (2)

Publication Number Publication Date
EP0006790A1 EP0006790A1 (fr) 1980-01-09
EP0006790B1 true EP0006790B1 (fr) 1981-09-02

Family

ID=9210133

Family Applications (1)

Application Number Title Priority Date Filing Date
EP79400378A Expired EP0006790B1 (fr) 1978-06-29 1979-06-12 Hexahydro-1,2,3,4,4a,9a anthracène-dione-9,10, sa préparation et son application à la délignification des matériaux lignocellulosiques

Country Status (14)

Country Link
US (1) US4235666A (no)
EP (1) EP0006790B1 (no)
JP (1) JPS559082A (no)
AT (1) ATE179T1 (no)
AU (1) AU527739B2 (no)
BR (1) BR7904062A (no)
CA (1) CA1117940A (no)
DE (1) DE2960731D1 (no)
ES (1) ES482028A1 (no)
FI (1) FI66832C (no)
FR (1) FR2435457A1 (no)
NO (1) NO151616C (no)
NZ (1) NZ190792A (no)
SU (2) SU965349A3 (no)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA2374780C (en) * 1999-06-15 2008-09-16 Kawasaki Kasei Chemicals Ltd. Cooking method for pulp
FI128736B (en) * 2018-03-09 2020-11-13 Valmet Automation Oy Method and measuring device for measuring the suspension

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US1821035A (en) * 1927-08-18 1931-09-01 Gen Aniline Works Inc Compounds of the anthracene series and process of preparing them
US1890040A (en) * 1928-05-07 1932-12-06 Gen Aniline Works Inc Production of anthraquinone and derivatives thereof
DE504646C (de) * 1928-09-13 1930-09-09 I G Farbenindustrie Akt Ges Verfahren zur Darstellung von Anthrachinon und seinen Abkoemmlingen
GB1130743A (en) * 1965-06-11 1968-10-16 Ici Ltd Organo-iridium complexes
CA1073161A (en) * 1975-09-05 1980-03-11 Canadian Industries Limited Delignification process
FR2373337A1 (fr) * 1976-12-07 1978-07-07 Hotchkiss Brandt Sogeme Dispositif automatique de tri d'objets, procede de mise en oeuvre de celui-ci et equipement comportant un tel dispositif
JPS5374101A (en) * 1976-12-10 1978-07-01 Honshu Paper Co Ltd Pulp making method
US4036681A (en) * 1976-12-14 1977-07-19 Canadian Industries, Ltd. Delignification of lignocellulosic material with an alkaline pulping liquor containing a Diels Alder adduct of benzoquinone or naphthoquinone

Also Published As

Publication number Publication date
ES482028A1 (es) 1980-07-01
NO151616C (no) 1985-05-08
NO792184L (no) 1980-01-03
JPS622569B2 (no) 1987-01-20
SU924034A1 (ru) 1982-04-30
NZ190792A (en) 1981-10-19
JPS559082A (en) 1980-01-22
SU965349A3 (ru) 1982-10-07
EP0006790A1 (fr) 1980-01-09
FR2435457A1 (fr) 1980-04-04
FI66832C (fi) 1984-12-10
US4235666A (en) 1980-11-25
BR7904062A (pt) 1980-03-11
AU4847379A (en) 1980-01-03
FR2435457B1 (no) 1981-01-30
DE2960731D1 (en) 1981-11-26
AU527739B2 (en) 1983-03-17
CA1117940A (fr) 1982-02-09
NO151616B (no) 1985-01-28
FI66832B (fi) 1984-08-31
FI792039A (fi) 1979-12-30
ATE179T1 (de) 1981-09-15

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