Ionic liquids in innovative technologies connected with processing of lignocellulosic raw materials

Out-of-print edition. Available in ITD’s reading room.

Collective work 
Edited by Jadwiga Zabielska-Matejuk  
Poznań, Instytut Technologii Drewna, 2012
ISBN  978-83-932284-3-0

(Polish language version)

Complimentary publication, issued within the framework of the project
"Ionic liquids in innovative technologies connected with processing of lignocellulosic raw materials"

CONTENTS

INTRODUCTION 9
1. ABOUT THE PROJECT 13
2. IONIC LIQUIDS 23 
    2.1. Ionic liquids - state of issue 
          Jadwiga Zabielska-Matejuk
25 
    2.2. Subject of research - ionic liquids - mixture with biocides
          Jadwiga Zabielska-Matejuk, Mariusz Kot  
39 
3. SYNTHESIS OF IONIC LIQUIDS OF NEW FUNCTIONAL PROPERTIES
    FOR THE WOOD INDUSTRY
47 
    3.1. Syntheses and properties of ionic liquids
          Mariusz Kot
49 
          3.1.1. Synthesis of aprotic ionic liquids  52 
          3.1.2. Synthesis of protic ionic liquids  58 
          3.1.3. Analysis of nuclear magnetic resonance spectra  62 
          3.1.4. Thermal analysis of ionic liquids  68 
          3.1.5. Solubility in organic solvents  73 
          3.1.6. Density measurement    75 
          3.1.7. Dynamic viscosity measurement  78 
          3.1.8. Refractive index measurement  81 
          3.1.9. Tebuconazole dissolution  86 
          3.1.10. Summary  88 
4. IONIC LIQUIDS IN INNOVATIVE TECHNOLOGIES FOR WOOD DURABILITY
    ENHANCEMENT
 
91 
    4.1. Tests of activity against fungi and algae - ionic liquids in contact with wood
          Jadwiga Zabielska-Matejuk, Anna Stangierska, Weronika Przybylska, 
          Piotr Przybylski
 
93 
          4.1.1. Test methods  93 
                   4.1.1.1. Biological tests  93 
                   4.1.1.2. Physical and chemical tests of adsorption and bonding of ionic liquids
                               with the ground
97 
                   4.1.1.3. Determination of penetration of the tested ionic liquids into Scots pine
                               wood 
100 
                   4.1.1.4. Leaching of ionic liquids from saturated wood  101 
                   4.1.1.5. Determination of corrosive aggressiveness of ionic liquids and their
                               mixtures with tebuconazole 
101 
                   4.1.1.6. Tests of hygroscopicity and absorptiveness of wood treated with ionic
                               liquids 
102 
                   4.1.1.7. Determination of inflammability resistance of wood protected with ionic 
                               liquids 
102 
          4.1.2. Test results and discussion  103 
                   4.1.2.1. Mycological tests  103 
                   4.1.2.2. Activity against algae  119 
                   4.1.2.3. Adsorption equilibriums and kinetics  120 
                   4.1.2.4. Bonding of ionic liquids with lignocellulosic material  132 
                   4.1.2.5. Corrosive aggressiveness of ionic liquids against steel  151 
                   4.1.2.6. Leaching from saturated Scots pine wood  153 
                   4.1.2.7. Absorptiveness and hygroscopicity of wood treated with ionic liquids   155 
                   4.1.2.8. Corrosive aggressiveness of ionic liquids against steel  157 
                   4.1.2.9. The influence of ionic liquids on wood inflammability  159 
    Literature  168 
    4.2. Strength tests of wood treated with selected ionic liquids
          Andrzej Fojutowski, Andrzej Noskowiak, Aleksandra Kropacz, Anna Stangierska 
171 
          4.2.1. Introduction  171 
          4.2.2. Test materials and methods  172 
                   4.2.2.1. Wood used in tests  172 
                   4.2.2.2. Ionic liquids  172 
                   4.2.2.3. Tested properties of wood and methods of their determination   173 
                   4.2.2.4. Preparation of wood specimens  173 
                   4.2.2.5. Wood impregnation with ionic liquids and preparation for tests  174 
                   4.2.2.6. Presentation of results  174 
          4.2.3. Results and their discussion  175 
                   4.2.3.1. Retention of ionic liquids in wood specimens  175 
                   4.2.3.2. Compression strength along the grain of oven-dry wood  176 
                   4.2.3.3. Compression strength along the grain of wood at equilibrium moisture
                               content 
178 
                   4.2.3.4. Bending strength and modulus of elasticity at bending  180 
          4.2.4. Summary  184 
          Literature  185 
    4.3. Change of colour of wood protected by colourful ionic liquids when exposed to light
          Magdalena Nowaczyk-Organista 
187 
          4.3.1. Introduction  187 
          4.3.2. Materials and methods  188 
          4.3.3. Results and discussion  188 
          4.3.4. Summary  190 
    Literature  190 
5. OF IONIC LIQUIDS IN TECHNOLOGIES OF PARTICLEBOARD AND PLYWOOD
    PROTECTION 
193 
     5.1. Ionic liquids in particleboard technology
          Iwona Frąckowiak, Cezary Andrzejak 
195 
          5.1.1. Introduction  195 
          5.1.2. Materials and methods  197 
          5.1.3. Results and discussion  199 
          5.1.4. Summary  206 
    Literature  206 
    5.2. Ionic liquids in plywood production technologies
          Mariusz Jóźwiak
209 
          5.2.1. Introduction  209 
          5.2.2. Material and methods  211 
                   5.2.2.1. Ionic liquids as hardeners of amino glue resins in the production
                              of plywood 
212 
                   5.2.2.2. Ionic liquids as preservatives protecting plywood against
                               microbiological decay 
214 
                   5.2.2.3. Test methods 218 
          5.2.3. Results and tests discussion  220 
          5.2.4. Summary  232 
    Literature 233 
    5.3. Assessment of particleboard and plywood resistance to basidiomycetes and mould
          fungi 
           Jadwiga Zabielska-Matejuk, Weronika Przybylska, Anna Stangierska  
237 
          5.3.1. Test methods  237 
                   5.3.1.1. Resistance to decay fungi 237 
                   5.3.1.2. Resistance to mould fungi  238 
          5.3.2. Results and tests discussion 239 
                   5.3.2.1. Protection of pine and beech plywood 239 
                   5.3.2.2. Protection of particleboards  261 
    Literature  267 
    5.4. Research on the influence of wood, particleboard and plywood protection with ionic
           liquids on the emission of volatile organic compounds (VOC) and formaldehyde
          Magdalena Czajka, Aleksandra Dziewanowska-Pudliszak 
269 
          5.4.1. Introduction  269 
          5.4.2. Materials and methods  270 
          5.4.3. Tests results 272 
          5.4.4. Summary  278 
    Literature 278 
6. IONIC LIQUIDS AS ENVIRONMENTALLY FRIENDLY EXTRACTANTS
    OF CELLULOSE FROM LIGNOCELLULOSIC RAW MATERIAL
281 
    6.1. Isolation of cellulose/carbohydrate fraction from various papermaking semi-products
          and raw materials with the use of ionic liquids and characteristics of regenerated
          materials 
           Barbara Surma- Ślusarska, Dariusz Danielewicz, Malwina Kaleta
281 
          6.1.1. Introduction  283 
          6.1.2. Aim and scope of research  284 
          6.1.3. Materials and methodology of research  285 
          6.1.4. Results  293 
                   6.1.4.1. Research on the process of cellulose dissolution in ionic liquids  293 
                   6.1.4.2. Research on the process of paper fibrous semi-products dissolution
                               in ionic liquids 
294 
                   6.1.4.3. Research on the process of various non-wood plants and secondary
                               fibers dissolution in ionic liquids 
296 
                   6.1.4.4. Research on the process of raw wood materials dissolution in ionic
                               liquids 
298 
                   6.1.4.5. Research on the process of paper semi-products and raw wood
                               materials dissolution in ionic liquids with enzymes 
303 
                   6.1.4.6. Research on the process of cellulose, carbohydrate fraction and
                               lignocellulosic material regeneration from solutions of ionic liquids 
305 
                   6.1.4.7. Characteristics of cellulose/lignocellulosic material after regeneration
                              from ionic liquids 
310 
                   6.1.4.8. Assessment of usefulness of materials dissolved in ionic liquids
                              and regenerated for specific applications 
330 
          6.1.5. Most important statements and conclusions  332 
    Literature  333 
7. BIODEGRADATION OF IONIC LIQUIDS IN THE ENVIRONMENT 337
    7.1. The influence of ionic liquids on aquatic environment
          Elżbieta Grabińska-Sota, Anna Arendarczyk, Aleksandra Zgórska 
339 
          7.1.1. Introduction  339 
          7.1.2. Materials and methods  340 
                   7.1.2.1. Materials  340 
                   7.1.2.2. Methods  341 
          7.1.3. Results and discussion  346 
          7.1.4. Summary  357 
    Literature  357 
    7.2. Biodegradation of ionic liquids in treated wood by mould fungi in soil environment  361 
          7.2.1. Introduction  361 
          7.2.2. Test methods 362 
          7.2.3. Tests results and discussion   363 
                   7.2.3.1. Tests of biodegradation in treated Scots pine wood  363 
                   7.2.3.2. Microscopic observations - SEM  366 
          7.2.4. Summary  372 
8. SUMMARY  375