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Liquid Rosin (Tall Oil) Production, Uses, Extraction, Processing, Compositions and Formulations Hand Book

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Preface

Tall oil, also called "liquid rosin" or tallol, is a viscous yellow-black odorous liquid obtained as a by-product of the Kraft process of wood pulp manufacture when pulping mainly coniferous trees. The name originated as an anglicization of the Swedish "tallolja" ("pine oil"). Tall oil is the third largest chemical by-product in a Kraft mill after lignin and hemicellulose; the yield of crude tall oil from the process is in the range of 30 - 50 kg / ton pulp. It may contribute to 1.0 - 1.5% of the mill's revenue if not used internally.

Manufacturing

In the Kraft Process, high alkalinity and temperature converts the esters and carboxylic acids in rosin into soluble sodium soaps of lignin, rosin, and fatty acids. The spent cooking liquor is called weak black liquor and is about 15% dry content. The black liquor is concentrated in a multiple effect evaporator and after the first stage the black liquor is about 20 - 30%. At this stage it is called intermediate liquor. Normally the soaps start to float in the storage tank for the weak or intermediate liquors and are skimmed off and collected. A good soap skimming operation reduces the soap content of the black liquor down to 0.2 - 0.4% w/w of the dry residue. The collected soap is called raw rosin soap or rosinate. The raw rosin soap is then allowed to settle or is centrifuged to release as much as possible of the entrained black liquor. The soap goes then to the acidulator where it is heated and acidified with sulfuric acid to produce crude tall oil (CTO).

The soap skimming and acidulator operation can be improved by addition of flocculants. A flocculant will shorten the separation time and give a cleaner soap with lower viscosity. This makes the acidulator run smoother as well.

Most pines give a soap yield of 5 - 25 kg/ton pulp, while Chir pine gives 20 - 50 kg/ton. Chir pine grown in the foot hills of Himalayas give a yield of even more than 50 kg/ton. Globally about 2 mill ton/year of CTO are refined.

Composition.

The composition of crude tall oil varies a great deal, depending on the type of wood used. A common quality measure for tall oil is acid number. With pure pines it is possible to have acid numbers in the range 160 - 165, while mills using a mix of softwoods and hardwoods might give acid numbers in the range of 125 - 135

Normally crude tall oil contains rosins (which contains resin acids (mainly abietic acid and its isomers), fatty acids (mainly palmitic acid, oleic acid and linoleic acid) and fatty alcohols), unsaponifiable sterols (5-10%), some sterols, and other alkyl hydrocarbon derivates.

By fractional distillation tall oil rosin is obtained, with rosin content reduced to 10-35%. By further reduction of the rosin content to 1-10%, tall oil fatty acid (TOFA) can be obtained, which is cheap, consists mostly of oleic acid, and is a source of volatile fatty acids.

Applications

The tall oil rosin finds use as a component of adhesives, rubbers, and inks, and as an emulsifier. The pitch is used as a binder in cement, an adhesive, and an emulsifier for asphalt.

TOFA is a low-cost and vegetarian lifestyle-friendly alternative to tallow fatty acids for production of soaps and lubricants. When esterified with pentaerythritol, it is used as a compound of adhesives and oil-based varnishes.

Tall oil is also used in oil drilling as a component of drilling fluids.

Tall oil fatty acids offer several distinctive advantages over alternate sources of fatty acids derived from animal or vegetable oils. Tall oil acids contain few highly unsaturated acids and thus possess better oxidative and color stability. Hence, products made from tall oil acids can provide better color and viscosity stability than products based on acids derived from animal or vegetable oils. Because tall oil is a by-product of the paper industry, the price and supply are regarded by users as more stable than acids derived from agricultural crops. Finally, tall oil acids are available in the free acid form, where as other oils must be hydrolyzed to liberate free fatty acids.

This manuscripts gives us many more valuable informations which are not yet published any where.This manuscript is valuable treasure of Indian Naval Stores which may be useful for Foresters,Research Scholars and Scientists.

Book Contains: Tall Oil (Liquid Rosin) Production and Processing, Composition of Distilled Tall Oils (DTO), Surfactants From Tall Oil Rosin, Crude Tall Oil for Wood Protection, Synthesis and characterization of tall oil fatty acid, Tall Oil Fatty Acid (Alkyd-resin, Alkyd Acrylic, Phytosterols, Phytostanols and Their Esters From Tall Oil (Liquid Rosin), Distilled Tall Oil (DTO), Antiproliferative evaluation of tall-oil docosanol and tetracosanol, Synthesis and Characterization of Novel, Production of Tall Oil Fatty Acid, Tall Oil (Liquid Rosins) Ester-acid Composition For Coating, Dicyclopentadiene Alcohol Rosin Derivatives, Manufacturing edible oils from tall oil fatty acids, Skin care product containing tall oil fatty acids and vegetable oils with manufacturing formula, Process For Manufacturing Valuable Products From Tall Oil Pitch, Chemically modified, maleated unsaturated fatty acids and the salts, Manufacture of A Tall Oil Rosin Ester, Production of Diesel Fuel From Crude Tall Oil, High Temperature Corrosion Inhibition, Hydraulic oil Based on Natural Fatty Acid Esters.

Contents

1. Tall Oil (Liquid Rosin) Production and Processing

Introduction
Composition
Fatty acids
Resin acids
Unsaponifiables
Uses of Liquid Rosins
Tall oil
Lignins
Calcium ions
Sulphide ions
Factors affecting quality of CTO
Dehydration
Depitching
Rosin separation
Heads separation
Fatty acid separation

2. Composition of Distilled Tall Oils (DTO)

Experimental Procedures
Results and Discussion

3. Surfactants From Tall Oil Rosin

Cationic Surfactants Experimental
Preparation of maleopimaric acid (MPA)
Preparation of rosin cationic surfactants (QRMAE)
Electrochemical measurement
Surface Activity of the prepared surfactants
Esterification of rosin
Esterification of RMA-MPEG 750
Characterization of the prepared Surfactants
Surface Activity of the prepared surfactants

4. Crude Tall Oil for Wood Protection

Sources, production and utilization of crude tall oil
Tall oil as a wood protection agent
Wood extractives and natural durability
Effect of tall oil on the biological durability of wood
Effect of tall oil on water repellency
Reducing the amount of oil needed
Enhancing the drying properties of crude tall oil
Enhancing the wood protection properties of tall oil
Biodegradability of tall oil-based wood preservatives

5. Synthesis and characterization of tall oil fatty acid

Resin synthesis
Materials
Curing process
Trial experiments for scheme 2 and scheme 3
Characterization of resins
Results and discussion of resins
FTIR analysis of the synthesized thermoset resins
Composite preparation
Hand lay-up impregnation
Characterization of composites
Flexural testing
Dynamic mechanical thermal analysis

6. Tall Oil Fatty Acid (Alkyd-resin, Alkyd Acrylic

Copolymers, Drying Processese
Introduction
Alkyd resin
Alkyd-acrylic copolymers
The drying process
Synthesis of copolymers
Celluloses used as fillers
Films and coatings
Characterization
Surface modification
Degree of substitution
Barrier properties

7. Phytosterols, Phytostanols and Their Esters From Tall Oil (Liquid Rosin)

Manufacturing
Production of sterols from vegetable oil distillates
Production of sterols from wood pulp/tall oil
Production of phytostanols from phytosterols
Production of phytosterol and phytostanol esters
Free fatty acid route
Methylester route
Commercial suppliers
Chemical Characterization
Composition and properties
Quality of phytosterols, phytostanols and their esters
Analytical methods
Regulatory status
Reactions and fate in foods
Stability at high temperatures

8. Distilled Tall Oil (DTO)

The BUS model

9. Antiproliferative evaluation of tall-oil docosanol and tetracosanol

Materials and Methods
Raw materials
Formulation of long-chain alcohols in Pluronic® F-68
Cell culture assays
Statistical analysis

10. Synthesis and Characterization of Novel

Polyurethanes Based on Tall Oil
Synthesis of polyols
Preparation and characterization of polyurethanes
Properties of polyols
Structure of polyols and polyurethanes
Properties of polyurethanes

11. Production of Tall Oil Fatty Acid

12. Tall Oil (Liquid Rosins) Ester-acid Composition For Coating

13. Dicyclopentadiene Alcohol Rosin Derivatives

14. Manufacturing edible oils from tall oil fatty acids

15. Skin care product containing tall oil fatty acids and vegetable oils with manufacturing formula

16. Process For Manufacturing Valuable Products From Tall Oil Pitch

17. Chemically modified, maleated unsaturated fatty acids and the salts

Ricinoleic Acid Modification
Polyamine Modification
Amino Alcohol Modification
Imidazoline Modification
Metal Chelate Modification
Ester Modification
Amino Acid Modification
Polyfunctional Corrosion Inhibitors
Sulfonate & Sulfate Modification
General Considerations
Maleation of Crude Tall Oil

18. Manufacture of A Tall Oil Rosin Ester

Detailed Description
Odor Level Comparison Tests

19. Production of Diesel Fuel From Crude Tall Oil

The Drawings
Description

20. High Temperature Corrosion Inhibition

Performance of Imidazoline and Amide
Experimental
Inhibitor Performance Evaluation
The tests are conducted as follows

21. Hydraulic oil Based on Natural Fatty Acid Esters

List of Tables

Table 2.1 Gross Compositional Characteristics of American Distilled Tall Oilsa
Table 2.2 Composition of Fatty and Resin Acids in American Distilled Tall Oils
Table 2.3 GLC Retention and NMR Characteristics of the Methyl Secodehydroabietatesa
Table 2.4 Composition of Pimaric-and Isopimaric-Type Acids Comprising Resin Acids of American Distilled Tall Oilsa
Table 4. 1. Composition of CTO
Table 4.2. Degree of water repellent efficiency (DEt) of tall oil-treated pine sapwood samples measured after 1 and 96 hours of water immersion
Table 4.3. Properties of the tall oil emulsions
Table 5.1: Different mass ratio of MA to HOTOFA
Table 5.2: DSC analysis table of all uncured resin samples
Table 5.3: TGA analysis for different cured resins
Table 5.4: Summary of the DMTA result
Table 5.5: Summary of charpy properties
Table 6.1. Fatty acid composition of various oils used in coatings
Table 6.2. Alkyd resins studied and used in copolymer synthesis
Table 6.3. Generalized recipe for copolymerizations
Table 6.4. Synthesized and studied copolymers
Table 6.5. Synthesized copolymer dispersions, which
were applied on paperboard
Table 6.6 Relative proportions of each proton and proton group in the polyol region
Table 6.7. Tg values of copolymer films and onset temperatures of the DMA measurements.The results are averages of five measurements
Table 6.8. Comparison of the quantity of fatty acids attached based on the integrated cellulose and acyl peaks in the 13C CPMAS NMR spectra
Table 6.9. Degree of substitution and O/C ratio calculated from XPS measurements
Table 6.10. Mechanical properties of copolymer films studied with DMA, the results are averages from 3 to 8 measurements
Table 7.1. Commercial suppliers of phytosterols, phytostanols and/or their esters; 1) TO: tall oil; VO: vegetable oil
Table 7.2: Physical characteristics and composition of different commercial phytosterols, phytostanols and their esters; 1) from TO sterols; 2) from VO sterols; 3) mainly sitosterol and campesterol
Table 7.3. Phytostanol concentrations in food products on the market, including portion sizes
Table 8.1: Composition of test materials
Table 8.2: Calculation of the MTT, PGE2, and (MTT + PGE2) combined score values
Table 8.3: Results from the MTT assay and the PGE2 determination for tissue treated with a single application of tall oils
Figure 8.1: Determination of the cytotoxicity of single and repeated applications of tall oils
Table 8.4: Results from the MTT assay and the PGE2 determination for tissue treated with repeated applications of tall oils
Table 9.1. Percentage of viability of CHO and melanoma cell cultures in the presence of long-chain aliphatic alcohols
Table 10.1. Specifications of oils
Table 10.2. Characteristics of polyols
Table 10.3. Thermal stability of polyurethanes

List of Figures

Figure 1 .1 The tall oil process
Figure 3.1. FTIR spectra of a) RMAE and b) QRMAE
Figure 3.2. 1HNMR spectra of a) RMAE and b) QRMAE
Figure 3.3 Relation between surface tension of QRMAE and time at different concentrations in a) water and b) 1M aqueous HCl solutions at 25°C.
Figure 3.4. Adsorption isotherms of QRMAE at different concentrations in a) water and b) 1M aqueous HCl solutions at 25°C.
Figure 3.5. FTIR Spectra of a) RMA and b) RMA-(MPEG 750)3
Figure 3.6. Relation between surface tension of R-MPEG 750 and time different concentrations in 1M aqueous HCl solutions.
Fig. 4.1. Simplified diagram of the tall oil distillation pr
Fig. 4.2. Fatty acids.
Fig. 4.3. Resin acids.
Fig. 4.4 Degree of efficiency after the initial wetting and drying cycle, measured after 1 hour of water immersion
Fig. 4.5 Degree of efficiency after the initial wetting and drying cycle, measured after 96 hours of water immersion
Fig. 4.6. Degree of efficiency after six wetting and drying cycles, measured after 1 hour of water immersion
Fig. 4.7. Degree of efficiency after six wetting and drying cycles, measured after 96 hours of water immersion
Fig. 4.8. DSC diagrams (110°C air flow) indicating the oil oxidation rate
Fig. 4.9. Water uptake by tall oil-treated pine sapwood in the seventh wetting and drying cycle
Fig. 4.10. Amounts of oil pressed out of the samples during the compression test
Fig. 4.11. Typical particle size distribution of a tall oil-based emulsion
Figure 5.1: synthesis scheme 1
Figure 5.2: synthesis scheme 2
Figure 5.3: synthesis scheme 3
Figure 5.4: Experimental set-up for synthesis of thermosetting resin
Figure 5.5: the obtained resins with three different mass ratio of MA to HOTOFA
Figure 5.6 : FTIR spectra comparison of TOFA and HOTOFA resins
Figure 5.7: FTIR spectra comparison of HOTOFA, MHOTOFA 1:1, MHOTOFA 1.5: 1 and MHOTOFA 1.76:1resins
Figure 5.8: DSC curve of uncured MHOTOFA 1to1 (no styrene) resin
Figure 5.9: DSC curve for cured MHOTOFA 1to1 resin (no styrene, room T for 1h and post cure in 150°C for another 1h)
Figure 5.10: Comparison of the DSC scan for cured and uncured MHOTOFA 1to1 (no styrene) resin
Figure 5.11: TGA analysis of cured MHOTOFA 1:1 resin (no styrene)
Figure 5.12: Viscose fiber and fiber mats lay-up orientation
Figure 5.13: Six different composites from 3 different resins (with or without styrene) reinforced by viscose fiber
Figure 5.14: Test specimens for flexural, DMTA, charpy, tensile
Figure 5.15: Flexural strength comparison of the composites
Figure 5.16: Flexural modulus comparison of the composites
Figure 5.17: Strain at break% comparison of the composites
Figure 5.18: variation in the storage modulus of the MHOTOFA composites
Figure 5.19: Tan delta curves of the MHOTOFA composites
Figure 5.20: the loss modulus curves of MHOTOFA composites
Figure 5.21: Comparison of the storage modulus between the reinforced resin (composite) and the unreinforced resin, both blended with styrene
Figure 5.22: Impact strength of the composites
Figure 6.1. Structure of typical alkyd resin
Figure 6.2. Miniemulsion and conventional emulsion polymerization
Figure 6.3. Schematic presentation of the oxidative drying of alkyd resin
Figure 6.5. SEC chromatograms of alkyd resins
Figure 6.6. Monomer conversion of copolymers with different wt% of conjugated alkyd resin (BA-MMA ratio is 80:20) (copolymers11-15 in Table 6.4)
Figure 6.7. Monomer conversion of copolymers with different wt% of nonconjugated Alkyd-TMP-3 and BA as monomer (copolymers 1-5 in Table 6.4)
Figure 6.8. Particle-size distribution of emulsion and dispersion with various alkyd contents (copolymers 1, 3, 5 in Table 6.4)
Figure 6.9. Grafting of acrylic macroradical to double bond (a-c) and bis-allylic site (d-f) in the fatty acid chain. a) Macroradical attacks DB in fatty acid chain. b) Grafting occurs and a new radical is formed. c) Polymerization continues at the new radical site. d) Macroradical attacks allylic hydrogen in fatty acid chain. e) Hydrogen is abstracted and a new radical is formed in fatty acid chain, where new radical approaches. f) Macroradical grafts to radical site in fatty acid chain
Figure 6.10. Monomer conversion and acrylic degree of grafting. BA-MMA ratio (wt%) was 80:20 in samples with conjugated alkyd (copolymers 11-15 in Table 6.4) and 100:0 in samples with nonconjugated alkyd (copolymers 1-5 in Table 6.4
Figure 6.11. a) Effect ofBA concentration on grafting site and efficiency. b) Effect of alkyd-acrylate ratio on various grafting sites (copolymers 16-20 in Table 6.4)
Figure 6.12. DSC thermograms of alkyd resin and copolymers (copolymers 16-20 in Table 6.4)
Figure 6.13. a) TG and b) DTG curves showing thermal stability of alkyd resin, alkyd-acrylic copolymers, and acrylic copolymer.
Figure 6.14. Two parts of FTIR spectra of neat whiskers and fatty acid-modified whiskers.The carbonyl peak at app. 1740 cm-1 is marked with dotted line
Figure 6.15. Thermal stability of neat whiskers and fatty acid-modified whiskers presented as TGA curves
Figure 6.16. a) ssNMR spectrum of copolymer film and freeze-dried copolymer. b) FTIR spectra of copolymer film after various drying times showing the decreasing intensity of the cis H-C=CH peak (marked with dotted line)
Figure 6.17. Stress-strain curves of copolymer films with various alkyd contents. One measurement of each film sample set is presented
Figure 6.18. Storage modulus of copolymer films with various alkyd contents. One measurement of each film sample set is presented
Figure 6.19. Figure 1 Water and oil absorbance of copolymer-coated cupboards (copolymers 30-37). Samples 34-37 were crosslinked with GMA
Figure 6.20. Effect of TOFA-modified whiskers on mechanical properties of films
Figure 6.21. Effect of various cellulose types on mechanical properties of the films
Figure 6.22. Effect of TOFA-modified cellulose on a) oxygen barrier properties (copolymers 32 and 33) and b) water and oil absorbance (copolymer 32) of copolymer-coated paperboards.
Figure 7.1. Steroid skeleton
Figure 7.2. Molecular structure of some phytosterols, phytostanols and a fatty acid ester
Figure 8.2: Determination of the irritancy potential of single and repeated applications of tall oils
Figure 8.3: The combined cytotoxicity and irritancy potential of single and repeated applications of tall oils
Fig. 9.1. Structure of long-chain aliphatic alcohol (polycosanols): docosanol and tetracosanol
Fig. 9.2. Effect of long-chain aliphatic alcohol type on CHO-K1 cell growth
Fig. 9.3. Effect of long-chain aliphatic alcohol type on melanoma cell growth
Fig. 10.1. Chemical structure of the synthesized polyols and polyurethanes, where R1 - residue of saturated and unsaturated fatty acids (C16-C24) and R2 - residue of aromatic diisocyanate
Fig. 10.2. IR-spectra of polyols (1, 2) and urethanes (3, 4), based on tall oil FOR2 esters (1, 3) and diethanolamides (2, 4)
Fig. 10.3. IR-spectra of tall oil diethanolamides (1, 2) and esters (3, 4), containing 2 % (1, 3) and 20 % (2, 4) of rosin acids
Fig. 10.4. IR-spectra of polyurethanes based on tall oil diethanolamides (1, 2) and esters (3, 4), containing 2 % (1, 3) and 20 % (2, 4) of rosin acids
Fig. 10.5. Density of polyurethanes versus the content of rosin acids
Fig. 10.6. Tg of polyurethanes versus the content of rosin acids
Fig. 10.7. Modulus of elasticity of polyurethanes versus the content of rosin acids
Fig. 10.8. Tensile strength of polyurethanes versus the content of rosin acids
Fig. 10.9. Elongation at break of polyurethanes versus the content of rosin acids
Fig. 10.10. Shear bond strength to wood (W) and aluminium (Al) for polyurethanes versus the content of rosin acids
Fig. 10.11. TGA curves of polyurethanes with the content of rosin acids of 2 %
Fig. 19.1 is a general flow scheme of one embodiment of the invention
Fig. 19.2 is a more detailed flow scheme of one embodiment of the invention

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