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Manufacturing Technology of Rosins, Turpentines, Pine Oil, Menthol, Camphor, Terpenes and Derivatives with Processing and Formulations

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The Book covers chapters on Wood Rosin, Process of Refining Wood Rosin, Esters of Pine Wood Pitch, Chemical composition and antioxidant activity of essential oil of pine cones of Pinus armandii, Chemical Composition of The Oil of Pinus Pinea L. Seeds, Resin Products from Pines, Process for the manufacturing of turpentine, pine oil and rosin from woody materials rich in oleoresin, Structural Determination, Menthol and Carvone, Bicyclic Monoterpenoids, Synthesis of A-Santalol, Production of a-Terpineol from a-Pinene, Menthol, Camphor, Synthesis and Characterization of Isolongifoline and Acetyl longifoline, Terpene Resins in Pressure Sensitive Adhesives, Terpene phenolic resins, Phenol-terpene-cyclic polyolefin polymer, The Insecticides Obtained from Turpentine, Pine oil cleaning composition, Terpene Polymer, Tackifier resin composition and process, Hot Melt Coating Composition Containing Polyterpene,Terpene Resins, Liquid Polymers of Turpentine, Flourinated Terpene Compounds, Adhesives tackified with low molecular weight terpene-phenolic resins, Terpene halo-alkyl-ether-amine condensation product, Process for preparing a floral odorous perfume, Phenolic-modified rosin terpene resin, Resins from thiophene and turpentine, Synthetic Camphor Manufacturing, Menthol Oil From Leaves And Menthol Crystals (Peppermint), Spray Drying of Menthol And Peppermint Oil, Project Profile of Turpentine Oil, Camphor Tablets.

Preface

Pines are known to mankind from the time immemorial. It offers both direct uses, as well as indirect uses specially soil conservation. Initially it was used mainly for fuel; their branches were used for festivals etc. Pines besides being a source of valuable timber, pulpwood, yield pitch, tar, rosin, colophony and turpentine, collectively known as naval stores, a term coined to these owning to their use for construction and maintenance of sailing vessels as sealing compounds for their wooden hulls. The genius pine species tapped for their oleoresin in different countries. A variety of oleoresins are extracted from various plants. Pine oleoresin being the most important one is extracted from pine trees. Turpentine and rosin are two constituent parts of the pine oleoresins. The composition of turpentine varies considerably according to the species of pine exploited. More and more specialised uses are being found for pine resin products, particularly those of high quality. Turpentine derived from pine resin is also used as a source of aroma chemicals in flavour and fragrance industry. Pinewood chemicals are effectively gained from the trees in three principal ways; treatment of exuded gum from living pines, processing the wood stumps and wastes of aged trees and treatment of black liquor obtained as a byproduct in wood pulp industry. There are two steps involved in production of oleoresin; olustee gum cleaning process and recovery of turpentine and rosin: batch and continuous process. The panorama of base catalysed isomerisations of terpenes is an important part of aroma chemistry. Major contributions in this area are presented here under sections on hydrocarbons, alcohols, aldehydes, ketones, acids, esters and epoxides. Tall oil is a by product of the pine wood use to make sulfate pulp. Tall oil products find use in many product applications because of their economy and ready availability. The principal industrial applications of tall oil products are numerous; adhesives, carbon paper, detergents, driers, drilling fluids, oils, gloss oils, paper size, plasticizers, printing inks, soaps, textile oils etc.

Some of the fundamentals are pine oleoresin extraction methods, occurrence, formation and exudation of oleoresin in pines, processing of oleoresin, rosin derivatives and its potential, new developments in rosin ester and dimer chemistry, terpene based adhesives, effect of solvent, ozone concentration and temperature on yields were investigated, sylvestrene and some of its derivatives, homopolymers and copolymers of acrylates, polymers and copolymers of vinyl pinolate, base catalysed isomerisations of terpenes, components of pine roots, insecticides based on turpentine, the general characteristics of dimer acids, structure and properties of dimer acids etc.

The present book has been published having in views the important uses of pines. The book contains manufacturing process of different products extracted from pines like oleoresin, rosin, turpentine derivatives, tall oil, resins and dimer acids etc. This is the first book of its kind which is very resourceful for all from researchers to professionals.

Contents

Wood Rosin

Introduction
Source or Origin of the Substance
Properties of the Substance
Uses of the Substance
Combinations of the Substance
Evaluation

Process of Refining Wood Rosin

Example

Esters of Pine Wood Pitch

Chemical composition and antioxidant activity

of essential oil of pine cones of Pinus armandii

Introduction
Materials and methods
Plant material
Hydrodistillation
Gas Chromatography
Gas Chromatography-mass Spectrometry
Qualitative and quantitative Analyses
Antioxidant activity

Chemical Composition of The Oil of Pinus

Pinea L. Seeds
INTRODUCTION
Determination of Composition
Conclusion

Resin Products from Pines

Products
Historical Aspects
Resin producing pines
Effects Of Resin Tapping On Pines
Plant material
Essential oil isolation
Chemical composition
GC-MS analysis
Antimicrobial assay
Microbial strains and culture media
Antioxidant activity
DPPH free radical-scavenging activity
Cytotoxic assessment
Human cell lines and culture
Cytotoxicity assay
Chemical composition
Antibacterial activity
Antioxidant activity
Cytotoxic activity

Process for the manufacturing of turpentine, pine oil and rosin from woody materials rich in oleoresin

Structural Determination

Myrcene
Other Monoterpenes
Citral
Geraniol
Linalool
Citronellol And Citronellal
Terpineol

Menthol and Carvone

Mint Components
Carvone

Bicyclic Monoterpenoids

Two Commercial Syntheses of Bicyclic
Monoterpenoids

Synthesis of A-Santalol

Synthesis of --Santalol
Sandalwood Substitutes
Synthesis of a-Atlantone from d-Limonene

Production of a-Terpineol from a-Pinene

Materials and Methods
Equipment and Procedures
Analysis
Results and Discussions
Steady State Condition and Feed Plate Optimum
Pressure
Ratio of Volumetric Flow

Menthol

Synthesis of menthol from Myrcene:

Camphor

Structure Determination
Synthesis of Camphor
The Properties of Camphor
Toxicity of Camphor

Synthesis and Characterization of Isolongifoline

and Acetyl longifoline

Analysis of Reaction product (Reaction Monitoring)
Washing and Distillation of Reaction product
Characterization of Isolongifoline and Acetyl
longifoline
Characterization was done by following methods.
FTIR Analysis
GC-FID analysis
GC-MS analysis
FT-IR Analysis of Isolongifoline
FT-IR Analysis of Acetyl Longifoline
GC-FID analysis of Acetyl longifoline
GC-MS analysis of Isolongifoline

Terpene Resins in Pressure Sensitive Adhesives

Terpene Tackifiers studied
Properties Evaluated
Tackifiers studied

Terpene phenolic resins

Phenol-terpene-cyclic polyolefin polymer

The Insecticides Obtained from Turpentine

Introduction
The thiocyanates
Chlorinated terpenes
Terpenes and derivatives
Terpene polymers

.Pine oil cleaning composition

Optional Ingredients
Method for cleaning a hard surface
Pine Oil Formulations

Terpene Polymer

Tackifier resin composition and process

Hot Melt Coating Composition Containing Polyterpene,Terpene Resins

Liquid Polymers of Turpentine

Flourinated Terpene Compounds

Fluorination of Paracymene
Fluorination of Myrcene

Adhesives tackified with low molecular weight

terpene-phenolic resins

Terpene halo-alkyl-ether-amine condensation product

Process for preparing a floral odorous perfume

Phenolic-modified rosin terpene resin

Resins from thiophene and turpentine

Synthetic Camphor Manufacturing

Menthol Oil From Leaves And Menthol Crystals (Peppermint)

Spray Drying of Menthol And Peppermint Oil

Project Profile of Turpentine Oil

Camphor Tablets

List of Tables

Table : Composition of Wood Rosin
Table : Chemical properties of wood rosin
Table : Selection of possible components for edible coatings patented for organic fruits
Table : Ecotoxicity data for wood rosin in aquatic life
Table : Summary of Human Health and Toxicity Parameters of wood rosin
Table Percentage component of the pine cone oils of Pinus armandii.
Table Radical scavenging activity of the pine cone oils of Pinus armandii, BHT and ascorbic acid with DPPH.
Table Larvicidal activity of Pine oil against different Mosquito
Table Efficacy of Pine oil as mosquito repellent on human volunteers
Table Efficacy of Pine oil mats for protection against mosquitoes
Table : Compounds obtained from GC/GC-MS analysis of Pinus pinea L. seed’s oils*
Table Important commercial sources of pine resin
Table : Beta-pinene properties
Table : d-limonene properties
Table : D--carene properties
Table : D-cadinene properties.
Table : Methyl mercaptan properties
Table : The different essential oil constituents identified
in the essential oils of Pinus roxburghii
Table : In-vitro antibacterial activity of essential oil of Pinus roxburghii and refrence antibiotic determined with Agar well Diffusion Method
Table : In-vitro cancer activity of Pinus roxburghii essential oil
Table Composition of solution of turpentine and a-pinene
Table shows the relationship of time and the yield of a-terpineol on a variety of feed plates.
Table Purity a-terpineol and a-pinene on the bottom of products for various times with position of the feed Plate
Table Relationships of volume ratio of chloroacetic acid and the a-pinene with the purity of waste and Byproducts
Table Characteristics of Ion Exchange Catalyst Indion
Table : Catalytic conversion of longifoline over Catalyst Indion-
Table : Adhesive formulations using blends of SIS and SBS
Table
Table . Results from Iron Oxide based Soil System
Table . Results from Oily Soil system
Table . Bloom Performance

List of Figures

Figure : Molecular structures for abietic, pimaric, and palustric acids
Figure : Chromatogram ofPinus pinea L.seeds oil of
plants collected from the northwest region of Khorasan, Iran
Figure : Chromatogram ofPinus pineaL.seeds oil of plants collected from the southern region of Khorasan, Iran
Figure : d-limonene. l-limonene.
Figure Series of research experiment
Figure Relationship of time and yield of a-terpineol on a variety of feed plates
Figure Yield of a-terpineol at various pressures
Figure Relationships of volume ratio of chloroacetic acid solution and the solution of a-pinene to yield a-terpineol
Figure Synthesis of byproduct of a-pinene
Figure Synthesis of Isolongifoline and
Longifoline derivatives
Figure Acid Catalyzed Rearrangement of Lonifoline
Figure Reaction Mechanism of Acylation process in Longifoline
Figure FT-IR spectra of Iso-Longifoline
Figure FT-IR spectra of Acetyl-Longifoline
Figure GC-FID chromatogram of Isolongifoline
Figure GC-FID chromatogram of Acetyl longifoline
Figure GC-MS Total ion chromatogram (TIC) of the Isolongifoline sample showing three major chemical constituents
Figure Structure and mass spectra of Isolongifoline
Figure Structure and mass spectra of Longifoline
Figure GC-MS Total ion chromatogram (TIC) of the Acetyl Longifoline sample showing three major chemical constituents
Figure Structure and mass spectra of Acetyl Longifoline
Figure Structure and mass spectra of Isolongifoline methyl ether
Figure : Terpenes for tackifiers

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