Manufacturing Technology Of Rosins,

Turpentines, Pine Oil, Menthol, Camphor,

Terpenes And Derivatives With
Processing And Formulations

Author: Dr. Himadri Panda

ISBN: 9788193563724
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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,
Santalol, Production of
a-Terpineol from a-Pinene,
Pinene, Menthol, Camphor, Synthesis and Characterization of Isolongifoline and
Acetyl longifoline, Terpene Resins in Pressure Sensitive Adhesives, Terpene phenolic resins, Phenol-
terpene-cyclic
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