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SYNTHESES BASED ON THE TELOMERIZATION REACTION
S.Z.Khudayberganova
S.I.Nomozov
D.P.Radjibayev
Tashkent State Technical University
https://doi.org/10.5281/zenodo.15395969
ARTICLE INFO
ABSTRACT
Qabul qilindi: 05-May 2025 yil
Ma’qullandi: 10- May 2025 yil
Nashr qilindi: 13-May 2025 yil
This article explores the synthesis of chemical compounds
through telomerization reactions. Telomerization is a
chain process involving the interaction between low-
molecular-weight telogens and monomers under
catalytic conditions, leading to the formation of products
referred to as telomers. The article specifically examines
the telomerization of unsaturated compounds with
alcohols, aldehydes, and peroxides, highlighting the roles
of radical and ionic mechanisms involved in these
reactions. The industrial significance of telomerization is
discussed, particularly its applications in the synthesis of
high-performance solvents, plasticizers, and lubricants,
as supported by scientific literature. The results
demonstrate the potential of this synthetic approach for
enabling innovative applications in the chemical
industry.
KEYWORDS
Telomerization
reaction,
telomers, telogen, monomer,
radical mechanism, catalyst,
aliphatic alcohols.
Due to the rapid advancement of chemistry and innovative technologies, various
methods for producing alcohols are currently being developed. Recent data indicate a growing
demand for the industrial-scale production of these types of organic compounds [1].
The term telomerization is derived from the Greek words telos — meaning end or
terminal, and meros — meaning part or segment. It describes a type of chain reaction in
which repeating monomer units (M) are inserted between the two fragments of a compound
X–Y (telogen), resulting in the formation of a homologous series of telomers with the general
formula X–Mₙ–Y (n = 2–40) [2].
One of the promising methods for utilizing natural and industrial gases in organic
synthesis is the telomerization reaction. This approach enables the production of various
mono-, bi-, and polyfunctional compounds of practical significance from simple olefins such as
ethylene and propylene [3]. At present, telomerization reactions are employed in the
manufacturing of synthetic disinfectants, as well as detergents, waxes, lubricants, varnishes,
solvents, dielectrics, plasticizers, resins, and synthetic fibers [4].
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Telomerization plays an important role in the advancement of chemical science. As the
number of carbon atoms in the molecule of an aliphatic compound increases, the complexity
of its synthesis rises sharply. As a result, only a limited number of compounds containing 15
or more carbon atoms are currently known. Existing experimental data indicate that
telomerization remains a relatively underexplored area within organic chemistry [5].
Depending on the nature of the X-group, the telomerization reaction can proceed via
coordination, free-radical, or ionic mechanisms. The general scheme of the telomerization
reaction can be represented as follows:
nRCH = CH
2
+ XY →
(initsiator)
X(RCHCH
2
)
n
Y
In this context, XY serves as the chain carrier in the reaction.
However, such generalized schemes do not necessarily imply that all studied
telomerization reactions exhibit a chain character [6]. In cases where the X–Y bond is
susceptible to homolytic cleavage, the telomerization reaction proceeds via a free radical
mechanism. It is not appropriate to include compounds containing only C–F bonds in such
reactions. Telomerization reactions involving aromatic compounds with non-activated C–N
bonds are typically inefficient, and in the case of acetylenic homologs, telomerization is almost
nonexistent [7]. Although C–H bonds in amino acids can participate in the reaction, C–N bonds
generally do not undergo telomerization. In cyclic compounds, the reaction may proceed
either with ring retention or ring opening [8].
Peroxides are the most commonly used initiators. Additionally, azo compounds, oxygen,
and ultraviolet (UV) or gamma (γ) radiation can also initiate the telomerization reaction.
Unsaturated compounds are most frequently used as monomers [9].
For radical telomerization reactions, the following schemes have been proposed to
illustrate the underlying mechanisms involved in these processes [10]:
Chain growth
Telomer
Chain termination
R
X
Y + R
RY + X
X + C
C
X
C
C
X
C
C + n C
C
X
(
C
C
)
n
C
C
X
(
C
C
)
n
C
C + X Y
X
(
C
C
)
n+1
Y + X
2X
(
C
C
)
n
C
C
[X
(
C
C
)
n+1
]
2
Initiation
Initiator
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This scheme is not universally applicable to all reactions, as there are known
telomerization reactions that do not conform to it. Additionally, the scheme does not account
for the formation of by-products [11].
Numerous scientists have made significant contributions to the development of this
field. For example, N. Semenov developed the theory of chain reactions; S. Medvedev and his
colleagues proposed mechanisms of chain transfer; and S. Bagdasaryan investigated the
mechanisms of initiation and inhibition in polymerization reactions. Their work has played an
important role in advancing telomerization research [12].
N. Nesmeyanov and his students conducted a series of studies on the telomerization of
olefins with carbon tetrachloride, chloroform, and silicon hydrides. The telomerization of
ethylene with carbon tetrachloride was carried out for the first time. In 1948, American
chemists R. Joyce, N. Hanford, and I. Harmon studied this reaction under pressure in the
presence of benzoyl peroxide. They successfully isolated the reaction products containing
between 3 and 9 carbon atoms and confirmed their structure as [Cl(CH₂CH₂)ₙCCl₃].
Subsequently, G. B. Ovakimyan and A. A. Beer developed and implemented a
straightforward continuous method for synthesizing such compounds on an industrial scale.
Research conducted by A. Karapetyan demonstrated that the composition of the telomer
mixture is primarily determined by the molar ratio of ethylene and carbon tetrachloride fed
into the reactor [13].
Takahashi and Smutny independently discovered the telomerization reaction of 1,3-
butadiene. In this process, telomerization involves the dimerization of 1,3-butadiene through
the addition of a telogen. The products of this reaction are referred to as telomers, and the
reaction scheme is presented below [14].
x
x
x
HX, [kat[
Products of the telomerization reaction of 1,3-butadiene
Multiple isomers can be formed in this reaction. In addition to 1,3-butadiene, other
dienes, including cyclic dienes such as cyclopentadiene, can also be used. A wide range of
compounds can serve as telogens, such as water, ammonia, alcohols, or acidic substances.
When water is used as the telogen, unsaturated alcohols are produced [15].
The Kuraray company has industrially produced 1-octanol at a scale of 5,000 tons per
year, primarily using organometallic compounds of palladium and nickel as catalysts. In 2008,
Dow Chemical initiated the industrial-scale production of 1-octene from butadiene in
Tarragona. In this process, the telomerization of butadiene with methanol in the presence of a
palladium catalyst yields 1-methoxy-2,7-octadiene, which is subsequently fully hydrogenated
to 1-methoxyoctane. In a final step, 1-methoxyoctane is converted into 1-octene and methanol
[16].
Regina Palkovits and her research team investigated the telomerization reactions of 1,3-
butadiene with various alcohols using different catalytic systems. Palladium and phosphine
were employed as catalysts in these reactions. Their research focused on the activity of
Pd/phosphine systems in telomerization and their involvement in nucleophilic reactions,
which contributed to advancing telomerization processes involving 1,3-butadiene and various
nucleophiles. In their study, alcohols such as ethylene glycol, 1- and 2-propanol (1-PrOH, 2-
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PrOH), 1,2- and 1,3-propanediol (1,2-PD, 1,3-PD), glycerol (Gly), and 1,2- and 1,4-butanediol
(1,2-BD, 1,4-BD) were used as nucleophiles [17].
Telomerization reaction of 1,3-butadiene with palladium and nickel catalysts
HO
OH
HO
HO
HO
OH
HO
OH
HO
OH
OH
OH
OH
HO
OH
EG
1-PrOH
2-PrOH
1,2-PD
1,2-PD
Gly
1,2-BD
1,4-BD
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In this study, the telomerization of 1,3-butadiene with 1,3-propanediol (1,3-PD) resulted
in
the
formation
of
the
following
products.
HO
OH
+
Pd/TOMPP
O
OH
Oktadienilefir (1)
O
O
Bis-oktadienilefir (2)
OH
2,7 - oktadienol (5)
1,4,7 - oktatrien (3)
4 - vinilsiklogeksen (4)
The products formed in this reaction include mono-telomers (octadienyl ethers) (1), di-
telomers (bis-octadienyl ethers) (2), and 2,7-octadienol (5), which is obtained through the
hydrolysis of the telomer products with water. Dimerization products such as 1,4,7-octatriene
(3) and 4-vinylcyclohexene (4) are also formed. The telomerization of 1,3-butadiene with
various alcohols and its interaction with diols has been studied using Pd/TOMPP catalysts
[18].
Raw materials capable of undergoing telomerization—such as ethylene, other olefins,
and their halogenated derivatives—enable the synthesis of highly functional mono- and
bifunctional compounds, including acids. The halogen-substituted acids obtained through
telomerization can be used for the synthesis of both saturated and unsaturated acids [19].
Several researchers—S. Bigot, J. Lai, I. Schweitzer, and M. Sauthier—have studied the
telomerization of 1,3-butadiene with glycerol under aqueous biphasic conditions, focusing on
the influence of reaction conditions on product yield. During the reaction, butadiene is
continuously supplied and the pressure is kept constant. To improve the activity and
selectivity of the resulting mono-, di-, and tri-telomers, various reaction parameters were
investigated.
Y. Chuamin and his students conducted telomerization reactions involving cyclopentane
and 2-pentene [20].
+
R
1
R
2
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R
1
R
2
+
R
1
R
1
R
2
R
2
+
+
R
1
R
1
+
R
2
R
2
C10
C9
11C
A. Rzhevsky, A. Topchiy, and their collaborators studied the telomerization of isoprene
with methanol in the absence of a solvent, in the presence of heterocyclic palladium
complexes. The telomerization processes of butadiene with arylamines in the presence of
palladium complexes were investigated by R. Aripov, Ye. Ganieva, R. Izhberdina, R.
Khusnutdinov, K. Khusnutdinova, and I. Abdurakhmanov. O.B. Penrhyn-Lowe and his students
studied the radical telomerization reactions of ethylene glycol dimethacrylate, 1,6-hexanediol
dimethacrylate, and 1,12-dodecanediol dimethacrylate. A. Bechkoff, M. Belbachir, B. Guyot,
and B. Boutevin researched the telomerization of styrene with mercaptans to produce
functional telomers of macromonomers with variable molecular masses [21].
Telomerization reactions are of significant practical importance in the production of
macrocyclic lactones, ω-amino acids, high-carbon fatty acids, and other organic compounds.
In the telomerization of ethylene, radical rearrangement has been extensively studied on
carboxylic acids and their derivatives. However, little research has been conducted on the
rearrangement during the telomerization of alcohols [22].
The article reviews various methods for synthesizing aliphatic alcohols and analyzes
research conducted by leading scientists from major scientific centers and educational
institutions worldwide. It covers both laboratory and industrial methods for synthesizing
saturated alcohols, producing alcohols from unsaturated hydrocarbons, and synthesis
reactions based on telomerization. It also discusses the achievements in alcohol synthesis,
their chemical transformations, kinetics, production technologies, and application areas.
Furthermore, the influence of the nature, structure, number, and spatial configuration of
radicals in starting materials, as well as the type, nature, and amount of solvents and catalysts
used in the process, has been analyzed. Researchers worldwide have studied intermediate
and by-products formed in these processes using various catalysts.
In conclusion, it can be stated that the synthesis of alcohols through telomerization and
the development of industrial-scale production technologies have been extensively analyzed.
The synthesis and large-scale production of such compounds—and the design of new organic
substances with unique properties based on them—are identified as urgent scientific and
practical issues.
Ethylene production through natural gas processing is of great importance. In these
processes, ethane and other various hydrocarbons serve as the primary raw materials.
Currently, most of the ethylene produced in our country is used for polyethylene synthesis.
Additionally, ethylene can be used in the synthesis of cycloalkanes, valuable olefins, flotation
reagents, technical cleaning agents, and the synthesis of synthetic fatty acids and alcohols.
The industrial-scale production of saturated alcohols from ethylene has great practical
significance. One of the unconventional methods for obtaining necessary alcohols in the
industry is the synthesis of higher alcohols from lower molecular weight alcohols via the
telomerization reaction. The reaction of saturated alcohols with ethylene proceeds via a free
radical telomerization mechanism. Initially, branching occurs in the carbon chain of the
growing telomer, as the growing radical undergoes homolytic rearrangement. In this
mechanism, various telomers are formed depending on the initial alcohol. Acetone was used
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as the catalyst in the telomerization reaction, while hydrogen peroxide and organic peroxides
(tert-butyl peroxide (TBP), benzoyl peroxides) were used as initiators.
In this article, the telomerization process of ethylene with methanol is thoroughly
analyzed. The reaction proceeds via a radical mechanism in the presence of hydrogen
peroxide (H₂O₂). Acetone was used as the solvent. Within the scope of the telomerization
reaction, the initiation, propagation, and termination stages occur at the molecular level.
Additionally, the physicochemical properties, selectivity, and industrial applications of the
resulting telomer products are discussed.
Telomerization is a chain radical process in which telomers with controlled molecular
weight and well-defined structures are formed through the interaction of a monomer and a
telogen. Unlike polymerization, this reaction results in low-molecular-weight products.
The ethylene molecule (CH₂=CH₂) possesses a pi-bond with high electron density,
making it reactive toward radical attack. Methanol acts as an easily accessible proton donor
and serves as the telogen. Hydrogen peroxide, chosen for initiation, is a strong oxidizing agent
that functions as a radical initiator. Acetone, used as the solvent, adjusts the dielectric
properties of the reaction medium and helps stabilize the radicals formed.
The radical mechanism of telomerization follows the conventional principles of chain
reactions and proceeds through three main stages:
This article presents a detailed analysis of the telomerization process of ethylene with
methanol.
The reaction was carried out via a radical mechanism in the presence of hydrogen
peroxide (H₂O₂). Acetone was used as the solvent. Within the telomerization process, the
initiation, propagation, and termination stages proceed at the molecular level. Additionally,
the physicochemical properties, selectivity, and industrial applications of the telomer
products were discussed.
Telomerization is a chain radical process in which telomers with a defined structure and
controlled molecular mass are formed from a monomer and a telogen. Unlike polymerization,
these reactions yield low molecular weight products. The ethylene molecule (CH₂=CH₂)
possesses a π-bond with high electron density. Methanol, being a good proton donor, acts as a
telogen. Hydrogen peroxide, chosen for initiation, is a strong oxidizing agent and serves as a
radical-forming compound. Acetone, used as the solvent, adjusts the dielectric properties of
the reaction medium and ensures the stability of radicals.
The radical mechanism of the telomerization reaction is based on the classical chain
reaction principle and proceeds in three main stages:
Initiation:
Hydrogen peroxide decomposes in the presence of metal ions to form radicals:
H₂O₂ → 2 HO•
The resulting hydroxyl radicals interact with methanol molecules to form methoxy
radicals:
HO• + CH₃OH → CH₃O• + H₂O
Propagation (Chain Growth):
The methoxy radical first adds to the ethylene molecule:
CH₃O• + CH₂=CH₂ → CH₃O–CH₂CH₂•
This radical then reacts with additional ethylene molecules:
CH₃O–CH₂CH₂• + nCH₂=CH₂ → CH₃O–(CH₂CH₂)ₙ–CH₂CH₂•
During this stage, the molecular weight of the product is relatively controlled—telogen
presence limits chain length.
Termination:
The chain is terminated by a free hydrogen radical or another methanol molecule:
CH₃O–(CH₂CH₂)ₙ–CH₂CH₂• + H• → CH₃O–(CH₂CH₂)ₙ–CH₂CH₃ or
CH₃O–(CH₂CH₂)ₙ–CH₂CH₂• + CH₃OH → CH₃O–(CH₂CH₂)ₙ–CH₂CH₂OH + CH₃O•
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This completes the active growth of the telomer molecule.
Physicochemical properties of telomer products — The general structure of the
resulting telomers is CH₃O–(CH₂CH₂)ₙ–X, where X = H or OH. These products possess the
following properties: relatively low boiling points (100–160°C), viscosity dependent on
telomer chain length, high polarity enabling them to dissolve a wide range of inorganic and
organic compounds, and good stability against light and oxygen—making them easy to store
and transport.
Industrial applications:
Ethylene–methanol telomerization products are used as organic solvents, plasticizers,
and lubricants in the following industrial sectors:
•Paints and coatings industry: Used as highly volatile solvents, especially for coating
metal surfaces.
•Polymer production: Telomers are added as plasticizers.
•Agrochemicals: Used as solvents in the formulation of pesticides and herbicides.
•Lubricants: Incorporated into specialized oils for mechanisms operating in harsh
environments.
The relevance of telomerization reactions has been increasing in recent years due to the
growing demand for organic synthesis, environmentally safe technologies, and high-value-
added products. Especially, the advantages of the ethylene–methanol system—its use of
inexpensive and readily available raw materials, the ability to obtain products with high
selectivity, and controlled molecular architecture—make this method widely applicable in
practice.
Another important aspect is that methanol is a renewable feedstock (e.g., derived from
biomass or synthesis gas), which brings the reaction closer to environmentally sustainable
technologies. Ethylene, a major olefin extensively produced in the petrochemical industry,
shows high reactivity in telomerization and helps reduce energy consumption.
Moreover, telomer products (e.g., polyethylene glycol ethers, solvents) are important
intermediates in pharmaceuticals, cosmetics, polymers, and agrochemicals. This makes the
process not only theoretically interesting but also a strategic technological link in global
production chains.
Today, reactions that comply with the principles of sustainable chemistry, green
chemistry, and waste-free technologies are of special interest. Telomerization falls into this
category, as it proceeds under low pressure, relatively low temperature, uses water-
generating initiators (H₂O₂), and yields selective products—significantly reducing industrial
waste. Furthermore, its consideration as an alternative pathway to polymer synthesis, ability
to generate flexible molecular architectures, and potential integration with nanotechnologies
make it a highly relevant subject for scientific research.
Industrial Applications
The telomerization products of ethylene and methanol are used as organic solvents,
plasticizers, and lubricants in various industrial sectors:
Paints and coatings industry: Utilized as highly volatile solvents, especially for coating
metal surfaces.
Polymer production: Telomers are added as plasticizers to enhance flexibility.
Agrochemicals: Serve as solvents in the formulation of pesticides and herbicides.
Lubricants: Used in special lubricating oils for mechanisms operating in harsh
environments.
The relevance of telomerization reactions has significantly increased in recent years due
to the growing demand for organic synthesis, environmentally safe technologies, and the
production of high value-added products. In particular, the advantages of the ethylene–
methanol system—based on inexpensive and readily available feedstocks, the ability to obtain
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products with high selectivity and controlled properties—make this method highly applicable
in practice.
An additional important factor is that methanol is a renewable feedstock (e.g., derived
from biomass or synthesis gas), which aligns the reaction with environmentally sustainable
technologies. Ethylene, a major olefin widely produced in the petrochemical industry, exhibits
high reactivity in the telomerization process and contributes to reduced energy consumption.
Moreover, telomerization products (e.g., polyethylene glycol ethers, solvents) are
important intermediates in the pharmaceutical, cosmetic, polymer, and agrochemical
industries. This highlights the process not only as a subject of theoretical interest but also as a
strategic technological link in global production chains.
Currently, reactions that comply with the principles of sustainable chemistry, green
chemistry, and zero-waste technologies are attracting considerable attention. Telomerization
belongs to this class of reactions, as it proceeds under low pressure, at relatively low
temperatures, utilizes water-forming initiators (like H₂O₂), and yields highly selective
products, thereby significantly reducing industrial waste. Additionally, its potential as an
alternative route to polymer synthesis, ability to construct flexible molecular architectures,
and compatibility with nanotechnological integration make it a highly relevant field for
scientific research.
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