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Heterocyclic Organic Corrosion Inhibitors: Principles and Applications

Heterocyclic Organic Corrosion Inhibitors: Principles and Applications

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Heterocyclic Organic Corrosion Inhibitors: Principles and Applications

Longueur:
545 pages
3 heures
Sortie:
Mar 7, 2020
ISBN:
9780128196946
Format:
Livre

Description

Heterocyclic Organic Corrosion Inhibitors: Principles and Applications aims to comprehend the synthesis and application of organic heterocyclic compounds as corrosion inhibitors in various corrosive environments. Considering the high importance of corrosion inhibitor development for different industries, the book provides the fundamentals and most recent advancements in this field. The book is an indispensable reference tool for industrialists and academicians working in the field of corrosion protection.

  • Provides a systematic overview of fundamentals and current advancements
  • Acts as a primary reference for beginner researchers in this arena
  • Presents a handy reference tool to different chemical industries
  • Covers fundamentals, industrial applications and most recent advancements in this area
Sortie:
Mar 7, 2020
ISBN:
9780128196946
Format:
Livre

À propos de l'auteur

Dr. Mumtaz A. Quraishi is a Chair Professor at the Center of Research Excellence in Corrosion at King Fahd University of Petroleum and Minerals, Saudi Arabia. He obtained Ph.D. in synthetic organic chemistry in 1986 from Kurukshetra University, and D.Sc. in corrosion inhibition in 2004 from Aligarh Muslim University. He has published more than 300 papers in reputed international journals and has been teaching for over 40 years. He is a fellow of Royal Society of Chemistry, UK. He has received several prestigious awards, including Life Time Achievement Award (International Science Congress Association, ISCA), Meritorious and Excellence in Corrosion Award (NACE, India), MASCOT award (ECI, India), Vigyan Ratna Award (CST, India) and is a member of Editorial Board of many International Journals. His current research area is designing of green corrosion inhibitors.

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Aperçu du livre

Heterocyclic Organic Corrosion Inhibitors - Mumtaz A. Quraishi

Heterocyclic Organic Corrosion Inhibitors

Principles and Applications

Mumtaz A. Quraishi

Dheeraj S. Chauhan

Viswanathan S. Saji

Table of Contents

Cover image

Title page

Copyright

Preface

Acknowledgment

List of abbreviations and symbols

1. Heterocyclic corrosion inhibitors

1.1. Introduction

1.2. Heterocyclic compounds

1.3. Important heterocyclic systems

1.4. Nomenclature of heterocyclic compounds

1.5. Heterocyclic systems as corrosion inhibitors

1.6. Effect of substituents on corrosion inhibition efficiency

Suggested reading

2. Experimental methods of inhibitor evaluation

2.1. Introduction

2.2. Gravimetric method

2.3. Adsorption parameters

2.4. Electrochemical methods

2.5. Surface analytical techniques

Suggested reading

3. Computational methods of inhibitor evaluation

3.1. Introduction

3.2. Density functional theory

3.3. DFT-based quantum chemical parameters

3.4. pKa analysis

3.5. Atomistic simulations

3.6. Application of atomistic simulation to corrosion inhibition studies

Suggested reading

4. Heterocyclic corrosion inhibitors for acid environments

4.1. Introduction

4.2. Acid pickling and acidizing processes

4.3. Corrosion and its inhibition in acid solutions

4.4. Heterocyclic corrosion inhibitors used for acid environments

4.5. Schemes for synthesis of heterocyclic corrosion inhibitors for acid environment

5. Heterocyclic corrosion inhibitors for sweet and sour environments

5.1. Introduction

5.2. Sweet corrosion

5.3. Sour corrosion

5.4. Heterocyclic inhibitors for sweet and sour environments

5.5. Schemes for synthesis of heterocyclic corrosion inhibitors for sweet/sour environment

6. Heterocyclic corrosion inhibitors for neutral environments

6.1. Introduction

6.2. Metallic corrosion and its inhibition in neutral environment

6.3. Heterocyclic corrosion inhibitors for neutral environments

6.4. Schemes for the synthesis of heterocyclic corrosion inhibitors for neutral environments

7. Heterocyclic corrosion inhibitors for alkaline environments

7.1. Introduction

7.2. Mechanism of corrosion in alkaline medium

7.3. Heterocyclic corrosion inhibitors for alkaline environments

8. Heterocyclic corrosion inhibitors for vapor-phase environments

8.1. Introduction

8.2. Mechanism and evaluation of corrosion inhibition using VCIs

8.3. Heterocyclic VCIs for ferrous and non-ferrous metals

9. Environmentally benign heterocyclic corrosion inhibitors

9.1. Introduction

9.2. Criteria for green corrosion inhibitors

9.3. Application of green chemistry metrics in the development of corrosion inhibitors

9.4. Application of greener techniques in the development of corrosion inhibitors

9.5. Types of environmentally benign corrosion inhibitors

9.6. Schemes for synthesis of heterocyclic ionic liquid based corrosion inhibitors

9.7. Schemes for chemical modification of chitosan for synthesis of corrosion inhibitors

9.8. Schemes for synthesis of heterocyclic corrosion inhibitors using MCRs

Index

Copyright

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Notices

Knowledge and best practice in this field are constantly changing. As new research and experience broaden our understanding, changes in research methods, professional practices, or medical treatment may become necessary.

Practitioners and researchers must always rely on their own experience and knowledge in evaluating and using any information, methods, compounds, or experiments described herein. In using such information or methods they should be mindful of their own safety and the safety of others, including parties for whom they have a professional responsibility.

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ISBN: 978-0-12-818558-2

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Preface

The science and technology of corrosion inhibitors is one of the most important areas in the field of corrosion. Among the different class of inhibitors, the heterocyclic organic inhibitors have attracted a great deal of attention due to the ease of synthesis and high corrosion inhibition attributes. Through the lone pair of electrons present in the heteroatoms such as O, N, S and P, they can be effectively chemisorbed on the metal surface. This books aims to provide a comprehensive overview of heterocyclic corrosion inhibitors in different applications.

Followed by the first chapter on basics of heterocyclic compounds, we have provided two chapters on various experimental and computational methods used to study corrosion inhibition. Chapters 4–7 highlight the heterocyclic corrosion inhibitors with reference to their aqueous/industrial applications, viz. acid pickling/acidizing, sweet/sour corrosion, and corrosion in neutral pH and alkaline environments. The last two chapters, respectively, explain heterocyclic vapor phase inhibitors and green inhibitors.

Chapter 1 provides an overview of the fundamentals of heterocyclic compounds with a view to their applications in corrosion inhibition. The chapter also describes the major heterocyclic corrosion inhibitors and the influence of various substituent groups on corrosion inhibition. Chapter 2 entirely focuses on various experimental methods which are used for evaluation of the inhibitor performance. The methods described include gravimetric weight loss, electrochemical techniques, surface characterization techniques, and adsorption isotherms. Chapter 3 gives a concise description of different computational approaches used in corrosion inhibition studies. Techniques such as density functional theory, Monte Carlo, and molecular dynamics simulations are described with emphasis on the different reactivity parameters that are calculated using these techniques.

Chapter 4 explains in detail the reported heterocyclic corrosion inhibitors for acidic environments. The severe/harsh corrosive environment created by the use of concentrated acids requires the use of thermally stable efficient corrosion inhibitors in applications such as acid pickling and acidization processes. Chapter 5 is specific for heterocyclic corrosion inhibitors for sweet and sour corrosion environment. The corrosion due to H2S and CO2 are very important in various industrial sectors such as oil and gas. Chapter 6 provides a good description on heterocyclic corrosion inhibitors that are being used in neutral environments, whereas Chapter 7 details the heterocyclic corrosion inhibitors for alkaline environments. Chapter 8 gives a concise description on heterocyclic volatile corrosion inhibitors. The last chapter (Chapter 9) highlights the important features of environmentally benign heterocyclic corrosion inhibitors. The criteria for classification of corrosion inhibitors according to PARCOM guidelines, the different green chemistry metrics, and the type of environmentally benign heterocyclic inhibitors are outlined. The environmental awareness and strict legislations related to the use of toxic corrosion inhibitors discussed. With each chapter, several tables and schemes are provided on the nature and type of inhibitors and their synthesis approaches.

We hope that the book will be a handy reference tool for students and researchers working in the field of corrosion inhibition.

M.A. Quraishi, D.S. Chauhan, V.S. Saji

Acknowledgment

We would like to express our gratitude to the Deanship of Scientific Research, King Fahd University of Petroleum and Minerals (KFUPM), Saudi Arabia, for providing funds on book writing project (BW 181003). We would also like to express our gratitude to all those who granted us the copyright permissions for reproducing illustrations. Our sincere thanks for the Elsevier team in evolving this book into its final shape.

List of abbreviations and symbols

1

Heterocyclic corrosion inhibitors

Abstract

The severe consequences of corrosion have become a problem with global implication. Corrosion loss causes a substantial economic and ecological impact on entire global infrastructure and consumes 3%–4% of the gross domestic product of industrialized countries. Among the various corrosion control strategies, the use of corrosion inhibitors is conceivably the simplest, economic and practical approach that are in routine use in industries. Organic compounds in general and heterocyclic compounds, in particular, are considered as potential corrosion inhibitors. This chapter provides a concise description of the fundamentals of heterocyclic compounds (types, structure, and nomenclature) and their application in corrosion inhibition.

Keywords

Corrosion; Corrosion inhibitor; Heteroatom; Heterocyclic compound; Organic inhibitor; Pyridine

1.1 Introduction

1.2 Heterocyclic compounds

1.3 Important heterocyclic systems

1.3.1 Azoles

1.3.2 Indoles

1.3.3 Pyridines

1.3.4 Diazines

1.3.5 Quinolines

1.4 Nomenclature of heterocyclic compounds

1.4.1 Common or trivial names

1.4.2 Hantzsch–Widman nomenclature

1.4.3 The replacement nomenclature

1.5 Heterocyclic systems as corrosion inhibitors

1.5.1 Five-membered heterocycles

1.5.2 Six-membered heterocycles

1.5.3 Macrocyclic compounds

1.6 Effect of substituents on corrosion inhibition efficiency

Suggested reading

References

1.1. Introduction

The term corrosion is usually referred to as the deterioration of metallic materials by its surrounding. In general, corrosion can be defined as a chemical or electrochemical reaction between a metal and its environment, which results in its deterioration. The serious consequences of corrosion have become a problem with global implication. Corrosion loss causes a substantial economic and ecological impact on entire global infrastructure and consumes 3%–4% of the gross domestic product of industrialized countries [1–5].

Selection and application of suitable corrosion prevention methods are hence highly essential for the protection and efficient use of metallic structures. Most of the industries including oil and gas, water desalination, and chemical industries are suffering from various corrosion issues resulting in enormous economic loss. The virtue is that by the adoption of suitable corrosion prevention strategies, a significant extent of the loss can be avoided. Among the various corrosion control strategies, the use of corrosion inhibitors is perhaps the simplest, economic, and effective approach that is in routine use in industries. A corrosion inhibitor can be defined as a substance that when added in suitable quantity to a corrosive environment lowers the corrosion rate significantly [1,2].

One way of classification of inhibitors is (i) inorganic and (ii) organic inhibitors. When compared to conventional surface passivating inorganic inhibitors, organic inhibitors (adsorption-type) in general are attractive due to their high efficiency and environmental friendliness. Organic inhibitors are widely employed in various industries for various aggressive environments. Their inhibition performance is correlated with their chemical structure and physicochemical properties such as the nature of functional groups, electron density at donor atoms, p-orbital character, and the molecular electronic structure. The inhibition is mainly attributed to adsorption and formation of a protective barrier film [1,2]. Among the various organic inhibitors, the best available class is perhaps the heterocyclic compounds. Organic compounds having heteroatoms such as O, N, and S are found to have higher basicity and electron density and thus act as better inhibitors.

The first part of the chapter provides a concise description of the fundamentals of heterocyclic compounds (types, structure, and nomenclature) with a view of their application in inhibition technology that is followed by an account on the basics of heterocyclic corrosion inhibitors. For more details on fundamentals of corrosion and corrosion inhibitors, the reader is referred to bonafide textbooks available [1–5].

1.2. Heterocyclic compounds

An organic compound containing the carbon atoms arranged in the form of a ring is called a carbocyclic compound. However, if an atom of a different element replaces one of the carbon atoms, then this compound is referred to as a heterocyclic compound [6,7]. Nitrogen (N), sulfur (S), and oxygen (O) are the most commonly occurring heteroatoms, although heteroaromatic rings containing other heteroatoms are also well known. It is noteworthy to mention that the heterocyclic compounds constitute the building blocks of many drugs. The phytochemicals found in different parts of a plant such as the root, stem, leaf, flower, seed, fruit etc., are also composed of complex heterocycles. In addition, several essential/nonessential amino acids, carbohydrates, proteins etc., are also made of heterocycles [7–10].

By definition, any atom other than carbon can be designated as a heteroatom, and the organic ring can be termed as a heterocycle. Among the heterocyclics, the compounds having N, S, O, and P are the most common (Fig. 1.1).

Figure 1.1 Examples of heterocyclic compounds.

In a heterocyclic corrosion inhibitor, the lone pair of electrons in the heteroatoms is readily available for donation to the targeted metal and that in effect can result in an effective chemical adsorption of the inhibitor molecule. Further, the heteroatoms when present in acid/alkaline media may undergo protonation/deprotonation resulting in the development of positive/negative charge on the atoms. This can promote either acceptance of electrons from the metal atoms via back donation or electron donation to the metal surface [6,7]. The following section describes an overview of the different types of heterocyclic compounds:

(1) Heterocycloalkanes: In these compounds, the ring is saturated, for example, dioxane, thiane, dithiane, piperidine, and piperazine (Fig. 1.2A).

Figure 1.2  Saturated and unsaturated heterocyclic compounds. 

Reproduced with permission from T. Eicher, S. Hauptmann, A. Speicher, The Chemistry of Heterocycles: Structures, Reactions, Synthesis, and Applications, Wiley, New Jersey, 2013; Copyright 2013 © John Wiley and Sons.

(2) Heterocycloalkenes (partially unsaturated systems): In these compounds, π bonds are present in ring (Fig. 1.2B). The heteroatom present in the ring can also be the part of a double bond inside the heterocycle. In the case of X=O+, the compounds act as oxenium salts, X=S+, sulfenium salts, and X=N, imines.

(3) Heteroaromatic systems: These are heterocyclic compounds that follow the Hückel's Rule, i.e., the rings possessing (4n+2) π-electrons. Prominent examples are furan, thiophene, pyrrole, pyridine, imidazole, and pyrimidine (Fig. 1.2C).

1.3. Important heterocyclic systems

In this section, we have given some of the important types of heterocyclic systems that constitute the major corrosion inhibitors.

1.3.1. Azoles

Heterocyclic compounds containing one N atom and at least one other noncarbon atoms (e.g., N, S, O) arranged in a five-membered ring are known as azoles. These compounds constitute a wide range of pharmaceutical compounds. Examples include pyrazoles, imidazoles, benzimidazole, benzotriazole, etc.

1.3.2. Indoles

Indole is a bicyclic structure, in which the benzene ring is fused to a five-membered pyrrole ring. These compounds show a wide range of biological activity and constitute an integral part of many drugs.

1.3.3. Pyridines

These are six-membered heterocycles with structure similar to that of benzene where one CH is replaced by N atom.

1.3.4. Diazines

Diazines are a class of organic compounds having molecular formula C4H4N2, that is, each diazine ring contains a benzene ring where N atoms replace two CH groups. Three isomers of diazines are given below:

1.3.5. Quinolines

These are heterocyclic compounds having chemical formula C9H7N, where the benzene ring is fused with pyridine. The isomer of quinoline is isoquinoline.

Fig. 1.3A–D shows examples of well-known heterocyclic organic compounds. For an easy understanding, the heterocycles are shown in red color throughout the book.

Figure 1.3A Examples of natural products based on heterocyclic compounds.

Figure 1.3B Examples of heterocyclic amino acids.

Figure 1.3C Examples of heterocyclic drugs.

Figure 1.3D Examples of heterocyclic vitamins.

1.4. Nomenclature of heterocyclic compounds

There are three important systems by which heterocyclic compounds are named: (i) common names, (ii) Hantzsch–Widman system, and (iii) replacement nomenclature.

1.4.1. Common or trivial names

The common names of heterocyclic compounds are based on the following guidelines:

(1) The names are based on occurrence, origin, and special properties. Examples: furan, thiophene, pyrrole, pyridine, indole, quinolone, etc.

(2) In a heterocyclic ring, numbering preferably commences at a saturated rather than at an unsaturated heteroatom (Fig. 1.4).

(3) If more than one type of the heteroatoms is present, the ring is numbered from the heteroatom of the higher priority (O>S>N). The numbering is done in such a way so that heteroatom gets the smallest value.

Figure 1.4  Numbering in the heterocyclic rings.

Figure 1.5A  Naming the heterocyclic ring according to the parent molecule.

Figure 1.5B  Nomenclature of partially hydrogenated systems.

(4) Name of the heterocyclic ring is chosen as the parent compound, and the names of the fused ring are attached as a prefix. The prefix in such names have the ending o, e.g., benzo, naptho, and so on (Fig. 1.5A).

(5) In partially hydrogenated systems, the terms dihydro, trihydro, etc. are used. The number indicates the location of hydrogenation. For example, 2-dihydropyran (2H-pyran), 4-dihydroydropyran (4H-pyran), 1,4-dihydropyridine, 2,3-dihydropyridine, etc. (Fig. 1.5B).

1.4.2. Hantzsch–Widman nomenclature

The Hantzsch–Widman nomenclature is based on the type of heteroatom, the ring size (n), and the nature of the ring, whether it is saturated or unsaturated. This nomenclature is based on the following guidelines:

(1) Type of heteroatom: The type of heteroatom is designated by a prefix, e.g., aza for N, thia for S, oxa for O, and phospha for P.

(2) Ring size: The ring size of the saturated/unsaturated systems is indicated by appropriate suffixes using Latin numerals as given in Table 1.1. The ending indicates the degree of unsaturation in the ring. For example, three-membered saturated and unsaturated heterocycles are named as irane and irine, respectively. Suffix ir represents the ring size. If N is present, the name will be iridine.

Table 1.1

(3) Monocyclic systems: The compound having the highest number of noncumulative double bonds is considered as the parent molecule. The nomenclature is done by linking one or more prefixes with a suffix [7].

• Monocyclic systems with one heteroatom: The numbering starts from heteroatom (Fig. 1.6).

• Monocyclic systems with two or more identical heteroatoms: The prefixes di-, tri-, tetra-, etc., are used. The numbering is done in such a way that heteroatoms get the smallest number (Fig. 1.7A).

• Monocyclic systems with two or more different heteroatoms: For different kinds of heteroatoms, prefixes are used, for example, the preference is as follows: S>N>O. The heteroatom highest in Table 2.1 is assigned the 1-position in the ring, and the left over heteroatoms are allocated the smallest possible set of number locants (Fig. 1.7B):

• Identical systems linked by a single bond: In such cases, prefixes bi-, ter-, quater-, etc., are used (Fig. 1.7C) [7].

The above structures in where two or more heterocyclic rings are separated by single bonds are known as isolated heterocyclic compounds.

(4) Heterocyclic systems fused with benzene rings: In this case, carbocyclic ring is designated as benzo and trivial name is given to heterocycle (Fig. 1.8).

Figure 1.6  Numbering in monocyclic systems with single heteroatom.

Figure 1.7  Numbering in monocyclic heterocycles (A) having more than one heteroatom, (B) having more than one heteroatom of different types, and (C) identical systems connected by a single bond.

Figure 1.8  Some of the common fused ring heterocycles.

Figure 1.9  Numbering in more than one heterocycles fused together. 

Reproduced with permission from T. Eicher, S. Hauptmann, A. Speicher, The Chemistry of Heterocycles: Structures, Reactions, Synthesis, and Applications, Wiley, New Jersey, 2013; Copyright 2013 © John Wiley and Sons.

(5) Heterocyclic systems fused with other heterocyclic rings: This category contains compounds where one heterocyclic ring is fused to one or more heterocyclic rings (Fig. 1.9).

Here, firstly, the system is divided into its components. The name of the fused component, by replacing the terminal ‘‘e’’ with ‘‘o’’ is added prior to base component's name. Numbers and letters in square brackets describe the atoms common to both rings, where the order of the numbers must agree to the direction of the lettering of the base component [7].

1.4.3. The replacement nomenclature

In replacement nomenclature, the parent compound is named as carbocyclic compound and the heteroatom as prefix aza, oxa, and thia for N, O, and S ring atom, respectively. The heterocyclic rings are numbered so that the heteroatom has the lowest possible number.

(1) Monocyclic systems: The type of heteroatom is indicated by a prefix (Table 1.1). The location and prefix of heteroatoms are written in front of the corresponding hydrocarbon name. The order and numbering of the heteroatoms

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