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Diethylamine

What Is Diethylamine?

Diethylamine is an organic nitrogen compound of secondary amines.

It is produced by amination with ethyl alcohol or by reductive amination with acetaldehyde. In either method, ethylamine, diethylamine, and triethylamine are produced simultaneously, and each is separated and purified by distillation.

Diethylamine is corrosive and causes severe skin burns when in contact with the skin.

Uses of Diethylamine

Diethylamine is widely used as a raw material for pharmaceuticals, dye intermediates, rubber chemicals, herbicides, insecticides, surfactants, paints, and synthetic resins. It is also used as a reagent in chemical analysis.

The Diethylamine-copper method is an absorption spectrophotometric method for quantitative analysis of substance concentrations.

Other applications include materials for electroplating baths, polymerization retardants (or polymerization inhibitors) added to monomers to prevent autopolymerization, and pH adjusters.

Properties of Diethylamine

1. Physical Properties

Diethylamine is an organic compound with chemical formula C4H11N, molecular weight 73.14, and CAS number 109-89-7. It is a colorless liquid with a characteristic ammonia-like odor. Its pH is strongly basic, viscosity is 0.319 cp (25°C), and specific gravity is 0.707.

It is a flammable liquid with a melting point of -50°C, a flash point of -26°C or less (in closed systems), a boiling point, first distillation point, and boiling range of 55.5°C, a lower explosive limit of 1.8 vol% and an upper explosive limit of 10.1 vol%, and a spontaneous combustion temperature of 312°C.

2. Chemical Properties

Diethylamine is miscible with water and soluble in alcohol, carbon tetrachloride, and chloroform. It is stable under normal conditions, but decomposes upon heating or combustion, producing toxic fumes such as carbon monoxide and nitrogen oxides.

Oxidizing agents and nitrocyanofurazan are listed as hazardous intermediates. When reacting with oxidizers, there is a risk of fire and explosion. Contact with nitrocyanofurazan will cause an immediate explosion, so care must be taken when handling to avoid contact with other incompatible hazardous substances.

Other Information on Diethylamine

1. Safety of Diethylamine

Diethylamine generates highly flammable liquid and vapor, which is harmful by skin contact, inhalation, and ingestion. It can also cause serious eye damage. Single exposure may cause respiratory and liver damage. Repeated exposure may further cause kidney damage.  It is hazardous to aquatic organisms.

When disposing of the product, it must be treated in accordance with relevant laws and local government standards. 

2.First Aid Measures for Diethylamine

If inhaled, contacted with skin or eyes, or ingested orally, contact a medical institution immediately. If inhaled, rest in a semi-recumbent position in a location with fresh air.

If on skin, it is important to rinse with plenty of water for at least 15 minutes, then remove clothing that is stained with the chemical, and further rinse.

If the chemical irritates your eyes, flush with plenty of water and remove contact lenses if possible. If ingested orally, do not force vomiting, rinse out the mouth, and follow medical advice. 

3. Handling Diethylamine

When handling diethylamine, wear appropriate respiratory protection, protective gloves (neoprene recommended), face protection, and full-body chemical protective clothing (e.g., acid-resistant suit) if necessary. Wash hands thoroughly after work and avoid contact with eyes and skin.

It is required to use explosion-proof electrical, ventilation, and lighting equipment, and take precautions against static discharge. It is highly recommended to install eye washers and safety showers in storage and handling areas.

When mist is generated in high heat processes, ventilation equipment should be installed to keep air contaminants below controlled and allowable concentrations. 

4. Fire Extinguishing Methods for Diethylamine

Fires should be extinguished using powder extinguishing agents, alcohol-resistant foam extinguishing agents, large amounts of water, and carbon dioxide. To prevent fire, naked flames, contact with sparks should be avoided, and the the area work area should be a no-smoking zone.

Also, the work area should be handled in a closed system or in a place with ventilation facilities. Care should be taken not to use compressed air when filling, unloading, and handling.

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Diethyl Ether

What Is Diethyl Ether?

Diethyl Ether is a compound consisting of two ethyl groups joined by oxygen. It is sometimes called ethyl ether or simply ether. In its IUPAC name, it is also called ethoxyethane.

Diethyl Ether is a light, volatile liquid with a specific odor. It is gradually oxidized in air to form dangerous peroxides. It has an extremely low flash point, so care must be taken when handling it.

Uses of Diethyl Ether

Diethyl Ether is used as an analytical reagent, a raw material for organic synthesis, an organic solvent for resins, rubber, fats, oils, and fragrances, and as a fuel. It has a low boiling point among organic solvents, so it can be easily removed from reaction systems when used in organic synthesis.

Diethyl Ether is also used in many other pharmaceutical applications, primarily in inhalation anesthetics. It is also used in the extraction separation of certain metal chlorides from hydrochloric acid solutions.

Diethyl Ether has a low flash point of 160°C. It has a high cetane number of 85-96 and can be used as a combustion aid in diesel engines.

Properties of Diethyl Ether

Diethyl Ether has a melting point of -116.3°C and a boiling point of 34.6°C. It is extremely soluble in ethanol, benzene, and chloroform, and somewhat soluble in water.

Diethyl Ether is oxidized by atmospheric oxygen and direct sunlight to form the explosive peroxide diethyl ether peroxides. Therefore, a small amount of dibutyl hydroxytoluene (BHT) may be added as an antioxidant.

Diethyl Ether is an organic compound with a molecular structure consisting of two ethyl groups connected by an ether bond. The specific formula is CH3CH2OCH2CH3 or (CH3CH2)2O. It has a molecular weight of 74.12 and a density of 0.708 g/cm3.

Other Information on Diethyl Ether

1. Synthesis of Diethyl Ether

Industrially, diethyl ether is obtained as a byproduct of the synthesis of ethanol from ethene. It can also be synthesized by vapor phase dehydration of ethanol using alumina as a catalyst.

Diethyl Ether can also be synthesized by dehydration-condensation of ethanol using an acid as a catalyst. First, ethanol is mixed with a strong acid such as sulfuric acid, which dissociates to form hydronium ions. The hydronium ion protonates the oxygen atom of ethanol, giving the ethanol molecule a positive charge. The oxygen atom of the unprotonated ethanol molecule is replaced by the water molecule of the protonated ethanol molecule, and diethyl ether can be formed.

However, since the reaction is reversible, diethyl ether must be distilled from the reaction system to increase the yield of diethyl ether. In addition, if the temperature is high, ethanol will dehydrate to ethylene, so the reaction is usually carried out at 150°C or lower.

2. Metabolism of Diethyl Ether

The metabolism of diethyl ether is thought to involve cytochrome P450, a general term for oxidoreductase. Diethyl ether is O-deethylated by cytochrome P450, yielding ethanol and acetaldehyde

3. Dangers of Diethyl Ether

Diethyl Ether has been used in the past as an alternative to ethanol for drinking. However, it is several times more orally toxic than ethanol, with a minimum lethal dose in humans of 260 mg/kg.

Diethyl Ether has a flash point of -45°C and is extremely flammable. Because of its high insulating properties, it is prone to static electricity, which can cause it to ignite by spark discharge. Note that because diethyl ether has a low flash point, it can be easily ignited by hot utensils even in the absence of flames or sparks.

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Diethanolamine

What Is Diethanolamine?

Diethanolamine is an organic compound of a secondary amine and a diol. It is often abbreviated as DEA. It is also known as diolamine, 2,2′-iminodiethanol, iminodiethyl alcohol, etc.

It is a substance that should be handled with care. It is irritating to the skin, causes serious eye damage, and is harmful if swallowed. It may also cause cancer and harm fertility.

Uses of Diethanolamine

Diethanolamine is used as an ingredient in cosmetics and shampoos, detergents and industrial cleaning agents, lubricants in metal processing, paints, pesticides and insecticides, gas absorbents, and metal corrosion inhibitors. It is also widely used as a processing material for rubber, paper, and textiles.

In addition, diethanolamine can be used to remove hydrogen sulfide and carbon dioxide from natural gas. Petroleum refineries commonly use aqueous diethanolamine solutions to remove hydrogen sulfide from acidic gases.

Diethanolamine is superior to monoethanolamine, which has the same corrosion potential, because it can be used at higher concentrations. Therefore, hydrogen sulfide can be cleaned with less energy use required for purification.

Properties of Diethanolamine

Diethanolamine has a melting point of 28°C and a boiling point of 217°C. It is a colorless or light yellow liquid at room temperature. It is highly water soluble and can be removed by washing with water after reaction. Like most amines, diethanolamine is a weak base.

A diol is a compound with two hydroxy groups in its molecule. The chemical formula of diethanolamine is expressed as C4H11NO2. Its molar mass is 105.14 g/mol and density is 1.090 g/cm3.

Other Information on Diethanolamine

1. Diethanolamine Synthesis

Monoethanolamine can be produced by the reaction of an aqueous solution of ammonia with ethylene oxide. Diethanolamine and triethanolamine can also be synthesized depending on the reaction conditions. The product ratio can be changed by controlling the stoichiometric ratio of the raw materials.

In the reaction of ethylene oxide with aqueous ammonia, monoethanolamine is formed first. When monoethanolamine reacts with ethylene oxide, Diethanolamine can be formed. Diethanolamine further reacts with ethylene oxide to produce triethanolamine.

2. Reaction of Diethanolamine

Diethanolamine is used as a raw material in the synthesis of morpholine. Diethanolamides are formed from diethanolamine and fatty acids.

Diethanolamine reacts with 2-chloro-4,5-diphenyloxazole to form ditazole. Removal of water and reaction of diethanolamine with isobutyraldehyde yields oxazolidine.

3. Uses of Diethanolamine Derivatives

Diethanolamides derived from diethanolamine and fatty acids are amphiphilic. Coconut fatty acid diethanolamide and lauryldiethanolamine can be used as surfactants. They are commonly used in shampoos and other soaps as ingredients that improve the creamy texture and lather.

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Diisopropanolamine

What Is Diisopropanolamine?

Diisopropanolamine is an organic compound classified as a secondary amine.

It is a clear colorless liquid with an amine or ammonia-like odor at room temperature.

Uses of Diisopropanolamine

Diisopropanolamine is widely used as an organic synthetic raw material for pharmaceuticals, dye intermediates, rubber chemicals, herbicides, and surfactants.

As a rubber chemical, it is added as an anti-aging agent in the rubber molding process. This prevents the deterioration of rubber caused by chemical reactions induced by heat, light, and ozone.

As a herbicide, it is used as a hormone-type selective herbicide with auxin-like action. However, it is only used for herbicidal purposes in non-farming areas.

Properties of Diisopropanolamine

Diisopropylamine has the chemical formula C6H15N. It has a melting point of -61°C, boiling point of 84°C, and is a clear, colorless liquid at room temperature. It has an amine or ammonia-like odor. Its molecular weight is 101.193, density 0.722 g/mL, a base dissociation constant pKb of 3.43, and an acid dissociation constant pKa of 11.07 (in water) for conjugated acids.

It is soluble in ethanol, acetone, and other organic solvents, specifically methanol, ether, ethyl acetate, aromatic and aliphatic hydrocarbons, fatty acids, mineral oils, and solid oils. It is also soluble in water.

Types of Diisopropanolamine

Diisopropanolamine is usually sold to the public as a reagent product for research and development. Capacity types include 25mL, 100mL, 500mL, and 2.5L, with different manufacturers offering different volume standards.

They are usually treated as reagent products that can be handled at room temperature. Reagent products are not intended for use other than for research and development purposes..

Other Information on Diisopropanolamine

1. Reactivity of Diisopropanolamine

Diisopropanolamine is a stable substance under normal handling conditions, but reacts violently with oxidizing agents, posing a risk of fire or explosion. It reacts with many compounds, including organic chlorides, nitriles, and oxides.

It is corrosive to copper and zinc and their alloys, galvanized steel, and aluminum, and produces hydrogen gas. When heated or burned, it produces toxic and corrosive fumes and gases such as carbon monoxide, carbon dioxide, and nitrogen oxides

2. Synthesis of Diisopropanolamine

Diisopropanolamine can be synthesized by reductive amination of acetone. Ammonia is used as a reactant against the raw material acetone in a hydrogen gas atmosphere, and a catalyst such as copper chromite is used.

It is distilled and purified in the presence of potassium hydroxide and can be stored in an inert gas atmosphere in the presence of sodium.

3. Preparation of Lithium Diisopropylamide (LDA)

One of the most important organic synthetic applications of diisopropanolamine is the preparation of lithium diisopropylamide (LDA). Lithium diisopropylamide (LDA) is a substance often used in organic synthesis as a strong base.

It has an acid dissociation constant pKa of about 34 in THF and can withdraw most acidic protons, including alcohols and carbonyl compounds.

Common methods of using LDA in reactions include:

  • In a dry ice/acetone bath (or dry ice/methanol bath at -78°C). Add 1 molar equivalent of n-butyl lithium (e.g., hexane solution) to diisopropanolamine in a tetrahydrofuran (THF) solution
  • Warm the reaction mixture to 0°C over 15 minutes to prepare the LDA solution in situ.
  • Use in subsequent reactions
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Dipentaerythritol

What Is Dipentaerythritol?

Dipentaerythritol, a polyhydric alcohol, is a solid, white, odorless substance at room temperature. It forms easily through esterification reactions with common organic acids, showcasing low hygroscopicity and air stability. Structurally, it appears as two bonded pentaerythritol molecules and is produced by reacting formaldehyde and acetaldehyde in an alkali presence, typically as a byproduct of pentaerythritol production.

Uses of Dipentaerythritol

Its applications span across creating alkyd resins for coatings, polyurethane resins for paints and adhesives, rosin esters for adhesives, synthetic lubricants, vinyl chloride plasticizers for soft PVC products, surfactants, cosmetics, cross-linking agents, and explosives. Dipentaerythritol-based products are essential in industries ranging from automotive to textiles and beyond.

Properties of Dipentaerythritol

Featuring six hydroxy groups, dipentaerythritol is hydrophilic, enabling water solubility despite its considerable molecular weight. It dissolves in water at a few grams per liter at 20°C and has a melting point between 210°C and 220°C.

Structure of Dipentaerythritol

The molecule consists of two pentaerythritol units linked together, with the chemical formula (HOCH2)3CCH2OCH2C(CH2OH)3. Its six hydroxy groups facilitate a wide range of synthetic reactions, leading to diverse derivative compounds.

Other Information on Dipentaerythritol

Cross-Linkers With Dipentaerythritol Structure

As a precursor for multifunctional cross-linkers, dipentaerythritol undergoes esterification with acrylic or methacrylic acid, producing compounds with acryloyl or methacryloyl groups. These cross-linkers enable the polymerization of monomers into highly crosslinked polymer compounds. Examples include dipentaerythritol triacrylate, tetraacrylate, pentaacrylate, and hexaacrylate, showcasing the versatility of dipentaerythritol in advanced material synthesis.

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Dicyclopentadiene

What Is Dicyclopentadiene?

Dicyclopentadiene, abbreviated as DCPD, is an organic compound with the chemical formula C10H12.

It has a molecular weight of 132.20, a melting point of 32.5°C, and a boiling point of 170°C. It is a colorless crystal or pale yellow powder at room temperature. It has a camphor-like aroma. Its density is 0.98 g/mL.

Structurally, endo and exo forms exist, but the CAS registry number for the mixture that does not distinguish between them is 77-73-6.

Dicyclopentadiene is soluble in organic solvents such as ethanol, ether, and benzene, and in acetic acid.

Uses of Dicyclopentadiene

Dicyclopentadiene’s main uses are in unsaturated polyester resins, coatings, and fragrances.

As a raw material for synthetic resins, dicyclopentadiene is used as a raw material for reaction injection molding resins and for various other resin materials such as epoxy, polyester, alkyd, and EP rubber, etc. It is called DCPD resin and is characterized by its rigidity and impact resistance. It is also used in inks, adhesives, or paints.

Dicyclopentadiene is also a useful organic synthetic compound. Cyclopentadiene, obtained by pyrolysis of dicyclopentadiene, is known as a conjugated diene that undergoes a Diels-Alder reaction with the parent diene agent.

It is also used industrially as a raw material for agrochemicals and insecticides.

Properties of Dicyclopentadiene

When dicyclopentadiene is heated above 150°C, the reverse Diels-Alder reaction yields cyclopentadiene. However, since this reaction is reversible, it slowly dimerizes back to dicyclopentadiene again at room temperature.

Hydrogenation of dicyclopentadiene also yields endo-tetrahydrodicyclopentadiene. When this compound is further heated with aluminum chloride, a rearrangement reaction occurs to form adamantane.

Types of Dicyclopentadiene

Dicyclopentadiene is commonly sold as a reagent product for research and development and as an industrial chemical. When used as a reagent product for research and development, it is mainly used as a raw material for organic synthesis, and is available in various capacities, including 25 mL, 500 mL, 100 g, 500 g, 1 kg, and 2.5 kg.

It is basically a reagent product that can be handled at room temperature. Industrial products are mainly used as a raw material for specialty resins and chemical synthesis products.

Other Information on Dicyclopentadiene

1. Production of Dicyclopentadiene

Dicyclopentadiene is a substance found in the low-boiling fractions of coal tar and in the by-products of naphtha thermal cracking. It is also co-produced in large quantities during the production of ethylene by steam cracking of naphtha and heavy oil. 

2. Dicyclopentadiene and Polymerization

Dicyclopentadiene undergoes a polymerization reaction. Homopolymers of dicyclopentadiene are produced, and copolymerization with ethylene or styrene using only the norbornene double bond has also been reported. Both reactions are carried out in the presence of a catalyst. Ring-opening metathesis polymerization also produces polydicyclopentadiene.

Dicyclopentadiene is stable under normal storage conditions, but exposure to air can cause polymerization reactions. Therefore, it is generally stored in the presence of butyl hydroxytoluene (BHT) as an antioxidant. 

3. Regulatory Information on Dicyclopentadiene

Dicyclopentadiene is known to be hazardous to human health due to its oral and dermal toxicity, skin irritation, potentially life-threatening by inhalation, eye irritation, damage to the respiratory system, liver, and kidneys, and possible drowsiness or dizziness. It is also a flammable substance with a low flash point of 26~38℃.

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p-Cymene

What Is P-Cymene?

p-Cymene is an organic compound in which two hydrogens of benzene are replaced by methyl and isopropyl groups.

Usually, p-Cymene (paracymene) has a structure in which a methyl group and an isopropyl group are substituted at the para-positions (1 and 4) of the benzene ring.

The CAS registration number is 99-87-6. However there are two positional isomers, o-cymene (CAS No. 527-84-4) and m-cymene (CAS No. 535-77-3), neither of which is found in nature.

Uses of P-Cymene

In nature, p-Cymene is found in the essential oils of shell ginger, cumin, and thyme. It is commonly used as a fragrance and is used in soaps. The substance has a citrus odor with a volatile oil smell.

p-Cymene is a useful substance as an organic synthetic raw material. It is used as a raw material for the synthesis of terephthalic acid and thymol.

Among the intermediates and building blocks that can be synthesized from p-Cymene are p-Cymene hydroperoxide, 4-methylacetophenone, 4-isopropylbenzyl alcohol, 4-isopropylbenzaldehyde, and 4-isopropylbenzoic acid. These substances are sometimes used to study oxidation reactions under various conditions.

Properties of P-Cymene

p-Cymene is an organic compound classified as a monoterpene (a 10-carbon hydrocarbon produced by plants, insects, fungi, and bacteria) and an aromatic hydrocarbon.

Its molecular formula is C10H14 and its molecular weight is 134.22. It has a melting point of -68.9°C, a boiling point of 177.10°C, and is a clear, colorless liquid at room temperature.

It has a characteristic aroma, sometimes described as citrusy, reminiscent of lemon. It is miscible with ethanol, acetone, benzene, carbon tetrachloride, and petroleum ether, but is virtually insoluble in water. It has a density of 0.857 g/mL.

Although p-Cymene is stable under normal handling conditions, it reacts with oxidizing agents and is believed to attack rubber. During storage, it is necessary to avoid mixing with these substances. p-Cymene is also used as a ligand for ruthenium. A typical example is dichloro(p-Cymene)ruthenium(II) (η6-cymene)2Ru2Cl4), which is usually sold in dimer form (CAS registration number 52462-29-0).

This complex is synthesized from ruthenium trichloride and α-ferlandrene and is used as a precursor to various ruthenium-cymene complexes. Other p-Cymene complexes of osmium are also known.

Types of P-Cymene

p-Cymene is commonly sold as an industrial raw material substance in reagent products for research and development and in fragrances. As mentioned above, p-Cymene is the most common.

p-Cymene is available as an R&D reagent product in a variety of capacities, including 25 mg, 25 mL, 500 mL, 1 kg, 8 kg, and 20 kg. Typically, these reagent products can be handled at room temperature.

Some reagent manufacturers offer o-Cymene and m-Cymene, but in small quantities of only a few hundred milligrams, and the price is also effective. As an industrial raw material, it is offered in units of 100 g, 1 kg, 25 kg, etc., and may also be customized to meet other demands.

Other Information on P-Cymene

1. P-Cymene Synthesis

p-Cymene is industrially produced by dehydrogenation of α-pinene with iodine (I2) or phosphorus trichloride (PCl3) or by the Friedel-Crafts alkylation reaction of toluene and propene.

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Citral

What Is Citral?

Citral is the name given to a mixture of a pair of isomers, the organic compounds neral and geranial. Its IUPAC nomenclature name is 3,7-dimethyl-2,6-octadienal, and it is also sometimes referred to by the alias lemonal.

Both isomers are monoterpene aldehydes with the molecular formula C10H16O and are cis-trans isomers: E is geranial and Z is neral. The CAS registration number of citral is 5392-40-5.

Uses of Citral

Citral has a lemon-like aroma, so it is used as an excipient in cosmetics and foods, as well as in various products such as perfumes, cosmetics, facial cleansers, body soaps, shampoos, detergents, and foods.

In natural products, it is a substance present in essential oils of lemongrass, lemon, mandarin, and various other fruits and spices. Because of its high volatility and strong aroma, it is used in top notes, which are the first to be perceived in fragrance formulations.

It is also used as a raw material for the production of other flavors and fragrances.

Citral is also a useful compound as a raw material for general organic synthesis. It is used as a raw material for synthesizing chemicals such as vitamin A and vitamin E

Properties of Citral

Citral is a mixture of geranial and neral. It has a molecular weight of 152.24, a melting point below -10°C, and a boiling point of 229°C. It is a colorless to pale yellow liquid at room temperature. It is susceptible to oxidation and gradually takes on a yellowish color upon exposure to air. It has a density of 0.893 g/mL

Citral is easily soluble in ethanol and ether, but insoluble in water. It has a characteristic aroma, of which geranial has a cool, strong lemon odor, while neral has a weak lemon odor and sweet taste.

Types of Citral

Citral is generally sold as a reagent product for research and development and as a raw material for fragrances. As a reagent product for research and development, it is available in various capacities, such as 1mg, 5mg, 5mL, 100mL, 500mL, 25g, 1kg, etc., depending on the manufacturer.

Reagent products may be treated as refrigerated reagents or as reagents that can be handled at room temperature.

Note that reagent products can only be used for research and development purposes, not for medical, clinical diagnostic, or food use in humans or animals.

Industrial products are sold by several companies, including fragrance and chemical manufacturers.

Sales are developed in a variety of packing sizes ranging from 1L bottles to ultra-large capacities such as 25L drums, 180kg drums, and 200L drums. The product offerings are tailored to factories and other manufacturing sites.

Other Information on Citral

1. Production and Synthesis of Citral

Citral is contained in various essential oils, so it can be produced by separation from essential oils. It can also be produced synthetically, sometimes using methyl heptenone as a raw material.

The following synthetic route is an example of synthesis:

  • Condensation reaction of methyl heptenone with ethoxyacetylene magnesium bromide
  • Catalytic partial hydrogenation (formation of enol ethers)
  • Hydrolysis and dehydration with phosphoric acid

One other synthetic example is via the dehydrolinalool intermediate produced by the condensation reaction of acetylene with methyl heptenone. This intermediate is rearranged at 140-150°C in the presence of a silicon sulfone catalyst in an inert solvent to give citral.

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Cyclohexylamine

What Is Cyclohexylamine?

Cyclohexylamine is an organic compound classified as an aliphatic amine. Other names include aminocyclohexane, aminohexahydrobenzene, and hexahydroaniline.

Its CAS registration number is 108-91-8 and its chemical formula is C6H13N. One hydrogen on cyclohexane is replaced by an amino group.

Uses of Cyclohexylamine

The main uses of cyclohexylamine are as a can cleaner, rust inhibitor, pigment and dye, rubber chemicals, dyeing aid, insecticide, and antifreeze solution. In particular, it is used as a flushing aid in the printing ink industry.

Cyclohexylamine is also used as an intermediate raw material for various compounds such as pharmaceuticals, since it is a useful substance in organic synthetic chemistry.

Major substances synthesized from cyclohexylamine include sulfenamide vulcanization accelerators, the herbicide hexazinone, grease, and the artificial sweetener cyclohexylamine.

In pharmaceuticals, it is often used as a raw material for drugs such as mucolytics, analgesics, and bronchodilators.

Properties of Cyclohexylamine

Cyclohexylamine has a molecular weight of 99.17, a melting point of -17.7 °C, and a boiling point of 134.5 °C. It is a colorless to yellow liquid at room temperature. It has a strong fish or ammonia-like odor.

It has a density of 0.8627 g/mL and an acid dissociation constant pKa of 10.64. It is soluble in alcohols, ethers, ketones, esters, aliphatic hydrocarbons, and aromatic hydrocarbons (common organic solvents).

Types of Cyclohexylamine

Cyclohexylamine is sold as R&D reagent products and industrial chemicals. R&D reagent products are available in 25mL, 500mL, and other volumes that are easy to handle in the laboratory.

Often used as raw material for organic synthesis, these reagent products can usually be handled at room temperature.

As industrial chemicals, it is supplied in 15 kg cans or drums of around 170 kg.

It is used in rubber chemicals, dyes, pigments, rust inhibitors, and antifreeze solutions, and is available in large capacities to meet the demands of factories and other applications.

Other Information on Cyclohexylamine

1. Synthesis of Cyclohexylamine

The main methods for synthesizing cyclohexylamine include hydrogenation of aniline with nickel or cobalt and alkylation of cyclohexanol with ammonia.

2. Reactivity of Cyclohexylamine

Cyclohexylamine is a strong base and reacts violently with acids. It decomposes by heating or combustion, producing toxic and corrosive fumes such as nitrogen oxides.

These substances react violently with strong oxidizers, posing a fire hazard, and they attack aluminum, copper, and zinc. When storing the product, it is necessary to avoid mixing with these substances. 

3. Safety Information for Cyclohexylamine

Cyclohexylamine is toxic by ingestion, skin contact, and inhalation. It is a flammable liquid with a low flash point of 26.5 ºC, and at temperatures above 26.5 ºC, an explosive vapor mixture may be generated.

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Cyclohexane

What Is Cyclohexane?

Cyclohexane_シクロヘキサン-1.

Figure 1. Basic information on cyclohexane

Cyclohexane is a type of cycloalkane formed by hydrogenation of benzene, etc. It is widely used as a solvent. It is also called hexamethylene or hexahydrobenzene.

Cyclohexane is a colorless liquid with an odor similar to gasoline. It has a molecular formula of C6H12, a molecular weight of 84.16, a boiling point of 80.74°C, and a density of 0.779 g/mL.

Cyclohexane exists in stereoisomers called chair, boat, half chair, and twisted boat forms, with the chair form being the most stable.

Uses of Cyclohexane

Cyclohexane is used as a raw material for caprolactam and adipic acid, which are synthetic intermediates of nylon, and is most commonly used in the manufacture of nylon.

Other uses include solvents for paints, ethers, waxes, and rubbers, oil and fat extraction, paint and varnish removers, solvent adhesives, and aerosol adhesives. As a solvent, it can be widely used for synthesis, cleaning, and other applications, as well as for analytical purposes, such as eluents for liquid chromatography analysis.

Properties of Cyclohexane

Cyclohexane is insoluble in polar solvents and soluble in organic solvents. It is highly volatile and extremely flammable.

Because of its anesthetic properties, it must be handled with care. For example, prolonged contact of cyclohexane with the skin, for example, can cause illnesses such as dermatitis. When inhaled, low concentrations can cause headaches, and high concentrations can cause disorientation. Particular attention should be paid to low concentrations, as it has almost no odor.

Structure of Cyclohexane

Cyclohexane_シクロヘキサン-2.

Figure 2. Conformation of cyclohexane

The most stable conformation of cyclohexane is chair-shaped, followed by twisted boat-shaped, boat-shaped, and semi-chair-shaped.

In the case of cyclohexane rings with substituents, other conformations may be more stable due to steric hindrance caused by the bulkiness of the substituents.

Other Information on Cyclohexane

1. Synthesis of Cyclohexane

Industrially, the majority of cyclohexane is produced by catalytic hydrogenation of benzene using palladium or nickel catalysts. Methylcyclopentane, produced in the process of petroleum reforming, can also be converted to cyclohexane using a catalyst.

Industrially obtained cyclohexane is converted to cyclohexanol and cyclohexanone, which are eventually converted to ε-caprolactam, hexamethylenediamine, and adipic acid. These compounds can be used as raw materials for 6-nylon and 6,6-nylon.

2. Ring inversion of Cyclohexane

Cyclohexane_シクロヘキサン-3.

Figure 3. Ring inversion of cyclohexane

In the chair conformation of cyclohexane and other cyclic compounds with a cyclohexane-type structure, a distinction is made between substituents parallel and perpendicular to the ring plane. Substituents parallel to the ring plane are called equatorial, and those perpendicular to the ring plane are called axial.

Because of free rotation at each of the bonding axes that form the ring, cyclohexane goes through a fuselage conformation and the two chair-shaped conformations swap places with each other. This is called ring inversion. Through ring inversion, it is possible for an equatorial to change to an axial orientation and an axial to an equatorial orientation. 

3. Cyclohexane Ring With Bulky Substituents

The distance between substituents is closer in the axial form than in the equatorial form. In the case of cyclohexane rings with bulky substituents, it is also known that the substituents avoid the axial form and predominantly take the equatorial form, since this affects the stability of the stereo conformation.