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108-93-0
futurechemical
108-93-0
Cyclohexanol is a secondary alcohol with the formula C6H12O and the structure (CH2)5CHOH and is obtained by replacing one atom of hydrogen in cyclohexane with a hydroxyl group. It is a thick transparent liquid. This is the backbone of the nylon industry. Millions of tons of cyclohexanol are oxidized to adipic acid and dehydrogenated to cyclohexanone every year, and then become the nylon 66 and nylon 6 fibers we wear, the adipic acid in engineering plastics, and the plasticizer in flexible PVC.
[Industry chain overview] Cyclohexane is oxidized by air in industry (cobalt catalysis) to obtain cyclohexanol and cyclohexanone at the same time, which is called KA oil (ketol oil). It is the main raw material for the production of adipic acid. Cyclohexanol can also be produced by hydrogenation of phenol. These are two major nylon industrial chains, i.e., “cyclohexane → cyclohexanol/cyclohexanone (KA oil) → adipic acid → nylon 66” and “cyclohexanol → cyclohexanone → caprolactam → nylon 6”. Cyclohexanol is a core position in the industrial chain and links the upstream and downstream processes.
Basic Information Molecular Formula C6H12O Molecular Weight 100.16 CAS Number 108-93-0 EC Number 203-630-6 In addition to the nylon industry chain, it is used in plasticizers, solvents, synthesis of organic compounds, and fragrance intermediates.
It is a colorless viscous liquid (melting point of the high-purity product is at 25.93 degreeC, and it may crystallize in a waxy manner at room temperature), with a camphor-like odor, and is hygroscopic; density is 0.9624 g/mL; boiling point is at 161.84 degreeC; slightly soluble in water (approximately 3.6 g/100 mL at 20 degreeC), readily soluble in organic solvents such as ethanol, ether, acetone, chloroform, and ethyl acetate; refractive index is 1.4641; flash point is at 67 degreeC, and autoignition temperature is at 300 degreeC.
Cyclohexanol is a typical secondary alcohol. It can be catalytically dehydrogenated or oxidized to cyclohexanone (oxidative cleavage can further yield adipic acid); it can be esterified with acids or anhydrides to form esters (such as dicyclohexyl phthalate and cyclohexyl acetate); it can be dehydrated under acid catalysis to form cyclohexene; it can dissolve resins, oils and waxes as a moderately polar alcohol solvent. Must be kept away from oxidizers, sources of ignition, sealed to protect from moisture
Its downstream esters, e.g., cyclohexyl acetate, are flavoring raw materials permitted for use in food flavorings (FEMA GRAS). Cyclohexanol itself is not a food additive.
From the point of view of its mechanism of action, cyclohexanol has an irreplaceable part due to its “four types of reactivity: oxidation/dehydrogenation/esterification/dehydration of secondary alcohol hydroxyl groups + moderate polarity and solubility”. The mechanisms of action in the various applications are:
Cyclohexanol (KA oil which consists of cyclohexanone) is oxidized by nitric acid or air and the secondary alcohol hydroxyl group is oxidized to ketone. Further oxidation and cleavage of the cyclic structure leads to adipic acid (nylon 66 monomer), which is the core reaction of the nylon industry chain.
The mechanism of cyclohexanone by dehydrogenation
The nylon 6 industrial chain is formed via the dehydrogenation of cyclohexanol over catalysts such as copper and zinc (or the oxidation of cyclohexane) to produce cyclohexanone, which is subsequently converted into cyclohexanone oxime and rearranged into caprolactam (nylon 6 monomer).
Macromolecular esters (dicyclohexyl phthalate, dicyclohexyl adipate) are obtained by the reaction of cyclohexanol with phthalic anhydride, adipic acid, etc. These esters are introduced into the polymer molecular chains, weakening the intermolecular forces and lowering the glass transition temperature, which softens rigid resins. It is a plasticizer for plastics like PVC.
Cyclohexanol is a moderately polar alcohol solvent because the polarity of the hydroxyl group is combined with the lipophilic skeleton of the cyclohexyl group. It dissolves alkyd resins, nitrocellulose, shellac, oils and waxes and is used in coatings and paint formulations.
Cyclohexanol is eliminated and dehydrated under acid catalysis to give cyclohexene (elimination reaction). Cyclohexene is an important intermediate for organic production, which can be further converted into a variety of fine chemicals.
Cyclohexanol is the "basket of the nylon industry". It is used in adipic acid, cyclohexanone, plasticizers and solvents, and runs through the core links of nylon fibers, engineering plastics and fine chemicals due to the oxidative, dehydrogenative, esterification and dehydration reactivity of secondary alcohol hydroxyl groups.
Application areas： Nylon 66, polymer industry.
Related Products: are adipic acid, nylon 66 fiber, nylon 66 engineering plastics, tire cord, automotive airbag fabric, carpet fiber, adipate ester plasticizer, polyurethane raw material, and adipic acidulant for food, etc.
Why it works for this type of application: Cyclohexanol (KA oil, made of cyclohexanone) is opened by oxidation with nitric acid or air to give adipic acid. Then adipic acid is condensed with hexamethylenediamine to get Nylon 66, which is the core raw material of the global Nylon 66 industry chain, and also determines the supply of engineering plastics and high-performance fibers.
Application areas：Nylon 6, solvent industry.
Related Products:Cyclohexanone, caprolactam, nylon 6 fiber, nylon 6 engineering plastics, cyclohexanone oxime, adipic acid co-production raw material, cyclohexanone industrial solvent, cleaning agents, etc.
Why it works for this purpose: Cyclohexanol is dehydrogenated to cyclohexanone which reacts with hydroxylamine to form an oxime which undergoes Beckmann rearrangement to form caprolactam. Caprolactam is polymerized by ring-opening to give nylon 6, a key intermediate in the value chain of nylon 6 fiber and engineering plastics.
Application areas: Plastic additives, PVC processing.
Related Products: Dicyclohexyl phthalate (DCHP), dicyclohexyl adipate, cyclohexyl fatty acid esters, polyvinyl chloride (PVC) flexible products, cellulose plasticizers, coating plasticizers, sealant plasticizers, etc.
Why it works for this purpose:Cyclohexanol esterifies with phthalic anhydride, adipic acid, etc. to produce macromolecular ester plasticizers. The esters are incorporated into the polymer molecular chains, which weaken the intermolecular forces and increase flexibility and processability. These are important types of plasticizer for flexible PVC products.
Application areas: Manufacturing of paints and coatings.
Related Products: Alkyd resin paint solvent, varnish and shellac solvent, nitrocellulose lacquer thinner, wood coating, paint remover, ink solvent, resin solvent, leather finishing agent, etc.
Why it works for this purpose: Cyclohexanol is a medium-polarity alcohol solvent that dissolves alkyd resins, nitrocellulose and shellac. It has moderate evaporation rate, improves film leveling and gloss and is a common solvent in coatings and paint remover formulations.
Application areas：Chemical intermediates, organic.
Related Products:cyclohexene, cyclohexanol derivative intermediates, adipaldehyde, cyclohexyl compounds, organic production intermediates, pesticide intermediates, etc.
Why it works for this purpose:Under acid catalysis cyclohexanol is dehydrated and eliminated to yield cyclohexene. Cyclohexene has a double bond, which can be subject to addition, oxidation and hydration reactions and as such is a useful intermediate in the synthesis of many fine chemicals.
Application areas： Fine chemicals and synthesis.
Related Products:Solvents of organic production reactions, solvents of extractions, media of recrystallizations, solvents of cleaning, carrying liquids of chemical reactions, media of polymerization reactions etc.
Why it works for this purpose:Cyclohexanol is a chemical with mild reactivity, a moderate boiling point (161.8℃) and wide solubility range. It is a reaction medium for a variety of organic reactions, and can also be used as an extraction and crystallization solvent and a commonly used alcohol solvent in fine chemicals.
Application areas： Flavor and Fragrance Industry.
Related Products: Cyclohexyl acetate (fruit flavor); cyclohexanol esters; food flavors (banana, apple, etc.); everyday fragrances; cosmetic fragrances; soap fragrances, etc.
Why it works for this purpose:Cyclohexanol reacts with acetic acid to produce cyclohexyl acetate and other esters with a sweet, fruity scent. It is a flavoring ingredient used in the preparation of fruit flavors in food and daily chemical products, and has a fresh and stable fragrance (cyclohexyl acetate is a flavoring ingredient approved for use in food flavors; cyclohexanol itself is not a food additive).
Application areas： scientific research laboratories and analytical chemistry.
Related products:analytical grade cyclohexanol, chromatographic analysis solvents, extraction reagents, solvents for the preparation of standard solutions, laboratory cleaning solvents, teaching reagents, etc.
Why it works for this purpose: Reagent-grade cyclohexanol is of high purity and good solubility. It is suitable as analytical solvent, extraction agent and preparation solvent, to ensure the accuracy of experiments and detections.
To summarize, cyclohexanol (CAS 108-93-0) is the "basket of the nylon industry. Its reactive properties in the oxidation, dehydrogenation, esterification and dehydration of secondary alcohol hydroxyl groups have applications in eight major sectors including adipic acid (nylon 66), cyclohexanone and caprolactam (nylon 6), plasticizers and esters, coating solvents, cyclohexene intermediates, organic production media, ester fragrances and analytical reagents. The industrial chains of adipic acid and cyclohexanone are the largest consumers of nylon, which is beneficial for nylon fibers, engineering plastics, and flexible PVC in everyday products. Note Cyclohexanol is moderately toxic (50 ppm in air), flammable (flash point 67 °C) and reacts violently with strong oxidizers. During handling strict measures for ventilation and fire prevention are required.
