All Topics  
Cyclohexanol

 

 
   Email Print
   Bookmark   Link
 

 

Cyclohexanol
 
 
  Topics Cyclohexanol Topic Home

Cyclohexanol is the organic compound
Organic compound

An organic compound is any member of a large class of chemical compounds whose molecules contain carbon. For historical reasons discussed below, a few types of compounds such as carbonates, simple oxides of carbon and cyanides, as well as the allotropes of carbon, are considered Inorganic compound....
 with the formula
Chemical formula

A chemical formula is a way of expressing information about the atoms that constitute a particular chemical compound, and how the relationship between those atoms changes in chemical reactions....
 (C
Carbon

Carbon is a chemical element with chemical symbol C and atomic number 6. As a member of group 14 on the periodic table, it is nonmetallic and tetravalence?making four electrons available to form covalent bond chemical bonds....
H
Hydrogen

Hydrogen is the chemical element with atomic number 1. It is represented by the chemical symbol H. At standard temperature and pressure, hydrogen is a colorless, odorless, nonmetallic, tasteless, highly combustion and explosive Diatomic molecule gas with the molecular formula H2....
2)5CHOH. The molecule is related to cyclohexane
Cyclohexane

Cyclohexane is a cycloalkane with the molecular formula Carbon6Hydrogen12. Cyclohexane is used as a nonpolar solvent for the chemical industry, and also as a raw material for the industrial production of adipic acid and caprolactam, both of which are intermediates used in the production of nylon....
 ring by replacement of one hydrogen atom by a hydroxyl group
Hydroxide

In chemistry, hydroxide is the name for the Diatomic molecule anion OH-, consisting of oxygen and hydrogen atoms, usually derived from the Dissociation of a base ....
. This compound exists deliquescent colorless solid, which, when very pure, melts near room temperature. Billions of kilograms are produced annually, mainly as a precursor to nylon
Nylon

Nylon is a generic designation for a family of synthetic polymers known generically as polyamides and first produced on February 28, 1935 by Wallace Carothers at DuPont....
.

ohexanol is produced by the oxidation of cyclohexane
Cyclohexane

Cyclohexane is a cycloalkane with the molecular formula Carbon6Hydrogen12. Cyclohexane is used as a nonpolar solvent for the chemical industry, and also as a raw material for the industrial production of adipic acid and caprolactam, both of which are intermediates used in the production of nylon....
 in air, typically using cobalt catalysts:
C6H12 + 1/2 O2 ? C6H11OH
This process co-forms cyclohexanone
Cyclohexanone

Cyclohexanone is the organic compound with the chemical formula...
, and this mixture ("KA oil" for ketone-alcohol oil) is the main feedstock for the production of adipic acid
Adipic acid

Adipic acid is the organic compound with the chemical formula 42. From the industrial perspective, it is the most important dicarboxylic acid: About 2.5 billion kilograms of this white crystalline powder are produced annually, mainly as a precursor for the production of nylon....
.






Discussion
Ask a question about 'Cyclohexanol'
Start a new discussion about 'Cyclohexanol'
Answer questions from other users
Full Discussion Forum



Encyclopedia


Cyclohexanol is the organic compound
Organic compound

An organic compound is any member of a large class of chemical compounds whose molecules contain carbon. For historical reasons discussed below, a few types of compounds such as carbonates, simple oxides of carbon and cyanides, as well as the allotropes of carbon, are considered Inorganic compound....
 with the formula
Chemical formula

A chemical formula is a way of expressing information about the atoms that constitute a particular chemical compound, and how the relationship between those atoms changes in chemical reactions....
 (C
Carbon

Carbon is a chemical element with chemical symbol C and atomic number 6. As a member of group 14 on the periodic table, it is nonmetallic and tetravalence?making four electrons available to form covalent bond chemical bonds....
H
Hydrogen

Hydrogen is the chemical element with atomic number 1. It is represented by the chemical symbol H. At standard temperature and pressure, hydrogen is a colorless, odorless, nonmetallic, tasteless, highly combustion and explosive Diatomic molecule gas with the molecular formula H2....
2)5CHOH. The molecule is related to cyclohexane
Cyclohexane

Cyclohexane is a cycloalkane with the molecular formula Carbon6Hydrogen12. Cyclohexane is used as a nonpolar solvent for the chemical industry, and also as a raw material for the industrial production of adipic acid and caprolactam, both of which are intermediates used in the production of nylon....
 ring by replacement of one hydrogen atom by a hydroxyl group
Hydroxide

In chemistry, hydroxide is the name for the Diatomic molecule anion OH-, consisting of oxygen and hydrogen atoms, usually derived from the Dissociation of a base ....
. This compound exists deliquescent colorless solid, which, when very pure, melts near room temperature. Billions of kilograms are produced annually, mainly as a precursor to nylon
Nylon

Nylon is a generic designation for a family of synthetic polymers known generically as polyamides and first produced on February 28, 1935 by Wallace Carothers at DuPont....
.

Production

Cyclohexanol is produced by the oxidation of cyclohexane
Cyclohexane

Cyclohexane is a cycloalkane with the molecular formula Carbon6Hydrogen12. Cyclohexane is used as a nonpolar solvent for the chemical industry, and also as a raw material for the industrial production of adipic acid and caprolactam, both of which are intermediates used in the production of nylon....
 in air, typically using cobalt catalysts:
C6H12 + 1/2 O2 ? C6H11OH
This process co-forms cyclohexanone
Cyclohexanone

Cyclohexanone is the organic compound with the chemical formula...
, and this mixture ("KA oil" for ketone-alcohol oil) is the main feedstock for the production of adipic acid
Adipic acid

Adipic acid is the organic compound with the chemical formula 42. From the industrial perspective, it is the most important dicarboxylic acid: About 2.5 billion kilograms of this white crystalline powder are produced annually, mainly as a precursor for the production of nylon....
. The oxidation involves radicals and the intermediacy of the hydroperoxide C6H11O2H. Alternatively, cyclohexanol can be produced by the hydrogenation
Hydrogenation

Hydrogenation is the chemical reaction that results from the addition of hydrogen . The process is usually employed to a redox or Saturation organic compounds....
 of phenol
Phenol

Phenol, also known as carbolic acid, is a toxic, white crystalline solid with a sweet tarry odor, commonly referred to as a "hospital smell"....
:
C6H5OH + 3 H2 ? C6H11OH
This process can also be adjusted to favor the formation of cyclohexanone.

Basic reactions

Cyclohexanol undergoes the main reactions expected for a secondary alcohol. Oxidation gives gives cyclohexanone
Cyclohexanone

Cyclohexanone is the organic compound with the chemical formula...
, which is converted on a large scale in industry to the oxime
Oxime

An oxime is one in a class of chemical compounds with the general formula R1R2carbonnitrogenoxygenhydrogen, where R1 is an organic compound side chain and R2 is either hydrogen, forming an aldoxime, or another organic group, forming a ketoxime....
, a precursor to caprolactam
Caprolactam

Caprolactam is an organic compound which is a lactam of 6-aminohexanoic acid . It can alternatively be considered cyclic amide of caproic acid....
. As a laboratory exercise, this oxidation can be effected with chromic acid
Chromic acid

Chromic acid generally refers to a collection of chemical compound generated by the acidification of solutions containing chromate and dichromate ion or the dissolving of chromium trioxide in sulfuric acid....
. Esterification
Esterification

Esterification is the general name for a chemical reaction in which two reactants form an ester as the product . Esters are common in organic chemistry and biological materials, and often have a characteristic pleasant, fruity odor....
 affords the commercially useful derivatives dicyclohexyladipate and dicyclohexylphthalate, which are used as plasticizer
Plasticizer

Plasticizers or Dispersants are additives that increase the plasticity or fluidity of the material to which they are added, these include plastics, cement, concrete, wallboard and clay bodies....
s. Heating in the presence of acid catalysts converts cyclohexanol to cyclohexene
Cyclohexene

Cyclohexene is a colorless clear liquid cycloalkene with an intense aversive characteristic sharp smell reminiscent of an oil refinery.It is not very stable upon long term storage with exposure to light and air and should be distilled before use to eliminate organic peroxide....
.

Applications

As indicated above, cyclohexanol is an important feedstock in the polymer industry, firstly as a precursor to Nylons, but also to various plasticizers. Small amounts are used as a solvent.

Safety

Cyclohexanol is somewhat toxic: the TLV
Threshold Limit Value

The Threshold Limit Value of a chemical substance is a level to which it is believed a worker can be exposed day after day for a working lifetime without adverse health effects....
 for the vapor for 8 h is 50 ppm
PPM

PPM may refer to:* In music:** Please Please Me, the first album by The Beatles.**Peter, Paul, and Mary , a 1960's folk music trio.* In computing:...
. Few studies have been done on its carcinogenicity, but one study on rats found it to have co-carcinogenic effects.