1-Tridecanol

Last updated
1-Tridecanol
Tridecanol.svg
Names
Preferred IUPAC name
Tridecan-1-ol
Other names
1-Tridecanol
Tridecyl alcohol
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.003.635 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
  • InChI=1S/C13H28O/c1-2-3-4-5-6-7-8-9-10-11-12-13/h13H,2-13H2,1H3 X mark.svgN
    Key: needed X mark.svgN
  • InChI=1/C13H28O/c1-2-3-4-5-6-7-8-9-10-11-12-13/h13H,2-13H2,1H3
    Key: needed
  • CCCCCCCCCCCCCO
Properties
C13H28O
Molar mass 200.366 g·mol−1
AppearanceWhite solid [1]
Density 0.84 g/cm3 [1]
Melting point 32 °C (90 °F; 305 K) [1]
Boiling point 274–280 °C (525–536 °F; 547–553 K) [1]
Practically insoluble in water [1]
Hazards
GHS labelling:
GHS-pictogram-exclam.svg
H315, H319, H335
P261, P264, P271, P280, P302+P352, P304+P340+P312, P305+P351+P338, P332+P313, P337+P313, P362, P403+P233, P405, P501
NFPA 704 (fire diamond)
NFPA 704.svgHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
2
1
0
Flash point 120 °C
260 °C
Lethal dose or concentration (LD, LC):
17200 mg/kg (rat, oral) [1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

1-Tridecanol is an alcohol with the formula C13H28OH. It is a colorless fatty alcohol that turns white when solid. 1-Tridecanol usually occurs as a mixture of different isomeric to compounds such as 2-tridecanol, 3-tridecanol, 4-tridecanol, 5-tridecanol, 6-tridecanol, and isotridecanol.

Contents

Use

1-Tridecanol is used as a lubricant and for the manufacture of surfactants and plasticizers.

Related Research Articles

<span class="mw-page-title-main">Fatty acid</span> Carboxylic acid

In chemistry, particularly in biochemistry, a fatty acid is a carboxylic acid with an aliphatic chain, which is either saturated or unsaturated. Most naturally occurring fatty acids have an unbranched chain of an even number of carbon atoms, from 4 to 28. Fatty acids are a major component of the lipids in some species such as microalgae but in some other organisms are not found in their standalone form, but instead exist as three main classes of esters: triglycerides, phospholipids, and cholesteryl esters. In any of these forms, fatty acids are both important dietary sources of fuel for animals and important structural components for cells.

Transesterification is the process of exchanging the organic functional group R″ of an ester with the organic group R' of an alcohol. These reactions are often catalyzed by the addition of an acid or base catalyst. Strong acids catalyze the reaction by donating a proton to the carbonyl group, thus making it a more potent electrophile. Bases catalyze the reaction by removing a proton from the alcohol, thus making it more nucleophilic. The reaction can also be accomplished with the help of other enzymes, particularly lipases.

<span class="mw-page-title-main">Alcoholic liver disease</span> Medical condition

Alcoholic liver disease (ALD), also called alcohol-related liver disease (ARLD), is a term that encompasses the liver manifestations of alcohol overconsumption, including fatty liver, alcoholic hepatitis, and chronic hepatitis with liver fibrosis or cirrhosis.

<span class="mw-page-title-main">Ketoacidosis</span> Medical condition

Ketoacidosis is a metabolic state caused by uncontrolled production of ketone bodies that cause a metabolic acidosis. While ketosis refers to any elevation of blood ketones, ketoacidosis is a specific pathologic condition that results in changes in blood pH and requires medical attention. The most common cause of ketoacidosis is diabetic ketoacidosis but can also be caused by alcohol, medications, toxins, and rarely, starvation.

Biodiesel production is the process of producing the biofuel, biodiesel, through the chemical reactions of transesterification and esterification. This involves vegetable or animal fats and oils being reacted with short-chain alcohols. The alcohols used should be of low molecular weight. Ethanol is the most used because of its low cost, however, greater conversions into biodiesel can be reached using methanol. Although the transesterification reaction can be catalyzed by either acids or bases, the base-catalyzed reaction is more common. This path has lower reaction times and catalyst cost than those acid catalysis. However, alkaline catalysis has the disadvantage of high sensitivity to both water and free fatty acids present in the oils. August 10 is international biodiesel day

<span class="mw-page-title-main">Fatty liver disease</span> Medical condition related to obesity

Fatty liver disease (FLD), also known as hepatic steatosis and steatotic liver disease (SLD), is a condition where excess fat builds up in the liver. Often there are no or few symptoms. Occasionally there may be tiredness or pain in the upper right side of the abdomen. Complications may include cirrhosis, liver cancer, and esophageal varices.

<span class="mw-page-title-main">Oleyl alcohol</span> Chemical compound

Oleyl alcohol, or cis-9-octadecen-1-ol, is an unsaturated fatty alcohol with the molecular formula C18H36O or the condensed structural formula CH3(CH2)7−CH=CH−(CH2)8OH. It is a colorless oil, mainly used in cosmetics.

Fatty alcohols (or long-chain alcohols) are usually high-molecular-weight, straight-chain primary alcohols, but can also range from as few as 4–6 carbons to as many as 22–26, derived from natural fats and oils. The precise chain length varies with the source. Some commercially important fatty alcohols are lauryl, stearyl, and oleyl alcohols. They are colourless oily liquids (for smaller carbon numbers) or waxy solids, although impure samples may appear yellow. Fatty alcohols usually have an even number of carbon atoms and a single alcohol group (–OH) attached to the terminal carbon. Some are unsaturated and some are branched. They are widely used in industry. As with fatty acids, they are often referred to generically by the number of carbon atoms in the molecule, such as "a C12 alcohol", that is an alcohol having 12 carbons, for example dodecanol.

Stearyl alcohol, or 1-octadecanol, is an organic compound classified as a saturated fatty alcohol with the formula CH3(CH2)16CH2OH. It takes the form of white granules or flakes, which are insoluble in water. It has a wide range of uses as an ingredient in lubricants, resins, perfumes, and cosmetics. It is used as an emollient, emulsifier, and thickener in ointments, and is widely used as a hair coating in shampoos and hair conditioners. Stearyl heptanoate, the ester of stearyl alcohol and heptanoic acid (enanthic acid), is found in most cosmetic eyeliners. Stearyl alcohol has also found application as an evaporation suppressing monolayer when applied to the surface of water.

Dodecanol, or lauryl alcohol, is an organic compound produced industrially from palm kernel oil or coconut oil. It is a fatty alcohol. Sulfate esters of lauryl alcohol, especially sodium lauryl sulfate, are very widely used as surfactants. Sodium lauryl sulfate, ammonium lauryl sulfate, and sodium laureth sulfate are all used in shampoos. Lauryl alcohol is tasteless and colorless with a floral odor.

Lignoceric acid, or tetracosanoic acid, is the saturated fatty acid with formula C23H47COOH. It is found in wood tar, various cerebrosides, and in small amounts in most natural fats. The fatty acids of peanut oil contain small amounts of lignoceric acid. This fatty acid is also a byproduct of lignin production.

1-Tetradecanol, or commonly myristyl alcohol (from Myristica fragrans – the nutmeg plant), is a straight-chain saturated fatty alcohol, with the molecular formula CH3(CH2)12CH2OH. It is a white waxy solid that is practically insoluble in water, soluble in diethyl ether, and slightly soluble in ethanol.

<span class="mw-page-title-main">1-Decanol</span> Chemical compound

1-Decanol is a straight chain fatty alcohol with ten carbon atoms and the molecular formula C10H21OH. It is a colorless to light yellow viscous liquid that is insoluble in water and has an aromatic odor. The interfacial tension against water at 20 °C is 8.97 mN/m.

<span class="mw-page-title-main">Steatohepatitis</span> Medical condition

Steatohepatitis is a type of fatty liver disease, characterized by inflammation of the liver with concurrent fat accumulation in liver. Mere deposition of fat in the liver is termed steatosis, and together these constitute fatty liver changes.

Cetrimonium chloride, or cetyltrimethylammonium chloride (CTAC), is a topical antiseptic and surfactant. Long-chain quaternary ammonium surfactants, such as cetyltrimethylammonium chloride (CTAC), are generally combined with long-chain fatty alcohols, such as stearyl alcohols, in formulations of hair conditioners and shampoos. The cationic surfactant concentration in conditioners is generally of the order of 1–2% and the alcohol concentrations are usually equal to or greater than those of the cationic surfactants. The ternary system, surfactant/fatty alcohol/water, leads to a lamellar structure forming a percolated network giving rise to a gel.

<span class="mw-page-title-main">Cetostearyl alcohol</span> Chemical compound

Cetostearyl alcohol, cetearyl alcohol or cetylstearyl alcohol is a mixture of fatty alcohols, consisting predominantly of cetyl and stearyl alcohols and is classified as a fatty alcohol. It is used as an emulsion stabilizer, opacifying agent, and foam boosting surfactant, as well as an aqueous and nonaqueous viscosity-increasing agent. It imparts an emollient feel to the skin and can be used in water-in-oil emulsions, oil-in-water emulsions, and anhydrous formulations. It is commonly used in hair conditioners and other hair products.

A wax ester (WE) is an ester of a fatty acid and a fatty alcohol. Wax esters comprise the main components of three commercially important waxes: carnauba wax, candelilla wax, and beeswax.

Oleochemistry is the study of vegetable oils and animal oils and fats, and oleochemicals derived from these fats and oils. The resulting product can be called oleochemicals (from Latin: oleum "olive oil"). The major product of this industry is soap, approximately 8.9×106 tons of which were produced in 1990. Other major oleochemicals include fatty acids, fatty acid methyl esters, fatty alcohols and fatty amines. Glycerol is a side product of all of these processes. Intermediate chemical substances produced from these basic oleochemical substances include alcohol ethoxylates, alcohol sulfates, alcohol ether sulfates, quaternary ammonium salts, monoacylglycerols (MAG), diacylglycerols (DAG), structured triacylglycerols (TAG), sugar esters, and other oleochemical products.

1-Tetracosanol is a fatty alcohol containing 24 carbon atoms, usually derived from the fatty acid lignoceric acid.

In organic chemistry, the Ziegler process is a method for producing fatty alcohols from ethylene using an organoaluminium compound. The reaction produces linear primary alcohols with an even numbered carbon chain. The process uses an aluminum compound to oligomerize ethylene and allow the resulting alkyl group to be oxygenated. The usually targeted products are fatty alcohols, which are otherwise derived from natural fats and oils. Fatty alcohols are used in food and chemical processing. They are useful due to their amphipathic nature. The synthesis route is named after Karl Ziegler, who described the process in 1955.

References