N-HEPTANOIC ACID

CAS No.: 111-14-8
EC No.: 203-838-7

Synonyms:
N-HEPTANOIC ACID; n-Heptanoic Acid; N-HEPTANOİK ASİT; n-Heptanoik Asit; n-heptanoic acid; 111-14-8 [RN]; 1744723 [Beilstein]; 1-heptanoic acid; 203-838-7 [EINECS]; 3348; Acide heptanoïque [French] [ACD/IUPAC Name]; Acido eptanoico [Italian]; ácido heptanoico [Spanish]; enanthic acid; Enanthyl alcohol; Heptanoic acid [ACD/Index Name] [ACD/IUPAC Name]; Heptansäure [German] [ACD/IUPAC Name]; MFCD00004426 [MDL number]; Oenanthic acid; 101488-09-9 [RN]; 130348-93-5 [RN]; 156779-04-3 [RN]; 1-Hexanecarboxylic acid; 352431-36-8 [RN]; 4-02-00-00214 [Beilstein]; 4-02-00-00958 (Beilstein Handbook Reference) [Beilstein]; N-HEPTANOIC ACID; n-Heptanoic Acid; N-HEPTANOİK ASİT; n-Heptanoik Asit; N-HEPTANOIC ACID; n-Heptanoic Acid; N-HEPTANOİK ASİT; n-Heptanoik Asit; EINECS 203-838-7; Enanthylic acid; Heptanoic Acid Natural; heptanoicacid; Heptansaeure; Hepthlic acid; heptoic acid; heptylic acid; KZH; Nat.Heptanoic Acid; n-Heptoic acid; n-Heptylic acid; Oenanthsaeure; oenanthylic acid; QV6 [WLN]; sec-Heptanoic acid; 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N-HEPTANOİK ASİT; n-Heptanoik Asit; E3F2CC4A-F2B5-4353-8922-355FA750FEAC; F0001-0233; Enanthic Acid, United States Pharmacopeia (USP) Reference Standard; N-HEPTANOIC ACID; n-Heptanoic Acid; N-HEPTANOİK ASİT; n-Heptanoik Asit; N-HEPTANOIC ACID; n-Heptanoic Acid; N-HEPTANOİK ASİT; n-Heptanoik Asit; n-heptanoic acid; 111-14-8 [RN]; 1744723 [Beilstein]; 1-heptanoic acid; 203-838-7 [EINECS]; 3348; Acide heptanoïque [French] [ACD/IUPAC Name]; Acido eptanoico [Italian]; ácido heptanoico [Spanish]; enanthic acid; Enanthyl alcohol; Heptanoic acid [ACD/Index Name] [ACD/IUPAC Name]; Heptansäure [German] [ACD/IUPAC Name]; MFCD00004426 [MDL number]; Oenanthic acid; 101488-09-9 [RN]; 130348-93-5 [RN]; 156779-04-3 [RN]; 1-Hexanecarboxylic acid; 352431-36-8 [RN]; 4-02-00-00214 [Beilstein]; 4-02-00-00958 (Beilstein Handbook Reference) [Beilstein]; N-HEPTANOIC ACID; n-Heptanoic Acid; N-HEPTANOİK ASİT; n-Heptanoik Asit; N-HEPTANOIC ACID; n-Heptanoic Acid; N-HEPTANOİK ASİT; n-Heptanoik Asit; EINECS 203-838-7; 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N-HEPTANOIC ACID 

Bio-Based n-Heptanoic acid
n-Heptanoic acid is a seven-carbon linear chain saturated fatty acid that can be used in the form of:

Esters in the flavors and fragrances industry, in cosmetics and in industrial lubricants (aviation, refrigeration, automobile, etc.)
Salts (sodium heptanoate) for corrosion inhibition
Identity
CAS number: 111-14-8
Chemical name: n-Heptanoic acid
Common name: n-Heptylic acid, Oenanthic acid, Heptanoic acid
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Key Properties
n-Heptanoic acid - CAS 111-14-8
Purity ≥ 99%
100% of vegetable oil origin (derived from castor oil)
100% linear and saturated carbon chain
Chemical formula: CH3-(CH2)5-COOH
Main Applications
Thanks to its outstanding anti-corrosion properties and its unique performance level at high and low temperatures, bio-based Oleris® n-heptanoic acid is mainly used in lubricants in refrigeration/air conditioning, aviation, aerospace, automotive, etc.

Also, it has interesting applications in the form of esters in the flavors and fragrances industry as well as in cosmetics.

Lubricant Applications
Seven carbon atoms in the linear chain yields a good balance in terms of low viscosity at low temperature and low volatility at high temperature.

Gears of Titanium and Steel
n-heptanoic acid is used in lubricants in the form of esters (e.g. neopolyol ester) with:

Improved fluidity at low temperature, higher than with nearby C6/C8/C10
High thermal stability
Good resistance to oxidation
These esters are used primarily in applications for the automotive sector (car motor oils), in metalworking fluids, and as plasticizers etc.

Flavors and Fragrances Applications
n-Heptanoic acid, of 100% of vegetable origin (bio-based), is used as a chemical intermediate in the synthesis of esters from C1 to C9 alcohols. These esters present fruity, green, herbal or floral notes.

Pink Perfume Bottles and Petals
More than 25 aromatic esters from heptanoic acid are possible, like:

In flavors: Ethyl heptanoate or allyl heptanoate with fruity or pineapple notes are commonly used
In fragrances: Nonyl heptanoate is particulary appreciated for its orange floral rose notes
Cosmetic Applications
Brown Make-up Pencil
n-Heptanoic acid is used as a chemical intermediate in the synthesis of bio-based cosmetics:

Emollients
Skin conditioning agents
Viscosity controlling agents
Like Stearyl heptanoate, Glyceryl triheptanoate, etc.

INCI name: heptanoic acid

Anti-corrosion Applications
n-Heptanoic acid is a very effective corrosion inhibitor to protect copper, iron, aluminum and zinc when used as a salt derivative (sodium heptanoate).

This heptanoic acid shows good stability in hard water which prevents the precipitation of calcium.

Coatings
This salt of heptanoic acid is widely used in:

Metalworking fluids
Water-based hydraulic fluids for anti-freeze application
Industrial water-based refrigerants
Temporary protection
Anticorrosion additive for paints
Cutting oils
n-heptanoic acid certifications
Ecocert Cosmetics logo

n-heptanoic acid is Kosher certificated, free of BSE-TSE and is GMO free
n-heptanoic acid is compliant with the raw materials standard that can be used in the formulation of cosmetics certified according to the Natural and Organic ECOCERT standard, and meets the specifications of the Food Chemical Codex, but is not intended for use as a direct food ingredient
For industrial use only

N-Heptanoic acid price More Price(18)
Manufacturer    Product number    Product description    CAS number    Packaging    Price    Updated    Buy
Sigma-Aldrich    146870    N-Heptanoic acid 96%    111-14-8    100ml    $29    2020-08-18    Buy
Sigma-Aldrich    43858    N-Heptanoic acid analytical standard    111-14-8    1ml    $73.5    2020-08-18    Buy
TCI Chemical    H0030    N-Heptanoic acid >98.0%(T)    111-14-8    25mL    $17    2020-06-24    Buy
TCI Chemical    H0030    N-Heptanoic acid >98.0%(T)    111-14-8    500mL    $53    2020-06-24    Buy
Alfa Aesar    A17704    N-Heptanoic acid, 98+%    111-14-8    500ml    $55.4    2020-06-24    Buy
N-Heptanoic acid Chemical Properties,Uses,Production
Description
As an organic compound, N-Heptanoic acid is a seven-carbon linear chain saturated fatty acid with an unpleasant, rancid and pungent odor, which is commonly used as a chemical intermediate in the synthesis of esters for products, such as ethyl heptanoate, that are used in fragrances and artificial flavors. It is also applied in cosmetics for the production of emollients, skin conditioning agents as well as viscosity controlling agents. Besides, N-Heptanoic acid can also act as a industrial lubricant applied in the fields of aviation, refrigeration, automobile, etc. due to its low viscosity at low temperature and low volatility at high temperature. Moreover, the good anti-corrosion property of N-Heptanoic acid results in the usage of metalworking fluids, industrial water-based refrigerants and anti-corrosion additive for paint. N-Heptanoic acid is also applied to esterify steroids in the field of pharmaceutical to produce drugs such as testosterone enanthate, trenbolone enanthate, drostanolone enanthate, methenolone enanthate and it is also one of numerous additives in cigarettes.
References
https://en.wikipedia.org/wiki/Heptanoic_acid
https://pubchem.ncbi.nlm.nih.gov/compound/8094#section=Top
http://www.arkema.com/en/products/product-finder/product-viewer/Oleris-n-Heptanoic-acid/
Description
N-Heptanoic acid, also called enanthic acid, is an organic compound composed of a seven - carbon chain terminating in a carboxylic acid. It is an oily liquid with an unpleasant, rancid odor. It contributes to the odor of some rancid oils. It is slightly soluble in water, but very soluble in ethanol and ether.
Chemical Properties
N-Heptanoic acid has a disagreeable rancid odor. The spectroscopically pure acid exhibits a faint tallow-like odor. N-Heptanoic acid may be prepared by oxidation of heptaldehyde with potassium permanganate in diluted sulfuric acid.
Chemical Properties
N-Heptanoic acid has a disagreeable rancid, sour, sweat-like, fatty odor The spectroscopically pure acid exhibits a faint fallow-like odor.
Chemical Properties
colourless liquid with a pungent and rancid odour
Occurrence
Reported as occurring naturally in calamus, hops, Acacia dealbata, and Japanese peppermint and violet leaves; its presence in rancid oils has been observed Also reported found in passion fruit, mandarin orange peel oil, guava, apple, banana, grapes, papaya, raspberry, strawberry, kiwi, baked potato, sauerkraut, tomato, breads, cheeses, butter, milk, fsh, fsh oil, meats, chicken fat, pork fat, hop oil, beer, cognac, brandy, rum, grape wines, sherry, whiskies, sake, peated malt, cocoa, coffee, tea, soy protein, peanuts, pecans, coconut, beans, mushroom, fenugreek, mango, fgs, licorice, corn oil, shrimps, scallops and other sources
Uses
Intermediates of Liquid Crystals
Uses
There are two major uses for N-Heptanoic acid. One is in vinyl plasticizers that are used primarily in the automotive market.This market is expected to grow 3 to 4% per year with GNP.The second is in synthetic lubricants, where N-Heptanoic acid is used in polyol esters.The market for polyol esters is primarily for use in commercial and military jet turbine lubricants.There is a small market for these esters in the automotive lubricant area, but there has been limited acceptance of these products by automakers and the public.The growth of the polyol ester market is expected to track GNP, unless automakers change to support synthetics or unless there is an elevation of military activity.
The use of N-Heptanoic acid in high-water metalworking fluids has grown in excess of 20% over the last several years.The amount of acid used in these products is small; therefore, a dramatic change from the traditional oil-based fluids would be required before there would be significant market impact.
Definition
ChEBI: A C7, straight-chain fatty acid that contributes to the odour of some rancid oils. Used in the preparation of esters for the fragrance industry, and as an additive in cigarettes.
Production Methods
The methyl ester of ricinoleic acid, obtained from castor bean oil is the main commercial precursor to N-Heptanoic acid. It is hydrolyzed to the methyl ester of [[undecenoic acid]] and heptanal, which is then air oxidized to the carboxylic acid. Approximately 20,000 tons were consumed in Europe and US in 1980.
Ricinoleic acid is the main precursor to N-Heptanoic acid. N-Heptanoic acid is used in the preparation of esters, such as ethyl heptanoate, which are used in fragrances and as artificial flavors. N-Heptanoic acid is used to esterify steroids in the preparation of drugs such as as testosterone enanthate, trenbolone enanthate, drostanolone enanthate and methenolone enanthate (Primobolan). It is also one of many additives in cigarettes.
Preparation
By oxidation of heptaldehyde with potassium permanganate in diluted sulfuric acid.
Taste threshold values
Taste characteristics at 5 ppm: waxy, cheesy, fruity, dirty and fatty.
Synthesis Reference(s)
Organic Syntheses, Coll. Vol. 2, p. 315, 1943
The Journal of Organic Chemistry, 58, p. 4745, 1993
Tetrahedron Letters, 21, p. 2181, 1980 DOI: 10.1016/S0040-4039(00)78992-1
General Description
A colorless liquid with a pungent odor. Less dense than water and poorly soluble in water. Hence floats on water. Very corrosive. Contact may likely burn skin, eyes, and mucous membranes. May be toxic by ingestion, inhalation and skin absorption. Flash point near 200°F.
Air & Water Reactions
Slightly soluble in water.
Reactivity Profile
N-Heptanoic acid reacts exothermically with bases. Can react, particularly if moist, with active metals to form gaseous hydrogen and a metal salt. Such reactions are slow if the acid remains dry. Corrodes or dissolves iron, steel, and aluminum parts and containers under ordinary conditions. Reacts with cyanide salts to generate gaseous hydrogen cyanide, particuarly if moist. May generate flammable and/or toxic gases with diazo compounds, dithiocarbamates, isocyanates, mercaptans, nitrides, and sulfides. Reacts with sulfites, nitrites, thiosulfates (to give H2S and SO3), dithionites (SO2), to generate flammable and/or toxic gases and heat. Reacts exothermically with carbonates and bicarbonates to generate a harmless gas (carbon dioxide). Can be oxidized exothermically by strong oxidizing agents and reduced exothermically by strong reducing agents. A wide variety of products is possible. May initiate polymerization reactions; may catalyze chemical reactions.
Hazard
Combustible.
Health Hazard
Harmful if swallowed, inhaled, or absorbed through skin. Extremely destructive to mucous membranes, upper respiratory tract, skin, and eyes. Inhalation may be fatal as a result of spasm, inflammation and edema of the larynx and bronchi, chemical pneumonitis, and pulmonary edema. Symptoms of exposure may include burning sensation, coughing, wheezing, laryngitis, shortness of breath, headache, nausea, and vomiting.
Fire Hazard
N-Heptanoic acid is probably combustible.
N-Heptanoic acid Preparation Products And Raw materials