143-08-8 Usage
Description
1-Nonanol, also known as nonyl alcohol, is a straight-chain fatty alcohol with nine carbon atoms and the molecular formula CH3(CH2)8OH. It is a colorless to slightly yellow liquid with a citrus odor similar to citronella oil. Nonanol occurs naturally in the orange oil and is characterized by its rose-orange odor and a slightly fatty, bitter taste reminiscent of orange. It is found in a variety of natural sources, including citrus oils, fruits, vegetables, and other food products.
Uses
1. Used in Flavor and Fragrance Industry:
1-Nonanol is used as a flavoring agent for its waxy, green, coconut, cheese, milky, and creamy taste with citrus orange nuances. It is also used as a fragrance ingredient due to its characteristic rose-orange odor and slightly fatty, bitter taste.
2. Used in the Manufacture of Artificial Lemon Oil:
1-Nonanol is primarily used in the production of artificial lemon oil, contributing to its citrus-like aroma and taste.
3. Used in Perfumery:
Various esters of 1-Nonanol, such as nonyl acetate, are utilized in the perfumery industry to create unique and pleasant scents.
4. Occurrence in Natural Sources:
1-Nonanol is reported to occur frequently in nature, both free and esterified, in essential oils of grapefruit, Guinea sweet orange, Italian and Israeli sweet orange, bitter orange, and oak musk concrete. It is also found in apple, citrus juices, many berries, currants, guava, grapes, papaya, melon, pineapple, asparagus, cucumber, leek, peas, potato, cheeses, butter, milk, cooked chicken, beef and pork, hop oil, beer, rum, grape wines, tea, pecan, peanut oil, soybean, olive, plum, rose apple, beans, mushroom, starfruit, cauliflower, tamarind, fig, cardamom, rice, prickly pear, sweet corn, malt, cherimoya, oysters, crab, crayfish, clam, nectarine, mate, pepino fruit (Solanum muricatum), apricot, tobacco, and wheat bread.
Chemical Properties:
1-Nonanol is a colorless to light yellow liquid that floats on water and has a freezing point of 23°F. It has a characteristic rose-orange odor and a slightly fatty, bitter taste reminiscent of orange. It may be synthesized by reduction of ethyl pelargonate or from heptaldehyde via heptanol and heptylmagnesium bromide with ethylene oxide.
Toxicity
1-Nonanol shares similar toxicological properties to those of other primary alcohols. It is poorly absorbed through the skin and is severely irritating to the eyes. Vapors can be damaging to the lungs, causing pulmonary edema in severe cases. Oral exposure results in symptoms similar to those of ethanol intoxication, and like ethanol consumption, can cause liver damage.
Metabolism of action
Nonanol, like other primary alcohols, undergoes two general reactions in vivo. The first is oxidation to the carboxylic acid derivative and next the direct conjugation with glucuronic acid. It was reported that nonanol undergoes direct glucuronic conjugation to the extent of 4.1%. This oxidation proceeds with very little inhibition as opposed to that shown by methyl amyl alcohol and 2-ethyl butyl alcohol which form ester glucuronides.
Methods of Manufacturing
Made by sodium or high-pressure catalytic reduction of esters of pelargonic acid; hydroformylation of C8 linear alpha-olefins or internal olefins (occurs in a mixt); natural constituent of rose, grapefruit & orange oils.
References
1.https://en.wikipedia.org/wiki/1-Nonanol
2. https://pubchem.ncbi.nlm.nih.gov/compound/1-Nonanol#section=Non-Human-Toxicity-Values
Preparation
By reduction of ethyl pelargonate; from heptaldehyde via heptanol and heptylmagnesium bromide with ethylene oxide.
Production Methods
1-Nonanol is produced by the high-pressure catalytic reduction
of esters of pelargonic acid.
Synthesis Reference(s)
Tetrahedron Letters, 32, p. 4235, 1991 DOI: 10.1016/S0040-4039(00)92136-1
Reactivity Profile
1-Nonanol is an alcohol. Flammable and/or toxic gases are generated by the combination of alcohols with alkali metals, nitrides, and strong reducing agents. They react with oxoacids and carboxylic acids to form esters plus water. Oxidizing agents convert them to aldehydes or ketones. Alcohols exhibit both weak acid and weak base behavior. They may initiate the polymerization of isocyanates and epoxides.
Health Hazard
Liquid irritates eyes.
Flammability and Explosibility
Notclassified
Chemical Reactivity
Reactivity with Water: No reaction; Reactivity with Common Materials: No reaction; Stability During Transport: Stable; Neutralizing Agents for Acids and Caustics: Not pertinent; Polymerization: Not pertinent; Inhibitor of Polymerization: Not pertinent.
Safety Profile
Mddly toxic by
ingestion, skin contact, and inhalation.
Experimental reproductive effects.
Combustible liquid. When heated to
decomposition it emits acrid smoke and
irritating fumes. See also ALCOHOLS.
Metabolism
See alcohol C-8
Check Digit Verification of cas no
The CAS Registry Mumber 143-08-8 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,4 and 3 respectively; the second part has 2 digits, 0 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 143-08:
(5*1)+(4*4)+(3*3)+(2*0)+(1*8)=38
38 % 10 = 8
So 143-08-8 is a valid CAS Registry Number.
InChI:InChI=1/C9H20O/c1-2-3-4-5-6-7-8-9-10/h10H,2-9H2,1H3
143-08-8Relevant articles and documents
Alcoholysis and carbonyl hydrosilylation reactions using a polymer- supported trialkylsilane
Hu, Yonghan,Porco Jr., John A.
, p. 2711 - 2714 (1998)
Polystyrene-diethylsilane (PS-DES) resin may be reacted with alcohols (alcoholysis) and carbonyl compounds (hydrosilylation) in 1-methyl-2- pyrrolidinone (NMP) using Wilkinson's catalyst (RhCl(PPh3)3) to afford the corresponding resin-bound silyl ethers. The silyl ethers formed were effectively cleaved using HF/pyridine solution in THF. Methoxytrimethylsilane was employed to scavenge excess HF from product solutions.
Covalent grafting of cobalt carbonyl cluster on functionalized mesoporous SBA- 15 molecular sieve and its applications towards hydroformylation of 1-octene
Ahmed, Maqsood,Sakthivel, Ayyamperumal
, p. 85 - 90 (2016)
Cobalt carbonyl cluster was anchored through a facile route on the surface of organo-functionalized SBA-15 molecular sieve by post-synthetic approach. The successful grafting of organofunctional ligand and cobalt carbonyl cluster was evident thorough 29Si-MAS NMR, 13C-MAS NMR and FT-IR studies. The resultant cobalt clusters anchored functionalized SBA-15 material (SBA-15-RCo) showed promising catalytic activity on hydroformylation of 1-octene (97% conversion) with excellent selective towards hydroformylated products (90%).
Development of a ruthenium/Phosphite catalyst system for domino hydroformylation-reduction of olefins with carbon dioxide
Liu, Qiang,Wu, Lipeng,Fleischer, Ivana,Selent, Detlef,Franke, Robert,Jackstell, Ralf,Beller, Matthias
, p. 6888 - 6894 (2014)
An efficient domino ruthenium-catalyzed reverse water-gas-shift (RWGS)-hydroformylation-reduction reaction of olefins to alcohols is reported. Key to success is the use of specific bulky phosphite ligands and triruthenium dodecacarbonyl as the catalyst. Compared to the known ruthenium/chloride system, the new catalyst allows for a more efficient hydrohydroxymethylation of terminal and internal olefins with carbon dioxide at lower temperature. Unwanted hydrogenation of the substrate is prevented. Preliminary mechanism investigations uncovered the homogeneous nature of the active catalyst and the influence of the ligand and additive in individual steps of the reaction sequence.
Iridium-Catalyzed Domino Hydroformylation/Hydrogenation of Olefins to Alcohols: Synergy of Two Ligands
Beller, Matthias,Huang, Weiheng,Jackstell, Ralf,Jiao, Haijun,Tian, Xinxin
supporting information, (2022/01/13)
A novel one-pot iridium-catalyzed domino hydroxymethylation of olefins, which relies on using two different ligands at the same time, is reported. DFT computation reveals different activities for the individual hydroformylation and hydrogenation steps in the presence of mono- and bidentate ligands. Whereas bidentate ligands have higher hydrogenation activity, monodentate ligands show higher hydroformylation activity. Accordingly, a catalyst system is introduced that uses dual ligands in the whole domino process. Control experiments show that the overall selectivity is kinetically controlled. Both computation and experiment explain the function of the two optimized ligands during the domino process.
Ruthenium-catalysed domino hydroformylation-hydrogenation-esterification of olefins
Beller, Matthias,Dühren, Ricarda,Franke, Robert,Jackstell, Ralf,Kucmierczyk, Peter,Schneider, Carolin
, p. 5777 - 5780 (2021/09/10)
A novel catalytic domino reductive hydroformylation-esterification of olefins is reported. The optimal protocol makes use of an inexpensive Ru carbonyl catalyst and uses acetic acid as both solvent and reactant. In general, moderate to good yields are obtained using aliphatic or aromatic olefins including industrially relevant di-isobutene. This atom-efficient catalytic transformation provides straightforward access to various acetate esters from unfunctionalized olefins.