143-08-8 Usage
Description
Different sources of media describe the Description of 143-08-8 differently. You can refer to the following data:
1. 1-Nonanol 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. The primary use of nonanol is in the manufacture of artificial lemon oil. Various esters of nonanol, such as nonyl acetate, are used in perfumery and flavors. Nonanol floats on water and its freezing point 23°F.
2. Nonyl alcohol has a characteristic rose-orange odor and a slightly fatty, bitter taste reminiscent of orange. May be synthesized by reduction of ethyl pelargonate; 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
Chemical Properties
Different sources of media describe the Chemical Properties of 143-08-8 differently. You can refer to the following data:
1. Nonyl alcohol has a characteristic rose–orange odor and a slightly fatty, bitter taste reminiscent of orange.
2. colourless to light yellow liquid
3. 1-Nonanol is found in a number of citrus oils. It is a
liquid.
Occurrence
Reported as occurring frequently in nature, free or esterified; in the essential oils of grapefruit, Guinea sweet
orange, Italian and Israeli sweet orange, bitter orange; and in oak musk concrete. Also reported 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, clary sage, oysters, crab, crayfish,
clam, nectarine, mate, pepino fruit (Solanum muricatum), apricot, tobacco, and wheat bread.
Uses
Different sources of media describe the Uses of 143-08-8 differently. You can refer to the following data:
1. 1-Nonanol is an chain fatty acid alcohol that naturally occurs in oil of orange. 1-Nonanol is used in the manufacture of artificial lemon oil.
2. In manufacture of artificial lemon oil.
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.
Aroma threshold values
Detection: 50 to 90 ppb; aroma characteristics at 1.0%: intensely waxy, sweet, green, citrus, orange-like,
creamy with fruity nuances of tamarind and melon.
Taste threshold values
Taste characteristics at 0.5 to 1.0 ppm: waxy, green, coconut, cheese, milky and creamy with citrus orange
nuances.
Synthesis Reference(s)
Tetrahedron Letters, 32, p. 4235, 1991 DOI: 10.1016/S0040-4039(00)92136-1
General Description
Colorless liquid with a rose or fruity odor. Floats on water. Freezing point 23°F.
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.
Method for producing a shaped catalyst body
-
Page/Page column 29-30, (2021/11/19)
Provided herein is a novel process for producing shaped catalyst bodies in which a mixture having aluminum contents of Al±0 in the range from 80 to 99.8% by weight, based on the mixture used, is used to form a specific intermetallic phase, shaped catalyst bodies obtainable by the process of the invention, a process for producing an active catalyst fixed bed including the shaped catalyst bodies provided herein, the active catalyst fixed beds and also the use of these active catalyst fixed beds for the hydrogenation of organic hydrogenatable compounds or for formate degradation.
Directing Selectivity to Aldehydes, Alcohols, or Esters with Diphobane Ligands in Pd-Catalyzed Alkene Carbonylations
Aitipamula, Srinivasulu,Britovsek, George J. P.,Nobbs, James D.,Tay, Dillon W. P.,Van Meurs, Martin
, p. 1914 - 1925 (2021/06/28)
Phenylene-bridged diphobane ligands with different substituents (CF3, H, OMe, (OMe)2, tBu) have been synthesized and applied as ligands in palladium-catalyzed carbonylation reactions of various alkenes. The performance of these ligands in terms of selectivity in hydroformylation versus alkoxycarbonylation has been studied using 1-hexene, 1-octene, and methyl pentenoates as substrates, and the results have been compared with the ethylene-bridged diphobane ligand (BCOPE). Hydroformylation of 1-octene in the protic solvent 2-ethyl hexanol results in a competition between hydroformylation and alkoxycarbonylation, whereby the phenylene-bridged ligands, in particular, the trifluoromethylphenylene-bridged diphobane L1 with an electron-withdrawing substituent, lead to ester products via alkoxycarbonylation, whereas BCOPE gives predominantly alcohol products (n-nonanol and isomers) via reductive hydroformylation. The preference of BCOPE for reductive hydroformylation is also seen in the hydroformylation of 1-hexene in diglyme as the solvent, producing heptanol as the major product, whereas phenylene-bridged ligands show much lower activities in this case. The phenylene-bridged ligands show excellent performance in the methoxycarbonylation of 1-octene to methyl nonanoate, significantly better than BCOPE, the opposite trend seen in hydroformylation activity with these ligands. Studies on the hydroformylation of functionalized alkenes such as 4-methyl pentenoate with phenylene-bridged ligands versus BCOPE showed that also in this case, BCOPE directs product selectivity toward alcohols, while phenylene-bridge diphobane L2 favors aldehyde formation. In addition to ligand effects, product selectivities are also determined by the nature and the amount of the acid cocatalyst used, which can affect substrate and aldehyde hydrogenation as well as double bond isomerization.
