1-Nonanol CAS 143-08-8

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1-Nonanol, a chemical substance, has the molecular formula of C9H20O. Colorless to light yellow viscous liquid with slight rose fragrance. Slightly soluble in water, soluble in ethanol and ether, and miscible in alcohol, ether and chloroform. Soluble in 3 volumes of 60% ethanol and oil, acid value<1.0. It has strong sweet and green rose wax and fruity fat wax aroma. There is some smell like orange and sweet orange. It is stable under normal temperature and pressure, and has no corrosion to metal. It has typical reactivity of higher primary alcohol. Store away from strong oxidants. It exists in flue-cured tobacco leaves. It naturally exists in grapefruit oil, sweet orange oil, rose oil, apple, cooked beef and cheese. It is used as solvent, wetting agent, defoamer, etc. for nitro paint and enamel, and also as raw material for the manufacture of surfactant and perfume.

1-Nonanol,The chemical name is 1-nonanol, and its molecular formula is C ₉ H ₂ ₀ O. It is a straight chain saturated monohydrate. It usually appears as a colorless transparent liquid with a special odor, insoluble in water, but soluble in various organic solvents such as ethanol, ether, etc. 1-Nonanol exists in some plant essential oils in nature and can also be prepared in large quantities through chemical synthesis methods. Due to its unique chemical structure and properties, 1-Nonanol has a wide range of applications in multiple fields and plays an important role in promoting the development of related industries.

Use in the field of spice and essence

 

1-Nonanol has a unique fragrance. Its fragrance is light and soft, with faint floral and fruity aromas. This aroma feature makes it one of the important raw materials in the spice essence industry. In the manufacture of perfume, 1-Nonnol can be used as a component of top note or middle note to add fresh and elegant fragrance levels to perfume. In terms of cosmetics essence, 1-Nonanol is commonly used in face cream, lotion, shampoo and other products. It can give cosmetics a pleasant aroma and enhance the user experience of the product. Compared to some strong spices, the mild aroma of 1-Nonanol is more suitable for use in daily cosmetics and does not provide users with an overly stimulating olfactory experience. At the same time, its good stability and volatility can ensure the persistence and uniform release of fragrance in cosmetics during storage and use. Flavor fixatives play a vital role in essence, which can extend the fragrance retention time of spices and make the aroma more durable and stable. Due to the presence of hydroxyl groups in its molecular structure, 1-Nonanol has certain polarity and hydrophilicity, and can form hydrogen bonds and interact with other components in the fragrance, thereby slowing down the volatilization rate of the fragrance. When preparing essence, add proper amount of 1-Nonanol as fixative, which can keep the aroma of essence stable for a long time and not easy to lose.

Application in the industrial field

 

In the coatings and ink industry, the selection of solvents is crucial for the performance and quality of products. 1-Nonanol has good solubility and can dissolve various resins, pigments, and additives. It is one of the commonly used solvents in coatings and inks. It can adjust the viscosity of coatings and inks, making them have good fluidity and coating performance, which is convenient for construction operations. Meanwhile, 1-Nonanol has moderate volatility and can gradually evaporate during the drying process of coatings and inks, resulting in a uniform and smooth surface of the coating. In the field of industrial cleaning, 1-Nonanol can be used as one of the effective ingredients in cleaning agents. It can dissolve oil stains, dust, and other impurities, and has good cleaning ability. 1-Nonanol can also participate in various chemical reactions as an intermediate in chemical production. For example, it can be used to prepare 1-nonanal through oxidation reaction. 1-nonanal is an important organic chemical raw material that can be used for the synthesis of fragrances, pharmaceutical intermediates, and other products. In addition, 1-Nonanol can also undergo esterification reactions with acids to produce various nonanoic acid ester compounds, which have wide applications in industries such as plastics, rubber, and coatings.

Preparation method of 1-Nonanol:

1. There are many production methods in industry. Propylene is polymerized in the presence of phosphoric acid or boron fluoride to obtain nonene, and nonanol is obtained by hydration of nonene. Isobutene in the butane-butene fraction is dimerized to obtain diisobutylene and mixed octene, and then carbonylated to obtain nonyl alcohol and mixed nonyl alcohol. Ethyl nonanoate and sodium metal were reduced in ethanol solution to obtain nonanol.

2. Nonyl alcohol can be obtained by the following reaction between heptane bromide and ethylene oxide.

3. It is obtained by reducing ethyl nonanoate and sodium metal in ethanol solution.

4. Tobacco: FC, 40.

5. Preparation method: Firstly, use 24.5g (1mol) magnesium chips, 179g (1.0mol) 1-bromoheptane and 300mL dibutyl ether ① to prepare Grignard reagent according to the conventional method. Cool it to 0 ℃, stir it violently, pass in filtered ethylene oxide (2), keep the temperature of the reaction system at about 0 ℃, and react for 1h after passing through. After that, the temperature was raised to 40 ℃ for reaction for 1h. Heat the reaction in water bath for 2h. After cooling, the reactant is poured into ice water and acidified with dilute sulfuric acid to dissolve the generated magnesium hydroxide. Ammonium is treated by the above 1-hexanol treatment method, and the distillate of 95~100 ℃/1.6kPa is collected to obtain 95g of 1-nonanol (1), with a yield of 69%.

Note: ① The purification method of dibutyl ether is as follows: wash it with sodium hydroxide solution and water in turn, dry it with anhydrous calcium chloride, and then fractionate it to collect the fraction at 140~142 ℃.

Hydroformylation of Octene
The most common method involves the hydroformylation of 1-octene (C₈H₁₆), an α-olefin derived from petroleum or bio-based feedstocks. The reaction, catalyzed by rhodium or cobalt complexes under high pressure (10–30 MPa) and temperature (80–150°C), adds carbon monoxide and hydrogen to the double bond, forming nonanal (C₉H₁₈O). Subsequent hydrogenation of nonanal yields 1-nonanol with high purity (typically >98%).

Key advantages:

High Selectivity: Modern catalysts achieve >90% yield of the linear alcohol.

Scalability: Suitable for large-volume production.

Hydrogenation of Nonanoic Acid
An alternative approach hydrogenates nonanoic acid (pelargonic acid), a naturally occurring fatty acid found in pelargonium oils. This method is less common due to the higher cost of nonanoic acid but may gain traction with advances in bio-based routes.

Bio-Based Synthesis
Emerging research explores microbial or enzymatic production of 1-nonanol from renewable resources. For instance, engineered Escherichia coli strains have been reported to produce nonanol via fatty acid biosynthesis pathways, though scalability and cost-effectiveness remain challenges.

Purification and Quality Control

Post-synthesis, 1-nonanol is purified via distillation, adsorption, or crystallization to remove impurities like residual catalysts, unreacted starting materials, or isomers. Quality control employs gas chromatography (GC) and nuclear magnetic resonance (NMR) spectroscopy to ensure compliance with industry standards (e.g., ASTM D1353).

Molecular Structure and Isomerism

1-Nonanol exists as a straight-chain alcohol, with the hydroxyl group at the terminal carbon (C1). Its linear structure imparts distinct physical properties compared to branched isomers (e.g., 2-nonanol).

Physical Properties

Boiling Point: 214–215°C (at 760 mmHg).

Melting Point: −7°C.

Density: 0.824 g/cm³ (at 20°C).

Solubility: Slightly soluble in water (0.3 g/100 mL at 20°C) but miscible with organic solvents like ethanol, ether, and chloroform.

Odor: Mild, fatty, or floral, characteristic of higher fatty alcohols.

Chemical Reactivity

1-Nonanol's hydroxyl group enables diverse reactions:

Esterification: Reacts with carboxylic acids to form esters, used in fragrances and plasticizers.

Oxidation: Converts to nonanoic acid or aldehydes (e.g., nonanal) under oxidative conditions.

Sulfation: Reacts with sulfuric acid to yield alkyl sulfates, common in detergents.

Toxicity and Biodegradability

1-Nonanol is classified as a low-toxicity compound, with oral LD50 values in rats exceeding 5 g/kg. However, its limited biodegradability in aquatic environments raises ecological concerns. Studies indicate that 1-nonanol may persist in sediment or soil, potentially affecting aquatic organisms.

Sustainability Initiatives

The industry is adopting green chemistry principles to reduce 1-nonanol's environmental impact:

Bio-Based Feedstocks: Using renewable resources (e.g., vegetable oils) instead of petrochemicals for hydroformylation.

Catalyst Recycling: Developing heterogeneous catalysts to simplify separation and reuse.

Waste Minimization: Optimizing reaction conditions to reduce byproducts and energy consumption.

Regulatory Compliance

1-Nonanol production and use adhere to regulations such as REACH (EU), TSCA (US), and the Globally Harmonized System (GHS). Occupational exposure limits (OELs) are set to protect workers from respiratory or dermal irritation, with recommended airborne concentrations below 10 ppm.

Bio-Synthesis and Biotechnology

Microbial Production: Engineering yeast or bacteria to produce 1-nonanol from sugars or lignocellulosic biomass.

Enzymatic Catalysis: Using lipases or dehydrogenases to synthesize 1-nonanol or its derivatives under mild conditions.

Advanced Materials

Nanocomposites: Integrating 1-nonanol-based polymers with nanoparticles (e.g., graphene, silica) to enhance mechanical or thermal properties.

Self-Assembling Systems: Exploring 1-nonanol's role in forming supramolecular structures for drug delivery or sensors.

Sustainable Agriculture

Bioherbicides: Developing 1-nonanol-based formulations for organic farming, reducing reliance on synthetic pesticides.

Insect Pheromones: Synthesizing 1-nonanol derivatives as mating disruptors for pest management.

Green Chemistry

Alternative Catalysts: Replacing noble metals with earth-abundant metals (e.g., iron, cobalt) in hydroformylation reactions.

Circular Economy: Designing recycling processes for 1-nonanol-containing products (e.g., detergents, plastics) to close material loops.

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