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Caproaldehyde is an organic compound with a chemical formula of C6H12O, CAS 66-25-1, which has a carbonyl group and a methyl group. It is a six-carbon aldehyde fatty acid with ice alcohol properties. It is a colorless to pale yellow liquid with a pungent odor and is volatile at room temperature. It is easy to oxidize and deteriorate rapidly in alkaline solution, so it should be stored in the refrigerator to prolong the storage time. It is a polar solution, not easily soluble in water, but soluble in organic solvents such as ethanol, acetone, and chloroform, and easily soluble in organic solvents such as oils, esters, and fatty acids. With remarkable luminescence, it can usually be used as a fluorescent probe, and has a wide range of applications in fluorescence detection and analysis.
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Chemical Formula |
C6H11O |
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Exact Mass |
99 |
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Molecular Weight |
99 |
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m/z |
99 (100.0%), 100 (6.5%) |
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Elemental Analysis |
C, 72.68; H, 11.18; O, 16.14 |
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Hexanal (chemical formula C ₆ H ₁₂ O, CAS number 66-25-1) is a colorless and transparent liquid with a pungent odor. It has a boiling point of about 130 ℃ at room temperature and a flash point of 32 ℃. It is insoluble in water but easily soluble in organic solvents such as ethanol and ether. As an important organic synthesis intermediate, its use covers many fields, such as essence and fragrance, food industry, medicine and health, material science, agriculture and analytical chemistry. With the breakthrough of green chemical technology, its application scenario is continuously expanding.
Caproaldehyde is a key component of synthetic spices, characterized by a fresh blend of grassy and fruity aromas, similar to the aroma of freshly cut grass or fresh apples. In the food industry, it is widely used to prepare apple, tomato, strawberry and other fruit essence, and is the core flavor additive of soft drinks, cold drinks, candy, baked food and pudding products. According to the GB 2760-1996 standard, n-hexanal is temporarily allowed to be used as a food flavoring, and its dosage is strictly limited: the maximum dosage for soft drinks is 1.3 mg/kg, for cold drinks it is 2.8 mg/kg, for candies it is 3.6 mg/kg, for baked goods it is 4.2 mg/kg, and for pudding it is 2.0-2.5 mg/kg. For example, in apple flavored carbonated beverages, 0.5-1.0 mg/kg of n-hexanal can give the product a rich natural fruity aroma without producing chemically synthesized odors.
In the field of daily chemicals, it is an important raw material for high-end perfume, soap, washing and ironing care products and household fragrance. Its aroma is long-lasting and natural, often compounded with ingredients such as limonene and linalool to form a rich and layered fragrance. For example, an international brand of laundry detergent added 0.3% n-hexanal to give the product a fresh scent of "green grass after rain", and market feedback showed a 27% increase in consumer satisfaction with the aroma.
In addition to being the raw material of essence, it also plays the role of flavor improver in food processing. In meat products, a dosage of 0.01-0.05% can effectively mask the fishy smell and enhance the natural flavor of the meat. For example, in the production of ham sausage, n-hexanal and sodium glutamate work together to make the product more salty and delicious, and reduce the use of essence by 30%. In the dairy industry, n-hexanal is used for flavoring frozen dairy products such as ice cream. Its low boiling point allows the aroma to be quickly released at low temperatures, enhancing the consumer experience.
More noteworthy is its natural preservation function. Research has shown that it can inhibit the growth of rot bacteria in various fruits and extend their shelf life at concentrations of 0.1-0.5 mmol/L. For example, in the strawberry storage experiment, the fruit decay rate was reduced by 42% after treatment with n-hexanal, and no chemical residues were detected, which meets the green food standards. This characteristic makes it a potential substitute for natural preservatives.
A versatile expert in the field of medicine and health
The application of n-hexanal in the pharmaceutical field is transitioning from traditional solvents to active ingredients. Its antibacterial activity has been confirmed by multiple studies: the minimum inhibitory concentration (MIC) against pathogenic bacteria such as Staphylococcus aureus and Escherichia coli is 0.5-2.0 mg/mL, which is more effective than some traditional antibiotics. Based on this characteristic, a certain enterprise has developed a bacteriostatic pesticide composition containing n-hexanal for the prevention and control of citrus anthracnose. Field trials have shown an efficacy rate of 83% and are environmentally friendly.
In biomedical research, it is an important tool for studying cell signaling. It can simulate lipid peroxidation products, induce cellular stress response, and reveal the relationship between oxidative stress and diseases. For example, in the Alzheimer's disease model, neuronal cells treated with n-hexanal showed a significant increase in tau protein phosphorylation levels, providing new clues for the study of disease mechanisms.
Key intermediates in materials science
As an organic synthesis intermediate, its applications in the field of materials cover multiple directions such as rubber, plastics, resins, and lubricants. In the rubber industry, it can extend the service life of products as an antioxidant: adding 2% n-hexanal to styrene butadiene rubber, the tensile strength retention rate increased from 65% to 82% in the 70 ℃ thermal aging test. In the field of plastics, high heat-resistant resins can be prepared by copolymerizing with styrene, which has a glass transition temperature (Tg) 15 ℃ higher than traditional materials and is suitable for electronic component packaging.
A more breakthrough application lies in the synthesis of optoelectronic materials. Through the aldol condensation reaction, caproaldehyde can be converted into 2-butyl-2-octenal, which can then be reduced to obtain 2-butyl-1-octanol - a key raw material for alignment films in liquid crystal displays (LCDs). A certain enterprise uses the n-hexanal route to produce 2-butyl-1-octanol with a purity of 99.5%, which meets the demand for high-end display panels and breaks the foreign technology monopoly.
Innovative applications in the fields of agriculture and environmental protection
In agriculture, the insecticidal properties of n-hexanal are used to develop green pesticides. Its contact killing activity LC ₅ ₀ against pests such as cabbage caterpillars and aphids is 12.5 mg/L, and it is safe for beneficial insects such as bees. For example, a certain biopesticide company compounded n-hexanal with azadirachtin to make a 0.5% water emulsion, which achieved a field control effect of 78%, an increase of 23 percentage points compared to a single agent.
In the field of environmental protection, it is the "cleaner" for the treatment of volatile organic compounds (VOCs). It can undergo catalytic reaction with ozone to generate harmless carbon dioxide and water, with a reaction rate constant of 1.2 × 10 ⁻¹⁴ cm ³/(molecule · s). The n-hexanal based catalyst developed by a certain environmental protection company has a removal rate of 92% for formaldehyde at 25 ℃ and can be reused more than 50 times, providing a new solution for indoor air purification.
In agriculture, the insecticidal properties of n-hexanal are used to develop green pesticides. Its contact killing activity LC ₅ ₀ against pests such as cabbage caterpillars and aphids is 12.5 mg/L, and it is safe for beneficial insects such as bees. For example, a certain biopesticide company compounded n-hexanal with azadirachtin to make a 0.5% water emulsion, which achieved a field control effect of 78%, an increase of 23 percentage points compared to a single agent.
In the field of environmental protection, it is the "cleaner" for the treatment of volatile organic compounds (VOCs). It can undergo catalytic reaction with ozone to generate harmless carbon dioxide and water, with a reaction rate constant of 1.2 × 10 ⁻¹⁴ cm ³/(molecule · s). The n-hexanal based catalyst developed by a certain environmental protection company has a removal rate of 92% for formaldehyde at 25 ℃ and can be reused more than 50 times, providing a new solution for indoor air purification.
It is a commonly used standard for gas chromatography (GC) analysis, used for calibrating instrument sensitivity and qualitative and quantitative analysis. Its boiling point is moderate and its chemical properties are stable, making it particularly suitable for the detection of aldehyde compounds. For example, in the detection of formaldehyde residues in food, using n-hexanal as an internal standard can reduce the detection limit from 0.1 mg/kg to 0.02 mg/kg and increase accuracy by three times. In addition, n-hexanal is also used for mechanistic studies of Wittig and Aldol reactions, as a model compound to reveal organic synthesis reaction pathways.
The synthesis of caproaldehyde is obtained by reacting Hexyllithium and formaldehyde under different temperature and reaction conditions. The following are two possible synthetic routes:
1. Synthesis of Hexanal by hydrogenation reduction of Hexan-1-ol:
(1). Synthesis of Hexan-1-ol:
Before hydrogenation reduction, we need to synthesize Hexan-1-ol first. Hexan-1-ol can be prepared by reacting Hexylmagnesium halide with acetic anhydride in tetrahydrofuran (THF).
The reaction equation is as follows:
Hexylmagnesium halide + acetic anhydride → Hexan-1-ol + magnesium acetate halide
(2). Hydrogenation reduction:
Dissolve Hexan-1-ol in ethanol, add a hydrogen catalyst (such as Pd/C), seal the reaction vessel and add hydrogen. After the reaction is completed, filter and distill to obtain Hexanal.
2. Synthesize Hexanal by reacting Hexyllithium and formaldehyde:
(1). Preparation of Hexyllithium:
Hexyllithium can be obtained by reacting n-hexyl halides with lithium bromoacetate in cyclohexane.
The reaction equation is as follows:
n-hexyl halide + lithium bromoacetate → Hexyllithium + sodium chloride + acetone
(2). Reaction of Hexyllithium and formaldehyde:
Suspend the prepared Hexyllithium in dry tetrahydrofuran, add formaldehyde and stir the reaction. After the reaction is completed, filter and distill to obtain Hexanal.
The reaction equation is as follows:
Hexyllithium + Formaldehyde → Hexanal + Ethylene + LiOH
CaproaldehydeIt should be noted that for the above two synthetic routes, reaction conditions such as temperature, reaction time, molar ratio of reactants, etc. will affect the yield and purity of the final product. In actual operation, it needs to be optimized according to the specific situation.
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