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Propionic acid oil, also known as primary oleic acid, is a short chain saturated fatty acid, chemical formula CH3CH2COOH, molecular weight 74.08. Propionic acid belongs to weak electrolyte (Ka=1.34 × 10-5), its aqueous solution is weakly acidic, but highly corrosive, and the steam is irritating to the skin and respiratory tract. Under normal temperature and pressure, propionic acid is a colorless, clear, oily liquid with an unpleasant rancidity and pungent smell. It is miscible with water, ethanol, chloroform and ether.
Propionic acid is mainly used as food preservative and mildew inhibitor, as well as as inhibitor of medium viscosity substances such as beer, nitrocellulose solvent and plasticizer, and it can also be used in the preparation of nickel plating solution, food flavor, medicine, pesticide, mildew inhibitor, etc.
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Chemical Formula |
C3H6O2 |
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Exact Mass |
74 |
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Molecular Weight |
74 |
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m/z |
74 (100.0%), 75 (3.2%) |
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Elemental Analysis |
C, 48.64; H, 8.16; O, 43.19 |
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Propionic acid oil, also known as primary oleic acid, is a short chain saturated fatty acid with the chemical formula CH3 CH ₂ COOH. Under its colorless and clear oily appearance, it hides an irritating rancid odor, but with its unique chemical properties - weak acidity (Ka=1.34 × 10 ⁻⁵), strong corrosiveness, and steam irritation to the skin and respiratory tract - it has become a core raw material in multiple industrial fields. From food preservation to pharmaceutical manufacturing, from chemical synthesis to agricultural applications, the value of propionic acid runs through every aspect of human production and life.
1. Food preservatives and mold inhibitors
One of the core applications of propionic acd is as a food preservative. It achieves broad-spectrum inhibition of fungi, yeast, and bacteria by inhibiting the synthesis of microbial cell membranes and disrupting enzyme system activity. In baked goods such as bread and pastries, adding 0.1% -0.3% calcium propionate or sodium propionate can extend the shelf life to over 30 days while maintaining the soft texture of the food. Experimental data shows that under the conditions of 25 ℃ and relative humidity of 75%, the growth delay time of bread mold with added calcium propionate is 5 times longer than that without added group.
In the field of grain preservation, propionic acd penetrates into the interior of grains and inhibits the metabolic activity of toxin producing fungi such as Aspergillus flavus and Aspergillus ochraceus.
For example, in corn storage, spraying 0.2% propionic acd solution can reduce the content of zearalenone in corn by 80%, providing a safety guarantee for long-term storage. In addition, propionic acd can also be used as a beverage preservative to inhibit the formation of viscous substances in beer production and prevent the turbidity of the beer body.
2. Fermentation agents and acidity regulators
Propionic acd is the 'invisible assistant' for bread fermentation. During the dough fermentation process, propionic acd activates yeast enzyme activity and promotes carbon dioxide generation by adjusting the pH to a weakly acidic environment of 4.5-5.0, resulting in a 20% -30% increase in dough expansion rate.
Meanwhile, its antibacterial properties can inhibit bacterial contamination and ensure the stability of the fermentation process.In cheese production, propionic acd, as a byproduct of lactic acd bacteria fermentation, gives Cheddar cheese a unique nutty flavor and inhibits the growth of spoilage bacteria by lowering the pH value.
3. Food spices and flavor enhancers
Propionic acd and its esters are important sources of food flavorings. Ethyl propionate has a pineapple aroma, while isoamyl propionate presents an apple flavor and is widely used as a seasoning in candies, beverages, and baked goods. In meat processing, adding 0.05% propionic acd can enhance the meat aroma, while inhibiting the halal flavor produced by fat oxidation, and improving the sensory quality of the product.
Medical field: diverse roles from formulation stability to disease treatment
1. Drug solvents and pH regulators
Propionic acid oil plays an "invisible supporting role" in pharmaceutical manufacturing. As a solvent, it can dissolve insoluble drugs such as vitamin B12 and adrenaline, improving their bioavailability. In the preparation of injection solutions, a 0.5% -1% propionic acd solution can stabilize the pH value of the drug within the appropriate range of 3.5-5.0, preventing drug hydrolysis and oxidative degradation. For example, adding propionic acid to penicillin G potassium salt injection can extend the drug's effective period from 6 hours to 24 hours.
2. Potential value of disease treatment
Propionic acid exhibits unique potential in the treatment of metabolic diseases. As a short chain fatty acd, it can be absorbed by colonic epithelial cells, promoting gluconeogenesis and fat metabolism. Animal experiments have shown that oral administration of propionic acd can reduce blood glucose levels in rats by 15%, while inhibiting liver fat synthase activity and reducing fat accumulation. In addition, propionic acd has an adjuvant therapeutic effect on inflammatory bowel diseases such as ulcerative colitis by regulating the balance of gut microbiota.
1. Moisturizing agents and skin conditioners
Propionic acid, with its small molecular structure and lipophilicity, has become the "water magnet" in cosmetics. It can penetrate into the stratum corneum, combine with water molecules to form a hydration membrane, and increase the skin's moisture content to 15% -20%. In the face cream formula, 1% -3% propionic acd can increase skin smoothness by 40%, and reduce transcutaneous water loss (TEWL) by 30%.
2. Core components of antibacterial and anti-corrosion system
The antibacterial properties of propionic acd make it a natural choice for cosmetic preservatives.
The diameter of its inhibition zone against Staphylococcus aureus and Escherichia coli can reach 12mm (0.1% concentration), and when combined with preservatives such as phenoxyethanol and p-hydroxyacetophenone, it can form a synergistic anti-corrosion network.
In shampoo formula, the combination of 0.05% propionic acid and 0.1% phenoxyethanol can extend the shelf life of the product to 36 months.
3. Acid base regulation and stability improvement
Propionic acd neutralizes alkaline components and adjusts the pH of cosmetics to a weakly acidic range of 4.5-6.5, which conforms to the natural pH environment of the skin. Adding 0.02% propionic acd to vitamin C essence can stabilize the pH of the product at 5.0-5.5, prevent the oxidative degradation of vitamin C, and reduce the irritation to the skin.
1. Raw materials for the synthesis of organic ester compounds
Propionic acid oil can generate various high value-added products through esterification reactions. Butyl propionate has a fruity aroma and is used in the synthesis of spices and solvents; Cellulose propionate acts as a plasticizer to enhance the flexibility and heat resistance of plastics. In the coating industry, propionic acd modified alkyd resin can shorten the drying time to 2 hours and increase the hardness of the paint film to 3H.
2. Metal surface treatment and cleaning agents
The acidity of propionic acd makes it a "green choice" for metal cleaning. It can dissolve metal oxides such as rust and oxide scale, and has lower corrosiveness to the substrate than hydrochloric acd and sulfuric acd. In the steel rust removal process, a 5% -10% propionic acid solution treated at 60 ℃ for 30 minutes can achieve a rust removal rate of 95%, while forming a dense passivation film to prevent secondary corrosion.
3. Additives in the electroplating industry
Propionic acid, as a buffer and brightener in nickel plating solution, can stabilize the pH value of the solution at 4.0-4.5 and prevent the precipitation of nickel hydroxide. At the same time, it can adsorb on the cathode surface, refine nickel grains, increase the brightness of the coating by 2 levels, and improve wear resistance by 30%.
4. Innovative applications in the field of environmental protection
Propionic acid and its salts show potential in exhaust gas treatment. Calcium propionate can absorb hydrogen sulfide (H ₂ S) from industrial waste gas, with an absorption capacity of 0.8g/g (calculated as calcium propionate), and the recycling rate after regeneration exceeds 90%. In addition, the propionic acd derivative polylactic acd (PLA), as a biodegradable plastic, can completely decompose into carbon dioxide and water within 6 months, providing a new solution to address "white pollution".
1. Feed mold inhibitors and nutrient fortifiers
Propionic acid is the "natural guardian" of feed preservation. It can penetrate into the interior of feed particles, inhibit the growth of molds such as Aspergillus flavus and Aspergillus ochraceus, and prevent fungal toxin contamination. Adding 0.2% calcium propionate to pig feed can reduce the feed mold rate from 15% to 2% and increase the feed conversion rate by 8%. In addition, propionic acd, as a regulator of rumen fermentation in ruminants, can promote propionic acid production and provide additional energy for animals.
2. Pesticide intermediates and green prevention and control
Propionic acid is a key synthetic material for various pesticides. Its derivative 2,4-D propionate is a selective herbicide that can damage the cell membrane of dicotyledonous weeds and is highly safe for crops such as wheat and corn.
In orchard management, spraying 0.5% propionic acid solution can inhibit the germination of apple rot pathogen spores, with a control effect of 85%, and there is no residual risk to the fruit.
3. Soil improvement and plant growth regulation
Propionic acd improves soil fertility by regulating soil pH and microbial community structure. In acidic soil, propionic acd can neutralize the toxicity of aluminum ions and increase crop root growth by 20%. Meanwhile, as a plant growth regulator, it can promote potato tuber enlargement and increase yield by 15% -20%.
Propionic acd, with its unique chemical properties and wide application value, has become a "chemical link" connecting fields such as food, medicine, chemical engineering, and agriculture. From preservatives that extend the shelf life of bread to potential drugs for treating metabolic diseases; From acid-base regulators that enhance the stability of cosmetics to biodegradable plastics that solve white pollution, the application boundaries of propionic acid are constantly expanding with technological innovation.
Preparation of propionic acid oil:
Microorganisms such as propionic acid can use a variety of fermentable sugars to produce propionic acid. In industry, a variety of biomass can be first hydrolyzed into monosaccharides such as glucose or xylose with acid or enzyme, and then introduced into a reactor for fermentation. After fermentation, add lime milk, precipitate, filter, add sodium sulfate for double decomposition reaction, filter and concentrate, add sulfuric acid for conversion, and then fractionate. The fermentation reactor can adopt the immobilized protoplast tower reactor, and the cells can be fixed in the following form: the surface of the pre sterilized packing ring is covered with a layer of sterilized solution containing 20% gelatin and 1.5% shellac by immersion method, and after drying, 2.5% glutaraldehyde aqueous solution is sprayed, so that the polymer on the surface of the packing ring is cross-linked to increase the strength. Rinse with sterile water, then sterilize with ethylene glycol, discharge ethylene glycol and blow it clean with sterile nitrogen. Thereafter, propionic acid bacteria culture liquid is added to the reactor filled with the filling ring to form a fixed cell membrane on the surface of the filling ring, and then continuous feeding can be carried out for fermentation.
Refining method:
Dry and distill with anhydrous sodium sulfate to collect 139~141 ℃ fraction. Distillate with a small amount of solid potassium permanganate and then distill. It can also be converted to ethyl ester for fractionation. The ethyl propionate was refined by hydrolysis.
The direct oxidation of low carbon hydrocarbons can produce formic acid and propionic acid when using low carbon hydrocarbons as raw materials to produce acetic acid, and propionic acid can be obtained after separation.
Propanoic acid was synthesized by one step reaction of ethylene with carbon monoxide and water under the catalysis of nickel carbonyl. The reaction conditions are 250 ～ 320 ℃ and 10 ～ 30MPa.
Oxidation of propionaldehyde In the presence of manganese propionate catalyst, propionaldehyde reacts with air or oxygen to generate propionic acid.
Propionitrile hydrolysis method is prepared by hydrolysis of propionitrile under the catalysis of concentrated sulfuric acid.
Acrylic acid method is prepared by hydrogenation and reduction of acrylic acid.
Ethanol carbonylation method Ethanol is prepared by reacting with carbon monoxide in the presence of catalyst.
Chemical properties of propionic acid oil:
React with inorganic substances
The hydrogen atom on the carboxyl group of propionic acid can be partially ionized into hydrogen ions (protons) in the aqueous solution and released, thus causing propionic acid to be acidic. Propionic acid is a weak monobasic acid in aqueous solution, pKa=4.87 (25 ℃).
1. Because propionic acid is an acid, propionic acid can neutralize with alkali to generate corresponding propionate:
Reaction of propionic acid and sodium hydroxide: CH3CH2COOH+NaOH=CH3CH2COONa+H2O
Reaction of propionic acid and calcium hydroxide: 2CH3CH2COOH+Ca (OH)2=(CH3CH2COO) 2Ca+2H2O
Reaction of propionic acid and ammonia: CH3CH2COOH+NH3 · H2O=CH3CH2COONH4+H2O
2. Propionic acid can undergo double decomposition reaction with weak acid salts such as carbonate:
Reaction of propionic acid and carbonate: 2CH3CH2COOH+CO32-=2CH3CH2COO -+H2O+CO2 ↑
3. Due to the weak acid nature of propionic acid, propionic acid is corrosive to many metals, such as iron, magnesium and propionic acid react to generate hydrogen and metal propionate.
Reaction of propionic acid with iron: Fe+2CH3CH2COOH=(CH3CH2COO) 2Fe+H2 ↑
Reaction of propionic acid and aluminum: 2Al+6CH3CH2COOH=2 (CH3CH2COO) 3Al+3H2 ↑
Reaction of propionic acid with magnesium: Mg+2CH3CH2COOH=(CH3CH2COO) 2Mg+H2 ↑
Substitution reaction of hydroxyl group on carboxyl group
The - OH in propionic acid can be used as a group and replaced by carboxyl, halogen or alkoxy to generate acid anhydride, acyl halide or ester and other propionic acid derivatives, respectively.
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