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Lauric acid

Lauric acid Background and overview

Lauric acid is a saturated linear aliphatic monobasic acid containing twelve carbon atoms. It is an important raw material for the manufacture of synthetic high-pressure polyethylene initiator B, vinyl chloride suspension polymerization initiator and polyvinyl chloride excellent heat stabilizer diethyl tin dilaurate. Coconut oil is a kind of natural vegetable oil rich in glyceryl laurate, and many countries use it as a raw material to prepare lauric acid. China's coconut oil production is very small, but it is rich in lime oil, mountain pepper oil and palm kernel oil. China is rich in natural vegetable oil resources. Camphor seed oil, laurel seed oil, palm kernel oil, etc. all contain a large amount of twelve-carbon fatty acids. Palm kernel oil is produced in China's Hainan Island, Guangxi and other places, and has been cultivated in large quantities by humans.
Lauric acid has the chemical properties of general saturated monocarboxylic acid, showing acidity and salt-forming effect. It can react with halide to generate corresponding acyl halide; it can react with ammonia to generate ammonium salt or amide; it can react with alcohol to generate ester; it can be reduced to alkane or alcohol. In recent years, with the rapid development of fine chemicals, the demand for various surfactants and daily cosmetics has also grown rapidly. Lauric acid is one of the main raw materials for the manufacture of various surfactants and daily chemicals, and its price rises rapidly with the increase in demand. In the late 1970s, lauric acid from Hunan, China was exported to Japan, Malaysia and Singapore, and the price of lauric acid continued to rise. With the development of various fine chemical products, it is expected that the demand for lauric acid will continue to grow in the future, and the application market for lauric acid will further expand.

Lauric acid characteristic

Also known as dodecanoic acid and decadioic acid. Those crystallized from ethanol are needle-like white to light yellow crystalline solids or crystalline powders. Slightly smell of laurel oil. The relative molecular mass is 200.33. The relative density is 0.8679 (0/4℃). The melting point is 44.2°C. Boiling point 298.9°C, 225°C (13.332×103Pa), 176°C (2.000×103Pa), 141°C (0.800×103Pa). The refractive index is 1.4304 (50°C). The viscosity is 7.30mPa·s (50°C). Insoluble in water, soluble in ethanol (126 at 0°C, 134 at 21°C), methanol (134 at 21°C), acetone (60.5 at 20°C), ether and petroleum ether, easily soluble in benzene (93.6 at 20°C) . Irritating to the skin. Mice were injected intravenously with LD50131±5.7mg/kg.

Lauric acid Technical index

Neutralization value is 277~284, iodine value is below 1, trace amount of water, trace amount of ash, trace amount of unsaponifiable matter, melting point 42~45℃. The basic specifications of lauric acid used in cosmetic raw materials are: acid value 275-285, iodine value below 1, melting point 32-45°C, ester value below 3, and strong heat residue below 0.1%. Lauric acid with an acid value above 277 mg KOH/g has a purity greater than 95%. The appearance of lauric acid can also reflect the purity of the product. Lauric acid with a purity of more than 99.5% appears on the surface after cooling and solidification, with large crystals and easy crushing. As the purity decreases, the "ice flower" pattern becomes less and less obvious, and the lauric acid below 95% can no longer form "ice flower" crystals. The specifications of China's lauric acid products are as follows:

Lauric acid Production Process

1.Extracted from coconut oil, Litsea cubeba seed oil, palm seed oil, mountain pepper seed oil, camphor seed oil and other kernel oils. Separate the essential oil components under high temperature and high pressure, and then rectify under reduced pressure to separate and refine the fatty acids. There are four main methods for obtaining lauric acid from vegetable oil: one is direct fatty acid distillation; the other is fatty acid methyl ester distillation, the third is solvent extraction, and the fourth is freezing crystallization. The direct fatty acid distillation method usually cracks the triglyceride fatty acid ester structure of the oil into fatty acids, and then performs vacuum distillation to obtain the required lauric acid. In order to convert fats into fatty acids, saponification acidification, pressurized catalytic cracking, atmospheric catalytic cracking, high-pressure hydrolysis, etc. have been used in the industry. Among them, the saponification acidification method is the oldest, high cost, and low efficiency. At present, most manufacturers use high-pressure and high-temperature hydrolysis. This method has a simple process and can obtain fat, fatty acid and glycerin, and can obtain the desired product through vacuum distillation. Fatty acid methyl esterification method is to first convert oil into fatty acid methyl ester, obtain methyl laurate by distillation, and then acidify and dry it by soap method to obtain lauric acid. The methyl esterification process can reduce the distillation temperature by 30-40°C, can reduce the breaking vibration of heat-sensitive substances, avoid the generation of thermal polymers, etc., has good thermal stability, and has little corrosion to equipment, which can reduce investment.

1)Coconut oil

The main component of coconut oil is C8~C18 fatty acids, which contain up to 45~80% of lauric acid. Many countries use it as a raw material to produce lauric acid, but the output of coconut oil in China is very small. The method of producing lauric acid from coconut oil has mostly adopted high-temperature and high-pressure hydrolysis: adding coconut oil, water and catalyst into an autoclave, heating to about 250°C and pressure reaching about 50 kg/cm2, at this time coconut oil is cracked Into various fatty acids and glycerin, and then use distillation method to obtain the required lauric acid. In large-scale production plants, a more advanced high-pressure continuous hydrolysis method is adopted.

2)Litsea cubeba kernel oil

Litsea cubeba is widely grown in various provinces south of the Yangtze River in China. It is a wild tree fruit. Litsea cubeba fruit contains a large amount of citral aromatic oil, which is an important raw material for flavoring and synthesizing ionone and vitamin A. Litsea cubeba kernel oil can be squeezed out from the core of the fruit. Litsea cubeba kernel oil is composed of C10~C18 fatty acid compounds, in which the content of lauric acid is 45-60%. The process of preparing lauric acid from Litsea cubeba kernel oil is: Litsea cubeba kernel oil-pickling-hydrolysis-fractionation-squeezing-rectification-crystallization-crushing-finished product.

3)Palm kernel oil

The largest palm oil producer in the world is Malaysia, which accounts for more than half of the world's total output. Palm kernel oil is composed of C6-C18 fatty acids, usually containing lauric acid The amount is 46-51%.

4)Mountain pepper seed oil

Mountain pepper belongs to Lauraceae and is a deciduous tree. The mountain pepper drupe is spherical, the fruit is green at first, and black when mature. Mountain pepper kernel oil contains more than 30% lauric acid.

5)Other vegetable oils

such as palm kernel oil, rubbing tree seed oil, tree seed oil, etc. also contain twelve-carbon fatty acids, which can be used to make lauric acid.

6)Extract lauric acid

Hydrotreating the remaining C12 fraction (containing large basins of dodecenoic acid) after extracting lauric acid can convert dodecenoic acid into lauric acid. Hydrogenation can be carried out under normal pressure, the conversion rate can reach above 86%, and the iodine value can be reduced from 5 to about 6.6. This method does not require catalysts and high temperature and high pressure equipment.

2、Use lipolytic enzymes to continuously decompose under normal temperature and pressure.

Lauric acid application

1. Used as surfactants, most of them are used as anionic surfactants, accounting for about 60%, part of them are used as nonionic surfactants, accounting for about 30%, and the rest are cationic and amphoteric surfactants. Anions include sodium laurate (emulsifier, foaming detergent, emulsion polymerization), ammonium laurate, triethanolamine laurate (liquid detergent raw material), metal laurate (zinc, cadmium, barium salt, metal soap and stabilizer) Agent), lauroyl sarcosinate (surfactant), lauryl ether sulfate (detergent, foaming agent); non-ionic surfactants include sorbitol monolauryl ester (emulsifying, dispersing, wetting agent), Polyoxyethylene sorbitol monolaurate (emulsifier, solubilizer, stabilizer), polyethylene glycol monolaurate (general emulsifier), polyoxyethylene laurate (emulsion, liquid detergent), lauric acid Diethanolamide (foaming agent, shampoo), diethylene glycol laurate (emulsifier, dispersant) and lauric acid chloride (foam stabilizer, organic synthesis intermediate); cationic surfactants include laurylamine (cation and Amphoteric surfactant, emulsification, dyeing auxiliary, flotation agent, dispersant), lauryl nitrile (surfactant), lauryl trimethylamine chloride (dyeing auxiliary, emulsifying, dispersing, antistatic, softening agent) , Laurylamine acetate (flotation agent, pigment surface treatment agent), lauryl dimethylamine (cationic surfactant), dilauryl monomethylamine (cationic surfactant), trilaurylamine (rare earth element extraction Agent); Amphoteric surfactants are lauryl betaine (washing, antistatic, foaming agent), lauryl dimethyl betaine (shampoo foaming, dyeing auxiliary), lauric acid imidazoline and its derivatives (antistatic Electrostatic agent). Lauric acid chloride is used as ultraviolet absorber, lauroyl peroxide (peroxide), methyl laurate (cellulose oil, cosmetic raw material), lauryl stearoyl acrylate (adhesive), methyl laurate Ester (fragrance), lauric aldehyde (fragrance). In addition, lauric acid is an edible defoamer and spice that is allowed to be used in China GB2760-1996.

1.Sterilization

From lauric acid and lauryl alcohol as raw materials, a surface active agent with sterilization and disinfection effects can be prepared. In other words, this type of product can be used not only as a surfactant, but also as a disinfectant. Dodecyl dimethyl benzyl ammonium chloride, also known as "Zermin" or 1227, is prepared by chlorinating and aminating lauryl alcohol and then condensing with benzyl chloride. The molecular formula of Zeolite is:
Zeolite is widely used in surgical instruments and wound surface disinfection. It has also been widely used in industry. For example, in the cooling water system of large-scale fertilizer, oil refining and alkylbenzene production equipment, it has achieved satisfactory results as a sterilization and algaecide for circulating water. It is also widely used as a disinfectant in agriculture and other fields, because compared with the traditional disinfectant formalin, it has the advantages of high efficacy, low cost, non-irritation, non-toxicity and low corrosion. It is also antibacterial for the skin. Special disinfectant. Dodecyl dimethyl benzyl ammonium bromide, also known as "Xinjiermi", has a similar effect to "Zermeni", and its molecular formula is as follows:
Dodecyl dimethyl (2-phenoxyethyl) ammonium bromide, also known as "Dumiphene" or "Xilining", is a disinfectant made from lauryl alcohol. Its molecular formula is:

3. Plastic additives

Phthalic acid dilaurate (DLP), prepared by the condensation of phthalic anhydride and lauric acid, is used as a plasticizer for polyvinyl chloride and its copolymer resins. DLP has low volatility, good temperature and cold resistance, and can be used to make films with strong tensile strength and good flexibility. It can also be used for PVC floor, wall decoration board, wire wrap, artificial leather, fire fighting equipment, etc. Diethylene glycol dilaurate can be used as a plasticizer, emulsifier, inhibitor, and a stationary liquid for gas chromatography analysis. Dilauryl thiodipropionate can be used as an antioxidant and stabilizer for polypropylene, polyethylene, polyvinyl chloride, ABS plastics, etc., as well as a plasticizer and softener, and can be used as a component of food packaging materials . It can also be used as an antioxidant for rubber, grease, soap, lubricating grease, and grease. It is particularly effective as a heat stabilizer for polypropylene processing. Dibutyltin dilaurate is a polyvinyl chloride stabilizer, mainly used in soft and semi-rigid polyvinyl chloride products, such as transparent films, pipes, and artificial leather. The same series of products still include: maleic acid monobutyl dibutyltin laurate, maleic acid monooctyl lauric acid, dibutyltin and more than ten varieties.

4. Food additives

Thiamine disulfate monolauryl ester salt can be used in lubricants, stabilizers, cosmetic compounding agents, thickeners, hydrophobic agents, etc. Zinc laurate can also be used in films for food packaging.

5. Perfume industry

The following spices or spice intermediates can be directly synthesized from lauric acid: lauramide, ethyl laurate, phenyl laurate, lauryl alcohol, lauric aldehyde, lauryl nitrile, lauryl ketone, lauryl formaldehyde, lauryl ether and so on.

6. Metal Lauric Acid

Sodium laurate can be used in cleaning agent, pharmaceutical industry and organic synthesis raw material. Zinc salt, barium salt, calcium salt of lauric acid, etc.

7. Other

Methyl laurate is a raw material for organic synthesis. It can also be used as fiber oil, cosmetic additives, and also used in gas chromatography stationary liquids. It is an important organic intermediate. Lauryl stearyl phthalate acrylate can be used as a mold release agent.