Sebacic acid CAS 111-20-6

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  • Appearance: White powder
  • Assay: 99. 0%min
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Basic Info of Sebacic acid

What is Sebacic acid?

Sebacic acid is an important fine chemical intermediate, which is widely used in the chemical industry. For example, it is used in the production of nylon engineering plastics, cold-resistant plasticizers, and high-temperature lubricants.

Sebacic acid is a white flaky crystal. Slightly soluble in water, soluble in ethanol and ether. Combustible. Basically non-toxic, but the production raw material cresol is toxic. Avoid contact with liquid acid and alkali during storage, store in a cool and ventilated place, fireproof and moisture-proof.

Castor oil is heated and hydrolyzed in the presence of alkali to produce sodium ricinoleate soap, and then acidified with sulfuric acid to produce ricinoleic acid. Then, in the presence of the diluent cresol, the mixture of ricinoleic acid and alkali is heated to 260-280 ° C for cracking to obtain disodium sebacate, 2-octanol and hydrogen. The product is diluted with water, heated with acid to convert disodium sebacate into monosodium salt, and then decolorized by activated carbon, boiled and added with acid, separated and separated into sebacic acid crystals and dried to obtain the finished product of sebacic acid.

Since China is currently the second largest producer of castor oil in the world, it is also the largest producer of sebacic acid in the world.

Sebacic acid Uses

Raw materials used as plasticizers, such as dioctyl sebacate (DOS), dibutyl sebacate (DBS), dimethyl sebacate (DMS), diethyl sebacate (DES), etc. Esters, with low volatility, excellent migration resistance and electrical properties, especially better cold resistance, are widely used as plasticizers for nylon resins, lubricating oils, wire sheaths, films, etc.; DBS is odorless, tasteless, cold-resistant, relatively Polyvinyl chloride is easier to process and is recognized by the FDA as a food packaging material; used as a raw material for cosmetics, medicine, fragrance, etc; polyethylene modifier; It has replaced other cross-linking agents; it is also used as a raw material for surfactants and reinforced polyester resins.

The alkaline cracking method of castor oil is commonly used in industry to produce sebacic acid. Castor oil is first saponified to form castor oil sodium salt, which is then subjected to a cracking reaction with sodium hydroxide at high temperature to form sebacic acid sodium salt. Sebacic acid can also be prepared by electrolytic coupling of adipic acid monoester and nitric acid oxidation of cyclodecane and cyclodecanol.

The main use of sebacic acid is in the manufacture of alkyd, polyester and polyurethane resins from which paints, films or machine parts can be made. The polycondensation of sebacic acid and decanediamine (see condensation polymerization) can produce nylon 1010, which is widely used in military meshes and other screen meshes, and can replace copper wire mesh. Polycondensation of sebacic acid and hexamethylene diamine can produce nylon 610, which can be made into electrical parts, insulating paint, etc. Esters of sebacic acid and branched alcohols are the main components of artificial lubricating oils. Esters of sebacic acid and monohydric alcohols are plasticizers for polyvinyl chloride plastics. Sebacic acid is also used in the fragrance industry.

Sebacic acid has a wide range of uses, mainly used to prepare sebacic acid esters, such as dioctyl sebacate, which can be used as a plasticizer for plastics and cold-resistant rubber, and can also be used to prepare polyamides, polyurethanes, alkyd resins, Synthetic lubricants, lubricant additives. Epoxy resin curing agent polysebacic anhydride, as well as fragrances, coatings, cosmetics, etc.

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Application of Sebacic acid

Sebacic acid is an important chemical synthesis raw material. In my country, sebacic acid is mainly used to synthesize sebacic acid diester series low-temperature plasticizer products, and reports in this regard have an upward trend in recent years. In foreign literature reports, sebacic acid is used more in medicinal chemical synthesis. The application of sebacic acid is reviewed below.

Most of the sebacic acid diester series products are used as low-temperature plasticizers in the plastics industry and the synthetic rubber industry. The two main products are dibutyl sebacate and di-n-hexyl sebacate. Dibutyl sebacate is a colorless and transparent liquid with fruit aroma and light oily odor. It is compatible with most resins and synthetic rubbers, so it can be used as the main plasticizer to make the product have excellent low temperature performance and oil resistance. . Dibutyl sebacate is non-toxic and has cold resistance. It has a wide range of applications in the food packaging material industry and synthetic fragrance industries. In addition, it can also be used as a solvent for some rubbers and resins. The traditional method for synthesizing dibutyl sebacate is to synthesize by esterification of sebacic acid and n-butanol under the catalysis of concentrated sulfuric acid. This method has disadvantages such as easy corrosion of equipment, long production process, unsatisfactory yield and purity. In recent years, many domestic scientific researchers have devoted themselves to developing new catalysts to replace concentrated sulfuric acid to catalyze the production of dibutyl sebacate. In recent years, using granular activated carbon-supported silicotungstic acid as catalyst, the optimal reaction conditions for the synthesis of butylene sebacate by orthogonal experiments are that the molar ratio of acid to alcohol is 1:3.5, and the amount of supported catalyst is the mass of sebacic acid. The final esterification rate of this method is 98.79%; the activated carbon-supported phosphotungstic acid is used as the catalyst, the molar ratio of acid to alcohol is 1:5, the amount of sebacic acid is 0.08mol, and the amount of catalyst is 0.08mol. 1.5g (solid load 25.3%), reaction time 3h, cyclohexane with water agent 10ml, reaction temperature 98-112℃ to synthesize dibutyl sebacate, the esterification rate reaches 98.1%; Ester is a non-toxic cold-resistant plasticizer with low volatility and low viscosity. It can be used as a plasticizer for agricultural films, wires, sheets, artificial leather, outdoor water pipes, frozen foods, and pharmaceutical packaging plastics. And because of its low viscosity, di-n-hexyl sebacate can also be used as a lubricant.

The traditional synthesis method of di-n-hexyl sebacate also uses sulfuric acid as catalyst. Using solid acid SO42-/TiO2-ZrO2 as catalyst, it was studied under the reaction conditions of reaction temperature of 220℃, reaction time of 2.5h, molar ratio of acid to alcohol 1:.3.25, and catalyst dosage of 0.8% of the total mass of the system. The yield of di-n-hexyl sebacate can reach the highest 98.41%. In addition, the synthesis of dihexyl sebacate was studied using silicotungstic heteropolyacid and activated carbon supported p-toluenesulfonic acid as catalysts, respectively. The optimal reaction conditions for the former synthesis of dihexyl sebacate were determined by orthogonal experiments: the amount of sebacic acid was 0.05mol, the molar ratio of acid to alcohol was 1:2.6, the catalyst was 0.5g, and the water agent toluene was 10ml, and the reaction time was 1h, the average esterification rate is 95.3%; the best reaction conditions for the latter are: the dosage of sebacic acid is 0.05mol, the dosage of n-hexanol is 0.13mol, the dosage of catalyst is 3g, the toluene with water agent is 15ml, and the reaction time is 1h. The average esterification rate under 98.2%.

Diethyl sebacate is a colorless and transparent liquid with fruit flavor. Its main purpose is to be used as food flavoring. In order to solve the defects of the traditional catalytic synthesis with concentrated sulfuric acid, the catalytic synthesis of diethyl sebacate by p-toluenesulfonic acid was studied. : 8:0.31, cyclohexane is a water-carrying agent, and the water is refluxed for 1 h. Under the reaction conditions, the ester yield reaches 96.9%. This method has the advantages of convenient operation, mild reaction, high product purity and yield; The acid cation exchange resin was used as the catalyst, and the optimal reaction conditions explored were that the molar ratio of acid to alcohol was 1:7, the amount of catalyst was 1.5g, and the amount of cyclohexane with water agent was 15ml (when the amount of sebacic acid was 0.1mol), Reaction at 80℃ for 7h, the esterification rate can reach 95.45%; gold nanocomposite solid superacid S2O82-/CoFe2O4 is prepared. The optimal reaction conditions of the catalyst are that the molar ratio of acid to alcohol is 1:4, sebacic acid is 0.1mol, The catalyst was 1.0g, the reaction time was 2.5h, and the esterification rate was 93.6% under this reaction condition.

Foreign researches related to the catalytic synthesis of diethyl sebacate also include research on titanium dioxide solid acid catalyst, which is made by impregnating powdered titanium dioxide in sulfuric acid solution. Catalytic performance in the esterification reaction of acid and ethanol, using this catalyst to participate in the esterification reaction of sebacic acid and ethanol, it will reach the reaction equilibrium point in about 80min.

Plastic products are one of the indispensable products in daily life. They are easy to process, light, and beautiful. With the improvement of the quality of life, plastic products are increasingly showing their irreplaceable status, but the problem of environmental pollution caused by waste plastics is also becoming more and more serious. Therefore, the development of materials to replace traditional plastics is also one of the important topics of contemporary environmental protection. Biodegradable aliphatic polyesters are ideal substitutes for traditional plastics. Using sebacic acid and hexanediol as raw materials and decalin as solvent for direct polymerization, degradable high molecular weight polyhexanediol sebacate was synthesized with a yield of 96%, and its melting point was determined to be 76.5 ℃, The crystallization temperature was 56°C.

After testing, polyhexylene sebacate has excellent mechanical properties, high strength and toughness, and can be used instead of traditional plastics. Biodegradable polyester materials also have a range of elastic aliphatic polyesters. This series of polyesters is prepared by a two-step reaction using sebacic acid, ethylene glycol and glycerol as raw materials. That is, sebacic acid and ethylene glycol are used to synthesize a prepolymer, and then the prepolymer and glycerin are mixed and reacted according to different ratios. The final product is a transparent polyester, which is tough, insoluble in organic solutions, and has a hydrophilic surface. At 37℃, the enzymatic degradation study was carried out with porcine pancreatic enzyme in phosphate buffer solution. The results showed that the enzymatic degradation degree of this series of polyesters increased with the increase of glycerol content. It is worth mentioning that the -COOC- group on the surface of the polyester is the decisive factor for the enzymatic degradation ability. In addition to biodegradable polyester materials, the synthetic green lubricant oleic acid neopentyl glycol sebacate mixed ester is prominent. The mixed ester is obtained by first synthesizing oligomers with sebacic acid and neopentyl glycol as raw materials, and then esterifying the oligomers with oleic acid. After testing, the mixed ester of oleic neopentyl glycol sebacate has good viscosity and thermal stability, and at the same time has good biodegradability, and can be used as a material to replace traditional mineral oil lubricants.

Sebacic acid is also widely used in medical synthetic chemistry. Aiming at the defect of strong hydrophobicity when polysebacic anhydride alone is used as a drug carrier for sustained and controlled drug release, a polysebacic anhydride-polyethylene glycol copolymer was synthesized from sebacic acid, acetic anhydride and PEG. In the copolymer, polyether PEG with oil-water amphiphilicity is introduced into the main chain of polysebacic anhydride, in order to achieve the purpose of improving the strong hydrophobicity of polysebacic anhydride. Through the determination of solubility, it was confirmed that the introduction of PEG indeed improved the solubility of the copolymer in polar solvents.

Preparation of Sebacic acid

Sebacic acid was first obtained by dry distillation of castor oil and alkali. Later, a synthetic method was developed. At present, a new route for sebacic acid by fermentation of petroleum n-alkane is being developed. The alkali hydrolysis of castor oil commonly used in industry is that in the reaction kettle, castor oil and lye undergo saponification reaction at 100 ℃ to generate sodium ricinoleate and glycerin. The sodium ricinoleate is separated and added with sulfuric acid to generate ricinoleic acid, which is then subjected to an alkaline hydrolysis reaction with an alkali. The reaction generates sebacic acid disodium salt and 2-octanol and hydrogen. Finally, the pure product is obtained by neutralization, decolorization, crystallization and drying with sulfuric acid, and the total yield is above 40%. Another production method of sebacic acid is the adipic acid electrolytic oxidation method developed by Japan’s Asahi Kasei Industrial Company. Compared with the castor oil alkali hydrolysis method, the cost is higher, so it is not produced on a large scale.

  1. Use castor oil as raw material, separate the ricinoleic acid in it, carry out alkali fusion with caustic soda at 280~300℃, and heat for 10h to obtain the sodium salt of sebacic acid, and by-product 2-Octanol. The sodium salt was dissolved in water, neutralized by adding sulfuric acid, and after decolorization, the solution was cooled to precipitate sebacic acid, washed with cold water, and finally recrystallized.
    2NaOH→CH3(CH2)5CH(OH)CH3+ NaOOC(CH2)8COONa+H2
    NaOOC(CH2)3COONa+H2SO4→ +Na2SO4
  2. It is synthesized from fatty acid (adipic acid) as raw material. Adipic acid and methanol undergo esterification reaction to generate dimethyl adipate, which is electrolytically oxidized to dimer, namely dimethyl sebacate, by ion exchange membrane, and then reacted with sodium hydroxide to generate disodium salt, Neutralization with hydrochloric acid (or sulfuric acid) can produce sebacic acid.


  1. Sebacic acid – WikiPedia
  2. Research progress on the preparation and application of sebacic acid

Sebacic acid Suppliers and Manufacturers

As a sebacic acid supplier and manufacturer with a strict standard product quality system certificate, Zhishang Chemical has long been providing the best sebacic acid raw materials to customers all over the world.

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