All of this adds to the operation costs with the result that sebacic acid is a relatively expensive chemical. It is resolved in ethanol, ether and soluble slightly in The temperature of reaction is above 175* C., preferably between 240" C. and 325' C., so special means, such as carrying out the reaction under a superatmospheric pressure at least equal to the vapor tension of the mixture at the temperature used, is necessary. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.) Ricinoleic acid was used- in a continuous manner as above with similar results. Derivatives, Castor Oil & Derivatives Sebacic acid is an alpha,omega-dicarboxylic acid that is the 1,8-dicarboxy derivative of octane. Its fine particle size allows it to be added to the grease during the The report analyzes, tracks, and presents the worldwide market size of the leading players in each region around … Although the … In a batch process, the mixture of castor oil or ricinoleic acid and aqueous alkali is added to an autoclave which may then be heated up and held at the desired temperature, or the autoclave may be maintained at reaction temperature and the charge pumped in. The amount of water used in making up the charging mixture can be varied considerably, although the best yields of sebacic acid are obtained when the amount of water is the minimum that can be employed and yet allow the reaction mixture to remain fluid and pumpable at reaction temperature. acetone, There are two primary methods: © 2004-2021 FreePatentsOnline.com. The yield of sebacic acid obtained was 49.8% by weight. Adipic acid is partially esterified to the monomethyl adipate. The product can be discharged by blowing out through a discharge pipe, utilizing the pressure in the autoclave, or it may be drained out at the bottom of the autoclave. In practicing this invention, we have found 16 that considerable variation may be made in the factors controlling the reaction without affecting the course of the reaction, except that the pressure developed depends upon the other factors and upon the amount of free space in the reaction vessel. US2815375A US550202A US55020255A US2815375A US 2815375 A US2815375 A US 2815375A US 550202 A US550202 A US 550202A US 55020255 A US55020255 A US 55020255A US 2815375 A US2815375 A US 2815375A Authority US United States Prior art keywords acid sebacic acid process … Furthermore, the process has always heretofore been of such a character as to be applicable only to batch operation; that is to say, a batch of castor oil and alkali hydroxide are heated together until the reaction is complete and the reaction kettle is then emptied to receive a fresh batch of castor oil and alkali. producer of SBA. A process of manufacturing sebacic acid which comprises heating castor oil with a member of the group consisting of alkali metal hydroxides and alkali metal carbonates in aqueous T5 solution at a temperature between 2500 C. and 300° C. under a superatmospheric pressure at least equivalent to the vapor tension of the reaction mixture. Sebacic Acid can be used as a corrosion ... View the Specifications Epoxidized Soybean Oil (ESO) CAS# 8013-07-8. This treatment results in saponification of the castor oil to ricinoleic acid that is then cleaved to give capryl alcohol (2-octanol) and sebacic acid. g5 The aqueous solution was almost colorless and contained the sebacic acid which was set free by further acidification with sulfuric acid. The fatty acid present and the octanol-2 separated into an oily layer and were removed. The reaction product was discharged into about four times its weight of water and heated to 95* C. with stirring. sebacate, 3. The products obtained were similar in quality and quantity to those obtained in the batch process. This process could not have been foreseen, since the alkali fusion method of the prior art is in reality an oxidation of the ricinoleic acid molecule by the action of molten alkali hydroxide, and it was extremely unlikely that an aqueous caustic alkali solution would behave as drastically as molten caustic on ricinoleic acid. Two derivatives of sebacic acid nomenclature, generation I derivatives include hydrogenated castor oil, sebacate/dibutyl sebacate) are synthetic base stocks that can replace the Electrolysis of the potassium & Castor Derivatives Sourcing, Uses of Castor Oil & Caster The process at best is, however, unsatisfactory. This invention relates to an improved process for manufacturing sebacic acid, and deals more particularly with a method for producing sebacic acid from ricinoleic acid or from its functional derivatives, more particularly from its salts, amides or esters, especially from castor oil. results in heptaldehyde and undecenoic acid. Sebacic acid is widely used in various end use industries including lubricants, plasticizers, hydraulic fluids, candles, and cosmetics. obtained from thousands of potential starting materials. The sebacic acid so obtained was a white, flaky material having a melting point of 1290-130° C. The capryl alcohol (octanol-2) was recovered from the fatty acid by-product by steam distillation. The global market for generation process for the production of sebacic acid diesters from adipic acid monoesters of higher alcohols by electrochemical condensation in methanolic solution using continuous or intermittent flow of current, in which a saturated monoor polyvalent ether or a lower alkanoic acid is added to the reaction mixture. It has been found advantageous to use sodium hydroxide as the caustic alkali, although other alkalies which give water-soluble salts of ricinoleic acid, such as potassium hydroxide, may be used, or the corresponding alkali metal carbonates or mixtures of any of these alkalies can be used. In the foregoing examples, given to illustrate the invention, ricinoleic acid and castor oil, the S2 most available materials, have been used as representative, but it is apparent that other functional derivatives of ricinoleic acid could be used in equivalent amounts.. Any ricinoleic acid derivative which, when treated with alkali, forms 80 a ricinoleic acid soap may be used as starting material in our process. Due to the fact that the reaction mixture remains in solution during the heating period, this process is particularly well adapted to large-scale use in a continuous manner in which a mixture of castor oil or ricinoleic acid and aqueous alkali is pumped through a suitable reaction vessel held at the desired temperature. The esters of sebacic acid also are used as It produces high purity sebacic acid from readily available adipic acid. Palletized CIF price: $3,686.00/MT - $3,704.00/MT, We were not able to get Example 3 The process was carried out in a continuous manner by adding castor oil to 354 aqueous sodium hydroxide at such a rate that there was approximately 3.5 equivalents of alkali per each equivalent of ricinoleic acid content. Due to the difficulties of stirring the reaction mass huge power-consuming scrapers and stirrers are re5a quired in order to prevent local overheating. Furthermore, all the products are obtained in better purity. Overall yields are reported to be 6. Sebacic acid (SA) is an aliphatic ten-carbon dicarboxylic acid (1,10-decanedioic acid) with a variety of industrial applications, including the production of plasticizers, lubricants, cosmetics, and plastics. For generation III derivatives, where half of the generation II derivatives are A process of manufacturing sebacic acid which comprises mixing approximately 30 parts by weight of a member of the group consisting of ricinoleic acid, its esters and salts with from 7 to 60 parts of water and an amount of an alkali metal hydroxide equivalent to from 8 to 16 parts of sodium hydroxide, heating said mixture in a closed vessel at a temperature of from 175° C. to 350" C. under conditions that prevent the escape 85 of water vapor, acidifying the reaction product to a pH of approximately 6 to separate liquid fatty acid by-products and octanol-2, removing said by-products from the water layer, and acidifying the water layer to a pH below 6 to precipitate the sebacic acid. If a great excess of water is employed, the yield of sebacic acid is decreased. Ricinoleic Acid  Alkali Fusion @ This area located at Umraya Village – on ECP Canal Road, about 20 kms from Vadodara in Gujarat. process. An isomer, isosebacic acid, has other applications in the candles. ether. Sebacic acid is a chemical compound primarily derived from castor oil with two primary uses: (1) as a reactant with other chemicals to produce distinct chemical compounds or polymers;1or (2) directly in formulated products such as antifreeze coolants, and as a corrosion inhibitor in … EC number: 203-845-5 | CAS number: 111-20-6 . per square inch. Sebacic acid is produced from castor oil by cleavage of ricinoleic acid, which is obtained from castor oil. caustic oxidation of castor oil. A process of manufacturing sebacic acid which comprises mixing approximately 30 parts by weight of castor oil with from 8 to 16 parts of sodium hydroxide and from 7 to 60 parts of water, heating said mixture at approximately 275° C. under a pressure above 800 lbs. Generation II castor oil derivatives include sebacic acid, undecyclenic per square inch. From time to time the material collected from the discharge was withdrawn and worked up in 16 batches as described in Example 2 to recover the capryl alcohol, fatty acid and sebacic acid. The aqueous layer containing the half salt is Pyrolysis of ricinoleic acid �         A large number of esters can be cool down period with no additional processing. A process of manufacturing sebacic acid which comprises heating a member of the group consisting of ricinoleic acid, its esters and salts with a member of the group consisting of alkali metal hydroxides and alkali metal carbonates in aqueous solution at a temperature between 250° C. and 300* C. under a superatmospheric pressure at least equivalent to the vapor tension of the reaction mixture. Sebacic Acid India, India�s They are used in the synthesis of polyamide aromatics, antiseptics and painting materials. The type of reaction used affects Some such agents appear to give somewhat better yields of sebacic acid than are otherwise obtained, notably with hydrogenation-dehydrogenation catalysts. Some catalytic materials, such as alumina, cause a decrease in the yield of sebacic acid obtained. The process consists of three steps. The quantity of alkali required is in excess of that required to saponify the castor oil or to form the soap of ricinoleic acid. Being non-toxic, used boiling range of 300 to 400 oC or the use of a mixture of cresols. It can also be obtained from decalin via the tertiary hydroperoxide, which gives cyclodecenone, a precursor to sebacic acid. This condition is conveniently attained by heating the mixture in a closed system which prevents the escape of all vapors and gases until after the reaction is completed. The Sebacic India ltd., Manufacturing Company, fully complies with REACH (Registration, Evaluation, and Authorization of Chemicals), the EU regulatory system for chemicals management AND have completed the Registration for volumes of even 1000 T/year or more for SEBACIC ACID. However, there is no further advantage gained by doing so. gage. The extremely difficult stirring of the old fusion process is eliminated. the traditional method uses castor oil as the starting point while a new method The pressure observed at the end of this time was 1500 lbs. crease in yield over prior processes. At our preferred temperature of about 275" C., the pressure usually observed is 800 to 1200 lbs. Since the reaction ordinarily requires from 8 to 24 hours for completion, depending upon the size of the batch and the efficiency of the heating and stirring, either a large number of small reaction vessels and the necessary stirring equipment are required, or else very expensive large capacity reactors are necessary in order to produce commercial quantities of sebacic acid of the order required for the coatings and plastics industry. A further object is to provide a continuous .process for manufacturing sebacic acid and octanol-2. Castor Oil, Turkey Red Oil, European increase to two moles of alkali/mole ricinoleate and at temperatures of 250 to intermediate for aromatics, antiseptics and painting materials. Omega-Dicarboxylic acid that is the aqueous alkali metal soaps remain in aqueous solution throughout the heating period to 95 C.... 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