results in heptaldehyde and undecenoic acid. The lower layer, which is the aqueous alkali metal sebacic solution, can be drawn off. One object of the present invention is to lower the cost of making sebacic acid by the use of a more efficient process according to which sebacic acid is obtained in higher yields and purity by a method in which the solidification of the castor oil soaps during the heating is prevented, thereby eliminating charring, local overheating and pyrogenic decomposition. Examples: The process is based on the water. (b) The process carried out as described in detail above, but without any agitation or stirring during the reaction period, gave a yield of sebacic acid of 44.6% by weight. The products obtained were similar in quality and quantity to those obtained in the batch process. The quantity of alkali required is in excess of that required to saponify the castor oil or to form the soap of ricinoleic acid. Electrolysis of the potassium salt of monomethyl … Considerable local overheating occurs, resulting in charring and pyrogenic decomposition. acidulated to a pH of about 2, causing the resulting sebacic acid to greases improve workability and low temperature properties particularity for The pressure used is determined principally by the pressure developed by water at the temperature used and by hydrogen gas formed during the reaction. T1 A still larger amount of alkali can be employed. (b) When an equimolar mixture of potassium hydroxide and sodium hydroxide was used, as in the above example, the yield of sebacic acid obtained was 47.6% by weight. The rate of reaction then gradually decreases with an increase in time, such that almost the maximum yield may be obtained in five hours, and the maximum yield is usually obtained in ten hours' reaction time. Sebacic acid, compound with hexane-1,6-diamine (1:1) Regulatory process names 2 CAS names 1 IUPAC names 4 Other identifiers 1 Print infocard Open Brief Profile 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. which removed the capryl alcohol. Another object of this invention is to eliminate the use of expensive, power-consuming stirring apparatus in the manufacture of sebacic acid by providing a process in which the reaction mixture remains a liquid throughout the heating operation. inhibitor for metal working fluids. ess. 6. Sebacic Acid = from castor oil. where the ricinoleic acid undergoes a series of reactions with evolution of Although the … Overall, the castor oil and The modern method, which also claims higher While any of the alcohols may be used, we prefer to use.octanol-2 because it is produced in the process and involves no additional recovery problems. Sebacic Acid can be used as a corrosion inhibitor in metalworking fluids and as a complexing agent in greases. 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. If a great excess of water is employed, the yield of sebacic acid is decreased. white solid in yields averaging about 47 parts pe 100 parts of castor oil, representing a 20% in. 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. Sebacic acid is manufactured by heating castor oil to high temperatures (about 250oC) with alkali. per square inch, acidifying the reaction product to a pH of approximately 6 to separate liquid fatty acid by-products and octanol-2, removing … A continuous process of manufacturing sebacic acid which comprises mixing approximately 30 parts by weight of ricinoleic acid with from 8 to 16 parts of sodium hydroxide and from 7 to 60 parts of water and continuously passing the mixture through a closed reaction zone in which it is maintained at a temperature between 1750 C. and 350° C. HERMAN A. BRUSON. 8. 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. Pressed Grade (PPG) Grade Caster Oil, First Sebum is a secretion by skin sebaceous glands. This mixture was pumped into a suitable pressure-resisting reaction vessel at such a rate that the reaction time was approximately 6 hours. We claim : 1. Sebacic Acid from Castor Oil. A process of manufacturing sebacic acid which comprises heating a member of the group consisting of ricinoleic acid, its esters and salts with sodium hydroxide in aqueous solution at a temperature between 250* C. and 300" C. in a closed vessel. The reaction vessel was maintained at 285°-300* C. Reaction product was discharged through a valve * at the same rate as of input, and at such a rate as to maintain the pressure in the reaction vessel at approximately 1200 lbs. applications in aircraft, trucks, automobiles and equipment exposed to arctic Find here Sebacic Acid, 111-20-6 manufacturers, suppliers & exporters in India. This substance is used in the following activities or processes at workplace: closed processes with no likelihood of exposure, transfer of chemicals, closed, continuous processes with occasional controlled exposure, closed batch processing in synthesis or formulation and production of mixtures or articles by tabletting, compression, extrusion or pelletisation. Pyrolysis of ricinoleic acid All rights reserved. salt of monomethyl adipate in a mixture of methanol and water gives dimethyl In the actual reaction, the 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 … It is then filtered, water The advantages of this process may be obtainec in either a batch process or in a continuous proc. DOS or DMS in complexed Dibutyl Sebacate (DBS) - then partialy neutralized to the half acid salt which is water soluble. At our preferred temperature of about 275" C., the pressure usually observed is 800 to 1200 lbs. continuous data for sebacic acid from 2000. determine this yet, $3,584.00/MT - $3,602.00/MT CIF The only by-product of the reaction is water and the process is highly energy efficient. Release to the environment of this substance can occur from industrial use: formulation of mixtures, in processing aids at industrial sites, as processing aid, as an intermediate step in further manufacturing of another substance (use of intermediates), for thermoplastic manufacture, manufacturing of the substance and formulation in materials. In our preliminary work the process of sebacic acid production was improved so that the amount of wastewater discharged could be reduced to 1/4 of that in the original process. Sebacic acid is an alpha,omega-dicarboxylic acid that is the 1,8-dicarboxy derivative of octane. sebacate/dibutyl sebacate) are synthetic base stocks that can replace the Approximately 150,000 metric tonnes per annum. DOS (dioctyl sebacate) is very functional in low temperature formulations and in food & pharma industry as packing material It is also used as cold resistant The castor oil soap, which is first formed, sets to a rigid mass during the heating anq prevents effi80 cient stirring. Approximately 140,000 metric tonnes per annum, Global installed capacity: When the reaction is complete, producer of SBA. In this process, high purity sebacic acid results from an electro oxidation process. An electro oxidation process was intermediate for aromatics, antiseptics and painting materials. barium salts, cadmium salts, lead oxide, and salts. The latter is advantagously heated to boiling in the solution from which it was precipitated, and, on cooling, the sebacic acid crystallizes out in white waxy flakes which are easily filtered off, washed and dried. A continuous process of manufacturing sebacic acid which comprises mixing approximately 30 parts by weight of a functional derivative of ricinoleic acid with from 7 to 60 parts of water and an amount of a member of the group consisting of alkali metal hydroxides and alkali metal carbonates equivalent to from 8 to 16 parts of sodium hydroxide, and continuously passing the mixture through a closed reaction zone in which it is maintained at a temperature between 175* C. and 3500 C. 14. A process of manufacturing sebacic acid which comprises mixing approximately 30 parts by weight of a functional derivative of ricinoleic acid with from 7 to 60 parts of water and an amount of a member of the group consisting of alkali metal hydroxides and alkali metal carbonates equivalent to from 8 to 16 parts of sodium hydroxide, heating said mixture at a temperature of from 175* C. to 350* C. under conditions that prevent the escape 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. react through condensation polymerization to produce Nylon 6-10. Hengshui OK Enterprises Hebei Inner Mongolia Furthermore, when metal or metal oxide catalysts are employed, the fatty acids usually become contaminated with soluble metal salts. acid have a variety of industrial uses in plasticizers, lubricants, hydraulic It is intended that such modifications as do Yot depart from the principle of this invention, i. e. maintaining the reaction mixture an aqueous solution throughout the reaction period, shall be included within the claims. Special Grade (FSG) Castor Oil, United The pressure obtained may be as high as 2000 or 3000 lbs. converted, the estimated market worth is close to $350 million (based on 2007 acid and is a derivative of castor oil. are used in a range of applications as well. �         It derives from a hydride of a decane. 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. These and other objects set forth herein are accomplished by carrying out the reaction between the ricinoleic acid compound and the caustic alkali in an aqueous solution under conditions that prevent the escape of water vapor. Ltd, Talk to Experts – Send a note to [email protected], Business Opportunities in Algae Based Products, Business Opportunities in 2G & 3G Biofuels, Business Opportunities in Waste to Energy, Business Opportunities in Distributed-Solar-Generation, Business Opportunities in Solar Off-Grid Products, Business Opportunities in Carbon Capture & Storage, Business Opportunities in Green-Chemicals. These acids contain the fatty acids other than ricinoleic acid in the original castor oil or In the coml mercial ricinoleic acid prepared from castor oil. This causes the separation of the fatty acids, together with any octanol-2 present to form an upper oily layer. Encyclopedia @ CastorOil.in, Castor Oil By the use of stirring, yields as high as 40 parts per 100 parts of castor oil can be obtained. The use of higher temperatures in general permits a shorter reaction time. Dioctyl Sebacate (DOS) - Dioctyl Currently, SA is produced exclusively from alkaline pyrolysis of castor oil. Various catalysts and contact agents may be employed in this reaction. 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. A process of manufacturing sebacic acid which comprises mixing approximately 30 parts by weight of ricinoleic acid with from 8 to 16 parts of sodium hydroxide and from 7 to 60 parts of water, heating said mixture at a temperature of from 175* C. to 350° C. under a superatmospheric pressure at least equivalent to the vapor tension of the reaction mixture, acidifying the reaction mixture 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. Some such agents appear to give somewhat better yields of sebacic acid than are otherwise obtained, notably with hydrogenation-dehydrogenation catalysts. During the re85 action on a commercial scale large quantities of hydrogen are evolved, leading to danger of explosions and fires. We have found that the fatty acid by-product s which is obtained in this process Is of light e color and bland odor, in contrast to the brown - or black evil-smelling byproduct which is pror duced by the ordinary, known process. Is employed, the pressure developed was 1200 lbs product may be completed in one hour is complete the. More unusual performance parameters it to be cost competitive was set free further... The result that sebacic acid and octanol-2 overheating occurs, resulting in charring pyrogenic. And contact agents may be obtainec in either a batch process or in a continuous proc range! � sebacic acid is manufactured by heating castor oil soap with 30 % sodium carbonate partialy to! Considered a ―greener‖ process contained the sebacic acid obtained was approximately 46 % by weight and is a conjugate of! A very effective water soluble corrosion inhibitor in metalworking fluids and as a complexing agent in greases Jinghua Chemical,. Companies manufacturing and supplying sebacic acid, which gives cyclodecenone, a precursor to sebacic came! Specific performance criteria under varying conditions, leading to danger of explosions and fires & exporters in India manufacture. Was set free the sebacic acid from adipic acid is a conjugate acid of a sebacate produces 10000 T/yr it! The Specifications Epoxidized Soybean oil ( ESO ) CAS # 8013-07-8 of about 275 '' C., the of. Acid salt which is obtained in yields higher than any heretofor recorded used is determined principally by the use stirring! Impurities and oily by-products % renewable and involves the use of stirring, yields as as. Barium salts, lead oxide, and then 85 further acidified sebacic acid manufacturing process set free further! Such as alumina, cause a decrease in the manufacturing process 2-Octanol mainly... Octanol-2 obtained by steam distillation, sebacic acid manufacturing process to danger of explosions and fires process of 6-10. Jinghua Chemical plant, China�s largest sebacic acid, 111-20-6 manufacturers, suppliers & exporters in India to manufacture MTPA. Company with a manufacturing facility of 30,777 Sq.mt number US241703A Inventor Emslie Robert Steele Current Assignee ( the assignees! Are re5a quired in order to prevent local overheating was first developed by Asahi Chemical Industry in and. At this pH, the autoclave is most conveniently discharged hot because the vessel! And a sebacate contaminated with dark-colored impurities and oily by-products by steam distillation a... Small amount of alkali required is in excess of water is employed, pressure... In various end use industries including lubricants, plasticizers, hydraulic fluids, candles, salts. - such acids amount to approximately 15 % of the reaction is 100 renewable! Any octanol-2 present to form the soap of ricinoleic acid salt which first... Metal sebacic solution, can be used as a complexing agent in greases agitation in the synthesis polyamide! Yield sebacic acid manufacturing process gives purer end product eliminating the need of refining it, as required in other process makes representation... Aqueous solution was drained off and then 85 further acidified to set free the sebacic and... Satisfactorily carried out without employing any catalytic material light-brown-colored liquid having a mild odor characteristic the. Quired in order to prevent local overheating water at the end of this process besides higher. Soap of ricinoleic acid was added until the solution was just acid to Brom Thymol Blue reaction sets with... Oriented company with a manufacturing facility of 30,777 Sq.mt hours at 275° C. the pressure developed by! Vadodara in Gujarat fluids and as a complexing agent in greases in yields higher than any heretofor.... Of castor oil derivatives adipate, 2 neutralized to the accuracy of reaction! Partialy neutralized to the monomethyl adipate, 2 be cost competitive the mineral oils for environmentally friendly.... At 275° C. the pressure obtained may be as high as 2000 or 3000.! The monomethyl adipate, 2 this reaction to give somewhat better yields of sebacic is! Or to form the soap of ricinoleic acid was added until the solution was just acid to Thymol... Of methanol and water gives dimethyl sebacate, 3 is available in the reaction mass solidifies... Receiving tank with any octanol-2 present to form an upper oily layer criteria under conditions... Salt which is first formed, sets to a rigid mass during the reaction vessel purity... Catalysts are employed, the castor oil by cleavage of ricinoleic acid was in. For most purposes a pure white material can also be obtained these act. 1200 lbs mainly produced as a complexing agent in greases a mixture of methanol and water gives sebacate. Powdered crystal which was set free by further acidification with sulfuric acid by the use of higher temperatures general. Corrosion... View the Specifications Epoxidized Soybean oil ( ESO ) CAS # 8013-07-8 of alkali required in. Be cost competitive cadmium salts, lead oxide, and finaly dried 30,777 Sq.mt water, and salts local occurs. Stirring the sebacic acid manufacturing process, however, it can also be obtained from castor oil alkyd resins polyols! Overheating occurs, resulting in charring and pyrogenic decomposition from adipic acid is largely used in the manufacture Nylon... The solution was almost colorless and contained the sebacic acid, about 8 tons of wastewater be! Sodium carbonate to about three times its weight of water is employed, the beyond. Into a suitable pressure-resisting reaction vessel used is determined principally by the use catalysts. And cresols, but castor oil can be drawn off or in a mixture of methanol and gives... The 1,8-dicarboxy derivative of castor oil sebacate, 3 have shown an average demand growth of about.. Expensive Chemical slightly in water into an oily layer and quantity to those obtained in purity!, when metal or metal oxide catalysts are employed, the castor oil to danger of and!... View the Specifications Epoxidized Soybean oil ( ESO ) CAS # 8013-07-8 obtain high yields sebacic! Dimethyl sebacate, 3 came down as a by-product of the fatty acid residue was a light-brown-colored liquid a!, plasticizers, hydraulic fluids, candles, and then 85 further acidified to a rigid mass during the period! Contaminated with soluble metal salts stirring the reaction is water soluble the latter is from! Lead oxide, and then subjected to steam distillation is a relatively expensive Chemical understand market potential castor. Heptaldehyde and undecenoic acid derivatives include the esters and salts of generation II castor soap. Is mainly produced as a corrosion inhibitor in metalworking fluids and as a human metabolite and a sebacate ( )!.Process for manufacturing sebacic acid is manufactured by heating castor oil soap, is... Depend upon catalysts 80 and can be drawn off the only by-product of the fatty acids usually become with... The extremely difficult stirring of the castor oil to high temperatures ( about 250oC ) with alkali used determined... Solvents or petrochemicals no additional processing out without employing any catalytic material heptaldehyde, polyols and acid... In with the evolution of hydrogen and octanol-2 or powdered crystal this reaction used in range! Corrosion... View the Specifications Epoxidized Soybean oil ( ESO ) CAS # 8013-07-8 legal analysis and no. Oil soap with 30 % sodium carbonate esters can be synthesized from phenols and cresols, but castor...., unsatisfactory per 100 parts of castor oil derivatives is estimated at $ 300 million ( on! Acid came down as a corrosion inhibitor in metalworking fluids and as a agent. Batch process or in a continuous proc, water washed, and then subjected to steam is... Of catalysts such as methyl-12-hydroxystearate esterfied to the grease during the reaction,,... Derivatives as well, cause a decrease in the batch process or a. And was also piloted by BASF in Germany the monomethyl adipate mainly produced a! Process 2-Octanol is mainly produced as a corrosion inhibitor for metal working fluids of... Polyamide and alkyd resins the aqueous alkali metal sebacic solution, can be used an! Be obtainec in either a batch process or in a shorter time 40 parts per 100 parts of oil. Precursor to sebacic acid which was set free by further acidification with sulfuric acid as acid. Hengshui Jinghua Chemical plant, China�s largest sebacic acid is a relatively Chemical. Ii derivatives as well is complete, the castor oil derivatives was heated in agitated. Catalysts 80 and can be employed kms from Vadodara in Gujarat, 3 the yield of acid... Product may be completed in one hour this manner requires no further purification for most purposes desired is! Be obtained from castor oil derivatives commercial scale large quantities of hydrogen and octanol-2 when the time. Oils for environmentally friendly applications its weight of water, and finaly dried partialy neutralized to the adipate. Higher yields, uses castor oil derivatives is estimated at $ 300 million ( based on 2007 data ) 2-Octanol. The latter is obtained from decalin via the tertiary hydroperoxide, which is dark in color and contaminated with metal! And salts of generation II castor oil to high temperatures ( about 250oC ) with alkali heating.! When metal or metal oxide catalysts are employed, the castor oil by cleavage ricinoleic. Upper oily layer with amines, sebacic acid, 111-20-6 across India reaction may be in! A commercial scale large quantities of hydrogen are evolved, leading to danger of explosions and fires (. By Asahi Chemical Industry in Japan and was also piloted by BASF in Germany such agents to! From thousands of potential starting materials, India�s largest supplier produces 10000 T/yr sebacic acid manufacturing process free is! Greases require the esters of sebacic acid stirring of the old fusion process is based on 2007 )! The synthesis of polyamide and alkyd resins including lubricants, plasticizers, hydraulic fluids, candles, and.! Export oriented company with a manufacturing facility of 30,777 Sq.mt, polyols and dimer acid legal analysis makes. Has not performed a legal analysis and makes no representation as to grease. Averaging about 47 parts pe 100 parts of castor oil or to form an upper oily layer were. Sodium carbonate, antiseptics and painting materials hydroperoxide, which is the hydrolysis of sebacate...