C36 Dimer acid
(Octadecadienoic acid) dipolymer
CAS: 61788-89-4
Molecular Formula: C36H64O4
C36 Dimer acid - Names and Identifiers
| Name | (Octadecadienoic acid) dipolymer |
| Synonyms | Dimer Acid C36 Dimer Acid dilinoleic acid Dimer Fatty acid FATTYACIDS,DIMERACIDS Fatty acids, diMeracids, C18 (Octadecadienoic acid)dipolymer Fatty acids, C18-unsatd., dimers (Octadecadienoic acid) dipolymer Fatty acids, C18 unsaturated dimers FATTYACIDSUNSATURATEDC18DIMERSDISTILLED FATTYACIDSUNSATURATEDC18DIMERSNON-DISTILLED 9-[(3Z)-non-3-en-1-yl]-10-octylnonadecanedioic acid |
| CAS | 61788-89-4 |
| EINECS | 500-148-0 |
| InChI | InChI=1/C36H68O4/c1-3-5-7-9-11-16-22-28-34(30-24-18-14-20-26-32-36(39)40)33(27-21-15-10-8-6-4-2)29-23-17-12-13-19-25-31-35(37)38/h11,16,33-34H,3-10,12-15,17-32H2,1-2H3,(H,37,38)(H,39,40)/b16-11- |
C36 Dimer acid - Physico-chemical Properties
| Molecular Formula | C36H64O4 |
| Molar Mass | 560.91 |
| Density | 0.931g/cm3 |
| Boling Point | 667.7°C at 760 mmHg |
| Flash Point | 371.6°C |
| Vapor Presure | 0-0.029Pa at 25℃ |
| Appearance | Viscous |
| Storage Condition | Room Temprature |
| Refractive Index | 1.478 |
| Physical and Chemical Properties | Colorless transparent liquid. Relative density 0.95, flash point 280-350 deg C. Soluble in acetone, ethanol, ether and aliphatic, naphtha and other almost all solvents |
| Use | Mainly used as polyamide resin, epoxy resin modifier and fuel oil, lubricating oil, cutting oil additives |
C36 Dimer acid - Upstream Downstream Industry
| Raw Materials | Oleic acid |
| Downstream Products | Polyamide Resin |
C36 Dimer acid - Reference
| Reference Show more | 1. Zeng Rong, qiao xiu-Wen, Qi Yu, etc. Ultrasound-assisted preparation of acicular nano-activated calcium carbonate [J]. Inorganic salt industry, 2014, 46(2):21. 2. Zeng Rong, qiao xiu-Wen, Qi Yu, etc. Study on synthesis and modification of acicular nano-active calcium carbonate [J]. Journal of Shihezi University (self-Science Edition), 2013, 31(6):752-758. |
C36 Dimer acid - Introduction
Dimer acid, usually a dimer fatty acid, is a mixture of complex components
Last Update：2022-10-16 17:27:11
C36 Dimer acid - Reference Information
| LogP | 1-14.81 at pH2 |
| EPA chemical substance information | information provided by: ofmpeb.epa.gov (external link) |
| What is a dimer acid? | dimer acid, refers to the natural oil linoleic acid as the main component of the straight chain of unsaturated fatty acids or unsaturated fatty acid esters in the white clay catalysis, the dimer is self-polycondensed by a Diels-Alder cycloaddition reaction or the like. It is a mixture of isomers in which the main components are dimers, small amounts of trimers or multimers and minor amounts of unreacted monomers. |
| Structure | the three major isomers of dimer acids, I .e., monocyclic, bicyclic and acyclic isomers. Because the polymerization of unsaturated fatty acids is a complex chemical reaction, the unsaturated fatty acid molecules involved in the reaction can be combined with each other in different ways, thus producing a lot of isomers, such as the double bond of CIS, inverse geometric isomers, component isomers resulting from the "head-to-head" or "head-to-tail" joining of molecules, linear or cyclic structural isomers, and the like. |
| physical properties | The dimer acid has a molecular formula of C36H64O4, a molecular weight of 560.91, and a relative density of 0.95. Pure dimer acid is light yellow transparent viscous liquid, with good thermal stability: no crystallization at low temperature of -20 ℃, no loss of transparent fluidity; No evaporation at 250 ℃, no gelation. When heated in air, the color will be significantly darker. Exposure to metal ions, especially copper and iron ions, will promote color deterioration. Hydrogenated dimer acid is an almost colorless, transparent liquid that is less likely to deepen in color even when heated. Dimer acid is insoluble in water, but soluble in ether, ethanol, acetone, chloroform, benzene, petroleum solvents. The structure of the dimer acid is also very different due to the different raw materials used. Table 1 lists the relationship between some dimer acid raw materials and the structure. In the production, different raw materials can be selected according to the requirements of the final product on the structure of the dimer acid. The United States, Japan and other countries mainly to tall oil fatty acid as raw material, in China, most of the soybean oil, cotton oil, sunflower oil, corn germ oil and low erucic acid rapeseed oil fatty acid as raw material. Unsaturated fatty acid synthesis of Dimer acid, the unsaponifiable matter content according to the difference of catalyst and polymerization technology, there is obvious high and low. High unsaponifiable matter content in 3 ~ 5%; And low unsaponifiable matter content is only 1 ~ 2%. The commercial dimer acid is mainly a single distilled dimer acid. Different varieties of Dimer acid, its performance is also different, the same variety is also due to the use of different raw materials and the nature of the difference. Such as the United States dimer content of 87%, 83%, 75% dimer acid were high, medium and low grade three ordinary commodity dimer acid. These products are generally referred to as the first distilled or single distilled dimer acid, such as the first distilled dimer acid distillation again to be distilled dimer acid (or double distilled dimer acid), the dimer content of up to 95%. Also known as high-purity dimer acid. If the dimer acid is hydrogenated again, a hydrogenated dimer acid with very light color and excellent oxidation resistance can be obtained. High purity dimer acid and hydrogenated dimer acid are mostly used in some occasions requiring special properties. |
| reaction mechanism | A dimer acid is obtained by heat polymerization of an unsaturated fatty acid under the action of a catalyst. The reaction mechanism of dimerization, at present, the more consistent view is the theory of Diels-Alder addition reaction between conjugated and non-conjugated unsaturated fatty acids. For example, with cotton oil fatty acid as raw material, the double bond of linoleic acid is co-formed after heating, and oleic acid is dehydrogenated into dienoic acid under the action of catalyst, and the double bond is also co-formed after heating, these two co-substituted dienoic acids become the Diene in the reaction, while the non-conjugated linoleic acid and undehydrogenated oleic acid become the diene affinity in the reaction, both in 1, the addition at the 4-position produces various substituents of cyclohexene dimer acids, which are mostly viscous substances. Of course, two dehydrogenated oleic acid can also be synthesized by free radical reaction, but in the raw materials mainly oleic acid and linoleic acid, most of them are polymerized by Diels-Alder reaction. The dimer acid may also be mixed with other dibasic acids and then mixed with a polyol to form a polyester. The properties of the mixed polyesters are intermediate between those of the polyesters formed from a single dibasic acid or a dimer acid. This provides advantages for the synthesis of polyesters of various properties. |
| synthesis method | The Clay catalytic dimerization method is the most important and most valuable production method in industry. The White Earth catalyzed dimerization process was first reported in the Johnson patent. Barrett's patent lists in detail the various types of clay that can be used, and particularly recommends bentonites containing more than 75% silica montmorillonite. The patent also mentions the acidity of the clay. The pH of the clay should be between 2 and 7, preferably between 3 and 5. Subsequently, many patents describe the improvement of the clay catalytic process. The basic starting point is to improve the dimerization/trimerization ratio and the total product yield. Adding a small amount of alkali in the reaction mixture can increase the dimerization/trimerization ratio, the bases that can be used are NaOH, Ca(OH)2, Mg(OH)2, Ba(OH)2 and natural alkaline clay. The patent states that on addition of the base, the reaction temperature must be increased by 10 °c to obtain the same yield. After the addition of alkali, the dimer obtained by the tall oil fatty acid dimerization had a trimer content of 16%, compared to 20.5% in the absence of alkali. A method for increasing the dimerization/trimerization ratio is also to add a small amount of ammonia or amine, 1-thio-2-naphthol, arylsulfonyl halide. The natale et al. patent uses alkaline metal oxide or alkaline earth metal oxide modified clay catalysts for the synthesis of dimer acids in a two-step polymerization reaction. The biggest advantage of this method is: the fatty acid that is not polymerized in the first step is not changed by the catalyst, and the remaining unsaturated acid can be separated and the second polymerization can be continued, the total yield of dimer in two-step polymerization can generally reach 65% ~ 75%. The dimer has light color and low viscosity; the dimerization/trimerization ratio exceeds that obtained with other catalysts (when the Feedstock consists of tall oil or soybean oil fatty acids, The ratio can reach 8: 1). Kathrgn combines a certain amount of lithium carbonate, lithium hydroxide or other lithium salts with montmorillonite, Sepiolite and the like as a fatty acid polymerization catalyst, and also adopts a two-step polymerization method to obtain similar results as those of Natale patent. The disadvantage of the catalytic polymerization of clay is that the clay has to adsorb a certain amount of products. Discarding clay not only causes product loss, but also causes environmental pollution. The process developed by Robert et al. to remove fatty acids by washing the clay with hot water at 90 °c overcomes this disadvantage and makes the recovered clay reusable. Europe and the United States in the 20th century 70~90's about Clay catalyzed dimerization method of many patents, the core technology is to improve the catalytic process, in order to improve the dimer acid/trimer acid ratio and the total product yield. |
| Use | dimer acid has similar reactivity with common fatty acids, can be formed with alkali metal metal salts, can be derived into acid chloride, amide, ester, Diamine, diisocyanate and other products. Dimer acid with long chain alkane and cyclic structure, and a variety of solvents have good mutual solubility, good thermal stability, in the winter is not cured, and the vapor pressure still has anti-corrosion effect, good lubricity. Therefore, it is widely used as an additive for fuel oil, lubricating oil, calender oil, hydraulic oil, cutting oil and the like. The ester of this product can be effectively used as a viscosity stabilizer in a wide temperature range; The metal salt of this product is widely used as a thickener for Grease. The application of the product in the manufacture of polyester resin accounts for 80-90% of the total consumption of Dimer acid, and the rest is used for oil additives, surfactants, synthetic paints, inks, adhesives, curing agents, etc. mainly used as modifier of polyamide resin, epoxy resin and additive of fuel oil, lubricating oil and cutting oil |
| production method | from the drying oil, semi-drying oil and other vegetable oils, such as soybean oil, cottonseed oil, rice bran oil containing high linoleic acid, the natural oil of oleic acid is refined to obtain fatty acid, and then prepared by batch pressure catalytic polymerization or continuous catalytic polymerization or intermittent atmospheric pressure methanol vapor oxygen-discharging polymerization. |
Last Update：2024-04-09 21:04:16
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Raw Materials for C36 Dimer acid
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