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Send Email| Name | Oleic acid |
| Synonyms | red oil oleoate Metaupon Oleic acid Oleic acid, AR Metal polish,red OmniPur Oleic Acid 9Octadecenoicacid(9Z) Polishing compound,red 9-cis-Octadecenoicacid cis-9-Octadecenoic acid 9-Octadecenoic acid, cis- Oleic acid CETEARYL ALCOHOL Manufacturer |
| CAS | 112-80-1 |
| EINECS | 204-007-1 |
| InChI | InChI=1/C18H34O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h9-10H,2-8,11-17H2,1H3,(H,19,20)/b10-9- |
| InChIKey | ZQPPMHVWECSIRJ-KTKRTIGZSA-N |
| Molecular Formula | C18H34O2 |
| Molar Mass | 282.46 |
| Density | 0.89 g/mL at 25 °C(lit.) |
| Melting Point | 13-14°C(lit.) |
| Boling Point | 360 °C |
| Flash Point | 133°F |
| JECFA Number | 333 |
| Water Solubility | negligible |
| Solubility | Insoluble in water, miscible in alcohol and ether, soluble in benzene and chloroform |
| Vapor Presure | 52 mm Hg ( 37 °C) |
| Vapor Density | 1.03 (vs air) |
| Appearance | oily |
| Specific Gravity | 0.892 (20/4℃) |
| Color | Colorless to pale yellow |
| Odor | Peculiar Lard-Like |
| Merck | 14,6828 |
| BRN | 1726542 |
| pKa | pKa 5.35(H2O,t =25) (Uncertain) |
| Storage Condition | -20°C |
| Stability | Stable. Combustible. Incompatible with strong oxidizing agents, aluminium. |
| Sensitive | Air Sensitive |
| Refractive Index | n20/D 1.377 |
| MDL | MFCD00064242 |
| Physical and Chemical Properties |
density 0.89
|
| Use | For soap, lubricants, flotation agent, ointment and oleate, etc. |
| Risk Codes | R23/24/25 - Toxic by inhalation, in contact with skin and if swallowed. R34 - Causes burns R40 - Limited evidence of a carcinogenic effect R43 - May cause sensitization by skin contact R36/37/38 - Irritating to eyes, respiratory system and skin. R38 - Irritating to the skin |
| Safety Description | S36/37 - Wear suitable protective clothing and gloves. S37/39 - Wear suitable gloves and eye/face protection S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S36 - Wear suitable protective clothing. S36/37/39 - Wear suitable protective clothing, gloves and eye/face protection. |
| UN IDs | UN 1198 3/PG 3 |
| WGK Germany | 2 |
| RTECS | LP8925000 |
| FLUKA BRAND F CODES | 10 |
| TSCA | Yes |
| HS Code | 29161500 |
| Toxicity | LD50 i.v. in mice: 230±18 mg/kg (Or, Wretlind) |
colorless or light yellow to red oily liquid with lard-like aroma and taste. Exposure to air can be gradually oxidized and dark color, strong heating in the air can lead to decomposition, almost insoluble in water, miscible in ethanol, ether, benzene and volatile and non-volatile oil. Oleic acid, together with other fatty acids, is present in all animal and vegetable fats and oils in the form of glycerides. Oleic acid and nitric acid, the isomerization of trans isomer, the melting point of oleic acid is 44~45 deg C; Hydrogenation of stearic acid; Potassium permanganate oxidation of N-nonanoic acid and azelaic acid mixture. Oleic acid as a result of double bonds, long-term storage in the air can occur during the oxidation, local transformation into carbonyl containing substances, there is a putrefaction of the Ha la flavor, which is the cause of deterioration of oil. Commercial oleic acid, generally containing 7%~ 12% of saturated fatty acids.
Use
It can be used as a lubricant for drilling mud. The sodium or potassium salt of oleic acid is one of the components of soap. Pure sodium oleate has good decontamination ability, can be used as emulsifier and other surfactants, and can be used for the treatment of cholelithiasis. Other metal salts of oleic acid can also be used in waterproof fabrics, lubricants, polishing agents, etc., and its barium salt can be used as a rodenticide.
Introduction
Biochemical research, gas chromatography to compare samples, verification of ammonia, calcium and copper, determination of calcium, magnesium and sulfur. Activate protein kinase C(protein kinase C) in liver cells.
Safety
mice were injected intravenously with LD50: (230±18) mg/kg.
Reference Information
| FEMA | 2815 | OLEIC ACID |
| hydrophilic and hydrophilic balance value (HLB value) | 1 |
| unsaturated fatty acid | oleic acid is an unsaturated fatty acid with a carbon-carbon double bond in its molecular structure, which is the fatty acid that makes up olein. One of the most widespread natural unsaturated fatty acids is present. Oleic acid can be obtained by hydrolysis of oil, and its chemical formula is CH3(CH2)7CH = CH(CH2)7 · COOH. Oleic glycerides are one of the main components of olive oil, palm oil, lard and other animal and vegetable oils. Industrial products often contain saturated fatty acids (palmitic acid, stearic acid) 7 ~ 12% and a small amount of other unsaturated fatty acids (linoleic acid). Colorless oily liquid. Specific gravity 0.895(25/25 ℃). Freezing point 4 ℃. Boiling point 286 ℃(13,332 Pa). Refractive index 1.463(18 ℃). Iodine value 89.9, acid value 198.6. Insoluble in water, soluble in alcohol, benzene, chloroform, ether and other volatile oils or non-volatile oils. When exposed to the air, especially when it contains some impurities, it is easy to be oxidized, the color turns yellow or brown, and has a rancidity smell. Decompose when heated to 80~100 ℃ under normal pressure. It is made from animal and vegetable oils through saponification and acidification. Oleic acid is an indispensable nutrient in animal food. Its lead salt, manganese salt, and cobalt salt are paint driers; copper salt is a fishing net preservative; aluminum salt can be used as a fabric waterproofing agent and a thickening agent for certain lubricating oils. Epoxidation of oleic acid can produce epoxy oleate (plasticizer). The production of azelaic acid (the raw material of polyamide resin) by oxidative cracking. Closed and dark storage. Oleic acid mainly exists in large quantities in animal and vegetable oils in the form of glycerides. Some simple oleic acid esters can be used in textile, leather, cosmetics and pharmaceutical industries. The alkali metal salt of oleic acid is soluble in water and is one of the main components of soap. Lead, copper, calcium, mercury, zinc and other salts of oleic acid are insoluble in water and can be used as dry lubricant, paint desiccant and waterproof agent. oleic acid mainly comes from nature. oleic acid can be obtained by saponification and acidification of oils with high oleic acid content. Oleic acid has cis and trans isomers. Natural oleic acid is a cis structure (the trans structure cannot be absorbed by the human body), which has a certain effect on softening blood vessels. It also plays an important role in the metabolism of humans and animals, but the human body itself The synthesized oleic acid cannot meet the needs and must be taken from food, so edible oil with higher acid content is good for health. |
| Determination of the unsaturation of oleic acid | There is an unsaturated double bond in the oleic acid molecule, which has the chemical properties of monounsaturated carboxylic acid and can undergo an addition reaction with bromine. Add 2ml of CCl4 and 0.5mL of oleic acid to the test tube and mix. Take another test tube, hold CCl4 1mL, add 1 drop of bromine, shake well. Drop the CCl4 solution of bromine into the CCl4 solution of oleic acid, shake the test tube, and the color of bromine recedes: C17H33COOH Br2 → C17H33Br2COOH. |
| main use | sodium or potassium salt of oleic acid is one of the ingredients of soap. Pure sodium oleate has good decontamination ability and can be used as surfactant such as emulsifier. The lead salt, manganese salt, and cobalt salt of oleic acid are paint driers; copper salt is a fishing net preservative; aluminum salt can be used as a fabric waterproofing agent and a thickening agent for certain lubricating oils. Other metal salts of oleic acid can also be used in polishing agents, etc., and its barium salt can be used as a rodenticide. The epoxidation of oleic acid can produce epoxy oleate (plasticizer). Azelaic acid is prepared by oxidation, which is the raw material of polyamide resin (nylon). Polymerization production of dimer acid, manufacture of semi-dry alkyd resin paint, paint, ink, paint. It can be used as raw materials for plastic plasticizers, engineering plastics, synthetic fibers, nylon 8 and 9, soft linen agents, wood preservative additives, leather auxiliaries, various textile oil additives, and finishing agents; it can be used to produce synthetic detergents, Washing soap, emulsifier S-80, surfactants and dispersants for various cosmetic products; used as printing ink solvents, composite adhesives; used as collectors and demulsifiers for mineral processing; it can also be used in metal processing and lubricating oils such as gear oil, rolling oil, hydraulic oil, metal cutting oil, etc. The wool spinning industry is used to prepare antistatic agents and lubricating softeners. The wood industry is used to prepare water-repellent paraffin emulsion. It can also be used as pesticide emulsifier, lubricant, printing and dyeing auxiliaries, industrial solvents, metal mineral flotation agents, mold release agents, grease hydrolysis agents, used to prepare carbon paper, typewriting paper, ballpoint pen oil and various oleates. As a chemical reagent, used as a chromatographic comparison sample and used for biochemical research, approved calcium, ammonia, copper, and determined magnesium, sulfur, etc. Activation of protein kinases in liver cells. 75% alcohol solution of oleic acid can be used as rust remover. |
| oleic acid and linoleic acid | oleic acid and linoleic acid are unsaturated long-chain fatty acids. The molecule contains one and two double bonds respectively. In addition to providing animal energy, it is also an indispensable nutrient. In animals, it cannot be synthesized from oils and carbohydrates, so it is called essential fatty acids. Some animals can produce linoleic acid from arachidonic acid. The two acids are mostly found in vegetable oils, and there is no shortage of poultry and pigs that ingest vegetable oil-containing feed. However, the required amount of linoleic acid has recently appeared in poultry breeding standards. Because linoleic acid is metabolized in the body and finally produces EPA (eicosapentaenoic acid). EPA is a series of n-6 fatty acids, which are responsible for important physiological functions in the body and are the components of phospholipids that constitute cell membranes. These metabolic end products starting from linoleic acid are mostly contained in fish oil. Adding fish oil containing EPA and DHA to the feed of laying hens can reduce cholesterol after eating the eggs. |
| preparation method | (1) oleic acid is directly extracted from vegetable oil, I .e. it is extracted by saponification method. under stirring, steam is blown into the oil to raise the temperature to 80~100 ℃, and then alkali liquid is added to hydrolyze the oil. After hydrolysis, mixed fatty acids are obtained, and they are separated by distillation and cooling. This method is labor-intensive, energy consumption, alkali consumption is large, generally not used. (2) oleic acid was prepared from vegetable oil or animal oil by atmospheric catalytic hydrolysis method, and alkylbenzene sulfonic acid was used as the catalyst. Intermittent medium pressure catalytic cracking method can also be used. Zinc oxide can be selected as the catalyst, the pressure is 10.13 × 105~35.46 × 105Pa, and the temperature is 150~230 ℃. Continuous, countercurrent and high-pressure cracking method can also be used, the pressure is 5~5.2MPa, the temperature is 260 ℃, and the catalyst can be zinc oxide. This method has higher benefits than the previous two, but it is not suitable for oils containing high unsaturation and hydroxyl groups. Using the above three methods, mixed fatty acids can be prepared, and then separated and refined. Firstly, distillation is used for crude separation, and distillation is carried out under reduced pressure (0.133 × 103~1.07 × 103Pa). Maintain distillation temperature not exceeding 260 ℃. The distilled fatty acids are further rectified using their boiling point difference. According to the different melting points of various fatty acids, the crystallization method can be used for refining. It can also be refined by solvent extraction. (3) synthetic oleic acid. In 1925, oleic acid was synthesized from ethyl acetoacetate. With the development of petrochemical industry, the process of synthesizing oleic acid has also been developed, and oleic acid can be produced from petroleum olefins. |
| toxicity | natural fatty acid, non-toxic. can be safely used in food (FDA,§ 172.862,2000). LD5074g/kg (rat, oral). |
| use limit | FEMA(mg/kg): soft drinks 0.25~0.40, cold drinks 30, candy 3.5, baked goods 25, seasoning 0.02. |
| use | GB 2760-96 specifies as a processing aid. Defoamer; perfume; binder; lubricant. It is used to make soap, lubricant, flotation agent, ointment and oleate, etc., and is also a good solvent for fatty acids and oil-soluble substances It is used for precision polishing of precious metals and non-metals such as gold and silver, Electroplating industry polishing Used as analytical reagent, solvent, lubricant and flotation agent, and also used in sugar processing industry Oleic acid is an organic chemical raw material, which can be produced by epoxidation Epoxy oleate, used as plastic plasticizer, azelaic acid can be produced by oxidation, which is the raw material of polyamide resin. In addition, oleic acid can also be used as pesticide emulsifier, printing and dyeing auxiliaries, industrial solvents, metal mineral flotation agents, mold release agents, etc., and can also be used as raw materials for the production of carbon paper, round bead crude oil and typing wax paper. Various oleate products are also important derivatives of oleic acid. As a chemical reagent, it is used as a chromatographic comparison sample and for biochemical research to detect calcium, copper, magnesium, sulfur and other elements. Biochemical research. Standard for analysis by gas chromatography. Verification of ammonia, calcium and copper. Determination of calcium, magnesium and sulfur biochemical research, gas chromatography comparison samples, verification of ammonia, calcium and copper, determination of calcium, magnesium and sulfur. Activate protein kinase C(protein kinase C) in liver cells. uncoupling of oxidative phosphorylation. Inhibition of 2, 4-dinitrophenol-activated ATPase. The addition of serum albumin has the opposite effect. Standard for gas chromatography analysis. Verification of ammonia, calcium and copper. Determination of calcium, magnesium and sulfur. Activation of protein kinase in hepatocytes C. |
| production method | oleic acid, together with other fatty acids, exists in all animal and vegetable oils in the form of glycerides. In animal fat, oleic acid accounts for about 40-50% of fatty acids. The content of vegetable oil varies greatly, up to 83% in tea oil, 54% in peanut oil and only 5-6% in coconut oil. Oleic acid is a co-product in the production of stearic acid. Industrial stearic acid and industrial oleic acid actually contain other fatty acids. There are many oil raw materials used to produce stearic acid and oleic acid. In industry, mixed oil formula is generally used, such as melted tallow 30%, melted pig fat 10%, bone fat 40% and cottonseed oil 20%. Among the mixed fatty acids obtained by refining and hydrolysis, the melting points of saturated acid and unsaturated acid are quite different. The yield of stearic acid and oleic acid is mainly determined by the oil ester formula. Under normal circumstances, 30-50% oleic acid and 50-70% stearic acid can be obtained by cold pressing. Hydrolysis of animal and vegetable fats and emulsions at 105 ℃, purification with stearic acid, removal of stearic acid by one pressing, separation of crude oleic acid, dehydration, distillation, freezing. The palmitic acid is removed by secondary pressing, and finally the finished product is obtained by dehydration and refining. This method can coproduce stearic acid. When stearic acid is also made from oleic acid, oleic acid will also be coproduced. Raw material consumption quota: 1950kg/t for animal and vegetable oils and 210kg/t for sulfuric acid (98%). Use oils and fats containing a certain amount of oleic acid as raw materials, such as tallow, lard, and palm oil, to decompose fatty acids, dissolve and cool the fatty acids with solvents, and remove solid fatty acids to obtain crude oleic acid. Then dissolve in solvent and cool at low temperature to crystallize oleic acid. |
| spontaneous combustion temperature | 363°C |