32953-65-4

Basic information

• Product Name: octyl oleate
• Synonyms: 9-Octadecenoic acid (9Z)-, octyl ester; Octyl oleate; octyl (9Z)-octadec-9-enoate
• CAS NO: 32953-65-4
• Molecular Formula: C₂₆H₅₀O₂
• Molecular Weight: 394.674
• EINECS: 251-304-7
• Mol File: 32953-65-4.mol

Chemical Properties

• Boiling Point: 469.2°C at 760 mmHg
• Flash Point: 82.2°C
• Density: 0.867g/cm³
• Vapor Pressure: 5.6E-09mmHg at 25°C
• Refractive Index: 1.459
• CAS DataBase Reference: octyl oleate(CAS DataBase Reference)
• NIST Chemistry Reference: octyl oleate(32953-65-4)
• EPA Substance Registry System: octyl oleate(32953-65-4)

Safety Data

• Hazardous Substances Data: 32953-65-4(Hazardous Substances Data)

Upstream product

• 111-87-5 octanol 
• 112-62-9 Methyl oleate 
• 112-80-1 cis-Octadecenoic acid 
• 143-28-2 oleoyl alcohol 

Downstream Products

• 106-84-3 octyl 3-octyloxiran-2-octanoate 

Relevant articles and documents

Guanidine based task specific ionic liquids for the synthesis of biolubricant range esters under solvent-free condition

Guanidine-based task specific ionic liquids (ILs) were synthesized from the reaction of 1,1,3,3-tetramethyl guanidine with protic acids and used for the synthesis of higher alcohol esters of fatty acids as biolubes under solvent free condition. The synthesized 1,1,3,3-tetramethylguanidinium hydrogen sulphate (TMG·HSO4) was found to be most effective among the different ILs including 1,1,3,3-tetramethylguanidinium acetate (TMG·Ac), 1,1,3,3-tetramethylguanidinium hydrogen phosphate (TMG·H2PO4) and 1,1,3,3-tetramethylguanidinium trifluoro acetate (TMG·TFA). The effect of various reaction parameters such as reaction temperature, reaction time, catalyst amount etc. has been studied. After completion the reaction the esterification product was isolated and the recovered IL was reused for several runs without loss in catalytic activity.

PROCESS FOR PREPARING BIODEGRADABLE LUBRICANT BASE OILS

The invention discloses an improved process for preparing fatty acid esters with 100 mol % selectivity suitable as biodegradable lubricant base oils, comprising contacting a fatty compound with an alcohol in presence of a solid, phosphonate catalyst having molecular formula: M(X)2-nYn.mH2O where X refers to phenyl phosphonate, Y refers to HPO42? or HPO32?, M refers to a metal or metalloid ion preferably taken from the group consisting of Zr, Zn, Cd, Al, Sn, La and Ce, the value of n varies from 0.2 to 1.8 and the value of m varies from 0 to 5, wherein the fatty compound is a fatty acid or fatty acid methyl or ethyl ester or vegetable oil or animal fat or their mixture thereof and alcohol is a monohydric alcohol with 6 to 22 carbon atoms or a polyol with at least two hydroxyl groups.

Esterification of oleic acid in [Bmim]BF4/[Hmim]HSO4 + TX-100/cyclohexane ionic liquid microemulsion

Esterification of oleic acid was carried out in a 1-butyl-3-methylimidazolium tetrafluoroborate ([Bmim]BF4)/Triton X-100 + 1-hexyl-3-methylimidazolium hydrogen sulfate ([Hmim]HSO4)/cyclohexane microemulsion. A pseudo ternary phase diagram of the designed systems was drawn to investigate the phase behavior of the microemulsion, with the surfactant [Hmim]HSO4 acting as a catalyst. The effects of various reaction parameters were explored. The results showed that the maximum yield of lauryl oleate reaches 91.17% and its selectivity reaches 98.55% under optimum reaction conditions. The reaction was carried out with 8 wt% catalyst at 373 K for 6 h. The molar ratios of [Bmim]BF4 to the surfactant and of oleic acid to lauryl alcohol were 0.24 and 0.2, respectively. Comparison reactions between different alcohols and oleic acid were also performed, and the results showed that long alkyl chain alcohols promote the reaction rate. UV-vis absorption spectra demonstrated that the generated water enters the [Bmim]BF4 microdomain of the ionic liquid microemulsions. A possible mechanism of the reaction was also presented. All the results indicate that the [Bmim]BF4/TX-100 + [Hmim]HSO4/cyclohexane microemulsion is a very efficient catalyst system for esterification reactions. This journal is

Studies on the lipase-catalyzed esterification of alkyl oleates in solvent-free systems

The alkyl oleates were prepared by esterification of oleic acid with alkyl alcohols catalyzed by the lipase from Candida sp. 99-125 in solvent-free system. The influence of several factors, including enzyme concentration, temperature, molar ratio between oleic acid and alkyl alcohols, the structure of alcohols and water content, was also investigated. The results indicated that the reactions catalyzed by Candida sp. lipase at 20 °C, in the presence of 5% (w/w) lipase, on the molar ratio of 1:1 between oleic acid and alcohols, afforded products in high yield and showed high selectivity to primary alcohols. The enzymatic synthesis gave purer products, compared with the conventional chemical synthesis. The lipase from Candida sp. 99-125 was identified to be an effective catalyst in the esterification of alcohol and oleic acid at low temperature.

Synthesis of biolubricants using sulfated zirconia catalysts

Synthesis of biomass-derived lubricants via esterification, transesterification, and simultaneous reactions of both was studied by using sulfated zirconia catalysts. Soybean oil or free fatty acids derived from soybean oil were used as a biomass-derived resource for the synthesis of biolubricants. Long chain alcohols (carbon number ≥ 8) or neo-polyols (e.g., 2,2-diethyl-1,3-propanediol, trimethylol propane, pentaerythritol) were used as co-reactants. The structure of the alcohol significantly affected the conversion and yield for the esterification with oleic acid. The esters produced showed kinematic viscosity and viscosity index comparable to commercial lubricants. Various sulfated zirconia catalysts were prepared and were characterized by X-ray diffraction, NH3 temperature-programmed desorption, Brunauer-Emmett-Teller isotherm, and tested for esterification. The type of zirconium precursor demonstrated a significant effect on the physical property of the catalyst and its catalytic activity. Interestingly, esters with fully saturated hydrocarbon chains were synthesized from unsaturated free fatty acids regardless of the absence of hydrogen gas. The sulfated zirconia could be recycled for up to five repeated reactions without any degradation. The effects of reaction time and temperature were also investigated.

Esterifications of carboxylic acids and alcohols catalyzed by Al 2(SO4)3 · 18H2O under solvent-free condition

Esterifications of equimolar mixture of carboxylic acids and alcohols can be effectively catalyzed by Al2(SO4)3 · 18H2O under solvent-free condition. The esterification catalyzed by Al2(SO4)3 · 18H2O is a promising green method thanks to no need of organic solvent, no pollution, no causticity and ease to handle after reaction. This catalyst is of a low toxicity (usually it is used as purifying agent for drinking water), low-cost compound and is easily separated from the reaction mixture by simple filtration. Moreover, the catalyst can be recycled for the further esterification and the conversion does not evidently decrease.

PROCESS OF MANUFACTURING OF FATTY ACID ALKYL ESTERS

Processes for preparation of fatty acid alkyl esters are described herein. The processes include contacting fatty acid glycerides with alcohols in the presence of a catalyst separating the reaction products from the catalyst, and separating the fatty acid alkyl esters from the reaction products. The catalyst includes a metal from Group VIB of the Periodic Table, a metal from Group IIIA of the Periodic Table, and an element from Group VA of the Periodic Table.

Melting points and viscosities of fatty acid esters that are potential targets for engineered oilseed

Our previous isolation of branched-chain fatty acid (BCFA) methyl esters from lanolin was improved and scaled up. Also, oleate esters of isopropanol, oleyl alcohol and normal alcohols of 1-12 carbons chain lengths were prepared. Esters were made by interesterification with sodium alcoholates and by esterification with Candida antarctica lipase. It proved easier to obtain pure esters by the enzymatic synthesis. Melting points and viscosities over the range of 0-70 °C were determined in order to better identify potential lubricant targets that might be produced by genetically modified oilseed crops. Isopropyl and butyl oleate have melting points of -33 and -32 °C, respectively and viscosities that range from ~17 cp (0 °C) to ~2.5 cp (70 °C). They should have suitable stability for lubricants. BCFA esters had viscosities similar to their straight chain analogs. Viscosities increased with alcohol chain length and decreased with temperature. The dependence of viscosity on temperature was fit with an equation based on Erying's rate equation. Some esters with branched acid or branched alcohol moieties, and some oleate esters might be utilized as biolubricants or biofuels on the basis of their melting points and viscosities.

Solvent-free esterification catalyzed by surfactant-combined catalysts at room temperature

Solvent-free esterifications of various carboxylic acids and alcohols can be catalyzed by surfactant-combined catalysts dodecylbenzene sulfonic acid (DBSA) and copper dodecylbenzene sulfonate (CDBS) in moderate to excellent yield at room temperature. The esterification method has two notable advantages: first, there is no need for any solvent, even water, and secondly, no need for energy, the reaction can proceed smoothly at room temperature. The Royal Society of Chemistry and the Centre National de la Recherche Scientifique.

Diesters from oleic acid: Synthesis, low temperature properties, and oxidation stability

Several diesters were prepared from commercially available oleic acid and common organic acids. The key step in the three step synthesis of oleochemical diesters entails a ring opening esterification of alkyl 9,10-epoxyoctadecanoates (alkyl: propyl, isopropyl, octyl, 2-ethylhexyl) using propionic and octanoic acids without the need for either solvent or catalyst. Each synthetic diester was evaluated for both low temperature operability and oxidation stability through measurement of cloud point, pour point, oxidation onset temperature, and signal maximum temperature. It was discovered that increasing chain length of the mid-chain ester and branching in the end-chain ester had a positive influence on the low temperature properties of diesters. Improved oxidation stability is achieved when the chain length of the mid-chain ester is decreased. Additionally, the mid-chain ester plays a larger role in oxidation stability than the end-chain ester. These products may prove useful in the search for bio-based industrial materials, such as lubricants, surfactants, and fuel additives.