Oleic acid reactor

There has been only one major use for ozone today in the field of chemical synthesis the ozonation of oleic acid to produce azelaic acid. Oleic acid is obtained from either tallow, a by-product of meat-packing plants, or from tall oil, a byproduct of making paper from wood. Oleic acid is dissolved in about half its weight of pelargonic acid and is ozonized continuously in a reactor with approximately 2 percent ozone in oxygen it is oxidized for several hours. The pelargonic and azelaic acids are recovered by vacuum distillation. The acids are then esterified to yield a plasticizer for vinyl compounds or for the production of lubricants. Azelaic acid is also a starting material in the production of a nylon type of polymer. 

The experiments were performed in a CINC V-02 separator also known as the CS-50 (15). Two Verder VL 500 control peristaltic tube pumps equipped with a double pump head (3,2 x 1,6 x 8R) were used to feed the CCS. In case of the enzymatic reaction, the low mix bottom plate was applied. To operate the reactor at a desired temperature, it was equipped with a jacket which was coimected to a temperature controlled water bath with an accuracy of 0.01°C. The CCS was fed with pure heptane and pure water, both with a flow rate of 6 mL/min. Subsequently, the centrifuge was started (40 Hz, which corresponds to 2400 rpm) and the set-up was allowed to equilibrate for a period of 1 h. At this point, the heptane feed stream was replaced by the organic feed stream (oleic acid (0.6M) and 1-bntanol (0.9M) in heptane). After equilibration for 10 minutes, the reaction in the CCS was started by replacing the water stream with the aqueous feed stream (0.1 M phosphate buffer pH 5.6 containing 1 g/1 of the lipase form Rhizomucor miehei). Samples were taken at regular intervals and analysed by GC. 

Chlorination of oleic acid dissolved in carbon tetrachloride was tested in a flow reactor. The data are at 12.8 C (Roper, Chem Eng Sci 227, 1953). The reactants were dissolved separately and mixed in the liquid phase at the inlet to the reactor. Show that the reaction is second order. 

Esterification between oleic acid and oleyl alcohol, catalyzed by the Mucor miehei immobihzed hpase in a batch-stirred tank reactor with supercritical carbon dioxide as solvent produced higher reaction rates at supercritical conditions than in the solvent-free system (Knez et al., 1995). 

Two segments of the some fixed bed reactor were used, with dehydration of the reactional medium on molecular sieve between each of them. With oleic acid, and an excess of 3 moles of glycerol per mole of acid, the yield was 44.7 % (molar) of monoolein after 2 hours. At the same time, only 2 % of di-olein were obtained (Fig. 6.). 

The enzymatic esterification of oleic acid and oleyl alcohol to obtain oleyl oleate, which is a synthetic analogue of jojoba oil, was studied. The reaction was catalyzed by a commercially available immobilized lipase from Rhizomucor miehei. As solvents, carbon dioxide and liquid n-butane were used. Reactions were performed in a batch and in continuously operating high pressure reactors. 

Reaction performance. Supercritical carbon dioxide was used as a reaction media for the enzymatic synthesis of oleyl oleate directly from oleic acid and oleyl alcohol. Reaction was catalyzed by immobilized lipase from Rhizomucor miehei-Ltpozyme IM. Reactions were carried out in the high pressure batch and continuous reactor. 

High pressure batch stirred tank reactor. Substrates (equimolar solution of oleic acid and oleyl alcohol) were filled into thermostated autoclave and mixed. Enzyme preparation was added and finally CO2 was pumped with a high pressure pump up to desired pressure. Reactor volume was 0.5 L (Pmax = 450 bar, Tmax = 200°C) (Figure 1). 

High pressure continuously operated reactor. The design of the continuously operated apparatus is shown in Figure 2. An air operated high pressure pump delivered CO2 in the system. The gaseous fluid was dried when passing through columns packed with molecular sieves. The flow rate of C02 was 1.0 L per min. Equimolar solution of substrates (oleic acid and oleyl alcohol) was pumped into the system with an HPLC pump. Carbon dioxide and substrates were equilibrated in the saturation column. The reaction was performed in a... 

In a typical reaction a 750-ml reactor was charged with styrene (962 mmol), oleic acid (21.2 mmol), and phenyl-t-butyl nitrone and then flushed with nitrogen. The mixmre was treated with a solution of K3PO4 (18.8 mmol), KOH (29.3 mmol + 2 mmol KOH per initator), and 4,4-azobis(4-cyanovaleric acid) (2.62 mmol) dissolved in 400 ml of water. In all cases an emulsion formed immediately. Reactors were flushed with nitrogen, sealed, and circulated on a rotating wheel in a water bath at 75°C, and the... 

A reactor was charged with 1 -hexene (25 g), n-butyl acrylate (25 g), dipyridyl (0.38 g), oleic acid (4.0 g), and ethyl 2-bromoisobutyrate (0.47 g) and then stirred until homogeneous. The mixture was next treated with 85% KOH (1.7 g) dissolved in... 

How should the reaction be carried out (e.g. type of reactor(s), volume, temperature, feed rate) to produce 100 kmol of oleic acid expoxide (E) per day There will be a prize for the solution that meets this criteria and minimizes the undesirable products. If equipment costs are available they should be included. 

Goddard R, Bosley J, Al-Duri B (2000) Esterification of oleic acid and ethanol in plug flow (packed bed) reactor under supercritical conditions—investigation of kinetics. J Supercrit Fluids 18 121-130... 

A membrane cell recycle reactor with continuous ethanol extraction by dibutyl phthalate increased the productivity fourfold with increased conversion of glucose from 45 to 91%.249 The ethanol was then removed from the dibutyl phthalate with water. It would be better to do this second step with a membrane. In another process, microencapsulated yeast converted glucose to ethanol, which was removed by an oleic acid phase containing a lipase that formed ethyl oleate.250 This could be used as biodiesel fuel. Continuous ultrafiltration has been used to separate the propionic acid produced from glycerol by a Propionibacterium.251 Whey proteins have been hydrolyzed enzymatically and continuously in an ultrafiltration reactor, with improved yields, productivity, and elimination of peptide coproducts.252 Continuous hydrolysis of a starch slurry has been carried out with a-amylase immobilized in a hollow fiber reactor.253 Oils have been hydrolyzed by a lipase immobilized on an aromatic polyamide ultrafiltration membrane with continuous separation of one product through the membrane to shift the equilibrium toward the desired products.254 Such a process could supplant the current energy-intensive industrial one that takes 3-24 h at 150-260X. Lipases have also been used to prepare esters. A lipase-surfactant complex in hexane was used to prepare a wax ester found in whale oil, by the esterification of 1 hexadecanol with palmitic acid in a membrane reactor.255 After 1 h, the yield was 96%. The current industrial process runs at 250°C for up to 20 h. 

A membrane reactor using a H-ZSM5 membrane was used by Bernal et al. [3.42] to carry out the esterification reaction of acetic acid with ethanol. An equimolar etha-nol/acetic acid liquid mixture was fed in the membrane interior, while He gas was used as an inert sweep on the shell-side. In this particular application the membrane, itself, provides the catalysis for the reaction. NaA and T-type zeolite membranes have been utilized for esterification reactions in a PVMR and in a vapor permeation membrane reactor (VPMR) by Tanaka et al [3.43, 3.44]. Both membranes are hydrophilic and show good separation characteristics towards a number of alcohols. The NaA membrane was used to study the oleic/acid esterification in a vapor permeation membrane reactor (VPMR) at 383... 

K. Okamoto, M. Yamamoto, S. Noda, T. Semoto, Y. Otsushi, K. Tanaka and H. Kita, Vapor-permeation-aided esterification of oleic acid, Ind. Eng. Chem., Res., 1994, 33, 849-853 B. Chemseddine and R. Audinos, Use of ion-exchange membranes in a reactor for esterification of oleic acid and methanol at room temperature, J. Membr. Sci., 1996, 115, 77-84. 

Bakr et al. reported the flow reactor synthesis of PbS quantum dots for applications in solar cells. They showed that the flow reactor products had comparable performance to the batch synthesized PbS nanoparticles. A dual-temperature-stage flow reactor synthesis was carried out to achieve optimum results. The flow reactor system is shown schematically in Fig. 11. In this method precursor A consists of lead oxide, oleic acid (OA), and octadecene (ODE) whereas precursor B contains bis(trimethylsilyl) sulfide (TMS) and ODE. The two precursors are injected under nitrogen. The mixed reactants proceed together to the nu-cleation stage that is temperature-controlled by thermocouple 1. The precursors react at the elevated temperatures to form nucleation seeds. The quantum dots are then isolated using acetone and re-dispersed in toluene. 

Son, S. M., Kimura, H., Kusakabe, K. (2011). Esterification of oleic acid in a three-phase, fixed-bed reactor packed with a cation exchange resin catalyst. Bioresource Technology, 102 2), 2130-2132. 

Lithium oleate was prepared by neutralization of oleic acid with lithium hydroxide in toluene under reflux and azeotropic removal of water. The solvent was evaporated and the residue washed twice with ether. The remaining traces of solvent were removed in vacuo. The ultrasonic reaction was performed in an ultrasonic laboratory reactor (35 kHz, 4 x 100 W transducers) from Allied Signal ELAC Nautic GmbH, 24118 Kiel, Germany. 

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