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WO2014140392A1 - Procédé intégré d'obtention d'alcools monoinsaturés, de biodiesel et de produits biodégradables à partir d'huile de jojoba - Google Patents

Procédé intégré d'obtention d'alcools monoinsaturés, de biodiesel et de produits biodégradables à partir d'huile de jojoba Download PDF

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Publication number
WO2014140392A1
WO2014140392A1 PCT/ES2014/000039 ES2014000039W WO2014140392A1 WO 2014140392 A1 WO2014140392 A1 WO 2014140392A1 ES 2014000039 W ES2014000039 W ES 2014000039W WO 2014140392 A1 WO2014140392 A1 WO 2014140392A1
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alcohols
different
mixture
jojoba
production
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English (en)
Spanish (es)
Inventor
José ARACIL MIRA
Mercedes MARTÍNEZ RODRÍGUEZ
El Boulifi NOUREDDIN
Marcos SÁNCHEZ RODRÍGUEZ
Marta SERRANO MARTÍNEZ
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Universidad Complutense de Madrid
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Universidad Complutense de Madrid
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C33/00—Unsaturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
    • C07C33/02—Acyclic alcohols with carbon-to-carbon double bonds
    • C07C33/025—Acyclic alcohols with carbon-to-carbon double bonds with only one double bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/128—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by alcoholysis
    • C07C29/1285—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by alcoholysis of esters of organic acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/74—Separation; Purification; Use of additives, e.g. for stabilisation
    • C07C29/76—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment
    • C07C29/78—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment by condensation or crystallisation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/03—Preparation of carboxylic acid esters by reacting an ester group with a hydroxy group
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/48—Separation; Purification; Stabilisation; Use of additives
    • C07C67/52—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/52—Esters of acyclic unsaturated carboxylic acids having the esterified carboxyl group bound to an acyclic carbon atom
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
    • Y02E50/00—Technologies for the production of fuel of non-fossil origin
    • Y02E50/10—Biofuels, e.g. bio-diesel

Definitions

  • the present invention relates to a process for carrying out the integrated obtaining of different mixtures composed of monounsaturated primary aliphatic alcohols and monoalkyl esters from Jojoba oil.
  • the procedure consists in the catalytic transesterification of Jojoba oil with short and medium chain alcohols which results in a mixture of monounsaturated primary aliphatic alcohols and monoalkyl esters of Jojoba acids and the subsequent separation thereof.
  • the alcohols obtained have between 18 and 24 carbon atoms.
  • These high purity blends are used in pharmaceutical compositions, food products and dietary supplements. More specifically for the topical treatment of subdermal infections such as herpes virus infections and transdermal administration of pharmacological agents for the treatment of various disorders.
  • the mixture of mono-alkyl esters can be used as biodiesel and as biodegradable products.
  • Jojoba oil (Simmonsdia chinensis) is a natural product that is extracted from the seeds of the plant that bears his name and that is a shrub originating in the Sonoran Desert, in northern Mexico and the southwestern United States. Unlike other oils obtained from plants or fish, Jojoba oil is not composed of triglycerides, but a mixture of linear esters composed mainly of alcohols and carboxylic acids both long chain (Wisniak, The Chemistry and technology of Jojoba oil , publ. by American Oil Chemists Society, Champaign, Illinois, 272 pp, 1987). These esters have two double bonds, in cis configuration, one on each side of the ester group at the 9-Omega position (Formula I).
  • Jojoba oil has been commercially available for more than fifty years, and several million kilos are used per year in pharmaceutical and cosmetic formulations. It is recognized as safe for cosmetic uses (J. Amer. Coll. Toxicol., 11 (1): 57-74, 1992). Numerous tests have shown that its topical use in humans is safe and non-toxic, as well as oral administration to mice, rats and rabbits (Taguchi and Kunimoto, cosmetics and toiletries, 92: 53-61, 1977; Clark and Yérmanos , Biochem. Biophys. Res. Commun., 102 (2): 1409-1415, 1981; Hamm, J. Food Sci., 49: 417-428, 1984; Verschuren and Nugteren, Food Chem.
  • Jojoba oil is also used as a promoter of therapeutic efficacy of other active ingredients, since it increases percutaneous absorption and accumulation in the epidermis, and is able to act as a carrier of the active ingredients to the deep layer of the skin to perform its function US6559182.
  • Jojoba oil itself used directly as a carrier is only capable of dissolving lipophilic active ingredients, but is not useful as a carrier of hydrophilic active ingredients.
  • Jojoba oil acts as an intestinal lubricant, and it is estimated that approximately 20 % Jojoba oil is hydrolyzed by esterases in the gastrointestinal system, thus producing Jojoba alcohols in situ. After dermal absorption, Jojoba oil is also partially metabolized to the corresponding alcohols. Therefore, a new carrier derived from Jojoba oil, such as the mixture of alcohols, may be able to transport a wide range of active ingredients, either lipophilic or hydrophilic, also presenting the advantages of aqueous carriers compared to oily ones. .
  • the preparation involves the hydrogenolysis of Jojoba oil with sodium bis (2-methoxyethoxy) aluminum hydride using dry toluene as solvent.
  • the same patent also describes the obtaining of a mixture of long chain alcohols such as those found in Jojoba oil from whale sperm oil, applying the same hydrogenolysis process mentioned above.
  • the first stage of the process described here is a procedure that involves subjecting Jojoba oil to decomposition through a transesterification reaction, using different alcohols of low and medium molecular weight.
  • the alcohols used are methanol and octanol of petrochemical origin, and on the other hand ethanol and butanol, obtained by fermentation of biomass. Enzymatic, heterogeneous and homogeneous catalysts have been used in said transesterification reaction.
  • the enzymes used in the present invention are of certain characteristics, making the transesterification reach conversions greater than 90%.
  • the catalytic systems referred to in the invention are enzymatic preparations consisting of lipases, triacylglycerol hydrolases (EC 3.1.1.3), produced by the fungal species Mucor miehi or the fungal species Candida antárctica, and immobilized on anionic exchange resins or macroporous acrylics , with different properties each of them.
  • the two enzyme species can exert the lipase action or the carboxylesterase action with high effectiveness and, in both cases, the specificity of said enzymes can be positional or not depending on the type of substrate to be modified with them.
  • the catalytic systems have an average diameter that is in the range of 50 to 400 A, preferably between 120 and 300 A, the range in which the specific surface is 10 to 150 m 2 / g, preferably between 25 and 100 m 2 / g.
  • Catalytic systems produced from the fungal species Mucor miehi have a (number of ⁇ of n-propyl laurate obtained from lauric acid and 1-propanol for a reaction time of 15 minutes, at a temperature of 60 ° C). activity that is in the range of 20 to 80 BIUS (number of ⁇ of palmitic acid transformed by triolein per minute using the immobilized enzyme at a temperature of 40 ° C).
  • Catalytic systems produced from the fungal species Candida antárctica have an activity that is in the range of 5000 to 12000 PLUS / g
  • the heterogeneous basic catalysts used in the present invention are: Na / y-AI 2 0 3 , ⁇ / ⁇ - ⁇ 2 ⁇ 3 ⁇ ⁇ / ⁇ - ⁇ 2 0 3 and Ca / y-AI 2 O 3 (10% content in metal) comprising a combination formed between a metal hydroxide (LiOH, NaOH, KOH, Ca (OH) 2 and Ba (OH) 2 .8H 2 0) and alumina ( ⁇ - ⁇ 2 0 3 ).
  • the homogeneous basic catalysts used are: NaOH and KOH with a purity of 99%, NaOCH 3 and KOCH 3 in the form of solutions in methanol (32%).
  • both stirred reactors can be used working in batch or in continuous, whether it is a stirred or fixed bed type.
  • the stirred reactor is charged with Jojoba oil, alcohol and catalyst and the transesterification reaction is carried out.
  • the reactor vessel In the case of using stirred reactors but working continuously, the reactor vessel is initially charged with the alcohol mixture and the catalyst and once the working conditions of the reaction are reached, the oil is fed with the required flow rate. . If a fixed bed type reactor is used, the catalyst is loaded into the reactor and once the catalytic bed reaches the working conditions of pressure and temperature, the oil-alcohol mixture is passed with the required flow rate.
  • the reaction is carried out in a temperature range between 60 and 95 ° C (depending on the alcohol and the catalyst system used), using an oil: alcohol molar ratio between 1: 1 and 1: 6 preferably (1: 1 -1: 4.5), the amount of catalyst used being between 5 and 7%, for heterogeneous and enzymatic catalysts and between 0.5 and 1.5% for homogeneous catalysts, with respect to the total reagent weight.
  • the reaction is carried out at atmospheric pressure, with a stirring speed of between 300 to 700 rpm and a reaction time of between 3 and 10h.
  • the alcohols and esters present in the reaction medium are subjected to a separation process.
  • the separation of transtesterified products can be carried out by flash column chromatography and subsequent fractionation of the alcohol mixture or by direct fractionation by recrystallization.
  • the mixture of aliphatic alcohols obtained from jojoba oil contain between 18 to 24 carbon atoms with the following quantitative composition:
  • the mixture of alcohols obtained by flash column chromatography is fractionated by cryogenic crystallization in solvent systems.
  • the procedure followed is as follows: a certain amount of polar solvent such as, for example, ethyl ether, acetone, tetrahydrofuran, dichloromethane, ethyl acetate, methanol or ethanol, is added hot to the mixture of alcohols obtained per column. It is stirred and after 10 minutes an apolar solvent such as hexane, pentane or heptane is added.
  • the concentration of the alcohol mixture is usually from 8 to 20 and, preferably from 12 to 15% by weight in a solvent system, which can be in pure form or in the form of a mixture of apolar: polar solvents.
  • the ratio of apolar / polar solvent is from 1 to 8 and, preferably, from 2 to 4.
  • the solution formed is allowed to crystallize at a temperature between -25 ° C and -15 ° C, preferably between -18 and -20 ° C for 24h.
  • the white solid obtained is filtered off using a Büchner funnel, which has been previously cooled and washed with a non-polar solvent at low temperature (hexane is used in most cases);
  • the solvent is removed under reduced pressure to give rise to the first solid fraction that contains the alcohol, C24: i-
  • the resulting mother liquors are concentrated, recycled by recrystallizing in the same way as the previous one, the only difference is that the concentration of the solute in the Solvent system is greater in this case than the first recrystallization.
  • the fraction obtained in the second recrystallization is liquid and it is enriched with alcohols; C22: i and C24: i.
  • the final mother liquors were concentrated to give rise to a liquid mixture of alcohols
  • the crude liquid mixture of alcohols obtained directly by column chromatography, or;
  • the 3 fractions obtained by cryogenic crystallization thereof can be used as is or reformulated for the topical treatment of subdermal infections such as herpes virus infections and the transdermal administration of pharmacological agents for the treatment of various disorders.
  • Jojoba alcohols are not limited to topical treatment of subdermal infections;
  • the US patent US5700453 describes its use together with a large number of compounds in the formulation of the lipstick, providing less dryness and greater durability.
  • Jojoba alcohols have also been used as excipients in US5750563 on kojic acid.
  • the use of Jojoba oil as a source of mixture of aliphatic alcohols offers numerous advantages over the use of other raw materials, such as beeswax or sugarcane. For example, there are factors associated with the purity of beeswax or sugarcane that are difficult to control, and therefore it is difficult to obtain a reliable source that meets the requirements to obtain a pure product.
  • alcohols obtained from beeswax and sugarcane are solid and require a carrier or surfactant to facilitate transdermal penetration.
  • Jojoba oil is used with the properties shown in Table 1.
  • Table 1 properties and composition of Jojoba oil
  • This example shows the influence of the enzymatic catalytic system obtained from the fungal species Mucor miehi, immobilized in anion exchange resin, with an average pore diameter of 176 A, a specific surface area of 60 m 2 / g and an activity of 60 BIUS.
  • the reaction is carried out in a complete mixing reactor of 250 ml capacity, equipped with a reflux refrigerant system. Oil and alcohol are introduced into the reactor in a 1: 3 molar ratio, with an initial enzyme catalyst concentration of 5% by weight.
  • the reaction temperature is maintained at 70 ° C and the stirring speed is 700 rpm. After 10 hours of reaction, the oil conversion was 77%.
  • This example shows the influence of the enzymatic catalytic system obtained from the fungal species Candida Antarctica, immobilized in macroporous acrylic resin, with an average pore diameter of 180 A, a specific surface area of 95 m 2 / g and an activity of 7000 PLUS / g.
  • the reaction is carried out in a complete mixing reactor of 250 ml capacity, equipped with a reflux refrigerant system. Oil and alcohol are introduced into the reactor in a 1: 3 molar ratio, with an initial concentration of enzyme catalyst of 5% by weight. The reaction temperature is maintained at 70 ° C and the stirring speed is 700 rpm. After 10 hours of reaction the oil conversion was 81%.
  • this example shows the influence of the enzymatic catalytic system obtained from the fungal species Candida Antarctica immobilized in macroporous acrylic resin with an average pore diameter of 210A, a specific surface area of 67 m 2 / g and an activity of 7800 PLUS / g.
  • the reaction is carried out in a complete mixing reactor of 250 ml capacity, equipped with a reflux refrigerant system.
  • the oil and alcohol are introduced into the reactor in a 1: 3 molar ratio, the initial catalyst concentration being 5% by weight.
  • the reaction temperature was maintained at 70 ° C and the stirring speed at 700 rpm After 10 hours of reaction the oil conversion was 72%.
  • This example shows the influence of the heterogeneous catalytic system ( ⁇ / ( ⁇ - ⁇ 2 0 3 ).
  • the reaction is carried out in a complete mixing reactor of 250 ml capacity, equipped with a reflux refrigerant system. Oil and alcohol are introduced into the reactor in a 1: 3 molar ratio, with a catalyst initial concentration of 5% by weight.
  • the reaction temperature is maintained at 70 ° C and the stirring speed is 700 rpm. After 10 hours of reaction the oil conversion was 82%.
  • This example shows the influence of the homogeneous catalytic system (NaOCH 3 ).
  • the reaction is carried out in a complete mixing reactor of 250 ml capacity, equipped with a reflux refrigerant system. Oil and alcohol are introduced into the reactor in a 1: 3 molar ratio, with a catalyst initial concentration of 1% by weight.
  • the reaction temperature is maintained at 70 ° C and the stirring speed is 700 rpm. After 10 hours of reaction the oil conversion was 84%.
  • Example 2 was repeated, with the same catalyst and identical operating conditions, except for the reaction temperature, which was maintained at 78 ° C. After 10 hours of reaction, the oil conversion was 89%.
  • Example 7
  • a bed of extensible capacity with a diameter of 1.6 cm and a height of 6 cm, provided with a jacket to thermostatize the operation, 4.5 g of immobilized enzyme are introduced. Through it a mixture of oil and alcohol is circulated in a 1: 3 molar ratio at a flow rate of 1ml / min.
  • the enzymatic catalyst used is that obtained from the fungal species Candida antárctica, immobilized in macroporous acrylic resin, with an average pore diameter of 180 A, a specific surface area of 95 m 2 / g and an activity of 7000 PLUS / g.
  • the reaction temperature was maintained at 70 ° C.
  • the average residence time was 1, 3 hours and the acid conversion was 18%.
  • Examples 10, 11 and 12 show the influence of the complexity of the alcohol chain used as a transesterification agent.
  • the catalyst used is obtained from the fungal species Candida Antarctica, immobilized in a macroporous acrylic resin, with an average pore diameter of 180 A, a specific surface area 95 m 2 / g. and an activity of 7000 PLUG / g.
  • Example 10
  • the reaction is carried out under the same conditions as in Example 8, except that the alcohol used in the transesterification is methanol and the reaction temperature is 60 ° C. After 10 hours of reaction, the oil conversion was 95%.
  • the reaction is carried out under the same conditions as in Example 8, except that the alcohol used in the transesterification is ethanol. After 10 hours of reaction, the oil conversion was 89%.
  • the reaction is carried out under the same conditions as in Example 8, except that the alcohol used in the transesterification is octanol. After 10 hours of reaction, the oil conversion was 84%.
  • Jojoba oil is used in the form of two solid and liquid fractions obtained by a controlled cryogenization process at temperatures between 6 and 10 ° C and operating time between 1 h and 36h. Said fractions have different compositions and properties. Table 2 shows the properties of the liquid and solid fraction.
  • Example 8 The reaction is carried out under the same conditions as in Example 8, except that the oil used in the transesterification is a liquid fraction of Jojoba oil obtained by a controlled cryogenic process. After 10 hours of reaction, the oil conversion was 93%. Unlike example 8, the proportions of the alcohols obtained in this example are: Ci 8: i: 0.8%, C 20: i: 51.2% ⁇ C 22: i: 41.5% and C 24: i: 6.3%.
  • the reaction is carried out under the same conditions as in Example 8, except that the oil used in the transesterification is a solid fraction of Jojoba oil obtained by a controlled cryogenic process. After 10 hours of reaction, the oil conversion was 92.5%. Unlike example 8, the proportions of the alcohols obtained in this example are: C 2 or: 31.4%; C 22 : 53.3% and C 2 : 15.3%.
  • Isolated alkyl alcohols and esters have been identified based on their spectroscopic and / or analytical data.
  • Table 3 shows the percentages of alcohols and alkyl esters obtained using different alcohols in the Jojoba oil transesterification process.
  • the mixture of alcohols obtained in example 15 was subjected to crystallization fractionation.
  • 50 g of the mixture, containing 4 alcohols (Ci 8: i, C20.1, C22.1 and C24.1) were dissolved in 200 ml of hot ethyl ether and subsequently diluted with 800 ml of hexane.
  • the mixture was kept at 30 ° C and with vigorous stirring for 10 min. Precipitation was caused by cooling of the mixture in a thermostatic bath at -20 0 C for 24 hours.
  • the solution was filtered using a Büchner funnel.
  • the white solid was washed with previously cooled hexane and dried under reduced pressure to give 4.2 g of the C 2 4: i alcohol.
  • Pentane / 3 1 47.3 97% (Ci 8 : 0.6; C 20 : 37.7; C 22 : 51.2; C 24 : 10.5) ethyl ether
  • Example 10 100 g of the resulting transesterification product in Example 10, containing alcohols and esters, was dissolved in 200 ml of hot ethyl ether and subsequently diluted with 800 ml of hexane. The mixture was kept at 30 ° C and with vigorous stirring for 10 min. Let stand at -20 ° C for 24 h. A solid appears that filters using a funnel Büchner and washed with hexane, both previously cooled. The solvent was removed under reduced pressure to give 21 g of a solid mixture of C22: i and C24: i alcohols in a ratio of 5.8: 1. at room temperature. The mother liquors were concentrated and subjected to two recrystallizations following the same procedure.
  • Example 11 100 g of the resulting transesterification product in Example 11, containing alcohols and esters, was dissolved in 200 ml of hot ethyl ether and subsequently diluted with 800 ml of hexane using a beaker. The mixture was kept at 30 ° C and with vigorous stirring for 10 min. Let stand at -20 ° C for 24 h. A solid appears which is filtered using a Büchner funnel and washed with hexane, both previously cooled. The solvent was removed under reduced pressure to give 18.5 gr. of a fraction of alcohols, solid at room temperature. The mother liquors were concentrated, and in the same way it is recrystallized again 2 more times.
  • Example 12 100 g of the resulting transesterification product in Example 12, containing alcohols and esters, was dissolved in 200 ml of hot ethyl ether and subsequently diluted with 800 ml of hexane using a beaker. The mixture was kept at 30 ° C and with vigorous stirring for 10 min. Let stand at -20 ° C for 24 h. A solid appears which is filtered using a Büchner funnel and washed with hexane, both previously cooled. The solvent was removed under reduced pressure to give 18.2 g of a solid alcohol fraction at room temperature. The mother liquors were concentrated, and in the same way it is recrystallized again 2 more times.
  • the content of aliphatic alcohols obtained varies greatly depending on the solvent system used in the crystallization, the concentration of the solute and also the alcohol used in the transesterification.
  • the content of aliphatic alcohols obtained during recrystallization is higher when butyl alcohol is used as a reagent in transesterification, because butyl esters have a lower melting point compared to methyl or ethyl esters.
  • the conversion of the oil is low compared to the transesterification with the other alcohols, whereby mixtures of alcohols are obtained with lower yield.
  • Figure 1 shows a diagram for the integrated obtaining of Jojoba alcohols and mono-alkyl esters from Jojoba oil.
  • Figure 3 shows the gas chromatogram: a) Jojoba oil; b) product of the transesterification reaction and c) isolated alcohols of Jojoba.
  • Figure 4 shows the structure and spectral data ( 1 H-NMR) of the Jojoba alcohol mixture.
  • Figure 5 shows the infrared spectrum of the alcohol mixture.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Cosmetics (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Medicinal Preparation (AREA)
  • Fats And Perfumes (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)

Abstract

Dans la présente invention, on effectue la transestérification d'huile de jojoba en présence d'alcools de masse moléculaire faible ou moyenne, au moyen de catalyseurs enzymatiques, hétérogènes ou homogènes. Le produit de réaction est ensuite soumis à diverses étapes de cristallisation dans un système de dissolvants organiques purs ou d'un mélange de dissolvant polaire/apolaire. Le procédé permet d'obtenir des mélanges différents d'alcools gras insaturés de haute pureté sous de liquide huileux utile pour l'administration transdermique d'agents pharmacologiques. On obtient, comme produit secondaire, des esters monoalkyliques qui peuvent être utilisés en tant que biodiesel ou en tant que produits biodégradables.
PCT/ES2014/000039 2013-03-15 2014-03-14 Procédé intégré d'obtention d'alcools monoinsaturés, de biodiesel et de produits biodégradables à partir d'huile de jojoba Ceased WO2014140392A1 (fr)

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ES201300261A ES2494620B2 (es) 2013-03-15 2013-03-15 Proceso integrado de obtención de alcoholes monoinsaturados, biodiesel y productos biodegradables a partir de aceite de Jojoba

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE102015207572A1 (de) 2015-04-24 2016-10-27 Henkel Ag & Co. Kgaa "Kosmetische Mittel enthaltend alkoxylierte Fettalkohole mit trans-ständigen Doppelbindungen"
US12180530B2 (en) 2014-12-19 2024-12-31 Cargill, Incorporated Processes and systems for catalytic manufacture of wax ester derivatives

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US5968530A (en) * 1997-10-17 1999-10-19 International Flora Technologies, Inc. Emollient compositions
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US6703052B2 (en) * 1998-06-01 2004-03-09 Anthony J. Verbiscar Long chain monounsaturated alcohol mixtures

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US5968530A (en) * 1997-10-17 1999-10-19 International Flora Technologies, Inc. Emollient compositions
US6703052B2 (en) * 1998-06-01 2004-03-09 Anthony J. Verbiscar Long chain monounsaturated alcohol mixtures
WO2003003833A1 (fr) * 2001-07-03 2003-01-16 International Flora Technologies, Ltd. Composition antivirale et procédé de traitement

Non-Patent Citations (2)

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Title
BOUAID, A. ET AL.: "Optimization of Biodiesel Production from Jojoba Oil''.", PROCESS SAFETY AND ENVIRONMENTAL PROTECTION, vol. 85, no. 5, 2007, pages 378 - 382, XP022618631, DOI: doi:10.1205/psep07004 *
CANOIRA, L. ET AL.: "Biodiesel from Jojoba oil-wax: Transesterification with methanol and properties as a fuel''.", BIOMASS AND BIOENERGY, vol. 30, no. 1, 2006, pages 76 - 81, XP027968694, DOI: doi:10.1016/j.biombioe.2005.07.002 *

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US12180530B2 (en) 2014-12-19 2024-12-31 Cargill, Incorporated Processes and systems for catalytic manufacture of wax ester derivatives
US12203122B2 (en) 2014-12-19 2025-01-21 Cargill, Incorporated Processes and systems for catalytic manufacture of wax ester derivatives
US12281350B2 (en) 2014-12-19 2025-04-22 Cargill, Incorporated Processes and systems for catalytic manufacture of wax ester derivatives
DE102015207572A1 (de) 2015-04-24 2016-10-27 Henkel Ag & Co. Kgaa "Kosmetische Mittel enthaltend alkoxylierte Fettalkohole mit trans-ständigen Doppelbindungen"

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