- A New and Efficient Approach to Macrocyclic Keto Lactones
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A new and efficient method for macrolactonization has been developed.The intramolecular nucleophilic displacement of chloride from the highly electrophilic α-chloro ketone moiety in 15 by a remote carboxylate nucleophile resulted in the clean formation of the 11-membered keto lactone 1.Relatively high substrate concentrations (up to 18 mM) could be employed without formation of dimeric or oligomeric byproducts.The slow mixing of substrate and base was not required.This macrolactonization reaction was studied in various solvents at a number of substrate concentrations and reaction temperatures in order to evaluate its scope and limitations.A low-temperature Ti(III) ion/peroxide induced radical addition reaction has been developed.The lowering of the reaction temperature from 0 deg C to -78 deg C consistently afforded a dramatic increase in product yield from such reactions.This lowering of the reaction temperature proved essential when the highly functionalized acetoxymethyl vinyl ketone was employed as the radical acceptor.
- Karim, Mohammad R.,Sampson, Paul
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Read Online
- γ-hydroxyalkenals are oxidatively cleaved through Michael addition of acylperoxy radicals and fragmentation of intermediate β-hydroxyperesters
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Oxidative cleavage of arachidonate (C20) and linoleate (C 18) phospholipids generates truncated C8 or C12 γ-hydroxyalkenal phospholipids as well as C5 or C9 carboxyalkanoate phospholipids,
- Balamraju, Yuvaraju N.,Sun, Mingjiang,Salomon, Robert G.
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- Microbial synthesis of medium-chain α,ω-dicarboxylic acids and ω-aminocarboxylic acids from renewable long-chain fatty acids
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Biotransformation of long-chain fatty acids into medium-chain α,ω-dicarboxylic acids or ω-aminocarboxylic acids could be achieved with biocatalysts. This study presents the production of α,ω-dicarboxylic acids (e.g., C9, C11, C 12, C13) and ω-aminocarboxylic acids (e.g., C 11, C12, C13) directly from fatty acids (e.g., oleic acid, ricinoleic acid, lesquerolic acid) using recombinant Escherichia coli-based biocatalysts. ω-Hydroxycarboxylic acids, which were produced from oxidative cleavage of fatty acids via enzymatic reactions involving a fatty acid double bond hydratase, an alcohol dehydrogenase, a Baeyer-Villiger monooxygenase and an esterase, were then oxidized to α,ω- dicarboxylic acids by alcohol dehydrogenase (ADH, AlkJ) from Pseudomonas putida GPo1 or converted into ω-aminocarboxylic acids by a serial combination of ADH from P. putida GPo1 and an ω-transaminase of Silicibacter pomeroyi. The double bonds present in the fatty acids such as ricinoleic acid and lesquerolic acid were reduced by E. coli-native enzymes during the biotransformations. This study demonstrates that the industrially relevant building blocks (C9 to C13 saturated α,ω- dicarboxylic acids and ω-aminocarboxylic acids) can be produced from renewable fatty acids using biocatalysis.
- Song, Ji-Won,Lee, Jung-Hoo,Bornscheuer, Uwe T.,Park, Jin-Byung
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- Preparation, characterization, and theoretical studies of azelaic acid derived from oleic acid by use of a novel ozonolysis method
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Environmentally friendly manufacture of organic compounds has been intensively reexamined in recent years. Many excellent methods have been devised to produce organic compounds from renewable resources. Azelaic acid has been produced by ozonolysis of oleic acid. The reaction was performed in a Bach bubbling reactor, with fine bubbles, at high temperature (150 °C) without utilizing any catalyst or any solvent. Yield of the reaction was 20% after 2 h. Production of azelaic acid was confirmed by use of FT-IR and 1H NMR spectroscopic data and high-performance liquid chromatography of both synthesized and reference azelaic acid. A theoretical study was performed to obtain quantum chemical data for azelaic acid and to optimize the molecule's geometry. Springer Science+Business Media B.V. 2011.
- Kadhum, Abdul Amir H.,Wasmi, Bilal A.,Mohamad, Abu Bakar,Al-Amiery, Ahmed A.,Takriff, Mohd S.
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- Thermoplastic polyester amides derived from oleic acid
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Three lipid-based Polyester Amides (PEAs) with varying ratios of ester and amide linkages were synthesized. Oleic acid was used as the starting material to produce the intermediates, characterized by MS and NMR, used for polymerization. PEAs were characterized by FTIR and GPC. The PEAs were constrained to have similar number average molecular weights, in the 2 × 104 range, thereby enabling comparison of their physical properties from a structural perspective. The thermal behavior of the polymers was assessed by DSC, DMA and TGA. Thermal degradation was not affected by ester/amide ratios, but Tg increased non-linearly with decreasing ester/amide ratios and correlated with hydrogen-bond density and repeating unit chain length. Crystallinity was studied by XRD and DSC. Degree of crystallization and multiple melting behavior as a function of cooling kinetics were explained well by hydrogen-bond density, repeating unit chain length and density of ester moieties. Mechanical properties were investigated by DMA and Tensile Analysis, with a non-linear increase of storage and tensile moduli recorded as a function of decreasing ester/amide ratios. The findings suggest how approaches to the synthesis of lipid-based PEAs can be targeted to the delivery of specific physical properties.
- Zuo, Jiaqing,Li, Shaojun,Bouzidi, Laziz,Narine, Suresh S.
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- Simultaneous Enzyme/Whole-Cell Biotransformation of C18 Ricinoleic Acid into (R)-3-Hydroxynonanoic Acid, 9-Hydroxynonanoic Acid, and 1,9-Nonanedioic Acid
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Regiospecific oxyfunctionalization of renewable long chain fatty acids into industrially relevant C9 carboxylic acids has been investigated. One example was biocatalytic transformation of 10,12-dihydroxyoctadecanoic acid, which was produced from ricinoleic acid ((9Z,12R)-12-hydroxyoctadec-9-enoic acid) by a fatty acid double bond hydratase, into (R)-3-hydroxynonanoic acid, 9-hydroxynonanoic acid, and 1,9-nonanedioic acid with a high conversion yield of ca. 70%. The biotransformation was driven by enzyme/whole-cell biocatalysts, consisting of the esterase of Pseudomonas fluorescens and the recombinant Escherichia coli expressing the secondary alcohol dehydrogenase of Micrococcus luteus, the Baeyer-Villiger monooxygenase of Pseudomonas putida KT2440 and the primary alcohol/aldehyde dehydrogenases of Acinetobacter sp. NCIMB9871. The high conversion yields and the high product formation rates over 20 U/g dry cells with insoluble reactants indicated that various (poly-hydroxy) fatty acids could be converted into multi-functional products via the simultaneous enzyme/whole-cell biotransformations. This study will contribute to the enzyme-based functionalization of hydrophobic substances. (Figure presented.).
- Cha, Hee-Jeong,Seo, Eun-Ji,Song, Ji-Won,Jo, Hye-Jin,Kumar, Akula Ravi,Park, Jin-Byung
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Read Online
- Scalable, sustainable and catalyst-free continuous flow ozonolysis of fatty acids
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A simple and efficient catalyst-free protocol for continuous flow synthesis of azelaic acid is developed from the renewable feedstock oleic acid. An ozone and oxygen mixture was used as the reagent for oxidative cleavage of double bond without using any metal catalyst or terminal oxidant. The target product was scaled up to more than 100 g with 86% yield in a white powder form. Complete recycling and reuse of the solvent were established making it a green method. The approach is significantly energy efficient and also has a very small chemical footprint. The methodology has been successfully tested with four fatty acids making it a versatile platform that gives value addition from renewable resources.
- Atapalkar, Ranjit S.,Athawale, Paresh R.,Srinivasa Reddy,Kulkarni, Amol A.
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supporting information
p. 2391 - 2396
(2021/04/07)
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- METHOD FOR MANUFACTURING PELARGONIC ACID AND AZELAIC ACID
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The present invention relates to a method for producing pelargonic acid and azelaic acid, and more specifically, provides a method for producing pelargonic acid and azelaic acid, which comprises the following steps of: a) reacting an unsaturated carboxylic acid compound under a tungstic acid catalyst to obtain an intermediate product comprising vicinal diol; and b) reacting the intermediate product under a transition metal hydroxide catalyst to obtain the pelargonic acid and azelaic acid. The production method is capable of producing the pelargonic acid and azelaic acid in a high yield from the unsaturated carboxylic acid compound.
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Paragraph 0055-0083
(2021/07/27)
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- Oxidative carbon-carbon bond cleavage of 1,2-diols to carboxylic acids/ketones by an inorganic-ligand supported iron catalyst
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The carbon-carbon bond cleavage of 1,2-diols is an important chemical transformation. Although traditional stoichiometric and catalytic oxidation methods have been widely used for this transformation, an efficient and valuable method should be further explored from the views of reusable catalysts, less waste, and convenient procedures. Herein an inorganic-ligand supported iron catalyst (NH4)3[FeMo6O18(OH)6]·7H2O was described as a heterogeneous molecular catalyst in acetic acid for this transformation in which hydrogen peroxide was used as the terminal oxidant. Under the optimized reaction conditions, carbon-carbon bond cleavage of 1,2-diols could be achieved in almost all cases and carboxylic acids or ketones could be afforded with a high conversion rate and high selectivity. Furthermore, the catalytic system was used efficiently to degrade renewable biomass oleic acid. Mechanistic insights based on the observation of the possible intermediates and control experiments are presented.
- Chen, Weiming,Xie, Xin,Zhang, Jian,Qu, Jian,Luo, Can,Lai, Yaozhu,Jiang, Feng,Yu, Han,Wei, Yongge
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p. 9140 - 9146
(2021/11/23)
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- FLOW CHEMISTRY SYNTHESIS OF ISOCYANATES
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The disclosure provides, inter alia, safe and environmentally-friendly methods, such as flow chemistry, to synthesize isocyanates, such as methylene diphenyl diisocyanate, toluene diisocyanate, hexamethylene diisocyanate, isophorone diisocyanate, and tetramethylxylene diisocyanate.
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Paragraph 0008; 0175; 0180
(2021/06/22)
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- Process for preparing azelaic acid
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A process for preparing azelaic acid is disclosed. In particular, the process for preparing azelaic acid is an ozone free process. The process for preparing azelaic acid comprises a step of decarboxylation of tetra-carboxylic acid in the presence of a organic sulfonic acid.
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Paragraph 0105-0108
(2021/02/19)
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- Reactive Species and Reaction Pathways for the Oxidative Cleavage of 4-Octene and Oleic Acid with H2O2over Tungsten Oxide Catalysts
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Oxidative cleavage of carbon-carbon double bonds (C-C) in alkenes and fatty acids produces aldehydes and acids valued as chemical intermediates. Solid tungsten oxide catalysts are low cost, nontoxic, and selective for the oxidative cleavage of C-C bonds with hydrogen peroxide (H2O2) and are, therefore, a promising option for continuous processes. Despite the relevance of these materials, the elementary steps involved and their sensitivity to the form of W sites present on surfaces have not been described. Here, we combine in situ spectroscopy and rate measurements to identify significant steps in the reaction and the reactive species present on the catalysts and examine differences between the kinetics of this reaction on isolated W atoms grafted to alumina and on those exposed on crystalline WO3 nanoparticles. Raman spectroscopy shows that W-peroxo complexes (W-(η2-O2)) formed from H2O2 react with alkenes in a kinetically relevant step to produce epoxides, which undergo hydrolysis at protic surface sites. Subsequently, the CH3CN solvent deprotonates diols to form alpha-hydroxy ketones that react to form aldehydes and water following nucleophilic attack of H2O2. Turnover rates for oxidative cleavage, determined by in situ site titrations, on WOx-Al2O3 are 75% greater than those on WO3 at standard conditions. These differences reflect the activation enthalpies (ΔH?) for the oxidative cleavage of 4-octene that are much lower than those for the isolated WOx sites (36 ± 3 and 60 ± 6 kJ·mol-1 for WOx-Al2O3 and WO3, respectively) and correlate strongly with the difference between the enthalpies of adsorption for epoxyoctane (ΔHads,epox), which resembles the transition state for epoxidation. The WOx-Al2O3 catalysts mediate oxidative cleavage of oleic acid with H2O2 following a mechanism comparable to that for the oxidative cleavage of 4-octene. The WO3 materials, however, form only the epoxide and do not cleave the C-C bond or produce aldehydes and acids. These differences reflect the distinct site requirements for these reaction pathways and indicate that acid sites required for diol formation are strongly inhibited by oleic acids and epoxides on WO3 whereas the Al2O3 support provides sites competent for this reaction and increase the yield of the oxidative cleavage products.
- Yun, Danim,Ayla, E. Zeynep,Bregante, Daniel T.,Flaherty, David W.
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p. 3137 - 3152
(2021/04/06)
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- Conversion of oleic acid into azelaic and pelargonic acid by a chemo-enzymatic route
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A chemo-enzymatic approach for the conversion of oleic acid into azelaic and pelargonic acid is herein described. It represents a sustainable alternative to ozonolysis, currently employed at the industrial scale to perform the reaction. Azelaic acid is produced in high chemical purity in 44% isolation yield after three steps, avoiding column chromatography purifications. In the first step, the lipase-mediated generation of peroleic acid in the presence of 35% H2O2 is employed for the self-epoxidation of the unsaturated acid to the corresponding oxirane derivative. This intermediate is submitted to in situ acid-catalyzed opening, to afford 9,10-dihydroxystearic acid, which readily crystallizes from the reaction medium. The chemical oxidation of the diol derivative, using atmospheric oxygen as a stoichiometric oxidant with catalytic quantities of Fe(NO3)3·9·H2O, (2,2,6,6-tetramethylpiperidin-1-yl)oxyl (TEMPO), and NaCl, affords 9,10-dioxostearic acid which is cleaved by the action of 35% H2O2 in mild conditions, without requiring any catalyst, to give pelargonic and azelaic acid.
- Brenna, Elisabetta,Colombo, Danilo,Di Lecce, Giuseppe,Gatti, Francesco G.,Ghezzi, Maria Chiara,Tentori, Francesca,Tessaro, Davide,Viola, Mariacristina
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- Synthesis of Branched Biolubricant Base Oil from Oleic Acid
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The mature manufacturing of synthetic lubricants (poly-α-olefins, PAO) proceeds through oligomerization, polymerization, and hydrogenation reactions of petrochemical ethylene. In this work, we utilize the inexpensive bio-derived oleic acid as raw material to synthesize a crotch-type C45 biolubricant base oil via a full-carbon chain synthesis without carbon loss. It contains several cascade chemical processes: oxidation of oleic acid to azelaic acid (further esterification to dimethyl azelate) and nonanoic acid (both C9 chains). The latter is then selectively hydrogenated to nonanol and brominated to the bromo-Grignard reagent. In a next step, a C45 biolubricant base oil is formed by nucleophilic addition (NPA) of excessive C9 bromo-Grignard reagent with dimethyl azelate, followed by subsequent hydrodeoxygenation. The specific properties of the prepared biolubricant base oil are almost equivalent to those of the commercial lubricant PAO6 (ExxonMobil). This process provides a new promising route for the production of value-added biolubricant base oils.
- Chen, Shuang,Wu, Tingting,Zhao, Chen
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p. 5516 - 5522
(2020/09/07)
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- Characterization of Bitter-Tasting Oxylipins in Poppy Seeds (Papaver somniferum L.)
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Activity-guided fractionation of poppy seed (Papaver somniferum L.) extracts and analysis of fatty acid oxidation model experiments, followed by liquid chromatography time-of-flight mass spectrometry, tandem mass spectrometry, and one-/two-dimensional nuclear magnetic resonance experiments, revealed the chemical structures of five bitter-tasting fatty acids (1-5), three monoglycerides (6-8), six C18-lipidoxidation products (9-14), and four lipid oxidation degradation products (15 and 17-19) as well as two previously unreported monoglyceride oxidation degradation products, namely, 9-(2′,3′-dihydroxypropyloxy)-9-oxononaic acid (1-azeloyl-rac-glycerol, 16) and 1-(2′,3′-dihydroxypropyl)-8-(5″-oxo-2″,5″-dihydrofruan-2″-yl)-octonoate (1-ODFO-rac-glycerol, 20). Sensory studies exhibited low bitter taste threshold concentrations between 0.08 and 0.29 mmol/L, particularly for the higher oxidated C18-fatty acids trihydroxyoctadecenoic acid (THOE, 12), 12,13-dihydroxy-9-oxo-10-octadecenoic acid (12,13-diOH-9-oxo, 13), and 9,10-dihydroxy-13-oxo-11-octadecenoic acid (9,10-diOH-13-oxo, 14) as well as for the lipidoxidation degradation products 4-hydroxy-2-noneic acid (4-HNA, 17), 4-hydroxy-2-docecendienoic acid (HDdiA, 18), and 8-(5′-oxo-2′,5′-dihydrofuran-2′-yl)-octanoic acid (ODFO, 20).
- Lainer, Johanna,Dawid, Corinna,Dunkel, Andreas,Glaser, Peter,Wittl, Stephanie,Hofmann, Thomas
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p. 10361 - 10373
(2020/01/31)
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- Direct and Selective Synthesis of Adipic and Other Dicarboxylic Acids by Palladium-Catalyzed Carbonylation of Allylic Alcohols
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A general and direct synthesis of dicarboxylic acids including industrially important adipic acid by palladium-catalyzed dicarbonylation of allylic alcohol is reported. Specifically, the combination of PdCl2 and a bisphosphine ligand (HeMaRaphos) promotes two different carbonylation reactions with high activity and excellent selectivity.
- Beller, Matthias,Ge, Yao,Huang, Weiheng,Jackstell, Ralf,Liu, Jiawang,Neumann, Helfried,Yang, Ji
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supporting information
p. 20394 - 20398
(2020/09/21)
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- Preparation method of biomass-based azelaic acid
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The invention discloses a preparation method of biomass-based azelaic acid. The method comprises the following steps: 1) in an aqueous solution, carrying out aldol condensation reaction on 5-formyl-2-furancarboxylic acid and pyruvic acid on a base catalyst to generate a C9 condensation product; 2) carrying out hydrogenation reaction on the C9 condensation product in the presence of a hydrogenationcatalyst to generate a C9 saturated product; and 3) performing hydrogenolysis reaction on the C9 saturated product on the hydrogenolysis catalyst to generate azelaic acid. According to the invention,biomass-based platform molecules are used as reaction raw materials, water is used as a reaction solvent, a heterogeneous catalyst which is easy to recycle is adopted, the catalyst has high catalyticactivity and cycling stability, and the reaction process is green, pollution-free and environment-friendly.
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Paragraph 0048; 0053
(2020/06/20)
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- Flexible polyurethanes, renewable fuels, and flavorings from a microalgae oil waste stream
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Renewable polymers have become an important focus in next-generation materials, and algae biomass offers an environmentally low-impact feedstock that can serve multiple uses. This study aims to develop a scalable methodology for production of microalgae-based polyols for polyurethane synthesis from waste oils derived from algae biomass. Following separation of omega-3 fatty acids from algae oil, residual oils can offer valuable building blocks for petrochemical replacements. However, unlike vegetable oils, algae oils contain organic contaminants, including photosynthetic pigments and hydrophobic cofactors that can complicate preparative methodologies. Here we convert and purify waste streams from omega-3 depleted Nannochloropsis salina algae oil, with major components consisting of palmitic and palmitoleic acid, into azelaic acid (AA) as a building block for flexible polyurethanes, with a simultaneous production of heptanoic acid (HA) as a flavor and fragrance precursor. Conversion of free fatty acid mixtures into a soft soap allows extraction of organic contaminants, and urea complexation provides isolated palmitoleic acid, which is subsequently ozonolyzed to produce AA and HA. Bio-based polyester diols are prepared from AA via esterification to provide a polyol monomer for flexible polyurethane foam preparation. The HA co-product is modified to produce the flavoring agent methyl heptanoate and also decarboxylated to produce hexane as a renewable solvent. This scalable process can be performed on oils from multiple algal species, offering valuable monomers from a highly sustainable source.
- Burkart, Michael D.,Griffin, Graham,Mayfield, Stephen P.,Neelakantan, Nitin,Phung Hai, Thien An,Pomeroy, Robert,Sherman, Suryendra D.,Tessman, Marissa
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supporting information
p. 3088 - 3094
(2020/06/17)
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- Method for preparing nonanoic acid and azelaic acid
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The invention belongs to a synthesis method, particularly a method for preparing nonanoic acid and azelaic acid by using oleic acid. According to the method, oleic acid and glacial acetic acid are subjected to ozone oxidation and oxidative cleavage, the reactants are further extracted and purified to respectively obtain high purity nonanoic acid and high purity azelaic acid, and a mass ratio of oleic acid to glacial acetic acid is 1:2-4. According to the present invention, the azelaic acid purification is performed with near boiling water without the additional catalyst, such that the method has advantages of simple process, low cost and environmental protection, and is suitable for large-scale production.
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Paragraph 0023-0049
(2019/01/23)
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- PRODUCTION OF CARBOXYLIC ACIDS FROM VICINAL DIOLS
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The present invention relates to a process of preparation of carboxylic acids by oxidative cleavage of at least one vicinal diol or an epoxide in the presence of an oxidant comprising molecular oxygen and a heterogeneous catalyst comprising a copper oxide.
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Page/Page column 13; 15; 16
(2019/06/11)
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- Synthesis of Azelaic Acid
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This invention concerns a method of synthesizing Azelaic Acid. Particular reference is made to providing a new synthetic process for preparing azelaic acid in large scale with high purity (e.g., >99.7% with any individual impurity not more than 0.1%), which can be used as an active pharmaceutical ingredient.
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Paragraph 0101-0107
(2019/07/10)
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- OXIDATIVE CLEAVAGE OF OLEFINS, EPOXIDES AND ALCOHOLS
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Provided is a process for producing a compound I comprising at least one functional group chosen in the group consisting of epoxy group, hydroxyl group and carbonyl group and by reacting a compound J comprising at least one functional group chosen in the group consisting of alkenyl group, epoxy group and hydroxyl group with an an oxidant in the presence of solid amphiphilic catalytic particles A and solid amphiphilic catalytic particles B.
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Page/Page column 24-25
(2019/02/06)
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- Sodium stannate promoted double bond cleavage of oleic acid by hydrogen peroxide over a heterogeneous WO3 catalyst
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The production of valuable mono- and dicarboxylic acids from abundant and renewable vegetable oil sources is of great industrial interest. It is demonstrated by a simple and eco-friendly heterogeneous catalytic system for direct oleic acid (OA) cleavage by hydrogen peroxide to produce azelaic acid (AA) and nonanoic acid (NA). Commercially available tungsten oxide was used as a heterogeneous catalyst without any modification or pretreatment, and sodium stannate was used as a H2O2 stabilizer to improve the efficiency of the oxidant. The sodium stannate additive notably improved the product yields and it could be recycled together with the tungsten oxide catalyst. Isolated product yields up to 89% for azelaic acid and 65% for nonanoic acid were achieved from oleic acid in this simple system, which should be among the best results for oleic acid cleavage in heterogeneous systems. This strategy is also applicable for other catalytic systems for the cleavage of OA or its derivatives. This work provides a potential method for the large scale upgrading of oleic acid.
- Li, Xiukai,Choo Ping Syong, Joel,Zhang, Yugen
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supporting information
p. 3619 - 3624
(2018/08/06)
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- Allene Oxide Synthase Pathway in Cereal Roots: Detection of Novel Oxylipin Graminoxins
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Young roots of wheat, barley, and sorghum, as well as methyl jasmonate pretreated rice seedlings, undergo an unprecedented allene oxide synthase pathway targeted to previously unknown oxylipins 1–3. These Favorskii-type products, (4Z)-2-pentyl-4-tridecene-1,13-dioic acid (1), (2′Z)-2-(2′-octenyl)-decane-1,10-dioic acid (2), and (2′Z,5′Z)-2-(2′,5′-octadienyl)-decane-1,10-dioic acid (3), have a carboxy function at the side chain, as revealed by their MS and NMR spectral data. Compounds 1–3 were the major oxylipins detected, along with the related α-ketols. Products 1–3 were biosynthesized from (9Z,11E,13S)-13-hydroperoxy-9,11-octadecadienoic acid, (9S,10E,12Z)-9-hydroperoxy-10,12-octadecadienoic acid (9-HPOD), and (9S,10E,12Z,15Z)-9-hydroperoxy-10,12,15-octadecatrienoic acid, respectively, via the corresponding allene oxides and cyclopropanones. The data indicate that conversion of the allene oxide into the cyclopropanone is controlled by soluble cyclase. The short-lived cyclopropanones are hydrolyzed to products 1–3. The collective name “graminoxins” has been ascribed to oxylipins 1–3.
- Grechkin, Alexander N.,Ogorodnikova, Anna V.,Egorova, Alevtina M.,Mukhitova, Fakhima K.,Ilyina, Tatiana M.,Khairutdinov, Bulat I.
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p. 336 - 343
(2018/06/04)
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- Method of preparing azelaic acid
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The invention relates to a method of preparing azelaic acid and provides a novel synthesizing and purifying process which is high in yield, simple to separate and purify, has a very high economical benefit, and is suitable for industrial production. The formula is as shown in the description.
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Page/Page column 3; 4; 5
(2018/07/30)
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- Sustainable Oxidative Cleavage of Vegetable Oils into Diacids by Organo-Modified Molybdenum Oxide Heterogeneous Catalysts
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Abstract: Exploiting vegetable oils to produce industrially valuable diacids via an eco-friendly process requires an efficient and recyclable catalyst. In this work, a novel catalytic system based on organo-modified molybdenum trioxide was synthesized by a green hydrothermal method in one simple step, using Mo powder as precursor, hydrogen peroxide, and amphiphilic surfactants cetyltrimethylammonium bromide (CTAB) and tetramethylammonium bromide (TMAB) as capping agents. The synthesized materials were first characterized by different techniques including XRD, SEM, TGA, and FT-IR. Interestingly, various morphologies were obtained depending on the nature of the surfactants and synthetic conditions. The synthesized catalysts were employed in oxidative cleavage of oleic acid, the most abundant unsaturated fatty acid, to produce azelaic and pelargonic acids with a benign oxidant, H2O2. Excellent catalytic activities resulting in full conversion of initial oleic acid were obtained, particularly for CTAB-capped molybdenum oxide (CTAB/Mo molar ratio of 1:3) that gave 83 and 68% yields of production of azelaic and pelargonic acids, respectively. These are the highest yields that have been obtained for this reaction by heterogeneous catalysts up to now. Moreover, the CTAB-capped catalyst could be conveniently separated from the reaction mixture by simple centrifugation and reused without significant loss of activity up to at least four cycles. Graphical Abstract: [Figure not available: see fulltext.].
- Ello, Aimé Serge,Enferadi-kerenkan, Amir,Trokourey, Albert,Do, Trong-On
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p. 1451 - 1461
(2017/09/27)
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- MIXED OXIDES FOR THE OXIDATIVE CLEAVAGE OF LIPIDS USING OXYGEN TO AFFORD MONO- AND DI-CARBOXYLIC ACIDS
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This invention relates to the synthesis of new catalysts based on earth crust abundant mixed oxides that can produce cleavage of fatty acids (FA), FA methyl esters, or even lipids in a single step using oxygen as oxidant in solventless conditions.
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Page/Page column 15-16
(2017/12/29)
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- Combined Biocatalytic and Chemical Transformations of Oleic Acid to ω-Hydroxynonanoic Acid and α,ω-Nonanedioic Acid
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A practical chemoenzymatic method for the synthesis of 9-hydroxynonanoic acid and 1,9-nonanedioic acid (i.e., azelaic acid) from oleic acid [(9Z)-octadec-9-enoic acid] was investigated. Biotransformation of oleic acid into 9-(nonanoyloxy)nonanoic acid via 10-hydroxyoctadecanoic acid and 10-keto-octadecanoic acid was driven by a C-9 double bond hydratase from Stenotrophomonas maltophilia, an alcohol dehydrogenase from Micrococcus luteus, and a Baeyer–Villiger monooxygenase (BVMO) from Pseudomonas putida KT2440, which was expressed in recombinant Escherichia coli. After production of the ester (i.e., the BVMO reaction product), the compound was chemically hydrolyzed to n-nonanoic acid and 9-hydroxynonanoic acid because n-nonanoic acid is toxic to E. coli. The ester was also converted into 9-hydroxynonanoic acid and the n-nonanoic acid methyl ester, which can be oxygenated into the 9-hydroxynonanoic acid methyl ester by the AlkBGT from P. putida GPo1. Finally, 9-hydroxynonanoic acid was chemically oxidized to azelaic acid with a high yield under fairly mild reaction conditions. For example, whole-cell biotransformation at a high cell density (i.e., 10 g dry cells/L) allowed the final ester product concentration and volumetric productivity to reach 25 mM and 2.8 mM h?1, respectively. The overall molar yield of azelaic acid from oleic acid was 58%, based on the biotransformation and chemical transformation conversion yields of 84% and 68%, respectively. (Figure presented.).
- Koppireddi, Satish,Seo, Joo-Hyun,Jeon, Eun-Yeong,Chowdhury, Partha Sarathi,Jang, Hyun-Young,Park, Jin-Byung,Kwon, Yong-Uk
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p. 3084 - 3092
(2016/10/09)
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- PROCESS FOR PREPARATION OF AZELAIC ACID
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Provided is a process for preparing azelaic acid.
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Paragraph 0132
(2016/05/19)
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- A hydrogen peroxide and potassium permanganate combined oxidation synthesis ninth stem method of the second acid
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The invention relates to a method for synthesizing anchoic acid through combined oxidation of hydrogen peroxide and potassium permanganate. The method comprises the following steps: mixing oleic acid, a phosphotungstic acid catalyst and benzyl triethyl ammonium chloride, and rapidly stirring and heating under the condition of introducing oxygen; adding potassium permanganate, adding a hydrogen peroxide solution, and separating the mixed liquid in a separating funnel after reaction is ended, wherein manganese dioxide is arranged at the lower part of a water layer; an oil layer is arranged on the water layer and is easy to separate; refrigerating and crystallizing the separated water phase, and separating out white powder; and carrying out suction filtration and drying, so as to obtain anchoic acid solid. According to the method disclosed by the invention, other chemical apparatuses do not need to be used in the overall reaction process, so that energy consumption is lowered; the reaction speed is increased; the time is saved; a lot of organic solvents are not required in the reaction; and the method is environment-friendly and relatively high in reaction yield; a one-step reaction process is simple; a reaction system is easy to separate; the production cost is effectively reduced; and the method is environment-friendly.
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Paragraph 0017-0018
(2017/04/03)
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- Processes for Making Azelaic Acid and Derivatives Thereof
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Methods of making azelaic acid, or derivatives thereof, from unsaturated monobasic acids or esters are disclosed herein. In some embodiments, the unsaturated monobasic acids or esters are C10-17 unsaturated monobasic acids or esters.
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Paragraph 0066
(2016/06/09)
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- COMBINED SYNTHESIS OF A NITRILE-ESTER/ACID AND OF A DIESTER/DIACID
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A method for the combined synthesis of a mono-unsaturated nitrile-ester(acid) and of a bi-functional carbonyl compound, wherein it includes a step including the cross metathesis mc1 of an unsaturated fatty acid/ester compound with an unsaturated nitrile compound, in which mc1 is performed with partial conversion such as to obtain and recover, separately, at least the following products: a mono-unsaturated nitrile-ester/acid and a symmetrical compound, diester or diacid respectively including a double bond located in the middle of the molecular chain of compound, and subsequently a step including the oxidation cleavage cp2 of the double bond of compound, such as to form a single type of carbonyl compound having formula R2-(CH2)n-COR′, in which R′ is H or OH, depending on the operating conditions selected for the oxidation cleavage cp2. Also, the production of monomers for the polymer industry.
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- Production of dicarboxylic acids from novel unsaturated fatty acids by laccase-catalyzed oxidative cleavage
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The establishment of renewable biofuel and chemical production is desirable because of global warming and the exhaustion of petroleum reserves. Sebacic acid (decanedioic acid), the material of 6,10-nylon, is produced from ricinoleic acid, a carbonneutral material, but the process is not eco-friendly because of its energy requirements. Laccase-catalyzing oxidative cleavage of fatty acid was applied to the production of dicarboxylic acids using hydroxy and oxo fatty acids involved in the saturation metabolism of unsaturated fatty acids in Lactobacillus plantarum as substrates. Hydroxy or oxo fatty acids with a functional group near the carbon-carbon double bond were cleaved at the carbon-carbon double bond, hydroxy group, or carbonyl group by laccase and transformed into dicarboxylic acids. After 8 h, 0.58 mM of sebacic acid was produced from 1.6 mM of 10-oxo-cis-12,cis-15-octadecadienoic acid (αKetoA) with a conversion rate of 35% (mol/mol). This laccase-catalyzed enzymatic process is a promising method to produce dicarboxylic acids from biomass-derived fatty acids.
- Takeuchi, Michiki,Kishino, Shigenobu,Park, Si-Bum,Kitamura, Nahoko,Watanabe, Hiroko,Saika, Azusa,Hibi, Makoto,Yokozeki, Kenzo,Ogawa, Jun
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p. 2132 - 2137
(2016/11/03)
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- ENHANCED DIACID PRODUCTION WITH GENETICALLY MODIFIED MICRO-ORGANISMS
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The present invention relates to a field of diacids, and more precisely to a method of producing diacids. The invention further relates to recombinant microorganisms comprising omega-oxidation and increased diacid production, and uses and methods related thereto.
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Page/Page column 27
(2016/12/12)
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- Process For Preparing A Carboxylic Acid
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A process for preparing a carboxylic acid, including a step of bringing at least one vicinal diol or at least one vicinal polyol into contact with an atmosphere including oxygen, and a catalyst, and in the absence of additional solvent.
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Paragraph 0122-0124
(2017/04/14)
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- Sustainable Process for Production of Azelaic Acid Through Oxidative Cleavage of Oleic Acid
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This work describes two sustainable methods for production and purification of azelaic acid (AA) to replace the current process of ozonolysis of oleic acid (OA). The first proceeds in two steps, coupling smooth oxidation of OA to 9,10-dihydroxystearic acid (DSA) with subsequent oxidative cleavage by sodium hypochlorite. An alternative methodology is also proposed, using a chemocatalytic system consisting of H2O2/H2WO4 for direct oxidative cleavage of the double bond of OA at 373 K. A convenient technique for separation and purification of azelaic acid is also proposed.
- Benessere, Vincenzo,Cucciolito, Maria E.,De Santis, Augusta,Di Serio, Martino,Esposito, Roberto,Ruffo, Francesco,Turco, Rosa
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p. 1701 - 1707
(2015/12/23)
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- Transformations of peroxide products of oleic acid ozonolysis at treatment with hydroxylamine and semicarbazide hydrochlorides
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Peroxide products of oleic acid ozonolysis treated with semicarbazide and hydroxylamine hydrochlorides in methanol are predominantly converted into methyl nonanoate and dimethyl nonanedioate, in 2-propanol, into isopropyl nonanoate and monoisopropyl ester of nonanedioic acid, and also into nonanenitrile, in tetrahydrofuran and in a mixture of acetic acid with dichloromethane, into nonanoic and nonanedioc acids, and also in nonanal oxime and 9-(hydroxyimino)nonanoic acid.
- Ishmuratov, G. Yu.,Yakovleva,Botsman,Legostaeva, Yu. V.,Nazarov,Baidimirov
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p. 610 - 614
(2015/07/02)
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- SELECTIVE EXTRACTION OF AN OMEGA-FUNCTIONALIZED ACID AFTER OXIDATIVE CLEAVAGE OF AN UNSATURATED FATTY ACID AND DERIVATIVES
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The invention relates to a process for the selective extraction of a reaction product, derived from an oxidative cleavage of an unsaturated fatty acid or of an ester derivative or of an unsaturated nitrile derivative, said reaction product being an ω-functionalized acid from among C6 to C15 diacids, acid esters and acid nitriles, using as selective extraction solvent a composition comprising a mixture of water and of C1-C4 carboxylic acid. The invention also relates to the use of said process and of the extraction solvent composition for the preparation of C6 to C15 amino acid, diacid or acid ester monomers for the preparation of polycondensation polymers, in particular polyamides.
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Paragraph 0058; 0059; 0060; 0061
(2015/11/18)
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- METHOD OF OXIDATIVE MOLECULAR CLEAVAGE OF A FATTY COMPOUND
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A method of oxidative molecular cleavage of a fatty compound, includes: —forming a liquid composition, referred to as a fatty composition, consisting of at least one aliphatic carboxylic acid, the fatty composition including the fatty compound; characterised in that it then involves: —adding, to the fatty composition, a solution of at least one quaternary ammonium salt in water capable of forming an emulsion from the fatty compound and water, then; —adding, to the emulsion, a liquid solution of at least one tungstophosphoric acid in a composition including hydrogen peroxide (H2O2), in such a way as to form, in situ in the emulsion, a quantity of a phase-transfer catalyst, formed from tungstophosphoric acid and at least one quaternary ammonium from the quaternary ammonium salt(s), and to allow the oxidative molecular cleavage of the fatty compound.
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Paragraph 0088
(2015/01/06)
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- Flammability and thermal properties of novel semi aromatic polyamide/organoclay nanocomposite
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The development of semi aromatic polyamide/organoclays nanocomposites (PANC) is reported in this communication. New polyamide (PA) was successfully synthesized through direct polycondensation reaction between bio-based diacid and aromatic diamine. PA exhibited strong UV-vis absorption band at 412 nm. Its photoluminescence spectrum showed maximum band at 511 nm in the green region. The surface modification of montmorillonite was carried out through ion-exchange reaction using 1,4-bis[4-aminophenoxy]butane (APB) as a modifier. Then PANCs containing 3 and 6 wt.% of the modified montmorillonite (MMT-APB) were prepared. Flammability and thermal properties of PA and the nanocomposites were studied by microscale combustion calorimeter (MCC), thermogravimetric analysis (TGA) and differential scanning calorimetry (DSC). TGA results in both air and nitrogen atmospheres indicated improving in thermal properties of PANCs compared to the neat PA. According to MCC analysis, a 31.6% reduction in pHRR value has been achieved by introducing 6 wt.% of the organoclay in PA matrix.
- Shabanian, Meisam,Mirzakhanian, Zeinab,Basaki, Nemat,Khonakdar, Hossein Ali,Faghihi, Khalil,Hoshyargar, Faegheh,Wagenknecht, Udo
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- Insights into gold-catalyzed synthesis of azelaic acid
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A novel green route for the synthesis of azelaic and pelargonic acid via aerobic gold-catalyzed cleavage of 9,10-dihydroxystearic acid (DSA) was investigated recently. In this study, the examination of the reaction mechanism is described. The results of the application of 18O-labeled molecular oxygen and sodium hydroxide as well as of diastereomeric pure erythro- and threo-DSA were discussed. Assumed reaction intermediates were synthesized and subjected to the same reaction conditions as with DSA. As a conclusion from the obtained data, an oxidative dehydrogenation mechanism was postulated. Additionally, the aging of the gold catalyst used under different storage conditions was explored. the Partner Organisations 2014.
- Kulik, Anna,Martin, Andreas,Pohl, Marga-Martina,Fischer, Christine,Koeckritz, Angela
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p. 1799 - 1806
(2014/04/17)
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- Whole-cell one-pot biosynthesis of azelaic acid
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Polymers benefit from the use of biogenic resources such as fatty acids. They enable easy access to valuable monomeric building blocks, which, in comparison to their exclusively fossil counterparts, lead to products with improved physicochemical properties. Monomers of special interest are medium-chain dicarboxylic acids, which are not easy to obtain by traditional chemical means. Previously, we established an in vitro pathway that combined a 9-lipoxygenase and a 9/13-hydroperoxide lyase, which enabled the conversion of linoleic acid via a hydroperoxy intermediate into 9-oxononanoic acid, the precursor of azelaic acid. Herein, we aimed for the further development of the multi-enzyme cascade, which included the oxidation of 9-oxononanoic acid and the establishment of a suitable whole-cell catalyst. A detailed investigation of the simultaneous in vitro reaction setup revealed that both lipoxygenase activation and the subsequent hydroperoxide lyase reaction depend on the hydroperoxide reaction intermediate. For the activation of lipoxygenase, the hydroperoxide lyase activity, therefore, has to be significantly reduced. In accordance with these observations, we established a suitable dual-expression system and we further demonstrated that endogenous E. coli redox enzymes are feasible to oxidize 9-oxononanoic acid to azelaic acid. The resulting whole-cell catalyst is, therefore, able to perform the direct bioconversion of linoleic acid into azelaic acid. The use of organic solvent as the second phase improved the overall performance of the E. coli host strain. The developed one-pot, single-step process afforded 29 mg L-1 of azelaic acid within 8 h with a substrate conversion of 34 % and a selectivity of 47 %. Tiny polymer factories: An E. coli whole-cell catalyst is developed for the bioconversion of linoleic acid to azelaic acid, an important building block for biopolymers. The catalytic machinery of the prokaryotic host is equipped with two plant enzymes, a lipoxygenase, and a hydroperoxide lyase. Together with an endogenous oxidoreductase, this three-enzyme cascade reaction catalyzes the oxidative cleavage of the fatty acid substrate.
- Otte, Konrad B.,Kittelberger, Jens,Kirtz, Marko,Nestl, Bettina M.,Hauer, Bernhard
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p. 1003 - 1009
(2014/05/06)
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- Ozonolysis of methyl oleate monolayers at the air-water interface: Oxidation kinetics, reaction products and atmospheric implications
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Ozonolysis of methyl oleate monolayers at the air-water interface results in surprisingly rapid loss of material through cleavage of the CC bond and evaporation/dissolution of reaction products. We determine using neutron reflectometry a rate coefficient of (5.7 ± 0.9) × 10-10 cm2 molecule-1 s-1 and an uptake coefficient of ～3 × 10-5 for the oxidation of a methyl ester monolayer: the atmospheric lifetime is ～10 min. We obtained direct experimental evidence that a minor change to the structure of the molecule (fatty acid vs. its methyl ester) considerably impacts on reactivity and fate of the organic film.
- Pfrang, Christian,Sebastiani, Federica,Lucas, Claire O. M.,King, Martin D.,Hoare, Ioan D.,Chang, Debby,Campbell, Richard A.
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p. 13220 - 13228
(2014/06/24)
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- METHOD FOR PREPARING CARBOXYLIC ACIDS BY OXIDATIVE CLEAVAGE OF A VICINAL DIOL
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The present invention relates to a method for preparing carboxylic acids, in particular mono- and dicarboxylic acids, by oxidative cleavage of a vicinal diol. According to the invention, said method consists of reacting a vicinal diol of formula I: where: p is an integer comprised between 1 and 6; R1 and R2 are, separately: an alkyl or hydroxyl group having 1 to 12 carbon atoms;a —(CH2)n—C02M group where n, which can be identical or different in R1 and R2, is an integer comprised between 1 and 11 and M is a hydrogen atom or an alkyl group having 1 to 4 carbon atoms or an alkaline cation; or R1 and R2 jointly form an alkylene —(CH2)m- group where m is an integer comprised between 2 and 10, preferably between 2 and 6; with industrial-grade sodium hypochlorite (or bleach), in the absence of an organic solvent and without adding a catalyst, preferably at room temperature. The invention can be used for recycling natural vegetable oils.
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- New environmentally friendly oxidative scission of oleic acid into azelaic acid and pelargonic acid
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Oleic acid (OA) is a renewable monounsaturated fatty acid obtained from high oleic sunflower oil. This work was focused on the oxidative scission of OA, which yields a mono-acid (pelargonic acid, PA) and a di-acid (azelaic acid, AA) through an emulsifying system. The conventional method for producing AA and PA consists of the ozonolysis of oleic acid, a process which presents numerous drawbacks. Therefore, we proposed to study a new alternative process using a green oxidant and a solvent-free system. OA was oxidized in a batch reactor with a biphasic organic-aqueous system consisting of hydrogen peroxide (H 2O2, 30 %) as an oxidant and a peroxo-tungsten complex Q3{PO4[WO(O2)2]4} as a phase-transfer catalyst/co-oxidant. Several phase-transfer catalysts were prepared in situ from tungstophosphoric acid, H2O2 and different quaternary ammonium salts (Q+, Cl-). The catalyst [C5H5N(n-C16H33)] 3{PO4[WO(O2)2]4} was found to give the best results and was chosen for the optimization of the other parameters of the process. This optimization led to a complete conversion of OA into AA and PA with high yields (>80 %) using the system OA/H 2O2/[C5H5N(n-C16H 33)]3{PO4[WO(O2)2] 4} (1/5/0.02 molar ratio) at 85 C for 5 h. In addition, a new treatment was developed in order to recover the catalyst.
- Godard, Anais,De Caro, Pascale,Thiebaud-Roux, Sophie,Vedrenne, Emeline,Mouloungui, Zephirin
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p. 133 - 140
(2013/03/13)
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- Efficient ruthenium-catalysed oxidative cleavage of methyl oleate with hydrogen peroxide as oxidant
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The oxidative cleavage of alkenes leads to the formation of carboxylic acids. One of the few technical processes using this reaction is the production of azelaic acid via the ozonolysis of oleic acid. Because of the need for stoichiometric amounts of the expensive oxidant ozone, together with safety hazards, there is still a requirement for a catalytic process using a cheap and environmentally friendly oxidant. In the present work, the oxidative cleavage of methyl oleate by hydrogen peroxide was catalysed by an easily available ruthenium precursor with dipicolinic acid as ligand. The systematic optimisation of the reaction led to the formation of azelaic acid monomethyl ester in high yields amounting to 86%. The investigation of the reaction pathway showed that the reaction proceeds via a tandem reaction of epoxidation and hydrolysis of the epoxide and oxidative cleavage of the vic-diol. The Royal Society of Chemistry.
- Behr, Arno,Tenhumberg, Nils,Wintzer, Andreas
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p. 172 - 180
(2013/04/23)
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- Process for Producing Nitrile-Fatty Acid Compounds
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The invention relates to a process for synthesizing a nitrile-fatty acid (heminitrile) from unsaturated fatty acids, in the form of an acid or a simple ester or a “complex” ester of triglyceride type, which is first of all converted into an unsaturated fatty nitrile which is subjected to oxidative cleavage using H2O2 as oxidizing agent. This process can be used for preparing polyamide monomers, such as ω-amino acids or diamines or diacids equivalent to said heminitrile and for obtaining polyamides from raw materials which are of natural origin and from a renewable source.
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Paragraph 0151-0160
(2014/02/15)
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- PROCESS FOR THE PREPARATION OF AZELEIC ACID FROM 9-OCTADECENEDIOIC ACID
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The invention relates to a process for the preparation of azelaic acid or alkyl azelate starting from mono-unsaturated 9-octadecenedioic acid or its corresponding alkylester characterized in that the process comprises at least the following step: ? reacting the mono-unsaturated 9-octadecene dioic acid or its corresponding alkylester with hydrogen peroxide in the presence of an organic carboxylic acid other than 9-octadecene dioic acid and a suitable catalyst to effect cleavage of the double bond in the mono-unsaturated 9-octadecene dioic acid or its corresponding alkylester. The invention further relates to the azelaic acid or alkyl azelate obtainable by the process according to the invention and to the use of azelaic acid or alkyl azelate or monomers derived there from for the preparation of a polymer, especially a polyamide.
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Page/Page column 8
(2013/07/05)
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- SYNTHESIS OF ALPHA,OMEGA-DICARBOXYLIC ACIDS AND ESTERS THEREOF FROM UNSATURATED FATTY ACID DERIVATIVES
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A process for preparing an alpha, omega-dicarboxylic acid or an ester thereof, which includes (a) subjecting at least one unsaturated fatty acid or fatty acid derivative to ozonolysis to obtain an ozonolysis reaction mixture; and (b) oxidizing the ozonolysis reaction mixture with an oxidizing agent in the presence of an acid catalyst to obtain an oxidized reaction mixture comprising at least one alpha, omega-dicarboxylic acid or ester; wherein the process is performed using a solvent and the acid catalyst has a pKa of less than or equal to zero, as measured at 25° C.
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Page/Page column 4-5
(2012/10/08)
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- CONTINUOUS PROCESS FOR THE PRODUCTION OF DERIVATIVES OF SATURATED CARBOXYLIC ACIDS
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There is described a continuous process for the oxidative cleavage of derivatives of unsaturated carboxylic acids for the production of saturated carboxylic acids and their derivatives comprising the steps of: a) feeding to a first reactor at least a derivative of an unsaturated carboxylic acid, an oxidizing compound and a catalyst capable of catalyzing the oxidation reaction of the olefinic double bond to obtain an intermediate compound containing vicinal diols, and ofb) feeding to a second reactor said intermediate compound, a compound containing oxygen and a catalyst capable of catalyzing the oxidation reaction of the vicinal diols to carboxylic groups, to obtain saturated monocarboxylic acids (i) and derivatives of saturated carboxylic acids with more than one acid function (ii);c) separating the saturated monocarboxylic acids (i) from the derivatives of carboxylic acids having more than one acid function (ii).
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Page/Page column 4
(2012/12/13)
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- CONTINUOUS PROCESS FOR THE PRODUCTION OF DERIVATIVES OF SATURATED CARBOXYLIC ACIDS
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There is described a continuous process for the oxidative cleavage of derivatives of unsaturated carboxylic acids for the production of saturated carboxylic acids and their derivatives comprising the steps of: a) feeding to a first reactor at least a derivative of an unsaturated carboxylic acid, an oxidizing compound and a catalyst capable of catalyzing the oxidation reaction of the olefinic double bond to obtain an intermediate compound containing vicinal diols, and of b) feeding to a second reactor said intermediate compound, a compound containing oxygen and a catalyst capable of catalyzing the oxidation reaction of the vicinal diols to carboxylic groups, to obtain saturated monocarboxylic acids (i) and derivatives of saturated carboxylic acids with more than one acid function (ii); c) separating the saturated monocarboxylic acids (i) from the derivatives of carboxylic acids having more than one acid function (ii).
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- METHOD FOR PRODUCING OXYGEN-CONTAINING COMPOUND
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[Problem] There is provided a method for producing an oxygen-containing compound safely and with improved reaction efficiency, in which an undesired peroxide is unlikely to be produced, and efficient heat exchange of the ozonization can be achieved. [Mean for solving the Problem] The method comprises an ozonization reaction step of continuously supplying, together with an organic compound, ozone having an oxygen content of less than 10% in a dissolved state in high-pressure carbon dioxide to an ozonization reaction section having a thin tubular shape, and reacting the ozone and the organic compound under conditions that suppress generation of oxygen due to thermal decomposition of the ozone, thereby continuously producing an ozonide; and a decomposition reaction step of continuously supplying the ozonide produced in the ozonization reaction step to a decomposition reaction section having a thin tubular shape, thereby continuously producing an oxygen-containing compound, the decomposition reaction step being provided in a manner continuous with the ozonization reaction step.
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Page/Page column 25
(2012/01/11)
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