Sodium stannate promoted double bond cleavage of oleic acid by hydrogen peroxide over a heterogeneous WO3catalyst

2018 ◽  
Vol 20 (15) ◽  
pp. 3619-3624 ◽  
Author(s):  
Xiukai Li ◽  
Joel Choo Ping Syong ◽  
Yugen Zhang
Keyword(s):  
Hydrogen Peroxide ◽  
Oleic Acid ◽  
Double Bond ◽  
Tungsten Oxide ◽  
Azelaic Acid ◽  
Bond Cleavage ◽  
Nonanoic Acid ◽  
Reaction Efficiency ◽  
Sodium Stannate

A sodium stannate additive notably improved the reaction efficiency of tungsten oxide catalysed oleic acid (OA) cleavage by hydrogen peroxide to produce azelaic acid and nonanoic acid.

Double Oxidants Combined Oxidation of Oleic Acid Preparation of Azelaic Acid

2013 ◽  
Vol 804 ◽  
pp. 94-97
Author(s):  
Chun Wei Shi ◽  
Xiao Yan Zhang ◽  
Shan Lin Zhao ◽  
Ping Chen ◽  
Yu Ting Bai
Keyword(s):  
Hydrogen Peroxide ◽  
Oleic Acid ◽  
Reaction Time ◽  
Reaction Temperature ◽  
Azelaic Acid ◽  
Phosphotungstic Acid ◽  
Hydrogen Peroxide Solution ◽  
Acid Hydrate ◽  
Major Factors

Oleic acid was oxidized to azelaic acid by ozone and hydrogen peroxide as an oxidant jointly in this paper. The effect of major factors, such as the volume and concentration of hydrogen peroxide, the volume and concentration of ozone. The results show that the yield of azelaic acid was up to 71 %, when the oxidation was taken under the following condition: oleic acid 20g, phosphotungstic acid hydrate 0.6g , 30% hydrogen peroxide solution 60ml, reaction temperature 70°C, reaction time 8h.

WO3-Polypyrrole Nanocomposite as Catalyst in Azelaic Acid Synthesis from Oleic Acid

2012 ◽  
Vol 620 ◽  
pp. 147-150 ◽  
Author(s):  
Khadijeh Beigom Ghoreishi ◽  
Mohd Ambar Yarmo
Keyword(s):  
Oleic Acid ◽  
Tungsten Oxide ◽  
Azelaic Acid ◽  
Acid Synthesis ◽  
Catalyst System ◽  
Ozone Generator ◽  
Reaction Products ◽  
Free Medium ◽  
Major Reaction ◽  
Ft Ir

Catalytic oxidation of oleic acid with ozone gas by using ozone-generator and solvent free medium in the presence of WO3-Polypyrrole (ppy) nanocomposite was studied. Azelaic acid (AA) and pelargonic acids (PA) are the major reaction products, however the percentage of AA production is significantly higher than PA. Experimental results concluded that tungsten oxide and tungten oxide on polypyrrole are suitable catalysts in terms of their selectivity and activity. Reaction is done in two steps within 90 minute, showing the reasonable promotion in selectivity to AA by using WO3-ppy catalyst system compared to reaction with WO3as catalyst. WO3-ppy nanocomposite is prepared by sonication method and characterized by FT-IR, XRD, and FESEM analysis. The products of ozonolysis are identified by GC-FID and GC-MS for measuring selectivity and reactivity as well.

Unusual carboncarbon double bond cleavage in thiophenohomotropone system promoted by ethanedithiol

1982 ◽  
Vol 23 (28) ◽  
pp. 2859-2862 ◽  
Author(s):  
Bernard Hanquet ◽  
Mohammed El Borai ◽  
Roger Guilard ◽  
Yves Dusausoy
Keyword(s):  
Double Bond ◽  
Bond Cleavage ◽  
Carbon Double Bond

Sustainable Process for Production of Azelaic Acid Through Oxidative Cleavage of Oleic Acid

2015 ◽  
Vol 92 (11-12) ◽  
pp. 1701-1707 ◽  
Author(s):  
Vincenzo Benessere ◽  
Maria E. Cucciolito ◽  
Augusta De Santis ◽  
Martino Di Serio ◽  
Roberto Esposito ◽  
...  
Keyword(s):  
Oleic Acid ◽  
Azelaic Acid ◽  
Oxidative Cleavage

scholarly journals Phenolation of vegetable oils

2011 ◽  
Vol 76 (4) ◽  
pp. 591-606 ◽  
Author(s):  
Mihail Ionescu ◽  
Zoran Petrovic
Keyword(s):  
Fatty Acids ◽  
Oleic Acid ◽  
Double Bond ◽  
Vegetable Oils ◽  
Raw Materials ◽  
Complex Mixture ◽  
Double Bonds ◽  
Triflic Acid ◽  
Model Compounds ◽  
Phenol Alkylation

Novel bio-based compounds containing phenols suitable for the synthesis of polyurethanes were prepared. The direct alkylation of phenols with different vegetable oils in the presence of superacids (HBF4, triflic acid) as catalysts was studied. The reaction kinetics was followed by monitoring the decrease of the double bond content (iodine value) with time. In order to understand the mechanism of the reaction, phenol was alkylated with model compounds. The model compounds containing one internal double bond were 9-octadecene and methyl oleate and those with three double bonds were triolein and high oleic safflower oil (82% oleic acid). It was shown that the best structures for phenol alkylation are fatty acids with only one double bond (oleic acid). Fatty acids with two double bonds (linoleic acid) and three double bonds (linolenic acid) lead to polymerized oils by a Diels Alder reaction, and to a lesser extent to phenol alkylated products. The reaction product of direct alkylation of phenol with vegetable oils is a complex mixture of phenol alkylated with polymerized oil (30-60%), phenyl esters formed by transesterification of phenol with triglyceride ester bonds (<10 %) and unreacted oil (30%). The phenolated vegetable oils are new aromatic-aliphatic bio-based raw materials suitable for the preparation of polyols (by propoxylation, ethoxylation, Mannich reactions) for the preparation of polyurethanes, as intermediates for phenolic resins or as bio-based antioxidants.

scholarly journals Nighttime oxidation of surfactants at the air–water interface: effects of chain length, head group and saturation

2018 ◽  
Vol 18 (5) ◽  
pp. 3249-3268 ◽  
Author(s):  
Federica Sebastiani ◽  
Richard A. Campbell ◽  
Kunal Rastogi ◽  
Christian Pfrang
Keyword(s):  
Oleic Acid ◽  
Double Bond ◽  
Methyl Ester ◽  
Reaction Kinetics ◽  
Chain Length ◽  
Rate Coefficients ◽  
Head Group ◽  
Water Interface ◽  
Organic Monolayers ◽  
Air Water Interface

Abstract. Reactions of the key atmospheric nighttime oxidant NO3 with organic monolayers at the air–water interface are used as proxies for the ageing of organic-coated aqueous aerosols. The surfactant molecules chosen for this study are oleic acid (OA), palmitoleic acid (POA), methyl oleate (MO) and stearic acid (SA) to investigate the effects of chain length, head group and degree of unsaturation on the reaction kinetics and products formed. Fully and partially deuterated surfactants were studied using neutron reflectometry (NR) to determine the reaction kinetics of organic monolayers with NO3 at the air–water interface for the first time. Kinetic modelling allowed us to determine the rate coefficients for the oxidation of OA, POA and MO monolayers to be (2.8±0.7) × 10−8, (2.4±0.5) × 10−8and (3.3±0.6) × 10−8 cm2 molecule−1 s−1 for fitted initial desorption lifetimes of NO3 at the closely packed organic monolayers, τd, NO3, 1, of 8.1±4.0, 16±4.0 and 8.1±3.0 ns, respectively. The approximately doubled desorption lifetime found in the best fit for POA compared to OA and MO is consistent with a more accessible double bond associated with the shorter alkyl chain of POA facilitating initial NO3 attack at the double bond in a closely packed monolayer. The corresponding uptake coefficients for OA, POA and MO were found to be (2.1±0.5) × 10−3, (1.7±0.3) × 10−3 and (2.1±0.4) × 10−3, respectively. For the much slower NO3-initiated oxidation of the saturated surfactant SA we estimated a loss rate of approximately (5±1) × 10−12 cm2 molecule−1 s−1, which we consider to be an upper limit for the reactive loss, and estimated an uptake coefficient of ca. (5±1) × 10−7. Our investigations demonstrate that NO3 will contribute substantially to the processing of unsaturated surfactants at the air–water interface during nighttime given its reactivity is ca. 2 orders of magnitude higher than that of O3. Furthermore, the relative contributions of NO3 and O3 to the oxidative losses vary massively between species that are closely related in structure: NO3 reacts ca. 400 times faster than O3 with the common model surfactant oleic acid, but only ca. 60 times faster with its methyl ester MO. It is therefore necessary to perform a case-by-case assessment of the relative contributions of the different degradation routes for any specific surfactant. The overall impact of NO3 on the fate of saturated surfactants is slightly less clear given the lack of prior kinetic data for comparison, but NO3 is likely to contribute significantly to the loss of saturated species and dominate their loss during nighttime. The retention of the organic character at the air–water interface differs fundamentally between the different surfactant species: the fatty acids studied (OA and POA) form products with a yield of  ∼ 20 % that are stable at the interface while NO3-initiated oxidation of the methyl ester MO rapidly and effectively removes the organic character ( ≤ 3 % surface-active products). The film-forming potential of reaction products in real aerosol is thus likely to depend on the relative proportions of saturated and unsaturated surfactants as well as the head group properties. Atmospheric lifetimes of unsaturated species are much longer than those determined with respect to their reactions at the air–water interface, so they must be protected from oxidative attack, for example, by incorporation into a complex aerosol matrix or in mixed surface films with yet unexplored kinetic behaviour.

BF3•OEt2 Catalysed chemoselective C=C bond cleavage of α,β-enones: An unexpected synthesis of 3-alkylated oxindoles and spiroindolooxiranes

2021 ◽  
Author(s):  
Sengodagounder Muthusamy ◽  
Ammasi Prabu
Keyword(s):  
Double Bond ◽  
Boron Trifluoride ◽  
Bond Cleavage ◽  
Boron Trifluoride Etherate ◽  
Cleavage Reaction ◽  
Bond Cleavage Reaction

A BF3•OEt2 catalyzed highly chemoselective formal C=C double bond cleavage reaction of α,β-enones with diazoamides for the synthesis of 3-alkylated oxindoles is developed. Boron trifluoride etherate is found to be...

Sign in / Sign up

Export Citation Format

Share Document