scholarly journals A Cost-Effective and Eco-Friendly Way to Dihydroxylate Terminal and Internal Alkenes Using Hydrogen Peroxide/formic Acid

Author(s):  
Chia-Wei Hsu ◽  
Trevor Dzwiniel ◽  
Krzysztof Pupek

<div> <p>Abstract In this report, we present a modified dihydroxylation procedure for terminal and internal alkenes under neat conditions using formic acid and hydrogen peroxide. Upon the <i>in situ</i> formation of performic acid, followed by the hydrolysis of hydroxy-formoxy compounds with excess water, we can obtain a series of diols without catalysts and bases.</p> </div>

2020 ◽  
Author(s):  
Chia-Wei Hsu ◽  
Trevor Dzwiniel ◽  
Krzysztof Pupek

<div> <p>Abstract In this report, we present a modified dihydroxylation procedure for terminal and internal alkenes under neat conditions using formic acid and hydrogen peroxide. Upon the <i>in situ</i> formation of performic acid, followed by the hydrolysis of hydroxy-formoxy compounds with excess water, we can obtain a series of diols without catalysts and bases.</p> </div>


2020 ◽  
Author(s):  
Chia-Wei Hsu ◽  
Trevor Dzwiniel ◽  
Krzysztof Pupek

<div> <p>Abstract In this report, we present a modified dihydroxylation procedure for terminal and internal alkenes under neat conditions using formic acid and hydrogen peroxide. Upon the <i>in situ</i> formation of performic acid, followed by the hydrolysis of hydroxy-formoxy compounds with excess water, we can obtain a series of diols without catalysts and bases.</p> </div>


Author(s):  
Mohd Azril Riduan ◽  
Mohd Jumain Jalil ◽  
Intan Suhada Azmi ◽  
Afifudin Habulat ◽  
Danial Nuruddin Azlan Raofuddin ◽  
...  

Background: Greener epoxidation by using vegetable oil to create an eco-friendly epoxide is being studied because it is a more cost-effective and environmentally friendly commodity that is safer than non-renewable materials. The aim of this research is to come up with low-cost solutions for banana trunk acoustic panels with kinetic modelling of epoxy-based palm oil. Method: In this study, the epoxidation of palm oleic acid was carried out by in situ performic acid to produce epoxidized palm oleic acid. Results: Banana trunk acoustic panel was successfully innovated based on the performance when the epoxy was applied. Lastly, a mathematical model was developed by using the numerical integration of the 4th order Runge-Kutta method, and the results showed that there is a good agreement between the simulation and experimental data, which validates the kinetic model. Conclusion: Overall, the peracid mechanism was effective in producing a high yield of epoxy from palm oleic acid that is useful for the improvement of acoustic panels based on the banana trunk.


2018 ◽  
Vol 20 (3) ◽  
pp. 53-59 ◽  
Author(s):  
Marlena Musik ◽  
Eugeniusz Milchert ◽  
Kornelia Malarczyk-Matusiak

Abstract The course of epoxidation of sesame oil (SO) with performic acid formed „in situ” by the reaction of 30 wt% hydrogen peroxide and formic acid in the presence of sulfuric acid(VI) as a catalyst was studied. The most advantageous of the technological independent parameters of epoxidation are as follows: temperature 80°C, H2O2/ C=C 3.5:1, HCOOH/C=C 0.8:1, amount of catalyst as H2SO4/(H2O2+HCOOH) 1 wt%, stirring speed at least 700 rpm, reaction time 6 h. The iodine number (IN), epoxy number (EN), a relative conversion to oxirane (RCO) and oxirane oxygen content (EOe) were determined every hour during the reaction. Under optimal conditions the sesame oil conversion amounted to 90.7%, the selectivity of transformation to epoxidized sesame oil was equal to 93.2%, EN = 0.34 mol/100 g, IN = 0.04 mol/100 g oil (10.2 g/100 g oil), a relative conversion to oxirane RCO = 84.6%, and oxirane oxygen content of EOe = 5.5%.


1984 ◽  
Vol 37 (8) ◽  
pp. 1721 ◽  
Author(s):  
RA Russell ◽  
GJ Collin ◽  
MP Crane ◽  
PS Gee ◽  
AS Krauss ◽  
...  

5,8-Dihydronaphthalene-1,4-diol, readily available from benzoquinone and buta-1,3-diene, is isomerized by heating with strong sodium hydroxide, and acetylated (Ac2O), in situ, to form 5,8-diacetoxy-1,2-dihydronaphthalene. Catalysed (AlCl3) addition of acetyl chloride followed by dehydrochlorination (LiCI/HCONMe2) yielded 5,8-diacetoxy-3-acetyl-1,2-dihydronaphthalene (11) in 82% overall yield. Base hydrolysis of (11), followed by methylation (Me2SO4) gives 3-acetyl-5,8-dimethoxy-1,2-dihydronaphthalene in 94% yield, the most direct route to this product so far described. More importantly, the diacetate (11) is selectively deacetylated at C5 (Cs2CO3 in tetrahydrofuran, or K2CO3 in Me2SO) to form the related phenol, alkylation of which produces the 5-alkoxy compound. Further hydrolysis followed by alkylation yields the unsymmetrically, but regiospecifically substituted, 3-acetyl-5,8-dialkoxy-1,2-dihydronaphthalenes. This method is specifically illustrated by the production of 3-acetyl-5-benzyloxy-8-methoxy-1,2-dihydronaphthalene which is formed in a short, cost effective synthesis in a moderate overall yield (25%) based upon benzoquinone as starting material;significantly, no chromatographic separations are required.


Studies on the epoxidation of rubber (Hevea brasiliensis) seed oil, a renewable source with formic acid was performed in the presence of 30% hydrogen peroxide at a of temperature 40, 50,60,70 oC. The process is favoured by an increase in temperature forming a product with high oxirane content which is as a result of mole ratios of formic acid and hydrogen peroxide. Products of high oxirane content are commercialy viable in the production of polyvinyl chloride (PVC). Natural rubber and other products can be obtained from this in- situ technique. Studies in this research shows that the rate of epoxidation increases with an increase in temperature.Oxirane values of 2.30, 3.62 and 4.73 for the various temperature. However high oxirane content of 6.22 was obtained at 70 oC which is in line with literature. FTIR analysis was also carried out on the epoxidized rubber seed oil which shows the peaks of oxirane cleavage.


1985 ◽  
Vol 50 (5) ◽  
pp. 1194-1200 ◽  
Author(s):  
Stanislav Kafka ◽  
Miloslav Ferles ◽  
Miloslav Richter

Hydroboration of 1-allyl-1,2,3,4-tetrahydroquinoline (I) with triethylamine-borane in the molar ratio 1 : 1 afforded a product from which 6,7-benzo-5-aza-1-boraspiro[4,5]decane (II) was isolated. Ethanolysis of II gave diethyl 3-(1,2,3,4-tetrahydro-1-quinolyl)propylboronate (III). Acid hydrolysis of the crude hydroboration product and subsequent oxidation with alkaline hydrogen peroxide led to a mixture of 3-(1,2,3,4-tetrahydro-1-quinolyl)-1-propanol (IV), 1,2,3,4-tetrahydroquinoline (V) and 1-propyl-1,2,3,4-tetrahydroquinoline (VI). Hydroboration of I with triethylamine-borane in the molar ratio 3 : 1, followed by oxidation, gave a mixture of IV, V, VI and 1-(1,2,3,4-tetrahydro-1-quinolyl)-2-propanol (VIII). Hydroboration of I with diborane in situ in diethylene glycol dimethyl ether at 20 °C and subsequent acid hydrolysis and oxidation with alkaline hydrogen peroxide afforded a mixture of IV, V and VIII when the hydroboration product was first heated to 150 °C and then subjected to the above-mentioned processing, only compounds IVand V were formed.


1961 ◽  
Vol 38 (4) ◽  
pp. 545-562 ◽  
Author(s):  
L. Kecskés ◽  
F. Mutschler ◽  
I. Glós ◽  
E. Thán ◽  
I. Farkas ◽  
...  

ABSTRACT 1. An indirect paperchromatographic method is described for separating urinary oestrogens; this consists of the following steps: acidic hydrolysis, extraction with ether, dissociation of phenol-fractions with partition between the solvents. Previous purification of phenol fraction with the aid of paperchromatography. The elution of oestrogen containing fractions is followed by acetylation. Oestrogen acetate is isolated by re-chromatography. The chromatogram was developed after hydrolysis of the oestrogens 'in situ' on the paper. The quantity of oestrogens was determined indirectly, by means of an iron-reaction, after the elution of the iron content of the oestrogen spot, which was developed by the Jellinek-reaction. 2. The method described above is satisfactory for determining urinary oestrogen, 17β-oestradiol and oestriol, but could include 16-epioestriol and other oestrogenic metabolites. 3. The sensitivity of the method is 1.3–1.6 μg/24 hours. 4. The quantitative and qualitative determination of urinary oestrogens with the above mentioned method was performed in 50 pregnant and 9 non pregnant women, and also in 2 patients with granulosa cell tumour.


Author(s):  
Xiaoyan Wang ◽  
Jinmei Du ◽  
Changhai Xu

Abstract:: Activated peroxide systems are formed by adding so-called bleach activators to aqueous solution of hydrogen peroxide, developed in the seventies of the last century for use in domestic laundry for their high energy efficiency and introduced at the beginning of the 21st century to the textile industry as an approach toward overcoming the extensive energy consumption in bleaching. In activated peroxide systems, bleach activators undergo perhydrolysis to generate more kinetically active peracids that enable bleaching under milder conditions while hydrolysis of bleach activators and decomposition of peracids may occur as side reactions to weaken the bleaching efficiency. This mini-review aims to summarize these competitive reactions in activated peroxide systems and their influence on bleaching performance.


Sign in / Sign up

Export Citation Format

Share Document