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100-79-8

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  • Solketal CAS 100-79-8 Factory 2,2-Dimethyl-1,3-dioxolane-4-methanol PRICE IN STOCK DL-1,2-Isopropylideneglycerol COA (+/-)-2,2-Dimethyl-1,3-dioxolane-4-methanol CAS 100-79-8

    Cas No: 100-79-8

  • USD $ 3.5-5.0 / Kiloliter

  • 5 Kiloliter

  • 3000 Metric Ton/Month

  • Chemwill Asia Co., Ltd.
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100-79-8 Usage

Chemical Properties

clear colourless liquid

Uses

Different sources of media describe the Uses of 100-79-8 differently. You can refer to the following data:
1. A MEK inhibitor
2. Solketal is useful for synthesis of mono-, di- and triglycerides. It is used as the starting reagent for synthesis of tulipaline derivatives. It acts as a fuel additive in gasoline. It is an inhibitor of Methyl ethyl ketone .
3. DL-1,2-Isopropylideneglycerol was used as the starting reagent for synthesis of tulipaline derivatives.

Synthesis Reference(s)

Tetrahedron, 52, p. 9387, 1996 DOI: 10.1016/0040-4020(96)00501-7The Journal of Organic Chemistry, 53, p. 2859, 1988 DOI: 10.1021/jo00247a043

General Description

DL-1,2-Isopropylideneglycerol undergoes effective isopropylidenation and deprotection reaction catalyzed by phosphotungstic acid.

Safety Profile

A poison by intravenous route. An eye irritant. Mutation data reported. A very dangerous fire hazard when exposed to heat or flame; can react vigorously with oxidizing materials. To fight fire, use alcohol foam, CO2, dry chemical. When heated to decomposition it emits acrid smoke and fumes.

Check Digit Verification of cas no

The CAS Registry Mumber 100-79-8 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,0 and 0 respectively; the second part has 2 digits, 7 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 100-79:
(5*1)+(4*0)+(3*0)+(2*7)+(1*9)=28
28 % 10 = 8
So 100-79-8 is a valid CAS Registry Number.
InChI:InChI=1/C6H12O3/c1-6(2)8-4-5(3-7)9-6/h5,7H,3-4H2,1-2H3/t5-/m0/s1

100-79-8 Well-known Company Product Price

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  • Alfa Aesar

  • (L02814)  Solketal, 97%   

  • 100-79-8

  • 100g

  • 206.0CNY

  • Detail
  • Alfa Aesar

  • (L02814)  Solketal, 97%   

  • 100-79-8

  • 500g

  • 515.0CNY

  • Detail
  • Alfa Aesar

  • (L02814)  Solketal, 97%   

  • 100-79-8

  • 2500g

  • 2010.0CNY

  • Detail
  • Aldrich

  • (122696)  DL-1,2-Isopropylideneglycerol  ≥97.0%

  • 100-79-8

  • 122696-100G

  • 205.92CNY

  • Detail
  • Aldrich

  • (122696)  DL-1,2-Isopropylideneglycerol  ≥97.0%

  • 100-79-8

  • 122696-500G

  • 498.42CNY

  • Detail
  • Aldrich

  • (122696)  DL-1,2-Isopropylideneglycerol  ≥97.0%

  • 100-79-8

  • 122696-3KG

  • 3,061.89CNY

  • Detail

100-79-8SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name DL-1,2-Isopropylideneglycerol

1.2 Other means of identification

Product number -
Other names (±)-2,2-Dimethyl-4-hydroxymethyl-1,3-dioxolane

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Solvents
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:100-79-8 SDS

100-79-8Related news

Glycerol to renewable fuel oxygenates. Part I: Comparison between Solketal (cas 100-79-8) and its methyl ether07/19/2019

Solketal methyl ether (SME) was synthesized from glycerol by conversion with methanol followed by ketalization with acetone. The values for the equilibrium constant of the ketalization of glycerol and glycerol 1-monomethyl ether in the temperature range of 298–323 K were determined experimental...detailed

100-79-8Relevant articles and documents

Acetalisation of bio-glycerol with acetone to produce solketal over sulfonic mesostructured silicas

Vicente, Gemma,Melero, Juan A.,Morales, Gabriel,Paniagua, Marta,Martin, Eric

, p. 899 - 907 (2010)

Sulfonic acid-functionalized mesostructured silicas have demonstrated excellent catalytic behaviour in the acetalisation of glycerol with acetone to yield 2,2-dimethyl-1,3-dioxolane-4-methanol, also known as solketal. This molecule constitutes an excellent compound for the formulation of gasoline, diesel and biodiesel fuels. The activity achieved with arenesulfonic acid-functionalized silica is comparable to that displayed by Amberlyst-15. Optimal production of solketal over arenesulfonic acid mesostructured silica has been established for a reaction system consisting of three consecutive 2-step batches (30 min under reflux and an evaporation step under vacuum), and using a 6/1 acetone/glycerol molar ratio. The use of lower grades of glycerol, such as technical (purity of 91.6 wt%) and crude (85.8 wt%) glycerol, has also provided high conversions of glycerol over sulfonic acid-modified heterogeneous catalysts (84% and 81%, respectively). For refined and technical glycerol the catalysts have been reused, without any regeneration treatment, up to three times, keeping the high initial activity. However, the high sodium content in crude glycerol deactivates the sulfonic acid sites by cation exchange. This deactivation is readily reversed by simple acidification of the catalyst after reaction.

Intramolecular Chirality Transfer [2 + 2] Cycloadditions of Allenoates and Alkenes

Xu, Yao,Hong, Young J.,Tantillo, Dean J.,Brown, M. Kevin

, p. 3703 - 3706 (2017)

Intramolecular chirality transfer [2 + 2] cycloaddition of enantiomerically enriched allenoates and alkenes is presented. The use of a chiral catalyst was found to be critical to achieve high levels of diastereoselectivity compared to use of an achiral catalyst. The method developed leads to highly substituted cyclobutanes that would be difficult to prepare by alternative methods.

Toward sustainable and eco-efficient novel catalytic distillation process for production of solketal using seepage catalytic packing internal

Cong, Haifeng,Gao, Xin,Lai, Jianing,Li, Hong,Li, Xingang,Shu, Chang,Wang, Yiwei,Zhao, Runnan

, (2020)

The initial aim of this paper is to dramatically improve the post-treatment stage of biodiesel production, which converts problematic glycerol to solketal (SK), by introduction of an eco-efficient integrated reactive and dividing wall distillation process. To overcome the chemical equilibrium limitations and the long post-treatment process with the high energy consumption and waste water emission, this study provides the potentially, sustainable and novel reactive distillation (RD) process for cleanly catalytic synthesis of SK, taking into account costs and environmental impact. The ketalization kinetics experiments were carried out to provide a basis for subsequent experiments and simulations. A reliable model was established for further RD technological design and validated by the pilot-scale experiments. Through sensitivity analysis, the effects of multiplex parameters in RD process were determined. The advanced intensification of SK production by reactive dividing wall column (RDWC) achieves reduction in energy, total annual cost (TAC) and CO2 emissions of 13.9 %, 18.2 % and 16.4 % (as oil resources), respectively, compared to the optimal SK production by RD process. This proposed technology is also compared with the conventional industrial route of ketalization with 18.7 % energy saving.

Choice of a catalyst and technological scheme for synthesis of solketal

Dmitriev,Terekhov,Zanaveskin,Khadzhiev,Zanaveskin,Maksimov

, p. 1619 - 1624 (2016)

Results are presented obtained in tests of various homogeneous and heterogeneous catalysts in a synthesis of solketal (2,2-dimethyl-4-hydroxymethyl-1,3-dioxolane). It is shown that, all other conditions being the same, the highest catalytic activity is observed for sulfuric acid and beta zeolite. Data are presented on how the equilibrium constant of the reaction of glycerol ketalization depends on temperature. A technological scheme of the process for synthesis of solketal is suggested and its description is presented.

Synthesis of glycerol-derived 4-alkyl-substituted 1,2,3-triazoles and evaluation of their fungicidal, phytotoxic, and antiproliferative activities

Costa, Adilson V.,Moreira, Luiza C.,Pinto, Roberta T.,Alves, Thammyres A.,Schwan, Vitor V.,de Queiroz, Vagner T.,Pra?a-Fontes, Milene M.,Teixeira, Róbson Ricardo,Morais, Pedro A.B.,de Jesus, Waldir C.

, p. 821 - 832 (2020)

Herein, the synthesis of nine novel glycerol-derived 4-alkyl-substituted 1,2,3-triazoles, using the CuI-catalyzed alkyne-azide cycloaddition reaction as the key step, is reported. The triazoles were characterized by infrared and nuclear magnetic resonance (NMR 1H and 13C) spectroscopy and mass spectrometry. The nine prepared compounds were evaluated with regard to their phytotoxic, antiproliferative, and fungicidal activities. The fungicidal activity was assessed on Colletotrichum gloeosporioides, the causative agent of papaya anthracnose. All compounds presented high efficiency (comparable to the commercial fungicide tebuconazole) in inhibiting C. gloeosporioides sporulation. The phytotoxicity of the triazoles was assessed against Lactuca sativa. Germination was the less-affected parameter, whereas the most pronounced effects of the triazoles were on the germination speed index and root growth of the L. sativa seedlings. As indicators of antiproliferative activity, the mitotic index was evaluated along with chromosomal and nuclear alterations, all of which were influenced to different degrees by the triazoles. In addition, all derivatives demonstrated aneugenic and clastogenic actions in meristematic cells of L. sativa roots. Therefore, these 4-alkyl-substituted triazoles may represent a scaffold to be explored for the development of new fungicidal agents.

Preparation of high-octane oxygenate fuel components from plant-derived polyols

Maksimov,Nekhaev,Ramazanov,Arinicheva,Dzyubenko,Khadzhiev

, p. 61 - 69 (2011)

The ketalization of polyols (glycerol, xylitol, xylose) in the presence of a number of heterogeneous acid catalysts has been studied. It has been shown that zeolite catalysts exhibit high activity in the formation of the acetone ketal of glucose in a flow system with the quantitative selectivity for the 1,2-product. The best catalyst is zeolite β in the presence of this zeolite and excess acetone, the yield is over 90% or, in the case of the structured reactor, even greater than 98% It has been shown that zeolite-based systems catalyze the formation of ketals of xylitol and xylose with a yield of up to 50% in the presence of excess acetone.

Synthesis of biodiesel without formation of free glycerol

Vol'eva,Belostotskaya,Komissarova,Koverzanova,Kurkovskaya,Usmanov,Gumerov

, p. 915 - 917 (2015)

A new approach to the synthesis of biodiesel has been developed on the basis of alcoholysis of a triglyceride in combination with acetalization of glycerol with lower carbonyl compounds or acetals derived therefrom. A model synthesis of biodiesel not involving free glycerol has been accomplished using rapeseed oil and acid catalysts, as well as without a catalyst under generation of ethanol supercritical fluid; in the latter case, monoalkyl glycerol ethers are formed in addition to the expected cyclic ketals.

Enzymatic enantioselective ester hydrolysis by carboxylesterase NP

Smeets, J. W. H.,Kieboom, A. P. G.

, p. 490 - 495 (1992)

The enzymatic hydrolysis of a series of carboxylic esters by carboxylesterase NP has been investigated in order to determine the scope and limitations of this enzyme. 2-Substituted propionates were hydrolyzed with high enantioselectivity when an aromatic moiety was part of the 2-substituent.Enantioselective hydrolysis could be accomplished with several 2-arypropionates, 2-(aryloxy)propionates and N-arylalanine esters.The propionate esters yielded propionic acids as (S) enantiomers, whereas the alanine esters yielded the (R) enantiomers.Without a 2-aryl substituent, the enzymatic hydrolysis of the propionates occurred at a lower rate without acceptable enantioselectivity.In addition to 2-substituted propionates, only a few other esters were hydrolyzed with high enantioselectivity by carboxylesterase NP, such as some prochiral disubstituted malonates. 1-Phenylethylacetate was the only substrate with chirality in the alcohol part of the ester that was found to be hydrolyzed enantioselectively.Carboxylesterase NP proved to be a powerful enzyme for kinetic resolution of propionate esters with an aromatic ring containing a 2-substituent.

Water-soluble meroterpenes containing an aminoglyceride fragment with geraniol residues: synthesis and membranotropic properties

Akhmedov, Alan A.,Shurpik, Dmitry N.,Plemenkov, Vitaliy V.,Stoikov, Ivan I.

, p. 29 - 31 (2019)

A number of new membrane anchors based on water-soluble aminoglycerides with geraniol fragments have been synthesized. A biomimetic approach was used based on the design of meroterpenes structurally similar to archaeal lipids. Turbidimetry and laser Doppler microelectrophoresis showed that the synthesized compounds were incorporated into unilamellar dipalmitoylphosphatidylcholine (DPPC) vesicles.

Highly Efficient Glycerol Acetalization over Supported Heteropoly Acid Catalysts

Chen, Lin,Nohair, Bendaoud,Zhao, Dongyuan,Kaliaguine, Serge

, p. 1918 - 1925 (2018)

The acetalization of glycerol with acetone to yield solketal was catalyzed by Cs2.5H0.5PW12O40 (Cs2.5) supported on mesoporous silica under mild conditions. It gave a high glycerol conversion and selectivity to the targeted product even at room temperature (23 °C). We studied the use of both bulk and supported Cs2.5 as catalysts in another highly efficient glycerol acetalization reaction with paraformaldehyde, which gave much higher activity than with formaldehyde solution. For the reaction with acetone, the supported Cs2.5 showed a higher activity than the bulk material because of the high surface area of the mesoporous support. Interestingly, the supported Cs2.5 gave a lower conversion than the bulk for the reaction with paraformaldehyde. This is probably because of the high viscosity of the reaction system with the solid reagent paraformaldehyde. Overall, there is a complex relationship between catalyst, reaction conditions, which include the molar ratio of reactants and temperature, reaction mechanism and thermodynamics that affects the achieved activity and byproduct formation. A discussion about these interactions is included for each reaction.

Design of highly efficient Mo and W-promoted SnO2 solid acids for heterogeneous catalysis: Acetalization of bio-glycerol

Mallesham, Baithy,Sudarsanam, Putla,Raju, Gangadhara,Reddy, Benjaram M.

, p. 478 - 489 (2013)

Development of highly promising solid acids is one of the key technologies to meet the essential challenges of economical and environmental concerns. Thus, novel molybdenum and tungsten promoted SnO2 solid acids (wet-impregnation) and pure SnO2 (fusion method) were prepared. The synthesized catalysts were systematically analyzed using various techniques, namely, XRD, BET surface area, pore size distribution, XPS, FTIR, FTIR of adsorbed pyridine, Raman, NH3-TPD, and H2-TPR. XRD results suggested formation of nanocrystalline SnO2 solid solutions due to the incorporation of molybdenum and tungsten cations into the SnO2 lattice. All the materials exhibited smaller crystallite size, remarkable porosity, and high specific surface area. Raman measurements suggested the formation of more oxygen vacancy defects in the doped catalysts, and the TPR results confirmed facile reduction of the doped SnO2. NH 3-TPD studies revealed the beneficial role of molybdenum and tungsten oxides on the acidic properties of the SnO2. FTIR studies of adsorbed pyridine showed the existence of a larger number of Bronsted acidic sites compared to Lewis acidic sites in the prepared catalysts. The resulting catalysts are found to be efficient solid acids for acetalization of glycerol with acetone, furfural, and its derivatives under solvent-free and ambient temperature conditions. Particularly, the Mo6+-doped SnO 2 catalyst exhibited excellent catalytic performance in terms of both glycerol conversion and selectivity of the products. The increased presence of acidic sites and enhanced specific surface area, accompanied by notable redox properties and superior lattice defects are found to be the decisive factors for better catalytic activity of the Mo6+-doped SnO2 sample. The investigated SnO2 solid acids represent a novel class of heterogeneous catalysts useful for the transformation of glycerol to value-added products in an eco-friendly manner.

Synthesis and properties of new fullerene C60 derivatives, containing acetonide and polyol fragments

Gilmutdinova, Alina A.,Gubskaya, Valentina P.,Fazleeva, Guzel M.,Latypov, Shamil K.,Zhelonkina, Tatyana A.,Sharafutdinova, Dilara R.,Nuretdinov, Ildus A.,Sinyashin, Oleg G.

, p. 5947 - 5953 (2014)

New mono- and hexa-methanofullerenes containing different number of acetonide groups are synthesized and characterized. Removing the acetonide protection leads to new chromatographically pure water-soluble polyol methanofullerenes with essentially quantitative yields.

Ga-MCM-41 nanoparticles: Synthesis and application of versatile heterogeneous catalysts

Collard, Xavier,Li, Li,Lueangchaichaweng, Warunee,Bertrand, Arnaud,Aprile, Carmela,Pescarmona, Paolo P.

, p. 184 - 192 (2014)

Ga-MCM-41 materials with nanosized particles (2-physisorption, TEM, SEM and EDX, while 71Ga MAS-NMR was employed to monitor the coordination of the gallium atoms. The two materials were tested as heterogeneous catalysts in three relevant reactions in the context of green production of valuable chemicals: (1) the reaction of glycerol with acetone to produce solketal; (2) the conversion of the triose sugar dihydroxyacetone to ethyl lactate; (3) the epoxidation of cyclooctene with aqueous hydrogen peroxide. The two nanosized Ga-MCM-41 materials show different catalytic behaviour in the various reactions, with the material prepared with lower Si/Ga displaying a higher versatility. This catalyst reaches higher turnover numbers compared to conventional Ga-MCM-41 reported in the literature. This result is ascribed to the higher specific surface area and to the shorter channels of the nanoparticles, which enhance the accessibility of the active sites.

Solketal Formation in a Continuous Flow Process over Hierarchical Zeolites

Kowalska-Ku?, Jolanta,Held, Agnieszka,Nowińska, Krystyna

, p. 510 - 519 (2020)

Glycerol ketalization with acetone to solketal, an oxygenate fuel additive, was demonstrated over hierarchical zeolites of ZSM5, Beta and Mordenite structure in a continuous flow system. Micro-mesoporous zeolites were prepared in two steps, by means of alkaline treatment with NaOH followed by the ionic exchange with NH4NO3 and a subsequent treatment with citric acid. The presence of mesopores in the applied catalysts was confirmed by N2 adsorption/desorption measurements and TEM microscopy. Hierarchical zeolites showed superior catalytic performance and lifetime over 24 hours under mild conditions (atmospheric pressure, acetone to glycerol molar ratio of 3 : 1, WHSV of 3–8 h?1, reaction temperature of 323 K). Glycerol conversion of about 90 % and selectivity to solketal up to 98 % have been obtained over micro-mesoporous catalysts within 24 h without any drop of performance and the symptoms of clogging. Among all hierarchical catalysts tested in a flow reactor, the very high activity defined as solketal yield (88 %) showed ZSM5 and Beta zeolites.

Interaction of triols with formaldehyde and acetone: Experimental and theoretical study

Sultanova, Rimma,Borisevich, Sophia,Raskil'dina, Gulnara,Borisova, Julianna,Baykova, Irina,Spirikhin, Leonid,Khursan, Sergey,Zlotsky, Simon

, p. 1144 - 1151 (2020)

Experimental and theoretical aspects of the condensation of glycerol and its homologs (1,2,3- and 1,2,4-butanetriols) with formaldehyde and acetone are studied under conditions of acid catalysis. Calculation of the thermodynamic parameters of the resulting products by the composite method CBS-QB3 shows that the six-membered heterocycles, the products of the interaction of triols with formaldehyde, are thermodynamically more stable than the five-membered acetals, while the reaction of the same triols with acetone is preferable for the formation of the five-membered acetals. This is due to the fact that the regioselectivity of the studied reactions is determined by the structural features and reactivity of the carbocations formed in a condensed medium during the course of the reaction. According to the theoretical data obtained experimentally, during the condensation of glycerol and 1,2,4-butanetriol with formaldehyde in the most stable form of the six-membered cyclic carbocation, intramolecular hydrogen bonding and anomeric stabilization due to the axially oriented hydroxyl group take place. As a result, cation 1b–1 is 1.2–1.6 kJ/mol more stable than its five-membered isomers (1a–1 and 1b–2). It leads to the predominant formation of 1,3-dioxane (3b). However, upon condensation of butanetriol-1,2,3 with formaldehyde, the intermediate cation 4a–1 turns out to be significantly more stable than the other isomers due to the strong intramolecular hydrogen bond in the six-membered ring with the participation of the hydroxyl group of the substituent and the hydroxyl group of the cationic center, leading to the predominant formation of the dioxolane 6a.

Mesoporous tin oxide: An efficient catalyst with versatile applications in acid and oxidation catalysis

Manjunathan, Pandian,Marakatti, Vijaykumar S.,Chandra, Prakash,Kulal, Atul B.,Umbarkar, Shubhangi B.,Ravishankar, Raman,Shanbhag, Ganapati V.

, p. 61 - 76 (2018)

Mesoporous tin oxide was prepared by template assisted and template-free methods. As-prepared materials were calcined at various temperatures to generate different nature (Br?nsted and Lewis), amount and strength of acidic sites. The physico-chemical properties of the catalysts were studied by XRD, N2 sorption, pyridine-FTIR, NH3-TPD, DRS UV-vis, TGA, SEM, TEM, 1H MAS and 119Sn MAS NMR analyses. The catalytic behavior of mesoporous tin oxide catalysts was evaluated for acetalization and ketalization of glycerol with benzaldehyde and acetone respectively under solvent free conditions. The catalytic performance of mesoporous tin oxide was compared with that of other conventional solid acid catalysts namely H-ZSM-5, H-mordenite, H-beta, Al-MCM-41, Al-SBA-15 and Al-TUD-1. The efficiency of mesoporous tin oxide was also tested for cyclohexene epoxidation reaction. The catalyst prepared by template assisted method showed excellent catalytic performance compared to other catalysts due the difference in nature and amount of acidic sites in the catalyst. Meso-SnO2-T-350 was stable and reusable catalyst for four cycles without any appreciable loss in activity, and therefore it offers a good catalyst for potentially wide applications.

Exploring the Br?nsted acidity of UiO-66 (Zr, Ce, Hf) metal-organic frameworks for efficient solketal synthesis from glycerol acetalization

Bakuru, Vasudeva Rao,Churipard, Sathyapal R.,Maradur, Sanjeev P.,Kalidindi, Suresh Babu

, p. 843 - 847 (2019)

Zr, Ce, Hf-based isostructural UIO-66 MOFs exhibited varying degree of Br?nsted acidity (UiO-66(Hf) > UiO-66(Ce) > UiO-66(Zr)) on their secondary building units owing to the differences in their oxophilicities. UIO-66(Hf) showed remarkable catalytic activity for solketal synthesis with a turnover frequency as high as 13?886 h?1, which is 90 times higher than that of UiO-66(Zr) and several orders of magnitude higher than that of H2SO4 or Zeolites.

Synthesis and immunological study of a wall teichoic acid-based vaccine against E. faecium U0317

Zhou, Zhifang,Ding, Wenzhang,Li, Chen,Wu, Zhimeng

, p. 205 - 219 (2017)

A repeat unit of cell wall teichoic acids (WTA) isolated from E. faecium U0317 was chemically synthesized efficiently by a stepwise strategy. It was derivatized with a 5-aminopentanyl linker to facilitate conjugation with carrier proteins KLH and HSA. Immunological studies of the KLH conjugate 1 demonstrated that it could provoke robust immune responses and high titers of IgG antibodies, which could successfully recognize the synthesized WTA repeat unit 3. This result suggested that synthetic glycoconjugate 1 could be a promising vaccine candidate against E. faecium for further studies.

Acetalization of glycerol with ketones and aldehydes catalyzed by high silica Hβ zeolite

Poly, Sharmin Sultana,Jamil, Md.A.R.,Touchy, Abeda S.,Yasumura, Shunsaku,Siddiki, S.M.A. Hakim,Toyao, Takashi,Maeno, Zen,Shimizu, Ken-ichi

, (2019)

In this work, proton-exchanged *BEA zeolite with a high Si/Al ratio of 75 (Hβ-75), was demonstrated as an effective catalyst for the acetalization of glycerol with carbonyl compounds. This catalyst system was applicable to various substrates and reusable for at least 4 times with slight decrease in activity. The turnover frequency, based on acid site concentration, increased as a function of Hβ Si/Al ratio, indicating the importance of the zeolite hydrophobic surface properties. The origin of the high efficiency exhibited by Hβ-75 is quantitatively discussed based on kinetic studies, hydrophobicity, and acid site concentration.

Continuous reactor technology for ketal formation: An improved synthesis of solketal

Clarkson, Jay S.,Walker, Andrew J.,Wood, Michael A.

, p. 630 - 635 (2001)

The development of a fully continuous process for the synthesis of solketal (4-hydroxymethyl-2,2-dimethyl-1,3-dioxolane) is described. The use of a heterogeneous catalyst, recycle of unreacted starting material, elimination of the need for an entraining solvent, and purification of the product in situ all afford improvements over existing processes. Data generated in model reactions is used to prove the applicability of the process to a counter-current distillation reactor design, and to compute the operating parameters of the reactor.

Dealuminated BEA zeolite for selective synthesis of five-membered cyclic acetal from glycerol under ambient conditions

Venkatesha,Bhat,Jai Prakash

, p. 18824 - 18833 (2016)

BEA zeolite was treated with phenoldisulfonic acid (PDSA) of different concentrations from 0.1 M to 1.0 M to obtain dealuminated zeolites. The treated BEA samples were characterized by XRD, 27Al-MAS NMR, SEM-EDX, TPD NH3, pyridine-FTIR and BET measurements. Modified zeolites showed an increase in surface area and pore volume and a decrease in acid amount with an increase in PDSA concentration. An untreated BEA sample catalyzed the reaction between glycerol and acetone to form glycerol acteals to yield two products, five-membered dioxalane and six-membered dioxane. Under optimized reaction conditions, the untreated BEA sample showed 83% dioxalane and 17% dioxane while the modified samples showed an increase in dioxalane selectivity with an increase in the acid concentration used for the treatment. The 1 M PDSA treated sample exhibited 100% selectivity for dioxalane. This is attributed to an increase in pore volume and decrease in acid amount of the modified BEA samples with an increase in PDSA concentration. The combined effect of pore volume and acidity in determining dioxalane selectivity is discussed.

Acetalization of acetone with glycerol catalyzed by niobium-aluminum mixed oxides synthesized by a sol–gel process

Rodrigues, Raphael,Mandelli, Dalmo,Gon?alves, Norberto S.,Pescarmona, Paolo P.,Carvalho, Wagner A.

, p. 122 - 130 (2016)

Niobium-aluminum-based catalysts were synthesized by a sol–gel process and successfully applied to the reaction of acetalization of acetone with glycerol yielding 2,2-dimethyl-1,3-dioxolane-4-methanol (solketal) and 2,2-dimethyl-1,3-dioxan-5-ol. The synthesis procedure was developed using high-throughput techniques and the materials prepared with molar ratio1 Metal (1Nb:xAl): 100H2O: 1.5NH4OH (in which x?=?1, 0.6, 0.3, 0.1 and 0.05) were selected to be further investigated. The obtained series of mixed oxides displayed high catalytic activity reaching glycerol conversion up to 84%, with 98% of selectivity towards solketal. The physicochemical properties of the investigated catalysts were characterized by N2-adorption/desorption, thermal analysis, X-rays diffraction, FTIR and Raman spectroscopy, and by adsorption of pyridine monitored by FT-IR spectroscopy and TGA. The catalysts are truly heterogeneous and can be reused in consecutive runs without loss of activity.

Water-tolerant zeolite catalyst for the acetalisation of glycerol

Da Silva, Carolina X. A.,Gonalves, Valter L. C.,Mota, Claudio J. A.

, p. 38 - 41 (2009)

We studied the acid-catalysed reaction of glycerol with aqueous formaldehyde and acetone in absence of solvents and using heterogeneous catalysts. The reactivity of acetone was usually higher than formaldehyde and the glycerol conversion was over 90% within 40 min of reaction time for all the heterogeneous acid catalysts studied. With aqueous formaldehyde solution, the glycerol conversion was within 60 to 80%, depending upon the acid catalyst used (Amberlyst-15, K-10 montmorillonite, p-toluene-sulfonic acid), due to the high amount of water in the reaction medium, which shifts the equilibrium and weakens the acid sites. However, the use of zeolite Beta, with Si/Al ratio of 16, leads to a conversion of over 95% within 60 min of reaction time. The hydrophobic character of the zeolite, due to the high silicon content, prevents the diffusion of the water to the interior of the pore, preserving the strength of the acid sites. In addition, the water formed during the acetalisation is expelled off from the pore environment, impairing the reverse reaction, and avoiding the use of hazard solvents, commonly employed to distil off the water formed.

Kinetics of the Formation of Solketal in the Presence of Sulfuric Acid

Dmitriev,Terekhov,Zanaveskin,Maksimov,Khadzhiev

, p. 504 - 508 (2018)

The kinetics of reversible solketal synthesis in the presence of sulfuric acid as a catalyst is studied. The parameters of kinetic equations describing direct and reverse reactions are found.

Amino acid ionic liquids as catalysts in a solvent-free Morita-Baylis-Hillman reaction

Pereira, Mathias Prado,Souza Martins, Rafaela De,De Oliveira, Marcone Augusto Leal,Bombonato, Fernanda Irene

, p. 23903 - 23913 (2018)

In the present work, we describe the preparation of ten amino acid ionic liquids (AAILs) formed from ammonium salts as cations, derivatives of glycerol, and natural amino acids as anions. All of them are viscous oils, colorless or pale yellow, and hygroscopic at room temperature. They have appreciable solubility in many protic and aprotic polar solvents. The AAILs were used as catalysts in a Morita-Baylis-Hillman (MBH) reaction. The ionic liquids derivative from l-proline and l-histidine demonstrated the ability to catalyze the reaction between methyl vinyl ketone and aromatic aldehydes differently substituted in the absence of an additional co-catalyst under organic solvent-free conditions. The AAIL derivatives from l-valine, l-leucine, and l-tyrosine catalyzed the MBH reaction only in the presence of imidazole. The MBH adducts were obtained in moderate to good yields. Although the catalytic site in the ILs was in its enantiomerically pure form, all the MBH adducts were obtained in their racemic form.

Green efficient synthesis of ketal under catalysis of ionic liquid TTPT

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Paragraph 0037-0040, (2021/08/07)

The invention discloses a method for green efficient synthesis of ketal under catalysis of ionic liquid TTPT. The method comprises the following steps: adding TTPT and a water-carrying agent into a raw material I and a raw material II, and carrying out a heating reflux reaction for 110-150 minutes, wherein R1 and R2 in formulas I and II are independently selected from a group consisting of a methyl group, an ethyl group and a phenyl group, or R1 and R2 are connected and cyclized to form a 5-to-10-membered naphthenic base; and R3 is selected from H or-OH. Compared with the prior art, the catalytic yield of the TTPT is remarkably improved, a good catalytic effect is achieved, and experimental operation is easy and convenient.

Preparation method of trans-1, 3-diolefine

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Paragraph 0068, (2021/03/18)

The invention discloses a preparation method of trans-1, 3-diolefine, which comprises the following step: under the action of 4-dimethylaminopyridine and triethylamine, reacting 2, 3-dihydroxy propyl(9E, 12E)-9, 12-octadecadienoic acid ester with (9E, 12E)-9, 12-octadecadienoyl chloride to obtain the trans-1, 3-diolefine. Compared with the prior art, the method disclosed by the invention is simpleto operate, high in reaction selectivity and high in product yield.

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