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Cascade conversion of furancarboxylic acid to butanediol diacetate over Pd/C and La(OTf)3 catalytic system
The conversion of biomass to a high value-added product 1, 4-butanediol (BDO) and its derivatives is of great economic significance. In this work, furancarboxylic acid (FCA) was adopted as the raw material to prepare BDO. The one-pot synthesis of 1, 4-butanediol diacetate (BDA) has been successfully prepared from FCA with metal triflates and Pd/C catalysts. The effect of reaction conditions was investigated and the reaction routes was systematically studied by 1H-NMR and GC. The tandem catalytic process from FCA to BDA mainly underwent three stages. Firstly, FCA was hydrogenated to tetrahydrofurfuric acid (THFCA) by Pd/C. Afterwards, THFCA was decarbonylated to form oxonium ions with metal triflates. Then the oxonium ions was rapidly hydrogenated to form tetrahydrofuran (THF) by Pd/C. Ultimately, THF was ring-opening esterified to BDA by metal triflates. This novel synthesis method of BDO from FCA provides a promising protocol for broadening the application of common biomass substrates.
Deng, Jin,Fu, Yao,Gong, Baoxiang,Zhou, Gongyu,Zhu, Rui
(2020/11/12)

Preparation method of 1,4-butanediol and dicarboxylic acid ester thereof
The invention relates to a preparation method of 1,4-butanediol and a dicarboxylic acid ester thereof. Specifically, the preparation method of 1,4-butanediol and the dicarboxylic acid ester thereof comprises the following steps: performing hydrodecarbonylation esterification ring-opening on a furoic acid compound, a trifluoromethanesulfonate, a hydrogenation catalyst in a carboxylic acid solvent to obtain a 1,4-butanediol dicarboxylic acid ester. The method has the characteristics of simple process, easy purification, high yield, green safety, and the like, and is suitable for large-scale industrial production.
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Paragraph 0032-0051; 0056; 0058

(2019/10/01)

Lipase-mediated selective acetylation of primary alcohols in ethyl acetate
An environmental friendly process to selectively acetylate primary alcohols was demonstrated. The esterification process consists of treatment of a primary alcohol in the presence of immobilized C. antarctica lipase (Novozyme-435) in ethyl acetate at room temperature. Primary alcohols were acetylated in the presence of secondary alcohols and phenols.
de Souza, Ernane C.,Romero-Ortega, Moises,Olivo, Horacio F.
supporting information
p. 287 - 290
(2017/12/29)

METHOD FOR PRODUCING 1,3-BUTADIENE FROM 1,4-BUTANEDIOL
A method for producing 1,3-butadiene from a 1,4-butanediol feedstock: One step for esterification of 1,4-butanediol,One step for pyrolysis of 1,4-butanediol diester, producing butadiene.
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Paragraph 0107

(2018/03/01)

Ethyl acetate as an acetyl surrogate for the iodine catalyzed acetylation of alcohols
The use of readily available ethyl acetate in the presence of iodine as an alternative acetylating agent is reported. Amines and phenols were unreactive under the examined reaction conditions, indicating that the method is highly chemoselective.
Basumatary, Grace,Bez, Ghanashyam
supporting information
p. 4312 - 4315
(2017/10/13)

Efficient acylation and transesterification catalyzed by dilithium tetra-tert-butylzincate at low temperatures
The acylation and transesterification of alcohols with vinyl acetate and carboxylic esters were investigated in the presence of a catalytic amount (1-10 mol %) of dilithium tetra-tert-butylzincate (TBZL) as a catalyst. The acylation proceeded quantitatively at 0 °C within 1 h. The transesterification occurred for a wide range of combinations of esters and alcohols at 0 to -40 °C. To the best of our knowledge, this is the first successful transesterification at such low temperatures. The time-conversion plots for the transesterification show that the reaction reached equilibrium within 5 min at 0 °C. The reaction proceeded quantitatively by addition of molecular sieves 4A. In addition, the transesterification proceeded even in the presence of H2O and amines.
Oshimura, Miyuki,Oda, Yuki,Kondoh, Keita,Hirano, Tomohiro,Ute, Koichi
p. 2070 - 2073
(2016/04/26)

Esterification of carboxylic acids with alkyl halides using imidazolium based dicationic ionic liquids containing bis-trifluoromethane sulfonimide anions at room temperature
Task-specific room temperature ionic liquids (RTILs) composed of symmetrical N-methylimidazolium rings linked with a short oligo (ethylene glycol) chain (cationic part) and bis-trifluoromethane sulfonimide (NTf2, anionic part) were successfully synthesized, and their physicochemical properties were determined by various modern analytical techniques. The catalytic activity of the synthesized RTILs was evaluated in the esterification reaction of acids with alkyl halides in solvent-free conditions at room temperature. From the screening test, all the synthesized RTILs showed a high yield with significant selectivity for respective esters in a very short reaction time. Especially, 0.1 equimolar of RTIL-1 ([tetraEG(mim)2][NTf2]2) was found to be, the most efficient and reusable catalyst for this reaction. As a result, 100% conversion and up to a 94% yield of the respective ester product was obtained in a 30 min reaction time. This might be due to their synergetic effect of Lewis acidity, wide liquid range, and high miscibility compared to the other homogeneous and heterogeneous catalysts. Beside this, RTIL was easily separated from the reaction mixture and reused several times without any significant loss of catalytic activity and structural property. The present dicationic ionic liquids (ILs) under a solvent-free catalytic system were found to be kinetically fast, naturally benign, and achieved good yields for esterification of carboxylic acids with alkyl halides.
Jadhav, Arvind H.,Lee, Kyuyoung,Koo, Sangho,Seo, Jeong Gil
p. 26197 - 26208
(2015/10/20)

Conformational characteristics and configurational properties of poly(ethylene succinate) and poly(butylene succinate) and structure-property-function relationships of representative biodegradable polyesters
Conformational characteristics and configurational properties of synthetic biodegradable polyesters, poly(ethylene succinate) and poly(butylene succinate), have been investigated by NMR experiments and molecular orbital calculations on their model compounds and the rotational isomeric state calculations for the two aliphatic polyesters. The results have been related to their crystal structures and thermal properties and compared with those obtained previously for poly((R)-3-hydroxybutyrate) and poly(lactic acid) to elucidate structureeproperty relationships of the representative biodegradable polyesters. In addition, selective affinities to degradative enzymes of the four polyesters have been satisfactorily explained in terms of their conformational characteristics and interactions with the depolymerases.
Sasanuma, Yuji,Nonaka, Yuta,Yamaguchi, Yuki
p. 327 - 339
(2015/03/03)

Magnetically separable γ-Fe2O3 nanoparticles: An efficient catalyst for acylation of alcohols, phenols, and amines using sonication energy under solvent free condition
This paper reports a facile synthesis of magnetically separable iron oxide (γ-Fe2O3) nanoparticles using thermolysis method. The structural and morphological study of the synthesized γ-Fe2O3 nanoparticles was carried out using X-ray diffraction (XRD), field emission gun-scanning electron microscopy (FEG-SEM), energy dispersive X-ray spectrum (EDS), transmission electron microscopy (TEM), Fourier transform infrared spectroscopy (FT-IR), thermogravimetric analysis (TGA), and X-ray photoelectron spectroscopy (XPS) techniques. The electron microscopy reveals that the γ-Fe2O3 nanoparticles have spherical morphology with a particle size in the range of 40-100 nm. The XPS study confirmed the Fe is in +3 oxidation state. The synthesized γ-Fe2O3 nanoparticles have been used as an efficient heterogeneous catalyst for the organic transformation between phenols, alcohols, and amines with acetic anhydride under sonication using mild reaction conditions. Various electrons withdrawing and electrons donating substrates show an excellent yield of desired products with the advantage of magnetic separation and reusability of γ-Fe2O3 nanocatalyst.
Bhosale, Manohar A.,Ummineni, Divya,Sasaki, Takehiko,Nishio-Hamane, Daisuke,Bhanage, Bhalchandra M.
p. 8 - 17
(2015/04/27)

Zinc-catalyzed depolymerization of polyethers to produce valuable building blocks
The recycling of polymers continues to be a significant matter for a sustainable society. In particular, the conversion of end-of-life polymers to monomers or suitable low-molecular weight chemicals creates a feedstock for new high-quality polymeric materials and contributes to conserve resources and allow overall an efficient waste-managing system. In the present study, we have set up a straightforward methodology for the depolymerization of artificial polyethers applying cheap and abundant zinc( II) salts as precatalysts. In the presence of bio-based fatty acid chlorides as depolymerization reagent well-defined chloroesters were accessible in good to excellent yields. Moreover, acetic anhydride and fatty acids were applied as depolymerization reagents resulting in the formation of diacetates in moderate yields. In both cases the obtained products (chloroesters, diacetates) can be useful building blocks in polymerization chemistry. Noteworthy, overall a recycling of polyethers are possible. Springer Science+Business Media New York 2014.
Enthaler, Stephan
p. 850 - 859
(2014/06/23)

Heterobimetallic dinuclear lanthanide alkoxide complexes as acid-base difunctional catalysts for transesterification
A practical lanthanide(III)-catalyzed transesterification of carboxylic esters, weakly reactive carbonates, and much less-reactive ethyl silicate with primary and secondary alcohols was developed. Heterobimetallic dinuclear lanthanide alkoxide complexes [Ln2Na8{(OCH2CH2NMe2)}12(OH)2] (Ln = Nd (I), Sm (II), and Yb (III)) were used as highly active catalysts for this reaction. The mild reaction conditions enabled the transesterification of various substrates to proceed in good to high yield. Efficient activation of transesterification may be endowed by the above complexes as cooperative acid-base difunctional catalysts, which is proposed to be responsible for the higher reactivity in comparison with simple acid/base catalysts.
Zeng, Ruijie,Sheng, Hongting,Zhang, Yongcang,Feng, Yan,Chen, Zhi,Wang, Junfeng,Chen, Man,Zhu, Manzhou,Guo, Qingxiang
p. 9246 - 9252
(2014/12/11)

Design of a highly active silver-exchanged phosphotungstic acid catalyst for glycerol esterification with acetic acid
A series of highly active, selective, and stable silver-exchanged phosphotungstic acid (AgPW) catalysts were prepared, characterized, and evaluated for bio-derived glycerol esterification with acetic acid to produce valuable biofuel additives. The structures, morphologies, acidities, and water tolerance of these samples were determined by FTIR, Raman, XRD, SEM-EDX, FT-IR of pyridine adsorption, and H2O-TPD. Several typical acidic catalysts were also performed for comparison. Among them, partially silver-exchanged phosphotungstic acid (Ag1PW) presented exceptionally high activity, with 96.8% conversion within just 15 min of reaction time and remarkable stability, due to the unique Keggin structure, high acidity as well as outstanding water-tolerance property. A plausible reaction mechanism was also proposed. In addition, this Ag1PW catalyst exhibited universal significance for esterification, holding great potential for a wide range of other acid-catalyzed reactions.
Zhu, Shanhui,Gao, Xiaoqing,Dong, Fang,Zhu, Yulei,Zheng, Hongyan,Li, Yongwang
p. 155 - 163
(2013/09/02)

Rational engineering of Candida antarctica lipase B for selective monoacylation of diols
The enzyme Candida antarctica lipase B was subjected to site directed mutagenesis suggested by molecular modelling. The selectivity for the enzyme increased towards a range of diols over their corresponding monoesters as an effect of the mutations. This journal is The Royal Society of Chemistry 2012.
Hamberg, Anders,Maurer, Steffen,Hult, Karl
supporting information
p. 10013 - 10015
(2012/10/30)

Investigation of steapsin lipase for kinetic resolution of secondary alcohols and synthesis of valuable acetates in non-aqueous reaction medium
In present study, the application of steapsin lipase (as a biocatalyst) was investigated for kinetic resolution of secondary alcohols (1-phenyl ethanol and their derivatives) using vinyl acetate as an activated acyl donor. The enzymatic protocol was optimized for various reaction parameters such as effect of the molar ratio, solvent, temperature, time and biocatalyst loading to obtain best reaction conditions. On optimization, developed enzymatic methodology provided considerable enantiomeric excess of the product (up to 92% ee) at 55 °C in n-hexane as a solvent. Furthermore using the developed protocol, synthesis of several industrially important acetates was successfully achieved with excellent yield (up to 99%). During acetate synthesis, the biocatalyst was remarkably reused for eight consecutive recycles without any significant loss in its catalytic activity. This revealed the good potential of steapsin lipase for application in organic solvents.
Dhake, Kishor P.,Deshmukh, Krishna M.,Wagh, Yogesh S.,Singhal, Rekha S.,Bhanage, Bhalchandra M.
experimental part
p. 15 - 23
(2012/06/29)

Synthesis of a novel multi-SO3H functionalized ionic liquid and its catalytic activities
A novel multi-SO3H functionalized ionic liquid is synthesized and a detailed account of its cata- lytic activities in acetalization and acetylation is given. The results showed that the ionic liquid is very efficient in the conventional acid-catalyzed reactions with good to excellent yields within a short reaction time. Oper- ational simplicity, small amounts required, low cost of the catalyst, high yields, scalability and reusability are the key features of this methodology, which indicates the high potentialities of the novel ionic liquid to be used in environmentally friendly processes. Pleiades Publishing, Ltd., 2012.
Xudong, Sun,Huiquan, Xiao,Yijun, Du,Jingjing, Zhang,Xuezheng, Liang,Chenze, Qi
p. 301 - 305
(2012/10/29)

Ionic liquid [BMIM]PF6 as a medium for the selective hydrogenation of 1,4-diacetoxybut-2-yne on the Pd-containing catalysts
A possibility of using a ionic liquid, 1-n-butyl-3-methylimidazolium hexafluorophosphate ([BMIM]PF6), as a reaction medium in the liquid-phase hydrogenation of 1,4-diacetoxybut-2-yne was examined. Two types of catalysts were studied: Pd(10%)/C and the palladium-containing catalytic system based on the biopolymer chitosan supported on silica gel (Pd(1%)/chitosan/SiO2). The data obtained indicate high selectivity of hydrogenation of 1,4-diacetoxybut-2-yne to cis-1,4-diacetoxybut-2-ene under selected conditions.
Tarasenko,Isaeva,Beletskaya,Kustov
experimental part
p. 179 - 181
(2011/08/10)

Effects of acidity and immiscibility of lactam-based Bronsted-acidic ionic liquids on their catalytic performance for esterification
Several lactam-based Bronsted-acidic ionic liquids with different acidities were synthesized and applied to the esterification of carboxylic acids with alcohols. High conversion and perfect selectivity were obtained under mild conditions. Among the ionic liquids investigated, those having a methyl sulfonate anion (which has weaker acidity than those with a tetrafluoroborate anion) afforded the highest activity for esterification. The results indicated that the acidity and immiscibility of Bronsted-acidic ionic liquids has a synergistic effect on their esterification performance. Furthermore, after removal of water under vacuum, such ionic liquids could be reused several times without substantial loss of activity.
Zhou, Hancheng,Yang, Jing,Ye, Linmin,Lin, Haiqiang,Yuan, Youzhu
experimental part
p. 661 - 665
(2010/08/22)

PROCESS FOR PREPARING 1,4-BUTANDIOL MONONITRATE
The present invention relates to a process for the preparation of 1,4-butanediol mononitrate as intermediate for large scale preparation of high purity nitrooxybutyl ester of pharmaceutically active compounds.
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Page/Page column 25-27

(2009/03/07)

Samarium trifluoromethanesulfonate: An efficient moisture tolerant acylation catalyst under solvent-free condition
Samarium trifluoromethanesulfonate catalyzed the acylation of phenols, alcohols, thiols, free reducing sugars, and glycosides in excellent yields at ambient temperature under solvent-free condition using stoichiometric amounts of various anhydrides. (Chemical Equation Presented). Copyright Taylor & Francis Group, LLC.
Roy, Bimalendu,Dasgupta, Somnath,Kumar Rajput, Vishal,Mukhopadhyay, Balaram
p. 1 - 9
(2008/09/21)

Erbium(III) chloride: A very active acylation catalyst
Erbium(iii) chloride is a powerful catalyst for the acylation of alcohols and phenols. The reaction works well for a large variety of simple and functionalized substrates by using different kinds of acidic anhydrides (Ac 2O, (EtCO)2O, (PriCO)2O, (Bu tCO)2O, and (CF3CO)2), without isomerization of chiral centres. Moreover, the catalyst can be easily recycled and reused without significant loss of activity. CSIRO 2007.
Dalpozzo, Renato,De Nino, Antonio,Maiuolo, Loredana,Oliverio, Manuela,Procopio, Antonio,Russo, Beatrice,Tocci, Amedeo
p. 75 - 79
(2008/02/10)

A mild and efficient acetylation of alcohols, phenols and amines with acetic anhydride using La(NO3)3·6H2O as a catalyst under solvent-free conditions
A wide variety of alcohols, phenols and amines are efficiently and selectively converted into the corresponding acetates by treatment with acetic anhydride in the presence of catalytic amounts of La(NO3)3·6H2O under solvent-free conditions at room temperature. The method is compatible with acid sensitive hydroxyl protecting groups such as TBDMS, THP, OBz, OBn, Boc and some isopropylidenes and offers excellent yields of the mono acetates of 1,3-, 1,4- and 1,5-diols.
Reddy, T. Srikanth,Narasimhulu,Suryakiran,Mahesh, K. Chinni,Ashalatha,Venkateswarlu
p. 6825 - 6829
(2007/10/03)

Ruthenium catalysed reduction of alkenes using sodium borohydride
The reduction of alkenes has been achieved using NaBH4 as the reducing agent using 0.5-1.0 mol % Ru(PPh3)4H2 in the presence of water.
Adair, Gareth R.A.,Kapoor, Kamal K.,Scolan, Alexandre L.B.,Williams, Jonathan M.J.
p. 8943 - 8944
(2007/10/03)

Acylative dimerization of tetrahydrofuran catalyzed by rare-earth triflates
Ytterbium, scandium, and lanthanum triflates catalyze the cleavage reactions of cyclic ethers to give various products. Most notable was the acylative cleavage of tetrahydrofuran with acetic anhydride catalyzed by Yb(triflate)3 to give the dime
Miles, William H.,Ruddy, Daniel A.,Tinorgah, Samira,Geisler, Rebecca L.
p. 1871 - 1880
(2007/10/03)

Sulfamic acid as a cost-effective catalyst instead of metal-containing acids for acetolysis of cyclic ethers
Sulfamic acid has been used as an efficient catalyst for acetolysis reaction of THF to produce 1,4-diacetoxybutane. This method is applicable also to the acetolysis of other cyclic ethers, such as methyl substituted THF and tetrahydropyran and 1,4-dioxane. Sulfamic acid has been used as an efficient catalyst and green alternative for metal-containing acidic materials to promote the acetolysis reaction of THF to produce 1,4-diacetoxybutane. This method is also applicable to the acetolysis of other cyclic ethers, such as methyl substituted THF and tetrahydropyran and 1,4-dioxane, which is less reactive.
Wang, Bo,Gu, Yanlong,Gong, Weizhong,Kang, Yuru,Yang, Liming,Suo, Jishuan
p. 6599 - 6602
(2007/10/03)

Erbium(III) triflate as an extremely active acylation catalyst
Erbium(III) triflate is a powerful catalyst for the acylation of alcohols and phenols. The reaction works well for a large variety of simple and functionalized substrates by using different kinds of acidic anhydrides {Ac 2O, (EtCO)2O, [(CH3)3CO] 2O, Bz2O, and (CF3CO)2O} without isomerisation of chiral centres. Moreover, the catalyst can be easily recycled and reused without significant loss of activity.
Procopio, Antonio,Dalpozzo, Renato,De Nino, Antonio,Maiuolo, Loredana,Russo, Beatrice,Sindona, Giovanni
p. 1465 - 1470
(2007/10/03)

P2O5 / SiO2 as a mild and efficient reagent for acylation of alcohols, phenols and amines under solvent-free conditions
P2O5 / SiO2 is a highly efficient reagent for the acetylations of a variety of alcohols, phenols and amines with acetic anhydride under solvent-free conditions. Primary, secondary, allylic and benzylic alcohols, diols and phenols with electron-donating or withdrawing substituents can be easily acetylated in good to excellent yield.
Eshghi, Hossein,Shafieyoon, Parvaneh
p. 802 - 805
(2007/10/03)

Highly efficient and versatile acetylation of alcohols catalyzed by cerium(III) triflate
Cerium(III) triflate is a powerful catalyst for the acetylation of alcohols. The reaction works well for a large variety of simple and functionalized alcohols, without isomerisation of chiral centres. Changes of hydroxyl protective groups are possible in a one-pot procedure. The catalyst can be easily recycled.
Dalpozzo, Renato,De Nino, Antonio,Maiuolo, Loredana,Procopio, Antonio,Nardi, Monica,Bartoli, Giuseppe,Romeo, Roberto
p. 5621 - 5624
(2007/10/03)

Aluminium dodecatungstophosphate (AlPW12O40) as a highly efficient catalyst for the selective acetylation of -OH, -SH and -NH2 functional groups in the absence of solvent at room temperature
AlPW12O40 was found to be an effective catalyst for the selective acetylation of alcohols, thiols, and amines in the absence of solvent at room temperature.
Firouzabadi, Habib,Iranpoor, Nasser,Nowrouzi, Farhad,Amani, Kamal
p. 764 - 765
(2007/10/03)

Indium triiodide catalysed one-step conversion of tetrahydropyranyl ethers to acetates with high selectivity
Chemoselective one-step conversion of tetrahydropyranyl ethers of primary alcohols to corresponding acetates was carried out. The reaction occurred through an indium triiodide catalyzed transesterification process in ethyl acetate. The method provided advantages such as operational simplicity, acceptable reaction conditions to acid-sensitive functional groups and good yield.
Ranu, Brindaban C.,Hajra, Alakananda
p. 355 - 357
(2007/10/03)

Highly selective one-pot conversion of THP and MOM ethers to acetates by indium triiodide-catalysed deprotection and subsequent transesterification by ethyl acetate
The chemoselective one-pot conversion of tetrahydropyranyl (THP) and methoxymethyl (MOM) ethers of primary alcohols to the corresponding acetates was presented. It was done using indium triiodide-catalysed deprotection and subsequent acetylation by ethyl acetate through a transesterification process. The advantages offered by the method included operational simplicity, 'green' methodology involving no toxic or hazardous chemicals and high yield.
Ranu, Brindaban C.,Hajra, Alakananda
p. 2262 - 2265
(2007/10/03)

Ring opening of cyclic ethers by sulfuric acid - Acetic anhydride
Cyclic ethers such as tetrahydrofuran or tetrahydropyran were easily cleaved at room temperature by sulfuric acid - acetic anhydride providing the corresponding diacetoxyalkanes in good yield. The ring opening was applicable to saturated cyclic ethers, regardless of the presence of substituent groups.
Tanoue,Hamada,Kai,Nagai,Sakata,Hashimoto,Morishita
p. 1351 - 1353
(2007/10/03)

Selective diesterification of diols through cyclic ketene acetal intermediates
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Wu, Zhihong,Stanley, Roy R.,Pittman Jr., Charles U.
p. 8386 - 8395
(2007/10/03)

Synthesis of a hydrogen-bond-degenerate tricyclic pyrrolopyrimidine nucleoside and of its 5′-triphosphate
The syntheses of a number of 7-(2-deoxyribofuranosyl)pyrrolo[2,3-d]pyrimidine derivatives are described. Of these the 2-methylsulfanyl-4-hydroxy-5-acetoxyethyl derivative 7 was conveniently formed by condensation of 2-methylsulfanyl-4-hydroxy-6-aminopyrimidine with 2-chloro-4-acetoxybutanal 6; it was then converted to the 4-chloro derivative 12 with phosphoryl trichloride and coupled to 3,5-di-p-toluoyl-2-deoxy-α-ribosyl chloride. Transformation to the 5-aminooxyethyl derivative and ring closure of the latter gave the tricyclic 2-(2-deoxyribosyl)-4-methylsulfonyl-7-oxa-2,3,5,6-tetraazabenz[cd]azulene. Hydrazinolysis of the methylsulfonyl residue, then mercury(II) oxide oxidation, led to the target nucleoside 4. For its study as a polymerase substrate for incorporation into DNA the 5′-triphosphate was synthesised.
Williams, David M.,Loakes, David,Brown, Daniel M.
p. 3565 - 3570
(2007/10/03)

Distannoxane-Catalyzed Highly Selective Acylation of Alcohols
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Orita, Akihiro,Mitsutome, Akihiro,Otera, Junzo
p. 2420 - 2421
(2007/10/03)

A remarkably simple process for monoprotecting diols
Lipase from pig pancreas (PPL) has been shown to catalyse selectively the hydrolysis of alkane-1,n-diol bis-acetates into the corresponding monoacetate.
Houille, Olivier,Schmittberger, Thierry,Uguen, Daniel
p. 625 - 628
(2007/10/02)

Highly Selective Monoacylation of Symmetric Diols Catalyzed by Metal Sulfates Supported on Silica Gel
Several 1,α-diols, ranging from 1,2-ethanediol to 1,16-hexadecanediol, were monoacylated with high selectivity by reaction with esters in the presence of metal sulfates or hydrogen sulfates, like Ce(SO4)2 and NaHSO4, supported on silica gel.Symmetrical secondary diols were also selectively monoformylated, by reaction with ethyl formate.This method of selective esterification is simple and practical.The yield of monoester depends upon both the composition and the volume of the solvent (an ester/alkane mixture).Unsupported NaHSO4 also catalyzed monoacylation, but the selectivity was less than in monoacylations catalyzed by the supported reagent.The selectivity can be explained by the following reasons: (1) monoacylated products are formed selectively because the diol, but not the monoester, is preferentially adsorbed on the surface of the catalysts, where esterification then occurs, and (2) thin diol layers are formed on the surface of the catalysts due to limited solubility of the diols in the solvent.
Nishiguchi, Takeshi,Kawamine, Katsumi,Ohtsuka, Tomoko
p. 312 - 316
(2007/10/02)

THE RELATIVE REACTIVITY OF 2-METHYL-1,3-DIOXOLANE IN RADICAL REACTION WITH UNSATURATED COMPOUNDS
The reactivity of 2-methyl-1,3-dioxolan-2-yl radicals toward α-olefins containing substituents with various polarities was studied.There is a substantial increase in the relative addition rate constant in the series consisting of vinyl butyl ether, 1-hexene, vinyl acetate, trimethylvinylsilane, methyl acrylate, and acrylonitrile.This indicates that the 2-methyl-1,3-dioxolan-2-yl radicals have clearly defined nucleophilic character.
Ryabinina, T. A.,Kruglov, D. E.,Pastushenko, E. V.,Terent'ev, A. B.
p. 602 - 605
(2007/10/02)

THE SOLUBILITY OF CARBON DIOXIDE IN SOME ACETIC ACID ESTERS
The absorption of carbon dioxide in organic solvents containing acetyl groups (ethylene glycol diacetate, diethylene glycol diacetate, triethylene glycol diacetate, propylene glycol diacetate, ethyl cellosolve acetate, 1,4-butanediol diacetate, glycerol triacetate and β-phenyl acetate) is studied. Bunsen absorption coefficients in the range of 5 to 50 atm and at 25 deg C are obtained. Some considerations about the correlation between absorptive capacity and the molecular structure of these organic compounds are presented.
Vilcu, Rodica,Gainar, Ion,Maior, Ovidiu,Anitescu, Gheorghe
p. 875 - 878
(2007/10/03)

Facile Acylation of Aclohols Using Esters and Silica Gel-supported Metallic Sulphates and Hydrogen Sulphates
Alcohols are acylated in a quite simple operation in high yields by being heated in esters in the presence of silica gel-supported metallic sulphates and hydrogen sulphates, such as Ce(SO4)2, Ti(SO4)2, Fe2(SO4)3, and NaHSO4.
Nishiguchi, Takeshi,Taya, Hisachi
p. 172 - 173
(2007/10/02)

Preparation of Carboxylate Esters of Polyhydric Alcohols by Using a Sulfonated Charcoal Catalyst
Ethane-1,2-diol, propane-1,2-diol, butane-1,4-diol and propane-1,2,3-triol are readily esterified by carboxylic acids in near quantitative yields in the presence of a sulfonated charcoal catalyst.
Prager, Rolf H.,Yurui, Zhang
p. 1003 - 1005
(2007/10/02)

Selective Monoacylation of 1,n-Diols Catalyzed by Metallic Sulfates Supported on Silica Gel
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Nishiguchi, Takeshi,Taya, Hisashi
p. 9102 - 9103
(2007/10/02)

Acetyl transfer reactions on AlPO4-Al2O3
An efficient acetylation of alcohols and aliphatic amines promoted by the AlPO4-Al2O3/ethyl acetate system is described.The solid catalist acts, at least in part, as the acetyl carrier.
Costa, Antonio,Riego, Juan Martin
p. 2327 - 2328
(2007/10/02)

Nucleophilic Substitution of Chloride by Acetate in Polyethylene Glycol 400
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Theil, Fritz,Schick, Hans,Schwarz, Sigfrid
p. 350 - 352
(2007/10/02)

OZONOLYSIS OF ALKENES AND REACTIONS OF POLYFUNCTIONAL COMPOUNDS. XIX. SYNTHESIS OF α,ω-BIFUNCTIONAL REGULAR (Z)-1,5-POLYENES
α,ω-Dihydroxy- and ω-oxo-α-carboxy-(Z)-1,5-polyene aliphatic compounds were synthesized by selective ozonolysis of (Z)-1,4-polybutadiene (synthetic divinyl rubber) followed by reduction or hydrolysis of the oligomeric ozonides.They were converted into bis(trimethylsilyl) ethers and diacetates or tetramethyl derivatives, differing in the number of (Z)-butenylene units in the aliphatic chain.
Odinokov, V. N.,Ignatyuk, V. K.,Tolstikov, G. A.,Rafikov, S. R.
p. 1220 - 1229
(2007/10/02)

TRANSFORMATIONS OF 1,3-DIOXACYCLANES BY THE ACTION OF THE Fe(II) + H2O2 + Fe(III) SYSTEM
The reaction of 1,3-dioxacyclanes with the Fe(II) + H2O2 + Fe(III) system in an aqueous medium leads to the formation of glycol monoesters, while the reaction in acetic acid leads to the formation of glycol diesters.The reaction takes place through the formation and one-electron oxidation of 1,3-dioxa-2-cycloalkyl radicals.If the ring is increased, the yield of the esters and the relative reactivity of the 1,3-dioxacyclanes are reduced. 2-Methyl-1,3-dioxacyclanes are more reactive than the corresponding formals.In the reaction of 1,3-dioxacyclanes with the Fe(II) + H2O2 + Fe(III) system in aqueous acetic acid a mixture of the monoesters and diesters is formed, and the ratios of their concentrations depends linearly on the ratio of the concentrations of water and acetic acid.
Trifonova, V.N.,Zorin, V.V.,Zlot-skii, S.S.,Rakhmankulov, D.L.
p. 909 - 912
(2007/10/02)

Entgiftung aliphatischer Dihalogenverbindungen durch fest-fluessig phasentransfer-katalysierte Diacetatbildung
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Martinetz, Dieter
p. 257 - 258
(2007/10/02)

Reactions of Tin Tetraacetate with Glycols
The reactions of tin tetraacetate with different glycols, G(OH)2 in equimolar ratio lead to the formation of an insoluble polymeric solid which corresponds mainly to the formula along with a small amount of the corresponding glycol diacetate (AcOGOAc).The reactions in 1:2 molar ratio yield insoluble polymers corresponding to .The reaction of tin tetraacetate with pinacol, on the other hand, yields tin diacetate monopinacolate and tin dipinacolate respectively.
Vasanta, E.N.,Srivastava, G.,Mehrotra, R. C.
p. 983 - 984
(2007/10/02)

SYNTHESIS AND SEVERAL REACTIONS OF 2-ETHYL-1,2-OXAALUMANE
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Kuchin, A. V.,Nurushev, R. A.,Valitov, F. Kh.,Tolstikov, G. A.
p. 373 - 375
(2007/10/02)

Rapid hydrolysis of esters
An organic ester e.g. 1,4-diacetoxybutane is hydrolyzed with an alkali metal or an alkaline earth metal hydroxide to a corresponding alcohol, the reaction being rapidly effected by having present a hydroxyl-containing compound. In a preferred embodiment, the hydroxyl-containing compound to be present is the very compound to be produced e.g. 1,4-butanediol is to be produced from 1,4-diacetoxybutane and there is present during the reaction of hydrolysis an earlier produced 1,4-butanediol.
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(2008/06/13)

THE CATALYSIS OF THE ELECTROCHEMICAL REDUCTION OF ALKYL BROMIDES BY NICKEL COMPLEXES: THE FORMATION OF CARBON-CARBON BONDS
The square planar, macrocyclic nickel complex, N,N'-ethylenebis(salicylidene-iminato)nickel(II), is shown to be an effective catalyst for the electrochemical reduction of substituted alkyl bromides; this indirect cathodic reduction can lead to a good yield of dimeric products.The reduction of alkyl bromides in the presence of an activated olefin is shown to lead to mixtures of products compatible with radical addition to the double bond.The mechanism of the reaction of nickel(I) complexes with alkyl bromides is discussed in the light of these results.
Gosden, Cary,Pletcher, Derek
p. 401 - 409
(2007/10/02)