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Synthesis of cyclic ethers from diols in the presence of copper catalysts
A number of cyclic ethers, namely tetrahydrofuran, 2,5-dimethyltetrahydrofuran, tetrahydropyran, 1,4-dioxane, oxepane, oxocane, and 1,4-oxathiane, have been synthesized in high yields by intramolecular dehydration of diols in the presence of copper-based catalysts.
Bayguzina,Gimaletdinova,Khusnutdinov
p. 1840 - 1843
(2017)
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Reaction of butyltin hydroxide oxide with p-toluenesulfonic acid: Synthesis, X-ray crystal analysis, and multinuclear NMR characterization of {(BuSn)12O14(OH)6}(4-CH3C 6H4SO3)2
The reaction of butyltin hydroxide oxide, BuSnO(OH), with p-toluenesulfonic acid, 4-CH3C6H4SO3H, yields the butyltin oxo cluster {(BuSn)12(μ3-O)14(μ2-OH) 6}2+ mixed with a soluble ill-defined butyltin oxo polymer, the presence of which was established by solid-state and quantitative solution 119Sn NMR. The reaction conditions were varied in order to optimize the yield of oxo cluster, which can be quantitatively isolated by crystallization as {(BuSn)12O14(OH)6}(4-CH3C 6H4SO3)2·C4H 8O2 (1·diox). The structure of the latter compound was determined by X-ray diffraction. 1·diox and {(BuSn)12O14(OH)6}-(4-CH3C 6H4SO3)2 (1) were also characterized by solid-state 119Sn MAS NMR and solution 119Sn, 1H, and 13C NMR. In 1·diox, the existence of weak Lewis interactions, taking place in the crystal between five-coordinate tin atoms and dioxane molecules, was evidenced by solid-state 119Sn NMR. 2D 1H-1H NOESY and ROESY experiments, along with ionic conductivity measurements, have proved that the ionic dissociation between {(BuSn)12O14(OH)6}2+ and 4-CH3C6H4SO3- (PTS-) does not take place in dichloromethane, while it does in the more polar and dissociating dimethyl sulfoxide. Using the 1H-119Sn J-HMQC NMR technique, the weak 2J(1H-O-119Sn) coupling constant between the μ2-OH and the six-coordinate tin nuclei was determined and shown to depend on the solvent.
Eychenne-Baron, Christophe,Ribot, Fran?ois,Steunou, Nathalie,Sanchez, Clément,Fayon, Franck,Biesemans, Monique,Martins, José C.,Willem, Rudolph
p. 1940 - 1949
(2000)
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Gordon et al.
p. 583,587
(1955)
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Synthesis of 1,4-dioxene from diethylene glycol in the presence of bifunctional copper-containing catalysts. Effect of support on the selectivity of dioxene formation
In the synthesis of 1,4-dioxene from diethylene glycol in the presence of a bifunctional copper-containing catalyst, the composition of the by-products has been studied and the effect of the support on the overall direction of the reactions has been investigated. It has been established that on Cu/SiO2, 1,4-dioxanone is formed together with dioxene, the yield of the former increasing with an increase in the content of copper in the catalyst. This is due to an increase in the dehydrogenating function of the latter. On the more acidic Cu/Al2O3, 1,4-dioxane is mainly obtained together with, to a lesser degree, methyl-1,3-dioxolane. This is due to the predominance of dehydration reactions followed by isomerization. Dioxene, dioxane, and methyldioxolane are formed on Cu/HNaY, and the yield of the latter increases with an increase in the degree of acidity (degree of decationization) of the zeolite. It is possible to increase the selectivity of dioxene formation substantially with the use of a catalyst with a moderately acidic zeolite, by varying its copper content and by dilution with water vapor. 1996 Plenum Publishing Corporation.
Gitis,Neumoeva,Isagulyants
p. 23 - 29
(1996)
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Stone,Emeleus
p. 2755,2757
(1950)
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Tratremouille et al.
p. 120,124
(1960)
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Catalysis, kinetic and mechanistical studies for the transformation of ethylene glycol by alumina and silica gel under autogenous pressure and solvent-free conditions
A kinetic and mechanistical studies of the new pathway for competitive transformation of ethylene glycol by alumina and silica gel have been described. Commercial alumina (Al com), synthetic alumina (Al syn), commercial silica gel (Si com) and synthetic silica gel (Si syn) were used for the transformation of ethylene glycol to a mixture of diethylene glycol, 1,4-dioxane and 2-methyl-1,3-dioxolane via acetaldehyde by heating at 150 °C under autogenous pressure without solvent. The results show that the yield of these three products strongly depends on the nature of the used catalyst and the reaction time.
Rohand, Taoufik,Tanemura, Kiyoshi
p. 387 - 394
(2021/06/25)

Iron-Catalyzed Ring-Closing C?O/C?O Metathesis of Aliphatic Ethers
Among all metathesis reactions known to date in organic chemistry, the metathesis of multiple bonds such as alkenes and alkynes has evolved into one of the most powerful methods to construct molecular complexity. In contrast, metathesis reactions involving single bonds are scarce and far less developed, particularly in the context of synthetically valuable ring-closing reactions. Herein, we report an iron-catalyzed ring-closing metathesis of aliphatic ethers for the synthesis of substituted tetrahydropyrans and tetrahydrofurans, as well as morpholines and polycyclic ethers. This transformation is enabled by a simple iron catalyst and likely proceeds via cyclic oxonium intermediates.
Biberger, Tobias,Makai, Szabolcs,Lian, Zhong,Morandi, Bill
supporting information
p. 6940 - 6944
(2018/05/14)

Synthesis of dioxolanes and oxazolidines by silica gel catalysis
Abstract: Ethylene glycol condensed with carbonyl compounds in the presence of silica gel or alumina, without solvent and under pressure, affords 1,3-dioxolanes. 2-Amino-2-methylpropanol also condensed with carbonyl compounds in the presence of silica gel or an acid-activated clay, without solvent and under pressure, produces oxazolidines. To explain these results, we propose that the glycol and the aminopropanol react with Br?nsted (H+) and Lewis acid sites (Si and Al) located on the surface of the catalysts, leading to the products via various ionic intermediates.
Rohand, Taoufik,Savary, Jér?me,Markó, István E.
p. 1429 - 1436
(2018/06/25)

Transition metal triflate catalyzed conversion of alcohols, ethers and esters to olefins
Herein, we report an efficient transition metal triflate catalyzed approach to convert biomass-based compounds, such as monoterpene alcohols, sugar alcohols, octyl acetate and tea tree oil, to their corresponding olefins in high yields. The reaction proceeds through C-O bond cleavage under solvent-free conditions, where the catalytic activity is determined by the oxophilicity and the Lewis acidity of the metal catalyst. In addition, we demonstrate how the oxygen containing functionality affects the formation of the olefins. Furthermore, the robustness of the used metal triflate catalysts, Fe(OTf)3 and Hf(OTf)4, is highlighted by their ability to convert an over 2400-fold excess of 2-octanol to octenes in high isolated yields.
Keskiv?li,Parviainen,Lagerblom,Repo
p. 15111 - 15118
(2018/05/04)

Thermal and hydrolytic decomposition mechanisms of organosilicon electrolytes with enhanced thermal stability for lithium-ion batteries
The high flammability and thermal instability of conventional carbonate electrolytes limit the safety and performance of lithiumion batteries (LIBs) and other electrochemical energy storage devices. Organosilicon solvents have shown promise due to their reduced flammability and greater chemical stability at high temperatures. A series of organosilicon electrolytes with different functional substituents were studied to understand the structural origins of this enhanced stability. The thermal and hydrolytic stability of organosilicon and carbonate solvents with LiPF6 was probed by storage at high temperatures and with added water. Quantitative monitoring of organosilicon and carbonate electrolyte decomposition products over time using NMR spectroscopy revealed mechanisms of degradation and led to the discovery of a key PF5-complex that forms in organosilicon electrolytes to inhibit further salt breakdown. Increased knowledge of specific structural contributions to electrolyte stability informs the development of future electrolyte solvents to enable the safer operation of high-performing lithium-ion batteries.
Guillot, Sarah L.,Pe?a-Hueso, Adrian,Usrey, Monica L.,Hamers, Robert J.
p. A1907 - A1917
(2018/02/28)

METHOD FOR PREPARING DOUBLE-SEALED-END GLYCOL ETHER
Disclosed is a method for preparing a double end capped glycol ether, the method comprising: introducing into a reactor a raw material comprising a glycol monoether and a monohydric alcohol ether, and enabling the raw material to contact and react with an acidic molecular sieve catalyst to generate a double end capped glycol ether, a reaction temperature being 50-300° C., a reaction pressure being 0.1-15 MPa, a WHSV of the glycol monoether in the raw material being 0.01-15.0 h?1, and a mole ratio of the monohydric alcohol ether to the glycol monoether in the raw material being 1-100:1. The method of the present invention enables a long single-pass lifespan of the catalyst and repeated regeneration, has a high yield and selectivity of a target product, low energy consumption during separation of the product, a high economic value of a by-product, and is flexible in production scale and application.
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Paragraph 0042; 0044; 0046

(2017/12/27)

Selective synthesis of dimethoxyethane via directly catalytic etherification of crude ethylene glycol
Etherification of ethylene glycol with methanol provides a sustainable route for the production of widely used dimethoxyethane; dimethoxyethane is a green solvent and reagent that is applied in batteries and used as a potential diesel fuel additive. SAPO-34 zeolite was found to be an efficient and highly selective catalyst for this etherification via a continuous flow experiment. It achieved up to 79.4% selectivity for dimethoxyethane with around 96.7% of conversion. The relationship of the catalyst's structure and the dimethoxyethane selectivity was established via control experiments. The results indicated that the pore structure of SAPO-34 effectively limited the formation of 1,4-dioxane from activated ethylene glycol, enhanced the reaction of the activated methanol with ethylene glycol in priority, and thus resulted in high selectivity for the desired products. The continuous flow technology used in the study could efficiently promote the complete etherification of EG with methanol to maintain high selectivity for dimethoxyethane.
Yu, Weiqiang,Lu, Fang,Huang, Qianqian,Lu, Rui,Chen, Shuai,Xu, Jie
supporting information
p. 3327 - 3333
(2017/07/28)

Manufacturing method and composition of alkylene ether of bisphenol compd. dioxyethylene
PROBLEM TO BE SOLVED: To provide a method for efficiently producing a dioxyalkylene ether of a bisphenol compound containing little amount of by-products and having high purity in industrialization in the method for producing a dioxyalkylene ether of a bisphenol compound from a bisphenol compound.SOLUTION: The method for producing a dioxyalkylene ether (B) of a bisphenol compound (A) by adding a 2-4C alkylene oxide to a bisphenol compound includes a step (I) of carrying out the reaction in the presence of a catalyst (C) in a mixed solvent (S) of water and the following solvent (S1) at a reaction temperature of 30-80°C. The solvent (S1): a solvent capable of dissolving ≥1 g of the dioxyalkylene ether (B) of the bisphenol compound in 100 g of the solvent.
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Paragraph 0025

(2017/05/12)

Production of aldehydes from 1,2-alkanediols over silica-supported WO3 catalyst
Vapor-phase dehydration of several 1,2-alkanediols, such as 1,2-ethanediol, 1,2-propanediol, 1,2-butanediol and 1,2-pentanediol, to produce corresponding aldehydes was investigated over silica-supported WO3 catalyst, which was prepared by impregnation method and then calcined at 320?°C. Higher than 90% yield of aldehydes could be achieved over WO3/SiO2 catalyst at 250?°C with a feed of 20% aqueous 1,2-alkanediol solution. Both Br?nsted and Lewis acid sites exist on WO3/SiO2 catalyst, while Br?nsted acid sites are proposed to be the active species for the formation of aldehyde. High concentrations of H2O were effective for inhibiting the intermolecular reaction and improving the selectivity to aldehydes. The dehydration of different 1,2-alkanediols was compared under different reaction conditions. The reactivity of 1,2-ethanediol was low and the product distribution was several comparing with those of the other 1,2-alkanediols. Cyclic acetal, which was generated by the cyclodehydration of the produced aldehyde with another 1,2-alkanediol, was a main by-product, and the formation of acetal was affected by both the temperature and the carbon-chain length of the 1,2-alkanediols.
Sun, Daolai,Yamada, Yasuhiro,Sato, Satoshi,Suganuma, Satoshi,Katada, Naonobu
p. 164 - 171
(2016/09/09)

A 1, 3-dioxolane preparing 1, 4-dioxane method
The invention provides a method used for preparing 1,4-dioxane from 1,3-dioxolane. According to the method, raw material gas containing 1,3-dioxolane and carrier gas is delivered into a reactor filled with a solid acid catalyst, and reaction is carried out at a reaction temperature of 120 to 160 DEG C, under a reaction pressure of 0.1 to 2.0MPa, and with gaseous hourly space velocity of 500 to 4500/h so as to obtain 1,4-dioxane, wherein partial pressure ratio of the carrier gas to 1,3-dioxolane in the raw material gas ranges from 1.0 to 50. The method is capable of realizing production of 1,4-dioxane under gas-solid reaction conditions; reaction conditions are mild; and separation of products from the catalyst is simple.
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Paragraph 0018

(2016/10/08)

Method for preparing 1, 4-dioxane
The invention provides a method for preparing anhydrous high-purity 1, 4-dioxane from glycol dimethyl ether through one step. Through the method, high-purity 1, 4-dioxane is prepared from the glycol dimethyl ether raw material at a low temperature at a high conversion rate. In the whole reaction process, water does not react and product water is not produced so that 1, 4-dioxane-containing industrial wastewater is prevented thoroughly. The glycol dimethyl ether raw material has a high conversion ratio at a low temperature, catalyst stability is good, product 1, 4-dioxane selectivity is high and the whole process is simple and environmentally friendly.
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Paragraph 0055; 0056; 0057; 0058; 0059

(2016/12/26)

Cyclodehydration of diethylene glycol over Ag-modified Al2O3 catalyst
Vapor-phase cyclodehydration of diethylene glycol (DEG) into 1,4-dioxane (DOX) were performed over several solid acid catalysts, such as Al2O3, SiO2-Al2O3, Beta and MFI zeolites. All the catalytic activity gradually decreased with time on stream, especially Beta and MFI zeolites with strong acidic property. The catalysts were modified with silver metal for stabilizing the catalytic activity: Al2O3 modified with 1 wt.% Ag2O showed the best catalytic performance. Characterizations such as XRD, TPD and FTIR were performed for analyzing the carbonaceous compound deposited on the catalysts after reaction and investigating the effect of the addition of Ag2O onto Al2O3. Polyethylene glycol was proposed as the carbonaceous compound by FTIR analysis. The modification of Ag was found to decrease the averaged acid strength of Al2O3, which is supposed to be effective for inhibiting carbon deposition and stabilizing the catalytic activity. It was also found that H2, as a carrier gas, was indispensable for stabilizing the conversion of DEG into DOX. Silver metal would work as a remover of the product on the catalyst surface together with H2 to prevent carbon deposition. Over Al2O3 modified with 1 wt.% Ag2O, a stable DOX selectivity of 90% with a complete conversion was achieved at 250 °C and a contact time of 156.8 g h mol-1.
Sun, Daolai,Wang, Junjie,Yamada, Yasuhiro,Sato, Satoshi
p. 422 - 430
(2015/10/28)

Phosphorescent OLED and hole transporting materials for phosphorescent OLEDs
The present invention relates to phosphorescent organic light-emitting diodes (OLEDs) comprising a hole-transporting or a hole-transporting and an electron-blocking layer comprising an N,N,N',N'-tetraaryl-phenylene-3,5-diamine or an N,N,N',N'-tetraaryl-1,1'-biphenyl-3,3'-diamine matrix compound and to new N,N,N',N'-tetraarylsubstituted m-arylene diamine compounds useful as hole-transporting and electron-blocking layer matrices in phosphorescent OLEDs.
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(2014/05/07)

Selective catalytic synthesis of unsymmetrical ethers from the dehydrative etherification of two different alcohols
The cationic ruthenium-hydride complex [(C6H6)(PCy3)(CO)RuH]+BF4- catalyzes selective etherification of two different alcohols to form unsymmetrically substituted ethers. The catalytic method exhibits a broad substrate scope while tolerating a range of heteroatom functional groups in forming unsymmetrical ethers, and it is successfully used to directly synthesize a number of highly functionalized chiral nonracemic ethers.
Kim, Junghwa,Lee, Dong-Hwan,Kalutharage, Nishantha,Yi, Chae S.
p. 3881 - 3885
(2015/01/16)

Waste-free technology for N-methylmorpholine synthesis
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Markosyan,Baghdasaryan,Hovhannisyan,Attaryan,Hasratyan
p. 845 - 847
(2014/02/14)

Activation reactions of 1,1-dialkoxoalkanes and unsaturated O-donors by titanium tetrafluoride
The reactivity of TiF4 with a variety of non cyclic 1,1-dialkoxoalkanes [CH2(OR)2, R = Me, Et, Me 2C(OMe)2, MeCH(OEt)2, ClCH2CH(OEt) 2, CH(OMe)3, PhCCCH(OEt)2], 1,3-dioxolane, N2CHCO2Et and 1,2-epoxybutane has been investigated. Activation, including fragmentation and/or rearrangement of the organic moiety, has been observed at room temperature in some cases; it generally occurs unselectively via C-O bond fission and the formation of new C-O, C-H and C-C bonds. Small differences in the structure of the organic substrate may determine significant differences in the reactivity with TiF4.
Marchetti, Fabio,Pampaloni, Guido,Biancalana, Lorenzo
experimental part
p. 135 - 139
(2012/05/20)

Synthesis, characterization and molecular structures of barium(II) trichloroacetate DME/1,4-dioxane compounds
Two new barium(II) trichloroacetate compounds, [Ba(H2O)(DME) (μ-O2CCCl3)2]n (1) and [{Ba(H2O)2(diox)0.5(μ-O2CCCl 3)2}(diox)]n (2) were synthesized and characterized by elemental analyses, physiochemical studies, FT-IR, 1H NMR, thermogravimetric analyses (TG/DTG/DSC) and single crystal X-ray studies. The reaction of hydrated barium(II) trichloroacetate monohydrate with excess DME (1,2-dimethoxyethane) and diox (1,4-dioxane) in methanol at room temperature led to the isolation of the novel compounds 1 and 2, respectively. Bridging trichloroacetate groups are anticipated on the basis of FT-IR studies and this was confirmed by the X-ray studies. Both compounds dissociate to produce ions in water, as shown by molar conductance values. 1H NMR spectroscopy confirms that DME and 1,4-dioxane are coordinated to the metal ion in these compounds. Single crystal X-ray diffraction studies reveal that the barium cation is coordinated to nine O atoms in a deformed coordination polyhedron in both compounds. Structural data of barium(II) trichloroacetates compounds have been obtained for the first time in the present investigation.
Singh, Sukhjinder,Saini, Deepika,Mehta,Kaur, Ravneet,Ferretti, Valeria
scheme or table
p. 202 - 209
(2012/03/10)

FUSED POLYCYCLIC COMPOUND AND ORGANIC LIGHT-EMITTING DEVICE USING THE COMPOUND
Provided are a fused polycyclic compound suitable for use mainly as a component for a blue-light-emitting device, and an organic light-emitting device using the compound. The fused polycyclic compound is represented by the general formulae (1), (2), (8) and (9).
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(2012/12/14)

The pentamethylcyclopentadienylsilicon(II) cation as a catalyst for the specific degradation of oligo(ethyleneglycol) diethers
Catalytic open sandwiches: Oligo(ethyleneglycol) diethers RO(CH 2CH2O)nR are degraded by the unusual catalyst Cp Si+ (see scheme). The open coordination sphere at silicon allows up to four Si-O contacts; crystal structure data of the reactive compounds [Cp Si(dme)]+BR4- and [Cp Si([12]crown-4)] +BR4- (R=C6F5) show weakly bound ether molecules. Copyright
Leszczynska, Kinga,Mix, Andreas,Berger, Raphael J. F.,Rummel, Britta,Neumann, Beate,Stammler, Hans-Georg,Jutzi, Peter
supporting information; experimental part
p. 6843 - 6846
(2011/09/19)

Further insights into the chemistry of niobium and tantalum pentahalides with 1,2-dialkoxyalkanes: Synthesis of bromo- and iodoalkoxides, spectroscopic and computational studies
The room temperature reactions of a series of 1,2-dialkoxyalkanes ROCH 2CH(R′)OR′′ with MX5 (M = Nb, Ta; X = Br, I) in 1:1 ratio result in single C-O bond cleavage and high-yield formation of the halo-alkoxides MBr4[κ2-OCH 2CH(R′)OR′′] or [NbI4{κ 1-OCH2CH(R′)OR′′}]2, and equimolar amounts of the corresponding alkyl halides RX. The reaction of NbBr5 with 1,2-dimethoxyethane, dme, proceeds with preliminary formation of the ionic species [NbBr4(κ2-dme) (κ1-dme)][NbBr6], 3b, which has been identified by solution NMR at low temperature and conductivity analyses. The gas-phase structure of 3b has been optimized by DFT calculations, confirming that the dme ligands adopt bidentate and monodentate coordination, respectively. Although the formation of NbOBr3(dme), 4b, 1,4-dioxane and MeBr from NbBr 5/dme (ratio 1:2) is an exoergonic process (calculated ΔGr° = -115.96 kcal mol-1), it is inhibited at room temperature. High temperature conditions enhance the production of 1,4-dioxane at the expense of selectivity. The dinuclear species NbOBr3(dme)NbBr5 (Nb-O-Nb), 5b, (X-ray) has been isolated in modest yield as byproduct of the room temperature reaction of NbBr5 with dme. In general, the 1:2 molar reactions of NbX5 (X = Br, I) with ROCH2CH(R′) OR′′ occur with the exclusion of nearly one equivalent of organic reactant.
Bini, Riccardo,Marchetti, Fabio,Pampaloni, Guido,Zacchini, Stefano
experimental part
p. 1412 - 1419
(2011/06/22)

PROCESS FOR THE PRODUCTION OF ETHYLENE GLYCOL
The present invention provides a process for the production of monoethylene glycol, said process comprising the steps of: (a) reacting ethylene oxide with a ketone in the presence of a solid acidic catalyst to form a ketal; and (b) hydrolysing the ketal with water to form monoethylene glycol, wherein the ketone contains in the range of from 4 to 20 carbon atoms.
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Page/Page column 10-12; 5/7; 7/7

(2011/02/24)

From 1,2-dialkoxyalkanes to 1,4-dioxanes. A transformation mediated by NbCl5via multiple C-O bond cleavage at room temperature
The formation of 1,4-dioxanes and alkyl chlorides from the reactions of polyethers (dme, diglyme, 1,2-diethoxyethane, 1,2-dimethoxypropane) with NbCl5 at room temperature is described; as far as dme is concerned, the reaction mainly occurs in two steps, consisting of (i) cleavage of one O-CH3 bond, followed by (ii) cleavage of the second O-CH3 bond and one of the two O-CH2 linkages. The characterization of intermediate complexes and the isolation of NbOCl3(dme) are reported. The Royal Society of Chemistry.
Marchetti, Fabio,Pampaloni, Guido,Zacchini, Stefano
body text
p. 3651 - 3653
(2009/02/05)

Synthesis of hydroxylated hydrocarbons
Ethylene glycol, other diols, triols, and polyols are made in an efficient manner by reacting dibromides with water in the presence of a metal oxide. An integrated process of dibromide formation, alcohol synthesis, metal oxide regeneration, and bromine recycling is also provided.
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(2008/06/13)

PREPARATION OF AN ALKOXYLATE COMPOSITION
Use of a double metal cyanide complex catalyst for reducing the level of free active hydrogen containing organic compound and/or 1,4-dioxane in an alkoxylate composition prepared by the reaction of a starting alcohol with an alkylene oxide.
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(2008/06/13)

Direct synthesis of di-heteroatom containing cyclic organic compounds
The present invention provides for the simplified, direct synthesis of di-heteroatom containing cyclic organic compounds by forming an aqueous mixture of material of the formula 1 wherein X and Y are heteroatoms which may be the same or different and X is selected from the group consisting of O, S and N, and both Y's are the same and are selected from the group consisting of O, S and N, and R1 through R8 are the same or different and are selected from the group consisting of H, C1 to C10 alkyl radicals, C1 to C10 aryl radicals, C1 to C10 alkyl aryl radicals, and z is zero when X and Y are O or S, and z is 1 when X and Y are N, and water at a mole ratio of water to material of formula I in the range of about 10:1 to about 0.001:1 and heating the mixture to a temperature in the range of about 250° C. to about 350° C. under autogeneous pressure for a time of from about 0.5 to 10 hours. Trace amounts of liquid, solid or gaseous acid can be present to further accelerate dehydration, dehydrosulfurization or deamination and cyclization.
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(2008/06/13)

METHOD OF PRODUCING GLYCOL ETHERS
The present invention provides a method of producing glycol ethers, which are also commonly known as glymes. The method according to the invention includes contacting a glycol with a monohydric alcohol in the presence of a polyperfluorosulfonic acid resin catalyst under conditions effective to produce the glyme. The method of the invention can be used to produce, for example, monoglyme, ethyl glyme, diglyme, ethyl diglyme, triglyme, butyl diglyme, tetraglyme, and their respective corresponding monoalkyl ethers. The present invention also provides a method of producing 1,4-dioxane from mono- or diethylene glycol and tetrahydrofuran from 1,4-butanediol.
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(2008/06/13)

Continuous chemoselective methylation of functionalized amines and diols with supercritical methanol over solid acid and acid-base bifunctional catalysts
The selective N-methylation of bifunctionalized amines with supercritical methanol (scCH3OH) promoted by the conventional solid acids (H-mordenite, β-zeolite, amorphous silica-alumina) and acid-base bifunctional catalysts (Cs-P-Si mixed oxide and γ-alumina) was investigated in a continuous-flow, fixed-bed reactor. The use of scCH 3OH in the reaction of 2-aminoethanol with methanol (amine/CH 3OH = 1/10.8) over the solid catalysts led to a significant improvement in the chemoselectivity of the N-methylation. Among the catalysts examined, the Cs-P-Si mixed oxide provided the most efficient catalyst performance in terms of selectivity and reactivity at 300 °C and 8.2 MPa; the N-methylation selectivity in the products reaching up to 94% at 86% conversion. The present selective methylation was successfully applied to the synthesis of N-methylated amino alcohols and diamines as well as O-methylated ethylene glycol. Noticeably, ethoxyethylamine was less reactive, suggesting that the hydroxy group of the amino alcohols is a crucial structural factor in determining high reactivity and selectivity, possibly because of the tethering effect of another terminus, a hydroxo group, to the catalyst surface. The magic-angle-spinning NMR spectroscopy and X-ray diffraction analysis of the Cs-P-Si mixed oxide catalyst revealed that the acidic and basic sites originate from P2O5/SiO2 and Cs/SiO2, respectively, and the weak acid-base paired sites are attributed to three kinds of cesium phosphates on SiO2. The weak acid-base sites on the catalyst surface might be responsible for the selective dehydrative methylation.
Oku, Tomoharu,Arita, Yoshitaka,Tsuneki, Hideaki,Ikariya, Takao
p. 7368 - 7377
(2007/10/03)

PROCESS FOR PRODUCING 3-AMINO-2-HYDROXYPROPIONIC ACID DERIVATIVES
The present invention provides a process for preparing 3-amino-2-hydroxypropionic acid derivatives (1) which does not use dangerous reagents, is economically advantageous, and is suitable for an industrial production, which process comprises:treating N-protected-3-amino-2-hydroxypropionic acid derivatives (2) having a steric configuration at 2-position carbon reverse to that of derivatives (1) with a leaving group-introducing agent to convert into N-protected-3-aminopropionic acid derivatives (3),then treating the derivatives with a basic substance to convert into substituted-3-amino-2-hydroxypropionic acid derivatives (4) having an inverted steric configuration at 2-position carbon,and then converting the derivatives into 3-amino-2-hydroxypropionic acid derivatives (1).
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(2008/06/13)

Generation of alkyl hypochlorites in oxidation of alcohols with carbon tetrachloride catalyzed by vanadium and manganese compounds
Primary alcohols and diols with various structures were subjected to transformations into esters, aldehydes, ketones, and lactones under the action of carbon tetrachloride in the presence of manganese compounds (MnCl 2, MnO2, Mn(OAc)2, Mn(acac)3) and vanadium compounds (VCl5, V2O5, VO(acac) 2) as catalysts. These transformation proceeded with the involvement of alkyl hypochlorites, which were generated in the course of oxidation of alcohols with carbon tetrachloride catalyzed by manganese or vanadium compounds. The optimum molar ratios between the catalyst and reagents were determined, and the reaction conditions for the highly selective synthesis of esters, aldehydes, ketones, and lactones from alcohols were found.
Khusnutdinov,Shchadneva,Baiguzina,Lavrentieva,Dzhemilev
p. 2074 - 2079
(2007/10/03)

Heteroaryl- phenyl heterobicyclic factor Xa inhibitors
The present application describes heteroaryl-phenyl heterobicycles and derivatives thereof, or pharmaceutically acceptable salt forms thereof, which are useful as inhibitors of factor Xa.
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(2008/06/13)

Nucleoside analogues
Nucleoside analogues containing the degenerate base analogue P and derivatives thereof are provided with reporter moieties preferably comprising signal moieties. The nucleoside analogues are useful for labeling DNA or RNA or for incorporating in oligonucleotides.
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(2008/06/13)

Phenethylamine derivatives
The present invention has as its object providing phenethylamine derivatives that typically function as a motilin receptor antagonist and which are useful as medicines. The invention provides compounds represented by the general formula (1): (wherein A is typically an amino acid residue, R1is typically R6—CO—, R2is typically a hydrogen atom, R3is typically —CO—R7, R4is typically an alkyl group, R5is typically a hydroxyl group, R6is typically an alkyl group, and R7is typically an amino group).
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(2008/06/13)

1,2,3-TRIAZOLO[4,5-D]PYRIMIDINES AS P2T RECEPTOR ANTAGONISTS
Compounds of formula having the following stereochemistrywherein R, R1, R2, R3 and R4 are as defined in the specification. The compounds are useful as P2T receptor antagonists
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(2008/06/13)

Cyclodehydration of some 1,n-diols catalysed by sulfated zirconia
Sulfated zirconia, a solid acid is found to be a good catalyst in the cyclodehydration of several diols.
Wali, Anil,Pillai, S. Muthukumaru
p. 326 - 327
(2007/10/03)

Process for nitrosation of C-H-acidic compounds
A process for nitrosating C-H-acidic compounds. The process substantially avoids producing polluted wastewater.
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(2008/06/13)

Fucose derivatives, drugs containing the same as active ingredient, and intermediates for producing the same
A compound of the formula (I): STR1 wherein X1 is a group of one of the following formulae (1), (2) and (3): STR2 R1 is a branched long chain alkyl group, R2 is --CONHR3, a carboxyl group or a hydrogen atom, n is an integer of 0, 1 or 2, and R3 is a lower alkyl group or a phenyl group, or a pharmaceutically acceptable salt thereof, which is useful as a selectin inhibitor, and can be used in the prophylaxis or treatment of various inflammatory diseases such as inflammatory dermatitis (e.g., atopic dermatitis, contact hypersensitivity, photodermatosis, etc.), autoimmune chronic diseases (e.g. rheumatoid arthritis, chronic thyroiditis, etc.), and ischemia-reperfusion injury.
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(2008/06/13)

Heterocyclic compounds for the treatment of CNS and cardiovascular disorders
Novel aromatic bicyclic amines of formula (I) STR1 are useful in treating central nervous system disorders and cardiac arrhythmias and cardiac fibrillation.
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(2008/06/13)

Antipicornaviral compounds and methods for their use and preparation
Picornaviral 3C protease inhibitors, obtainable by chemical synthesis, inhibit or block the biological activity of picornaviral 3C proteases. These compounds, as well as pharmaceutical compositions that contain these compounds, are suitable for treating patients or hosts infected with one or more picornaviruses. Several novel methods and intermediates can be used to prepare the novel picornaviral 3C protease inhibitors of the present invention.
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(2008/06/13)

The continuous acid-catalyzed dehydration of alcohols in supercritical fluids: A new approach to the cleaner synthesis of acetals, ketals, and ethers with high selectivity
We report a new continuous method for forming ethers, acetals and ketals using solid acid catalysts, DELOXAN ASP or AMBERLYST 15, and supercritical fluid solvents. In the case of ether formation, we observe a high selectivity for linear alkyl ethers with little rearrangement to give branched ethers. Such rearrangement is common in conventional syntheses. Our approach is effective for a range of n-alcohols up to n-octanol and also for the secondary alcohol 2-propanol. In the reaction of phenol with an alkylating agent, the continuous reaction can be tuned to give preferential O- or C- alkylation with up to 49% O-alkylation with supercritical propene. We also investigate the synthesis of a range of cyclic ethers and show an improved method for the synthesis of THF from 1,4-butandiol under very mild conditions.
Gray, William K.,Smail, Fiona R.,Hitzler, Martin G.,Ross, Stephen K.,Poliakoff, Martyn
p. 10711 - 10718
(2007/10/03)

6-Carboxamido dihydropyran derivatives
Compounds of formula (I), STR1 wherein R1 represents OR5, SR5, NR5 R6, N(OR5)R6 or N(NR5 R6)R6 ; X represents OH, N3, NR3 R4 or NR4 CO2 R15 ; Y represents H or NHR2 ; R2 represents a group SO2 R7 or COR7 ; R3 represents H, C1-6 alkyl or C(=NR8)NR9 R10 ; R4 represents H or C1-6 alkyl; R5 represents H, C1-20 alkyl, C3-8 cycloalkyl, C2-20 alkenyl, C2-20 alkynyl, CHR11 COR12 or C1-20 alkyl substituted by one or more groups selected from NR13 R14, NR13 COR14, CO2 R13, OR13, C3-8 cycloalkyl and optionally substituted aryl; each R6 independently represents H, C1-6 alkyl, C3-8 cycloalkyl, C2-6 alkenyl, C2-20 alkynyl, aryl or C1-4 alkyl substituted by one or more groups selected from NR13 R14, COR13, C3-8 cycloalkyl, CN, N3, OR13 and optionally substituted aryl; or R5 and R6 together form a C2-6 hydrocarbon chain which may optionally contain a group NR13 which chain is optionally substituted by 1, 2, 3 or 4 groups selected from oxo and C1-6 alkyl groups which groups may optionally be substituted by hydroxy or optionally substituted aryl; R7 represents C1-6 alkyl optionally substituted by one or more halogen atoms, C3-8 cycloalkyl or optionally substituted aryl; R8, R9 and R10 each independently represent H, C1-6 alkyl, amino, hydroxy, cyano or nitro; R11 represents the side chain of a D- or L-amino acid; R12 represents NR13 R14, OR13 or R13 ; each R13 and each R14 independently represents H, C1-6 alkyl or optionally substituted arylC1-4 alkyl; R15 represents C1-6 alkyl; and their pharmaceutically acceptable derivatives are neuraminidase inhibitors useful in the treatment of viral infections.
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(2008/06/13)

Synthesis of alkyl-substituted 1,3-dioxolanes by catalytic dehydration of 1,2-glycols
The kinetics of the acid-catalyzed reactions of dehydration of ethylene glycol and 1,2-propylene glycol to respectively acetaldehyde and propionic aldehyde and of condensation of the aldehydes with the glycols were studied. The dependences of the apparent rate constants on temperature and catalyst concentration were determined. A mathematical model of the reactions studied was proposed.
Balashov,Danov,Chernov,Kvashennikov
p. 1418 - 1420
(2007/10/03)

Thermolysis of the benzene anion radical 18-crown-6 complex
The C-O and G-H bonds of 18-crown-6 are activated when 18-crown-6 is complexed with the potassium salt of the benzene anion radical. Evacuated glass bulbs containing the solid anion radical salt of potassium 18-crown-6 benzene anion radical were plunged into a bath at 320 C, resulting in mini-explosions and generating a series of compounds including dioxane, 2-methyl1,3-dioxolane, divinyl ether, hydrogen, methane, and 15-crown-5. Deuterium labeling studies proved that all of these compounds originated from the 18-crown-6. Further, these labeling studies were an aid in discerning the mechanism of the decomposition. Benzene, 1,4-cyclohexadiene, and cyclohexene were also generated. The last two originated from the reaction of the anion radical of benzene with hydrogen.
Stevenson, Cheryl D.,Morgan, Grant
p. 7694 - 7697
(2007/10/03)

Chiral phosphorus(III) triflates. On the nature of the phosphorus-oxygen interaction
Reaction of chiral phosphorodiamidites with trimethylsilyltriflate affords chiral phophorus(III) triflate species, such as 1-trifluoromethylsulfonato-2,9-(dibenzyl)diaza-1-phospha[4.0.3]bicyclononane 4, which has been examined by a combination of solution and solid state analytical techniques. Arguably the most important feature of this molecule is the nature of the interaction between phosphorus and triflate oxygen atoms. Single crystal X-ray diffraction analysis reveals that the phosphorus atom interacts principally with two oxygen atoms from two different triflate groups in the solid state, implying overall four-coordination at phosphorus. At distances of 2.841 and 2.755 A, these interactions are well within the van der Waals distance for a phosphorus-oxygen [P-O] interaction (ca. 3.35 A) but are nevertheless over 1 A longer than expected for a single [P-O] covalent bond. Investigations in solution via a combination of 31P, 19F, 13C, variable concentration, variable temperature NMR spectroscopy and solution conductivity provide support for a phosphorus-oxygen interaction which is intermediate between 'ionic' (two-coordinate phosphorus) and 'covalent' (three-coordinate phosphorus) and which possesses dynamic character in solution. Indeed, it has proved possible to calculate a relative equilibrium constant between 'ionic' and 'covalent' forms of 4 using empirical NMR data (13C and 19F; CH2Cl2 solvent; 300 K). These calculations return an equilibrium constant of ca. 3 (2.8 using 13C-NMR data and 3.3 using 19F-NMR data) in favour of the ionic form, a result commensurate with those suggested from variable temperature 19F-NMR and solution conductivity studies. Indeed, that the triflate group in 4 is capable of being displaced readily has been demonstrated by reaction with two-electron nitrogen, oxygen and phosphorus donor molecules. We have found 13C{1H}-NMR spectroscopy to be an extremely valuable probe of the ionic character of the triflate group in such systems providing a quantitative measure of the relative strength of interaction (relative basicity Br) between donor molecule and phosphorus atom of 4; the stronger the interaction, the more ionic the character of the triflate group and the lower the value of Br. Indeed, Br values for various ligands correlate well with steric and electronic properties of the latter and 31P-NMR resonances of the adducts themselves. As expected, the relative basicity of a given ligand correlates to the equilibrium constants K for adduct formation, which range from 39 M-1 for the weakest binding ligand studied (1,4-dioxane) to 5.4×104 M-1 for the strongest binding ligand (4-Me2N-NC5H4).
Jones, Victoria A.,Sriprang, Sarin,Thornton-Pett, Mark,Kee, Terence P.
p. 199 - 218
(2007/10/03)

Hydrogen bonding Part 44 1Thermodynamics of complexation of 3,5-dichlorophenol with ketones and ethers in cyclohexane: The badger-Bauer relationship
Equilibrium constants for 1 : 1 hydrogen bond complexation between 3,5-dichioropheno' (DCP) and 17 ketones and 12 ethers in cyclohexane solution have been obtained by an FTIR method that takes into account both diiaerization of the acid and formation of 2 :1 complexes. Enthalpies of complexation for the same ketones and ethers have been determined by a calorimeiric method, leading to values of log K, AG, AH and AS0 for 1 :1 complexation in the 29 systems, as well as log K2 for the 2 :1 complexation between 2 mol of acid and 1 mol of base. For the ketone systems there is very little variation in the three thermodynamic parameters with alkyl substitution, but for the ethers there are systematic variations depending on the alkyl substituent or if the ethers are cyclic. Values of the OH stretching frequency in the DCP complexes with the ketones and ethers in cyclohexane have been obtained. The band shapes for the DCP-ketone complexes are very asymmetric, possibly due to the presence of stereoisomeric complexes, but the VOH band for DCP-ether complexes is symmetric and very suitable for the evaluation of any relationship between v()H and A/f. It is found that for the complexation of DCP with the 12 aliphatic ethers in cyclohexane, there is almost no connection between the calorimetrically determined AH° values and values of AvOH.
Abraham, Michael H.,Prior, David V.,Schulz, Ronald A.,Morris, Jeffrey J.,Taylor, Peter J.
p. 879 - 885
(2007/10/03)

Substituted diether diols by ring-opening of carbocyclic and stannylene acetals
Reduction of malonaldehyde bis(ethylene and propylene acetals) with borane or monochloroborane produces diether diols 1 and 2 in high yield. Similar reduction of glyoxal his(ethylene acetals) has only limited utility for the preparation of tetrasubstituted triethylene glycols 3. Organotin chemistry is complementary: stannylene acetals prepared from disubstituted vicinal diols can be alkylated with half an equivalent of 1,2-dibromoethane to produce tetrasubstituted triethylene glycols 3, or with two equivalents of 2-chloroethanol to produce disubstituted triethylene glycols 4.
Martinez-Bernhardt, Rolando,Castro, Peter P.,Godjoian, Gayane,Gutierrez, Carlos G.
p. 8919 - 8932
(2007/10/03)

Oxazolidine dione derivatives
Compounds of the formula: STR1 or tautomeric forms and a pharmaceutically acceptable salt, and pharmaceutically acceptable solvates thereof, wherein: A1 is a substituted or unsubstituted oxazole substituted by up to 4 substituents selected from the group consisting of C1-6 -alkyl, C1-6 -alkoxy, phenyl, and halogen or any two substituents on adjacent carbon atoms, together with the carbon atoms to which they are attached, form a benzene ring, and wherein the carbon atoms of the benzene ring represented by the said two substituents are unsubstituted or substituted with up to three groups selected from halogen, C1-6 -alkyl, phenyl, C1-6 -alkoxy, halo-C1-6 -alkyl, hydroxy, amino, nitro, carboxy, C1-6 -alkoxycarbonyl, C1-6 -alkoxycarbonyl-C1-6 -alkyl, C1-6 -alkylcarbonyloxy, and C1-5 -alkylcarbonyl; Rl is a hydrogen atom, a C1-6 -alkyl group, a C1-6 -alkylcarbonyloxy group, a phenyl-C1-6 -alkyl group, wherein the phenyl moiety may be substituted or unsubstituted, or a substituted or unsubstituted phenyl group, wherein the said phenyl groups may be substituted with up to three groups selected from halogen, C1-6 -alkyl, phenyl, C1-6 -alkoxy, halo-C1-6 -alkyl, hydroxy, amino, nitro, carboxy, C1-6 -alkoxycarbonyl, C1-6 -alkoxycarbonyl-C1-6 -alkyl, C1-6 -alkylcarbonyloxy, and C1-6 -alkylcarbonyl; A2 is a benzene ring having in total up to five substituents wherein three optional substituents are selected from halogen, C1-6 -alkyl, phenyl, C1-6 -alkoxy, halo-C1-6 -alkyl, hydroxy, amino, nitro, carboxy, C1-6 -alkoxycarbonyl. C1-6 -alkoxycarbonyl-C1-6 -alkyl, C1-6 -alkylcarbonyloxy, and C1-6 -alkylcarbonyl; and n is an integer from 2 to 6, are disclosed as hypoglycemics, hypolipidemics and antihypertensives.
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(2008/06/13)

Acylsulfonamido- and sulfonamidopyridine-2-carboxylic acid esters and their pyridine N-oxides, processes for their preparation and their use as medicaments
The invention relates to acylsulfonamido- and sulfonamidopyridine-2-carboxylic acid esters and their pyridine N-oxides of the formula I STR1 in which ______________________________________A = R3 and B = X--NR5 R6 orB = R3 and A = X--NR5 R6.______________________________________ The compounds are suitable as medicaments against fibrotic diseases.
-
(2008/06/13)

Chemical Properties

Appearance/Colour :colourless liquid
Melting Point: 12 °C
Boiling Point: 102.9 °C at 760 mmHg
Flash Point:12.2 °C
Density: 0.995 g/cm³
Solubility:Soluble in acetone, alcohol, benzene, and ether (Weast, 1986). Miscible with most organic solvents (Huntress and Mulliken, 1941) including 2-methylpropanol, toluene, cychexanone, and cyclopentanone.
Storage Temp.:Flammables area
Vapor Density: 3 (vs air)
Vapor Pressure: 27 mm Hg ( 20 °C)
Refractive Index: n20/D 1.422(lit.)
Explosive Limit: 1.7-25.2%(V)
Sensitive: Hygroscopic
Merck: 14,3300
BRN: 102551
PSA: 18.46000
LogP: 0.03320

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123-91-1

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Chemical Properties

Appearance/Colour :colourless liquid

Melting Point: 12 °C

Boiling Point: 102.9 °C at 760 mmHg

Flash Point:12.2 °C

Density: 0.995 g/cm³

Solubility:Soluble in acetone, alcohol, benzene, and ether (Weast, 1986). Miscible with most organic solvents (Huntress and Mulliken, 1941) including 2-methylpropanol, toluene, cychexanone, and cyclopentanone.

Storage Temp.:Flammables area

Vapor Density: 3 (vs air)

Vapor Pressure: 27 mm Hg ( 20 °C)

Refractive Index: n20/D 1.422(lit.)

Explosive Limit: 1.7-25.2%(V)

Sensitive: Hygroscopic

Merck: 14,3300

BRN: 102551

PSA: 18.46000

LogP: 0.03320

Global suppliers and manufacturers of 123-91-1total 163 suppliers on LookChem

Article Database

123-91-1

Articles about 123-91-1Total 90 be found

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Chemical Properties

Appearance/Colour :colourless liquid

Melting Point: 12 °C

Boiling Point: 102.9 °C at 760 mmHg

Flash Point:12.2 °C

Density: 0.995 g/cm3

Solubility:Soluble in acetone, alcohol, benzene, and ether (Weast, 1986). Miscible with most organic solvents (Huntress and Mulliken, 1941) including 2-methylpropanol, toluene, cychexanone, and cyclopentanone.

Storage Temp.:Flammables area

Vapor Density: 3 (vs air)

Vapor Pressure: 27 mm Hg ( 20 °C)

Refractive Index: n20/D 1.422(lit.)

Explosive Limit: 1.7-25.2%(V)

Sensitive: Hygroscopic

Merck: 14,3300

BRN: 102551

PSA: 18.46000

LogP: 0.03320

Global suppliers and manufacturers of 123-91-1total 163 suppliers on LookChem

Density: 0.995 g/cm³