- Synthesis and surface activity study of novel branched zwitterionic heterogemini fluorosurfactants with CF3CF2CF2C(CF3)2 group
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In this work, we report a facile synthesis of four fluorinated zwitterionic heterogemini surfactants bearing branched CF3CF2CF2C(CF3)2- group with perfluoro-2-methyl-2-pentene as starting material. The surface activities of as-prepared four surfactants were found to be better than that of sodium perfluorooctanoate. Meanwhile, our fluorinated surfactants with double hydrophobic chains showed much better surface activities than the monomeric fluorinated surfactant. With the introduction of an alkyl chain, the CMC could be reduced more than 200 times to 6.30 × 10?5 mol/L, together with a surface tension of 18.66 mN/m. When a new fluorinated chain was introduced in the molecular structure, the CMC could be as low as 1.74 × 10?6 mol/L, along with a surface tension of 18.42 mN/m. When the alkyl chain length is 7, the surfactant has the same ability with the double fluorinated chain one to reduce the surface tension.
- Lin, Chao,Pan, Renming,Xing, Ping,Jiang, Biao
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- Physicochemical properties of tungstate-based room-temperature ionic liquids
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Tungstate-functionalized room-temperature ionic liquids (ILs), 1-alkyl-3-methylimidazolium tungstates [RMIm]2 [WO4] (R = C6H13 or C12H25), were synthesized and the IL's structure has been proved by NMR, Fourier transform IR, and elemental analysis. The physicochemical characteristics of the tungstate-based ILs have been determined by using methods of conductivity, viscosity, and cyclic voltammetry measurements, in comparison with those of the conventional ILs such as 1-hexyl-3-methylimidazolium methanesulfonate and 1-hexyl-3-methylimidazolium hexafluorophosphate. The influences of anions and the length of alkyl chain linked to the imidazolium ring on physicochemical properties of the ILs were examined in detail. All ILs owned higher conductivities and lower viscosities at higher temperatures. The strong intramolecular hydrogen bonds were found in the tungstate-based ILs. Cyclic voltammograms of the functionalized ILs illustrated that they were quite electrochemically stable. In general, the understanding of electrochemical properties of imidazolium ILs can facilitate their possible applications in electrochemistry.
- Qiao, Yunxiang,Hu, Jun,Li, Huan,Hua, Li,Hu, Yu,Feng, Bo,Hou, Zhenshan
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- Peroxopolyoxometalate-based room temperature ionic liquid as a self-separation catalyst for epoxidation of olefins
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A new peroxopolyoxometalate-based room temperature ionic liquid (POM-RTIL) has been synthesized and used as catalyst for efficient epoxidation of various olefins. The RTIL catalyst was found to be well dissolved in the solvent (ethyl acetate) during the reaction, while it can self-separate from the reaction media at room temperature after the reaction completed, which made the recovery and reuse of the IL catalyst convenient. The POM-RTIL catalyst can be recycled for five times without significant loss of activity.
- Li, Huan,Hou, Zhenshan,Qiao, Yunxiang,Feng, Bo,Hu, Yu,Wang, Xiangrui,Zhao, Xiuge
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- 1-Alkyl-3-methylimidazolium alkanesulfonate ionic liquids, [C nH2n+1mim][CkH 2k+1SO3]: Synthesis and physicochemical properties
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A set of 1-alkyl-3-methylimidazolium alkanesulfonate ionic liquids, [C nmim][CkSO3], formed by the variation of the alkyl chain lengths both in the cation and the anion (n = 1-6, 8, or 10; k = 1-4, or 6), was synthesised, with sixteen of them being novel. The ionic liquids were characterised by 1H and 13C NMR spectroscopy, and mass spectrometry. Their viscosities and densities as a function of temperature, as well as melting points and decomposition temperatures, were determined. The molecular volumes, both experimental and calculated, were found to depend linearly on the sum (n + k). the Owner Societies 2009.
- Blesic, Marijana,Swadzba-Kwasny, Malgorzata,Belhocine, Tayeb,Gunaratne, H. Q. Nimal,Lopes, Jose N. Canongia,Gomes, Margarida F. Costa,Padua, Agilio A. H.,Seddon, Kenneth R.,Rebelo, Luis Paulo N.
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- Efficient synthesis of organic thioacetates in water
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Thioacetates as precursors of thiols are interesting starting points for synthesizing other organosulfur compounds. Herein, we propose a simple, efficient and fast method to obtain organic thioacetates using water as a solvent. Taking into account the great attention that has been paid toward environmentally friendly synthetic procedures in the past decades, we prove the role and the strength of the thioacetate anion as a nucleophile for nucleophilic displacement reactions in an aqueous medium. The reactions were carried out under pH control, to prevent the decomposition of the mesylate starting materials, using potassium carbonate as a safe and mild base. A simple work up allows products to be obtained with excellent yield and acceptable purity.
- Olivito,Costanzo,Di Gioia,Nardi,Oliverio,Procopio
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- Enantiomeric synthesis of natural alkylglycerols and their antibacterial and antibiofilm activities
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Alkylglycerols (AKGs) are bioactive natural compounds that vary by alkyl chain length and degree of unsaturation, and their absolute configuration is 2S. Three AKGs (5l–5n) were synthesised in enantiomerically pure form, and were characterised for the first time together with 12 other known and naturally occurring AKGs (5a–5k, 5o). Their structures were established using 1H and 13C APT NMR with 2D-NMR, ESI-MS or HRESI-MS and optical rotation data, and they were tested for their antibacterial and antibiofilm activities. AKGs 5a–5m and 5o showed activity against five clinical isolates and P. aeruginosa ATCC 15442, with MIC values in the range of 15–125 μg/mL. In addition, at half of the MIC, most of the AKGs reduced S. aureus biofilm formation in the range of 23%–99% and P. aeruginosa ATCC 15442 biofilm formation in the range of 14%–64%. The antibiofilm activity of the AKGs assessed in this work had not previously been studied.
- Fernández Montoya, Deicy J.,Contreras Jordan, Luis A.,Moreno-Murillo, Bárbara,Silva-Gómez, Edelberto,Mayorga-Wandurraga, Humberto
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p. 2544 - 2550
(2019/11/13)
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- A preparing method of diethylamino hydroxybenzoyl hexylbenzoate
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The present invention relates to a method for the preparation of diethylamino hydroxybenzoyl hexyl benzoate. Specifically, the present invention relates to a method for preparing diethylamino hydroxybenzoyl hexyl benzoate which is easy to manufacture and commercially available in mass production, and diethylamino hydroxybenzoyl hexyl benzoate crystalline particles prepared thereby. According to the present invention, diethylamino hydroxybenzoyl hexyl benzoate crystalline particles having excellent UV blocking effect can be obtained in a stable and high yield.COPYRIGHT KIPO 2020
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Paragraph 0077-0079
(2020/03/28)
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- Multi-Gram Scale Synthesis of 1,2,3-Triazolium Ionic Liquids and Assay of Their Resistance towards Bases
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An easily upscalable synthesis method for 1,2,3-triazolium ionic liquids is presented. Several ionic liquids were synthesized and characterized. The influence of the side chain structure on the base-stability was investigated. One example, functionalized with linear alkyl side chains, was found to exhibit excellent stability against hot concentrated NaOH solutions and Grignard reagents.
- Raiguel, Stijn,Thomas, Joice,Binnemans, Koen,Dehaen, Wim
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supporting information
p. 4850 - 4856
(2018/09/06)
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- Hexyl triazabutadiene as a potent alkylating agent
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Alkyl diazonium ions are among the most reactive alkylating agents in the synthetic chemists’ arsenal. That said, there are precious few methods by which one can selectively and safely utilize this chemistry. Herein, we show the use of a bench stable hexyl triazabutadiene as a source of reactive diazonium ions that undergo substitution chemistry with weak nucleophiles, such as carboxylates and even sulfonates. In the absence of a nucleophile, elimination was observed to occur. To overcome issues stemming from side-product inhibition of the reaction, we show that the triazabutadiene can be pre-activated with tosyl isocyanate.
- Knyazeva, Diana C.,Kimani, Flora W.,Blanche, Jean-Laurent,Jewett, John C.
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supporting information
p. 2700 - 2702
(2017/06/23)
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- Molybdenum oxide-mediated facile aliphatic nucleophilic fluorination
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A facile aliphatic nucleophilic fluorination with cesium fluoride in the presence of molybdenum oxide as a catalyst has been demonstrated. Reactivity of molybdenum oxide in nanocrystal form was found to be chemoselective in the presence of water. Furthermore, the reaction is highly specific with alkyl sulfonate substrates.
- Said, Madhukar S.,Khandare, Lina,Shinde, Sandip S.
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supporting information
p. 59 - 62
(2016/12/23)
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- Polyoxometalate-based protic alkylimidazolium salts as reaction-induced phase-separation catalysts for olefin epoxidation
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Two protic alkylimidazolium polyoxometalates, together with two corresponding aprotic N-methyl-alkylimidazolium polyoxometalates were synthesized and characterized by the methods of NMR, IR and TGA etc. Then, these salts were employed as catalysts for the epoxidation of cyclooctene in different media. The novel protic N-dodecylimidazolium peroxotungstate [HDIm]2[{WO(O2)2}2(μ-O)] was found to be a room temperature liquid molten salt (ionic liquid) and the most effective catalyst for the epoxidation of cyclooctene among these salts. The ionic liquid catalyst [HDIm]2[{WO(O2)2} 2(μ-O)] can also be extended to the epoxidation of some other substrates. On the basis of this experimental observation, an efficient reaction-induced phase-separation catalyst system has been developed in this work. The reaction system can switch from tri-phase to emulsion and then to biphase and finally to all the catalyst self-precipitating at the end of the reaction, which made the recovery and reuse of the present catalyst very convenient.
- Qiao, Yunxiang,Hou, Zhenshan,Li, Huan,Hu, Yu,Feng, Bo,Wang, Xiangrui,Hua, Li,Huang, Qingfa
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experimental part
p. 1955 - 1960
(2010/06/15)
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- Bna Conjugates and Methods of Use
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Modified natriuretic compounds and conjugates thereof are disclosed in the present invention. In particular, conjugated forms of hBNP are provided that include at least one modifying moiety attached thereto. The modified natriuretic compound conjugates retain activity for stimulating cGMP production, binding to NPR-A receptor, decreasing arterial blood pressure and in some embodiments an improved half-life in circulation as compared to unmodified counterpart natriuretic compounds. Oral, parenteral, enteral, subcutaneous, pulmonary, and intravenous forms of the compounds and conjugates may be prepared as treatments and/or therapies for heart conditions particularly congestive heart failure. Modifying moieties comprising oligomeric structures having a variety of lengths and configurations are also disclosed. Analogs of the hBNP compound are also disclosed, having an amino acid sequence that is other than the native sequence.
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Page/Page column 32
(2008/12/08)
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- Process for preparation of oxyglutaric acid ester derivatives
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A process for preparing an oxyglutaric acid ester derivative of the formula: STR1 in which each of R1 and R2 is C1-5 alkoxy, C1-7 aralkyloxy, C7-9 halogenated aralkyloxy or phenyl, R4 is a hydroxyl-protecting group, and R5 is C1-10 alkyl which may have a substituent, comprises the steps of reacting a methyl phosphonate derivative or methyl phosphine oxide derivative with an oxyglutaric acid mono-ester to give a reaction product which comprises an oxyglutaric acid derivative having a phosphorus-containing group and a pentenedioic acid mono-ester (by-product), removing the pendenedioic acid mono-ester from the reaction product to isolate the oxyglutaric acid derivative, and converting the isolated oxyglutaric acid derivative into the oxyglutaric acid ester derivative. A process for obtaining an optically active oxyglutaric acid ester derivative is also disclosed.
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- Sulphonate Esters as Sources of Sulphonyl Radicals; Ring-closure Reactions of Alk-4- and -5-enesulphonyl Radicals
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Alkyl alkanesulphonates and arenesulphonates were found to be useful sources of sulphonyl radicals, particularly for spectroscopic work, when treated with organotin or organosilyl radicals.Allyl, propynyl and penta-2,4-dienyl methanesulphonates gave, however, allyl, propynyl and pentadienyl radicals, respectively.Sulphonyl radicals generated in this way added efficiently to alk-1-enes with electron-releasing substituents, and the EPR spectra of the adduct radicals were recorded.A variety of radical initiation systems were tried on pent-4-enesulphonyl chloride.The pent-4-enesulphonyl radical cyclised mainly in the endo mode to give the six-membered-ring sulphone.Similarly, the hex-5-enesulphonyl radical cyclised to give thiepane 1,1-dioxide, with a seven-membered ring.The cyclohex-2-enylethanesulphonyl radical cyclised mainly in the exo mode to give 2-chloro-9-thiabicyclononane 9,9-dioxide.The mechanisms of these reactions are discussed.
- Culshaw, Peter N.,Walton, John C.
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p. 1201 - 1208
(2007/10/02)
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- Benzophenone Dicarboxylic Acid Antagonists of Leukotriene B4. 2. Structure-Activity Relationships of the Lipophilic Side Chain
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A series of lipophilic benzophenone dicarboxylic acid derivatives were found to inhibit the binding of the potent chemotoxin leukotriene B4 (LTB4) to its receptor on intact human neutrophils.Activity at the LTB4 receptor was determined by using a 3H>LTB4-binding assay.The structure-activity relationship for the lipophilic side chain was systematically investigated.Compounds with n-alkyl side chains of varying lengths were prepared and tested.Best inhibition of 3H>LTB4 binding was observed with the n-decyl derivative.Analogues with alkyl chains terminated with an aromatic ring showed improved activity.The 6-phenylhexyl side chain was optimal.Substitution on the terminal aromatic ring was also evaluated.Methoxyl, methylsulfinyl, and methyl substituents greatly enhanced the activity of the compound.For a given substituent, the para isomer had the best activity.Thus the nature of the lipophilic side chain can greatly influence the ability of the compounds to inhibit the binding of LTB4 to its receptor on intact human neutrophils.The most active compound from this series, 84 (LY223982), bound to the LTB4 receptor with the affinity approaching that of the agonist.
- Gapinski, D. Mark,Mallett, Barbara E.,Froelich, Larry L.,Jackson, William T.
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p. 2807 - 2813
(2007/10/02)
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- GENERATION OF SULPHONYL RADICALS FROM SULPHONATE ESTERS
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Alkane alkylsulphonates and arylsulphonates are useful sources of sulphonyl radicals on treatment with organotin radicals.EPR spectra of the adduct radicals from CH3SO2* and alkenes containing donor substituents were observed.
- Culshaw, Peter N.,Walton, John C.
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p. 2457 - 2460
(2007/10/02)
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- Oxidatively Assisted Nucleophic Substitution of Iodine in Alkyl Iodides by Nucleofugic Anions
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The reaction of alkyl iodides with chlorine or nitronium tetrafluoroborate in the presence of salts of perchloric or substitued sulfonic acids gave alkyl perchlorates or sulfonates as principal products.Some mechanistic aspects of this new reaction are discussed.
- Zefirow, Nikolai S.,Zhdankin, Victor V.,Makhon'kova, Galina V.,Dan'kov, Yuri V.,Koz'min, Anatoly S.
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p. 1872 - 1876
(2007/10/02)
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- Diethoxytriphenylphosphorane: A Mild, Regioselective Cyclodehydrating Reagent for Conversion of Diols to Cyclic Ethers. Stereochemistry, Synthetic Utility, and Scope
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Diethoxytriphenylphosphorane, Ph3P(OEt)2, prepared by reaction of triphenylphosphine and diethyl peroxide, is a "hydrolytically active" dioxyphosphorane which promotes mild cyclodehydration (40-110 deg C) of diols to cyclic ethers in neutral media.The regioselectivity in the closure of (S)-(+)-propane-1,2-diol and (R)-(-)-pentane-1,4-diol with Ph3P(OEt)2 is high (81-82 percent) while the cyclodehydration of (S)-(+)-phenylethane-1,2-diol gives racemized (+/-)-styrene oxide.Simple 1,2-, 1,4-, and 1,5-diols afford good yields of the cyclic ethers but 1,3-propanediol and 1,6-hexanediol give mainly 3-ethoxy-1-propanol and 6-ethoxy-1-hexanol, respectively with Ph3P(OEt)2.Tri- and tetra-substituted 1,2-diols afford the relatively stable 1,3,2-dioxaphospholanes (or ?-dioxyphosphoranes) in the presence of Ph3P(OEt)2, and, depending on conditions, the 1,3,2-dioxaphospholanes are selectively converted to epoxides, ketones or allylic alcohols.The carbonyl compounds arise from 1,2-hydride and 1,2-methyl migrations; the allylic alcohols are derived from thermolytic eliminations. trans-1,2-Cyclohexanediols afford essentially quantitative yields (>95 percent) of the cyclohexene oxides while cis-1,2-cyclohexanediol gives the stable 1,3,2-dioxaphospholane with Ph3P(OEt)2 which decomposes under thermal conditions to cyclohexanone (90 percent).Ph3P(OEt)2 is extremely useful for conversion of "sensitive" 1,2-diols to acidic and /or thermally labile epoxides as demonstrated by the quantitative conversion of 9,10-dihydro-trans-9,10-phenanthrenediol to 9,10-dihydrophenanthrene oxide and 2α,10-pinanediol to 2α,10-epoxypinane.
- Robinson, Philip L.,Barry, Carey N.,Kelly, Jeffery W.,Evans, Slayton A.
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p. 5210 - 5219
(2007/10/02)
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