- SYNTHESE ET CARACTERISTIQUES SPECTRALES DE F-ALKYL-2-DIHYDRO-3,4 OXO-4 QUINAZOLINES
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In this paper we report the preparation of a series of 4(3H) quinazolinones substituted in the 2 position by a linear perfluoroalkyl-chain with RF as Cn F2n+1 (n=1,3,5,7).These compounds are obtained in two steps, action of F-acid chlorides on 2-aminobenzonitrile which affords the corresponding F-amides followed by cyclization of this intermediate with alkaline hydrogen peroxide.We isolated a reaction intermediate in the cyclization of N-(2-cyanophenyl)F-octanamide.All compounds were identified by the usual spectroscopic methods (IR, NMR 1H, 19F, mass spectrometry).
- Greiner, Jacques,Pastor, Raphael,Cambon, Aime
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- Synthesis and characterization of a novel fluorine-containing polymer emulsion with core/shell structure
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A novel fluorine-containing polymer emulsion 4 with core/shell structure was synthesized in water phase by a two-stage emulsion polymerization technique using monomer 3 (i.e., 2-methacryloyloxyethyl perfluorooctanoate (MAEF)) reacting with the monomers such as butyl acrylate (BA), acrylic acid (AA) and styrene (ST). The monomer 3 was synthesized from the intermediate 2 (pentadecafluoro-octanoyl chloride) reacting with β-hydroxyethyl methacrylate (HEMA). Polymer film were prepared by coating emulsion 4 directly on a cleaned glass plate and allowed to dry at room temperature. Moreover, the characteristics of polymer film such as hydrophobicity, chemical resistance, surface composition, thermal stability, emulsion particle morphology, as well as the film-forming property were also studied.
- Gao, Jinzhang,Wang, Xuemei,Wei, Yunxia,Yang, Wu
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- N-alkyl perfluoroalkanamides as low molecular-mass organogelators
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A new class of low molecular-mass organogelators (LMOGs), N-alkyl perfluoroalkanamides, F(CF2)nCONH(CH2) mH, is described. The molecules are designed to exploit the incompatibilities of their three molecular parts, and the results demonstrate that this strategy can be used to tune molecular aggregation and gel stability. The gelating properties of these LMOGs have been examined in a wide variety of organic liquids (including alkanes, alcohols, toluene, n-perfluorooctane, CCl4, and DMSO) as a function of the N-alkyl and perfluoroalkyl chain lengths by x-ray diffraction, polarizing optical microscopy, infrared spectroscopy, differential scanning calorimetry, and small-angle neutron scattering (SANS). The gels are thermally reversible and require generally very low concentrations (2)nCO2(CH2)mH) and diblock perfluoroalkylalkanes (F(CF2)n(CH 2)mH) indicate that additional ordering within the aggregate units is enforced by the intermolecular H bonding among amide groups that is evidenced by IR spectroscopy. Analyses of these results and structure/solvent correlations are provided.
- George, Mathew,Snyder, Samuel L.,Terech, Pierre,Glinka, Charles J.,Weiss, Richard G.
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- Perfluoropolyether ester derivative as well as preparation method and application thereof
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The invention discloses a perfluoropolyether ester derivative as well as a preparation method and application thereof. The preparation method of the perfluoropolyether ester derivative comprises the following steps: (1) performing acyl chlorination on pentafluorobenzoic acid to obtain pentafluorobenzoyl chloride; and (2) carrying out an esterification reaction on the pentafluorobenzoyl chloride and perfluoropolyether alcohol to obtain the perfluoropolyether ester derivative. In perfluoropolyether derivative molecules provided by the invention, a perfluoropolyether part provides compatibility with perfluoropolyether, and an ester group and a pentafluorophenyl part provide enhanced lubricity and bearing capacity; a large number of fluorine atoms contained in molecules can better generate friction chemical reaction with the metal surface, so that a film structure is easily formed on the surface of a friction pair, and the lubricating effect is promoted. The perfluoropolyether derivative also has good thermal stability and can still keep a certain lubricating effect at 150 DEG C. The perfluoropolyether ester derivative has good antifriction and antiwear properties when used as a lubricating grease additive.
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Paragraph 0041-0046
(2020/06/20)
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- Preparation method of fluorine-containing carboxylic acid
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The invention discloses a preparation method of fluorine-containing carboxylic acid. The method comprises the following steps: reacting fluorine-containing carboxylate used as a raw material with an acylating chlorination reagent to obtain a corresponding mixture of fluorine-containing acyl chloride and fluorine-containing anhydride, and hydrolyzing and drying the mixture of fluorine-containing acyl chloride and fluorine-containing anhydride to obtain high-purity fluorine-containing carboxylic acid. The method provided by the invention is suitable for post-treatment of fluorine-containing carboxylic acid prepared by a fluorine-containing olefin (monoolefine, diene, cycloolefin and the like) oxidation method, replaces the traditional strong acid acidification and ether continuous extractionprocess, and is simpler, more convenient and more applicable; and the method can also be used for recovering and purifying a fluorine-containing carboxylate emulsifier. The purity of the fluorine-containing carboxylic acid prepared by the method can reach 98% or above.
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Paragraph 0056-0057
(2020/07/12)
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- A method of preparing liquid carbon dioxide thickening agent (by machine translation)
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The invention relates to a method for conventional oil and gas reservoir development of thickening agent preparation method of liquid carbon dioxide. It can solve the conventional mining method to the problem of oil-gas reservoir damage, the technical proposal: first to the bottle adding toluene and water, then adding serinol, in 0 °C [...] carbon acid tert-butyl ester, in the 25 °C reaction 4 hours, the distillation get intermediate (1), in the other a bottle after adding perfluroalkyl octoate, in 75 °C by adding thionyl chloride and N, N - dimethyl formamide, reaction 2 hours, distillation get intermediate (2); then in another bottle into the intermediate product in (1), raising the temperature to 75 °C dropping intermediate product (2), in the 75 °C reaction 12 hours to make the intermediate product (3); the final in a bottle by adding methylene chloride and trifluoroacetic acid, then adding the intermediate product (3), in the 25 °C reaction 2 hours, extraction after vacuum drying, adding 1, 6 - has been diisocyanate reaction 2 min to obtain the final product. The thickening agent can increase the viscosity of the carbon dioxide, can be used for fracturing. (by machine translation)
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Paragraph 0020; 0021; 0029; 0030; 0038; 0039
(2019/10/22)
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- Gemini type air humidity reversal agent compound as well as preparation method and application thereof
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The invention relates to a gemini type air humidity reversal agent compound as well as a preparation method and application thereof. The gemini type air humidity reversal agent compound is N,N-di(perfluoro-capryloyl) imine carboxylate. The invention also provides a preparation method of the gemini type air humidity reversal agent compound. The gemini type air humidity reversal agent compound is easy to prepare, relatively high in yield, can be prepared into an aqueous solution with water in any proportion and can change liquid humidity of the surface of a shale reservoir into air humidity, oil-gas recovery ratio is increased, and field application is facilitated.
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Paragraph 0077; 0079
(2018/05/16)
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- PH-responsive superomniphobic nanoparticles as versatile candidates for encapsulating adhesive liquid marbles
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Conventional adhesives are rarely used in sophisticated applications such as micro-fluidic devices or 'operations of bonding from a distance' due to their permanent wetting characteristics. Liquid marbles offer exceptional switching between non-wetting and wetting on demand. In this contribution, we present a novel approach to encapsulate both hydrophilic (epoxy resin) and hydrophobic (siloxane polymer) liquids via wrapping them with superomniphobic nanoparticles. The free energy for marble formation is lower for a hydrophobic liquid (0.931 × 10-16 J), whereas a hydrophilic liquid registers a higher value of 1.86 × 10-16 J. The mechanical bursting energy for hydrophobic marbles (20 μJ) is lower than that for their hydrophilic counterpart (48.6 μJ). The static friction coefficients of epoxy-based liquid marble are between 0.015 and 0.020 on glass, aluminium and stainless steel substrates. As a highlight, the nanoparticle coating is responsive to pH, and the bursting time of the liquid marbles can be tuned from 1 minute to several hours. It is demonstrated that the adhesive strength of cross-linked epoxy obtained by a liquid marble route is higher than that obtained vis-a-vis a conventional wetting route. The liquid marbles presented in this work can be ruptured by changing the pH, have a lower friction coefficient compared to the bare liquids (more rolling distance, which is highly essential for bonding of an intricate space from a distance) and are useful as dry adhesives.
- Chandan,Ramakrishna,Sunitha,Chandran, M. Satheesh,Kumar, K. S. Santhosh,Mathew, Dona
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p. 22813 - 22823
(2017/11/14)
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- An efficient, overall [4+1] cycloadditon of 1,3-dienes and nitrene precursors
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Intermolecular cycloadditions of conjugated dienes and nitrene precursors usually produce aziridines. A generally useful method was lacking to directly provide the [4+1] cycloadducts, 3-pyrrolines. We have realized this transformation by using an uniquely active catalyst, copper(II) 1,1,1,5,5,5-hexafluoroacetylacetonate ([Cu(hfacac)2]). The method is applicable to a wide array of dienes with good yields. When 1,4-disubsituted dienes are used as substrates, good-to-excellent cis or trans selectivity can be obtained. Interestingly, the cis or trans preference depends on the nature of the substituents, rather than diene geometry. Mechanistic studies reveal that the [4+1] cycloaddition proceeds through diene aziridination and subsequent ring expansion. Among common copper catalysts, only [Cu(hfacac)2] can efficiently catalyze both steps, which explains the unique efficiency of the catalyst.
- Wu, Qiong,Hu, Jian,Ren, Xinfeng,Zhou, Jianrong
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supporting information; experimental part
p. 11553 - 11558
(2011/11/29)
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- PERFLUOROCARBON-SOLUBLE COMPOUNDS
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The invention describes syntheses and purifications of several perfluorocarbon-soluble compounds having a general formula RF - L - X or RF - L - X - L - RF, wherein RF is a perfluorocarbon group, X is a hydrophilic moiety, and L is an amide linkage of general structure -CO-NH-. The invention also provides microemulsions comprising a PFC forming an oil phase, water or aqueous solution forming a water phase, and a PEG-based fluorosurfactant with an HFB (hydrophilic groups to fluorophilic groups balance) value from about 7 to about 13. The invention also provides a method of amidification of a fluorocompound. The method involves mixing perfluoracid chloride of a general formula CnF2n+1COCI with a compound containing an amine group with a general structure R-NH2 under reaction conditions sufficient to obtain a product having a general formula CnF2n+1-CONH-R.
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Page/Page column 17
(2008/06/13)
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- A Lewis acid catalytic process for preparing fluorocarboxylic acid halides
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Selected Group III and Group V Lewis acids were found to catalyze the isomerization and rearrangement of halosulfonyldifluoromethyl group (Rf-CF2SO2X, where X is either chlorine or fluorine) to form fluorocarboxylic acid halides (RfCOX). Fluorodesulfoxylation of the halosulfonyldifluoromethyl group yielded SOF2 as one of the two sulfur-containing oxides. Product analysis would suggest that both Lewis acid catalyzed and halogen exchange reactions are occurring and are dependent upon the starting halosulfonyldifluoromethyl material and Lewis acid.
- Behr,Cheburkov
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p. 369 - 372
(2007/10/03)
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- Multiple pathways in cyclodextrin-catalyzed hydrolysis of perfluoroalkylamides
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The hydrolysis of p-nitroanilide of perfluoroalkanoic acids, CF3(CF2)nCO-, with n = 1, 2, 3, 5, 6, and 7, 1a-f, was studied in the presence of β-cyclodextrin (CD). All reactions were catalyzed by CD through the formation of a 1:1 and 1:2 inclusion complexes. The association equilibrium constants for the 1:1 complexes were dependent on the number of carbons of the fluoroalkyl chain, whereas those of the 1:2 complexes were almost independent. These results indicate that, in the former case, the perfluoroalkyl chain is included, while in the latter, the CD unit encloses the aryl ring. For compounds 1a,b both complexes were more reactive than the substrate itself. The ratio of the reaction of complexed to uncomplexed substrate had its highest value for 1a in the case of the 1:1 complex, and for 1b, the 1:2 complex. This is attributed to the geometry of the complexes. Although compounds 1c-e reacted at the same rates in the free or 1:1 complexed form, CD accelerated the reactions because of an increase of the pKa of the substrate, which results in a higher concentration of the neutral reactive substrate at the same pH. Compound 1f formed aggregates even at 10-6 M concentration, and CD-induced deaggregation resulted in catalysis of the reaction.
- Granados, Alejandro,De Rossi, Rita H.
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p. 3690 - 3696
(2007/10/02)
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- AMINE(POLYFLUOROALKOXYACYL)IMIDE SURFACTANTS
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Twenty-one examples (10a-d, 11a-l and 12a-e) of a new class of surfactants, the amine(polyfluoroalkoxyacyl)imides, were prepared by the reaction of esters containing polyfluoroalkoxy groups with tertiary alkylaminimides and hydroxyalkylaminimides.Included are five examples of difunctional aminacylimides that contain the hydrophilic portion of the molecule in the middle.These new surfactants are among the most potent known in their ability to form aqueous solutions with very low surface tensions and can be used to prepare stable emulsions of perfluorodecalin in water.Two new esters (ethyl perfluorooctyloxyacetate, 7, and ethyl 1H,1H-perfluorooctyloxyacetate, 9) used as intermediates to the surfactants were prepared by the alkylation of perfluoro- and 1H,1H-perfluorooctanol salts with ethyl bromoacetate.Other esters used in the preparation of the surfactants were derived from oligomers of hexafluoropropene oxide.
- Haywood, Lisa,McKee, Sean,Middleton, W. J.
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p. 419 - 431
(2007/10/02)
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- SYNTHESES OF PERFLUOROALKYL N-POLYETHOXYLATED AMIDES
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Monodisperse perfluoroalkyl N-polyethoxylated amides, CnF2n+1CONH(CH2CH2O)mH, with n = 6, 7, 8 and 9 and m = 2, 3, and 4 are potential nonionic fluorinated surfactants.The syntheses of these comounds are described.
- Afzal, Jalees,Fung, B. M.,O'Rear, Edgar A.
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p. 385 - 394
(2007/10/02)
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- REGIOSPECIFIC PREPARATION OF α,α-DIHALOFLUOROMETHYL PERFLUOROALKYL KETONES.
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Acylation of F-phosphoranium salts with F-acyl chlorides gives the corresponding Z-perfluoro betaine in high yield.Subsequent chlorination or bromination regiospecifically yields the α,α-dihalofluoromethyl perfluoroalkyl ketones.
- Jeong, In Howa,Burton, Donald J.,Cox, Daryl G.
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p. 3709 - 3712
(2007/10/02)
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- Thermal Decomposition of Some Perfluoro- and Polyfluorodiacyl Peroxides
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Seven polyfluoroacyl peroxides were synthesized, some of them by a new procedure involving the direct interaction of an acyl fluoride with hydrogen peroxide.In the temperature range of 20-40 deg C, all these peroxides undergo first-order decomposition in dilute 1,1,2-trichloro-1,2,2-trifluoroethane (Freon-113) solutions (F-RF.Differing from other perfluoro or polyfluoro radicals, the perfluoro-α-isopropoxyethyl radicals (10) undergo substantial β scission to form perfluoroisopropyl radicals (11) during their lifetime.The ΔHexc. values for the perfluoroacyl peroxides are about 24 kcal mol-1, or about 5 kcal lower than that of the nonfluorinated diacyl peroxides (ca. 29 kcal mol-1).Apparently, the higher relative rates for 3 and 7 are caused by different factors.The latter peroxide (7) decomposes with a more favorable ΔSexc. term, whereas the former (3) decomposes with lower values of both ΔHexc. and ΔSexc..Thus, weakening of the peroxide bond by H bonding of the peroxide oxygen atom with the acidic ω-hydrogen atom seems to be implicated in the decomposition of 3.With a half-life of 81 min at 20 deg C, 3 may become a useful low-temperature initiator for free-radical reactions and polymerization.
- Chengxue, Zhao,Renmo, Zhou,Heqi, Pan,Xiangshan, Jin,Yangling, Qu,et al.
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p. 2009 - 2013
(2007/10/02)
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