- Catalytic synthesis method for 2-hydroxyethyl n-octyl sulfide
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The invention relates to a catalytic synthesis method for 2-hydroxyethyl n-octyl sulfide. The method includes: taking 1-octanethiol and ethylene carbonate as the raw materials, adopting an alkali metal salt or inorganic porous carrier loaded alkali metal salt as the catalyst, carrying out reaction at 120DEG C and under atmospheric pressure for 0.5-3h without any solvent to prepare 2-hydroxyethyl n-octyl sulfide, and monitoring the release amount of carbon dioxide gas to monitor the reaction process. Compared with the prior art, the method has the beneficial effects that: (1) ethylene carbonateis cheap and easily available, the production cost is low, the reaction by-product is carbon dioxide, which is gas under room temperature and pressure, and is easily separated from the product, and the carbon dioxide gas by-product does not pollute the environment; (2) the reaction has no need for any solvent, and the subsequent solvent recovery process is simplified; (3) the reaction is carriedout under normal pressure, and the reaction conditions are mild; and (4) the alkali metal salt catalyst is incompatible with the product, effective separation can be realized smoothly by filtration, the separation process is simple, and 2-hydroxyethyl n-octyl sulfide with a purity of 98% or above can be obtained without further treatment of the oil phase, thus greatly saving the product separationcost.
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Page/Page column 0023-0047
(2019/02/13)
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- Method for catalyzing n-octylmercaptan and ethylene carbonate to react through organic tertiary amine
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The invention provides a method for catalyzing n-octylmercaptan and ethylene carbonate to react through organic tertiary amine and relates to a synthesis method of organic thioether in synthesis of fine chemicals. The method comprises the following steps: taking the n-octylmercaptan and the ethylene carbonate as raw materials and the organic tertiary amine as a catalyst; reacting for 0.5 to 3h at120 DEG C under the conditions of no any solvent and normal pressure, so as to prepare 2-hydroxyethyl n-octylmercaptan; tracking a reaction progress by utilizing a water discharging method until no carbon dioxide gas is released; cooling a reaction mixture; and adsorbing the organic tertiary amine catalyst through strong-acid cationic exchange resin to prepare a product. The invention aims at providing a novel industrialized technological method for synthesizing 2-(octylthio)ethanol and the method has the advantages that the price of the raw materials is low, the 2-(octylthio)ethanol is synthesized under the condition of no any solvent, reaction conditions are moderate, the product is simple to separate after reaction, and energy saving and energy consumption are realized.
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Paragraph 0024-0027
(2019/04/13)
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- A mechanism of alkali metal carbonates catalysing the synthesis of β-hydroxyethyl sulfide with mercaptan and ethylene carbonate
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The reaction of β-hydroxyethylation is essential to the current practice of organic chemistry. Here, we proposed a new and green route to synthesize 2-hydroxyethyl n-alkyl sulfide with n-alkyl mercaptan and ethylene carbonate (EC) in the presence of alkali carbonates as catalysts and revealed the mechanism by experiments and theoretical calculations. The reaction reported proceeds rapidly with high yields when it is performed at 120 °C and the catalytic loading is ~1 mol%. This protocol is applicable to other mercaptans to synthesize the corresponding β-hydroxyethyl sulfide. Density functional theory-based calculations show the energy profile for the reaction pathway. The rate-determining step is the ring-opening of EC. A negatively charged O atom of alkali carbonates approaches the S atom of -SH under the influence of hydrogen bonds. An activated S atom that carries more negative charge serves as a nucleophilic reagent and assists in the ring-opening of EC by reducing the Mayer bond orders of the C1-O1 bond in EC. Alkali cations also contribute to the C1-O1 bond cleavage. The energy barrier for the ring-opening of EC decreases with the decrease of electronegativity of alkali cations. Subsequent transference of a H atom leads to the formation of β-hydroxyethyl sulfide, the dissociation of CO2 and the reduction of K2CO3
- Liu, Dongliang,Thomas, Tiju,Gong, Hong,Li, Fei,Li, Qiang,Song, Lijuan,Azhagan, Tamil,Jiang, Heng,Yang, Minghui
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p. 9367 - 9374
(2019/11/13)
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- Sulfur makes the difference: Synthesis and mesomorphic properties of novel thioether-functionalized imidazolium ionic liquid crystals
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Novel thioether-linked imidazolium ionic liquid crystals were synthesized starting from methyl 2-mercaptoacetate. The mesomorphic properties were determined by differential scanning calorimetry (DSC), polarizing optical microscopy (POM), and X-ray diffraction. All mesogens displayed smectic A mesophase geometries with strongly interdigitated bilayer structures. Comparison of the thioether-linked imidazolium salts with the corresponding amine- and amide-linked imidazolium salts as well as simple N-alkyl-imidazolium salts showed that both mesophase width and stability increased with increasing softness of the linking unit, thus indicating the beneficial effect of sulfur. Additionally, an increase of the length of the linking unit decreased the interdigitation of the alkyl chains.
- Mansueto, Markus,Kre?, Katharina Christina,Laschat, Sabine
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p. 6258 - 6264
(2015/03/30)
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- Chemical Structure and Thermodynamics of Amphiphile Solutions. 1. Solubility of Alkylthiooligooxyethylene Glycols in Water
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Solubilities of individual alkylthiooligooxyethylene glycols CnH2n+1SCH2CH2(OCH2CH2)zOH (alkyl: n-C4H9, ..., n-C9H19; and z = 0, ..., 3) in water at 298.15 K have been determined.A quantitative correlation has been found between the standard free energy for transfer from aqueous solution to pure liquid phase, ΔGot, and the structure of the studied sulfides and of oligooxyethylenated alcohols as well by using the appropriate multiple regression equation.It has been found that the thioethylene group, -SCH2CH2-, is hydrophobic.The standard free energy contribution, ΔGot, is -3.4 kJ mol-1.The interaction between methylene groups, -CH2-, of the hydrocarbon chain and the -OCH2CH2- groups of the oligooxyethylene chain is statistically significant and has an influence on the total value of ΔGot.Furthermore, the ΔGot and ΔGot are not constant.For the sulfides studied, ΔGot increases linearly with hydrocarbon chain length.For example, ΔGot for the series of butyl and nonyl derivatives is +0.24 and +0.81 kJ mol-1, respectively.The ΔGot for the series of alkyl-2-hydroxyethyl sulfides (z=0) and alkylthiotetraoxyethylene glycol (z=3) is -3.43 and -3.10 kJ mol-1, and the ΔGot and ΔGot for the group of oxyethylenated alcohols are +0.53 and -3.13 kJ mol-1, respectively.
- Sokolowski, Adam
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p. 8223 - 8226
(2007/10/02)
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- REACTIONS OF OXIRANES WITH ALKYLTHIOLS
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Alkyl-2-hydroxyalkyl sulfides and their oxyalkylenated adducts were obtained in the reaction of oxirane or methyloxirane with C4-C12 alkylthiols in presence of basic or acidic catalysts.The sulfides were further oxidized to sulfoxides and sulfones.
- Chlebicki, Jan,Cichacz, Zbigniew
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p. 485 - 494
(2007/10/02)
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- Organotin-containing composition for the stabilization of polymers of vinyl chloride
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An organotin-containing composition for the stabilization of polymers or copolymers of vinyl chloride in which there is incorporated a stabilizing amount of an organotin compound containing at least two tin atoms and which is a mercapto, hydroxy or alkoxy substituted ester of a mercapto acid substituted organotin mercapto acid diester.
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