- Synthesis of Fluorinated Dialkyl Carbonates from Carbon Dioxide as a Carbonyl Source
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Fluorinated dialkyl carbonates (DACs), which serve as environmentally benign phosgene substitutes, were produced successfully from carbon dioxide either directly or indirectly. Nucleophilic addition of 2,2,2-trifluoroethanol to carbon dioxide and subsequent reaction with 2,2,2-trifluoroethyltriflate (3 a) afforded bis(2,2,2-trifluoroethyl) carbonate (1) in up to 79 % yield. Additionally, carbonate 1 was obtained through the stoichiometric reaction of 3 a and cesium carbonate. Although bis(1,1,1,3,3,3-hexafluoro-2-propyl) carbonate (4) was difficult to obtain by either of the above two methods, it could be synthesized through the transesterification of carbonate 1.
- Sugiyama, Masafumi,Akiyama, Midori,Nishiyama, Kohei,Okazoe, Takashi,Nozaki, Kyoko
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- Photo-on-Demand Base-Catalyzed Phosgenation Reactions with Chloroform: Synthesis of Arylcarbonate and Halocarbonate Esters
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Carbonate esters are utilized as solvents and reagents for C1 building blocks in organic synthesis. This study reports a novel photo-on-demand in situ synthesis of carbonate esters with CHCl3 solutions containing a mixture of an aromatic or haloalkyl alcohol having relatively high acidity, and an organic base. We found that the acid-base interaction of the alcohol and base in the CHCl3 solution plays a key role in enabling the photochemical reaction. This reaction allows practical syntheses of diphenyl carbonate derivatives, haloalkyl carbonates, and polycarbonates, which are important chemicals and materials in industry.
- Dai, Namin,Eda, Kazuo,Harada, Hidefumi,Hashimoto, Yuka,Hosokawa, Sasuga,Kakiuchi, Toshifumi,Liang, Fengying,Okazoe, Takashi,Suzuki, Yuto,Tana, Gegen,Tsuda, Akihiko
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p. 9811 - 9819
(2021/07/20)
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- Continuous method for preparing carbonate esters
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In one embodiment, a continuous process for preparing organic carbonate solvent of Formula (I) as described herein comprises contacting a first reactant (an alcohol) with a reactive carbonyl source (carbonyldiimidazole (CDI) or an alkylchloroformate) in the presence of a catalyst in reaction stream flowing through a continuous flow reactor at temperature 20° C. to about 160° C. and at a flow rate providing a residence time in the range of about 0.1 minute to about 24 hours; collecting a reactor effluent exiting from the continuous flow reactor; recovering a crude product from the reactor effluent; and distilling the crude product to obtain the organic carbonate compound of Formula (I). In another embodiment, the first reactant is an epoxide and the carbonyl source is carbon dioxide.
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Page/Page column 13-14
(2021/06/09)
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- Synthesis method of bis (2, 2, 2-trifluoroethyl) carbonate
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The invention discloses a synthesis method of bis (2, 2, 2-trifluoroethyl) carbonate, and belongs to the technical field of battery electrolytic solution additives. The preparation method comprises the following steps: adding dichloromethane and N, N '-carbonyldiimidazole into a reaction kettle, starting to dropwise add trifluoroethanol, after 1.5-2 hours of dropwise adding, heating to reflux, stopping heating after 2-2.5 hours, adding the system into cold water, cooling to the temperature T of less than or equal to 20 DEG C, adding concentrated hydrochloric acid to adjust the pH value to 1-2, stirring for 0.5-1 hour, separating liquid, drying, carrying out suction filtration, removing a solvent through pressure reducing, and rectifying to obtain the bis (2, 2, 2-trifluoroethyl) carbonate. The purity of the product synthesized by the method is more than 99%, and the water content is less than 100ppm.
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Paragraph 0023-0034
(2021/06/06)
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- METHOD OF PRODUCING FLUORINE-CONTAINING CARBONIC ACID ESTER
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PROBLEM TO BE SOLVED: To provide a novel method of producing a fluorine-containing carbonic acid ester. SOLUTION: In a method of producing a fluorine-containing carbonic acid ester, a compound represented by formula (A1), a compound represented by formula (A2) and carbon dioxide are reacted in the presence of a base thereby producing a fluorine-containing carbonic acid ester represented by formula (A3), where formula (A1) is Ra1-OH, formula (A2) is Ra2-CHRa3-Lv, and formula (A3) is Ra1-O-CO-O-CHRa3-Ra2. SELECTED DRAWING: None COPYRIGHT: (C)2020,JPOandINPIT
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Paragraph 0071
(2020/05/02)
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- A containing alkyl straight chain carbon and its synthesis method (by machine translation)
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The invention discloses a containing alkyl straight chain carbon and its synthesis method, the fluorine-containing alkyl straight chain carbon esters include alkyl alkyl carbonate and double-(alkyl) carbon ester; the synthetic method, adopts the one-pot synthesis phenol [...] exchange circulation reaction, comprises the following steps: (1) a transesterification reaction; (2) secondary ester exchange reaction; (3) separating and purifying; (4) phenol recycling, to obtain the alkyl alkyl carbonate and double-(fluoroalkyl) carbonate. The invention relates to a containing alkyl straight chain carbon acid ester synthetic method, adopts the one-pot synthesis phenol [...] exchange circulation reaction for preparing fluorine-containing alkyl straight chain carbon ester, realize the phenol a feeding, recycled many times the new process; synthesis method of the invention, which can effectively save the cost of material, the generation of reducing waste and waste liquid, realize green circulation type production, high product yield, purity of 99.9% or more, can meet the requirements of the lithium battery electrolyte. (by machine translation)
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Paragraph 0047-0051
(2019/05/08)
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- Improved Synthesis of Unsymmetrical Carbonate Derivatives Using Calcium Salts
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An effective synthetic method for unsymmetrical carbonate species has been developed. Calcium oxide and calcium hydroxide were found to be highly effective for this reaction, affording unsymmetrical carbonates in high yield and purity. Calcium chloride, which is a coproduct, serves as a water scavenger that can be easily removed. Additional drying processes and complicated purification steps are not necessary in this reaction. This improved process is important in terms of green sustainable chemistry principles.
- Hamada, Tomohito,Okada, Michiaki,Yamauchi, Akiyoshi,Kishikawa, Yosuke
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p. 667 - 673
(2019/04/25)
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- PROCESS FOR PRODUCING FLUORINATED ELECTROLYTE SOLVENT
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The invention provides a method for producing halogenated carbonates, the method comprising reacting a halogenated alcohol or diol with a solid source of carbonyl moiety as a base in an ether.
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Paragraph 0039; 0040; 0041; 0042; 0043; 0044
(2018/04/13)
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- Trifluorolactic methyl ester carbonate containing straight chain
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Disclosed is a trifluoromethyl straight-chain carbonic ester preparation method. Preparation steps are: mixing trifluoromethyl saturated monohydric alcohol or a mixture of trifluoromethyl saturated monohydric alcohol and saturated straight-chain monohydric alcohol with triphosgene; and under an organic amine acid-binding agent, adjusting a temperature to 25 to 80 °C, reacting for 1 to 10 h, to obtain mixed liquor containing the trifluoromethyl straight-chain carbonic ester; and performing filtering and separation, and performing distillation and purification on the mixed liquor containing the trifluoromethyl straight-chain carbonic ester, to obtain the trifluoromethyl straight-chain carbonic ester. The trifluoromethyl straight-chain carbonic acid obtained by using the process disclosed by the present invention is a high-voltage solvent of a power lithium battery, which can greatly improve thermal stability, cycle performance, and high-voltage characteristics of the power lithium battery. The preparation method has simple process, high yield, and low costs. At the same time, the triphosgene has strong stability, and has little resolution under a boiling point of 200°C, and therefore, problems of major security and environmental protection do not exist in the preparation process.
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Paragraph 0011; 0012
(2016/12/22)
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- METHOD FOR PRODUCING CARBAMATE COMPOUND, CARBAMATE COMPOUND, AND METHOD FOR PRODUCING ISOCYANATE COMPOUND USING SAME
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The present invention relates to a method of producing a carbamate compound, comprising reacting a fluorine-containing carbonic diester compound represented by formula (1) and a non-aromatic diamine compound represented by formula (2) without using a catalyst, to thereby produce a carbamate compound represented by formula (3), and a method of producing an isocyanate compound represented by formula (20) from the carbamate compound without using a catalyst, wherein R represents a fluorine-containing monovalent aliphatic hydrocarbon group, and A represents a divalent aliphatic hydrocarbon group, a divalent alicyclic hydrocarbon group or a divalent aromatic-aliphatic hydrocarbon group. [Chem. 2] ????????H2N-A-NH2?????(2) [Chem. 4] ????????O=C=N-A-N=C=O?????(20)
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Paragraph 0068
(2013/03/26)
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- A facile synthesis of unsymmetrical ureas
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A facile and versatile method for the synthesis of unsymmetrical ureas from readily available reagents is reported. In the first step trifluoroethylchloroformate is reacted with a stoichiometric amount of a primary amine to give an intermediate trifluoroethyl carbamate. The addition of a second amine (primary or secondary) to the trifluoroethyl carbamate furnishes corresponding unsymmetrical ureas in 75-85% yield. A simple workup procedure, the high yields obtained, and the purity of the isolated products are suitable for the parallel synthesis of combinatorial libraries of unsymmetrical ureas with high structural and functional diversity.
- Bogolubsky, Andrey V.,Ryabukhin, Sergey V.,Pipko, Sergey E.,Lukin, Oleg,Shivanyuk, Alexander,Mykytenko, Dmytro,Tolmachev, Andrey
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experimental part
p. 3619 - 3623
(2011/06/21)
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- METHOD FOR PRODUCING CARBONATE COMPOUND
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The present invention is to provide a production process capable of selectively producing various kinds of fluorine-containing carbonate compounds without any inhibition in high yields without using phosgene and without producing hydrogen chloride as a by-product. The present invention relates to a process for producing a fluorine-containing compound having a carbonate bond by reacting a compound (1) with a fluorine-containing compound having an OH group. In the formula (1) shown below, X1 to X6 each represents a hydrogen atom or a halogen atom, at least one of X1 to X3 is a halogen atom, and at least one of X4 to X6 is a halogen atom.
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Page/Page column 21; 22
(2010/08/22)
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- Fluorocarbanion Chemistry. A Versatile Synthesis of Functionalized Fluoro Ketones
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Fluorocarbanions generated by the addition of an anion to a fluoro olefin can be trapped by fluoro esters, thereby providing a versatile, one-step synthesis of functionalized fluoro ketones.The most efficient anions include CN-, N3-, C6H5O-, RO-, and RS-.The reaction has been extended in one case to prepare a sulfinate ester.
- Krespan, Carl G.,Smart, Bruce E.
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p. 320 - 326
(2007/10/02)
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- Monocarbonate transesterification process
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A monocarbonate transesterification process comprising contacting in the presence of a base, a beta-fluoroaliphatic carbonate and a compound selected from the class consisting of monohydroxy aliphatic alcohols, phenols and ortho-positioned dihydroxy aromatic compounds. The resulting monocarbonates are useful as monocarbonates, per se, or useful in the preparation of polycarbonates which can be molded or formed into films, laminates or reinforced plastics by conventional techniques.
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