- Practical syntheses of neopentyl alcohol and sec-butyl ethyl ether using Marukasol as a solvent
-
By using Marukasol, neopentyl alcohol and sec-butyl ethyl ether have been obtained in good yields with easy operations. Thus, neopentyl alcohol was obtained from tert-butylmagnesium chloride and paraformaldehyde in 76% isolated yield with >99% purity using Marukasol as an effective extraction solvent On the other hand, sec-butyl ethyl ether was obtained from sodium sec-butoxide with ethyl iodide in Marukasol in 67% yield with >99% purity.
- Yuasa, Yoshifumi,Kato, Yasushi
-
-
Read Online
- METHOD FOR PRODUCING FLUORINATED HYDROCARBONS
-
Provided is a method for industrially advantageously producing a fluorinated hydrocarbon (3). The disclosed method for producing a fluorinated hydrocarbon represented by formula (3) includes bringing into contact, in a hydrocarbon-based solvent, a secondary or tertiary ether compound represented by formula (1) below with an acid fluoride represented by formula (2) in the presence of lithium salt or sodium salt (in the formulae, R1 and R2 each represent a C1-3 alkyl, and R1 and R2 may be bonded to each other to form a ring structure; R3 represents a hydrogen atom, methyl, or ethyl; and R4 and R5 each represent methyl or ethyl).
- -
-
Paragraph 0095-0097
(2020/01/12)
-
- MANUFACTURING METHOD OF FLUORINATED HYDROCARBON
-
PROBLEM TO BE SOLVED: To provide a method for industrially advantageously manufacturing fluorinated hydrocarbon (3). SOLUTION: There is provided a method for manufacturing fluorinated hydrocarbon represented by the formula (3), including contacting a secondary or tertiary ether compound represented by the formula (1) and acid fluoride represented by the formula (2) in the presence of a silver salt in a hydrocarbon solvent. R1 and R2 are each independently a C1 to 3 alkyl group, R1 and R2 may bind to form a ring structure, R3 is H, a methyl group or an ethyl group, R4 and R5 are each independently a methyl group or an ethyl group. SELECTED DRAWING: None COPYRIGHT: (C)2018,JPOandINPIT
- -
-
Paragraph 0049
(2018/05/08)
-
- METHOD FOR MANUFACTURING FLUORINATED HYDROCARBON
-
The present invention is a method for producing a fluorinated hydrocarbon represented by a structural formula (3), wherein an ether compound represented by a structural formula (1) and an acid fluoride represented by a structural formula (2) are brought into contact with each other in a hydrocarbon-based solvent, in the presence of a catalyst in which boron trifluoride is supported on a metal oxide: wherein R1 and R2 represent an alkyl group having 1 to 3 carbon atoms, R3 represents a hydrogen atom, a methyl group or an ethyl group, and R4 and R5 represent a methyl group or an ethyl group; and R4 and R2 may be bonded to each other to form a cyclic structure. Through the present invention, a method for industrially advantageously producing 2-fluorobutane is provided.
- -
-
Paragraph 0081; 0082; 0083
(2018/08/20)
-
- METHOD FOR PRODUCING FLUORINATED HYDROCARBON
-
The present invention is a method for producing a fluorohydrocarbon represented by a structural formula (3) comprising bringing a secondary or tertiary ether compound represented by a structural formula (1) into contact with an acid fluoride represented by a structural formula (2) in a hydrocarbon-based solvent in the presence of a boron trifluoride complex. (In structural formulae (1) to (3), each of R1 and R2 represents an alkyl group having 1 to 3 carbon atoms, R3 represents a hydrogen atom, a methyl group, or an ethyl group, and each of R4 and R5 represents a methyl group or an ethyl group, provided that R1 and R2 are optionally bonded to each other to form a ring structure.)
- -
-
Paragraph 0052; 0053; 0054
(2017/07/14)
-
- The fluorinated hydrocarbon production (by machine translation)
-
2 - fluorobutane industrially advantageous production method [a]. (1) the ether compound represented by the formula [a], equation (2) as shown in the di-acid, a hydrocarbon-based solvent, in the presence of boron trifluoride catalyst is carried on a polyvinylpyrrolidone, contacting, formula (3) represented by the production of fluorinated hydrocarbons. (R1 And R2 The alkyl groups are independently C1 a-3; R1 And R2 The coupling may form a ring structure; R3 Is H, a methyl group or an ethyl group; R4 Is a methyl group or an ethyl group; R5 Is a methyl group or ethyl group)[Drawing] no (by machine translation)
- -
-
Paragraph 0051
(2017/09/02)
-
- METHOD FOR PRODUCING FLUORINATED HYDROCARBON
-
PROBLEM TO BE SOLVED: To provide an industrially advantageous method for producing a fluorinated hydrocarbon such as 2-fluorobutane useful as etching gas for a dry etching process. SOLUTION: There is provided a method for producing a fluorinated hydrocarbon represented by formula (3) by bringing an ether compound represented by formula (1) into contact with an acid fluoride represented by formula (2) in a halogenated hydrocarbon solvent in the presence of a metal halide represented by formula (4): MX3 (M represents a metal atom; X represents a chlorine atom or a bromine atom) (R1 and R2 each independently represent an alkyl group having 1-3 carbon atoms; R1 and R2 may be bonded to form a ring structure; R3 represents H, a methyl group or an ethyl group; R4 and R5 each independently represent a methyl group or an ethyl group.) SELECTED DRAWING: None COPYRIGHT: (C)2017,JPOandINPIT
- -
-
Paragraph 0050
(2017/10/31)
-
- METHOD FOR PRODUCING FLUORINATED HYDROCARBON
-
PROBLEM TO BE SOLVED: To provide a method for industrially advantageously producing a fluorinated hydrocarbon. SOLUTION: The method for producing a fluorinated hydrocarbon represented by formula (3) comprises bringing a secondary or tertiary ether compound represented by formula (1) into contact with an acid fluoride represented by formula (2) in the presence of a compound having an N-X bond (X is a halogen atom selected from a chlorine atom, a bromine atom, and an iodine atom) in a halogenated hydrocarbon-based solvent. (R1 and R2 are each independently a C1-C3 alkyl group; R3 is H, a methyl group, or an ethyl group; R4 and R5 are each a methyl group or an ethyl group; and R1 and R2 may be bonded together to form a ring structure.) SELECTED DRAWING: None COPYRIGHT: (C)2018,JPOandINPIT
- -
-
Paragraph 0047
(2018/03/09)
-
- SNAAP sulfonimidate alkylating agent for acids, alcohols, and phenols 1
-
Stable, crystalline ethyl N-tert-butyl-4-nitrobenzenesulfonimidate has been prepared in high yield by direct O-ethylation of N-tert-butyl-4- nitrobenzenesulfonamide with iodoethane and silver(I) oxide in dichloromethane. This sulfonimidate directly ethylates various acids to esters; the stronger the acid, the faster it alkylates and in higher yield. It readily ethylates alcohols and phenols to ethers at room temperature in the presence of tetrafluoroboric acid catalyst without molecular rearrangements or racemization. We have defined these reactions as SNAAP alkylations: [substitution, nucleophilic of acids, alcohols and phenols]. The hard sulfonimidate alkylating agent is chemoselective, preferring oxygen > nitrogen > sulfur. The sulfonamide byproduct of alkylation is readily recycled to the sulfonimidate. Georg Thieme Verlag Stuttgart . New York.
- Maricich, Tom J.,Allan, Matthew J.,Kislin, Brett S.,Chen, Andrea I-T.,Meng, Fan-Chun,Bradford, Christine,Kuan, Nai-Chia,Wood, Jeremy,Aisagbonhi, Omonigho,Poste, Alethea,Wride, Dustin,Kim, Sylvia,Santos, Therese,Fimbres, Michael,Choi, Dianne,Elia, Haydi,Kaladjian, Joseph,Abou-Zahr, Ali,Mejia, Arturo
-
p. 3361 - 3368
(2014/01/06)
-
- Byproducts formation in the ethyl tert-butyl ether (ETBE) synthesis reaction on macroreticular acid ion-exchange resins
-
Ethyl tert-butyl ether (ETBE) production is one of the industrial processes of major importance today in Europe. However, the study of side reactions in this synthesis reaction appears scarcely in the open literature. Side reactions take place along with the etherification of C4 olefinic cuts with ethanol, catalyzed by acidic ion-exchange resins. In this work, byproducts formation is studied in a batch reactor. The presence of diethyl ether (DEE), ethyl sec-butyl ether (ESBE), dimers of isobutene (2,4,4-trimethyl-1-pentene (TMP-1) and 2,4,4-trimethyl-2-pentene (TMP-2)) and tert-butyl alcohol (TBA) has been studied in terms of production and selectivity. The effect of temperature, ranging from 323 to 383 K, and the influence of initial molar ratio ethanol/isobutene (R A/O), ranging from 0.5 to 2.0, on byproducts formation have been analyzed. All byproducts formation was favored by high temperatures. A low initial molar ratio ethanol/isobutene favored the formation of DEE, ESBE, TMP-1 and TMP-2, whereas high molar ratios favored TBA formation.
- Badia,Fité,Bringué,Ramírez,Cunill
-
p. 384 - 394
(2013/10/22)
-
- γ-Ray-induced reduction of sterically hindered alkyl carboxylates with trichlorosilane in the presence of hydrogen chloride. Two-step mechanism for the formation of alkanes via the alkyl chloride
-
γ-Irradiation of a mixture of 1-adamantyl acetate and trichlorosilane (TCS) in the presence of hydrogen chloride yields adamantane. The first step of this reaction entails cleavage of the alkyloxygen bond by the action of HCl and TCS to give the alkyl chloride. The chloride, in the second step, is dechlorinated by TCS by a known, free-radical mechanism. t-Amyl and benzyl acetates react analogously to 1-adamantyl acetate in this system to give isopentane and toluene, whereas other primary and secondary alkyl derivatives produce the corresponding dialkyl ethers by a known, free-radical mechanism.
- Oka, Kunio,Nakao, Ren
-
-
- Organomagnesium Inner Complexes, Part I. Bis(dialkylaminoalkyl)- and Bis(alkoxybutyl)magnesium Compounds
-
A series of magnesium inner complexes has been prepared by reacting MgH2 (prepared by homogeneous catalysis) with dialkylallyl- and -3-butenylamines and -3-butenylethers in the presence of catalytic amounts of ZrCl4.The monomeric nature of bis(4-methoxybutyl)magnesium has been confirmed by X-ray diffraction.The analogous syntheses of bis(3-alkoxypropyl)magnesium compounds failed: cleavage of the allyl ether with elimination of propene occurred.This cleavage reaction is accelerated by catalytic amounts of NiCl2 or ZrCl4. - Keywords: Magnesium, Inner Complexes, Crystal Structure, X-Ray
- Angermund, Klaus,Bogdanovic, Borislav,Koppetsch, Gudrun,Krueger, Carl,Mynott, Richard,et al.
-
p. 455 - 466
(2007/10/02)
-
- Chemistry of Carbenes: Part III - Reaction of Methylene with Ethyl n-Propyl Ether
-
The bond reactivities for ethyl n-propyl ether, based on unity for the primary bonds of ethyl group, again prove the discriminate attack of methylene.All secondary bonds are attacked faster than the primary bonds of ethyl, the 2 C-H of ethyl itself being attacked 1.83 times, which is higher than the attack on secondary αC-H (1.74) and βC-H (1.29) bonds.The descending order of reactivities of C-H bonds in propyl is α > β > γ.Additional evidence of the electrophilic effect of ethereal oxygen on the insertion reactions as also on the displacement reaction where methylene gives a methyl alkyl ether and displaces an olefin has been obtained.Similarly, the predicted formation of aldehydes resulting from the abstraction reactions of methylene has been observed.These results obtained in gas phase contrasted with the liquid phase work of Doering et al who found the attack to be indiscriminate.This work further confirms the difference between the two phases.
- Mehta, R. K. S.
-
-
- Deamination Reactions, 41. Reactions of Aliphatic Diazonium Ions and Carbocations with Ethers
-
Aliphatic diazonium ions and carbocations were generated by deacylation of appropriate nitrosoureas (1, 5, 9) in alcohol-ether mixtures or in 2-alkoxyethanols.Ethers were generally inferior to alcohols in capturing cationic intermediates.Formation of trialkyloxonium ions led to alkyl exchange or ring opening.The observed reactivity orders were n-butyl > isobutyl for the diazonium ions, allyl > sec-butyl > tert-butyl for the carbocations, methoxy > ethoxy and oxirane > oxetane > tetrahydrofuran for the ethers, indicating the predominance of steric effects.Neighboring group participation in 4-methoxy-1-butanediazonium ions (58) and 4,5-epoxy-1-pentanediazonium ions (74) was detectable but inefficient ( 20percent of cyclic oxonium ions).
- Kirmse, Wolfgang,Jansen, Ulrich
-
p. 2607 - 2625
(2007/10/02)
-
