Method for producing chloroformate compound

A manufacturing method and technology of chloroformate, applied in the preparation of organic carbonate, preparation of phosgene or haloformate, organic chemistry, etc., can solve problems such as phosgene gas release

Active Publication Date: 2019-04-02
KANEKA CORP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

For the method of this patent document 5, first mix phosgene and alcohol and then drive out the remaining phosgene gas, since the theoretical amount of phosgene is equimolar with alcohol, the theoretical amount of amine hydrochloride produced It is also beneficial that it can be reduced to equimolarity with alcohol, but there is a danger that phosgene gas will be released outside the system

Method used

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  • Method for producing chloroformate compound
  • Method for producing chloroformate compound
  • Method for producing chloroformate compound

Examples

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Embodiment

[0056] Hereinafter, the present invention will be described more specifically with examples given, but the present invention is of course not limited to the following examples, and can be implemented with appropriate changes within the scope of the aforementioned / later-described gist, All of them are included in the technical scope of the present invention.

reference example 1

[0058] 1 g of various amines shown in Table 1 below was added to 10 mL of each solvent shown in Table 1 below to prepare a solution with a concentration of 10% (weight / volume). A n-propanol solution of hydrochloric acid (hydrochloric acid concentration: 34% by weight) was added to this solution until it became 1.1 equivalent (=molar amount of hydrogen chloride / molar amount of amine), and stirred at room temperature for 1 hour. After stirring, the presence or absence of solid precipitation was confirmed visually. In the table, ○ means that no solid was precipitated, and x means that a solid was precipitated.

[0059]

[0060] *1: Using amine

[0061] Triethylamine (TEA), diisopropylethylamine (DIPEA), tripropylamine (TPA), tributylamine (TBA), trioctylamine (TOA), 1,8-diazabicyclo[5,4 ,0] Undec-7-ene (DBU), 2,6-Lutidine (LTD)

[0062] *2: Solvents are used

[0063] Tetrahydrofuran (THF), methyl tert-butyl ether (MTBE), isopropyl acetate (IPRA), acetone (ACE), N,N-dimethy...

Embodiment 1

[0075] 25.49 g of toluene was put into 0.61 g of triphosgene to prepare a homogeneous solution, which was used as liquid A. Separately, 22.81 g of toluene was put into 1.42 g of tributylamine and 1.00 g of 9-fluorenylmethanol to prepare a homogeneous solution, which was used as liquid B. Put the T-shaped mixer (inner diameter: 2mm, material: polytetrafluoroethylene (PTFE)) and retention line (tube inner diameter: 2mm, material: polytetrafluoroethylene (PTFE)) in a constant temperature bath at 0°C, and Liquid A and liquid B were fed with a diaphragm pump (manufactured by KNF) at a rate of 2 ml / min (linear velocity: 127 cm / min), mixed with a T-shaped mixer, and circulated in the retention line for 1 minute to react. The reaction liquid was quenched with stirring in 34.85 g of 13% phosphoric acid water charged to the flask, and after liquid separation, 66.24 g of an organic layer containing 1.19 g of 9-fluorenylmethyl chloroformate was obtained (yield 90%). It should be noted th...

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Abstract

Provided is a method for producing a chloroformate compound safely, with high efficiency and in a large quantity. A chloroformate compound can be produced by mixing a solution of triphosgene, an amineand an alcohol compound together in a flow-type reactor to cause the reaction of these components. Alternatively, a chloroformate compound can be produced by mixing a solution of triphosgene with a solution of an amine and an alcohol compound in a flow-type reactor to cause the reaction of these components. The amine is preferably tributylamine, and the amine is preferably used in an amount of 0.8 to 3 equivalents relative to the amount of the alcohol compound.

Description

technical field [0001] The present invention relates to a method for producing a chloroformate compound using a flow reactor. Background technique [0002] Chloroformic acid ester compounds are very useful as raw materials and intermediates of pharmaceuticals, agricultural chemicals, etc. due to their high reactivity, and the development of production methods capable of synthesizing these compounds safely and at high yields at low cost is desired. As a method for producing a chloroformate compound, it is generally a method of reacting phosgene gas, or phosgene generated in the system from diphosgene or triphosgene, with an alcohol compound in a batch reaction tank. Specifically, there is known a method for producing corresponding 9-fluorenylmethyl chloroformate by dissolving phosgene gas in tetrahydrofuran in a batch reaction tank and then adding 9-fluorenylmethanol (Patent Document 1). Alternatively, there is also known a method of dissolving phosgene gas in dichloromethan...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C68/02C07C69/96
CPCC07C69/96C07C68/06C07C68/02B01J2219/00166B01J2219/00051
Inventor 安河内宏昭舟桥诚西山章武田俊弘满田胜
Owner KANEKA CORP
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