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EP-4737392-A1 - METHOD FOR PRODUCING CARBONYL HALIDE

EP4737392A1EP 4737392 A1EP4737392 A1EP 4737392A1EP-4737392-A1

Abstract

The objective of the present invention is to provide a method for producing a carbonyl halide safely at a low cost and a low environmental load. The method for producing a carbonyl halide according to the present invention is characterized in comprising the step of irradiating a light to a mixed gas comprising methane, a halogen molecule gas and oxygen.

Inventors

  • TSUDA, AKIHIKO

Assignees

  • National University Corporation Kobe University

Dates

Publication Date
20260506
Application Date
20241011

Claims (14)

  1. A method for producing a carbonyl halide, the method comprising the step of: irradiating a light to a mixed gas comprising methane, a halogen molecule gas and oxygen.
  2. The method according to claim 1, wherein the carbonyl halide is carbonyl chloride, and the halogen molecule gas is a chlorine gas.
  3. The method according to claim 1, wherein the light has a peak wavelength of 360 nm or more and 830 nm or less.
  4. The method according to claim 1, wherein the light is irradiated to the mixed gas at an atmospheric temperature.
  5. The method according to claim 1, wherein the shortest distance between a light source to irradiate the light and the mixed gas is 1 m or less.
  6. The method according to claim 1, further comprising the step of producing a sodium halide aqueous solution by neutralizing a hydrogen halide with a basic sodium salt, wherein the hydrogen halide is produced as a side product by irradiating the light to the mixed gas.
  7. The method according to claim 1, further comprising the step of electrolyzing the sodium halide aqueous solution to produce the halogen molecule and sodium hydroxide.
  8. A method for producing a carbonate compound, the method comprising the steps of: producing a carbonyl halide by the method according to any one of claims 1 to 7, and reacting an alcohol compound and the carbonyl halide.
  9. A method for producing a halogenated formate ester compound, the method comprising the steps of: producing a carbonyl halide by the method according to any one of claims 1 to 7, and reacting an alcohol compound and the carbonyl halide.
  10. A method for producing an isocyanate compound, the method comprising the steps of: producing a carbonyl halide by the method according to any one of claims 1 to 7, and reacting a primary amine compound and the carbonyl halide.
  11. A method for producing a carbamoyl halide compound, the method comprising the steps of: producing a carbonyl halide by the method according to any one of claims 1 to 7, and reacting a secondary amine compound and the carbonyl halide.
  12. A method for producing an amino acid-N-carboxylic anhydride, the method comprising the steps of: producing a carbonyl halide by the method according to any one of claims 1 to 7, and reacting an amino acid compound represented by the following formula (VII) and the carbonyl halide, wherein the amino acid-N-carboxylic anhydride is represented by the following formula (VIII): wherein R 4 is an amino acid side chain group wherein a reactive group is protected, R 5 is H or P 1 -[-NH-CHR 6 -C(=O)-] l - wherein R 6 is an amino acid side chain group wherein a reactive group is protected, P 1 is a protective group of the amino group, 1 is an integer of 1 or more, and when 1 is an integer of 2 or more, a plurality of R 6 may be the same as or different from each other.
  13. A method for producing a Vilsmeier reagent, wherein the Vilsmeier reagent is a salt represented by the following formula (X): wherein R 7 is a hydrogen atom, a C 1-6 alkyl group or an optionally substituted C 6-12 aromatic hydrocarbon group, R 8 and R 9 are independently a C 1-6 alkyl group or an optionally substituted C 6-12 aromatic hydrocarbon group, or R 8 and R 9 may form a 4 or more and 7 or less-membered ring structure together with each other, X is a halogeno group selected from the group consisting of chloro, bromo and iodo, Y - is a counter anion, the method comprising the steps of: producing a carbonyl halide by the method according to any one of claims 1 to 7, and reacting the carbonyl halide and an amide compound represented by the following formula (IX): wherein R 7 to R 9 have the same meanings as the above.
  14. A method for producing a urea compound, the method comprising the steps of: producing a carbonyl halide by the method according to any one of claims 1 to 7, and reacting a primary amine compound or a secondary amine compound and the carbonyl halide.

Description

TECHNICAL FIELD The present invention relates to a method for safely producing a carbonyl halide at a lower cost. BACKGROUND ART A carbonyl halide such as carbonyl chloride is very important as a synthetic intermediate for various compounds. For example, a carbonate derivative is generally produced from carbonyl chloride and a nucleophilic functional group-containing compound. Carbonyl chloride is however very toxic. For example, carbonyl chloride is easily reacted with water to generate hydrogen chloride and has a history of use as a poisonous gas. In general, carbonyl chloride is produced by a high-heat-generating gas phase reaction of an anhydrous chlorine gas with high purity carbon monoxide in the presence of an activated carbon catalyst (Patent document 1 or the like). Carbon monoxide used in this reaction is also toxic. The basic process to produce carbonyl chloride has not changed much since the 1920s. Such a process to produce carbonyl chloride requires expensive large-scale facilities. An extensive safety assurance is essential in plant design due to the high toxicity of carbonyl chloride and leads to increased production costs. In addition, a process to produce carbonyl chloride in a large scale may possibly cause many environmental problems. Further, carbonyl chloride may be also produced by decomposing triphosgene [bis(trichloromethyl) carbonate] or diphosgene (trichloromethyl chloroformate) with a base such as triethylamine. But it is known that triphosgene and diphosgene are expensive reagents, may be potentially decomposed into carbonyl chloride by some physical or chemical stimuli, and are known to be highly toxic themselves. The inventor of the present invention has developed the method for producing a halogen and/or a carbonyl halide by irradiating light to a halogenated hydrocarbon in the presence of oxygen (Patent document 2). The method is safe, since the carbonyl halide produced by the method can be immediately reacted with a coexistent amine compound or alcohol compound to be reacted. The carbonyl halide which has not been used for the reaction can be collected not to be leaked outside by using a trap. For example, the inventor also has developed the method for producing a halogenated carboxylate ester by irradiating light to a mixture containing a halogenated hydrocarbon and an alcohol in the presence of oxygen (Patent document 3). The inventor also has developed the method for producing a carbonate derivative by irradiating light to a composition containing a halogenated hydrocarbon, a nucleophilic functional group-containing compound and a base in the presence of oxygen (Patent document 4 and Patent document 5). PRIOR ART DOCUMENT PATENT DOCUMENT Patent document 1: JP H9-59012 APatent document 2: JP 2013-181028 APatent document 3: WO 2015/156245Patent document 4: WO 2018/211952Patent document 5: WO 2018/211953 DISCLOSURE OF THE INVENTION PROBLEMS TO BE SOLVED BY THE INVENTION The inventor of the present invention has developed the method for producing a carbonyl halide by irradiating light to a halogenated hydrocarbon in the presence of oxygen as described above. The halogenated hydrocarbon may be once used and reused. But since many reusable halogenated hydrocarbons have been once used as a solvent and is liquid under atmospheric temperature and atmospheric pressure, the halogenated hydrocarbon has to be easily purified and the energy to gasify the halogenated hydrocarbon is required for the reaction in a gas phase. In addition, a halogenated hydrocarbon is relatively expensive. Methane is inexpensive and is required to be actively consumed, since the global warming potential of methane as a greenhouse gas is about 25 times as that of carbon dioxide. Thus, the objective of the present invention is to provide a method for producing a carbonyl halide safely at a low cost and a low environmental load. MEANS FOR SOLVING THE PROBLEMS The inventor of the present invention repeated intensive studies in order to solve the above-described problems. As a result, the inventor completed the present invention by finding that the reaction of methane in the presence of oxygen may possibly cause explosion but a carbonyl halide can be safely produced by irradiating light to a mixed gas containing methane, a halogen molecule and oxygen. The present invention is hereinafter described. [1] A method for producing a carbonyl halide, the method comprising the step of: irradiating a light to a mixed gas comprising methane, a halogen molecule gas and oxygen.[2] The method according to the above [1], wherein the carbonyl halide is carbonyl chloride, and the halogen molecule gas is a chlorine gas.[3] The method according to the above [1] or [2], wherein the light has a peak wavelength of 360 nm or more and 830 nm or less.[4] The method according to any one of the above [1] to [3], wherein the light is irradiated to the mixed gas at an atmospheric temperature.[5] The method according to any one of the above