Classifications

• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D223/00—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom
  • C07D223/02—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom not condensed with other rings
  • C07D223/06—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom not condensed with other rings with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
  • C07D223/08—Oxygen atoms
  • C07D223/10—Oxygen atoms attached in position 2
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
  • C07C227/12—Formation of amino and carboxyl groups

Definitions

• ⁇ -Caprolactam is an important chemical raw material that is a raw material for polyamide, and is industrially produced all over the world, and most of it is used as a raw material for nylon 6, which is a polyamide.
• As an industrial production method for ⁇ -caprolactam a production method using a Beckmann rearrangement reaction from cyclohexanone oxime with fuming sulfuric acid is widely adopted. However, since a large amount of ammonium sulfate is by-produced in the neutralization step in the Beckmann rearrangement reaction, development of a method for producing ⁇ -caprolactam that does not by-produce ammonium sulfate is required.
• ⁇ -caprolactam can be produced from 5-cyanobarrel amide in a high yield while reducing the environmental load and the energy load.
• 5-Cyanovaleramide is a cyano group-containing carboxylic acid amide, also called 5-cyanopentanamide.
• 5-Cyanobarrelamide is a hydration of one cyano group of adiponitrile (eg, Bioorganic and Medicinal Chemistry, vol. 7, 2239-2245 (1999)), dehydration of one amide group of adipamide (eg, US No. 3331866). It can be synthesized according to the specification).
• Hydrogen to react with 5-cyanobarrel amide may be added to the reactor all at once or sequentially.
• the 5-cyanobarrelamide hydrogenation reaction mixture which is the product of step (A), is a reaction of 5-cyanobarrelamide in an aqueous solvent in the presence of a hydrogenation catalyst as described above. Means a mixture of multiple products produced by. That is, the 5-cyanobarrelamide hydrogenation reaction mixture contains 6-aminocaproic acid amide as a main component, and in addition, a dimer of 6-aminocaproic acid amide, an oligomer, ⁇ -caprolactam, and unreacted 5-cyano. It is a substance containing barrel amide and the like. Therefore, pure 6-aminocaproic acid amide is inconsistent with the 5-cyanobarrel amide hydrogenation reaction mixture.
• Step (B) The aqueous solution containing the 5-cyanobarrelamide hydrogenation reaction mixture obtained in the step (A) was added again to a stainless steel autoclave (manufactured by Pressure Resistant Glass Industry Co., Ltd.) having an internal volume of 0.2 L. After purging the inside of the autoclave with nitrogen, nitrogen gas was introduced so that the partial pressure of nitrogen in the autoclave was 0.5 MPa (gauge pressure). Next, the temperature inside the autoclave was raised to 250 ° C. After holding at 250 ° C. for 1 hour, the mixture was allowed to cool to room temperature, the gas in the autoclave was released and returned to normal pressure, and then the reaction solution was recovered and analyzed by HPLC. The results are shown in Table 1-1.

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• Chemical & Material Sciences (AREA)
• Organic Chemistry (AREA)
• Other In-Based Heterocyclic Compounds (AREA)
• Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
• Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

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• 2020
  • 2020-11-18 WO PCT/JP2020/042999 patent/WO2021100759A1/ja not_active Ceased
  • 2020-11-18 EP EP20890793.1A patent/EP4063345A4/en active Pending
  • 2020-11-18 US US17/777,739 patent/US12365652B2/en active Active
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