Process for preparing an N-methyl-substituted triacetonamine compound

Patent metadata

Field	Value
Publication number	US-9617245-B2
Application number	US-201615003978-A
Country	US
Kind code	B2
Filing date	Jan 22, 2016
Priority date	Jan 22, 2015
Publication date	Apr 11, 2017
Grant date	Apr 11, 2017

Abstract

An N-methyl-substituted triacetonamine compound is prepared by reacting at least one triacetonamine compound (I) with formaldehyde under reductive conditions, in the presence of hydrogen and in the presence of a supported catalyst, wherein the supported catalyst contains at least one metal M, wherein the metal M is selected from the group consisting of V, Cr, Mo, Mn, Ni, Pd, Pt, Fe, Ru, Os, Co, Rh, Ir, and Cu.

First claim

The invention claimed is:

1. A process for preparing at least one N-methyl-substituted triacetonamine compound, comprising:
reacting at least one triacetonamine compound (I) with formaldehyde under reductive conditions,
wherein the reductive conditions comprise reacting the at least one triacetonamine compound (I) with formaldehyde in the presence of hydrogen and a supported catalyst comprising at least one metal M selected from the group consisting of V, Cr, Mo, Mn, Ni, Pd, Pt, Fe, Ru, Os, Co, Rh, Ir, and Cu, and
the triacetonamine compound (I) is selected from the group consisting of the chemical structures (I-B), (I-C), (I-D), (I-E), (I-F), (I-G), and (I-H)

wherein n 1 , n 2 are each independently an integer from the range of 1 to 20;
wherein p 1 , p 2 , p 3 , p 4 , p 5 , p 6 , p 7 , p 8 , p 9 , p 10 , p 11 , p 12 , p 13 , p 14 , p 15 , p 16 , p 17 , p 18 , p 19 , p 20 are each independently 0 or 1;
wherein X 1 is selected from the group consisting of OH, —O., unbranched or branched alkyl group having 1 to 10 carbon atoms, and unbranched or branched alkoxy group having 1 to 10 carbon atoms;
wherein X 2 , X 3 are each independently selected from the group consisting of hydrogen, OH, —O., unbranched or branched alkyl group having 1 to 10 carbon atoms, and unbranched or branched alkoxy group having 1 to 10 carbon atoms, and wherein X 2 , X 3 are each selected independently, with the exclusion of: X 2 ═X 3 =hydrogen;
wherein X 4 , X 5 , X 6 , X 7 , X 8 are each independently selected from the group consisting of hydrogen, OH, —O., unbranched or branched alkyl group having 1 to 10 carbon atoms, and unbranched or branched alkoxy group having 1 to 10 carbon atoms;
wherein Y 1 , Y 2 , Y 3 , Y 4 , Y 5 , Y 6 , Y 7 , Y 8 , Y 9 , Y 10 are each independently selected from the group consisting of
an unbranched or branched alkylene group having 1 to 30 carbon atoms,
a divalent saturated hydrocarbyl group having 3 to 30 carbon atoms and having at least one saturated ring comprising 3 to 30 carbon atoms,
a divalent hydrocarbyl group having 6 to 30 carbon atoms, of which at least 6 carbon atoms are present in an aromatic system and the other carbon atoms, which are optionally present, are saturated, and
a bridging radical having a chemical structure selected from the group consisting of (i), and (ii)

wherein
Q 1 , Q 2 are each independently selected from the group consisting of —O—, —S—, —NH— and —NR′— with R′=unbranched or branched alkyl group having 1 to 6 carbon atoms,
wherein a is an integer selected from the range of 1 to 50,
wherein b is an integer selected from the range of 0 to 50,

and wherein Y 1 , if at least one of p 1 and p 2 has the value of 1, is selected from the group consisting of an unbranched or branched alkylene group having 1 to 30 carbon atoms; a divalent saturated hydrocarbyl group having 3 to 30 carbon atoms and having at least one saturated ring comprising 3 to 30 carbon atoms; a divalent hydrocarbyl group having 6 to 30 carbon atoms, of which at least 6 carbon atoms are present in an aromatic system and the other carbon atoms, which are optionally present, are saturated; a bridging radical having the chemical structure of (i) or (ii); and a direct bond,
and wherein Y 2 , if at least one of p 3 and p 4 has the value of 1, is selected from the group consisting of an unbranched or branched alkylene group having 1 to 30 carbon atoms; a divalent saturated hydrocarbyl group having 3 to 30 carbon atoms and having at least one saturated ring comprising 3 to 30 carbon atoms; a divalent hydrocarbyl group having 6 to 30 carbon atoms, of which at least 6 carbon atoms are present in an aromatic system and the other carbon atoms, which are optionally present, are saturated; a bridging radical having the chemical structure of (i) or (ii); and a direct bond,
and wherein Y 3 , if at least one of p 5 and p 6 has the value of 1, is selected from the group consisting of an unbranched or branched alkylene group having 1 to 30 carbon atoms, a divalent saturated hydrocarbyl group having 3 to 30 carbon atoms and having at least one saturated ring comprising 3 to 30 carbon atoms; a divalent hydrocarbyl group having 6 to 30 carbon atoms, of which at least 6 carbon atoms are present in an aromatic system and the other carbon atoms, which are optionally present, are saturated; a bridging radical having the chemical structure of (i) or (ii); and a direct bond,
and wherein Y 4 , if at least one of p 7 and p 8 has the value of 1, is selected from the group consisting of an unbranched or branched alkylene group having 1 to 30 carbon atoms, a divalent saturated hydrocarbyl group having 3 to 30 carbon atoms and having at least one saturated ring comprising 3 to 30 carbon atoms; a divalent hydrocarbyl group having 6 to 30 carbon atoms, of which at least 6 carbon atoms are present in an aromatic system and the other carbon atoms, which are optionally present, are saturated; a bridging radical having the chemical structure of (i) or (ii); and a direct bond,
and wherein Y 5 , if at least one of p 11 and p 12 has the value of 1, is selected from the group consisting of an unbranched or branched alkylene group having 1 to 30 carbon atoms; a divalent saturated hydrocarbyl group having 3 to 30 carbon atoms and having at least one saturated ring comprising 3 to 30 carbon atoms; a divalent hydrocarbyl group having 6 to 30 carbon atoms, of which at least 6 carbon atoms are present in an aromatic system and the other carbon atoms, which are optionally present, are saturated; a bridging radical having the chemical structure of (i) or (ii); and a direct bond,

and wherein Y 6 , if at least one of p 13 and p 14 has the value of 1, is selected from the group consisting of an unbranched or branched alkylene group having 1 to 30 carbon atoms; a divalent saturated hydrocarbyl group having 3 to 30 carbon atoms and having at least one saturated ring comprising 3 to 30 carbon atoms; a divalent hydrocarbyl group having 6 to 30 carbon atoms, of which at least 6 carbon atoms are present in an aromatic system and the other carbon atoms, which are optionally present, are saturated; a bridging radical having the chemical structure of (i) or (ii); and a direct bond,
and wherein Z 1 , Z 2 , Z 3 , Z 4 are each independently selected from the group consisting of —O—, —S—, and —NR 30 —;
wherein the R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 , R 19 , R 20 , R 30 radicals are each independently selected from the group consisting of
hydrogen,
an unbranched or branched alkyl group which has 1 to 30 carbon atoms and in which at least one hydrogen radical may be replaced by a radical selected from the group consisting of —OH, —NH 2 , —OCH 3 , —OCH 2 CH 3 , —NH(CH 3 ), —N(CH 3 ) 2 , —NH(CH 2 CH 3 ), —N(CH 2 CH 3 ) 2 , and —N(CH 3 )(CH 2 CH 3 ),
an unbranched or branched acyl group which has 1 to 30 carbon atoms and in which at least one hydrogen radical may be replaced by a radical selected from the group consisting of —OH, —NH 2 , —OCH 3 , —OCH 2 CH 3 , —NH(CH 3 ), —N(CH 3 ) 2 , —NH(CH 2 CH 3 ), —N(CH 2 CH 3 ) 2 , and —N(CH 3 )(CH 2 CH 3 ), and
a radical having a chemical structure selected from the group consisting of (iii), (iv), (v), (vi), (vii), (vi

Assignees

• Niemeyer Jochen
• Willy Benjamin
• Nissen Felix
• Neumann Manfred
• Kreilkamp Guenter
• Schering Sabine
• Evonik Degussa Gmbh

Inventors

• Niemeyer Jochen
• Willy Benjamin
• Nissen Felix
• Neumann Manfred
• Kreilkamp Guenter
• Schering Sabine

Classifications

• C07D211/74

  Oxygen atoms · CPC title

• C07D211/46

  having a hydrogen atom as the second substituent in position 4 · CPC title

• C07D401/14 Primary

  containing three or more hetero rings · CPC title

• C07D211/58 Primary

  attached in position 4 · CPC title

• C07D413/14

  containing three or more hetero rings · CPC title