Synthesis of triacetonediamine compounds by reductive amination proceeding from triacetonediamine and derivatives thereof

Patent metadata

Field	Value
Publication number	US-10227300-B2
Application number	US-201615004062-A
Country	US
Kind code	B2
Filing date	Jan 22, 2016
Priority date	Jan 22, 2015
Publication date	Mar 12, 2019
Grant date	Mar 12, 2019

Abstract

An N-substituted triacetonediamine compound is prepared by reacting 4-amino-2,2,6,6-tetramethylpiperidine or a derivative thereof with a carbonyl compound in a reductive amination, wherein reductive conditions are established by conducting the reaction in the presence of hydrogen and in the presence of a supported catalyst, wherein the supported catalyst includes 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 an N-substituted triacetonediamine compound, comprising:
reacting at least one triacetonediamine compound (I) with at least one carbonyl compound (II) under reductive conditions to obtain the N-substituted triacetonediamine compound,
wherein the triacetonediamine compound (I) is selected from the group consisting of the chemical structures (I-A), (I-B), (I-C), (I-D), and (I-E):

wherein the carbonyl compound (II) is selected from the group consisting of the chemical structures (II-A), (II-B), and (II-C):

and
wherein reductive conditions are established by reacting the at least one triacetonediamine compound (I) with the at least one carbonyl compound (II) in the presence of hydrogen and in the presence of a supported catalyst, wherein the supported catalyst comprises 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,
wherein in chemical structures (I-A), (I-B), (I-C), (I-D), and (I-E)
n is 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 are each independently 0 or 1;
wherein X 1 , X 2 , X 3 , X 4 , X 5 , X 6 , X 7 , X 8 , X 9 , X 10 , X 11 , X 12 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 are each independently selected from the group consisting of
unbranched or branched alkylene group having 1 to 30 carbon atoms,
divalent saturated hydrocarbyl group having 3 to 30 carbon atoms and having at least one saturated ring comprising 3 to 30 carbon atoms,
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, if present, are saturated, and
a bridging radical having a chemical structure selected from the group consisting of (i), (ii) with

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 list above including 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 list above including 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 list above including 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 list above including a direct bond,
and wherein Y 5 , if at least one of p 9 and p 10 has the value of 1, is selected from the list above including a direct bond,
wherein the R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 1 , R 8 , R 9 , R 10 , R 11 radicals are each independently selected from the group consisting of
hydrogen,
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 ),
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), (viii), and (ix) with

wherein J 1 , J 2 are each independently selected from the group consisting of CH, and N,
wherein K 1 , K 2 are each independently selected from the group consisting of —O—, —NH—, —N(CH 3 )—, —N(CH 2 CH 3 )—, —S—, and —CH 2 —,
wherein V 1 , V 2 , V 3 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 W 1 , W 2 , W 3 are each independently selected from the group consisting of H, methyl, and ethyl,
wherein c, d, e, f, g, h are each independently an integer from the range of 0 to 50,
wherein X 13 is 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, in the chemical structures (iii), (iv), (v), (vi), (vii), (viii), and (ix), at least one hydrogen radical bonded to a carbon atom 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 );
wherein the R 12 , R 13 , R 14 , R 15 , R 16 , R 17 radicals are each independently selected from the group consisting of

hydrogen,
unbranched or branched alkyl group having 1 to 30 carbon atoms, and
a group having the chemical structure (x) with

wherein the R 18 , R 19 , R 20 , R 21 , R 22 , R 23 radicals are each independently selected from the group consisting of
hydrogen,
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 ),
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 (xi), (xii), (xiii), (xiv), (xv), (xvi), and (xvii) with

wherein J 3 , J 4 are each independently selected from the group consisting of CH, and N,
wherein K 3 , K 4 are each independently selected from the group consisting of —O—, —NH—, —N(CH 3 )—, —N(CH 2 CH 3 )—, —S—, and —CH 2 —,
wherein V 4 , V 5 , V 6 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 W 4 , W 5 , W 6 are each independently selected from the group consisting of H, methyl, and ethyl,
wherein j, k, m, q, r, s are each independently an integer from the range of 0 to 50,
wherein X 14 is selected from the group

Assignees

• Willy Benjamin
• Niemeyer Jochen
• Kreilkamp Guenter
• Vom Bruch Beatrix
• Neumann Manfred
• Keup Michael
• Evonik Degussa Gmbh

Inventors

• Willy Benjamin
• Niemeyer Jochen
• Kreilkamp Guenter
• Vom Bruch Beatrix
• Neumann Manfred
• Keup Michael

Classifications

• C07D401/12

  linked by a chain containing hetero atoms as chain links · CPC title

• C07D211/58 Primary

  attached in position 4 · CPC title

• C07D401/14

  containing three or more hetero rings · CPC title