Aminophosphonium compounds

Details Aminophosphonium compounds Aminophosphonium compounds

2000-07-17

2002-10-15

Raymond, Richard L. (Department: 1624)

Organic compounds -- part of the class 532-570 series

Organic compounds

Chalcogen in the nitrogen containing substituent

C544S121000, C544S337000, C546S186000, C546S207000, C514S231500, C514S252120, C514S343000

Reexamination Certificate

active

06465643

ABSTRACT:

BACKGROUND OF THE INVENTION
The present invention relates to novel aminophosphonium compounds, to substance mixtures containing them, and to the preparation and use thereof.
Aminophosphonium compounds are used, as is evident from WO 98/32532 and WO 98/22413, as catalysts for preparing fluorine-containing compounds by a halogen/fluorine exchange reaction (halex reaction). Although the tetrakis(diethylamino)phosphonium bromide used in WO 98/32532 and WO 98/22413 gives good results, it has a very high dermal toxicity which stands in the way of industrial use, however.
SUMMARY OF THE INVENTION
The object is to provide novel compounds which are suitable as catalyst or component of catalyst systems for phase-transfer reactions, in particular for halogen-fluorine exchange reactions, have a lower dermal toxicity and achieve or even exceed the results obtainable on use of tetrakis(diethylamino)phosphonium bromide.
DESCRIPTION OF THE PREFERRED EMBODIMENTS
This object is achieved by compounds of the formula
in which one, two or three of the radicals R
1
, R
2
, R
3
and R
4
are
where m and n are an integer from 1 to 10, R
5
, R
6
, R
7
and R
8
are, independently of one another, identical or different and are a straight-chain or branched alkyl radical having 1 to 10 carbon atoms, and the remaining radical(s) R
1
to R
4
are
or —NR
9
R
10
, where R
9
and R
10
are identical or different and are a straight-chain or branched alkyl radical having 1 to 10 carbon atoms,
and X
−
is an inorganic or organic anion or an equivalent of a multiply charged inorganic or organic anion.
Compounds of interest are those of the formula (1) in which one or two of the radicals R
1
, R
2
, R
3
and R
4
are
and the remaining radicals R
1
to R
4
are
or —NR
9
R
10
.
Importance further attaches to compounds of the formula (1) in which m and n are an integer from 1 to 6, and R
5
, R
6
, R
7
, R
8
, R
9
and R
10
are identical or different and are a straight-chain or branched alkyl radical having 1 to 4 carbon atoms.
The aforementioned radicals R
1
, R
2
, R
3
and R
4
are, in particular,
preferably —N{(CH
2
—CH
2
—O)
m
R
5
}
2
or —N{(CH
2
—CH
2
—N(R
7
))
n
R
8
}
2
, particularly preferably —N{(CH
2
—CH
2
—O)
m
R
5
}
2
.
The aforementioned remaining radical(s) R
1
to R
4
are, in particular,
In the compounds of the formula (1), X
−
is F
−
, Cl
−
, Br
−
, I
−
, ClO
4
−
, BF
4
−
, PF
6
−
, NO
3
−
, HSO
4
−
, ½ SO
4
2−
, H
2
PO
4
−
, ½ HPO
4
2−
, ⅓ PO
4
3−
, R′—COO
−
, where R′ is an alkyl radical having 1 to 9 carbon atoms, a phenyl radical, benzyl radical or naphthyl radical, R″—SO
3
−
, where R″ is an alkyl radical having 1 to 18 carbon atoms, a phenyl radical, tolyl radical or naphthyl radical, HCO
3
−
, ½ CO
3
2−
or ½ C
6
H
4
(COO
−
)
2
.
X
−
is, in particular, F
−
, Cl
−
, Br
−
, I
−
, BF
4
−
, PF
6
−
or ½ SO
4
−
, preferably F
−
, Cl
−
, or Br
−
, particularly preferably Cl
−
.
The following aminophosphonium compounds (aminophosphonium salts) may be mentioned as examples without claiming completeness.
Bis(2-methoxyethyl)amino-tris(pyrrolidino)phosphonium chloride
Di(bis(2-methoxyethyl)amino)-bis(pyrrolidino)phosphonium chloride
Tri(bis(2-methoxyethyl)amino)-(pyrrolidino)phosphonium chloride
Bis(methyl-diethoxyethylene)amino-tris(pyrrolidino)phosphonium chloride
Di(bis(methyl-diethoxyethylene)amino)-bis(pyrrolidino)phosphonium chloride
Tri(bis(methyl-diethoxyethylene)amino)-(pyrrolidino)phosphonium chloride
Bis(methyl-tetraethoxyethylene)amino-tris(pyrrolidino)phosphonium chloride
Di(bis(methyl-diethoxyethylene)amino)-(pyrrolidino)phosphonium chloride
Tri(bis(methyl-tetraethoxyethylene)amino)-(pyrrolidino)phosphonium chloride
Morpholino-tris(pyrrolidino)phosphonium chloride
Dimorpholino-bis(pyrrolidino)phosphonium chloride
Trimorpholino-(pyrrolidino)phosphonium chloride
Bis(2-methoxyethyl)amino-tris(piperidino)phosphonium chloride
Di(bis(2-methoxyethyl)amino)-bis(piperidino)phosphonium chloride
Tri(bis(2-methoxyethyl)amino)-(piperidino)phosphonium chloride
Bis(methyl-diethoxyethylene)amino-tris(piperidino)phosphonium chloride
Di(bis(methyl-diethoxyethylene)amino)-bis(piperidino)phosphonium chloride
Tri(bis(methyl-diethoxyethylene)amino)-(piperidino)phosphonium chloride
Bis(methyl-tetraethoxyethylene)amino-tris(piperidino)phosphonium chloride
Di(bis(methyl-tetraethoxyethylene)amino)-bis(piperidino)phosphonium chloride
Tri(bis(methyl-tetraethoxyethylene)amino)-(piperidino)phosphonium chloride
Morpholino-tris(piperidino)phosphonium chloride
Dimorpholino-bis(piperidino)phosphonium chloride
Bis(2-methoxyethyl)amino-tris(diethylamino)phosphonium chloride
Di(bis(2-methoxyethyl)amino)-bis(diethylamino)phosphonium chloride
Tri(bis(2-methoxyethyl)amino)-(diethylamino)phosphonium chloride
Bis(methyl-tetraethoxyethylene)amino-tris(diethylamino)phosphonium chloride
Di(bis(methyl-tetraethoxyethylene)amino)-bis(diethylamino)phosphonium chloride
Tri(bis(methyl-tetraethoxyethylene)amino)-(diethylamino)phosphonium chloride
Morpholino-tris(diethylamino)phosphonium chloride
Dimorpholino-bis(diethylamino)phosphonium chloride
Trimorpholino-(diethylamino)phosphonium chloride
Bis(2-methoxyethyl)amino-tris(dimethylamino)phosphonium chloride
Di(bis(2-methoxyethyl)amino)-bis(dimethylamino)phosphonium chloride
Tri(bis(2-methoxyethyl)amino)-(dimethylamino)phosphonium chloride
Bis(methyl-bisethoxyethylene)amino-tris(dimethylamino)phosphonium chloride
Di(bis(methyl-bisethoxyethylene)amino)-bis(dimethylamino)phosphonium chloride
Tri(bis(methyl-bisethoxyethylene)amino)-(dimethylamino)phosphonium chloride
Bis(methyl-tetraethoxyethylene)amino-tris(dimethylamino)phosphonium chloride
Di(bis(methyl-tetraethoxyethylene)amino)-bis(dimethylamino)phosphonium chloride
Tri(bis(methyl-tetraethoxyethylene)amino)-(dimethylamino)phosphonium chloride
Tris(dimethylamino)-morpholino-phosphonium chloride
Bis(dimethylamino)-dimorpholino-phosphonium chloride
Dimethylamino-trimorpholino-phosphonium chloride
Bis(2-methoxyethyl)amino-tris(butyl-ethylamino)phosphonium chloride
Di(bis(2-methoxyethyl)amino)-bis(butyl-ethylamino)phosphonium chloride
Tri(bis(2-methoxyethyl)amino)-(butyl-ethylamino)phosphonium chloride
Bis(methyl-tetraethoxyethylene)amino-tris(butyl-ethylamino)phosphonium chloride
Di(bis(methyl-tetraethoxyethylene)amino)-bis(butyl-ethylamino)phosphonium chloride
Tri(bis(methyl-tetraethoxyethylene)amino)-(butyl-ethylamino)phosphonium chloride
Tris(butyl-ethylamino)-morpholino-phosphonium chloride
Bis(butyl-ethylamino)-dimorpholino-phosphonium chloride
(Butyl-ethylamino)-trimorpholino-phosphonium chloride
N-Methylpiperazino-tris(pyrrolidino)phosphonium chloride
Bis(N-methylpiperazino)-bis(pyrrolidino)phosphonium chloride
Tris(N-methylpiperazino)-(pyrrolidino)phosphonium chloride
N-Methylpiperazino-tris(diethylamino)phosphonium chloride
Bis(N-methylpiperazino)-bis(diethylamino)phosphonium chloride
Tris(N-methylpiperazino)-(diethylamino)phosphonium chloride
N-Methylpiperazino-tris(dimethylamino)phosphonium chloride
Bis(N-methylpiperazino)-bis(dimethylamino)phosphonium chloride
Tris(N-methylpiperazino)-(dimethylamino)phosphonium chloride
N-Methylpiperazino-tris(butyl-ethylamino)phosphonium chloride
Bis(N-methylpiperazino)-bis(butyl-ethylamino)phosphonium chloride
Tris(N-methylpiperazino)-(butyl-ethylamino)phosphonium chloride
In place of the listed aminophosphonium chlorides it is also possible to employ, for example, the corresponding bromides, iodides, fluorides, sulfates, hydrogen sulfates, acetates or phthalates.
The present invention also relates to mixtures of substances comprising at least one compound of the formula
in which R
1
, R
2
, R
3
, R
4
and X
−
have the above meaning, and at least one compound selected from the group of quaternary ammonium compounds of the formula
quaternary ammonium salts or phosphonium salts of the formula
pol

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