Process for preparing phosphorus containing cyanohydrins
The present invention relates primarily to a process for preparing certain phosphorus-containing cyanohydrins of the formula (I), and also to certain phosphorus-containing cyanohydrins per se and to their use for the preparation of glufosinate and/or glufosinate salts. The present invention further relates to certain mixtures particularly suitable for preparing the phosphorus-containing cyanohydrins of the formula (I).
1. An apparatus comprising a first mixture of one or more compounds of the formula (IV) and one or more compounds of the formula (II) in a vessel
and
a second mixture comprising:
one or more compounds of the formula (II) and one or more compounds of the formula (III) in a separate vessel,
where the compounds of the formula (II) and (III) are as follows:
R 1 is (C 1 -C 12 )-alkyl, (C 1 -C 12 )-haloalkyl, (C 6 -C 10 )-aryl, (C 6 -C 10 )-haloaryl, (C 7 -C 10 )-aralkyl, (C 7 -C 10 )-haloaralkyl, (C 4 -C 10 )-cycloalkyl or (C 4 -C 10 )-halocycloalkyl,
R 2 is (C 1 -C 12 )-alkyl, (C 1 -C 12 )-haloalkyl, (C 6 -C 10 )-aryl, (C 6 -C 10 )-haloaryl, (C 7 -C 10 )-aralkyl, (C 7 -C 10 )-haloaralkyl, (C 4 -C 10 )-cycloalkyl or (C 4 -C 10 )-halocycloalkyl,
R 3 and R 4 are in each case independently of one another hydrogen, (C 1 -C 4 )-alkyl, phenyl or benzyl,
X is oxygen or sulphur, and
n is 0 or 1
and the compounds of the formula (IV) have the structure as follows:
where
R 5 is methyl, ethyl, 2,2-dimethylpropyl or phenyl,
R 6 independently at each occurrence is (C 1 -C 10 )-alkyl,
and
R 7 is hydrogen or (C 1 -C 10 )-alkyl.
2. The apparatus according to claim 1 , wherein the second mixture contains no compound of the formula (IV) and/or no compound of the formula (I), wherein the compound of the formula (I) has the structure as follows:
3. The apparatus according to claim 1 , where the compounds of the formula (II) and (III) have the structure as follows:
where:
R 1 is (C 1 -C 6 )-alkyl, (C 1 -C 6 )-haloalkyl, (C 6 -C 8 )-aryl, (C 6 -C 8 )-haloaryl, (C 7 -C 10 )-aralkyl, (C 7 -C 10 )-haloaralkyl, (C 5 -C 8 )-cycloalkyl or (C 5 -C 8 )-halocycloalkyl,
R 2 is (C 1 -C 6 )-alkyl, (C 1 -C 6 )-haloalkyl, (C 6 -C 8 )-aryl, (C 6 -C 8 )-haloaryl, (C 7 -C 10 )-aralkyl, (C 7 -C 10 )-haloaralkyl, (C 5 -C 8 )-cycloalkyl or (C 5 -C 8 )-halocycloalkyl
and the compounds of the formula (IV) are selected from the group consisting of tert-butyl peroxypivalate, tert-amyl peroxypivalate, tert-butyl peroxyneodecanoate, 1,1,3,3-tetramethylbutyl peroxyneodecanoate, tert-butylperoxy-2-ethylhexanoate, 1,1,3,3-tetramethylbutyl peroxy-2-ethylhexanoate, tert-amyl peroxyneodecanoate, cumyl peroxyneodecanoate, cumyl peroxyneoheptanoate, and cumyl peroxypivalate.
4. The apparatus according to claim 1 , wherein
R 6 independently at each occurrence is (C 1 -C 6 )-alkyl,
and
R 7 is hydrogen or (C 1 -C 6 )-alkyl.
5. The apparatus according to claim 1 , wherein
R 1 is (C 1 -C 4 )-alkyl or (C 1 -C 4 )-haloalkyl,
R 2 is (C 1 -C 6 )-alkyl or (C 1 -C 6 )-haloalkyl,
R 3 and R 4 are in each case independently of one another hydrogen or methyl,
X is oxygen, and
n is 1.
6. The apparatus according to claim 1 , wherein
R 1 is methyl or ethyl, R 2 is (C 3 -C 6 )-alkyl, R 3 and R 4 are hydrogen or methyl, n is 1, and X is oxygen.
7. The apparatus according to claim 1 , wherein
R 1 is methyl, R 2 is n-butyl or n-pentyl, R 3 and R 4 are hydrogen, n is 1, and X is oxygen.
8. The apparatus according to claim 1 , wherein
R 3 and R 4 are in each case independently of one another hydrogen or methyl, and
the compounds of the formula (IV) are selected from the group consisting of tert-butyl peroxyneodecanoate, 1,1,3,3-tetramethylbutyl peroxyneodecanoate, tert-butylperoxy-2-ethylhexanoate, 1,1,3,3-tetramethylbutyl peroxy-2-ethylhexanoate, and cumyl peroxyneodecanoate.
9. The apparatus according to claim 1 , wherein
R 3 and R 4 are hydrogen, and
the compounds of the formula (IV) are selected from the group consisting of 1,1,3,3-tetramethylbutyl peroxyneodecanoate, tert-butyl peroxyneodecanoate, and tert-butylperoxy-2-ethylhexanoate.
10. The apparatus according to claim 1 , wherein the compounds of the formula (IV) are selected from the group consisting of tert-butyl peroxyneodecanoate, 1,1,3,3-tetramethylbutyl peroxyneodecanoate, tert-butylperoxy-2-ethylhexanoate, 1,1,3,3-tetramethylbutyl peroxy-2-ethylhexanoate, and cumyl peroxyneodecanoate.
11. The apparatus according to claim 1 , wherein the compounds of the formula (IV) are selected from the group consisting of 1,1,3,3-tetramethylbutyl peroxyneodecanoate, tert-butyl peroxyneodecanoate, and tert-butylperoxy-2-ethylhexanoate.
12. An apparatus comprising a first mixture of one or more compounds of the formula (IV) and one or more compounds of the formula (III) in a vessel
and
a second mixture comprising
one or more compounds of the formula (II) and one or more compounds of the formula (III) in a separate vessel,
where the compounds of the formula (II) and (III) are as follows:
R 1 is (C 1 -C 12 )-alkyl, (C 1 -C 12 )-haloalkyl, (C 6 -C 10 )-aryl, (C 6 -C 10 )-haloaryl, (C 7 -C 10 )-aralkyl, (C 7 -C 10 )-haloaralkyl, (C 4 -C 10 )-cycloalkyl or (C 4 -C 10 )-halocycloalkyl,
R 2 is (C 1 -C 12 )-alkyl, (C 1 -C 12 )-haloalkyl, (C 6 -C 10 )-aryl, (C 6 -C 10 )-haloaryl, (C 7 -C 10 )-aralkyl, (C 7 -C 10 )-haloaralkyl, (C 4 -C 10 )-cycloalkyl or (C 4 -C 10 )-halocycloalkyl,
R 3 and R 4 are in each case independently of one another hydrogen, (C 1 -C 4 )-alkyl, phenyl or benzyl,
X is oxygen or sulphur, and
n is 0 or 1
and the compounds of the formula (IV) have the structure as follows:
where
R 5 is methyl, ethyl, 2,2-dimethylpropyl or phenyl,
R 6 independently at each occurrence is (C 1 -C 10 )-alkyl,
and
R 7 is hydrogen or (C 1 -C 10 )-alkyl.
13. The apparatus according to claim 12 , wherein the second mixture contains no compound of the formula (IV) and/or no compound of the formula (I), wherein the compound of the formula (I) has the structure as follows:
14. The apparatus according to claim 12 , wherein
R 6 independently at each occurrence is (C 1 -C 4 )-alkyl,
and
R 7 is hydrogen or (C 1 -C 4 )-alkyl.
15. The apparatus according to claim 12 , wherein
R 1 is (C 1 -C 4 )-alkyl or (C 1 -C 4 )-haloalkyl,
R 2 is (C 1 -C 6 )-alkyl or (C 1 -C 6 )-haloalkyl,
R 3 and R 4 are in each case independently of one another hydrogen or methyl,
X is oxygen, and
n is 1.
16. The apparatus according to claim 12 , wherein
R 1 is methyl or ethyl, R 2 is (C 3 -C 6 )-alkyl, R 3 and R 4 are hydrogen or methyl, n is 1, and X is oxygen.
17. The apparatus according to claim 12 , wherein
R 1 is methyl, R 2 is n-butyl, R 3 and R 4 are hydrogen, n is 1, and X is oxygen.
18. The apparatus according to claim 12 , where the compounds of the formula (II) and (III) have the structure as follows:
where:
R 1 is (C 1 -C 6 )-alkyl, (C 1 -C 6 )-haloalkyl, (C 6 -C 8 )-aryl, (C 6 -C 8 )-haloaryl, (C 7 -C 10 )-aralkyl, (C 7 -C 10 )-haloaralkyl, (C 5 -C 8 )-cycloalkyl or (C 5 -C 8 )-halocycloalkyl,
R 2 is (C 1 -C 6 )-alkyl, (C 1 -C 6 )-haloalkyl, (C 6 -C 8 )-aryl, (C 6 -C 8 )-haloaryl, (C 7 -C 10 )-aralkyl, (C 7 -C 10 )-haloaralkyl, (C 5 -C 8 )-cycloalkyl or (C 5 -C 8 )-halocycloalkyl
and the compounds of the formula (IV) are selected from the group consisting of tert-butyl peroxypivalate, tert-amyl peroxypivalate, tert-butyl peroxyneodecanoate, 1,1,3,3-tetramethylbutyl peroxyneodecanoate, tert-butylperoxy-2-ethylhexanoate, 1,1,3,3-tetramethylbutyl peroxy-2-ethylhexanoate, tert-amyl peroxyneodecanoate, cumyl peroxyneodecanoate, cumyl peroxyneoheptanoate, and cumyl peroxypivalate.
19. The apparatus according to claim 12 , wherein the compounds of the formula (IV) are selected from the group consisting of tert-butyl peroxyneodecanoate, 1,1,3,3-tetramethylbutyl peroxyneodecanoate, tert-butylperoxy-2-ethylhexanoate, 1,1,3,3-tetramethylbutyl peroxy-2-ethylhexanoate, and cumyl peroxyneodecanoate.
20. The apparatus according to claim 12 , wherein the compounds of the formula (IV) are selected from the group consisting of 1,1,3,3-tetramethylbutyl peroxyneodecanoate, tert-butyl peroxyneodecanoate, and tert-butylperoxy-2-ethylhexanoate.