Organopolysiloxanes containing phosphonic groups, method for the production and use thereof

• US 20060241314A1
• Filed: 06/19/2006
• Published: 10/26/2006
• Est. Priority Date: 01/09/2001
• Status: Active Grant

• Current Assignee: Phosphonics Ltd. (Carbosynth Holdings Ltd.)
• Original Assignee: Phosphonics Ltd. (Carbosynth Holdings Ltd.)
• Inventors: Sullivan, Alice Caroline, Wilson, John Robert Howe
• Granted Patent: US 7,728,159 B2
• Time in Patent Office: Days
• US Class Current: 556/9
• CPC Class Codes: B01J 39/19 obtained otherwise than by reactions only involving unsaturated carbon-to-carbon bonds
• CPC Class Codes: C07C 41/56 by condensation of aldehydes, paraformaldehyde, or ketones
• CPC Class Codes: C07C 43/307 having acetal carbon atoms bound to carbon atoms of six-membered aromatic rings
• CPC Class Codes: C07C 45/515 the singly bound functional group being an acetalised, ketalised hemi-acetalised, or hemi-ketalised hydroxyl group cyclic acetals or ketals C07C45/59, C07C45/60
• CPC Class Codes: C07C 45/52 by dehydration and rearrangement involving two hydroxy groups in the same molecule
• CPC Class Codes: C07C 45/72 by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups
• CPC Class Codes: C07C 45/74 combined with dehydration
• CPC Class Codes: C07C 49/04 Saturated compounds containing keto groups bound to acyclic carbon atoms
• CPC Class Codes: C07C 49/78 Acetophenone
• CPC Class Codes: C07C 49/796 polycyclic
• CPC Class Codes: C07C 51/29 with halogen-containing compounds which may be formed in situ
• CPC Class Codes: C07C 63/06 Benzoic acid
• CPC Class Codes: C07C 63/10 Halides thereof
• CPC Class Codes: C07C 67/03 by reacting an ester group with a hydroxy group
• CPC Class Codes: C07C 67/08 by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
• CPC Class Codes: C07C 69/58 Esters of straight chain acids with eighteen carbon atoms in the acid moiety
• CPC Class Codes: C07D 301/12 with hydrogen peroxide or inorganic peroxides or peracids
• CPC Class Codes: C07D 303/04 containing only hydrogen and carbon atoms in addition to the ring oxygen atoms
• CPC Class Codes: C07F 9/4012 substituted by B, Si, P or a metal C07F9/4025 takes precedence
• CPC Class Codes: C08G 77/30 phosphorus-containing groups

Abstract

The invention relates to new compounds of the formula, wherein R and R¹ are each independently hydrogen, a linear or branched C_1-40 alkyl, C_2-40 alkenyl or C_2-40 alkynyl group, an aryl or C_1-40 alkylaryl group or an optionally complex metal ion Mⁿ⁺/n wherein n is an integer from 1 to 8; the free valences of the silicate oxygen atoms are saturated by one or more of: silicon atoms of other groups of the formula, hydrogen, a linear or branched C_1-12 alkyl qroup or by cross-linking bridge members R³_qM¹(OR²)_mO_k/2 or Al(OR²)_3·pO_p/2 or R³Al(OR²)_2·rO_r/2; where M¹ is Si or Ti; R² is linear or branched C_1-12 alkyl group; and R³ is a linear or branched C_1-6 alkyl group; k is an integer from 1 to 4 and q and m are integers from 0 to 2; such that m+k+q=4; and p is an integer from 1 to 3; and r is an integer from 1 to 2; or other known oxo metal bridging systems; x, y and z are integers such that the radio of x:y+z, varies from 0.00001 to 100,000 with the fragments [O_3/2SiCH(CH₂PO(OR)(OR¹))CH₂CH₂SiO_3/2]_X and [O_3/2SiCH₂CH₂PO(OR)(OR¹)]_Y always present whilst the integer z varies from 0 to 200y. The compounds are useful as catalysts for a wide variety of reactions and have the advantages that they can be prepared in a one-pot reaction and have functional group losding can be tailored to be at a required level. In addition, the compounds have high chemical and thermal stability, fixed and rigid structures, are insoluble in organic solvents, high resistance to ageing, and can easily be purified and reused.

Claims

1. A compound of General Formula 1:

29. The process for conducting an acid catalyzed reaction, the process comprising employing as a catalyst the compound of claim 1, wherein either or both of R and R¹ is hydrogen.

30. The process for conducting an acid catalyzed reaction, the process comprising employing as a catalyst the compound of claim 1, wherein one of R and R¹ is hydrogen and the other is C_1-40 alkyl, C_2-40 alkenyl, C_2-40 alkynyl, aryl, C_1-8 alkylaryl or a metal ion derived from a lanthanide, actinide, main group or transition metal.

31. The process for conducting an acid catalyzed reaction, the process comprising employing as a catalyst the compound of claim 1, wherein one of R or R¹ is hydrogen and the other is C_1-4 alkyl, phenyl, or C_1-8 alkylaryl.

32. The process for conducting an oxidation, reduction, alkylation, polymerization, hydroformylation, arylation, acylation, isomerization, alkylation, carboxylation, carbonylation, esterification, trans-esterification or rearrangement reaction, the process comprising employing as a catalyst the compound of claim 1, wherein one of R or R¹ is hydrogen or Mⁿ⁺/n and the other is C_12-40 alkyl, C_12-40 alkenyl, C_12-40 alkynyl, C_12-40 alkylaryl or aryl.

33. The process for conducting an oxidation, reduction, alkylation, polymerization, hydroformylation, arylation, acylation, isomerization, alkylation, carboxylation, carbonylation, esterification, trans-esterification or rearrangement reaction, the process comprising employing as a catalyst the compound of claim 1, wherein either or both of R and R¹ is Mⁿ⁺/n.

34. The process for conducting an oxidation, reduction, alkylation, polymerization, hydroformylation, arylation, acylation, isomerization, alkylation, carboxylation, carbonylation, esterification, trans-esterification or rearrangement reaction, the process comprising employing as a catalyst the compound of claim 1, wherein one of R and R¹ is Mⁿ⁺/n and the other is hydrogen or a C_1-12 alkyl, C_1-12 alkenyl, C_1-12 alkynyl, aryl or C_1-12 alkylaryl group.

35. The process for conducting an oxidation, reduction, alkylation, polymerization, hydroformylation, arylation, acylation, isomerization, alkylation, carboxylation, carbonylation, esterification, trans-esterification or rearrangement reaction, the process comprising employing as a catalyst the compound of claim 1, wherein one or both of R and R¹ is Mⁿ⁺/n, and Mⁿ⁺ is derived from a lanthanide, actinide, main group or transition metal.

36. The process for conducting an ion exchange process comprising the use of the compound of claim 1 as a cation exchanger, wherein one of R or R¹ is hydrogen or Mⁿ⁺/n and the other is C_12-40 alkyl, C_12-40 alkenyl, C_12-40 alkynyl, C_12-40 alkylaryl or aryl.

37. The process for conducting an ion exchange process comprising the use of the compound of claim 1 as a cation exchanger, wherein either or both of R and R¹ is Mⁿ⁺/n.

38. The process for conducting an ion exchange process comprising the use of the compound of claim 1 as a cation exchanger, wherein one of R and R¹ is Mⁿ⁺/n and the other is hydrogen or a C_1-12 alkyl, C_1-12 alkenyl, C_1-12 alkynyl, aryl or C_1-12 alkylaryl group.

39. The process for conducting an ion exchange process comprising the use of the compound of claim 1 as a cation exchanger, wherein one or both of R and R¹ is Mⁿ⁺/n, and Mⁿ⁺ is derived from a lanthanide, actinide, main group or transition metal.

40. The process for the separation of amines, including optically active amines, the process comprising contacting the amines with the compound of claim 1, wherein either or both of R and R¹ is hydrogen.

41. The process for the separation of amines, including optically active amines, the process comprising contacting the amines with the compound of claim 1, wherein one of R and R¹ is hydrogen and the other is C_1-40 alkyl, C_2-40 alkenyl, C_2-40 alkynyl, aryl, C_1-8 alkylaryl or a metal ion derived from a lanthanide, actinide, main group or transition metal.

42. The process for the separation of amines, including optically active amines, the process comprising contacting the amines with the compound of claim 1, wherein one of R or R¹ is hydrogen and the other is C_1-4 alkyl, phenyl, or C_1-8 alkylaryl.

43. The process for the separation of amines, including optically active amines, the process comprising contacting the amines with the compound of claim 1, wherein one of R or R¹ is hydrogen or Mⁿ⁺/n and the other is C_12-40 alkyl, C_12-40 alkenyl, C_12-40 alkynyl, C_12-40 alkylaryl or aryl.

44. The process for the separation of amines, including optically active amines, the process comprising contacting the amines with the compound of claim 1, wherein either or both of R and R¹ is Mⁿ⁺/n.

45. The process for the separation of amines, including optically active amines, the process comprising contacting the amines with the compound of claim 1, wherein one of R and R¹ is Mⁿ⁺/n and the other is hydrogen or a C_1-12 alkyl, C_1-12 alkenyl, C_1-12 alkynyl, aryl or C_1-12 alkylaryl group.

46. The process for the separation of amines, including optically active amines, the process comprising contacting the amines with the compound of claim 1, wherein one or both of R and R¹ is Mⁿ⁺/n, and Mⁿ⁺ is derived from a lanthanide, actinide, main group or transition metal.

2-28. -28. (canceled)