Esterification catalysts and processes therefor and therewith

Abstract

A catalyst composition is disclosed. The composition comprises a titanium compound, a complexing agent, hypophosphorous acid or its metal salt, water and optionally a solvent. The complexing agent can be hydroxycarboxylic acid, alkanolamines, aminocarboxylic acids, or combinations of two or more thereof. The solvent can be water, ethanol, propanol, isopropanol, butanol, ethylene glycol, propylene glycol, isopropylene glycol, butylene glycol, 1-methyl propylene glycol, pentylene glycol, or combinations of two or more thereof. The titanium compound can be combined with a zirconium compound. Also disclosed is a process for using the composition for producing an ester or a polyester. The process comprises contacting a carbonyl compound, in the presence of the compositions, with an alcohol under a condition suitable for esterification, transesterification, polymerization, or combinations of two or more thereof.

1. A composition comprising a titanium compound, a complexing agent, and an aqueous solution of hypophosphorous acid or a salt thereof wherein said complexing agent is selected from the group consisting of hydroxycarboxylic acids, alkanolamines, aminocarboxylic acids, and combinations of two or more thereof. 
     
     
       2. A composition according to  claim 1  wherein said titanium compound has the formula Ti(OR) 4  and each R is independently selected from the group consisting of an alkyl radical, a cycloalkyl radical, aralkyl radical, and combinations of two or more thereof and contains from 1 to about 30 carbon atoms per radical. 
     
     
       3. A composition according to  claim 1  wherein said titanium compound is selected from the group consisting of tetra isopropyl titanate, tetra n-butyl titanate, and combinations thereof. 
     
     
       4. A composition according to  claim 1  further comprising a solvent. 
     
     
       5. A composition according to  claim 4  wherein said solvent is selected from the group consisting of water, ethanol, propanol, isopropanol, butanol, ethylene glycol, propylene glycol, isopropylene glycol, butylene glycol, 1-methyl propylene glycol, pentylene glycol, and combinations of two or more thereof. 
     
     
       6. A composition according to  claim 4  wherein said solvent is selected from the group consisting of water, ethylene glycol, and combinations thereof. 
     
     
       7. A composition according to  claim 1  wherein
 said titanium compound has the formula Ti(OR) 4 , each R is independently selected from the group consisting of an alkyl radical, a cycloalkyl radical, aralkyl radical, and combinations of two or more thereof and contains from 1 to about 30 carbon atoms per radical;    said complexing agent is selected from the group consisting of a hydroxycarboxylic acid, an alkanolamine and combinations thereof, and    said composition further comprises a solvent selected from the group consisting of water, ethanol, propanol, isopropanol, butanol, ethylene glycol, propylene glycol, isopropylene glycol, butylene glycol, 1-methyl propylene glycol, pentylene glycol, and combinations of two or more thereof.    
     
     
       8. A composition according to  claim 7  wherein said titanium compound is selected from the group consisting of tetra isopropyl titanate, tetra n-butyl titanate, and combinations thereof; and said solvent is selected from the group consisting of water, ethylene glycol, and combinations thereof. 
     
     
       9. A composition according to any of  claims 4  to  8  wherein said solvent is water. 
     
     
       10. A composition according to any of  claims 4  to  8  wherein said solvent is ethylene glycol. 
     
     
       11. A composition according to  claim 9  wherein said solvent further comprises ethylene glycol. 
     
     
       12. A composition according to any of claims  1 - 8  and  11  wherein said titanium compound is combined with a zirconium compound. 
     
     
       13. A composition according to  claim 9  wherein said titanium compound is combined with a zirconium compound. 
     
     
       14. A composition according to  claim 10  wherein said titanium compound is combined with a zirconium compound. 
     
     
       15. A composition according to  claim 12  wherein said zirconium compound is selected from the group consisting of zirconium tetraethoxide, zirconium tetrapropoxide, zirconium tetraisopropoxide, zirconium tetra-n-butoxide, zirconium tetrahexoxide, zirconium tetra 2-ethylhexoxide, zirconium tetraoctoxide, and combinations of two or more thereof. 
     
     
       16. A composition according to  claim 13 ,  14 , or  15  wherein said zirconium compound is selected from the group consisting of zirconium tetraethoxide, zirconium tetrapropoxide, zirconium tetraisopropoxide, zirconium tetra-n-butoxide, zirconium tetrahexoxide, zirconium tetra 2-ethylhexoxide, zirconium tetraoctoxide, and combinations of two or more thereof. 
     
     
       17. A composition according to  claim 16  wherein the molar ratio of Ti/Zr is in the range of from about 0.001:1 to about 10:1. 
     
     
       18. A composition according to any of claims  1 - 8 ,  11 ,  13 ,  14 ,  15 , and  17  wherein said complexing agent is selected from the group consisting of an α-hydroxycarboxylic acid, an α-aminocarboxylic acid, an alkanolamine, and combinations of two or more thereof. 
     
     
       19. A composition according to  claim 9  wherein said complexing agent is selected from the group consisting of an α-hydroxycarboxylic acid, an α-aminocarboxylic acid, an alkanolamine, and combinations of two or more thereof. 
     
     
       20. A composition according to  claim 10  wherein said complexing agent is selected from the group consisting of an α-hydroxycarboxylic acid, an α-aminocarboxylic acid, an alkanolamine, and combinations of two or more thereof. 
     
     
       21. A composition according to  claim 16  wherein said complexing agent is selected from the group consisting of an α-hydroxycarboxylic acid, an α-aminocarboxylic acid, an alkanolamine, and combinations of two or more thereof. 
     
     
       22. A composition according to any of claims  1 - 8 ,  11 ,  13 ,  14 ,  15 , and  17  wherein said complexing agent is selected from the group consisting of lactic acid, glycolic acid, citric acid, tartaric acid, malic acid, diethanolamine, triethanolamine, tetrahydroxyisopropylethylenediamine, glycine, bis-hydroxyethyl glycine, hydroxyethyl glycine, and combinations of two or more thereof. 
     
     
       23. A composition according to  claim 19 ,  20 , or  21  wherein said complexing agent is selected from the group consisting of lactic acid, glycolic acid, citric acid, tartaric acid, malic acid, diethanolamine, triethanolamine, tetrahydroxyisopropylethylenediamine, glycine, bis-hydroxyethyl glycine, hydroxyethyl glycine, and combinations of two or more thereof. 
     
     
       24. A composition according to any of  claims 1  to  3  and wherein said composition is produced by combining said organic titanium compound, said complexing agent, and said hypophosphorous acid or its salt; and said complexing agent is selected from the group consisting of hydroxycarboxylic acids, aminocarboxylic acids, alkanolamines, and combinations of two or more thereof. 
     
     
       25. A composition according to  claim 24  further comprising combining said titanium compound, said complexing agent, and said hypophosphorous acid or its salt with a solvent selected from the group consisting of water, ethanol, propanol, isopropanol, butanol, ethylene glycol, propylene glycol, isopropylene glycol, butylene glycol, 1-methyl propylene glycol, pentylene glycol, and combinations of two or more thereof. 
     
     
       26. A composition according to  claim 25  wherein said titanium compound is selected from the group consisting of tetra isopropyl titanate, tetra n-butyl titanate, and combinations thereof, complexing agent is selected from the group consisting of lactic acid, glycolic acid, citric acid, tartaric acid, malic acid, diethanolamine, triethanolamine, tetrahydroxyisopropylethylenediamine, and combinations of two or more thereof; and said solvent is selected from the group consisting of water, ethylene glycol, and combinations thereof. 
     
     
       27. A composition according to  claim 25  or  26  wherein said titanium compound is combined with a zirconium compound selected from the group consisting of zirconium tetraethoxide, zirconium tetrapropoxide, zirconium tetraisopropoxide, zirconium tetra-n-butoxide, zirconium tetrahexoxide, zirconium tetra 2-ethylhexoxide, zirconium tetraoctoxide, and combinations of two or more thereof. 
     
     
       28. A composition comprising a titanium compound, a complexing agent, and hypophosphorous acid or a salt thereof, and a solvent wherein
 said titanium compound has the formula Ti(OR) 4 , each R is independently selected from the group consisting of an alkyl radical, a cycloalkyl radical, aralkyl radical, and combinations of two or more thereof and contains from 1 to about 30 carbon atoms per radical;    said complexing agent is selected from the group consisting of a hydroxycarboxylic acid, alkanolamines, and combinations thereof; and    said solvent is selected from the group consisting of water, ethanol, propanol, isopropanol, butanol, ethylene glycol, propylene glycol, isopropylene glycol, butylene glycol, 1-methyl propylene glycol, pentylene glycol, and combinations of two or more thereof.    
     
     
       29. A composition according to  claim 28  wherein said titanium compound is selected from the group consisting of tetra isopropyl titanate, tetra n-butyl titanate, and combinations thereof; said complexing agent is selected from the group consisting of lactic acid, glycolic acid, citric acid, tartaric acid, malic acid, diethanolamine, triethanolamine, tetrahydroxyisopropylethylenediamine, and combinations of two or more thereof; and said solvent is selected from the group consisting of water, ethylene glycol, and combinations thereof. 
     
     
       30. A composition according to  claim 28  or  29  wherein said solvent is water. 
     
     
       31. A composition according to  claim 30  wherein said solvent further comprises ethylene glycol. 
     
     
       32. A composition according to  claim 29  or  31  wherein said titanium compound is combined with a zirconium compound selected from the group consisting of zirconium tetraethoxide, zirconium tetrapropoxide, zirconium tetraisopropoxide, zirconium tetra-n-butoxide, zirconium tetrahexoxide, zirconium tetra 2-ethylhexoxide, zirconium tetraoctoxide, and combinations of two or more thereof. 
     
     
       33. A composition comprising a titanium compound, a complexing agent, and hypophosphorous acid or a salt thereof, and a solvent wherein
 said titanium compound is selected from the group consisting of tetra isopropyl titanate, tetra n-butyl titanate, and combinations thereof;    said complexing agent is selected from the group consisting of lactic acid, glycolic acid, citric acid, tartaric acid, malic acid, diethanolamine, triethanolamine, tetrahydroxyisopropylethylenediamine, and combinations of two or more thereof; and    said solvent is selected from the group consisting of water, ethylene glycol, and combinations thereof.    
     
     
       34. A composition according to  claim 33  wherein said solvent is water. 
     
     
       35. A composition according to  claim 34  wherein said solvent further comprises ethylene glycol. 
     
     
       36. A composition comprising a titanium complex and hypophosphorous acid or its salt wherein said titanium complex is a complex of a titanium compound and a complexing agent wherein said titanium compound has the formula Ti(OR) 4 , each R is independently selected from the group consisting of an alkyl radical, a cycloalkyl radical, aralkyl radical, and combinations of two or more thereof and contains from 1 to about 30 carbon atoms per radical; and said complexing agent is selected from the group consisting of an α-hydroxycarboxylic acid, alkanolamines, aminocarboxylic acids, and combinations of two or more thereof. 
     
     
       37. A composition according to  claim 36  wherein said titanium compound is selected from the group consisting of tetra isopropyl titanate, tetra n-butyl titanate, and combinations thereof; and said complexing agent is selected from the group consisting of lactic acid, glycolic acid, citric acid, tartaric acid, malic acid, diethanolamine, triethanolamine, tetrahydroxyisopropylethylenediamine, and combinations of two or more thereof. 
     
     
       38. A composition according to  claim 36  or  37  wherein said composition further comprises a solvent selected from the group consisting of water, ethanol, propanol, isopropanol, butanol, ethylene glycol, propylene glycol, isopropylene glycol, butylene glycol, 1-methyl propylene glycol, pentylene glycol, and combinations of two or more thereof. 
     
     
       39. A composition according to  claim 38  said solvent is selected from the group consisting of water, ethanol, and combinations thereof. 
     
     
       40. A composition according to  claim 39  wherein said titanium complex is TYZOR® LA(bis-ammonium lactate titanate). 
     
     
       41. A process comprising contacting, in the presence of a catalyst composition, a carbonyl compound and an alcohol wherein said catalyst comprises a titanium compound, a complexing agent, and hypophosphorous acid or its salt wherein said complexing agent is selected from the group consisting of hydroxycarboxylic acids, alkanolamines, aminocarboxylic acids, and combinations of two or more thereof. 
     
     
       42. A process according to  claim 41  wherein said titanium compound has the formula Ti(OR) 4  and each R is independently selected from the group consisting of an alkyl radical, a cycloalkyl radical, aralkyl radical, and combinations of two or more thereof and contains from 1 to about 30 carbon atoms per radical. 
     
     
       43. A process according to  claim 41  wherein said titanium compound is selected from the group consisting of tetra isopropyl titanate, tetra n-butyl titanate, and combinations thereof. 
     
     
       44. A process according to  claim 41 ,  42 , or  43  wherein said catalyst further comprises a solvent selected from the group consisting of water, ethanol, propanol, isopropanol, butanol, ethylene glycol, propylene glycol, isopropylene glycol, butylene glycol, 1-methyl propylene glycol, pentylene glycol, and combinations of two or more thereof. 
     
     
       45. A process according to  claim 44  wherein said solvent is selected from the group consisting of water, ethylene glycol, and combinations thereof. 
     
     
       46. A process according to  claim 41  wherein
 said titanium compound has the formula Ti(OR) 4  wherein each R is independently selected from the group consisting of an alkyl radical, a cycloalkyl radical, aralkyl radical, and combinations of two or more thereof and contains from 1 to about 30 carbon atoms per radical;    said complexing agent is selected from the group consisting of α-hydroxycarboxylic acids, alkanolamines, and combinations thereof; and    said catalyst further comprises a solvent selected from the group consisting of ethanol, propanol, isopropanol, butanol, ethylene glycol, propylene glycol, isopropylene glycol, butylene glycol, 1-methyl propylene glycol, pentylene glycol, and combinations of two or more thereof.    
     
     
       47. A process according to  claim 46  wherein said titanium compound is selected from the group consisting of tetra isopropyl titanate, tetra n-butyl titanate, and combinations thereof, said complexing agent is selected from the group consisting of lactic acid, glycolic acid, citric acid, tartaric acid, malic acid, diethanolamine, triethanolamine, tetrahydroxyisopropylethylenediamine, and combinations of two or more thereof; and said solvent is selected from the group consisting of water, ethylene glycol, and combinations thereof. 
     
     
       48. A process according to  claim 41  wherein said catalyst composition is a titanium complex produced by combining a titanium compound and a complexing agent; said titanium compound is selected from the group consisting of tetra isopropyl titanate, tetra n-butyl titanate, and combinations thereof; and said complexing agent selected from the group consisting of lactic acid, glycolic acid, citric acid, tartaric acid, malic acid, diethanolamine, triethanolamine, tetrahydroxyisopropylethylenediamine, and combinations of two or more thereof. 
     
     
       49. A process according to  claim 48  wherein said catalyst composition further comprises combining said titanium complex and said hypophosphorous acid or its salt with a solvent selected from the group consisting of water, ethylene glycol, and combinations thereof. 
     
     
       50. A process according to any of claims  41 - 43  and  45  to  49  wherein said carbonyl compound has the formula of R 2 COOR 2 ; each R 2  is independently selected from the group consisting of (1) hydrogen, (2) hydrocarboxyl radical having a carboxylic acid group at the terminus, or (3) hydrocarbyl radical in which each radical has 1 to about 30 carbon atoms per radical which is alkyl, alkenyl, aryl, alkaryl, or aralkyl radical, (4) a 5-sulfo isophthalate metal salt or its ester, and (5) combinations of two or more thereof. 
     
     
       51. A process according to  claim 50  wherein said alcohol is selected from the group consisting of ethylene glycol, propylene glycol, isopropylene glycol, butylene glycol, 1-methyl propylene glycol, pentylene glycol, and combinations of two or more thereof. 
     
     
       52. A process according to  claim 51  wherein said alcohol is ethylene glycol. 
     
     
       53. A process according to  claim 50  wherein said carbonyl compound is selected from the group consisting of terephthalic acid, dimethyl terephthalate, isophthalic acid, naphthalic acid, succinic acid, adipic acid, phthalic acid, glutaric acid, acrylic acid, oxalic acid, benzoic acid, maleic acid, propenoic acid, bis-glycolate ester of 5-sulfo isophthalate sodium salt, and combination of two or more thereof. 
     
     
       54. A process according to  claim 51  or  52  wherein said carbonyl compound is selected from the group consisting of terephthalic acid, dimethyl terephthalate, isophthalic acid, naphthalic acid, succinic acid, adipic acid, phthalic acid, glutaric acid, acrylic acid, oxalic acid, benzoic acid, maleic acid, propenoic acid, bis-glycolate ester of 5-sulfo isophthalate sodium salt, and combination of two or more thereof. 
     
     
       55. A process according to  claim 51 ,  52 , or  53  wherein said carbonyl compound is terephthalic acid. 
     
     
       56. A process according to  claim 55  wherein said carbonyl compound comprises a mixture of terephthalic acid and bis-glycolate ester of 5-sulfo isophthalate sodium salt. 
     
     
       57. A composition comprising, or produced by combining, a titanium compound, a complexing agent, and an aqueous solution of hypophosphorous acid or a salt thereof wherein said complexing agent is selected from the group consisting of hydroxycarboxylic acids, alkanolamines, aminocarboxylic acids, and combinations of two or more thereof. 
     
     
       58. A composition according to  claim 57  wherein said titanium compound has the formula Ti( OR ) 4    and each R is independently selected from the group consisting of an alkyl radical, a cycloalkyl radical, an aralkyl radical, and combinations of two or more thereof and contains from  1  to about  30  carbon atoms per radical.   
     
     
       59. A composition according to  claim 57  wherein said titanium compound is selected from the group consisting of tetra isopropyl titanate, tetra n- butyl titanate, and combinations thereof.   
     
     
       60. A composition according to  claim 57  further comprising a solvent. 
     
     
       61. A composition according to  claim 60  wherein said solvent is selected from the group consisting of water, ethanol, propanol, isopropanol, butanol, ethylene glycol, propylene glycol, isopropylene glycol, butylene glycol,  1 - methyl propylene glycol, pentylene glycol, and combinations of two or more thereof.   
     
     
       62. A composition according to  claim 60  wherein said solvent is selected from the group consisting of water, ethylene glycol, and combinations thereof. 
     
     
       63. A composition according to  claim 57  wherein
   said titanium compound has the formula Ti ( OR ) 4   , each R is independently selected from the group consisting of an alkyl radical, a cycloalkyl radical, aralkyl radical, and combinations of two or more thereof and contains from  1  to about  30  carbon atoms per radical;        said complexing agent is selected from the group consisting of a hydroxycarboxylic acid, an aminocarboxylic acid, an alkanolamine and combinations of two or more thereof; and        said composition further comprises a solvent selected from the group consisting of water, ethanol, propanol, isopropanol, butanol, ethylene glycol, propylene glycol, isopropylene glycol, butylene glycol,  1   - methyl propylene glycol, pentylene glycol, and combinations of two or more thereof.     
     
     
       64. A composition according to  claim 63  wherein said titanium compound is selected from the group consisting of tetra isopropyl titanate, tetra n- butyl titanate, and combinations thereof; and said solvent is selected from the group consisting of water, ethylene glycol, and combinations thereof.   
     
     
       65. A composition according to any of  claims 57  to  59  and  61  to  64  wherein said solvent is water. 
     
     
       66. A composition according to any of  claims 57  to  59  and  61  to  64  wherein said solvent is ethylene glycol. 
     
     
       67. A composition according to  claim 66  wherein said solvent further comprises water. 
     
     
       68. A composition according to any of  claims 57  to  64  wherein said titanium compound is combined with a zirconium compound. 
     
     
       69. A composition according to  claim 65  wherein said titanium compound is combined with a zirconium compound. 
     
     
       70. A composition according to  claim 66  wherein said titanium compound is combined with a zirconium compound. 
     
     
       71. A composition according to  claim 67  wherein said titanium compound is combined with a zirconium compound. 
     
     
       72. A composition according to  claim 68  wherein said zirconium compound is selected from the group consisting of zirconium tetraethoxide, zirconium tetrapropoxide, zirconium tetraisopropoxide, zirconium tetra- n - butoxide, zirconium tetrahexoxide, zirconium tetra  2   - ethylhexoxide, zirconium tetraoctoxide, and combinations of two or more thereof.   
     
     
       73. A composition according to  claim 69  wherein said zirconium compound is selected from the group consisting of zirconium tetraethoxide, zirconium tetrapropoxide, zirconium tetraisopropoxide, zirconium tetra- n - butoxide, zirconium tetrahexoxide, zirconium tetra  2   - ethylhexoxide, zirconium tetraoctoxide, and combinations of two or more thereof.   
     
     
       74. A composition according to  claim 70  wherein said zirconium compound is selected from the group consisting of zirconium tetraethoxide, zirconium tetrapropoxide, zirconium tetraisopropoxide, zirconium tetra- n - butoxide, zirconium tetrahexoxide, zirconium tetra  2   - ethylhexoxide, zirconium tetraoctoxide, and combinations of two or more thereof.   
     
     
       75. A composition according to  claim 71  wherein said zirconium compound is selected from the group consisting of zirconium tetraethoxide, zirconium tetrapropoxide, zirconium tetraisopropoxide, zirconium tetra- n - butoxide, zirconium tetrahexoxide, zirconium tetra  2   - ethylhexoxide, zirconium tetraoctoxide, and combinations of two or more thereof.   
     
     
       76. A composition according to  claim 72  wherein the molar ratio of Ti/Zr is in the range of from about  0 . 001 : 1  to about  10 : 1 . 
     
     
       77. A composition according to  claim 73  wherein the molar ratio of Ti/Zr is in the range of from about  0 . 001 : 1  to about  10 : 1 . 
     
     
       78. A composition according to  claim 64  wherein the molar ratio of Ti/Zr is in the range of from about  0 . 001 : 1  to about  10 : 1 . 
     
     
       79. A composition according to  claim 75  wherein the molar ratio of Ti/Zr is in the range of from about  0 . 001 : 1  to about  10 : 1 . 
     
     
       80. A composition according to any of  claims 57  to  62  wherein said complexing agent is selected from the group consisting of an α- hydroxycarboxylic acid, an  α- aminocarboxylic acid, an alkanolamine, and combinations of two or more thereof.   
     
     
       81. A composition according to  claim 65  wherein said complexing agent is selected from the group consisting of an α- hydroxycarboxylic acid, an α - aminocarboxylic acid, an alkanolamine, and combinations of two or more thereof.   
     
     
       82. A composition according to  claim 66  wherein said complexing agent is selected from the group consisting of an α- hydroxycarboxylic acid, an α - aminocarboxylic acid, an alkanolamine, and combinations of two or more thereof.   
     
     
       83. A composition according to  claim 67  wherein said complexing agent is selected from the group consisting of an α- hydroxycarboxylic acid, an α - aminocarboxylic acid, an alkanolamine, and combinations of two or more thereof.   
     
     
       84. A composition according to  claim 68  wherein said complexing agent is selected from the group consisting of an α- hydroxycarboxylic acid, an α - aminocarboxylic acid, an alkanolamine, and combinations of two or more thereof.   
     
     
       85. A composition according to  claim 69  wherein said complexing agent is selected from the group consisting of an α- hydroxycarboxylic acid, an α - aminocarboxylic acid, an alkanolamine, and combinations of two or more thereof.   
     
     
       86. A composition according to  claim 70  wherein said complexing agent is selected from the group consisting of an α- hydroxycarboxylic acid, an α - aminocarboxylic acid, an alkanolamine, and combinations of two or more thereof.   
     
     
       87. A composition according to  claim 71  wherein said complexing agent is selected from the group consisting of an α- hydroxycarboxylic acid, an α - aminocarboxylic acid, an alkanolamine, and combinations of two or more thereof.   
     
     
       88. A composition according to any of  claims 57  to  64  wherein said complexing agent is selected from the group consisting of lactic acid, glycolic acid, citric acid, tartaric acid, malic acid, diethanolamine, triethanolamine, tetrahydroxyisopropylethylenediamine, glycine, bis- hydroxyethyl glycine, hydroxyethyl glycine, and combinations of two or more thereof.   
     
     
       89. A composition according to  claim 65  wherein said complexing agent is selected from the group consisting of lactic acid, glycolic acid, citric acid, tartaric acid, malic acid, diethanolamine, triethanolamine, tetrahydroxyisopropylethylenediamine, glycine, bis- hydroxyethyl glycine, hydroxyethyl glycine, and combinations of two or more thereof.   
     
     
       90. A composition according to  claim 66  wherein said complexing agent is selected from the group consisting of lactic acid, glycolic acid, citric acid, tartaric acid, malic acid, diethanolamine, triethanolamine, tetrahydroxyisopropylethylenediamine, glycine, bis- hydroxyethyl glycine, hydroxyethyl glycine, and combinations of two or more thereof.   
     
     
       91. A composition according to  claim 67  wherein said complexing agent is selected from the group consisting of lactic acid, glycolic acid, citric acid, tartaric acid, malic acid, diethanolamine, triethanolamine, tetrahydroxyisopropylethylenediamine, glycine, bis- hydroxyethyl glycine, hydroxyethyl glycine, and combinations of two or more thereof.   
     
     
       92. A composition according to  claim 76  wherein said complexing agent is selected from the group consisting of lactic acid, glycolic acid, citric acid, tartaric acid, malic acid, diethanolamine, triethanolamine, tetrahydroxyisopropylethylenediamine, glycine, bis- hydroxyethyl glycine, hydroxyethyl glycine, and combinations of two or more thereof.   
     
     
       93. A composition according to  claim 77  wherein said complexing agent is selected from the group consisting of lactic acid, glycolic acid, citric acid, tartaric acid, malic acid, diethanolamine, triethanolamine, tetrahydroxyisopropylethylenediamine, glycine, bis- hydroxyethyl glycine, hydroxyethyl glycine, and combinations of two or more thereof.   
     
     
       94. A composition according to  claim 78  wherein said complexing agent is selected from the group consisting of lactic acid, glycolic acid, citric acid, tartaric acid, malic acid, diethanolamine, triethanolamine, tetrahydroxyisopropylethylenediamine, glycine, bis- hydroxyethyl glycine, hydroxyethyl glycine, and combinations of two or more thereof.   
     
     
       95. A composition according to  claim 79  wherein said complexing agent is selected from the group consisting of lactic acid, glycolic acid, citric acid, tartaric acid, malic acid, diethanolamine, triethanolamine, tetrahydroxyisopropylethylenediamine, glycine, bis- hydroxyethyl glycine, hydroxyethyl glycine, and combinations of two or more thereof.   
     
     
       96. A composition according to any of  claims 57  to  59  and wherein said composition is produced by combining said organic titanium compound, said complexing agent, and said hypophosphorous acid or its salt; and said complexing agent is selected from the group consisting of hydroxycarboxylic acids, aminocarboxylic acids, alkanolamines, and combinations of two or more thereof. 
     
     
       97. A composition according to  claim 96  further comprising combining said titanium compound, said complexing agent, and said hypophosphorous acid or its salt with a solvent selected from the group consisting of water, ethanol, propanol, isopropanol, butanol, ethylene glycol, propylene glycol, isopropylene glycol, butylene glycol,  1 - methyl propylene glycol, pentylene glycol, and combinations of two or more thereof.   
     
     
       98. A composition according to  claim 97  wherein said titanium compound is selected from the group consisting of tetra isopropyl titanate, tetra n- butyl titanate, and combinations thereof; complexing agent is selected from the group consisting of lactic acid, glycolic acid, citric acid, tartaric acid, malic acid, diethanolamine, triethanolamine, tetrahydroxyisopropylethylenediamine, glycine, bis - hydroxyethyl glycine, hydroxyethyl glycine, and combinations of two or more thereof; and said solvent is selected from the group consisting of water, ethylene glycol, and combinations thereof.   
     
     
       99. A composition according to  claim 97  wherein said titanium compound is further combined with a zirconium compound selected from the group consisting of zirconium tetraethoxide, zirconium tetrapropoxide, zirconium tetraisopropoxide, zirconium tetra- n - butoxide, zirconium tetrahexoxide, zirconium tetra  2   - ethylhexoxide, zirconium tetraoctoxide, and combinations of two or more thereof.   
     
     
       100. A composition according to  claim 98  wherein said titanium compound is further combined with a zirconium compound selected from the group consisting of zirconium tetraethoxide, zirconium tetrapropoxide, zirconium tetraisopropoxide, zirconium tetra- n - butoxide, zirconium tetrahexoxide, zirconium tetra  2   - ethylhexoxide, zirconium tetraoctoxide, and combinations of two or more thereof.   
     
     
       101. A composition comprising, or produced by combining, a titanium compound, a complexing agent, and hypophosphorous acid or a salt thereof, and a solvent wherein
   said titanium compound has the formula Ti ( OR ) 4   , each R is independently selected from the group consisting of an alkyl radical, a cycloalkyl radical, aralkyl radical, and combinations of two or more thereof and contains from  1  to about  30  carbon atoms per radical;        said complexing agent is selected from the group consisting of hydroxycarboxylic acids, an aminocarboxylic acid, an alkanolamine and combinations of two or more thereof; and        said solvent is selected from the group consisting of water, ethanol, propanol, isopropanol, butanol, ethylene glycol, propylene glycol, isopropylene glycol, butylene glycol,  1   - methyl propylene glycol, pentylene glycol, and combinations of two or more thereof.     
     
     
       102. A composition according to  claim 101  wherein said titanium compound is selected from the group consisting of tetra isopropyl titanate, tetra n- butyl titanate, and combinations thereof; said complexing agent is selected from the group consisting of lactic acid, glycolic acid, citric acid, tartaric acid, malic acid, diethanolamine, triethanolamine, tetrahydroxyisopropylethylenediamine, glycine, bis - hydroxyethyl glycine, hydroxyethyl glycine, and combinations of two or more thereof.   
     
     
       103. A composition according to  claim 101  wherein said solvent is water. 
     
     
       104. A composition according to  claim 102  wherein said solvent is water. 
     
     
       105. A composition according to  claim 103  wherein said solvent further comprises ethylene glycol. 
     
     
       106. A composition according to  claim 104  wherein said solvent further comprises ethylene glycol. 
     
     
       107. A composition according to any of  claims 102  to  106  wherein said titanium compound is further combined with a zirconium compound selected from the group consisting of zirconium tetraethoxide, zirconium tetrapropoxide, zirconium tetraisopropoxide, zirconium tetra- n - butoxide, zirconium tetrahexoxide, zirconium tetra  2   - ethylhexoxide, zirconium tetraoctoxide, and combinations of two or more thereof.   
     
     
       108. A composition comprising, or produced by combining, a titanium compound, a complexing agent, a solvent, and optionally hypophosphorous acid or a salt thereof wherein
   said titanium compound is selected from the group consisting of tetra isopropyl titanate, tetra n - butyl titanate, and combinations thereof;        said complexing agent is selected from the group consisting of lactic acid, glycolic acid, citric acid, tartaric acid, malic acid, diethanolamine, triethanolamine, tetrahydroxyisopropylethylenediamine, glycine, bis - hydroxyethyl glycine, hydroxyethyl glycine, and combinations of two or more thereof;        said solvent is selected from the group consisting of water, ethylene glycol, and combinations thereof; and        said hypophosphorous acid or a salt thereof is sodium hypophosphite.     
     
     
       109. A composition according to  claim 108  wherein said solvent is water. 
     
     
       110. A composition according to  claim 109  wherein said solvent further comprises ethylene glycol. 
     
     
       111. A composition comprising, or produced by combining, a titanium complex and hypophosphorous acid or its salt wherein said titanium complex is a complex of a titanium compound and a complexing agent wherein said titanium compound has the formula Ti( OR ) 4   , each R is independently selected from the group consisting of an alkyl radical, a cycloalkyl radical, aralkyl radical, and combinations of two or more thereof and contains from  1  to about  30  carbon atoms per radical; and said complexing agent is selected from the group consisting of an α - hydroxycarboxylic acid, alkanolamines, α - aminocarboxylic acids, and combinations of two or more thereof.   
     
     
       112. A composition according to  claim 111  wherein said titanium compound is selected from the group consisting of tetra isopropyl titanate, tetra n- butyl titanate, and combinations thereof; and said complexing agent is selected from the group consisting of lactic acid, glycolic acid, citric acid, tartaric acid, malic acid, diethanolamine, triethanolamine, bis - hydroxyethyl glycine, tetrahydroxyisopropylethylenediamine, glycine, hydroxyethyl glycine, and combinations of two or more thereof.   
     
     
       113. A composition according to  claim 111  or  112  wherein said composition further comprises a solvent selected from the group consisting of water, ethanol, propanol, isopropanol, butanol, ethylene glycol, propylene glycol, isopropylene glycol, butylene glycol,  1 - methyl propylene glycol, pentylene glycol, and combinations of two or more thereof.   
     
     
       114. A composition according to  claim 113  said solvent is selected from the group consisting of water, ethylene glycol, and combinations thereof. 
     
     
       115. A composition according to  claim 114  wherein said titanium complex is TYZOR® LA ( bis - ammonium lactate titanate ). 
     
     
       116. A process comprising contacting, in the presence of a catalyst composition, a carbonyl compound and an alcohol wherein said catalyst comprises, or is produced by combining, a titanium compound, a complexing agent, and hypophosphorous acid or its salt wherein said complexing agent is selected from the group consisting of hydroxycarboxylic acids, alkanolamines, aminocarboxylic acids, and combinations of two or more thereof. 
     
     
       117. A process according to  claim 116  wherein said titanium compound has the formula Ti( OR ) 4    and each R is independently selected from the group consisting of an alkyl radical, a cycloalkyl radical, an aralkyl radical, and combinations of two or more thereof and contains from  1  to about  30  carbon atoms per radical.   
     
     
       118. A process according to  claim 116  wherein said titanium compound is selected from the group consisting of tetra isopropyl titanate, tetra n- butyl titanate, and combinations thereof.   
     
     
       119. A process according to  claim 116 ,  117 , or  118  wherein said catalyst further comprises a solvent selected from the group consisting of water, ethanol, propanol, isopropanol, butanol, ethylene glycol, propylene glycol, isopropylene glycol, butylene glycol,  1 - methyl propylene glycol, pentylene glycol, and combinations of two or more thereof.   
     
     
       120. A process according to  claim 119  wherein said solvent is selected from the group consisting of water, ethylene glycol, and combinations thereof. 
     
     
       121. A process according to  claim 116  wherein
   said titanium compound has the formula Ti ( OR ) 4    wherein each R is independently selected from the group consisting of an alkyl radical, a cycloalkyl radical, an aralkyl radical, and combinations of two or more thereof and contains from  1  to about  30  carbon atoms per radical;        said complexing agent is selected from the group consisting of α - hydroxycarboxylic acids, alkanolamines, α - aminocarboxylic acids, and combinations of two or more thereof; and        said catalyst further comprises a solvent selected from the group consisting of ethanol, propanol, isopropanol, butanol, ethylene glycol, propylene glycol, isopropylene glycol, butylene glycol,  1   - methyl propylene glycol, pentylene glycol, and combinations of two or more thereof.     
     
     
       122. A process according to  claim 121  wherein said titanium compound is selected from the group consisting of tetra isopropyl titanate, tetra n- butyl titanate, and combinations thereof; said hypophosphorous acid or a salt thereof is sodium hypophosphite; said complexing agent is selected from the group consisting of lactic acid, glycolic acid, citric acid, tartaric acid, malic acid, diethanolamine, triethanolamine, tetrahydroxyisopropylethylenediamine, glycine, bis - hydroxyethyl glycine, hydroxyethyl glycine, and combinations of two or more thereof; and said solvent is selected from the group consisting of water, ethylene glycol, and combinations thereof.   
     
     
       123. A process according to  claim 116  wherein said catalyst composition is a titanium complex produced by combining said titanium compound and said complexing agent; said titanium compound is selected from the group consisting of tetra isopropyl titanate, tetra n- butyl titanate, and combinations thereof; and said complexing agent selected from the group consisting of lactic acid, glycolic acid, citric acid, tartaric acid, malic acid, diethanolamine, triethanolamine, tetrahydroxyisopropylethylenediamine, glycine, bis - hydroxyethyl glycine, hydroxyethyl glycine, and combinations of two or more thereof.   
     
     
       124. A process according to  claim 123  wherein said catalyst composition further comprises combining said titanium complex and sodium hypophosphite with a solvent selected from the group consisting of water, ethylene glycol, and combinations thereof. 
     
     
       125. A process according to any of  claims 116  to  118  and  121  to  123  wherein said carbonyl compound has the formula of R 2   COOR   2   ; each R   2    is independently selected from the group consisting of  (   1   )  hydrogen,  (   2   )  hydrocarboxyl radical having a carboxylic acid group at the terminus, or  (   3   )  hydrocarbyl radical in which each radical has  1  to about  30 , preferably about  3  to about  15  carbon atoms per radical which can be alkyl, alkenyl, aryl, alkaryl, aralkyradical,  (   4   )  a  5   - sulfo isophthalate metal salt or its ester, and  (   5   )  combinations of two or more thereof.   
     
     
       126. A process according to  claim 120  wherein said carbonyl compound has the formula of R 2   COOR   2   ; each R   2    is independently selected from the group consisting of  (   1   )  hydrogen,  (   2   )  hydrocarboxyl radical having a carboxylic acid group at the terminus, or  (   3   )  hydrocarbyl radical in which each radical has  1  to about  30 , preferably about  3  to about  15  carbon atoms per radical which can be alkyl, alkenyl, aryl, alkaryl, aralkyradical,  (   4   )  a  5   - sulfo isophthalate metal salt or its ester, and  (   5   )  combinations of two or more thereof.   
     
     
       127. A process according to  claim 125  wherein said alcohol is selected from the group consisting of ethylene glycol, propylene glycol, isopropylene glycol, butylene glycol,  1 - methyl propylene glycol, pentylene glycol, and combinations of two or more thereof.   
     
     
       128. A process according to  claim 126  wherein said alcohol is selected from the group consisting of ethylene glycol, propylene glycol, isopropylene glycol, butylene glycol,  1 - methyl propylene glycol, pentylene glycol, and combinations of two or more thereof.   
     
     
       129. A process according to  claim 127  wherein said alcohol is ethylene glycol. 
     
     
       130. A process according to  claim 128  wherein said alcohol is ethylene glycol. 
     
     
       131. A process according to  claim 127  wherein said carbonyl compound is selected from the group consisting of terephthalic acid, dimethyl terephthalate, isophthalic acid, naphthalic acid, succinic acid, adipic acid, phthalic acid, glutaric acid, acrylic acid, oxalic acid, benzoic acid, maleic acid, propenoic acid, bis- glycolate ester of  5   - sulfo isophthalate sodium salt, and combination of two or more thereof.   
     
     
       132. A process according to  claim 128  wherein said carbonyl compound is selected from the group consisting of terephthalic acid, dimethyl terephthalate, isophthalic acid, naphthalic acid, succinic acid, adipic acid, phthalic acid, glutaric acid, acrylic acid, oxalic acid, benzoic acid, maleic acid, propenoic acid, bis- glycolate ester of  5   - sulfo isophthalate sodium salt, and combination of two or more thereof.   
     
     
       133. A process according to  claim 129  wherein said carbonyl compound is terephthalic acid. 
     
     
       134. A process according to  claim 130  wherein said carbonyl compound is terephthalic acid. 
     
     
       135. A process according to  claim 129  wherein said carbonyl compound comprises a mixture of terephthalic acid and bis- glycolate ester of  5   - sulfo isophthalate sodium salt.   
     
     
       136. A process according to  claim 130  wherein said carbonyl compound comprises a mixture of terephthalic acid and bis- glycolate ester of  5   - sulfo isophthalate sodium salt.