STABILIZED LEVULINIC ESTER KETALS

1 . A composition comprising a plasticizer comprising at least 2 alkyl ketal ester moieties and having a molecular weight of greater than 300; and

at least one of an antioxidant, a UV stabilizer, a thermal stabilizer or mixtures thereof, present in the composition from about 0.01 to about 5.0 percent by weight of the total composition.

2 . The composition of claim 1 , wherein the plasticizer comprises a formula of:

combinations thereof, wherein

each a, independently, is from 0 or an integer of 1 to 12;

each b, independently, is 0 or 1;

c is from 0 to 12;

d is 0 or 1;

each e, independently, is from 0 to 12;

each f, independently, is from 0 to 12;

each i is 0 or 1;

each j, independently, is 0 to 100;

each R 1 , independently, is a hydrogen, a hydrocarbyl group, or a substituted hydrocarbyl group;

each R 2 , R 3 and R 4 are independently methylene, alkylmethylene, or dialkylmethylene;

R 5 is a hydrogen or

R 6 is a hydrocarbyl group or a substituted hydrocarbyl group;

each R 7 , independently, is a hydrogen, a hydrocarbyl or a substituted hydrocarbyl group;

each R 8 , independently, is a hydrogen, a hydrocarbyl or a substituted hydrocarbyl group;

each R 10 , independently, is a hydrocarbyl or a substituted hydrocarbyl group;

R 11 is a hydrocarbyl, a substituted hydrocarbyl, or a hydrocarbyl group terminated with one or more heteroatoms to form a cyclic membered ring and which can include one or more of —O—, —NH—, —NR—, wherein R is a hydrocarbyl or a substituted hydrocarbyl;

R 12 , is a covalent bond, a hydrocarbyl group or a substituted hydrocarbyl group;

each R 14 , independently, is a hydrogen, a hydrocarbyl, or a substituted hydrocarbyl group;

each R 15 , independently, is a hydrogen, a hydrocarbyl, or a substituted hydrocarbyl group;

each R 19 , independently, is a hydrocarbyl, a substituted hydrocarbyl, or a hydrocarbyl group substituted with up to 5 hydroxyl groups;

each R 23 is a hydrocarbyl group or substituted hydrocarbyl group having between 1 and 12 carbon atoms

each Z, independently, is —O—, —NH— or —NR— where R is a hydrocarbyl or a substituted hydrocarbyl group;

n is from 1 to 100;

s is at least one;

v is from 0 to 100;

w is from 1 to 100;

x is at least 1;

y is 0 or a positive number; and

z is 0 or a positive number provided that z is at least one when R 5 is hydrogen.

3 . The composition of claim 2 , wherein the plasticizer is the compound of formula (IV) wherein R 11 is a C4 alkyl.

4 . The composition of claim 3 , wherein each a=2 and each b=0.

5 . A plasticizer comprising at least 2 alkyl ketal ester moieties, the plasticizer having a molecular weight of greater than 300 comprising a formula of:

combinations thereof, wherein

each a, independently, is from 0 or an integer of 1 to 12;

each b, independently, is 0 or 1;

c is from 0 to 12;

d is 0 or 1;

each e, independently, is from 0 to 12;

each f, independently, is from 0 to 12;

each i is 0 or 1;

each j, independently, is 0 to 100;

each R 1 , independently, is a hydrogen, a hydrocarbyl group, or a substituted hydrocarbyl group;

each R 2 , R 3 and R 4 are independently methylene, alkylmethylene, or dialkylmethylene;

R 5 is a hydrogen or

R 6 is a hydrocarbyl group or a substituted hydrocarbyl group;

each R 7 , independently, is a hydrogen, a hydrocarbyl or a substituted hydrocarbyl group;

each R 8 , independently, is a hydrogen, a hydrocarbyl or a substituted hydrocarbyl group;

each R 10 , independently, is a hydrocarbyl or a substituted hydrocarbyl group;

R 11 is a hydrocarbyl, a substituted hydrocarbyl, or a hydrocarbyl group terminated with one or more heteroatoms to form a cyclic membered ring and which can include one or more of —O—, —NH—, —NR—, wherein R is a hydrocarbyl or a substituted hydrocarbyl;

R 12 , is a covalent bond, a hydrocarbyl group or a substituted hydrocarbyl group;

each R 14 , independently, is a hydrogen, a hydrocarbyl, or a substituted hydrocarbyl group;

each R 15 , independently, is a hydrogen, a hydrocarbyl, or a substituted hydrocarbyl group;

each R 19 , independently, is a hydrocarbyl, a substituted hydrocarbyl, or a hydrocarbyl group substituted with up to 5 hydroxyl groups;

each R 23 is a hydrocarbyl group or substituted hydrocarbyl group having between 1 and 12 carbon atoms

each Z, independently, is —O—, —NH— or —NR— where R is a hydrocarbyl or a substituted hydrocarbyl group;

n is from 1 to 100;

s is at least one;

v is from 0 to 100;

w is from 1 to 100;

x is at least 1;

y is 0 or a positive number; and

z is 0 or a positive number provided that z is at least one when R 5 is hydrogen, wherein the plasticizer has a color index (YI) of less than 50 measured by ASTM method E313 and has a purity of at least 90%.

6 . The plasticizer of claim 5 , wherein the plasticizer is the compound of formula (IV) wherein R 11 is a C4 alkyl.

7 . The plasticizer of claim 6 , wherein each a=2 and each b=0.

8 . A plasticizer comprising at least 2 alkyl ketal ester moieties, the plasticizer having a molecular weight of greater than 300 comprising a formula of:

combinations thereof, wherein

each a, independently, is from 0 or an integer of 1 to 12;

each b, independently, is 0 or 1;

c is from 0 to 12;

d is 0 or 1;

each e, independently, is from 0 to 12;

each f, independently, is from 0 to 12;

each i is 0 or 1;

each j, independently, is 0 to 100;

each R 1 , independently, is a hydrogen, a hydrocarbyl group, or a substituted hydrocarbyl group;

each R 2 , R 3 and R 4 are independently methylene, alkylmethylene, or dialkylmethylene;

R 5 is a hydrogen or

R 6 is a hydrocarbyl group or a substituted hydrocarbyl group;

each R 7 , independently, is a hydrogen, a hydrocarbyl or a substituted hydrocarbyl group;

each R 8 , independently, is a hydrogen, a hydrocarbyl or a substituted hydrocarbyl group;

each R 10 , independently, is a hydrocarbyl or a substituted hydrocarbyl group;

R 11 is a hydrocarbyl, a substituted hydrocarbyl, or a hydrocarbyl group terminated with one or more heteroatoms to form a cyclic membered ring and which can include one or more of —O—, —NH—, —NR—, wherein R is a hydrocarbyl or a substituted hydrocarbyl;

R 12 , is a covalent bond, a hydrocarbyl group or a substituted hydrocarbyl group;

each R 14 , independently, is a hydrogen, a hydrocarbyl, or a substituted hydrocarbyl group;

each R 15 , independently, is a hydrogen, a hydrocarbyl, or a substituted hydrocarbyl group;

each R 19 , independently, is a hydrocarbyl, a substituted hydrocarbyl, or a hydrocarbyl group substituted with up to 5 hydroxyl groups;

each R 23 is a hydrocarbyl group or substituted hydrocarbyl group having between 1 and 12 carbon atoms

each Z, independently, is —O—, —NH— or —NR— where R is a hydrocarbyl or a substituted hydrocarbyl group;

n is from 1 to 100;

s is at least one;

v is from 0 to 100;

w is from 1 to 100;

x is at least 1;

y is 0 or a positive number; and

z is 0 or a positive number provided that z is at least one when R 5 is hydrogen, wherein the mass loss is less than 2% after 10 days at 110° C. and less than 15% RH.

9 . The plasticizer of claim 8 , wherein the plasticizer is the compound of formula (IV) wherein R 11 is a C4 alkyl.

10 . The plasticizer of claim 9 , wherein each a=2 and each b=0.

11 . A process to prepare a plasticizer comprising at least 2 alkyl ketal ester moieties, the plasticizer having a molecular weight of greater than 300, comprising the step:

contacting under reaction conditions an alkyl ketal ester having an acid number less than 0.3 as determined by ASTM method D664, a multihydric hydrocarbyl moiety, or a monohydric alkyl ketal ester; and

a catalyst, wherein a plasticizer comprising at least 2 alkyl ketal ester moieties is obtained with a molecular weight of greater than 300.

12 . The process of claim 11 , wherein the plasticizer has a formula comprising:

combinations thereof, wherein

each a, independently, is from 0 or an integer of 1 to 12;

each b, independently, is 0 or 1;

c is from 0 to 12;

d is 0 or 1;

each e, independently, is from 0 to 12;

each f, independently, is from 0 to 12;

each i is 0 or 1;

each j, independently, is 0 to 100;

each R 1 , independently, is a hydrogen, a hydrocarbyl group, or a substituted hydrocarbyl group;

each R 2 , R 3 and R 4 are independently methylene, alkylmethylene, or dialkylmethylene;

R 5 is a hydrogen or

R 6 is a hydrocarbyl group or a substituted hydrocarbyl group;

each R 7 , independently, is a hydrogen, a hydrocarbyl or a substituted hydrocarbyl group;

each R 8 , independently, is a hydrogen, a hydrocarbyl or a substituted hydrocarbyl group;

each R 10 , independently, is a hydrocarbyl or a substituted hydrocarbyl group;

R 11 is a hydrocarbyl, a substituted hydrocarbyl, or a hydrocarbyl group terminated with one or more heteroatoms to form a cyclic membered ring and which can include one or more of —O—, —NH—, —NR—, wherein R is a hydrocarbyl or a substituted hydrocarbyl;

R 12 , is a covalent bond, a hydrocarbyl group or a substituted hydrocarbyl group;

each R 14 , independently, is a hydrogen, a hydrocarbyl, or a substituted hydrocarbyl group;

each R 15 , independently, is a hydrogen, a hydrocarbyl, or a substituted hydrocarbyl group;

each R 19 , independently, is a hydrocarbyl, a substituted hydrocarbyl, or a hydrocarbyl group substituted with up to 5 hydroxyl groups;

each R 23 is a hydrocarbyl group or substituted hydrocarbyl group having between 1 and 12 carbon atoms

each Z, independently, is —O—, —NH— or —NR— where R is a hydrocarbyl or a substituted hydrocarbyl group;

n is from 1 to 100;

s is at least one;

v is from 0 to 100;

w is from 1 to 100;

x is at least 1;

y is 0 or a positive number.

13 . The process of claim 12 , wherein the plasticizer is the compound of formula (IV) wherein R 11 is a C4 alkyl.

14 . The process of claim 13 , wherein each a=2 and each b=0.

15 . A process to prepare a plasticizer in at least a 90% yield, wherein the plasticizer has a molecular weight of greater than 300 with at least 2 alkyl ketal ester moieties, comprising the step:

contacting under reaction conditions, an alkyl ketal ester, a multihydric hydrocarbyl moiety, or a monohydric alkyl ketal ester;

a catalyst; and

an antioxidant, a thermal stabilizer or mixtures thereof, wherein a plasticizer comprising at least 2 alkyl ketal ester moieties is obtained with a molecular weight of greater than 300 and is produced in at least a 90% yield.

16 . The process of claim 15 , wherein the plasticizer has a formula comprising:

combinations thereof, wherein

each a, independently, is from 0 or an integer of 1 to 12;

each b, independently, is 0 or 1;

c is from 0 to 12;

d is 0 or 1;

each e, independently, is from 0 to 12;

each f, independently, is from 0 to 12;

each i is 0 or 1;

each j, independently, is 0 to 100;

each R 1 , independently, is a hydrogen, a hydrocarbyl group, or a substituted hydrocarbyl group;

each R 2 , R 3 and R 4 are independently methylene, alkylmethylene, or dialkylmethylene;

R 5 is a hydrogen or

R 6 is a hydrocarbyl group or a substituted hydrocarbyl group;

each R 7 , independently, is a hydrogen, a hydrocarbyl or a substituted hydrocarbyl group;

each R 8 , independently, is a hydrogen, a hydrocarbyl or a substituted hydrocarbyl group;

each R 10 , independently, is a hydrocarbyl or a substituted hydrocarbyl group;

R 11 is a hydrocarbyl, a substituted hydrocarbyl, or a hydrocarbyl group terminated with one or more heteroatoms to form a cyclic membered ring and which can include one or more of —O—, —NH—, —NR—, wherein R is a hydrocarbyl or a substituted hydrocarbyl;

R 12 , is a covalent bond, a hydrocarbyl group or a substituted hydrocarbyl group;

each R 14 , independently, is a hydrogen, a hydrocarbyl, or a substituted hydrocarbyl group;

each R 15 , independently, is a hydrogen, a hydrocarbyl, or a substituted hydrocarbyl group;

each R 19 , independently, is a hydrocarbyl, a substituted hydrocarbyl, or a hydrocarbyl group substituted with up to 5 hydroxyl groups;

each R 23 is a hydrocarbyl group or substituted hydrocarbyl group having between 1 and 12 carbon atoms

each Z, independently, is —O—, —NH— or —NR— where R is a hydrocarbyl or a substituted hydrocarbyl group;

n is from 1 to 100;

s is at least one;

v is from 0 to 100;

w is from 1 to 100;

x is at least 1;

y is 0 or a positive number.

17 . The process of claim 16 , wherein the plasticizer is the compound of formula (IV) wherein R 11 is a C4 alkyl.

18 . The process of claim 17 , wherein each a=2 and each b=0.

19 . A process to prepare a plasticizer, wherein the plasticizer has a molecular weight of greater than 300 with at least 2 alkyl ketal ester moieties, comprising the step:

contacting under reaction conditions an alkyl ketal ester, a multihydric hydrocarbyl moiety, or a monohydric alkyl ketal ester;

a catalyst; and

an adsorbent, carbon, alumina, a buffer solution, a basic solution or mixtures thereof, wherein a plasticizer comprising at least 2 alkyl ketal ester moieties with a molecular weight of greater than 300 is obtained.

20 . The process of claim 19 , wherein the plasticizer has a formula comprising:

combinations thereof, wherein

each a, independently, is from 0 or an integer of 1 to 12;

each b, independently, is 0 or 1;

c is from 0 to 12;

d is 0 or 1;

each e, independently, is from 0 to 12;

each f, independently, is from 0 to 12;

each i is 0 or 1;

each j, independently, is 0 to 100;

each R 1 , independently, is a hydrogen, a hydrocarbyl group, or a substituted hydrocarbyl group;

each R 2 , R 3 and R 4 are independently methylene, alkylmethylene, or dialkylmethylene;

R 5 is a hydrogen or

R 6 is a hydrocarbyl group or a substituted hydrocarbyl group;

each R 7 , independently, is a hydrogen, a hydrocarbyl or a substituted hydrocarbyl group;

each R 8 , independently, is a hydrogen, a hydrocarbyl or a substituted hydrocarbyl group;

each R 10 , independently, is a hydrocarbyl or a substituted hydrocarbyl group;

R 11 is a hydrocarbyl, a substituted hydrocarbyl, or a hydrocarbyl group terminated with one or more heteroatoms to form a cyclic membered ring and which can include one or more of —O—, —NH—, —NR—, wherein R is a hydrocarbyl or a substituted hydrocarbyl;

R 12 , is a covalent bond, a hydrocarbyl group or a substituted hydrocarbyl group;

each R 14 , independently, is a hydrogen, a hydrocarbyl, or a substituted hydrocarbyl group;

each R 15 , independently, is a hydrogen, a hydrocarbyl, or a substituted hydrocarbyl group;

each R 19 , independently, is a hydrocarbyl, a substituted hydrocarbyl, or a hydrocarbyl group substituted with up to 5 hydroxyl groups;

each R 23 is a hydrocarbyl group or substituted hydrocarbyl group having between 1 and 12 carbon atoms

each Z, independently, is —O—, —NH— or —NR— where R is a hydrocarbyl or a substituted hydrocarbyl group;

n is from 1 to 100;

s is at least one;

v is from 0 to 100;

w is from 1 to 100;

x is at least 1;

y is 0 or a positive number.

21 . The process of claim 20 , wherein the plasticizer is the compound of formula (IV) wherein R 11 is a C4 alkyl.

22 . The process of claim 21 , wherein each a=2 and each b=0.

23 . A process to prepare a plasticizer, wherein the plasticizer comprises at least 2 alkyl ketal ester moieties with a molecular weight of greater than 300, comprising the step:

contacting an alkyl ketal ester, a multihydric hydrocarbyl moiety, or a monohydric alkyl ketal ester;

a catalyst; and

optionally, an antioxidant under reaction conditions, wherein the reaction is conducted without the substantial presence of air, providing a plasticizer that has a color index (YI) of less than 50 measured by ASTM method E313 having at least 2 alkyl ketal ester moieties with a molecular weight of greater than 300.

24 . The process of claim 23 , wherein the plasticizer has a formula comprising:

combinations thereof, wherein

each a, independently, is from 0 or an integer of 1 to 12;

each b, independently, is 0 or 1;

c is from 0 to 12;

d is 0 or 1;

each e, independently, is from 0 to 12;

each f, independently, is from 0 to 12;

each i is 0 or 1;

each j, independently, is 0 to 100;

each R 1 , independently, is a hydrogen, a hydrocarbyl group, or a substituted hydrocarbyl group;

each R 2 , R 3 and R 4 are independently methylene, alkylmethylene, or dialkylmethylene;

R 5 is a hydrogen or

R 6 is a hydrocarbyl group or a substituted hydrocarbyl group;

each R 7 , independently, is a hydrogen, a hydrocarbyl or a substituted hydrocarbyl group;

each R 8 , independently, is a hydrogen, a hydrocarbyl or a substituted hydrocarbyl group;

each R 10 , independently, is a hydrocarbyl or a substituted hydrocarbyl group;

R 11 is a hydrocarbyl, a substituted hydrocarbyl, or a hydrocarbyl group terminated with one or more heteroatoms to form a cyclic membered ring and which can include one or more of —O—, —NH—, —NR—, wherein R is a hydrocarbyl or a substituted hydrocarbyl;

R 12 , is a covalent bond, a hydrocarbyl group or a substituted hydrocarbyl group;

each R 14 , independently, is a hydrogen, a hydrocarbyl, or a substituted hydrocarbyl group;

each R 15 , independently, is a hydrogen, a hydrocarbyl, or a substituted hydrocarbyl group;

each R 19 , independently, is a hydrocarbyl, a substituted hydrocarbyl, or a hydrocarbyl group substituted with up to 5 hydroxyl groups;

each R 23 is a hydrocarbyl group or substituted hydrocarbyl group having between 1 and 12 carbon atoms

each Z, independently, is —O—, —NH— or —NR— where R is a hydrocarbyl or a substituted hydrocarbyl group;

n is from 1 to 100;

s is at least one;

v is from 0 to 100;

w is from 1 to 100;

x is at least 1;

y is 0 or a positive number.

25 . The process of claim 24 , wherein the plasticizer is the compound of formula (IV) wherein R 11 is a C4 alkyl.

26 . The process of claim 25 , wherein each a=2 and each b=0.

27 . A process to prepare a plasticizer, wherein the plasticizer comprises at least 2 alkyl ketal ester moieties with a molecular weight of greater than 300, comprising the step:

contacting the plasticizer with a molecular weight of greater than 300 and at least 2 alkyl ketal ester moieties with hydrogen under hydrogenation conditions, providing a purified plasticizer that has a color index (YI) of less than 50 measured by ASTM method E313 having at least 2 alkyl ketal ester moieties with a molecular weight of greater than 300.

28 . The process of claim 27 , wherein the plasticizer has a formula comprising:

combinations thereof, wherein

each a, independently, is from 0 or an integer of 1 to 12;

each b, independently, is 0 or 1;

c is from 0 to 12;

d is 0 or 1;

each e, independently, is from 0 to 12;

each f, independently, is from 0 to 12;

each i is 0 or 1;

each j, independently, is 0 to 100;

each R 1 , independently, is a hydrogen, a hydrocarbyl group, or a substituted hydrocarbyl group;

each R 2 , R 3 , and R 4 are independently methylene, alkylmethylene, or dialkylmethylene;

R 5 is a hydrogen or

R 6 is a hydrocarbyl group or a substituted hydrocarbyl group;

each R 7 , independently, is a hydrogen, a hydrocarbyl or a substituted hydrocarbyl group;

each R 8 , independently, is a hydrogen, a hydrocarbyl or a substituted hydrocarbyl group;

each R 10 , independently, is a hydrocarbyl or a substituted hydrocarbyl group;

R 11 is a hydrocarbyl, a substituted hydrocarbyl, or a hydrocarbyl group terminated with one or more heteroatoms to form a cyclic membered ring and which can include one or more of —O—, —NH—, —NR—, wherein R is a hydrocarbyl or a substituted hydrocarbyl;

R 12 , is a covalent bond, a hydrocarbyl group or a substituted hydrocarbyl group;

each R 14 , independently, is a hydrogen, a hydrocarbyl, or a substituted hydrocarbyl group;

each R 15 , independently, is a hydrogen, a hydrocarbyl, or a substituted hydrocarbyl group;

each R 19 , independently, is a hydrocarbyl, a substituted hydrocarbyl, or a hydrocarbyl group substituted with up to 5 hydroxyl groups;

each R 23 is a hydrocarbyl group or substituted hydrocarbyl group having between 1 and 12 carbon atoms

each Z, independently, is —O—, —NH— or —NR— where R is a hydrocarbyl or a substituted hydrocarbyl group;

n is from 1 to 100;

s is at least one;

v is from 0 to 100;

w is from 1 to 100;

x is at least 1;

y is 0 or a positive number.

29 . The process of claim 28 , wherein the plasticizer is the compound of formula (IV) wherein R 11 is a C4 alkyl.

30 . The process of claim 29 , wherein each a=2 and each b=0.