Adipate-type compounds and a process of preparing it
The present invention regards new adipate-type compounds suitable as an intermediate in organic chemistry, a platform chemical for the production of other chemicals, and as a monomer and co-monomer useful for the preparation of polymers and copolymers. The invention also regards the process of preparing the new adipate-type compounds from bio-based raw materials such as sugars.
1. A compound of the formula I:
wherein either:
R 1 is selected from the group consisting of —H and C 1 -C 2 alkyl; and
R 2 is —CH 3 ,
or
R 1 is CH 3 ; and
R 2 is selected from the group consisting of —H and —CH 3 .
2. The compound according to claim 1 , wherein R 1 is —CH 3 and R 2 is —H.
3. The compound according to claim 1 , wherein R 1 is selected from the group consisting of —H, —CH 3 , and —CH 2 CH 3 and R 2 is —CH 3 .
4. The compound according to claim 1 , wherein R 1 and R 2 each are —CH 3 .
5. The compound according to claim 1 , wherein the C—C double bond of Compound (I) is in (E) configuration.
6. A composition comprising a compound of formula (I) according to claim 1 .
7. The composition according to claim 6 , further comprising a solvent.
8. The composition according to claim 6 , wherein at least 80 wt % of the compound of formula (I) is in (E)-configuration.
9. A process comprising the steps of:
i) providing a compound of the formula:
wherein
R 1 is selected from the group consisting of —H and C 1 -C 2 alkyl; and
R 2 is selected from the group consisting of —H and —CH 3 ;
ii) providing a catalyst material catalyzing a metathesis reaction;
iii) converting the compound of i) in the presence of the catalytic material of ii); and
iv) recovering a reaction product comprising a compound of formula (I):
wherein R 1 and R 2 are as defined in formula (II).
10. The process according to claim 9 , wherein the conversion temperature of iii) is in the range of from 20 to 120° C.
11. The process according to claim 9 , wherein step iii) is continued for a period of time in the range of from 5 minutes to 24 hours.
12. The process according to claim 9 , wherein the conversion step of iii) is conducted at a pressure in the range of from 1 to 1000 kPa.
13. The process according to claim 9 , wherein the conversion step of iii) is conducted without the addition of solvent.
14. The process according to claim 13 , wherein the compound of the formula (II) is provided in a feed comprising at least 50 wt % of the compound (II).
15. The process according to claim 9 , wherein the conversion step of iii) is conducted in the presence of an alkyl lactate.
16. The process according to claim 9 conducted under continuous conditions.
17. The process according to claim 9 , wherein:
R 1 is —H; and
R 2 is —H.
18. The process according to claim 9 , wherein:
R 1 is —H; and
R 2 is —CH 3 .
19. The process according to claim 9 , wherein:
R 1 is —CH 3 ; and
R 2 is —H.
20. The process according to claim 9 , wherein:
R 1 is —CH 3 ; and
R 2 is —CH 3 .
21. The process according to claim 9 , wherein:
R 1 is —CH 2 CH 3 ; and
R 2 is —H.
22. The process according to claim 9 , wherein:
R 1 is —CH 2 CH 3 ; and
R 2 is —CH 3 .
23. The compound according to claim 1 , wherein R 1 is —H and R 2 is —CH 3 .
24. The compound according to claim 1 , wherein R 1 is —CH 2 CH 3 and R 2 is —CH 3 .