Process for preparation of methyl methacrylate by esterification during oxidation

1. A process comprising:

at least partially oxidizing a feed composition comprising (i) a main compound which is at least isobutylene, and (ii) at least one co-compound selected from the group consisting of methanol, dimethyl ether, ethanol, methyl tert-butyl ether, ethyl tert-butyl ether and formaldehyde, in a catalytic reaction zone to obtain an oxidation phase comprising methacrylic acid as the main product, and

optionally, esterifying at least a part of the oxidation phase, wherein

said process occurs at least partially in the gas phase,

the feed composition is obtained by splitting of methyl tert-butyl ether or of ethyl tert-butyl ether,

the oxidation takes place in at least two separate oxidation stages, which comprise a first oxidation to form methacrolein as the main product and a second oxidation to form methacrylic acid as the main product.

2. The process according to claim 1 , further comprising:

esterifying at least a part of said at least one co-compound.

3. The process according to claim 1 , wherein the feed composition has a content of not less than 5 ppm of the at least one co-compound.

4. The process according to claim 1 , wherein the feed composition comprises the at least one co-compound in a range from 0.0005 to 10 wt. % based on the total weight of main compound and co-compound in the feed composition.

5. The process according to claim 1 , wherein the oxidation phase comprises at least 0.0005 wt. % methyl methacrylate, based on the hydrocarbons in the oxidation phase.

6. The process according to claim 2 , wherein the at least one part of said at least one co-compound is at least 90 wt. % of the at least one co-compound.

7. The process according to claim 1 , wherein said process is performed in an apparatus for production of methacrylic acid, said apparatus comprising:

i) a supply for a feed composition comprising a main compound which is at least isobutylene, and at least one co-compound selected from the group consisting of methanol, dimethyl ether, ethanol, methyl tert-butyl ether, ethyl tert-butyl ether and formaldehyde; in fluid communication with

ii) a catalytic reaction zone for at least partial conversion of the feed composition into methacrylic acid as the main product; in fluid communication with

iii) optionally, at least one first purification unit.

8. A process for preparation of a methacrylate ester with formula [CH 2 ═C(CH 3 )C(═O)O] n —R, comprising:

α1 preparing methacrylic acid according to the process of claim 1 ; and

α3 reacting the methacrylic acid obtained in α1 with an alcohol of formula R(OH) m ,

wherein n and m represent an integer from 1 to 10, and

R is at least one selected from the group consisting of a linear hydrocarbon, a branched hydrocarbon, a saturated hydrocarbon, an unsaturated hydrocarbon, an aliphatic hydrocarbon, an aromatic hydrocarbon, a ring hydrocarbon, a straight chain hydrocarbon, a linear heteroatom-comprising hydrocarbon, a branched heteroatom-comprising hydrocarbon, a saturated heteroatom-comprising hydrocarbon, an unsaturated heteroatom-comprising hydrocarbon, an aliphatic heteroatom-comprising hydrocarbon, an aromatic heteroatom-comprising hydrocarbon, a ring heteroatom-comprising hydrocarbon, and a straight chain heteroatom-comprising hydrocarbon.

9. A process for producing a polymer comprising at least one monomer unit selected from methacrylic acid, methyl methacrylate and a methacrylic ester with formula [CH 2 ═C(CH 3 )C(═O)] n —R, wherein

n represents an integer from 1 to 10, and

R is at least one selected from the group consisting of a linear hydrocarbon, a branched hydrocarbon, a saturated hydrocarbon, an unsaturated hydrocarbon, an aliphatic hydrocarbon, an aromatic hydrocarbon, a ring hydrocarbon, a straight chain hydrocarbon, a linear heteroatom-comprising hydrocarbon, a branched heteroatom-comprising hydrocarbon, a saturated heteroatom-comprising hydrocarbon, an unsaturated heteroatom-comprising hydrocarbon, an aliphatic heteroatom-comprising hydrocarbon, an aromatic heteroatom-comprising hydrocarbon, a ring heteroatom-comprising hydrocarbon, and a straight chain heteroatom-comprising hydrocarbon,

comprising:

A1. preparing at least one of methacrylic acid according to a process of subjecting a feed composition comprising (i) a main compound which is at least isobutylene, and (ii) at least one co-compound selected from the group consisting of methanol, dimethyl ether, ethanol, methyl tert-butyl ether, ethyl tert-butyl ether and formaldehyde, in a catalytic reaction zone to obtain an oxidation phase comprising methacrylic acid as the main product, methyl methacrylate, and at least one methacrylate ester according to a process according to claim 8 ,

A2a. polymerizing at least one of the methacrylic acid, the methyl methacrylate and the at least one methacrylate ester obtained in A1, and

A2b. optionally polymerizing at least one co-monomer which is co-polymerisable with at least one of methacrylic acid, methyl methacrylate and methacrylate ester.

10. The process according to claim 9 , wherein the at least one co-monomer is at least one co-monomer selected from the group consisting of: styrene, butadiene, acrylonitrile, butyl acrylate, vinyl acetate, and methyl acrylate.

11. A process for producing a composition comprising at least a first component selected from methacrylic acid, methyl methacrylate, at least one methacrylate ester, and a polymer comprising at least one monomer unit selected from methacrylic acid, methyl methacrylate and a methacrylate ester, comprising:

B1. obtaining at least one first component selected from methacrylic acid, methyl methacrylate, a methacrylate ester and a polymer according to the process of claim 9 ;

B2. optionally combining the at least one first component obtained in B1 with at least one further component.

12. The process according to claim 11 , wherein the at least one further component is at least one component selected from a substituted polystyrene, an unsubstituted polystyrene, a poly-n-butyl acrylate, a polyacrylonitrile, a polysaccharide, a silica and a nanomaterial.

13. The process for preparation of a methacrylate ester according to claim 8 , wherein said process for the preparation of methacrylic acid is performed in an apparatus for production of methacrylic acid, said apparatus comprising:

i) a supply for a feed composition comprising a main compound which is at least isobutylene and at least one co-compound selected from the group consisting of methanol, dimethyl ether, ethanol, methyl tert-butyl ether, ethyl tert-butyl ether and formaldehyde; in fluid communication with

ii) a catalytic reaction zone for at least partial conversion of the feed composition into methacrylic acid as the main product; in fluid communication with

iii) optionally, at least one first purification unit.

14. The process for preparation of a methacrylate ester according to claim 8 , wherein said process for the preparation of methyl methacrylate is performed in an apparatus for production of methyl methacrylate, said apparatus comprising:

i) a supply for a feed composition comprising a main compound which is at least isobutylene and at least one co-compound selected from the group consisting of methanol, dimethyl ether, ethanol, methyl tert-butyl ether, ethyl tert-butyl ether and formaldehyde; in fluid communication with

ii) a catalytic reaction zone for at least partial conversion of the feed composition into methacrylic acid as the main product; in fluid communication with

iii) optionally, at least one first purification unit; in fluid communication with

iv) an esterification unit;

optionally, a conduit unit; in fluid communication with at least the supply and the esterification unit.

15. A process for producing a polymer according to claim 9 , wherein said process for the preparation of methacrylic acid is performed in an apparatus for production of methacrylic acid, said apparatus comprising:

i) a supply for a feed composition comprising a main compound which is at least isobutylene and at least one co-compound selected from the group consisting of methanol, dimethyl ether, ethanol, methyl tert-butyl ether, ethyl tert-butyl ether and formaldehyde; in fluid communication with

ii) a catalytic reaction zone for at least partial conversion of the feed composition into methacrylic acid as the main product; in fluid communication with

iii) optionally, at least one first purification unit.

16. A process for producing a polymer according to claim 9 , wherein said methyl methacrylate is obtained by the process of:

a) subjecting a feed composition comprising a main compound which is at least isobutylene and at least one co-compound selected from the group consisting of methanol, dimethyl ether, ethanol, methyl tert-butyl ether, ethyl tert-butyl ether and formaldehyde, in the presence of a first part of said at least one co-compound to a catalytic reaction zone and obtaining an oxidation phase comprising methacrylic acid as the main product; and

b) esterification of at least a part of the oxidation phase obtained a).

17. A process for producing a polymer according to claim 16 , wherein said process for the preparation of methyl methacrylate is performed in an apparatus for production of methyl methacrylate, comprising:

i) a supply for a feed composition comprising a main compound which is at least isobutylene and at least one co-compound selected from the group consisting of methanol, dimethyl ether, ethanol, methyl tert-butyl ether, ethyl tert-butyl ether and formaldehyde; in fluid communication with

ii) a catalytic reaction zone for at least partial conversion of the feed composition into methacrylic acid as the main product; in fluid communication with

iii) optionally, at least one first purification unit; in fluid communication with

iv) an esterification unit;

optionally, a conduit unit; in fluid communication with at least the supply and the esterification unit.

18. A process for producing a composition according to claim 11 , wherein the methacrylic acid is obtained by the following process:

subjecting a feed composition comprising a main compound which is at least isobutylene, and at least one co-compound selected from the group consisting of methanol, dimethyl ether, ethanol, methyl tert-butyl ether, ethyl tert-butyl ether and formaldehyde, in the presence of a first part of said at least one co-compound to a catalytic reaction zone and obtaining an oxidation phase comprising methacrylic acid as the main product.

19. A process for producing a composition according to claim 11 , wherein the methyl methacrylate is obtained by the following process:

a) subjecting a feed composition comprising a main compound which is at least isobutylene and at least one co-compound selected from the group consisting of methanol, dimethyl ether, ethanol, methyl tert-butyl ether, ethyl tert-butyl ether and formaldehyde, in the presence of a first part of said at least one co-compound to a catalytic reaction zone and obtaining an oxidation phase comprising methacrylic acid as the main product; and

b) esterification of at least a part of the oxidation phase obtained a).

20. A process for producing a composition according to claim 11 , wherein the methacrylate ester has a formula [CH 2 ═C(CH 3 )C(═O)] n —R, wherein

n represents an integer from 1 to 10, and

R is at least one selected from the group consisting of a linear hydrocarbon, a branched hydrocarbon, a saturated hydrocarbon, an unsaturated hydrocarbon, an aliphatic hydrocarbon, an aromatic hydrocarbon, a ring hydrocarbon, a straight chain hydrocarbon, a linear heteroatom-comprising hydrocarbon, a branched heteroatom-comprising hydrocarbon, a saturated heteroatom-comprising hydrocarbon, an unsaturated heteroatom-comprising hydrocarbon, an aliphatic heteroatom-comprising hydrocarbon, an aromatic heteroatom-comprising hydrocarbon, a ring heteroatom-comprising hydrocarbon, and a straight chain heteroatom-comprising hydrocarbon.

21. The process of claim 1 , wherein the oxidizable compounds of the feed composition consist of the main compound and the co-compound.