Process for making allyl succinic anhydride
View Patent ↗A process for the production of allyl succinic anhydride comprising reacting a mixture of propene with maleic anhydride in the presence of a catalyst comprised of an alkyl tin chloride as provided. The process can be run efficiently at temperatures below about 200° C. without and the formation of polymer or decomposition by-products.
1. A process for the production of allyl succinic anhydride, comprising reacting propene with maleic anhydride in the presence of a catalytically effective amount of an organotin chloride catalyst.
2. The process of claim 1 , wherein the organotin chloride catalysts are those according to formula (1) below:
wherein
R 1 , R 2 are each independently alkyl, alkenyl, alkynyl, or phenyl,
R 3 is Cl or alkyl, alkenyl, or alkynyl.
3. The process of claim 2 , wherein R 1 and R 2 are each independently (C 1 -C 6 )alkyl or phenyl and R 3 is Cl or (C 1 -C 6 )alkyl.
4. The process of claim 1 , wherein the catalyst comprises one or more compound selected from the group consisting of methyl tin dichloride, dimethyl tin dichloride, ethyl tin dichloride, diethyl tin dichloride, n-butyl tin trichloride, di-n-butyl tin dichloride, s-butyl tin dichloride, di s-butyl tin dichloride, t-butyl tin dichloride, di t-butyl tin dichloride, n-pentyl tin trichloride, di n-pentyl tin dichloride, n-hexyl tin trichloride, di n-hexyl tin dichloride, and phenyl tin dichloride.
5. The process of claim 1 wherein the catalyst comprises one or more compound selected from the group consisting of n-butyl tin trichloride, diphenyl tin dichloride, divinyl tin dichloride, dimethyl tin dichloride, di n-butyl tin dichloride, and di t-butyl tin dichloride.
6. The process of claim 1 wherein said catalyst comprises one or more compound selected from the group consisting of dimethyl tin dichloride, dibutyl tin dichloride, and butyl tin trichloride.
7. The process of claim 1 wherein the reaction is conducted at a temperature of less than about 200° C.
8. The process of claim 1 where the mixture conducted at a temperature of less than about 180° C.
9. The process of claim 1 , wherein the reaction mixture initially comprises substantially equimolar amounts propene and maleic anhydride.
10. The process of claim 1 , wherein the reaction mixture initially comprises a molar excess of propene relative to the amount of maleic anhydride.
11. The process of claim 1 , the reaction mixture initially comprises a molar excess, of up to about 10 mole %, of propene relative to the amount of maleic anhydride.
12. The process of claim 1 , wherein the process is carried out in a hydrocarbon solvent.
13. The process of claim 1 , wherein the process is conducted at a pressure of from about 100 to about 10,000 pounds per square inch above atmospheric pressure.
14. The process of claim 1 , wherein the process is conducted in the presence of a free radical scavenger.