Production of Mixed Aldol Products from the Products of Hydroformylation Reactions

Abstract

A method for producing mixed aldol products from the products of hydroformylation reactions. In one embodiment, the method comprises mixing hydroformylation reaction products comprising aldehydes with a catalyst inside a reactor to create a mixture. The method also includes agitating the mixture at a temperature in a range of between about 200° F. to about 275 ° F. to create a reacted mixture. The reacted mixture is then cooled in the reactor to create an organic phase and an aqueous phase. The organic phase is pumped out of the reactor and may then be transferred to a distillation tower. The organic phase may be distilled until any mixed aldol products are isolated, wherein the mixed aldol products may be subsequently removed.

What is claimed is: 
     
         1 . A method for producing mixed aldol products from products of hydroformylation reactions, the method comprises:
 (A) mixing hydroformylation products comprising aldehydes with a catalyst inside a reactor to create a mixture, wherein the catalyst is sodium hydroxide;   (B) agitating the mixture at a temperature in a range of between about 200° F. to about 275 ° F. to create a reacted mixture;   (C) cooling the reaction mixture in the reactor to phase separate the reacted mixture into an organic phase and an aqueous phase, wherein the reacted mixture is cooled by a temperature gradient of about 1° F. to about 25° F.;   (D) removing the organic phase out of the reactor;   (E) transferring the organic phase to a distillation tower;   (F) distilling the organic phase until mixed aldol products are isolated, wherein the distilling is performed with a vacuum of 24 inches to 28 inches of mercury, wherein distilling is performed with nitrogen sparging; and   (G) removing the mixed aldol products.   
     
     
         2 . The method of  claim 1 , wherein the hydroformylation products comprise methanol, propanol, isobutyl alcohol, n-butyl alcohol, 2-methyl-1-butanol, acetaldehyde, propionaldehyde, isobutyraldehyde, butyraldehyde, 2-methyl-1-butanal, valeraldehyde, 2-methyl-2-pentanal, or any combinations thereof. 
     
     
         3 . The method of  claim 1 , wherein a ratio of the hydroformylation products to the catalyst is in a range of between about 10:1 to about 1:10. 
     
     
         4 . The method of  claim 1 , wherein the reactor is a batch reactor. 
     
     
         5 . The method of  claim 1 , wherein the reaction temperature is between about 190° F. to about 240° F. 
     
     
         6 . The method of  claim 1 , wherein the mixed aldol products comprise C 6 -C 20  aldehydes. 
     
     
         7 . The method of  claim 1 , wherein the mixed aldol products comprise 2-ethyl-2-heptenal, 2-ethyl-2-hexenal, 2-propyl-2-heptenal, 2-ethyl-2-pentenal, 2-methyl-2-heptenal, 2-propyl-2-hexenal, 1, 2-methyl-2-hexenal, 2-methyl-2-pentenal, 2-propyl-2-pentenal, ethyl octenal, derivatives thereof, or any combinations thereof. 
     
     
         8 . The method of  claim 1 , wherein the mixed aldol products have a flashpoint greater than 110° F. 
     
     
         9 . The method of  claim 1 , further comprising a phase transfer catalyst. 
     
     
         10 . The method of  claim 9 , wherein the phase transfer catalyst is tetra butyl ammonium bromide, tetra butyl ammonium hydrogen sulfate, or combinations thereof. 
     
     
         11 . The method of  claim 9 , wherein the phase transfer catalyst is present in the reactor in an amount of about 0.1% to about 10% by volume. 
     
     
         12 . A method for producing mixed aldol products from products of hydroformylation reactions, the method comprises:
 (A) mixing hydroformylation products comprising aldehydes with a catalyst inside a reactor to create a mixture, wherein the catalyst is sodium hydroxide;   (B) agitating the mixture at a temperature in a range of between about 200° F. to about 275 ° F. to create a reacted mixture;   (C) cooling the reacted mixture in the reactor to phase separate the reacted mixture into an organic phase and an aqueous phase, wherein the reacted mixture is cooled by a temperature gradient of about 1° F. to about 25° F.;   (D) removing the organic phase out of the reactor;   (E) transferring the organic phase to a distillation tower;   (F) distilling the organic phase until mixed aldol products are isolated from hydroformylation products;   (G) removing the mixed aldol products; and   (H) recycling unreacted hydroformylation products into a feed supply to the reactor.   
     
     
         13 . The method of  claim 12 , further comprising removing spent catalyst from the reactor after step (C) and recycling the spent catalyst by mixing of the spent catalyst with an amount of a concentrated catalyst and then introducing the mixture to the reactor. 
     
     
         14 . The method of  claim 13 , wherein the concentrated catalyst comes from a concentrated catalyst source that is diluted with water. 
     
     
         15 . The method of  claim 12 , wherein the hydroformylation products comprise methanol, propanol, isobutyl alcohol, n-butyl alcohol, 2-methyl-1-butanol, acetaldehyde, propionaldehyde, isobutyraldehyde, butyraldehyde, 2-methyl-1-butanal, valeraldehyde, 2-methyl-2-pentanal, or any combinations thereof. 
     
     
         16 . The method of  claim 12 , wherein a ratio of the hydroformulation products to the catalyst is in a range of between about 10:1 to about 1:10. 
     
     
         17 . The method of  claim 12 , wherein the reactor is a batch reactor. 
     
     
         18 . The method of  claim 12 , wherein the reaction temperature is between about 190° F. to about 240° F. 
     
     
         19 . The method in  claim 12 , wherein the mixed aldol products comprise C 6 -C 20  unsaturated aldehydes. 
     
     
         20 . A method for producing mixed aldol products from products of hydroformylation reactions, the method comprises:
 (A) mixing hydroformylation products comprising aldehydes with a catalyst inside a reactor to create a mixture, wherein the catalyst is sodium hydroxide;   (B) agitating the mixture at a temperature in a range of between about 200° F. to about 275° F. to create a reacted mixture;   (C) cooling the reacted mixture in the reactor to phase separate the reacted mixture into an organic phase and an aqueous phase, wherein the reacted mixture is cooled by a temperature gradient of about 1° F. to about 25° F.;   (D) removing the organic phase out of the reactor, wherein the organic phase comprises mixed aldol products, unreacted hydroformylation reaction products, mixed alcohol products, or any combination thereof;   (E) transferring the organic phase to a distillation tower;   (F) distilling the organic phase until mixed aldol products are isolated from hydroformylation products;   (G) removing the mixed aldol products;   (H) removing the mixed alcohol products; and   (I) recycling the unreacted hydroformylation products into a feed supply to the reactor.