Invented by Scott D. Allen, Ronald R. Valente, Han Lee, Anna E. Cherian, Donald L. Bunning, Nye A. Clinton, Olan Stanley Fruchey, Bernard Duane Dombek, Novomer Inc
The Novomer Inc invention works as followsThe present invention describes a method of producing a beta-lactone product. This method involves the following steps: reacting an electrolyte with a solvent with a carbonylation catalyst and carbon monoxide to create a reaction stream containing a beta lactone. The reaction stream then separates a portion from the solvent and carbonylation catalyst to produce: i. a beta lactone stream with the betalactone; ii. a catalyst recycling stream which includes the carbonylation catalyst and high boiling solvent. Finally, the feed stream.
Background for Processing for beta-lactone manufacturing
Beta lactones can be useful intermediates in the production of other chemical compounds, such as acrylic acid or acrylates. Acrylic acid can be used in many industries. Acrylic acid is usually made from propene, which itself is a byproduct of gasoline and ethylene production. There are many other ways to produce acrylic acid and otheracrylates, depending on economic and environmental conditions. Epoxides are another option.
The present invention includes the following steps: reacting the contents a feed stream, including an epoxide and a solvent with carbonylation catalyst and carbon monoxide to create a reaction productstream including a beta lactone. Separating a portion from the solvent and carbonylation catalyst to produce a stream containing the beta-lactone and ii) a catalyst recycle stream including the carbonylation catalyst; and finally adding the catalyst recycling stream into the feed stream.
In some embodiments, treatment of the beta-lactone stream is also included under conditions to convert it into a compound from the following group: acrylic acid,methyl acrylate and ethylacrylate.
In some embodiments, a solvent’s boiling point is higher than that of the beta-lactone at the same pressure.” Some embodiments have a boiling point that is lower than the boiling temperature of the beta-lactone at the same pressure.
In some embodiments, the Beta-lactone stream contains a portion the solvent and/or carbonylation catalyst. Some embodiments include a portion the epoxide in the beta-lactone stream. Some embodiments include beta-lactone in the recycling stream. Some embodiments include a portion or all of the epoxide in the reaction product stream.
In some embodiments, sufficient epoxide is present in the reaction product stream to prevent anhydride from being formed. Some embodiments contain at least 10% epoxide and at most about 5% epoxide.
In some embodiments, the reaction products stream contains less than 5% anhydride or less than 1% anhydride.” Some embodiments leave the reaction product stream virtually free of anhydride.
In some embodiments, this method also includes the treatment of the catalyst recycling stream prior to the addition step. This can include adding new carbonylation catalyst, removing old carbonylation catalyst; adding solvent, adding epoxide or adding a portion the beta-lactone stream; or any combination of several of these.
In some embodiments, the separation step involves exposing the reaction product stream at elevated temperatures. Some embodiments allow for an elevated temperature that is higher than the boiling points of the beta-lactone, but lower than the boiling points of the solvent.
In some embodiments, the separation step involves exposing the reaction product stream under reduced pressure and at elevated temperatures.
In certain embodiments, the method also includes the step of condensing volatilized beta lactone from the separation step.
Some embodiments include adding a portion the beta-lactone stream into the feed stream. The beta-lactone stream can be added to the feed until it reaches a weight percent of 10% to 90%. After that, a portion is removed from the stream to keep the percent of beta lactone in reaction product stream at 10% to 90%. Some embodiments add the beta lactone stream to the feed until the percent weight of beta-lactone is within the range of 30% to about 65 percent. Then, a portion is taken out of the beta lactone stream to maintain the percent weight of beta-lactone contained in the reaction stream, which is between 30% and 65%. Some embodiments add the beta lactone stream to the feed until the percent weight of beta-lactone is between about 43% and about 53%. Then, a portion is taken out of the beta lactone stream to preserve the percent weight of beta-lactone within the reaction product streams in the range from about 43% up to 53%.
In some embodiments, this method also includes the addition of a second solvent before the step to further treat the beta-lactone stream in conditions that convert the beta lactone.
In some embodiments, further treatment of the beta-lactone stream under conditions for converting the beta lactone can be done in the gas phase.
In certain embodiments, the formula of the epoxide is
Where R1 or R2 are independently selected from the following group:?H, optionally substituted C1-6 aliphatic, phenyl, optionally substitution C1-6heteroaliphatic, optionally substitued 3-to 6-membered carbocycle, and optionally substituted 3 to 6-membered heterocycle. R1 or R2 can optionally also be combined with intervening atoms in order to form an optionally subordinated ring containing one, more, or all heteroatoms
In some embodiments, the epoxide is chosen from the group consisting of: ethylene oxide; propylene oxide; 1,2-butylene oxide; 2,3-butylene oxide; epichlorohydrin; cyclohexene oxide; cyclopentene oxide; 3,3,3-Trifluoro-1,2-epoxypropane, styrene oxide; a glycidyl ether; and a glycidyl ester. In some embodiments, ethylene oxide is the epoxide. In some embodiments, epoxide can be propylene oxide.
In some embodiments, further treatment of the beta-lactone stream is done in the presence a compound from the group consisting: an alcohol, amine, and a trihalomethane, under conditions that yield the corresponding acrylic ester or acrylamide respectively.Click here to view the patent on Google Patents.