Organic compounds -- part of the class 532-570 series – Organic compounds – Carbonate esters
Reexamination Certificate
2001-03-30
2003-01-14
McKane, Joseph K. (Department: 1626)
Organic compounds -- part of the class 532-570 series
Organic compounds
Carbonate esters
C210S790000
Reexamination Certificate
active
06506924
ABSTRACT:
BACKGROUND OF THE INVENTION
The present invention is directed to a method for recovering catalyst components from organic reaction mixtures and, more specifically, to a method for recovering a substantially water-soluble solvent from an organic reaction mixture comprising carbonylation reaction products.
Aromatic carbonates find utility, inter alia, as intermediates in the preparation of polycarbonates. For example, a popular method of polycarbonate preparation is the melt transesterification of aromatic carbonates with bisphenols.
Various methods for preparing aromatic carbonates have been previously described in the literature and/or utilized by industry. A method that has enjoyed substantial popularity in the literature involves the direct carbonylation of aromatic hydroxy compounds with carbon monoxide and oxygen catalyzed by at least one Group 8,9, or 10 metal source. Further refinements to the carbonylation catalyst composition include the identification of co-catalysts.
The utility of the carbonylation process is strongly dependent on the number of moles of aromatic carbonate produced per mole of metal catalyst utilized (i.e. “catalyst turnover number or “TON””). Consequently, much work has been directed to the identification of efficacious process and catalyst variations that increase catalyst turnover and yield of aromatic carbonate. For example, in U.S. Pat. No. 5,498,789 a catalyst system for carbonylation has been disclosed which consists of a palladium catalyst, lead compound, and an organic bromide. GB 2311777A discloses a catalyst system which comprises a palladium catalyst, a lead compound, a cobalt compound, and a halide. More efficient catalyst systems for carbonylation are reported, for example, in U.S. Pat. Nos. 6,114,564, 6,172,254, and 6,180,812, all assigned to the assignee of the present invention, in which catalyst systems may comprise alkali metal halides and an activating solvent (sometimes known as a “promoter compound”).
Recovery and reuse of all catalyst and recyclable components from a carbonylation reaction are imperative if a process to prepare aromatic carbonates is to be economically viable and environmentally safe. In particular, when an activating solvent is present in a carbonylation reaction mixture, then the activating solvent must be recovered and recycled efficiently.
Often, it is desirable to retain an activating solvent in an organic phase until it can be separated, for example by distillation. Since separation by distillation is often a high temperature process, decomposition and transesterification of aromatic carbonate product may occur, for example, if other catalyst components such as metals are present during a distillative separation of activating solvent and product. One possible method of removal of metallic or other catalyst components is by an aqueous extraction. In this case it is often desirable that an activating solvent remain in an organic phase during an aqueous extraction process so that it does not finally have to be separated from an aqueous stream containing other catalyst components such as metals. Many disclosed activating solvents such as polyethers tend to have a high solubility in water. A problem to be solved is to devise a method for efficient recovery of substantially water-soluble activating solvents from complex carbonylation reaction mixtures without the necessity of separating such solvents from a aqueous stream.
SUMMARY OF THE INVENTION
After diligent experimentation the present inventors have discovered a method for recovery of substantially water-soluble solvents from carbonylation reaction mixtures. Thus, in one embodiment, the present invention provides a method for recovering a substantially water-soluble solvent from a reaction mixture comprising at least about 35% by weight aromatic hydroxy compound, which comprises the steps of: (i) extracting a reaction mixture at least once with aqueous acid wherein the solvent remains substantially in the organic phase; and (ii) recovering solvent from the organic phase.
Various other features, aspects, and advantages of the present invention will become more apparent with reference to the following description and appended claims.
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Grade Marsha Mottel
Ofori John Yaw
Pressman Eric James
Brown S. Bruce
General Electric Company
Johnson Noreen C.
McKane Joseph K.
Saeed Kamal
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