Recovery of glycols from glycol-containing streams from depolymerised polyesters

Abstract: A process for recovering glycols produced during recycling of polyester comprising the step of extracting aromatic contaminants from the glycols. Extracting the aromatic contaminants is accomplished by: providing a glycol rich stream from a process to recycle polyester. The glycol rich stream comprised glycols, water, and aromatic contaminants. A solvent is added to the glycol rich stream to form a mixture. The mixture is resolved to form a glycol rich component and an aromatic contaminant rich component. The glycols are recovered from the glycol rich component.

Description: This invention is directed to a process for recovering glycols from a process to recycle polyester via depolymerization. Background of the Invention Scrap polyethylene terephthalate (PET) and PET production wastes are often landfilled. Landfilling of these materials represents, among other things, a loss of raw material, and a potential ecological problem, if improperly landfilled. Accordingly, an economical process for recycling of these materials is desirable. The recycling of scrap PET and PET production waste, in general, is known. The materials can be reacted with methanol, i.e. "methanolysis", to produce dimethyl terephthalate (DMT). For example, see U. S. Patent Nos. 2,884,443; 3,037,050; 3,148,208; 3,321,510; 3,488,298; 3,907,868; 4,163,860; 4,578,502; 5,051,528; 5,298,530; 5,391,263; 5,414,022; and Canadian Patent Application No. 2,104,253. Scrap PET can be reacted with ethylene glycol, i.e. "glycolysis", to produce bis-(2-hydroxyethyl) terephthalate (BHET), a PET monomer. For example, see U. S. Patent No. 4,078,143, column 1. PET scrap can be melted and reformed without depolymerization. For example, see U. S. Patent Nos. 5,225,130; and 5,248,041. Additionally, there are known methods by which catalysts can be removed from PET production waste. For example, see U. S. Patent No. 4,013,519 and 4,118,582. WO-A-95/11876 discloses that a glycol solution which is contaminated with hydrocarbons resulting from oil or gas production effluent processing, is purified by adding water to the contaminated glycol solution to form a hydrocarbon phase and a glycol phase which are separated from another, followed by desalination and steam stripping of the separated glycol phase. One problem arising during the recycling of PET scrap and PET production waste is the effective separation of glycols (e.g. ethylene glycol) from the glycol waste stream produced by the process for recycling the polyester. These glycols are contaminated with, not only water, but also aromatic contaminants. These aromatic contaminants must be removed, so that the glycols may be reused effectively. Accordingly, there is a need for a process in which the glycols (e.g. ethylene glycol) can be efficiently removed (i.e. in a cost effective and efficient manner) from the glycol waste stream produced by the process for recycling the polyester. Summary of the Invention The invention relates to a method for recovering glycols from depolymerized polyester comprising extracting aromatic contaminants from the glycols by: providing a glycol rich stream from a process to depolymerize polyester, the glycol rich stream comprising glycols, water, and aromatic contaminants; adding a solvent selected from the group consisting of p-xylene, o-xylene and m-xylene to the glycol rich stream to form a mixture; resolving the mixture to form a glycol rich component and an aromatic contaminant rich component; and recovering glycols from the glycol rich component. The invention further relates to recovering of the glycols by the further steps of: resolving the glycol rich component, the glycol rich component comprising glycols and water, into the glycols and water. Description of the Drawing For the purpose of illustrating the invention, there is shown in the drawing a form which is presently preferred; it being understood, however, that this invention is not limited to the precise arrangement and instrumentalities shown. Figure 1 is a schematic of the present invention. Detailed description of the Invention Referring to Figure 1, there is shown a process 10 for recovering glycols from a process to recycle (or depolymerize) polyester. A process for recycling (or depolymerizing) polyester 12 produces a dimethyl terephthalate rich stream 14 and a glycol rich stream 16. Glycol rich stream 16 is fed to a separator 20. A solvent stream 18 is also fed to separator 20. Separator 20 resolves the mixture into an aromatic contaminant rich component 22 and a glycol rich component 24. Preferably, separator 20 is a liquid-liquid extractor. Glycol rich component 24 is fed to a dehydrator 26. Dehydrator 26 resolves a glycol rich component into an aqueous stream 28 and a glycol stream 30. Glycol stream 30 is fed to a still 32. Still 32 resolves the glycol stream 30 into a waste stream 34 and an ethylene glycol stream 36. A preferred process for recycling (or depolymerizing) polyester is set forth in U.S. Patent Nos. 5,414,106; 5,414,107 and 5,502,239. Additional processes for depolymerizing polyester are disclosed in U.S. Patent Nos. 2,884,443; 3,037,050; 3,148,208; 3,221,510; 3,488,298; 3,907,868; 4,578,502; 5,051,528; 5,298,530; 5,391,263; 5,414,022; and Canadian Patent application No. 2,104,253. Aromatic contaminants comprise methyl benzoate, mono-methyl terephthalate, dimethyl terephthalate, methyl-p-toluate, terephthalic acid, and p-toluic acid. The aromatic contaminants mostly comprise methyl benzoate and mono-methyl terephthalate. A glycol rich stream comprises 1 to 50% by weight ethylene glycol and 0.45 to 5% by weight diethylene glycol with trace amounts of higher glycols. The stream may comprise 5 to 20% by weight ethylene glycol and 0.45 - 2% by weight diethylene glycol with trace amounts of higher glycols. The solvent comprises p-xylene, o-xylene, m-xylene, and methyl-p-toluate. The preferred solvent is p-xylene. Further details regarding the invention are set forth in the non-limiting example which follows. Example An aqueous stream (463g) containing 13.1% by weight ethylene glycol, 0.45% by weight methyl benzoate, and 0.03% by weight mono-methyl terephthalate was heated on a steam bath to 50°C and vigorously shaken with 203g of p-xylene (at 50°C). The organic and aqueous phases were allowed to separate. Both phases were analyzed by gas chromatography (GC) with the results (% by weight) listed in the table below: Feed Aqueous Phase Organic Phase ethylene glycol 13.1 13.05 0.05 methyl benzoate 0.45 not detected 1.1 mono-methyl terephthalate 0.03 0.009 0.02

Claims: A method for recovering glycols from depolymerized polyester comprising extracting aromatic contaminants from the glycols by: providing a glycol rich stream from a process to depoly merize polyester, the glycol rich stream comprising glycols, water, and aromatic contaminants; adding a solvent selected from the group consisting of p-xylene, o-xylene and m-xylene to the glycol rich stream to form a mixture; resolving the mixture to form a glycol rich component and an aromatic contaminant rich component; and recovering glycols from the glycol rich component. The method according to claim 1 wherein recovering glycols further comprises the steps of: resolving the glycol rich component, the glycol rich component comprising glycols and water, into the glycols and water. A method according to claim 1 or 2 wherein the glycol rich stream is from a process to depolymerize polyethylene terephthalate. A method according to any one of claims 1 to 3, wherein the glycol rich stream comprises 1 to 50 % by weight ethylene glycol, 0.45 to 5 % by weight diethylene glycol and trace amounts of higher glycols. A method according to claim 4 wherein the aromatic contaminants in the glycol rich stream and the aromatic contaminant rich component comprise methyl benzoate. A method according to claim 5 wherein the aromatic contaminants in the glycol rich stream and the aromatic rich component comprise methyl benzoate and monomethyl terephthalate. A method according to claim 6 wherein the solvent is p-xylene.

Inventors: SMITH BRAD L, WILKINS GARY E, SMITH, BRAD L., WILKINS, GARY E.
Applicants: ARTEVA TECH SARL, ARTEVA TECHNOLOGIES S.A.R.L.
Application year: 1997
Main classification: C07C29
IPC codes: C08L67, C07C29, C08G63, C08J11