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KR-20260062995-A - SYSTEMS AND METHODS FOR SEPARATING (E)-1-CHLORO-3,3,3-TRIFLUOROPROPENE, HF, AND A HEAVY ORGANIC AND REACTOR PURGE

KR20260062995AKR 20260062995 AKR20260062995 AKR 20260062995AKR-20260062995-A

Abstract

The present invention provides a separation process for removing heavy organic matter formed in various production processes of HCFO-1233zd(E). Such a separation process enables the recovery and/or separation of heavy organic matter from reactants used to form HCFO-1233zd(E), which includes HF. Such a separation or recovery process may utilize various separation techniques (e.g., decanting, liquid-liquid separation, distillation, and flash distillation) and may also utilize the unique properties of azeotropic or azeotropic mixture-like compositions. The recovery of heavy organic matter in the substantial absence of HF may enable its use in subsequent manufacturing processes or disposal.

Inventors

  • 치우, 위온
  • 세리, 구스타보
  • 코트렐, 스테판, 에이.
  • 맥크레인, 제니퍼, 더블유.
  • 왕, 타오
  • 싱, 라지브, 라트나
  • 바나바리, 라지브

Assignees

  • 허니웰 인터내셔날 인코포레이티드

Dates

Publication Date
20260507
Application Date
20180103
Priority Date
20171221

Claims (10)

  1. As a method for cleaning a reactor, (E) Step of removing reactor purge containing 1-1-chloro-3,3,3-trifluoropropene, HF and at least one heavy organic substance, A step of separating an HF phase and an organic phase comprising (E)-1-chloro-3,3,3-trifluoropropene and at least one heavy organic substance, A step of distilling the organic phase, and A method comprising the step of recovering at least one heavy organic material.
  2. In paragraph 1, The above heavy organic material has a weight average molecular weight (Mw) of about 500 g/mol to about 7,000 g/mol, optionally 600 g/mol to 6,000 g/mol, a method.
  3. In paragraph 1, The above heavy organic material comprises tar or a tar-like substance, method.
  4. In paragraph 1, The above heavy organic material has a boiling point of 120°C to 300°C at a pressure of 3 psia to 73 psia, method.
  5. In paragraph 1, (E) A method further comprising the step of adding a washing fluid to a mixture of 1-1-chloro-3,3,3-trifluoropropene, HF, and at least one heavy organic substance.
  6. In paragraph 5, A method wherein the washing fluid comprises at least one of 1-chloro-3,3,3-trifluoropropene, 1,1,1,3,3-pentachloropropane, 1,1,1,3-tetrachloro-3-fluoropropane, 1,1,1-trichloro-3,3-difluoropropane, HCl, or a mixture thereof.
  7. In paragraph 1, A method further comprising the step of forming an azeotropic or azeotropic mixture-like composition comprising HF and at least one of 1,1,1,3,3-pentachloropropane (240fa), 1,1,1,3-tetrachloro-3-fluoropropane (241fa), 1,1,1-trichloro-3,3-difluoropropane (242fa) or a combination thereof.
  8. In Paragraph 7, The above azeotrope or azeotrope mixture-like composition comprises HF and (E)-1-chloro-3,3,3-trifluoropropene and has a boiling point of 0°C to 60°C at a pressure of 3 to 73 psia, method.
  9. (E) A method for separating 1-1-chloro-3,3,3-trifluoropropene, HF, and heavy organic matter, (E) A step of providing a mixture of 1-chloro-3,3,3-trifluoropropene, HF, and heavy organic matter; A step of separating an HF stream and an organic stream comprising (E)-1-chloro-3,3,3-trifluoropropene and at least one heavy organic substance, wherein the separation of the HF stream and the organic stream comprises at least one of decanting, centrifugation, liquid-liquid extraction, distillation, flash distillation, or a combination thereof; and A method comprising the step of distilling an HF stream to form an HF-rich overhead and a light organic stream.
  10. A method for producing (E)-1-chloro-3,3,3-trifluoropropene by a fluorination reaction, A method in which a reactor is cleaned according to any one of the methods of claims 1 to 9.

Description

Systems and methods for separating (E)-1-chloro-3,3,3-trifluoropropene, HF, and a heavy organic and reactor purge Cross-reference regarding related applications This application claims the benefit under U.S. Provisional Patent Application No. 62/443,349, filed January 6, 2017, titled "SYSTEMS AND METHODS FOR SEPARATING (E)-1-CHLORO-3,3,3-TRIFLUOROPROPENE, HF, AND A HEAVY ORGANIC AND REACTOR PURGE," the entire disclosure of which is expressly incorporated herein by reference. Technology field The present invention relates to the separation of HF from heavy organic matter. More specifically, the present invention relates to the separation and recovery of heavy organic matter from the production of ((E)-1-chloro-3,3,3-trifluoropropene (HCFO-1233zd(E)). Fluorocarbon fluids have been widely used in numerous applications in industry, including as refrigerants, aerosol propellants, foaming agents, heat transfer media, and gaseous dielectrics. Due to suspected environmental issues associated with the use of some of these fluids, including their relatively high global warming potential, it is desirable to use fluids that have the lowest possible global warming potential (GWP) in addition to having an ozone depletion potential (ODP) of zero. Therefore, there is significant interest in developing more environmentally friendly materials for the aforementioned applications. Hydrochlorofluoroolefins (HCFOs) with zero ozone depletion and a low global warming potential have been identified as potentially meeting this need. However, the toxicity, boiling point, and other physical properties of such chemicals vary significantly between isomers. One HCFO with valuable properties is (E)-1-chloro-3,3,3-trifluoropropene (HCFO-1233zd(E)), which has been proposed as a next-generation non-ozone depletion and low global warming potential solvent. The method of producing HCFO-1233zd(E) generates various by-products, such as various heavy organic materials. Furthermore, as disclosed in U.S. Patents No. 7,829,747, No. 8,217,208, No. 8,835,700, and No. 9,045,386, which are incorporated herein by reference, HCFC-1233zd(Z) and HCFC-244fa are also intermediates in the production of HCFO-1233zd(E). As used herein, the term “heavy organic material” or “heavy organic material phase” may include tar or tar-like material, or oligomers formed from the production of HCFO-1233zd(E). The term “heavy organic material” may be understood as an organic composition (e.g., chains of C, H, O, F, Cl, etc. and combinations thereof) having a weight average molecular weight (M W ) of about 500 g/mol to about 7,000 g/mol. For example, heavy organic matter may have a molecular weight as small as 500 g/mol, 550 g/mol, 590 g/mol, 600 g/mol, 800 g/mol, or 1,000 g/mol, or as large as 1,200 g/mol, 3,000 g/mol, 4,000 g/mol, 5,000 g/mol, 6,000 g/mol, or 7,000 g/mol, or may be within any range defined between any two of the aforementioned values, such as, for example, 500 g/mol to 700 g/mol, 600 g/mol to 6,000 g/mol, and 1,000 g/mol to 1,200 g/mol. Furthermore, the term “heavy organic material” may be understood to include organic compounds composed of a single unit or monomer, may include various comonomers, and may have a degree of polymerization of 1 to 15 (including the end point). For example, the degree of polymerization may be as small as 1, 2, 4, or 5, or as large as 9, 10, 12, or 15, or within any range defined between any two of the aforementioned values, such as, for example, 1 to 15, 2 to 12, 4 to 10, and 5 to 9 (e.g., 1 to 15 (including the end point), 2 to 10 (including the end point), and 5 to 9 (including the end point)). In various embodiments, the heavy organic material may have a boiling point of about 120°C to about 300°C at a pressure of about 3 psia to about 73 psia. The boiling point may be about 60°C, 80°C, or 100°C lower, or 350°C, 400°C, or 500°C higher, or within any range defined between any two of the aforementioned values (e.g., about 60°C to about 500°C). Because the boiling point of HCFO-1233zd(E) is similar to that of other reactants/products including HCFO-1233zd(Z), 1,1,1,3,3-pentachloropropane (240fa), 1,1,1,3-tetrachloro-3-fluoro-propane (241fa), and 1,1,1-trichloro-3,3-difluoro-propane (242fa), and because many intermolecular forces exist, conventional separation techniques may prove somewhat difficult to achieve. Furthermore, since some azeotropic mixtures and/or heteroazeotropic mixtures may be formed among various combinations of the aforementioned compounds, effective separation of the aforementioned compounds from heavy organic matter is required. In addition, since HF is an effective solvent, efficient removal of HF from heavy organic matter is required. Since HF must be removed from heavy organic matter before it can be used in a subsequent process or discarded, there is a need to address the separation of heavy organic matter in the purge stream from a reactor producing 1233zd(E) from other compounds containing HF. The pres