公开(公告)号：US11220472B2

公开(公告)日：2022-01-11

申请号：US16468416

申请日：2017-12-14

Applicant: Arkema Inc.

Inventor： Jay F. Miller ,  John A. Wismer

IPC: C07C17/383 ,  C07C17/386 ,  C07C21/18

Abstract: Aspects of the invention relate to systems and processes for recovering R1233zd in purified form from compositions additionally comprising hydrogen fluoride. In accordance with one aspect, the invention provides a process that includes separating a feed stream comprised of hydrogen fluoride and R1233zd using azeotropic distillation in a first distillation column to produce a first distillate stream comprised of hydrogen fluoride and R1233zd and a first bottoms stream consisting essentially of hydrogen fluoride. The first distillation column is operated at a first pressure. The process further includes separating the first distillate stream using azeotropic distillation in a second distillation column to produce a second distillate stream comprised of hydrogen fluoride and R1233zd and a second bottoms stream consisting essentially of R1233zd. The second distillation column is operated at a second pressure that may be different than the first pressure of the first distillation column.

公开(公告)号：US20200010392A1

公开(公告)日：2020-01-09

申请号：US16468416

申请日：2017-12-14

Applicant: Arkema Inc.

Inventor： Jay F. Miller ,  John A. Wismer (Deceased)

IPC: C07C17/386 ,  C07C21/18

Abstract: Aspects of the invention relate to systems and processes for recovering R1233zd in purified form from compositions additionally comprising hydrogen fluoride. In accordance with one aspect, the invention provides a process that includes separating a feed stream comprised of hydrogen fluoride and R1233zd using azeotropic distillation in a first distillation column to produce a first distillate stream comprised of hydrogen fluoride and R1233zd and a first bottoms stream consisting essentially of hydrogen fluoride. The first distillation column is operated at a first pressure. The process further includes separating the first distillate stream using azeotropic distillation in a second distillation column to produce a second distillate stream comprised of hydrogen fluoride and R1233zd and a second bottoms stream consisting essentially of R1233zd. The second distillation column is operated at a second pressure that may be different than the first pressure of the first distillation column.

公开(公告)号：US11555002B2

公开(公告)日：2023-01-17

申请号：US17293645

申请日：2019-10-10

Applicant: Arkema Inc.

Inventor： Anne M. Pigamo ,  Jay F. Miller ,  Emmanuel D. Boussaire ,  Kevin Hisler

IPC: C07C17/395 ,  C07C17/42

Abstract: Disclosed is a step in the purification process of hydrochlorofluoroolefin refrigerants that are made from processes wherein 1,1,3,3 tetrachloropropene (R1230za) or 1,1,1,3,3-pentachloropropane (R240fa) is reacted with HF in excess. The purification process employs a cold-temperature reaction with a base to remove the HF and any HCl. The process prevents an increase in unwanted organic side-products, particularly trifluoropropyne (TPS), and simultaneously does not reduce the amount of the desired hydrochlorofluoroolefin refrigerant produced. The process also can have an optional step whereby hydrochlorofluoroolefin refrigerant and other organics are removed from aqueous process stream or streams resulting from the reaction with the base. The organics removed can be recycled. This optional step advantageously can increase the yield of the desired refrigerant, while decreasing the environmental load of the plant, by purifying the resulting aqueous process streams.

公开(公告)号：US11286223B2

公开(公告)日：2022-03-29

申请号：US17293639

申请日：2019-10-10

Applicant: Arkema Inc.

Inventor： Anne M. Pigamo ,  Kevin Hisler ,  Wayne Brooks ,  Jay F. Miller ,  Bertrand Louis Maurice Collier ,  Emmanuel D. Boussarie

IPC: C07C17/395 ,  C07C17/42 ,  C07C17/383

Abstract: Disclosed is a method of purifying a stream of crude hydrochlorofluoroolefin refrigerant produced by the reaction of 1,1,3,3 tetrachloropropene (R1230za) or 1,1,1,3,3-pentachloropropane (R240fa) with HF. The process includes a step of removing the cis-(Z) isomer by distillation of the crude refrigerant stream prior to a step of reacting the crude refrigerant stream with a base. The reaction with the base is a necessary step in production of the refrigerant and is done to remove HF and residual HCl from the crude refrigerant stream. Removal of the cis-(Z) isomer before the reaction with the base reduces the amount of toxic flammable trifluoropropyne (TFP) that is produced as a side-reaction during the reaction with the base. In addition, temperature control during the reaction with the base is less critical to minimizing the TFP production if the cis-(Z) isomer is first removed.

公开(公告)号：US10669232B2

公开(公告)日：2020-06-02

申请号：US16485464

申请日：2018-05-08

Applicant: Arkema Inc.

Inventor： Jay F. Miller ,  Gary S. Smith ,  George C. Fortman ,  Vijay R. Srinivas

IPC: C07C303/44 ,  C07C309/04

Abstract: Aspects of the invention relate to systems and processes for recovering methanesulfonic acid, in a purified form, from a composition additionally including sulfur trioxide. In accordance with one aspect, the invention provides a process that includes separating a feed stream comprised of hydrocarbons, methanesulfonic acid, sulfur trioxide, and optionally sulfuric acid to produce a light stream comprised of hydrocarbons and a heavy stream comprised of methanesulfonic acid and sulfur trioxide; contacting (e.g., by mixing) the heavy stream with a reactive additive capable of reacting with sulfur trioxide, under conditions effective to cause reaction of the reactive additive with the sulfur trioxide to produce a heavy reaction product having a boiling point higher than the boiling point of methanesulfonic acid; and separating the heavy stream using a distillation column to produce a distillate stream consisting essentially of methanesulfonic acid and a bottoms stream comprising the heavy reaction product.