Arkema France

Arkema Inc.

Anne Marie Pigamo

Laurent Wendlinger

Dominique Deur-Bert

Bertrand Collier

Nicolas Doucet

Philippe Bonnet

Dominique Garrait

Michel Devic

Kevin Hisler

Audrey Riehl

John A Wismer

Emmanuel Boussarie

Jay Fingeret Miller

David Andre

Joaquin Lacambra

Cédric Lavy

Maher Y Elsheikh

Robert George Syvret

Sri Ram Seshadri

Bertrand Louis Maurice Collier

Emmanuel D Boussarie

Daniel Alford, Jr

Pierre Ricou

Dominique Duer-Bert

Nicolas Brusadelli

Emmanuel D Boussaire

Wayne Brooks

Jr Daniel Alford

The present invention relates to a process for modifying the fluorine distribution in a hydrocarbon compound, comprising a step of placing in contact between a hydrocarbon compound and a catalytic composition comprising a chromium-based catalyst, said process being performed in a reactor made of a material comprising a base layer made of a material M1 and an inner layer made of a material M2, said base layer and said inner layer being laid against each other, characterized in that the material M2 comprises at least 80% by weight of nickel on the basis of the total weight of the material M2, advantageously at least 90% by weight, preferably at least 95% by weight, in particular at least 99% by weight of nickel on the basis of the total weight of the material M2.

Method for modifying the fluorine distribution in a hydrocarbon compound

A composition including at least 98 mol % of (E/Z)-1-chloro-3,3,3-trifluoropropene and less than 0.5 mol % of coproducts selected from 1,3,3,3-tetrafluoropropene and 1,1,1,3,3-pentafluoropropane. A composition obtained from a process for producing 1-chloro-3,3,3-trifluoropropene, including the step i) of contacting hydrofluoric acid (HF) in a reactor with a starting composition including at least one of the chloro compounds selected from 1,1,3,3-tetrachloropropene (1230za), 1,3,3,3-tetrachloropropene (1230zd) and 1,1,1,3,3-pentachloropropane (240fa), or a mixture thereof, to produce a stream A including 1-chloro-3,3,3-trifluoropropene (1233zd), wherein the step i) is carried out in a low-HF liquid phase.

Method for producing 1-chloro-3,3,3-trifluoropropene

The present invention relates to a process for neutralizing a composition A comprising 1-chloro-3,3,3-trifluoropropene, 1,1-dichloro-1,3,3-trifluoropropane and one or more acid compound(s) of formula HX with X═F or Cl; said process comprising the step a) of bringing said composition A into contact with a solution B under conditions capable of limiting the formation of 1-chloro-1,3,3-trifluoropropene.

Process for purifying 1-chloro-3,3,3-trifluoropropene

The present invention relates to a process for purifying 1-chloro-3,3,3-trifluoropropene comprising the steps of: a) providing a stream comprising 1-chloro-3,3,3-trifluoropropene and at least one compound of formula HX wherein X is F or Cl; b) bringing the stream from step a) into contact with a solution A comprising at least one sulfite salt of formula YSOwherein Y is an alkali or alkaline-earth metal, n=1 or 2, and m=2 when n=1 or m=1 when n=2; in order to form a neutralized stream A1 comprising 1-chloro-3,3,3-trifluoropropene.

Method for purifying 1-chloro-3,3,3-trifluoropropene

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.

Method to neutralize and remove HF from a crude stream containing hydrochlorofluoroolefin

A process for manufacturing tetrafluoropropene, including, alternately: at least one step of reacting a chlorinated compound with hydrofluoric acid in the gas phase, in the presence of a fluorination catalyst, the proportion of oxygen optionally present being less than 0.05 mol. % relative to the chlorinated compound; a step of regenerating the fluorination catalyst by bringing the fluorination catalyst into contact with a regeneration stream including an oxidizing agent. Also, equipment suitable for carrying out this process.

Process for manufacturing tetrafluoropropene

The present invention relates to a process for producing 1-chloro-3,3,3-trifluoropropene (HCFO-1233zd), comprising: i) providing a stream A1 comprising HF, a stream A2 comprising 1,1,3,3-tetrachloropropene and/or 1,3,3,3-tetrachloropropene, and a reactor containing a liquid phase, ii) in said reactor, contacting, in said liquid phase, said stream A1 comprising HF with said stream A2 comprising 1,1,3,3-tetrachloropropene and/or 1,3,3,3-tetrachloropropene under conditions which are sufficient to produce a stream C comprising 1-chloro-3,3,3-trifluoropropene, HF and HCl, iii) recovering said stream C, characterized in that said reactor is provided with means for stirring said liquid phase so as to keep the temperature of said liquid phase substantially constant during step ii).

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.

Method to purify a crude stream containing hydrochlorofluoroolefin

A process for producing 2,3,3,3-tetrafluoropropene comprises the steps: i) in a first adiabatic reactor comprising a fixed bed composed of an inlet and an outlet, bringing 2-chloro-3,3,3-trifluoropropene into contact with hydrofluoric acid in the gas phase in the presence of a catalyst to produce a stream A comprising 2,3,3,3-tetrafluoropropene, HF and unreacted 2-chloro-3,3,3-trifluoropropene; and ii) in a second adiabatic reactor comprising a fixed bed composed of an inlet and an outlet, bringing hydrofluoric acid into contact in the gas phase, optionally in the presence of a catalyst, with at least one chlorinated compound to produce a stream B comprising 2-chloro-3,3,3-trifluoropropene. The stream A obtained in step i) feeds said second reactor. The inlet temperature of the fixed bed of one of said first or second reactors is between 300&#xb0; C. and 400&#xb0; C. The longitudinal temperature difference between the inlet and the outlet of the fixed bed in question is less than 20&#xb0; C.

Process for producing 2,3,3,3-tetrafluoropropene, and reactor for carrying out said process

The present invention relates to a process for producing 1-chloro-3,3,3-trifluoropropene, comprising the step i) of contacting hydrofluoric acid (HF) in a reactor with a starting composition comprising at least one of the chloro compounds selected from the group consisting of 1,1,3,3-tetrachloropropene (1230za), 1,3,3,3-tetrachloropropene (1230zd) and 1,1,1,3,3-pentachloropropane (240fa), or a mixture thereof, to produce a stream A comprising 1-chloro-3,3,3-trifluoropropene (1233zd), characterized in that said step i) is carried out in a low-HF liquid phase.

Method for producing 1-chloro-3,3,3- trifluoropropene

A process for the production of trans-1-chloro-3,3,3-trifluoropropene comprises the steps of: i) providing a reactor comprising a cover, a bottom, sidewalls connecting said bottom and said cover, at least one reagent supply line and at least one line for drawing off the products formed, said reactor further containing a liquid phase A; ii) providing a stream B comprising hydrofluoric acid heated to a temperature T1 of from 100&#xb0; C. to 170&#xb0; C. and providing a stream C comprising 1,1,3,3-tetrachloropropene and/or 1,3,3,3-tetrachloropropene; stream B and stream C supplying said reactor via said at least one reagent supply line; iii) reacting, in liquid phase A, stream B with stream C to form a stream D comprising trans-1-chloro-3,3,3-trifluoropropene. Step iii) is carried out at a temperature T2 of between 50&#xb0; C. and 110&#xb0; C., and the temperature difference between temperature T1 and temperature T2 is greater than 30&#xb0; C.

Process for the production of trans-1-chloro-3,3,3-trifluoropropene

The present invention relates to a process for producing 2-chloro-3,3,3-trifluoropropene, comprising the steps: i) providing a stream A comprising at least one chlorinated compound selected from the group consisting of 2,3-dichloro-1,1,1-trifluoropropane, 1,1,1,2,3-pentachloropropane, 1,1,2,3-tetrachloropropene and 2,3,3,3-tetrachloropropene; and ii) in an adiabatic reactor comprising a fixed bed composed of an inlet and an outlet, bringing said stream A into contact, in the presence or absence of a catalyst, with HF in order to produce a stream B comprising 2-chloro-3,3,3-trifluoropropene, characterized in that the temperature at the inlet of the fixed bed of said adiabatic reactor is between 300&#xb0; C. and 400&#xb0; C. and the longitudinal temperature difference between the inlet of the fixed bed and the outlet of the fixed bed of said reactor is less than 20&#xb0; C.

Method for producing 2-chloro-3,3,3-trifluoropropene and facility for implementing same

A process for producing 2,3,3,3-tetrafluoropropene comprises i) in a first adiabatic reactor comprising a fixed bed composed of an inlet and an outlet, bringing hydrofluoric acid into contact, in the gas phase with at least one chlorinated compound in order to produce a stream A comprising 2-chloro-3,3,3-trifluoropropene, ii) in a second adiabatic reactor comprising a fixed bed composed of an inlet and an outlet, bringing the stream A into contact, in the gas phase in the presence of a catalyst, with hydrofluoric acid, to produce a stream B comprising 2,3,3,3-tetrafluoropropene. The temperature at the inlet of the fixed bed of one of said first or second reactors is between 300&#xb0; C. and 400&#xb0; C. The longitudinal temperature difference between the inlet and the outlet of the fixed bed of the reactor is less than 20&#xb0; C.

Process for producing 2,3,3,3-tetrafluoropropene, and system for carrying out same

The present invention relates to a process for producing 2,3,3,3-tetrafluoropropene, comprising the steps: i) providing a stream A comprising at least one starting compound selected from the group consisting of 2-chloro-3,3,3-trifluoropropene and 2,3-dichloro-1,1,1-trifluoropropane; and ii) in an adiabatic reactor comprising a fixed bed composed of an inlet and an outlet, bringing said stream A into contact, in the presence or absence of a catalyst, with HF in order to produce a stream B comprising 2,3,3,3-tetrafluoropropene, characterized in that the temperature at the inlet of the fixed bed of said adiabatic reactor is between 300&#xb0; C. and 400&#xb0; C. and the longitudinal temperature difference between the inlet of the fixed bed and the outlet of the fixed bed of said reactor is less than 20&#xb0; C.

Method for producing 2,3,3,3-tetrafluoropropene and facility for implementing said method

A process for the production of 2,3,3,3-tetrafluoropropene including the stages: i) in a first reactor, bringing a stream A including 2-chloro-3,3,3-trifluoropropene into contact with hydrofluoric acid in the gas phase in the presence of a catalyst in order to produce a stream B including 2,3,3,3-tetrafluoropropene, HCl, HF and unreacted 2-chloro-3,3,3-trifluoropropene; and ii) in a second reactor, bringing hydrofluoric acid into contact, in the gas phase in the presence or not of a catalyst, with a stream including at least one chlorinated compound selected from the group of 1,1,1,2,3-pentachloropropane, 2,3-dichloro-1,1,1-trifluoropropane, 2,3,3,3-tetrachloropropene and 1,1,2,3-tetrachloropropene, in order to produce a stream C including 2-chloro-3,3,3-trifluoropropene, wherein the stream B obtained in stage i) feeds the second reactor used for stage ii); and wherein the electrical conductivity of the stream A provided in stage i) is less than 15 mS/cm.

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Francheville, France

Anne Marie Pigamo