US 2012/0059199 A1Published application

Continuous low-temperature process to produce trans-1-chloro-3,3,3-trifluoropropene

AssigneeHoneywell International Inc.

InventorsKonstantin A. Pokrovski, Daniel C. Merkel, Hsueh Sung Tung

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Abstract

Disclosed is process for the production of (E) 1-chloro-3,3,3-trifluoropropene (HCFO-1233zd(E)) by conducting a continuous reaction without the use of a catalyst. Also disclosed is an integrated system for producing hydrofluoro olefins, particularly 1233zd(E). The manufacturing process includes six major unit operations: (1) a fluorination reaction of HCC-240fa (in continuous or semi-batch mode) using HF with simultaneous removal of by-product HCl and the product 1233zd(E); (2) recycle of unreacted HCC-240fa and HF together with under-fluorinated by-products back to (1); (3) separation and purification of by-product HCl; (4) separation of excess HF back to (1); (5) purification of final product, 1233zd(E); and (6) isomerization of by-product 1233zd(Z) to 1233zd(E) to maximize the process yield.

Claims20

Dependent claims

A method for the production of (E)1-chloro-3,3,3-trifluoropropene without the use of a catalyst comprising the steps of;

(a) operating a series of one or more agitated reaction vessels, each vessel in succession converting a portion of the original reactants fed to the first of the reaction vessels, with all of the reaction vessels being run simultaneously and operating in a continuous fashion;
(b) conducting, in each of the reaction vessels, a series of fluorination reactions of a starting material selected from the group consisting of 1,1,1,3,3-pentachloropropane, 1,1,1,3,3-pentachloropropane, 1,1,3,3-tetrachloropropene, and 1,3,3,3-tetrachloropropene, and any mixtures thereof, using HF with simultaneous removal of by-product HCl and the product (E)1-chloro-3,3,3-trifluoropropene;
(c) recycling at least a portion of any unreacted starting material and HF together with any under-fluorinated by-products back to step (b);
(d) separating and purifying by-product HCl;
(e) separating excess HF back to step (b);
(f) purifying the desired product, (E)1-chloro-3,3,3-trifluoropropene;
and
(g) isomerization any by-product (Z)1-chloro-3,3,3-trifluoropropene to (E)1-chloro-3,3,3-trifluoropropene to maximize the process yield.

5 more elements

A method for producing a hydrochlorofluoroalkene in a series of one or more agitated reaction vessels, comprising the following steps:

(a) providing a liquid reaction admixture in at least one of the reaction vessels, said admixture comprising hydrogen fluoride, and a reactant composition selected from the group consisting of 1,1,1,3,3-pentachloropropane, 1,1,3,3-tetrachloropropene, 1,3,3,3-tetrachloropropene, and any mixtures thereof, wherein the hydrogen fluoride and the reactant composition are present in a molar ratio of greater than about 3:1;
(b) reacting the hydrogen fluoride and the reactant composition in a liquid phase using one or more agitated reactors in series to produce one or more reaction product streams selected from the group consisting of (E)1-chloro-3,3,3-trifluoropropene, hydrogen chloride, hydrogen fluoride, (Z)1-chloro-3,3,3-trifluoropropene and unreacted compounds of the reactant composition and/or under-fluorinated intermediates, wherein each reaction product stream has a weight ratio of (E)1-chloro-3,3,3-trifluoropropene to (Z)1-chloro-3,3,3-trifluoropropene of greater than 1;
and
(c) wherein optionally, each individual reaction vessel in the series may be equipped with a rectifying column that returns some of the unreacted HF, and the majority of unreacted 1,1,1,3,3-pentachloropropane, and/or 1,1,3,3-tetrachloropropene and/or 1,3,3,3-tetrachloropropene and/or under-fluorinated intermediates back to the reaction vessel;
and
(d) combining the one or more resulting reaction product streams into a single combined reaction product stream.

3 more elements

An integrated system for producing a hydrochlorofluoroolefin, wherein the system comprises:

(a) one or more feed streams cumulatively comprising hydrogen fluoride and a reactant composition selected from the group consisting of 1,1,1,3,3-pentachloropropane, or 1,1,1,3,3-pentachloropropane, and/or 1,1,3,3-tetrachloropropene, and/or 1,3,3,3-tetrachloropropene;
(b) a liquid phase reactor system consisting of a series of one or more agitated reactors, each fed by its predecessor, and wherein the liquid phase reactor series is fluidly connected to the one or more feed streams;
(c) an optional recycle system comprising a recycle distillation column, a reflux stream fluidly connected to the top of the reactor and a combined first crude product stream fluidly connected to the top of the reactor, wherein the reflux stream is fluidly connected to the lead liquid phase reactor;
(d) a hydrogen chloride removal system comprising a first distillation column, a hydrogen chloride by-product stream fluidly connected to the first distillation column, and a second crude product stream fluidly connected to the first distillation column, wherein the first distillation column is fluidly connected to the stripping column;
(e) a hydrogen fluoride recovery system comprising a sulfuric acid absorption and recycle system or a phase separation vessel, a second recycle stream comprising hydrogen fluoride fluidly connected to the sulfuric acid absorption and recycle system or a phase separation vessel;
(f) a third product stream comprising (E) and (Z) 1-chloro-3,3,3-trifluoropropene fluidly connected to the sulfuric acid absorption and recycle system or a phase separation vessel, wherein the sulfuric acid absorption and recycle system or a phase separation vessel is fluidly connected to the second crude product stream and a 1-chloro-3,3,3-trifluoropropene purification system comprising a second distillation column fluidly connected to the third product stream and
(g) a final product stream comprising (E)1-chloro-3,3,3-trifluoropropene fluidly connected to the second distillation column;
a second by-product stream fluidly connected to the distillation column, an isomerization reactor fluidly connected to the second by-product stream;
and a product recycle stream fluidly connected to the isomerization reactor and the second distillation column.

6 more elements

Dependencies are inferred from the claim text.

Facts

Application: 13/220,212Filed 29 Aug 2011
Priority: 3 Sep 2010
Published: 8 Mar 2012
Term ends: Not estimatedThe source records don’t support an estimate.

Classification14 codes

C07C 17/20
By replacement by halogens: of halogen atoms by other halogen atoms
B01D 3/009
Distillation or related exchange processes in which liquids are contacted with gaseous media, e.g. stripping: in combination with chemical reactions
C01B 7/0706
Purification ; Separation: of hydrogen chloride
C01B 7/0712
Of hydrogen chloride: by distillation