Methods for producing 1-chloro-3,3,3-trifluoropropene from 2-chloro-3,3,3-trifluoropropene
AssigneeHoneywell International Inc.
InventorsHaiyou Wang, Hsueh Sung Tung
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Abstract
The present invention provides processes for the production of HCFO-1233zd, 1-chloro-3,3,3-trifluoropropene, from the starting material, 2-chloro-3,3,3-trifluoropropene (HCFO-1233xf). In a first process, HCFO-1233zd is produced by the isomerization of HCFO-1233xf. In a second process, HCFO-1233zd is produced in a two-step procedure which includes (i) dehydrochlorination of HCFO-1233xf into trifluoropropyne; and (ii) hydrochlorination of the trifluoropropyne into HCFO-1233zd.
Claims31
A process for making 1-chloro-3,3,3-trifluoropropene (HCFO-1233zd) from 2-chloro-3,3,3-trifluoropropene (HCFO-1233xf) comprising:
- (a) isomerization of HCFO-1233xf to yield HCFO-1233zd;
- wherein the isomerization reaction of HCFO-1233xf is conducted in a vapor phase reactor charged with an isomerization catalyst comprising fluorinated chromia catalyst pellets;
- and
- wherein the isomerization reaction is carried out at 0.0 psig and at 350° C. to attain a HCFO-1233xf conversion of about 50%.
A process for the production of HCFO-1233zd, wherein the HCFO-1233zd is produced through a two-step process, which comprises
- (i) dehydrochlorination of HCFO-1233xf into trifluoropropyne in a vapor phase reactor optionally using a dehydrochlorination catalyst selected from the group consisting of, halogenated metal oxides, metals, metal alloys, and mixtures thereof;
- wherein the reaction is conducted at a temperature in the range of 200° C. to 800° C. solid, and
- (ii) hydrochlorination of the resultant trifluoropropyne into HCFO-1233zd in a vapor phase or a liquid phase reactor, charged with a hydrochlorination catalyst,
- wherein the hydrochlorination catalyst is selected from the group consisting of chromium, aluminum, cobalt, manganese, nickel and iron oxides, hydroxides, halides, oxyhalides, inorganic salts thereof and their mixtures.
A process for making 1-chloro-3,3,3-trifluoropropene (HCFO-1233zd) from 2-chloro-3,3,3-trifluoropropene (HCFO-1233xf) comprising:
- a two-step procedure which comprises (i) dehydrochlorination of HCFO-1233xf into trifluoropropyne;
- and (ii) hydrochlorination of the trifluoropropyne into HCFO-1233zd;
- wherein the HCFO-1233zd is produced through a two-step process, which comprises:
- (i) dehydrochlorination of HCFO-1233xf into trifluoropropyne in a vapor phase reactor wherein the reaction is conducted at a temperature in the range of 200° C. to 800° C. and
- (ii) hydrochlorination of the resultant trifluoropropyne into HCFO-1233zd in a vapor phase or a liquid phase reactor, charged with a hydrochlorination catalyst;
- wherein the second step of the two-step process comprises the reaction of HCl with the trifluoropropyne formed in the first step in the presence of a hydrochlorination catalyst under conditions effective to facilitate a hydrochlorination reaction and to form a product stream comprising HCFO-1233zd;
- and
- wherein the hydrochlorination catalyst comprises a chromium (III) oxide selected from the group consisting of crystalline chromium oxide and amorphous chromium oxide.
A process for making 1-chloro-3,3,3-trifluoro-propene (HCFO-1233zd) from 2-chloro-3,3,3-trifluoropropene (HCFO-1233xf) comprising:
- a two-step procedure which comprises (i) dehydrochlorination of HCFO-1233xf into trifluoropropyne;
- and (ii) hydrochlorination of the trifluoropropyne into HCFO-1233zd;
- wherein the second step of the two-step process comprises the reaction of HCl with the trifluoropropyne formed in the first step in the presence of a hydrochlorination catalyst which facilitates a hydrochlorination reaction and to form a product stream comprising HCFO-1233zd;
- wherein the hydrochlorination catalyst is selected from the group consisting of chromium, aluminum, cobalt, manganese, nickel and iron oxides, hydroxides, halides, oxyhalides, inorganic salts thereof and their mixtures;
- and
- wherein the hydrochlorination catalyst is supported on a substrate selected from the group consisting of activated carbon, alumina, fluorinated alumina, aluminum fluoride, alkaline earth metal oxides, fluorinated alkaline earth metal oxides, zinc oxide, zinc fluoride, tin oxide, and tin fluoride.
Dependencies are inferred from the claim text.