STABILIZER AND INHIBITOR FOR CHLOROPROPENES, SUCH AS TETRACHLOROPROPENE 1,1,2,3-TETRACHLOROPROPENE (1230xa), USED IN THE MANUFACTURE OF 2,3,3,3-TETRAFLUOROPROPENE (1234yf)
AssigneeHoneywell International Inc.
InventorsHaluk KOPKALLI, Haiyou WANG, Hsueh SUNG TUNG, Daniel C. MERKEL
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Abstract
The present invention relates in part to a method of stabilizing chloropropenes, such as 1,1,2,3-tetrachloropropene, otherwise known to decompose and degrade, and to the resulting stabilized chloropropene, using a morpholine compound and/or a trialkyl phosphate compound as defined herein. Such stabilized chloropropenes are useful in the manufacture of hydrofluoroolefins such as 2,3,3,3-tetrafluoroprop-1-ene (1234yf).
Claims31
A method for stabilizing a chloropropene comprising:
- (a) providing a chloropropene;
- and
- (b) adding to said chloropropene a stabilizingly effective amount of at least one stabilizer compound selected from (i) or (ii) and combinations thereof:
- (i) a morpholine compound having the formula:
- wherein R is H or a C1-C6 alkyl,
- (ii) a trialkyl phosphate compound having the formula R′3PO4,
- wherein R′ is a C1-C6 alkyl.
A composition comprising a chloropropene and at least one stabilizer compound selected from (i) or (ii) and combinations thereof:
- (i) a morpholine compound having the formula:
- wherein R is H or C1-C6 alkyl,
- (ii) a trialkyl phosphate compound having the formula R′3PO4,
- wherein R′ is a C1-C6 alkyl.
A method for preparing 2-chloro-3,3,3-trifluoropropene (1233xf) comprising:
- (a) providing a starting composition comprising a chloropropene and a stabilizingly effective amount of at least one stabilizer compound selected from (i) or (ii) and combinations thereof:
- (i) a morpholine compound having the formula:
- wherein R is H or C1-C6 alkyl,
- (ii) a trialkyl phosphate compound having the formula R′3PO4,
- wherein R′ is a C1-C6 alkyl;
- (b) contacting said starting composition with a fluorinating agent under conditions effective to produce a first composition comprising 2-chloro-3,3,3-trifluoropropene,
- wherein in step (b) said stabilizer compound is optionally removed from said starting composition prior to said contacting.
A method for preparing 2,3,3,3-tetrafluoroprop-1-ene (1234yf) comprising:
- a) providing a starting composition comprising at least one compound having a structure selected from Formula I and II:
- 1) CX2═CCl—CH2X (Formula I)
- 2) CX3—CCl═CH2 (Formula II)
- wherein X is independently selected from F, Cl, Br and I, provided that at least one of X is not F, and a stabilizingly effective amount of at least one stabilizer compound selected from (i) or (ii) and combinations thereof:
- (i) a morpholine compound having the formula:
- wherein R is H or C1-C6 alkyl,
- (ii) a trialkyl phosphate compound having the formula R′3PO4,
- wherein R′ is a C1-C6 alkyl;
- b) contacting said starting composition with a first fluorinating agent to produce a first intermediate composition comprising 2-chloro-3,3,3-trifluoropropene and a first chlorine-containing byproduct, wherein in step (b) said stabilizer compound is optionally removed from said starting composition prior to said contacting;
- c) contacting said first intermediate composition with a second fluorinating agent to produce a second intermediate composition comprising 2-chloro-1,1,1,2-tetrafluoropropane;
- and
- d) dehydrochlorinating at least a portion of said 2-chloro-1,1,1,2-tetrafluoropropane to produce a reaction product comprising 2,3,3,3-tetrafluoroprop-1-ene and a second chlorine-containing byproduct.
Dependencies are inferred from the claim text.