IP Library Granted Patent US 12,606,728
Granted Patent B2
US 12,606,728 · App. 17/774,057 · Granted Apr 21, 2026

Azeotrope or azeotrope-like compositions of 2-chloro-1,1,1,2-tetrafluoropropane (HCFC-244bb) and water

Inventors: Haluk Kopkalli (Staten Island, NY); Daniel C. Merkel (Orchard Park, NY); Hang T. Pham (Amherst, NY)
Assignee: Solstice Advanced Materials US, Inc.
C09K5/044C07C17/25C09K5/048C09K2205/126C09K2205/32
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Quick Facts
Patent No.
US 12,606,728
App. No.
17/774,057
Granted
Apr 21, 2026
Kind
B2
Abstract

Heterogenous azeotrope or azeotrope-like compositions comprising 2-chloro-1,1,1,2-tetrafluoropropane (HCFC-244bb) and water which may include from about 0.05 wt. % to about 92.01 wt. % 2-chloro-1,1,1,2-tetrafluoropropane (HCFC-244bb) and from about 7.99 wt. % to about 99.95 wt. % water and having a boiling point between about −13.5° C. and about 14.5° C. at a pressure of between about 12.5 psia and about 16.5 psia. The azeotrope or azeotrope-like compositions may be used to separate impurities from 2-chloro-1,1,1,2-tetrafluoropropane (HCFC-244bb).

Claims (21)

1 . A composition comprising a heterogeneous azeotrope or azeotrope-like composition consisting essentially of from about 0.05 wt. % to about 92.01 wt. % 2-chloro-1,1,1,2-tetrafluoropropane (HCFC-244bb) and from about 7.99 wt. % to about 99.95 wt. % water.

2 . The composition of claim 1 , wherein the heterogeneous azeotrope or azeotrope-like composition consists essentially of from about 61 wt. % to about 90 wt. % 2-chloro-1,1,1,2-tetrafluoropropane (HCFC-244bb) and from about 10 wt. % to about 39 wt. % water.

3 . The composition of claim 1 , wherein the heterogeneous azeotrope or azeotrope-like composition has a boiling point between about 13.5° C. and about 14.5° C. at a pressure of between about 12.5 psia and about 16.5 psia.

4 . A method of forming a heterogeneous azeotrope or azeotrope-like composition as defined in claim 1 , comprising the step of combining 2-chloro-1,1,1,2-tetrafluoropropane (HCFC-244bb) and water to form the azeotrope or azeotrope-like composition.

5 . A method of separating 2-chloro-1,1,1,2-tetrafluoropropane (HCFC-244bb) from a primary composition comprising 2-chloro-1,1,1,2-tetrafluoropropane (HCFC-244bb), water, and at least one other substance, comprising the steps of:

subjecting the primary composition to conditions effective to form a heterogeneous azeotrope or azeotrope-like composition consisting essentially of from about 0.05 wt. % to about 92.01 wt. % 2-chloro-1,1,1,2-tetrafluoropropane (HCFC-244bb) and from about 7.99 wt. % to about 99.95 wt. % water; and

separating the heterogeneous azeotrope or azeotrope-like composition from the primary composition.

6 . The method of claim 5 , wherein the at least one other substance comprises 2,3,3,3-tetrafluoropropene (HFO-1234yf), and wherein the separation step comprises at least one of phase separation, distillation, and fractionation.

7 . The method of claim 5 , further comprising converting at least some of the 2-chloro-1,1,1,2-tetrafluoropropane (HCFC-244bb) present in the heterogeneous azeotrope or azeotrope-like composition into 2,3,3,3-tetrafluoropropene (HFO-1234yf).

8 . The method of claim 7 , wherein converting at least some of the 2-chloro-1,1,1,2-tetrafluoropropane (HCFC-244bb) into 2,3,3,3-tetrafluoropropene (HFO-1234yf) comprises reacting the 2-chloro-1,1,1,2-tetrafluoropropane (HCFC-244bb) with a base.

9 . The method of claim 8 , wherein the base is an alkali metal hydroxide.

10 . The method of claim 7 , wherein converting the 2-chloro-1,1,1,2-tetrafluoropropane (HCFC-244bb) into 2,3,3,3-tetrafluoropropene (HFO-1234yf) occurs in an aqueous environment in the presence of a phase transfer catalyst.

11 . The method of claim 7 , wherein converting the 2-chloro-1,1,1,2-tetrafluoropropane (HCFC-244bb) into 2,3,3,3-tetrafluoropropene (HFO-1234yf) occurs at a temperature of from about 0° C. to about 100° C.

12 . The method of claim 7 , wherein the heterogeneous azeotrope or azeotrope-like composition is present in a recycle line that transfers 2-chloro-1,1,1,2-tetrafluoropropane (HCFC-244bb) to the reaction that converts 2-chloro-1,1,1,2-tetrafluoropropane (HCFC-244bb) into 2,3,3,3-tetrafluoropropene (HFO-1234yf).

13 . The method of claim 10 , wherein the phase transfer catalyst is an ammonium halide.

14 . The method of claim 10 , wherein the phase transfer catalyst is a trialkylammonium halide or a tetraalkylammonium halide.

15 . The method of claim 10 , wherein converting the 2-chloro-1,1,1,2-tetrafluoropropane (HCFC-244bb) into 2,3,3,3-tetrafluoropropene (HFO-1234yf) occurs at a temperature of from 20° C. to 90° C.

16 . The method of claim 10 , wherein converting the 2-chloro-1,1,1,2-tetrafluoropropane (HCFC-244bb) into 2,3,3,3-tetrafluoropropene (HFO-1234yf) occurs at a temperature of from 50° C. to 90° C.

17 . The method of claim 7 , wherein converting at least some of the 2-chloro-1,1,1,2-tetrafluoropropane (HCFC-244bb) into 2,3,3,3-tetrafluoropropene (HFO-1234yf) comprises reacting the 2-chloro-1,1,1,2-tetrafluoropropane (HCFC-244bb) in a vapor phase dehydrochlorination reaction.

18 . The method of claim 7 , wherein the vapor phase dehydrochlorination reaction is conducted in the presence of a catalyst.

19 . The method of claim 5 , wherein the at least one other substance comprises hydrogen fluoride (HF), and wherein the separation step comprises at least one of phase separation, distillation, and fractionation.

Assignments (3)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 13, 2026
From: HONEYWELL INTERNATIONAL INC.
To: SOLSTICE ADVANCED MATERIALS US, INC.
Reel/Frame 074068/0530 →
SECURITY INTEREST Recorded Jan 12, 2026
From: SOLSTICE ADVANCED MATERIALS US, INC.
To: JPMORGAN CHASE BANK, N.A., AS ADMINISTRATIVE AGENT
Reel/Frame 074569/0260 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 22, 2025
From: KOPKALLI, HALUK; MERKEL, DANIEL C.; PHAM, HANG T.
To: HONEYWELL INTERNATIONAL INC.
Reel/Frame 071797/0172 →
Continuity (2)
Provisional Application 62931494 · Nov 6, 2019
Related Publication 20230002657A1 · Jan 5, 2023
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