Method for removal of fluorinated organics from byproduct anhydrous or aqueous hydrochloric acid in the 1234yf via 1230xa process

Patent metadata

Field	Value
Publication number	US-2018318788-A1
Application number	US-201615773769-A
Country	US
Kind code	A1
Filing date	Nov 4, 2016
Priority date	Nov 5, 2015
Publication date	Nov 8, 2018
Grant date	—

Abstract

Disclosed is a process to separate halogenated organic contaminants such as 2-chloro-3,3,3-trifluoropropene (HCFO-1233xf), 2,3,3,3-tetrafluoropropene (HFO-1234yf), trifluoropropyne (TFPY) from hydrochloric acid (HCl) with an adsorbent selected from an activated carbon, an MFI molecular sieve, a carbon molecular sieve, silica, and combinations thereof.

First claim

1 . A separation process comprising contacting a composition comprising hydrochloric acid (HCl) and trifluoropropyne (TFPY) with an adsorbent selected from activated carbon, MFI molecular sieve, carbon molecular sieve, silica, and combinations thereof, under conditions effective to separate the TFPY from the HCl.

2 . The process of claim 1 wherein the composition further comprises 2-chloro-3,3,3-trifluoropropene (HCFO-1233xf), 2,3,3,3-tetrafluoropropene (HFO-1234yf), or mixtures thereof, and wherein the contacting is under conditions effective to separate the HCFO-1233xf and HFO1234yf from the HCl.

3 . The process of claim 1 wherein TFPY is present in the composition at greater than 25 ppm by weight.

4 . The process of claim 1 further comprising absorbing the HCl from which the TFPY has been separated into water under conditions effective to form solution wherein TFPY is present at 25 ppm by weight or less.

5 . The process of claim 1 wherein the MFI molecular sieve is ZSM-5 or silicalite.

6 . The process of claim 1 wherein the composition further comprises hydrogen fluoride (HF) and the process further comprises contacting the composition with silica prior to contacting the composition with said adsorbent, the contacting with silica under conditions effective to remove the HF.

7 . A process for removing a halogenated organic from hydrochloric acid comprising
a) contacting a composition comprising hydrochloric acid (HCl), hydrogen fluoride (HF) and at least one halogenated organic with an adsorbent comprising silica under conditions effective to adsorb HF to produce a first composition comprising HCl and said at least one halogenated organic; b) contacting the first composition with an adsorbent comprising activated carbon, zeolite molecular sieve, carbon molecular sieve, or combinations thereof, under conditions effective to adsorb the halogenated organic to produce a second composition comprising HCl.

8 . The process of claim 7 further comprising contacting the second composition with water under conditions effective to absorb the HCl to produce an aqueous solution comprising HCl.

9 . The process of claim 8 wherein the aqueous solution comprising HCl has a concentration of about 7 Baume to about 23 Baume.

10 . (canceled)

11 . (canceled)

12 . The process of claim 7 wherein the halogenated organic is selected from TFPY, HCFO-1233xf, HFO-1234yf, 1232xf, 244bb, 245cb, or mixtures thereof.

13 . The process for removing a halogenated organic from hydrochloric acid comprising
a) contacting a composition comprising hydrochloric acid (HCl), hydrogen fluoride (HF) and at least one halogenated organic with an adsorbent comprising silica under conditions effective to adsorb HF to produce a first composition comprising HCl and said at least one halogenated organic; b) contacting the first composition with water under conditions effective to absorb the HCl to produce a second composition comprising an aqueous solution comprising HCl and said at least one halogenated organic; c) contacting the second composition with adsorbent comprising activated carbon, zeolite molecular sieve, carbon molecular sieve, or combinations thereof, under conditions effective to adsorb the at least one halogenated organic to produce a third composition comprising HCl.

14 . The process of claim 13 wherein the third composition comprising HCl has a concentration of about 7 Baume to about 23 Baume.

15 . (canceled)

16 . (canceled)

17 . The process of claim 13 wherein the halogenated organic is selected from TFPY, HCFO-1233xf, HFO-1234yf, 1232xf, 244bb, 245cb, and mixtures thereof.

18 . A separation process comprising contacting a composition comprising hydrochloric acid (HCl) and 2,3,3,3-tetrafluoropropene (HFO-1234yf) with an adsorbent selected from activated carbon, MFI molecular sieve, carbon molecular sieve, silica, and combinations thereof, under conditions effective to separate HFO-1234yf from the HCl.

19 . The process of claim 18 , wherein the adsorbent is activated carbon, which may optionally be granulated, or MFI molecular sieve.

20 . (canceled)

21 . (canceled)

22 . The process of claim 18 where the activated carbon has a minimum Iodine number of 900.

23 . (canceled)

24 . (canceled)

25 . (canceled)

26 . (canceled)

27 . The process of claim 18 , further comprising producing HFO-1234yf and HCl from 2-chloro-1,1,1,2-tetrafluoropropane (HCFC-244bb).

28 . A composition comprising hydrochloric acid (HCl) and at least one halogenated organic compound selected from the group consisting of trifluoropropyne (TFPY), 2-chloro-3,3,3-trifluoropropene (HCFO-1233xf), and 2,3,3,3-tetrafluoropropene (HFO-1234yf), a total amount of the halogenated organic compounds present in an amount between 0.1 ppm and 25 ppm and which may optionally additionally comprise 2-chloro-1,1,1,2-tetrafluoropropene (HCFO-244bb).

29 . (canceled)

30 . (canceled)

31 . (canceled)

32 . The composition of claim 28 , wherein at least one of the halogenated organic compounds is present in an amount of 5 ppm or less.

33 . (canceled)

34 . The composition of claim 28 , wherein the HFO-1234yf is present in an amount ranging from about 0.1 ppm to 5 ppm and TFPY is present in an amount of about 0.1 ppm to about 5 ppm.

35 . (canceled)

36 . (canceled)

37 . (canceled)

38 . (canceled)

39 . (canceled)

40 . (canceled)

Assignees

• Honeywell Int Inc

Inventors

• Horwath Richard Durick
• Chiu Yuon
• Kopkalli Haluk
• Smith Robert A
• Wang Haiyou
• Gatter Michael
• Tung Hsueh Sung
• Merkel Daniel C

Classifications

• C02F1/283

  using coal, charred products, or inorganic mixtures containing them · CPC title

• B01J20/3416

  of sorbents or filter aids comprising free carbon, e.g. activated carbon · CPC title

• B01J20/103 Primary

  comprising silica · CPC title

• B01J20/18

  Synthetic zeolitic molecular sieves · CPC title

• B01D35/02

  Filters adapted for location in special places, e.g. pipe-lines, pumps, stop-cocks, (B01D35/05 takes precedence; {water pipe system filters E03B3/18, E03B7/07; dirt catchers in sewers E03F; filters or strainers for pipe-lines in general B08B, E03F; object or dirt catching devices in sinks or the like E03C1/26; suction strainers or filters for pumps F04B53/005, F04D29/70}) · CPC title