1-Chloro-3,3,3-trifluoropropene

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1-Chloro-3,3,3-trifluoropropene
1-Chloro-3,3,3-trifluoropropene.svg
Names
Preferred IUPAC name
1-Chloro-3,3,3-trifluoroprop-1-ene
Other names
1-Chloro-3,3,3-trifluoropropene
HCFO-1233zd
HCFC-1233zd
r-1233zd
Solstice zd (Honeywell brand name)
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.215.615 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
  • mixture of E- and Z- isomers:InChI=1S/C3H2ClF3/c4-2-1-3(5,6)7/h1-2H
    Key: LDTMPQQAWUMPKS-UHFFFAOYSA-N
  • E-isomer:InChI=1S/C3H2ClF3/c4-2-1-3(5,6)7/h1-2H/b2-1+
    Key: LDTMPQQAWUMPKS-OWOJBTEDSA-N
  • Z-isomer:InChI=1S/C3H2ClF3/c4-2-1-3(5,6)7/h1-2H/b2-1-
    Key: LDTMPQQAWUMPKS-UPHRSURJSA-N
  • FC(F)(F)C=CCl
Properties
C3H2ClF3
Molar mass 130.49 g·mol−1
AppearanceColorless liquid
Boiling point 39.6 °C (Z)
18.5 °C (E)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

1-Chloro-3,3,3-trifluoropropene (HFO-1233zd) is the unsaturated chlorofluorocarbon with the formula HClC=C(H)CF3. The compound exists as E- (trans-) and Z- (cis-) isomers. The cis- isomer of this colorless gas is of interest as a more environmentally friendly (lower GWP; global warming potential) refrigerant in air conditioners(cis-isomer) or solvent(trans-isomer). [1] The trans-isomer is of interest as a more environmentally friendly (lower GWP; global warming potential) solvent. [2]

Production

It can be prepared by fluorination and dehydrohalogenation/dehydrochlorination reactions starting with 1,1,1,3,3-pentachloropropane [3] or 1,1,3,3-tetrachloropropane using the below steps: [4]

  1. In a liquid phase reactor, HFO-240fa (or 1,1,3,3-tetrachloropropene and derivatives such as 1,3,3,3-tetrachloropropene) are converted to HF in the presence of a catalyst forming a mixture of 245fa, 244fa, 1234ze, and 1233zd;
  2. Removal of HCl and HF.
  3. In a liquid or gas phase reactor, the organic mixture is reacted with HCl in the presence of a catalyst to convert unsaturated olefins to alkanes.
  4. Isolating and purifying the HFO-245fa product
  5. HFO-243fa and HFO-244fa are dehydrochlorinated with a caustic solution in the liquid phase or with a catalyst in the vapor phase to form HFO-1233zd and trans-1234ze(E-isomer).
  6. Isolation and purifying the HFO-1233zd product into its isomers.

References

  1. ↑ Cheryl Hogue (2011). "Replacing the Replacements". Chemical & Engineering News . 89 (49): 31–32. doi:10.1021/cen-v089n049.p031. Archived from the original on 2020-09-23.
  2. ↑ JP6382374B2,ウォン，ハイユー; マーケル，ダニエル・シー& ポクロフスキ，コンスタンティン・エイet al.,"１，１，１，３，３−ペンタフルオロプロパン、トランス−１−クロロ−３，３，３−トリフルオロプロペン、及びトランス−１，３，３，３−テトラフルオロプロペンを共製造するための統合方法",issued 2018-08-29
  3. ↑ Tung, Hseuh Sung; Ulrich, Kevin D.; Merkel, Daniel C. "Low-temperature catalytic fluorination process for the manufacture of 1-chloro-3,3,3-trifluoropropene from 1,1,1,3,3-pentachloropropane and hydrogen fluoride" U.S. (2005), US 6844475 B2 20050118 to Honeywell International Business Machines.
  4. ↑ JP6382374B2,ウォン，ハイユー; マーケル，ダニエル・シー& ポクロフスキ，コンスタンティン・エイet al.,"１，１，１，３，３−ペンタフルオロプロパン、トランス−１−クロロ−３，３，３−トリフルオロプロペン、及びトランス−１，３，３，３−テトラフルオロプロペンを共製造するための統合方法",issued 2018-08-29
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