1-Chloro-3,3,3-trifluoropropene

1-Chloro-3,3,3-trifluoropropene
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
CAS Number	2730-43-0 mixture of E- and Z- isomers; 102687-65-0 E-isomer; 99728-16-2 Z-isomer;
3D model (JSmol)	Interactive image;
ChemSpider	10331370 mixture of E- and Z- isomers; 4647642 E-isomer; 9833033 Z-isomer;
ECHA InfoCard	100.215.615
PubChem CID	2779022 mixture of E- and Z- isomers; 5709018 E-isomer; 11658298 Z-isomer;
UNII	4B96DT2BYB ;
CompTox Dashboard (EPA)	DTXSID70950023 ;
	InChI 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;
	SMILES FC(F)(F)C=CCl;
Properties
Chemical formula	C3H2ClF3
Molar mass	130.49 g·mol−1
Appearance	Colorless 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). Infobox references

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]

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;
Removal of HCl and HF.
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.
Isolating and purifying the HFO-245fa product
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).
Isolation and purifying the HFO-1233zd product into its isomers.

References

^ 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.
^ 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
^ 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.
^ 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

[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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