CN105939986A - Process for the manufacture of hydrochlorofluoroolefins - Google Patents
Process for the manufacture of hydrochlorofluoroolefins Download PDFInfo
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- CN105939986A CN105939986A CN201580006311.1A CN201580006311A CN105939986A CN 105939986 A CN105939986 A CN 105939986A CN 201580006311 A CN201580006311 A CN 201580006311A CN 105939986 A CN105939986 A CN 105939986A
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- isomerization
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/35—Preparation of halogenated hydrocarbons by reactions not affecting the number of carbon or of halogen atoms in the reaction
- C07C17/358—Preparation of halogenated hydrocarbons by reactions not affecting the number of carbon or of halogen atoms in the reaction by isomerisation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
- C07C17/20—Preparation of halogenated hydrocarbons by replacement by halogens of halogen atoms by other halogen atoms
- C07C17/202—Preparation of halogenated hydrocarbons by replacement by halogens of halogen atoms by other halogen atoms two or more compounds being involved in the reaction
- C07C17/206—Preparation of halogenated hydrocarbons by replacement by halogens of halogen atoms by other halogen atoms two or more compounds being involved in the reaction the other compound being HX
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C21/00—Acyclic unsaturated compounds containing halogen atoms
- C07C21/02—Acyclic unsaturated compounds containing halogen atoms containing carbon-to-carbon double bonds
- C07C21/18—Acyclic unsaturated compounds containing halogen atoms containing carbon-to-carbon double bonds containing fluorine
Abstract
The disclosure provides a process for the manufacture of trans 1-chloro3,3,3-trifluoropropene (trans 1233zd) by fluorinating 1230za and/or 240fa to a cis/trans mixture of 1233zd, separating the trans isomer followed by an isomerization of cis 1233zd to trans 1233zd in the fluorination step. The fluorination step is carried out in the gas phase or the liquid phase. The isomerization is carried out in the gas phase with a high surface area heterogeneous Cr catalyst, supported or unsupported.
Description
Invention field
The present invention relates to a kind of method for manufacturing hydrogen chlorine fluoroolefins.
Background of invention
Montreal Protocol order for ozonosphere protection is phased out the use of Chlorofluorocarbons (CFCs) (CFC).
The material more " friendly " to ozone layer, such as hydrofluoroalkane (HFC) (such as 134a) instead of Chlorofluorocarbons (CFCs).
The compound of the latter has turned out to be greenhouse gases, causes global warming and can be subject to the capital about climate change
All protocols are administered.Need environmentally to can accept, i.e. there is negligible ODP (ODP)
And the substitution material of acceptable low global warming up trend (GWP).The present invention describes for manufacturing
Hydrogen chlorine fluoroolefins, the method for trans 1233zd (E-1233zd, 1-chloro-3,3,3 ,-trifluoropropene), this hydrogen chlorine
Fluoroolefins is as the foaming agent (for thermosetting and thermoplastic foam), molten of low ODP and low GWP
Agent, heat transfer fluid (such as in heat pump) and cold-producing medium (such as the low pressure refrigerant of cooler)
It is useful.
US patent publication US 2008/0051610 and US 2008/0103342 discloses following side
Method, the method includes the isoversion step of cis 1234ze to trans 1234ze.US 7,420,094
Disclose use catalyst based on Cr and 1234ze is isomerizated into 1234yf.US 2008/0051611 drapes over one's shoulders
Reveal and from the mixture including cis 1234ze and trans 1234ze, reclaimed trans 1234ze by distillation.
Summary of the invention
The present invention relates to a kind of for manufacturing this hydrogen chlorine fluoroolefins, trans 1-chloro-3,3,3 ,-trifluoropropene
(E-1233zd) method.The method includes from cis 1233zd (Z-1233zd) to trans 1233zd
(E-1233zd) isomerization steps.
Accompanying drawing summarizes
Fig. 1 is the schematic diagram of the liquid phase process according to the present invention.
Fig. 2 is the schematic diagram of the gas phase process according to the present invention.
Fig. 3 is the schematic diagram of the liquid phase process of the recirculation including 1233zd according to the present invention.
Fig. 4 is the schematic diagram of the gas phase process of the recirculation including 1233zd according to the present invention.
Detailed description of the invention
The invention provides a kind of for manufacturing trans 1-'s chloro-3,3,3-trifluoro propene (E-1233zd)
Method.The first step of the method includes 1,1,3,3-tetrachloropropylene (1230za, CCl2=CH-CHCl2)
And/or 1,1,1,3,3-pentachloropropane (240fa) is fluorinated into cis 1233zd (Z-1233zd) with trans
The mixture of 1233zd (E-1233zd).The second step of the method includes to be formed in first step
Mixture separate to isolate cis 1233zd (Z-1233zd) from this mixture.The method
Third step includes cis 1233zd (Z-1233zd) is isomerizated into trans 1233zd (E-1233zd).
The 1230za used in the first step can pass through CCl4With Vinyl Chloride Monomer (VCM,
CH2=CHCl) forming 1,1,1,3,3-pentachloropropane (240fa) (can be by its dehydrochlorination to produce
Reaction 1230za) and obtain.
The present invention be directed to a kind of by 1,1,3,3-tetrachloropropylene (1230za), (CCl2=CH-CHCl2)
And/or 1,1,1,3,3-pentachloropropane (240fa) produces trans 1-chloro-3,3,3-trifluoro propene (E-1233zd)
Method, the method comprises the following steps:
A) by 1,1,3,3-tetrachloropropylene (1230za, CCl2=CH-CHCl2) and/or 1,1,1,3,3-
Pentachloropropane (240fa) is fluorinated or in the gas phase by 1230za liquid-phase fluorination, to obtain cis (Z)
3,3,3 trifluoro propene (1233zd, CFs chloro-with trans (E) 1-3-CH=CHCl) mixture；Connect
?
B) by cis (Z) 1-chloro-3,3,3 ,-trifluoropropene (1233zd, CF3-CH=CHCl) and anti-
Formula (E) 1-chloro-3,3,3 ,-trifluoropropene (1233zd, CF3-CH=CHCl) separate；Then
C) cis 1233zd (Z-1233zd) isomerization from second step is trans to be formed
1233zd(E-1233zd)。
The first step of the method, is 1233zd or general by 1230za and/or 240fa gas phase fluorination
1230za liquid-phase fluorination is 12333zd, can carry out by means of any method known in the art.Example
As: in the US patent No. 5,877,359, disclose the uncatalyzed liquid-phase fluorination of 1230za；At US
The patent No. 5,811,603 discloses the gas phase fluorination of the catalysis of 1230za；The US patent No. 6,166,274
Disclose and in the presence of catalyst (such as trifluoroacetic acid or trifluoromethanesulfonic acid), 1230za is fluorinated into
1233zd.Fluorination catalyst, such as TiCl4、TiF4、SnCl4、SnF4、SbF5、SbCl5、SbFxCly
Or ionic liquid is described in U.S. Patent number 6,881,698 (x+y=5).Work as use
During the catalyst of Sb type, preferably feed low-level Cl2So that these Sb species are maintained work
Property form.
The second step of the method includes the cis 1233zd formed in first step and trans
1233zd is separated by suitable separation means (as distillation, liquid phase separation or extraction separate).
The cis 1233zd and the trans 1233zd that are formed in the first step may comprise HF and HCl.Preferably
Ground, first removes HCl in the first distillation column.Hereafter, it is possible to use combine azeotropic distillation
Liquid phase separation removes HF.The boiling point difference of cis 1233zd and trans 1233zd allows them to
By conventional distillation, the most under atmospheric pressure separated.
The third step of the method relates to being isomerizated into trans by the cis 1233zd from second step
1233zd.This isomerization steps can use heterogeneous or homogeneous in gas phase or liquid phase accordingly
Catalyst is carried out.
This isomerization steps is to use gas phase process attainable in the presence of heterogeneous catalysis.
Suitable heterogeneous catalysis is the high surface Cr of support type or non-loading type(III)Catalyst, this catalysis
Agent can optionally comprise one or more promoters low-level, these promoters selected from cobalt,
Nickel, zinc or manganese.For loaded catalyst, this catalyst carrier can be selected from being known in the art
The material compatible with high temperature and pressure process.Such as, the work that the aluminium oxide of fluorination, HF processed
Property charcoal or carbon graphite are suitable catalyst carriers.Preferably catalyst is the unsupported of high surface
Chromium oxide catalyst, it activates with HF before use, is optionally at the pressure higher than 50psi
Under.When it is present, the level of promoter can be from the 1wt% to 10wt% of this catalyst, preferably
Ground changes from 1wt% to 5wt%.Promoter can add this by method as known in the art and urge
Agent, as adsorbed, then carrying out solvent evaporation from aqueous or organic solvent.
Suitably heterogeneous catalysis is also selected from: selected from SbV、TiIV、SnIV、MoVI、Nbv
And TavLewis acid load catalyst.Carrier itself is selected from lower group, and this group is: be such as fluorinated
Aluminium oxide, the chromium oxide of fluorination, HF activated carbon or graphitic carbon.The antimony halogenide of load is (such as SbF5)
The US patent No. 6,528,691 is described and it is preferred catalyst.Can also be used it
His solid catalyst, asType polymer, acidic molecular sieve and zeolite.
For this gas phase process, temperature can be between 20 DEG C-500 DEG C, preferably at 100 DEG C-400 DEG C
Between change.Time of contact can be from change in 0.5 to 100 second.Can be with the volume hundred between 0.01-0.1
Proportion by subtraction uses low-level oxidant (such as oxygen or oxygen-containing gas such as air, or chlorine) to extend this catalysis
The life-span of agent.
This isomerization steps is also attainable in liquid phase process in the presence of homogeneous catalyst, and this is equal
Phase catalyst is preferably chosen from the 3rd, 4,5,13,14 and 15 of the periodic table of elements (IUPAC 1988)
The metallic compound of race and their mixture (be previously referred to as IIIA, IVa, IVb, Va, Vb and
The race of the periodic table of elements of VIb).The compound of these metals be intended to include these metals hydroxide,
Oxide and organic or inorganic salt, together with their mixture.Preferably aluminum, titanium, tantalum, molybdenum,
Boron, stannum and antimony derivant, such as AlCl3、TiCl4、TaCl5、MoCl6、BF3、SnCl4, and SbCl5.
In the method according to the invention, preferred metal derivative be salt and these be preferably chosen from halogenide also
And it is chosen more particularly from chloride, fluoride and chlorofluoride, such as AlF3、TiF4、TaF5、MoF6、SnF4、
SbF5、SbFxCly(x+y)=5.This catalyst must stand activation before isomerization steps and (pass through HF
Maybe can exchange any molecule of fluorine).In the case of the catalyst of antimony type, it is possible to use low-level
This antimony catalyst is maintained the oxidation state of pentavalent by chlorine as oxidant.Except above-mentioned lewis acid is urged
Outside agent, the ionic liquid derived from antimony, titanium, niobium and tantalum is also suitable for liquid-phase fluorination process.Special at US
Profit number 6,881,698 discloses the explanation preparing this kind of catalyst.
Homogeneous catalyst for liquid phase process is also selected from the acid of Bronsted categorical series, as (but
It is not limited to) sulphuric acid H2SO4；The acid of sulfonic acid type, such as ClSO3H or FSO3H or trifluoromethanesulfonic acid
CF3SO3H or methanesulfonic acid CH3SO3H.For this liquid phase process, operation temperature can be at about 20 DEG C-200 DEG C
Between change, wherein time of contact is between about 0.5-50 hour.
Isomerization is it is also possible that in primary 1233zd reactor, or in gas phase or completes in the liquid phase.
This allows to be recycled back in these primary reactions by isolated Z-1233zd and avoided for individually
The demand of isomerization reactor RI-1 and RI-2.See Fig. 3 and 4.It is believed that this recirculation will cause
Z-1233zd horizontal accumulation to reaching ability, after this this Z-1233zd will in RFL-1 or RFG-2 with
Form its same speed isomerization.
The method of the present invention can include the separating step added between each step.These mesh separated
May is that
1. from this stream, completely or partially remove any hydracid (HF, HCl), if require
Words, or
2. isolate desired product to be fed in step subsequently, or
3. purified product and remove organic impurities or by-product, or
4. desciccate (H2The removal of O).
The means being used for realizing these additional steps are known in the art and include but not limited to: distillation,
Extractive distillation or absorption.
The method of the present invention illustrates in the accompanying drawings, and these accompanying drawings list the gas phase according to the present invention and liquid
The frame flow chart of phase process.Process in these figures is to list with the form of procedure module, these moulds
Block is designed to realize specific purpose and is the method according to the invention and arranges.These module bags
Include:
RFL-includes liquid phase fluorination reactor and distillation system, and this distillation system includes being connected on rectifying column
Without stirring jacketed pressure container.This reactor also serves as the reboiler of this rectifying column.By HF and having
Machine thing (1230za) is directly fed in this reactor.HF and organic molar feed ratio are by reacting
Stoichiometry and leave the amount of HF of this reactor and the overhead of rectifying column and liquid phase purge
(purge) instruction.Mixing is provided by the wallop of reactor content.For the overwhelming majority, instead
Device ejection is answered to leave this reactor vessel as gas and enter the bottom of this rectifying column.From liquid phase
A small amount of purge can remove any nonvolatile matter that may be formed in this course of reaction.This rectifying column
Comprising filler or tower tray, these fillers or tower tray are designed to provide between up flow type gas and downflow system liquid
Good quality transmission.Condenser in this column top leads to supercooled water, chilled water or certain type of system
Cool down.This condenser is fractional condenser, and wherein this liquid emission is directly recirculated back in this post.
Steam ejection is made up of HCl, HF and multiple organic component.
DH-includes that HCl Distallation systm, the purest HCl are removed from the top of distillation column.This
Post can run between 100psig and 300psig.More typically, this HCl is higher than 120psig
Under be distilled to allow to use conventional (-40C) refrigeration at the top of this HCl post.The end of this post
Portion's thing comprises HF and Organic substance and a small amount of remaining HCl.The ratio of HF and organic component is typically
It is to form close to azeotropic.
PS-include liquid phase separator in order to separate two liquid phases, one is main by HCFC (HCFC)
Form and another is mainly made up of HF.This HF phase is typically the densest, and so it is from this
The top of phase separator is left and HCFC leaves mutually as bottom.HCFC phase exists
HF and there are some HCFC in the HF phase.But, the composition of the two phase and any azeotropic group
One-tenth differs greatly.The operation temperature of this phase separator can be between-40 DEG C and+20 DEG C.But,
Temperature is the lowest, is separated the best.
DA-includes azeotropic distillation post, and this post distills out HF and organic Azeotrope compositions at top,
This Organic substance is made up of one or more HCFC (HCFC) and HFC (hydrofluoroalkane).This
A little organic compound can be saturated or olefinic.Bottoms compositions or be entirely HF or complete
Organic substance entirely, depend on the feed composition of this post be at this azeotropic mixture rich in HF side also
It is rich in Organic substance side.If bottoms is HF, this stream is the most generally made to be recycled back into this anti-
Answer device.If bottoms is Organic substance, then it is passed to Distallation systm (the distillation of routine
train)。
DS-includes the straight run generally completed under stress.
RI-includes that gas phase isomerization is reacted, this reaction typically at a temperature of higher than 400 DEG C in thermal insulation
Packed bed reactor in complete.This module is by feeding vaporizer and superheater forms.It can include
" saver ", thus the ejection of heat is fed to the side of heat exchanger and relatively cool anti-
Device feed gas is answered to be fed to opposite side.The gas of discharge is cold taking a step forward of entrance distillation column
But.Isomerization reaction can be carried out with the conversion ratio of change according to the equilibrium assignmen of isomer.These
The isomer discharged can have boiling point the most closely.But, they typically show and connect
Nearly preferably behavior, therefore can be separated by conventional distillation.As the replacement scheme of this gas phase,
This reaction can complete as the liquid phase reactor of homogeneous catalysis.In this configuration, this reactor will
Being the tank of continuous stirring, wherein ejection is removed to realize separating with this catalyst as steam.
RFG-includes gas phase fluorination device, and this reactor is by above gas-phase feed to solid catalyst
Adiabatic packed bed reactor.Need not cooling, because this reactor has low conversion per pass
And high HF molar feed ratio.This heat-insulating heat release is typically less than 100 DEG C.Charging HF
Evaporate in common vaporizer with Organic substance and be heated excessively to this temperature of reactor.This common steaming
If sending out device to allow 1230za and/or 240fa possible temperature when being evaporated as pure component than it
Evaporate under degree lower temperature, thus make thermal degradation minimize.This module can also include " saving
Device ", thus the ejection of heat is fed to the side of heat exchanger and relatively cool reactor enters
Material gas is fed to opposite side.By the gas of discharge in the cooling that takes a step forward entering distillation column.Instead
Answering temperature is between 200 DEG C and 400 DEG C.This pressure is sufficiently high to allow HCl by-product by often
The refrigeration (preferably between 100psig and 200pisg) of rule is distilled.
Being used for identifying the lower case of these modules, to have distinguished the module of same type in same process many
Secondary appearance.
Fig. 1 is the side that 1230za is changed into E-1233zd by liquid-phase fluorination step used according to the invention
The frame flow chart of method.This figure combines and is as described above procedure module.Fig. 1 discloses one
Method, is wherein fed to 1230za and HF in reaction module RFL-1.Typically, this reaction exists
Mainly occur under there is no catalyst rich in the medium of HF.HCl and 1233zd/HF leaves RFL-1
The top of rectifying column.The steam ejection of RFL-1 enters DH-1 so that using HCl as pure tower top
Product removes.The bottoms of DH-1 is mainly by 1233zd (E and the Z isomer two formed close to azeotropic
Person) and HF composition.It is fed in module PS-1 to carry out liquid phase separation.By the richness at top
Delivering to module DA-1a mutually containing HF, HF is separated as bottoms there, for recirculation
To this reactor.The azeotropic mixture of 1233zd Yu HF at top is recycled back into DH-1, to permit
Permitted the HCl of any remnants and lightweight Organic substance before this azeotropic mixture is recycled to be separated at this
Post is stripped out.Bottoms from PS-1 enters module DA-1b, and this module will lack
The organic streams of HF removes as bottoms.It is recycled to DH-1 for by DA-1a azeotropic mixture
Same cause, the overhead from DA-1b is recycled to DH-1.By the end of DA-1b
Portion's thing delivers to procedure module DS-1, and any heavier substances is separated by this module with 1233zd.From DS-1
Overhead be E-1233zd, desired transisomer.Z-1233zd be higher boiling also
And be recycled for being fed to procedure module RI-1.Ejection from this isomerization reactor is followed again
Ring is to DS-1, and this module carries out E and separates with Z isomer.
Alternately, as figure 3 illustrates, the Z-1233zd from DS-1 can be directly by again
Being recycled in RFL-1, wherein isomerization can occur so that by the Z-1233zd concentration in RFL-1
It is restricted to equilibrium level.
Fig. 2 is that 1230za or 240fa is changed into by gas phase fluorination step used according to the invention
The frame flow chart of the method for E-1233zd.This figure combines and is as described above procedure module.?
In Fig. 2, the method is similar to Fig. 1, except such as this liquid phase fluorination reactor (RFL-1) is by gas phase
Fluorination reactor (RFG-1) and azeotropic distillation post (DA-2a) are substituted.
The method summarized such as Fig. 2 includes being fed to 1230za and/or 240fa and HF react mould
In block RFG-2.This reaction uses catalyst to carry out in the gas phase.Reactor ejection mainly by HCl,
The HF composition of 1233zd, unreacted 1230za and excess.The reactor ejection of RFG-2 enters
Enter in DA-2a HF and unreacted F1230za to be removed as bottoms, bottom this
Thing is recycled to this reactor.Will be mainly by HCl and HF and 1233zd (E and Z isomer two
Person) azeotropic mixture composition overhead deliver to DH-2, this module using HCl as pure tower
Top product removes.The bottoms of DH-2 is mainly by 1233zd (E and the Z isomer formed close to azeotropic
The two) and HF composition.It is fed in module PS-2 to carry out liquid phase separation.Top is rich
Delivering to module DA-2b mutually containing HF, HF is separated as bottoms there, for recirculation
To this reactor.The azeotropic mixture of 1233zd Yu HF at top is recycled back into DH-2, to permit
Permitted the HCl of any remnants and lightweight Organic substance before this azeotropic mixture is recycled to be separated at this
Post is stripped out.Bottoms from PS-2 enters module DA-2c, and this module will lack
The organic streams of HF removes as bottoms.It is recycled to DH-2 for by DA-2b azeotropic mixture
Same cause, the overhead from DA-2c is recycled to DH-2.By the end of DA-2c
Portion's thing delivers to procedure module DS-2, and any heavier substances is separated by this module with 1233zd.From DS-2
Overhead be E-1233zd, desired transisomer.Z-1233zd be higher boiling also
And be recycled for feeding to procedure module RI-2.Ejection from this isomerization reactor is followed again
Ring is to DS-2, and this module carries out E and separates with Z isomer.
Alternately, as figure 4 illustrates, Z-1233zd can directly be recycled to RFL-2
In, wherein isomerization can occur so that the Z-1233zd concentration in RFL-2 is restricted to equilibrium water
Flat.
Claims (8)
1. one kind is used for by 1,1,3,3-tetrachloropropylene (1230za) and/or 1,1,1,3,3-pentachloropropane
(240fa) method manufacturing chloro-3,3,3 trifluoro propenes (E-1233zd) of trans 1-, the method includes
Following steps:
By 1,1,3,3-tetrachloropropylene (1230za) and/or 1,1,1,3,3-pentachloropropane (240fa) is fluorinated into bag
Containing cis 1233zd (Z-1233zd) and the mixture of trans 1233zd (E-1233zd)；Then
Described cis 1233zd (Z-1233zd) is separated with described trans 1233zd (E-1233zd)；
Then
Described cis 1233zd (Z-1233zd) is recycled to wherein by described cis 1233zd
(Z-1233zd) in the isomerization described fluorination step with the trans 1233zd of formation (E-1233zd).
2. the method for claim 1, wherein said fluorination step is to enter in gas phase or liquid phase
Row.
3. method as claimed in claim 2, wherein said fluorination step is to use in the liquid phase to be selected from
The homogeneous catalyst of lower group is carried out, and this group is made up of the following: solvable lewis acid catalyst and
Bronsted acid catalyst.
4. method as claimed in claim 3, wherein said solvable lewis acid catalyst is selected from
SbV、TiIV、SnIV、MoVI、NbV、TaV, oxide carried catalyst, the aluminium oxide of fluorination, fluorine
The chromium oxide changed, fluoridized activated carbon, graphitic carbon, SiC, Sb5。
5. method as claimed in claim 4, wherein said oxide carried catalyst is selected from lower group,
This group is by Al2O3And TiO2Composition.
6. method as claimed in claim 3, wherein said Bronsted acid catalyst is selected from lower group,
This group is made up of the following: trifluoromethanesulfonic acid, methanesulfonic acid, sulphuric acid and sulfonic acid.
7. method as claimed in claim 2, wherein said isomerization is to use high surface in the gas phase
Long-pending support type or the heterogeneous Cr catalyst of non-loading type are carried out.
8. method as claimed in claim 7, wherein said catalyst farther includes selected from lower group
Promoter, this group is made up of the following: Co, Ni, Zn and Mn.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US14/167,150 US8987534B2 (en) | 2008-11-19 | 2014-01-29 | Process for the manufacture of hydrochlorofluoroolefins |
| US14/167,150 | 2014-01-29 | ||
| PCT/US2015/013202 WO2015116629A1 (en) | 2014-01-29 | 2015-01-28 | Process for the manufacture of hydrochlorofluoroolefins |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN105939986A true CN105939986A (en) | 2016-09-14 |
| CN105939986B CN105939986B (en) | 2018-11-20 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201580006311.1A Active CN105939986B (en) | 2014-01-29 | 2015-01-28 | Method for manufacturing hydro-chloro fluoroolefin |
Country Status (7)
| Country | Link |
|---|---|
| EP (1) | EP3099655A4 (en) |
| JP (1) | JP2017507121A (en) |
| KR (1) | KR20160113669A (en) |
| CN (1) | CN105939986B (en) |
| CA (1) | CA2938370C (en) |
| MX (1) | MX2016009803A (en) |
| WO (1) | WO2015116629A1 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114262254A (en) * | 2022-03-02 | 2022-04-01 | 北京宇极科技发展有限公司 | Method for preparing E-1-chloro-3, 3, 3-trifluoropropene |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20180194703A1 (en) * | 2017-01-06 | 2018-07-12 | Honeywell International Inc. | Systems and methods for separating (e)-1-chloro-3,3,3-trifluoropropene, hf, and a heavy organic and reactor purge |
| BR112021008031A2 (en) * | 2018-11-15 | 2021-07-27 | Arkema Inc. | method for purifying a crude stream containing hydrochlorofluoro-olefin |
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| US5710352A (en) * | 1996-09-19 | 1998-01-20 | Alliedsignal Inc. | Vapor phase process for making 1,1,1,3,3-pentafluoropropane and 1-chloro-3,3,3-trifluoropropene |
| US20080103342A1 (en) * | 2006-10-27 | 2008-05-01 | Honeywell International Inc. | Processes for geometric isomerization of halogenated olefins |
| CN102216247A (en) * | 2008-11-19 | 2011-10-12 | 阿科玛股份有限公司 | Process for the manufacture of hydrochlorofluoroolefins |
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|---|---|---|---|---|
| US8987534B2 (en) * | 2008-11-19 | 2015-03-24 | Arkema Inc. | Process for the manufacture of hydrochlorofluoroolefins |
| US9045386B2 (en) * | 2010-02-18 | 2015-06-02 | Honeywell International Inc. | Integrated process and methods of producing (E)-1-chloro-3,3,3-trifluoropropene |
| US8704017B2 (en) * | 2010-09-03 | 2014-04-22 | Honeywell International Inc. | Continuous low-temperature process to produce trans-1-chloro-3,3,3-trifluoropropene |
| US8436217B2 (en) * | 2011-04-25 | 2013-05-07 | Honeywell International Inc. | Integrated process to co-produce 1,1,1,3,3-pentafluoropropane, trans-1-chloro-3,3,3-trifluoropropene and trans-1,3,3,3-tetrafluoropropene |
| JP6107465B2 (en) * | 2012-06-29 | 2017-04-05 | セントラル硝子株式会社 | Process for producing 1-chloro-3,3,3-trifluoropropene |
-
2015
- 2015-01-28 JP JP2016549084A patent/JP2017507121A/en active Pending
- 2015-01-28 CA CA2938370A patent/CA2938370C/en active Active
- 2015-01-28 KR KR1020167023301A patent/KR20160113669A/en not_active Application Discontinuation
- 2015-01-28 CN CN201580006311.1A patent/CN105939986B/en active Active
- 2015-01-28 EP EP15743421.8A patent/EP3099655A4/en not_active Withdrawn
- 2015-01-28 MX MX2016009803A patent/MX2016009803A/en unknown
- 2015-01-28 WO PCT/US2015/013202 patent/WO2015116629A1/en active Application Filing
Patent Citations (3)
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| US5710352A (en) * | 1996-09-19 | 1998-01-20 | Alliedsignal Inc. | Vapor phase process for making 1,1,1,3,3-pentafluoropropane and 1-chloro-3,3,3-trifluoropropene |
| US20080103342A1 (en) * | 2006-10-27 | 2008-05-01 | Honeywell International Inc. | Processes for geometric isomerization of halogenated olefins |
| CN102216247A (en) * | 2008-11-19 | 2011-10-12 | 阿科玛股份有限公司 | Process for the manufacture of hydrochlorofluoroolefins |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114262254A (en) * | 2022-03-02 | 2022-04-01 | 北京宇极科技发展有限公司 | Method for preparing E-1-chloro-3, 3, 3-trifluoropropene |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2017507121A (en) | 2017-03-16 |
| MX2016009803A (en) | 2016-11-14 |
| KR20160113669A (en) | 2016-09-30 |
| EP3099655A4 (en) | 2017-06-07 |
| EP3099655A1 (en) | 2016-12-07 |
| CN105939986B (en) | 2018-11-20 |
| CA2938370A1 (en) | 2015-08-06 |
| CA2938370C (en) | 2022-07-12 |
| WO2015116629A1 (en) | 2015-08-06 |
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