CN1207723A - Production of chloro-2,2,2-trifluoroethane - Google Patents
Production of chloro-2,2,2-trifluoroethane Download PDFInfo
- Publication number
- CN1207723A CN1207723A CN 96199775 CN96199775A CN1207723A CN 1207723 A CN1207723 A CN 1207723A CN 96199775 CN96199775 CN 96199775 CN 96199775 A CN96199775 A CN 96199775A CN 1207723 A CN1207723 A CN 1207723A
- Authority
- CN
- China
- Prior art keywords
- chloro
- halothane
- tetrafluoroethane
- mixture
- distillation
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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Classifications
-
- 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
- C07C17/21—Preparation of halogenated hydrocarbons by replacement by halogens of halogen atoms by other halogen atoms with simultaneous increase of the number of halogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/38—Separation; Purification; Stabilisation; Use of additives
- C07C17/383—Separation; Purification; Stabilisation; Use of additives by distillation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C19/00—Acyclic saturated compounds containing halogen atoms
- C07C19/08—Acyclic saturated compounds containing halogen atoms containing fluorine
- C07C19/10—Acyclic saturated compounds containing halogen atoms containing fluorine and chlorine
- C07C19/12—Acyclic saturated compounds containing halogen atoms containing fluorine and chlorine having two carbon atoms
Abstract
A process for producing chloro-2,2,2-trifluoroethane as a co-product of the production of 1,1,1,2-tetrafluoroethane by hydrofluorination of trichloroethylene which comprises (i) treating the 1,1,1,2-tetrafluoroethane product stream containing chloro-2,2,2-trifluoroethane and hydrogen fluoride to form a mixture of 1,1,1,2-tetrafluoroethane and chloro-2,2,2-trifluoroethane, and (ii) distilling said mixture to separate essentially pure chloro-2,2,2-trifluoroethane from the mixture. A preferred distillation in step (ii) comprises (iia) distilling the mixture to separate essentially pure 1,1,1,2-tetrafluoroethane and form a second mixture of 1,1,1,2-tetrafluoroethane and chloro-2,2,2-trifluoroethane and (iib) distilling said second mixture to separate essentially pure chloro-2,2,2-trifluoroethane from the second mixture.
Description
The present invention relates to produce chloro-2,2 2-Halothane, HCFC 133a and be particularly related to from trieline co-production 1,1,1 2-Tetrafluoroethane and chloro-2,2, the method for 2-Halothane from trieline.Concrete especially scheme of the present invention relates to by following two-step reaction from 1,1, and 1, obtain chloro-2,2 as the common property thing in the production of 2-Tetrafluoroethane, the 2-Halothane: (i) trieline and hydrogen fluoride reaction form chloro-2,2,2-Halothane and (ii) chloro-2,2, the 2-Halothane makes chloro-2,2 being circulated to step (i), 2-Halothane and hydrogen fluoride reaction produce 1,1,1, the 2-Tetrafluoroethane.
In vapor phase, for example in the presence of chromic oxide or the chromium oxide-based catalyst, trieline and hydrogen fluoride two-step reaction are produced chloro-2,2 at fluorination catalyst, 2-Halothane and 1,1,1, the 2-Tetrafluoroethane is known, with be that some produce 1,1,1, the basis of 2-Tetrafluoroethane factory.This reaction can be carried out in the single reaction zone or carry out two-step reaction at the conversion zone that separates.This reaction produces a lot of by products, particularly hydrogenchloride and various saturated and undersaturated Chlorofluorocarbons (CFCs) and chloro-2,2, the 2-Halothane generates 1,1,1, the molecular balance of 2-Tetrafluoroethane is limited, thus gained 1,1,1,2-Tetrafluoroethane product steam contains usually and is less than 1,1 of 20% weight, 1, the hydrogenchloride of 2-Tetrafluoroethane and vast scale, unreacted chloro-2,2,2-Halothane and hydrogen fluoride (excessively using in a large number usually).
1,1,1,2-Tetrafluoroethane product steam is generally handled through several steps, comprise distillation, reclaim hydrogenchloride and pure substantially 1,1,1, the 2-Tetrafluoroethane mainly comprises chloro-2,2 with providing, 2-Halothane and hydrofluoric rough recirculation steam, but also comprise various Chlorofluorocarbons (CFCs) by products.So far nobody attempts from 1,1,1, reclaims as 1,1,1 the pure substantially chloro-2,2 of the common property thing of 2-Tetrafluoroethane production method, 2-Halothane in the 2-Tetrafluoroethane product steam.
The present invention relates to chloro-2,2, the production method of 2-Halothane wherein contains chloro-2,2,2-Halothane and hydrofluoric 1,1,1,2-Tetrafluoroethane product steam is treated and reclaim pure substantially chloro-2,2,2-Halothane and pure substantially 1,1,1, the 2-Tetrafluoroethane.
The invention provides and a kind ofly produce 1,1,1 in the trieline hydrofluorination, in the 2-Tetrafluoroethane as the chloro-2 of common property thing, 2, the production method of 2-Halothane, this method comprise that (i) processing contains chloro-2,2,2-Halothane and hydrofluoric 1,1,1,2-Tetrafluoroethane product steam, make it form 1,1,1,2-Tetrafluoroethane and chloro-2,2, the mixture of 2-Halothane and (ii) distill this mixture, from mixture, separate pure substantially chloro-2,2,2-Halothane.
The distillation that step is (ii) carried out can be the single phase distillation, directly separates chloro-2,2,2-Halothane from mixture; Maybe can pass through two stages or multistage fractionation by distillation chloro-2,2,2-Halothane.
In the single phase distillation, with 1,1,1 of step (i) formation, 2-Tetrafluoroethane and chloro-2,2, the chloro-2,2 as end cut, 2-Halothane are directly reclaimed in the mixture adding distillation column neutralization of 2-Halothane from post.It should be understood that this stage is described to single phase distillation, still, it can carry out in surpassing a distillation column.
Chloro-2,2,1,1,1 of 2-Halothane dilution, 2-Tetrafluoroethane product steam residuum can be as the top vapor recovery with by further processing recovery 1,1,1,2-Tetrafluoroethane from post, for example this steam is turned back to 1,1,1 of factory, in the 2-Tetrafluoroethane purification route.If desired, through further processing separation 1,1,1, before the 2-Tetrafluoroethane, the steam that obtains from distillation column can loop back distillation column to separate other a certain amount of chloro-2,2,2-Halothane at steam.
1,1,1 of the middle formation of step (i), 2-Tetrafluoroethane and chloro-2,2, the mixture of 2-Halothane are gone up not fluorinated hydrogen and hydrogenchloride substantially, but contain Chlorofluorocarbons (CFCs) by product in a small amount usually.In step single phase distillation (ii), these by products are retained in the post and with 1,1,1,2-Tetrafluoroethane steam reclaims together.Yet in the concrete scheme of single phase distillatory, boiling point is 1,1,1,2-Tetrafluoroethane and chloro-2,2, and the by product between the 2-Halothane can be used as side stream and reclaims from post.
Step distillation (ii) can be two stages or multistage operation and the distillation of preferred two stages, and wherein the fs (iia) comprises 1,1 of the middle formation of distilation steps (i), 1,2-Tetrafluoroethane and chloro-2,2, the mixture of 2-Halothane separates pure substantially 1,1 as tops from post, 1, the 2-Tetrafluoroethane also forms 1,1,1,2-Tetrafluoroethane and chloro-2,2, second mixture of 2-Halothane, and subordinate phase (iib) comprises this second mixture of distillation, separates pure substantially chloro-2,2 as end cut, the 2-Halothane also forms 1,1,1,2-Tetrafluoroethane and chloro-2,2, the 3rd mixture of 2-Halothane.
Therefore, this preferred concrete scheme provides in the trieline hydrofluorination and has produced 1,1,1, in the 2-Tetrafluoroethane as the chloro-2,2 of common property thing, the production method of 2-Halothane contains chloro-2,2 comprising (i) processing, 2-Halothane and hydrofluoric 1,1,1,2-Tetrafluoroethane product steam makes and forms 1,1,1,2-Tetrafluoroethane and chloro-2,2, first mixture of 2-Halothane, (iia) distill this first mixture to separate pure substantially 1,1,1, the 2-Tetrafluoroethane also forms 1,1,1,2-Tetrafluoroethane and chloro-2,2, second mixture of 2-Halothane distills this second mixture to separate pure substantially chloro-2 with (iib), 2, the 2-Halothane also forms 1,1,1,2-Tetrafluoroethane and chloro-2,2, the 3rd mixture of 2-Halothane.
1,1,1 of the middle acquisition of step (iia), 2-Tetrafluoroethane and chloro-2,2, the 3rd mixture of 2-Halothane can be recycled to 1,1,1, any step of 2-Tetrafluoroethane production method or loop back before thick 1,1,1 of the inventive method step (i) is in the 2-Tetrafluoroethane product steam.
Add thick 1,1,1 in present method step (i), 2-Tetrafluoroethane product steam does not preferably have hydrogenchloride.Therefore, method of the present invention preferably includes the other step of handling the crude product steam, for example by distillation, and separating hydrogen chloride before (i) handles set by step.
Typical 1,1,1, in the 2-Tetrafluoroethane production method, can be from 1,1,1, separate 1,1,1 roughly in the 2-Tetrafluoroethane product vapor, 2-Tetrafluoroethane, chloro-2,2,2-Halothane and hydrofluoric mixture, for example as the top steam of distillation column, also can be from mainly containing chloro-2,2,2-Halothane and hydrofluoric mixture for example from the liquid bottom steam and/or the gaseous state side line steam of distillation column, separate above mixture roughly.Chloro-2,2,2-Halothane/carbon hydrogen fluoride mixture preferred cycle returns 1,1,1,2-Tetrafluoroethane production method, with regard to two-step approach or loop back chloro-2,2,2-Halothane step of converting or loop back the trieline step of converting.
After removing de-chlorine hydride, from mainly containing chloro-2,2, separate 1,1 in 2-Halothane and the hydrofluoric circulation steam, 1,1,1,1 of 2-Tetrafluoroethane and hydrofluoric mixture, the distillation of 2-Tetrafluoroethane product steam is 1,1,1, the habitual step that the 2-Tetrafluoroethane is produced.Still-process is quite thick, so that habitual distillating method is isolating 1,1,1, and 2-Tetrafluoroethane and hydrofluoric mixture may contain chloro-2,2, the 2-Halothane, its afterwards the stage remove with recirculation and return 1,1,1, in the 2-Tetrafluoroethane production method.Yet conventional distillation is in designed condition (temperature and pressure) operation down, so that reduce chloro-2,2, and 2-Halothane and 1,1,1,2-Tetrafluoroethane and hydrofluoric mutual conversion thereby reduce the heavy burdens for later separating step.The processing of step of the present invention (i), operating under the distillatory condition under for example high temperature and/or the low pressure, thereby, in separating mixture, there is considerable chloro-2,2, the 2-Halothane is so that be recirculation 1,1,1,2-Tetrafluoroethane production method provides the chloro-2 as the common property thing, 2, the source of 2-Halothane.
Chloro-2,2 in the isolating mixture in the step (i), the amount of 2-Halothane and the chloro-2,2 that can get as the common property thing, the amount of 2-Halothane relies on also thereby is subjected to the control of distillation column operational condition.For the operator, the selection operation condition to be being suitable for the chloro-2,2 as the common property thing, any special needs of 2-Halothane, and this is very easy thing.As guidance, the post pressure scope of operation is about 10-20barg usually.
Isolating 1,1,1 from the product steam, 2-Tetrafluoroethane, chloro-2,2,2-Halothane and hydrofluoric mixture are treatedly then removed hydrogen fluoride and are formed 1,1,1,2-Tetrafluoroethane and chloro-2,2, the mixture of 2-Halothane.Can remove hydrogen fluoride effectively by the technology that is fit to arbitrarily, for example water or basic solution purging compound.
Present method is usually included in step (i) and removes hydrogen fluoride and the step step additional processing between (ii) distilling, to reclaim pure substantially chloro-2,2,2-Halothane.As previously discussed, step (i) generally includes simple distillation 1,1,1, and 2-Tetrafluoroethane product vapor is to separate 1,1,1,2-Tetrafluoroethane, chloro-2,2,2-Halothane and hydrofluoric mixture.Yet, 1,1,1,2-Tetrafluoroethane product vapor contains several other chlorine fluorine (hydrogen) hydrocarbon components usually and they are divided into " light materials " and " heavy substance " in the isolating mixture of step (i).May contain one or more " light materials " components in the mixture that obtains in the step (i) and they are handled by for example distillation usually, so that (ii) remove these components before the charging in step." light materials " component of removing in the reason process herein is not suitable for 1,1,1 usually, and therefore the recirculation of 2-Tetrafluoroethane production method can for example discharge in hot oxidant and handle.The operational condition of separating " light materials " component is known and/or easy decision, but as instructing, normally used post is pressed and is 10-20barg.
The step of present method (ii) in, pure substantially chloro-2,2, the 2-Halothane is separated.In preferred two stages distillation, in step (iia), pass through distillation from chloro-2,2,2-Halothane and a small amount of 1,1,1, separate 1 in second mixture of 2-Tetrafluoroethane, 1,1, the 2-Tetrafluoroethane, then, back one mixture pure substantially chloro-2,2 of fractionation by distillation in step (iib), the 2-Halothane.The operator determines the operational condition of distillation column easily, but as instructing, post is pressed and is about 1-15barg usually, is to press for about 1-10barg post in 5-12barg and the step (iib) in the step (iia).As previously mentioned, from 1,1 of step (iib), 1,2-Tetrafluoroethane and chloro-2,2, any residue (the 3rd) mixture of 2-Halothane can for example loop back from 1,1 to reclaim product in order further to handle in recirculation, 1,1,1 of 2-Tetrafluoroethane production method, 1,2-Tetrafluoroethane product vapor or 1,1,1, the spawn separating treatment step of 2-Tetrafluoroethane production method or any step.
1,1,1,2-Tetrafluoroethane product vapor can be to produce 1,1,1 from the trieline hydrofluorination, any method of 2-Tetrafluoroethane and the invention is not restricted to produce 1,1,1 from trieline, any special methods of 2-Tetrafluoroethane.
The inventive method also can be carried out with batch methods, though our preferred continuous production.Our preferred continuous production in two stage distillation procedures is at least to comprising step (iia).Step (iib) can be included in the continuous flow procedure, but if desired, from the chloro-2,2 of step (iia), 2-Halothane and 1,1,1, second mixture of 2-Tetrafluoroethane can store and step (iib) in the batch operation separating treatment.
Claims (10)
1. produce chloro-2,2, the method for 2-Halothane for one kind, this method comprise (i) handle by trieline hydrofluorination gained and contain chloro-2,2,2-Halothane and hydrofluoric 1,1,1,2-Tetrafluoroethane product vapor, form 1,1,1,2-Tetrafluoroethane and chloro-2,2, the mixture of 2-Halothane and (ii) distill this mixture from the pure substantially chloro-2 of mixture separation, 2, the 2-Halothane.
2. the process of claim 1 wherein that step (ii) comprises the distillation of two steps to separate 1,1,1 in the first step, the 2-Tetrafluoroethane separates chloro-2,2,2-Halothane with going on foot second.
3. claim 1 or 2 method, comprise (i) handle by trieline hydrofluorination gained and contain chloro-2,2,2-Halothane and hydrofluoric 1,1,1,2-Tetrafluoroethane product vapor is to form 1,1,1,2-Tetrafluoroethane and chloro-2,2, first mixture of 2-Halothane, (iia) distill this first mixture to separate pure substantially 1,1,1, the 2-Tetrafluoroethane also forms 1,1,1,2-Tetrafluoroethane and chloro-2,2, second mixture of 2-Halothane distills this second mixture to separate pure substantially chloro-2 with (iib), 2, the 2-Halothane also forms 1,1,1,2-Tetrafluoroethane and chloro-2,2, the 3rd mixture of 2-Halothane.
4. the process of claim 1 wherein step (ii) comprise single phase distillation with form from step (i) 1,1,1,2-Tetrafluoroethane and chloro-2,2, the chloro-2,2 that 2-Halothane mixture separation is pure substantially, 2-Halothane.
5. the method for claim 4, wherein chloro-2,2, the 2-Halothane is discharged from distillation column as end cut and 1,1,1,2-Tetrafluoroethane product vapor from capital discharge and wherein in the middle of the by product of boiling point discharge from post as the side line steam.
6. arbitrary method of claim 1-5, wherein rough 1,1,1,2-Tetrafluoroethane product vapor is processed before to remove de-chlorine hydride in step (i).
7. the method for claim 6, this processing that wherein removes de-chlorine hydride comprises distillation.
8. arbitrary method of requiring of aforesaid right is wherein separated chloro-2,2, and the product vapor after the 2-Halothane is recycled step (i) or step (ii).
9. arbitrary method of aforesaid right requirement is wherein separated chloro-2,2, and the product vapor after the 2-Halothane is sent back to 1,1,1,2-Tetrafluoroethane production method again.
10. arbitrary method of requiring of aforesaid right, this method is carried out with continuation method.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB9524268.1 | 1995-11-28 | ||
| GBGB9524268.1A GB9524268D0 (en) | 1995-11-28 | 1995-11-28 | Production of chloro-2,2,2-trifluoroethane |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN1207723A true CN1207723A (en) | 1999-02-10 |
Family
ID=10784536
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN 96199775 Pending CN1207723A (en) | 1995-11-28 | 1996-11-26 | Production of chloro-2,2,2-trifluoroethane |
Country Status (9)
| Country | Link |
|---|---|
| EP (1) | EP1021390A1 (en) |
| JP (1) | JP2000501391A (en) |
| CN (1) | CN1207723A (en) |
| AU (1) | AU7635596A (en) |
| BR (1) | BR9611660A (en) |
| CA (1) | CA2238508A1 (en) |
| GB (1) | GB9524268D0 (en) |
| MX (1) | MX9804231A (en) |
| WO (1) | WO1997019903A1 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112250540A (en) * | 2020-10-14 | 2021-01-22 | 太仓中化环保化工有限公司 | Method for separating R134a, R133a and R124 from rectification heavy components |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP3173154B2 (en) * | 1992-07-27 | 2001-06-04 | 昭和電工株式会社 | Method for producing 1,1,1,2 tetrafluoroethane |
| JP3173155B2 (en) * | 1992-07-27 | 2001-06-04 | 昭和電工株式会社 | Method for producing 1,1,1,2 tetrafluoroethane |
| TW227550B (en) * | 1992-08-05 | 1994-08-01 | Showa Denko Kk | |
| TW228512B (en) * | 1992-08-10 | 1994-08-21 | Showa Denko Kk |
-
1995
- 1995-11-28 GB GBGB9524268.1A patent/GB9524268D0/en active Pending
-
1996
- 1996-11-26 AU AU76355/96A patent/AU7635596A/en not_active Abandoned
- 1996-11-26 EP EP96939223A patent/EP1021390A1/en not_active Withdrawn
- 1996-11-26 CA CA 2238508 patent/CA2238508A1/en not_active Withdrawn
- 1996-11-26 JP JP9520266A patent/JP2000501391A/en active Pending
- 1996-11-26 BR BR9611660A patent/BR9611660A/en unknown
- 1996-11-26 CN CN 96199775 patent/CN1207723A/en active Pending
- 1996-11-26 WO PCT/GB1996/002909 patent/WO1997019903A1/en not_active Application Discontinuation
-
1998
- 1998-05-28 MX MX9804231A patent/MX9804231A/en unknown
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112250540A (en) * | 2020-10-14 | 2021-01-22 | 太仓中化环保化工有限公司 | Method for separating R134a, R133a and R124 from rectification heavy components |
| CN112250540B (en) * | 2020-10-14 | 2023-10-31 | 太仓中化环保化工有限公司 | Method for separating R134a, R133a and R124 from rectification heavy component |
Also Published As
| Publication number | Publication date |
|---|---|
| AU7635596A (en) | 1997-06-19 |
| WO1997019903A1 (en) | 1997-06-05 |
| BR9611660A (en) | 1999-02-23 |
| MX9804231A (en) | 1998-09-30 |
| GB9524268D0 (en) | 1996-01-31 |
| CA2238508A1 (en) | 1997-06-05 |
| EP1021390A1 (en) | 2000-07-26 |
| JP2000501391A (en) | 2000-02-08 |
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