CN105622331A - Preparation method of fluorine-containing olefin - Google Patents
Preparation method of fluorine-containing olefin Download PDFInfo
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- CN105622331A CN105622331A CN201610097726.0A CN201610097726A CN105622331A CN 105622331 A CN105622331 A CN 105622331A CN 201610097726 A CN201610097726 A CN 201610097726A CN 105622331 A CN105622331 A CN 105622331A
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- Prior art keywords
- fluorine containing
- containing olefine
- preparation
- fluorine
- catalyst
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- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 title claims abstract description 39
- 229910052731 fluorine Inorganic materials 0.000 title claims abstract description 39
- 239000011737 fluorine Substances 0.000 title claims abstract description 39
- 238000002360 preparation method Methods 0.000 title claims abstract description 16
- 150000001336 alkenes Chemical class 0.000 title abstract 6
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 title abstract 6
- 239000003054 catalyst Substances 0.000 claims abstract description 22
- 238000006243 chemical reaction Methods 0.000 claims abstract description 15
- NSGXIBWMJZWTPY-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropane Chemical compound FC(F)(F)CC(F)(F)F NSGXIBWMJZWTPY-UHFFFAOYSA-N 0.000 claims abstract description 11
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 claims abstract description 11
- 239000006227 byproduct Substances 0.000 claims abstract description 11
- 229910000040 hydrogen fluoride Inorganic materials 0.000 claims abstract description 11
- MSSNHSVIGIHOJA-UHFFFAOYSA-N pentafluoropropane Chemical compound FC(F)CC(F)(F)F MSSNHSVIGIHOJA-UHFFFAOYSA-N 0.000 claims abstract description 11
- 230000009471 action Effects 0.000 claims abstract description 10
- 238000009835 boiling Methods 0.000 claims abstract description 7
- 239000007789 gas Substances 0.000 claims abstract description 7
- 238000006317 isomerization reaction Methods 0.000 claims abstract description 7
- 238000000034 method Methods 0.000 claims abstract description 7
- 239000000126 substance Substances 0.000 claims abstract description 7
- 238000000926 separation method Methods 0.000 claims abstract description 4
- PNEYBMLMFCGWSK-UHFFFAOYSA-N Alumina Chemical compound [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 21
- 238000005516 engineering process Methods 0.000 claims description 12
- 239000000047 product Substances 0.000 claims description 10
- 239000013067 intermediate product Substances 0.000 claims description 9
- 239000002994 raw material Substances 0.000 claims description 7
- KLZUFWVZNOTSEM-UHFFFAOYSA-K Aluminium flouride Chemical compound F[Al](F)F KLZUFWVZNOTSEM-UHFFFAOYSA-K 0.000 claims description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 6
- 230000000694 effects Effects 0.000 claims description 6
- 238000005984 hydrogenation reaction Methods 0.000 claims description 6
- 238000004821 distillation Methods 0.000 claims description 4
- NDMMKOCNFSTXRU-UHFFFAOYSA-N 1,1,2,3,3-pentafluoroprop-1-ene Chemical compound FC(F)C(F)=C(F)F NDMMKOCNFSTXRU-UHFFFAOYSA-N 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 3
- 230000003197 catalytic effect Effects 0.000 claims description 3
- 238000003682 fluorination reaction Methods 0.000 claims description 3
- HCDGVLDPFQMKDK-UHFFFAOYSA-N hexafluoropropylene Chemical compound FC(F)=C(F)C(F)(F)F HCDGVLDPFQMKDK-UHFFFAOYSA-N 0.000 claims description 3
- 239000011261 inert gas Substances 0.000 claims description 3
- 229910052751 metal Inorganic materials 0.000 claims description 3
- 239000002184 metal Substances 0.000 claims description 3
- 229910052756 noble gas Inorganic materials 0.000 claims description 3
- 229910052763 palladium Inorganic materials 0.000 claims description 3
- 208000012839 conversion disease Diseases 0.000 abstract description 6
- 230000008901 benefit Effects 0.000 abstract description 3
- 238000005796 dehydrofluorination reaction Methods 0.000 abstract 1
- -1 hexafluoropropylene, pentafluoropropylene Chemical group 0.000 abstract 1
- 239000012528 membrane Substances 0.000 abstract 1
- 239000003507 refrigerant Substances 0.000 description 7
- 238000004378 air conditioning Methods 0.000 description 3
- PGJHURKAWUJHLJ-UHFFFAOYSA-N 1,1,2,3-tetrafluoroprop-1-ene Chemical compound FCC(F)=C(F)F PGJHURKAWUJHLJ-UHFFFAOYSA-N 0.000 description 2
- FXRLMCRCYDHQFW-UHFFFAOYSA-N 2,3,3,3-tetrafluoropropene Chemical compound FC(=C)C(F)(F)F FXRLMCRCYDHQFW-UHFFFAOYSA-N 0.000 description 2
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 2
- 239000005431 greenhouse gas Substances 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- LVGUZGTVOIAKKC-UHFFFAOYSA-N 1,1,1,2-tetrafluoroethane Chemical compound FCC(F)(F)F LVGUZGTVOIAKKC-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000033228 biological regulation Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 238000005057 refrigeration Methods 0.000 description 1
- 230000004083 survival effect Effects 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
Classifications
-
- 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
- C07C17/354—Preparation of halogenated hydrocarbons by reactions not affecting the number of carbon or of halogen atoms in the reaction by hydrogenation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/25—Preparation of halogenated hydrocarbons by splitting-off hydrogen halides from halogenated hydrocarbons
-
- 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
- C07C17/38—Separation; Purification; Stabilisation; Use of additives
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a preparation method of fluorine-containing olefin.The preparation method comprises the following steps that 1, hexafluoropropylene, pentafluoropropylene and H2 generate hexafluoropropane and pentafluoropropane under the action of a hydrogenated catalyst; 2, hexafluoropropane and pentafluoropropane are subjected to a dehydrofluorination reaction; 3, the fluorine-containing olefin and hydrogen fluoride azeotrope are separated from other high-boiling point substances through a normal-pressure rectification technique; 4, the fluorine-containing olefin and hydrogen fluoride are separated through a variable-pressure rectification technique; 5, the finished fluorine-containing olefin and a by-product are separated through a fluorine-containing gas separation membrane, and the by-product makes contact with an isomerization catalyst in a reactor to obtain the finished fluorine-containing olefin.In this way, the preparation method has the advantages that the reaction temperature can be lowered, and the reaction conversion rate can be increased.
Description
Technical field
The present invention relates to tetrafluoropropene technical field, the preparation method particularly relating to a kind of Fluorine containing olefine.
Background technology
Depletion of the ozone layer is one of global problem being related to environment for human survival now. Ozonosphere protection is taken action, be 20 the end of the century whole world science and technology, industrial quarters be the once successfully international cooperation that ecological environment carries out of preserving our planet. Two international treaty and the countries concerned, area action scheme promotion under, within short 10 years, succeed in developing a collection of ODS substitute to ozone layer without destruction and the low substitute of greenhouse effect.
In order to realize reduction of greenhouse gas discharge comprehensively, national governments have put into effect a series of policies and measures in succession, and the air-conditioning refrigerant use of global warming coefficient value (GWP) is any limitation as.
" instruction about automotive air-conditioning system emission " regulation that European Parliament and EU Council put into effect on May 17th, 2006: on January 1st, 2011 plays all new approval car model and will prohibit the use of the GWP value cold-producing medium more than 150; On January 1st, 2017 plays all vehicles newly dispatched from the factory and will prohibit the use of the GWP value cold-producing medium more than 150. The U.S. and Japanese government have also explicitly indicated that and to be phased out high GWP value car air conditioner refrigerant.
Low GWP value succedaneum technology lacks the bottleneck becoming restriction reduction of greenhouse gas discharge action. National governments, each big business, research institutions put into huge fund one after another and research and develop novel succedaneum. It may be said that who has grasped succedaneum technology, the cold-producing medium market who has just grasped future.
Current China has become refrigerant product production base, the whole world. Under this background, the international trend of refrigerant replacement technology must be paid close attention to, the China of investigation in time refrigerant replacement technology path, exploitation adapts to alternative refrigerant and the correlation technique that China's national situation can be had the advantage again in international competition, fulfil Chinese government's promise to international community, promote the sustainable development of China's refrigeration subject and industry.
HFO-1234yf, as young mobile air-conditioning refrigerant, has outstanding environmental-protecting performance, and its GWP is only 4, far below the 1300 of existing automobile refrigerating agent HFC-134a.
The initiation material that the preparation method of existing HFO-1234yf adopts is difficult to produce and not easily obtain, and reaction condition is violent, and reaction reagent is expensive, low conversion rate.
Summary of the invention
What present invention mainly solves technical problem is that: for the deficiencies in the prior art, it is provided that the preparation method of a kind of Fluorine containing olefine, it is possible to reduce reaction temperature, improves reaction conversion ratio.
For solving above-mentioned technical problem, the technical scheme that the present invention adopts is: the preparation method providing a kind of Fluorine containing olefine, comprises the following steps:
1) by raw material hexafluoropropene and pentafluoropropene and H2Intermediate products HFC-236fa and pentafluoropropane is generated under the effect of hydrogenation catalyst;
2) intermediate products HFC-236fa and pentafluoropropane carry out de-HF reaction under catalyst action, obtain Fluorine containing olefine and hydrogen fluoride azeotrope and other high boiling substance;
3) adopt atmospheric distillation technology Fluorine containing olefine and hydrogen fluoride azeotrope and other high boiling substance to be separated in rectifying column, obtain Fluorine containing olefine and hydrogen fluoride azeotrope;
4) adopt variable-pressure rectification technology Fluorine containing olefine and fluohydric acid gas to be separated again in rectifying column, obtain finished product Fluorine containing olefine and side-product;
5) adopt fluoro-gas separation film finished product Fluorine containing olefine and side-product to be separated, then adopt catalytic isomerization technique to be contacted in the reactor with isomerization catalyst by side-product, obtain finished product Fluorine containing olefine.
In a preferred embodiment of the present invention, hydrogenation catalyst described in step 1) is aluminium oxide or the aluminium fluoride of supported palladium.
In a preferred embodiment of the present invention, step 2) described in catalyst be aluminium oxide or alumina load metal.
In a preferred embodiment of the present invention, step 2) it is specially intermediate products HFC-236fa and pentafluoropropane under catalyst action, carries out fluorination reaction, and react in the presence of an inert gas.
In a preferred embodiment of the present invention, described noble gas is N2��
The invention has the beneficial effects as follows: by Rational choice raw material and processing arrangement, adopt the low raw material easily produced of cost and each catalyst so that reaction condition is gentle, it is possible to reduce reaction temperature, improve reaction conversion ratio.
Detailed description of the invention
Below presently preferred embodiments of the present invention is described in detail, so that advantages and features of the invention can be easier to be readily appreciated by one skilled in the art, thus protection scope of the present invention being made apparent clear and definite defining.
The present invention specifically includes:
The preparation method of a kind of Fluorine containing olefine, comprises the following steps:
1) by raw material hexafluoropropene and pentafluoropropene and H2Intermediate products HFC-236fa and pentafluoropropane is generated under the effect of hydrogenation catalyst;
2) intermediate products HFC-236fa and pentafluoropropane carry out de-HF reaction under catalyst action, obtain Fluorine containing olefine and hydrogen fluoride azeotrope and other high boiling substance;
3) adopting atmospheric distillation technology Fluorine containing olefine and hydrogen fluoride azeotrope and other high boiling substance to be separated in rectifying column, obtain Fluorine containing olefine and hydrogen fluoride azeotrope, pressure during described atmospheric distillation is 0.2-0.4MPa;
4) adopting variable-pressure rectification technology Fluorine containing olefine and fluohydric acid gas to be separated again in rectifying column, obtain finished product Fluorine containing olefine and side-product, described rectifying column is the rectification double tower adopting two different pressures operations;
5) adopt fluoro-gas separation film finished product Fluorine containing olefine and side-product to be separated, then adopt catalytic isomerization technique to be contacted in the reactor with isomerization catalyst by side-product, obtain finished product Fluorine containing olefine.
Wherein, hydrogenation catalyst described in step 1) is aluminium oxide or the aluminium fluoride etc. of supported palladium, it is possible to decrease reaction temperature, improves reaction conversion ratio.
Step 2) described in catalyst be aluminium oxide or alumina load metal.
Step 2) it is specially intermediate products HFC-236fa and pentafluoropropane under catalyst action, carries out fluorination reaction, and react in the presence of an inert gas, described noble gas is N2, it is possible to decrease reaction temperature, improves reaction conversion ratio.
Described rectifying column adopts Sulzer tray type liquid redistributor and catcher to coordinate perforated plate corrugated Mellapak series filler, improves tetrafluoropropene purity, and obtaining final finished purity is 99.9%.
The preparation method that present invention is disclosed a kind of Fluorine containing olefine, by Rational choice raw material and processing arrangement, adopts the low raw material easily produced of cost and each catalyst so that reaction condition is gentle, it is possible to reduce reaction temperature, improves reaction conversion ratio.
The foregoing is only embodiments of the invention; not thereby the scope of the claims of the present invention is limited; every equivalent structure utilizing description of the present invention to make or equivalence flow process conversion; or directly or indirectly it is used in other relevant technical fields, all in like manner include in the scope of patent protection of the present invention.
Claims (5)
1. the preparation method of a Fluorine containing olefine, it is characterised in that comprise the following steps:
1) by raw material hexafluoropropene and pentafluoropropene and H2Intermediate products HFC-236fa and pentafluoropropane is generated under the effect of hydrogenation catalyst;
2) intermediate products HFC-236fa and pentafluoropropane carry out de-HF reaction under catalyst action, obtain Fluorine containing olefine and hydrogen fluoride azeotrope and other high boiling substance;
3) adopt atmospheric distillation technology Fluorine containing olefine and hydrogen fluoride azeotrope and other high boiling substance to be separated in rectifying column, obtain Fluorine containing olefine and hydrogen fluoride azeotrope;
4) adopt variable-pressure rectification technology Fluorine containing olefine and fluohydric acid gas to be separated again in rectifying column, obtain finished product Fluorine containing olefine and side-product;
5) adopt fluoro-gas separation film finished product Fluorine containing olefine and side-product to be separated, then adopt catalytic isomerization technique to be contacted in the reactor with isomerization catalyst by side-product, obtain finished product Fluorine containing olefine.
2. the preparation method of Fluorine containing olefine according to claim 1, it is characterised in that hydrogenation catalyst described in step 1) is aluminium oxide or the aluminium fluoride of supported palladium.
3. the preparation method of Fluorine containing olefine according to claim 1, it is characterised in that step 2) described in catalyst be aluminium oxide or alumina load metal.
4. the preparation method of Fluorine containing olefine according to claim 3, it is characterised in that step 2) it is specially intermediate products HFC-236fa and pentafluoropropane under catalyst action, carries out fluorination reaction, and react in the presence of an inert gas.
5. the preparation method of Fluorine containing olefine according to claim 4, it is characterised in that described noble gas is N2��
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
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| CN201610097726.0A CN105622331A (en) | 2016-02-23 | 2016-02-23 | Preparation method of fluorine-containing olefin |
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| CN201610097726.0A CN105622331A (en) | 2016-02-23 | 2016-02-23 | Preparation method of fluorine-containing olefin |
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| CN105622331A true CN105622331A (en) | 2016-06-01 |
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| CN201610097726.0A Withdrawn CN105622331A (en) | 2016-02-23 | 2016-02-23 | Preparation method of fluorine-containing olefin |
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108458344A (en) * | 2018-06-28 | 2018-08-28 | 中化蓝天霍尼韦尔新材料有限公司 | A kind of pre-processing device and its processing method of Antimonous Oxide from Wasted Antimonic Chloride Catalyst |
| CN112142572A (en) * | 2020-09-18 | 2020-12-29 | 浙江巨化技术中心有限公司 | Continuous production method for synthesizing hydrofluoroether |
| CN112218843A (en) * | 2018-05-30 | 2021-01-12 | Ａｇｃ株式会社 | Method for producing (Z)-1-chloro-2,3,3,4,4,5,5-heptafluoro-1-pentene |
| CN116874345A (en) * | 2023-09-06 | 2023-10-13 | 北京宇极科技发展有限公司 | Method for the gas phase continuous production of E-1, 4, 5-heptafluoro-4- (trifluoromethyl) pent-2-ene |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101351428A (en) * | 2005-11-01 | 2009-01-21 | 纳幕尔杜邦公司 | Azeotrope compositions comprising 2,3,3,3-tetrafluoropropene and hydrogen fluoride and uses thereof |
| CN101544536A (en) * | 2008-03-14 | 2009-09-30 | 霍尼韦尔国际公司 | Process for the manufacture of fluorinated olefins |
| CN102164882A (en) * | 2008-08-22 | 2011-08-24 | 大金工业株式会社 | Process for preparing 2,3,3,3-tetrafluoropropene |
| WO2015006258A1 (en) * | 2013-07-12 | 2015-01-15 | Arkema Inc. | Method of separating organofluorine compounds using membrane |
| CN105037076A (en) * | 2008-05-15 | 2015-11-11 | 墨西哥化学阿玛科股份有限公司 | Process for the preparation of 2, 3, 3, 3-trifluoropropene |
-
2016
- 2016-02-23 CN CN201610097726.0A patent/CN105622331A/en not_active Withdrawn
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101351428A (en) * | 2005-11-01 | 2009-01-21 | 纳幕尔杜邦公司 | Azeotrope compositions comprising 2,3,3,3-tetrafluoropropene and hydrogen fluoride and uses thereof |
| CN101544536A (en) * | 2008-03-14 | 2009-09-30 | 霍尼韦尔国际公司 | Process for the manufacture of fluorinated olefins |
| CN105037076A (en) * | 2008-05-15 | 2015-11-11 | 墨西哥化学阿玛科股份有限公司 | Process for the preparation of 2, 3, 3, 3-trifluoropropene |
| CN102164882A (en) * | 2008-08-22 | 2011-08-24 | 大金工业株式会社 | Process for preparing 2,3,3,3-tetrafluoropropene |
| WO2015006258A1 (en) * | 2013-07-12 | 2015-01-15 | Arkema Inc. | Method of separating organofluorine compounds using membrane |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112218843A (en) * | 2018-05-30 | 2021-01-12 | Ａｇｃ株式会社 | Method for producing (Z)-1-chloro-2,3,3,4,4,5,5-heptafluoro-1-pentene |
| CN112218843B (en) * | 2018-05-30 | 2023-11-17 | Ａｇｃ株式会社 | Method for producing (Z)-1-chloro-2,3,3,4,4,5,5-heptafluoro-1-pentene |
| CN108458344A (en) * | 2018-06-28 | 2018-08-28 | 中化蓝天霍尼韦尔新材料有限公司 | A kind of pre-processing device and its processing method of Antimonous Oxide from Wasted Antimonic Chloride Catalyst |
| CN108458344B (en) * | 2018-06-28 | 2023-09-26 | 中化蓝天霍尼韦尔新材料有限公司 | Pretreatment equipment and treatment method of antimony pentachloride waste catalyst |
| CN112142572A (en) * | 2020-09-18 | 2020-12-29 | 浙江巨化技术中心有限公司 | Continuous production method for synthesizing hydrofluoroether |
| CN116874345A (en) * | 2023-09-06 | 2023-10-13 | 北京宇极科技发展有限公司 | Method for the gas phase continuous production of E-1, 4, 5-heptafluoro-4- (trifluoromethyl) pent-2-ene |
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