JPS62252736A - Production of trifluoroethylene - Google Patents
Production of trifluoroethyleneInfo
- Publication number
- JPS62252736A JPS62252736A JP61093414A JP9341486A JPS62252736A JP S62252736 A JPS62252736 A JP S62252736A JP 61093414 A JP61093414 A JP 61093414A JP 9341486 A JP9341486 A JP 9341486A JP S62252736 A JPS62252736 A JP S62252736A
- Authority
- JP
- Japan
- Prior art keywords
- catalyst
- chlorotrifluoroethylene
- hydrogen
- compound
- trifluoroethylene
- 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.)
- Pending
Links
- MIZLGWKEZAPEFJ-UHFFFAOYSA-N 1,1,2-trifluoroethene Chemical group FC=C(F)F MIZLGWKEZAPEFJ-UHFFFAOYSA-N 0.000 title claims description 14
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- 239000003054 catalyst Substances 0.000 claims abstract description 19
- UUAGAQFQZIEFAH-UHFFFAOYSA-N chlorotrifluoroethylene Chemical group FC(F)=C(F)Cl UUAGAQFQZIEFAH-UHFFFAOYSA-N 0.000 claims abstract description 13
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims abstract description 11
- 229910052751 metal Inorganic materials 0.000 claims abstract description 10
- 239000002184 metal Substances 0.000 claims abstract description 10
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical group [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims abstract description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 8
- 239000001257 hydrogen Substances 0.000 claims abstract description 8
- 229910052763 palladium Inorganic materials 0.000 claims abstract description 4
- 238000000034 method Methods 0.000 claims description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract description 5
- 150000001875 compounds Chemical class 0.000 abstract description 5
- 239000002994 raw material Substances 0.000 abstract description 5
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 abstract description 3
- 229910052707 ruthenium Inorganic materials 0.000 abstract description 3
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 abstract description 2
- 230000015572 biosynthetic process Effects 0.000 abstract description 2
- 229910052731 fluorine Inorganic materials 0.000 abstract description 2
- 239000011737 fluorine Substances 0.000 abstract description 2
- 238000003786 synthesis reaction Methods 0.000 abstract description 2
- 238000010438 heat treatment Methods 0.000 abstract 2
- 239000003863 metallic catalyst Substances 0.000 abstract 2
- 239000002904 solvent Substances 0.000 abstract 2
- 239000003125 aqueous solvent Substances 0.000 abstract 1
- 229910052799 carbon Inorganic materials 0.000 abstract 1
- 238000004821 distillation Methods 0.000 abstract 1
- 229910000765 intermetallic Inorganic materials 0.000 abstract 1
- 229920000642 polymer Polymers 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 2
- 239000010948 rhodium Substances 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- 239000011701 zinc Substances 0.000 description 2
- AJDIZQLSFPQPEY-UHFFFAOYSA-N 1,1,2-Trichlorotrifluoroethane Chemical compound FC(F)(Cl)C(F)(Cl)Cl AJDIZQLSFPQPEY-UHFFFAOYSA-N 0.000 description 1
- BQCIDUSAKPWEOX-UHFFFAOYSA-N 1,1-Difluoroethene Chemical compound FC(F)=C BQCIDUSAKPWEOX-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 229910021639 Iridium tetrachloride Inorganic materials 0.000 description 1
- 101100030361 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) pph-3 gene Proteins 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 229910021120 PdC12 Inorganic materials 0.000 description 1
- 229910019029 PtCl4 Inorganic materials 0.000 description 1
- 229910019891 RuCl3 Inorganic materials 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 229920002313 fluoropolymer Polymers 0.000 description 1
- 239000004811 fluoropolymer Substances 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 229910052762 osmium Inorganic materials 0.000 description 1
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 description 1
- RFLFDJSIZCCYIP-UHFFFAOYSA-L palladium(2+);sulfate Chemical compound [Pd+2].[O-]S([O-])(=O)=O RFLFDJSIZCCYIP-UHFFFAOYSA-L 0.000 description 1
- GPNDARIEYHPYAY-UHFFFAOYSA-N palladium(II) nitrate Inorganic materials [Pd+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O GPNDARIEYHPYAY-UHFFFAOYSA-N 0.000 description 1
- 229910000364 palladium(II) sulfate Inorganic materials 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- YBCAZPLXEGKKFM-UHFFFAOYSA-K ruthenium(iii) chloride Chemical compound [Cl-].[Cl-].[Cl-].[Ru+3] YBCAZPLXEGKKFM-UHFFFAOYSA-K 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- FBEIPJNQGITEBL-UHFFFAOYSA-J tetrachloroplatinum Chemical compound Cl[Pt](Cl)(Cl)Cl FBEIPJNQGITEBL-UHFFFAOYSA-J 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Description
゛本発明は、トリフルオロエチレンをクロロトリフルオ
ロエチレンから選択的に製造することにある。゛The present invention is to selectively produce trifluoroethylene from chlorotrifluoroethylene.
本発明により製造されるトリフルオロエチレンは、近年
、フッ素化学の進展に伴いフッ素高分子合成分野におい
て非常に重要視される化合物に成長した０例えば、ビニ
リデンフルオライドとトリフルオロエチレンの共重合体
は、電気的、機械的作用により応答を示す良好な高分子
圧電体であり、ヘッドフオンスピーカーあるいは圧電型
キーボードの変換素子として実用化が検討されている。Trifluoroethylene produced by the present invention has recently grown into a compound that has become very important in the field of fluoropolymer synthesis with the progress of fluorine chemistry.For example, a copolymer of vinylidene fluoride and trifluoroethylene , a polymeric piezoelectric material that exhibits good response due to electrical and mechanical effects, is being considered for practical use as a conversion element for headphone speakers or piezoelectric keyboards.
従来、トリフルオロエチレンを製造する方法としては、
クロロトリフルオロエチレンと臭化水素とを反応させた
後、亜鉛を用いメタノール中で脱ハロゲン化して得る方
法が知られている（Ｊ、Ａｍ、 Ｃｈｅｍ、’ Ｓｏｓ
、、 ７３．２３３９（１９４９）及びＪ、Ａｍ。
Ｃｈｅｗ、 Ｓｏｃ、、 ７３．７１１（ｔ９５１）
参照〕。Conventionally, the methods for producing trifluoroethylene are as follows:
A method is known in which chlorotrifluoroethylene is reacted with hydrogen bromide and then dehalogenated in methanol using zinc (J, Am, Chem, 'Sos
, 73.2339 (1949) and J. Am. Chew, Soc, 73.711 (t951)
reference〕.
しかしながら、従来の方法は、クロロトリフルオロエチ
レンから５０％近い収率でトリフル才口エチレンを得る
ことができるが、クロロトリフルオロエチレンから二工
程を必要とし、操作が繁雑である。また、非常に高価な
臭化水素を用いていることが欠点である。このためより
簡便かつ安価にトリフルオロエチレンを製造する方法の
開発が強く望まれていた。However, although the conventional method can obtain trifluoroethylene with a yield of nearly 50% from chlorotrifluoroethylene, it requires two steps from chlorotrifluoroethylene and is complicated to operate. Another drawback is that it uses very expensive hydrogen bromide. Therefore, there has been a strong desire to develop a method for producing trifluoroethylene more simply and inexpensively.
本発明者等は、従来の欠点を克服すべく検討した結果、
クロロトリフルオロエチレンを原料に収率よく一段でト
リフルオロエチレンを製造できる方法を見出し本発明を
完成した。As a result of studies to overcome the conventional drawbacks, the inventors of the present invention found that
The present invention was completed by discovering a method for producing trifluoroethylene in one step with good yield from chlorotrifluoroethylene as a raw material.
本発明は、第■族白金族金属触媒の存在下、クロロトリ
フルオロエチレンと水素とを反応させることにより、ト
リフルオロエチレンを製造するものである。
本発明の原料であるクロロトリフルオロエチレンは、１
，１．２−トリクロロ−１，２，２−トリフルオロエタ
ンをメタノール中、亜鉛あるいはナトリウム存在下に処
理することにより容易に得られる化合物である。
本発明は、第■族白金族金属触媒の存在下に行うことを
必須の要件とする。第■族白金族金属触媒としては、白
金、パラジウム、ロジウム、イリジウム、ルテニウム、
オスミウムを使用することができる。これらの金属は、
例えば、Ｐｄ（ＮＯ３）２゜Ｐｄ（ＣＨ３（００）２．
ＰｄＳＯ４，ＰｄＣ１２，Ｋ２ＰｄＣＩ４． Ｎａ２
ＰｄＣ１４゜（Ｎ１１４）２ＰｄＣ１４，Ｐｄ（ＰＰｈ
３）２Ｃ１２，ＲｕＣｌ３． ＲｕＢｒ３゜Ｒｕｃ１２
（ＯＨ）、ＰｔＣｌ４，１ｔ２ＰｔＣ１６，に２ＰｔＣ
１４，０３ＣＩ３゜（Ｎｕｔ４）３ＲｈＣ１６，ＲｈＣ
ｌ３．Ｒｈ（ＮＯ３）３．ＩｒＣｌ４．Ｈａ２ＩｒＣ１
６等の化合物を使用し、担体担持して用いることができ
る。前記した金属触媒のうち、殊に、高収率で目的物を
得るにはパラジウム又はルテニウムの使用が好ましい、
金属の担持量は、０．０５％以上であるならば目的とす
るトリフルオロエチレンが好収率で得られるが、収率よ
く経済的にトリフルオロエチレンを得るには、０．１〜
５％の範囲が好ましい。
本触媒に使用できる担体としては、活性炭、アルミナ等
を例示することができる０本触媒は、前処理し、更に水
素で加熱還元処理することにより調製することができる
０以上のごとくして得られた触媒は、以下に述べる条件
下に使用するものである。
本発明は、前記記載の方法により調製された触媒の存在
下、クロロトリフルオロエチレンと水素とを反応させる
ことにより、トリフルオロエチレンを製造することがで
きる。原料の導入にあたっては、クロロトリフルオロエ
チレンと水素とのモル比を１：１〜２０の範囲で導入す
るが、好事よく反応を行うにはそのモル比は、１：２〜
７の範囲が好ましい。触媒に対する原料の空間速度は、
５０〜１０００ｈｒ’の範囲を選択することができるが
、目的物を効率よく得るには１００〜５００ｈｒ’の範
囲が好ましい。
反応温度は、使用する触媒・の活性や空間速度等に依存
して適宜状められるが、通常は、５０〜３００℃の範囲
で円滑に反応が進行する。
尚、反応に供した触媒は、再度還元処理を行うことによ
り、再使用が可能である。
以下、実施例により本発明を更に詳細に説明する。
実施例 １
水１００ｃｃ及び１−Ｎ硝酸１００ｃｃにＰｄ（ＮＯ３
）２１ｇを溶解させ、活性炭１００ｇを浸漬させた。
浸漬後、水と硝酸をロータリーエバポレーターを用い除
去し、反応管に入れ更に窒素気流中、１００℃で１時間
還元処理した後、以下の実施例に示す反応に使用した。
尚、反応器の内容積は、９５ｃｃである。
実施例２〜９
実施例１と同様の方法で触媒を調製した。その結果を表
１に示した。
実施例 １０〜１８
実施例１〜９で得られた触媒を用いてトリフルオロエチ
レンの合成を行った。その結果を表２に示した。同様に
他の触媒について行った結果を表２に合わせて記載した
。The present invention is to produce trifluoroethylene by reacting chlorotrifluoroethylene with hydrogen in the presence of a Group (I) platinum group metal catalyst. The raw material of the present invention, chlorotrifluoroethylene, has 1
, 1,2-trichloro-1,2,2-trifluoroethane in methanol in the presence of zinc or sodium. The present invention requires that the reaction be carried out in the presence of a Group (I) platinum group metal catalyst. Group III platinum group metal catalysts include platinum, palladium, rhodium, iridium, ruthenium,
Osmium can be used. These metals are
For example, Pd(NO3)2°Pd(CH3(00)2.
PdSO4, PdC12, K2PdCI4. Na2
PdC14゜(N114)2PdC14,Pd(PPh
3) 2C12, RuCl3. RuBr3゜Ruc12
(OH), PtCl4, 1t2PtC16, 2PtC
14,03CI3゜(Nut4)3RhC16,RhC
l3. Rh(NO3)3. IrCl4. Ha2IrC1
A compound such as No. 6 can be used and supported on a carrier. Among the metal catalysts mentioned above, it is particularly preferable to use palladium or ruthenium in order to obtain the target product in high yield.
If the amount of metal supported is 0.05% or more, the desired trifluoroethylene can be obtained in a good yield, but in order to economically obtain trifluoroethylene with a good yield, it is necessary to
A range of 5% is preferred. Examples of carriers that can be used for this catalyst include activated carbon and alumina.The catalyst can be prepared by pretreatment and further heat reduction treatment with hydrogen. The catalyst was used under the conditions described below. In the present invention, trifluoroethylene can be produced by reacting chlorotrifluoroethylene with hydrogen in the presence of a catalyst prepared by the method described above. When introducing the raw materials, the molar ratio of chlorotrifluoroethylene to hydrogen is introduced in the range of 1:1 to 20, but for a successful reaction, the molar ratio should be 1:2 to 20.
A range of 7 is preferred. The space velocity of the feedstock relative to the catalyst is
Although a range of 50 to 1000 hr' can be selected, a range of 100 to 500 hr' is preferable in order to efficiently obtain the desired product. The reaction temperature is determined as appropriate depending on the activity and space velocity of the catalyst used, but the reaction usually proceeds smoothly within the range of 50 to 300°C. Note that the catalyst used in the reaction can be reused by performing reduction treatment again. Hereinafter, the present invention will be explained in more detail with reference to Examples. Example 1 Pd(NO3
) was dissolved and 100 g of activated carbon was immersed. After immersion, water and nitric acid were removed using a rotary evaporator, and the sample was placed in a reaction tube and further subjected to reduction treatment at 100° C. for 1 hour in a nitrogen stream, and then used in the reactions shown in the following examples. Note that the internal volume of the reactor was 95 cc. Examples 2-9 Catalysts were prepared in the same manner as in Example 1. The results are shown in Table 1. Examples 10-18 Trifluoroethylene was synthesized using the catalysts obtained in Examples 1-9. The results are shown in Table 2. Similarly, results for other catalysts are also shown in Table 2.
Claims (2)
ルオロエチレンと水素とを反応 させることからなる、トリフルオロエチ レンの製造方法。(1) A method for producing trifluoroethylene, which comprises reacting chlorotrifluoroethylene with hydrogen in the presence of a Group VIII platinum group metal catalyst.
特許請求の範囲第（１）項に記 載の方法。(2) the Group VIII platinum group metal catalyst is palladium;
A method according to claim (1).
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP61093414A JPS62252736A (en) | 1986-04-24 | 1986-04-24 | Production of trifluoroethylene |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP61093414A JPS62252736A (en) | 1986-04-24 | 1986-04-24 | Production of trifluoroethylene |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS62252736A true JPS62252736A (en) | 1987-11-04 |
Family
ID=14081638
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP61093414A Pending JPS62252736A (en) | 1986-04-24 | 1986-04-24 | Production of trifluoroethylene |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS62252736A (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH07265717A (en) * | 1994-03-31 | 1995-10-17 | Tokuyama Corp | Regeneration of hydrogen reducing reaction catalyst of organic chlorinated substance |
| EP1789373A2 (en) * | 2004-08-26 | 2007-05-30 | PCBU Services, Inc. | Chemical production processes and systems |
| US20140303411A1 (en) * | 2010-07-01 | 2014-10-09 | Solvay Specialty Polymers Italy S.P.A. | Process for the synthesis of trifluoroethylene |
| JP2015513545A (en) * | 2012-02-28 | 2015-05-14 | アルケマ フランス | Method for the synthesis of trifluoroethylene from chlorotrifluoroethylene |
| CN116120146A (en) * | 2022-08-18 | 2023-05-16 | 浙江省化工研究院有限公司 | Production method and system of hexafluorobutadiene |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS57122021A (en) * | 1980-12-09 | 1982-07-29 | Airando Corp | Prescription of chlorotrifluoroethylene and trifluoroethylene |
-
1986
- 1986-04-24 JP JP61093414A patent/JPS62252736A/en active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS57122021A (en) * | 1980-12-09 | 1982-07-29 | Airando Corp | Prescription of chlorotrifluoroethylene and trifluoroethylene |
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH07265717A (en) * | 1994-03-31 | 1995-10-17 | Tokuyama Corp | Regeneration of hydrogen reducing reaction catalyst of organic chlorinated substance |
| EP1789373A2 (en) * | 2004-08-26 | 2007-05-30 | PCBU Services, Inc. | Chemical production processes and systems |
| EP1789373A4 (en) * | 2004-08-26 | 2009-01-21 | Great Lakes Chemical Corp | Chemical production processes and systems |
| US7884255B2 (en) | 2004-08-26 | 2011-02-08 | Vicki Hedrick | Chemical production processes and systems |
| US20140303411A1 (en) * | 2010-07-01 | 2014-10-09 | Solvay Specialty Polymers Italy S.P.A. | Process for the synthesis of trifluoroethylene |
| US9403742B2 (en) * | 2010-07-01 | 2016-08-02 | Solvay Specialty Polymers Italy S.P.A. | Process for the synthesis of trifluoroethylene |
| JP2015513545A (en) * | 2012-02-28 | 2015-05-14 | アルケマ フランス | Method for the synthesis of trifluoroethylene from chlorotrifluoroethylene |
| CN116120146A (en) * | 2022-08-18 | 2023-05-16 | 浙江省化工研究院有限公司 | Production method and system of hexafluorobutadiene |
| CN116120146B (en) * | 2022-08-18 | 2024-01-16 | 浙江省化工研究院有限公司 | Production method and system of hexafluorobutadiene |
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