JPH0413638A - Preparation of trifluorochloroethylene - Google Patents
Preparation of trifluorochloroethyleneInfo
- Publication number
- JPH0413638A JPH0413638A JP2113542A JP11354290A JPH0413638A JP H0413638 A JPH0413638 A JP H0413638A JP 2113542 A JP2113542 A JP 2113542A JP 11354290 A JP11354290 A JP 11354290A JP H0413638 A JPH0413638 A JP H0413638A
- Authority
- JP
- Japan
- Prior art keywords
- catalyst
- group
- hydrogen
- trichloro
- weight
- 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
- UUAGAQFQZIEFAH-UHFFFAOYSA-N chlorotrifluoroethylene Chemical group FC(F)=C(F)Cl UUAGAQFQZIEFAH-UHFFFAOYSA-N 0.000 title description 6
- 239000003054 catalyst Substances 0.000 claims abstract description 30
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 11
- 239000001257 hydrogen Substances 0.000 claims abstract description 11
- 229910052763 palladium Inorganic materials 0.000 claims abstract description 11
- AJDIZQLSFPQPEY-UHFFFAOYSA-N 1,1,2-Trichlorotrifluoroethane Chemical compound FC(F)(Cl)C(F)(Cl)Cl AJDIZQLSFPQPEY-UHFFFAOYSA-N 0.000 claims abstract description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 9
- 229910052709 silver Inorganic materials 0.000 claims abstract description 9
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 16
- 238000004519 manufacturing process Methods 0.000 claims description 8
- 239000004332 silver Substances 0.000 claims description 6
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 2
- 239000005977 Ethylene Substances 0.000 claims description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract description 15
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 abstract description 6
- 238000000034 method Methods 0.000 abstract description 6
- 239000002994 raw material Substances 0.000 abstract description 4
- 238000002844 melting Methods 0.000 abstract description 2
- 230000008018 melting Effects 0.000 abstract description 2
- 239000000126 substance Substances 0.000 abstract 2
- 229910052799 carbon Inorganic materials 0.000 abstract 1
- 125000001153 fluoro group Chemical group F* 0.000 abstract 1
- 229920005989 resin Polymers 0.000 abstract 1
- 239000011347 resin Substances 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 4
- 239000007789 gas Substances 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- MIZLGWKEZAPEFJ-UHFFFAOYSA-N 1,1,2-trifluoroethene Chemical group FC=C(F)F MIZLGWKEZAPEFJ-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 229910001961 silver nitrate Inorganic materials 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- UJPMYEOUBPIPHQ-UHFFFAOYSA-N 1,1,1-trifluoroethane Chemical compound CC(F)(F)F UJPMYEOUBPIPHQ-UHFFFAOYSA-N 0.000 description 1
- 235000013162 Cocos nucifera Nutrition 0.000 description 1
- 244000060011 Cocos nucifera Species 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- HUVUPOLYFFAVIJ-UHFFFAOYSA-N barium(2+) chromium(3+) manganese(2+) oxocopper oxygen(2-) Chemical compound [O-2].[Mn+2].[O-2].[Ba+2].[O-2].[Cr+3].[Cu]=O HUVUPOLYFFAVIJ-UHFFFAOYSA-N 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- QPAXMPYBNSHKAK-UHFFFAOYSA-N chloro(difluoro)methane Chemical compound F[C](F)Cl QPAXMPYBNSHKAK-UHFFFAOYSA-N 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000006298 dechlorination reaction Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 239000010903 husk Substances 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- SWELZOZIOHGSPA-UHFFFAOYSA-N palladium silver Chemical compound [Pd].[Ag] SWELZOZIOHGSPA-UHFFFAOYSA-N 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- 239000011592 zinc chloride Substances 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
【発明の詳細な説明】
［産業上の利用分野］
本発明は、フッ素樹脂等の原料として有用な三フッ化塩
化エチレン（以下ＣＴＦＥと略記する。）の製造法に関
するものである。DETAILED DESCRIPTION OF THE INVENTION [Industrial Application Field] The present invention relates to a method for producing trifluorochloroethylene (hereinafter abbreviated as CTFE), which is useful as a raw material for fluororesins and the like.
［従来技術］
従来、工業的なＣＴＦＥの製造法としては、１１．２−
トリクロロ−１，２，２−）リフルオロエタン（以下Ｃ
ＦＣ−１１３と記す。）を亜鉛により脱塩素する液相法
（特公昭４７−４５３２２号、特公昭５７−５２０７、
特公昭５７−５２０８号）がおこなわれている。しかし
、これらの方法は反応操作が複雑でかつ製造コストが高
くなり、さらに副生ずる塩化亜鉛の処理等のｖＵＢ点が
ある。その解決方法として、触媒を用いてＣＦＣ−１１
３を水素により気相で還元する方法が提案されており、
ヤシガラ炭等の活性炭触媒上で、反応温度４００〜６０
０℃で製造する方法（特公昭６３−４６０４９号）、銅
酸化物−クロム酸化物−バリウム酸化物−マンガン酸化
物触媒上で、反応温度２００〜３００℃で製造する方法
（特公昭６４−２９３２８号）がある。しかし、触媒寿
命の観点から、より工業的な触媒としては耐酸性に強い
パラジウム、白金等の貴金属触媒の適用が望まれるが、
例えばパラジウムのみを担体に担持した触媒を用いて、
ＣＦＣ−１１３を水素で還元すると、目的とするＣＴＦ
Ｅは殆ど生成せず、三フッ化エチレンを主に生成するた
めに困難であった。（特公昭４３−８４５４号）。[Prior Art] Conventionally, as an industrial method for manufacturing CTFE, 11.2-
Trichloro-1,2,2-)trifluoroethane (hereinafter referred to as C
It is written as FC-113. ) using zinc for dechlorination (Japanese Patent Publication No. 47-45322, Japanese Patent Publication No. 57-5207,
Special Publication No. 57-5208) was carried out. However, these methods require complicated reaction operations and high production costs, and also have vUB points such as processing of zinc chloride produced as a by-product. As a solution to this problem, using a catalyst, CFC-11
A method has been proposed in which 3 is reduced in the gas phase with hydrogen,
On an activated carbon catalyst such as coconut husk charcoal, the reaction temperature is 400 to 60℃.
A method for producing at 0°C (Japanese Patent Publication No. 63-46049), a method for producing at a reaction temperature of 200 to 300°C over a copper oxide-chromium oxide-barium oxide-manganese oxide catalyst (Japanese Patent Publication No. 64-29328) No.). However, from the viewpoint of catalyst life, it is desirable to use noble metal catalysts such as palladium and platinum, which have strong acid resistance, as more industrial catalysts.
For example, using a catalyst in which only palladium is supported on a carrier,
When CFC-113 is reduced with hydrogen, the desired CTF
E was hardly produced, and it was difficult to produce mainly trifluoroethylene. (Special Publication No. 43-8454).
［問題点を解決するための手段］
本発明者らはかかる従来技術の問題点に鑑み、鋭意検討
の結果、耐ハロゲン性の強いパラジウムに銀を添加した
触媒を用いて、ＣＦＣ−１１３を水素で還元すると、低
温で、かつ選択的にＣＴＦＥが生成することを見出し、
本発明に到達した。[Means for Solving the Problems] In view of the problems of the prior art, the present inventors conducted extensive studies and found that CFC-113 can be converted into hydrogen by using a catalyst made by adding silver to palladium, which has strong halogen resistance. discovered that CTFE was selectively produced at low temperatures when reduced with
We have arrived at the present invention.
すなわち本発明は１，１．２−トリクロロ−１，２，２
−）リフルオロエタンをパラジウムおよび銀を必須成分
とする触媒の存在下水素で還元することを特徴とする三
フッ化塩化エチレンの製造法である。That is, the present invention provides 1,1,2-trichloro-1,2,2
-) A method for producing ethylene trifluorochloride, which is characterized by reducing refluoroethane with hydrogen in the presence of a catalyst containing palladium and silver as essential components.
パラジウム−銀系触媒は活性炭、アルミナ、チタニア等
の種々の担体が使用可能であるが活性炭、アルミナが推
奨される。担体重量に対するパラジウムの担持量は０．
０１〜１０重量％、好ましくは０．１〜５重量％の範囲
のものが推奨される。Various carriers such as activated carbon, alumina, and titania can be used for the palladium-silver catalyst, but activated carbon and alumina are recommended. The amount of palladium supported relative to the carrier weight is 0.
A range of 0.01 to 10% by weight, preferably 0.1 to 5% by weight is recommended.
銀の担持量は１〜３０重量％、好ましくは５〜２５重量
％のものが推奨される。The amount of silver supported is recommended to be 1 to 30% by weight, preferably 5 to 25% by weight.
担持方法としてはパラジウムと銀を同時に担持させても
、２回に分けて別々に担持させてもよい。As for the supporting method, palladium and silver may be supported simultaneously or separately in two steps.
また触媒寿命および選択率をさらに向上させるためにｉ
［ａ族、ＩＶａ族、Ｖａ族、ＶＩａ族、■ａ族、■族、
Ｉｂ族の融点が１０００℃以上の一種または二種以上の
元素（ただし、パラジウム、銀を除（）を添加するのを
妨げない。In order to further improve catalyst life and selectivity, i
[Group a, Group IVa, Group Va, Group VIa, Group ■a, Group ■,
One or more elements of group Ib having a melting point of 1000° C. or higher (excluding palladium and silver) may be added.
水素の使用量は原料のＣＦＣ−１１３に対しで０．５〜
４倍モル量の範囲が好ましく、より好ましくは等モル−
３倍モルの範囲である。また、所望により窒素等の不活
性ガスで希釈してもよい。The amount of hydrogen used is 0.5 to 0.5 to the raw material CFC-113.
A range of 4 times the molar amount is preferred, more preferably an equimolar amount.
The range is 3 times the mole. Further, it may be diluted with an inert gas such as nitrogen if desired.
反応温度は転化率、選択率および触媒活性の寿命に関係
するが５０〜４００℃、より好ましくは２００〜３００
℃の範囲が推奨される。この範囲より低い場合には転化
率が低く、この範囲を越えると選択率が低下する。反応
は気相、液相のいずれでもおこなえ、反応圧力としては
常圧または常圧以上の圧力を使用し得る。気相で反応を
おこなう場合の接触時間としては０．１秒から３００秒
の範囲が適用できるが、好ましくは５〜１００秒の範囲
である。The reaction temperature is related to conversion rate, selectivity and catalyst activity life, but is preferably 50 to 400°C, more preferably 200 to 300°C.
°C range is recommended. If it is lower than this range, the conversion rate will be low, and if it exceeds this range, the selectivity will decrease. The reaction can be carried out in either a gas phase or a liquid phase, and the reaction pressure can be normal pressure or a pressure higher than normal pressure. When the reaction is carried out in the gas phase, the contact time can range from 0.1 seconds to 300 seconds, preferably from 5 to 100 seconds.
以下、実施例により本発明の詳細な説明する。Hereinafter, the present invention will be explained in detail with reference to Examples.
調整例１
活性炭と同体積の純水中に硝Ｍ銀を金属成分の重量とし
て活性炭重量の１０％を溶解させた。この溶液中に活性
炭を１２時間浸漬させた後、活性炭を濾過し、水分を蒸
発乾燥させた。この触媒を４００℃において４時間焼成
した。Preparation Example 1 In pure water of the same volume as activated carbon, 10% of the weight of activated carbon was dissolved in silver nitrate as a metal component. After immersing the activated carbon in this solution for 12 hours, the activated carbon was filtered and water was evaporated to dryness. This catalyst was calcined at 400°C for 4 hours.
調整例２
１１１ＨＦ１１で１ｉｌｌた触媒と同体積の純水中（９
０℃）に、塩化パラジウムを金属成分の重量として触媒
重量の１％だけ溶解させ、塩酸を少量加えてｐＨを調節
した。Preparation Example 2 1ill of 111HF11 and the same volume of pure water (9
(0°C), palladium chloride was dissolved in an amount of 1% of the weight of the catalyst based on the weight of the metal component, and a small amount of hydrochloric acid was added to adjust the pH.
この溶液に調整例１で調整した触媒を１２時間浸漬させ
た後、水分を蒸発乾燥させ、４時間４００℃で焼成した
。After the catalyst prepared in Preparation Example 1 was immersed in this solution for 12 hours, water was evaporated to dryness, and the catalyst was calcined at 400° C. for 4 hours.
調製例３
γ−アルミナと、同体積の純水中に硝酸銀を金属成分の
重量としてアルミナ重量の５％を溶解させた。この溶液
にアルミナを１２時間浸漬させた後、水分を蒸発乾燥さ
せ、４時間４００℃で焼成した。Preparation Example 3 In pure water of the same volume as γ-alumina, silver nitrate was dissolved in an amount of 5% of the weight of the alumina based on the weight of the metal component. After immersing alumina in this solution for 12 hours, the water was evaporated to dryness and calcined at 400° C. for 4 hours.
８１１例４
ｓｉｎ例３でＩｉｌした触媒と同体積の純水中（９０℃
）に、塩化パラジウムを金属成分の重量として触媒重量
の１％だけ溶解させ、塩酸を少量加えてｐＨを調節した
。811 Example 4 In the same volume of pure water (90℃
), palladium chloride was dissolved in an amount of 1% of the weight of the catalyst based on the weight of the metal component, and a small amount of hydrochloric acid was added to adjust the pH.
この溶液に調製例３で調製した触媒を１２時間浸漬させ
た後、水分を蒸発乾燥させ、４時間４００℃で焼成した
。After the catalyst prepared in Preparation Example 3 was immersed in this solution for 12 hours, water was evaporated to dryness, and the catalyst was calcined at 400° C. for 4 hours.
実施例１
ｔ１Ｍ整例２て調製した触媒５Ｑｃｃおよび触媒層の前
後に各５Ｑｃｃの４ ｍ ｍφガラスピーズを充填した
内径２．５ｃｍ、長さ４０ｃｍの石英製反応管に水素を
流しながら電気炉を用い加熱した。Example 1 An electric furnace was heated while flowing hydrogen into a quartz reaction tube with an inner diameter of 2.5 cm and a length of 40 cm filled with 5 Qcc of the catalyst prepared in t1M Preparation Example 2 and 5 Qcc of 4 mm diameter glass beads before and after the catalyst layer. and heated.
３００℃で１２時間水素で触媒を還元した後、２００℃
まで冷却し、ＣＦＣ−１１３と水素をそれぞれ４０ｃｃ
／分、６０ ｃ ｃ／分の流量で予熱器械を介して反応
管に導入した。反応温度を２７５℃、接触時間３０秒に
した時の結果を第１表に示す。After reducing the catalyst with hydrogen at 300°C for 12 hours, the catalyst was reduced to 200°C.
Cool to 40cc each of CFC-113 and hydrogen.
/min, 60 cc/min into the reaction tube via the preheating device. Table 1 shows the results when the reaction temperature was 275°C and the contact time was 30 seconds.
実施例２
反応温度を２５０℃とするほかは実施例１と同様にして
反応をおこなった。この結果を第１表に示した。Example 2 A reaction was carried out in the same manner as in Example 1 except that the reaction temperature was 250°C. The results are shown in Table 1.
実施例３
ＣＦＣ−１１３と水素の供給量をそれぞれ４０ｃｃ／分
、１２０ｃｃ／分および接触時間１９秒とするほかは実
施例２と同様にして反応をおこなった。この結果を第１
表に示した。Example 3 A reaction was carried out in the same manner as in Example 2, except that the supply rates of CFC-113 and hydrogen were 40 cc/min and 120 cc/min, respectively, and the contact time was 19 seconds. This result is the first
Shown in the table.
実施例４
調製例４で調製した触媒を用いることおよび反応温度を
２４０℃とするほかは実施例１と同様にして反応をおこ
なった。この結果を第１表に示した。Example 4 A reaction was carried out in the same manner as in Example 1, except that the catalyst prepared in Preparation Example 4 was used and the reaction temperature was 240°C. The results are shown in Table 1.
第１表から明らかなとおり本発明によれば目的のＣＴＦ
Ｅを選択率よく製造できるものであり、反応操作も簡単
であり工業的に優れた方法である。As is clear from Table 1, according to the present invention, the target CTF
E can be produced with high selectivity, the reaction operation is simple, and it is an industrially excellent method.
第１表 表中の各記号は次の化合物を示す。Table 1 Each symbol in the table represents the following compound.
ＣＴＦＥ： ＣＨＦ＝ＣＦ２
ＴｒＦＥ： ＣＨＦ＝ＣＦ２
Ｒ−１２３ａ ： ＣＣｌＦ２ ＣＨＣＩＦ［発明の効
果］
本発明の方法によれば、フッ素樹脂の原料等として工業
的に重要な三フッ化エチレンを高選択率で製造すること
ができるものである。CTFE: CHF=CF2 TrFE: CHF=CF2 R-123a: CClF2 CHCIF [Effects of the invention] According to the method of the present invention, trifluoroethylene, which is industrially important as a raw material for fluororesins, can be produced with high selectivity. It is something that can be done.
Claims (1)
タンをパラジウムおよび銀を必須成分とする触媒の存在
下水素で還元することを特徴とする三フッ化塩化エチレ
ンの製造法。A method for producing ethylene trifluorochloride, which comprises reducing 1,1,2-trichloro-1,2,2-trifluoroethane with hydrogen in the presence of a catalyst containing palladium and silver as essential components.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2113542A JPH0413638A (en) | 1990-04-27 | 1990-04-27 | Preparation of trifluorochloroethylene |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2113542A JPH0413638A (en) | 1990-04-27 | 1990-04-27 | Preparation of trifluorochloroethylene |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH0413638A true JPH0413638A (en) | 1992-01-17 |
Family
ID=14614955
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2113542A Pending JPH0413638A (en) | 1990-04-27 | 1990-04-27 | Preparation of trifluorochloroethylene |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0413638A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH04117333A (en) * | 1990-05-31 | 1992-04-17 | Daikin Ind Ltd | Production of 1-chloro-1,2,-trifluoroethylene and 1,2,2-trifluoroethylene |
| KR100761553B1 (en) * | 2005-04-06 | 2007-09-27 | 스템코 주식회사 | Reel transference system |
| US7473810B1 (en) | 2007-10-12 | 2009-01-06 | Honeywell International Inc. | Method of dechlorinating organic compounds comprising vicinal chlorides |
-
1990
- 1990-04-27 JP JP2113542A patent/JPH0413638A/en active Pending
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH04117333A (en) * | 1990-05-31 | 1992-04-17 | Daikin Ind Ltd | Production of 1-chloro-1,2,-trifluoroethylene and 1,2,2-trifluoroethylene |
| KR100761553B1 (en) * | 2005-04-06 | 2007-09-27 | 스템코 주식회사 | Reel transference system |
| US7473810B1 (en) | 2007-10-12 | 2009-01-06 | Honeywell International Inc. | Method of dechlorinating organic compounds comprising vicinal chlorides |
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