JPH01301631A - Production of 1,1,1,3,3,3-hexafluoropropan-2-ol - Google Patents
Production of 1,1,1,3,3,3-hexafluoropropan-2-olInfo
- Publication number
- JPH01301631A JPH01301631A JP63131455A JP13145588A JPH01301631A JP H01301631 A JPH01301631 A JP H01301631A JP 63131455 A JP63131455 A JP 63131455A JP 13145588 A JP13145588 A JP 13145588A JP H01301631 A JPH01301631 A JP H01301631A
- Authority
- JP
- Japan
- Prior art keywords
- hydrogen
- hydrate
- reaction
- hfa
- alumina
- 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
- 238000004519 manufacturing process Methods 0.000 title claims description 7
- BYEAHWXPCBROCE-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropan-2-ol Chemical compound FC(F)(F)C(O)C(F)(F)F BYEAHWXPCBROCE-UHFFFAOYSA-N 0.000 title abstract 2
- 239000003054 catalyst Substances 0.000 claims abstract description 20
- 239000001257 hydrogen Substances 0.000 claims abstract description 20
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 20
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 18
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims abstract description 18
- 229910052763 palladium Inorganic materials 0.000 claims abstract description 9
- 239000007791 liquid phase Substances 0.000 claims abstract description 8
- 238000007327 hydrogenolysis reaction Methods 0.000 claims abstract description 6
- HEBNOKIGWWEWCN-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropan-2-one;hydrate Chemical compound O.FC(F)(F)C(=O)C(F)(F)F HEBNOKIGWWEWCN-UHFFFAOYSA-N 0.000 claims abstract description 4
- VBZWSGALLODQNC-UHFFFAOYSA-N hexafluoroacetone Chemical compound FC(F)(F)C(=O)C(F)(F)F VBZWSGALLODQNC-UHFFFAOYSA-N 0.000 abstract description 26
- 238000000034 method Methods 0.000 abstract description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 5
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 abstract description 4
- 150000001875 compounds Chemical class 0.000 abstract description 3
- 239000002994 raw material Substances 0.000 abstract description 3
- 239000003905 agrochemical Substances 0.000 abstract description 2
- 239000003814 drug Substances 0.000 abstract description 2
- 239000003193 general anesthetic agent Substances 0.000 abstract description 2
- 239000002904 solvent Substances 0.000 abstract description 2
- 239000000126 substance Substances 0.000 abstract description 2
- 229940079593 drug Drugs 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 31
- 230000007423 decrease Effects 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 239000007789 gas Substances 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 101000843477 Escherichia coli (strain K12) RNA-binding protein Hfq Proteins 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000005984 hydrogenation reaction Methods 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 229940035674 anesthetics Drugs 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000004517 catalytic hydrocracking Methods 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 238000002144 chemical decomposition reaction Methods 0.000 description 1
- 239000007809 chemical reaction catalyst Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- -1 lithium aluminum hydride Chemical compound 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 231100000167 toxic agent Toxicity 0.000 description 1
- 239000003440 toxic substance Substances 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 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
Abstract
Description
【発明の詳細な説明】
〔産業上の利用分野〕
本発明は１，１．、Ｌ３，３．３−ヘキサフルオロプロ
パン−２−オール（ＨＦＩＰ）の製造法に関する。[Detailed Description of the Invention] [Industrial Application Field] The present invention comprises 1.1. , relates to a method for producing L3,3,3-hexafluoropropan-2-ol (HFIP).
ＨＦＩＰはそれ自体特異な溶解力を有する溶媒として有
用であるばかりでなく麻酔剤の中間体をはじめ医農薬の
中間体および化学製品の中間体としても有用な化合物で
ある。HFIP is a compound that is not only useful as a solvent having a unique dissolving power, but also as an intermediate for anesthetics, pharmaceuticals and agricultural chemicals, and intermediates for chemical products.
＝１−
ＨＦＩＰの公知の製造方法には、■ヘキサフルオロアセ
トン（ＨＦＡ）の水素化ホウ素すｌ・リウム（ソ連特許
第１３８６０４号）あるいは水素化アルミニウムリチウ
ム（米国特許第３２２７６７４号）を用いた液相還元法
、■米国特許第３６０７９５２号に代表されるＨＦＡを
液相で貴金属触媒の存在下水素化する方法、■ドイツ特
許第１９５６６２９号に代表されるＨＦＡを気相で水素
とともに触媒層を通ずことによる（接触水素化）方法が
ある。=1- Known methods for producing HFIP include: ■ Hexafluoroacetone (HFA) liquid using sulfur borohydride (USSR Patent No. 138604) or lithium aluminum hydride (US Patent No. 3227674); Phase reduction method, ■ A method of hydrogenating HFA in the liquid phase in the presence of a noble metal catalyst, as typified by US Pat. There is a catalytic hydrogenation method.
これらはいずれも原料としてＨＦＡを使用するものであ
るが、ＨＦＡは常温では気体（ｂｐ、−２８°Ｃ）であ
る有毒物質であり、その取扱、貯蔵、運搬等には非常に
注意を要するものである。また、■の方法は工業的な製
造方法とはいえず、また■ではＨＦＡがそれ自体液化ガ
スであるため可及的に、その反応温度でＨＦＡが液相で
あるためには大きな反応圧力が必要であり、反応容器と
しては特殊なものが要求される。■では常圧下連続的に
水素化せしめることが可能であるが、水素化反応が発熱
をともなうため触媒層に熱点を作るなど反応温度の制御
は非常に困難である。充填触媒は活性が経時的に低下す
ることが避けられず、製品の経時的な確認および反応条
件の適性化操作といった煩雑さを免れない。またＨＦＡ
の十分なる転化を期すためには過剰量の水素を用いるこ
とが一般的であるが、過剰水素の損失は製造コストの上
昇を招き、回収のためには特に装置が必要である。All of these use HFA as a raw material, but HFA is a toxic substance that is a gas (BP, -28°C) at room temperature, and requires extreme care when handling, storing, and transporting it. It is. In addition, method (2) cannot be called an industrial production method, and in (2), HFA itself is a liquefied gas, so in order for HFA to be in a liquid phase at the reaction temperature, a large reaction pressure is required. A special reaction vessel is required. In case (2), it is possible to carry out hydrogenation continuously under normal pressure, but since the hydrogenation reaction generates heat, it is very difficult to control the reaction temperature, such as by creating hot spots in the catalyst layer. The activity of packed catalysts inevitably decreases over time, and it is unavoidable that it is complicated to check the product over time and to optimize the reaction conditions. Also HFA
Although it is common to use an excess amount of hydrogen to ensure sufficient conversion of hydrogen, the loss of excess hydrogen increases production costs and requires special equipment for recovery.
ＨＦＡは液化ガスであり、また毒性を有するため取扱が
難しいが、かかるＨＦＡを用いる不利を克服する方法と
して、ＨＦＡの水和物を用い、気相でニッケル系触媒ま
たはパラジウム系触媒存在下、水素化分解することによ
るＨＦＩＰの製造法については既に本出願人が特開昭５
７−８１４２４号により提案しているところであるが、
しかしこの方法もＨＦ Ａを用いる■における問題点が
そのまま適用される。HFA is difficult to handle because it is a liquefied gas and has toxicity. However, as a method to overcome the disadvantages of using HFA, a hydrate of HFA is used to react with hydrogen in the gas phase in the presence of a nickel-based or palladium-based catalyst. Regarding the production method of HFIP by chemical decomposition, the present applicant has already published Japanese Patent Application Laid-open No. 5
As proposed by No. 7-81424,
However, the problems in (2) using HFA are also applied to this method.
かかる不都合のないＨＦ Ｉ Ｐの製造法として、ＨＦ
Ａの水和物を液相にて炭素担持パラジウム触媒存在下、
水素化分解する方法が提案されており、例えば特開昭５
９−２０４１４２号等に示されている。As a method for producing HF I P without such inconveniences, HF
A hydrate in the liquid phase in the presence of a carbon-supported palladium catalyst,
Hydrogenolysis methods have been proposed, for example, in JP-A-5
No. 9-204142, etc.
本発明者らはＨＦＡ水和物の液相水素化分解の触媒とし
てアルミナ担持パラジウム触媒が特異的に優れた触媒活
性を示すことを見出し本発明に到達したものである。す
なわち本発明はへキサフルオロアセトン水和物を、アル
ミナ担持パラジウム触媒の存在下、液相状態で水素と接
触せしめ水素化分解をおこなうことを特徴とするＬＬＩ
、３，３．３−ヘキサフルオロプロパン−２−オールの
製造法である。本発明においてＨＦＡ水和物とはＨＦＡ
を水に吸収せしめることにより容易に得られ、製造方法
によってはＨＦＡを取り扱うことなく直接製造すること
もできるＨＦＡと水のモル比が約３で１０６°Ｃの低沸
点液状組成物を指すものである。The present inventors have arrived at the present invention by discovering that an alumina-supported palladium catalyst exhibits uniquely excellent catalytic activity as a catalyst for liquid phase hydrogenolysis of HFA hydrate. That is, the present invention provides an LLI characterized in that hexafluoroacetone hydrate is brought into contact with hydrogen in a liquid phase state in the presence of an alumina-supported palladium catalyst to perform hydrogenolysis.
, 3,3.3-hexafluoropropan-2-ol. In the present invention, HFA hydrate refers to HFA
It refers to a low boiling point liquid composition with a molar ratio of HFA and water of about 3 and a temperature of 106°C, which can be easily obtained by absorbing HFA in water, and depending on the production method, it can also be produced directly without handling HFA. be.
本発明において用いる水素化分解触媒はアルミナ担持パ
ラジウム触媒が好ましく、その使用量はＨＦＡ水和物に
対して０．１〜５．０重量％の範囲が好ましく、これよ
り少ないと触媒活性が寸分ではなく、またこれより多く
しても添加量に見合った効果はなく経済的ではない。ア
ルミナ中のパラジウム担持量は通常用いられる０、５〜
５重量％で十分である。また反応温度は６０〜１００
’Ｃの範囲が好ましく、これより低い温度では反応が十
分に進行せず、これより高い場合には生成したＨＦＩＰ
の蒸気圧が大きくなり一定圧力下での水素の分圧が相対
的に低下し、また１００℃以上にしなくとも十分な反応
速度を有しているため、経済的には１００°Ｃ以下が好
ましい。The hydrocracking catalyst used in the present invention is preferably an alumina-supported palladium catalyst, and the amount used is preferably in the range of 0.1 to 5.0% by weight based on the HFA hydrate. Moreover, even if the amount is increased, the effect is not commensurate with the amount added and is not economical. The amount of palladium supported in alumina is usually 0.5~
5% by weight is sufficient. In addition, the reaction temperature is 60 to 100
'C range is preferable; at temperatures lower than this, the reaction does not proceed sufficiently, and at temperatures higher than this, the produced HFIP
The vapor pressure of hydrogen increases, the partial pressure of hydrogen under a constant pressure decreases relatively, and the reaction rate is sufficient even if the temperature does not exceed 100°C, so it is economically preferable to set the temperature below 100°C. .
また、水素圧力は４〜１５ｋｇ／ｃｎ（の範囲が好まし
く、これより小さい場合には反応が進行するに従って生
成したＨ Ｆ ｒ Ｐが反応温度においてかなりの蒸気
圧を有するため相対的に水素圧が減少するため反応速度
が小さくなり、好ましくない。一方水素圧をこれより大
きくすると反応速度は高まるが反応容器に制約が生し、
特にこれより大きくしなくとも十分な反応速度を有して
いるため、必ずしも必要ない。In addition, the hydrogen pressure is preferably in the range of 4 to 15 kg/cn (if it is smaller than this, the H F r P produced as the reaction progresses will have a considerable vapor pressure at the reaction temperature, so the hydrogen pressure will be relatively low). As the hydrogen pressure decreases, the reaction rate decreases, which is undesirable.On the other hand, increasing the hydrogen pressure higher than this increases the reaction rate, but places constraints on the reaction vessel.
In particular, it is not necessary because the reaction rate is sufficient even if it is not made larger than this.
本発明は気液反応であり、攪拌は反応速度に大きな影響
を与え、十分な攪拌をおこなうことが好ましい。The present invention is a gas-liquid reaction, and stirring has a large effect on the reaction rate, so it is preferable to perform sufficient stirring.
ＨＦＡ水和物が十分に反応した時点で加熱および攪拌を
停止し、触媒が反応容器底部に沈降したのち上澄を生成
物として回収する。反応器内には上記の反応生成物の一
部および触媒と水素か残存するが、さらに原料ＨＦＡ水
和物を添加して再度反応をおこなうことができ、触媒、
水素は損失なしに再使用できるとともに改めて反応容器
を水素で置換する操作も省略できる。触媒は反応を繰り
返すことにより漸次活性が低下して（るので通常は毎回
当初使用触媒の１／１０程度補充することにより、毎回
好ましい反応速度および反応生成物を与える。When the HFA hydrate has sufficiently reacted, heating and stirring are stopped, and after the catalyst has settled to the bottom of the reaction vessel, the supernatant is collected as a product. Although some of the above reaction products, catalyst, and hydrogen remain in the reactor, the raw material HFA hydrate can be further added to carry out the reaction again, and the catalyst,
Hydrogen can be reused without loss, and the operation of replacing the reaction vessel with hydrogen again can be omitted. The activity of the catalyst gradually decreases as the reaction is repeated (therefore, by replenishing about 1/10 of the initially used catalyst each time, a desired reaction rate and reaction product can be obtained each time.
本発明においては反応は目的物であるＨ Ｆ Ｉ Ｐや
水あるいはその他年活性な有機溶媒（エーテル、エタノ
ール、メタノール等）中でも実施でき、その他励触媒、
受酸剤としてカーボン、水酸化アルミニウム等を用いる
こともできる。In the present invention, the reaction can be carried out in the target H F I P, water or other active organic solvents (ether, ethanol, methanol, etc.), and can be carried out in the presence of other active catalysts,
Carbon, aluminum hydroxide, etc. can also be used as the acid acceptor.
本発明により製造されるＨＦＩＰは水および場合によっ
ては未反応ＨＦ Ａ水和物、またある場合−〇−
には副生成物との混合物であるが、この粗ＨＦＩＰは通
常の常圧蒸留により収率よく分別精製される。本発明に
おいて反応容器の材質は特に限定されず、ガラス、ガラ
スライニング、フッ素樹脂ライニング、ステンレス鋼な
どが好適である。The HFIP produced by the present invention is a mixture of water and possibly unreacted HF A hydrate, and in some cases by-products, and the crude HFIP can be recovered by conventional atmospheric distillation. It is efficiently fractionated and purified. In the present invention, the material of the reaction vessel is not particularly limited, and glass, glass lining, fluororesin lining, stainless steel, etc. are suitable.
以下実施例を挙げさらに本発明の詳細な説明する。The present invention will be further explained in detail with reference to Examples below.
実施例Ｉ
攪拌装置を備えた２００ｃ ｃ ５ＵＳ−３１６オート
クレープに３０ ｇ （０，］、３６ｍｏｌ）のＨＦＡ
水和物を入れ５％パラジウム−アルミナ担持触媒０．５
重量％を添加した。容器内を水素で置換し油浴にて９５
°Ｃに昇温した。水素圧力を７ ｋｇ ／ ｃｎｌに保
ちマグネチソクスターラにて攪拌を開始すると水素の吸
収が始まった。８時間後に加熱・攪拌を止め分析したと
ころＨＦＡ水和物の反応率は９４．７％、ＨＦＩＰの選
択率は９９゜３％であった。Example I 30 g (0,], 36 mol) of HFA in a 200cc 5US-316 autoclave equipped with a stirrer
Add hydrate and 5% palladium-alumina supported catalyst 0.5
% by weight was added. The inside of the container was replaced with hydrogen and heated to 95% in an oil bath.
The temperature was raised to °C. When the hydrogen pressure was maintained at 7 kg/cnl and stirring was started using a magnetic stirrer, hydrogen absorption began. After 8 hours, heating and stirring were stopped and analysis revealed that the reaction rate of HFA hydrate was 94.7% and the selectivity of HFIP was 99.3%.
実施例２
添加剤として０．１０重量％のカーボン粉末を添加した
ほかは実施例１と同様にして反応をおこなった。反応を
８時間おこなったのち分析したところＨＦＡ水和物の反
応率は９６．３％、ＨＦＩＰの選択率は９９．４％であ
った。Example 2 A reaction was carried out in the same manner as in Example 1 except that 0.10% by weight of carbon powder was added as an additive. After the reaction was carried out for 8 hours, analysis revealed that the reaction rate of HFA hydrate was 96.3% and the selectivity of HFIP was 99.4%.
実施例３
添加剤として０．３０重量％の水酸化アルミニウムを添
加したほかは実施例１と同様にして反応をおこなった。Example 3 A reaction was carried out in the same manner as in Example 1 except that 0.30% by weight of aluminum hydroxide was added as an additive.
反応を８時間おこなったのち分析したところ ＨＦ Ａ
水和物の反応率は９４．３％、ＨＦＩＰの選択率は９９
，３％であった。After 8 hours of reaction, analysis showed that HF A
Hydrate reaction rate is 94.3%, HFIP selectivity is 99
, 3%.
本発明によれば取扱の容易なＨＦＡ水和物から収率よ＜
ＨＦ Ｉ Ｐを得ることができ、触媒の寿命も長く工
業的に優れた方法である。According to the present invention, the yield from HFA hydrate, which is easy to handle, is
It is an industrially excellent method that can yield HF I P and has a long catalyst life.
Claims (1)
ジウム触媒の存在下、液相状態で水素と接触せしめ水素
化分解をおこなうことを特徴とする１，１，１，３，３
，３−ヘキサフルオロプロパン−２−オールの製造法1, 1, 1, 3, 3 characterized in that hexafluoroacetone hydrate is brought into contact with hydrogen in a liquid phase state in the presence of an alumina-supported palladium catalyst to perform hydrogenolysis.
, 3-hexafluoropropan-2-ol manufacturing method
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP63131455A JPH01301631A (en) | 1988-05-31 | 1988-05-31 | Production of 1,1,1,3,3,3-hexafluoropropan-2-ol |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP63131455A JPH01301631A (en) | 1988-05-31 | 1988-05-31 | Production of 1,1,1,3,3,3-hexafluoropropan-2-ol |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH01301631A true JPH01301631A (en) | 1989-12-05 |
Family
ID=15058359
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP63131455A Pending JPH01301631A (en) | 1988-05-31 | 1988-05-31 | Production of 1,1,1,3,3,3-hexafluoropropan-2-ol |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH01301631A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7524995B1 (en) | 2008-06-12 | 2009-04-28 | E.I. Du Pont De Nemours And Company | Continuous process to produce hexafluoroisopropanol |
| WO2010125899A1 (en) | 2009-04-28 | 2010-11-04 | セントラル硝子株式会社 | Process for producing fluoromethyl hexafluoroisopropyl ether |
| US9637435B1 (en) | 2016-11-16 | 2017-05-02 | Central Glass Company, Limited | Method for producing hexafluoroisopropanol and fluoromethyl hexafluoroisopropyl ether (sevoflurane) |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5781424A (en) * | 1980-11-11 | 1982-05-21 | Central Glass Co Ltd | Preparation of 1,1,1,3,3,3-hexafluoropropane-2-ol |
| JPS59204142A (en) * | 1983-04-28 | 1984-11-19 | Nippon Mektron Ltd | Production of hexafluoroisopropyl alcohol |
| JPS6069047A (en) * | 1983-09-27 | 1985-04-19 | Central Glass Co Ltd | Production of 1,1,1,3,3,3-hexafluoropropan-2-ol |
-
1988
- 1988-05-31 JP JP63131455A patent/JPH01301631A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5781424A (en) * | 1980-11-11 | 1982-05-21 | Central Glass Co Ltd | Preparation of 1,1,1,3,3,3-hexafluoropropane-2-ol |
| JPS59204142A (en) * | 1983-04-28 | 1984-11-19 | Nippon Mektron Ltd | Production of hexafluoroisopropyl alcohol |
| JPS6069047A (en) * | 1983-09-27 | 1985-04-19 | Central Glass Co Ltd | Production of 1,1,1,3,3,3-hexafluoropropan-2-ol |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7524995B1 (en) | 2008-06-12 | 2009-04-28 | E.I. Du Pont De Nemours And Company | Continuous process to produce hexafluoroisopropanol |
| WO2010125899A1 (en) | 2009-04-28 | 2010-11-04 | セントラル硝子株式会社 | Process for producing fluoromethyl hexafluoroisopropyl ether |
| US8865946B2 (en) | 2009-04-28 | 2014-10-21 | Central Glass Company, Limited | Process for producing fluoromethyl hexafluoroisopropyl ether |
| US9637435B1 (en) | 2016-11-16 | 2017-05-02 | Central Glass Company, Limited | Method for producing hexafluoroisopropanol and fluoromethyl hexafluoroisopropyl ether (sevoflurane) |
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