JPS60136536A - Production of 2,2,3-trifluoropropinonyl fluoride - Google Patents
Production of 2,2,3-trifluoropropinonyl fluorideInfo
- Publication number
- JPS60136536A JPS60136536A JP58251070A JP25107083A JPS60136536A JP S60136536 A JPS60136536 A JP S60136536A JP 58251070 A JP58251070 A JP 58251070A JP 25107083 A JP25107083 A JP 25107083A JP S60136536 A JPS60136536 A JP S60136536A
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- Japan
- Prior art keywords
- fluoride
- reaction
- catalyst
- carried out
- alkali metal
- Prior art date
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Classifications
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- 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
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- Catalysts (AREA)
- 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】
本発明は、２，２，３−トリフルオロプロピオニルフル
オライドの製法に関し、更に詳しくは１゜１．２．２−
テトラフルオロオキセタンを原料とする２、２．３−）
リフルオロプロピオニルフルオライドの製法に関する。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a method for producing 2,2,3-trifluoropropionyl fluoride, more specifically, 1°1.2.2-
2,2.3-) made from tetrafluorooxetane
This invention relates to a method for producing refluoropropionyl fluoride.
２．２．３−トリフルオロプロピオニルフルオライドは
、医薬、農薬の中間体として、また強酸触媒として有用
であり、さらにエヌテル化して溶媒として、脱フッ化水
素してモノマーとして利用できる。2.2.3-Trifluoropropionyl fluoride is useful as an intermediate for medicines and agricultural chemicals and as a strong acid catalyst, and can be further used as a solvent by enetherization and as a monomer by dehydrofluorination.
２．２＋３−トリーｙｔｖ４−ロプロピオニルフルオラ
イドは、これまでプロピオン酸クロライドをフツ化コノ
旬しト触媒の存在下にフッ素化して得られる多種の生成
物の中の一化合物として得られることが知られている（
Ｊ、ｏｆ Ｆｌｕｏｒｉｎｅ Ｃｈｅｍｉｓｔｒｙ。2.2+3-triytv4-lopropionyl fluoride has been known to be obtained as one compound among various products obtained by fluorinating propionic acid chloride in the presence of a fluorination catalyst. (
J, of Fluorine Chemistry.
＋９７３（３）、３２９−３０．Ｊ、Ｃ，Ｔａｔｌｏｗ
ｅｔ。+973(3), 329-30. J.C.Tatlow
etc.
ａｌ 参照）。al).
本発明者らは、２，２．３−）リフルオロプロピオニフ
ルオライドを純粋にかつ効率よく製造すべく研究を重ね
た結果、本発明を完成するに至ったものである。The present inventors have completed the present invention as a result of repeated research to produce 2,2.3-)lifluoropropionifluoride in a pure and efficient manner.
本発明の要旨は、１，１，２．２−テトラフルオロオキ
セタンを触媒の存在下に開環反応させることを特徴とす
る２、２．３−トリフルオロプロピオニルフルオライド
の製法に存スル。The gist of the present invention is a method for producing 2,2,3-trifluoropropionyl fluoride, which comprises subjecting 1,1,2,2-tetrafluorooxetane to a ring-opening reaction in the presence of a catalyst.
原ｒ１である１、１，２．２−テトラフルオロオキセタ
ンは、既知化合物であって、テトラフルオロエチレンと
ホルムアルデヒドとを反応させることにより容易に製造
することができる。1,1,2,2-tetrafluorooxetane, which is the raw material r1, is a known compound and can be easily produced by reacting tetrafluoroethylene and formaldehyde.
開環反応の触媒としては、フッ化アルカリ金属まだはル
イス酸が好ましく用いられる。As a catalyst for the ring-opening reaction, an alkali metal fluoride or a Lewis acid is preferably used.
フッ化アルカリ金属としては、たとえばフッ化ナトリウ
ム、フン化カリウム、フッ化セシウムなどが好ましく用
いられる。As the alkali metal fluoride, for example, sodium fluoride, potassium fluoride, cesium fluoride, etc. are preferably used.
ルイス酸としては、ＡｌＣｌ３、Ｓ ｌ） Ｆ５などが
好ましく用いられる。As the Lewis acid, AlCl3, S1) F5, etc. are preferably used.
本発明の方法は、液相または気相のいずれでも実施する
ことができる。The method of the invention can be carried out in either liquid or gas phase.
液相で反応を行う場合、フッ化アルカリ金属はアブロテ
ィツク溶媒、たとえばジグライム、テトラグライム、ア
セトニトリルなどに溶解され、俗ｉ中に１，１，２．２
−テトラフルオロオキセタンを加えて反応させる。また
、ＡｌＣｌ３は、好マしくはＣＨＣ１２、ＣＨＣ１３、
ＣＣ１４などに溶解できるが、これらに（奴定されるも
のではない。Ｓ ｂ Ｆ２の場合、特に溶媒を必要とし
ない。When carrying out the reaction in the liquid phase, the alkali metal fluoride is dissolved in an abrotic solvent such as diglyme, tetraglyme, acetonitrile, etc.
-Add tetrafluorooxetane and react. Moreover, AlCl3 is preferably CHC12, CHC13,
It can be dissolved in CC14, etc., but is not limited to these. In the case of S b F2, no particular solvent is required.
反応は、８０°Ｃから溶媒の沸点までの温度、通常８０
〜２００°Ｃの温度で行われる。反応時間は、反応温度
、触媒の種類や量などに依存するが、通常１〜２４時間
である。The reaction is carried out at a temperature from 80°C to the boiling point of the solvent, usually 80°C.
It is carried out at a temperature of ~200°C. The reaction time depends on the reaction temperature, type and amount of catalyst, etc., but is usually 1 to 24 hours.
液相におけるフン化アルカリ金属としては、フッ化カリ
ウムおよびフッ化セシウムか好ましい。As the alkali metal fluoride in the liquid phase, potassium fluoride and cesium fluoride are preferred.
フッ系アニオンは、反応系中に触媒用、たとえば１．１
，２．２−テトラフルオロオキセタンに対して１〜５０
モル％存在すればよい。The fluorine anion is used as a catalyst in the reaction system, for example, 1.1
, 1 to 50 for 2.2-tetrafluorooxetane
It only needs to be present in mol%.
気相における反応は、通常５００ ′Ｃ以下、好ましく
は２００〜４５０°Ｃの温度で行われる。５００“Ｃ以
上では１．１，２．２−テトラフルオロオキセタンか熱
分１ｑ；ｄする。反応圧力は、気相を保つならば加圧で
も減圧でもよい。空間速度は、１０〜］０００１１ｒ
の範囲から、他の条件を考慮して選択すればよい。また
、原料化合物を窒素などの不活性な気体で希釈してもよ
い。The reaction in the gas phase is usually carried out at a temperature below 500'C, preferably between 200 and 450C. At temperatures above 500"C, the heat content of 1,1,2,2-tetrafluorooxetane is 1q; d.The reaction pressure may be increased or reduced as long as the gas phase is maintained.The space velocity is 10~]00011r
It may be selected from the range of , taking other conditions into account. Further, the raw material compound may be diluted with an inert gas such as nitrogen.
気相反応では、触媒は、活性炭、アスベスト、ニッケル
オキサイド、シリカゲル、モレキュラーシーブなどの担
体に担持させて用いる。相体としては、活性炭が好まし
い。In the gas phase reaction, the catalyst is supported on a carrier such as activated carbon, asbestos, nickel oxide, silica gel, or molecular sieve. Activated carbon is preferred as the phase.
次に実施例を示し、本発明を具体的に説明する。Next, examples will be shown to specifically explain the present invention.
実施例１
内容積ＪＯＱ＋ｎｌのヌテンレス製オートクレーブに、
ジグライム１５ｍ１、フッ化カリウム１．８ｇ。Example 1 In a Nutenless autoclave with an internal volume of JOQ+nl,
15ml of diglyme, 1.8g of potassium fluoride.
および１，１，２．２−テトラフルオロオキセタン１３
ｇ（０，１０モル）を仕込み、攪拌下、１５０°Ｃに８
時間保った。生成物および未反応原料を蒸留して回収し
た所、混合物で１２．８ｇ回収された。and 1,1,2,2-tetrafluorooxetane 13
g (0.10 mol) and heated to 150°C with stirring.
Saved time. When the product and unreacted raw materials were recovered by distillation, 12.8 g of the mixture was recovered.
ＧＬＣ、ＪＲ，ＭＳ 、ＮＭＲで分析した結果、２．２
．３−）す７／Ｌ’オロプロピオニルフルオライドが６
５モル条含まれていることがわかった。As a result of analysis by GLC, JR, MS, and NMR, 2.2
．． 3-) Su7/L'olopropionyl fluoride is 6
It was found that it contained 5 moles.
実施例２
直径４望ｄ、長さ６酊のペレット状活性炭にフッ化カリ
ウム水溶液を含浸せしめた後、乾燥して活性炭に担持し
たフッ化カリウム触媒（フッ化カリウム担持量：活性炭
重量の３０重量））を得た。Example 2 A potassium fluoride catalyst (supported amount of potassium fluoride: 30% of the weight of the activated carbon) was prepared by impregnating pellet-like activated carbon with a diameter of 4 mm and a length of 6 mm with an aqueous solution of potassium fluoride, then drying and supporting the activated carbon. )) was obtained.
該触ｆｆ５０ｎ／を３／４インチハステロイーＣ製反応
管に充填し、内部温度を３８０°Ｃに保つに−８１，１
，２，２−テトラフルオロオキセタンに窒素ガスを吹き
込み、１，１，２．２−テトラフルオロオキセタンを同
伴させて、５時間にわたり３０ｆを反応管に通じた。出
口ガスをドライアイス−メタノールで冷却したトラップ
で捕集したところ、捕集量は２９．４Ｍであった。ＧＬ
Ｃによる分析の結果、未反応原料は痕跡量程度であり、
残シの９９．３モル％＋１２，２．３−）リフルオロプ
ロピオニルフルオライドであった。-81,1 to fill a 3/4 inch Hastelloy C reaction tube and maintain the internal temperature at 380°C.
, 2,2-tetrafluorooxetane was blown with nitrogen gas, 1,1,2,2-tetrafluorooxetane was entrained, and 30f was passed through the reaction tube for 5 hours. When the outlet gas was collected in a trap cooled with dry ice-methanol, the amount collected was 29.4M. GL
As a result of analysis by C, there were only trace amounts of unreacted raw materials.
The residue was 99.3 mol%+12,2.3-)lifluoropropionyl fluoride.
実施例３
ドライアイスコンデンサーおよび滴下ロートを＠ｉ エ
た３００−フラスコに、四塩化炭素１００ｍ１および’
ｊＬ化アルミニウム５．０ｇを加え、４０℃で攪拌した
。次に、２，２，３．３−テトラフルオロオキセタン１
５０ｇを滴下し、約２時間攪拌を続けた。冷却後、精留
して２，２，３７７−）１Ｊフルオロプロピオニルフル
オライド１２５Ｆを１４だ。Example 3 A 300-ml flask with a dry ice condenser and dropping funnel was charged with 100 ml of carbon tetrachloride and
5.0 g of aluminum chloride was added and stirred at 40°C. Next, 2,2,3,3-tetrafluorooxetane 1
50 g was added dropwise and stirring was continued for about 2 hours. After cooling, it is rectified to obtain 2,2,377-)1J fluoropropionyl fluoride 125F.
実施例４
ドライアイスコンデンサーおよび滴下ロートを備えた５
０ｍ１フラスコに、５ｂＦ５５．ＯＦを加え、２＋！、
７１ｉ７＋で攪拌しながら２，２，３．３−テトラフル
オロオキセタン３０．０ｇを滴下した。還流が停止卜し
だ後単蒸留して２ 、２’、 ３−トリフルオロプロピ
オニルフルオライド２３．５Ｆを得た。Example 4 5 with dry ice condenser and dropping funnel
Into a 0ml flask, add 5bF55. Add OF, 2+! ,
30.0 g of 2,2,3.3-tetrafluorooxetane was added dropwise to the mixture while stirring with a 71i7+. After the reflux stopped, simple distillation was performed to obtain 2,2',3-trifluoropropionyl fluoride 23.5F.
特許出願人 ダイキン］−業株式会社
代理 人弁理士肯山葆（外２名）
手続補正書（崎
１事件の表示
昭和５８年特許願第 ２５１０７０ 号２発明の名称
２．２．３− ）リフルオロプロピオニルフルオライド
の製法３、補正をする者
事件との関係 特許出願人
ｆｔ所 大阪府大広市北区梅川１丁旧２番３９１）ｉ阪
急ピル名称 （２８５） ダイキン工業株式会社代表者
山 １） 稔
４代理人
７、補１１）内容
明細；１１の発明の詳細な説明の欄中、次の箇所を補正
します。Patent applicant Daikin] - Gyo Co., Ltd. Agent Patent attorney Kenzanbo (2 others) Procedural amendment (Representation of Saki 1 case Patent application No. 251070 1988 2 Name of invention 2.2.3-) Manufacturing method for fluoropropionyl fluoride 3, relationship with the amended case Patent applicant ft. 391 Umekawa 1-chome, Kita-ku, Daihiro City, Osaka Prefecture) Hankyu Pill name (285) Daikin Industries, Ltd. Representative Yama 1 ) Minoru 4 Agent 7, Supplement 11) Details of contents; In the detailed explanation of the invention in 11, the following parts are amended.
（＋）＝１頁１１〜１４行、［また、Ａ Ｉ ＣＩ ３
・・・・・・必要としない。］とあるを削除。(+) = Page 1, lines 11-14, [Also, AI CI 3
······do not need. ]Deleted.
（２）５ｉ′ｊ１５行、「好ましい。」の後に、「また
、ＡＩ’ＣｌＪ等のルイス酸触媒を用すする場合は、５
これらは好ましくはＣｌＩＣ＋２、Ｃｌ−１ＣＩ、、Ｃ
Ｃｌ４などに溶解して用いることができるが、これらに
限定されるものではない。Ｓ Ｉ＋ Ｆ ５の場合、特
に溶媒を必要としない。この場合、反応は室温から５１
’ｌ ’Ｃが１１ｊ’ましい。」を挿入。(2) Line 5i'j 15, after ``preferable.'', ``Also, when using a Lewis acid catalyst such as AI'ClJ, 5
These are preferably ClIC+2, Cl-1CI, ,C
It can be used by dissolving it in Cl4 or the like, but is not limited thereto. In the case of S I+ F 5, no particular solvent is required. In this case, the reaction starts from room temperature at 51
'l 'C is 11j'. ” inserted.
以」：
手続補正書（。５．）
昭和５９年２月１ ｉｉ日
特許庁長官 殿
１、事件の表示
昭和５８年特許願第 ２５１１１７０ 号２発明の名称
２．２．３− ） リフルオロプロピオニルフルオライ
ドの製法３、補正をする者
事件との関係 特許出願人
代表者 山 １） 稔
４、代理人
住所 大阪府大阪市東区本町２−１０ 本町ビル内７、
補１■ミの内容
明細−：中成の箇所を補正します。2.2.3-) Lifluoropropionyl Fluoride manufacturing method 3, relationship with the amended case Patent applicant representative Yama 1) Minoru 4, agent address 7 Honmachi Building, 2-10 Honmachi, Higashi-ku, Osaka-shi, Osaka Prefecture;
Supplement 1■ Details of contents of Mi -: Correct the missing parts.
１、特許請求の範囲の欄 別紙の通り。1. Claims column As per attached sheet.
１１、発１１）１の訂細な説１１５１の欄（１）第２頁
第１（）〜１１行、ｔｊｒＪ３頁第１０行第１０行１・
１行、第・１頁第１０行、第５頁第２行、第に１ｔおよ
び末社、第６０末７行および末６行、［１，１，２，２
−１とあるを、それぞれｒ２，２．３；ｊ）−１と訂正
。11, Issue 11) Detailed explanation of 1, Column 1151 (1) Page 2, lines 1 () to 11, tjrJ page 3, line 10, line 10 1.
1st line, 1st page, 10th line, 5th page, 2nd line, 1t and the end of the 60th line, 7th line at the end and 6th line at the end, [1, 1, 2, 2
-1 was corrected to r2, 2.3;j)-1, respectively.
（２）第５百第４行、［反応は、−１の次に、「フッ化
アルカリ金属を触媒として用いた場合１，１を挿入。(2) No. 500, line 4, [In the reaction, after -1, insert ``1,1 when an alkali metal fluoride is used as a catalyst.
以 −に
（別紙）
特ｊｊＪ＋請求の範囲
（＋）２□え□影、λクテトラフルオロオキセクンを触
媒の存在下に開環反応させることを特徴とする２、２．
３−トリフルオロプロピオニルフルオライドの製法。Hereinafter (attached sheet) Particulars jjJ+Claims (+)2□e□Shadow, 2,2.
Method for producing 3-trifluoropropionyl fluoride.
（２）フッ化アルカリ金属またはルイス酸の存在下に行
う特許請求の範囲第１項記載の製法。(2) The manufacturing method according to claim 1, which is carried out in the presence of an alkali metal fluoride or a Lewis acid.
（３）フッ化アルカリ金属をアブロティツク溶媒中に溶
解させて用い、反応を８０〜２（冒）℃で行う特許請求
の範囲＠１項記載の製法。(3) The manufacturing method according to claim 1, wherein the alkali metal fluoride is dissolved in an abrotic solvent and the reaction is carried out at 80 to 2 (°C).
（４）アブロティツク溶媒が、ジグライム、トリグライ
ム、テトラグライムまたはアセトニトリルである特許請
求の範囲第３７Ｉ’？記載の製法。(4) Claim 37I', wherein the abrotic solvent is diglyme, triglyme, tetraglyme or acetonitrile? Manufacturing method described.
（５）フッ化アルカリ金属を担体に担持して用い、反応
を２００〜４５０°Ｃで行う特許請求の範囲第２項記載
の製法。(5) The manufacturing method according to claim 2, in which the alkali metal fluoride is supported on a carrier and the reaction is carried out at 200 to 450°C.
（６）担体が、活性炭、アスベスト、酸化ニッケル、シ
リカゲルまたはモレキュラーシーブである特許請求の範
囲第５項記載の製法。(6) The method according to claim 5, wherein the carrier is activated carbon, asbestos, nickel oxide, silica gel, or molecular sieve.
（７）ルイス酸の存イ「下に行う特許請求の範囲第１項
記載の製法。(7) Presence of Lewis acid A. The manufacturing method according to claim 1 below.
（８）ルイス酸が、ノ＼１Ｃ１３または５ｌ）Ｆ、であ
る特１１゛１請求の範囲第７項記載の製法。(8) The production method according to claim 7, wherein the Lewis acid is <\1C13 or <5l>F.
Claims (1)
セタンを触媒の庁在下に開板反応させることを特徴とす
る２、２，３−トリフルオロプロピオニルフルオライド
の製法。 （２）フッ化アルカリ金属またはルイス酸の存在下に行
う特許請求の範囲第１項記載の製法。 （３）フッ化アルカリ金属をアブロティツク溶媒中に溶
解させて用い、反応を８０〜２００°Ｃで行う特許請求
の範囲第１項記載の製法。 （４）アブロティツク溶啄が、ジグライム、トリグライ
ム、テトラグライムまたはアセトニトリルである特許請
求の範囲第３項記戦の製法。 （５）フッ化アルカリ金属を担体に担持して用い、反Ｌ
ｅｙを２００〜４５０°Ｃで行う特許請求の範囲第２項
ａ己１１戊の製法。 （６）担体が、活性炭、アスベスト、酸化ニッケル、シ
リカゲルまたはモレギュラーシーブである特許請求の範
囲第５項記載の製法。 （７）ルイス酸の存在下に行う特許請求の範囲第１項記
載の製法。 （８））ｖイヌ酸が、ＡｌＣｌ３ またはＳｂＦ５であ
る特許請求の範囲・第７項記載の製法。[Claims] (A method for producing 2,2,3-trifluoropropionyl fluoride, characterized by subjecting 2,2,2-tetrafluorooxetane to an opening reaction in the presence of a catalyst. (2) The manufacturing method according to claim 1, which is carried out in the presence of an alkali metal fluoride or a Lewis acid. (3) A patent in which the alkali metal fluoride is dissolved in an abrotic solvent and the reaction is carried out at 80 to 200°C. The manufacturing method according to claim 1. (4) The manufacturing method according to claim 3, wherein the abrotic solution is diglyme, triglyme, tetraglyme, or acetonitrile. (5) Using an alkali metal fluoride as a carrier. Supported and used, anti-L
Claim 2: A method for producing the same, wherein the heating is carried out at 200 to 450°C. (6) The method according to claim 5, wherein the carrier is activated carbon, asbestos, nickel oxide, silica gel, or monoregular sieve. (7) The manufacturing method according to claim 1, which is carried out in the presence of a Lewis acid. (8)) The manufacturing method according to claim 7, wherein the inucic acid is AlCl3 or SbF5.
Priority Applications (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP58251070A JPS60136536A (en) | 1983-12-26 | 1983-12-26 | Production of 2,2,3-trifluoropropinonyl fluoride |
| KR1019840008099A KR870002015B1 (en) | 1983-12-26 | 1984-12-19 | Process for preparation of 2,2-difuoropropionic acid |
| US06/684,344 US4719052A (en) | 1983-12-26 | 1984-12-20 | 2,2-difluoropropionic acid derivatives |
| DE8787113971T DE3483535D1 (en) | 1983-12-26 | 1984-12-21 | METHOD FOR PRODUCING 2,2,3-TRIFLUORPROPIONIC ACID FLUORIDE. |
| EP87113971A EP0258911B1 (en) | 1983-12-26 | 1984-12-21 | Process for preparing 2,2,3-trifluoropropionyl fluoride |
| EP84116103A EP0148490B1 (en) | 1983-12-26 | 1984-12-21 | 2,2-difluoropropionic acid derivatives and a process for preparing the same |
| DE8484116103T DE3482258D1 (en) | 1983-12-26 | 1984-12-21 | 2,2-DIFLUORPROPIONIC ACID DERIVATIVES AND METHOD FOR THE PRODUCTION THEREOF. |
| CA000470916A CA1293739C (en) | 1983-12-26 | 1984-12-21 | Process for preparing 2,2,3-trifluoropropionyl fluoride |
| CA000616011A CA1318327C (en) | 1983-12-26 | 1991-02-27 | 2,2-difluoropropionic acid derivatives |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP58251070A JPS60136536A (en) | 1983-12-26 | 1983-12-26 | Production of 2,2,3-trifluoropropinonyl fluoride |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS60136536A true JPS60136536A (en) | 1985-07-20 |
| JPH0149340B2 JPH0149340B2 (en) | 1989-10-24 |
Family
ID=17217173
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP58251070A Granted JPS60136536A (en) | 1983-12-26 | 1983-12-26 | Production of 2,2,3-trifluoropropinonyl fluoride |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS60136536A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1857485A1 (en) * | 2005-02-10 | 2007-11-21 | Daicel Chemical Industries, Ltd. | Ring-opening polymerization method and activated carbon catalyst for ring-opening polymerization |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP4786637B2 (en) | 2005-02-10 | 2011-10-05 | ダイセル化学工業株式会社 | Ring-opening polymerization method of lactone compound and activated carbon catalyst for ring-opening polymerization |
-
1983
- 1983-12-26 JP JP58251070A patent/JPS60136536A/en active Granted
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1857485A1 (en) * | 2005-02-10 | 2007-11-21 | Daicel Chemical Industries, Ltd. | Ring-opening polymerization method and activated carbon catalyst for ring-opening polymerization |
| EP1857485A4 (en) * | 2005-02-10 | 2008-12-31 | Daicel Chem | Ring-opening polymerization method and activated carbon catalyst for ring-opening polymerization |
| US7851583B2 (en) | 2005-02-10 | 2010-12-14 | Daicel Chemical Industries, Ltd. | Process and activated carbon catalyst for ring-opening polymerization |
| JP5094383B2 (en) * | 2005-02-10 | 2012-12-12 | 株式会社ダイセル | Ring-opening polymerization method and activated carbon catalyst for ring-opening polymerization |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0149340B2 (en) | 1989-10-24 |
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