JPH0155261B2 - - Google Patents
Info
- Publication number
- JPH0155261B2 JPH0155261B2 JP1661784A JP1661784A JPH0155261B2 JP H0155261 B2 JPH0155261 B2 JP H0155261B2 JP 1661784 A JP1661784 A JP 1661784A JP 1661784 A JP1661784 A JP 1661784A JP H0155261 B2 JPH0155261 B2 JP H0155261B2
- Authority
- JP
- Japan
- Prior art keywords
- fluorine
- production method
- acid derivative
- elimination reaction
- reduced pressure
- 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.)
- Expired
Links
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 12
- 229910052731 fluorine Inorganic materials 0.000 claims description 12
- 239000011737 fluorine Substances 0.000 claims description 12
- 238000004519 manufacturing process Methods 0.000 claims description 12
- 150000001252 acrylic acid derivatives Chemical class 0.000 claims description 7
- 150000001875 compounds Chemical class 0.000 claims description 6
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical group [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 5
- 150000005599 propionic acid derivatives Chemical class 0.000 claims description 5
- 239000011701 zinc Substances 0.000 claims description 5
- 229910052725 zinc Inorganic materials 0.000 claims description 5
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 229910052708 sodium Inorganic materials 0.000 claims description 3
- 239000011734 sodium Substances 0.000 claims description 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 2
- 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 claims description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 2
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 2
- 229910052802 copper Inorganic materials 0.000 claims description 2
- 239000010949 copper Substances 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002366 halogen compounds Chemical class 0.000 claims description 2
- 150000002367 halogens Chemical group 0.000 claims description 2
- 229910052742 iron Inorganic materials 0.000 claims description 2
- 239000011777 magnesium Substances 0.000 claims description 2
- 229910052749 magnesium Inorganic materials 0.000 claims description 2
- 229910052718 tin Inorganic materials 0.000 claims description 2
- 239000011135 tin Substances 0.000 claims description 2
- 238000003379 elimination reaction Methods 0.000 claims 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- QEWYKACRFQMRMB-UHFFFAOYSA-N fluoroacetic acid Chemical compound OC(=O)CF QEWYKACRFQMRMB-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 3
- 238000004817 gas chromatography Methods 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000001577 simple distillation Methods 0.000 description 3
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 231100000331 toxic Toxicity 0.000 description 2
- 230000002588 toxic effect Effects 0.000 description 2
- OFWDLJKVZZRPOX-UHFFFAOYSA-N 2,2,3,3-tetrafluorooxetane Chemical compound FC1(F)COC1(F)F OFWDLJKVZZRPOX-UHFFFAOYSA-N 0.000 description 1
- LOMVENUNSWAXEN-UHFFFAOYSA-N Methyl oxalate Chemical compound COC(=O)C(=O)OC LOMVENUNSWAXEN-UHFFFAOYSA-N 0.000 description 1
- 229930040373 Paraformaldehyde Natural products 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- 150000002731 mercury compounds Chemical class 0.000 description 1
- SCTINZGZNJKWBN-UHFFFAOYSA-M mercury(1+);fluoride Chemical compound [Hg]F SCTINZGZNJKWBN-UHFFFAOYSA-M 0.000 description 1
- 239000013307 optical fiber Substances 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 229920002866 paraformaldehyde Polymers 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 235000003270 potassium fluoride Nutrition 0.000 description 1
- 239000011698 potassium fluoride Substances 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- -1 α-fluoroacrylic acid ester Chemical class 0.000 description 1
Description
【発明の詳細な説明】
本発明は、含フツ素アクリル酸誘導体の製法に
関し、更に詳しくは含フツ素プロピオン酸から脱
ハロゲンすることから成る含フツ素アクリル酸誘
導体の製法に関する。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a method for producing a fluorine-containing acrylic acid derivative, and more particularly to a method for producing a fluorine-containing acrylic acid derivative, which comprises dehalogenating fluorine-containing propionic acid.
一般式：＝CH2＝CFCOY (1)
（式中、Ｙはハロゲンまたは低級アルコキシ基を
表わす。）
で示される含フツ素アクリル酸誘導体は、医薬
（たとえば抗生物質）の中間体、光学繊維のさや
材用材料の中間体、塗料用材料の中間体、更に半
導体レジスト材料の中間体として有用である。 The fluorine-containing acrylic acid derivative represented by the general formula: =CH 2 =CFCOY (1) (in the formula, Y represents a halogen or lower alkoxy group) is used as an intermediate for pharmaceuticals (such as antibiotics) and as an optical fiber. It is useful as an intermediate for sheath materials, a paint material intermediate, and a semiconductor resist material intermediate.
従来該化合物(1)、たとえば、α−フルオロアク
リル酸エステルは、α，α，β−トリブロモプロ
ピオン酸エステルをフツ化水銀でフツ素化して
α，β−ジブロモ−α−フルオロプロピオン酸を
得、これを脱臭素する方法（ジヤーナル・オブ・
ケミカル・ソサエテイ、第75巻、第479〜481頁、
1954年発行）や、モノクロロ酢酸エステルをフツ
化カリウムでフツ素化してモノフルオロ酢酸を
得、次いでこれをエーテル中シユウ酸ジメチルと
反応させ、さらにパラホルムアルデヒド、メトキ
シナトリウムと反応させる方法（マクロモレキユ
ールズ、第13巻、第1031〜1036頁、1980年発行）
により製造されることが知られている。 Conventionally, the compound (1), for example, α-fluoroacrylic acid ester, is obtained by fluorinating α,α,β-tribromopropionic acid ester with mercury fluoride to obtain α,β-dibromo-α-fluoropropionic acid. , how to debromine this (Journal of
Chemical Society, Vol. 75, pp. 479-481,
(published in 1954), a method in which monofluoroacetic acid is fluorinated with potassium fluoride to obtain monofluoroacetic acid, which is then reacted with dimethyl oxalate in ether, and further reacted with paraformaldehyde and sodium methoxy (macromolecule). Yules, Vol. 13, pp. 1031-1036, published 1980)
It is known that it is manufactured by
しかし、前者の方法では、毒性の強い水銀化合
物を用いなければならず、収率も10％と低く、一
方後者の方法でも、毒性の強いモノフルオロ酢酸
を経由しなければならず、収率も30％程度であ
り、しかも溶媒として引火性の大きなエーテルを
使用することなどの問題がある。 However, the former method requires the use of highly toxic mercury compounds and the yield is as low as 10%, while the latter method also requires the use of highly toxic monofluoroacetic acid and has a low yield. 30%, and there are problems such as the use of highly flammable ether as a solvent.
本発明者らは、該化合物(1)の製法について研究
を行ない、対応する含フツ素プロピオン酸誘導体
を脱ハロゲンすることにより該化合物(1)が容易に
得られることを見い出し、本発明を完成するに至
つた。 The present inventors conducted research on the method for producing the compound (1) and found that the compound (1) can be easily obtained by dehalogenating the corresponding fluorine-containing propionic acid derivative, and completed the present invention. I came to the conclusion.
すなわち、本発明の要旨は、一般式：
XCH2CF2COY (2)
（式中、Ｙは前記と同意義。Ｘはハロゲンを表わ
す。）
で示される含フツ素プロピオン酸誘導体から脱ハ
ロゲン化剤の存在下、０〜150℃の温度で
一般式：XF (3)
（式中、Ｘは前記と同意義。）
で示されるハロゲン化合物を脱離して
一般式：
CH2＝CFCOY (1)
（式中、Ｙは前記と同意義。）
で示される化合物を得ることを特徴とする含フツ
素アクリル酸誘導体の製法に存する。 That is, the gist of the present invention is to dehalogenate a fluorine-containing propionic acid derivative represented by the general formula: XCH 2 CF 2 COY (2) (wherein, Y has the same meaning as above. In the presence of an agent, at a temperature of 0 to 150°C, the halogen compound represented by the general formula: XF ( 3 ) (wherein, (In the formula, Y has the same meaning as defined above.) A method for producing a fluorine-containing acrylic acid derivative is provided, which is characterized by obtaining a compound represented by the following formula.
出発物質である含フツ素プロピオン酸誘導体(2)
は、たとえば２，２，３，３−テトラフルオロオ
キセタンをヨウ化ナトリウムで処理することによ
り容易に得られる。 Starting material, fluorine-containing propionic acid derivative (2)
is easily obtained, for example, by treating 2,2,3,3-tetrafluorooxetane with sodium iodide.
脱ハロゲン化剤としては、既知のもの、たとえ
ば亜鉛、ナトリウム、マグネシウム、錫、銅、鉄
などが用いられる。 As the dehalogenating agent, known ones such as zinc, sodium, magnesium, tin, copper, iron, etc. can be used.
反応温度は、一般に０〜150℃、好ましくは30
〜80℃、より好ましくは40〜60℃である。 The reaction temperature is generally 0 to 150°C, preferably 30°C.
-80°C, more preferably 40-60°C.
反応圧力は、常圧でもよいが、200mmHg以下、
好ましくは20〜50mmHgの減圧下で行なうと自身
重合しやすい生成物含フツ素アクリル酸誘導体の
重合が防止されてその収率が向上する。 The reaction pressure may be normal pressure, but should not exceed 200 mmHg.
Preferably, when the reaction is carried out under a reduced pressure of 20 to 50 mmHg, polymerization of the product fluorine-containing acrylic acid derivative, which tends to self-polymerize, is prevented and the yield thereof is improved.
また、反応は溶媒中で行なうのが好ましく、溶
媒としては、極性溶媒、たとえばジメチルホルム
アミド（DMF）、アセトニトリル、アセトンなど
が挙げられる。 Further, the reaction is preferably carried out in a solvent, and examples of the solvent include polar solvents such as dimethylformamide (DMF), acetonitrile, and acetone.
本発明においては、反応を環流下に行なつて反
応終了後生成物を減圧蒸留により回収してもよい
が、前記重合防止がより効果的に達成されるとい
う利点から、反応中に生成物を連続的に回収する
のが望ましい。 In the present invention, the reaction may be carried out under reflux and the product may be recovered by distillation under reduced pressure after the completion of the reaction. Continuous collection is desirable.
次ぎに、実施例を示し、本発明の製法を具体的
に説明する。 Next, the manufacturing method of the present invention will be specifically explained with reference to Examples.
実施例 １
5l四つ口フラスコ中、亜鉛373ｇのDMF2500ｇ
懸濁液に50〜60℃でICH2CF2COF1042ｇ（4.378
モル）を滴下した後、１時間撹拌した。次いで、
反応混合物を42〜45℃、50mmHgで減圧単蒸留し
て粗CH2＝CFCOF162ｇを得た。収率37.6％。ガ
スクロマトグラフイによる純度分析は93.5％であ
つた。Example 1 2500 g of DMF with 373 g of zinc in a 5l four-necked flask
1042 g of ICH 2 CF 2 COF (4.378
mol) was added dropwise, and the mixture was stirred for 1 hour. Then,
The reaction mixture was subjected to simple distillation under reduced pressure at 42-45° C. and 50 mmHg to obtain 162 g of crude CH 2 =CFCOF. Yield 37.6%. Purity analysis by gas chromatography was 93.5%.
実施例 ２
実施例１と同様の仕込量を用いたが、
ICH2CF2COFは50〜60℃、20mmHgの減圧下に環
流しながら滴下した。滴下終了後、実施例１と同
様に減圧蒸留して粗CH2＝CFCOF274ｇを得た。
収率62.0％。ガスクロマトグラフイによる純度分
析は91.2％であつた。Example 2 The same loading amount as in Example 1 was used, but
ICH 2 CF 2 COF was added dropwise at 50 to 60° C. under reduced pressure of 20 mmHg while refluxing. After completion of the dropwise addition, vacuum distillation was performed in the same manner as in Example 1 to obtain 274 g of crude CH 2 =CFCOF.
Yield 62.0%. Purity analysis by gas chromatography was 91.2%.
実施例 ３
減圧度を40mmHg、反応温度を50〜60℃とし、
生成物を蒸留塔頂温度38〜40℃で連続的に回収す
る以外は実施例２の手順を繰り返して、粗CH2＝
CFCOF343ｇを得た。収率80.6％。ガスクロマト
グラフイによる純度分析は94.8％であつた。Example 3 The degree of reduced pressure was 40 mmHg, the reaction temperature was 50 to 60°C,
The procedure of Example 2 was repeated except that the product was continuously recovered at a distillation overhead temperature of 38-40° C. to produce crude CH 2 =
343g of CFCOF was obtained. Yield 80.6%. Purity analysis by gas chromatography was 94.8%.
実施例 ４
1l四つ口フラスコ中、亜鉛93ｇのアセトニトリ
ル500ｇ懸濁液に50〜60℃で
BrCH2CF2COOCH3194ｇ（0.956モル）を滴下し
た後、１時間撹拌した。次いで、反応混合物を減
圧単蒸留して粗CH2＝CFCOOCH340.7ｇを得た。
GC−MS：104（M+）、59（COOCH3）、45（CH2＝
CF）。Example 4 A suspension of 93 g of zinc in 500 g of acetonitrile at 50-60°C in a 1 L four-necked flask.
After 194 g (0.956 mol) of BrCH 2 CF 2 COOCH 3 was added dropwise, the mixture was stirred for 1 hour. Then, the reaction mixture was subjected to simple distillation under reduced pressure to obtain 40.7 g of crude CH 2 =CFCOOCH 3 .
GC-MS: 104 (M + ), 59 (COOCH 3 ), 45 (CH 2 =
CF).
実施例 ５
1l四つ口フラスコ中、亜鉛70ｇのDMF500ｇ懸
濁液に50〜60℃でICH2CF2COCl210ｇ（0.825モ
ル）を滴下した後、１時間撹拌した。次いで、反
応混合物を減圧単蒸留して粗CH2＝CFCOCl49.5
ｇを得た。GC−MS：108（M+）、63（COCl）、45
（CH2＝CF）。Example 5 210 g (0.825 mol) of ICH 2 CF 2 COCl was added dropwise to a suspension of 70 g of zinc in 500 g of DMF at 50 to 60° C. in a 1-liter four-necked flask, followed by stirring for 1 hour. The reaction mixture was then subjected to simple distillation under reduced pressure to obtain crude CH 2 =CFCOCl49.5
I got g. GC−MS: 108 (M + ), 63 (COCl), 45
( CH2 =CF).
Claims (1)
アルコキシ基を表わす。） で示される含フツ素プロピオン酸誘導体から、脱
ハロゲン化剤の存在下、０〜150℃の温度で 一般式：XF （式中、Ｘは前記と同意義。） で示されるハロゲン化合物を脱離して 一般式： CH2＝CFCOY （式中、Ｙは前記と同意義。） で示される化合物を得ることを特徴とする含フツ
素アクリル酸誘導体の製法。 ２ 脱離反応を200mmHg以下の減圧下に行なう特
許請求の範囲第１項記載の製法。 ３ 脱離反応を20〜50mmHgの減圧下に行なう特
許請求の範囲第１項または第２項記載の製法。 ４ 脱離反応中、含フツ素アクリル酸誘導体を連
続的に回収、取得する特許請求の範囲第１〜３項
のいずれかに記載の製法。 ５ 脱ハロゲン化剤が、亜鉛、ナトリウム、マグ
ネシウム、錫、銅または鉄である特許請求の範囲
第１〜４項のいずれかに記載の製法。 ６ 脱離反応を40〜60℃の温度で行なう特許請求
の範囲第１〜５項のいずれかに記載の製法。 ７ Ｙがハロゲンである特許請求の範囲第１〜６
項のいずれかに記載の製法。[Claims] 1. A dehalogenating agent derived from a fluorine-containing propionic acid derivative represented by the general formula: XCH 2 CF 2 COY (wherein, In the presence of the compound, a halogen compound represented by the general formula: Same meaning.) A method for producing a fluorine-containing acrylic acid derivative, which is characterized by obtaining a compound represented by: 2. The production method according to claim 1, wherein the elimination reaction is carried out under reduced pressure of 200 mmHg or less. 3. The production method according to claim 1 or 2, wherein the elimination reaction is carried out under reduced pressure of 20 to 50 mmHg. 4. The production method according to any one of claims 1 to 3, wherein the fluorine-containing acrylic acid derivative is continuously recovered and obtained during the elimination reaction. 5. The production method according to any one of claims 1 to 4, wherein the dehalogenating agent is zinc, sodium, magnesium, tin, copper, or iron. 6. The production method according to any one of claims 1 to 5, wherein the elimination reaction is carried out at a temperature of 40 to 60°C. 7 Claims 1 to 6 in which Y is halogen
The manufacturing method described in any of the paragraphs.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1661784A JPS60158137A (en) | 1984-01-30 | 1984-01-30 | Preparation of fluorine-containing acrylic acid derivative |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1661784A JPS60158137A (en) | 1984-01-30 | 1984-01-30 | Preparation of fluorine-containing acrylic acid derivative |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS60158137A JPS60158137A (en) | 1985-08-19 |
| JPH0155261B2 true JPH0155261B2 (en) | 1989-11-22 |
Family
ID=11921289
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP1661784A Granted JPS60158137A (en) | 1984-01-30 | 1984-01-30 | Preparation of fluorine-containing acrylic acid derivative |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS60158137A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2014522398A (en) * | 2011-06-01 | 2014-09-04 | ロディア オペレーションズ | Method for preparing fluorinated organic compounds |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3915754A1 (en) * | 1989-05-13 | 1990-11-15 | Bayer Ag | METHOD FOR PRODUCING (ALPHA) FLUORACRYLIC ACID DERIVATIVES AND NEW 1,1-DIFLUOR-2-HALOGENETHYL (HALOGEN) METHYL KETONE |
| FR2812632B1 (en) * | 2000-08-07 | 2003-03-07 | Solvay | PROCESS FOR THE SYNTHESIS OF FLUOROORGANIC COMPOUNDS |
-
1984
- 1984-01-30 JP JP1661784A patent/JPS60158137A/en active Granted
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2014522398A (en) * | 2011-06-01 | 2014-09-04 | ロディア オペレーションズ | Method for preparing fluorinated organic compounds |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS60158137A (en) | 1985-08-19 |
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