JPH03123751A - Fluorine-containing aldehyde derivative and its production - Google Patents
Fluorine-containing aldehyde derivative and its productionInfo
- Publication number
- JPH03123751A JPH03123751A JP26020089A JP26020089A JPH03123751A JP H03123751 A JPH03123751 A JP H03123751A JP 26020089 A JP26020089 A JP 26020089A JP 26020089 A JP26020089 A JP 26020089A JP H03123751 A JPH03123751 A JP H03123751A
- Authority
- JP
- Japan
- Prior art keywords
- group
- fluorine
- integer
- formula
- atom
- 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
- 229910052731 fluorine Inorganic materials 0.000 title claims abstract description 33
- 239000011737 fluorine Substances 0.000 title claims abstract description 23
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 title claims abstract description 22
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 title claims abstract description 6
- 238000004519 manufacturing process Methods 0.000 title claims description 14
- -1 aldehyde compound Chemical class 0.000 claims abstract description 29
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 8
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 8
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 7
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims abstract description 7
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 17
- 125000001153 fluoro group Chemical group F* 0.000 claims description 9
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 7
- 125000005843 halogen group Chemical group 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- 239000000126 substance Substances 0.000 claims 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 2
- 229910052799 carbon Inorganic materials 0.000 claims 2
- 150000002978 peroxides Chemical class 0.000 abstract description 11
- 150000001875 compounds Chemical class 0.000 abstract description 9
- 229910052739 hydrogen Inorganic materials 0.000 abstract description 8
- 239000003905 agrochemical Substances 0.000 abstract description 4
- 239000003814 drug Substances 0.000 abstract description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 4
- 239000007809 chemical reaction catalyst Substances 0.000 abstract description 3
- 229940079593 drug Drugs 0.000 abstract description 3
- 229910052736 halogen Inorganic materials 0.000 abstract description 3
- 150000002367 halogens Chemical group 0.000 abstract description 3
- 239000005871 repellent Substances 0.000 abstract description 3
- 230000002940 repellent Effects 0.000 abstract description 2
- 239000000463 material Substances 0.000 abstract 1
- 150000001299 aldehydes Chemical class 0.000 description 15
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 10
- 238000005259 measurement Methods 0.000 description 8
- 239000002904 solvent Substances 0.000 description 7
- 238000000034 method Methods 0.000 description 6
- 238000000921 elemental analysis Methods 0.000 description 5
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 5
- RGHHSNMVTDWUBI-UHFFFAOYSA-N 4-hydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C=C1 RGHHSNMVTDWUBI-UHFFFAOYSA-N 0.000 description 4
- 125000001931 aliphatic group Chemical group 0.000 description 4
- 125000003709 fluoroalkyl group Chemical group 0.000 description 4
- ZRSNZINYAWTAHE-UHFFFAOYSA-N p-methoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C=C1 ZRSNZINYAWTAHE-UHFFFAOYSA-N 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- 150000001491 aromatic compounds Chemical class 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- JUTIIYKOQPDNEV-UHFFFAOYSA-N 2,2,3,3,4,4,4-heptafluorobutanoyl 2,2,3,3,4,4,4-heptafluorobutaneperoxoate Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(=O)OOC(=O)C(F)(F)C(F)(F)C(F)(F)F JUTIIYKOQPDNEV-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- HZGKPVOSCUJONN-UHFFFAOYSA-N FC1C(C(C(C(=O)F)(C=C1)F)(F)F)(F)F Chemical compound FC1C(C(C(C(=O)F)(C=C1)F)(F)F)(F)F HZGKPVOSCUJONN-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- FXLOVSHXALFLKQ-UHFFFAOYSA-N p-tolualdehyde Chemical compound CC1=CC=C(C=O)C=C1 FXLOVSHXALFLKQ-UHFFFAOYSA-N 0.000 description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- SLGOCMATMKJJCE-UHFFFAOYSA-N 1,1,1,2-tetrachloro-2,2-difluoroethane Chemical compound FC(F)(Cl)C(Cl)(Cl)Cl SLGOCMATMKJJCE-UHFFFAOYSA-N 0.000 description 1
- UGCSPKPEHQEOSR-UHFFFAOYSA-N 1,1,2,2-tetrachloro-1,2-difluoroethane Chemical compound FC(Cl)(Cl)C(F)(Cl)Cl UGCSPKPEHQEOSR-UHFFFAOYSA-N 0.000 description 1
- AJDIZQLSFPQPEY-UHFFFAOYSA-N 1,1,2-Trichlorotrifluoroethane Chemical compound FC(F)(Cl)C(F)(Cl)Cl AJDIZQLSFPQPEY-UHFFFAOYSA-N 0.000 description 1
- OVZATIUQXBLIQT-UHFFFAOYSA-N 1,2-dibromo-1-chloro-1,2,2-trifluoroethane Chemical compound FC(F)(Br)C(F)(Cl)Br OVZATIUQXBLIQT-UHFFFAOYSA-N 0.000 description 1
- JRHNUZCXXOTJCA-UHFFFAOYSA-N 1-fluoropropane Chemical compound CCCF JRHNUZCXXOTJCA-UHFFFAOYSA-N 0.000 description 1
- LFCQGZXAGWRTAL-UHFFFAOYSA-N 2,2,3,3,4,4,5,5,6,6,7,7,7-tridecafluoroheptanoyl 2,2,3,3,4,4,5,5,6,6,7,7,7-tridecafluoroheptaneperoxoate Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(=O)OOC(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F LFCQGZXAGWRTAL-UHFFFAOYSA-N 0.000 description 1
- ZPGMWBFCBUKITA-UHFFFAOYSA-N 2,2,3-trichloro-1,1,1,3,4,4,4-heptafluorobutane Chemical compound FC(F)(F)C(F)(Cl)C(Cl)(Cl)C(F)(F)F ZPGMWBFCBUKITA-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 101100356682 Caenorhabditis elegans rho-1 gene Proteins 0.000 description 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 1
- 125000004744 butyloxycarbonyl group Chemical group 0.000 description 1
- 101150102523 cdc12 gene Proteins 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- KVBKAPANDHPRDG-UHFFFAOYSA-N dibromotetrafluoroethane Chemical compound FC(F)(Br)C(F)(F)Br KVBKAPANDHPRDG-UHFFFAOYSA-N 0.000 description 1
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 125000005252 haloacyl group Chemical group 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 101150070545 ycf2 gene Proteins 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
【発明の詳細な説明】
〈産業上の利用分野〉
本発明は、含フツ素アルデヒド誘導体及びその製造方法
に関する。DETAILED DESCRIPTION OF THE INVENTION <Industrial Application Field> The present invention relates to a fluorine-containing aldehyde derivative and a method for producing the same.
〈従来の技術〉
有機化合物中に、フルオロアルキル基を含有する化合物
は、生理活性等の有用な性質を示すものとして近年注目
を集めている。特にアルデヒド化合物中にフルオロアル
キル基が導入された含フツ素アルデヒド誘導体は、医薬
、農薬、界面活性剤等の合成中間体として有用であると
考えられている。従来含フツ素アルデヒド誘導体を合成
する方法としては、例えば芳香核へフッ素原子を導入す
る方法（特開昭６３−１７０３３２号公報）、ペンゾト
リフルオリドにホルミル基を導入する方法［Ｊ、Ａｍ、
Ｃｈｅｍ、Ｓｏｃ、 、６８，４２６（１９４６） ］
又はジフルオロメチル基をホルミル基に変換する方法（
米国特許第２１８０７７２号明細書）が提供されている
。<Prior Art> Compounds containing a fluoroalkyl group among organic compounds have attracted attention in recent years as they exhibit useful properties such as physiological activity. In particular, fluorine-containing aldehyde derivatives in which a fluoroalkyl group is introduced into an aldehyde compound are considered to be useful as synthetic intermediates for pharmaceuticals, agricultural chemicals, surfactants, and the like. Conventional methods for synthesizing fluorine-containing aldehyde derivatives include, for example, a method of introducing a fluorine atom into an aromatic nucleus (JP-A-63-170332), a method of introducing a formyl group into penzotrifluoride [J, Am,
Chem, Soc, 68, 426 (1946)]
Or a method of converting a difluoromethyl group to a formyl group (
No. 2,180,772).
このようにフルオロアルキル基を含有するアルデヒド化
合物の製造方法及びその方法によって得られた含フツ素
アルデヒド誘導体は、フッ素原子が導入された芳香族化
合物および特定のトリフルオロメチル基が導入された芳
香族化合物を除いては、殆ど知られていないのが実状で
ある。The method for producing an aldehyde compound containing a fluoroalkyl group and the fluorine-containing aldehyde derivative obtained by the method include aromatic compounds into which a fluorine atom is introduced and aromatic compounds into which a specific trifluoromethyl group is introduced. The reality is that almost nothing is known about it except for compounds.
〈発明が解決しようとする課題〉
本発明の目的は、撥水Ｍ油剤、医薬、農薬等の合成中間
体として利用可能なフルオロアルキル基を含有する含フ
ツ素アルデヒド誘導体及びその製造方法を提供すること
にある。<Problems to be Solved by the Invention> An object of the present invention is to provide a fluorine-containing aldehyde derivative containing a fluoroalkyl group that can be used as a synthetic intermediate for water-repellent M oil agents, medicines, agricultural chemicals, etc., and a method for producing the same. There is a particular thing.
本発明の別の目的は、反応触媒及び特殊な装置を用いず
、高収率かつ容易に含フツ素アルデヒド誘導体を製造す
ることが可能な方法を提供することにある。Another object of the present invention is to provide a method for easily producing a fluorine-containing aldehyde derivative in high yield without using a reaction catalyst or special equipment.
く課題を解決するための手段〉
本発明によれば、一般式（１）
（式中Ｒは、ハロゲン原子、炭素数１〜４のアルキル基
、炭素数１〜４のアルコキシ基、炭素数１〜４のアルコ
キシカルボニル基、カルボキシル基。According to the present invention, the general formula (1) (wherein R is a halogen atom, an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, or a C 1 to 4 alkoxy group) ~4 alkoxycarbonyl group, carboxyl group.
水酸基又は炭素数１〜４のアルカンスルホニル基を示す
。Ｘはフッ素原子、塩素原子又は水素原子を示し、ｎ□
は１〜１０の整数をｂｎ２は０〜４の整数を示す。ただ
し、ｎ２が０又はｎ２が１であり、且っＲがハロゲン原
子の場合、ｎｌは２〜１０の整数である。）で表わされ
る含フツ素アルデヒド誘導体が提供される。It represents a hydroxyl group or an alkanesulfonyl group having 1 to 4 carbon atoms. X represents a fluorine atom, a chlorine atom, or a hydrogen atom, and n□
represents an integer of 1 to 10, and bn2 represents an integer of 0 to 4. However, when n2 is 0 or n2 is 1 and R is a halogen atom, nl is an integer of 2 to 10. ) is provided.
また本発明によれば、一般式（ｎ）
るアルデヒド化合物とを反応させることを特徴とする前
記含フツ素アルデヒド誘導体の製造方法が提供される。Further, according to the present invention, there is provided a method for producing the fluorine-containing aldehyde derivative, which comprises reacting the aldehyde compound with the aldehyde compound represented by the general formula (n).
以下本発明を更に詳細に説明する。The present invention will be explained in more detail below.
本発明の含フツ素アルデヒド誘導体は、下記−般式（１
）で表わすことができ、
（式中Ｘは、フッ素原子、塩素原子、水素原子を示し、
ｎｌは１〜１ｏの整数を示す）で表わされるジ（ハロア
シル）ペルオキシドと一般式（ｍ）（式中Ｒは、ハロゲ
ン原子、炭素数１〜４のアルキル基、炭素数１〜４のア
ルコキシ基、炭素数１〜４のアルコキシカルボニル基、
カルボキシル基、水酸基又は炭素数１〜４のアルカンス
ルホニル基を示し、ｎ２は０〜４の整数を示す）で表わ
され式中Ｒは、フッ素原子、塩素原子、臭素原子、沃素
原子からなるハロゲン原子；メチル基、エチル基、ｎ−
プロピル基、ｉ−プロピル基、ｎ−ブチル基、ｔ−ブチ
ル基等の炭素数１〜４のアルキル基；メトキシ基、エト
キシ基、ｉ−プロポキシ基、ｔ−ブトキシ基等の炭素数
１〜４のアルコキシ基；メトキシカルボニル基、エトキ
シカルボニル基、ｎ−プロポキシカルボニル基、ｉ−プ
ロポキシカルボニル基、ｎ−ブトキシカルボニル基、ｔ
−ブトキシカルボニル基等の炭素数１〜４のアルコキジ
カルボニル基；カルボキシル基；水酸基又はメタンスル
ホニル基、エタンスルホニル基、ｎ−プロパンスルホニ
ル基、ｎ−ブタンスルホニル基。The fluorine-containing aldehyde derivative of the present invention has the following general formula (1
), (wherein X represents a fluorine atom, a chlorine atom, or a hydrogen atom,
nl is an integer of 1 to 1o) and a di(haloacyl)peroxide represented by the general formula (m) (wherein R is a halogen atom, an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms) , an alkoxycarbonyl group having 1 to 4 carbon atoms,
represents a carboxyl group, a hydroxyl group, or an alkanesulfonyl group having 1 to 4 carbon atoms, and n2 represents an integer of 0 to 4), where R is a halogen consisting of a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom. Atom; methyl group, ethyl group, n-
Alkyl groups having 1 to 4 carbon atoms such as propyl group, i-propyl group, n-butyl group, t-butyl group; 1 to 4 carbon atoms such as methoxy group, ethoxy group, i-propoxy group, t-butoxy group Alkoxy group; methoxycarbonyl group, ethoxycarbonyl group, n-propoxycarbonyl group, i-propoxycarbonyl group, n-butoxycarbonyl group, t
-C1-C4 alkoxycarbonyl group such as butoxycarbonyl group; carboxyl group; hydroxyl group or methanesulfonyl group, ethanesulfonyl group, n-propanesulfonyl group, n-butanesulfonyl group.
ｔ−ブタンスルホニル基等の炭素数１〜４のアルカンス
ルホニル基を示す。Ｘはフッ素原子、塩素原子、水素原
子を示し、ｎｌは１〜１０の整数を、ｎ２はＯ〜４の整
数を示す。ただし、ｎ２がＯ又はｎ２が１であり、且つ
Ｒがハロゲン原子の場合、ｎ□は２〜１０の整数である
。この際Ｒが炭素数５以上のアルキル基、アルコキシ基
、アルコキシカルボニル基又はアルカンスルホニル基で
ある場合には製造が困難であるので使用できない。前記
一般式（１）で示される含フツ素アルデヒド誘導体にお
いて、適用可能な含フツ素脂肪族基、すなわち一般式Ｘ
（ＣＦ２） ｎ、−は、ＣＦ。It represents an alkanesulfonyl group having 1 to 4 carbon atoms such as t-butanesulfonyl group. X represents a fluorine atom, a chlorine atom, or a hydrogen atom, nl represents an integer of 1 to 10, and n2 represents an integer of O to 4. However, when n2 is O or n2 is 1 and R is a halogen atom, n□ is an integer of 2 to 10. In this case, when R is an alkyl group, an alkoxy group, an alkoxycarbonyl group, or an alkanesulfonyl group having 5 or more carbon atoms, it cannot be used because production is difficult. In the fluorine-containing aldehyde derivative represented by the general formula (1), an applicable fluorine-containing aliphatic group, that is, the general formula
(CF2) n, - is CF.
Ｆ （ｃ Ｆ２） ２−１Ｆ （ＣＦ２） ３Ｆ （Ｃ
Ｆ、） ４＋、Ｆ （ｃ ｐｚ） ｓＦ （ＣＦ２）
、＋、Ｆ （ＣＦ２） ７Ｆ （ＣＦ２） 、−１Ｆ（
ＣＦ２）。F (c F2) 2-1F (CF2) 3F (C
F, ) 4+, F (c pz) sF (CF2)
, +, F (CF2) 7F (CF2) , -1F(
CF2).
Ｆ （ＣＦ２） 、。−１ＣＭＣＦ２
ＣＱ （ＣＦ２）ｚ−１ＣＱ （ＣＦ２）３ＣＱ
（ＣＦ２） ４＋、Ｃｆｌ （ｃＦｚ）５ＣＩｔ
（ＣＦ２）、＋、ＣΩ （ＣＦ２）？ＣＱ （ＣＦ２
）、＋、ｃ Ｑ （ＣＦ２）９ＣＱ （ＣＦ、） 、
。−１ＨＣＦ２−１Ｈ（ｃ ｐｚ）ｚＨ（ＣＦ２） ３
−１Ｈ（ＣＦり４
Ｈ（ｃ ＦＺ）５−１Ｈ（ｃ Ｆｚ）ｓＨ（ｃ ｒ’ａ
）ｖ−１Ｈ（ｃ Ｆ２）ｓＨ（ＣＦ２） ！−１Ｈ（Ｃ
Ｆ２）□。−である。この際、含フツ素脂肪族基の炭素
数、すなわちｎｌが１０を超える場合には、溶媒に対す
る溶解性が低下するので、１０以下とする必要がある。F (CF2),. -1CMCF2 CQ (CF2)z-1CQ (CF2)3CQ
(CF2) 4+, Cfl (cFz)5CIt
(CF2), +, CΩ (CF2)? CQ (CF2
), +, c Q (CF2)9CQ (CF,) ,
. -1HCF2-1H(c pz)zH(CF2) 3
-1H(CFri4H(c FZ)5-1H(c Fz)sH(c r'a
)v-1H(c F2)sH(CF2)! -1H(C
F2) □. − is. At this time, if the number of carbon atoms in the fluorine-containing aliphatic group, that is, nl, exceeds 10, the solubility in the solvent will decrease, so it needs to be 10 or less.
前記−般式（１）で表わされる含フツ素アルデヒド誘導
体としては、例えばヘプタフルオロプロピルベンズアル
デヒド、ヘプタフルオロプロピル−ｐ−アニスアルデヒ
ド、ヘプタフルオロプロピル−４−ヒドロキシベンズア
ルデヒド、ヘプタフルオロプロピル−ｐ−トルアルデヒ
ド、トリデカフルオロへキシルベンズアルデヒド等を好
ましく挙げることができる。Examples of the fluorine-containing aldehyde derivative represented by the general formula (1) include heptafluoropropylbenzaldehyde, heptafluoropropyl-p-anisaldehyde, heptafluoropropyl-4-hydroxybenzaldehyde, and heptafluoropropyl-p-tolualdehyde. , tridecafluorohexylbenzaldehyde and the like can be preferably mentioned.
本発明の製造方法では、特定のジ（ハロアシル）ペルオ
キシドと、特定のアルデヒド化合物とを反応させて、前
記一般式（１）で示される含フツ素アルデヒド誘導体を
製造することを特徴とする。The production method of the present invention is characterized in that a specific di(haloacyl)peroxide and a specific aldehyde compound are reacted to produce a fluorine-containing aldehyde derivative represented by the general formula (1).
本発明の製造方法に用いるジ（ハロアシル）ペルオキシ
ドは、下記一般式（■）で表わすことができ、
式中Ｘは、フッ素原子、塩素原子、水素原子を示し、ｎ
工は１〜１０の整数を示す。ｎ□が１１以上の場合には
、溶媒の存在下において反応させる際に前記一般式（Ｉ
Ｉ）にて示されるジ（ハロアシル）ペルオキシドの溶解
性に問題が生ずる。前記一般式（Ｉｔ）で示されるジ（
ハロアシル）ペルオキシドのｘ （ｃ Ｆ２） ｎｌ−
は、前記一般式（１）中の含フツ素脂肪族基より適宜選
択して用いることができる。The di(haloacyl)peroxide used in the production method of the present invention can be represented by the following general formula (■), where X represents a fluorine atom, a chlorine atom, or a hydrogen atom, and n
is an integer from 1 to 10. When n□ is 11 or more, when reacting in the presence of a solvent, the general formula (I
A problem arises with the solubility of the di(haloacyl)peroxide shown in I). Di(
haloacyl) peroxide x (c F2) nl-
can be appropriately selected and used from the fluorine-containing aliphatic groups in the general formula (1).
本発明の製造方法に用いる前記特定のアルデヒド化合物
は、下記一般式（ＩＩ［）で表わすことができ。The specific aldehyde compound used in the production method of the present invention can be represented by the following general formula (II[).
式中Ｒは、前記一般式（１）中のＲと同様であり、ｎ２
は０〜４の整数を示す。前記一般式（ＩＩＩ）で表わさ
れるアルデヒド化合物としては、例えばベンズアルデヒ
ド、ｐ−アニスアルデヒド、４−ヒドロキシベンズアル
デヒド、ｐ−トルアルデヒド等を好ましく挙げることが
できる。本発明の製造方法において、前記ジ（ハロアシ
ル）ペルオキシドと、アルデヒド化合物とを反応させる
にあたり、前記ジ（ハロアシル）ペルオキシドと前記ア
ルデヒド化合物との仕込みモル比は、１：０．５〜１０
が好ましく、特に１：１〜５であることが望ましい。前
記仕込みモル比が０．５未満では生成する含フツ素アル
デヒド誘導体の収率が低下する傾向にあり、また１０を
超えると反応終了後の未反応芳香族化合物が残存し、目
的とする生成物の単離が困難となるので好ましくない。In the formula, R is the same as R in the general formula (1), and n2
represents an integer from 0 to 4. Preferred examples of the aldehyde compound represented by the general formula (III) include benzaldehyde, p-anisaldehyde, 4-hydroxybenzaldehyde, and p-tolualdehyde. In the production method of the present invention, when reacting the di(haloacyl)peroxide and the aldehyde compound, the molar ratio of the di(haloacyl)peroxide and the aldehyde compound is 1:0.5 to 10.
The ratio is preferably 1:1 to 5. When the charging molar ratio is less than 0.5, the yield of the fluorine-containing aldehyde derivative produced tends to decrease, and when it exceeds 10, unreacted aromatic compounds remain after the reaction is completed, and the desired product cannot be obtained. This is not preferred because it makes isolation difficult.
ま、た、反応は常圧で行なうことが可能であり、かつ反
応温度は通常０〜１５０℃、好ましくは１０〜１ｏｏ℃
の範囲であることが望ましい。前記反応温度が０℃未満
では反応時間が長くなり、１５０℃を超えると反応時の
圧力が高くなって、反応操作が困難であるので好ましく
ない。更に反応時間は通常３０分〜２０時間の範囲で行
なうことができるが、実用的には３〜１０時間になるよ
うに条件を設定することが望ましい。Furthermore, the reaction can be carried out at normal pressure, and the reaction temperature is usually 0 to 150°C, preferably 10 to 10°C.
It is desirable that it be within the range of . If the reaction temperature is less than 0°C, the reaction time becomes long, and if it exceeds 150°C, the pressure during the reaction becomes high, making the reaction operation difficult, which is not preferable. Furthermore, although the reaction time can be generally within the range of 30 minutes to 20 hours, it is practically desirable to set the conditions so that the reaction time is 3 to 10 hours.
本発明の製造方法では前記種々の反応条件下において、
前記ジ（ハロアシル）ペルオキシドと前記アルデヒド化
合物とを反応させることにより。In the production method of the present invention, under the various reaction conditions,
By reacting the di(haloacyl)peroxide and the aldehyde compound.
目的の含フツ素アルデヒド誘導体を得ることができるが
、前記ジ（ハロアシル）ペルオキシドの取扱い及び反応
を、より円滑に行なうために溶媒を用いることが好まし
い。前記溶媒としては水素原子を含有しないハロゲン化
脂肪族溶媒が特に好ましく、具体的には例えば２−クロ
ロ−１，２−ジブロモ−１，１，２−トリフルオロエタ
ン、１゜２−ジブロモへキサフルオロプロパン、１，２
−ジブロモテトラフルオロエタン、１，１−ジフルオロ
テトラクロロエタン、１，２−ジフルオロテトラクロロ
エタン、フルオロトリクロロメタン、ヘプタフルオロ−
２，３，３−トリクロロブタン、１．１，１．３−テト
ラクロロテトラフルオロプロパン、１．１．１−トリク
ロロペンタフルオロプロパン、１，１．２−トリクロロ
トリフルオロエタン等を用いることができ、特に工業的
には、１．１．２−トリクロロトリフルオロエタンを好
ましく挙げる。二とができる。前記溶媒を使用する場合
、通常溶媒中の前記ジ（へロアシル）ペルオキシドの濃
度は、１〜３０重量％程度であることが望ましい。Although the desired fluorine-containing aldehyde derivative can be obtained, it is preferable to use a solvent in order to more smoothly handle and react the di(haloacyl)peroxide. The solvent is particularly preferably a halogenated aliphatic solvent that does not contain a hydrogen atom, and specifically, for example, 2-chloro-1,2-dibromo-1,1,2-trifluoroethane, 1°2-dibromohexane, etc. Fluoropropane, 1,2
-dibromotetrafluoroethane, 1,1-difluorotetrachloroethane, 1,2-difluorotetrachloroethane, fluorotrichloromethane, heptafluoro-
2,3,3-trichlorobutane, 1.1,1.3-tetrachlorotetrafluoropropane, 1.1.1-trichloropentafluoropropane, 1,1.2-trichlorotrifluoroethane, etc. can be used. , 1.1.2-trichlorotrifluoroethane is particularly preferred from an industrial perspective. I can do two things. When using the above solvent, it is usually desirable that the concentration of the di(heroacyl)peroxide in the solvent is about 1 to 30% by weight.
本発明の製造方法により得られる反応生成物は公知の方
法で精製することが可能である。The reaction product obtained by the production method of the present invention can be purified by a known method.
〈発明の効果〉
本発明の含フツ素アルデヒド誘導体は、新規な化合物で
あり、Ｊ９水撥油剤、医薬、農薬等の合成中間体として
利用することができる。また本発明の製造方法により含
フツ素アルデヒド誘導体を。<Effects of the Invention> The fluorine-containing aldehyde derivative of the present invention is a novel compound and can be used as a synthetic intermediate for J9 water and oil repellents, medicines, agricultural chemicals, and the like. Further, a fluorine-containing aldehyde derivative can be produced by the production method of the present invention.
短時間で高収率かつ容易に、しかも反応触媒及び特殊な
装置を使用せずに製造することができる。It can be produced easily in a short time with high yield and without using a reaction catalyst or special equipment.
〈実施例〉
以下本発明を実施例にもとすいて具体的に説明するが、
本発明はこれらに限定されるものではない。<Example> The present invention will be specifically explained below using Examples.
The present invention is not limited to these.
去」１」Ｌ
ビス（ヘプタフルオロブチリル）ペルオキシド０．４３
ｇ （１ｍｍｏＱ）を含むｌ、１．２−トリクロロトリ
フルオロエタン溶液８．５ｇ中に。1"L Bis(heptafluorobutyryl)peroxide 0.43
g (1 mmoQ) in 8.5 g of a l,1,2-trichlorotrifluoroethane solution.
ベンズアルデヒド０．１６ｇ （１，５ｍｍｏＱ）を添
加した窒素気流下、４０℃において５時間反応させた。0.16 g (1.5 mmoQ) of benzaldehyde was added and the mixture was reacted at 40° C. for 5 hours under a nitrogen stream.
反応終了後反応物を３０ｍＱの水で洗浄し、更に３０ｍ
Ｑの飽和重曹水、３０ｍＱの飽和食塩水で洗浄し、硫酸
マグネシウムで乾燥後１反応生成物をガスクロマトグラ
フィー、ＧＣ−ＭＳ、■Ｒ，ＮＭＲ１元素分析により分
析した。その結果、ヘプタフルオロプロピルベンズアル
デヒドが９０％の収率で得られたことが判った。得られ
た化合物の構造式及び測定結果を以下に示す。After the reaction was completed, the reaction product was washed with 30 mQ of water, and further washed with 30 mQ of water.
After washing with Q saturated sodium bicarbonate solution and 30 mQ saturated saline and drying over magnesium sulfate, the reaction product 1 was analyzed by gas chromatography, GC-MS, 1R, and NMR 1 elemental analysis. As a result, it was found that heptafluoropropylbenzaldehyde was obtained with a yield of 90%. The structural formula and measurement results of the obtained compound are shown below.
Ｇ Ｃ−Ｍ Ｓ ２７４（Ｍ”）、１５５
，１２７Ｉ Ｒ（ｃｍ−１） １７００（ｙ
Ｃ）ｔｏ）、１３２５（ｖ ＣＦ３）。G C-M S 274 (M”), 155
,127I R(cm-1) 1700(y
C) to), 1325 (v CF3).
１２２０（ヤＣＦ２）
”Ｈ−ＮＭＲ（ＣＤＣｌ２） δ＝１０．０８（ＬＨ
，Ｓ）。1220 (YCF2) ”H-NMR (CDCl2) δ=10.08 (LH
,S).
７．８Ｆｒ７．２０（４Ｈ，ｍ）
元素分析 理論値 Ｃ：４３．８１対 Ｈ：１．８
４％実測値 Ｃ：４３．５２”ｌｌ ）ｌ：２．０１
対ヌ」１１炎
ベンズアルデヒドの代わりにｐ−アニスアルデヒド０．
２０ｇ （１，５ｍｍｏｎ）を用いた以外は実施例１と
同様に反応を行なったところ、ヘプタフルオロプロピル
−ｐ−アニスアルデヒドが８２％の収率で得られた。次
いで実施例１と同様に各測定を行った。得られた化合物
の構造式及び測定結果を以下に示す。7.8Fr7.20 (4H, m) Elemental analysis Theoretical value C: 43.81 vs. H: 1.8
4% actual value C: 43.52”ll)l: 2.01
11 p-anisaldehyde instead of benzaldehyde 0.
When the reaction was carried out in the same manner as in Example 1 except that 20 g (1.5 mmon) was used, heptafluoropropyl-p-anisaldehyde was obtained in a yield of 82%. Next, measurements were performed in the same manner as in Example 1. The structural formula and measurement results of the obtained compound are shown below.
ＧＣ−ＭＳ ３０４（Ｍ＋）、１８５ＩＲ
（ロー１） １６９０（νＣＨＯ） 、 １３
３０ （νＣＦ、）。GC-MS 304 (M+), 185IR
(Rho 1) 1690 (νCHO), 13
30 (νCF,).
１２６０（ｖ Ｐｈ０ＣＩＩａ）、１２２０（ｖ ＣＦ
２）Ｊ（−ＮＭＲ（ＣＤＣｌ２） δ＝１０．０１（
ｌｔｌ、ｓ）。1260 (v Ph0CIIa), 1220 (v CF
2) J(-NMR(CDCl2) δ=10.01(
ltl, s).
７．８４−７．３５（３Ｈ，ｍ） 。7.84-7.35 (3H, m).
４．０２（３Ｈ，ｓ）
元ＩＡ分析理論値 Ｃ：４３．４４％ Ｈ：２．３２
％実測値 Ｃ：４３．２９％ Ｈ：２．４６％犬】１１
走
ベンズアルデヒドの代わりに４−ヒドロキシベンズアル
デヒド０ 、１８ ｇ （１、５ｍ ｍ ｏ Ｑ ）を
用いた以外は実施例１と同様に反応を行なったところ、
ヘプタフルオロプロピル−４−ヒドロキシベンズアルデ
ヒドが８０％の収率で得られた。次いで実施例１と同様
に各測定を行った。得られた化合物の構造式及び測定結
果を以下に示す。4.02 (3H, s) Original IA analysis theoretical value C: 43.44% H: 2.32
% Actual value C: 43.29% H: 2.46% dog] 11
The reaction was carried out in the same manner as in Example 1, except that 0.18 g (1.5 m m o Q) of 4-hydroxybenzaldehyde was used instead of benzaldehyde.
Heptafluoropropyl-4-hydroxybenzaldehyde was obtained with a yield of 80%. Next, measurements were performed in the same manner as in Example 1. The structural formula and measurement results of the obtained compound are shown below.
ＧＣ−ＭＳ ２９０（Ｍ”）、１７１１
Ｒ（Ｃ１１１−” ） ３１８０（ｖ ＯＨ
） 、 １６７０（ｙ Ｃｌｌ０） 。GC-MS 290 (M”), 1711
R(C111-”) 3180(v OH
), 1670 (y Cll0).
１３３０（νＣＦ、）、１２２０（ｖＣＦ２）１Ｈ−Ｎ
ＭＲ（ＣＤＣｌ２） δ：１０．０２（ＩＨ，ｓ）
、７．２０−７．９０（３Ｎ、ｍ）元素分析 理論
値 Ｃ：４１．４０％ Ｈ：１．７４％実測値 Ｃ：４
Ｌ１７％ Ｈ：１．９８％去】１」先
ベンズアルデヒドの代わりにｐ−トルアルデヒド０．１
８ｇ （１，５ｍｍｏＱ）を用いた以外は実施例１と同
様に反応を行なったところ、ヘプタフルオロプロピル−
ｐ−トルアルデヒドが８０％の収率で得られた０次いで
実施例１と同様に各測定を行った。得られた化合物の構
造式及び結果を以下に示す。1330 (νCF, ), 1220 (vCF2) 1H-N
MR (CDCl2) δ: 10.02 (IH, s)
, 7.20-7.90 (3N, m) Elemental analysis Theoretical value C: 41.40% H: 1.74% Actual value C: 4
L17% H: 1.98% 1" p-tolualdehyde 0.1 instead of benzaldehyde
When the reaction was carried out in the same manner as in Example 1 except that 8 g (1.5 mmoQ) was used, heptafluoropropyl-
p-Tolualdehyde was obtained in a yield of 80%.Next, measurements were carried out in the same manner as in Example 1. The structural formula and results of the obtained compound are shown below.
Ｇ Ｃ−Ｍ Ｓ ２８８（Ｍ”）、１６９
Ｉ Ｒ（ａｎ−１） １７００（ｖｃＨｏ）
、１３３０（ｖＣＦ、）。G C-M S 288 (M”), 169
IR(an-1) 1700(vcHo)
, 1330 (vCF,).
１２２０（νＣＦ、 ）
’Ｈ−ＮＭＲ（ＣＤＣ１２） δ＝１０．０２（ＬＨ
，ｓ） 、７．８５−７．２０（３Ｈ，ｍ）２．５２（
３Ｈ，ｓ）
元素分析 理論値 Ｃ：４５．８５％ Ｈ：２．４
５％実測値 Ｃ：４５．７７％ Ｈ：２．６６％去】１
」ｉ
ビス（ヘプタフルオロブチリル）ペルオキシドの代わり
にビス（トリデカフルオロヘプタノイル）ペルオキシド
を用いた以外は実施例１と同様に反応を行なったところ
、トリデカフルオロへキシルベンズアルデヒドが８６％
の収率で得られた。次いで実施例１と同様に各測定を行
った。得られた化合物の構造式及び測定結果を以下に示
す。1220(νCF, )'H-NMR(CDC12) δ=10.02(LH
,s) ,7.85-7.20(3H,m)2.52(
3H,s) Elemental analysis Theoretical value C: 45.85% H: 2.4
5% actual value C: 45.77% H: 2.66%] 1
"i The reaction was carried out in the same manner as in Example 1 except that bis(tridecafluoroheptanoyl) peroxide was used instead of bis(heptafluorobutyryl) peroxide, and tridecafluorohexylbenzaldehyde was 86%
was obtained in a yield of . Next, measurements were performed in the same manner as in Example 1. The structural formula and measurement results of the obtained compound are shown below.
Ｇ Ｃ−Ｍ Ｓ ４２４ （Ｍ”）、 １
５５Ｉ Ｒ（Ｑｌ＋−’） １７００（ｖｃＨ
ｏ）、１３２５（ｖ ＣＦ、）。G C-M S 424 (M”), 1
55I R(Ql+-') 1700(vcH
o), 1325 (v CF,).
１２２０（νＣＦ、 ）
”Ｈ−ＮＭＲ（ＣＤＣｌ２）δ＝１０．０９（ＩＨ，ｓ
） 、７．８６−７．２０（４Ｈ，ｍ）元素分析
理論値 Ｃ：３６．８１％ Ｈ：１．１９％実測値 Ｃ
：３６．５８％ Ｈ：１．３３％歩」ｕ」Ｌ
実施例１により得られたヘプタフルオロベンズアルデヒ
ドは、 ブロモメタンと、 トリフェニルフォスフイン
より誘導されるイリドとを反応させることより、容易に
ヘプタフルオロプロピルスチレンを収率７５％で得るこ
とができた。1220(νCF, )”H-NMR(CDCl2)δ=10.09(IH,s
), 7.86-7.20 (4H, m) elemental analysis
Theoretical value C: 36.81% H: 1.19% Actual value C
Heptafluorobenzaldehyde obtained in Example 1 can be easily converted to heptafluorobenzaldehyde by reacting bromomethane with a ylide derived from triphenylphosphine. Fluoropropylstyrene could be obtained with a yield of 75%.
Claims (1)
、炭素数１〜４のアルコキシ基、炭素数１〜４のアルコ
キシカルボニル基、カルボキシル基、水酸基又は炭素数
１〜４のアルカンスルホニル基を示す。Ｘはフッ素原子
、塩素原子又は水素原子を示し、ｎ＿１は１〜１０の整
数を、ｎ＿２は０〜４の整数を示す。ただし、ｎ＿２が
０又はｎ＿２が１であり、且つＲがハロゲン原子の場合
、ｎ＿１は２〜１０の整数である。）で表わされる含フ
ッ素アルデヒド誘導体。 ２）一般式（II） ▲数式、化学式、表等があります▼・・・（II） （式中Ｘは、フッ素原子、塩素原子、水素原子を示し、
ｎ＿１は１〜１０の整数を示す）で表わされるジ（ハロ
アシル）ペルオキシドと一般式（III）▲数式、化学式
、表等があります▼・・・（III） （式中Ｒは、ハロゲン原子、炭素数１〜４のアルキル基
、炭素数１〜４のアルコキシ基、炭素数１〜４のアルコ
キシカルボニル基、カルボキシル基、水酸基又は炭素数
１〜４のアルカンスルホニル基を示し、ｎ＿２は０〜４
の整数を示す）で表わされるアルデヒド化合物とを反応
させることを特徴とする請求項１記載の含フッ素アルデ
ヒド誘導体の製造方法。[Claims] 1) General formula (I) ▲There are numerical formulas, chemical formulas, tables, etc.▼... (I) (In the formula, R is a halogen atom, an alkyl group having 1 to 4 carbon atoms, or a carbon number 1 -4 alkoxy group, C1-4 alkoxycarbonyl group, carboxyl group, hydroxyl group, or C1-4 alkanesulfonyl group. X represents a fluorine atom, chlorine atom, or hydrogen atom, and n_1 is 1- 10, and n_2 is an integer of 0 to 4.However, when n_2 is 0 or n_2 is 1, and R is a halogen atom, n_1 is an integer of 2 to 10. Fluorine aldehyde derivative. 2) General formula (II) ▲There are mathematical formulas, chemical formulas, tables, etc.▼...(II) (In the formula, X represents a fluorine atom, a chlorine atom, a hydrogen atom,
n_1 represents an integer from 1 to 10) and the general formula (III) ▲ Numerical formulas, chemical formulas, tables, etc. ▼ ... (III) (In the formula, R is a halogen atom, a carbon An alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, an alkoxycarbonyl group having 1 to 4 carbon atoms, a carboxyl group, a hydroxyl group, or an alkanesulfonyl group having 1 to 4 carbon atoms, and n_2 is 0 to 4.
2. The method for producing a fluorine-containing aldehyde derivative according to claim 1, wherein the fluorine-containing aldehyde derivative is reacted with an aldehyde compound represented by the following integer.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP26020089A JPH03123751A (en) | 1989-10-06 | 1989-10-06 | Fluorine-containing aldehyde derivative and its production |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP26020089A JPH03123751A (en) | 1989-10-06 | 1989-10-06 | Fluorine-containing aldehyde derivative and its production |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH03123751A true JPH03123751A (en) | 1991-05-27 |
Family
ID=17344724
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP26020089A Pending JPH03123751A (en) | 1989-10-06 | 1989-10-06 | Fluorine-containing aldehyde derivative and its production |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH03123751A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2009292777A (en) * | 2008-06-06 | 2009-12-17 | Univ Meijo | Method for introducing perfluorohydrocarbon group |
| WO2019159652A1 (en) | 2018-02-16 | 2019-08-22 | ダイキン工業株式会社 | Perfluoro diacyl peroxide, solution, polymerization initiator, polymer preparation method, and perfluoro acyl chloride |
-
1989
- 1989-10-06 JP JP26020089A patent/JPH03123751A/en active Pending
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2009292777A (en) * | 2008-06-06 | 2009-12-17 | Univ Meijo | Method for introducing perfluorohydrocarbon group |
| WO2019159652A1 (en) | 2018-02-16 | 2019-08-22 | ダイキン工業株式会社 | Perfluoro diacyl peroxide, solution, polymerization initiator, polymer preparation method, and perfluoro acyl chloride |
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