JPH01153654A - Production of ammonium fluorine-containing carboxylate - Google Patents
Production of ammonium fluorine-containing carboxylateInfo
- Publication number
- JPH01153654A JPH01153654A JP31217887A JP31217887A JPH01153654A JP H01153654 A JPH01153654 A JP H01153654A JP 31217887 A JP31217887 A JP 31217887A JP 31217887 A JP31217887 A JP 31217887A JP H01153654 A JPH01153654 A JP H01153654A
- Authority
- JP
- Japan
- Prior art keywords
- fluorine
- ether
- carboxylic acid
- containing carboxylic
- solvent
- 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.)
- Granted
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- VYOZKLLJJHRFNA-UHFFFAOYSA-N [F].N Chemical compound [F].N VYOZKLLJJHRFNA-UHFFFAOYSA-N 0.000 title abstract 2
- 150000007942 carboxylates Chemical class 0.000 title abstract 2
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims abstract description 33
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 33
- 239000011737 fluorine Substances 0.000 claims abstract description 33
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract description 27
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims abstract description 17
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims abstract description 16
- 238000000034 method Methods 0.000 claims abstract description 10
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims abstract description 8
- 229910021529 ammonia Inorganic materials 0.000 claims abstract description 6
- 239000007810 chemical reaction solvent Substances 0.000 claims abstract description 6
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 claims abstract description 4
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 claims abstract description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims abstract description 4
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 3
- QQQCWVDPMPFUGF-ZDUSSCGKSA-N alpinetin Chemical compound C1([C@H]2OC=3C=C(O)C=C(C=3C(=O)C2)OC)=CC=CC=C1 QQQCWVDPMPFUGF-ZDUSSCGKSA-N 0.000 claims abstract description 3
- ABDBNWQRPYOPDF-UHFFFAOYSA-N carbonofluoridic acid Chemical compound OC(F)=O ABDBNWQRPYOPDF-UHFFFAOYSA-N 0.000 claims abstract description 3
- 239000002904 solvent Substances 0.000 claims description 17
- -1 carboxylic acid ammonium salt Chemical class 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 abstract description 11
- 239000004210 ether based solvent Substances 0.000 abstract description 6
- 238000000746 purification Methods 0.000 abstract description 3
- 239000000654 additive Substances 0.000 abstract description 2
- 150000001875 compounds Chemical class 0.000 abstract description 2
- 230000000996 additive effect Effects 0.000 abstract 1
- ORBBVPFDROYXQS-UHFFFAOYSA-N ammonium perfluorononanoate Chemical compound N.OC(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F ORBBVPFDROYXQS-UHFFFAOYSA-N 0.000 abstract 1
- 238000005530 etching Methods 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 description 7
- 229910052799 carbon Inorganic materials 0.000 description 5
- 239000000047 product Substances 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- 150000001735 carboxylic acids Chemical class 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 238000005273 aeration Methods 0.000 description 2
- 150000003863 ammonium salts Chemical class 0.000 description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- BOSAWIQFTJIYIS-UHFFFAOYSA-N 1,1,1-trichloro-2,2,2-trifluoroethane Chemical compound FC(F)(F)C(Cl)(Cl)Cl BOSAWIQFTJIYIS-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- ATRRKUHOCOJYRX-UHFFFAOYSA-N Ammonium bicarbonate Chemical compound [NH4+].OC([O-])=O ATRRKUHOCOJYRX-UHFFFAOYSA-N 0.000 description 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 235000012501 ammonium carbonate Nutrition 0.000 description 1
- 239000001099 ammonium carbonate Substances 0.000 description 1
- 238000007664 blowing Methods 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 238000011090 industrial biotechnology method and process Methods 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- UZUFPBIDKMEQEQ-UHFFFAOYSA-N perfluorononanoic acid Chemical compound OC(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F UZUFPBIDKMEQEQ-UHFFFAOYSA-N 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
【発明の詳細な説明】
〔発明の利用分野〕
本発明は、含フッ素カルボン酸アンモニウム塩の製造方
法に関するものである。含フッ素カルボン酸アンモニウ
ム塩は、その特異な表面特性から界面活性剤として特に
、フッ素樹脂重合用乳化剤あるいはメツキエツチング浴
添加剤などに使用され産業上有用な化合物である。DETAILED DESCRIPTION OF THE INVENTION [Field of Application of the Invention] The present invention relates to a method for producing a fluorine-containing carboxylic acid ammonium salt. Owing to its unique surface properties, fluorine-containing carboxylic acid ammonium salts are industrially useful compounds that are used as surfactants, particularly as emulsifiers for fluororesin polymerization or as additives for metskiating baths.
含フッ素カルボン酸アンモニウム塩の従来法としては、
含フッ素カルボン酸と炭酸アンモニウムとを水溶液中で
反応する方法（例えば、ジャーナル オブ フロリン
ケミストリー（Ｊ、 ＦｔｕｏｒｉｎｅＯｈｅｍ ）、
第２５巻、５０５〜５１２頁１９８４年）あるいは、含
フッ素カルボン酸の四塩化炭素溶液中にアンモニアガス
を吹き込むことにより合成する方法（例えば、旭硝子研
究報告、第３２巻、１２９〜１５９頁、１９８２年）が
知られている。The conventional method for producing fluorine-containing carboxylic acid ammonium salts is as follows:
A method in which a fluorine-containing carboxylic acid and ammonium carbonate are reacted in an aqueous solution (for example, Journal of Florin
Chemistry (J, FtuorineOhem),
(Vol. 25, pp. 505-512, 1984), or by blowing ammonia gas into a carbon tetrachloride solution of a fluorine-containing carboxylic acid (e.g., Asahi Glass Research Report, Vol. 32, pp. 129-159, 1982). year) is known.
しかしながら、水溶液中で反応した場合には、生成する
塩が溶解すること、また界面活性剤であるために発泡す
るなどして分離・精製が極めて困難である。また、四塩
化炭素溶媒では、含フッ素カルボン酸の溶解度が小さく
、多量の溶媒が必要であると同時に、生成沈殿物を分離
精製する場合に、トリクロロ−トリフルオロエタンなど
で洗浄する必要がある。したがって、これら従来法は工
業的技術として充分満足できるものとは言い難い。However, when reacting in an aqueous solution, the resulting salt dissolves, and since it is a surfactant, it foams, making separation and purification extremely difficult. Furthermore, the solubility of fluorine-containing carboxylic acids is low in carbon tetrachloride solvents, and a large amount of solvent is required. At the same time, when separating and purifying the produced precipitate, it is necessary to wash it with trichloro-trifluoroethane or the like. Therefore, these conventional methods cannot be said to be fully satisfactory as industrial techniques.
本発明者らは、上記の如き状況に鑑み、温和な条件で簡
便にかつ高収率で含フッ素カルボン酸アンモニウム塩を
合成し、容易に単離・精製できる方法につき鋭意研究を
行った結果、エーテル系溶媒は含フッ素カルボン酸の溶
解度が太き（かつ含フッ素カルボン酸アンモニウム塩の
溶解度は非常に小さいことに着目し、本発明を完成させ
る忙至った。In view of the above-mentioned circumstances, the present inventors have conducted extensive research on a method for easily synthesizing, easily isolating and purifying fluorine-containing carboxylic acid ammonium salts under mild conditions and in high yields. Focusing on the fact that ether solvents have a high solubility for fluorine-containing carboxylic acids (and that ammonium salts of fluorine-containing carboxylic acids have very low solubility), we have been busy completing the present invention.
すなわち、本発明は一般式Ｒｆｃｏ、ａ（但し、Ｒｆは
炭素数１〜２０の直鎖又は分枝鎖を有する含フッ素脂肪
族基を示す）であらわされる含フッ素カルボン酸とアン
モニアを反応させる事により、一般式Ｒｆｃｏ、Ｎｎ、
（但し、Ｒｆは前記に同じ）を製造する方法において、
畳応溶媒としてエーテル系溶媒を使用することを特徴と
する含フッ素カルボン酸アンモニウム塩の製造方法忙係
るものである。That is, the present invention involves reacting a fluorine-containing carboxylic acid represented by the general formula Rfco, a (where Rf represents a straight chain or branched fluorine-containing aliphatic group having 1 to 20 carbon atoms) with ammonia. According to the general formula Rfco, Nn,
(However, Rf is the same as above) In the method of manufacturing
This invention relates to a method for producing a fluorine-containing carboxylic acid ammonium salt, which is characterized in that an ether solvent is used as a reaction solvent.
以下、本発明について詳細に説明する。The present invention will be explained in detail below.
本発明の方法で使用される一般式ＲｆＯＯ！Ｈ（Ｒｆは
前記に同じ）であらわされる含フッ素カルボン酸として
は、種々のものを用いることができる。The general formula RfOO! used in the method of the invention! As the fluorine-containing carboxylic acid represented by H (Rf is the same as above), various types can be used.
例えば、一般式０ｎＰ１．＋、Ｃｏ、Ｈ（但し、ｎは２
８以下の自然数）であらわされる直鎖あるいは分枝した
ペルフルオロカルボン酸さらに具体的には、ＯＦ、Ｃｏ
、Ｈ，Ｃ！、？、（！Ｏ，Ｈ，Ｏ８Ｆ、Ｃｏ、Ｈ，Ｃ！
、Ｆ、Ｃｏ、Ｈ，Ｃ！、Ｆ１３Ｃｏ、Ｈ。For example, the general formula 0nP1. +, Co, H (however, n is 2
More specifically, OF, Co
,H,C! ,? , (!O,H,O8F,Co,H,C!
,F,Co,H,C! , F13Co, H.
Ｃ？′ＦｌｌｌＣｏｆｆｉＨ＊ Ｃ１１Ｆｌ？ＣＯ！Ｈ
ｓ ｃ（１’１９ｃｏ！Ｌ ｃｌｌｌ’１ｌｃｏＩＬ０
１、Ｆ、、Ｃｏ、Ｈ，（ａｙ、）ｌｃｙａｏ、ａ、 （
ａｙ３）、ａｙ（ａｙ晶ｃｏ、ｎなどを例示できる。特
に、エーテル系溶媒への生成物との溶解度差が大きい前
記Ｒｆの炭素数が６〜１２のものが特に好ましい。また
これら含フッ素カルボン酸は単独でもあるいは炭素数の
異なるものどの混合物でも使用可能である。C? 'FllllCoffiH* C11Fl? CO! H
s c(1'19co!L cll'1lcoIL0
1,F,,Co,H,(ay,)lcyao,a,(
Examples include ay3), ay (ay crystal co, n, etc.) In particular, Rf having a carbon number of 6 to 12 is particularly preferable because it has a large solubility difference with the product in an ether solvent.Also, these fluorine-containing carbon atoms Acids can be used alone or in any mixture of acids having different carbon numbers.
また、ａｙ、−Ｃ！Ｆ（ＯＦＩ）ｍｏ０２Ｈ、６ｐ３（
ａＦｌ、）ｍａｙ−０−００，Ｈ（ＯＦＪｚ？
（但し、ｍ及びｔは０又は１以上の整数）等で表わされ
る分子内に二重結合を有するペルフルオロカルボン酸、
また、例えばＰ（ａｙ、）ｍａＨ，（ａＦ、’）ｚｃｏ
、ａ 。Also, ay, -C! F(OFI)mo02H,6p3(
aFl, )may-0-00,H(OFJz? (where m and t are integers of 0 or 1 or more), etc.) A perfluorocarboxylic acid having a double bond in the molecule,
Also, for example, P(ay,)maH, (aF,')zco
,a.
ＯＩＦ、（ＯＦ、）ｍＯＨ，ＯＨ，Ｃｏ、Ｈ，ＨＣＦ、
（ｃＰ、）ｍＣ！Ｏ，Ｈ（但しｍ。OIF, (OF,)mOH,OH,Co,H,HCF,
(cP,)mC! O, H (However, m.
ｔは前記に同じ）等であらわされる分子鎖の一部に水素
原子が結合された含フッ素カルボン酸も使用可能である
。但し、含フッ素カルボン酸の溶媒に対する溶解性を考
慮すれば、前記Ｒｆ基の炭素数は２０以下であることが
好ましい。It is also possible to use a fluorine-containing carboxylic acid in which a hydrogen atom is bonded to a part of the molecular chain, such as (t is the same as above). However, in consideration of the solubility of the fluorine-containing carboxylic acid in a solvent, the number of carbon atoms in the Rf group is preferably 20 or less.
本発明の方法においては、反応溶媒としてニーチル系溶
媒を使用する。エーテル系溶媒としては例エバ、メチル
エーテル、エチルエーテル、ｎ−プロピルエーテル、イ
ソプロピルエーテル、ブチルエーテル、テトラヒドロフ
ラン、１．４−ジオキサン、フェニルエーテル、アニソ
ールなどが挙げられる。上記溶媒は、単独でもあるいは
二種以上の混合系でも使用可能である。特に、含フッ素
カルボン酸の溶解度が太き（、かつ含フッ素カルボン酸
アンそニウム塩の溶解度が小さいエチルエーテル、ｎ−
７’ロピルエーテル、イソプロピルエーテル、ブチルエ
ーテル、テトラヒドロフランが特に好ましい。上記した
溶媒の使用量は、反応温度含フッ素カルボン酸の種類に
より若干異なるが、通常含フッ素カルボン酸の濃度が５
〜８０重量パーセントの範囲で使用される。５重量パー
セント以下では、使用する溶媒量が多量となり、また８
０重量パーセント以上では、系中に析出する生成物の懸
＃Ａ−拌が困難となる。反応操作、生成物の分離をより
簡便とするために、特に２０〜５０重量パーセントで一
部することが好ましい。In the method of the present invention, a nityl solvent is used as a reaction solvent. Examples of ether solvents include Eva, methyl ether, ethyl ether, n-propyl ether, isopropyl ether, butyl ether, tetrahydrofuran, 1,4-dioxane, phenyl ether, and anisole. The above solvents can be used alone or in a mixed system of two or more. In particular, ethyl ether, n-
Particularly preferred are 7'lopyl ether, isopropyl ether, butyl ether and tetrahydrofuran. The amount of the above-mentioned solvent used varies slightly depending on the reaction temperature and the type of fluorine-containing carboxylic acid, but usually the concentration of the fluorine-containing carboxylic acid is 5.
-80 weight percent. If it is less than 5% by weight, a large amount of solvent will be used, and
If it is more than 0 weight percent, it becomes difficult to suspend and stir the product precipitated in the system. In order to simplify reaction operations and product separation, it is particularly preferable to use a portion of 20 to 50% by weight.
本発明の方法では、アンモニアはガス状で反応系に通気
することが好ましい。使用量は含フッ素カルボン酸に対
して当量で充分であるが、反応効率を高めるために少過
剰量（〜１．３当量）使用することができる。大過剰量
使用すると、過剰のアンモニアの除去が必要となりまた
製品着色等の問題が発生し好ましくない場合がある。通
気速度は特に限定されないが発熱量あるいは反応時間の
短縮等の観点から、１〜５０ ｍｍｏＬ／ｘ１１１ｎの
範囲で通気することが好ましく、特に５〜２０ｍｍ０Ｌ
／ｍ１ｎが好ましい。In the method of the invention, ammonia is preferably passed through the reaction system in gaseous form. An equivalent amount to the fluorine-containing carboxylic acid is sufficient, but a slight excess (up to 1.3 equivalents) may be used to increase reaction efficiency. If a large excess amount is used, it may be undesirable to remove excess ammonia and cause problems such as coloring of the product. The aeration rate is not particularly limited, but from the viewpoint of shortening the calorific value or reaction time, it is preferable to aerate in the range of 1 to 50 mm0L/x111n, particularly 5 to 20 mm0L.
/m1n is preferred.
本発明の反応は、広い温度範囲で行ない得るが、通常は
０〜１００℃の温度範囲で行なうことが望ましい。０℃
以下では、含フッ素カルボン酸のエーテル系溶媒への溶
解度が小さ（なり、多量の溶媒を必要とする。１００℃
以上では、使用する溶媒の沸点等を考慮すると反応操作
が複雑となり好ましくない。The reaction of the present invention can be carried out in a wide temperature range, but it is usually desirable to carry out the reaction in a temperature range of 0 to 100°C. 0℃
Below, the solubility of the fluorine-containing carboxylic acid in the ether solvent is small (and a large amount of solvent is required.
In the above case, the reaction operation becomes complicated when considering the boiling point of the solvent used, etc., which is not preferable.
反応は、上記した含フッ素カルボン酸をエーテル系溶媒
に溶解し、所定の温度下にアンモニアガスを通気すると
とＫより行なう事ができる。生成する含フッ素カルボン
酸アンモニウム塩は、エーテル系溶媒に対する溶解度が
小さいことから、反応中糸中に析出し懸濁状態となる。The reaction can be carried out using K by dissolving the above-mentioned fluorine-containing carboxylic acid in an ether solvent and passing ammonia gas through the solution at a predetermined temperature. Since the produced fluorine-containing carboxylic acid ammonium salt has low solubility in ether solvents, it precipitates in the reaction medium and becomes suspended.
但し、反応中均−溶液とする為に加熱、加温することは
可能である。反応後を、これを必要な場合には冷却した
後ろ別分離、同溶媒で洗浄することにより含フッ素カル
ボン酸アンモニウム塩を容易に分離精製できる。However, it is possible to heat the mixture to form a homogeneous solution during the reaction. After the reaction, the fluorine-containing carboxylic acid ammonium salt can be easily separated and purified by cooling if necessary, followed by separate separation and washing with the same solvent.
本発明の方法によれば、反応溶媒としてエーテル系溶媒
を使用することにより含フッ素カルボン酸をほぼ定量的
に目的とする含フッ素カルボン酸アンモニウム塩に変換
することができかつ精製工程も簡便となり単離操作が容
易となるなどの効果をもたらす。According to the method of the present invention, by using an ether solvent as a reaction solvent, a fluorine-containing carboxylic acid can be almost quantitatively converted into the target fluorine-containing carboxylic acid ammonium salt, and the purification process is also simple and simple. This brings about effects such as ease of release operation.
以下、実施例により、本発明を更に詳細忙説明するが、
本発明はこれらに限定されるものではない。Hereinafter, the present invention will be explained in more detail with reference to Examples.
The present invention is not limited to these.
実施例
アンモニアガスの通気管及び還流冷却器を備え、底部抜
き出し孔を設けた２０ｔの４０フラスコにヘプタデカフ
ルオロノナン酸９００９（１，９４モル）及びインフロ
ビルエーテル２１００ ｙ全加工、室温下に攪拌し完全
に溶解した。次いで、同温度下にアンモニアガス５７．
４９（２，２モル）を４６時間かけて通気した。通気後
、懸濁液をろ別し、得られる白色結晶を２００ｇのイン
フロビルエーテルで洗浄、乾燥し、９１５９（１，９モ
ル）のへブタデカフルオロノナン酸アンモニウム塩を得
た。Example: Heptadecafluorononanoic acid 9009 (1.94 mol) and Inflovir ether 2100 y were completely processed in a 20 t 40 flask equipped with an ammonia gas vent pipe and a reflux condenser and a bottom extraction hole at room temperature. Stir to completely dissolve. Next, 57.5% of ammonia gas was added at the same temperature.
49 (2.2 mol) was bubbled through over 46 hours. After aeration, the suspension was filtered, and the resulting white crystals were washed with 200 g of inflovir ether and dried to obtain 9159 (1.9 mol) of hebutadecafluorononanoic acid ammonium salt.
（収率９８チ）(Yield 98 cm)
Claims (3)
２０の直鎖又は分岐鎖を有する含フッ素脂肪族基を示す
）であらわされる含フッ素カルボン酸とアンモニアを反
応させる事により、一般式ＲｆＣＯ＿２ＮＨ＿４（但し
、Ｒｆは前記に同じ）で表わされる含フッ素カルボン酸
アンモニウム塩を製造する方法において、反応溶媒とし
てエーテル系溶媒を使用することを特徴とする含フッ素
カルボン酸アンモニウム塩の製造方法。(1) General formula RfCO_2H (however, Rf has 1 to 1 carbon atoms
By reacting a fluorine-containing carboxylic acid represented by a fluorine-containing aliphatic group having a straight chain or branched chain with ammonia, a fluorine-containing carboxylic acid represented by the general formula RfCO_2NH_4 (however, Rf is the same as above) is produced. A method for producing a fluorine-containing carboxylic acid ammonium salt, the method comprising using an ether solvent as a reaction solvent.
＋＿１ＣＯ＿２Ｈ（但し、ｎは２０以下の自然数）であ
らわされるペルフルオロカルボン酸である特許請求の範
囲第１項に記載の方法。(2) The fluorine-containing carboxylic acid has the general formula CnF_2_n_
The method according to claim 1, which is a perfluorocarboxylic acid represented by +_1CO_2H (where n is a natural number of 20 or less).
ルエーテル、イソプロピルエーテル、ブチルエーテル、
テトラヒドロフランである特許請求の範囲の第１項から
第２項に記載の方法。(3) The ether solvent is ethyl ether, n-propyl ether, isopropyl ether, butyl ether,
The method according to claims 1 to 2, wherein tetrahydrofuran is used.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP62312178A JP2535987B2 (en) | 1987-12-11 | 1987-12-11 | Method for producing fluorinated carboxylic acid ammonium salt |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP62312178A JP2535987B2 (en) | 1987-12-11 | 1987-12-11 | Method for producing fluorinated carboxylic acid ammonium salt |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH01153654A true JPH01153654A (en) | 1989-06-15 |
| JP2535987B2 JP2535987B2 (en) | 1996-09-18 |
Family
ID=18026160
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP62312178A Expired - Lifetime JP2535987B2 (en) | 1987-12-11 | 1987-12-11 | Method for producing fluorinated carboxylic acid ammonium salt |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2535987B2 (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1995000469A1 (en) * | 1993-06-18 | 1995-01-05 | Idemitsu Petrochemical Co., Ltd. | Process for producing ammonium salt of perfluoro carboxylic acid |
| US5591877A (en) * | 1993-06-02 | 1997-01-07 | Hoechst Ag | Process for the recovery of fluorinated carboxylic acids |
| US7074953B2 (en) * | 2001-12-04 | 2006-07-11 | Basf Aktiengesellschaft | Production of ammonium salts of aromatic carboxylic acids |
| WO2016021441A1 (en) * | 2014-08-08 | 2016-02-11 | ユニマテック株式会社 | Mixture of polyfluoroalkene carboxylic acid or salt thereof and production method therefor |
-
1987
- 1987-12-11 JP JP62312178A patent/JP2535987B2/en not_active Expired - Lifetime
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5591877A (en) * | 1993-06-02 | 1997-01-07 | Hoechst Ag | Process for the recovery of fluorinated carboxylic acids |
| WO1995000469A1 (en) * | 1993-06-18 | 1995-01-05 | Idemitsu Petrochemical Co., Ltd. | Process for producing ammonium salt of perfluoro carboxylic acid |
| US7074953B2 (en) * | 2001-12-04 | 2006-07-11 | Basf Aktiengesellschaft | Production of ammonium salts of aromatic carboxylic acids |
| WO2016021441A1 (en) * | 2014-08-08 | 2016-02-11 | ユニマテック株式会社 | Mixture of polyfluoroalkene carboxylic acid or salt thereof and production method therefor |
| JP5896094B1 (en) * | 2014-08-08 | 2016-03-30 | ユニマテック株式会社 | Mixture of polyfluoroalkenecarboxylic acid or salt thereof and process for producing the same |
| US9873654B2 (en) | 2014-08-08 | 2018-01-23 | Unimatec Co., Ltd. | Mixture of polyfluoroalkene carboxylic acids or salts thereof and process for producing the same |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2535987B2 (en) | 1996-09-18 |
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