JPS63190893A - Production of phosphonium carboxylic acid salt - Google Patents
Production of phosphonium carboxylic acid saltInfo
- Publication number
- JPS63190893A JPS63190893A JP2278687A JP2278687A JPS63190893A JP S63190893 A JPS63190893 A JP S63190893A JP 2278687 A JP2278687 A JP 2278687A JP 2278687 A JP2278687 A JP 2278687A JP S63190893 A JPS63190893 A JP S63190893A
- Authority
- JP
- Japan
- Prior art keywords
- phosphonium
- carboxylic acid
- acid
- production
- formula
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 7
- -1 phosphonium carboxylic acid salt Chemical class 0.000 title claims description 20
- DJFBJKSMACBYBD-UHFFFAOYSA-N phosphane;hydrate Chemical compound O.P DJFBJKSMACBYBD-UHFFFAOYSA-N 0.000 claims abstract description 7
- 150000004714 phosphonium salts Chemical class 0.000 claims abstract description 7
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 claims abstract description 5
- 239000003456 ion exchange resin Substances 0.000 claims abstract description 5
- 229920003303 ion-exchange polymer Polymers 0.000 claims abstract description 5
- 230000003472 neutralizing effect Effects 0.000 claims abstract description 4
- 150000001735 carboxylic acids Chemical class 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract description 12
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 abstract description 8
- 238000005349 anion exchange Methods 0.000 abstract description 6
- 150000001450 anions Chemical class 0.000 abstract description 6
- 239000005711 Benzoic acid Substances 0.000 abstract description 4
- 125000000217 alkyl group Chemical group 0.000 abstract description 4
- 125000003118 aryl group Chemical group 0.000 abstract description 4
- 235000010233 benzoic acid Nutrition 0.000 abstract description 4
- 239000003054 catalyst Substances 0.000 abstract description 2
- IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical compound COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 abstract description 2
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 abstract 2
- WPWHSFAFEBZWBB-UHFFFAOYSA-N 1-butyl radical Chemical compound [CH2]CCC WPWHSFAFEBZWBB-UHFFFAOYSA-N 0.000 abstract 1
- 235000011054 acetic acid Nutrition 0.000 abstract 1
- 235000006408 oxalic acid Nutrition 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000000243 solution Substances 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 239000002994 raw material Substances 0.000 description 7
- 239000002904 solvent Substances 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
- 239000012670 alkaline solution Substances 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 239000003957 anion exchange resin Substances 0.000 description 3
- 150000007942 carboxylates Chemical class 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 229910001507 metal halide Inorganic materials 0.000 description 3
- 150000005309 metal halides Chemical class 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- TWWBIMNLBUYJKB-UHFFFAOYSA-N phosphanyl acetate Chemical compound CC(=O)OP TWWBIMNLBUYJKB-UHFFFAOYSA-N 0.000 description 3
- 229910052709 silver Inorganic materials 0.000 description 3
- 239000004332 silver Substances 0.000 description 3
- 235000011121 sodium hydroxide Nutrition 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 2
- 238000005342 ion exchange Methods 0.000 description 2
- ADZWSOLPGZMUMY-UHFFFAOYSA-M silver bromide Chemical compound [Ag]Br ADZWSOLPGZMUMY-UHFFFAOYSA-M 0.000 description 2
- 125000000547 substituted alkyl group Chemical group 0.000 description 2
- 125000003107 substituted aryl group Chemical group 0.000 description 2
- GFZMLBWMGBLIDI-UHFFFAOYSA-M tetrabutylphosphanium;acetate Chemical compound CC([O-])=O.CCCC[P+](CCCC)(CCCC)CCCC GFZMLBWMGBLIDI-UHFFFAOYSA-M 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 241000212977 Andira Species 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- SQVRNKJHWKZAKO-UHFFFAOYSA-N beta-N-Acetyl-D-neuraminic acid Natural products CC(=O)NC1C(O)CC(O)(C(O)=O)OC1C(O)C(O)CO SQVRNKJHWKZAKO-UHFFFAOYSA-N 0.000 description 1
- 229910002090 carbon oxide Inorganic materials 0.000 description 1
- 150000001734 carboxylic acid salts Chemical class 0.000 description 1
- 239000003518 caustics Substances 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 125000000962 organic group Chemical group 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- SQVRNKJHWKZAKO-OQPLDHBCSA-N sialic acid Chemical compound CC(=O)N[C@@H]1[C@@H](O)C[C@@](O)(C(O)=O)OC1[C@H](O)[C@H](O)CO SQVRNKJHWKZAKO-OQPLDHBCSA-N 0.000 description 1
- CQLFBEKRDQMJLZ-UHFFFAOYSA-M silver acetate Chemical compound [Ag+].CC([O-])=O CQLFBEKRDQMJLZ-UHFFFAOYSA-M 0.000 description 1
- 229940071536 silver acetate Drugs 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- BJQWBACJIAKDTJ-UHFFFAOYSA-N tetrabutylphosphanium Chemical compound CCCC[P+](CCCC)(CCCC)CCCC BJQWBACJIAKDTJ-UHFFFAOYSA-N 0.000 description 1
- RKHXQBLJXBGEKF-UHFFFAOYSA-M tetrabutylphosphanium;bromide Chemical compound [Br-].CCCC[P+](CCCC)(CCCC)CCCC RKHXQBLJXBGEKF-UHFFFAOYSA-M 0.000 description 1
Abstract
Description
【発明の詳細な説明】
（産業上の利用分野）
この発明は、ホスホニウムカルボン酸塩の製法に関する
ものである。この発明のホスホニウムカルボン酸塩は、
例えばメタノール、−酸化炭素及び酸素とから炭酸ジメ
チルを製造する際の触媒成分として使用することができ
る。DETAILED DESCRIPTION OF THE INVENTION (Industrial Field of Application) The present invention relates to a method for producing a phosphonium carboxylate. The phosphonium carboxylate of this invention is
For example, it can be used as a catalyst component in the production of dimethyl carbonate from methanol, carbon oxide and oxygen.
（従来技術および問題点） 従来、ホスホニウムカルボン酸塩は例えばＪ。(Prior art and problems) Conventionally, phosphonium carboxylates have been described, for example, in J.
Ｏｒｇ、 Ｃｈｅｍ、、 ２８．１１３３ （１９６３
）に記載されているように、ホスホニウムハライドとカ
ルボン酸塩とから製造されている。例えば（式１）のよ
うにしてテトラブチルホスホニウムアセテートは製造さ
れる。Org, Chem, 28.1133 (1963
), it is produced from a phosphonium halide and a carboxylate salt. For example, tetrabutylphosphonium acetate is produced as shown in (Formula 1).
Ｂｕ４Ｐ Ｂｒ ＋ Ａｇ０Ａｃ−＋Ｂｕ４ＰＯＡｃ
＋ ＡｇＢｒ （式−１）副生ずる臭化銀は、溶媒（
メタノール）に対する溶解度が低いため、殆んど固体と
して存在するだめ、濾過により比較的容易に溶媒（メタ
ノール）に溶解しているホスホニウムアセテートを単離
できる。しかしこの方法は原料であるカルボン酸塩が非
常に高価であるという欠点がある。Bu4PBr + Ag0Ac-+Bu4POAc
+AgBr (Formula-1) The silver bromide produced as a by-product is
Because phosphonium acetate has low solubility in the solvent (methanol), it exists mostly as a solid, so phosphonium acetate dissolved in the solvent (methanol) can be isolated relatively easily by filtration. However, this method has the disadvantage that the raw material, the carboxylic acid salt, is very expensive.
一方銀の代りにより安価な他の金属（例えばカリウム）
のカルボン酸塩を用いる方法もあるが、この場合、副生
ずる金属ハライドは、銀ハライドに比べて溶媒に対する
溶解度が著しく大きいために、生成するホスホニウムカ
ルボン酸塩とともに溶媒に一部溶解しており、濾過によ
って得られるホスホニウムカルボン酸塩中には、金属ハ
ライドが混入してしまうという欠点がある。while other less expensive metals (e.g. potassium) can be substituted for silver.
There is also a method of using a carboxylate of phosphonium carboxylate, but in this case, the by-product metal halide has significantly higher solubility in the solvent than silver halide, so it is partially dissolved in the solvent together with the phosphonium carboxylate that is produced. The phosphonium carboxylate obtained by filtration has the disadvantage that metal halides are mixed therein.
本発明は、上記の点に鑑み、高価なカルボン酸塩を使用
することなく、また、金属ハライドの混入のない、安価
なホスホニウムカルボン酸塩の製法を提供することを目
的とするものである。In view of the above points, it is an object of the present invention to provide an inexpensive method for producing phosphonium carboxylates without using expensive carboxylates and without contamination with metal halides.
（問題点を解決するための手段）
本発明はホスホニウム塩をイオン交換樹脂でアニオン交
換することにより得られたホスホニウムヒドロキシドを
カルデン酸で中和することを特徴とするホスホニウムカ
ルボン酸塩の製法である。(Means for Solving the Problems) The present invention is a method for producing a phosphonium carboxylate, which is characterized in that phosphonium hydroxide obtained by anion exchange of a phosphonium salt with an ion exchange resin is neutralized with caldic acid. be.
本発明のホスホニウム塩は（式−２）で示されるもので
ある。The phosphonium salt of the present invention is represented by (Formula-2).
式中Ｒ，％Ｒ，はアルキル基、アリール基、置換アルキ
ル基、又は置換アリール基を示し、同一でも異なってい
ても良い。又式中のＸはｎ価の陰イオン部を示し・・ラ
イドイオン、硫酸イオン、硝酸イオン、炭酸イオン、カ
ルボン酸イオン等であり、具体的には例えば
（ｎ −Ｃ４Ｉ（９） ａ ｐ ｃｚ、（ｎ −Ｃ４Ｈ
９） ４ＰＢｒ ＋ （ｎ −Ｃ４Ｈ９）ＰＩ（Ｃ６Ｈ
５）４ＰＣ１，（Ｃ６Ｈ５）４ＰＢｒ、（Ｃ６Ｈ５）Ｐ
Ｃｔ［（ｎ−Ｃ４Ｈ２）４Ｐ］２Ｓ０４．テトラ（）ぞ
ラシアノフェニル）ホスホニウムプロミドなどが挙げら
れる。In the formula, R and %R represent an alkyl group, an aryl group, a substituted alkyl group, or a substituted aryl group, and may be the same or different. In addition, X in the formula represents an n-valent anion moiety, such as a ride ion, sulfate ion, nitrate ion, carbonate ion, carboxylate ion, etc. Specifically, for example, (n -C4I(9) a p cz , (n-C4H
9) 4PBr + (n -C4H9)PI(C6H
5) 4PC1, (C6H5)4PBr, (C6H5)P
Ct[(n-C4H2)4P]2S04. Examples include tetra()zolacyanophenyl)phosphonium bromide.
カルピン酸は式−４で示され
ＲＣ０ＯＨ（式−４）
式中Ｒはアルキル、アリール、及び置換アルキル及び置
換アリールであり、例えば
酢酸、安息香酸、・やラシア７安息香酸、マロン酸、シ
ーウ酸などが挙げられる。Carpinic acid is represented by the formula-4, RCOOH (formula-4), where R is alkyl, aryl, substituted alkyl, and substituted aryl, such as acetic acid, benzoic acid, racia benzoic acid, malonic acid, and sialic acid. Examples include.
アニオン交換には、アニオン交換樹脂が用いられるが、
原料のホスホニウム塩の性質やアニオン交換時に使用さ
れる溶媒の性質によって交換基の種類や、樹脂の構造を
適宜選択することができる。Anion exchange resin is used for anion exchange, but
The type of exchange group and the structure of the resin can be appropriately selected depending on the properties of the raw material phosphonium salt and the properties of the solvent used during anion exchange.
具体的なアニオン交換樹脂としては例えば、日本オルガ
ノ商会製のアンバーライ） ＩＲＡ−４００■やＩＲＡ
９００■などが用いられる。これらのアニオン交換樹脂
はカラムに充填して通常の方法（例えば苛性ソーダ水溶
液で交換基のアニオンをヒドロキシイオンに交換したあ
と、残留する苛性ソーダを純水で洗浄する）で交換基の
アニオ／をヒドロキシイオンに交換することができる。Examples of specific anion exchange resins include Amberly) IRA-400■ and IRA manufactured by Nippon Organo Shokai.
900■ etc. are used. These anion exchange resins are packed in a column and the exchange group anions are exchanged with hydroxy ions using a caustic soda aqueous solution, and then the remaining caustic soda is washed with pure water to convert the exchange group anions to hydroxy ions. can be exchanged for.
続いて原料のホスホニウム塩を水溶液または、メタノー
ル等の有機溶媒の溶液の形で流してアニオン交換を行い
、含水ホスホニウムヒドロキシド溶液を得ることができ
る。Subsequently, the raw material phosphonium salt is passed in the form of an aqueous solution or a solution of an organic solvent such as methanol to perform anion exchange, thereby obtaining a hydrous phosphonium hydroxide solution.
又交換基のアニオンをヒドロキシイオンに交換し、水洗
した後、充分脱水した水と相容性のあるメタノール、ア
セトンなどの有機溶媒を流して、カラム内の水分を除き
、続いて、カラムにホスホニウム塩の充分脱水した有機
溶媒の溶液を流すことにより、ホスホニウムヒドロキシ
ドを非水の型で得ることもできる。また、一度アニオン
交換したカラムハ置換基のアニオ／をヒドロキシイオン
に交換すること（例えば苛性ノーグ水溶液による交換及
び水洗）により何回でも再使用が可能である。In addition, after exchanging the anion of the exchange group with hydroxy ion and washing with water, water in the column is removed by flowing an organic solvent such as methanol or acetone that is compatible with sufficiently dehydrated water. Phosphonium hydroxide can also be obtained in non-aqueous form by running a solution of the salt in a fully dehydrated organic solvent. Further, the column can be reused any number of times by exchanging the anion/substituent of the column with a hydroxy ion (for example, exchanging with a caustic Nog aqueous solution and washing with water).
このようにして得られたホスホニウムヒドロキシド溶液
にほぼ当量のカルピン酸を加えて中和することにより目
的のホスホニウムカルボン酸塩が得られる。The desired phosphonium carboxylate salt is obtained by neutralizing the phosphonium hydroxide solution obtained in this manner by adding approximately an equivalent amount of carpinic acid.
（発明の効果） 本発明は次のような利点がある。(Effect of the invention) The present invention has the following advantages.
（１）高価なカルブ／酸銀を原料としないので、安価に
ホスホニウムカルボン酸塩を得ることができる。(1) Since expensive carb/acid silver is not used as a raw material, phosphonium carboxylate can be obtained at low cost.
（２）金属カルボン酸塩を原料としないので、ホスホニ
ウムカルボン酸塩を該金属を含有しない純粋な形で得る
ことができる。(2) Since a metal carboxylate is not used as a raw material, the phosphonium carboxylate can be obtained in a pure form that does not contain the metal.
（３）原料のホスホニウム塩、及び原料のカルピン酸の
種類を変えることによって、任意のホスホニウムカルボ
ン酸塩を製造することができる。(3) Any phosphonium carboxylate can be produced by changing the type of phosphonium salt as a raw material and carpic acid as a raw material.
以下実施例により本発明を具体的に説明する。The present invention will be specifically explained below using Examples.
実施例１
（１）内径５１０１ｍのガラスカラムにオルガノ商会製
アニオン交換樹脂ＩＲＡ−９００■を１１．湿式％式％
（２）続いて８ｗｔ％苛性ソーダのイオン交換水溶液２
．６１を１．６．／／ｈの流速で流した。Example 1 (1) 11. Wet % formula % (2) Next, 8 wt% caustic soda ion exchange aqueous solution 2
．． 61 to 1.6. It was flowed at a flow rate of //h.
（３）続いて、イオン交換水１．１１を１．６１／ｈの
流速で流した。(3) Subsequently, 1.1 l of ion-exchanged water was flowed at a flow rate of 1.61/h.
（４）続いて、イオン交換水４０１を７．１！／ｈの流
速で流した。(4) Next, add ion exchange water 401 to 7.1! It was flowed at a flow rate of /h.
（５）続いて、脱水メタノール４．３１を１．６１／ｈ
の流速で流した。(5) Next, add 4.31 dehydrated methanol at 1.61/h.
It was flowed at a flow rate of
（６）続いて、テトラブチルホスホニウムプロミド１６
６５１−（０，４９４モル）の脱水メタノール溶液（３
０ｗｔ％）を１．６１／ｈの流速で流した。(6) Subsequently, tetrabutylphosphonium bromide 16
651-(0,494 mol) in dehydrated methanol solution (3
0 wt%) was flowed at a flow rate of 1.61/h.
（７）続いて、脱水メタノールを１．６Ａ’／ｈの流速
で流し、カラムから流出してくるアルカリ性溶液を１１
１２Ｐ分取した。(7) Next, dehydrated methanol was flowed at a flow rate of 1.6 A'/h, and the alkaline solution flowing out from the column was
12P was fractionated.
（８）該アルカリ性溶液の一部をｏ、 ｉ ＮＨｃｔで
中和滴定したところ、１１当り、０．３８８ミリモルの
アルカリ成分（全アルカリ性溶液中のアルカリ成分量と
して０．４．３１モル）が存在することがわかった。(8) When a part of the alkaline solution was neutralized and titrated with o, i NHct, 0.388 mmol of alkaline component (0.4.31 mol as the amount of alkaline component in the total alkaline solution) was present per 11 I found out that it does.
（９）残った該アルカリ性溶液１１００ｆｉ’にアルカ
リ成分量と当量の酢酸２５．６３ ｇ−（０，４２７モ
ル）を加え中和した。その結果、テトラブチルホスホニ
ウムアセテート１３５．９６ Ｐ （０，４２７モル〕
のメタノール溶液１１２６７を得た。該溶液を減圧下に
溶媒を除去して得られた粘稠な液体の赤外吸収スペクト
ルは、１４０８α−１と１５７０の−１にアセテートの
吸収を示し、別途酢酸銀法で合成したホスホニウムアセ
テートと同一であった。(9) 25.63 g (0,427 mol) of acetic acid equivalent to the amount of the alkaline component was added to the remaining 1100 fi' of the alkaline solution to neutralize it. As a result, 135.96 P (0,427 mol) of tetrabutylphosphonium acetate
A methanol solution of 11267 was obtained. The infrared absorption spectrum of the viscous liquid obtained by removing the solvent from the solution under reduced pressure shows absorption of acetate at 1408α-1 and 1570-1, which is similar to phosphonium acetate synthesized separately by the silver acetate method. They were the same.
実施例２
実施例１で使用したカラムを、純水１．１１を１．６１
／ｈで流し、以下実施例１の（２）以降の操作を行い、
計４回イオン交換樹脂の再使用を行い、実施例１と同様
の結果を得た。Example 2 The column used in Example 1 was used to convert pure water 1.11 to 1.61
/h, and perform the operations from (2) onwards in Example 1.
The ion exchange resin was reused a total of four times, and the same results as in Example 1 were obtained.
実施例３
酢酸の代りに、安息香酸を用いた他は実施例１の方法を
繰り返した。その結果、テトラブチルホスホニウムベン
ゾニー） １６５．５１７（０，４３５モル）のメタノ
ール溶液１１５：ｌを得た。Example 3 The method of Example 1 was repeated except that benzoic acid was used instead of acetic acid. As a result, a 115:l methanol solution of 165.517 (0,435 mol) of tetrabutylphosphonium benzony was obtained.
Claims (1)
とにより得られたホスホニウムヒドロキシドをカルボン
酸で中和することを特徴とするホスホニウムカルボン酸
塩の製法A method for producing a phosphonium carboxylate salt, which comprises neutralizing a phosphonium hydroxide obtained by anion-exchanging a phosphonium salt with an ion exchange resin with a carboxylic acid.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2278687A JPS63190893A (en) | 1987-02-03 | 1987-02-03 | Production of phosphonium carboxylic acid salt |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2278687A JPS63190893A (en) | 1987-02-03 | 1987-02-03 | Production of phosphonium carboxylic acid salt |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS63190893A true JPS63190893A (en) | 1988-08-08 |
Family
ID=12092358
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2278687A Pending JPS63190893A (en) | 1987-02-03 | 1987-02-03 | Production of phosphonium carboxylic acid salt |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS63190893A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1270583A1 (en) * | 2001-06-19 | 2003-01-02 | Basf Aktiengesellschaft | Process for the purification of phosphonium salts |
| US20160260645A1 (en) * | 2015-01-30 | 2016-09-08 | Panasonic Intellectual Property Management Co., Ltd. | Sealing epoxy resin composition, hardened product, and semiconductor device |
-
1987
- 1987-02-03 JP JP2278687A patent/JPS63190893A/en active Pending
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1270583A1 (en) * | 2001-06-19 | 2003-01-02 | Basf Aktiengesellschaft | Process for the purification of phosphonium salts |
| US20160260645A1 (en) * | 2015-01-30 | 2016-09-08 | Panasonic Intellectual Property Management Co., Ltd. | Sealing epoxy resin composition, hardened product, and semiconductor device |
| US9633922B2 (en) * | 2015-01-30 | 2017-04-25 | Panasonic Intellectual Property Management Co., Ltd. | Sealing epoxy resin composition, hardened product, and semiconductor device |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| KR101109177B1 (en) | Penam crystal and process for producing the same | |
| EP0306924B1 (en) | Process for preparing penicillanic acid derivatives | |
| CN110294712A (en) | A kind of preparation method of high-purity imidazole acetate ionic liquid | |
| JPS63190893A (en) | Production of phosphonium carboxylic acid salt | |
| US3760070A (en) | Manufacture of copper oxide | |
| JPH10505084A (en) | Method for producing tetrabromobisphenol-A by reducing formation of methyl bromide | |
| JP2897372B2 (en) | Production method of high quality tetrabromobisphenol A | |
| JP3394981B2 (en) | Method for producing free hydroxylamine aqueous solution | |
| RU2026280C1 (en) | Method of synthesis of 2,2-bis-(3',5'-dibromo-4'-hydroxyphenyl)-propane | |
| JP4300407B2 (en) | Method for producing tetraalkylammonium hydroxide | |
| JPS5865241A (en) | Carbonylation of secondary benzylhalide | |
| EP0341694B1 (en) | Method for production of 3-exomethylenecepham derivatives | |
| JPH0116815B2 (en) | ||
| US7138545B2 (en) | Metal salts | |
| KR20220026456A (en) | organic compounds containing 2-cyanoethyl group and preparing method thereof | |
| JP3043106B2 (en) | Method for producing water-soluble polyvinyl acetal resin | |
| JP2002338239A (en) | Method for synthesizing zeolite | |
| JPH11263602A (en) | Preparation of periodate | |
| JP3008552B2 (en) | Method for producing high quality tetrabromobisphenol A | |
| KR920006418B1 (en) | Process for the preparation of 1-(2-tetrahydrofuryl)-s-fluorouracil | |
| JPH10130181A (en) | Production of ethylene oxide adduct | |
| CN108047276A (en) | A kind of method for synthesizing acetylacetone,2,4-pentanedione ruthenium (III) | |
| JP4088076B2 (en) | Method for producing alkali iodine salt | |
| JPH0544957B2 (en) | ||
| JP2000095789A (en) | Production of phosphonium sulfoisophthalate derivative |