JPH02139046A - Separation recovery of transition metal catalyst - Google Patents
Separation recovery of transition metal catalystInfo
- Publication number
- JPH02139046A JPH02139046A JP63291948A JP29194888A JPH02139046A JP H02139046 A JPH02139046 A JP H02139046A JP 63291948 A JP63291948 A JP 63291948A JP 29194888 A JP29194888 A JP 29194888A JP H02139046 A JPH02139046 A JP H02139046A
- Authority
- JP
- Japan
- Prior art keywords
- transition metal
- catalyst
- reaction product
- metal catalyst
- recovered
- 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
- 229910052723 transition metal Inorganic materials 0.000 title claims abstract description 35
- 150000003624 transition metals Chemical class 0.000 title claims abstract description 33
- 239000003054 catalyst Substances 0.000 title claims abstract description 32
- 238000011084 recovery Methods 0.000 title claims description 9
- 238000000926 separation method Methods 0.000 title claims description 6
- 238000000034 method Methods 0.000 claims abstract description 22
- 239000007795 chemical reaction product Substances 0.000 claims abstract description 20
- 150000003464 sulfur compounds Chemical class 0.000 claims abstract description 8
- -1 H2S Chemical class 0.000 abstract description 3
- 229910052742 iron Inorganic materials 0.000 abstract description 2
- 239000010948 rhodium Substances 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 8
- 239000007788 liquid Substances 0.000 description 8
- 238000000605 extraction Methods 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 229910052703 rhodium Inorganic materials 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- VDQVEACBQKUUSU-UHFFFAOYSA-M disodium;sulfanide Chemical compound [Na+].[Na+].[SH-] VDQVEACBQKUUSU-UHFFFAOYSA-M 0.000 description 3
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 3
- 229910052979 sodium sulfide Inorganic materials 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 229910052759 nickel Inorganic materials 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- 229910052697 platinum Inorganic materials 0.000 description 2
- 238000001179 sorption measurement Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000007664 blowing Methods 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000001354 calcination Methods 0.000 description 1
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 238000003795 desorption Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 235000019441 ethanol Nutrition 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product 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
- 238000010992 reflux Methods 0.000 description 1
- 150000003284 rhodium compounds Chemical class 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/584—Recycling of catalysts
Landscapes
- Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Description
【発明の詳細な説明】
〔産業上の利用分野〕
本発明は遷移金属触媒を用いた化学合成プロセスに於い
て、使用した触媒を反応生成物中から分離回収する方法
に関するものである。DETAILED DESCRIPTION OF THE INVENTION [Industrial Application Field] The present invention relates to a method for separating and recovering a used catalyst from a reaction product in a chemical synthesis process using a transition metal catalyst.
〔従来の技術及び発明が解決しようとする課題〕化学合
成プロセスにおいて遷移金属触媒は、目的とする反応速
度を目覚ましく向上させることにより、その経済性を高
めている。特に、いわゆるＣ１化学ではＣｏ、 Ｎｉ、
Ｒｈ、 Ｐｄ、 Ｐｔ等の遷移金属触媒がよく用いら
れる。これらの触媒を用いた化学合成プロセスでは、生
成物中から触媒を分離する必要があり、特にＲｈ、 ｐ
ｄ、 ｐｔ、 ｌｒ等の高価な触媒を用いる場合には、
触媒を分離、回収する際の回収率がプロセスの経済性に
対して大きな影響を与える。[Prior Art and Problems to be Solved by the Invention] In chemical synthesis processes, transition metal catalysts dramatically improve the desired reaction rate, thereby increasing their economic efficiency. In particular, in so-called C1 chemistry, Co, Ni,
Transition metal catalysts such as Rh, Pd, and Pt are often used. In chemical synthesis processes using these catalysts, it is necessary to separate the catalysts from the products, especially Rh, p
When using expensive catalysts such as d, pt, lr,
The recovery rate when separating and recovering the catalyst has a major impact on the economics of the process.
従来知られている触媒を分離する方法としては、先ず反
応生成物が比較的低沸点であることを利用して、これを
フラッシュすることにより不揮発性触媒と分離する方法
がある。例えば、メタノール法酢酸合成プロセスにおけ
る酢酸とＲｈ触媒の分離にはこのフラッシュが用いられ
る。As a conventionally known method for separating a catalyst, there is a method that first takes advantage of the fact that the reaction product has a relatively low boiling point and flashes it to separate it from a non-volatile catalyst. For example, this flash is used to separate acetic acid and Rh catalyst in the methanol method acetic acid synthesis process.
また、反応生成物と触媒の溶解性の差を利用し、抽出分
離する方法がある。例えば、α−７エニルプロピオン酸
誘導体を含有する反応液に、水又は水と酢酸等の混合物
を抽出溶媒として添加し、反応生成物相と水相に二相分
離させ、水相に触媒として使用したロジウム化合物を抽
出し分離する方法（特開昭６３−１４９３４１．特開昭
６３−１６２６５３）などがある。There is also a method of extraction and separation that takes advantage of the difference in solubility between the reaction product and the catalyst. For example, water or a mixture of water and acetic acid, etc. is added as an extraction solvent to a reaction solution containing an α-7enylpropionic acid derivative, the reaction product phase and an aqueous phase are separated, and the aqueous phase is used as a catalyst. There are methods for extracting and separating the rhodium compounds (JP-A-63-149341, JP-A-63-162653).
さらに、触媒の回収率を上げ、プロセスの経済性を高め
るためには、上記のフラッシュ、抽出分離等の方法によ
り回収しきれなかった反応生成物中に残存する触媒を回
収することが必要であり、その手段としては、活性炭等
により吸着し、分離、回収する方法が提案されている（
特開昭６３−１６２０４４）。Furthermore, in order to increase the recovery rate of the catalyst and improve the economic efficiency of the process, it is necessary to recover the catalyst remaining in the reaction products that could not be recovered by the above-mentioned methods such as flashing and extraction separation. As a means of achieving this, a method has been proposed that involves adsorption, separation, and recovery using activated carbon, etc. (
JP-A-63-162044).
しかしながら、これらの方法においては、特に微量の遷
移金属の回収について不十分であったり、吸着、脱着等
に多大な設備やエネルギーを必要とする等、効率的では
なかった。However, these methods are not efficient, such as insufficient recovery of particularly trace amounts of transition metals, or requiring a large amount of equipment and energy for adsorption, desorption, etc.
本発明は遷移金属触媒を用いて得られた反応生成物中に
残存する遷移金属を簡単な方法により効率的に回収する
ことを目的とするものである。The object of the present invention is to efficiently recover transition metals remaining in reaction products obtained using transition metal catalysts by a simple method.
本発明者らは、かかる情況に鑑み鋭意研究を重ねた結果
、意外にも触媒を含む反応生成物に硫黄化合物を添加す
るだけでほぼ１００％まで遷移金属が回収できることを
見出し、本発明に到った。The present inventors have conducted extensive research in view of the above circumstances, and have unexpectedly discovered that almost 100% of transition metals can be recovered by simply adding a sulfur compound to a reaction product containing a catalyst, and have thus arrived at the present invention. It was.
即ち本発明は、遷移金属触媒を用いて得られた反応生成
物中に残存する遷移金属を、硫黄化合物を用いて分離回
収することを特徴とする遷移金属触媒の分離回収方法で
ある。That is, the present invention is a method for separating and recovering a transition metal catalyst, characterized in that the transition metal remaining in a reaction product obtained using a transition metal catalyst is separated and recovered using a sulfur compound.
以下に本発明の実施条件について述べる。The conditions for implementing the present invention will be described below.
本発明によって回収される遷移金属としては、一般に触
媒として用いられるＦｅ、 Ｃｏ、 Ｎｉ、 Ｃｒ。The transition metals recovered by the present invention include Fe, Co, Ni, and Cr, which are generally used as catalysts.
Ｃｕ、 Ｒｈ、 Ｐｄ、 Ｐｔ、 Ｉｒ等がある。これ
ら遷移金属を含有する反応生成物に添加する硫黄化合物
としては１１２ｓ、 Ｎａ２Ｓ、 Ｎａ５Ｈ等があり、
これらはどのような状態のものでもよく、反応生成物液
中に於ける遷移金属触媒との接触効率によって適宜決定
できる。又、添加量としては回収しようとする遷移金属
量に対して当モル量以上であればよい。Examples include Cu, Rh, Pd, Pt, and Ir. Sulfur compounds added to reaction products containing these transition metals include 112s, Na2S, Na5H, etc.
These may be in any state and can be appropriately determined depending on the contact efficiency with the transition metal catalyst in the reaction product liquid. Further, the amount added may be at least an equivalent molar amount to the amount of transition metal to be recovered.
本発明が適用される反応生成物は、前述したような遷移
金属触媒を用いて得られた反応液そのものでもよいが、
これらをフラッシュ、抽出等により大部分の触媒を分離
した後の反応生成物であってもよい。The reaction product to which the present invention is applied may be the reaction solution itself obtained using the transition metal catalyst as described above, but
These may be reaction products after most of the catalyst has been separated by flashing, extraction, etc.
通常この様な反応生成物には５０００〜５ｐｐｍ程度の
遷移金属が含まれている。なお、経済的な効率を考慮す
れば、フラッシュ、抽出等により大部分の触媒を分離し
た後の５００〜２０ｐｐｍ程度の遷移金属を含む反応生
成物に好ましく適用される。Typically, such reaction products contain about 5000 to 5 ppm of transition metals. Note that, in consideration of economic efficiency, this method is preferably applied to reaction products containing about 500 to 20 ppm of transition metals after most of the catalyst has been separated by flashing, extraction, etc.
反応生成物と硫黄化合物を接触させる方法としては、撹
拌槽を用いる等、−数的な方法が利用できる。As a method for bringing the reaction product into contact with the sulfur compound, a numerical method such as using a stirring tank can be used.
例えば、撹拌槽を使用する場合、遷移金属含有液に対し
てＮａ５Ｈフレークを投入し、十分撹拌した後、沈降し
た遷移金属硫化物を通常の固液分離操作によって回収す
る。このようにして回収された遷移金属硫化物は、焼成
等の操作によって高価な遷移金属として容易に回収する
ことができる。For example, when using a stirring tank, Na5H flakes are added to the transition metal-containing liquid, and after sufficient stirring, the precipitated transition metal sulfide is recovered by a normal solid-liquid separation operation. The transition metal sulfide thus recovered can be easily recovered as an expensive transition metal through operations such as calcination.
従って本発明の方法により、反応液中もしくは抽出液中
に含有される遷移金属触媒を何ら特殊な装置を使用せず
、簡単で効率的に分離回収できる。Therefore, according to the method of the present invention, the transition metal catalyst contained in the reaction solution or extract can be easily and efficiently separated and recovered without using any special equipment.
以下に本発明の詳細な説明するための実施例を示すが、
本発明はこれらの実施例により限定されるものではない
。Examples for explaining the present invention in detail are shown below.
The present invention is not limited to these examples.
実施例１
０ジウム触媒を用いて２−（４−インブチルフェニル）
エチルアルコールと一酸化炭素カラ２− （４−インブ
チルフェニル）プロピオン酸を合成した際に、抽出法に
よって大部分のロジウムを分離した反応液［２−（４−
インブチルフェニル）プロピオン酸２５ＩＩｌｔ％、ヘ
キサン７５ｗｔ％〕中に１４２ＭＪｍのロジウムが残存
した。Example 1 2-(4-inbutylphenyl) using 0dium catalyst
When ethyl alcohol and carbon monoxide were synthesized, most of the rhodium was separated by an extraction method [2-(4-
25 IIlt% of imbutylphenyl)propionic acid and 75 wt% of hexane], 142 MJm of rhodium remained.
この反応液５００１ｎｌを１１の３日フラスコに仕込み
、常温にてＨ２Ｓガスを１００ｍｊ２／ｍｉｎの流量で
通気撹拌を行った。１２０分の後、ガス吹き込みを停止
した時点でフラスコ底部に黒色沈殿が存在した。この後
、液中溶存Ｈ２Ｓガスの追い出しのため、ヘキサンの還
流温度（約７０℃）にて１時間加熱処理を行い、グラス
フィルターにて濾過し、液中ロジウム濃度を分析したと
ころ、０．３ｐｐｍまで減少していた。本摸作によるＲ
ｈ回収率は９９．７９％であった。5001 nl of this reaction solution was charged into a 3-day flask (No. 11), and aerated with H2S gas at a flow rate of 100 mj2/min at room temperature. After 120 minutes, a black precipitate was present at the bottom of the flask when gas blowing was stopped. After this, in order to drive out H2S gas dissolved in the liquid, heat treatment was performed for 1 hour at the reflux temperature of hexane (approximately 70°C), and the rhodium concentration in the liquid was analyzed and found to be 0.3 ppm. had decreased to. R by this copy
h recovery rate was 99.79%.
実施例２
実施例１と同様の反応液１５０ｒｒｔｆ！とＮａ２Ｓ
・９Ｈ２０１ｇを３００ｍ７！の電磁撹拌機付きオート
クレーブに仕込み、常温で１時間、４００ｒ、 ｐ、
ｍ、にて撹拌した後、グラスフィルターにて濾過した。Example 2 150rrtf of the same reaction solution as in Example 1! and Na2S
・9H201g 300m7! Place in an autoclave equipped with a magnetic stirrer and heat at room temperature for 1 hour at 400 r/p.
After stirring at m, it was filtered through a glass filter.
この液中のＲｈａ度を分析したところ、２゜！５ｐｐｍ
であった。（Ｒｈ回収率９８．５２％）
実施例３
実施例１と同様の反応液をさらに塩酸水溶液で抽出した
下層液（７％塩酸水溶液、Ｒｈ濃度８６ｐｐｍ＞ １０
０ｍ１にＮａ２Ｓ ｊ ９１４２ｏ １ ｇを添加し、
常温にて１０分間撹拌した。次いで加熱、濾過を行い、
液中Ｒｈ濃度を測定したところ、０．０ｉｐｐｍにまで
減少していた。（Ｒｈ回収率９９．９９％）〔発明の効
果〕
上記実施例からも明らかなように、本発明の方法によっ
て反応液中もしくは抽出液中に含有される遷移金属触媒
を何ら特殊な装置を使用することなく、非常に効率的に
分離回収できる。When we analyzed the Rha degree in this liquid, it was 2°! 5ppm
Met. (Rh recovery rate 98.52%) Example 3 Lower layer liquid obtained by further extracting the same reaction solution as in Example 1 with an aqueous hydrochloric acid solution (7% aqueous hydrochloric acid solution, Rh concentration 86 ppm > 10
Add 1 g of Na2S j 9142o to 0 ml,
The mixture was stirred at room temperature for 10 minutes. Then heating and filtration are performed,
When the Rh concentration in the liquid was measured, it was found to have decreased to 0.0 ippm. (Rh recovery rate 99.99%) [Effects of the invention] As is clear from the above examples, the method of the present invention does not require any special equipment to remove the transition metal catalyst contained in the reaction solution or extract. can be separated and recovered very efficiently without any
Claims (1)
する遷移金属を、硫黄化合物を用いて分離回収すること
を特徴とする遷移金属触媒の分離回収方法。 ２ 硫黄化合物がＨ＿２Ｓ、ＮａＳＨ又はＮａ＿２Ｓで
ある請求項１記載の分離回収方法。[Scope of Claims] 1. A method for separating and recovering transition metal catalysts, which comprises separating and recovering transition metals remaining in a reaction product obtained using a transition metal catalyst using a sulfur compound. 2. The separation and recovery method according to claim 1, wherein the sulfur compound is H_2S, NaSH or Na_2S.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP63291948A JP2580290B2 (en) | 1988-11-18 | 1988-11-18 | Method for separating and recovering transition metal catalyst |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP63291948A JP2580290B2 (en) | 1988-11-18 | 1988-11-18 | Method for separating and recovering transition metal catalyst |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH02139046A true JPH02139046A (en) | 1990-05-29 |
| JP2580290B2 JP2580290B2 (en) | 1997-02-12 |
Family
ID=17775532
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP63291948A Expired - Lifetime JP2580290B2 (en) | 1988-11-18 | 1988-11-18 | Method for separating and recovering transition metal catalyst |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2580290B2 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2004069802A1 (en) * | 2003-02-06 | 2004-08-19 | Shionogi & Co., Ltd. | Process for producing 2-amino-3-substituted pyridine |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5437113A (en) * | 1977-08-29 | 1979-03-19 | Tokyo Shibaura Electric Co | Method of making ceramic sintered body |
| JPS557302A (en) * | 1978-06-29 | 1980-01-19 | Nippon Zeon Co | Method of sounddproofing existing house |
| JPS6311517A (en) * | 1986-03-31 | 1988-01-19 | ケミカル アンド メタル インダストリ−ズ，インコ−ポレイテイド | Recollection of valuables from used alumina-carried catalyst |
| JPS63270549A (en) * | 1982-10-08 | 1988-11-08 | オウトクンプ オイ | Recovery of noble metal from used catalyst for extracting sulfur from crude oil |
-
1988
- 1988-11-18 JP JP63291948A patent/JP2580290B2/en not_active Expired - Lifetime
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5437113A (en) * | 1977-08-29 | 1979-03-19 | Tokyo Shibaura Electric Co | Method of making ceramic sintered body |
| JPS557302A (en) * | 1978-06-29 | 1980-01-19 | Nippon Zeon Co | Method of sounddproofing existing house |
| JPS63270549A (en) * | 1982-10-08 | 1988-11-08 | オウトクンプ オイ | Recovery of noble metal from used catalyst for extracting sulfur from crude oil |
| JPS6311517A (en) * | 1986-03-31 | 1988-01-19 | ケミカル アンド メタル インダストリ−ズ，インコ−ポレイテイド | Recollection of valuables from used alumina-carried catalyst |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2004069802A1 (en) * | 2003-02-06 | 2004-08-19 | Shionogi & Co., Ltd. | Process for producing 2-amino-3-substituted pyridine |
| JPWO2004069802A1 (en) * | 2003-02-06 | 2006-05-25 | 塩野義製薬株式会社 | Method for producing 2-amino-3-substituted pyridine |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2580290B2 (en) | 1997-02-12 |
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