JPH0338531A - How to remove mercaptans - Google Patents
How to remove mercaptansInfo
- Publication number
- JPH0338531A JPH0338531A JP17189889A JP17189889A JPH0338531A JP H0338531 A JPH0338531 A JP H0338531A JP 17189889 A JP17189889 A JP 17189889A JP 17189889 A JP17189889 A JP 17189889A JP H0338531 A JPH0338531 A JP H0338531A
- Authority
- JP
- Japan
- Prior art keywords
- mercaptan
- copper
- lead
- replaced
- mercaptans
- 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
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 title description 6
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 claims description 15
- 239000000203 mixture Substances 0.000 claims description 13
- 239000005749 Copper compound Substances 0.000 claims description 10
- 150000001880 copper compounds Chemical class 0.000 claims description 10
- 150000002611 lead compounds Chemical class 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 9
- 238000004821 distillation Methods 0.000 claims description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 18
- WQAQPCDUOCURKW-UHFFFAOYSA-N butanethiol Chemical compound CCCCS WQAQPCDUOCURKW-UHFFFAOYSA-N 0.000 description 16
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical group CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 229910000831 Steel Inorganic materials 0.000 description 3
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 3
- 239000012535 impurity Substances 0.000 description 3
- KZCOBXFFBQJQHH-UHFFFAOYSA-N octane-1-thiol Chemical compound CCCCCCCCS KZCOBXFFBQJQHH-UHFFFAOYSA-N 0.000 description 3
- 239000010959 steel Substances 0.000 description 3
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- 150000001879 copper Chemical class 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- YADSGOSSYOOKMP-UHFFFAOYSA-N dioxolead Chemical compound O=[Pb]=O YADSGOSSYOOKMP-UHFFFAOYSA-N 0.000 description 2
- DNJIEGIFACGWOD-UHFFFAOYSA-N ethanethiol Chemical compound CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- SUVIGLJNEAMWEG-UHFFFAOYSA-N propane-1-thiol Chemical compound CCCS SUVIGLJNEAMWEG-UHFFFAOYSA-N 0.000 description 2
- 238000001577 simple distillation Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical group [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- JGFBQFKZKSSODQ-UHFFFAOYSA-N Isothiocyanatocyclopropane Chemical compound S=C=NC1CC1 JGFBQFKZKSSODQ-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- 150000001241 acetals Chemical class 0.000 description 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- PWLNAUNEAKQYLH-UHFFFAOYSA-N butyric acid octyl ester Natural products CCCCCCCCOC(=O)CCC PWLNAUNEAKQYLH-UHFFFAOYSA-N 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- -1 copper carboxylates Chemical class 0.000 description 1
- 229940120693 copper naphthenate Drugs 0.000 description 1
- OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 description 1
- SVOAENZIOKPANY-CVBJKYQLSA-L copper;(z)-octadec-9-enoate Chemical compound [Cu+2].CCCCCCCC\C=C/CCCCCCCC([O-])=O.CCCCCCCC\C=C/CCCCCCCC([O-])=O SVOAENZIOKPANY-CVBJKYQLSA-L 0.000 description 1
- SEVNKWFHTNVOLD-UHFFFAOYSA-L copper;3-(4-ethylcyclohexyl)propanoate;3-(3-ethylcyclopentyl)propanoate Chemical compound [Cu+2].CCC1CCC(CCC([O-])=O)C1.CCC1CCC(CCC([O-])=O)CC1 SEVNKWFHTNVOLD-UHFFFAOYSA-L 0.000 description 1
- ZKXWKVVCCTZOLD-UHFFFAOYSA-N copper;4-hydroxypent-3-en-2-one Chemical compound [Cu].CC(O)=CC(C)=O.CC(O)=CC(C)=O ZKXWKVVCCTZOLD-UHFFFAOYSA-N 0.000 description 1
- HFDWIMBEIXDNQS-UHFFFAOYSA-L copper;diformate Chemical compound [Cu+2].[O-]C=O.[O-]C=O HFDWIMBEIXDNQS-UHFFFAOYSA-L 0.000 description 1
- FWBOFUGDKHMVPI-UHFFFAOYSA-K dicopper;2-oxidopropane-1,2,3-tricarboxylate Chemical compound [Cu+2].[Cu+2].[O-]C(=O)CC([O-])(C([O-])=O)CC([O-])=O FWBOFUGDKHMVPI-UHFFFAOYSA-K 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- MNWFXJYAOYHMED-UHFFFAOYSA-N heptanoic acid Chemical compound CCCCCCC(O)=O MNWFXJYAOYHMED-UHFFFAOYSA-N 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 229910000464 lead oxide Inorganic materials 0.000 description 1
- UUIQMZJEGPQKFD-UHFFFAOYSA-N n-butyric acid methyl ester Natural products CCCC(=O)OC UUIQMZJEGPQKFD-UHFFFAOYSA-N 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- YEXPOXQUZXUXJW-UHFFFAOYSA-N oxolead Chemical compound [Pb]=O YEXPOXQUZXUXJW-UHFFFAOYSA-N 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 238000011002 quantification Methods 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
- 150000003839 salts Chemical class 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Landscapes
- Removal Of Specific Substances (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
(57)【要約】本公報は電子出願前の出願データであるた
め要約のデータは記録されません。(57) [Summary] This bulletin contains application data before electronic filing, so abstract data is not recorded.
Description
【発明の詳細な説明】
〔産業上の利用分野〕
本発明は微量のメルカプタンを含有する混合物からメル
カプタンを除去する方法に関する。DETAILED DESCRIPTION OF THE INVENTION Field of the Invention The present invention relates to a method for removing mercaptans from mixtures containing trace amounts of mercaptans.
〔従来の技術及び発明が解決しようとする問題点〕メル
カプタンは極微量存在しても特有の臭気を発し、取扱い
上問題を有する。炭化水素、芳香族化合物等に含まれる
メルカプタンの除去方法としては、硫酸洗浄、アルカリ
洗浄及び水洗による方法が一般的であるが、この方法は
工程が複雑であり、また硫酸やアルカリに不活性な液体
でないと使用ができないなど制約を有する。[Problems to be Solved by the Prior Art and the Invention] Mercaptans emit a characteristic odor even when present in extremely small amounts, posing problems in handling. The common methods for removing mercaptans contained in hydrocarbons, aromatic compounds, etc. include sulfuric acid washing, alkaline washing, and water washing, but these methods require complicated steps and are inert to sulfuric acid and alkalis. It has limitations such as it cannot be used unless it is liquid.
また、メルカプタンのみを選択的に抽出、蒸留等により
完全に除去することも困難である。Furthermore, it is also difficult to completely remove only mercaptan by selective extraction, distillation, etc.
従って簡便かつ効果的にメルカプタンの除去法の開発が
望まれていた。Therefore, it has been desired to develop a simple and effective method for removing mercaptans.
本発明は、微量のメルカプタンを不純物として含む混合
物を鉛化合物及び/又は銅化合物で処理することを特徴
とするメルカプタンの除去法である。The present invention is a mercaptan removal method characterized by treating a mixture containing a trace amount of mercaptan as an impurity with a lead compound and/or a copper compound.
本発明で使用する鉛化合物としては例えば四酸化二鉛、
酸化鉛、二酸化鉛及びこれらの混合物等が挙げられる。Examples of lead compounds used in the present invention include dilead tetroxide,
Examples include lead oxide, lead dioxide, and mixtures thereof.
また銅化合物としては、例えば蟻酸銅、酢酸銅、くえん
酸銅、オレイン酸銅、ナフテン酸銅等のカルボン酸銅(
[I)塩が好ましい。そのほか例えば硫酸鋼、塩化鋼等
の無機銅塩、銅アセチルアセトナート等の銅錯体及びこ
れらの混合物を用いることもできる。これら鉛及び銅化
合物はそれぞれ単独で使用しても、また併用しても効果
を発揮する。Examples of copper compounds include copper carboxylates such as copper formate, copper acetate, copper citrate, copper oleate, and copper naphthenate.
[I) Salt is preferred. In addition, for example, inorganic copper salts such as sulfuric acid steel and chlorinated steel, copper complexes such as copper acetylacetonate, and mixtures thereof can also be used. These lead and copper compounds are effective when used alone or in combination.
本発明のメルカプタン含有の混合物としては、ヘキサン
、オクタン、石油エーテル、ベンゼン、トルエン、キシ
レン、エチルベンゼン、ナフタリン、テトラリン等の炭
化水素、ハロゲン化炭化水! 、アルコール、エーテル
、アセタール、ケトン、酢酸メチル、酪酸メチル等のエ
ステル、酢酸、プロピオン酸、酪酸等のカルボン酸、フ
ェノール類、水及びこれらの混合物が挙げられる。Examples of the mercaptan-containing mixture of the present invention include hydrocarbons such as hexane, octane, petroleum ether, benzene, toluene, xylene, ethylbenzene, naphthalene, and tetralin, and halogenated hydrocarbons! , alcohols, ethers, acetals, ketones, esters such as methyl acetate and methyl butyrate, carboxylic acids such as acetic acid, propionic acid and butyric acid, phenols, water and mixtures thereof.
メルカプタンとしては例えばメチルメルカプタン、エチ
ルメルカプタン、プロピルメルカプタン、ブチルメルカ
プタン、オクチルメルカプタンねと及びこれらの混合物
等が挙げられる。Examples of the mercaptan include methyl mercaptan, ethyl mercaptan, propyl mercaptan, butyl mercaptan, octyl mercaptan, and mixtures thereof.
本発明を実施するに際しては、まず微量のメルカプタン
を含有する混合物に鉛及び/又は銅化合物を添加する。In carrying out the present invention, first a lead and/or copper compound is added to a mixture containing a trace amount of mercaptan.
微量のメルカプタンを含有する混合物とは、通常は約0
.3重量%以下のメルカプタンを含有するものを意味す
るが、これ以上含有していてもよい。A mixture containing trace amounts of mercaptan is usually about 0
.. This means that it contains 3% by weight or less of mercaptan, but it may contain more than this.
鉛及び銅化合物は粉末、顆粒等にして用いることが好ま
しい。It is preferable to use the lead and copper compounds in the form of powder, granules, or the like.
鉛及び/銅化合物の添加量は、不純物として含まれるメ
ルカプタン1重量部当り、0.05〜5重量部が好まし
い。The amount of lead and/or copper compound added is preferably 0.05 to 5 parts by weight per 1 part by weight of mercaptan contained as an impurity.
次いで鉛及び/又は銅化合物を添加した混合物を好まし
くは攪拌しながら0.5〜10時間保持する。処理温度
は0〜60℃好ましくは室温々いし40℃である。The mixture with the addition of lead and/or copper compounds is then maintained, preferably with stirring, for 0.5 to 10 hours. The treatment temperature is 0 to 60°C, preferably room temperature to 40°C.
こうして処理することにより、不純物として含まれてい
たメルカプタンを除去することができる。By this treatment, mercaptan contained as an impurity can be removed.
得られた処理液を蒸留することもできる。この場合は、
濾過、遠心分離等により鉛及び/又は銅化合物を除去し
たのち、又は除去せずにそのまま蒸留することができる
。The obtained treatment liquid can also be distilled. in this case,
After removing lead and/or copper compounds by filtration, centrifugation, etc., or without removing lead and/or copper compounds, distillation can be performed as is.
以下に実施例により本発明を更に詳しく説明する。The present invention will be explained in more detail with reference to Examples below.
実施例1
攪拌機付き300m1三ツロフラスコにブチルメルカプ
タン11000ppを含むヘキサ7200gを入れ、四
酸化二鉛0.5gを加え、25℃で30 Orpmで2
時間攪拌する。処理後、リービッヒの冷却管を付し、ヘ
キサンを約98%単蒸留で取り出し、留出液について水
素炎型ガスクロマトグラフ法でブチルメルカプタンを定
量すると、定量限界(10pp)以下であった。Example 1 7200 g of hexa containing 11000 pp of butyl mercaptan was placed in a 300 m1 Mitsuro flask equipped with a stirrer, 0.5 g of dilead tetroxide was added, and the mixture was heated at 25°C and 30 Orpm.
Stir for an hour. After the treatment, a Liebig condenser was attached and about 98% hexane was removed by simple distillation, and the distillate was quantified for butyl mercaptan by hydrogen flame gas chromatography, and it was found to be below the quantification limit (10 pp).
実施例2
実施例1においてヘキサンをトルエンに代え、その池は
同様に処理した結果、蒸留液中にブチルメルカプタンは
検出されなかった。Example 2 As a result of replacing hexane with toluene in Example 1 and treating the same pond in the same manner, butyl mercaptan was not detected in the distillate.
実施例3
実施例1においてヘキサンを酢酸に代え、四酸化二鉛を
酢酸鋼に代えて処理した。処理後の液中にはブチルメル
カプタンは検出されなかった。Example 3 In Example 1, hexane was replaced with acetic acid and dilead tetroxide was replaced with acetic acid steel. Butyl mercaptan was not detected in the liquid after treatment.
実施例4
実施例1においてへキサンを酢酸エチルに代え、また四
酸化二鉛をす7テン酸銅IIに代えて処理した。処理液
中にも、更に実施例1と同様に単蒸留した留出液中にも
ブチルメルカプタンは検出されなかった。Example 4 In Example 1, hexane was replaced with ethyl acetate, and dilead tetroxide was replaced with copper II heptanoate. Butyl mercaptan was not detected in the treated liquid or in the distillate obtained by simple distillation in the same manner as in Example 1.
実施例5
実施例3において酢酸を水に代え、その他は同様に処理
した。処理後の液中にはブチルメルカプタンは検出され
なかった。Example 5 The same procedure as in Example 3 was carried out except that acetic acid was replaced with water. Butyl mercaptan was not detected in the liquid after treatment.
実施例6
実施例1において、ブチルメルカプタンをオクチルメル
カプタンに代え、またへキサンを水に代え、その他は同
様に処理した。処理後の液中にはオクチルメルカプタン
は検出されなかった。Example 6 The same procedure as in Example 1 was carried out except that butyl mercaptan was replaced with octyl mercaptan, and hexane was replaced with water. No octyl mercaptan was detected in the liquid after treatment.
Claims (1)
び/又は銅化合物で処理することを特徴とするメルカプ
タンの除去法。 2、メルカプタン含有混合物を処理した後、蒸留を行う
ことを特徴とする第1請求項に記載の方法。[Claims] 1. A method for removing mercaptan, which comprises treating a mixture containing a trace amount of mercaptan with a lead compound and/or a copper compound. 2. The method according to claim 1, characterized in that distillation is carried out after the mercaptan-containing mixture has been treated.
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP17189889A JPH0338531A (en) | 1989-07-05 | 1989-07-05 | How to remove mercaptans |
| EP19900401660 EP0404643B1 (en) | 1989-06-22 | 1990-06-14 | Method for removing mercaptans |
| DE1990601099 DE69001099T2 (en) | 1989-06-22 | 1990-06-14 | METHOD FOR REMOVING MERCAPTANS. |
| CA 2019488 CA2019488A1 (en) | 1989-06-22 | 1990-06-21 | Method for removing mercaptans |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP17189889A JPH0338531A (en) | 1989-07-05 | 1989-07-05 | How to remove mercaptans |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH0338531A true JPH0338531A (en) | 1991-02-19 |
Family
ID=15931857
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP17189889A Pending JPH0338531A (en) | 1989-06-22 | 1989-07-05 | How to remove mercaptans |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0338531A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2007008024A (en) * | 2005-06-30 | 2007-01-18 | Anyk:Kk | Calendar device for personal computer |
| JP2007255816A (en) * | 2006-03-24 | 2007-10-04 | Mitsubishi Heavy Ind Ltd | Waste supply device and waste treatment device |
-
1989
- 1989-07-05 JP JP17189889A patent/JPH0338531A/en active Pending
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2007008024A (en) * | 2005-06-30 | 2007-01-18 | Anyk:Kk | Calendar device for personal computer |
| JP2007255816A (en) * | 2006-03-24 | 2007-10-04 | Mitsubishi Heavy Ind Ltd | Waste supply device and waste treatment device |
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