JPH0367740B2 - - Google Patents
Info
- Publication number
- JPH0367740B2 JPH0367740B2 JP58032270A JP3227083A JPH0367740B2 JP H0367740 B2 JPH0367740 B2 JP H0367740B2 JP 58032270 A JP58032270 A JP 58032270A JP 3227083 A JP3227083 A JP 3227083A JP H0367740 B2 JPH0367740 B2 JP H0367740B2
- Authority
- JP
- Japan
- Prior art keywords
- anion exchange
- carbon disulfide
- exchange resin
- acid
- remove
- 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.)
- Expired - Lifetime
Links
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 claims description 69
- 239000003957 anion exchange resin Substances 0.000 claims description 34
- 229930195733 hydrocarbon Natural products 0.000 claims description 15
- 239000004215 Carbon black (E152) Substances 0.000 claims description 14
- 150000002430 hydrocarbons Chemical class 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 6
- 230000001172 regenerating effect Effects 0.000 claims description 6
- QGJOPFRUJISHPQ-NJFSPNSNSA-N carbon disulfide-14c Chemical compound S=[14C]=S QGJOPFRUJISHPQ-NJFSPNSNSA-N 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- 239000012492 regenerant Substances 0.000 claims description 5
- 239000003513 alkali Substances 0.000 claims description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- -1 chlorine ions Chemical class 0.000 description 5
- 239000011347 resin Substances 0.000 description 4
- 229920005989 resin Polymers 0.000 description 4
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000011069 regeneration method Methods 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 230000003213 activating effect Effects 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 239000005416 organic matter Substances 0.000 description 2
- 125000002924 primary amino group Chemical class [H]N([H])* 0.000 description 2
- 125000001453 quaternary ammonium group Chemical group 0.000 description 2
- 238000001179 sorption measurement Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000000895 extractive distillation Methods 0.000 description 1
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 235000014413 iron hydroxide Nutrition 0.000 description 1
- NCNCGGDMXMBVIA-UHFFFAOYSA-L iron(ii) hydroxide Chemical compound [OH-].[OH-].[Fe+2] NCNCGGDMXMBVIA-UHFFFAOYSA-L 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000007420 reactivation Effects 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000002791 soaking Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 150000003464 sulfur compounds Chemical class 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B60—VEHICLES IN GENERAL
- B60S—SERVICING, CLEANING, REPAIRING, SUPPORTING, LIFTING, OR MANOEUVRING OF VEHICLES, NOT OTHERWISE PROVIDED FOR
- B60S1/00—Cleaning of vehicles
- B60S1/02—Cleaning windscreens, windows or optical devices
- B60S1/04—Wipers or the like, e.g. scrapers
- B60S1/06—Wipers or the like, e.g. scrapers characterised by the drive
- B60S1/08—Wipers or the like, e.g. scrapers characterised by the drive electrically driven
Landscapes
- Engineering & Computer Science (AREA)
- Mechanical Engineering (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
Description
【発明の詳細な説明】
本発明はC5炭化水素留分中に含まれる二硫化
炭素を除去するために使用された陰イオン交換樹
脂の再生方法に関するものである。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a method for regenerating anion exchange resins used to remove carbon disulfide contained in C5 hydrocarbon fractions.
一般に、炭化水素留分特にC5炭化水素留分は
二硫化炭素、硫化水素、メルカプタン類などを微
量含有していることが多く、この中でも特に二硫
化炭素は他の硫黄化合物に比較して含有量も多
く、蒸留、抽出蒸留などの分離精製工程において
も除去されにくいために分離された製品中に同伴
してくることになる。この二硫化炭素は分離され
た製品、例えばイソブレンを重合用モノマーとし
て使用する際に反応を阻害する原因となるので製
品からできる限り除去することが好ましい。 In general, hydrocarbon fractions, especially C5 hydrocarbon fractions, often contain trace amounts of carbon disulfide, hydrogen sulfide, mercaptans, etc. Among these, carbon disulfide is particularly contained compared to other sulfur compounds. Since the amount is large and it is difficult to remove even in separation and purification processes such as distillation and extractive distillation, it ends up being entrained in the separated product. Since this carbon disulfide causes inhibition of the reaction when the separated product, for example isobrene, is used as a monomer for polymerization, it is preferable to remove it from the product as much as possible.
本発明者らは先に二硫化炭素を含有するC5炭
化水素あるいはC5炭化水素混合物を塩基性陰イ
オン交換樹脂と接触せしめて二硫化炭素を除去す
るC5炭化水素の精製方法を提案した（特願昭57
−45814）。この方法によれば簡略化された工程に
よつて効率よく二硫化炭素が除去できるが、二硫
化炭素を吸着しその機能を失つた陰イオン交換樹
脂は水酸化ナトリウム等の通常の再生剤を通液せ
しめただけでは充分に再生できないことが判つ
た。 The present inventors previously proposed a method for purifying C5 hydrocarbons in which carbon disulfide is removed by contacting a C5 hydrocarbon or C5 hydrocarbon mixture containing carbon disulfide with a basic anion exchange resin. (Special request 1987)
−45814). According to this method, carbon disulfide can be efficiently removed through a simplified process, but the anion exchange resin, which has absorbed carbon disulfide and has lost its function, is passed through ordinary regenerants such as sodium hydroxide. It was found that it was not possible to regenerate the material sufficiently just by soaking it with liquid.
従つて、本発明の目的はC5炭化水素留分中の
二硫化炭素の除去に使用された陰イオン交換樹脂
の再生方法を提供することにあり、この目的は二
硫化炭素を吸着した陰イオン交換樹脂を予め酸で
処理した後に水酸基を有するアルカリ再生剤で賦
活することによつて達成される。 Therefore, it is an object of the present invention to provide a method for regenerating anion exchange resins used for the removal of carbon disulfide in C5 hydrocarbon fractions. This is achieved by treating the exchange resin with an acid in advance and then activating it with an alkali regenerant having a hydroxyl group.
一般に、水処理方法において水溶液中の不純物
イオンを除去する為に陰イオン交換樹脂が使用さ
れており、その再生方法は塩化ナトリウム、水酸
化ナトリウム等により行われている。また、この
際前処理として酸を利用することもあるが、その
目的は水処理使用後の陰イオン交換樹脂の内部に
蓄積された有機物の除去あるいは水酸化鉄の沈澱
物の皮膜除去にある。 Generally, anion exchange resins are used in water treatment methods to remove impurity ions in aqueous solutions, and their regeneration methods are carried out using sodium chloride, sodium hydroxide, and the like. Further, at this time, an acid may be used as a pretreatment, but the purpose thereof is to remove organic matter accumulated inside the anion exchange resin after water treatment or to remove a film of iron hydroxide precipitate.
しかるに、本発明はC5炭化水素留分中の二硫
化炭素を除去するために使用された陰イオン交換
樹脂の再生方法に関するものであつて、従来の方
法とは対象を異にしている。二硫化炭素を含む
C5炭化水素留分を陰イオン交換樹脂により処理
していくと、陰イオン交換樹脂の末端基である
１、２級アミン基あるいは４級アンモニウム基と
二硫化炭素とが吸着反応を起すため陰イオン交換
樹脂は徐々にその機能を果さなくなる。このよう
に活性を失つた陰イオン交換樹脂は有機物を熱窒
素ガスあるいは真空乾燥にて完全に除去した後
に、通常の陰イオン交換樹脂を再生せしめる如く
水酸化ナトリウム等の再生剤を通液しても全く再
生できなかつた。 However, the present invention relates to a method for regenerating an anion exchange resin used to remove carbon disulfide in a C5 hydrocarbon fraction, and is different from conventional methods. Contains carbon disulfide
When a C5 hydrocarbon fraction is treated with an anion exchange resin, an adsorption reaction occurs between the primary and secondary amine groups or quaternary ammonium groups, which are the end groups of the anion exchange resin, and carbon disulfide. Ion exchange resins gradually cease to perform their function. After completely removing organic substances from anion exchange resins that have lost their activity using hot nitrogen gas or vacuum drying, they are treated with a regenerating agent such as sodium hydroxide, which is used to regenerate ordinary anion exchange resins. could not be played at all.
本発明は単なるイオン交換としてではなく、反
応吸着に利用された場合の陰イオン交換樹脂の再
生方法に係るもので、まず最初に塩酸等の酸を二
硫化炭素を吸着した陰イオン交換樹脂に通液し塩
素イオン（Cl-）等を陰イオン交換樹脂末端基の
１、２級アミン基に吸着させ水洗後、水酸化ナト
リウム等の水酸基を有するアルカリ再生剤を通液
し塩素イオン等とイオン交換させる際に同時に二
硫化炭素を陰イオン交換樹脂から除去させること
によつて陰イオン交換樹脂の賦活が図られる。 The present invention relates to a method for regenerating anion exchange resins when used for reaction adsorption, not just ion exchange. First, an acid such as hydrochloric acid is passed through an anion exchange resin that has adsorbed carbon disulfide. In the liquid, chlorine ions (Cl - ), etc. are adsorbed on the primary and secondary amine groups of the anion exchange resin terminal groups, and after washing with water, an alkaline regenerant having a hydroxyl group such as sodium hydroxide is passed through to exchange ions with chlorine ions, etc. At the same time, the anion exchange resin is activated by simultaneously removing carbon disulfide from the anion exchange resin.
本発明においては使用される陰イオン交換樹脂
としては第４級アンモニウム基を交換基とする
型および型の強塩基性陰イオン交換樹脂、第１
級、第２級または第３級アミンを交換基とする弱
塩基性陰イオン交換樹脂が相当するが、これらの
うち弱塩基性陰イオン交換樹脂は二硫化炭素の除
去効率にすぐれるので賞用される。陰イオン交換
樹脂は多量の二硫化炭素の除去によりその能力を
低下させるが、再生賦活により再使用が可能とな
る。 In the present invention, the anion exchange resins used include strongly basic anion exchange resins of types and types having a quaternary ammonium group as an exchange group,
This corresponds to weakly basic anion exchange resins with secondary, secondary, or tertiary amines as exchange groups, but among these, weakly basic anion exchange resins are prized because they have excellent carbon disulfide removal efficiency. be done. Although the ability of anion exchange resin is reduced by removing a large amount of carbon disulfide, it can be reused by reactivation.
本発明の再生方法で使用される酸としては塩
酸、硫酸、リン酸、硝酸などが挙げられ、また水
酸基を有するアルカリ再生剤としては水酸化ナト
リウム、水酸化カリウム、水酸化アンモニウムな
どが挙げられる。 Examples of the acid used in the regeneration method of the present invention include hydrochloric acid, sulfuric acid, phosphoric acid, and nitric acid, and examples of the alkali regenerant having a hydroxyl group include sodium hydroxide, potassium hydroxide, ammonium hydroxide, and the like.
C5炭化水素留分中の二硫化炭素の除去に使用
され失活した陰イオン交換樹脂は予め酸で処理し
た後に水酸基を有するアルカリ再生剤で賦活する
ことにより再生される。本発明のこの方法によれ
ば二硫化炭素の吸着に使用される前と同程度の交
換容量を有する陰イオン交換樹脂に再生すること
が可能であり経済的に利点を有する。 The deactivated anion exchange resin used to remove carbon disulfide from the C5 hydrocarbon fraction is regenerated by treating it with an acid in advance and then activating it with an alkali regenerant having a hydroxyl group. According to this method of the present invention, it is possible to regenerate the anion exchange resin into an anion exchange resin having the same exchange capacity as before it was used for adsorbing carbon disulfide, which is economically advantageous.
次に、本発明を実施例により具体的に説明す
る。 Next, the present invention will be specifically explained using examples.
実施例
直径20mmの充填塔に陰イオン交換樹脂（商品名
ダイヤイオンWA−21、三菱化成工業株式会社
製）を20ml充填し、100ppmの二硫化炭素を含む
C5炭化水素留分を空間速度5Hr-1で通液したとこ
ろ150時間で二硫化炭素を除去することができな
くなつた。Example A packed tower with a diameter of 20 mm was filled with 20 ml of anion exchange resin (trade name Diaion WA-21, manufactured by Mitsubishi Chemical Industries, Ltd.), containing 100 ppm of carbon disulfide.
When a C 5 hydrocarbon fraction was passed through the solution at a space velocity of 5 Hr -1 , carbon disulfide could no longer be removed after 150 hours.
この二硫化炭素を除去できなくなつた陰イオン
交換樹脂に、まず1Nの塩酸を空間速度5Hr-1で
300ｇ／（樹脂）通液し過剰の塩酸を水洗した
後、1Nの水酸化ナトリウムを空間速度5Hr-1で
300ｇ／（樹脂）通液し水洗することにより再
生した。 First, 1N hydrochloric acid was applied to the anion exchange resin that could no longer remove carbon disulfide at a space velocity of 5 Hr -1 .
After passing 300g/(resin) and washing excess hydrochloric acid with water, add 1N sodium hydroxide at a space velocity of 5Hr -1.
It was regenerated by passing 300 g/(resin) of liquid and washing with water.
この方法で再生した陰イオン交換樹脂に
100ppmの二硫化炭素を含むC5炭化水素留分を空
間速度5Hr-1で通液した結果、二硫化炭素が
5ppm以下のC5炭化水素留分を10生産できた。
新しい陰イオン交換樹脂の場合、同様の実験条件
では11の生産であることから本発明の方法で再
生を行えば使用前と同程度の交換容量を有する陰
イオン交換樹脂に再生できることが判つた。 The anion exchange resin regenerated using this method
As a result of passing a C 5 hydrocarbon fraction containing 100 ppm carbon disulfide at a space velocity of 5 Hr -1 , carbon disulfide was
We were able to produce 10 C5 hydrocarbon fractions below 5ppm.
In the case of the new anion exchange resin, the production was 11 under the same experimental conditions, indicating that if the method of the present invention is used for regeneration, the anion exchange resin can be regenerated into an anion exchange resin having the same exchange capacity as before use.
比較例
実施例と同じの二硫化炭素を除去できなくなつ
た陰イオン交換樹脂をまず窒素により有機物を除
去した後、1Nの水酸化ナトリウムを空間速度
5Hr-1で300ｇ／（樹脂）通液し水洗し再生し
た。この陰イオン交換樹脂に実施例と同じく
100ppmの二硫化炭素を含むC5炭化水素留分を空
間速度5Hr-1で通液したところ、充填塔入口、出
口とも二硫化炭素の濃度は100ppmであり全く再
生できていないことが判つた。Comparative Example The same anion exchange resin as in the example, which could no longer remove carbon disulfide, was first removed with nitrogen to remove organic matter, and then 1N sodium hydroxide was added at a space velocity.
300g/(resin) was passed through for 5Hr -1 , washed with water, and regenerated. This anion exchange resin is
When a C 5 hydrocarbon fraction containing 100 ppm of carbon disulfide was passed through the tank at a space velocity of 5 Hr -1 , it was found that the concentration of carbon disulfide was 100 ppm at both the inlet and outlet of the packed column, indicating that it could not be regenerated at all.
Claims (1)
除去に使用された陰イオン交換樹脂を、予め酸で
処理した後に水酸基を有するアルカリ再生剤で賦
活することを特徴とする二硫化炭素を吸着した陰
イオン交換樹脂の再生方法。1 Carbon disulfide, which is characterized in that the anion exchange resin used to remove carbon disulfide contained in the C5 hydrocarbon fraction is previously treated with acid and then activated with an alkali regenerant having a hydroxyl group. A method for regenerating adsorbed anion exchange resin.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP58032270A JPS59156439A (en) | 1983-02-28 | 1983-02-28 | Regeneration of anion exchange resin |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP58032270A JPS59156439A (en) | 1983-02-28 | 1983-02-28 | Regeneration of anion exchange resin |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS59156439A JPS59156439A (en) | 1984-09-05 |
| JPH0367740B2 true JPH0367740B2 (en) | 1991-10-24 |
Family
ID=12354302
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP58032270A Granted JPS59156439A (en) | 1983-02-28 | 1983-02-28 | Regeneration of anion exchange resin |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS59156439A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2018029661A1 (en) * | 2016-08-12 | 2018-02-15 | Reliance Industries Limited | Process for reducing the amount of carbon disulphide (cs 2) in a hydrocarbon feed |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6245128B1 (en) * | 1999-06-15 | 2001-06-12 | Mobil Oil Corporation | Process for the reclamation of spent alkanolamine solution |
-
1983
- 1983-02-28 JP JP58032270A patent/JPS59156439A/en active Granted
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2018029661A1 (en) * | 2016-08-12 | 2018-02-15 | Reliance Industries Limited | Process for reducing the amount of carbon disulphide (cs 2) in a hydrocarbon feed |
| US11299681B2 (en) | 2016-08-12 | 2022-04-12 | Reliance Industries Limited | Process for reducing the amount of carbon disulphide (CS2) in a hydrocarbon feed |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS59156439A (en) | 1984-09-05 |
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