JPH047036A - Production of niobic acid catalyst - Google Patents
Production of niobic acid catalystInfo
- Publication number
- JPH047036A JPH047036A JP2109838A JP10983890A JPH047036A JP H047036 A JPH047036 A JP H047036A JP 2109838 A JP2109838 A JP 2109838A JP 10983890 A JP10983890 A JP 10983890A JP H047036 A JPH047036 A JP H047036A
- Authority
- JP
- Japan
- Prior art keywords
- niobic acid
- acid catalyst
- reaction
- isobutylene
- catalyst
- 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
- 239000003377 acid catalyst Substances 0.000 title claims abstract description 34
- 238000006243 chemical reaction Methods 0.000 claims abstract description 29
- 230000000694 effects Effects 0.000 claims abstract description 22
- 229930195733 hydrocarbon Natural products 0.000 claims abstract description 17
- 150000002430 hydrocarbons Chemical class 0.000 claims abstract description 17
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 claims abstract description 15
- 239000004215 Carbon black (E152) Substances 0.000 claims abstract description 9
- 239000007791 liquid phase Substances 0.000 claims abstract description 9
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 claims abstract description 8
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 claims abstract description 5
- LPIQUOYDBNQMRZ-UHFFFAOYSA-N cyclopentene Chemical compound C1CC=CC1 LPIQUOYDBNQMRZ-UHFFFAOYSA-N 0.000 claims abstract 4
- BKOOMYPCSUNDGP-UHFFFAOYSA-N 2-methylbut-2-ene Chemical group CC=C(C)C BKOOMYPCSUNDGP-UHFFFAOYSA-N 0.000 claims abstract 2
- NRWBPJIUSMMBPU-UHFFFAOYSA-N Dimethylhexa-1,4-diene Chemical compound C=CC(C)C=C(C)C NRWBPJIUSMMBPU-UHFFFAOYSA-N 0.000 claims abstract 2
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 claims abstract 2
- AMIMRNSIRUDHCM-UHFFFAOYSA-N Isopropylaldehyde Chemical compound CC(C)C=O AMIMRNSIRUDHCM-UHFFFAOYSA-N 0.000 claims description 20
- 238000000034 method Methods 0.000 claims description 16
- 230000003247 decreasing effect Effects 0.000 claims description 13
- 230000001172 regenerating effect Effects 0.000 claims description 6
- RYPKRALMXUUNKS-UHFFFAOYSA-N 2-Hexene Natural products CCCC=CC RYPKRALMXUUNKS-UHFFFAOYSA-N 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 239000003054 catalyst Substances 0.000 abstract description 11
- 238000006297 dehydration reaction Methods 0.000 abstract description 3
- 230000018044 dehydration Effects 0.000 abstract description 2
- 238000006471 dimerization reaction Methods 0.000 abstract description 2
- 230000002194 synthesizing effect Effects 0.000 abstract description 2
- 239000002253 acid Substances 0.000 description 5
- 238000011069 regeneration method Methods 0.000 description 4
- 230000007423 decrease Effects 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 239000011949 solid catalyst Substances 0.000 description 2
- 238000010478 Prins reaction Methods 0.000 description 1
- 229910021536 Zeolite Inorganic materials 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 1
- 238000010304 firing Methods 0.000 description 1
- 239000003292 glue Substances 0.000 description 1
- 238000006703 hydration reaction Methods 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- 229910052758 niobium Inorganic materials 0.000 description 1
- 239000010955 niobium Substances 0.000 description 1
- GUCVJGMIXFAOAE-UHFFFAOYSA-N niobium atom Chemical compound [Nb] GUCVJGMIXFAOAE-UHFFFAOYSA-N 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
- 239000010457 zeolite 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〉
本発明は反応に使用して活性が低下したニオブ酸触媒の
再生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 regenerating a niobic acid catalyst whose activity has decreased after use in a reaction.
ニオブ酸触媒は、脱水反応、水和反応、プリンス反応、
脱水縮合反応その他、広範な反応に有効な触媒として１
幅広い用途がある。Niobic acid catalysts can be used for dehydration reactions, hydration reactions, Prins reactions,
1 as an effective catalyst for a wide range of reactions including dehydration condensation reactions
It has a wide range of uses.
〈従来の技術〉
ニオブ酸触媒は、ノリ力・アルミナ触媒やゼオライト触
媒などの固体触媒と同様、使用中にその活性が低下する
ことが知られている。<Prior Art> It is known that the activity of niobic acid catalysts decreases during use, similar to solid catalysts such as glue/alumina catalysts and zeolite catalysts.
ところで、使用中に活性が低下した固体触媒の活性を復
活させる。いわゆる再生方法としては、高温の空気によ
り焼成する方法が知られている。By the way, the activity of a solid catalyst whose activity has decreased during use is restored. As a so-called regeneration method, a method of firing using high-temperature air is known.
しかしながら、ニオブ酸触媒は、４２５℃付近に転移点
を有するため、ニオブ酸触媒に対して上記の高温空気に
よる再生方法を施した場合、ニオブ酸が結晶化し、その
結果、ニオブ酸触媒本来の触媒機能が失なわれる。すな
わち、ニオブ酸触媒に対しては、有効な再生方法が見い
出されておらず、そのため、使用中に活性が低下したニ
オブ酸触媒は、廃棄せざるを得ないのが現状であった。However, since the niobic acid catalyst has a transition point around 425°C, when the niobic acid catalyst is subjected to the above-mentioned regeneration method using high-temperature air, the niobic acid crystallizes, and as a result, the original catalyst of the niobic acid catalyst Function is lost. That is, no effective regeneration method has been found for niobic acid catalysts, and therefore, niobic acid catalysts whose activity has decreased during use have no choice but to be discarded.
〈発明が解決しようとする課題〉
かかる現状に鑑み１本発明の課題は、使用中に活性が低
下したニオブ酸触媒の再生方法を提供することにある。<Problems to be Solved by the Invention> In view of the current situation, an object of the present invention is to provide a method for regenerating a niobic acid catalyst whose activity has decreased during use.
〈課題を解決するための手段〉
本発明者らは、上記の課題を達成すべく、鋭意検討の結
果９本発明に到達したものである。<Means for Solving the Problems> In order to achieve the above-mentioned problems, the present inventors have arrived at the present invention as a result of intensive studies.
すなわち本発明は９反応に使用して活性が低下したニオ
ブ酸触媒を、室温〜１００℃の温度範囲で、炭素数４〜
６の液相の炭化水素で接触処理することを特徴とするニ
オブ酸触媒の再生方法に係るものである。That is, the present invention uses a niobic acid catalyst whose activity has decreased after being used in 9 reactions in a temperature range of room temperature to 100°C, with a carbon number of 4 to 4.
The present invention relates to a method for regenerating a niobic acid catalyst characterized by carrying out a contact treatment with a liquid-phase hydrocarbon as described in No. 6.
以下、詳細に説明する。This will be explained in detail below.
本発明のニオブ酸触媒とは、ニオブ酸単味。The niobic acid catalyst of the present invention is simple niobic acid.
又は担体に担持されたニオブ酸触媒をいう。担体として
は、特に制限されるものではないが。Or it refers to a niobic acid catalyst supported on a carrier. The carrier is not particularly limited.
通常Ｓｌｏ ２ 、 Ａ１２０３等が用いられる。ニオ
ブ触媒の形状としては、粉末状でもよいが、打錠成型機
、ペレタイザー等によって成型されたものが好ましい。Usually, Slo 2 , A1203, etc. are used. Although the niobium catalyst may be in powder form, it is preferably molded using a tablet molding machine, pelletizer, or the like.
本発明の方法により再生し得るニオブ酸触媒は１反応に
使用して活性が低下した。前記のニオブ酸触媒である。The niobic acid catalyst that can be regenerated by the method of the present invention has decreased activity after being used in one reaction. The above-mentioned niobic acid catalyst.
ここで、対象とする反応の範囲に特に制限はないが、イ
ソブチレンとイソブチルアルデヒドから２．４−ジメチ
ル−２５ヘキサジエンを合成する反応や、イソブチレン
による２量化反応を対象とする場合は１本発明の効果が
特に著しい。Here, there is no particular restriction on the scope of the target reaction, but if the target is a reaction for synthesizing 2,4-dimethyl-25hexadiene from isobutylene and isobutyraldehyde or a dimerization reaction using isobutylene, one of the methods of the present invention is applicable. The effect is particularly remarkable.
本発明の接触処理に用いられる炭化水素は。The hydrocarbons used in the contact treatment of the present invention are:
後述の接触処理条件において液相を保ち得る炭素数４〜
６の炭化水素であれば特に制限されないが、好ましくは
不飽和炭化水素であり、更に好ましくはイソブチン又は
１−ブテンである。A carbon number of 4 or more that can maintain a liquid phase under the contact treatment conditions described below.
The hydrocarbon of No. 6 is not particularly limited, but is preferably an unsaturated hydrocarbon, and more preferably isobutyne or 1-butene.
なお、二種以上の炭化水素を混合して用いてもよい。Note that two or more types of hydrocarbons may be used in combination.
ここで９本発明の方法によらず、気相の炭化水素を用い
た場合、用いた炭化水素自身の反応が起き、再生の効果
は失われる。Here, if gas-phase hydrocarbons are used instead of the method of the present invention, the hydrocarbons used themselves will undergo a reaction, and the regeneration effect will be lost.
本発明の炭化水素による接触処理は、室温〜１００℃の
温度範囲で行なわれる。１００℃を超えて処理を行なう
と、使用した炭化水素自身の反応が起き１本発明の効果
は失われる。なお、接触処理をする時の温度は一定に保
つ必要はなく 、 １００℃から室温までの範囲で降温
させながら処理をしても良い。接触処理をするときの圧
力としては、室温から１００℃の温度において用いた炭
化水素が液相を保つ圧力であれば、特に限定はない。The contact treatment with hydrocarbons of the present invention is carried out at a temperature range of room temperature to 100°C. If the treatment is carried out at a temperature exceeding 100°C, the hydrocarbon itself will react and the effect of the present invention will be lost. Note that it is not necessary to keep the temperature constant during the contact treatment, and the treatment may be performed while decreasing the temperature in the range from 100° C. to room temperature. The pressure during the contact treatment is not particularly limited as long as the pressure allows the hydrocarbon used to maintain a liquid phase at temperatures ranging from room temperature to 100°C.
接触処理をする具体的な方法としては、特に限定されな
いが、液相の炭化水素を、再生すべきニオブ酸触媒が充
填された層に流通させる方法が好ましい。このときの炭
化水素の流量及び接触処理時間については、とくに限定
されないが。A specific method for carrying out the contact treatment is not particularly limited, but a method in which liquid-phase hydrocarbons are passed through a bed filled with a niobic acid catalyst to be regenerated is preferred. The flow rate of the hydrocarbon and the contact treatment time at this time are not particularly limited.
通常はニオブ酸触媒の充填体積に対し、１時間あたり１
〜５倍体積量で、２時間以上流通されて行なわれる。Usually 1 hour per hour for the packed volume of niobic acid catalyst.
~5 times the volume and passed for more than 2 hours.
本発明は、上記説明のとおり、比較的簡単な方法により
、広汎な範囲の反応に使用されて活性が低下したニオブ
酸触媒の再生を可能とするものである。本発明の方法に
よりニオブ酸触媒の再生が行なわれる機構の詳細につい
ては、必液相の炭化水素が、洗浄、除去する。いわゆる
洗浄効果による部分も大きいと推定される。As explained above, the present invention makes it possible to regenerate a niobic acid catalyst whose activity has decreased due to its use in a wide range of reactions by a relatively simple method. Regarding the details of the mechanism by which the niobic acid catalyst is regenerated by the method of the present invention, hydrocarbons in the essential liquid phase are washed and removed. It is estimated that a large portion is due to the so-called cleaning effect.
なお９本発明を実施するための再生装置の型式について
は、特に限定されないが、上記の観点から、液相の炭化
水素を連続的に供給、抜出し得る。いわゆる連続反応装
置が好ましい。Note that the type of regenerator for carrying out the present invention is not particularly limited, but from the above point of view, liquid-phase hydrocarbons can be continuously supplied and extracted. So-called continuous reactors are preferred.
以下、実施例によって本発明を更に具体的に説明するが
９本発明の範囲はこれによって制限をうけるものではな
い。EXAMPLES Hereinafter, the present invention will be explained in more detail with reference to Examples, but the scope of the present invention is not limited thereby.
〈実施例〉
実施例１
イソブチレン４５．０ｇ／ｈ、 イソブチルアルデヒド
１４．５ ｇ ／ｈ、 ２５０℃，１０ｋｇ／ｃｍ２Ｇ
の反応条件下、 ２．４・−ジメチル−２５−ヘキサ
ンエンの製造の反応に９７６時間使用し、イソブチルア
ルデヒド基準の転化率が１反応開始時における８６．４
９６から２８，３％まで低下したニオブ酸触媒（ＣＢＭ
ｈ・１社製、ニオブ酸単味）４０ｇに対し、 ４０’Ｃ
，５ｋｇ／Ｃｍ２Ｇでイソブチレンを９０ｇ／ｈで８時
間流し接触処理をした。該接触処理後のニオブ酸触媒を
用い、再度イソブチレンとイソブチルアルデヒドの反応
を、前記と同様の条件で行なったところ、イソブチルア
ルデヒド基準の転化率は７４．０％まで回復した。また
、 再生触媒を用いた場合の２．４−ジメチル２．５−
へキサンエンへの選択率、及び使用中における活性低下
の傾向は。<Example> Example 1 Isobutylene 45.0 g/h, Isobutyraldehyde 14.5 g/h, 250°C, 10 kg/cm2G
It was used for 976 hours in the reaction to produce 2.4-dimethyl-25-hexaneene under the reaction conditions, and the conversion rate based on isobutyraldehyde was 86.4 at the start of the reaction.
Niobic acid catalyst (CBM) decreased from 96 to 28,3%
40'C for 40g of niobic acid (manufactured by h.1)
, 5 kg/Cm2G and isobutylene was flowed at 90 g/h for 8 hours for contact treatment. When the reaction between isobutylene and isobutyraldehyde was carried out again under the same conditions as above using the niobic acid catalyst after the contact treatment, the conversion rate based on isobutyraldehyde was recovered to 74.0%. In addition, when using a regenerated catalyst, 2.4-dimethyl 2.5-
What is the selectivity to hexaneene and the tendency for activity to decrease during use?
新触媒の場合と、はぼ同等であった。It was almost the same as the case with the new catalyst.
比較例１
実施例１と同様の反応で９７６時間使用し、イソブチル
アルデヒド基準の転化率が８５．６９６から３１，０％
まで低下したニオブ酸触媒（実施例１のものと同種）４
０ｇに、８０℃＋ ５ ｋｇ／ ｃｍ２Ｇでスチームを
９０ ｇ／ ｈで８時間流した。該ニオブ酸を用い。Comparative Example 1 The same reaction as in Example 1 was used for 976 hours, and the conversion rate based on isobutyraldehyde was 85.696 to 31.0%.
Niobic acid catalyst (same as that of Example 1) reduced to 4
0 g, steam was flowed at 90 g/h for 8 hours at 80 °C + 5 kg/cm2G. using the niobic acid.
イソブチレンとインブチルアルデヒドの反応ラスチーム
処理前と同様の条件で行なったところ。The reaction between isobutylene and inbutyraldehyde was carried out under the same conditions as before the last steam treatment.
インブチルアルデヒド基準の転化率は４２．６％までし
か回復しなかった。また、スチーム処理後の触媒を用い
た場合、２，４−ツメチル−２，５−へキサジェノへの
選択率、及び使用中における活性低下の傾向は、新触媒
の場合と、はぼ同等であった。The conversion rate based on inbutyraldehyde was only recovered to 42.6%. Furthermore, when using a catalyst after steam treatment, the selectivity to 2,4-tmethyl-2,5-hexageno and the tendency of activity decline during use were almost the same as when using a new catalyst. Ta.
比較例２
実施例１と同様の反応で９７６時間使用し、イソブチル
アルデヒド基準の転化率か８７．２％から２９．５％ま
で低下したニオブ酸触媒（実施例１のものと同種）４０
ｇに対し、５００℃で、空気による焼成処理を５時間行
なった。該処理を行なったニオブ酸に対し、イソブチレ
ンとイソブチルアルデヒドの反応を処理前と同様の条件
で行なったところ、イソブチルアルデヒド基準の転化率
は３．２％であり、処理前より活性が低下した。Comparative Example 2 Niobic acid catalyst (same type as in Example 1) 40 which was used for 976 hours in the same reaction as in Example 1, and the conversion rate based on isobutyraldehyde decreased from 87.2% to 29.5%.
A baking treatment using air was performed at 500° C. for 5 hours. When the treated niobic acid was subjected to a reaction between isobutylene and isobutyraldehyde under the same conditions as before the treatment, the conversion rate based on isobutyraldehyde was 3.2%, indicating that the activity was lower than before the treatment.
〈発明の効果〉 以上説明したとおり９本発明により、従来。<Effect of the invention> As explained above, nine aspects of the present invention can be achieved using conventional methods.
難しいとされてきたニオブ酸触媒の再生方法であって、
ニオブ酸触媒本来の触媒機能を失うことなく、効率良く
再生する方法を提供することができた。This is a method for regenerating niobic acid catalysts, which has been considered difficult.
It was possible to provide a method for efficiently regenerating a niobic acid catalyst without losing its original catalytic function.
Claims (1)
室温〜１００℃の温度範囲で、炭素数４〜６の液相の炭
化水素で接触処理することを特徴とするニオブ酸触媒の
再生方法。（２）炭素数４〜６の液相の炭化水素として
、イソブチレン、１−ブテン、イソアミレン、シクロペ
ンテン、１−ヘキセン、又は２−ヘキセンを用いること
を特徴とする請求項（１）記載の方法。 （３）反応に使用して活性が低下したニオブ酸触媒が、
イソブチレンとイソブチルアルデヒドから２，４−ジメ
チル−２，５−ヘキサジエンを製造する反応に使用して
活性が低下したニオブ酸触媒であり、炭素数４〜６の液
相の炭化水素が、液相のイソブチレンである請求項（１
）記載の方法。[Claims] (1) A niobic acid catalyst whose activity has decreased due to use in the reaction,
A method for regenerating a niobic acid catalyst, comprising contact treatment with a liquid-phase hydrocarbon having 4 to 6 carbon atoms at a temperature ranging from room temperature to 100°C. (2) The method according to claim (1), wherein isobutylene, 1-butene, isoamylene, cyclopentene, 1-hexene, or 2-hexene is used as the liquid phase hydrocarbon having 4 to 6 carbon atoms. (3) The niobic acid catalyst whose activity has decreased after being used in the reaction is
This is a niobic acid catalyst whose activity has decreased when used in the reaction to produce 2,4-dimethyl-2,5-hexadiene from isobutylene and isobutyraldehyde. Claim (1) which is isobutylene
) method described.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2109838A JPH089000B2 (en) | 1990-04-24 | 1990-04-24 | Niobate catalyst regeneration method |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2109838A JPH089000B2 (en) | 1990-04-24 | 1990-04-24 | Niobate catalyst regeneration method |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH047036A true JPH047036A (en) | 1992-01-10 |
| JPH089000B2 JPH089000B2 (en) | 1996-01-31 |
Family
ID=14520488
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2109838A Expired - Lifetime JPH089000B2 (en) | 1990-04-24 | 1990-04-24 | Niobate catalyst regeneration method |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH089000B2 (en) |
-
1990
- 1990-04-24 JP JP2109838A patent/JPH089000B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| JPH089000B2 (en) | 1996-01-31 |
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