CN104437659A - Preparation method of homogeneous molybdenum-based epoxy catalyst - Google Patents
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Abstract
The invention relates to a preparation method for a homogeneous molybdenum-based epoxy catalyst, which is mainly used for solving the problems of low conversion rate of organic peroxides and low selectivity of epoxy products in the prior art. The preparation method for the homogeneous molybdenum-based epoxy catalyst comprises the following steps: (a) dissolving a molybdenum source, water and a peroxide into a solvent to obtain a mixture I; (b) adding acidic materials into the mixture I, and reacting for 0.5-2 hours at 40-80 DEG C to obtain a mixture II; and (c) adding an alkaline material into the mixture II, and stirring for 0.5-72 hours at the room temperature to obtain the homogeneous molybdenum-based epoxy catalyst. According to the technical scheme of the preparation method for the homogeneous molybdenum-based epoxy catalyst, the problems can be well solved, and the preparation method can be used for industrial production of epoxy propane by epoxidation of cumyl hydroperoxide and propylene.
Description
Technical field
The present invention relates to a kind of preparation method of homogeneous phase molybdenum basic ring oxidation catalyst.
Background technology
Expoxy propane is very important basic organic chemical industry raw material, is the second largest derivative of propylene.Existing Synthesis of Propylene Oxide is mainly chlorohydrination and conjugated oxidation (also known as peroxidating method or indirect oxidation method).The advantage of chlorohydrination is that flow process is short, technical maturity, operating flexibility large, little to raw material propylene purity requirement, equipment investment is few.But, often produce 1 ton of expoxy propane by-product 40 ~ 50 tons in chlorohydrination technical process containing 2 ~ 3 % by weight CaCl
2with the waste water of organochlorine, environmental problem becomes increasingly conspicuous.Conjugated oxidation refers to and utilizes the organic peroxide such as TBHP or ethylbenzene hydroperoxide, and cooxidation propylene generates expoxy propane.The method produces a large amount of joint product tert-butyl alcohols or styrene, and substantially often producing 1 ton of expoxy propane about has 2.5 tons of tert-butyl alcohols or 1.8 tons of styrene, thus constrains its application.And CHP method refers to dicumyl peroxide to be oxidant, propylene oxide produces expoxy propane, and produces dimethyl benzyl alcohol, and then dimethyl benzyl alcohol is through dehydration hydrogenation regeneration isopropylbenzene, and recovery reenters reaction system, therefore this technique will not produce any co-product.
For heterogeneous catalytic reaction, activated centre only only has active atomic or the avtive spot of catalyst surface; And in homogeneous catalytic reaction, metallic atoms all in catalyst is all activated centre.Therefore, homogeneous catalysis has high-activity high-selectivity and the feature such as reaction speed is fast.In addition, relative to heterogeneous catalysis, in homogeneous catalytic reaction, reactant can spread rapidly, avoids causing catalysqt deactivation because reacting sharply heat release.
Document CN201110369705.7 discloses a kind of method of propylene liquid phase oxidation expoxy propane, and the preparation method of the catalyst used in the method comprises the following steps: inorganic molybdenum source is dissolved in acid solution or 30 % by weight hydrogenperoxide steam generator in; Molybdenum solution after dissolving completely is at 150 ~ 180 DEG C, and hydrothermal recrystallization method 24 ~ 48 hours, through being separated, washing the powder catalyst obtaining white.But this catalyst is solid, be liquid-solid heterogeneous reaction in the reaction for propylene liquid phase oxidation expoxy propane, active poor, organic peroxide low conversion rate, epoxidation product is selective also low.
Summary of the invention
Technical problem to be solved by this invention is that prior art is when existing the reaction of catalyst with base of molybdenum for propylene liquid phase oxidation expoxy propane, organic peroxide low conversion rate, the selective low problem of epoxidation product, provides a kind of preparation method of new homogeneous phase molybdenum basic ring oxidation catalyst.Catalyst prepared by the method, in organic peroxide and epoxidation reaction of olefines, has that organic peroxide conversion ratio is high, the selective high feature of epoxidation product.
For solving the problems of the technologies described above, the technical solution used in the present invention is as follows: a kind of preparation method of homogeneous phase molybdenum basic ring oxidation catalyst, comprises the following steps:
A) molybdenum source, water and peroxide are dissolved in solvent, obtain mixture I;
B) in mixture I, add acidic materials, react 0.5 ~ 2 hour under 40 ~ 80 DEG C of conditions, obtain mixture II;
C) in mixture II, add alkaline matter, stirring at room temperature 0.5 ~ 72 hour, namely obtain described homogeneous phase molybdenum basic ring oxidation catalyst;
Wherein, described molybdenum source is selected from least one in molybdenum oxide, molybdic acid, acetyl acetone, ammonium dimolybdate or ammonium heptamolybdate;
Described peroxide is selected from least one in hydrogen phosphide cumene, hydrogen peroxide ethylbenzene or hydrogen peroxide;
Described solvent is selected from ethylbenzene, α, at least one in alpha-alpha-dimethyl benzylalcohol, xylyl alcohol or isopropylbenzene;
Described acidic materials are selected from least one in isooctyl acid, aphthenic acids, 2-Cyclopentylacetic acid, caproic acid, hydrochloric acid, sulfuric acid or nitric acid;
Described alkaline matter is selected from least one in sodium naphthenate, sodium carbonate, carbonyl magnesium, sodium acid carbonate or sodium acetate;
The weight ratio of molybdenum source and water is 1:(1 ~ 20), the weight ratio of molybdenum source and peroxide is 1:(0.1 ~ 20), the weight ratio of molybdenum source and solvent is 1:(2 ~ 10), the weight ratio of molybdenum source and acid flux material is 1:(5 ~ 20), the weight ratio of molybdenum source and alkaline matter is 1:(10 ~ 50).
In technique scheme, preferably, described molybdenum source is selected from least one in molybdenum oxide, ammonium dimolybdate or ammonium heptamolybdate.
In technique scheme, preferably, described peroxide is selected from least one in the cumene solution of hydrogen phosphide cumene, the ethylbenzene solution of hydrogen peroxide ethylbenzene or the aqueous solution of hydrogen peroxide.More preferably, described peroxide is selected from least one in the cumene solution of hydrogen phosphide cumene or the ethylbenzene solution of hydrogen peroxide ethylbenzene.
In technique scheme, preferably, described acidic materials are selected from least one in isooctyl acid or aphthenic acids.
In technique scheme, preferably, described solvent is selected from least one in ethylbenzene or isopropylbenzene.
In technique scheme, preferably, described alkaline matter is selected from least one in sodium naphthenate or sodium acetate.
In technique scheme, preferably, the weight ratio of molybdenum source and water is 1:(5 ~ 15), the weight ratio of molybdenum source and peroxide is 1:(0.5 ~ 10), the weight ratio of molybdenum source and solvent is 1:(4 ~ 8), the weight ratio of molybdenum source and acid flux material is 1:(10 ~ 15), the weight ratio of molybdenum source and alkaline matter is 1:(15 ~ 30).
In technique scheme, preferably, in described catalyst, molybdenum content is 0.01 ~ 5 % by weight.More preferably, in described catalyst, molybdenum content is 0.1 ~ 2 % by weight.
During the epoxidation reaction of the homogeneous phase molybdenum basic ring oxidation catalyst prepared of the inventive method for organic peroxide and alkene, alkene, organic peroxide are contacted with described homogeneous phase molybdenum basic ring oxidation catalyst, obtains epoxide.Wherein, reaction temperature is 40 ~ 130 DEG C, and preferable range is 60 ~ 110 DEG C; Reaction time is 0.5 ~ 3 hour, and preferable range is 0.5 ~ 2 hour; Reaction pressure is 0.1 ~ 5MPa, and preferable range is 0.3 ~ 2MPa; The mol ratio of alkene and organic peroxide is 1 ~ 20, and preferable range is 1 ~ 10; The consumption of catalyst is counted with molybdenum: the content of molybdenum in reaction raw materials is 1 ~ 1000ppm, and preferable range is 5 ~ 500ppm.
Adopt homogeneous phase molybdenum basic ring oxidation catalyst prepared by the inventive method, for in the epoxidation reaction of hydrogen phosphide cumene and propylene, the conversion ratio of hydrogen phosphide cumene can reach 99.9%, and the selective of expoxy propane reaches 99.9%, achieves good technique effect.
Accompanying drawing explanation
The infrared absorption pattern of the catalyst M-1 that Fig. 1 synthesizes for [embodiment 1].
The infrared absorption pattern of the catalyst M-2 that Fig. 2 synthesizes for [embodiment 2].
The infrared absorption pattern of the catalyst M-3 that Fig. 3 synthesizes for [embodiment 3].
The infrared absorption pattern of the catalyst M-4 that Fig. 4 synthesizes for [embodiment 4].
In Fig. 1 ~ 4, at 1033cm
-1and 1810cm
-1near there is Mo-O vibration absorption peak, prove that Mo species have entered in skeleton, form organic metal molybdenum compound.
Below by embodiment, the present invention is further elaborated.
Detailed description of the invention
[embodiment 1]
Get 1 gram of molybdenum trioxide, add deionized water 5 grams, after add 1 gram of cumene solution containing 50 % by weight hydrogen phosphide cumenes, stir, after add 10 grams of isooctyl acids and 4 grams of isopropylbenzenes, be heated to 50 DEG C, stir 2 hours, molybdenum compound progressively dissolves, and mixture color progressively changes brown into by glassy yellow; Then add sodium naphthenate 15 grams, stir 0.5 hour, obtain homogeneous phase organic-molybdenum catalyst M-1.M-1 catalyst is at 1033cm
-1and 1810cm
-1near there is Mo-O vibration absorption peak, see Fig. 1.
In molybdenum in MO-1, molybdenum content is 1.9 % by weight.
Get 0.01 gram of M-1 catalyst, pass into 50 kilograms of propylene and the double centner cumene solution containing 50 % by weight hydrogen phosphide cumenes, reaction temperature 60 DEG C, reaction pressure 0.3MPa.Terminate after 0.5 hour reaction time, record hydrogen phosphide cumene conversion ratio 99.9 % by weight, selective 99.5% of expoxy propane.
[embodiment 2]
Get 1 gram of ammonium dimolybdate, add deionized water 10 grams, add 4 grams of ethylbenzene solutions containing 50 % by weight hydrogen peroxide ethylbenzene, stir, after add 12 grams of aphthenic acids and 6 grams of ethylbenzene, be heated to 60 DEG C, stir 1 hour, molybdenum compound progressively dissolves, and mixture color progressively changes brown into by glassy yellow; Then add sodium naphthenate 20 grams, stir 12 hours, obtain homogeneous phase organic-molybdenum catalyst M-2.M-2 catalyst is at 1033cm
-1and 1810cm
-1near there is Mo-O vibration absorption peak, see Fig. 2.
In molybdenum in M-2, molybdenum content is 1.1 % by weight.
Get 0.1 gram of M-2 catalyst, pass into 5 kilograms of propylene and 10 kilograms of cumene solutions containing 50 % by weight hydrogen phosphide cumenes, reaction temperature 80 DEG C, reaction pressure 0.8MPa.Terminate after 1 hour reaction time, record hydrogen phosphide cumene conversion ratio 99.7 % by weight, selective 99.9% of expoxy propane.
[embodiment 3]
Get 1 gram of ammonium heptamolybdate, add deionized water 15 grams, add 16 grams of cumene solutions containing 50 % by weight hydrogen phosphide cumenes, stir, after add 15 grams of isooctyl acids and 5 grams of isopropylbenzenes, be heated to 65 DEG C, stir 2 hours, molybdenum compound progressively dissolves, and mixture color progressively changes brown into by glassy yellow; Then add sodium naphthenate 15 grams, stir 24 hours, obtain homogeneous phase organic-molybdenum catalyst M-3.M-3 catalyst is at 1033cm
-1and 1810cm
-1near there is Mo-O vibration absorption peak, see Fig. 3.
In molybdenum in M-3, molybdenum content is 0.8 % by weight.
Get 1.3 grams of M-3 catalyst, pass into 0.5 kilogram of propylene and 1 kilogram of cumene solution containing 50 % by weight hydrogen phosphide cumenes, reaction temperature 110 DEG C, reaction pressure 2MPa.Terminate after 0.5 hour reaction time, record hydrogen phosphide cumene conversion ratio 99.9 % by weight, selective 99.5% of expoxy propane.
[embodiment 4]
Get 1 gram of ammonium heptamolybdate, add deionized water 5 grams, add 20 grams of cumene solutions containing 50 % by weight hydrogen phosphide cumenes, stir, after add 15 grams of isooctyl acids and 8 grams of isopropylbenzenes, be heated to 70 DEG C, stir 1.5 hours, molybdenum compound progressively dissolves, and mixture color progressively changes brown into by glassy yellow; Then add sodium naphthenate 30 grams, stir 36 hours, obtain homogeneous phase organic-molybdenum catalyst M-4.
In molybdenum in M-4, molybdenum content is 0.8 % by weight.M-4 catalyst is at 1033cm
-1and 1810cm-
1near there is Mo-O vibration absorption peak, see Fig. 4.
Get 1 gram of M-4 catalyst, pass into 0.3 kilogram of propylene and 0.7 kilogram of cumene solution containing 50 % by weight hydrogen phosphide cumenes, reaction temperature 100 DEG C, reaction pressure 1.5MPa.Terminate after 2 hours reaction time, record hydrogen phosphide cumene conversion ratio 99.9 % by weight, selective 99.5% of expoxy propane.
[comparative example 1]
Prepare molybdenum oxide catalyst according to method disclosed in document CN201110369705.7 embodiment 3 and carry out propylene ring oxidation reaction.
Commodity molybdenum oxide powder is joined 30%H
2o
2solution in, stirring at room temperature 3 days, then adds 2 grams of macro porous silica gels, and 50 DEG C are stirred 2 hours, get 70 ml solns and transfer to water and strangle in reactor, keep 24 hours at 180 DEG C of baking ovens.Then take out, centrifugation, adopt deionized water to wash 3 times, then ethanol washs 3 times, and it is molybdenum oxide catalyst that low temperature drying obtains white powder.
Above-mentioned molybdenum oxide catalyst good for compression molding is got 1 gram, carries out epoxidation of propylene experiment.It is the hydrogen phosphide cumene 190 grams of 27.2% by weight fraction, solvent isopropylbenzene 90 grams and 1 gram of catalyst join in the autoclave of 1 liter, then propylene liguid is passed into autoclave, propylene/hydrogen phosphide cumene mol ratio is 2/100, then be heated to 100 DEG C, and keep 2 little the reaction times.After reaction terminates, record hydrogen phosphide cumene conversion ratio 89.5 % by weight, selective 56.1% of expoxy propane.
Claims (10)
1. a preparation method for homogeneous phase molybdenum basic ring oxidation catalyst, comprises the following steps:
A) molybdenum source, water and peroxide are dissolved in solvent, obtain mixture I;
B) in mixture I, add acidic materials, react 0.5 ~ 2 hour under 40 ~ 80 DEG C of conditions, obtain mixture II;
C) in mixture II, add alkaline matter, stirring at room temperature 0.5 ~ 72 hour, namely obtain described homogeneous phase molybdenum basic ring oxidation catalyst;
Wherein, described molybdenum source is selected from least one in molybdenum oxide, molybdic acid, acetyl acetone, ammonium dimolybdate or ammonium heptamolybdate;
Described peroxide is selected from least one in hydrogen phosphide cumene, hydrogen peroxide ethylbenzene or hydrogen peroxide;
Described solvent is selected from ethylbenzene, α, at least one in alpha-alpha-dimethyl benzylalcohol, xylyl alcohol or isopropylbenzene;
Described acidic materials are selected from least one in isooctyl acid, aphthenic acids, 2-Cyclopentylacetic acid, caproic acid, hydrochloric acid, sulfuric acid or nitric acid;
Described alkaline matter is selected from least one in sodium naphthenate, sodium carbonate, carbonyl magnesium, sodium acid carbonate or sodium acetate;
The weight ratio of molybdenum source and water is 1:(1 ~ 20), the weight ratio of molybdenum source and peroxide is 1:(0.1 ~ 20), the weight ratio of molybdenum source and solvent is 1:(2 ~ 10), the weight ratio of molybdenum source and acid flux material is 1:(5 ~ 20), the weight ratio of molybdenum source and alkaline matter is 1:(10 ~ 50).
2. the preparation method of homogeneous phase molybdenum basic ring oxidation catalyst according to claim 1, is characterized in that molybdenum source is selected from least one in molybdenum oxide, ammonium dimolybdate or ammonium heptamolybdate.
3. the preparation method of homogeneous phase molybdenum basic ring oxidation catalyst according to claim 1, is characterized in that described peroxide is selected from least one in the cumene solution of hydrogen phosphide cumene, the ethylbenzene solution of hydrogen peroxide ethylbenzene or the aqueous solution of hydrogen peroxide.
4. the preparation method of homogeneous phase molybdenum basic ring oxidation catalyst according to claim 3, is characterized in that described peroxide is selected from least one in the cumene solution of hydrogen phosphide cumene or the ethylbenzene solution of hydrogen peroxide ethylbenzene.
5. the preparation method of homogeneous phase molybdenum basic ring oxidation catalyst according to claim 1, is characterized in that described acidic materials are selected from least one in isooctyl acid or aphthenic acids.
6. the preparation method of homogeneous phase molybdenum basic ring oxidation catalyst according to claim 1, is characterized in that described solvent is selected from least one in ethylbenzene or isopropylbenzene.
7. the preparation method of homogeneous phase molybdenum basic ring oxidation catalyst according to claim 1, is characterized in that described alkaline matter is selected from least one in sodium naphthenate or sodium acetate.
8. the preparation method of homogeneous phase molybdenum basic ring oxidation catalyst according to claim 1, it is characterized in that the weight ratio of molybdenum source and water is 1:(5 ~ 15), the weight ratio of molybdenum source and peroxide is 1:(0.5 ~ 10), the weight ratio of molybdenum source and solvent is 1:(4 ~ 8), the weight ratio of molybdenum source and acid flux material is 1:(10 ~ 15), the weight ratio of molybdenum source and alkaline matter is 1:(15 ~ 30).
9. the preparation method of homogeneous phase molybdenum basic ring oxidation catalyst according to claim 1, is characterized in that in described catalyst, molybdenum content is 0.01 ~ 5 % by weight.
10. the preparation method of homogeneous phase molybdenum basic ring oxidation catalyst according to claim 9, is characterized in that in described catalyst, molybdenum content is 0.1 ~ 2 % by weight.
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Cited By (6)
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| CN106582879A (en) * | 2016-11-11 | 2017-04-26 | 万华化学集团股份有限公司 | Epoxidation catalyst and preparation method thereof, epoxidation catalyst system and preparation method of epoxidation catalyst system |
| CN111018809A (en) * | 2019-12-24 | 2020-04-17 | 万华化学集团股份有限公司 | Load system and method for treating styrene epoxidation reaction liquid |
| CN111715292A (en) * | 2020-06-29 | 2020-09-29 | 万华化学集团股份有限公司 | Preparation method and application of molybdenum catalyst |
| CN113117755A (en) * | 2021-04-14 | 2021-07-16 | 万华化学集团股份有限公司 | Preparation method and application of molybdenum catalyst |
| CN113636991A (en) * | 2021-08-13 | 2021-11-12 | 中国天辰工程有限公司 | Synthesis method of epoxy cyclohexane |
| CN114426547A (en) * | 2020-09-29 | 2022-05-03 | 中国石油化工股份有限公司 | Method for producing dicyclopentadiene dioxide by using molybdenum-based homogeneous catalyst and obtained dicyclopentadiene dioxide |
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| CN106582879A (en) * | 2016-11-11 | 2017-04-26 | 万华化学集团股份有限公司 | Epoxidation catalyst and preparation method thereof, epoxidation catalyst system and preparation method of epoxidation catalyst system |
| CN106582879B (en) * | 2016-11-11 | 2018-10-16 | 万华化学集团股份有限公司 | A kind of epoxidation catalyst and preparation method thereof, a kind of epoxidation catalyst system and preparation method thereof |
| CN111018809A (en) * | 2019-12-24 | 2020-04-17 | 万华化学集团股份有限公司 | Load system and method for treating styrene epoxidation reaction liquid |
| CN111018809B (en) * | 2019-12-24 | 2022-08-05 | 万华化学集团股份有限公司 | Load system and method for treating styrene epoxidation reaction liquid |
| CN111715292A (en) * | 2020-06-29 | 2020-09-29 | 万华化学集团股份有限公司 | Preparation method and application of molybdenum catalyst |
| CN111715292B (en) * | 2020-06-29 | 2022-07-12 | 万华化学集团股份有限公司 | Preparation method and application of molybdenum catalyst |
| CN114426547A (en) * | 2020-09-29 | 2022-05-03 | 中国石油化工股份有限公司 | Method for producing dicyclopentadiene dioxide by using molybdenum-based homogeneous catalyst and obtained dicyclopentadiene dioxide |
| CN114426547B (en) * | 2020-09-29 | 2024-01-05 | 中国石油化工股份有限公司 | Method for producing dicyclopentadiene dioxide by molybdenum-based homogeneous catalyst and obtained dicyclopentadiene dioxide |
| CN113117755A (en) * | 2021-04-14 | 2021-07-16 | 万华化学集团股份有限公司 | Preparation method and application of molybdenum catalyst |
| CN113636991A (en) * | 2021-08-13 | 2021-11-12 | 中国天辰工程有限公司 | Synthesis method of epoxy cyclohexane |
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