CN104437659B - Preparation method of homogeneous molybdenum-based epoxy catalyst - Google Patents
Preparation method of homogeneous molybdenum-based epoxy catalyst Download PDFInfo
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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 molybdenum base epoxidation catalyst.
Background technology
Expoxy propane is highly important basic organic chemical industry raw material, is the second largest derivative of propylene.Existing epoxy third
Alkane production technology is mainly chlorohydrination and conjugated oxidation（Also known as peroxidating method or indirect oxidation method）.The advantage of chlorohydrination is flow process
Short, technical maturity, operating flexibility are big, little to raw material propylene purity requirement, equipment investment is few.But, chlorohydrination technical process
In often produce 40 ~ 50 tons of 1 ton of expoxy propane by-product and contain 2 ~ 3 weight % CaCl2With the waste water of organochlorine, environmental problem is increasingly prominent
Go out.Conjugated oxidation refers to that, using organic peroxides such as TBHP or ethylbenzene hydroperoxides, cooxidation propylene generates
Expoxy propane.The method produces the substantial amounts of joint product tert-butyl alcohol or styrene, substantially often produces 1 ton of expoxy propane and there are about 2.5
The ton tert-butyl alcohol or 1.8 tons of styrene, thus constrain its application.And CHP method refers to dicumyl peroxide as oxidant, oxidation
Production of propylene expoxy propane, and produce dimethyl benzyl alcohol, then dimethyl benzyl alcohol regenerates isopropylbenzene through dehydration hydrogenation, and returns
Receipts reenter reaction system, and 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, in catalyst, all of metallic atom is all activated centre.Therefore, homogeneous catalysis has high activity Gao Xuan
The features such as selecting property and reaction speed are fast.In addition, with respect to heterogeneous catalysis, in homogeneous catalytic reaction, reactant can expand rapidly
Dissipate, it is to avoid cause catalyst to inactivate because reacting drastically heat release.
Document CN201110369705.7 discloses a kind of method of propylene liquid phase oxidation expoxy propane, makes in the method
The preparation method of catalyst comprises the following steps：Inorganic molybdenum source is dissolved in acid solution or the peroxidating of 30 weight %
In hydrogen solution；Molybdenum solution after being completely dissolved at 150 ~ 180 DEG C, hydrothermal recrystallization method 24 ~ 48 hours, separating, washing obtains
The powder catalyst of white.But, this catalyst is solid, is liquid in the reaction for propylene liquid phase oxidation expoxy propane
Gu heterogeneous reaction, activity is poor, and organic peroxide conversion ratio is low, and epoxidation product is selectively also low.
Content of the invention
The technical problem to be solved is that prior art has catalyst with base of molybdenum for propylene liquid phase oxidation ring
During the reaction of Ethylene Oxide, organic peroxide conversion ratio is low, the selectively low problem of epoxidation product, provides a kind of new homogeneous
The preparation method of molybdenum base epoxidation catalyst.The catalyst of the method preparation is used for organic peroxide and epoxidation reaction of olefines
In, have the characteristics that organic peroxide high conversion rate, epoxidation product are selectively high.
For solving above-mentioned technical problem, the technical solution used in the present invention is as follows：A kind of homogeneous molybdenum base epoxidation catalyst
Preparation method, comprise the following steps：
a）Molybdenum source, water and peroxide are dissolved in solvent, obtain mixture I；
b）Add acidic materials in mixture I, react 0.5 ~ 2 hour under the conditions of 40 ~ 80 DEG C, obtain mixture II；
c）Add alkaline matter in mixture II, be stirred at room temperature 0.5 ~ 72 hour, that is, obtain described homogeneous molybdenum base epoxy
Change catalyst；
Wherein, described molybdenum source is selected from least in molybdenum oxide, molybdic acid, acetyl acetone, ammonium dimolybdate or ammonium heptamolybdate
Kind；
Described peroxide is selected from least one in cumyl hydroperoxide, hydrogen peroxide ethylbenzene or hydrogen peroxide；
Described solvent is selected from least one in ethylbenzene, alpha, alpha-dimethyl benzyl alcohol, xylyl alcohol or isopropylbenzene；
Described acidic materials are selected from isooctyl acid, aphthenic acids, 2-Cyclopentylacetic acid, caproic acid, hydrochloric acid, sulfuric acid or nitric acid at least
A kind of；
Described alkaline matter is selected from least one in sodium naphthenate, sodium carbonate, carbonyl magnesium, sodium acid carbonate or sodium acetate；
The weight of molybdenum source and water is than for 1:(1 ~ 20), the weight of molybdenum source and peroxide is than for 1:(0.1 ~ 20), molybdenum source with
The weight of solvent is than for 1:(2 ~ 10), the weight of molybdenum source and acid flux material is than for 1:The weight of (5 ~ 20), molybdenum source and alkaline matter
Than for 1:(10~50).
It is preferable that described molybdenum source is selected from least in molybdenum oxide, ammonium dimolybdate or ammonium heptamolybdate in technique scheme
Kind.
It is preferable that described peroxide is selected from the cumene solution of cumyl hydroperoxide, peroxide in technique scheme
Change at least one in the ethylbenzene solution of hydrogen ethylbenzene or the aqueous solution of hydrogen peroxide.It is highly preferred that described peroxide was selected from
At least one in the ethylbenzene solution of the cumene solution of hydrogen oxide isopropylbenzene or hydrogen peroxide ethylbenzene.
It is preferable that described acidic materials are selected from least one in isooctyl acid or aphthenic acids in technique scheme.
It is preferable that described solvent is selected from least one in ethylbenzene or isopropylbenzene in technique scheme.
It is preferable that described alkaline matter is selected from least one in sodium naphthenate or sodium acetate in technique scheme.
It is preferable that the weight of molybdenum source and water is than for 1 in technique scheme:The weight of (5 ~ 15), molybdenum source and peroxide
Than for 1:(0.5 ~ 10), the weight of molybdenum source and solvent is than for 1:(4 ~ 8), the weight of molybdenum source and acid flux material is than for 1:(10 ~ 15),
The weight of molybdenum source and alkaline matter is than for 1:(15~30).
In technique scheme it is preferable that in described catalyst molybdenum content be 0.01 ~ 5 weight %.It is highly preferred that described urge
In agent, molybdenum content is 0.1 ~ 2 weight %.
The homogeneous molybdenum base epoxidation catalyst of the inventive method preparation is used for organic peroxide and the epoxidation of alkene is anti-
At once, so that alkene, organic peroxide is contacted with described homogeneous molybdenum base epoxidation catalyst, obtain epoxide.Wherein, instead
Temperature is answered to be 40 ~ 130 DEG C, preferred scope is 60 ~ 110 DEG C；Reaction time is 0.5 ~ 3 hour, and preferred scope is 0.5 ~ 2 hour；
Reaction pressure is 0.1 ~ 5MPa, and preferred scope is 0.3 ~ 2MPa；Alkene is 1 ~ 20 with the mol ratio of organic peroxide, preferably model
Enclose for 1 ~ 10；The consumption of catalyst is calculated as with molybdenum：Content in reaction raw materials for the molybdenum be 1 ~ 1000ppm, preferred scope be 5 ~
500ppm.
Using the homogeneous molybdenum base epoxidation catalyst of the inventive method preparation, for the ring of cumyl hydroperoxide and propylene
In oxidation reaction, up to 99.9%, the selectivity of expoxy propane, up to 99.9%, achieves relatively the conversion ratio of cumyl hydroperoxide
Good technique effect.
Brief description
Fig. 1 is【Embodiment 1】The infrared absorption pattern of the catalyst M-1 of synthesis.
Fig. 2 is【Embodiment 2】The infrared absorption pattern of the catalyst M-2 of synthesis.
Fig. 3 is【Embodiment 3】The infrared absorption pattern of the catalyst M-3 of synthesis.
Fig. 4 is【Embodiment 4】The infrared absorption pattern of the catalyst M-4 of synthesis.
In Fig. 1 ~ 4, in 1033cm-1And 1810cm-1Nearby occur in that Mo-O vibration absorption peak it was demonstrated that Mo species have entered
Enter in skeleton, form organic metal molybdenum compound.
Below by embodiment, the present invention is further elaborated.
Specific embodiment
【Embodiment 1】
Take 1 gram of molybdenum trioxide, add 5 grams of deionized water, add 1 gram of isopropyl containing 50 weight % cumyl hydroperoxides afterwards
Benzole soln, stirring, add 10 grams of isooctyl acids and 4 grams of isopropylbenzenes afterwards, be heated to 50 DEG C, stir 2 hours, molybdenum compound is progressively molten
Solution, mixture color is progressively changed into brown by glassy yellow；It is subsequently adding 15 grams of sodium naphthenate, stirs 0.5 hour, obtain homogeneous
Organic molybdenum catalyst M-1.M-1 catalyst is in 1033cm-1And 1810cm-1Nearby occur in that Mo-O vibration absorption peak, see Fig. 1.
In MO-1 in terms of molybdenum, molybdenum content is 1.9 weight %.
Take 0.01 gram of M-1 catalyst, be passed through 50 kilograms of propylene and double centner contains the different of 50 weight % cumyl hydroperoxides
Propyl benzene solution, 60 DEG C of reaction temperature, reaction pressure 0.3MPa.Terminate after 0.5 hour reaction time, record cumyl hydroperoxide
Conversion ratio 99.9 weight %, the selectivity 99.5% of expoxy propane.
【Embodiment 2】
Take 1 gram of ammonium dimolybdate, add 10 grams of deionized water, add 4 grams of ethylbenzene containing 50 weight % hydrogen peroxide ethylbenzene molten
Liquid, stirring, add 12 grams of aphthenic acids and 6 grams of ethylbenzene afterwards, be heated to 60 DEG C, stir 1 hour, molybdenum compound progressively dissolves, mixing
Thing color is progressively changed into brown by glassy yellow；It is subsequently adding 20 grams of sodium naphthenate, stir 12 hours, obtain homogeneous organic-molybdenum and urge
Agent M-2.M-2 catalyst is in 1033cm-1And 1810cm-1Nearby occur in that Mo-O vibration absorption peak, see Fig. 2.
In M-2 in terms of molybdenum, molybdenum content is 1.1 weight %.
Take 0.1 gram of M-2 catalyst, be passed through 5 kilograms of propylene and 10 kilograms of isopropylbenzenes containing 50 weight % cumyl hydroperoxides
Solution, 80 DEG C of reaction temperature, reaction pressure 0.8MPa.Terminate after 1 hour reaction time, record cumyl hydroperoxide conversion ratio
99.7 weight %, the selectivity 99.9% of expoxy propane.
【Embodiment 3】
Take 1 gram of ammonium heptamolybdate, add 15 grams of deionized water, add 16 grams of isopropyls containing 50 weight % cumyl hydroperoxides
Benzole soln, stirring, add 15 grams of isooctyl acids and 5 grams of isopropylbenzenes afterwards, be heated to 65 DEG C, stir 2 hours, molybdenum compound is progressively molten
Solution, mixture color is progressively changed into brown by glassy yellow；It is subsequently adding 15 grams of sodium naphthenate, stirs 24 hours, obtain homogeneous
Organic molybdenum catalyst M-3.M-3 catalyst is in 1033cm-1And 1810cm-1Nearby occur in that Mo-O vibration absorption peak, see Fig. 3.
In M-3 in terms of molybdenum, molybdenum content is 0.8 weight %.
Take 1.3 grams of M-3 catalyst, be passed through 0.5 kilogram of propylene and 1 kilogram of isopropyl containing 50 weight % cumyl hydroperoxides
Benzole soln, 110 DEG C of reaction temperature, reaction pressure 2MPa.Terminate after 0.5 hour reaction time, record cumyl hydroperoxide and turn
Rate 99.9 weight %, the selectivity 99.5% of expoxy propane.
【Embodiment 4】
Take 1 gram of ammonium heptamolybdate, add 5 grams of deionized water, add 20 grams of isopropylbenzenes containing 50 weight % cumyl hydroperoxides
Solution, stirring, add 15 grams of isooctyl acids and 8 grams of isopropylbenzenes afterwards, be heated to 70 DEG C, stir 1.5 hours, molybdenum compound is progressively molten
Solution, mixture color is progressively changed into brown by glassy yellow；It is subsequently adding 30 grams of sodium naphthenate, stirs 36 hours, obtain homogeneous
Organic molybdenum catalyst M-4.
In M-4 in terms of molybdenum, molybdenum content is 0.8 weight %.M-4 catalyst is in 1033cm-1And 1810cm-1Nearby occur in that
Mo-O vibration absorption peak, is shown in Fig. 4.
Take 1 gram of M-4 catalyst, be passed through 0.3 kilogram of propylene and 0.7 kilogram of isopropyl containing 50 weight % cumyl hydroperoxides
Benzole soln, 100 DEG C of reaction temperature, reaction pressure 1.5MPa.Terminate after 2 hours reaction time, record cumyl hydroperoxide and turn
Rate 99.9 weight %, the selectivity 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 added to 30%H2O2Solution in, be stirred at room temperature 3 days, be subsequently adding 2 grams of macro porous silica gels,
50 DEG C are stirred 2 hours, take 70 milliliters of solution to transfer to water and strangle in reactor, keep 24 hours in 180 DEG C of baking ovens.Then take out,
Centrifugation, adopts and is washed with deionized 3 times, then ethanol washing 3 times, and low temperature drying obtains white powder and is catalyzed for molybdenum oxide
Agent.
Above-mentioned molybdenum oxide catalyst good for compression molding is taken 1 gram, carries out epoxidation of propylene experiment.Weight fraction is
190 grams of 27.2% cumyl hydroperoxide, 90 grams and 1 gram catalyst of solvent isopropylbenzene is added in 1 liter of autoclave,
Then it is passed through propylene liguid to autoclave, propylene/cumyl hydroperoxide mol ratio is 2/100, is then heated to 100
DEG C, and keep 2 little the reaction times.After reaction terminates, record cumyl hydroperoxide conversion ratio 89.5 weight %, expoxy propane
Selectivity 56.1%.
Claims (10)
1. a kind of preparation method of homogeneous molybdenum base epoxidation catalyst, comprises the following steps：
A) molybdenum source, water and peroxide are dissolved in solvent, obtain mixture I；
B) add acidic materials in mixture I, react 0.5～2 hour under the conditions of 40～80 DEG C, obtain mixture II；
C) add alkaline matter in mixture II, be stirred at room temperature 0.5～72 hour, that is, obtain described homogeneous molybdenum base epoxidation and urge
Agent；
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 cumyl hydroperoxide, hydrogen peroxide ethylbenzene or hydrogen peroxide；
Described solvent is selected from least one in ethylbenzene, alpha, alpha-dimethyl benzyl alcohol, xylyl alcohol or isopropylbenzene；
Described acidic materials are selected from least in isooctyl acid, aphthenic acids, 2-Cyclopentylacetic acid, caproic acid, hydrochloric acid, sulfuric acid or nitric acid
Kind；
Described alkaline matter is selected from least one in sodium naphthenate, sodium carbonate, carbonyl magnesium, sodium acid carbonate or sodium acetate；
The weight of molybdenum source and water is than for 1:(1～20), the weight of molybdenum source and peroxide is than for 1:(0.1～20), molybdenum source with molten
The weight of agent is than for 1:(2～10), the weight of molybdenum source and acidic materials is than for 1:The weight of (5～20), molybdenum source and alkaline matter
Than for 1:(10～50).
2. according to claim 1 the preparation method of homogeneous molybdenum base epoxidation catalyst it is characterised in that molybdenum source is selected from oxidation
At least one in molybdenum, ammonium dimolybdate or ammonium heptamolybdate.
3. according to claim 1 the preparation method of homogeneous molybdenum base epoxidation catalyst it is characterised in that described peroxide
In the cumene solution of cumyl hydroperoxide, the ethylbenzene solution of hydrogen peroxide ethylbenzene or the aqueous solution of hydrogen peroxide extremely
Few one kind.
4. according to claim 3 the preparation method of homogeneous molybdenum base epoxidation catalyst it is characterised in that described peroxide
At least one in the cumene solution of cumyl hydroperoxide or the ethylbenzene solution of hydrogen peroxide ethylbenzene.
5. according to claim 1 the preparation method of homogeneous molybdenum base epoxidation catalyst it is characterised in that described acidic materials
At least one in isooctyl acid or aphthenic acids.
6. according to claim 1 the preparation method of homogeneous molybdenum base epoxidation catalyst it is characterised in that described solvent is selected from
At least one in ethylbenzene or isopropylbenzene.
7. according to claim 1 the preparation method of homogeneous molybdenum base epoxidation catalyst it is characterised in that described alkaline matter
At least one in sodium naphthenate or sodium acetate.
8. according to claim 1 the preparation method of homogeneous molybdenum base epoxidation catalyst it is characterised in that the weight of molybdenum source and water
Amount ratio is 1:(5～15), the weight of molybdenum source and peroxide is than for 1:(0.5～10), the weight of molybdenum source and solvent is than for 1:(4
～8), the weight of molybdenum source and acidic materials is than for 1:(10～15), the weight of molybdenum source and alkaline matter is than for 1:(15～30).
9. according to claim 1 the preparation method of homogeneous molybdenum base epoxidation catalyst it is characterised in that in described catalyst
Molybdenum content is 0.01～5 weight %.
10. according to claim 9 the preparation method of homogeneous molybdenum base epoxidation catalyst it is characterised in that in described catalyst
Molybdenum content is 0.1～2 weight %.
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Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
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| 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 |
| 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 |
| 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 |
| 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 |
| CN113117755B (en) * | 2021-04-14 | 2022-08-05 | 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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| CN1900071A (en) * | 2005-07-21 | 2007-01-24 | 中国科学院大连化学物理研究所 | Process for preparing epoxy chloropropane |
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