CN102452899A - Method for preparing propylene glycol from propylene - Google Patents
Method for preparing propylene glycol from propylene Download PDFInfo
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- CN102452899A CN102452899A CN2010105145047A CN201010514504A CN102452899A CN 102452899 A CN102452899 A CN 102452899A CN 2010105145047 A CN2010105145047 A CN 2010105145047A CN 201010514504 A CN201010514504 A CN 201010514504A CN 102452899 A CN102452899 A CN 102452899A
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- 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
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- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
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- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
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Abstract
The invention discloses a method for preparing propylene glycol from propylene. The method comprises a step that: under the existence of a titanium silicalite molecular sieve composite catalyst, propylene and hydrogen peroxide are directly subject to an epoxidation and ring-opening hydration one-step reaction in a reactor, such that propylene glycol is prepared. The catalyst is composed of titanium silicalite molecular sieve, acidic molecular sieve and resin. According to the invention, a fixed-bed propylene glycol preparation technology is realized by using the titanium silicalite molecular sieve composite catalyst, wherein propylene glycol directly prepared from propylene. Traditionally, propylene is subject to epoxidation, such that propylene oxide is produced; and propylene oxide is subject to ring-opening hydration, such that propylene glycol is prepared. With the method provided by the invention, problems such as complicated reaction steps and high energy consumption of the traditional two-step reaction are solved, and the reaction efficiency is improved.
Description
Technical field
The invention belongs to a kind of preparation method of Ucar 35, be suitable for that propylene, ydrogen peroxide 50 directly carry out epoxidation, open loop hydration single step reaction prepares in the catalytic reaction process of Ucar 35.
Background technology
Since synthetic first lattice oxygen selective oxidation titanium-silicon molecular sieve catalyst TS-1 of Italian Enichem company's nineteen eighty-three; Owing to its excellent oxidation selectivity and gentle reaction conditions become the focus that oxide catalyst is studied, this discovery is regarded as a quantum jump of environment-friendly catalyst exploitation.
Titanium-silicon molecular sieve catalyst for the epoxidation reaction of low-carbon alkene, is a catalyzer with the HTS having important effect aspect the epoxidation catalysis of alkene, and hydrogen peroxide is the liquid phase epoxidation process of oxygenant; Because reaction conditions is gentle, selectivity of product is high, environmental friendliness etc., and the low-carbon alkene epoxidation that is considered to have very much application potential prepares the catalytic conversion process of epoxy compounds and derived product thereof.
Ucar 35 has another name called 1,2-Ucar 35,1, and the 2-dihydroxypropane is to be raw material with the propylene oxide, makes a kind of Chemicals that hydrolysis under the condition of catalyzer or direct hydrolysis make at sulfuric acid.It also can be used as the raw material of producing softening agent, tensio-active agent, emulsifying agent and emulsion splitter mainly as the raw material of producing unsaturated polyester.In foodstuffs industry, Ucar 35 can be used as solvent, the mould inhibitor of spices, food pigment.Food emulsifier and the fruit sanitas that accelerates the ripening.In medicine industry, Ucar 35 is commonly used to make solvent, tenderizer and the vehicle of all kinds of ointment, ointment and pill.In cosmetic industry, Ucar 35 can be used to produce solvent and tenderizer.In addition, Ucar 35 also can be used as the tobacco moistening agent, agent is frozen on rank and thermal barrier uses.
Prepare in the reaction process of Ucar 35 in epoxidation of propylene, open loop hydration, the conversion from the propylene to the Ucar 35 is the successive reaction in two steps, relates to two kinds of catalystic converter systems of selective oxidation and acid catalysis.In traditional production process; Epoxidation of propylene generates propylene oxide and follow-up propylene oxide open loop hydration reaction is separately carried out; Mainly be because the reaction conditions of these two reactions differs too big, the required water of propylene oxide hydration adds in the reaction of second step.The industrial process of Ucar 35 is at first to produce propylene oxide, and the employing propylene is a raw material, and the peroxo-ethylbenzene is an oxygenant; Catalyzer is the compound that is carried on vanadium, tungsten, molybdenum or titanium on the silicon-dioxide; Mol ratio at propylene and ethylbenzene superoxide is 6: 1, and temperature of reaction is 80～90 ℃, and pressure is that 33MPa and duration of contact are under the reaction conditions of 30min; The superoxide transformation efficiency is 97%, and the propylene oxide selectivity is 91%～95%.Then propylene oxide and water carry out open loop hydration reaction generation Ucar 35, and reaction soln obtains Ucar 35 and other sub product through fractionation.CN1678598A has proposed a kind of continuous method for preparing Ucar 35; At first generate the Ucar 35 of propylene oxide and part through propylene and hydroperoxidation; Propylene oxide and water react the method for preparing Ucar 35 with continuous mode in thermal coupling tower subsequently then. and it is starting raw material with the pure propylene oxide that this method has well solved the Ucar 35 industrial preparation; Process is complicated; The shortcoming that sub product is many, but still exist propylene to generate propylene oxide, and the propylene oxide hydration prepares the deficiency that Ucar 35 is a proceed step by step in two reactor drums.
Summary of the invention
For overcoming the deficiency that prior art exists, the invention provides a kind of adopt that fixed-bed process, technology simply realizes in a reactor drum produce the method for Ucar 35 by propylene.
What the present invention proposed is the method for being produced Ucar 35 by propylene, and this method adopts fixed-bed reactor, comprising: in the presence of the HTS composite catalyst; Propylene, ydrogen peroxide 50 carry out epoxidation, open loop hydration reaction one goes on foot and makes Ucar 35, and the HTS composite catalyst that is wherein adopted comprises HTS, acidic molecular sieve and resin; Weight with catalyzer is benchmark; The total content of HTS and acidic molecular sieve is 1%～50%, is preferably 10%～25%, and the content of resin is 50%～99%; Be preferably 75%～90%, wherein the weight ratio of HTS and acidic molecular sieve is 5: 1～20: 1.
The character of the HTS composite catalyst that is adopted is following: specific surface area is 70～260m
2/ g, pore volume are 0.15～0.50cm
3/ g, intensity is 8～25N.mm
-1
Described acidic molecular sieve is meant the molecular sieve with acid catalysis function; Be selected from but be not limited to following molecular sieve: one or more in Si-Al molecular sieve, the silicoaluminophosphamolecular molecular sieves; Be preferably in beta-molecular sieve, ZSM series molecular sieve, mordenite, faujusite, erionite, A type zeolite, MCM series molecular sieve, the SAPO series molecular sieve one or more; ZSM series molecular sieve can be among ZSM-5, ZSM-8, ZSM-11, the ZSM-35 one or more; SAPO series molecular sieve can be among SAPO-5, the SAPO-11 one or more; MCM series molecular sieve can be in MCM-22, the MCM-41 molecular sieve one or more, further is preferably in beta-molecular sieve, ZSM-5 molecular sieve, mordenite, the Y zeolite one or more.Said acidic molecular sieve is one or more in hydrogen type molecular sieve and modified molecular screen, polyvalent cation exchange molecular sieve and the modified molecular screen thereof, is preferably in hydrogen type molecular sieve and the modified molecular screen thereof one or more.Described hydrogen type molecular sieve can obtain after the ammonium exchange in the decomposition or the hydrogen ion exchange of ammonium ion; Described polyvalent cation exchange molecular sieve is that exchange obtains through polyvalent cation, such as alkaline earth metal cation-exchanged molecular sieve, rare earth metal cationic exchange molecular sieve etc.Described modified molecular screen includes but not limited to adopt the molecular sieve that obtains after adjusting acidic zeolite, pore structure, silica alumina ratio, the isoparametric method modification of non-framework aluminum.
Described resin is the polymkeric substance of vinylbenzene and polyene-based compound, and both weight ratios are 2: 1～5: 1.Described polyene-based compound can be one or more in divinylbenzene, divinyl toluene and the biethenyl-xylene, is preferably divinylbenzene.
The preparation method of HTS composite catalyst of the present invention comprises:
Polymerization single polymerization monomer and perforating agent thorough mixing that HTS powder, acidic molecular sieve powder, preparation resin are used; In the presence of initiator, at 60～150 ℃, preferably 80～90 ℃ were carried out polyreaction 3～10 hours; Preferably 4～6 hours, obtain the blocks of solid catalyzer; Obtain the catalyst solid particle through fragmentation then, above-mentioned catalyst solid particle is added in the halohydrocarbon after the swelling, adopt solvent extraction, obtain HTS composite catalyst of the present invention.
In the inventive method, the add-on of said perforating agent is 30%～60% of the polymerization single polymerization monomer gross weight used of HTS powder, acidic molecular sieve powder and preparation resin.
In the polymerization single polymerization monomer that described preparation resin is used, a kind of is polymerization single polymerization monomer vinylbenzene, another kind of polymerization single polymerization monomer polyene-based compound, and both weight ratios are 2: 1～5: 1.
Described polymerization single polymerization monomer polyene-based compound can be one or more in vinylbenzene, divinylbenzene, divinyl toluene, the biethenyl-xylene.
Described perforating agent can be gasoline, C
5～C
13Normal paraffin, C
4～C
12In the Fatty Alcohol(C12-C14 and C12-C18) one or more, preferably C
5～C
13In the normal paraffin one or more.
Described initiator can be Lucidol and/or azo two isopropylcarbinols, and add-on is 0.5%～2.5% of the polymerization single polymerization monomer gross weight used of HTS powder, acidic molecular sieve powder and preparation resin.
Described halohydrocarbon can be C
1～C
4Halohydrocarbon, wherein preferably 1,2-ethylene dichloride, described swelling time are 3～8 hours, preferably 5～6 hours.
Described extraction solvent can be one or more in benzene,toluene,xylene, ETHYLE ACETATE, butylacetate, ethanol, the butanols etc.Described extractive reaction temperature is 30～60 ℃, preferably 50～60 ℃; The described extracting time is 2～8 hours, preferably 4～6 hours.
In the described method of being produced Ucar 35 by propylene, the volumetric concentration of raw material hydrogen peroxide is 1%～35%, is preferably 3%～25%.
Described propylene is produced in the method for Ucar 35, and raw material propylene and ydrogen peroxide 50 mol ratio 1.0～5.0 are preferably 1.0～3.0.
It is following that described propylene is produced the reaction conditions of Ucar 35: temperature of reaction is 35～100 ℃, and reaction pressure is 0.1～4.5MPa, and the volume space velocity of ydrogen peroxide 50 is 0.01～3.0h
-1, preferred reaction conditions is following: temperature of reaction is 40～95 ℃, and reaction pressure is 0.9～3.5MPa, volume space velocity is 0.1～2.0h during the liquid of ydrogen peroxide 50
-1
Compared with prior art, the inventive method has following characteristics:
1, the inventive method adopts the HTS composite catalyst; Have epoxidation and acid catalyzed dual catalytic function; Can the open loop hydration reaction of propylene ring oxidation reaction and epoxy compounds be coupled together; Realize the single step reaction of propylene, can shorten the technical process that for example traditional Ucar 35 is produced greatly, simplify technology to Ucar 35.
2, can adopt fixed-bed reactor after the HTS composite catalyst moulding that the inventive method adopts, the catalyzer and the reaction solution that have solved the Ti-Si catalyst powder are difficult to isolating problem, have improved reaction efficiency.
3, the HTS composite catalyst that adopts of the inventive method in catalytic reaction process because the diluting effect of a large amount of inertia dispersion agents; HTS is existed with isolated form; So the oxidizing reaction heat effect relaxes, can reduce side reaction and take place, improved reaction preference.
4, after the HTS composite catalyst moulding that the inventive method adopts; Do not need high temperature (＞500 ℃) roasting to remove the perforating agent that adds in the moulding process; Only need low temperature (＜150 ℃) extracting activation; Can avoid causing framework of molecular sieve to cave in or titanium detaches skeleton, fully keep HTS active.
5, the HTS composite catalyst resin matrix of the inventive method employing is highly stable in ydrogen peroxide 50, can guarantee that catalyzer is activity stabilized in the reaction atmosphere.
Embodiment
The specific surface area of catalyzer and pore volume are to adopt the low temperature liquid nitrogen determination of adsorption method among the present invention, and the intensity of catalyzer is to adopt QCY-602 type catalyst strength determinator to measure.
The concrete preparation process of the HTS composite catalyst that the inventive method is used is following:
(1), polymerization
In polymeric kettle; Add HTS powder, acidic molecular sieve powder, polymerization single polymerization monomer vinylbenzene, polymerization single polymerization monomer polyene-based compound, perforating agent; After mixing, warming-in-water adds initiator when being preferably in 60～90 ℃; Under 60～150 ℃, carry out polyreaction 3～10 hours, and obtained block HTS composite catalyst.
(2), solvent extraction activation
Above-mentioned block HTS composite catalyst is carried out broken granulation, choose the catalyzer that particle diameter is 1 * 1～5 * 5mm after the screening, add halohydrocarbon and carry out swelling; The volume of catalyzer and halohydrocarbon is 1: 10～1: 1, dissolved expanding 3～8 hours, pour out halohydrocarbon after; Add extraction solvent again and carry out extracting; It is that the volume ratio of extraction solvent and catalyzer is 1: 1～5: 1,30～60 ℃ of extractive reaction temperature, 2～6 hours extracting time; Extracting number of times 2～5 times obtains HTS composite catalyst of the present invention.
Below in conjunction with embodiment the present invention is done further detailed description; Following examples are not the restriction to protection domain of the present invention; Those skilled in the art combines specification sheets of the present invention and can do suitable expansion in full, and these expansions all should be protection scope of the present invention.
Embodiment 1
In polymeric kettle, add HTS powder 5.5g, H β zeolite 1g, polymerization single polymerization monomer vinylbenzene 90g and divinylbenzene 30g; Perforating agent liquid wax 60g; After mixing, during warming-in-water to 60 ℃, add initiator Lucidol 1.5g; 90 ℃ of following polymeric reaction temperatures 6 hours, obtain block HTS composite catalyst.Carry out broken granulation then, choose the catalyzer of suitable particle diameter after the screening, add 1,2-ethylene dichloride 250ml carries out swelling, dissolved expanding 5 hours.Pour out 1, behind the 2-ethylene dichloride, add ETHYLE ACETATE 200ml again and carry out solvent extraction, 55 ℃ of extractive reaction temperature, 4 hours extracting time, carry out three extractings with quadrat method, obtain HTS composite catalyst A, its physico-chemical property is seen table 1.
Embodiment 2
In polymeric kettle, add HTS powder 15g, H-ZSM-5 molecular sieve 3g, polymerization single polymerization monomer vinylbenzene 90g, divinyl toluene 15g, biethenyl-xylene 25g, perforating agent C
5Fatty Alcohol(C12-C14 and C12-C18) 60g after mixing, during warming-in-water to 80 ℃, adds initiator azo two isopropylcarbinol 2.0g, 100 ℃ of following polymeric reaction temperatures 6 hours, obtains block titanium-silicon molecular sieve catalyst.Carry out broken granulation then, choose the catalyzer of suitable particle diameter after the screening, add 1,2-ethylene dichloride 250ml carries out swelling, dissolved expanding 5 hours.Pour out 1, behind the 2-ethylene dichloride, add YLENE 200ml again and carry out solvent extraction, 55 ℃ of extractive reaction temperature, 4 hours extracting time, carry out three extractings with quadrat method, obtain HTS composite catalyst B, its physico-chemical property is seen table 1.
Embodiment 3
The weight of HTS powder among the embodiment 1 is become 30g, add mordenite 3g in addition, all the other obtain HTS composite catalyst C with embodiment 1, and its physico-chemical property is seen table 1.
Embodiment 4
The weight of HTS powder among the embodiment 1 is become 45g, add Y zeolite 5g in addition, all the other obtain HTS composite catalyst D with embodiment 1, and its physico-chemical property is seen table 1.
Embodiment 5
The weight of HTS powder among the embodiment 1 is become 60g add HZSM-5 molecular sieve 3g in addition, all the other obtain HTS composite catalyst E with embodiment 1, and its physico-chemical property is seen table 1.
Embodiment 6
The weight of HTS powder among the embodiment 1 is become 75g, H β zeolite 10g, all the other obtain HTS composite catalyst F with embodiment 1, and its physico-chemical property is seen table 1.
The physico-chemical property of table 1 catalyzer
| Catalyzer | Specific surface area, m 2.g -1 | Pore volume, ml.g -1 | Intensity, N.mm -1 |
| A | 79.6 | 0.23 | 17.9 |
| B | 96.7 | 0.18 | 14.3 |
| C | 111.3 | 0.22 | 11.5 |
| D | 141.5 | 0.30 | 10.1 |
| E | 165.1 | 0.32 | 9.2 |
| F | 211.7 | 0.21 | 8.4 |
Embodiment 7～12
(particle diameter 2 * 2mm) the 50ml diameter 20mm that packs in the fixed-bed reactor of long 1200mm, carries out epoxidation, the open loop hydration reaction of propylene, makes Ucar 35 to get the catalyzer of embodiment 1～6.The analytical procedure of Ucar 35 adopts HP6890 gas chromatographic analysis, fid detector, HP-INNOWAX capillary column, H
2O
2Analytical procedure adopts the redox titration potassium permanganate process, and reaction conditions and result see table 2.
Table 2
Percentage ratio in the table 2 is percent by volume.
Claims (17)
1. method of producing Ucar 35 by propylene; This method adopts fixed-bed reactor; Comprise: in the presence of the HTS composite catalyst, propylene, ydrogen peroxide 50 carry out epoxidation, open loop hydration single step reaction makes Ucar 35, the HTS composite catalyst that is wherein adopted; Weight with catalyzer is benchmark; The total content of HTS and acidic molecular sieve is 1%～50%, and the content of resin is 50%～99%, and wherein the weight ratio of HTS and acidic molecular sieve is 5: 1～20: 1.
2. according to the described method of claim 1, the HTS composite catalyst that it is characterized in that being adopted is a benchmark with the weight of catalyzer, and the total content of HTS and acidic molecular sieve is 10%～25%, and the content of resin is 75%～90%.
3. according to the described method of claim 1, the character of the HTS composite catalyst that it is characterized in that being adopted is following: specific surface area is 70～260m
2/ g, pore volume are 0.15～0.50cm
3/ g, intensity is 8～25N.mm
-1
4. according to the described method of claim 1, it is characterized in that described acidic molecular sieve is one or more in Si-Al molecular sieve, the silicoaluminophosphamolecular molecular sieves.
5. the method for stating according to claim 1 is characterized in that described acidic molecular sieve is one or more in beta-molecular sieve, ZSM series molecular sieve, mordenite, faujusite, erionite, A type zeolite, MCM series molecular sieve, the SAPO series molecular sieve.
6. according to the described method of claim 5; It is characterized in that described ZSM series molecular sieve is one or more among ZSM-5, ZSM-8, ZSM-11, the ZSM-35; SAPO series molecular sieve is one or more among SAPO-5, the SAPO-11, and MCM series molecular sieve is one or more in MCM-22, the MCM-41 molecular sieve.
7. according to the described method of claim 1, it is characterized in that described acidic molecular sieve is one or more in beta-molecular sieve, ZSM-5 molecular sieve, mordenite, the Y zeolite.
8. according to the arbitrary described method of claim 1-7, it is characterized in that said acidic molecular sieve is one or more in hydrogen type molecular sieve and modified molecular screen, polyvalent cation exchange molecular sieve and the modified molecular screen thereof.
9. according to the arbitrary described method of claim 1-7, it is characterized in that said acidic molecular sieve is one or more in hydrogen type molecular sieve and the modified molecular screen thereof.
10. according to the described method of claim 1, it is characterized in that described resin is the polymkeric substance of vinylbenzene and polyene-based compound, both weight ratios are 2: 1～5: 1.
11., it is characterized in that described polyene-based compound is one or more in divinylbenzene, divinyl toluene and the biethenyl-xylene according to the described method of claim 10.
12., it is characterized in that described polyene-based compound is a divinylbenzene according to the described method of claim 10.
13., it is characterized in that the volumetric concentration of raw material hydrogen peroxide is 1%～35% according to the described method of claim 1, raw material propylene and ydrogen peroxide 50 mol ratio 1.0～5.0.
14., it is characterized in that the volumetric concentration of raw material hydrogen peroxide is 3%～25% according to the described method of claim 1, raw material propylene and ydrogen peroxide 50 mol ratio 1.0～3.0.
15., it is characterized in that the reaction conditions of this method is following according to the described method of claim 1: temperature of reaction is 35～100 ℃, and reaction pressure is 0.1～4.5MPa, and the volume space velocity of ydrogen peroxide 50 is 0.01～3.0h
-1
16., it is characterized in that the reaction conditions of this method is following according to the described method of claim 1: temperature of reaction is 40～95 ℃, and reaction pressure is 0.5～3.5MPa, and volume space velocity is 0.1～2.0h during the liquid of ydrogen peroxide 50
-1
17., it is characterized in that described Ucar 35 is 1, the 2-Ucar 35 according to the described method of claim 1.
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105237356A (en) * | 2015-09-29 | 2016-01-13 | 华东师范大学 | Method for producing cyclohexanol through cyclohexene hydration |
| CN107879893A (en) * | 2016-09-29 | 2018-04-06 | 中国石油化工股份有限公司 | A kind of method that catalytic oxidation prepares vicinal diamines class compound |
| CN108658727A (en) * | 2017-03-30 | 2018-10-16 | 中国石油化工股份有限公司 | Propylene method for oxidation |
| CN110156571A (en) * | 2018-02-13 | 2019-08-23 | 中国石油化工股份有限公司 | Propylene method for oxidation |
| CN113058643A (en) * | 2021-03-29 | 2021-07-02 | 北京化工大学 | Modified TS-1 molecular sieve composite catalyst and preparation method and application thereof |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN105439815B (en) * | 2014-08-21 | 2017-12-22 | 中国石油化工股份有限公司 | A kind of method for preparing propane diols |
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Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105237356A (en) * | 2015-09-29 | 2016-01-13 | 华东师范大学 | Method for producing cyclohexanol through cyclohexene hydration |
| CN107879893A (en) * | 2016-09-29 | 2018-04-06 | 中国石油化工股份有限公司 | A kind of method that catalytic oxidation prepares vicinal diamines class compound |
| CN107879893B (en) * | 2016-09-29 | 2022-11-22 | 中国石油化工股份有限公司 | Method for preparing o-diol compound by catalytic oxidation method |
| CN108658727A (en) * | 2017-03-30 | 2018-10-16 | 中国石油化工股份有限公司 | Propylene method for oxidation |
| CN108658727B (en) * | 2017-03-30 | 2022-06-28 | 中国石油化工股份有限公司 | Propylene oxidation process |
| CN110156571A (en) * | 2018-02-13 | 2019-08-23 | 中国石油化工股份有限公司 | Propylene method for oxidation |
| CN110156571B (en) * | 2018-02-13 | 2022-03-11 | 中国石油化工股份有限公司 | Propylene oxidation process |
| CN113058643A (en) * | 2021-03-29 | 2021-07-02 | 北京化工大学 | Modified TS-1 molecular sieve composite catalyst and preparation method and application thereof |
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|---|---|
| CN102452899B (en) | 2014-03-05 |
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