CN103752342B - Preparation method of catalyst for synthesizing hexafluoropropene tripolymer - Google Patents
Preparation method of catalyst for synthesizing hexafluoropropene tripolymer Download PDFInfo
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- CN103752342B CN103752342B CN201410006152.2A CN201410006152A CN103752342B CN 103752342 B CN103752342 B CN 103752342B CN 201410006152 A CN201410006152 A CN 201410006152A CN 103752342 B CN103752342 B CN 103752342B
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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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Abstract
The invention provides a preparation method of a catalyst for synthesizing a hexafluoropropene tripolymer. The preparation method disclosed by the invention comprises the following steps: (1), reacting after mixing potassium fluoride aqueous solution, 2,2-dipyridyl and a succinic acid derivative according to the mass ratio of 100:(1-5):(0.1-0.5) at 30-100 DEG C for 3-10 h, and obtaining a complex after reacting, for further use; and (2), immersing resin-based spherical activated carbon in an ethanol solvent for 3-10 h, wherein the mass ratio of the resin-based spherical activated carbon to the ethanol solvent is 1:(3-10), and reacting by adding the complex prepared in the step (1), wherein the mass of the complex is 10-30% of that of the resin-based spherical activated carbon; the reaction temperature is 0-30 DEG C; the reaction time is 3-25 h; after reacting, washing, drying and roasting, and obtaining the catalyst for synthesizing the hexafluoropropene tripolymer. The preparation method disclosed by the invention has the advantages of being good in activity of the prepared catalyst, recycled, high in reaction yield and good in selectivity.
Description
Technical field
The present invention relates to the preparation method of catalyst, be specifically related to a kind of preparation method synthesizing hexafluoropropylene trimer catalyst.
Background technology
Oligomerization of hexafluoropropylene obtains dimer and trimer is all very useful industrial chemicals, can derive many fluorine-containing surfactants.The perfluor carbochain of hexafluoropropene oligomers hydrophobic has height collateralization, compared with general straight chain perfluorinated surfactant, adds the physical property that some are special.It can be used alone and also jointly can use with other surfactants, thus can at washing agent, plastic paint, weaving, leather, oil, electronics, and the fields such as pigment play unique effect.Such as: the perfluoroalkyl ether that the oligomer of hexafluoropropene and phenol reactant generate, react with oleum, can be made into sulfonate type fluorine surfactant.Perfluoroalkyl ether and chlorosulfonic acid react then can introduce sulfuryl chlorio on phenyl ring, and reaction can be made into various fluorine surfactant further.The fluorine-containing surfactant prepared by oligomerization of hexafluoropropylene derivative has and reduces interfacial surface tension and oriented attachment form the characteristic of glue card in the solution, makes the field such as its extensive use and washing, plastics, metal, coating, textile, leather, household article, petroleum product, electronics industry thus.
At present, hexafluoropropylene trimer mainly adopts liquid phase method to synthesize, and mainly contains three kinds of isomers (IIIA, IIIB and IIIC), can transform between various isomers in product.Liquid phase method oligomerization of hexafluoropropylene technique is dissolved in aprotic polar solvent by catalyst and additive thereof, and then logical people's hexafluoropropene reacts, its process can be interval also can be continuous print.The product of oligomerisation reaction is insoluble in a solvent substantially, after the completion of reaction, can form obvious two-phase, convenient separation, but product mutually in, must a small amount of solvent and catalyst be contained, therefore before carrying out the rectifying of product, must wash, to remove desolventizing and catalyst.The solvent of washing removing generally cannot reclaim, and wherein the recovery of catalyst is also very difficult.Due in liquid phase method oligomerization of hexafluoropropylene technical process, the separation of catalysts and solvents must be considered, the series of problems such as reclaim and reuse, therefore its post processing is general all more loaded down with trivial details.
As in US Patent No. 4093670, using the complex of KF-crown ether as catalyst in dimethyl formamide, " crown ether " comprises each large cyclic ethers, and (its oxygen atom can be substituted by nitrogen at least in part, sulphur and/or phosphorus), catalyst has strong dissociable compound, such as alkali metal cation halide, this catalyst can activate corresponding anion in the reaction, shows high catalytic activity.
Pointing out in Japan Patent JP50-117705, is catalyst with KF, heats (IIA), make it change IIB in cyclobutane.But this type of reaction needs the high temperature of more than 100 DEG C usually, and the very long reaction time.
Mainly based on fluoride, as potassium fluoride etc., there is poor catalyst activity, catalyst recovery difficulty, reaction yield be low, the selective shortcoming such as lower in catalyst that above patented technology uses.
Summary of the invention
Technical problem to be solved by this invention overcomes the deficiencies in the prior art, provides a kind of good catalyst activity prepared, reusable edible; The preparation method of high, the selective good synthesis hexafluoropropylene trimer catalyst of reaction yield.
In order to solve above technical problem, present invention employs following technical scheme: a kind of preparation method synthesizing hexafluoropropylene trimer catalyst, comprises the following steps:
(1) react after potassium fluoride aqueous solution, 2,2-bipyridyls and butanedioic acid derivative in mass ratio 100:1-5:0.1-0.5 mixing, reaction temperature is 30 ~ 100 DEG C, and the reaction time is 3-10h, and reaction end obtains complex, for subsequent use;
(2) resin based sphere active carbon is soaked 3 ~ 10h in alcohol solvent, resin based sphere active carbon and alcohol solvent mass ratio are 1:3-10, add the complex that step (1) prepares again to react, described complex quality is 10 ~ 30% of resin based sphere active carbon quality, reaction temperature is 0 ~ 30 DEG C, and the reaction time is 3 ~ 25h;
(3) reaction terminates rear washing, dry, roasting, namely obtains synthesis hexafluoropropylene trimer catalyst.
Butanedioic acid derivative described in step (1) is preferably the one in 2-dimethyl succinic acid, 2-methylene-succinic acid, 2-dimercaptosuccinic acid, 2-bromo succinic acid, 2-hydroxysuccinic acid.
Resin based sphere active carbon sphere diameter described in step (2) is preferably 0.3-1.2mm, and specific area is preferably 950-1200m
2/ g, pore volume is preferably 0.6-0.75ml/g.
Reaction temperature described in step (1) is preferably 50 ~ 90 DEG C, and the reaction time is preferably 4 ~ 7h.
Complex Functionality, quality and appealing design described in step (2) elects 15 ~ 25% of resin based sphere active carbon quality as.
Reaction temperature described in step (2) is preferably 15 ~ 25 DEG C, and the reaction time is preferably 10 ~ 20h.
The present invention there is the resin based sphere active carbon of high-ratio surface sum microcellular structure for carrier, by liquid deposition method carrying potassium oxide, and butanedioic acid derivative and 2,2-bipyridyl (C
10h
8n
2) part, then through washing, dry, roasting, namely obtains synthesis hexafluoropropylene trimer catalyst.Catalyst of the present invention is very effective to suppression side reaction for the synthesis of hexafluoropropylene trimer, the potassium fluoride of load and butanedioic acid derivative and 2,2-bipyridyl (C
10h
8n
2) form firmly complex, for catalyst provides stable active sites, thus catalyst still can keep higher activity after long period of operation, and energy Reusability, decrease the generation of waste residue, and the service life of catalyst can be improved.
Resin based sphere active carbon in the present invention has high-ratio surface sum microcellular structure, can more effective carrying potassium oxide and butanedioic acid derivative and 2,2-bipyridyl (C
10h
8n
2) part, further enhancing catalytic activity, very effective to suppression side reaction.The preferred sphere diameter of resin based sphere active carbon in the present invention is 0.3-1.2mm, and specific area is 950-1200m
2/ g, pore volume is the resin based sphere active carbon of 0.6-0.75ml/g.Resin based sphere active carbon in the present invention can commercially availablely obtain, as the resin based sphere active carbon can selecting Shanxi Cui Hong Science and Technology Ltd., Langfang Ai Er blood purification equipment Chang Deng enterprise produces.
Butanedioic acid derivative in the present invention and 2,2-bipyridyl (C
10h
8n
2) act synergistically as part and potassium fluoride, further enhancing catalytic activity, suppress the generation of side reaction.The butanedioic acid derivative mixture of one or more can selected in 2-dimethyl succinic acid, 2-methylene-succinic acid, 2-dimercaptosuccinic acid, 2-bromo succinic acid, 2-hydroxysuccinic acid etc., be preferably the one in 2-dimethyl succinic acid, 2-methylene-succinic acid, 2-dimercaptosuccinic acid, 2-bromo succinic acid, 2-hydroxysuccinic acid, be more preferably 2-dimercaptosuccinic acid.
Compared with prior art, the present invention has following beneficial effect:
1, the catalyst prepared is good for the synthesis of activity during hexafluoropropylene trimer, accessory substance is few, and resin based sphere active carbon has high-ratio surface sum microcellular structure, can effectively carrying potassium oxide and butanedioic acid derivative and 2,2-bipyridyl (C
10h
8n
2) part, strengthen catalytic activity, butanedioic acid derivative and 2,2-bipyridyl (C
10h
8n
2) forming firmly complex as part and potassium fluoride, synergy, further enhancing catalytic activity, inhibit the generation of side reaction, catalyst of the present invention is for the synthesis of hexafluoropropylene trimer, and when first time uses, reaction yield is more than 93%, reaches as high as 99%; Selective more than 95%, reach as high as 100%;
2, the catalyst prepared for the synthesis of long service life during hexafluoropropylene trimer, reusable edible, the potassium fluoride of load and butanedioic acid derivative and 2,2-bipyridyl (C
10h
8n
2) form firmly complex, for catalyst provides stable active sites, still can keep higher activity after long-term use, and can recycle, decrease the generation of waste residue, and the service life of catalyst can be improved, after reusing five times, reaction yield is more than 90%, reach as high as 98%, hexafluoropropylene trimer is selective more than 90%, reaches as high as 99%.
Detailed description of the invention
Below in conjunction with specific embodiment, illustrate the present invention further, but these embodiments are only for explaining the present invention, instead of for limiting the scope of the invention.
Resin based sphere active carbon used in embodiment: Shanxi Cui Hong Science and Technology Ltd. produce, sphere diameter at 0.3-1.2mm, specific area (BET) 950-1200m
2/ g, pore volume 0.6-0.75ml/g.
Embodiment 1:
Synthesize a preparation method for hexafluoropropylene trimer catalyst, comprise the following steps:
(1) prepare
complex:
In 500L reactor, add the potassium fluoride aqueous solution 333Kg of mass percentage content 30%, 2,2-bipyridyl 2.5Kg, 2-dimercaptosuccinic acid 0.2Kg reacts, and reaction temperature is 70 DEG C, and the reaction time is 5h, and reaction end obtains complex, for subsequent use;
(2) load operation of catalyst
By 100Kg resin based sphere active carbon, (sphere diameter is 0.9mm, and specific area is 1027m
2/ g, pore volume is 0.66ml/g) in 500Kg alcohol solvent, soak 4h, the above-mentioned steps (1) adding 20Kg obtains
complex, at 20 DEG C, react 15h, reaction terminates rear washing, dry, roasting, and namely obtain synthesis hexafluoropropylene trimer catalyst, production code member JH-1, performance is in table 1.
Embodiment 2
Synthesize a preparation method for hexafluoropropylene trimer catalyst, comprise the following steps:
(1) prepare
complex:
In 500L reactor, add mass percentage content 30% potassium fluoride aqueous solution 333Kg, 2,2-bipyridyl 1Kg, 2-dimercaptosuccinic acid 0.2Kg reacts, and reaction temperature is 100 DEG C, and the reaction time is 4h, and reaction end obtains complex, for subsequent use;
(2) load operation of catalyst
By 100Kg resin based sphere active carbon, (sphere diameter is 0.3mm, and specific area is 953m
2/ g, pore volume is 0.61ml/g) in 1000Kg alcohol solvent, soak 3h, the above-mentioned steps (1) adding 20Kg obtains
complex, at 0 DEG C, react 20h, reaction terminates rear washing, dry, roasting, and namely obtain synthesis hexafluoropropylene trimer catalyst, production code member JH-2, performance is in table 1.
Embodiment 3
Synthesize a preparation method for hexafluoropropylene trimer catalyst, comprise the following steps:
(1) prepare
complex:
In 500L reactor, add mass percentage content 30% potassium fluoride aqueous solution 333Kg, 2,2-bipyridyl 5Kg, 2-dimercaptosuccinic acid 0.2Kg reacts, and reaction temperature is 30 DEG C, and the reaction time is 10h, and reaction end obtains complex, for subsequent use;
(2) load operation of catalyst
By 100Kg resin based sphere active carbon, (sphere diameter is 1.2mm, and specific area is 1197m
2/ g, pore volume is 0.73ml/g) in 300Kg alcohol solvent, soak 10h, the above-mentioned steps (1) adding 20Kg obtains
complex, at 20 DEG C, react 3h, reaction terminates rear washing, dry, roasting, and namely obtain synthesis hexafluoropropylene trimer catalyst, production code member JH-3, performance is in table 1.
Embodiment 4
The 2-dimercaptosuccinic acid of 0.1Kg is added, the other the same as in Example 1 in step (1).Production code member JH-4, performance is in table 1.
Embodiment 5
Add the 2-dimercaptosuccinic acid of 0.5Kg in step (1), it is with embodiment 1.Production code member JH-5, performance is in table 1.
Embodiment 6
The 2-dimethyl succinic acid adding 0.2Kg in step (1) replaces 2-dimercaptosuccinic acid; The complex of 10Kg is added, the other the same as in Example 1 in step (2).Production code member JH-6, performance is in table 1.
Embodiment 7
The 2-methylene-succinic acid adding 0.2Kg in step (1) replaces 2-dimercaptosuccinic acid; The complex of 10Kg is added, the other the same as in Example 2 in step (2).Production code member JH-7, performance is in table 1.
Embodiment 8
The 2-bromo succinic acid adding 0.2Kg in step (1) replaces 2-dimercaptosuccinic acid; The complex of 10Kg is added, the other the same as in Example 3 in step (2).Production code member JH-8, performance is in table 1.
Embodiment 9
The 2-hydroxysuccinic acid adding 0.1Kg in step (1) replaces 2-dimercaptosuccinic acid; The complex of 10Kg is added, the other the same as in Example 4 in step (2).Production code member JH-9, performance is in table 1.
Embodiment 10
The complex of 10Kg is added, the other the same as in Example 5 in step (2).Production code member JH-10, performance is in table 1.Embodiment 11
Add the complex of 30Kg in step (2), at 25 DEG C, react 10h, the other the same as in Example 1.Production code member JH-11, performance is in table 1.
Embodiment 12
Add the complex of 15Kg in step (2), at 10 DEG C, react 18h, the other the same as in Example 2.Production code member JH-12, performance is in table 1.
Embodiment 13
Add the complex of 25Kg in step (2), at 15 DEG C, react 5h, the other the same as in Example 3.Production code member JH-13, performance is in table 1.
Embodiment 14
Reaction temperature in step (1) is 50 DEG C, and the reaction time is 7h, adds the complex of 30Kg, the other the same as in Example 4 in step (2).Production code member JH-14, performance is in table 1.
Embodiment 15
Reaction temperature in step (1) is 90 DEG C, and the reaction time is 3h, adds the complex of 30Kg, the other the same as in Example 5 in step (2).Production code member JH-15, performance is in table 1.
Comparative example 1
Step does not add 2-dimercaptosuccinic acid, the other the same as in Example 1 in (1).Production code member JH-16, performance is in table 1.
Comparative example 2
Step does not add complex, the other the same as in Example 1 in (2).Production code member JH-17, performance is in table 1.
The evaluation that the catalyst that embodiment 1 ~ 15 and comparative example 1-2 prepare reacts for the preparation of hexafluoropropylene trimer:
Add 50ml dimethyl formamide DMF in the reactor, 4g solid catalyst, then the logical people's hexafluoropropene gas of metering, stirs, is heated to 100 DEG C, reaction 10h, and reaction terminates filtering recovering catalyst while hot, weighs after filtrate cooling.Reactant transfer to separatory funnel, after separatory, obtain fluorocarbons, washing and drying, namely obtain hexafluoropropylene trimer.Product through gas chromatographic analysis, calculated yield and hexafluoropropylene trimer selective, data are in table 1.
Table 1: the catalyst that embodiment 1 ~ 15 and comparative example 1-2 prepare is for the preparation of the yield of hexafluoropropylene trimer and selective
As shown in Table 1, the synthesis hexafluoropropylene trimer catalyst that method of the present invention prepares is very effective to suppression side reaction, the potassium fluoride of load and butanedioic acid derivative and 2,2-bipyridyl (C
10h
8n
2) complex be that catalyst provides stable active sites, thus catalyst still can keep higher activity after long period of operation, and can Reusability, decreases the generation of waste residue, and can improve the service life of catalyst.
Claims (5)
1. synthesize a preparation method for hexafluoropropylene trimer catalyst, it is characterized in that comprising the following steps:
(1) by potassium fluoride aqueous solution, 2,2-bipyridyl and butanedioic acid derivative in mass ratio 100:1-5:0.1-0.5 react after mixing, described butanedioic acid derivative is the one in 2-dimethyl succinic acid, 2-methylene-succinic acid, 2-dimercaptosuccinic acid, 2-bromo succinic acid, 2-hydroxysuccinic acid, reaction temperature is 30 ~ 100 DEG C, reaction time is 3-10h, reaction end obtains complex, for subsequent use;
(2) resin based sphere active carbon is soaked 3 ~ 10h in alcohol solvent, described resin based sphere active carbon and alcohol solvent mass ratio are 1:3-10, add the complex that step (1) prepares again to react, described complex quality is 10 ~ 30% of resin based sphere active carbon quality, reaction temperature is 0 ~ 30 DEG C, and the reaction time is 3 ~ 25h;
(3) reaction terminates rear washing, dry, roasting, namely obtains synthesis hexafluoropropylene trimer catalyst.
2. the preparation method of catalyst according to claim 1, it is characterized in that the resin based sphere active carbon sphere diameter described in step step (2) is 0.3-1.2mm, specific area is 950-1200m
2/ g, pore volume is 0.6-0.75ml/g.
3. the preparation method of catalyst according to claim 1, it is characterized in that the reaction temperature described in step (1) is 50 ~ 90 DEG C, the reaction time is 4 ~ 7h.
4. the preparation method of catalyst according to claim 1, is characterized in that the complex quality described in step (2) is 15 ~ 25% of resin based sphere active carbon quality.
5. the preparation method of catalyst according to claim 1, it is characterized in that the reaction temperature described in step (2) is 15 ~ 25 DEG C, the reaction time is 10 ~ 20h.
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| CN1095367A (en) * | 1992-12-28 | 1994-11-23 | 美国3M公司 | The preparation of hexafluoropropene oligomers |
| CN101020620A (en) * | 2007-03-14 | 2007-08-22 | 浙江工业大学 | Process of preparing hexafluoropropylene oligomer |
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2014
- 2014-01-06 CN CN201410006152.2A patent/CN103752342B/en active Active
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|---|---|---|---|---|
| US4296265A (en) * | 1979-07-19 | 1981-10-20 | Daikin Kogyo Co., Ltd. | Process for preparing hexafluoropropene oligomers |
| CN1095367A (en) * | 1992-12-28 | 1994-11-23 | 美国3M公司 | The preparation of hexafluoropropene oligomers |
| CN101020620A (en) * | 2007-03-14 | 2007-08-22 | 浙江工业大学 | Process of preparing hexafluoropropylene oligomer |
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Effective date of registration: 20180914 Address after: 324004 Zhejiang Quzhou Juhua Group Co., Ltd. Patentee after: Juhua Group Co., Ltd. Address before: 324004 Zhejiang Quzhou City Kecheng District Juhua Group Technology Center Patentee before: Technology Center of Juhua Group |
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