CN106608809A - Separation and purification method for 2,6-diisopropylnaphthalene - Google Patents
Separation and purification method for 2,6-diisopropylnaphthalene Download PDFInfo
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- CN106608809A CN106608809A CN201510686007.8A CN201510686007A CN106608809A CN 106608809 A CN106608809 A CN 106608809A CN 201510686007 A CN201510686007 A CN 201510686007A CN 106608809 A CN106608809 A CN 106608809A
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Abstract
The invention relates to a separation and purification method for 2,6-diisopropylnaphthalene. The method is mainly used for solving the technical problem that the product purity is low when 2,6-diisopropylnaphthalene is separated and purified in the prior art. According to the adopted technical scheme, the method comprises the following steps that a liquid mixture containing 2,6-diisopropylnaphthalene enters a rectifying tower, naphthalene, isopropylnaphthalene and other light components are removed, the light-component-removed materials enter a first crystallizer, a material flow containing crude 2,6-diisopropylnaphthalene crystals is obtained through a suspension crystallization process, the crude crystals enter a second crystallizer, and a material flow containing the high-purity 2,6-diisopropylnaphthalene product is obtained through a solvent crystallization, washing and drying process. Accordingly, the technical problem is well solved, and the method can be used in industrial production for separating and purifying 2,6-diisopropylnaphthalene.
Description
Technical field
The present invention relates to a kind of process for separation and purification of 2,6-DIPN, can be used for separating-purifying 2,6-DIPN
In commercial production.
Background technology
2,6-DIPN (2,6-DIPN) is a kind of important Organic Chemicals, oxidized generation NDA,
The latter can be used to prepare various high-performance polymers, the PEN that the esterification of itself and ethylene glycol, polycondensation are obtained
(PEN), as the rigidity of naphthalene nucleus in molecular structure is more than phenyl ring, therefore, compare poly terephthalic acid second general at present
Diol ester (PET), PEN have higher physical and mechanical propertiess, gas barrier property, chemical stability and heat-resisting, resistance to
The performances such as ultraviolet, radiation hardness, are a kind of high performance polyester materials, can be processed into thin film, fiber, hollow container and
Sheet material etc., is with a wide range of applications.In recent years, with the continuous expansion of PEN ranges of application, to raw material 2,6- bis- is different
The demand of propyl group naphthalene is also gradually increasing, and the developed country such as America and Europe, Japan has all competitively researched and developed 2,6-DIPN
Preparation and purifying technique, China starts late, and the separation of 2,6-DIPN is difficult in addition, still rely primarily at present into
Mouthful, therefore, technique is researched and developed as early as possible, especially the purification technique of 2,6-DIPN has very heavy
The meaning wanted.
Mainly there is alkylated reaction with propylene or isopropanol under catalyst action by naphthalene and generate in 2,6- diisopropyl naphthalenes
's.Research with regard to catalyst at present also reaches far away industrialized requirement, and selectivity of catalyst and reaction yield are relatively low,
Cause catalysate numerous.In product of the naphthalene with propylene isopropylation, outside 2,6-DIPN, also containing single isopropyl
Base naphthalene (MIPN, such as 2-IPN, 1-IPN), other diisopropyl naphthalene isomerss (DIPN, such as 1,3-DIPN, 1,6-DIPN,
1,7-DIPN, 2,7-DIPN etc.), triisopropyl naphthalene (TIPN, such as 1,3,5-TIPN, 1,3,6-TIPN, Isosorbide-5-Nitrae, 6-TIPN etc.),
Many isopropyl naphthalenes (PIPN), and the naphthalene that unreacted is complete.As in product, impurity is more, and diisopropyl naphthalene is same
The enantiomers up to content of 10, especially 2,7-DIPN is suitable with the content of 2,6-DIPN, causes 2,6-DIPN's
Product purity is relatively low, and when being used to synthesize NDA, its purity requirement in terms of mass fraction is not less than 95%, because
This, needs to carry out above-mentioned product separating-purifying and just can be used for synthesizing NDA, and then prepare PEN.
In above-mentioned product, due to diisopropyl naphthalene and naphthalene, single isopropyl naphthalene, between triisopropyl naphthalene and many isopropyl naphthalenes
Boiling point has differences, and the method for simple rectification can be adopted to be separated, the mixture of diisopropyl naphthalene is obtained, but product
The isomerss species of middle diisopropyl naphthalene is more, and boiling point is also very close, between 308.6～319.6 DEG C, especially
2,7-DIPN, its boiling point with 2,6-DIPN is differed only by less than 2 DEG C (the former is 317 DEG C, and the latter is 319.6 DEG C), in addition
Which is suitable with the content of 2,6-DIPN, it is clear that be to obtain high-purity 2,6-DIPN products using the method for conventional rectification,
Therefore, in the method for separating-purifying 2,6-DIPN, the separation of diisopropyl naphthalene isomerss is key, especially
It is that 2,6-DIPN is separated with 2,7-DIPN.
At present the method for separating-purifying 2,6-DIPN mainly includes rectification method, crystallization process, complexation-crystallization method, absorption method,
And their combined methods each other：
Variant with the boiling point of other components based on diisopropyl naphthalene, CN1112539 proposes a kind of isopropyl naphthalene mixture
Three tower batch rectification methods, but which mainly carries out the cutting of above-mentioned fraction, by other diisopropyl naphthalene isomerss boiling points
Close impact, it is impossible to directly obtain 2,6-DIPN products.
Fusing point based on diisopropyl naphthalene isomerss is variant, except the fusing point of 2,6-DIPN higher (67～70 DEG C) outward,
The fusing point of other diisopropyl naphthalene isomerss is relatively low, and especially the fusing point of 2,7-DIPN is only -3 DEG C,
CN1793088A proposes naphthalene can be faced hydrogen isopropyl by the method for vacuum distillation and first stage suspension crystallization plus the crystallization of one-level laminar
2,6-DIPN in glycosylation reaction product is separated, but which does not limit the operating condition of explanation vacuum distillation, and two steps yet
The temperature of crystallization process is all than relatively low (- 20 DEG C or so), in addition, 2, the 6-DIPN products in order to obtain purity >=99%, need
Multiple laminar crystallization is carried out, technique and operation are relative complex.
Variant based on diisopropyl naphthalene isomerss dissolubility in a solvent, CN101130478A proposes naphthalene and propylene
Product pass through the method for vacuum distillation and solvent crystallization and can obtain 2, the 6-DIPN products that purity is 99.0～99.5%,
But which does not limit the operating condition of explanation vacuum distillation, including the number of rectifying column, number of theoretical plate, operating pressure, reflux ratio
Deng, and the method only with solvent crystallization separates 2,6-DIPN and 2,7-DIPN, and not only the time of crystallization process is very long
(20～36 hours), and need to carry out single-stage or multistage recrystallization, cause the consumption of solvent very big.
Complex can be formed with other compounds based on 2,6-DIPN, and easily crystalline deposit is separated out, US4962274 is carried
Go out with 9,9 '-two anthracenes for chelating agent, with acetone as solvent, by the complex for reacting 2,6-DIPN of production, complex crystallization
After precipitation, then Jing is filtered, is washed, being dried, the method that heating under reduced pressure decomposes can obtain the 2,6-DIPN of purity 99.8%, but its
Operation is more, and flow process is relative complex, and condition during heating under reduced pressure harsher (200 DEG C of pressure 25mmHg, temperature),
It is unfavorable for industrial amplification.
It is different from adsorbent surface inter-molecular binding force based on diisopropyl naphthalene isomerss, US4929796,
US5012039 with CN 101130481A propose to separate 2,6-DIPN and 2,7-DIPN, but product using the method for absorption
Purity not high (80.1～93.2%), it is still necessary to further to separate；US4992622 and US4950824 is it is also proposed that using suction
Attached method is capable of achieving the separating-purifying of 2,6-DIPN, although its product purity and yield are of a relatively high, in general
Absorbing process is more complicated, and the selectivity of adsorbent, adsorption capacity and desorption process all limit the effect of absorbing process,
There is not cost-effective adsorbent yet at present, constrain its industry and amplify.
Therefore, the purification technique of effective 2,6-DIPN is developed for the development for promoting China's polyester industrial has
Highly important meaning.More meaningful, due to rich coal resources in China, the separation for developing 2,6-DIPN is carried
Pure technology, the naphthalene for being beneficial to make full use of in China's coal tar, is the high-purity 2,6-DIPN of raw material production with which,
And then raw material is provided to produce PEN, so as to greatly improve the utilization rate of resource.
The content of the invention
Flow process when being prior art separating-purifying 2,6- diisopropyl naphthalenes to be solved by this invention is complicated, product purity is low, no
The technical problem of easy industrial applications.There is provided a kind of process for separation and purification of new 2,6-DIPN, the method is used for
During separating-purifying 2,6-DIPN, have the advantages that flow process is simple, product purity is high, be easy to industrial applications.
In order to solve above-mentioned technical problem, the technical solution used in the present invention is as follows：Mixed liquor containing 2,6- diisopropyl naphthalenes
I enters rectifying column, separated, and tower top obtains stream I I containing naphthalene, single isopropyl naphthalene, tower reactor obtain containing diisopropyl naphthalene,
Stream I II of triisopropyl naphthalene and other heavy constituents；Stream I II enters the first crystallizer, and Jing suspension crystallization processes are obtained containing thick
Stream I V and logistics V containing first degree crystalline mother solution of 2,6- diisopropyl naphthalene crystal；Stream I V enters the second crystallizer, with
The solvent stream VI of addition, Jing solvent crystallizations, washing and dry run obtain logistics VII containing high-purity 2,6-DIPN
And logistics VIII containing secondary crystallization mother solution.
In above-mentioned technical proposal, in mixed liquor I, 2,6-DIPN content by weight percentage is 10～35%, its
In its impurity, naphthalene content by weight percentage is that 3～20%, 2,7- diisopropyl naphthalenes content by weight percentage is
10～40%, the heavy constituent of the isomerss and naphthalene containing triisopropyl of other diisopropyl naphthalenes, many isopropyl naphthalenes is with weight hundred
The content than meter is divided to be 5～20%；The number of theoretical plate of rectifying column is 15～30 pieces, and stream I is entered from the middle part of tower, charging aperture
Positioned at the 6th～20 piece of theoretical plate of tower, operating pressure is calculated as 5～30KPa with absolute pressure, and reflux ratio is 0.3～3.0, tower point
It is the combination of filler, column plate or filler and column plate from element；Containing diisopropyl naphthalene, triisopropyl naphthalene and other restructuring after separation
Stream I II divided enters the first crystallizer, uses suspension crystallization process, and crystallization temperature is -25～5 DEG C；After filtration
Coarse-grain IV travels further into the second crystallizer Jing after melting, and uses solvent crystallization process, and crystallization temperature is -5～18 DEG C,
Solvent for use is alcohol compound, including methanol, ethanol, propanol, isopropanol etc., wherein solvent crystallization and washing process institute
Solvent can be with identical or differ.
As it was previously stated, in product of the naphthalene with propylene isopropylation, being close to 2,6-DIPN boiling point containing more
Diisopropyl naphthalene isomerss, high-purity 2,6-DIPN product cannot be obtained using the method for rectification directly, together
When, as the fusing point (80.1 DEG C) of naphthalene in product is higher than (67～70 DEG C) of the fusing point of 2,6-DIPN, directly adopt
Method with crystallization will separate out the crystal containing a large amount of naphthalenes, cannot also obtain high-purity 2,6-DIPN product.The present invention is adopted
The separating-purifying of 2,6-DIPN is carried out with the group technology of rectification-crystallization, i.e., first by using suitable distillation operation
Condition, realizes preferable fraction cutting effect, it is ensured that naphthalene and Dan Yi are not contained in the feed composition of later crystallization separation process
Propyl group naphthalene, it is to avoid the condition milder that separates out the adverse effect brought first, make crystallization process of naphthalene during later crystallization,
Reduce the difficulty of separation process；Secondly, based on other diisopropyl naphthalene isomers, triisopropyl naphthalene in the fraction after cutting
And many isopropyls fusing point how has bigger difference with 2,6-DIPN, first separated out rich in 2,6- using the method for suspension crystallization
The crystal of diisopropyl naphthalene, realizes 2,6-DIPN and other impurity, mainly triisopropyl naphthalene, many isopropyl naphthalenes
And efficiently separating except the isomerss outside 2,7- diisopropyl naphthalenes, while being greatly reduced 2,7- diisopropyls in coarse-grain
The content of naphthalene；Then, based on alcohol compound, such as ethanol, propanol, isopropanol etc. are at different temperatures to 2,6- diisopropyls
The dissolubility of base naphthalene has a notable difference, and alcohols material polarity is relatively low compared with strong, boiling point, and cheap and easy to get, then with above-mentionedization
Compound is solvent, realizes the further purification of product using the method for solvent crystallization, especially realizes and connect with boiling point the most
Near 2,7- diisopropyl naphthalenes are efficiently separated, so as to obtain high-purity 2,6-DIPN product.
From the comparison of embodiment and comparative example can be seen that for cut after the light components such as naphthalene, single isopropyl naphthalene containing 2,6-
It is for the mixed liquor of diisopropyl naphthalene, during the method crystallized using first solvent crystallization settling flux as shown in Figure 2, not only molten
In agent crystallization process, crystallization time is very long, and also different containing more 2,7- bis- in the 2,6-DIPN product after separating
Propyl group naphthalene, now again by the method for suspension crystallization, it is impossible to effectively remove 2,7- diisopropyl naphthalenes therein, cause product pure
Degree is low；When directly using the method for solvent crystallization as shown in Figure 3, due to impurity content height, in order to improve product purity,
One or more levels recrystallization must be carried out, need to consume more solvents, at the same further increase solvent crystallization process when
Between；During using the first suspension crystallization as shown in Figure 4 method that laminar is crystallized again, although not using solvent, in order to improve product
Product purity, it is also necessary to carry out multistage low temperature laminar crystallization, however, as impurity is easily attached on plane of crystal, product purity
Raising it is limited, in addition laminar crystallization process be intermittently operated, be unfavorable for industrial amplification.And using the knot that first suspends in embodiment
The method of brilliant solvent crystallization again, not only crystallization time is short, solvent load is few, and process is simple, product purity are higher, because
This, can more preferable separating-purifying 2,6-DIPN using rectification of the present invention-crystallization combined method.
Using technical scheme, by the compound mode of first suspension crystallization solvent crystallization again, ensureing product purity
Meanwhile, the consumption of solvent is not only reduced, and shortens crystallization time, reduce cost.Compared with prior art, originally
Invention have the advantages that flow process simply, product purity can improve more than 4%, achieve good technique effect.
Description of the drawings
Fig. 1 is the process for separating and purifying flow chart of 2,6- diisopropyl naphthalenes involved in the present invention
The process chart of Fig. 2,3,4 for separation 2,6- diisopropyl naphthalenes
In Fig. 1, B1 is that to cut the rectifying column of fraction, C1 for the crystallizer of suspension crystallization process, C2 be solvent crystallization mistake
The crystallizer of journey.It is containing naphthalene, single isopropyl that logistics (101) is the mixed liquor containing 2,6- diisopropyl naphthalenes, logistics (102)
The overhead of the rectifying column B1 of base naphthalene, logistics (103) are containing diisopropyl naphthalene, triisopropyl naphthalene and other heavy constituents
The tower reactor distillation of rectifying column B1, logistics (104) be rich in 2,6- diisopropyl naphthalenes after crystallizer C1 is separated
Magma, logistics (105) be through crystallizer C1 separate after containing other diisopropyl naphthalene isomerss, triisopropyls
The first degree crystalline mother solution of naphthalene and other heavy constituents, logistics (106) for add during solvent crystallization solvent, logistics (107)
Be 2,6- diisopropyl naphthalene products after the further separating-purifyings of crystallizer C2, logistics (108) be through crystallizer
Rich solvent-laden secondary crystallization mother solution after C2 separation.
In Fig. 2, D1 is that to cut the rectifying column of fraction, E1 for the crystallizer of solvent crystallization process, E2 be suspension crystallization mistake
The crystallizer of journey.Logistics (201)～logistics (203) is with the logistics (101) in Fig. 1～logistics (103), logistics (204)
It is rich in 2,6- diisopropyls after crystallizer E1 is separated for the solvent that adds during solvent crystallization, logistics (205)
The magma of naphthalene, logistics (206) be through crystallizer E1 separate after rich solvent-laden first degree crystalline mother solution, logistics (207)
Be 2,6- diisopropyl naphthalene products after the further separating-purifyings of crystallizer E2, logistics (208) be through crystallizer E2
The secondary crystallization mother solution containing other diisopropyl naphthalene isomerss after separation.
In Fig. 3, D1 still for the cutting rectifying column of fraction, F1 be the first degree crystalline device of solvent crystallization process, F2 be solvent
The secondary crystallizer of recrystallization process.Logistics (301)～logistics (306) with the logistics (201) in Fig. 2～logistics (206),
Logistics (307) be 2,6- diisopropyl naphthalene products after the further separating-purifying of recrystallization, logistics (308) be through
The secondary crystallization mother solution rich in solvent He other diisopropyl naphthalene isomerss after recrystallization separation.
In Fig. 4, D1 still for the cutting rectifying column of fraction, G1 be the crystallizer of suspension crystallization process, G2 be laminar crystallization
The crystallizer of process.Logistics (401)～logistics (405) is with the logistics (101) in Fig. 1～logistics (105), logistics (406)
Be 2,6- diisopropyl naphthalene products after the further separating-purifyings of crystallizer G2, logistics (407) be through crystallizer
The secondary crystallization mother solution containing other diisopropyl naphthalene isomerss after G2 separation.
Below by embodiment, the invention will be further elaborated.
Specific embodiment
【Embodiment 1】
Using the flow process shown in Fig. 1, logistics (101) is the mixed liquor containing 2,6-DIPN, with weight percentage
Consist of：Naphthalene 19.28%, single isopropyl naphthalene 49.03%, 2,6- diisopropyl naphthalenes 10.77%, 2,7- diisopropyl naphthalenes 11.12%,
The heavy constituent such as other diisopropyl naphthalenes and triisopropyl naphthalene 9.8%.
The number of theoretical plate of rectifying column B1 is 30, and logistics (101) is entered from the 20th piece of theoretical plate, and operating pressure is 10KPa,
Reflux ratio is 0.5, and tower top temperature is 157.07 DEG C, bottom temperature is 222.27 DEG C, does not contain naphthalene after separation in logistics (103),
2,6- diisopropyl naphthalenes by weight percentage consist of 34.74%；Logistics (103) is into crystallizer C1, crystallization temperature
For -15 DEG C, crystallization time is 6hr, Jing suspension crystallization and filter after, in the crystal of logistics (104) 2,6-DIPN with
The purity of percentage by weight meter is 76.84%；Logistics (104) goes successively to crystallizer C2, and solvent is ethanol, crystallization temperature
For 5 DEG C, crystallization time is 6hr, after Jing solvent crystallizations, washing with alcohol, and filtration, drying, the product of logistics (106)
In product, 2,6-DIPN purity by weight percentage is 99.52%, and wherein solvent and the mass ratio of raw material are 0.93:1.
【Embodiment 2】
Constituted using flow process same as Example 1 and raw material.The number of theoretical plate of rectifying column B1 is 20, logistics (101)
Enter from the 12nd piece of theoretical plate, operating pressure is 30KPa, and reflux ratio is 1.2, tower top temperature is 193.89 DEG C, tower reactor temperature
Spend for 262.08 DEG C, in the logistics (103) after separation, do not contain naphthalene, 2,6-DIPN consisting of by weight percentage
34.74%；Logistics (103) is -20 DEG C into crystallizer C1, crystallization temperature, and crystallization time is 7hr, and Jing suspension crystallizations are simultaneously
After filtration, in the crystal of logistics (104), 2,6-DIPN purity by weight percentage is 73.09%；Logistics (104)
Go successively to crystallizer C2, solvent is ethanol, and crystallization temperature is 0 DEG C, crystallization time is 7hr, Jing solvent crystallizations, methanol
After washing, and filtration, drying, 2,6-DIPN purity by weight percentage in the product of logistics (106)
For 99.50%, wherein solvent and the mass ratio of raw material are 0.88:1.
【Embodiment 3】
Using the flow process shown in Fig. 1, logistics (101) is the mixed liquor containing 2,6-DIPN, with weight percentage
Consist of：Naphthalene 11.39%, single isopropyl naphthalene 31.53%, 2,6- diisopropyl naphthalenes 20.18%, 2,7- diisopropyl naphthalenes 21.19%,
The heavy constituent such as other diisopropyl naphthalenes and triisopropyl naphthalene 15.71%.
The number of theoretical plate of rectifying column B1 is 25, and logistics (101) is entered from the 17th piece of theoretical plate, and operating pressure is 5KPa,
Reflux ratio is 0.9, and tower top temperature is 138.27 DEG C, bottom temperature is 199.99 DEG C, is not contained in the logistics (103) after separation
Naphthalene, 2,6-DIPN by weight percentage consist of 36.04%；Logistics (103) is into crystallizer C1, crystallization
Temperature is -10 DEG C, and crystallization time is 5hr, Jing suspension crystallization and after filtration, 2,6- diisopropyls in the crystal of logistics (104)
Naphthalene purity by weight percentage is 77.71%；Logistics (104) goes successively to crystallizer C2, and solvent is propanol, crystallization
Temperature is 8 DEG C, and crystallization time is 5.5hr, after Jing solvent crystallizations, washing with alcohol, and filtration, drying, logistics (106)
Product in 2,6-DIPN purity by weight percentage be 99.55%, wherein solvent with the mass ratio of raw material is
1.73:1。
【Embodiment 4】
Constituted using flow process same as Example 3 and raw material.The number of theoretical plate of rectifying column B1 is 15, logistics (101)
Enter from the 6th piece of theoretical plate, operating pressure is 20KPa, and reflux ratio is 2.0, tower top temperature is 180.74 DEG C, tower reactor temperature
Spend for 245.98 DEG C, in the logistics (103) after separation, do not contain naphthalene, 2,6-DIPN consisting of by weight percentage
36.03%；Logistics (103) is -15 DEG C into crystallizer C1, crystallization temperature, and crystallization time is 6hr, and Jing suspension crystallizations are simultaneously
After filtration, in the crystal of logistics (104), 2,6-DIPN purity by weight percentage is 75.48%；Logistics (104)
Go successively to crystallizer C2, solvent is isopropanol, and crystallization temperature is 3 DEG C, crystallization time is 6.5hr, Jing solvent crystallizations,
Isopropanol is washed, and after filtering, being dried, in the product of logistics (106), 2,6-DIPN is by weight percentage
Purity be 99.51%, wherein the mass ratio of solvent and raw material is 1.60:1.
【Embodiment 5】
Using the flow process shown in Fig. 1, logistics (101) is the mixed liquor containing 2,6-DIPN, with weight percentage
Consist of：Naphthalene 5.79%, single isopropyl naphthalene 13.62%, 2,6- diisopropyl naphthalenes 30.48%, 2,7- diisopropyl naphthalenes 32.62%,
The heavy constituent such as other diisopropyl naphthalenes and triisopropyl naphthalene 17.49%.
The number of theoretical plate of rectifying column B1 is 25, and logistics (101) is entered from the 17th piece of theoretical plate, and operating pressure is 15KPa,
Reflux ratio is 2.5, and tower top temperature is 168.84 DEG C, bottom temperature is 235.20 DEG C, is not contained in the logistics (103) after separation
Naphthalene, 2,6-DIPN by weight percentage consist of 37.82%；Logistics (103) is into crystallizer C1, crystallization
Temperature is -8 DEG C, and crystallization time is 4.5hr, Jing suspension crystallization and after filtration, 2,6- diisopropyls in the crystal of logistics (104)
Base naphthalene purity by weight percentage is 79.67%；Logistics (104) goes successively to crystallizer C2, and solvent is methanol, knot
Brilliant temperature is 10 DEG C, and crystallization time is 5hr, after Jing solvent crystallizations, washing with alcohol, and filtration, drying, logistics (106)
Product in 2,6-DIPN purity by weight percentage be 99.58%, wherein solvent with the mass ratio of raw material is
2.54:1。
【Embodiment 6】
Constituted using flow process same as Example 5 and raw material.The number of theoretical plate of rectifying column B1 is 20, logistics (101)
Enter from the 12nd piece of theoretical plate, operating pressure is 20KPa, and reflux ratio is 2.9, tower top temperature is 178.43 DEG C, tower reactor temperature
Spend for 245.56 DEG C, in the logistics (103) after separation, do not contain naphthalene, 2,6-DIPN consisting of by weight percentage
37.82%；Logistics (103) is -5 DEG C into crystallizer C1, crystallization temperature, and crystallization time is 4hr, and Jing suspension crystallizations are simultaneously
After filtration, in the crystal of logistics (104), 2,6-DIPN purity by weight percentage is 80.10%；Logistics (104)
Go successively to crystallizer C2, solvent is propanol, and crystallization temperature is 12 DEG C, crystallization time is 4.5hr, Jing solvent crystallizations, second
Alcohol is washed, and after filtering, being dried, 2,6-DIPN by weight percentage pure in the product of logistics (106)
Spend for 99.61%, wherein solvent and the mass ratio of raw material are 2.78:1.
【Embodiment 7】
Using the flow process shown in Fig. 1, logistics (101) is the mixed liquor containing 2,6-DIPN, with weight percentage
Consist of：Naphthalene 5.06%, single isopropyl naphthalene 13.14%, 2,6- diisopropyl naphthalenes 34.71%, 2,7- diisopropyl naphthalenes 37.49%,
The heavy constituent such as other diisopropyl naphthalenes and triisopropyl naphthalene 9.60%.
The number of theoretical plate of rectifying column B1 is 25, and logistics (101) is entered from the 17th piece of theoretical plate, and operating pressure is 25KPa,
Reflux ratio is 2.2, and tower top temperature is 188.67 DEG C, bottom temperature is 256.52 DEG C, is not contained in the logistics (103) after separation
Naphthalene, 2,6-DIPN by weight percentage consist of 43.06%；Logistics (103) is into crystallizer C1, crystallization
Temperature is 0 DEG C, and crystallization time is 3hr, Jing suspension crystallization and after filtration, 2,6- diisopropyls in the crystal of logistics (104)
Naphthalene purity by weight percentage is 80.53%；Logistics (104) goes successively to crystallizer C2, and solvent is ethanol, crystallization
Temperature is 16 DEG C, and crystallization time is 4hr, after Jing solvent crystallizations, washing with alcohol, and filtration, drying, logistics (106)
Product in 2,6-DIPN purity by weight percentage be 99.67%, wherein solvent with the mass ratio of raw material is
3.15:1。
【Comparative example 1】
Using the flow process shown in Fig. 2, constituted using raw material same as Example 1, the operating condition of rectifying column D1 is with real
The rectifying column B1 in example 1 is applied, naphthalene in the logistics (203) after separation, is not contained, 2,6-DIPN is by weight percentage
Consist of 34.74%；Into crystallizer E1, logistics (204) is molten for the ethanol of solvent crystallization process for logistics (203)
Agent, solvent are 1 with the mass ratio of raw material:1, crystallization temperature is 25 DEG C, and crystallization time is 36 hours, and Jing is filtered, ethanol is more
After secondary washing, in the crystal of logistics (205), 2,6-DIPN purity by weight percentage is 88.35%, wherein
2,7- diisopropyl naphthalenes content by weight percentage is 10.19%；Logistics (205) goes successively to crystallizer E2, crystallization
Temperature is 40 DEG C, and crystallization time is 5hr, Jing suspension crystallization, after filtering and being dried, 2,6- in the product of logistics (207)
Diisopropyl naphthalene purity by weight percentage is 91.74%, wherein 2,7- diisopropyl naphthalenes content by weight percentage
For 7.28%.
【Comparative example 2】
Using the flow process shown in Fig. 3, constituted using raw material same as Example 1, the behaviour of rectifying column D1 and crystallizer F1
Make condition with the rectifying column D1 and crystallizer E1 in comparative example 1, after separation, the composition of logistics (305) is with comparative example 1
In logistics (205)；Logistics (305) goes successively to crystallizer F2 and carries out recrystallization, and crystallization temperature is 45 DEG C, during crystallization
Between be 20hr, Jing recrystallization, filter and be dried after, in the product of logistics (307), 2,6-DIPN is with weight percent
Purity than counting is 95.15%, wherein 2,7- diisopropyl naphthalenes content by weight percentage is 4.55%, total solvent is used
Amount is 2.22 with the mass ratio of raw material:1.
【Comparative example 3】
Using the flow process shown in Fig. 4, constituted using raw material same as Example 1, rectifying column D1's and crystallizer G1
Operating condition with the rectifying column B1 and crystallizer C1 in embodiment 1, after separation, the same embodiment of composition of logistics (404)
Logistics (104) in 1；Logistics (404) goes successively to crystallizer G2 and carries out laminar crystallization, and crystallization temperature is 45 DEG C, knot
The brilliant time is 4hr, and after crystallized, diaphoresis, 2,6-DIPN is by weight percentage in the product of logistics (406)
Purity is 92.68%, wherein 2,7- diisopropyl naphthalenes content by weight percentage is 7.11%.
Claims (10)
1. a kind of process for separation and purification of 2,6-DIPN, comprises the following steps：
A the mixed liquor I of () containing 2,6-DIPN enters rectifying column, separated, and tower top is obtained containing naphthalene, single isopropyl
Stream I I of naphthalene, tower reactor obtain stream I II containing diisopropyl naphthalene, triisopropyl naphthalene and other heavy constituents；
B () above-mentioned logistics III enters the first crystallizer, Jing suspension crystallization processes are obtained containing thick 2,6-DIPN crystal
Stream I V and logistics V containing first degree crystalline mother solution；
C () above-mentioned stream I V enters the second crystallizer, with the solvent stream VI for adding, Jing solvent crystallizations, washing and drying
Process obtains logistics VII containing high-purity 2,6- diisopropyl naphthalenes and logistics VIII containing secondary crystallization mother solution.
2. the process for separation and purification of 2,6-DIPN according to claim 1, it is characterised in that mixed liquor I
Middle 2,6- diisopropyl naphthalenes content by weight percentage is 10～35%.
3. the process for separation and purification of 2,6-DIPN according to claim 1, it is characterised in that mixed liquor I
Middle impurity content by weight percentage is 65～90%, and wherein naphthalene content by weight percentage is 3～20%, 2,7-
Diisopropyl naphthalene content by weight percentage is the isomer of 10～40%, other diisopropyl naphthalenes and contains triisopropyl
Naphthalene, the heavy constituent content by weight percentage of many isopropyl naphthalenes are 5～20%.
4. the process for separation and purification of 2,6-DIPN according to claim 1, it is characterised in that the reason of rectifying column
It it is 15～30 pieces by plate number；Mixed liquor I is entered from the middle part of tower, and charging aperture is located at the 6th～20 piece of theoretical plate of tower；Behaviour
Make pressure and 5～30KPa is calculated as with absolute pressure；Reflux ratio is 0.3～3.0.
5. the process for separation and purification of the 2,6-DIPN according to claim 1 or 4, it is characterised in that rectifying column
Resolution element be filler, column plate or filler and column plate combination.
6. the process for separation and purification of 2,6-DIPN according to claim 1, it is characterised in that the first crystallizer
In use suspension crystallization process, crystallization temperature is -25～5 DEG C.
7. the process for separation and purification of 2,6-DIPN according to claim 1, it is characterised in that the second crystallizer
In use solvent crystallization process, crystallization temperature is -5～18 DEG C.
8. the process for separation and purification of the 2,6-DIPN according to claim 1 or 7, it is characterised in that used molten
Agent is alcohol compound.
9. the process for separation and purification of the 2,6-DIPN according to claim 1 or 8, it is characterised in that solvent is tied
Solvent used by brilliant and washing process is identical.
10. the process for separation and purification of the 2,6-DIPN according to claim 1 or 8, it is characterised in that solvent is tied
Solvent used by brilliant and washing process is different.
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| CN201510686007.8A CN106608809A (en) | 2015-10-21 | 2015-10-21 | Separation and purification method for 2,6-diisopropylnaphthalene |
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1793088A (en) * | 2005-12-19 | 2006-06-28 | 鞍山科技大学 | Process for preparing 2.6-naphthalene diisoproply by essential naphthalene critical hydrogen isopropylation |
| CN101130478A (en) * | 2006-08-25 | 2008-02-27 | 北京石油化工学院 | Method for preparing high purity2, 6-diisopropyl naphthalene |
-
2015
- 2015-10-21 CN CN201510686007.8A patent/CN106608809A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1793088A (en) * | 2005-12-19 | 2006-06-28 | 鞍山科技大学 | Process for preparing 2.6-naphthalene diisoproply by essential naphthalene critical hydrogen isopropylation |
| CN101130478A (en) * | 2006-08-25 | 2008-02-27 | 北京石油化工学院 | Method for preparing high purity2, 6-diisopropyl naphthalene |
Non-Patent Citations (1)
| Title |
|---|
| 李文艳: "2,6-二异丙基萘分离精制方法的研究", 《中国优秀博硕士学位论文全文数据库（硕士） 工程科技I辑》 * |
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