CN103664582A - Solvent replacement method of coarse 2,6-naphthalic acid oxidation slurry - Google Patents

Solvent replacement method of coarse 2,6-naphthalic acid oxidation slurry Download PDF

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CN103664582A
CN103664582A CN201210324512.4A CN201210324512A CN103664582A CN 103664582 A CN103664582 A CN 103664582A CN 201210324512 A CN201210324512 A CN 201210324512A CN 103664582 A CN103664582 A CN 103664582A
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filter cake
slurry
solvent exchange
thick
flash distillation
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CN103664582B (en
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张海涛
司丹
畅延青
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China Petroleum and Chemical Corp
Sinopec Shanghai Research Institute of Petrochemical Technology
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China Petroleum and Chemical Corp
Sinopec Shanghai Research Institute of Petrochemical Technology
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/42—Separation; Purification; Stabilisation; Use of additives

Abstract

The invention relates to a solvent replacement method of coarse 2,6-naphthalic acid oxidation slurry, which mainly solves the problem of low washing efficiency in the prior art. According to the technical scheme of the invention, the solvent replacement method comprises the following steps: filtering flash evaporation slurry I to obtain a filter cake II and a filtrate III; purging the inside of the filter cake II with oxygen-containing airflow, thus removing residual impurities in the filter cake II in an airflow carrying manner to obtain a filter cake IV and purging tail gas A; washing the filter cake IV with a washing solution composed of 0-95wt% of water and 5-100wt% of ROCH2CH2OH to obtain a filter cake V and a filtrate VI, wherein R is C1-4 alkyl; and purging the inside of the filter cake V with oxygen-containing airflow, thus removing residual impurities in the filter cake V in an airflow carrying manner to obtain a filter cake VII and purging tail gas B. Thus, the problem is well solved; and the solvent replacement method can be used for industrial production of purifying 2,6-naphthalic acid oxidation slurry.

Description

The method of thick NDA oxidation slurry solvent exchange
Technical field
The present invention relates to a kind of method of thick NDA oxidation slurry solvent exchange.
Background technology
2,6-naphthalic acid (is called for short 2,6-NDCA) be the important monomer of preparation various polyester, urethane and vibrin, due to high symmetry in its structure, with ethylene glycol polymerization obtain poly-2,6-naphthalic acid diethyl alcohol ester (PEN) has the characteristic of straight-chain polymer, is a kind of good rigidly, intensity is large, hot workability is good material, can be used for manufacturing backing tape, fiber, food-drink container etc.Polyethylene terephthalate (PET) with widespread use is at present compared, the aspects such as its resistance toheat, barrier properties for gases, mechanical property, chemical stability are more superior, be polyester material of new generation, in fields such as fiber, film, packaging vessels, have a wide range of applications.2, 6-NDCA production technique comprises oxidation, refining two sections of operations, its oxidation operation be take acetic acid as solvent, adopt cobalt-manganese-bromide catalizer, pass into oxygen-containing gas (conventionally adopting air), 2, 6-dimethylnaphthalene or 2, it is thick 2 of solvent that the oxidation of 6-diisopropylnaphthalene high-temperature liquid-phase obtains acetic acid, 6-naphthalic acid oxidation slurry, because refining step adopts pure water as solvent, therefore oxidation operation need to be obtained thick 2, acetic acid solvent in 6-naphthalic acid oxidation slurry is replaced into water solvent, reclaim simultaneously, reduce acetic acid wherein, the content of the components such as catalyzer, it controls index: acetic acid, the content of catalyzer all not higher than 1000ppm(otherwise will affect follow-up unifining process and cause material consumption to exceed standard), in the process of this solvent exchange in the art, be referred to as solvent exchange method.
By thick 2, acetic acid solvent in 6-naphthalic acid oxidation slurry is replaced into water solvent, the water that washings can adopt CN1911895A to mention, p-Xylol or the ethyl acetate that also can adopt CN1129693A to mention, while adopting above-mentioned 2 kinds of washingss washing, acetic acid in cleaning product, catalyzer, washings and other impurity residual quantity are higher, therefore while adopting above-mentioned 2 kinds of washingss to carry out solvent exchange washing, can cause detersive efficiency lower.
Summary of the invention
Technical problem to be solved by this invention is the problem that exists detersive efficiency low in prior art, provide a kind of new thick 2, the method of 6-naphthalic acid oxidation slurry solvent exchange, the impurity that the method can lower in cleaning product-filter cake is preferably residual, has and simplifies working process and energy-saving and cost-reducing feature.
In order to solve the problems of the technologies described above, the technical solution used in the present invention is as follows: a kind of method of thick NDA oxidation slurry solvent exchange, comprises following process:
A) filter flash distillation slurry I, obtain filter cake and filtrate
Figure 55397DEST_PATH_IMAGE002
;
B) with oxygen flow, purge filter cake
Figure 915029DEST_PATH_IMAGE001
inside, the residual impurity that the mode of carrying secretly by air-flow is removed in filter cake II obtains filter cake I
Figure 310238DEST_PATH_IMAGE003
with purging tail gas A;
C) with by weight percentage by the ROCH of 0 ~ 95% water and 5 ~ 100% 2cH 2the washings washing leaching cake I that OH forms
Figure 186927DEST_PATH_IMAGE003
obtain filter cake
Figure 9390DEST_PATH_IMAGE003
and filtrate
Figure 338740DEST_PATH_IMAGE004
, wherein R is C1 ~ C4 alkyl;
D) with oxygen flow, purge filter cake inside, the mode of carrying secretly by air-flow is removed filter cake
Figure 268836DEST_PATH_IMAGE003
in residual impurity obtain filter cake with purging tail gas B.
In technique scheme, the ROCH2CH2OH that the washings in described step c) is preferably by weight percentage by 50 ~ 95% water and 5 ~ 50% forms; Described R is preferably ethyl; Flash distillation slurry I in described step a) is more excellent to be obtained by oxidation reactor thick NDA oxidation slurry vacuum flashing out.The physical property condition optimization of flash distillation slurry I in described step a) is: volume space velocity 5-25hr-1, by weight percentage, NDA concentration 10 ~ 35%, temperature normal temperature ~ 150 ℃, pressure 0 ~ 10kg/cm2; During described filtration flash distillation slurry I, adopt positive press filtration, pressure reduction is 0.1 ~ 6.0 kg/cm2 preferably; Described step b) and step e) in oxygen flow volume space velocity and step a) ratio of the volume space velocity of middle flash distillation slurry I be preferably 0.5 ~ 6.0:1; The volume space velocity of the washings being formed by the ROCH2CH2OH of 0 ~ 95% water and 5 ~ 100% by weight percentage described step c) and step a) in the ratio of volume space velocity of flash distillation slurry I be preferably 0.1 ~ 2.0:1; Described step b) and steps d) in oxygen level in oxygen flow in volume percent, be preferably 15 ~ 35%.
The key problem in technology of the inventive method is ROCH 2cH 2oH when R be that C1-C4 especially has more suitably lipophilicity and wetting ability when R is C2 simultaneously, with washing leaching cake
Figure 78846DEST_PATH_IMAGE002
in remaining acetic acid mutual solubility fabulous, easily by oxygen flow, carried secretly.The filter cake that step d) of the present invention obtains
Figure 815858DEST_PATH_IMAGE006
can be mixed to ingredients concentration with water can, directly as the hydrorefined charging of NDA, simplify working process and energy-saving and cost-reducing feature therefore the present invention has.Experimental result shows: under the same terms, and washings employing-ROCH 2cH 2oH(R=C1 ~ C4) be ethylene glycol monoethyl ether, monomethyl ether, single isopropyl ether and mono-n-butyl ether and employing ethyl acetate, p-Xylol and water comparison, the solvent exchange product-filter cake obtaining
Figure 401560DEST_PATH_IMAGE005
middle catalyzer, acetic acid, washings content all reduce more than 30%, and meet the charging requirement of follow-up hydrogenation refining step completely.
Accompanying drawing explanation
Below in conjunction with accompanying drawing, the present invention is described in detail.
Fig. 1 is process flow diagram of the present invention.
In Fig. 1,1 is thick NDA oxidation flash distillation slurry I, and 2 is filtrate
Figure 831404DEST_PATH_IMAGE002
, 3 is filter operation, 4 is filter cake
Figure 135346DEST_PATH_IMAGE001
, 5 is purge operations, and 6 is oxygen flow, and 7 for purging tail gas A, and 8 is filter cake I
Figure 410470DEST_PATH_IMAGE003
, 9 is that washings is (by water, ROCH 2cH 2oH forms), 10 is washing operation, 11 is filtrate
Figure 116258DEST_PATH_IMAGE004
, 12 is filter cake , 13 is oxygen flow, and 14 is purge operations, and 15 is filter cake
Figure 242663DEST_PATH_IMAGE005
, 16 for purging tail gas B.
As shown in Figure 1, it is 0.1 ~ 6.0 kg/cm that the thick NDA oxidation flash distillation slurry I1 that the NDA oxidation slurry that oxidation reactor obtains containing NDA, acetic acid and catalyzer etc. obtains after vacuum flashing carries out pressure reduction 2filter operation 3, the physical property condition of thick NDA oxidation flash distillation slurry I1 is: by weight percentage, and 2,6-naphthalic acid concentration is 10 ~ 35%, catalyzer 0.1 ~ 0.5%, acetic acid concentration 54.5 ~ 84.9%, other impurity of other impurity 5.0 ~ 10.0%(refer in this material except 2, the general designation of all components outside 6-naphthalic acid, acetic acid, catalyzer, lower same), temperature is room temperature ~ 150 ℃, pressure is 0 ~ 10kg/cm 2.Thick NDA oxidation flash distillation slurry I1 is with air speed 5-25hr -1carrying out pressure reduction is 0.1 ~ 6.0 kg/cm 2filter operation 3, obtain respectively filter cake
Figure 321477DEST_PATH_IMAGE001
4 and mainly contain the filtrate of acetic acid, catalyzer and other impurity 2.
6 pairs of filter cakes of oxygen flow
Figure 653418DEST_PATH_IMAGE001
4 carry out purge operations 5, obtain purging tail gas A7 and filter cake I
Figure 666374DEST_PATH_IMAGE003
8, the oxygen level of oxygen flow 6 is in volume percent, and 15 ~ 35%, the volume space velocity of oxygen flow 6 is 0.5 ~ 6.0:1 with the volume space velocity ratio of thick NDA oxidation flash distillation slurry 1.
Washings 9(is comprised of the ROCH2CH2OH of 50 ~ 95% water and 5 ~ 50% by weight percentage) to adopt with the ratio of the volume space velocity of thick NDA oxidation flash distillation slurry 1 be that 0.1 ~ 2.0:1 is to filter cake I
Figure 611196DEST_PATH_IMAGE003
8 carry out washing operation 10, obtain respectively filtrate
Figure 963680DEST_PATH_IMAGE004
11 and filter cake
Figure 968545DEST_PATH_IMAGE003
12.
13 pairs of filter cakes of oxygen flow
Figure 406480DEST_PATH_IMAGE003
12 carry out purge operations 14, obtain purging tail gas B16 and filter cake
Figure 889414DEST_PATH_IMAGE005
15, the oxygen level of oxygen flow 13 is in volume percent, and 15 ~ 35%, oxygen flow 13 is 0.5 ~ 6.0:1 with the volume space velocity ratio of thick NDA oxidation flash distillation slurry 1.
Embodiment
[embodiment 1]
As shown in Figure 1, getting thick NDA oxidation flash distillation slurry I1 that NDA oxidation slurry that 1000.0g obtains containing NDA, acetic acid and catalyzer etc. from oxidation reactor obtains after vacuum flashing, to carry out pressure reduction be 2.5kg/cm 2filter operation 3, obtains respectively filter cake
Figure 361983DEST_PATH_IMAGE001
4 and mainly contain the filtrate of acetic acid, catalyzer and other impurity
Figure 537750DEST_PATH_IMAGE002
2, and analyze filtrate
Figure 525297DEST_PATH_IMAGE002
2 form, and calculate the separating effect (being decreasing ratio) of respective components, and wherein the physical property condition of thick NDA oxidation flash distillation slurry 1 is: air speed is 22hr -1, by weight percentage, NDA 26.79%, catalyzer 0.21%, acetic acid concentration 64.50%, other impurity 8.50%, temperature is 100 ℃, pressure is 4.0kg/cm 2.
6 pairs of filter cakes of oxygen flow 4 to carry out pressure reduction be 2.5kg/cm 2purge operations 5, obtains purging tail gas A7 and filter cake I
Figure 879278DEST_PATH_IMAGE003
8, oxygen flow 6 is air 6, and its volume space velocity is 44hr -1, temperature is room temperature.
It is 11hr that washings (ethylene glycol monoethyl ether by 65% water and 35% forms by weight percentage) 9 adopts volume space velocity -1, temperature is that room temperature is to filter cake I
Figure 225946DEST_PATH_IMAGE003
8 to carry out pressure reduction be 2.5kg/cm 2washing operation 10, obtains respectively filtrate
Figure 638473DEST_PATH_IMAGE004
11 and filter cake
Figure 728789DEST_PATH_IMAGE003
12.
13 pairs of filter cakes of oxygen flow
Figure 910371DEST_PATH_IMAGE003
12 to carry out pressure reduction be 2.5kg/cm 2purge operations 14, obtains purging tail gas B16 and filter cake 15, analyze filter cake
Figure 62184DEST_PATH_IMAGE005
15 form, and oxygen flow 13 is air 13, and its volume space velocity is 44hr -1, temperature is room temperature.Filter cake 15 add and become water-soluble NDA slurry after pure water batching and can be used as NDA hydrofining reaction raw material and directly enter hydrofining operation, the results are shown in Table 1.
[embodiment 2 ~ 8]
As shown in Figure 1, only change the variation that forms in washings in embodiment 1 (being comprised of water, ethylene glycol monoethyl ether) 9, other all correspondingly remains unchanged, and the results are shown in Table 1.
[embodiment 9 ~ 11]
As shown in Figure 1, ethylene glycol monoethyl ether in washings in embodiment 1 (being comprised of water, ethylene glycol monoethyl ether) 9 is formed to the monomethyl ether that replaces with respectively equal in quality percentage composition, single isopropyl ether, mono-n-butyl ether according to it, other all correspondingly remains unchanged, and the results are shown in Table 2.
[embodiment 12 ~ 15]
As shown in Figure 1, only change the air speed of (being formed by water, ethylene glycol monoethyl ether) 9 of washings in embodiment 1 and air 6,13, the results are shown in Table 3
[comparative example 1 ~ 3]
As shown in Figure 1, the ethylene glycol monoethyl ether in washings in embodiment 1 (being comprised of water, ethylene glycol monoethyl ether) 9 is replaced with respectively to ethyl acetate, p-Xylol, the water of equal in quality, other all correspondingly remains unchanged, and the results are shown in Table 4.
[comparative example 4,5]
As shown in Figure 1, the ethylene glycol monoethyl ether in washings in embodiment 1 (being comprised of water, ethylene glycol monoethyl ether) 9 is replaced with respectively to diethylene glycol monoethyl ether, the ethanol of equal in quality percentage composition, other all correspondingly remains unchanged, and the results are shown in Table 4.
table 1
Figure 992280DEST_PATH_IMAGE008
* in table 1 ~ 4:
?
table 2
? Embodiment 9 Embodiment 10 Embodiment 11
ROCH in washings 9 2CH 2OH Monomethyl ether Single isopropyl ether Mono-n-butyl ether
Catalyst removal rate *, % 94.0 94.0 94.0
Acetic acid decreasing ratio *, % 95.3 95.3 95.3
Other impurity removal percentages *, % 95.0 95.0 95.0
Filter cake
Figure 234408DEST_PATH_IMAGE005
Catalyzer in 15, ppm 		4.4 6.4 8.1
Filter cake
Figure 187321DEST_PATH_IMAGE005
Acetic acid in 15, ppm 		151.0 167.3 186.3
Filter cake ROCH in 15 2CH 2OH，ppm 214.6 200.3 219.0
Filter cake
Figure 655528DEST_PATH_IMAGE005
Other foreign matter contents in 15, ppm 		3012 2943 3192
table 3
? Embodiment 12 Embodiment 13 Embodiment 14 Embodiment 15
The air speed of washings 9, hr -1 2.2 22 33 44
Washings 9 and flash distillation slurry I1 volume space velocity ratio 0.1 1.0 1.5 2.0
The air speed of air 6,13, hr -1 22 66 88 110
Air 6,13 and flash distillation slurry I1 volume space velocity ratio 1:1 3:1 4:1 5:1
Catalyst removal rate, % 94.0 94.0 94.0 94.0
Acetic acid decreasing ratio, % 95.3 95.3 95.3 95.3
Other impurity removal percentages, % 95.0 95.0 95.0 95.0
Filter cake
Figure 829021DEST_PATH_IMAGE005
Catalyst content in 15, ppm 		2.3 1.6 1.4 1.1
Filter cake
Figure 902019DEST_PATH_IMAGE005
Acetic acid content in 15, ppm 		236.7 120.8 113.3 108.2
Filter cake
Figure 869975DEST_PATH_IMAGE005
Ethylene glycol monoethyl ether content in 15, ppm 		233.0 162.1 154.4 145.3
Filter cake Other foreign matter contents in 15, ppm 3111.9 2560.9 2489.2 2360.3
table 4
? Comparative example 1 Comparative example 2 Comparative example 3 Comparative example 4 Comparative example 5
Washings 9 forms Ethyl acetate P-Xylol Water Diethylene glycol monoethyl ether, water Ethanol, water
Catalyst removal rate *, % 94.0 94.0 94.0 94.0 94.0
Acetic acid decreasing ratio *, % 95.3 95.3 95.3 95.3 95.3
Other impurity removal percentages *, % 95.0 95.0 95.0 95.0 95.0
Filter cake
Figure 802345DEST_PATH_IMAGE005
Catalyzer in 15, ppm 		11.2 10.5 18.2 8.1 6.4
Filter cake
Figure 667532DEST_PATH_IMAGE005
Acetic acid in 15, ppm 		425.3 461.4 514.0 228.3 204.2
Filter cake
Figure 868707DEST_PATH_IMAGE005
The washings of remnants in 15 (dewatering outer), ppm 		476.8 498.4 - 276.5 202.8
Filter cake
Figure 452135DEST_PATH_IMAGE005
Other impurity in 15, ppm 		5217.1 5823.0 5788.3 3937.8 3192.8

Claims (9)

1. a method for thick NDA oxidation slurry solvent exchange, comprises following process:
A) filter flash distillation slurry I, obtain filter cake
Figure 2012103245124100001DEST_PATH_IMAGE001
and filtrate
Figure 505901DEST_PATH_IMAGE002
;
B) with oxygen flow, purge filter cake
Figure 491174DEST_PATH_IMAGE001
inside, the residual impurity that the mode of carrying secretly by air-flow is removed in filter cake II obtains filter cake I
Figure 2012103245124100001DEST_PATH_IMAGE003
with purging tail gas A;
C) with by weight percentage by the ROCH of 0 ~ 95% water and 5 ~ 100% 2cH 2the washings washing leaching cake I that OH forms
Figure 925567DEST_PATH_IMAGE003
obtain filter cake
Figure 996291DEST_PATH_IMAGE003
and filtrate , wherein R is C1 ~ C4 alkyl;
D) with oxygen flow, purge filter cake
Figure 11182DEST_PATH_IMAGE003
inside, the mode of carrying secretly by air-flow is removed filter cake
Figure 491842DEST_PATH_IMAGE003
in residual impurity obtain filter cake
Figure 2012103245124100001DEST_PATH_IMAGE005
with purging tail gas B.
2. the method for thick NDA oxidation slurry solvent exchange according to claim 1, is characterized in that described step c) in washings by weight percentage by the ROCH of 50 ~ 95% water and 5 ~ 50% 2cH 2oH forms.
3. the method for thick NDA oxidation slurry solvent exchange according to claim 1 and 2, is characterized in that described R is ethyl.
4. the method for thick NDA oxidation slurry solvent exchange according to claim 1, is characterized in that in described step a) that flash distillation slurry I obtains by oxidation reactor thick NDA oxidation slurry vacuum flashing out.
5. the method for thick NDA oxidation slurry solvent exchange according to claim 1, is characterized in that the physical property condition of the flash distillation slurry I in described step a) is: volume space velocity 5-25hr -1, by weight percentage, NDA concentration 10 ~ 35%, temperature normal temperature ~ 150 ℃, pressure 0 ~ 10kg/cm 2.
6. the method for thick NDA oxidation slurry solvent exchange according to claim 1 and 2, while it is characterized in that filtering flash distillation slurry I, adopting positive press filtration, pressure reduction is 0.1 ~ 6.0 kg/cm 2.
7. the method for thick NDA oxidation slurry solvent exchange according to claim 1 and 2, is characterized in that step b) and steps d) in oxygen flow volume space velocity and step a) ratio of the volume space velocity of middle flash distillation slurry I be 0.5 ~ 6.0:1.
8. the method for thick NDA oxidation slurry solvent exchange according to claim 1 and 2, is characterized in that step c) in by weight percentage by the ROCH of 0 ~ 95% water and 5 ~ 100% 2cH 2the volume space velocity of the washings that OH forms and step a) ratio of the volume space velocity of middle flash distillation slurry I are 0.1 ~ 2.0:1.
9. the method for thick NDA oxidation slurry solvent exchange according to claim 1 and 2, is characterized in that step b) and steps d) in oxygen level in oxygen flow in volume percent, be 15 ~ 35%.
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Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1911895A (en) * 2003-12-29 2007-02-14 扬子石油化工股份有限公司 Method of separating and purifying terephthalic acid
CN101244997A (en) * 2007-02-16 2008-08-20 北京石油化工学院 Process for producing 2,6-naphthalenedicarboxylic acid
CN101395122A (en) * 2006-03-01 2009-03-25 伊士曼化工公司 Methods and apparatus for producing a low-moisture carboxylic acid wet cake

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1911895A (en) * 2003-12-29 2007-02-14 扬子石油化工股份有限公司 Method of separating and purifying terephthalic acid
CN101395122A (en) * 2006-03-01 2009-03-25 伊士曼化工公司 Methods and apparatus for producing a low-moisture carboxylic acid wet cake
CN101244997A (en) * 2007-02-16 2008-08-20 北京石油化工学院 Process for producing 2,6-naphthalenedicarboxylic acid

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