The method of obtaining 2,6-di-tert-butyl-phenol

 

(57) Abstract:

The invention relates to petrochemical synthesis of 2,6-di-tert-butyl-phenol alkylation of phenol isobutylester fraction in the presence of a catalyst of aluminum, dissolved in phenol, followed by separation of the desired product and impurities of alkyl phenols by distillation. After highlighting a clear rectification of 2,6-di-tert-butyl-phenol is subjected to successive cooling down/warming at (35,0 + 0,1)oWith and (36,0 + 0,1)oS, respectively. Additionally allocate 2,6-di-tert-butyl-phenol flows from impurities by distillation. The technical result - obtaining 2,6-di-tert-butyl-phenol with a purity of 99.99 - 100 wt.%. 1 C.p. f-crystals, 7 tab., 4 Il.

The invention relates to petrochemical synthesis shielded phenol antioxidants for rubbers, polymers, food products, in particular the production of 2,6-di-tert-butyl-phenol.

A method of obtaining 2,6-di-tert-butyl-phenol (2,6-di-TBP) by alkylation of phenol with isobutylene at 100-105oC and 15-18 ATA using as stereoregular catalyst aluminum. (Centuries Ershov. Spatial employed phenols. M, Chemistry, 1968, S. 37).

The alkylation is conducted, how great is TBP) - 9%, 2,4,6-tri-tert-butyl-phenol (2,4,6-tri-TBP) - 9% and 2,4-di-tert-butyl-phenol (2,4-di-TBP). The catalyst destroy water, separating 2,6-di-TBP distillation distillation.

The disadvantages of this method are the low yield of 2,6-di-TBP and lack of cleanliness of the product.

Known methods for producing 2,6-di-TBP high degree of purity of 99.98% - 100%) and yield up to 87 wt.%, including the alkylation of phenol isobutylester fraction using modified alkylation catalysts that increase the selectivity of the process. (RF patent 1679753, C 07 C 39/06, 37/14, Appl. 11.01.95, publ. 10.11.96, bull. N 31).

The catalyst inactivate water or propylene oxide and produce 2,6-di-TBP by distillation under vacuum of 20 mm RT.art., at 132oC. the Obtained 2,6-di-TBP does not contain impurities.

However, the implementation of the method in industrial production is problematic due to the complexity of the preparation of the used catalysts and scarcity of their components - products of interaction tetrafunctional acid with 2,2-dimethylamino in the first of these methods and tetraphenoxyaluminium aluminum in the second.

In the industrial production of 2,6-di-TBP as catalysts for alkylation ispolsu, CL 12 G 16, publ. 1965, A. C. the USSR 783297, C 07 C 39/06, 37/14).

When used as alkylating agent isobutylester faction or isobutylene and the selection of the target product by distillation receive 2,6-di-TBP with access to 78 wt.%, clean a 99.6 wt.%.

When implementing these methods on an industrial scale cannot achieve a higher purity of the product; the performance increase of columns, reflux ratio entails costs, not worth the slight increase in the quality of 2,6-di-TBP.

Closest to the claimed technical substance is used in the production method of obtaining 2,6-di-TBP, including the alkylation of phenol isobutylester fraction at 90-110oC and 6-10 ATA, using as a catalyst of aluminum, dissolved in phenol (0.1 to 0.2 wt.% Al), then stage decontamination aluminum water vapor with the Department of aluminium hydroxide from the alkylate and the allocation of the residual fraction C4, distillation selection (series) ortho-TBP, 2,6-di-TBP, 2,4-di-TBP and 2,4,6-tri-TBP. (The installation process procedure for the synthesis of 2,6-di-tert-butyl-phenol. JSC "Sterlitamak petrochemical plant", decl. 05.09.97 activating the catalyst agent water vapor - 4-4,5 mol of water per 1 mol of the catalyst.

The method is carried out according to the following scheme (Fig. 1).

In the alkylation reactor 1 above serves phenol and catalyst ratio (phenol:aluminum, wt.% - 1:(0,001-0,002), bottom serves technical isobutylester fraction containing 45-85 wt.% isobutylene, butadiene-1,3, butylene.

The alkylation proceeds under the above conditions for 8-10 hours at a molar ratio of isobutylene:phenol, 2,2:1,0.

From the top of the reactor alkylation deduce the fraction of C4containing 2-5 wt.% of isobutylene, from a bottom - alkylate containing up to 85% 2,6-di-TBP, and as impurities - ortho-TBP, 2,4-di-TBP 2,4,6-tri-TBP.

Alkylate is sent to the debutanization column 2. Countercurrent serves water vapor, from the top remove the residual fraction C4with bottom - alkylate and aluminium hydroxide is separated at the exit from the column. The product is then sent to the distillation column 3 to highlight ortho-TBP. From the bottom of column 3 output alkylate containing 2,6-di-TBP, 2,4-di-TBP 2,4,6-tri-TBP, phenol, which is sent to distillation column 4. From the top of column 4 in 102oC and 10-15 mm RT.article output of the target product is 2,6-di-TBP.

VAT description the monitor on isomerization in the production Department 2,4-di-TBP. CBM product - 2,4-three-TBP is used as a stabilizer oils.

The method allows to obtain 2,6-di-TBP with access to 84 wt.%, purity 98-99,6 wt.%, tomelting point- in 35.5 to 36.5oC.

The quality of the product meets the requirements of THE 38.103378-86 2,6-di-tert-butyl-phenol, designed to obtain 2,6-diretional of butylparaben and other phenolic stabilizers.

When you need to improve the quality of 2,6-di-TBP, for example, when the supply contracts, which usually stipulates a higher degree of purity required or additional cleaning with known methods (for example, recrystallization), or you may want to increase the performance of the distillation equipment, reflux ratio of columns, which is associated with high energy consumption and a rise in the cost of the product.

In get for additional purification of the product content of 2,6-di-TBP is 99,60-99,90 wt.%, tomelting pointit is not below 36,5oC crystals - white. (Appendix 1 to the other contract 1180/14/008-93 from 26.04.93 g).

However, some areas use of 2,6-di-TBP (pharmaceuticals, synthesis of some phenolic, STABILO 2,6-di-tert-butyl-phenol.

The purpose of the proposed invention is to improve the quality of 2,6-di-tert-butyl-phenol.

This goal is achieved by the fact that they use the method comprising the alkylation of phenol isobutylester fraction in the catalyst is aluminum, dissolved in phenol at 90-110oC and 6-10 ATA, dezaktivaciu of the catalyst separation fraction4the allocation of ortho-TBP, then 2,6-di-TBP, treatment allocated by the rectification of 2,6-di-TBP by cooling down/warming in a special apparatus with the conclusion in the liquid phase of high-purity 2,6-di-TBP, the allocation of the resulting flows of impurities additional quantity of 2,6-di-TBP and distillation separation of these threads 2,4-di-TBP and 2,4,6-tri-TBP.

Cooling down the selected rectification of 2,6-di-TBP carried out at (350,1)oC, heating at (360,1)oC.

To output high-purity 2,6-di-TBP product in the apparatus tahaliyani/heating heated to 50-55oC. After cooling, get a white crystalline 2,6-di-TBP with tomelting point= 39oC and basic substance content of 99.99-100 wt.%.

Threads impurities 2,4-di-TBP and 2,4,6-tri-TBP containing 14-20 wt.% from the amount of 2,6-di-TBP received on cooling down/heat is">

For the successful implementation of the method it is very important that procedures are consistent tahaliyani/heating ("sweating") were conducted in a strictly isothermal mode.

To reduce energy consumption, especially when a large impurity content of 2,4-di-TBP and 2,4,6-tri-TBP in the selected rectification of 2,6-di-TBP (1.0 to 1.4 wt. %) procedures tahaliyani/heating can be performed in two, three steps, increasing at each step the temperature tahaliyani (0,50,1)oC, and the temperature of the heating on (0,7)0,1)oC, bringing the final stage at the above temperature (350,1)oC and (36,00,1)oC, respectively.

The essence of the proposed method is based on the discovery of the existence of a low-melting eutectic with a pronounced extremum 2,6-di-tert-butylphenol with APS-impurities.

So, if 2,6-di-TBP melts at 39oC, and 2,4-di-TBP melts at 55oC, the authors found that a mixture containing 65 wt.% 2,6-di-TBP and 35 wt.% 2,4-di-TBP melts at 14.5oC (extreme) (Fig. 2).

The presence of pronounced eutectic authors can be explained by the tendency partially shielded phenols to the formation of clathrate structures.

Ability 2,dividing the last of 2,6-di-tert-butylphenol "cooling down"/"vpotevanie" (by heating).

Temperature regimes procedures tahaliyani/heating the purified 2,6-di-TBP for the quantitative separation from him to 11.4% (total) 2,4-di-TBP and 2,4,6-tri-TBP and were determined based on the detected eutectic curve when using artificially prepared mixtures of these ALKYLPHENOLS in different proportions.

The method is as follows. (Fig. 3, Fig. 4)

In terms of the way the prototype conducting the alkylation reactor 1, debutanizer alkylate in the destruction of the alkylation catalyst in the debutanization column 2, the allocation of ortho-TBP in a distillation column 3, the allocation of 2,6-di-TBP from the top of distillation column 4, treatment of selected 2,6-di-TBP by cooling down/warming in a vertical apparatus 5 in one-three stages at (35,00,1)oC and (36,00,1)oC, respectively, at the final stage of purification for 30 min at stage I and 30-40 min - II. Purified 2,6-di-TBP stage after "sweating" (heat) is heated to 50-55oC and in the liquid phase output as the target product.

The basic substance content in the product - 99,99 -100 wt.%, tomelting point= 39,0oC. Upon cooling, crystals are formed white.

With Lonny rectification 6 (Fig. 3) or recycling in a distillation column 4 (Fig. 4).

Total flows of impurities distillation products of columns 4 and 6 are sent to a rectification column 7 (Fig. 3) or column 6 (Fig. 4), where they produce 2,4-di-TBP and 2,4,6-tri-TBP.

In case of separation of 2,6-di-TBP flows from impurities in parallel to the rectification column 6 receive a product containing up to 98.5-99 wt.% 2,6-di-TBP and meet the requirements of THE 38.103378-86 2,6-di-TBP synthesis. If the flow direction of impurities recycle in the same distillation column highlight 4 extra amount together with the basic with the top of the column arrives at a clearing in the apparatus 5. Thus, a combination of distillation and purification by cooling down/warming method allows to obtain high-purity 2,6-di-TBP with minimal losses of the target product. Below are examples of the practical implementation of the methods of obtaining 2,6-di-TBP.

Example 1 (the prototype)

In the upper part of the alkylation reactor 1 (Fig. 1) serves 1025 g of phenol, containing 1.0% of dissolved aluminum, with a speed of 1 mol/h for 11 o'clock

Counter-current with a speed of 4 mol/h serves technical fraction C4containing, wt.%: isobutylene - 50, butadiene - 1, is eactor 1 deduce the fraction of C4containing 2.8% of isobutylene.

From a bottom - alkylate composition, wt.% phenol - 0,20; ortho-TBP - 8,90, 2,6-di-TBP - 86,95; 2,4-di-TBP - 1,75; 2,4,6-tri-TBP - of 2.21.

Alkylate is sent to the debutanization column 2 modes of operation: totop- 114oC, tocube- 116oC, a pressure of 2 ATA.

From the bottom of the column serves water vapor from the calculation of 4.5 mol of water per 1 mol of the catalyst.

From the top of the column output residual fraction C4water.

Product composition (excluding the content of phenol), wt.%: ortho-TBP - 8,90; 2,6-di-TBP - 87,15; 2,4-di-TBP - 1,75; 2,4,6-tri-TBP - 2,20, sent to the distillation column 3 with a capacity of 40 practical plates (so so ), with a reflux ratio (PL. h) - 5,0, totop- 96oC, tocube- 180oC, the pressure of the top of the column 10-15 mm RT.article.

From the top of the column output ortho-TBP, with the bottom product composition, wt.%: 2,6-di-TBP - 95,70; 2,4-di-TBP - 1,90; 2,4,6-tri-TBP - 2,40.

The product is sent to distillation column 4 performance 41 Ave so , with a reflux ratio of 2.3, totop- 102oC, tocube- 188oC, a pressure of 10-15 mm RT.article.

From the top of the column output 2,6-di-TBP composition, wt.%: 2,6-di-TBP - to 99.00;s in the distillation column 5 performance 56 Ave so (the lattice), with PL.h. 2,3, totop- 146oC, tocube- 205oC, a pressure of 20 mm RT.article.

From the top of column 5 output product containing 91,05 wt.% 2,4-di-TBP.

Product in an industrial environment are sent to isomerization in the production Department 2,4-di-TBP.

VAT residue column 5 contains 97,90 wt.% 2,4,6-tri-TBP and is used as a stabilizer oils.

Receive 2,6-di-TBP with access 83,90 wt.% in the calculation of the original with a basic substance content rate of 99.0 wt.%, tomelting point= 36,5oC. the Crystals are pale yellow color.

The product meets the performance requirements of THE 38.103378-86 2,6-di-tert-butyl-phenol, intended for use in the synthesis of phenolic stabilizers.

The content of the components of the product at each stage of its receipt are shown in table 1.

Example 2

In the conditions of example 1 carried out the alkylation of phenol isobutylester faction in the alkylation reactor 1 (Fig. 3), decontamination of alkylate in column 2, the allocation of ortho-TBP in a distillation column 3 and the allocation of 2,6-di-TBP in a distillation column 4.

Receive 2,6-di-TBP containing, wt.%: 2,6-di-TBP - 99,0; 2,4-di-TBP - 0,8 the cleaning of the cooling down/warming. The temperature of the cooling stage I - (34,50,1)oC, the temperature at the stage of heating at the I stage (35,30,1)oC.

The cooling temperature at the second stage (35,00,1)oC, heating - (36,00,1)oC.

The cooling time at each step of 30 min, heat - 30-40 minutes, until the termination of the allocation of the liquid phase.

Released during these procedures, the impurities mentioned in table 2, "2,4-fraction", is sent to distillation column 6, working in the mode column 4.

Purified 2,6-di-TBP named in table 2, "2,6-faction, heated to 50-55oC and in the liquid phase output as the target product. The product yield is 87,50 wt.% from admitted to treatment in the apparatus 5.

The basic substance content in the product is 100 wt.%, tomelting point= 39oC, upon cooling, forms white crystals, do not change it, even after prolonged storage.

The compositions of the streams of particles ("2,4-fraction") and the purified product (2,6-fraction") are shown in table 2.

Submitted to distillation column 6 threads 2,4-faction" share with the separation of 2,6-di-TBP with the top of the column and a mixture of 2,4-di-TBP 2,4,6-tri-TBP as the cubic product.

CBM product coke 5 of example 1.

Derived from the top of column 6 of 2,6-di-TBP has a composition, wt.%: 2,6-di-TBP - 98,90; 2,4-di-TBP - 0,40; 2,4,6-tri-TBP - 0,70.

Yield - 12,10 wt.% from admitted to treatment in the apparatus 5.

The product meets the performance requirements of THE 38.103378-86 and is used for the synthesis of alkyl phenols.

When the separation of the distillation product of columns 4 and 6 in column 7 receive the distillate containing 86,10 wt.% 2,4-di-TBP and CBM product containing 95,90 wt. % 2,4,6-tri-TBP. The total yield of 2,6-di-TBP was 83.6 wt.% (73,4% high-purity) in the calculation of the original phenol.

The composition of the product at all stages of receipt of 2,6-di-TBP are shown in table 3.

Example 3

In the conditions of example 1 are conducted alkylation, skipping isobutylester fraction through 1010 g of phenol dissolved 1.2 g of aluminum (Fig. 3).

Get the alkylate composition, wt.%: phenol - 0,15; ortho-TBP - 9,62; 2,6-di-TBP - 85,80; 2,4-di-TBP - 1,18; 2,4,6-tri-TBP - 3,25.

Alkylate enters the debutanization column 2 on the destruction of the catalyst under the conditions of example 1.

From the top of the column output residual fraction C4from the bottom product composition (without phenol), wt.%: ortho-TBP - 9,62; 2,6-di-TBP - 85,96; 2,4-di-TBP - 1,18; 2,4,6-tri-TBP - 3,24.

Prodprotect composition, wt.%: 2,6-di-TBP - 95,20; 2,4-di-TBP - 1,28; 2,4,6-tri-TBP - 3,52.

CBM product column 3 enters the distillation column 4, running the example 1. From the top of the column output 2,6-di-TBP containing, wt.%: 2,6-di-TBP - 98,60; 2,4-di-TBP - 0,58; 2,4,6-tri-TBP - 0,82.

From the bottom of the column 4 remove impurities coming into the distillation column 7.

2,6-di-TBP enters the apparatus tahaliyani/heating 5, where it is cleaned from impurities 2,4-di-TBP and 2,4,6-tri-TBP in three stages for 30 min under Sahelian and 30-40 minutes under heating at each stage of purification. On the first stage of cleaning, the temperature tahaliyani is (34,00,1)oC, the temperature of the heating (34,70,1)oC, stage II - (34,50,1)oC and (35,30,1)oC and stage III - (35,00,1)oC and (36,00,1)oC, respectively. The compositions of the streams of impurities and the purified product when cleaning the device 5 is shown in table 4. After heating to 50-55oC 2,6-di-TBP display in the liquid phase as the target product. Receive 2,6-di-TBP 100% purity with a yield 79,30% of those admitted to treatment in the apparatus 5.

The melting point of 2,6-di-TBP 39,0oC, upon cooling, forms white crystals.

Threads impurities, tx2">

From the top of the column 66 deduce 2,6-di-TBP composition, wt.%: 2,6-di-TBP - 98,80; 2,4-di-TBP - 0,45; 2,4,6-tri-TBP - 0,75.

The output from the bottom of the column 6 impurities together with kubovy the product column 4 is sent to distillation column 7, in which the mode of operation column 5 of example 1 divide them into 2,4-di-TBP and 2,4,6-tri-TBP.

The composition of the product at each stage of its receipt are given in table 5.

Example 4

In the conditions of example 1 are conducted alkylation, skipping isobutylester fraction of example 1 through 100 g of phenol dissolved 0.12 g of aluminum.

In the alkylation reactor 1 (Fig. 4) get the alkylate composition, 5 wt.%: phenol - 0,20; ortho-TBP - 8,90; 2,6-di-TBP - 86,40; 2,4-di-TBP - 1,80; 2,4,6-tri-TBP - 2,70.

Alkylate is sent to the debutanization column 2, from the top of which in the conditions of example 1 display the residual fraction C4from the bottom product composition, wt.%: ortho-TBP - 8,90; 2,6-di-TBP - 86,60; 2,4-di-TBP - 1,80; 2,4,6-tri-TBP - 2,70.

The product is sent to the column 3 to highlight ortho-TBP output from the top of the column. The process is carried out in the conditions of example 1.

CBM product column 3 composition, wt.%: 2,6-di-TBP - 95,05; 2,4-di-TBP - 2,00; 2,4,6-tri-TBP - 2,95; send in column 4.

From the top of the column 485,84 wt.% in the calculation of the original phenol) has tomelting point36,8oC.

2,6-di-TBP direct in the apparatus 5, in which in one step are cleaned from impurities "cooling down" at (35,00,1)oC for 30 min, then heated at (36,00,1)oC for 30 minutes

Upon termination of the allocation of impurity flow ("2,4-faction") in the apparatus in the solid phase 2,6-di-TBP heated to 50-55oC and output as the target product with a basic substance content of 99.99 wt.% and tomelting point39oC.

The output of high-purity 2,6-di-TBP is of 91.5 wt.% from admitted to treatment in the apparatus 5.

The compositions of the streams when cleaning the cooling down/warming are shown in table 6.

The flow of impurities from the apparatus 5 ("2,4-fraction") sent to the recycle column 4.

CBM product column 4 is sent to a rectification column 6, working in the mode column 5 of example 1.

The composition of the product at each stage of obtaining 2,6-di-TBP are shown in table 7.

The execute method of producing 2,6-di-TBP scheme providing for recycling the flow of impurities from the apparatus 5 in the distillation column selection 2,6-di-TBP 4 (Fig. 4) is technically easier than using additional rectifications it up to 10-20%. Both flow cleaning impurities exclude loss of 2,6-di-TBP at the stage of selection, allowing you to 79,0 wt.% product highlight in "ultra-pure" form, the rest of his return recycle, or give 2,6-di-TBP brand "synthesis" on THE other 38.103378-86.

When the content in the selected rectification of 2,6-di-TBP impurities in the amount of 1.50 wt. percent or more, the process of obtaining high-purity 2,6-di-TBP becomes multistage and energy-intensive. During purification is observed as would be the reverse process of "clogging" of the target product impurities. Perhaps the process requires practical improvements, but as long as option cleaning product with impurities in it more than 1.4 wt.% using the technique tahaliyani/heating is not realized.

Temperature Sahelian and heating (35,00,1)oC and (36,00,1)oC at the final stage and the corresponding temperature at the intermediate stages is determined based on the detected existence of the eutectic 2,6-di-TBP with "impurity" ALKYLPHENOLS and practical experiences with the use of the control mixtures.

When the deviation from the specified temperature conditions at each of the stages of tahaliyani/heating more than 0.1oC is not in the unit, then tahaliyani/heating is necessary and sufficient for full output in the liquid phase from the process schema.

The compositions of the products at each stage of obtaining 2,6-di-TBP determine chromatography according to THE 38.103378-86.

Used in the alkylation of phenol corresponds to GOST 23519-79, aluminum - GOST 11070-74, isobutylester fraction C4corresponds to THE 38.303-05-31-92 on butylene-isobutilene faction.

Sources of information

1. SU 1351562 A1, 15.11.1987.

2. Zhuravleva I. E. Technology for confectionery production. M: Food industry, 1968, S. 315 - 325.

1. The method of obtaining 2,6-di-tert-butyl-phenol, comprising the alkylation of phenol isobutylester fraction C4in the presence of a catalyst of aluminum, dissolved in phenol, the deactivation of the catalyst, separation of residual fraction C4, selects a clear distillation of impurities APS: ortho-tert-butyl-phenol, 2,4-di-tert-butyl-phenol, 2,4,6-tri-tert-butyl-phenol and the target product, wherein the selected clear rectification of 2,6-di-tert-butyl-phenol is subjected to successive cooling down/warming at (35,0 0,1)oWith and (36,0 0,1)oWith, respectively, emitting subsequent heating of high-purity 2,6-di-tert-butyl-phenol, and the streams leaving the impurities of the point-butyl-phenol by p. 1, characterized in that the cleaning of the cooling down/warming spend two, three steps, increasing at each step the temperature tahaliyani on (0,5 0,1)oC, and the temperature of the heating on (0,7 0,1)oC.

 

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EFFECT: obtaining prenylated phenols with high yield and content of ortho-prenylphenols.

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