CS202607B1 - Process for the alkylation of phenole and/or alkylphenole - Google Patents

Abstract

The invention relates to a method for the alkylation of phenol and / or alkylphenol 8 using unconventional Petrochemical alkylating agents with the compounds of the formula R10C (CH3) 3, wherein R * is alkyl of carbon atoms of 1 to 12, alkenyl of carbon atoms of 3 to 12 or cycloalkyl carbon atoms of 6 to 8, and / or aqueous a solution of 30 to 99.5% tert-butyl alcohol, and starting materials ea to the alkylation rates lead to eamoetatnb, or together, continuously, semi-continuously or continuously and obtained products are isolated and non-converted baseline euros, as well as formed lzobutene ea s advantageously recirculated.

Description

A method for alkylating phenol and / or alkylphenol

The invention provides a method of alkylating phenol and / or alkylphenol 8 using non-traditional petrochemical alkylating agents which are compounds of the formula R < ₁₀ &_gt; C (CH3) ₃ wherein R * is alkyl of 1-12, alkenyl of 3-3 12 or cycloalkyl having a carbon number of 6 to 8, and / or an aqueous solution containing 30 to 99.5% tert-butyl alcohol, and the starting materials ea are fed to the alkylation environment or together, continuously, semicontinuously or continuously, and the products obtained isolate and unconverted the initial euro coins as well as the formed lobutene e and are preferably recirculated.

202 607

202 607

The invention solves the apAeob alkylation of phenol and / or alkylphenol 8 using non-traditional petrochemical alkylating agents.

Well known phenol alkylating agents include alcohols, alkyl halides and olefins. Even the first work on the alkylation of phenol with alcohols was already done in the last century β using eiric acid £ Paterno E, Fileti M .: Gazz. Chim. Ital. £, 381 (1875) - and zinc chloride catalysts [Liebmann A .: Ber. 14, 1842 (1881); Ber. 15, 547 (1882); Senkowski M ,: Ber. 24, 2947 (1891); Fischer B., Griitzner B. Ber. 26, 1646 (1893). Their common drawback, however, is the low yield of alkylphenols and considerable catalyst consumption. Much better results have been obtained in the non-reaction of phenol with isobutanol on both cation exchangers and Balchl acid catalysts, but in particular with tert-butyl alcohol and alkenes of Bal PSa co: Chl. prom. 1962, no. 7, 480; Žur. Ex. chim. 37, 162 (1964); Khartchenko LS Zavgorodnyi SV: Zur. Ex. chim. 37, 165 (1964); Nametkin N, S. and epolupr. Neftechimija 14, 121 (19740), as well as alkenylation with allyl alcohol £ Niederl 3. B. and lni: 3. Am. Chem. Soc., 53, 3390 (1931); Shujkin NI and lni: Izv AN AN USSR otd. However, the disadvantage is the need for pure starting materials. In the case of using the available butadiene-depleted pyrolysis C ₄ -fraction to produce 4-tert-butylphenol using polyphosphate. The disadvantage is not a substantially lower alkylation rate than 8 pure isobatene than the need for regeneration or de-catalysting from the crude product. RL: Chem. Rev. 54, 615 (19540 eo by releasing ethers as alkylating agents, but probably because of the need for challenging reaction conditions such as temperatures above 400 ° C ^ Bamb 19, 1818 (18860), but also the observation that arylalkyl ethers switch to the alkylphanols of pTron. V., Ladigina LV: Ber. 62, 2844 (1929); Hennion GF et al.: 3. Aa. Chem., Soc. 55. 2857 (19330), essentially ropes in the study of the intermolecular acid-catalyzed isomerization of arylalkylate to alkyl- to trialkylphenols, Stroh R. et al., Chim prom. However, in the context of solving a simple process for the production of alkyl tert-butyl ethers as well as isolation of isobutane, in particular from the de-butadieneized pyrolysis fraction C C or from the products of catalytic cracking, via the intermediate formation of an aqueous solution of tert-butyl alcohol. (Cf. author's certificate 173 934), the raw material preconditions for the application of the novel phenol alkylation phenol solved by the present invention have also been created.

In the case of the alkylation of phenol and / or alkylphenol by at least 8 one alkyl having a number of carbon atoms of 1 to 4 in the liquid and / or gas phase, by treating the alkylating agent or mixture of alkylating agents in a molar ratio to phenol of 0.5 to 4: 1 strong mineral acids and / or aneoleic acids, preferably a cation exchanger in the H form and / or at least one phosphorus oxide on carriers, at a temperature of 30 to 250 ° C, preferably BO to 170 ° C, also in the presence of solvents and carrier gas by alkylation

202 007 is a reagent of a compound of formula R'OC (CH ₃ ) ₃ , wherein R * is alkyl of 1 to 12 carbon atoms, alkenyl of 3 to 12 carbon atoms or cycloalkyl of 6 to 8 carbon atoms and / or aqueous solution e containing 30 to 99.5% tert-butyl alcohol, preferably in the presence of isobutene, wherein the starting materials aa are introduced into the alkylation environment separately and / or together, continuously, semi-continuously or interrupted and the products collected are generally isolated, preferably by rectification under reduced pressure and / or crystallization and the unconverted starting materials as well as the isobutene formed and preferably recirculated.

An advantage of the apdeob of the present invention is the ability to potentiate the phenol or alkylphenol with one substance and two different alkyls, but, for example, in the case of isobutyl tert-butyl ether with one alkyl (tert-butyl), reep. one tert-butyl and alkenyl, such as in the case of application of allyl tert-butyl ester as alkylating agent; Another advantage is the possibility, in close connection with the isolation of isobutene from the hydrocarbon mixture by elective hydretation to form an aqueous solution of tert-butyl alcohol, which can be used directly for the alkylation of phenols without the need for dewatering or post-deposition. The advantage is also easy transport and storage of these non-traditional alkylating agents, as well as minimal energy consumption.

The alkylation according to the invention can be carried out in the liquid and / or gaseous phase, the vapor phase being also understood as a vapor phase. Steam and / or gas phase alkylation, in particular in the case of heterogeneous catalysts, has a clear advantage in the purity of the crude product, as in preventing waste water contamination and, last but not least, in the simplest catalyst regeneration. However, under the present technical measures, similar advantages can be achieved with liquid phase alkylation.

As catalysts ea, they mainly use substances of the protocyanic and protonic acids type. These include mainly aluminum chloride, boron trifluoride, phosphoric acid, p-toluane sulfonic acid and others. Newer and more suitable catalysts are aulfonated polymers and copolymers, such as copolymers of sulfonic phenol-formaldehyde and 8-styran-divinylbenzane resins, i.e., cation exchangers in the H form, phosphorus pentoxide itself and, in particular, naphthenic, polyphosphoric acid and polyphosphoric acid. tetraphosphoric acid, and the acid carrier may also be aneolytically acidic, as in the case of phosphorus oxides or polyphosphoric acid on aluminosilicate. optionally activated, such as me. bleaching clay. A suitable catalyst is also aluminum phenolate, especially if it is to alkylate the phenols at the 2 and 6 positions.

Alkylating agents! eu ethers of the formula R'OC (CH _{3) 3,} wherein R AU alkyl groups of carbon number 1 to 12, or alkenyl of a carbon number of 3-12, a cycloalkyl group having a carbon number of 6 to 8, wherein the ether can be relatively easily and on produced by the reaction of the respective alcohols ROH & isobutane, reep. and a mixture of alkanes, alkanes and even dianes containing isobutane, under the catalytic action of acids, e.g. sulfuric acid or cation exchange resin in H-form at temperatures of 80-90 ° C. Further, it is an aqueous solution of tert-butyl alcohol prepared by acid catalyzed addition of water to isobutane, especially e.g. by electrolytically hydrating lzobutane, e.g. in crude or de-butadiene-pyrolyzed C 1 -fraction, in gas-2 607 blades from catalytic cracking, or in isobutene-containing raw materials, under the catalytic effect of katsxes in the H-form, respectively. sulfonated plastic and thermosetting polymers and copolymers etc. Because there is usually no complete conversion! The isobutene formed under the conditions of alkylation of the phenols and optionally of ethers and tert-butyl alcohol can be recirculated and advantageously.

The alkylation feedstocks may be introduced separately and / or together, and inert solvents may also be used and, depending on availability, care should be taken to have a low boiling point,

In the case of continuous production, it is also advisable to use a carrier gas, which may be mainly inert gases (nitrogen, nitrogen and low oxygen content, carbon dioxide and the like at low pressure and lower temperatures).

Unconverted low boiling raw materials are first isolated from the crude alkylation aa ' alkylphenols and finally t-butylphenols, reap. alkyl tert-butylphenols, most often by differential distillation, rectification, distillation under reduced pressure, and crystallization, optionally by means of the well-known isolation methods.

Further details of the process according to the invention are apparent from the examples.

Example 1

To the top of a heavy-duty glass reactor containing 50 cm cation exchange resin in H-form (Oetion KS) based on sulfonated ethylene-divinylbenzene copolymer β with -SO3H functionalities with a total exchange capacity of 5.59 mmol equivalents / g converted into H-form by sodium exchange of cations and hydrochloric acid at a concentration of 5% by weight, is forged at -3.3 -1 -3 -1 at a dual flow rate of 37 cm • cm | _cat .h 0.231 9-cm _cat .h of phenol: tert-butyl alcohol in a molar ratio of 1: 1, wherein the t-butanol containing 2.7% by weight. water. The effect of temperature on the conversion and selectivity of tert-butylphenol formation is investigated. The crude product leaving the reactor was cooled, weighed and analyzed. The results are shown in Table i.

Table 1

Heat- the / ®C / conv ( Arzi Selectivity of tert-butyl alcohol conversions (in%) per; selectivity ZVJ conversion of phenol í / na: Λ X 4 3 3 * H X O 1 X by 0 kett ΦΗ in Q and «Η ABOUT C • M- C • Φ 44 3 X ABOUT N • H row * φ 4 » 9 X ABOUT N • H • H Ό I rh X 4 * and X 0 Urh W O w C 1 0 CM M- rh X 4 * and X 1 at u rH © 0 + »c 1 φ OH at 0 © c 4 # Φ 1 * · • Η rH Ό X 1 w co a • X CM 1 1 OH at 0 © c κ Φ 1 * • H iH Ό X 1 44 * 2 • X CM 1 -J- L Φ 4 »rH 1 0 • H C k Φ 4 * ΜΙ rH (0 X * 4 *) 12 * X CM 1 1 rh X 4 * and X I about U iH Φ O 4 * c 1 Φ CM rh X 44 and X 1 0 k «H Φ O V c 1 Φ and O rH k 0 Φ c 44 Φ 1 H • H rH Ό X 1 4 * 10 3 »X CM 1 1 O «H u 0 Φ c 44 φ 1 ΜΗ rH 'O X 1 4 » 15 CM 1 and at Φ 4 # iH 1 0 Ή C U Φ 4r ΜΙ <H (0 »» 44) 2 * X CM 1 81 91 100 110 120 135 89.2 96.6 98.8 99.2 99.4 99.6 47.5 57.4 57.3 61.3 68.1 73.2 47.6 41.6 36.0 33.2 33.1 33.9 0.6 0.5 0.7 0.7 0.6 0.4 23.1 22.3 22.7 18.9 14.6 2.9 16.6 16.6 20.4 26.4 33,2 46.5 0.7 0.8 0.5 0.4 0.2 0.0 10.6 16.6 17.5 18.9 17.6 16,0 0.8 1.6 2.2 1.6 0.6 0.3 44.6 38.6 35.6 28.4 20.6 4.4 32.0 28.7 31.9 39.7 47.0 70.7 1.4 1.4 0.8 0.6 0.3 0.0 20.6 28.8 27.5 28.6 31.7 24.4 1.6 2.8 3.9 2.4 0.9 0.5

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Example 2

The procedure is similar to that of Example 1, with the temperature difference being the same

120 + 1 ° C aa moni loaded the catalyser with an equialar dipped phenol-tert-butyl alcohol in -3 «1 range 0,10 to 1,35 9 · ° (ς _βί ^« Results are summarized in Table 2 «

Table 2

Catalyst load equimo- 14rnou zna- aou phenol tert-butyl alcohol M conversion · (%) Selectivity of praalene tert-butyl alcohol (%) nai Phenol (X) preaien selectivity to t I H <9 w and λ a 1 H U O ux Φ o V X 3 H ABOUT C • * · C w and X about N • rl row * in and about N • d • d •about 1 H X w 3 JB 1 ABOUT LH O O w C 1 o 01 * 1 rh > and X 1 IIH 28 42 1 íírH 28 1 · • d * Ό d 42 <4i 1 about kd • about w e i e D * - from 1 X t ' <M> 1 about to • WH 1 o • d c k · W «to • <0 X • w you 01 1 4 X w and ύ Urh 28 <42 4 X it and X 1 about UH 28 42 L 28 I · DK from 42 " • 3 NX 1 8. 28 42 from 1 X *with 0 l> 2,4,6-tri-t butylphenol 0.10 0.16 0.18 0.23 0.28 0.43 0.88 1.35 99.4 99.2 99.2 98.8 98.9 98.5 98.4 98.3 63.8 67.9 69.8 65.9 85.9 57.6 53.4 43.9 27.4 32.8 32.0 33.0 33.3 39.8 44.4 51.0 0.5 0.5 6.5 0.6 0.7 0.9 1.0 0.9 8.5 11.5 12.2 12.9 13.4 13.9 16.3 15.6 44.4 36.4 36.8 33.1 32.2 28.8 21.8 17.4 0.1 0.2 0.2 0.2 0.2 0.3 0.3 0Λ 18.5 18.5 18.8 19.6 19.5 17.2 14.9 13.3 0.4 0.4 0.4 0.6 0.7 1.1 1.6 1.4 11.9 17.2 18.1 19.4 20.6 23.9 30.0 32.5 61.1 54.2 52.9 49.0 48.8 45.2 39.8 36.0 0.2 0.3 0.3 0.3 0.3 0.5 0.5 0.9 25.8 27.7 28.0 29.4 29.8 29.2 27.5 27.0 1.3 0.7 0.5 0.9 1.0 1.8 2.7 3.0

of the cataiyzator

Example 3

The procedure is similar to that of Example i, except that for an etal heat of 120 ° C and the etonone load equivalents of phenol · tert-butyl alcohol -3 -1

0.231 9 '* c «| _(at , h there is no flow due to dueika as carrier gas. Fully eu results in Table 3.

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Table 3

flow nitrogen * -1 H 1 JC • w n « I β about • what about 1 d conversion (%) Selectivity of tert-butyl alcohol (%) on: Phenol selectivity (%) on the: tert-butyl alcohol phenol isobutane disodiobutane 2-tert-butyl phenol 4-tert-butyl phenol 2,6-di-t butylphenol 2,4-di-t butylphenol 2,4,6-tri-t butylphenol 2-tert-butyl phenol 4-tert-butyl phenol 1 υ U r-l Φ O 4- »C 1 Φ • H MUM 1> 10 «» • 3 N-Os 2,4-di-t butylphenol 2,4,6-tri-t butylphenol 55 37 19 10 0 98.2 98.8 99.0 99.1 99.6 49.7 65.9 70.4 67.0 66.1 43.0 33.0 32.5 31.7 32.3 0.7 0.6 0.8 1.2 1.4 10.7 12.9 11.9 15.6 16.9 25.8 33.1 34.1 29.7 28.7 0.2 0.2 0.3 0.3 0.4 18.9 19.6 19.9 20.3 19.0 0.7 0.6 0.7 1.2 1.3 17.5 19.3 17.8 23.1 25.5 50.3 49.5 51.2 43.9 43.1 0.3 0.3 0.4 0.4 0.6 30.9 29.4 29.9 30.2 28.7 1.2 0.9 1.1 1.8 1.9

Example 4

The procedure is similar to that of Example 1, except that at a standard temperature of 120 + 1 ° C and a catalyst loading of 0.231% ^{in the} feed mixture the moles are formed in the first experiment. ratio of phenol to tert-butyl alcohol 2: 1 and in the second experiment 1: 2. the phenol: tert-butyl alcohol ratio of -2: 1 the conversion of tert-butyl alcohol is

99.8% and phenol 37.9. The selectivity of tert-butyl alcohol conversions (in%) to isobutone is 59.6; diisobutanes 0.2; 2-tert-butylphenol 2.8; 4-tert-butylphenol 31.4; 2,6-di-tert-butylphenol 0.1; 2,4,6-tri-tert-butylphenol 0.2. Phenol selectivity (%) to 2-tert-butylphenol 7.1; 4-tert-butylphenol 78.4; 2,6-di-tert-butylphenol 0.1; 2,4-di-tert-butylphenol 14.5;

2.4.6- Tri-tert-butylphenol 0.5. At a molar ratio of phenol: tert-butyl alcohol> 1: 2, the conversion of tert-butyl alcohol is 98.6 and phenol 93.0. The selectivity of tert-butyl alcohol (%) is

55.8 ne isobutane; 0.95 not diisobutanes; 6.4 to 2-tert-butylphenol; 13.8% 4-tert-butylphenol; 0.4% 2,6-di-tert-butylphenol; 21.4 to 2,4-di-tert-butylphenol and 1.3 to 2,4,6-tri-tert-butylphenol. The phenol selectivity (in%) forms 13.2 over 2-tert-butylphenol; 39.0% 4-tert-butylphenol; 0.8 to 2,6-di-tert-butylphenol; 44.1% 2,4-di-tert-butylphenol and 2.7% na

2.4.6- tri-tert-butylphenol.

Example 5

The procedure is similar to that of Example 1. p-cresol is used instead of phenol in an equimolar mixture of 8 aqueous tert-butyl alcohol solution. At 120 ° C the catalyst loading is 0.131 9 cm ^CM * Conversion of p-cresol reaches 75.3% and tert-butyl alcohol

98.3%. The selectivity of tert-butyl alcohol to isobutane conversions (%) is 42.6; for diisob2O2 607 thenes 1.24 and tert-butylrazoles 86.2.

Example 6

The procedure is similar to that of Example 1 except that an equimolar mixture of phenol and methyl tert-butyl ether is added to the top of the reactor at a temperature of 128 ° C, with a phenol conversion of 74.6% and methyl tert-butyl ether. 99.4%. Phenol selectivity to 2-tarobutylphenol 2.6% t to 4-tert-butylphenol 72.0% t to 2,4-di-tert-butylphenol 25.2% t to 2,6-di-tert-butylphenol 0.2 % and 0.37% to 2,4,6-trl-tert-butylphenol. The selectivity of the methyl-tert-butyl ether (%) to the isobutenes is 0.3; tert-butyl alcohol 1,3; 2-tert-butylphenol 9.1; 4-tert-butylphenol 55.6%; 2,6-di-tert-butylphenol 0.1%; 2,4-dl-tert-butylphenol 19 * 5 a

2,4,6-trl-tert-butylphenol 0.3.

Example 7

Per head of reactor and containing 50 cm @ 2 of a phosphate catalyst having a grain size of 1.25-5 mm and a content of 22.61 wt. P and £ l 'le kyaloatl 298 mg KOH / g and on portions at 160 + 1 DEG equimolar zmee phenol much aqueous solution of tert-butyl alcohol, ipeclflkovaná in Example 1 in an amount of 0.230' b ^{'1 R} • ucman prletoku duelka 37 cm ³ , cmjj ³ t .h ^-1 ,

Conversion of tert-butyl alcohol reaches 99.9 and phenol 67.0% · The selectivity (in%) of the conversion of tert-butyl alcohol to lzobutene is 34.9; to the isobutenes 2.2; 2-tert-butylphenol 4.7; 4-tert-butylphenol 53.9 and 2,4-di-tert-butylphenol 4.7, Selectivity (in%) of phenol strands to

2-tert-butylphenol forms 7.3; to 4-tert-butylphenol 85.7 and 2,4-di-tert-butylphenol 7.4.

Example 8

Following the procedure and similar to Example 7, only the temperature of the reactor (catalyst) is 160 ° C and 200 ° C. The conversion of tert-butyl alcohol is 99.9 and phenol 38.6%. Source selectivity (%) of tert-butyl alcohol on isobutene is 87.3; to the isobutenes 2.5; 2-tert-butylphenol 3.8; 4-tert-butylphenol 34.6 and 2,4-di-tert-butylphenol 1.42. Selectivity (in%) of phenol over

2-tert-butylphenol reaches 9.4 and 4-tert-butylphenol 86.6.

Example 9

The catalyst described in Example 7 is dosed in a similar manner with aquimo • 3 L.

% phenol and methyl-tert-butyl ether in an amount of 0.123 .mu.m @ -1 cm @ -1 at a catalyst temperature of 137 ° C. The phenol conversion reached 42.4 and the methyl tert-butyl ether 98.8

The selectivity (in%) of phenol to 2-tert-butylphenol is 8.2; to 4-tert-butylphenol 75.9; on the

2,4-di-tert-butylphenol 14.4; to 2,6-di-tert-butylphenol 0.1 and to 2,4,6-trl-tert-butylphenol

2.9. Selectivity (%) to tert-butyl alcohol Ja 0.4; dibutobutenes 0.3; 2-t-butyl alcohol

202 607

3.7; 4-tert-butyl alcohol 45.6; 2,4-di-tert-butylfanol 8.6 and 2,4,6-tri-tert-butylfanol 0.6

Example 10

In a similar manner to Example 7, the catalyst is metered in foeforačnanový Pria duelka flow of 37 cm ³ .cm th ^ ^{3 "1} konStentnaj a temperature of 160 ± 1 ° C 0.25 g» cm ^ ³ t h ^-1, a phenol compound upon setting akvimolárnej - isobutyl-tert-butyl ether. The phenol conversion reached 97.6 and the isobutyl-tert-butyl ether 96.9%, and the phenol selectivity (in%) to 2-tert-butylfanol 3.9; 4-tert-butylphenol 68.9; 2,6-di-tert-butylfanol 0.1; 2,4-di-tert-butylphenol 30.3; The selectivity (in%) of the isobutyl tert-butyl ether conversions to isobutene is 44.1; for dlisobutenes 3.7; to 2-tert-butylphenol 2.0; to 4-tert-butylphenol 34.7; on the

2,6-di-tert-butylphenol 0.05; to 2,4-di-tar-butylphenol 15.2 and to 2,4,6-tri-tar-butylphenol 0.2.

Example 11

In a similar manner to Example 7 aa for the phosphate catalyst at a temperature η o of 1

120 + 1 C and a flow rate of 37 cm. Cm &lt; 3 _{&gt; t} &lt; -1 &gt;, adds an aquimolar mixture of phenol and an aqueous solution of tert-butyl alcohol with 8 different water contents. -butyl alcohol 70 to 90 wt.

-3 -1

At concentrations of 0.12 and 99.5% _at 0.10 g.cm ^ 'h. Achieved eu results in Table 4.

Table 4

Concentration tration tert butyl the alcoholic lu (% wt. conversion (%) Selectivity of tert-butyl alcohol (%) sat Phenol selectivity (in on: tert-butyl alcohol phenol isobutene dlizobutény 2-butyl-TARC phenol 1 3 Λ ABOUT LH Φ o W C 1 Φ 2,6-di-t-butylphenol 2,4-di-TARC-butylphenol 2,4,6-tri- tarc- butylphenol 2-TARC-butylphenol 4-TARC-butylphenol 2,4-di-tarc- butylphenol 2,4,6-tri-tarc- butylfanol 70 90 99.5 98.1 98.4 99.9 50.2 62.0 67.0 49.4 35.4 34.3 0.6 0.5 2.2 6.8 6.6 4.7 40.8 51.6 54.0 0.0 0.0 0.0 2.3 5.3 4.7 0.1 0.5 0.1 13.2 10.5 7.9 79.5 81.8 85.7 4.6 8.3 7.4 0.3 0.9 0.1

EXAMPLE 12 Stainless steel rotary autoclave of 1 dm aa weighs 5 g of cation exchangers in the H-form specified in Example 1 and 10 g of the phosphate catalyst specified in Example 7. Further aa add 94.1 g of phenol and 88 g of methyl tert-butyl ether . After blowing ·

The autoclave content of the autoclave was heated to 14 ° C ± 2 ° C and kept at this temperature for a period of 4 hours after cooling the autoclave to 20 ° C and evacuating gaseous fractions, starting from 15.4% by weight. isobutene and 84.6% haot, dimethylether. Then, 170 g of the liquid product are withdrawn from the autoclave. The conversion of phenol to 66.3% and methyl tert-butylate 96.4%. The selectivity of phenol to 2-tert-butylphenol is 38.6%; to 4-tert-butyl ether 31.0% t to 2,4-di-tert-butylphenol 27.9% and to 2,4,6-trl-tert-butyl ether

1.3% · The selectivity of matyl-tert-butyl ether to dilzobutane reaches 5.1% and 2-tert-butylphenol 26.8% t to 4-tert-butylphenol 21.5%; to 2,4-di-tert-butylphanol 19.3 and to 2,4,8-tri-tert-butylphenol 0.9%.

Claims (1)

Method of alkylating phenol and / or alkylphenol with at least one alkyl having a number of carbon atoms of 1 to 4 in the liquid and / or gaseous phase, by the action of an alkylating agent or a mixture of alkylating agents in molar ratio to phenol 0.5 to 4: 1; % of mineral acids and / or anaolvokyelin, and preferably a cation exchange resin in the H form and / or at least one phosphorus oxide per carrier at a temperature of 30 to 250 ° C, preferably 80 to 170 ° C, also in the presence of solvents and carrier gas, and wherein the alkylating agent is a compound of formula R * OC (CH ₃ ) ₃ wherein R 'is alkyl of 1 to 12 carbon atoms, alkanyl of 3 to 12 carbon atoms, weak cycloalkyl of 6 to 8 carbon atoms and / or an aqueous solution containing from 30 to 99.5% of tert-butyl alcohol, preferably in the presence of isobutene, wherein the feedstocks are introduced into the alkylalkyl environment separately, or epol, continuously The resulting products are isolated, preferably by rectification and / or crystallization and unconverted starting materials, as well as the isobutene formed and preferably recirculated.