DE1518650C - Process for the production of alkyl aromatics - Google Patents

Description

high proportion of monoalkyl. Further omitted in the method of the invention that in the known method according to the United States patent 2,949,492 required laborious separation of the reaction product mixture obtained in the dimerization and costs for the dimerization catalyst, since for dimerization the one obtained during the alkylation Catalyst sludge is used.

More useful as examples of the method of the invention Olefins with 3 to 18 carbon atoms may be mentioned: propene, butene, pentene, hexene, heptene, Octene, nones, decene, undecene, dodecene, tridecene, tetradecene, pentadecene, hexadecene, heptadecene and Octadecs. The olefins can be straight-chain or branched. In addition, the starting material Contain olefins with more than 18 carbon atoms, but which do not dimerize. Particularly suitable are the olefins having 5 to 12 carbon atoms, both branched and straight-chain.

A preferred olefin feedstock for the process of the invention is one under the name catalytic polymer gasoline known mixture of predominantly branched olefins with generally 5 to 12 carbon atoms obtained by polymerizing propylene. It is made by passing propylene through a catalytic polymerisation plant. This procedure is in "Hydrocarbon Processing and Petroleum Refiner", Bl. 41 (September 1962), page 190, described. the Analysis of a typical sample of this material shows the following composition:

Number of carbon atoms

8th

7o

16

35

17th

11th

(The analytical method was vapor phase chromatography).

Another preferred olefin starting material are dodecene fractions from a catalytic polymerization unit, obtained by circulating a mixture of olefins through the unit for so long until a "peak" of 12 is reached, i.e. until the olefin with 12 carbon atoms is the largest individual Share in the mixture. A typical dodecene sample shows the following properties:

Because of its lower cost and accessibility, it is generally preferred polymer catalytic gasoline is used as a starting material. '

As to dimerizing olefinic expediently uses a Dodecenfraktiori or a catalytic 'polymer gasoline having an initial boiling point of between 30 and 26O ° C, preferably 57-182 ° C, a 50% distillation point 37-260 ⁰ C, preferably 138-196 ° C, and a final boiling temperature between 52 and 399 ° C, preferably between 218 and

274 ° c. ^; ■■■ · ■ · ■■ ■ '·' · ■ · ■. ■■ ·: ■ "

In general, pressure, temperature and residence time are not critical for the dimerization. For economic reasons it is preferable to work at atmospheric pressure, although somewhat increased or decreased pressures are also applicable. The suitable range for the reaction temperature is -10 to 75 ° C, preferably 20 to 55 ° C. A residence time greater than 5 minutes is satisfactory.

As already mentioned, the Invention used to dimerize as a catalyst the sludge involved in the alkylation of the aromatic hydrocarbon with the olefin dimers in the presence of a Friedel-Crafts catalyst accrues. A corresponding material can be used as the “starting sludge” for the dimerization by alkylation a suitable hydrocarbon, e.g. Benzene, with a suitable olefin, e.g. B. catalytic Polymer gasoline. When the procedure is underway, an appropriate amount will be paid of the sludge from the alkylation stage of the process is used in the dimerization stage. Suitable Amounts are 0.25 to 4.0 parts by weight, preferably 0.75 to 1.25 parts by weight per part by weight of olefin. In general, the use of smaller amounts results in a smaller degree of dimerization, while the use of larger amounts is uneconomical.

Temperature, pressure and dwell time are as before

mentioned, not critical. What has been said above applies to the latter two quantities. Suitable temperatures are between 15 to 75 ° C, preferably between 30 to 55 ° C. The reaction mixture is completely transferred to the alkylation stage.

A typical olefin dimer has the following boiling point analysis values on:

ASTM Distillation D-86.

Beginning of boiling .............. 173 ° C

178 ° C

.5%
10%
50%,
90%
95%
97%

179 ^C

".. 210 ° C

219 ° C

.. 224 ° C

Ending point .........:. 229 ° C

Recovery .......... 98% i

Specific weight at. 15.5 ⁰ C ................ 0.8146

Molecular weight .......:. 160 (cryoscopic

in benzene) aniline point .............. 51 ° C

^v c ν (ASTM D-611)

Refractive index (25 ° C) 1.4450

Beginning of boiling ......... 76 ° C

■■ ^; '· 5%.-..... ■ 87 ° C

10% 93 ° C -

20% 116 ° C; j:

30% .. 166 ° C

40% 199 ° C

50% 239 ° C

60% 273 ° C

. 70% ... 302 ⁰ C

95% ...... ..... decomposition

Final boiling point -

As aromatic hydrocarbons, < in general, all alkylatable substances of this group can be used. All are particularly suitable Xylene isomers, ethylbenzene, naphthalene and preferred

wise benzene and toluene. Mixtures of these aromatic hydrocarbons can also be used; all commercial degrees of purity can be used. Refined products are particularly suitable which contain substantial amounts of aromatic hydrocarbons, e.g. B. as a mixed component »ABC«, known in aviation, which mainly consists of toluene and small amounts of benzene and contains xylene isomers.

In the alkylation, the aromatic hydrocarbons are used in amounts from about 0.2 to 10 parts by weight, preferably from 1 to 3 parts by weight, are used per part by weight of dimeric olefin.

A Friedel-Crafts catalyst is used for the alkylation reaction used. If the alkylation sludge is used as a catalyst for the dimerization, thus the addition of "rejuvenation" catalyst is usually necessary for the alkylation reaction. All Friedel-Crafts catalysts are suitable for the process of the invention; is preferred Aluminum chloride as well as aluminum chloride produced in situ, i.e. the product of. reaction of aluminum metal with hydrogen chloride.

In some cases it is desirable to add a proton donor in addition to the Friedel-Crafts catalyst use. Suitable compounds are hydrogen chloride and water. The amount of proton donor added is (for water) 0.1 to 30 percent by weight, preferably 3 to 10 percent by weight of the aluminum chloride used. Used aluminum metal and hydrogen chloride as a catalyst is used, a range of 4 to 25 percent by weight applies to the addition of water.

Aluminum chloride as a catalyst is used in amounts of 0.02 to 0.25 parts by weight, preferably 0.08 up to 1.12 parts by weight per part by weight of olefin feedstock is used. For aluminum chloride formed in situ the same amounts apply. In this case, hydrogen chloride is in excess over the stoichiometric Amount used. ,

In the alkylation, pressure, residence time and temperature are not critical. The latter is usually in the range of 5 to 75 ° C, preferably 25 to 55 ⁰ C.

After the alkylation has ended, the reaction product is washed with a basic solution. In some cases it is desirable to also use an acidic solution and / or water to wash. These methods are known to the person skilled in the art.

The basic washed reaction product is then subjected to distillation. Not implemented Aromatics are distilled off, the intermediate products are removed. Thereby remain as soil fraction the desired alkyl aromatics back. The latter are those above 162.7 ° C / Torr, preferably above 204.4 ° C / torr boiling fractions. Usually done the fractionation of the product in the following way:

. ■.

fraction “5 benzene Temperature range
° c. pressure
(Torr) Beginning of boiling until 200 65 (or 200 Intermediate product Soil temperature) Group A
On Intermediate product Start of boiling up to 125 20th Group B 125 to 163 20th

In some cases it may be desirable to recycle the material identified above as Intermediate Fraction B back into the alkylation reaction.
The alkyl aromatics obtained according to the invention have excellent properties. They are an excellent starting material for sulfonation. They have a particularly high monoalkyl content. This is in contrast to the nature of the dodecylbenzene tail which consists primarily of dialkyl material. The alkyl radicals of the products prepared according to the invention are long (17 carbon atoms and more) and branched. In the following, “monoalkyl content” means those compounds which have a single long branched alkyl group on the aromatic nucleus; ie that a toluene alkylated by the process of the invention is referred to as monoalkyl toluene, although an alkyl group with a carbon atom is still present. The high monoalkyl content of the product prepared according to the invention appears to be responsible for the excellent qualities of the sulfonates which can be obtained therefrom. The properties are briefly summarized below:

suitable

characteristic
more suitable

preferred

° / q monoalkyl content *)

Average molecular weight

Boiling range, ° C / Torr

*) Calculated on mole percent of all aromatics.

above 50
above 320
above 163

above 70
above 350
above 190

above 90

375 to 478

above 204

The use of the product is generally given by the safety code. So serves that above material designated as preferred after sulfonation for the production of overbased detergents for lubricants, as well as the material boiling above 190 "C. However, those above are also 163 '' ("boiling alkyl aromatics for the production (after sulfonation) of rust inhibitors and limulgicnnitlcln suitable.

The method of the invention is explained below with reference to the figure. -

With the one in the drawing as a simplified block diagram reproduced embodiment of the invention is catalytic polymer gasoline via a Line 1 fed into a dimerization actuator 3, which is equipped with a stirrer 4. In addition, the Dimcrisicrungsreaktor 3 in. Circles led Aluminum chloride sludge from an alkylation

reactor 9 via lines 10 and 2 supplied. The reaction mixture leaving the dimerization reactor 3 is fed into the alkylation reactor via a line 5 9 fed, from a line 6 benzene, a line 7 fresh catalyst and from a Line 8 serving as a reaction promoter water is fed. From the alkylation reactor 9 is withdrawn crude reaction product mixture via line 10, which in aluminum chloride sludge, the it is returned to the dimerization reactor 3 via line 2, and crude alkylate is separated, which is fed via a line 11 into a scrubber 13, where it is supplied with a via a line 12 basic washing solution is treated. The used washing solution is via a line 14 drained. The alkylate is transferred via lines 14 and 15 to a second scrubber 16, where it is treated with washing water supplied via a line 17. The used washing water is via a line 18 removed. The washed raw ao Alkylate passes through line 18 and a line 19 ^ in a fractionating column 20, from which a Line 21 benzene, via line 22 an intermediate product fraction A boiling at up to 125 ° C./20 Torr and via a line 23 an intermediate product fraction B boiling at from 125 to 163 ° C. at 20 torr is pulled. The fraction containing the desired alkyl aromatics is at the bottom by a Line 24 withdrawn and transferred to a (not shown) storage container.

In the figure there is only one fractionation column for simplicity shown. In practice a number of fractionating columns are commonly used.

The examples illustrate the invention.

Catalytic , LhSII 1 Iv ι Co Polymer gasoline 40.7 API density 58.8 ASTM distillation according to D-86, ⁰ C 76 Start of boiling 51 87 5% 116 93 10% ■ 125 116 20% 132 .165 30% ■ '.: ·. 136 199 40% 139 238 50% - 144 273 60% 149 302 70% 157 323 80% 172 359 90% 194 cracked 95% 218 End of boiling 226

Book Ib:

Dimerization of a "broad fraction of dodecene" using aluminum chloride sludge
as a catalyst. .

Experiment Ia is repeated with the change that a catalytic polymer gasoline is used as the starting material, the constituents of which ^{boiling below 177 °} C. are separated off. The following table shows the boiling analysis characteristics of the product in comparison to those of the starting material:

35

B is ρ ie 1 1
Try Ia:

Dimerization of polymer catalytic gasoline using aluminum chloride sludge

"as a catalyst.

The reaction is carried out in a 3 liter flask equipped with a stirrer, a reflux condenser, a thermometer and a 1 liter dropping funnel, in which 566.6 g of catalytic polymer gasoline are placed, to which the same amount of AlCl ₃ catalyst sludge there. During the first 10 minutes of the addition, the reaction mixture is heated from 24 ° to 34 ° C. using a heating mantle. The temperature is maintained at 35 ° C. for the remainder of the addition. At this temperature, the reaction mixture is stirred for a further 1 hour after the addition of the catalyst sludge has ended. The contents of the flask are then transferred to a separatory funnel. The mixture separates into two phases overnight. (When the process is usually carried out, the entire reaction product is used for the alkylation. The separation is only carried out here in order to be able to determine the properties of the dimer.) 602.4 g of sludge and 298.9 g of dimeric product are obtained. The following table compares the boiling point analysis values of the starting olefin with those of the product. . _: -,. ·.

Source material Dimers
product ⁴⁰ API density 37.4 ASTM distillation - according to D-86, ⁰ C Start of boiling 179 78 5%: 183 86 ⁴⁵ 10% 185 '88 ■■ ..- 20% 187 117 30% . 188 , 187: '40%;.: .. .. • .. · ■ 189 . 205 . - 50%. 190 236 ⁵⁰ 60% ._. .:. . 192 295 70% ν. ■ - - 196 329 80% / 202 ' 350 90% 216 - ■■. '■ ··· ". · 95% ■. · ... 251 cracked ⁵⁵ End of boiling 262 Recovery,% 97.0

Try Ic:

This experiment explains the influence of temperature in the dimerization of catalytic

Polymer gasoline.

Experiment la is repeated with the change that the dimerization is carried out at 25, 30, 45 or 55 "C. will.

. . 309 6Π / 140

25 "C 30 ⁰ C 45 ° C 55 ° C API density 42.4 42.0 41.0 40.5 ASTM distillation according to D-86, ⁰ C Boil begin n 51 - - _ 57o ' 28 - 93 - 107ο 97 98 97 92 207ο '- 131 134 132 131 307ο 166 173 178 171 407ο 214 229 232 226 507ο ■■■ 252 265 270 268 607ο 283 293 311 300 707ο 312 322 330 330 807ο 348 354 351 351 907ο 377 379 - -

'Group No. Boiling range Weight ° C / 20 Torr G Batch; 1698.0 1 (benzene _rJ until 18 1214.Ό -.... ■ .. · ,, (at 200 Torr) 2 ' Tv · " to 51 115.4 3 51 to 96 184.5. 4- .. 96 to 111, 49.0 Soil fraction. over 111 117.7 loss (Trap etc.) - ■ ■ 67.4

Example 3

B is ρ ie 1 2
Alkylation of benzene with dimerized

using catalytic polymer gasoline
of aluminum metal and hydrochloric acid as fresh
- added catalyst.

The dimer prepared according to Example 1 (Experiment Ia) is used. The response is in carried out a 5 liter flask equipped with a stirrer, a reflux condenser, a thermometer and a 1 liter dropping funnel that can be heated and cooled.

A glass tube with a frit is used to introduce the hydrogen chloride into the reaction mixture. Excess HCl gas is scrubbed out of the vapors. The flask is filled with 1500 g of benzene, 509.4 g of spent AlC ^ catalyst sludge, such as it is described in experiment Ia, charged 5.05 g of aluminum metal and 2.5 g of water. This mixture are removed from the dropping funnel while stirring 477.4 g of dimer with simultaneous introduction of hydrogen chloride (1.007 ml per minute) added. After adding the first and second third of the dimer, 2.6 g of aluminum and 2.5 g of water were added. The temperature is kept at 40 ° C. After the addition of the dimer is complete (30 minutes) the reaction mixture is at the same temperature while increasing the HCl flow stirred for a further 1 hour to 2.014 ml per minute. The reaction mixture is then in a 4 liter separating funnel transferred, in which it is allowed to sit for 1 hour, whereupon 781 g of AlCl, catalyst sludge removed. The product is then washed with 250 ml of 257% sodium hydroxide solution. The used washing solution is separated off after 30 minutes. For the distillation 1702 g of product are obtained obtained, which has the following boiling analysis data:

Alkylation of toluene with dimerized
using catalytic polymer gasoline
an AlC ^ catalyst and recirculation

an intermediate fraction.

The alkylating agent used in Example I (experiment Fa) produced dimer is used. The reaction is in a heatable and coolable, with a ίο stirrer, a reflux condenser, a thermometer and a 1 liter dropping funnel equipped "5 liter flask, where the following raw materials are used:

1500 g toluene,
. 417.3 g of consumed AlCla dimerization ₍

mud,.

500 g intermediate product from a same
Test (boiling range 51 to 96 ° C /
20 Torr),
542.3 g dimer,

50, OgAlCl _3,.

2.0 g of water as a reaction promoter.

In the flask, the toluene, the AlCl ₃ -Dimerir sationsschlamm and 4as intermediate product are mixed with half of the AlCl ₃ (25.0 g) and the water (1.0 g) while stirring, whereupon the dimer from the Dropping funnel added dropwise. After adding the first and the second third of the dimer, 12.5 g of AlCl ₃ and 0.5 g of water are added. The reaction mixture is further stirred for half an hour at 4O ⁰ C. After sitting for 1 hour in a 4 liter separating funnel, 601.5 g of AlCl ₃ sludge are separated off. The remaining product is then washed with 250 ml of 257% sodium hydroxide solution. After sitting for one hour, 2379 g of product are obtained for the distillation. .

⁴⁰ parliamentary group no. Boiling range Weight ° C / 20 Torr G Batch 2368.1 1 up to 29 (200 Torr) 1357.1 45 2 to 51 83.9 51 to 96 - 696.3 ⁴ : '■. ' 96 to 111 59.2 Soil fraction above 111 .., ■ 159.2 , Loss (cases, etc.) ■ · .— ■ 12.4 /

The fractions are further characterized by the following analytical values:

. · Group 2 ' , 3 4th floor Bromine number. 0.30 0.16 0.32 0.41 Molecular weight 170 233. 311 418 Ratio of
aliphatic to the
aromatic
Protons 7.7 '·. 8.2 11.3 13.9 Estimated share
of the free aliphatics
by kernmagneti
cal resonance
analysis 34. - ..1
21 18th 8th

11 12

The sulfonation of the combined fractions 4 and 5 of the reaction mixture from the dimerization reactor into the

with 20% oleum gives 0.94 kg of alkylation reactor per kg of alkylate (R).

RSO ₃ H. In held at 38 to 4O ⁰ C Dimerisierreaktor

Example 4 per minute are jell g of catalytic polymer gasoline

~. _, ..,. , ,, », ,,,,, 5 and AlCU catalyst sludge / alkylation sludge)

This example shows the high monoalkyl content _ei ^. _The residence time is 30 minutes,

of the prepared by the process of the invention. The reaction mixture from the dimerization reactor

Alkyl aromatics. _{is transferred to the} alkylation reactor and at

Analogously to Example 1, Experiment Ia, 38 ^° C. are maintained from 500 g each. In addition, the following substances

catalytic polymer gasoline and AlC ^ -Catalyst- io fed into the alkylation reactor:

sludge 588 g of raw dimer and 388 g of catalysis benzene 33 a / min

satorschlarnm manufactured according to Example 1, Ver Aluminiununeialf '.'. '.'. '.'. '.'. '.'. '.'. '. 0.26 g / min.

seek Hb, but using benzene on water 0.05 g / min

Place of the toluene to be processed. Except ttq q \ "yxr- * \

the raw dining and the catalyst sludge 15 '

the dimerization are in the reaction *) This amount corresponds to S times the stoichiometric

iznn ~ tj ^ "™ i zn " λι / -ί ι " \\ r" a 1 Qi amount that would be necessary to completely immerse the aluminum

1500 g of benzene, 50 g of AlCl ₃ , 2 g of water and 183 g of _{Alcla to be} transferred.

one boiling between 125 and 218 ° C / 20 Torr

Intermediate fraction used. In the case of fractional by fractional distillation of the washed

Distillation of the washed crude alkylate gives 20 crude alkylate, a bottom fraction is obtained in

one 189 g of a boiling above 218 ° C / 20 Torr an amount of 4.02 g / minute, corresponding to one

Soil fraction. The monoalkyl content of the Bodenfrak yield of 36.5% of theory, based on one

tion is 94%; "their molecular weight 406th set catalytic polymer gasoline, the mono-

_. . alkyl content 95% and its molecular weight 375

^{Example 5 is} 25.

Example 4 is repeated, the first being to demonstrate the favorable ^ properties Process Step 534 grams of crude dimer and 439 grams of alkaryls obtainable by the process of the invention Receives catalyst sludge. The alkylation step transforms into dimerized catalytic polymer however, the amount of intermediate gasoline and dimerized dodecene used has more than one dimer fraction increased to 384 g. 196 g of over 30 alkylate bottom fractions are obtained, from which then 218 ° C / 20 Torr boiling bottom fraction with a sulfonic acid can be obtained, which one after Monoalkyl content of 90% and a molecular process of US Pat. No. 2,861,951 in excess weight transferred from 388. basic sulfonates. Lubricating oils with one

_. 1 _ή addition of such sulfonates show good engine test-

ΰ e 1 s ρ 1 el ö _{35 values> This is how} the majority of the tested mini

This example shows that the inventions method ran a 480 hour run at the Caterpillar

running continuously and the entire S-l test.

1 sheet of drawings

Claims (2)

fall in addition to the main product, dodecylbenzene, claims: further alkyl aromatic hydrocarbon fractions. The distillation of the crude alkylation 1. Process for the production of alkylaromatic reaction product. Bottom fraction is a by alkylating aromatic hydrocarbons 5 mainly composed of didodecylbenzene in the presence of Friedel-Crafts catalytic hydrogen mixture, which is often called dodecylbenzene . sators, optionally with the addition of pro-run. Dodecylbenzene tailings are clay donors as activators with which, although a very useful starting material in the polymerization of olefins with 3 to 18 carbons for the production of oil-soluble sulfonates, it does not provide material atoms in the presence of Friedel-Crafts ίο but is still not an ideal raw material basis for the Obtained per catalysts, mainly dimeric. The production of such sulfonates is because its production of the reaction mixture containing olefins, that is coupled with the production of dodecylbenzene, is characterized by the fact that it is the main product. Furthermore, a reaction mixture alkylating agent is used from US Pat. No. 2,949,492 a Verdet which is known by dimerizing the abovementioned 15 drives of the type described at the outset, in the case of olefins in the presence of an aromatic with olefins during the alkylation of the aromatic compound used for alkylating the aromatic compounds with a Friedel-Crafts any way and with any catalysts, catalyst obtained as a by-product catalyst including Friedel-Crafts catalysts, satorschlamms was obtained and polymerized olefins are used. However, this process, which is known from the subsequent alkylation stage ao, is laborious and expensive at least 50% monoalkylaromatics with driving is technically complex and branched to generate {■ $ alkyl otherwise hardly economically separated manner known per se significant amounts. . .35 usable by-products, i.e. ^ -waste products. 2. The method according to claim 1, characterized in that also provide for the olefin polymerization indicates, that one uses an alkylating agent required catalysts at a considerable cost, about 0.25 to factor in its manufacture. 4.0 parts by weight of catalyst sludge per weight The invention is therefore based on the object partly olefin were used. 3 ° a process for the production of alkyl aromatics to create the disadvantages of the known method 'overcomes, and in particular it enables the desired alkyl aromatics economically as the main The invention relates to a process for the production of product and to obtain the olefin polymers required as alkylating agents of alkylaromatics by alkylating aromatic 35 without costly separating hydrocarbons in the presence of Friedel methods, practically lossless with the lowest possible Crafts catalysts, optionally with the addition of catalyst costs ,
of proton donors as activators, with which it has now been found that this object of the polymerization of olefins having 3 to 18 carbons can surprisingly be achieved by a process of the initially described material atoms in the presence of Friedel-Crafts catalyst mainly dimeric olefins obtained as a result of the fact that the alkylating agent used is a reaction mixture containing reactants. In modern technology, there are many uses of the above-mentioned olefins in the presence of one of the possibilities for producing oil-soluble sulfonates. Large amounts of alkylation of aromatics with olefins are used, for example, as additives for lubricants 45 Friedel-Crafts catalyst as a by-product. For this purpose, the sulfonates falling catalyst sludge are obtained and as such or in the form of so-called overbased a reaction product obtained from the subsequent alkyl detergent is used One of the oldest methods of producing an oil fraction boiling over 162.7 ° C with a 20 Torr fraction Soluble sulfonates is the treatment of aromatic contents of at least 50% monoalkylaromatic compounds Petroleum fractions with sulfuric acid. The branched alkyl radicals obtained in this way are known per se Sulphonates are separated under the designation »Mahogany way. sulfonates «known. In general, these sulfo- "" "Dimerize" means in conjunction with the nate as a by-product in the manufacture of basic. Method of the invention that a substantial amount Lubricating oils and cylinder oils. Since 55 of the olefins used in the reaction are obtained in this way, they form dimers Sulphonates are by-products, their production is implemented. In addition, it occurs during depending on the amount of acid-treated base- the reaction to form other polymers. So lubricating oils. The development of improved processes can convert, for example, C ₅ -olefins to Ci ₅ - or Q-olefins to To produce base lubricating oils, the process has to be polymerized with _{C 18} or C _{20 olefins.}
The use of mahogany ^{sulphonates is much less expensive than} the known processes wrestles. Methods of the invention in particular, among other things More recently, a by-product "which has the advantage that the alkylaromatics produced is obtained in the production of dodecylbenzene, has become the main product of the reaction and is not a side effect of a particularly favorable source of product for production such as, for example, the dodecylbenzene tailings Sulfonates of suitable alkyl aromatics. Dode- ⁶ 5 second are those according to the process of the invention. Cylbenzene is known to be prepared by alkylating prepared alkyl aromatic hydrocarbons benzene with tetrameric propylene using an improved starting material for the preparation of a Friedel-Crafts catalyst is probably on that