The way isomerization of olefins

 

(57) Abstract:

Isomerization of olefins with external links contained in the hydrocarbon loading, olefins with external links with a greater degree of substitution is carried out in the presence of a catalyst based on palladium and hydrogen at 20 - 300oC, 1 to 50 bar, a volumetric hourly rate of 50 to 600 h-1and a molar ratio of H2: olefins = 0,01 - 1. When this catalyst before it is loaded into the isomerization reactor is treated with at least one sulfur-containing compound diluted with a solvent so that the catalyst contains 0.05 to 10 wt.% sulfur. Addition of organic sulfur-containing compounds, inhibits the hydrogenation and improves the isomerizing activity of the catalyst. 13 C. p. F.-ly, 1 table.

The present invention relates to a method of isomerization of olefins, more precisely isomerization of olefins with external bonds in olefins with internal links and / or isomerization of olefins with a low degree of substitution in the olefins with external links with a greater degree of substitution that is in a liquid hydrocarbon fractions WITH4WITH5and C6after vapor or catalytic pyrolysis or oligomerization, from which previously removed n the activity of the isomerization of olefins with external bonds in olefins with internal connections due to their use in alkylation or esterification.

In particular, the known isomerization of 4-methyl-1-pentene (olefin with external connections and a low degree of substitution) in 2-methyl-1-penten (olefin with external links and a higher degree of substitution) and 2-methyl-2-penten (olefin with internal links) and the isomerization of 4-methyl-2-pentene (olefin with internal links) 2-methyl-2-penten (olefin with internal links) and 2-methyl-1-penten.

Isomerization leading to catalysts on the basis of at least one metal of group VIII deposited on amorphous or crystalline substrate.

If the original load entering the isomerization does not contain or contains little diolefines, additional difficulties arise because in conditions close to the state of thermodynamic equilibrium, it is difficult to carry out the isomerization of olefins with external bonds in olefins with internal links, while limiting the hydrogenation of olefins to paraffins. The method of controlled selective hydrogenation of n-olefins? for example, by adding sulfur to the mixture described in U.S. patent N 4724274.

This patent describes, in particular, the method of obtaining 2-methyl-2-butene (olefin with internal links) from a fraction WITH5containing 2-methyl-1-butene (olefin with external links) and IU the sulfur (H2S thiol, thiophene), contained in a fraction in the amount of 2-50 ppm. Linear olefins selectively hydronauts and butene-1 isomerized in butene-2. In the absence of sulfur in the download is the hydrogenation of isopentanol, which reduces the yield of the final product.

The aim of the present invention is the suppression of hydrogenation reactions, in order to favor isomerization using appropriately treated catalyst.

More specifically, the present invention relates to a method of isomerization of olefins with external links contained in the download, olefins with external links with a greater degree of substitution and / or olefins with internal links, and the download contains practically no diolefin, in the presence of a catalyst based on palladium and in the presence of hydrogen at a temperature of 20-200oC, a pressure of 1-50 bar, volumetric hourly rate of 0.5-10 h-1, a molar ratio of H2: olefins = 0.01 to 1, the distinctive feature of which is that you load it into the isomerization reactor, the catalyst is treated with at least one sulfur compound, diluted with solvent, the treated catalyst containing 0.05-10 wt.% sulfur is loaded into the reactor isomers the me clock speed 50-600 h-1, and serves the load for contacting the activated catalyst. Unexpectedly it was found that the addition of organic compounds containing sulfur, can improve isomerizing activity of the catalyst.

As sulfur compounds can be used sulfides and, in particular, organic sulfides, degradable when activated catalyst in the reactor.

Activation of the catalyst are in a neutral or reducing environment at a temperature of 20-300 (preferably 60-210oC), a pressure of 1-50, preferably 3-20) bar, volumetric hourly speed 50-600 (preferably 100-200) h-1.

As organic sulfides in the present invention using alkylsulfate, arylsulfonyl, alkylarylsulfonate or arylalkylamine, for example, utilityscale, diallyl sulfide, dibutyltin, dipropylacetic, thiophene, dimethylthiophene, ethylthiophen.

You can also apply thiols (tosporte, mercaptans, thiophenol) of the formula R1SH, where R1organic radical, the thioethers of the formula R1SR2where R1and R2- same or different; organic disulfides of the formula R1SSR2and the disulfides of the formula HOR1SSR2OH,the organic timeslot, thioamides, thioesters, thiophenols. As an example named diamentina acid, thiocresol, 3,3-thiodipropionic acid, 2,3,6-trimethylsilanol, methylthiophenol, naphthalene-2-thiol, phenyl-ISO-thiocyanate, 2-phenylthiophene, thioacetamide, thiobenzamide, 2,6-dimethylthiophenol, 3,5-dimethylthiophenol, 2,21-dinitrodiphenylamine, 2,5-dithiodimorpholine, ethyldiglycol, 2-methoxythiophene, 3-methoxythiophene.

The method can also be carried out in the presence of other types of sulfur-containing additives. For example, you can apply mercaptopurine formula:

< / BR>
where m and n are integers;

R1, R2, R3and R4identical or different, denote hydrogen atoms or organic radicals, the alkyl, aryl, aralkyl and the other containing 1-20, preferably 1-6) atoms in the molecule; preferably n = 1-10 (examples 1-2) and m = 1-10 (example 1).

You can use monotypical, for example, monothioglycerol, dithioglycolic, for example, dithiodipropionic, dithiobenzoate, for example, detioration, heterocyclic compounds, substituted mercapto groups, for example, mercaptopyridine, mercaptopyrimidine and so on; dioxyalkylene, for example, thiodiethanol [S(CH2CH2OH)2] tailslide, cyclic thioethers and their substituted derivatives (tylenchid, thiophene, thiazole, thiopyran, thioxanthone, Dicastery, 1,4-dioxan and so on), heterocyclic S-containing alkylamine, substituted mercaptans (2-methylthio-4,6-diaminopirimidina and so on).

Among the above compounds, it is most preferable to use dimethyl sulfoxide, ethylthioethyl, thioglycolic acid, dithioglycolic and organic disulfides of the formula HOR1SSR2OH (as above) or formula ,

where R1and R2as stated above;

x, x' and x" are the same or different, denote integers.

As an example, diethanolamide or 2,2-dithio-bis(ethanol) (DEODS) formula HOC2H4SSC2H4OH, soluble in water, glycols and polyglycols.

You can also apply a polysulfide of the formula RSnR1,

where n is an integer of 3 to 20 (preferably 4-8, better 5-7); R and R1- same or different represent organic radicals, each containing 1-150 carbon atoms, preferably 5-40, better 7-16 C atoms, these radicals selected from saturated or unsaturated, linear or branched or naphthenic type Akilov, arrow, alkylaryl, S="ptx2">

The most preferred example of the polysulfide is dicret. todatetimeoffset (n= 5), where R and R1every radical tert.- didodecyl. This product is made by the company Elf Acetan under the trademark TPS 32 (sulfur content of 32 wt.%).

An example is dicret.dinonylphenol (n=5), where R and R1every radical tert.Neil.

Agent pretreatment using dilute adequate amount of solvent, the choice of which depends on the nature of the sulfonation agent.

The solvent may be selected from the following compounds, used separately or in a mixture: a light gasoline fraction, for example, so Kip. 60-95oC; hexane fraction with so Kip. 63-68oC; gasoline fraction F (the content of aromatic hydrocarbons 10-20%, preferably 15% by volume) so Kip. 100-160oC; white spirit (the content of aromatic hydrocarbons 14-22, preferably 17% by volume) so Kip. 150-250oC; any hydrocarbon or non-hydrocarbonaceous fraction, similar to the previous gasoline.

The sulfonation agent can be used in solvents such as alcohols (methanol, ethanol, propanol), aldehydes, ketones, ethers and esters, polyalcohol, acid as solvent.

After sulfur impregnation, the catalyst is subjected to heat treatment at a temperature of 100-200oC.

In accordance with the invention, in the catalyst, it is advisable to enter of 0.05-10 wt.% preferably 0.02 to 1 wt.% sulfur on the catalyst inventory.

The catalyst also contains 0.02 to 2 wt.% preferably, 0.05 to 1 wt.%, most preferably, 0.05 to 0.5 wt.% palladium.

Pre-sulfated activate the catalyst in the isomerization reactor before the introduction of the boot.

The isomerization reaction is carried out under a pressure of 1-50, preferably 5-30) bar, a temperature of 20-200, preferably 50-150)oC, at a volumetric hourly rate of 0.5-10 (preferably 1-6) h-1when the molar ratio of H2: olefins = 0.01 to 1, preferably of 0.02 to 0.2).

Sulfa sulfur compound may be added in the download.

The following examples illustrate the invention.

Example 1 (comparative)

100 cm3catalyst LD265 (catalyst A) firm Societe Procatalyse, containing 0.3 wt.% palladium on Al2O3placed in a steel tube with a diameter of 3 see This catalyst commonly used for selective hydrogenation of fractions, poluri 200oC hydrogen supplied for 5 h at 30 l/h, and then cooled in a stream of hydrogen and nitrogen purge.

Then measure isomerizing and hydrogenating activity of the catalyst with the hydrocarbon loading composition in wt.% specified in the table.

For this purpose, the load is passed in the form of a downward flow of hydrogen through the catalyst bed under conditions shown in the table.

Emerging from the reactor flows analyzed by chromatography in the vapor phase in PONA capillary column 50 m height.

The results of the study are presented in the column "Example 1" of the table.

One advantage of the invention consists in the possibility of carrying out the sulfonation on specialized units, designed only for this reaction, and the avoidance of contamination of the isomerization reactor (and other future devices) sulfur compounds. Another advantage is that the pre-sulfated catalyst can africasat with air when it is loaded into the reactor. This fact greatly facilitates the conditioning and transport of the catalyst.

Examples 2-6 (in accordance with the invention)

100 with oputyvayut dry aqueous solution of formic acid concentration of 2.2 mol/l, and deoxidised concentration of 0.15 mol/l and dried 6 hours at 120oC. the Treated catalyst (catalyst B) was placed in a steel tube with a diameter of 3 cm and subjected to activation by reduction with hydrogen at a temperature of 200oC, submitted for 5 h at 30 l/h with subsequent cooling of the catalyst in a stream of hydrogen by purging with nitrogen. Then measure isomerizing and hydrogenating activity of the catalyst with the hydrocarbon loading, the composition of which is specified in the table. To this end, skip this load in the form of a downward flow of hydrogen through the catalyst bed under the conditions listed in the table.

Emerging from the reactor flows analyzed by chromatography in the vapor phase in PONA capillary column 50 m height.

The results of the study are presented in columns "Examples 2-6 table of example 1. The table shows that according to the invention the quantity of olefins type 2-methyl-pentanol (most desired olefins) in examples 2-6, the most high, while the ratio of alkanes to misappropriation of olefins is reduced compared to the results of example 1.

1. The way isomerization of olefins with external links contained in the hydrocarbon loading, not containing virtually diolefines in olefins with external links with the pain of the hydrogen at a temperature of 20 200oC, a pressure of 1 to 50 bar, a volumetric hourly rate of 0.5 - 10 h-1and a molar ratio of H2: olefins = 0,01 - 1,0 characterized in that the catalyst before it is loaded into the isomerization reactor is treated with at least one sulfur-containing compound, diluted with solvent, and the treated catalyst containing 0.05 - 10 wt.% sulfur is loaded into the reactor and activated in a neutral or reducing environment at a temperature of 20 - 300oC, a pressure of 1 to 50 bar and a volumetric hourly rate of 50 to 600 h-1and the hydrocarbon loading in contact at isomerization conditions with an activated catalyst.

2. The method according to p. 1, wherein the load is a fraction of C5and C6obtained in a vapor-phase catalytic pyrolysis or by oligomerization and contains practically no diolefines.

3. The method according to p. 1, characterized in that the catalyst consists of palladium deposited on alumina.

4. The method according to PP.1 to 3, characterized in that the sulfur-containing compound selected from organic alkylsulfides, arylsulfatase, alkylarylsulfonate or organic arylalkylamines, thiols, thiadiazole, organic timeslot, thioamides, tio is storytell choose from gasoline and hydrocarbon fractions.

6. The method according to PP. 1 to 5, characterized in that the solvent used alcohols, aldehydes, ketones, ethers and esters, polyalcohol, acid, polyacid, glycols.

7. The method according to p. 1, characterized in that the solvent is water.

8. The method according to PP. 1 to 7, characterized in that the activation is carried out at a temperature of 60 - 210oC, a pressure of 3 to 20 bar and a volumetric hourly rate of 100 - 200 h-1.

9. The method according to PP.1 to 8, characterized in that the isomerization is carried out at a temperature of 50 to 150oC, a pressure of 5 to 30 bar, an hourly volume rate of 1 to 6 h-1and a molar ratio of H2: olefins = 0,02 - 0,2.

10. The method according to PP.1 to 9, characterized in that the sulfur compound injected in the download.

11. The method according to PP.1 to 10, characterized in that the catalyst contains 0.2 - 1 wt.% sulphur.

12. The method according to PP.1 - 11, characterized in that the catalyst contains 0.02 to 2.0 wt.% palladium.

13. The method according to PP.1 - 12, characterized in that the catalyst contains 0.05 to 1.0 wt.% palladium.

14. The method according to PP.1 - 13, characterized in that the catalyst contains 0.05 - 0.5 wt.% palladium.

 

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