Triptane production process

FIELD: petrochemical processes.

SUBSTANCE: hydrocarbon feedstock containing at least 1 vol % of at least one 5- or 6-membered cyclic hydrocarbon is subjected to preliminary processing, which consists in that feedstock is brought into contact with catalyst in presence of hydrogen under conditions favorable for selective opening of the cycle of cyclic hydrocarbon followed by isomerization stage wherein preliminarily processed feedstock comes into contact with isomerization catalyst to produce triptane-containing product stream.

EFFECT: increased selectivity of process.

34 cl

 

The present invention relates to an improved process for the preparation of triptan.

Triptan or 2,2,3-trimethylbutane is a hydrocarbon, which can be used in the preparation of unleaded motor and aviation gasoline (see WO 98/22556 and WO 99/49003). Due to its highly branched structure, it is particularly effective in increasing the octane number of the fuel determined by the motor method (OCM).

There are various methods of obtaining triptan. For example, triptan can be obtained by the reaction of the hydrocarbon starting material, such as gasoline, ligroin fraction, using an isomerization catalyst (US 3766286 and application GB 0024888.0, published as WO 02/31089).

The source of gasoline, ligroin fraction typically include acyclic paraffins and cyclic hydrocarbons such as naphthenes, and aromatics. Under reaction conditions acyclic paraffins in the original gasoline-ligroin faction easily isomerized in highly branched hydrocarbons, such as triptan.

It was found that cyclic compounds are more prone to side reactions, resulting in less chance of them becoming a target tryptanol product.

In accordance with this invention proposes a method of obtaining triptan, and this JV the property includes the following stages:

the preparation of the hydrocarbon starting material containing at least 1 vol.% at least one cyclic hydrocarbon containing ring C5and/or C6; pre-treatment of hydrocarbon source material by the introduction of the hydrocarbon starting material in contact with the catalyst in the presence of hydrogen under conditions acceptable to selective disclosure ring cyclic hydrocarbon;

isomerization pre-processed source material by the introduction of pre-processed source material into contact with an isomerization catalyst to obtain a stream CryptoStorage product.

Hydrocarbon source material may be a stream of hydrocarbons boiling in the range from 50 to 110°C. In the preferred embodiment, the hydrocarbon stream is characterized by a boiling within 60 to 105°S, more preferably from 75 to 100°C. the Hydrocarbon stream may be a stream of alkylates, or preferably the flow of the gasoline-ligroin faction. In a more preferred embodiment, the flow of gasoline, ligroin fraction represents the flow of gasoline, ligroin fraction comprising at least 30 wt.%, preferably at least 50 wt.%, for example from 60 to 90 wt.%, With7of hydrocarbons.

Hydrocarbon source material including the AET at least 1 vol.% at least one cyclic hydrocarbon, containing ring5and/or C6. In a preferred embodiment, the hydrocarbon source material includes from 2 to 60 vol.%, more preferably from 5 to 40 vol.%, and even more preferably from 10 to 30 vol.%, at least one cyclic hydrocarbon containing ring5and/or C6. Cyclic hydrocarbons which may be contained include naphthenes, and aromatic compounds.

Such compounds can be substituted, for example, alkyl substituents containing from 1 to 6 carbon atoms, preferably from 1 to 4 carbon atoms, more preferably containing 3 or less carbon atoms, and most preferably containing less than 3 carbon atoms.

In the presence of naphthenes they can be saturated or unsaturated. The preferred naphthenic contain from 6 to 20 carbon atoms, more preferably from 6 to 12 carbon atoms, for example from 6 to 8 carbon atoms. Specific examples include cyclopentane, Methylcyclopentane, dimethylcyclopentane (for example, 1,1-dimethylcyclopentane, 1,2-dimethylcyclopentane and 1,3-dimethylcyclopentane), ethylcyclopentane, cyclohexane, methylcyclohexane, dimethylcyclohexane, ethylcyclohexane and n-pentylcyclohexane.

In a preferred embodiment, the content of naphthenes in the hydrocarbon source material is the t 0 to 60 wt.%, more preferably from 25 to 50 wt.%, and most preferably from 30 to 40 wt.%. In the most preferred embodiment, the source of gasoline, ligroin fraction comprises from 10 to 35 wt.%, preferably from 15 to 25 wt.%, methylcyclohexane. The source of gasoline, ligroin fraction may also include cyclohexane (for example, from 1 to 5 wt.%), 1,1-dimethylcyclopentane (for example, from 1 to 5 wt.%) and/or 1,3-dimethylcyclopentane (for example, from 2 to 10 wt.%).

In the presence of aromatic compounds they may contain from b to 20 carbon atoms, preferably from 7 to 12 carbon atoms. Specific examples include benzene, toluene, xylene, ethylbenzene and n-butylbenzoyl. In a preferred embodiment, the content of aromatic compounds in the hydrocarbon source material is from 0 to 10 wt.%, more preferably from 1 to 5 wt.%. In the most preferred embodiment, the source of gasoline, ligroin fraction comprises from 0 to 5 wt.%, preferably from 0 to 2 wt.%, benzene and/or toluene.

In a preferred embodiment, the source material includes as naphthenes, and aromatic compounds.

The remaining part of the hydrocarbon starting material may be in the proportion of acyclic paraffins. Such waxes can be from 1 to 99 vol.% all of the hydrocarbon starting material. In a preferred embodiment, such parafi the s make up at least 30 vol.%, for example from 50 to 80 vol.%, more preferably from 60 to 80 vol.%, hydrocarbon source material. Acyclic paraffins can contain from 4 to 20 carbon atoms, preferably from 6 to 10 carbon atoms, and more preferably from 6 to 8 carbon atoms. Examples of acyclic alkanes that may be contained in the source material, include isopentane, 3-methylpentane, n-hexane, 2,2-dimethylpentane, 2,4-dimethylpentane, 3,3-dimethylpentane, 2,3-dimethylpentane, 2-methylhexan, 3-methylhexan, 3-ethylpentane, n-heptane, dimethylhexane and formed.

In a preferred embodiment, the hydrocarbon starting material is a stream of gasoline, ligroin fraction comprising as a main component With7hydrocarbons and a small amount of5-With6- and/or C8of hydrocarbons. Examples5hydrocarbons which may be contained include isopentane. Examples6hydrocarbons which may be contained include 3-methylpentane, n-hexane, cyclohexane and benzene. Examples7hydrocarbons which may be contained include 2,2-dimethylpentane, 2,4-dimethylpentane, 3,3-dimethylpentane, 1,1-dimethylcyclopentane, 1,3-dimethylcyclopentane, 2,3-dimethylpentane, 2-methylhexan, 3-methylhexan, 3-ethylpentane, n-heptane, methylcyclohexane and toluene. Examples8hydrocarbons which may be contained include dimethylhexane and formed. Hydrocarbon source material may include:

from 25 to 40 vol.% n-heptane;

from 10 to 28 vol.% With7hydrocarbons with one side group;

from 5 to 15 vol.% With7hydrocarbons with two side groups;

from 20 to 40 vol.% naphthenes and from

About up to 5% vol. aromatic compounds.

At the stage of preliminary processing of the hydrocarbon starting material in the presence of hydrogen is introduced into contact with the catalyst. In such reaction conditions selectively disclosed at least some amount of ring C5- and/or C6structures contained in the hydrocarbon source material, with the formation of linear or branched aliphatic structures. For example, in the preferred embodiment, the entire methylcyclohexane, part of the hydrocarbon starting material, is converted into 2,4-dimethylpentan.

The result of these reactions the disclosure of the ring is to reduce the number of ring structures in the hydrocarbon source material and simultaneously, in the preferred embodiment, eliminates visible dealkylation all lateral substituents on the ring. Thus, in preferred versions of the invention there is almost no fragmentation of cyclic compounds. In a preferred embodiment, the selectivity for the formation of the ring extending t is at least 10%, preferably at least 50%, for example from 80 to 99%.

In addition to the above reactions disclosure ring in the preferred embodiment, is the accession of a hydrogen atom at the unsaturated bonds. This process may also be accompanied by rearrangement reactions. For example, in the preferred embodiment, all of the benzene contained in the original material, in such reaction conditions are subjected to hydrogenation to obtain cyclohexane. Further, the ring opening of this circular connection with obtaining, for example, 2-methylpentane.

Acceptable catalysts disclosure rings contain both metal functional group and an acid group. The presence of metal functional group can be achieved using an effective amount of a metal of group VIII. Acceptable metals of group VIII include Fe, Ru, Os, Co, Rh, Ir, Ni, Pd, and mixtures thereof. Which one is preferable Rh, Ir and Ru. Especially preferred Ir. The amount of the metal used may be in the range from 0.01 to 10 wt.%, preferably from 0.02 to 5 wt.%, more preferably from 0.05 to 3 wt.%, and most preferably from 0.1 to 1 wt.%.

The presence of acid groups can be provided zeolite material. Such zeolite materials can be used as a substrate for the above-described metals. In predpochtite the flax version using zeolite material poetichnogo type, which is the ratio Si/M is at least 30 and in which M denotes at least one element selected from Al, Ga, In, Zn, Re and Cr. In a preferred embodiment, M represents Al, and the value of the ratio Si/Al in the zeolite material is at least 60. Examples of preferred zeolite materials described in US 4714601 (materials ECR-4), US 4879103 (materials ECR-30), US 4931267 (materials ECR-32), US 5116590 (materials ECR-35), US 3415736 (materials ZSM-C) and US 3972983 (materials ZSM-20). Can also be used analogues of such zeolites, such as materials EMS-1 EMS-2 (Delpratop et al., Zeolites, 10,. 546-552 (1990)). Other examples of suitable zeolite materials include mordenite, Y-zeolite, beta zeolite, MSM materials, clay, montmorillonite material ITQ-6. The material ITQ-6 is an oxide, which in its calcined form has an x-ray, which is characterized by a digital data presented in the table below. The material ITQ-6 has a specific surface area of micropores (as it is determined by the method of adsorption/desorption of N2at least 400 m2/g and the specific external surface area (defined by the method of adsorption/desorption of N2at least 350 m2/year / Material ITQ-6 described in the application PCT/GB 99/02567, which is incorporated into this description by reference.

Tabled (in angstroms)I/Io*1OO9,50+/-0,19f7,10+/-0,14f6,62+/-O.I3m5,68+/-0,11dof 3.97+/-0,08fto 3.73+/-0,07f3,53+/-0,07mf3,16+/-0,06m

Used in this table, the letters have the following meanings:

f indicates a strong, 40-60%relative intensity

mf means very strong, 60-100%relative intensity

m means medium, 20-40%relative intensity

d means weak, 0-20%relative intensity

In a preferred embodiment, the stage of pre-treatment is carried out at a temperature of from 150 to 400°S, more preferably from 225 to 350°C. Working gauge pressure may be from 0 to 208,6 bar (0 to 3000 psig), preferably from 6.9 to 151,7 bar (100 to 2200 psi), and more preferably from 6.9 to 103.4 bar (100 to 1500 psi). Hydrocarbon source material you can skip over the catalyst at an average hourly rate of liquid supply from 0.1 to 10, preferably from 0.5 to 5, SCSI (h-1). In preferred variants of the e flow of gaseous hydrogen during processing support level from 60 to 2000 m 3hydrogen on m3the hydrocarbon reactant, preferably from 100 to 600 m3hydrogen on m3the hydrocarbon reactant.

The reaction disclosure rings described in WO 97/09288, WO 97/09290 and US 5763731.

After pre-treatment of hydrocarbon source material is introduced into contact with an isomerization catalyst to obtain a stream CryptoStorage product.

In the preferred embodiment, as the isomerization catalyst used sverhchistoty. Acceptable superacids include Lewis acid of the formula MXnwhere M denotes the element selected from groups 13, 14, 15 and 16 of the Periodic table, X denotes a halogen atom, and n denotes an integer from 3 to 6. The preferred element M selected from groups 13 and 15 of the Periodic table. A more preferred value of M is Sb. X may denote F, Cl, Br or I, and in a preferred embodiment denotes F or Cl. In preferred versions of the invention, the element M is used in the state of its higher valency selected halogen atom. Thus, in the preferred embodiment, the Lewis acid is a SbF5.

In a preferred embodiment, the Lewis acid is used in combination with acid Branstad, for example with HX (where X denotes a halogen atom), ferternal acid, trifloromethyl the background acid and/or triperoxonane acid. Preferred examples of acceptable isomerization catalysts are HSO3F-SbF5and SbF5-HF. The molar ratio between the acid Bronsted and Lewis acid may be in the range from about 20:1 to 1:5. In a preferred embodiment, the molar ratio is from 5:1 to 1:1. The amount of catalyst based on the total amount of hydrocarbon may be in the range from about 0.01 to 100 miscast. catalyst on the mass of the hydrocarbons. Preferred the amount used is from 1 to 10 miscast. catalyst on the mass of the hydrocarbons.

The catalyst can be used in the form of undiluted liquid, in the form of a dilute solution or adsorbed on a solid substrate. As for the diluted catalyst, you can use any thinner, in a reaction inert conditions. For optimal results, the diluents can be pre-treated to remove catalyst poisons such as water, unsaturated compounds, etc. Typical diluents include sulfurylchloride, sulfurylchloride, fluorinated hydrocarbons and mixtures thereof. As diluents can be used by themselves proton acids, including persero acid, sulfuric acid, triftormetilfullerenov KIS the GTC, etc. About"lending ratio of diluent/catalyst may be in the range from about 50:1 to 1:1, and preferably from 10:1 to 2:1.

Alternatively the catalyst can be entered together with a suitable solid carrier or substrate. You can use any solid substrate for the catalyst, which in respect of the catalyst under reaction conditions is practically inert. The substrate can be pretreated, in particular by heating, chemical treatment or coating, to remove essentially all water and/or hydroxyl sites that you may have. Active substrates can be given the inertia of application of the coating of inert material, such as antimony TRIFLUORIDE and aluminum TRIFLUORIDE. Acceptable solid substrate include treated with fluoride or provided with a coating resin such as sulfonated cation exchange resin treated with fluoride sour helicity, such as aluminum oxide and silicates, and acid-resistant molecular sieves, such as zeolite, for example tasit. Deposited on the substrate catalysts can be prepared by any suitable method, such as conventional methods, including dry mixing, coprecipitation and impregnation. In one embodiment, deposited on a substrate, the catalyst is prepared by impregnation acceptable deactivated padlock the metal fluoride, such as pentatonic antimony, and then acid Bronsted, such as porsenna acid.

When they are deposited on the catalyst substrate, the mass ratio between the Lewis acid and the substrate may be in the range from 1:100 to 1:10, and preferably from 1:50 to 1:35. The mass ratio between the acid Bronsted and the substrate may be in the range from 1:100 to 1:10, and preferably from 1:50 to 1:35.

The isomerization reaction can be conducted at a temperature of from -50 to 100°C. In the preferred embodiment, the reaction temperature is from -30 to 25°S, more preferably from -25 to 10°C, preferably from -15 to 5°S, most preferably from -10 to 0°C.

The duration of contact may range from 0.01 to 150 hours, preferably from 0.05 to 50 hours, more preferably from 0.08 to 24 h, however, even more preferably from 0.1 to 15 hours, and most preferably from 4 to 6 o'clock

The preferred selectivity in respect of triptan is at least 7%, more preferably at least 9%. For example, the selectivity in respect of triptan may be in the range of 9 and 60% in terms of the initial hydrocarbon material.

Conditions of isomerization of hydrocarbon raw materials in General are described in the patent application GB 0024888.0 (published as WO 02/31089) and US 3766286.

1. The method receiving the Oia triptan, incorporating the following stages:

preparation of the hydrocarbon starting material containing at least 1 vol.% at least one cyclic hydrocarbon containing ring5and/or C6;

pre-treatment of hydrocarbon source material by the introduction of the hydrocarbon starting material in contact with the catalyst in the presence of hydrogen under conditions acceptable to selective disclosure ring cyclic hydrocarbon; and

isomerization pre-processed source material by the introduction of pre-processed source material into contact with an isomerization catalyst to obtain a stream CryptoStorage product.

2. The method according to claim 1, wherein the hydrocarbon source material is a stream of hydrocarbons boiling in the range from 50 to 110°C.

3. The method according to claim 2, in which the flow of hydrocarbons is a stream of alkylates, or the flow of naphtha fractions.

4. The method according to claim 3, in which the flow naphtha fraction comprises at least 30 wt.%, preferably at least 50 wt.%, for example from 60 to 90 wt.%, With7of hydrocarbons.

5. The method according to claim 1, wherein the hydrocarbon source material includes from 2 to 60 vol.%, more preferably from 5 to 40 vol.%, and even more preferably from 10 to 30 vol.% on ENISA least one cyclic hydrocarbon, containing ring C5and/or C6.

6. The method according to claim 1, in which at least one cyclic hydrocarbon selected from naphthenes and aromatic compounds, optionally substituted, for example, alkyl substituents containing from 1 to 6 carbon atoms, preferably from 1 to 4 carbon atoms, more preferably 3 or less carbon atoms, and most preferably less than 3 carbon atoms.

7. The method according to claim 6, in which the naphthenic independently include from 6 to 20 carbon atoms, more preferably from 6 to 12 carbon atoms, for example from 6 to 8 carbon atoms, and aromatic compounds include from 6 to 20 carbon atoms, preferably from 7 to 12 carbon atoms.

8. The method according to claim 7, in which at least one cyclic hydrocarbon selected from the group including cyclopentane, Methylcyclopentane, dimethylcyclopentane (for example, 1,1-dimethylcyclopentane, 1,2-dimethylcyclopentane and 1,3-dimethylcyclopentane), ethylcyclopentane, cyclohexane, methylcyclohexane, dimethylcyclohexane, ethylcyclohexane, n-pentylcyclohexane, benzene, toluene, xylene, ethylbenzene and n-butylbenzoyl.

9. The method according to claim 5, in which at least one cyclic hydrocarbon selected from naphthenes and aromatic compounds, optionally substituted, for example, alkyl substituents containing the mi from 1 to 6 carbon atoms, preferably from 1 to 4 carbon atoms, more preferably 3 or less carbon atoms, and most preferably less than 3 carbon atoms.

10. The method according to claim 9, in which the naphthenic independently include from 6 to 20 carbon atoms, more preferably from 6 to 12 carbon atoms, for example from 6 to 8 carbon atoms, and aromatic compounds include from 6 to 20 carbon atoms, preferably from 7 to 12 carbon atoms.

11. The method according to claim 10, in which at least one cyclic hydrocarbon selected from the group including cyclopentane, Methylcyclopentane, dimethylcyclopentane (for example, 1,1-dimethylcyclopentane, 1,2-dimethylcyclopentane and 1,3-dimethylcyclopentane), ethylcyclopentane, cyclohexane, methylcyclohexane, dimethylcyclohexane, ethylcyclohexane, n-pentylcyclohexane, benzene, toluene, xylene, ethylbenzene and n-butylbenzoyl.

12. The method according to claim 1, wherein the hydrocarbon source material includes:

from 25 to 40 vol.% n-heptane;

from 10 to 28 vol.% With7hydrocarbons with one side group;

from 5 to 15 vol.% With7hydrocarbons with two side groups;

from 20 to 40 vol.% naphthenes and

from 0 to 5% vol. aromatic compounds.

13. The method according to claim 1, in which the catalyst disclosure ring contains as metal group and an acid group.

14. The method according to claim 5, which which the catalyst disclosure ring contains as a metal band, and acid group.

15. The method according to claim 6, in which the catalyst disclosure ring contains as metal group and an acid group.

16. The method according to item 12, in which the catalyst disclosure ring contains as metal group and an acid group.

17. The method according to item 13, in which the presence of a metal of groups provide an effective amount of a metal of group VIII, preferably selected from a range that includes Fe, Ru, Os, Co, Rh, Ir, Ni, Pd, and mixtures thereof.

18. The method according to item 13, in which the presence of acid groups is provided a zeolite material.

19. The method according to 17, in which the presence of acid groups is provided a zeolite material.

20. The method according to clause 16, in which the presence of a metal of groups provide an effective amount of a metal of group VIII, preferably selected from a range that includes Fe, Ru, Os, Co, Rh, Ir, Ni, Pd and mixtures thereof, and the presence of acid groups is provided a zeolite material.

21. The method according to claim 1, wherein the isomerization catalyst is sverhchistoty.

22. The method according to item 13, in which the isomerization catalyst is sverhchistoty.

23. The method according to clause 16, in which the isomerization catalyst is sverhchistoty.

24. The method according to claim 19, in which the isomerization catalyst is sverhchistoty.

25. The method according to claim 20, in which the isomerization catalyst serve sverhchistoty.

26. The method according to item 21, in which sverhchistoty is a Lewis acid of the formula MXnwhere M denotes the element selected from groups 13, 14, 15 and 16 of the Periodic table, X denotes a halogen atom, and n denotes an integer from 3 to 6.

27. The method according to p, in which the Lewis acid is used in combination with acid Branstad.

28. The method according to item 27, in which the acid Bronsted represents HX (where X denotes a halogen atom), forcerenew acid, triftormetilfullerenov acid and/or triperoxonane acid.

29. The method according to paragraph 24, in which sverhchistoty is a Lewis acid of the formula MXnwhere M denotes the element selected from groups 13, 14, 15 and 16 of the Periodic table, X denotes a halogen atom, and n denotes an integer from 3 to 6.

30. The method according to clause 29, in which the Lewis acid is used in combination with acid Branstad.

31. The method according to item 30, in which the acid Bronsted represents HX (where X denotes a halogen atom), forcerenew acid, triftormetilfullerenov acid and/or triperoxonane acid.

32. The method according A.25, in which sverhchistoty is a Lewis acid of the formula MXnwhere M denotes the element selected from groups 13, 14, 15 and 16 of the Periodic table, X denotes a halogen atom, and n denotes an integer from 3 to 6.

33. The method according to p in which acid L the ISA used in combination with acid Branstad.

34. The method according to p, in which the acid Bronsted represents HX (where X denotes a halogen atom), forcerenew acid, triftormetilfullerenov acid and/or triperoxonane acid.



 

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