Heavy alkylbenzene production through oligomerization (UOP)

CATEGORY: ALKYLBENZENE
Heavy alkylbenzene production through oligomerization (UOP)

Type	Patent
Inventor	Andrea G. Bozzano
Inventor	Jeffery C. Bricker
URL	Free Full Text Source:  http://www.google.com/patents/EP2828360A1
Assignee	Uop Llc
Patent Number	EP2828360 A1
Issue Date	Jan 28, 2015
Abstract	A process for producing heavy alkyl aromatics is presented. The process utilizes low molecular weight hydrocarbons for generating larger alkyl groups. The hydrocarbons can be generated from a variety of sources including Fischer-Tropsch liquids. The process includes oligomerization of low molecular weight olefins to larger olefins. The larger olefins are passed to an alkylation reactor to alkylate aromatic compounds.

Methods for producing linear alkylbenzenes, paraffins, and olefins from natural oils and kerosene (UOP)

PATENT
Methods for producing linear alkylbenzenes, paraffins, and olefins from natural oils and kerosene (UOP)
Publication number
US8502005 B1
Application number
US 13/427,718
Publication date
Aug 6, 2013
Inventors
Andrea G. Bozzano, Stephen Wayne Sohn
Original Assignee
Uop Llc
Abstract
A method for producing a linear paraffin product from natural oil and kerosene includes providing a first feed stream comprising kerosene, pre-fractionating the first feed stream to produce a heart cut paraffin stream comprising paraffins in a heart cut range, and combining the heart cut paraffin stream with a second feed stream comprising natural oil to form a combined stream. The method further includes deoxygenating the natural oil and fractionating the combined stream to remove paraffins that are heavier than the heart cut range.
FIELD OF THE INVENTION
The present invention relates generally to methods for producing renewable detergent compounds, and more particularly relates to methods for producing linear alkylbenzenes, paraffins, and olefins from natural oils and kerosene.
BACKGROUND OF THE INVENTION
While detergents made utilizing linear alkylbenzene-, paraffin-, and olefin-based surfactants are biodegradable, processes for creating linear alkylbenzenes, paraffins, and olefins are not based on renewable sources. Specifically, linear alkylbenzenes, paraffins, and olefins are traditionally produced from kerosene extracted from the earth. Due to the growing environmental concerns over fossil fuel extraction and economic concerns over exhausting fossil fuel deposits, there is a demand for incorporating alternate feed sources with the traditional kerosene feed source for producing biodegradable surfactants for use in detergents and in other industries.
Accordingly, it is desirable to provide methods for producing linear alkylbenzenes, paraffins, and olefins from a feed source that includes natural oils, i.e., oils that are not extracted from the earth, in addition to kerosene. Furthermore, other desirable features and characteristics of the present invention will become apparent from the subsequent detailed description of the invention and the appended claims, when taken in conjunction with the accompanying drawing and this background of the invention.
SUMMARY OF THE INVENTION
Methods for producing a linear alkylbenzene, paraffin, or olefin product from a natural oil and kerosene feed source are provided herein. In accordance with an exemplary embodiment, a method for producing a linear paraffin product from natural oil and kerosene includes providing a first feed stream comprising kerosene, pre-fractionating the first feed stream to produce a heart cut paraffin stream comprising paraffins in a heart cut range, and combining the heart cut paraffin stream with a second feed stream comprising natural oil to form a combined stream. The method further includes deoxygenating the natural oil and fractionating the combined stream to remove paraffins that are heavier than the heart cut range.
In another exemplary embodiment, a method for producing a linear olefin product from natural oil and kerosene includes providing a first feed stream comprising kerosene, pre-fractionating the first feed stream to produce a first heart cut paraffin stream comprising paraffins in a heart cut range, and combining the first heart cut paraffin stream with a second feed stream comprising natural oil to form a combined stream. The method further includes deoxygenating the natural oil, fractionating the combined stream and removing paraffins that are heavier than the heart cut range to form a second heart cut paraffin stream, and dehydrogenating the second heart cut paraffin stream to form a stream comprising olefins.
In accordance with yet another exemplary embodiment, a method for producing a linear alkylbenzene product from natural oil and kerosene includes providing a first feed stream comprising kerosene, pre-fractionating the first feed stream to produce a first heart cut paraffin stream comprising paraffins in a heart cut range, and combining the first heart cut paraffin stream with a second feed stream comprising natural oil to form a combined stream. The method further includes deoxygenating the natural oil, fractionating the combined stream and removing paraffins that are heavier than the heart cut range to form a second heart cut paraffin stream, dehydrogenating the second heart cut paraffin stream to form a stream comprising olefins, and alkylating the stream comprising olefins with a third feed stream comprising benzene to form a stream comprising alkylbenzenes.
Free Full Text Source: http://www.google.com/patents/US8502005

Method Of Producing Alkylbenzene And Catalyst Used Therefor

CATEGORY: ALKYLBENZENE
PATENT
Method Of Producing Alkylbenzene And Catalyst Used Therefor
United States Patent Application 20120000819
Inventors:
Matsushita, Koichi (Tokyo, JP)
Application Number:
13/259781
Publication Date:
01/05/2012
Assignee:
Jx Nippon Oil & Energy Corporation (Tokyo, Jp)
Japan Petroleum Energy Center (Tokyo, Jp)
Abstract:
A method that efficiently produces an alkylbenzene with a high added value from a 1.5-cyclic aromatic hydrocarbon while suppressing excessive hydrocracking and nuclear hydrogenation, and preventing a decrease in catalytic activity due to deposition of carbon during a hydrocracking reaction, and a catalyst used therefor, are disclosed. A method of producing an alkylbenzene includes causing a hydrocarbon oil feedstock containing an alkylbenzene content of less than 20 vol %, a bicyclic aromatic hydrocarbon content of less than 30 vol %, and a 1.5-cyclic aromatic hydrocarbon content of 25 vol % or more to come in contact with a hydrocracking catalyst that includes a solid acid having a maximum acid strength of Brönsted acid of 110 kJ/mol or more and less than 140 kJ/mol.
Description:

TECHNICAL FIELD

The invention relates to a method for efficiently producing an alkylbenzene with a high added value, and a catalyst used therefor, wherein the method allows a minimum naphthene ring-opening reaction to occur by causing an appropriate hydrocracking reaction without causing unnecessary nuclear hydrogenation.

BACKGROUND ART

In the petroleum refining field, an alkylbenzene such as benzene, toluene, and xylene (BTX) has been produced by a catalytic reforming process. A catalytic reforming reaction basically does not cause a change in the number of carbon atoms of the feedstock. Attempts have been made to convert heavy oil having a large number of carbon atoms into light oil (e.g., gasoline fraction). A solid acid has been known as a catalyst for a cracking reaction that reduces the number of carbon atoms of the feedstock.

For example, Patent Literatures 1 and 2 disclose a method of upgrading a light cycle oil (LCO) using a catalyst that contains molybdenum and β zeolite or a group VIII or VI metal in the periodic table and ultrastable Y zeolite as the solid acid. However, this method aims at producing gasoline, and does not selectively produce BTX and the like. When separating BTX and the like as a product, the amount of alkylbenzene produced by this method is insufficient.

Patent Literatures 3, 4, and 5 disclose a method of producing a lubricant base oil or a middle distillate using a solid acid having specific acidity containing ultrastable Y zeolite, an amorphous cracking component, and a group VIII or VI metal in the periodic table. However, a method that efficiently produces an alkylbenzene from a 1.5-cyclic aromatic hydrocarbon that has one benzene ring and one naphthene ring has not been disclosed.

Patent Literature 6 discloses a method of producing a high-octane gasoline blending component by hydrocracking a petroleum hydrocarbon having an aromatic hydrocarbon content of 40 mass % or more using a catalyst obtained by causing a group VIII metal and a group VI metal in the periodic table having hydrogenation activity to be supported on crystalline aluminosilicate zeolite containing particles having particle diameters of 0.5 μm or less in an amount of 80 vol % or more. However, this method aims at producing a gasoline blending component, and does not selectively produce an alkylbenzene. Moreover, since the crystalline aluminosilicate zeolite having an MFI structure represented by the so-called ZSM-5 has a maximum acid strength as high as 140 kJ/mol or more, the yield of gasoline is less than 70 vol %, and the reaction liquid yield is low due to a high cracking rate.

The inventor of the invention proposed a method that selectively produces a monocyclic aromatic hydrocarbon by hydrocracking a polycyclic aromatic hydrocarbon in the presence of a zeolite catalyst (Patent Literature 7), and a method that produces an alkylbenzene by hydrocracking a refilled oil obtained by refining a heavy hydrocarbon in the presence of a zeolite catalyst (Patent Literature 8). However, the method disclosed in Patent Literature 7 produces an alkylbenzene from an aromatic hydrocarbon having two or more rings (e.g., naphthalene rings). Since the hydrocracking catalyst used in Patent Literature 8 has a high maximum acid strength of Brönsted acid, only a small amount of alkylbenzene is produced. Therefore, an increase in the production amount of alkylbenzene has been desired.
Free Full Text Source: http://www.freepatentsonline.com/y2012/0000819.html

Method Of Producing Alkylbenzene And Catalyst Used Therefor

PATENT
Method Of Producing Alkylbenzene And Catalyst Used Therefor
United States Patent Application 20120000819
Inventors:
Matsushita, Koichi (Tokyo, JP)
Application Number: 13/259781
Publication Date: 01/05/2012
Assignee:
JX NIPPON OIL & ENERGY CORPORATION (Tokyo, JP)
JAPAN PETROLEUM ENERGY CENTER (Tokyo, JP)
Abstract:
A method that efficiently produces an alkylbenzene with a high added value from a 1.5-cyclic aromatic hydrocarbon while suppressing excessive hydrocracking and nuclear hydrogenation, and preventing a decrease in catalytic activity due to deposition of carbon during a hydrocracking reaction, and a catalyst used therefor, are disclosed. A method of producing an alkylbenzene includes causing a hydrocarbon oil feedstock containing an alkylbenzene content of less than 20 vol %, a bicyclic aromatic hydrocarbon content of less than 30 vol %, and a 1.5-cyclic aromatic hydrocarbon content of 25 vol % or more to come in contact with a hydrocracking catalyst that includes a solid acid having a maximum acid strength of Brönsted acid of 110 kJ/mol or more and less than 140 kJ/mol.
TECHNICAL FIELD
The invention relates to a method for efficiently producing an alkylbenzene with a high added value, and a catalyst used therefor, wherein the method allows a minimum naphthene ring-opening reaction to occur by causing an appropriate hydrocracking reaction without causing unnecessary nuclear hydrogenation.
BACKGROUND ART
In the petroleum refining field, an alkylbenzene such as benzene, toluene, and xylene (BTX) has been produced by a catalytic reforming process. A catalytic reforming reaction basically does not cause a change in the number of carbon atoms of the feedstock. Attempts have been made to convert heavy oil having a large number of carbon atoms into light oil (e.g., gasoline fraction). A solid acid has been known as a catalyst for a cracking reaction that reduces the number of carbon atoms of the feedstock.
For example, Patent Literatures 1 and 2 disclose a method of upgrading a light cycle oil (LCO) using a catalyst that contains molybdenum and β zeolite or a group VIII or VI metal in the periodic table and ultrastable Y zeolite as the solid acid. However, this method aims at producing gasoline, and does not selectively produce BTX and the like. When separating BTX and the like as a product, the amount of alkylbenzene produced by this method is insufficient.
Patent Literatures 3, 4, and 5 disclose a method of producing a lubricant base oil or a middle distillate using a solid acid having specific acidity containing ultrastable Y zeolite, an amorphous cracking component, and a group VIII or VI metal in the periodic table. However, a method that efficiently produces an alkylbenzene from a 1.5-cyclic aromatic hydrocarbon that has one benzene ring and one naphthene ring has not been disclosed.
Patent Literature 6 discloses a method of producing a high-octane gasoline blending component by hydrocracking a petroleum hydrocarbon having an aromatic hydrocarbon content of 40 mass % or more using a catalyst obtained by causing a group VIII metal and a group VI metal in the periodic table having hydrogenation activity to be supported on crystalline aluminosilicate zeolite containing particles having particle diameters of 0.5 μm or less in an amount of 80 vol % or more. However, this method aims at producing a gasoline blending component, and does not selectively produce an alkylbenzene. Moreover, since the crystalline aluminosilicate zeolite having an MFI structure represented by the so-called ZSM-5 has a maximum acid strength as high as 140 kJ/mol or more, the yield of gasoline is less than 70 vol %, and the reaction liquid yield is low due to a high cracking rate.
The inventor of the invention proposed a method that selectively produces a monocyclic aromatic hydrocarbon by hydrocracking a polycyclic aromatic hydrocarbon in the presence of a zeolite catalyst (Patent Literature 7), and a method that produces an alkylbenzene by hydrocracking a refilled oil obtained by refining a heavy hydrocarbon in the presence of a zeolite catalyst (Patent Literature 8). However, the method disclosed in Patent Literature 7 produces an alkylbenzene from an aromatic hydrocarbon having two or more rings (e.g., naphthalene rings). Since the hydrocracking catalyst used in Patent Literature 8 has a high maximum acid strength of Brönsted acid, only a small amount of alkylbenzene is produced
Free Full Text Source: http://www.freepatentsonline.com/y2012/0000819.html