Device for producing linear alkylbenzene

Abstract

The utility model relates to a device for producing straight-chain alkylbenzene, which comprises a deoxidation unit communicated with a triglyceride feeding pipeline; the C9-C14 pipeline and the C14 + pipeline are communicated with the deoxidation unit; a separate straight-chain selective cracking unit in communication with the C14 + line; a first line and a second line; the single linear-chain selective cracking unit is communicated with a single linear-chain selective cracking unit; the purification unit is communicated with the first pipeline; a first purification line communicating with the purification unit; the dehydrogenation unit is communicated with the first purification pipeline; a dehydrogenation line communicating with the dehydrogenation unit; a selective hydrogenation unit in communication with the dehydrogenation line; a monoolefine line in communication with the selective hydrogenation unit; an alkylation unit in communication with the monoolefine line; and an alkylation effluent line in communication with the alkylation unit. According to the utility model, alkylbenzene is produced from triglyceride, wherein some triglyceride can produce a large amount of n-paraffin with 16-24 carbon atoms after dehydrogenation.

Description

[0001] Priority Claim

[0002] This application claims priority to U.S. Provisional Patent Application Serial No. 63 / 504,879, filed May 30, 2023, and U.S. Patent Application Serial No. 18 / 500,161, filed Nov. 2, 2023, the entire contents of which are incorporated herein by reference. Technical Field

[0003] The present utility model relates to a method for producing alkylbenzene from triglycerides, particularly triglycerides that produce 60 wt% or more of normal alkanes having fewer than 16 carbon atoms after hydrogenation. Some of these triglycerides also produce a large amount (e.g., 20% to 30%) of normal alkanes having 16 to 24 carbon atoms after dehydrogenation. These alkanes are longer than the alkanes required for producing detergent products. Background Art

[0004] Linear alkylbenzene is an organic compound having the formula C 6 H 5 C n H 2n+1 . While the alkyl carbon number "n" can have any practical value, detergent manufacturers desire alkylbenzene to have an alkyl carbon number in the range of 9 to 16, and preferably in the range of 9 to 14. These specific ranges are typically required when alkylbenzene is used as an intermediate in the production of surfactants for detergents. An alkyl carbon number in the range of 9 to 14 meets the specifications of the detergent industry.

[0005] Since the surfactants produced from alkylbenzene are biodegradable, the production of alkylbenzene has grown rapidly since its initial use in detergent production in the 1960s. The straight-chainness of the alkane chain in alkylbenzene is crucial for the biodegradability of the material and its effectiveness as a detergent. The main factor in the final straight-chainness of alkylbenzene is the straight-chainness of the alkane component.

[0006] Although detergents prepared using alkylbenzene-based surfactants are biodegradable, the methods previously used to produce alkylbenzene are not based on renewable sources. Specifically, alkylbenzene is currently produced from kerosene refined from crude oil extracted from the earth. Due to the increasing environmental bias against fossil fuel extraction and the economic concerns about depleting fossil fuel deposits, there may be support for alternative sources of biodegradable surfactants in the detergent and other industries.

[0007] Accordingly, there is a desire to provide linear alkylbenzenes made from bio-renewable sources rather than extracted from the earth. Additionally, there is a desire to provide renewable linear alkylbenzenes from triglycerides and fatty acids that are easily processed from plants, animals, nuts, and / or seed oils. Palm kernel oil, coconut oil, and babassu oil have a relatively high composition within the desired range of C9-C14 normal alkanes, which is consistent with the alkyl carbon number range required by the detergent industry. Such renewable sources also have a large amount of nC16 to nC18 feed, and there is a desire to convert those feeds to nC9 to nC14 feeds with a high single-pass yield. These nC9 to nC14 intermediates can be used to ultimately prepare detergents of the linear alkylbenzene type through additional process steps. It is further desired that the resulting nC9 to nC14 alkanes be linear products with a minimum of branched isomer products. BRIEF DESCRIPTION OF THE DRAWINGS

[0008] Figure 1 is a schematic diagram of one embodiment of a method for producing alkylbenzenes from triglycerides according to the present invention.

[0009] Figure 2 is a graph of normal alkane mass % versus deoxygenation temperature according to Example 2. SUMMARY OF THE UTILITY MODEL

[0010] The present utility model includes the following technical solutions:

[0011] 1. An apparatus for the production of linear alkylbenzenes, the apparatus for the production of linear alkylbenzenes comprising:

[0012] A deoxygenation unit in communication with a triglyceride feed line;

[0013] A C9 to C14 line and a C14+ line, wherein the C9 to C14 line and the C14+ line are in communication with the deoxygenation unit;

[0014] A separate linear selectivity cracking unit in communication with the C14+ line;

[0015] A first line and a second line;

[0016] wherein the first line and the second line are in communication with the separate linear selectivity cracking unit;

[0017] A purification unit in communication with the first line;

[0018] A purified first line in communication with the purification unit;

[0019] A dehydrogenation unit in communication with the purified first line;

[0020] A dehydrogenation line in communication with the dehydrogenation unit;

[0021] A selective hydrogenation unit, which is connected to the dehydrogenation pipeline;

[0022] A monoolefin pipeline, which is connected to the selective hydrogenation unit;

[0023] An alkylation unit, which is connected to the monoolefin pipeline;

[0024] An alkylation effluent pipeline, which is connected to the alkylation unit.

[0025] 2. The apparatus for the production of linear alkylbenzene according to item 1, wherein the apparatus for the production of linear alkylbenzene further comprises:

[0026] A benzene separation unit, which is connected to the alkylation effluent pipeline, and a linear alkylbenzene product pipeline and a benzene recycle pipeline, which are connected to the benzene separation unit.

[0027] 3. The apparatus for the production of linear alkylbenzene according to item 1 or 2, wherein the benzene recycle pipeline is connected to the alkylation unit, and the benzene recycle pipeline recycles to the alkylation unit.

[0028] 4. The apparatus for the production of linear alkylbenzene according to item 1, wherein the C9 - C14 pipeline is connected to the purification unit.

[0029] 5. The apparatus for the production of linear alkylbenzene according to item 1, wherein the apparatus for the production of linear alkylbenzene further comprises:

[0030] An aromatic compound pipeline and a light fraction pipeline, wherein the aromatic compound pipeline and the light fraction pipeline are connected to the selective hydrogenation unit. Detailed Description

[0031] The present invention relates to a method for producing alkylbenzene from triglycerides, in particular triglycerides that produce 60 wt% or more of normal alkanes having less than 16 carbon atoms after hydrogenation. Some of these triglycerides also produce a large amount (e.g., 20% to 30%) of normal alkanes having 16 to 24 carbon atoms after dehydrogenation. These alkanes are longer than the alkanes required for producing detergent products.

[0032] In some embodiments, the amount of normal alkanes having 16 carbon atoms after dihydrogenation is less than 20%, or less than 15%, or less than 10%.

[0033] Triglycerides are derived from natural oils. Natural oils are not based on kerosene or other fossil fuels. Natural oils include those derived from plant or algal materials or animal fats, nut and / or seed oils, and oils containing triglycerides, and are commonly referred to as renewable oils. Natural oils typically contain triglycerides, free fatty acids, or combinations thereof. Natural oils include, but are not limited to, peanut oil (Arachis oil) (peanut oil; groundnut oil), babassu oil, coconut oil, cottonseed oil, grapeseed oil, maize oil (corn oil), mustard oil, palm kernel oil, palm oil, palm olein (the liquid fraction obtained by fractionation of palm oil), palm stearin (the high melting point fraction obtained by fractionation of palm oil), rapeseed oil, rapeseed oil - low erucic acid (low erucic acid turnip rape oil; low erucic acid colza oil; canola oil), safflower oil (safflower oil; carthamus oil; kurdee oil), high oleic acid safflower oil (high oleic acid safflower oil; high oleic acid carthamus oil; high oleic acid kurdee oil), sesame seed oil (sesame oil; gingelly oil; benne oil; ben oil; till oil; tillie oil), soya bean oil (soybean oil), sunflower seed oil (sunflower oil), and high oleic acid sunflower seed oil (high oleic acid sunflower oil).

[0034] In some embodiments, the triglycerides, upon deoxygenation, produce at least 15 wt% of n - alkanes having 12 or 14 carbon atoms. In some embodiments, the triglycerides, upon deoxygenation, produce at least 10 wt% of n - alkanes having 12 carbon atoms.

[0035] The method for preparing alkylbenzene from triglycerides according to the present invention comprises deoxygenating the triglycerides to form alkanes. The alkanes are separated (by fractionation, distillation, etc.) into a C9 - C14 stream containing C9 - C14 alkanes and a C14+ stream containing C14+ alkanes (i.e., having a carbon chain containing C15 - C28). The C14+ stream is sent to a separate linear - selective cracking unit to crack the C14+ alkanes; the cracked alkanes are fractionated into a first stream containing C9 - C14 normal alkanes and lightly - branched alkanes and a second stream containing isoalkanes. Contaminants, which include but are not limited to sulfur compounds, or nitrogen compounds, or phosphorus compounds, or oxygen - containing compounds, or aromatic compounds or combinations thereof, are removed from the C9 - C14 stream and the first stream. The purified stream is dehydrogenated to form olefins, dienes, and aromatic compounds. The dienes are selectively hydrogenated to form additional olefins, and the aromatic compounds are separated and removed, forming an aromatic - compound stream containing aromatic compounds and a mono - olefin stream containing mono - olefins. Benzene is alkylated with the olefins, and the alkylation effluent contains alkylbenzene and benzene. Then the alkylbenzene is separated.

[0036] The linear - selective cracking step will be further described. The linear - selective cracking is carried out in a separate unit rather than in the bottom bed of the first - stage hydrocracking reactor because sulfur and nitrogen contaminants from the first stage can poison the metal - based hydrocracking catalyst. The C14+ alkanes are selectively cracked prior to C9 - C14 due to their higher absorption energy.

[0037] Selecting specific metal catalysts, including noble metals (such as ruthenium and platinum) and nickel, can produce normal alkanes having 9 to 14 carbons in much higher yields than previous methods. Suitable catalysts include but are not limited to Ru / ZrO 2 、Pt - Al 2 O 3 、Ni - alumina or NiO x / clay. Using these catalysts, the C14+ stream can produce linear cracking products without significant amounts of branched - chain isomers being produced.

[0038] Among the preferred catalysts, the Ru catalyst exhibits much higher activity and single - pass nC9 - nC14 yields than other catalysts. Under optimized reaction conditions, it also produces very small amounts of methane and isomerization products. It has been found to be the best catalyst for such chemical conversion methods. The Pt - Al 2 O 3 catalyst can produce an even lower methane yield than the Ru - based catalyst, with a slightly lower linear - product yield.

[0039] To limit catalyst deactivation, the feed is treated prior to hydrodeoxygenation to remove sulfur, chlorides, and metal contaminants. Otherwise, sulfur, chlorides, and metals accumulate on the catalyst, and this results in deactivation. High-temperature hydrogenation treatment has been shown to restore some of the lost activity. The degree of hydrodeoxygenation can affect the selectivity to each n-alkane in the range of 9 to 14 carbons. A high degree of hydrodeoxygenation can cause the hydrodeoxygenation composition to be strongly biased towards n-dodecane and n-decane to the detriment of n-undecane and n-tridecane. A low degree of hydrodeoxygenation can cause the hydrodeoxygenation composition to be biased towards n-undecane and n-tridecane to the detriment of n-dodecane and n-decane.

[0040] The hydrodeoxygenation reactor temperature is kept low, less than 343 °C (650 °F) for typical biorecyclable feeds and less than 304 °C (580 °F) for feeds with a high free fatty acid (FFA) concentration, to avoid polymerization of the olefins present in the FFA. Typically, a hydrodeoxygenation reactor pressure of 700 kPa (100 psig) to 21 MPa (3000 psig) is suitable.

[0041] The overall process will now be described.

[0042] The linearity of the alkylbenzene product depends mainly on the linearity of the alkane used to alkylate benzene. A common rule of thumb for those skilled in the art is that after dehydrogenation and alkylation, the linearity of the alkane feed drops by 5 wt% - 7 wt%. Thus, an alkane with 97 wt% linearity (or alternatively 3 wt% isoalkane) will produce an alkylbenzene product with a linearity of about 90 wt% - 92 wt%. This sets a requirement for the linearity of the alkane that is 5 wt% - 7 wt% higher than the specification of the alkylbenzene product. Typically, the linearity of the alkane product is measured by the UOP 621, UOP 411, or UOP 732 standard test methods purchased from ASTM, which are hereby incorporated by reference in their entirety. Linear alkylbenzenes can be analyzed using ASTM standard test method D4337, which is hereby incorporated by reference in its entirety.

[0043] In the drawings, an exemplary system 100 for producing an alkylbenzene product from a specific triglyceride feed is illustrated.

[0044] In an exemplary embodiment, a selected triglyceride feed 105 is delivered to a deoxygenation unit 110, which also receives a hydrogen feed (not shown). In the deoxygenation unit 110, the fatty acids in the selected triglyceride feed 105 are deoxygenated and converted to n-alkanes. Triglycerides are structurally formed from three generally different fatty acid molecules that are bonded together by a glycerol bridge. The glycerol molecule contains three hydroxyl groups (HO--) and each fatty acid molecule has a carboxyl group (COOH). In a triglyceride, the hydroxyl groups of glycerol bond with the carboxyl groups of the fatty acids to form ester bonds. Thus, during deoxygenation, the fatty acids are released from the triglyceride structure and converted to n-alkanes. Glycerol is converted to propane, and the oxygen in the hydroxyl and carboxyl groups is converted to water, carbon dioxide, or carbon monoxide. The deoxygenation reactions of fatty acids and triglycerides are shown respectively as:

[0045]

[0046] During the deoxygenation reaction, the resulting alkane chain R n will vary in length by a value depending on the exact reaction pathway. It should be understood that deoxygenation includes at least one of hydrodeoxygenation, decarboxylation, and decarbonylation reactions or any combination thereof. For example, if carbon dioxide is formed, the chain will have one less carbon than the fatty acid source. If water is formed, the chain will match the length of the fatty acid source.

[0047] The operating conditions of the deoxygenation unit include a pressure in the range of 250 psig to 800 psig (1724 kPa to 5516 kPa) and a temperature in one embodiment of 274 °C to 371 °C (525 °F to 700 °F), in another embodiment of 274 °C to 338 °C (525 °F to 640 °F), and in another embodiment of 274 °C to 310 °C (525 °F to 590 °F). The catalyst can include those catalysts containing one or more of Ni, Mo, Co, P (such as Ni--Mo, Ni--Mo--P, Ni--Co--Mo, or Co--Mo) on alumina, silica, titania, zirconia, and mixtures thereof. Suitable hydrogen-to-hydrocarbon molar ratios include 1500 to 10,000, 4000 to 9000, and 5000 to 8000 standard cubic feet per barrel of feed (scf / B). Suitable space velocities include 0.2 hr -1 -3.0 hr -1 LHSV. The conditions are selected to minimize alkane cracking or isomerization.

[0048] The deoxygenation product containing normal paraffins, water, carbon dioxide, carbon monoxide, and propane is fractionated into a C9 to C14 stream 115 and a C14+ stream 120. The separation can be carried out in a multi-stage fractionation unit, a distillation system, or similar known equipment. In any case, the separator removes water, carbon dioxide, carbon monoxide, and propane from the deoxygenation product. It is also possible to form a naphtha stream (not shown) of paraffins having a carbon chain length of C 5 to C 9 .

[0049] The C14+ stream 120 is sent to a straight-chain selective cracking unit 125, where the stream is selectively cracked to form a first stream 130 containing C9 to C14 normal paraffins or lightly branched paraffins as described above and a second stream 135 containing isoparaffins.

[0050] The C9 to C14 stream 115 from the deoxygenation unit 110 and the first stream 130 from the straight-chain selective cracking unit 125 are sent to a purification unit 140. The purification unit 140 removes contaminants from the C9 to C14 paraffins in the C9 to C14 stream 115 and the first stream 130 in an adsorption system. The contaminants include but are not limited to sulfur compounds, nitrogen compounds, phosphorus compounds, oxygen-containing compounds, aromatic compounds, or combinations thereof.

[0051] The purified stream 145 is sent to a dehydrogenation unit 150, where hydrogen is removed to produce a dehydrogenated stream 155 containing monoolefins, diolefins, and aromatic compounds. In the dehydrogenation unit 150, the paraffins are dehydrogenated to monoolefins having the same number of carbon atoms as the paraffins. Generally, dehydrogenation is carried out by known catalytic methods, such as the commercially popular Pacol method. Diolefins (i.e., dienes) and aromatic compounds are also produced as undesirable results of the dehydrogenation reaction, as shown by the following reaction equations:

[0052] Formation of monoolefins: C x H 2x+2 →C x H 2x +H 2

[0053] Formation of diolefins: C x H 2x →C x H 2x-2 +H 2

[0054] Formation of aromatic compounds: C x H 2x-2 →C x H 2x-6 +2H 2

[0055] The operating conditions of the dehydrogenation unit 150 include a space velocity of 5 LHSV to 50 LHSV and 20 LHSV to 32 LHSV; a pressure of 1 kPa(g) to 1013 kPa(g) (0.1 psig to 150 psig): a temperature of 400 °C to 500 °C and 440 °C to 490 °C, and a hydrogen-to-hydrocarbon molar ratio of 1 to 12 and 3 to 7. Examples of suitable catalysts are Pt / alumina catalysts in which the platinum is attenuated with an attenuating metal. Another suitable catalyst is described in U.S. Patent 6,177,381, which is hereby incorporated by reference in its entirety. The dehydrogenation unit 150 may be operated dry or with up to 2000 mass ppm of water injected. Hydrogen may be recycled upstream of the deoxygenation unit.

[0056] The dehydrogenated feed stream 155 is sent to a selective hydrogenation unit 160, such as a DeFine reactor, where at least a portion of the dienes are hydrogenated to form additional monoolefins. As a result, the monoolefin stream 170 has an increased monoolefin concentration compared to the dehydrogenated feed stream 155. The aromatic compounds are separated and removed in the form of an aromatic stream 165. A light distillate stream 167 containing any light components (such as butane, propane, ethane, and methane) generated by cracking or other reactions during upstream processing may also be removed.

[0057] The monoolefin stream 170 containing monoolefins is sent to an alkylation unit 175 together with a benzene stream 180. The benzene is alkylated with the monoolefins to form alkylbenzenes. The alkylation unit 175 contains a catalyst that supports the alkylation of benzene with monoolefins, such as a solid acid catalyst. Fluorinated silica-alumina, hydrogen fluoride (HF), aluminum chloride (AlCl 3 ), zeolites, and ionic liquid catalysts are examples of the main catalysts commercially used for the alkylation of benzene with linear monoolefins and may be used in the alkylation unit 175. As a result of the alkylation, alkylbenzenes, commonly referred to as linear alkylbenzenes (LAB), are formed according to the following reaction:

[0058] C 6 H 6 +C x H 2x →C 6 H 5 C x H 2x+1

[0059] Suitable operating conditions for the alkylation unit 175 include a space velocity of 1 LHSV to 10 LHSV, a pressure that maintains liquid-phase operation such as 2068 kPa(g) to 4137 kPa(g) (300 psig to 600 psig), a temperature in the range of 80 °C to 180 °C and 120 °C to 170 °C, and a benzene-to-olefin molar ratio of 3 to 40 and 8 to 35.

[0060] An excess of benzene is supplied to the alkylation unit 175 to achieve the desired high degree of alkylation. Thus, the alkylation effluent 185 leaving the alkylation unit 175 contains alkylbenzene and unreacted benzene. In addition, the alkylation effluent 185 may also include some unreacted paraffins. The alkylation effluent 185 is passed to a benzene separation unit 190, such as a fractionation tower, to separate the unreacted benzene and paraffins from the alkylation effluent 185. The unreacted benzene leaves the benzene separation unit 190 in the form of a benzene recycle stream 195, which can be sent back to the alkylation unit 175 to maintain the desired benzene / olefin ratio (e.g., 1 - 50) to reduce the volume of fresh benzene required. The fresh benzene requirement (i.e., net benzene) is determined by the net olefins entering the alkylation unit. The paraffin stream 200 can also be separated out and recycled to the dehydrogenation unit 150.

[0061] As a result of the post - alkylation separation process, a linear alkylbenzene product 205 is separated out. It should be noted that such a separation method is not necessary in all embodiments for separating the linear alkylbenzene product 205.

[0062] The linear alkylbenzene product 205 is a linear alkylbenzene product comprising: alkylbenzenes having the formula C 6 H 5 C n H 2n+1 where n is from 9 to 14. In some embodiments, at least 80 mass%, or at least 90 mass% of the alkylbenzenes have linear alkyl groups.

[0063] The linear alkylbenzene can be sulfonated to provide a linear alkylbenzene sulfonate product, which comprises: alkylbenzene sulfonate compounds having the formula C n H 2n+ 1 C 6 H 4 SO 3 H, where n is from 10 to 14, or where n is from 11 to 13.

[0064] As used herein, the term "separator" means a vessel that has one inlet and at least one overhead vapor outlet and one bottoms liquid outlet, and may also have an aqueous stream outlet from a boot. A flash drum is a type of separator that can be in downstream communication with a separator that can operate at a higher pressure. The term "in communication" means that fluid flow is operably permitted between the recited components, which can be characterized as "in fluid communication". The term "downstream communication" means that at least a portion of the fluid flowing towards the body in the downstream communication can flow operably from an object in fluid communication therewith.

[0065] The term "column" means one or more distillation columns used to separate one or more components having different volatilities. Unless otherwise specified, each column includes a condenser at the top of the column for condensing a portion of the overhead stream and returning it as reflux to the top of the column, and a reboiler at the bottom of the column for vaporizing a portion of the bottoms stream and returning it to the bottom of the column. The feed to the column may be preheated. The top pressure is the pressure of the overhead vapor at the vapor outlet of the column. The bottom temperature is the liquid bottoms outlet temperature. Unless otherwise specified, the overhead line and the bottoms line refer to the net lines from downstream of the column where any reflux or reboiler takeoff occurs to the column. A stripper column may omit the reboiler at the bottom of the column and instead provide the heating requirements and separation driving force for a liquefied inert medium such as steam.

[0066] As used herein, the term "component-rich stream" or "component stream" means a stream exiting a vessel having a greater concentration of the component than the feed to the vessel. As used herein, the term "component-lean stream" means a lean stream exiting a vessel having a smaller concentration of the component than the feed to the vessel.

[0067] Embodiment

[0068] Embodiment 1

[0069] Coconut oil feed is deoxygenated to form paraffins, dehydrogenated to form monoolefins, and benzene is alkylated with the monoolefins to form an alkylbenzene product having a modern carbon content of 62 mass % modern carbon as determined by ASTM D6866 compared to a theoretical modern carbon content of 66.4 mass %, a bromine value of 1 g Br per gram of sample as determined by UOP Standard Test Method 304, and a straight-chain degree of 92 mass %.

[0070] Embodiment 2

[0071] The oil is deoxygenated using a catalyst at a pressure of 480 psig H, with a bio-oil ratio of 7200 scf / B and an LHSV of 1 hr⁻¹. During operation, the deoxygenation reaction temperature is gradually increased from 315 °C (600 °F) to 349 °C (660 °F), then to 377 °C (710 °F) and 404 °C (760 °F) to monitor the response of the straight-chain degree in the final product to the reaction temperature. The results are shown in Figure 2 which is a plot of the concentration (in mass %) of C10 - C13 normal paraffins versus the reaction temperature. Figure 2 Clearly shows that as the deoxygenation reaction temperature increases, the concentration of normal paraffins decreases. Controlling the temperature below 404 °C (760 °F) produces greater than 92 mass % normal paraffins.

[0072] Note: Example 1 and Example 2 were previously included as Example 3 and Example 4 in U.S. Patent 9,079,814.

[0073] Specific implementation plan

[0074] Although the following is described in conjunction with specific embodiments, it should be understood that the description is intended to illustrate and not limit the scope of the foregoing description and the appended claims.

[0075] A first embodiment of the present invention is a method for producing a linear alkylbenzene product derived from triglycerides, the method comprising deoxygenating the triglycerides, which after deoxygenation produces 60% or more of normal alkanes having fewer than 16 carbon atoms, thereby forming an alkane stream comprising 60% or more of normal alkanes having fewer than 16 carbon atoms; fractionating the alkane stream to form a C9 - C14 stream comprising C9 - C14 alkanes and a C14+ stream comprising C14+ alkanes; subjecting the C14+ stream to linear selective cracking in a separate linear selective cracking unit in the presence of a linear selective cracking catalyst under linear selective cracking conditions to form a first stream comprising C9 - C14 normal alkanes or lightly branched alkanes and a second stream comprising isoalkanes; removing contaminants from the C9 - C14 stream and the first stream to form a purified stream, wherein the contaminants comprise sulfur compounds, or nitrogen compounds, or phosphorus compounds, or oxygen-containing compounds, or aromatic compounds or combinations thereof; dehydrogenating the purified stream to provide a dehydrogenated stream comprising monoolefins, diolefins and aromatic compounds; selectively hydrogenating the diolefins in the dehydrogenated stream to form additional monoolefins, and separating and removing the aromatic compounds from the monoolefins to form an aromatic compound stream comprising the aromatic compounds and a monoolefin stream comprising the monoolefins; alkylating benzene with the monoolefins under alkylation conditions to provide an alkylation effluent comprising alkylbenzenes and benzene; separating the alkylbenzenes to provide the alkylbenzene product derived from the triglycerides. One embodiment of the present invention is one, any or all of the foregoing embodiments in this paragraph to the first embodiment in this paragraph, wherein the C9 - C14 stream and the first stream are combined before removing the contaminants from the C9 - C14 stream and the first stream to form the purified stream. One embodiment of the present invention is one, any or all of the foregoing embodiments in this paragraph to the first embodiment in this paragraph, wherein the linear selective cracking catalyst comprises a ruthenium, platinum and nickel supported catalyst or a mixture thereof. One embodiment of the present invention is one, any or all of the foregoing embodiments in this paragraph to the first embodiment in this paragraph, wherein the linear selective cracking conditions include a temperature in the range of 290 °C to 455 °C, or a pressure in the range of 2.8 MPa to 17.5 MPa, or a combination thereof. One embodiment of the present invention is one, any or all of the foregoing embodiments in this paragraph to the first embodiment in this paragraph, wherein the amount of the alkylbenzene product is greater than the amount of alkylbenzene produced in a method without the linear selective cracking step. One embodiment of the present invention is one, any or all of the foregoing embodiments in this paragraph to the first embodiment in this paragraph, wherein the alkylbenzene product comprises alkylbenzenes having C9 - C14 chains.One embodiment of the present invention is one, any, or all of the foregoing embodiments in this paragraph to the first embodiment in this paragraph, wherein the alkylbenzene product comprises alkylbenzenes having C10 to C13 chains. One embodiment of the present invention is one, any, or all of the foregoing embodiments in this paragraph to the first embodiment in this paragraph, wherein the triglyceride produces 0.1 wt% to 20 wt% of n-alkanes having 16 carbon atoms after dehydrogenation. One embodiment of the present invention is one, any, or all of the foregoing embodiments in this paragraph to the first embodiment in this paragraph, wherein the C14+ stream comprises C16 to C18 alkanes. One embodiment of the present invention is one, any, or all of the foregoing embodiments in this paragraph to the first embodiment in this paragraph, wherein the triglyceride produces not less than 15 wt% of n-alkanes having 12 or 14 carbon atoms after deoxygenation. One embodiment of the present invention is one, any, or all of the foregoing embodiments in this paragraph to the first embodiment in this paragraph, wherein the triglyceride produces not less than 10 wt% of n-alkanes having 12 carbon atoms after deoxygenation.

[0076] A second embodiment of the present invention is a method for producing an alkylbenzene product derived from triglycerides, the method comprising deoxygenating the triglycerides, which after deoxygenation produces 60% or more of normal alkanes having fewer than 16 carbon atoms, thereby forming an alkane stream comprising 60% or more of normal alkanes having fewer than 16 carbon atoms; fractionating the alkane stream to form a C9-C14 stream comprising C9-C14 alkanes and a C14+ stream comprising C14+ alkanes; subjecting the C14+ stream to straight-chain selective cracking in a separate straight-chain selective cracking unit in the presence of a straight-chain selective cracking catalyst under straight-chain selective cracking conditions to form a first stream comprising C9-C14 normal alkanes or lightly branched alkanes and a second stream comprising isoparaffins, wherein the straight-chain selective cracking catalyst comprises a ruthenium, platinum and nickel supported catalyst or a mixture thereof; removing contaminants from the C9-C14 stream and the first stream to form a purified stream, wherein the contaminants comprise sulfur compounds, or nitrogen compounds, or phosphorus compounds, or oxygen-containing compounds, or aromatic compounds or a combination thereof; dehydrogenating the purified stream to provide a dehydrogenated stream comprising monoolefins, diolefins and aromatic compounds; selectively hydrogenating the diolefins in the dehydrogenated stream to form additional monoolefins, and separating and removing the aromatic compounds from the monoolefins to form an aromatic compound stream comprising the aromatic compounds and a monoolefin stream comprising the monoolefins; alkylating benzene with the monoolefins under alkylation conditions to provide an alkylation effluent comprising alkylbenzenes and benzene; separating the alkylbenzenes to provide the alkylbenzene product derived from the triglycerides; wherein the alkylbenzene product comprises alkylbenzenes having C9-C14 chains. One embodiment of the present invention is one, any or all of the foregoing embodiments in this paragraph to the second embodiment in this paragraph, wherein the C9-C14 stream and the first stream are combined before removing the contaminants from the C9-C14 stream and the first stream to form the purified stream. One embodiment of the present invention is one, any or all of the foregoing embodiments in this paragraph to the second embodiment in this paragraph, wherein the straight-chain selective cracking conditions include a temperature in the range of 290 °C to 455 °C, or a pressure in the range of 2.8 MPa to 17.5 MPa, or a combination thereof. One embodiment of the present invention is one, any or all of the foregoing embodiments in this paragraph to the second embodiment in this paragraph, wherein the amount of the alkylbenzene product is greater than the amount of alkylbenzene produced in a method without the straight-chain selective cracking step. One embodiment of the present invention is one, any or all of the foregoing embodiments in this paragraph to the second embodiment in this paragraph, wherein the triglycerides produce 0.1 wt% to 20 wt% of normal alkanes having 16 carbon atoms after deoxygenation.One embodiment of the present invention is one, any, or all of the foregoing embodiments in this paragraph to the second embodiment in this paragraph, wherein the triglyceride produces no less than 15% by weight of n-alkanes having 12 or 14 carbon atoms after deoxygenation. One embodiment of the present invention is one, any, or all of the foregoing embodiments in this paragraph to the second embodiment in this paragraph, wherein the triglyceride produces no less than 10% by weight of n-alkanes having 12 carbon atoms after deoxygenation.

[0077] Although no further detailed description is provided, it is believed that those skilled in the art can make the most of the present invention by using the foregoing description and can easily determine the basic features of the present invention without departing from the essence and scope of the present invention to make various changes and modifications thereto and adapt it to various uses and conditions. Therefore, the foregoing preferred specific embodiments should be understood as being merely illustrative and not limiting the remainder of the disclosure in any way, and are intended to cover various modifications and equivalent arrangements included within the scope of the appended claims.

[0078] In the foregoing, all temperatures are shown in degrees Celsius, and all parts and percentages are by weight unless otherwise indicated.

Claims

1. A device for producing linear alkylbenzene, characterized in that: The device for producing linear alkylbenzene comprises: a deoxygenation unit in communication with the triglyceride feed line; A C9 to C14 pipeline and a C14+ pipeline, wherein the C9 to C14 pipeline and the C14+ pipeline are connected to a deoxygenation unit; a separate linear selective cracking unit in communication with the C14+ line; a first pipeline and a second pipeline; wherein the first pipeline and the second pipeline are in communication with a separate linear selective cracking unit; a purification unit, which is in communication with the first pipeline; a purification pipeline, which is connected to the purification unit; a dehydrogenation unit, which is in communication with the purification line; a dehydrogenation pipeline connected to the dehydrogenation unit; a selective hydrogenation unit in communication with the dehydrogenation line; a monoolefin line communicating with the selective hydrogenation unit; an alkylation unit in communication with the monoolefin line; An alkylation effluent line communicating with the alkylation unit.

2. The device for producing linear alkylbenzene according to claim 1, characterized in that: The device for producing linear alkylbenzene further comprises: a benzene separation unit in communication with the alkylation effluent line, and A linear alkylbenzene product line and a benzene recycle line are in communication with the benzene separation unit.

3. The device for producing linear alkylbenzene according to claim 2, characterized in that: The benzene recycle line is in communication with the alkylation unit and is recycled to the alkylation unit.

4. The device for producing linear alkylbenzene according to claim 1, characterized in that: The C9 to C14 pipeline is connected to the purification unit.

5. The device for producing linear alkylbenzene according to claim 1, characterized in that: The device for producing linear alkylbenzene further comprises: An aromatics line and a light ends line, wherein the aromatics line and the light ends line are in communication with the selective hydrogenation unit.

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