CN108569945B - Process for producing linear alkylbenzene - Google Patents
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- CN108569945B CN108569945B CN201710147816.0A CN201710147816A CN108569945B CN 108569945 B CN108569945 B CN 108569945B CN 201710147816 A CN201710147816 A CN 201710147816A CN 108569945 B CN108569945 B CN 108569945B
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Abstract
The invention relates to a production method of linear alkylbenzene, which mainly solves the problems of low selectivity of 2-phenyl isomer and easy inactivation of a catalyst in the prior art. The method comprises the steps of contacting long-chain olefin and benzene with a catalyst under alkylation reaction conditions; the catalyst comprises the following components in parts by weight: a) 40-90 parts of organic silicon zeolite; b) 10-60 parts of a binder; the organosilicone zeolite comprises a composition having a molar relationship: (1/n) Al2O3：SiO2: the technical scheme of (m/n) R, wherein n is 5-250, m is 0.01-50, and R is at least one of alkyl, alkenyl or phenyl, solves the problem well, and can be used in the industrial production of linear alkylbenzene.
Description
Technical Field
The invention relates to a production method of linear alkylbenzene.
Background
Linear alkylbenzene LAB is an important raw material for synthesizing detergents and is generated by the alkylation reaction of benzene and long-chain olefin under the action of an acid catalyst. The detergent synthesized by LAB has the characteristics of high surface activity and good biodegradability. HF or AlCl with strong corrosiveness and toxicity is mostly used in the current production process3This causes problems such as difficulty in handling product residues, corrosion of equipment, and environmental pollution, for the catalyst. Therefore, it is increasingly important to develop a new generation of non-polluting, non-corrosive catalysts and related processes.
Benzene is alkylated with long alkenes to give linear alkylbenzenes which are mixtures of various isomers, important considerations for commercial alkylbenzene products include the 2-phenyl isomer content and the linearity of the alkyl substituents. Alkylbenzenes with higher 2-phenyl content are desired in efficacy because they tend to provide surfactants with better soil release when sulfonated.
At present, there are two main types of industrial synthetic methods for linear alkylbenzenes, one is the use of strong acid catalysts such as hydrogen fluoride, and the other is the development of SiO containing fluorine by cooperation of UOP and Petresa, Spanish2-Al2O3A solid acid catalyst. Although such processes result in high conversions, after the alkylation reaction has continued for 24 hours, the catalyst is regenerated by washing with benzene. The 2-phenyl isomer selectivity is typically 30% or less. Although the documents report that the catalysts such as mordenite, potassium zeolite and the like have high selectivity for 2-phenyl isomer, the industrial application is difficult because the catalytic performance is unstable and is easy to activate. To date, there has been no report of stable molecular sieve catalysts with 2-phenyl isomer selectivity greater than 40%, and therefore the selection of stable, highly selective 2-phenyl isomer alkylbenzene catalysts is highly desirable to detergent manufacturers.
Disclosure of Invention
The invention aims to solve the technical problems of low selectivity of 2-phenyl isomer and easy inactivation of a catalyst in the prior art, and provides a novel production method of linear alkylbenzene. The method has the characteristics of high selectivity of the 2-phenyl isomer, less carbon deposition during long-time operation and long service life of the catalyst.
In order to solve the technical problems, the technical scheme adopted by the invention is as follows: a process for the production of linear alkylbenzenes comprising the steps of contacting a long chain olefin and benzene under alkylation reaction conditions with a catalyst; the catalyst comprises the following components in parts by weight:
a) 40-90 parts of organic silicon zeolite;
b) 10-60% of a binder;
the organosilicone zeolite comprises a composition having a molar relationship: (1/n) Al2O3：SiO2: (m/n) R, wherein n is 5-250, m is 0.01-50, and R is at least one of alkyl, alkenyl or phenyl. Si of the zeolite29The NMR solid nuclear magnetic spectrum at least comprises one Si between-80 and +50ppm29Peaks in nuclear magnetic resonance spectroscopy; the X-ray diffraction pattern of the zeolite has d-space maximum values at 12.4 +/-0.2, 10.5 +/-0.3, 9.3 +/-0.3, 6.8 +/-0.2, 6.1 +/-0.2, 5.5 +/-0.2, 4.4 +/-0.2, 4.0 +/-0.2, 3.5 +/-0. l, 3.4 +/-0.1 and 3.3 +/-0.1 angstroms.
In the technical scheme, n is 10-100, and m is 0.05-20.
In the technical scheme, the alkyl is an alkyl with 1-8 carbon atoms, and is preferably methyl or ethyl; the alkyl alkenyl group is an alkyl alkenyl group having 2-10 carbon atoms, and preferably a vinyl group.
In the above technical scheme, the long-chain olefin is a linear olefin having 8 to 28 carbon atoms, preferably 10 to 16 carbon atoms.
In the above technical solution, the binder is at least one selected from alumina, titania, zinc oxide, and zirconia.
In the technical scheme, the molar ratio of benzene to long-chain olefin is (2-100): 1.
In the above technical scheme, the alkylation reaction conditions include: the reaction temperature is 100-270 ℃, and preferably 120-250 ℃; the reaction pressure is 0.1-15 MPa, preferably 0.1-3 MPa; the space velocity of the long-chain olefin is 0.1-2 hours-1Preferably 0.5 to 1 hrTime of flight-1。
In the technical scheme, the catalyst also comprises a component c) 0.05-2 parts of fluorine.
The synthesis method of the organic silicon zeolite in the method comprises the following steps:
a) mixing organic silicon source, inorganic silicon source, aluminum source, alkali, organic amine template agent and water, and using SiO in inorganic silicon source2On a molar basis, the reaction mixture is: SiO 22/Al2O35-250 parts of organic silicon source/SiO2＝0.001～1，OH-/SiO2＝0.01～5.0，H2O/SiO25-100 of organic amine/SiO2＝0.01～2.0；
b) And (3) reacting the reaction mixture for 1-100 hours at the crystallization reaction temperature of 90-200 ℃, taking out, washing with water, and drying to obtain the organic silicon zeolite.
In the above technical solution, the inorganic silicon source is at least one selected from silica sol, solid silica, silica gel, silicate ester, diatomaceous earth or water glass. The organic silicon source is at least one selected from halogen silane, silazane or alkoxy silane; wherein the halosilane is at least one selected from the group consisting of trimethylchlorosilane, dimethyldichlorosilane, triethylchlorosilane, diethyldichlorosilane, dimethylchlorobromosilane, dimethylethylchlorosilane, dimethylbutylchlorosilane, dimethylphenylchlorosilane, dimethylisopropylchlorosilane, dimethyl-t-butylchlorosilane, dimethyloctadecylchlorosilane, methylphenylvinylchlorosilane, vinyltrichlorosilane, and diphenyldichlorosilane; the silazane is at least one selected from hexamethyldisilazane, heptamethyldisilazane, tetramethyldisilazane, divinyltetramethyldisilazane or diphenyltetramethyldisilazane; the alkoxy silane is at least one selected from trimethylethoxysilane, dimethyldiethoxysilane, trimethylmethoxysilane, dimethyldimethoxysilane, trimethoxyphenylsilane or diphenyldiethoxysilane. The aluminum source is at least one selected from sodium aluminate, sodium metaaluminate, aluminum sulfate, aluminum nitrate, aluminum chloride, aluminum hydroxide, alumina, kaolin or montmorillonite. The alkali is inorganic alkali and is at least one selected from lithium hydroxide, sodium hydroxide, potassium hydroxide, rubidium hydroxide and cesium hydroxide. The organic template agent is at least one selected from ethylenediamine, hexamethylenediamine, cyclohexylamine, hexamethyleneimine, heptamethyleneimine, pyridine, hexahydropyridine, butylamine, hexylamine, octylamine, decylamine, dodecylamine, hexadecylamine and octadecylamine.
Reaction mixture with SiO in inorganic silicon source2Based on the molar ratio, the preferable range is as follows: SiO 22/Al2O310 to 100 parts of organic silicon source/SiO2＝0.005～0.5，OH-/SiO2＝0.05～1.0，H2O/SiO210-80 parts of organic template agent/SiO20.05 to 1.0. The preferable range of the crystallization reaction temperature is 100-180 ℃, and the preferable range of the crystallization reaction time is 2-60 hours. The preferable scheme during the synthesis is that the reaction mixture is aged for 2-100 hours at 10-80 ℃ before crystallization.
The preparation method of the catalyst used in the method of the invention is as follows:
mixing the synthesized organic silicon zeolite with a binder, wherein the content of the zeolite is 40-90 wt%. Then adding 2.5 wt% of dilute nitric acid solution, kneading, molding, drying, and roasting in air to 480-600 ℃ for 1-15 hours to obtain the finished catalyst. When carrying fluorine, the organosilicon zeolite is treated by adopting a fluorine-containing compound solution isovolumetric impregnation method, and then is formed. The fluorine-containing compound is at least one selected from the group consisting of ammonium fluoride, sodium fluoride and potassium fluoride.
The invention adopts the organic silicon zeolite as the catalyst active main body, the zeolite is in a stable single sheet thin layer MWW structure, the catalyst has more exposed surface acid sites, so the catalyst has higher activity, and the single sheet thin layer structure and the twelve-membered ring super cage are beneficial to the transfer of long chain olefin and generated long chain alkylbenzene between layers, thereby greatly improving the stability of the catalyst. The confinement effect of the semi-supercage is beneficial to the generation of a product with higher linearity, and the product has higher selectivity on a 2-phenyl isomer when being used for the preparation reaction of linear alkylbenzene. Under the condition of 180 ℃, after 1000 hours of operation, the conversion rate of long alkene is still kept above 99%, the selectivity of 2-phenyl isomer reaches 55%, the catalyst has no sign of inactivation, and a better technical effect is achieved. Further, partial Si-O-Al bonds in the molecular sieve are converted into Al-F species through fluorine-carrying modification treatment, and the surface acidity of the organic zeolite molecular sieve is adjusted, so that the stability of the catalyst can be further improved.
Drawings
FIG. 1 is a plot of olefin conversion versus time [ example 3 ].
FIG. 2 is [ example 3 ] a plot of 2-phenyl isomer selectivity over time.
The invention is further described below by means of specific embodiments.
Detailed Description
[ example 1 ]
Sodium aluminate (42.0 wt% Al)2O3)6.1 g was dissolved in 288 g of water, and 1.0 g of sodium hydroxide was added thereto to dissolve it. Then, 34.0 g of piperidine is added under the condition of stirring, 60 g of solid silicon oxide and 5.5 g of trimethylchlorosilane are added, and the material ratio (molar ratio) of the reactants is as follows: SiO 22/Al2O3＝40，NaOH/SiO20.025 parts of chlorotrimethylsilane/SiO20.05, piperidine/SiO2＝0.50，H2O/SiO216. After the reaction mixture is stirred uniformly, the mixture is put into a stainless steel reaction kettle and crystallized for 50 hours at 135 ℃ under the condition of stirring. Taking out, filtering, washing and drying. Si thereof29The NMR spectrum of the solid showed a peak at-18 ppm in nuclear magnetic resonance. After 10 hours of baking at 500 ℃, the X-ray diffraction data are shown in Table 1.
TABLE 1
A50 g sample of the synthesized powder was calcined at 550 ℃ for 5 hours, then exchanged 3 times with 1M ammonium nitrate, filtered and dried. Then, the catalyst is fully mixed with 20 g of alumina, added with 5 percent (by weight) of nitric acid for kneading, extruded into strips with the diameter of 1.6 multiplied by 2 mm, dried at 120 ℃, and roasted at 550 ℃ for 10 hours to prepare the required catalyst.
5 g of the catalyst prepared above were charged in a fixed bed reactor and then a mixture of benzene and 1-dodecene (benzene to olefin ratio 10:1) was passed through. The reaction conditions are as follows: the weight space velocity of 1-dodecene is 0.75 h-1The reaction temperature is 150 ℃, and the reaction pressure is 1.7 MPa.
After 100 hours of reaction, the reaction results were: the conversion rate of 1-dodecene is 99.45 percent, and the selectivity of 2-phenyl isomer is 54.73 percent.
[ example 2 ]
3.0 g of alumina was dissolved in 450 g of water, and 16.0 g of sodium hydroxide was added thereto to dissolve it. Then, 34.7 g of hexamethyleneimine, 60 g of solid silicon oxide and 5.9 g of dimethyldiethoxysilane are added under the condition of stirring, and the material ratio (mol ratio) of the reactants is as follows: SiO 22/Al2O3＝30，NaOH/SiO20.2, (. sup.2) dimethyldiethoxysilane/SiO20.04 parts by weight of hexamethyleneimine/SiO2＝0.35，H2O/SiO2After the reaction mixture was stirred uniformly, the mixture was put into a stainless steel reaction vessel and crystallized at 145 ℃ for 70 hours with stirring. Taking out, filtering, washing and drying. Si thereof29The NMR spectrum of the solid showed a peak at 6ppm in nuclear magnetic resonance. After 10 hours of baking at 500 ℃, the X-ray diffraction data are shown in Table 2.
TABLE 2
A50 g sample of the synthesized powder was taken and the catalyst was prepared as in [ example 1 ]. 5 g of the catalyst prepared above were charged in a fixed bed reactor and then a mixture of benzene and 1-dodecene (benzene to olefin ratio 12:1) was passed through. The reaction conditions are as follows: the weight space velocity of 1-dodecene is 0.9 h-1The reaction temperature is 170 ℃ and the reaction pressure is 2.1 MPa.
After 100 hours of reaction, the reaction results were: the conversion rate of 1-dodecene is 99.65%, and the selectivity of 2-phenyl isomer is 55.28%.
[ example 3 ]
Using the catalyst synthesized in [ example 2 ], 5 g of the catalyst was charged in a fixed bed reactor, and then a mixture of benzene and 1-dodecene was introduced (benzene-to-olefin ratio 15: 1). The reaction conditions are as follows: the weight space velocity of 1-dodecene is 0.4 h-1The reaction temperature is 180 ℃, and the reaction pressure is 2.0 MPa. After 1000 hours of continuous alkylation reaction, the conversion rate of olefin is always over 99.0 percent, and the selectivity of 2-phenyl isomer is about 55.05 percent. The catalyst has good activity stability under the operation condition, and the stable operation time of the device is long.
FIG. 1 is a plot of olefin conversion versus time and FIG. 2 is a plot of 2-phenyl isomer selectivity versus time. As can be seen from FIGS. 1 and 2, the catalyst has high catalytic activity and activity stability, and at the same time, the catalyst has high selectivity to the 2-phenyl isomer.
[ example 4 ]
Using the catalyst synthesized in example 2, 5 g of the catalyst was charged in a fixed bed reactor, and then a mixture of benzene and 1-tridecene was passed through (benzene-to-olefin ratio 15: 1). The reaction conditions are as follows: weight space velocity of 1-tridecene is 0.4 h-1The reaction temperature is 180 ℃, and the reaction pressure is 2.0 MPa.
After 900 hours of reaction, the reaction results were: the conversion of 1-tridecene was 99.32%, and the selectivity of 2-phenyl isomer was 50.93%.
[ example 5 ]
Using the catalyst synthesized in [ example 2 ], 5 g of the catalyst was charged in a fixed bed reactor, and then a mixture of benzene and tetradecene was introduced (benzene-to-olefin ratio 15: 1). The reaction conditions are as follows: weight space velocity of tetradecene is 0.4 h-1The reaction temperature is 180 ℃, and the reaction pressure is 2.0 MPa.
After 420 hours of reaction, the reaction result was: tetradecene conversion was 99.07%, and 2-phenyl isomer selectivity was 50.91%.
[ example 6 ]
Using the catalyst synthesized in example 2, 5 g of the catalyst was charged in a fixed bed reactor and then introduced into the reactorMixtures of benzene and tetracosene (benzene to olefin ratio 15: 1). The reaction conditions are as follows: weight space velocity of tetracosene is 0.4 h-1The reaction temperature is 200 ℃ and the reaction pressure is 2.0 MPa.
After 200 hours of reaction, the reaction results were: the conversion of eicosatetraene was 98.72% and the selectivity of the 2-phenyl isomer was 46.12%.
[ example 7 ]
Using the catalyst synthesized in [ example 2 ], 5 g of the catalyst was charged in a fixed bed reactor, and then a mixture of benzene and nonaene was introduced (benzene-to-olefin ratio 15: 1). The reaction conditions are as follows: weight space velocity of nonaene is 0.4 h-1The reaction temperature is 160 ℃, and the reaction pressure is 2.0 MPa.
After 550 hours of reaction, the reaction results were: the conversion rate of nonaene is 99.32%, and the selectivity of 2-phenyl isomer is 50.56%.
[ example 8 ]
The organosilicon zeolite synthesized in [ example 2 ] and 0.1M ammonia fluoride solution were used to obtain a fluorine-carrying modified organosilicon zeolite by an equivalent volume impregnation method, the fluorine carrying amount per 100 parts of zeolite was 0.4 parts, and further the finished catalyst was obtained by the same catalyst preparation method as in [ example 1 ], 5 g of which was packed in a fixed bed reactor, and then a mixture of benzene and nonaene was introduced (benzene to olefin ratio 15: 1). The reaction conditions are as follows: weight space velocity of nonaene is 0.4 h-1The reaction temperature is 160 ℃, and the reaction pressure is 2.0 MPa.
After 550 hours of reaction, the reaction results were: the conversion rate of nonaene is 99.45%, and the selectivity of 2-phenyl isomer is 50.61%. After 1000 hours of reaction, the reaction results were: the conversion rate of nonaene is 99.28%, and the selectivity of 2-phenyl isomer is 50.08%.
[ COMPARATIVE EXAMPLE 1 ]
Using a commercially available MCM-22 catalyst (silica-alumina molar ratio of 30), 5 g were charged in a fixed bed reactor, and then a mixture of benzene and 1-dodecene was passed through (benzene-olefin ratio 15: 1). The reaction conditions are as follows: the weight space velocity of 1-dodecene is 0.4 h-1The reaction temperature is 180 ℃, and the reaction pressure is 2.0 MPa. After 60 hours of continuous alkylation reaction, the conversion rate of olefin is reduced to be below 80.0 percent, and the selectivity of 2-phenyl isomer is 43.85％。
[ COMPARATIVE EXAMPLE 2 ]
Using a commercially available mordenite catalyst (silica to alumina molar ratio of 10), 5 g were charged in a fixed bed reactor and then a mixture of benzene and 1-dodecene was passed through (benzene to olefin ratio 15: 1). The reaction conditions are as follows: the weight space velocity of 1-dodecene is 0.4 h-1The reaction temperature is 180 ℃, and the reaction pressure is 2.0 MPa. After 5.5 hours of continuous alkylation reaction, the conversion rate of the olefin dropped below 80.0%, and the catalyst was rapidly deactivated.
[ COMPARATIVE EXAMPLE 3 ]
Using a commercially available HY catalyst (Si/Al molar ratio of 5), 5 g of the mixture was charged in a fixed bed reactor, and then a mixture of benzene and 1-dodecene was passed through the reactor (benzene/olefin ratio 15: 1). The reaction conditions are as follows: the weight space velocity of 1-dodecene is 0.4 h-1The reaction temperature is 180 ℃, and the reaction pressure is 2.0 MPa. After 34 hours of continuous alkylation, the olefin conversion dropped below 80.0% and the 2-phenyl isomer selectivity was only 29.17%.
Claims (9)
1. A process for the production of linear alkylbenzenes comprising the steps of contacting a long chain olefin and benzene under alkylation reaction conditions with a catalyst; the catalyst comprises the following components in parts by weight:
a) 40-90 parts of organic silicon zeolite;
b) 10-60 parts of a binder;
c) 0.05-2 parts of fluorine;
the organosilicone zeolite comprises a composition having a molar relationship: (1/n) Al2O3：SiO2: (m/n) R, wherein n is 5-250, m is 0.01-50, and R is at least one of alkyl, alkenyl or phenyl; si of the zeolite29The NMR solid nuclear magnetic spectrum at least comprises one Si between-80 and +50ppm29Peaks in nuclear magnetic resonance spectroscopy; the X-ray diffraction pattern of the zeolite has d-space maximum values at the angstrom positions of 12.4 +/-0.2, 10.5 +/-0.3, 9.3 +/-0.3, 6.8 +/-0.2, 6.1 +/-0.2, 5.5 +/-0.2, 4.4 +/-0.2, 4.0 +/-0.2, 3.5 +/-0. l, 3.4 +/-0.1 and 3.3 +/-0.1;
the long chain olefins are linear olefins having from 8 to 28 carbon atoms.
2. The method for producing a linear alkylbenzene as claimed in claim 1, wherein n is 10 to 100 and m is 0.05 to 20.
3. The method for producing a linear alkylbenzene as claimed in claim 1, wherein the alkyl group is an alkyl group having 1 to 8 carbon atoms, and the alkenyl group is an alkenyl group having 2 to 10 carbon atoms.
4. The method for producing a linear alkylbenzene as claimed in claim 3, wherein the alkyl group is a methyl group or an ethyl group, and the alkenyl group is a vinyl group.
5. The process for producing a linear alkylbenzene as claimed in claim 1, wherein the long-chain olefin has 10 to 16 carbon atoms.
6. The method for producing linear alkylbenzenes according to claim 1, wherein the binder is at least one selected from the group consisting of alumina, titania, zinc oxide, and zirconia.
7. The process for producing a linear alkylbenzene as claimed in claim 1, wherein the molar ratio of benzene to long-chain olefin is (2-100): 1.
8. The process for the production of linear alkylbenzenes according to claim 1, wherein the alkylation reaction conditions comprise: the reaction temperature is 100-270 ℃, the reaction pressure is 0.1-15 MPa, and the space velocity of the long-chain olefin is 0.1-2 hours-1。
9. The process for the production of linear alkyl benzene as recited in claim 8, wherein the alkylation reaction conditions include: the reaction temperature is 120-250 ℃, the reaction pressure is 0.1-3 MPa, and the space velocity of the long-chain olefin is 0.5-1 hour-1。
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