CN112851457B - Method for converting low-carbon olefin into isooctene by catalyzing low-carbon olefin with chemically immobilized Br phi sted acidic ionic liquid - Google Patents
Method for converting low-carbon olefin into isooctene by catalyzing low-carbon olefin with chemically immobilized Br phi sted acidic ionic liquid Download PDFInfo
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- C07C2/02—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons
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- C07C2/06—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons by oligomerisation of well-defined unsaturated hydrocarbons without ring formation of alkenes, i.e. acyclic hydrocarbons having only one carbon-to-carbon double bond
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- B01J31/0278—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides comprising ionic liquids, as components in catalyst systems or catalysts per se, the ionic liquid compounds being used in the molten state at the respective reaction temperature containing nitrogen as cationic centre
- B01J31/0281—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides comprising ionic liquids, as components in catalyst systems or catalysts per se, the ionic liquid compounds being used in the molten state at the respective reaction temperature containing nitrogen as cationic centre the nitrogen being a ring member
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Abstract
The invention provides a chemical immobilization method
A method for converting low-carbon olefin into isooctene by using acidic ionic liquid as catalyst. The chemical immobilization
The acidic ionic liquid takes micron-sized resin particles which contain halogen X-I, Br or Cl and are within the range of 0.50-2000 mu m as a carrier material, is chemically modified by an N heterocyclic compound, is linked with sulfonate functional groups through covalent bonds to form N heterocyclic modified sulfonate ampholytic salt resin particles, and is finally protonated by sulfuric acid or phosphoric acid solution to prepare the chemically immobilized resin
Acidic ionic liquid applied to catalyzing low-carbon olefin isobutene to synthesize a dimerization product isooctene product in a high-selectivity manner and chemical immobilization
Description
Technical Field
The invention belongs to the technical field of energy catalysis, and relates to chemical immobilization
A method for synthesizing medium-high-carbon olefin products by catalyzing low-carbon olefins with acidic ionic liquid.
Background
The low-carbon olefin can be catalyzed and oligomerized to generate medium-carbon chain olefin products with high market utilization value, including C8 ＝、C12 ＝And C16 ＝Etc. wherein C8 ＝The gasoline additive can be used as a gasoline blender, can enable oil products to achieve high octane value or high combustion rate, and produces higher value-added products. In addition, the method can also be applied to synthesizing octylphenol and preparing fine chemicals such as nonionic surfactants, phenolic resins, printing ink, antirust paint and the like; other olefin products can also be used in the fields of food additives, surfactants and the like. At present, the technology is widely used by Europe, America and other countries to replace the traditional MTBE process which pollutes the environment seriously, which is beneficial to forming and developing environment-friendly chemical technology and constructing good social and economic benefits and market prospects.
Concentrated H is generally selected in the traditional isobutene oligomerization process2SO4HF, etc. liquid strong acid as catalyst, dimerization C8 ＝The selectivity of the product is not high, the problems of equipment corrosion, environmental pollution and the like exist, the separation of the catalyst and the product is realized by working procedures such as distillation or solvent extraction, the equipment investment cost is high, and the application and popularization of the catalyst are limited. Loading liquid acid on SiO by dipping method2[ Dioscorea nipponica Makino, Cyperus paniculata, Cynanchum yunnanense, Spirodela polyrhiza ] catalyst for selective dimerization of isobutene Chinese patent of invention No. 2005, CN 1810373A.]、Al2O3The invention relates to a catalyst and a process for preparing octaene and dodecene by oligomerization of/X-amorphous aluminum silicate [ Hongqing yao, Sunwa, Wangbuliang ] butene.]MCM-56 molecular sieve [ Songweihong, Jinzhuansheng, Zhoushanchun, Gushihua, Huangzujuan.]、ZSM-5[Garwood W E,Caesar P D,Brennan J A.Light olefin processing.US 4150062.]Or ZSM-35 [ Liyunlong, Lvjianggang, Jinzhuang, Jinliang, Zhoushanchun, Huangzujuan, Sun lan Lianping, carbon four-olefin oligomerization method for preparing gasoline component.]And on inorganic carriers, the obtained solid phosphoric acid SPA catalytic active center diffuses into an isobutene reaction system, so that the loss of an acid catalyst and the unstable activity are easily caused. Loading metal sulfate on SiO2、γ-Al2O3Or SiO2-Al2O3Can be catalyzed at a lower reaction temperature of 20-70℃ on an inorganic carrierIsobutene oligomerization reaction, highest isobutene conversion rate of 91%, and selectivity corresponding to dimerization product of 47% [ Tianfuping, Chua Tianxi, congratulatory, Sude fragrance, Jimin, Zhang Jia4The isobutene in the catalyst has a supported solid acid catalyst with selective oligomerization, the invention of Chinese patent No. CN 101332432A.]. In addition, the polystyrene sulfonic acid resin coated metal and metal sulfate catalyst, particularly the transition metal nickel catalyst, catalyzes the oligomerization reaction of isobutene, the conversion rate of isobutene is 41-69%, and the selectivity of generated dimerization products is more than 90% (Yuansai, Huanggufeng, He-Shi, Li-Yuan, Wang-Zhong, Lvyanhong, Song-Weifeng, Dong-Long, Liu-Zheng-Feng, Zhili-school-Li).]。
The ionic liquid can also be used for catalyzing oligomerization of isobutene after being modified by transition metal, but often shows medium catalytic activity and low dimerization product selectivity. Yang et al [ Yang S Q, Liu Z C, Meng X H, Xu C M. oligomerization of isobutene catalyzed by Iron (III) chloride ionic liquids. Energ. Fuel,2009,23:70-73.]Ferric chloride is introduced into an alkylamine ionic liquid catalyst as an anion structural unit, and is sensitive to air and water, so that the catalytic activity of the isobutene oligomerization is not high, the conversion rate of isobutene is only 3-85%, the selectivity of dimerization products is 14-40%, and polymerization products such as trimerization, tetramerization and the like are more; a homogeneous ionic liquid loaded transition metal catalyst for oligomerization of isobutene is prepared from vanadium, chromium, manganese, iron, cobalt, nickel, copper or zinc through standing for direct separation, cyclic use for five times, and the conversion rate of isobutene is still about 87%, but the selectivity of dimerization product is less than 50% [ Huang Shao, Jiang Qing Mei, Yuan, Ri Yuan, and Nippon ], and the catalyst is prepared and used in oligomerization of alkene.]. Yet simple physical impregnation process to obtain SiO2The activity loss of the loaded ionic liquid catalyst is serious, the reaction time is as long as 5 hours, the catalytic efficiency is seriously influenced, and the method is urgently neededSo as to improve the catalytic efficiency and the activity stability of the catalyst [ Feh e r C, Kriv n E, Hancs Lo k J,
R.Oligomerisation of isobutene with silica supported ionic liquid catalysts.Green Chem.,2012,14:403-409.]。
disclosure of Invention
The purpose of the present invention is to provide a chemical immobilization
The acidic ionic liquid catalyst is used for catalyzing the catalytic conversion of low-carbon olefins, synthesizing isooctene products with high efficiency and high selectivity, solving the problems of loss of active components, poor stability, overhigh catalyst consumption and long-time reaction caused by the physical impregnation technology of the immobilized catalyst, finally reducing the catalyst consumption, shortening the reaction time, improving the catalytic efficiency of the immobilized catalyst and improving the stability of the catalytic activity. The related chemical immobilized ionic liquid catalyst takes halogen-containing micron-sized resin particles as a carrier material, utilizes an N heterocyclic compound to link sulfonate functional groups in a covalent bond mode to form resin amphoteric salt solid particles, generates immobilized ionic liquid catalyst particles containing protonic acid after being treated by protonic strong acid, and is applied to the catalytic polymerization process of low-carbon olefin, the dosage of the catalyst is obviously reduced, the catalytic conversion efficiency is obviously improved, the dosage is shortened to be less than 50min from the original 5h, the catalyst can be recycled for 5 times, and the activity stability and the selectivity of high-value-added isooctene products are basically kept unchanged. The technical scheme of the invention is as follows:
1. chemical immobilization
Preparation of acidic ionic liquid catalyst
The micron-sized resin particle carrier material containing halogen X is chemically modified by an N heterocyclic compound in a solvent A, and then purified by an organic solvent B by utilizing a covalent bond chain sulfonate functional group to form resin amphoteric salt solid particles, namely resin amphoteric salt solid particlesThen protonating by strong acid solution to obtain chemical immobilization
Acidic ionic liquid catalyst M. Wherein X is any one of I, Cl and Br; the micron-sized resin particles have any size within the range of 0.50-2000 mu m; the solvent A is any one of dichloromethane, acetonitrile, toluene, trimethylbenzene, N-dimethylformamide and chloroform; the sulfonate is any one of butyl sulfonate, propyl sulfonate and homologues thereof; the organic solvent B is any one of toluene, chloroform, anhydrous ether, ethyl acetate, n-hexane, dichloromethane or petroleum ether; the N heterocyclic compound is any one of imidazole, methylimidazole, ethylimidazole, propylimidazole, butylimidazole and derivatives thereof, and vinyl imidazole or pyridine derivatives; the chemical modification by the N heterocyclic compound refers to any one of substitution reaction or addition reaction, wherein the reaction condition of the chemical modification is that the temperature is 80-120 ℃, and the reaction time is 12-24 h; the strong acid solution is any one of sulfuric acid, hydrochloric acid or phosphoric acid, wherein the protonation condition is room temperature, the reaction time is 2-48 h, and vacuum drying is carried out at 45 ℃ for 2-12 h.
2. Oligomerization of isobutene
After a 100mL stainless steel reaction kettle is replaced by inert gas, chemical immobilization is carried out
Putting the acidic ionic liquid catalyst M into a kettle, filling the isobutene raw material mixed gas to a pressure value required by the reaction, sealing, starting a stirring and heating controller, observing that a high-precision pressure gauge is continuously kept at a fixed value along with the reaction, stopping heating, immediately quenching the reaction to return to room temperature, collecting reaction liquid and the mixed gas, filtering the reaction liquid by a standing ultrafiltration membrane, purifying and recovering a reaction product and the catalyst M, and quantitatively analyzing the composition of the product by chromatography; determining components of the unreacted mixed gas by a gas chromatography-mass spectrometry technology, and calculating the conversion rate of isobutene and the selectivity of the obtained dimerization product by combining with the analysis result of the product. Wherein the dosage of the catalyst M accounts for 1.0-15 wt% of the mass of the isobutene, and the reaction temperature isThe temperature is 70-120 ℃, the reaction time is 20-50 min, and the reaction pressure is 1.0-3.0 MPa.
The invention provides chemical immobilization
The acidic ionic liquid catalyst is used for catalyzing the catalytic conversion of low-carbon olefin and synthesizing a dimerization product isooctene by high-efficiency and high-selectivity catalysis, and has the following effects and benefits:
1. the halogen-containing micron-sized resin particles are bonded with the acidic imidazolyl ionic liquid through chemical bonds, so that the problems of active component loss, poor stability, overhigh catalyst consumption and long-time reaction caused by the immobilized catalyst physical impregnation technology are solved, the reaction time can be shortened, and the reaction efficiency is improved.
2. The catalyst can provide a high-efficiency high-selectivity dimerization reaction catalytic system for the catalytic polymerization of the low-carbon olefin, the dosage of the catalyst is reduced to be below 15 wt% in the oligomerization reaction of the isobutene, the reaction time is shortened to be within 60min, the conversion rate of the low-carbon olefin is improved to 99%, and the selectivity of a dimerization product is obviously improved.
3. The activity stability of the catalyst is improved, the catalyst can be recycled for 5 times, the activity and the selectivity are basically kept unchanged, the cost of the catalyst can be obviously reduced, and the catalyst has an application value of industrial popularization for developing high-value utilization of low-carbon olefins.
Detailed Description
Chemical immobilization used in the present invention
The acidic ionic liquid catalyst is used for the catalytic polymerization of lower olefins, and the specific embodiment is described below, which is specific for understanding the content of the research in the present invention, but does not represent or limit the scope of the protection of the present invention and does not limit the content of the present invention in any way without departing from the spirit of the present invention.
Example 1 chemical immobilization
Synthesis of acidic Ionic liquid M
Sequentially washing and drying micron-sized resin carrier particles containing Cl substituent groups by toluene and absolute ethyl alcohol, adding the micron-sized resin carrier particles into a three-neck round-bottom flask containing 50mL of acetonitrile solvent, uniformly mixing, adding equimolar imidazole for chemical modification, slowly heating to 85 ℃, carrying out reflux reaction for 24h, stopping the reaction process, simply filtering and drying a catalyst in vacuum to obtain micron-sized resin particles modified by imidazole functional groups, connecting 1, 4-butyl sultone through covalent bonds to form resin amphoteric salt solid particles, protonating the resin amphoteric salt solid particles by using a sulfuric acid solution, washing and purifying the resin amphoteric salt solid particles by using the acetonitrile solvent, and drying the resin amphoteric salt solid particles in vacuum at 45 ℃ for 6h to obtain the chemical immobilized compound
And (3) an acidic ionic liquid M.
EXAMPLE 2 oligomerization of isobutylene
0.20g of immobilization was charged into a 100mL autoclave
The acidic ionic liquid catalyst M is replaced by inert gas, mixed gas containing 3.30g of isobutene is input into a reaction kettle, the pressure in the reaction kettle is increased to 2.0MPa, the reaction kettle is heated to 80 ℃, stirred and reacted for 50min, the temperature of an ice water bath is rapidly reduced to terminate the reaction, the catalyst and liquid phase mixed reaction liquid is recovered through simple filtration, and then the conversion rate of the isobutene and the selectivity of a generated dimerization product isooctene mixture are obtained by quantitative analysis of gas chromatography.
Example 3
0.20g of the same catalyst M as in example 1 was charged into a 100mL autoclave, the reaction was terminated in the same manner as in example 2 except that the reaction pressure was 2.5 MPa, the reaction temperature was 70 ℃ and the reaction was terminated for 60 minutes, and the reaction mixture was quantitatively analyzed by gas chromatography to obtain 94% conversion of isobutylene and 77% selectivity of the mixture to the dimerization product, isooctene.
Example 4
0.20g of the same catalyst M as in example 1 was charged into a 100mL autoclave, the reaction was terminated at 90 ℃ under a pressure of 2.0MPa in the same manner as in example 2 except for the other operating steps, and the reaction was terminated after 40 minutes, and the reaction mixture was quantitatively analyzed by gas chromatography to obtain 99% conversion of isobutylene and 85% selectivity of the mixture to the dimerization product isooctene.
Example 5
0.20g of the same catalyst M as in example 1 was charged into a 100mL autoclave, the reaction was terminated at 90 ℃ under a pressure of 2.0MPa in the same manner as in example 2 except for the other operating steps, and the reaction was terminated after 20 minutes, and the reaction mixture was quantitatively analyzed by gas chromatography to obtain an isobutylene conversion of 49% and a selectivity of 93% for a mixture of isooctenes as a dimerization product.
Example 6
0.10g of the same catalyst M as in example 1 was charged into a 100mL autoclave, the reaction was terminated at 70 ℃ under a pressure of 2.0MPa in the same manner as in example 2 except for the other operating steps, and the reaction was terminated after 50 minutes, and the reaction mixture was quantitatively analyzed by gas chromatography to obtain a mixture having an isobutylene conversion of 50% and an isooctene selectivity of 91% as a dimerization product.
Example 7
0.10g of the catalyst M of example 1 was charged into a 100mL autoclave, the other operation steps were the same as in example 2, the reaction pressure was 2.0MPa, the reaction temperature was 90 ℃, the reaction was terminated in 50min, and the reaction liquid was quantitatively analyzed by gas chromatography to obtain 97% conversion of isobutylene and 81% selectivity for the mixture of the dimerization product isooctene.
Example 8
0.05g of the catalyst M of example 1 was charged into a 100mL autoclave, the other operation steps were the same as in example 2, the reaction pressure was 2.0MPa, the reaction temperature was 100 ℃, the reaction was terminated in 50min, and the reaction liquid was subjected to gas chromatography quantitative analysis to obtain an isobutene conversion of 69% and a selectivity of 86% for the mixture of the dimerization product isooctene.
Example 9 Recycling of catalyst M
Putting the catalyst M recovered in the embodiment 4 into a 100mL high-pressure reaction kettle, and performing other operation steps as described in the embodiment 2, wherein the reaction pressure is 2.0MPa, the reaction temperature is 90 ℃, the reaction is terminated for 40min, the reaction is terminated, the separation of the catalyst and the reaction liquid is realized by ultrafiltration membrane filtration, the recovered catalyst is dried and enters the next recycling process, and the reaction liquid is subjected to gas chromatography quantitative analysis to obtain the conversion rate and the selectivity of the isobutene. The chemical immobilized catalyst M can be recycled for 5 times, the conversion rate of isobutene is basically kept to be more than 90%, and the selectivity of the obtained dimerization product is more than 80%, and the results are shown in Table 1.
TABLE 1 catalyst M recycle results
Although the invention has been described in detail with respect to the general description and the specific embodiments, it will be apparent to those skilled in the art that certain modifications or improvements may be made thereto based on the invention. Accordingly, such modifications and improvements are intended to be within the scope of this invention as defined by the appended claims.
Claims (5)
1. Chemical immobilization
A method for converting low-carbon olefin into isooctene by using acidic ionic liquid as catalyst, relating to chemical immobilization
The acidic ionic liquid catalyst is used for catalyzing the reaction of converting isobutene into isooctene product, and is characterized in that: the preparation method comprises the following steps of chemically modifying halogen-containing micron-sized resin carrier particles with an N heterocyclic compound in a solvent A, connecting sulfonate functional groups by using a covalent bond, purifying by using a solvent B to form resin amphoteric salt solid particles, and finally protonating by using a strong acid proton solution to prepare the chemically immobilized resin carrier particles
Acidic ionic liquid catalyst applied to catalytic oligomerization reaction in which isobutene participatesAnd after 20-60 min of ultrafiltration membrane separation, recycling the chemical immobilized catalyst, and analyzing the reaction liquid by a gas chromatography-mass spectrometer to obtain the conversion rate and selectivity of isobutene, wherein the N heterocyclic compound is any one of imidazole, methylimidazole, ethylimidazole, propylimidazole and butylimidazole, the sulfonate functional group is any one of butyl sulfonate and propyl sulfonate, and the strong-acid proton solution is any one of sulfuric acid or hydrochloric acid.
2. The chemical immobilization method of claim 1
The method for converting low-carbon olefin into isooctene by using acidic ionic liquid as catalyst is characterized by comprising the following steps: micron-sized resin carrier particles containing halogen, wherein halogen means any one of X ═ I, Br or Cl, and wherein the size of the resin carrier particles is any size within the range of 0.50 to 2000 μm.
3. The chemical immobilization method of claim 1
The method for converting low-carbon olefin into isooctene by using acidic ionic liquid as catalyst is characterized by comprising the following steps: and chemically modifying the N-heterocyclic compound in a solvent A, wherein the solvent A refers to any one of dichloromethane, acetonitrile, toluene, trimethylbenzene, N-dimethylformamide and chloroform, and the chemical modification refers to one of substitution reaction or addition reaction under the conditions that the temperature is 80-120 ℃ and the reaction time is 12-24 hours.
4. The chemical immobilization method of claim 1
The method for converting low-carbon olefin into isooctene by using acidic ionic liquid as catalyst is characterized by comprising the following steps: purifying with solvent B to obtain resin amphoteric salt solid particles, wherein solvent B is toluene,And performing protonation on any one of chloroform, anhydrous ether, ethyl acetate, normal hexane, dichloromethane or petroleum ether under the reaction conditions of room temperature, reaction time of 2-48 h and vacuum drying at 45 ℃ for 2-12 h.
5. The chemical immobilization method of claim 1
The method for converting low-carbon olefin into isooctene by using acidic ionic liquid as catalyst is characterized by comprising the following steps: the catalyst is applied to catalytic oligomerization reaction in which catalytic isobutene participates, the dosage of the catalyst accounts for 1.0-15 wt% of the mass of the isobutene, the reaction temperature is 70-120 ℃, and the reaction pressure is 1.0-3.0 MPa.
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Citations (3)
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| CN103657720A (en) * | 2013-12-10 | 2014-03-26 | 王金明 | Post-ether carbon-four polymerized catalyst as well as preparation method and application thereof |
| CN107812538A (en) * | 2017-11-22 | 2018-03-20 | 林州市科能材料科技有限公司 | A kind of preparation method of support type glyoxaline ion liquid catalyst |
| CN109433263A (en) * | 2018-12-11 | 2019-03-08 | 中国科学院过程工程研究所 | A kind of method of the ionic liquid-catalyzed isobutene oligomerisation of proton acid type pyridyl group |
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| US8017821B2 (en) * | 2009-03-24 | 2011-09-13 | Cpc Corporation, Taiwan | Process for isomerization of tetrahydrodicyclopentadiene using supported acidic ionic liquid as a catalyst |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103657720A (en) * | 2013-12-10 | 2014-03-26 | 王金明 | Post-ether carbon-four polymerized catalyst as well as preparation method and application thereof |
| CN107812538A (en) * | 2017-11-22 | 2018-03-20 | 林州市科能材料科技有限公司 | A kind of preparation method of support type glyoxaline ion liquid catalyst |
| CN109433263A (en) * | 2018-12-11 | 2019-03-08 | 中国科学院过程工程研究所 | A kind of method of the ionic liquid-catalyzed isobutene oligomerisation of proton acid type pyridyl group |
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