CN114014775A - Functionalized surface active ionic liquid and preparation method and application thereof - Google Patents
Functionalized surface active ionic liquid and preparation method and application thereof Download PDFInfo
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- CN114014775A CN114014775A CN202111423640.XA CN202111423640A CN114014775A CN 114014775 A CN114014775 A CN 114014775A CN 202111423640 A CN202111423640 A CN 202111423640A CN 114014775 A CN114014775 A CN 114014775A
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- 239000002608 ionic liquid Substances 0.000 title claims abstract description 95
- 238000002360 preparation method Methods 0.000 title claims abstract description 15
- 238000006243 chemical reaction Methods 0.000 claims abstract description 32
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 claims abstract description 25
- 239000003054 catalyst Substances 0.000 claims abstract description 18
- 239000002994 raw material Substances 0.000 claims abstract description 13
- 239000003377 acid catalyst Substances 0.000 claims abstract description 10
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 34
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 27
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 24
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 20
- 150000001767 cationic compounds Chemical class 0.000 claims description 19
- 229940098779 methanesulfonic acid Drugs 0.000 claims description 17
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 15
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 15
- 238000002156 mixing Methods 0.000 claims description 15
- 150000001449 anionic compounds Chemical class 0.000 claims description 14
- KBPLFHHGFOOTCA-UHFFFAOYSA-N caprylic alcohol Natural products CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 claims description 14
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 claims description 14
- 230000035484 reaction time Effects 0.000 claims description 13
- 238000010438 heat treatment Methods 0.000 claims description 12
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 10
- 239000003960 organic solvent Substances 0.000 claims description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 9
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 claims description 8
- HLZKNKRTKFSKGZ-UHFFFAOYSA-N tetradecan-1-ol Chemical compound CCCCCCCCCCCCCCO HLZKNKRTKFSKGZ-UHFFFAOYSA-N 0.000 claims description 7
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 6
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 claims description 5
- 125000005466 alkylenyl group Chemical group 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 230000001681 protective effect Effects 0.000 claims description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 3
- 238000005804 alkylation reaction Methods 0.000 abstract description 10
- 230000003197 catalytic effect Effects 0.000 abstract description 10
- 239000002253 acid Substances 0.000 abstract description 8
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 abstract description 8
- 230000000694 effects Effects 0.000 abstract description 7
- 239000004215 Carbon black (E152) Substances 0.000 abstract description 6
- 150000002430 hydrocarbons Chemical class 0.000 abstract description 5
- 229930195733 hydrocarbon Natural products 0.000 abstract description 4
- 239000001282 iso-butane Substances 0.000 abstract description 4
- 239000007788 liquid Substances 0.000 abstract description 3
- 239000004094 surface-active agent Substances 0.000 abstract description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 abstract 1
- -1 alcohol amine Chemical class 0.000 abstract 1
- 150000001408 amides Chemical class 0.000 abstract 1
- 150000008050 dialkyl sulfates Chemical class 0.000 abstract 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 21
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 125000000129 anionic group Chemical group 0.000 description 8
- 239000000203 mixture Substances 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 150000001450 anions Chemical class 0.000 description 5
- 230000008901 benefit Effects 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 238000006555 catalytic reaction Methods 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 239000005457 ice water Substances 0.000 description 4
- 238000005956 quaternization reaction Methods 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical compound COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 description 3
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 238000004817 gas chromatography Methods 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 description 2
- 230000029936 alkylation Effects 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000005034 decoration Methods 0.000 description 2
- 238000013461 design Methods 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- IAQRGUVFOMOMEM-ONEGZZNKSA-N trans-but-2-ene Chemical compound C\C=C\C IAQRGUVFOMOMEM-ONEGZZNKSA-N 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- FLTJDUOFAQWHDF-UHFFFAOYSA-N trimethyl pentane Natural products CCCCC(C)(C)C FLTJDUOFAQWHDF-UHFFFAOYSA-N 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 238000003442 catalytic alkylation reaction Methods 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000012295 chemical reaction liquid Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 238000003487 electrochemical reaction Methods 0.000 description 1
- 238000004945 emulsification Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- UQSQSQZYBQSBJZ-UHFFFAOYSA-N fluorosulfonic acid Chemical compound OS(F)(=O)=O UQSQSQZYBQSBJZ-UHFFFAOYSA-N 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000010327 methods by industry Methods 0.000 description 1
- KWKAKUADMBZCLK-UHFFFAOYSA-N methyl heptene Natural products CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 1
- 238000010606 normalization Methods 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 238000004445 quantitative analysis Methods 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000013557 residual solvent Substances 0.000 description 1
- 238000002390 rotary evaporation Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 238000005728 strengthening Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/89—Carboxylic acid amides having nitrogen atoms of carboxamide groups quaternised
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- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/0277—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
- 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
- B01J31/0279—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 cationic portion being acyclic or nitrogen being a substituent on a ring
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/0277—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
- 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
- B01J31/0285—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 also containing elements or functional groups covered by B01J31/0201 - B01J31/0274
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2/00—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms
- C07C2/54—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition of unsaturated hydrocarbons to saturated hydrocarbons or to hydrocarbons containing a six-membered aromatic ring with no unsaturation outside the aromatic ring
- C07C2/56—Addition to acyclic hydrocarbons
- C07C2/58—Catalytic processes
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- C07C2/00—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms
- C07C2/54—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition of unsaturated hydrocarbons to saturated hydrocarbons or to hydrocarbons containing a six-membered aromatic ring with no unsaturation outside the aromatic ring
- C07C2/56—Addition to acyclic hydrocarbons
- C07C2/58—Catalytic processes
- C07C2/62—Catalytic processes with acids
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C213/08—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reactions not involving the formation of amino groups, hydroxy groups or etherified or esterified hydroxy groups
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
- C07C215/02—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C215/40—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton with quaternised nitrogen atoms bound to carbon atoms of the carbon skeleton
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/24—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of esters of sulfuric acids
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- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/32—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of salts of sulfonic acids
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- C07C305/00—Esters of sulfuric acids
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- C07C305/04—Esters of sulfuric acids having oxygen atoms of sulfate groups bound to acyclic carbon atoms of a carbon skeleton being acyclic and saturated
- C07C305/06—Hydrogenosulfates
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- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/01—Sulfonic acids
- C07C309/02—Sulfonic acids having sulfo groups bound to acyclic carbon atoms
- C07C309/03—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
- C07C309/04—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton containing only one sulfo group
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- C10L1/14—Organic compounds
- C10L1/16—Hydrocarbons
- C10L1/1691—Hydrocarbons petroleum waxes, mineral waxes; paraffines; alkylation products; Friedel-Crafts condensation products; petroleum resins; modified waxes (oxidised)
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- B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
- B01J2231/30—Addition reactions at carbon centres, i.e. to either C-C or C-X multiple bonds
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Abstract
The invention provides a functionalized surface active ionic liquid, a preparation method and application thereof, belonging to the technical field of ionic liquid surfactants. According to the invention, dialkyl amide/dialkyl alcohol amine and dialkyl sulfate/dialkyl carbonate are used as raw materials to prepare a functionalized surface active ionic liquid, and the functionalized surface active ionic liquid is successfully applied to an isobutane alkylation reaction as a catalytic assistant according to the surface activity characteristics of the functionalized surface active ionic liquid, and is used for catalyzing the alkylation reaction in cooperation with an acid catalyst, so that the surface tension of an acid-hydrocarbon interface is reduced, and further, the high-octane alkylate oil is obtained. The ionic liquid has simple preparation method and low cost, has catalytic activity and surface activity, can improve the conversion rate of main reaction, maintain the activity of the catalyst, reduce the interfacial tension of acid hydrocarbon and improve the octane number of the alkylate product when being applied to the liquid acid alkylation reaction.
Description
Technical Field
The invention relates to the technical field of ionic liquid surfactants, in particular to a functionalized surface active ionic liquid and a preparation method and application thereof.
Background
The ionic liquid is low-temperature molten salt formed by specific anions and cations, has the advantages of low vapor pressure, low melting point and high chemical stability, and can achieve the adjustment of the structure and the function of the ionic liquid by regulating the length of an alkyl carbon chain and changing the type of the anions. Therefore, the ionic liquid has been widely studied and applied in the fields of catalytic reactions, polymerization reactions, electrochemical reactions, and the like. However, in the practical application process of the ionic liquid, the problems of complex synthesis process, high raw material cost, high finished product viscosity, difficult separation and recovery and the like are faced, and the industrial production and application of the ionic liquid are greatly limited, so that the design and synthesis of the ionic liquid which is simple in synthesis process, low in comprehensive cost and easy to separate and recover is the key for solving the problems. Currently, ionic liquids are generally very expensive in cost, and alternative low-cost ionic liquids are lacking.
The alkylate oil is used as a gasoline blending component with the highest comprehensive performance, has the advantages of high octane number, no nitrogen and sulfur component, low vapor pressure and the like, and has the reputation of liquid gold. The alkylate is produced by taking low-carbon olefin (generally butylene) and isoparaffin (generally isobutane) as raw materials under the condition of strong acid, the octane number (RON) of the alkylate can reach 94.5, and compared with C5/C6 isomerized oil (87.5) and straight-run light gasoline (68.0), the alkylate has the advantage that the octane number is respectively 7.0 and 26.5 units higher. The mainstream alkylation process is mainly a concentrated sulfuric acid process represented by DuPont Stratco, and by 3 months in 2017, 74 sulfuric acid process alkylation devices are totally arranged in China, the capacity of the traditional sulfuric acid alkylation process occupies 90% of the total production capacity of the alkylate oil, and in 41 new alkylation industrial devices which are newly built before 2020, the traditional sulfuric acid process also occupies more than 80% of the new production capacity. The addition of the catalytic assistant can effectively improve the catalytic activity of the catalyst, reduce the interfacial tension and thickness of acid hydrocarbon, improve the mass transfer efficiency and achieve the purposes of improving the octane number of the alkylate oil product and reducing the acid consumption of the process on the basis of not changing the original reaction equipment. The fluorosulfonic acid catalyst (CN106944132A) proposed by the process engineering research of chinese academy of sciences can shorten the reaction time under the condition of low acid-hydrocarbon ratio and effectively improve the selectivity of C8 in the alkylated product and the selectivity and octane number of Trimethylpentane (TMP) with high octane number in the C8 component.
The addition of the catalytic assistant in the alkylation reaction has the advantages that although the product quality is obviously improved, the use benefit in the actual process is not obvious, the ionic liquid is difficult to prepare in a large scale and generally high in manufacturing cost, the ionic liquid capable of assisting in catalyzing the alkylation reaction often contains halogen elements, the ionic liquid after the reaction is difficult to treat and recover, and the equipment is easy to corrode after long-term use.
Therefore, how to obtain an ionic liquid which is low in cost, environment-friendly and free of corrosion to equipment for preparing alkylate is a technical problem which is urgently needed to be solved at present.
Disclosure of Invention
The invention aims to provide a functionalized surface active ionic liquid, a preparation method and application thereof, the functionalized surface active ionic liquid has low cost, easily obtained raw materials and simple synthesis, and when the functionalized surface active ionic liquid is applied to the preparation of alkylate, the octane number can be obviously improved, the acid consumption can be reduced, and the high activity of a catalytic system can be maintained.
In order to achieve the above object, the present invention provides the following technical solutions:
the invention provides a functionalized surface active ionic liquid, which comprises an anionic compound and a cationic compound, wherein the cationic compound comprises at least one of structures shown in a formula I, the anionic compound comprises at least one of structures shown in a formula II,
in the formula I, R1a、R1b、R1c、R2a、R2b、R2c、R3a、R3b is independently C1-16Alkyl or phenyl of (a);
in the formula II, m is an integer of 1-16.
The invention provides a preparation method of functionalized surface active ionic liquid, which comprises the following steps:
1) dissolving a cationic compound in an organic solvent, adding an anionic compound under a protective atmosphere, and heating for reaction to obtain a functionalized short-branched-chain surface active ionic liquid;
2) and mixing monohydric alcohol, methanesulfonic acid and the functionalized short-chain branched surface active ionic liquid, and reacting to obtain the functionalized long-chain branched surface active ionic liquid.
Further, the cationic compound is a dialkylamide or a dialkanolamine, the dialkylamide comprising N, N-dimethylformamide and/or N, N-dimethylacetamide; the dialkanolamine comprises N, N-dimethylethanolamine.
Further, the organic solvent comprises one or more of toluene, tetrahydrofuran, methanol, ethanol, acetone and dichloromethane;
the mass volume ratio of the cationic compound to the organic solvent is 1 g: 5-8 ml.
Further, the monohydric alcohol comprises one or more of n-tetradecanol, n-decanol, n-octanol, n-pentanol and n-butanol.
Further, the mass ratio of the cationic compound to the anionic compound is 1: 0.5 to 2.0.
Further, the mass ratio of the monohydric alcohol to the functionalized short-chain branched surface active ionic liquid to the methanesulfonic acid is 1: 0.2-0.8: 0.05 to 0.15.
Further, the heating reaction temperature in the step 1) is 60-80 ℃, and the heating reaction time is 3-15 hours;
the mixing speed in the step 2) is 100-600 rpm, the mixing time is not less than 12 hours, the reaction temperature is 70-90 ℃, and the reaction time is 10-14 hours.
The invention provides application of a functionalized surface active ionic liquid in preparation of alkylate, which comprises a raw material of alkylate, a catalyst and the functionalized surface active ionic liquid.
Further, the raw material of the alkylate oil comprises a raw material with a volume ratio of 1-30: 1, said catalyst comprising an acid catalyst; the mass volume ratio of the raw material of the alkylate oil, the catalyst and the functionalized surface active ionic liquid is 0.5-1.5 ml: 2-4 g: 0.05 to 5.0 g.
The invention has the beneficial effects that:
1. the functionalized surface active ionic liquid prepared by the invention is a novel functionalized material which is low in cost, does not contain halogen elements, can design and regulate the chain length of a carbon chain and has catalytic activity and surface activity;
2. the functionalized surface active ionic liquid prepared by the invention can be directly applied to the process of generating alkylate by carbon tetra-alkylation catalysis in the field of petrochemical industry, plays the roles of catalysis assistance, interface activation and emulsification and prolonging the service life of an acid catalyst, and obtains better application effect.
Detailed Description
The invention provides a functionalized surface active ionic liquid, which comprises an anionic compound and a cationic compound, wherein the cationic compound comprises at least one of structures shown in a formula I, the anionic compound comprises at least one of structures shown in a formula II,
in the formula I, R1a、R1b、R1c、R2a、R2b、R2c、R3a、R3b is independently C1-16Alkyl or phenyl of (3), preferably C5～10Alkyl or phenyl of (a);
in the formula II, m is an integer of 1-16, and specifically can be 1, 2, 3, 5, 7, 9, 10, 12, 13 and 16.
The invention provides a preparation method of functionalized surface active ionic liquid, which comprises the following steps:
1) dissolving a cationic compound in an organic solvent, adding an anionic compound under a protective atmosphere, and heating for reaction to obtain a functionalized short-branched-chain surface active ionic liquid;
2) and mixing monohydric alcohol, methanesulfonic acid and the functionalized short-chain branched surface active ionic liquid, and reacting to obtain the functionalized long-chain branched surface active ionic liquid.
In the present invention, the cationic compound is a dialkylamide or dialkanolamine, the dialkylamide comprising N, N-dimethylformamide and/or N, N-dimethylacetamide, preferably N, N-dimethylacetamide; in the present invention, the dialkanolamine is preferably N, N-dimethylethanolamine.
In the present invention, the organic solvent comprises one or more of toluene, tetrahydrofuran, methanol, ethanol, acetone and dichloromethane, preferably one or more of toluene, methanol, ethanol and acetone, and more preferably one or more of toluene, ethanol and acetone.
In the present invention, the mass-to-volume ratio of the cationic compound to the organic solvent is 1 g: 5-8 ml, preferably 1 g: 5.5 to 7.5ml, more preferably 1 g: 6.9 ml.
In the present invention, the monohydric alcohol comprises one or more of n-tetradecanol, n-decanol, n-octanol, n-pentanol and n-butanol, preferably one or more of n-tetradecanol, n-pentanol and n-butanol, and more preferably n-butanol.
In the present invention, the mass ratio of the cationic compound to the anionic compound is 1: 0.5 to 2.0, preferably 1: 0.8 to 1.5, and more preferably 1: 1.2.
in the invention, the mass ratio of the monohydric alcohol to the functionalized short-chain branched surface active ionic liquid to the methanesulfonic acid is 1: 0.2-0.8: 0.05-0.15, preferably 1: 0.3-0.7: 0.08 to 0.12, and more preferably 1: 0.5: 0.1.
in the invention, the heating reaction in the step 1) is carried out at the temperature of 60-80 ℃ for 3-15 h; preferably, the heating reaction temperature is 65-75 ℃, and the heating reaction time is 4-12 h; further preferably, the heating reaction temperature is 70 ℃, and the heating reaction time is 5-10 h.
In the invention, the cationic compound dissolved in the organic solvent needs to be cooled to 10-15 ℃ in an ice water bath before the heating reaction in the step 1), and the temperature is preferably 12 ℃.
In the invention, the anionic compound in the step 1) is added dropwise, and the anionic compound is added while stirring and mixing at a rotation speed of 50-80 rpm, preferably 60-70 rpm.
In the invention, the rotation speed of the mixing in the step 2) is 100-600 rpm, the mixing time is more than or equal to 12 hours, the reaction temperature is 70-90 ℃, and the reaction time is 10-14 hours; preferably, the mixing speed is 200-500 rpm, the mixing time is more than or equal to 13 hours, the reaction temperature is 75-85 ℃, and the reaction time is 11-13 hours; further preferably, the mixing speed is 300-400 rpm, the mixing time is not less than 14h, the reaction temperature is 80 ℃, and the reaction time is 12 h.
The invention provides application of a functionalized surface active ionic liquid in preparation of alkylate, which comprises a raw material of alkylate, a catalyst and the functionalized surface active ionic liquid.
In the invention, the raw material of the alkylate oil comprises the following components in a volume ratio of 1-30: 1, preferably 5 to 20: 1, more preferably 10: 1; in the present invention, the catalyst comprises an acid catalyst, which is preferably sulfuric acid.
In the invention, the mass volume ratio of the raw material of the alkylate oil, the catalyst and the functionalized surface active ionic liquid is 0.5-1.5 ml: 2-4 g: 0.05-5.0 g, preferably 0.8-1.2 ml: 2-3 g: 0.1 to 4.0g, more preferably 1.0 ml: 2 g: 1.0 to 30 g.
In the present invention, the alkylate is prepared under the following conditions: the reaction temperature is-10-15 ℃, the reaction time is 0.1-20 min, the reaction pressure is 0.02-10 MPa, and the stirring speed is 100-5000 rpm; preferably, the reaction temperature is-5-10 ℃, the reaction time is 5-15 min, the reaction pressure is 0.1-9 MPa, and the stirring speed is 500-4000 rpm; further preferably, the reaction temperature is-2-8 ℃, the reaction time is 8-10 min, the reaction pressure is 5-8 MPa, and the stirring speed is 1000-2000 rpm.
In the present invention, the term "C1-16Alkyl "refers to a straight or branched chain saturated hydrocarbon group having 1 to 16 carbon atoms.
In the present invention, all percentages are by weight, and all equipment and materials are commercially available or commonly used in the industry, unless otherwise specified.
The technical solutions provided by the present invention are described in detail below with reference to examples, but they should not be construed as limiting the scope of the present invention.
Example 1
Preparing functionalized short-chain branched surface active ionic liquid:
dissolving N, N-dimethylformamide (0.10mol) in toluene (50mL), cooling the solution to 10 deg.C in ice water bath under nitrogen protection, slowly adding dimethyl sulfate (0.11mol) dropwise to obtain mixture, stirring for 3h, and rotary evaporating at 70rpm and 75 deg.CFor 3h, washing with ethyl acetate, removing residual ethyl acetate under reduced pressure, and drying the resulting white solid under high vacuum for 12h to give [ N1,1,1,1][C1SO4]。
Preparation of alkylate:
331.2g of sulfuric acid and 3.31g of the obtained [ N ]1,1,1,1][C1SO4](the addition amount is 1.0 wt% of sulfuric acid) is added into a 1L glass reaction kettle, the pressure in the kettle is set to be 0.5MPa, the reaction temperature is 8 ℃, 120ml of raw material gas (isobutane and trans-2-butene, the volume ratio of the isobutane to the trans-2-butene is 6.5:1) is added and stirred, the stirring speed is 3000rpm, the reaction time is 15min, after the reaction is finished, the reaction liquid is transferred into a separating funnel, standing and layering are carried out, the upper layer is alkylate oil, the lower layer is catalyst, and an alkylate oil product and catalyst are obtained after separation.
Example 2
The difference from example 1 is that the surface active ionic liquid is obtained by quaternization of N, N-dimethyl acetamide and dimethyl sulfate in toluene solvent.
Example 3
The difference from example 1 is that the surface active ionic liquid is obtained by quaternization of N, N-dimethylethanolamine with dimethyl sulfate in a toluene solvent.
Example 4
Dissolving N, N-dimethylformamide (0.10mol) in methanol (50mL), cooling the solution to 12 ℃ in an ice-water bath under the protection of nitrogen, slowly dropwise adding dimethyl carbonate (0.11mol) to obtain a mixture, stirring at 100 ℃ for 12h, performing rotary evaporation at 70rpm and 75 ℃ for 3h, washing with ethyl acetate, removing residual ethyl acetate under reduced pressure, and drying the obtained white solid under high vacuum for 12h to obtain the corresponding surface active ionic liquid.
Example 5
The difference from example 4 is that the surface active ionic liquid is obtained by quaternization of N, N-dimethylacetamide with dimethyl carbonate in methanol solvent.
Example 6
The difference from example 4 is that the surface active ionic liquid is obtained by quaternization of N, N-dimethylethanolamine with dimethyl carbonate in a methanol solvent.
Example 7
Preparing a functionalized long-chain branched surface active ionic liquid:
n-tetradecanol (0.10mol) was added to the short-chain branched surface active ionic liquid (0.01mol) obtained in example 1, and stirred at 500rpm to completely dissolve it, followed by addition of methanesulfonic acid (0.001mol) to obtain a mixture, and the mixture was stirred at 80 ℃ for 12 hours, and the methanol formed was continuously removed by vacuum distillation. After the methanol was removed, the mixture was cooled to room temperature and diethyl ether was added to the mixture after the formation of a white solid was observed and the reaction flask was placed in an ice-water bath to ensure complete precipitation of the product. And centrifuging the precipitated mixture at 9000rpm for 3min, filtering, washing the solid with diethyl ether, removing residual solvent under reduced pressure, and drying the obtained white solid under high vacuum for 12 hr to obtain the surface active ionic liquid with the anion branch chain length of 14.
The alkylate was prepared as in example 1.
Example 8
The difference from example 7 is that the ionic liquid obtained in example 1 is dissolved in n-decanol, and methanesulfonic acid is added to react to obtain the surface active ionic liquid with the anion branch length of 10.
Example 9
The difference from example 7 is that the ionic liquid obtained in example 1 was dissolved in n-octanol, and methanesulfonic acid was added to react to obtain a surface active ionic liquid having an anionic branched chain length of 8.
Example 10
The difference from example 7 is that the ionic liquid obtained in example 2 is dissolved in n-tetradecanol, and methanesulfonic acid is added to react to obtain a surface active ionic liquid with an anionic branched chain length of 14.
Example 11
The difference from example 7 is that the ionic liquid obtained in example 2 is dissolved in n-decanol, and methanesulfonic acid is added to react to obtain the surface active ionic liquid with the anion branch length of 10.
Example 12
The difference from example 7 is that the ionic liquid obtained in example 2 was dissolved in n-octanol, and methanesulfonic acid was added to react to obtain a surface active ionic liquid having an anionic branched chain length of 8.
Example 13
The difference from example 7 is that the ionic liquid obtained in example 3 is dissolved in n-decanol, and methanesulfonic acid is added to react to obtain a surface active ionic liquid with an anionic branched chain length of 10.
Example 14
The same as example 7, except that the ionic liquid obtained in example 3 was dissolved in n-octanol, and methanesulfonic acid was added to react, thereby obtaining a surface-active ionic liquid having an anionic branched chain length of 8.
Example 15
The difference from example 7 is that the ionic liquid obtained in example 4 was dissolved in n-tetradecanol, and methanesulfonic acid was added to react to obtain a surface active ionic liquid having an anionic branch length of 14.
Example 16
The difference from example 7 is that the ionic liquid obtained in example 5 is dissolved in n-decanol, and methanesulfonic acid is added to react to obtain a surface active ionic liquid with an anionic branched chain length of 10.
Example 17
The same as example 7, except that the ionic liquid obtained in example 6 was dissolved in n-octanol, and methanesulfonic acid was added to react, thereby obtaining a surface-active ionic liquid having an anionic branched chain length of 8.
1. Detection of octane number
Product analysis of the alkylate oil samples obtained in the experiment by gas chromatography: agilent Technology GC7890B gas chromatography, HP-PONA (50 m.times.0.2 mm. times.0.5 μm) capillary chromatography column, quantitative method using area normalization.
The alkylate prepared in examples 1-17 and the blank (without addition of the functionalized surface active ionic liquid prepared according to the present invention) was tested by gas chromatography and the octane number measured is shown in table 1.
TABLE 1 octane number test values for alkylate obtained in examples 1-17 and blank set
From the above embodiments, the invention provides a functionalized surface active ionic liquid, and a preparation method and an application thereof. As can be seen from Table 1, the octane number of the alkylate prepared by using the functionalized surfactant ionic liquid as a catalytic auxiliary in cooperation with a sulfuric acid catalytic alkylation reaction is 0.78-3.27 units higher than that of the alkylate prepared by using pure sulfuric acid without adding any auxiliary.
2. The composite catalyst of the functionalized surface active ionic liquid and the sulfuric acid prepared in the examples 1 to 17 is recycled for 8 times, and the experimental result shows that: after 8 times of cyclic reaction, the octane number of the alkylate oil obtained by the reaction is still kept above 92, which shows that the functionalized surface active ionic liquid prepared by the invention has good stability and high catalytic efficiency.
Comparative example 1
The difference from example 10 is that the amount of the catalyst promoter added is 0.3 wt% based on the acid catalyst.
As a result, it was found that: octane number 95.12
Comparative example 2
The same as example 10 except that the amount of the catalyst promoter added was 3.0% by weight based on the acid catalyst.
As a result, it was found that: octane number 95.56
Comparative example 3
The difference from example 1 is that the amount of the catalyst promoter added is 5.0 wt% based on the acid catalyst.
As a result, it was found that: octane number 93.86
It can be seen from the above comparative experiments that when the addition amount is increased from 0.3 wt% to 3.0 wt%, the octane number of the alkylate increases from 95.12 to 95.56, since the carbon chain of the long-chain branched ionic liquid tends to be perpendicular to the reaction acid/hydrocarbon interface, thereby reducing the interfacial tension, making the two-phase contact of the acid and the hydrocarbon more sufficient, and promoting the interface mass transfer. However, when the amount of addition reaches 5.0 wt%, the octane number is significantly reduced by 1.5 units, because the acidity of the liquid acid catalyst is diluted when more ionic liquid is added, and the reaction strengthening effect is not achieved, and the catalytic activity of the catalyst is reduced, but still 1.77 units higher than that of the alkylate (92.09) obtained by the catalysis of pure sulfuric acid.
The foregoing is only a preferred embodiment of the present invention, and it should be noted that, for those skilled in the art, various modifications and decorations can be made without departing from the principle of the present invention, and these modifications and decorations should also be regarded as the protection scope of the present invention.
Claims (10)
1. A functionalized surface active ionic liquid, characterized in that the functionalized surface active ionic liquid comprises an anionic compound and a cationic compound, wherein the cationic compound comprises at least one of the structures shown in the formula I, and the anionic compound comprises at least one of the structures shown in the formula II,
in the formula I, R1a、R1b、R1c、R2a、R2b、R2c、R3a、R3b is independently C1-16Alkyl or phenyl of (a);
in the formula II, m is an integer of 1-16.
2. The method for preparing the functionalized surface active ionic liquid according to claim 1, which comprises the following steps:
1) dissolving a cationic compound in an organic solvent, adding an anionic compound under a protective atmosphere, and heating for reaction to obtain a functionalized short-branched-chain surface active ionic liquid;
2) and mixing monohydric alcohol, methanesulfonic acid and the functionalized short-chain branched surface active ionic liquid, and reacting to obtain the functionalized long-chain branched surface active ionic liquid.
3. The method of claim 2, wherein the cationic compound is a dialkylamide or a dialkanolamine, the dialkylamide comprising N, N-dimethylformamide and/or N, N-dimethylacetamide; the dialkanolamine comprises N, N-dimethylethanolamine.
4. The method for preparing the functionalized surface active ionic liquid according to claim 2 or 3, wherein the organic solvent comprises one or more of toluene, tetrahydrofuran, methanol, ethanol, acetone and dichloromethane;
the mass volume ratio of the cationic compound to the organic solvent is 1 g: 5-8 ml.
5. The method of claim 4, wherein the monohydric alcohol comprises one or more of n-tetradecanol, n-decanol, n-octanol, n-pentanol, and n-butanol.
6. The method for preparing the functionalized surface active ionic liquid according to claim 2 or 5, wherein the mass ratio of the cationic compound to the anionic compound is 1: 0.5 to 2.0.
7. The method for preparing the functionalized surface active ionic liquid according to claim 6, wherein the mass ratio of the monohydric alcohol to the functionalized short-chain branched surface active ionic liquid to the methanesulfonic acid is 1: 0.2-0.8: 0.05 to 0.15.
8. The preparation method of the functionalized surface active ionic liquid according to claim 7, wherein the heating reaction in the step 1) is carried out at a temperature of 60-80 ℃ for 3-15 h;
the mixing speed in the step 2) is 100-600 rpm, the mixing time is not less than 12 hours, the reaction temperature is 70-90 ℃, and the reaction time is 10-14 hours.
9. Use of a functionalized surface active ionic liquid according to claim 1 for the preparation of an alkylate comprising an alkylate feedstock, a catalyst and a functionalized surface active ionic liquid.
10. The use according to claim 9, wherein the alkylate feedstock comprises, by volume, from 1 to 30: 1, said catalyst comprising an acid catalyst; the mass volume ratio of the raw material of the alkylate oil, the catalyst and the functionalized surface active ionic liquid is 0.5-1.5 ml: 2-4 g: 0.05 to 5.0 g.
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