CN101962318A - Method for synthesizing polymethoxy dimethyl ether under catalysis of geminal dicationic ionic liquid - Google Patents
Method for synthesizing polymethoxy dimethyl ether under catalysis of geminal dicationic ionic liquid Download PDFInfo
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- ionic liquid
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- 238000000034 method Methods 0.000 title claims abstract description 21
- 239000002608 ionic liquid Substances 0.000 title claims abstract description 10
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 title claims description 24
- 238000006555 catalytic reaction Methods 0.000 title claims description 4
- 230000002194 synthesizing effect Effects 0.000 title abstract 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 75
- 238000006243 chemical reaction Methods 0.000 claims abstract description 33
- 239000002994 raw material Substances 0.000 claims abstract description 14
- 239000003054 catalyst Substances 0.000 claims abstract description 10
- -1 polyoxymethylene dimethyl ether Polymers 0.000 claims abstract description 7
- BGJSXRVXTHVRSN-UHFFFAOYSA-N 1,3,5-trioxane Chemical group C1OCOCO1 BGJSXRVXTHVRSN-UHFFFAOYSA-N 0.000 claims description 28
- 150000002500 ions Chemical class 0.000 claims description 16
- 239000007788 liquid Substances 0.000 claims description 7
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 claims description 5
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 4
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 4
- 125000002091 cationic group Chemical group 0.000 claims description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 4
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 2
- 241000370738 Chlorion Species 0.000 claims description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 230000008878 coupling Effects 0.000 claims description 2
- 238000010168 coupling process Methods 0.000 claims description 2
- 238000005859 coupling reaction Methods 0.000 claims description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-M dihydrogenphosphate Chemical compound OP(O)([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-M 0.000 claims description 2
- 150000002460 imidazoles Chemical class 0.000 claims description 2
- YPJKMVATUPSWOH-UHFFFAOYSA-N nitrooxidanyl Chemical compound [O][N+]([O-])=O YPJKMVATUPSWOH-UHFFFAOYSA-N 0.000 claims description 2
- 150000003235 pyrrolidines Chemical class 0.000 claims description 2
- 230000035484 reaction time Effects 0.000 claims description 2
- 239000002283 diesel fuel Substances 0.000 abstract description 9
- 229930040373 Paraformaldehyde Natural products 0.000 abstract description 3
- 239000000654 additive Substances 0.000 abstract description 3
- 230000000996 additive effect Effects 0.000 abstract description 3
- 208000012839 conversion disease Diseases 0.000 abstract description 3
- 229920002866 paraformaldehyde Polymers 0.000 abstract description 3
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 238000003786 synthesis reaction Methods 0.000 abstract 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 16
- NKDDWNXOKDWJAK-UHFFFAOYSA-N dimethoxymethane Chemical compound COCOC NKDDWNXOKDWJAK-UHFFFAOYSA-N 0.000 description 12
- 230000009466 transformation Effects 0.000 description 9
- 238000004587 chromatography analysis Methods 0.000 description 8
- 239000007789 gas Substances 0.000 description 8
- 229910052757 nitrogen Inorganic materials 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- 239000003921 oil Substances 0.000 description 5
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 230000003197 catalytic effect Effects 0.000 description 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 238000005260 corrosion Methods 0.000 description 2
- 230000007797 corrosion Effects 0.000 description 2
- 238000007599 discharging Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
- 230000003628 erosive effect Effects 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000000779 smoke Substances 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 238000007171 acid catalysis Methods 0.000 description 1
- 239000011831 acidic ionic liquid Substances 0.000 description 1
- 229910000323 aluminium silicate Inorganic materials 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 150000001983 dialkylethers Chemical class 0.000 description 1
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000295 fuel oil Substances 0.000 description 1
- 239000002638 heterogeneous catalyst Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 239000011973 solid acid Substances 0.000 description 1
- 239000011949 solid catalyst Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000002341 toxic gas Substances 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
Landscapes
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
本发明公开了一种哑铃型离子液体催化合成聚甲氧基二甲醚的方法。该方法使用甲醇和三聚甲醛为反应原料，采用哑铃型离子液体作为催化剂，在反应温度333～423K，反应压力0.5MPa～3MPa的反应条件下催化合成聚甲氧基二甲醚。本发明反应转化率最高可达91.5％，产物选择性高，有效柴油添加组分DMM3-8的含量可达49.6％。The invention discloses a method for catalyzing and synthesizing polyoxymethylene dimethyl ether with a dumbbell-shaped ionic liquid. The method uses methanol and paraformaldehyde as reaction raw materials, adopts dumbbell-shaped ionic liquid as a catalyst, and catalyzes the synthesis of polyoxymethylene dimethyl ether under the reaction conditions of reaction temperature 333-423K and reaction pressure 0.5MPa-3MPa. The reaction conversion rate of the invention can reach up to 91.5%, the product selectivity is high, and the content of the effective diesel oil additive component DMM 3-8 can reach up to 49.6%.
Description
Technical field
The present invention relates to a kind of method by ionic liquid-catalyzed methyl alcohol of dumbbell shape and the synthetic polymethoxy dimethyl ether of trioxymethylene reaction.
Background technology
Diesel engine is because of its thermo-efficiency height, and oil consumption is less etc., and characteristics come into one's own in recent years, and automotive diesel oil changes into and is trend.And along with the continuous increase of consumption of petroleum amount and the enhancing of people's Environmental awareness, oil consumption and smoke intensity to oil engine require harsh day by day, how to guarantee cetane value (cetane number, CN) enlarge production of diesel oil under the situation, perhaps how to improve the diesel oil service efficiency, realize fuel-economizing, reduce noxious gas emission and become the problem that active demand solves.A kind of method easier, economic and effectively easily row is to add additive in fuel oil.Diesel-fuel cetane number is an important indicator weighing diesel fuel characteristics.Improve cetane value, can effectively suppress the discharging of black smoke.And oxygenated additive from the oxygen supply ability, in promoting oil inflame, obvious effect is arranged.Polymethoxy dialkyl ether (RO (CH
2O)
mR), have very high CN value and oxygen level (methyl series 42-49%, ethyl series 30-43%), in diesel oil, can add 10%～20%, significantly reduce NO
xDischarging with CO.At present, China's traffic surpasses 1.2 hundred million tons with diesel oil, if according to～15% adding proportion, to DMM
3-8Annual requirement above 1,800 ten thousand tons.
Polymethoxy dimethyl ether (DMM
m) to adopt methyl alcohol, formaldehyde, Paraformaldehyde 96 or ethylene glycol acetal in early days be raw material, synthetic under sulfuric acid or hydrochloric acid catalysis.In recent years, be representative (WO2006/045506A1) with BASF AG, use liquid acid such as sulfuric acid, trifluoromethanesulfonic acid to be catalyzer, methyl alcohol, methylal, Paraformaldehyde 96, trioxymethylene etc. are raw material, have obtained the series product of m=1～10.But catalytic erosion, products distribution are unreasonable, transformation efficiency and to can be used for the component concentration of oil dope not high.Japan company of Asahi Chemical Industry adopts Zeo-karb (CN 1042664A1), crystalline aluminosilicate (DE 2205070A1, EP0327343A2, US 4967014) etc. solid acid catalyst, studied formaldehyde and methyl alcohol prepared in reaction methylal, in industry, to use.With BP company is the study group of representative, has developed heterogeneous catalytic systems (US 6160174, and US 62655284) such as borosilicate molecular sieve, sulfonic group Zeo-karb.They are reaction raw materials with methyl alcohol, formaldehyde, dme or methylal, adopt multistep technology, obtain polymethoxy dimethyl ether.But heterogeneous catalyst is because acidity is inhomogeneous, and the selectivity of its catalytic chemical reaction often is difficult to control.Simultaneously,, make this catalyzer in catalyzed reaction, inevitably want frequent regeneration, shorten life of catalyst greatly because organism forms close-burning in solid catalyst surface easily.
The old people of waiting quietly (CN 101182367) has reported the reaction of presence of acidic ionic liquid catalyst methyl alcohol and trioxymethylene, and reaction conversion ratio can reach 90.3%, can be used for diesel-dope component DMM
3-8Selectivity can reach 43.7%.In addition, this research group has also reported the technical process (application number 200810150868.4) of ionic liquid-catalyzed synthetic polymethoxy dimethyl ether, use methyl alcohol or methylal, trioxymethylene to be reaction raw materials, ionic liquid is a catalyzer, has realized separating and recycling of catalyzer and each material.
Summary of the invention
The object of the present invention is to provide the method for the synthetic polymethoxy dimethyl ether of ionic liquid-catalyzed methyl alcohol of a kind of dumbbell shape and trioxymethylene reaction.
Contain two pairs of zwitterion centers in the dumbbell shape ionic liquid, shown better characteristic than general ionic liquid at aspects such as hydrothermal stability, acid-basicity and volatility.The present invention is a catalyzer with the dumbbell shape ionic liquid, and under mild conditions, efficient, environmental friendliness, technology have realized that simply methyl alcohol and trioxymethylene reaction synthesize polymethoxy dimethyl ether (DMM
3-8) method.
Reaction formula of the present invention is:
Wherein: m is 1 to 11 integer.
The method of the ionic liquid-catalyzed synthetic polymethoxy dimethyl ether of a kind of dumbbell shape, it is characterized in that this method uses methyl alcohol and trioxymethylene to be reaction raw materials, adopt the dumbbell shape ionic liquid as catalyzer, at temperature of reaction 333～423K, the synthetic polymethoxy dimethyl ether of catalysis under the reaction conditions of reaction pressure 0.5MPa～3MPa; The ion liquid cationic moiety of described dumbbell shape is selected from a kind of in bi-quaternary ammonium salt cationoid, two imidazoles positively charged ion, bipyridines positively charged ion, two pyroles positively charged ion, two pyrrolidines positively charged ion, Bispiperidines positively charged ion, the dimorphine quinoline cationoid, and anionicsite is selected from a kind of in p-methyl benzenesulfonic acid root, trifluoromethane sulfonic acid root, trifluoroacetic acid root, methylsulphonic acid root, bisulfate ion, dihydrogen phosphate, nitrate radical, chlorion, the bromide anion.
The ion liquid cationic structural formula of the used coupling dumbbell shape of the present invention is:
Wherein: R, R
1, R
2Be alkyl or aryl, n is the integer of 0-15, and m is 3 or 4.
The ion liquid anionicsite of dumbbell shape of the present invention is preferably p-methyl benzenesulfonic acid root, trifluoromethane sulfonic acid root or bisulfate ion.
Catalyst consumption of the present invention is 0.01～10wt.% of the total charging capacity of reaction raw materials, preferred 0.5～4wt.%.
The mass ratio of reaction raw materials trioxymethylene of the present invention and methyl alcohol is 1: 0.5～10, preferred 1: 0.8～1.6.
The preferred temperature of reaction of the present invention is 363～413K.
Reaction times of the present invention is 0.5～6 hour.
The present invention has the following advantages:
1, dumbbell shape ionic liquid catalyst activity height, reaction conversion ratio reaches as high as 91.5%.
2, catalyst levels is few, only is 0.01～10wt.% of the total charging capacity of reaction raw materials.
3, catalytic erosion is low, and reaction unit is not had particular requirement.
4, selectivity of product height, effectively diesel oil adds component DMM
3-8Content can reach 49.6%.
5, reaction conditions gentleness, temperature 333～423K, pressure 0.5MPa～3MPa.Easy, the easy operation of reaction process, controllability are strong.
6, the product component can be regulated by factors such as raw material ratio, temperature of reaction, catalyzer as required.Methyl alcohol and trioxymethylene raw material ratio are more little, and temperature of reaction is high more, and catalyst concn is big more, and it is high more that the product medium high carbon is counted components contents.
Embodiment
Catalyzer is expressed as follows:
Embodiment 1:
In the 100mL reactor, add 0.202g catalyzer 1 successively, 3.982g methyl alcohol, 5.572g trioxymethylene.Inflated with nitrogen is heated to 353K and stirs 4h to pressure 2.7MPa, and through gas chromatographic analysis, the trioxymethylene transformation efficiency is 85.4%, relative content, methylal (m=1), 50.1%; M=2,32.3%; M=3～8,17.6%; M＞8 do not detect.
Embodiment 2:
With embodiment 1, add 0.156g catalyzer 2 successively, 6.441g methyl alcohol, 10.213g trioxymethylene.Inflated with nitrogen to pressure is 3.0MPa, is heated to 423K and stirs 1h, and through gas chromatographic analysis, the trioxymethylene transformation efficiency is 57.5%, relative content, methylal (m=1), 30.9%; M=2,26.6%; M=3～8,41.4%; M＞8,1.1%.
Embodiment 3:
With embodiment 1, add 0.091g catalyzer 3 successively, 3.474g methyl alcohol, 7.237g trioxymethylene.Inflated with nitrogen to pressure is 2.2MPa, is heated to 393K and stirs 6h, and through gas chromatographic analysis, the trioxymethylene transformation efficiency is 91.2%, relative content, methylal (m=1), 24.9%; M=2,41.9%; M=3～8,33.2%; M＞8 do not detect.
Embodiment 4:
With embodiment 1, add 0.204g catalyzer 4 successively, 3.215g methyl alcohol, 7.258g trioxymethylene.Inflated with nitrogen to pressure is 2.3MPa, is heated to 393K and stirs 2h, and through gas chromatographic analysis, the trioxymethylene transformation efficiency is 91.5%, relative content, methylal (m=1), 22.8%; M=2,27.6%; M=3～8,49.6%; M＞8 do not detect.
Embodiment 5:
With embodiment 1, add 0.204g catalyzer 5 successively, 3.230g methyl alcohol, 7.198g trioxymethylene.Inflated with nitrogen to pressure is 2.1MPa, is heated to 373K and stirs 4h, and through gas chromatographic analysis, the trioxymethylene transformation efficiency is 77.2%, relative content, methylal (m=1), 26.6%; M=2,28.5%; M=3～8,44.9%; M＞8 do not detect.
Embodiment 6:
With embodiment 1, add 0.578g catalyzer 6 successively, 3.289g methyl alcohol, 7.229g trioxymethylene.Inflated with nitrogen to pressure is 2.3MPa, is heated to 393K and stirs 2h, and through gas chromatographic analysis, the trioxymethylene transformation efficiency is 53.36%, relative content, methylal (m=1), 79.2%; M=2,13.5%; M=3～8,7.3%; M＞8 do not detect.
Embodiment 7:
With embodiment 1, add 0.194g catalyzer 7 successively, 3.228g methyl alcohol, 7.218g trioxymethylene.Inflated with nitrogen to pressure is 2.5MPa, is heated to 413K and stirs 3h, and through gas chromatographic analysis, the trioxymethylene transformation efficiency is 86.7%, relative content, methylal (m=1), 42.2%; M=2,34.6%; M=3～8,23.2%; M＞8 do not detect.
Embodiment 8:
With embodiment 1, add 0.913g catalyzer 8 successively, 6.476g methyl alcohol, 15.131g trioxymethylene.Inflated with nitrogen to pressure is 1.9MPa, is heated to 393K and stirs 4h, and through gas chromatographic analysis, the trioxymethylene transformation efficiency is 89.6%, relative content, methylal (m=1), 31.4%; M=2,25.3%; M=3～8,43.3%; M＞8 do not detect.
Embodiment 9:
Adopt catalyzer 1, compound concentration is 10% methanol solution, in the teflon-lined autoclave pressure is arranged, keeps 393K, pressure 3MPa, and 316L stainless steel lacing film is measured its corrodibility, and annual corrosion rate is 0.004mm/a.Belong to mild corrosion.
Claims (9)
1. the method for the ionic liquid-catalyzed synthetic polymethoxy dimethyl ether of dumbbell shape, it is characterized in that this method uses methyl alcohol and trioxymethylene to be reaction raw materials, adopt the dumbbell shape ionic liquid as catalyzer, at temperature of reaction 333～423K, the synthetic polymethoxy dimethyl ether of catalysis under the reaction conditions of reaction pressure 0.5MPa～3MPa; The ion liquid cationic moiety of described dumbbell shape is selected from a kind of in bi-quaternary ammonium salt cationoid, two imidazoles positively charged ion, bipyridines positively charged ion, two pyroles positively charged ion, two pyrrolidines positively charged ion, Bispiperidines positively charged ion, the dimorphine quinoline cationoid, and anionicsite is selected from a kind of in p-methyl benzenesulfonic acid root, trifluoromethane sulfonic acid root, trifluoroacetic acid root, methylsulphonic acid root, bisulfate ion, dihydrogen phosphate, nitrate radical, chlorion, the bromide anion.
2. the method for claim 1 is characterized in that the ion liquid cationic structural formula of coupling dumbbell shape is:
Wherein: R, R
1, R
2Be alkyl or aryl, n is the integer of 0-15, and m is 3 or 4.
3. the method for claim 1 is characterized in that the ion liquid anionicsite of dumbbell shape is p-methyl benzenesulfonic acid root, trifluoromethane sulfonic acid root or bisulfate ion.
4. the method for claim 1 is characterized in that catalyst consumption is 0.01～10wt.% of the total charging capacity of reaction raw materials.
5. method as claimed in claim 4 is characterized in that catalyst consumption is 0.5～4wt.% of the total charging capacity of reaction raw materials.
6. the method for claim 1, the mass ratio that it is characterized in that trioxymethylene and methyl alcohol is 1: 0.5～10.
7. method as claimed in claim 6, the mass ratio that it is characterized in that trioxymethylene and methyl alcohol is 1: 0.8～1.6.
8. the method for claim 1 is characterized in that temperature of reaction is 363～413K.
9. the method for claim 1 is characterized in that the reaction times is 0.5～6 hour.
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Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102019202A (en) * | 2010-09-30 | 2011-04-20 | 南京工业大学 | Sulfonic acid dual-core ionic liquid catalyst and method for synthesizing poly (butylene succinate) by using same |
| CN102688774A (en) * | 2012-05-30 | 2012-09-26 | 凯瑞化工股份有限公司 | Resin catalyst for light gasoline etherification and preparation method thereof |
| CN102757323A (en) * | 2011-04-26 | 2012-10-31 | 中国科学院兰州化学物理研究所 | Method for preparing alkoxy ether compounds |
| WO2013029236A1 (en) * | 2011-08-30 | 2013-03-07 | 海洋王照明科技股份有限公司 | Double-center quaternary ammonium salt ion liquid, preparation method therefor and use thereof |
| CN104045530A (en) * | 2014-05-15 | 2014-09-17 | 上海盘马化工工程技术有限公司 | System using supported ionic liquid catalyst for continuous preparation of polyoxymethylene dimethyl ether |
| CN104086380A (en) * | 2014-07-07 | 2014-10-08 | 中国科学院山西煤炭化学研究所 | Preparation method of polyoxymethylene dimethyl ethers |
| EP2905293A1 (en) * | 2013-12-09 | 2015-08-12 | Lanzhou Institute Of Chemical Physics Chinese Academy of Sciences | Process for catalytic synthesis of low-carbon polyether-based compound by using acidic ionic liquid |
| CN106866388A (en) * | 2017-01-12 | 2017-06-20 | 中国科学院兰州化学物理研究所 | A kind of method of ionic liquid-catalyzed synthesis diethoxymethane |
| CN110511125A (en) * | 2019-09-23 | 2019-11-29 | 辽宁石油化工大学 | A kind of method that adopts sulfuric acid type deep eutectic solvent to synthesize polymethoxydimethyl ether |
| CN118516045A (en) * | 2024-07-19 | 2024-08-20 | 齐芯微(绍兴)电子材料科技有限公司 | A chemical mechanical polishing liquid |
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2009
- 2009-07-24 CN CN2009101596478A patent/CN101962318A/en active Pending
Cited By (14)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN102019202B (en) * | 2010-09-30 | 2013-02-06 | 南京工业大学 | Sulfonic acid dual-core ionic liquid catalyst and method for synthesizing poly (butylene succinate) by using same |
| CN102019202A (en) * | 2010-09-30 | 2011-04-20 | 南京工业大学 | Sulfonic acid dual-core ionic liquid catalyst and method for synthesizing poly (butylene succinate) by using same |
| CN102757323A (en) * | 2011-04-26 | 2012-10-31 | 中国科学院兰州化学物理研究所 | Method for preparing alkoxy ether compounds |
| WO2013029236A1 (en) * | 2011-08-30 | 2013-03-07 | 海洋王照明科技股份有限公司 | Double-center quaternary ammonium salt ion liquid, preparation method therefor and use thereof |
| CN102688774A (en) * | 2012-05-30 | 2012-09-26 | 凯瑞化工股份有限公司 | Resin catalyst for light gasoline etherification and preparation method thereof |
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