CN1196670C - Method for preparing tetraethyl ammonium hydroxide - Google Patents
Method for preparing tetraethyl ammonium hydroxide Download PDFInfo
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- CN1196670C CN1196670C CN 00126629 CN00126629A CN1196670C CN 1196670 C CN1196670 C CN 1196670C CN 00126629 CN00126629 CN 00126629 CN 00126629 A CN00126629 A CN 00126629A CN 1196670 C CN1196670 C CN 1196670C
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- triethylamine
- acetone
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- monochloroethane
- acetonitrile
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- 229940073455 tetraethylammonium hydroxide Drugs 0.000 title claims abstract description 34
- LRGJRHZIDJQFCL-UHFFFAOYSA-M tetraethylazanium;hydroxide Chemical compound [OH-].CC[N+](CC)(CC)CC LRGJRHZIDJQFCL-UHFFFAOYSA-M 0.000 title claims abstract description 34
- 238000000034 method Methods 0.000 title claims abstract description 7
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims abstract description 124
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims abstract description 101
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims abstract description 52
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims abstract description 36
- HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 claims abstract description 32
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims abstract description 30
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims abstract description 30
- YMBCJWGVCUEGHA-UHFFFAOYSA-M tetraethylammonium chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC YMBCJWGVCUEGHA-UHFFFAOYSA-M 0.000 claims abstract description 21
- 238000002360 preparation method Methods 0.000 claims abstract description 13
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims abstract description 12
- 239000003093 cationic surfactant Substances 0.000 claims abstract description 11
- AVQQQNCBBIEMEU-UHFFFAOYSA-N 1,1,3,3-tetramethylurea Chemical compound CN(C)C(=O)N(C)C AVQQQNCBBIEMEU-UHFFFAOYSA-N 0.000 claims abstract description 10
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims abstract description 10
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 claims abstract description 10
- 239000003960 organic solvent Substances 0.000 claims abstract description 10
- 239000011347 resin Substances 0.000 claims abstract description 6
- 229920005989 resin Polymers 0.000 claims abstract description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 18
- 238000006243 chemical reaction Methods 0.000 claims description 16
- 230000035484 reaction time Effects 0.000 claims description 9
- RAOIDOHSFRTOEL-UHFFFAOYSA-N tetrahydrothiophene Chemical compound C1CCSC1 RAOIDOHSFRTOEL-UHFFFAOYSA-N 0.000 claims description 9
- 239000004408 titanium dioxide Substances 0.000 claims description 9
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N titanium dioxide Inorganic materials O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 claims description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
- 125000000129 anionic group Chemical group 0.000 claims description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
- 239000001301 oxygen Substances 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- HWCKGOZZJDHMNC-UHFFFAOYSA-M tetraethylammonium bromide Chemical compound [Br-].CC[N+](CC)(CC)CC HWCKGOZZJDHMNC-UHFFFAOYSA-M 0.000 claims description 4
- 238000010790 dilution Methods 0.000 claims description 3
- 239000012895 dilution Substances 0.000 claims description 3
- 239000012153 distilled water Substances 0.000 claims description 3
- 239000011261 inert gas Substances 0.000 claims description 3
- 239000000243 solution Substances 0.000 claims description 3
- 238000007789 sealing Methods 0.000 claims description 2
- 230000008901 benefit Effects 0.000 abstract description 4
- 239000002808 molecular sieve Substances 0.000 abstract description 4
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 abstract description 4
- 238000004519 manufacturing process Methods 0.000 abstract description 2
- 150000001450 anions Chemical class 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 229960003750 ethyl chloride Drugs 0.000 abstract 1
- 239000013067 intermediate product Substances 0.000 abstract 1
- 239000000047 product Substances 0.000 abstract 1
- 230000002194 synthesizing effect Effects 0.000 abstract 1
- -1 template synthetic β Chemical compound 0.000 description 12
- 230000000052 comparative effect Effects 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- 239000013543 active substance Substances 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 229910021536 Zeolite Inorganic materials 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 239000010457 zeolite Substances 0.000 description 3
- 229910004339 Ti-Si Inorganic materials 0.000 description 2
- 229910010978 Ti—Si Inorganic materials 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 238000010792 warming Methods 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium group Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000005336 cracking Methods 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- BCDGQXUMWHRQCB-UHFFFAOYSA-N glycine methyl ketone Natural products CC(=O)CN BCDGQXUMWHRQCB-UHFFFAOYSA-N 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
Abstract
The invention provides a preparation method of tetraethyl ammonium hydroxide for synthesizing a molecular sieve template agent. Mixing quaternary ammonium salt cationic surfactant, organic solvent selected from acetone, acetonitrile, dimethyl sulfoxide, nitromethane, dimethylformamide, dimethylacetamide, tetramethylurea, 1-tetrahydrothiophene dioxide or diether of ethylene glycol, triethylamine and chloroethane, reacting at a certain temperature, exchanging intermediate product tetraethylammonium chloride by strong basic anion resin to prepare tetraethylammonium hydroxide dilute solution, and concentrating under reduced pressure to obtain the tetraethylammonium hydroxide product. The method has short production period and high economic benefit, is a simple and economic preparation method, and has good application prospect.
Description
The present invention relates to a kind of method for preparing tetraethyl ammonium hydroxide, or rather, relate to a kind of preparation method who is used for the tetraethyl ammonium hydroxide of synthesis of molecular sieve template.
One of very important purposes of tetraethyl ammonium hydroxide is exactly as zeolite molecular sieves such as template synthetic β, Ti-Si, ZSM series, beta-zeolite has good application prospects in the FCC cracking catalyst, the Ti-Si molecular sieve is the aromatic hydrocarbon oxidation catalyst of excellent property, and ZSM zeolite is widely used in petroleum chemical industry because of it possesses unique shape selective catalysis performance.The conventional method for preparing tetraethyl ammonium hydroxide is that (1) adds acetone and triethylamine in one encloses container, with the air of inert gas replacement in it to oxygen level less than 1.0% (volume), introduce monochloroethane again, the mol ratio of triethylamine and monochloroethane is 1: 0.5～1: 1.4, and the mol ratio of triethylamine and acetone is 1: 1.8; (2) under 50～120 ℃ of temperature of reaction, stirring, reacted at least 168 hours, then, cool off, isolate crystalloid etamon chloride; (3) with dissolved in distilled water, dilute this etamon chloride, through strongly basic anionic resin exchange, make the tetraethyl ammonium hydroxide dilute solution; (4) concentrating under reduced pressure obtains the tetraethyl ammonium hydroxide product.Because this reaction is the gas-liquid two-phase reaction, therefore, exposure level between speed of response and yield and the reactant two-phase is closely related, and the method for prior art makes its application be subjected to considerable restraint just because of above-mentioned former thereby cause long reaction time under the situation of identical yield.
Purpose of the present invention is exactly to overcome the long reaction time that exists in the prior art, and the defective that economic benefit is low is developed a kind of preparation method easily and economically.
The method for preparing tetraethyl ammonium hydroxide of the present invention is: (1) is earlier with quaternary ammonium salt cationic surfactant, be selected from acetone, acetonitrile, dimethyl sulfoxide (DMSO), Nitromethane 99Min., dimethyl formamide, N,N-DIMETHYLACETAMIDE, tetramethyl-urea, 1, the organic solvent of the bis ether of 1-titanium dioxide tetramethylene sulfide or ethylene glycol and triethylamine add in the encloses container, sealing back with inert gas replacement go out in the reactor air to oxygen level less than 1.0% (volume) after, monochloroethane is introduced in this encloses container again, the mol ratio of triethylamine and monochloroethane is 1: 0.5～1: 4.0, be preferably 1: 1.5～1: 3.0, three second ammoniums be selected from acetone, acetonitrile, dimethyl sulfoxide (DMSO), Nitromethane 99Min., dimethyl formamide, N,N-DIMETHYLACETAMIDE, tetramethyl-urea, 1, the mol ratio of the organic solvent of the bis ether of 1-titanium dioxide tetramethylene sulfide or ethylene glycol is 1: 1.0～1: 2.8, be preferably 1: 1.3～1: 2.0, the mol ratio of triethylamine and quaternary ammonium salt cationic surfactant is 1: 0.10～1: 0.30, is preferably 1: 0.15～1: 0.30; (2) 50～120 ℃ of temperature of reaction, be preferably 80～110 ℃, reacted 12～96 hours, be preferably 36～60 hours, then, cool off, isolate crystalloid product etamon chloride; (3) with dissolved in distilled water, dilute this etamon chloride, through strongly basic anionic resin exchange, make the tetraethyl ammonium hydroxide dilute solution; (4) concentrating under reduced pressure obtains the tetraethyl ammonium hydroxide product.
The used quaternary ammonium salt cationic surfactant of the present invention, be selected from acetone, acetonitrile, dimethyl sulfoxide (DMSO), Nitromethane 99Min., dimethyl formamide, N,N-DIMETHYLACETAMIDE, tetramethyl-urea, 1, the water content of the organic solvent of the bis ether of 1-titanium dioxide tetramethylene sulfide or ethylene glycol, monochloroethane, triethylamine is all less than 3.0% (weight).
The present invention is used is selected from acetone, acetonitrile, dimethyl sulfoxide (DMSO), Nitromethane 99Min., dimethyl formamide, N,N-DIMETHYLACETAMIDE, tetramethyl-urea, 1, and the organic solvent of the bis ether of 1-titanium dioxide tetramethylene sulfide or ethylene glycol is preferably acetone, acetonitrile or dimethyl sulfoxide (DMSO).
The used quaternary ammonium salt cationic surfactant of the present invention is meant etamon chloride or tetraethylammonium bromide.
The present invention compared with prior art has following advantage:
Because the present invention has introduced quaternary ammonium salt cationic surfactant in reaction, thereby the reactant molecule of gas-liquid two-phase can fully be contacted, two alternate obstacles have been eliminated to greatest extent, accelerated speed of response, therefore under the situation that obtains identical yield, shortened the reaction required strategic point time widely, thereby reduced production cost, improved economic benefit, made the present invention possess good application prospects.
The following examples will the present invention is further illustrated.
Comparative Examples 1
It is in 1 liter the autoclave that 121 gram (1.2 moles) triethylamines and 100 milliliters of acetone solvents are added a volume, carry out after airtight nitrogen replacement to oxygen level less than 1.0% (volume), introduce 153 gram (2.4 moles) monochloroethane again, be warming up to 100 ℃ of constant temperature, stir reaction down 48 hours, cooling, separated product, obtain etamon chloride solid 83 grams, then, with this etamon chloride of water dissolution, dilution, through strongly basic anionic resin exchange, concentrating under reduced pressure makes the tetraethyl ammonium hydroxide finished product again, and its yield is that 40.6% (amount that transforms with triethylamine serves as to calculate benchmark by weight percentage, the results are shown in table 1 down together).
Comparative Examples 2
Except that the reaction times extended to 168 hours, all the other conditions are with Comparative Examples 1, and the tetraethyl ammonium hydroxide yield is 90.0%, the results are shown in table 1.
Embodiment 1
It is in 1 liter the autoclave that 121 gram (1.2 moles) triethylamines, 36 gram etamon chlorides and 100 milliliters of acetone are added volume, airtight back with nitrogen replacement to oxygen level less than 1.0% (volume), introduce 153 gram (2.4 moles) monochloroethane again, be warming up to 100 ℃ of constant temperature, stirring reaction 48 hours, cooling, separated product, then, with this product of water dissolution and dilution, exchange through strongly basic anionic resin again, concentrating under reduced pressure makes the tetraethyl ammonium hydroxide finished product, and its yield is 89.6%, and the result lists in table 1,2,3,4,5,6,7,8 respectively.
Embodiment 2
60 gram (0.6 mole) triethylamines, 18 gram etamon chlorides, 50 milliliters of acetone, 77 gram (1.2 moles) monochloroethane, all the other conditions are with embodiment 1, and the tetraethyl ammonium hydroxide yield is 90.1%, the results are shown in table 1.
By embodiment in the table 11,2 and Comparative Examples 1 data as can be seen, in the identical reaction times, add the above two of etamon chloride tensio-active agent, its yield is higher than the latter who does not add tensio-active agent far away, compare with Comparative Examples 2 data, under identical yield, the above two reaction times only need the latter 1/3 a little less than.
Table 1.
Triethylamine/acetone triethylamine/etamon chloride triethylamine/monochloroethane reaction times yield
Numbering
/ mol ratio/mol ratio/mol ratio/hour/% (weight)
Embodiment 11: 1.82 1: 0.18 1: 2 48 89.6
Embodiment 21: 1.82 1: 0.18 1: 2 48 90.1
Comparative Examples 11: 1.82/1: 2 48 40.6
Comparative Examples 21: 1.82/1: 2 168 90.0
Embodiment 3
121 gram (1.2 moles) triethylamines, 36 gram etamon chlorides, 100 milliliters of acetone, 77 gram (1.2 moles) monochloroethane, all the other are with embodiment 1, and the tetraethyl ammonium hydroxide yield is 74.2%, the results are shown in table 2.
Embodiment 4
121 gram (1.2 moles) triethylamines, with 36 gram etamon chlorides, 50 milliliters of acetone, 231 gram (3.6 moles) monochloroethane, all the other conditions are with embodiment 1, and the tetraethyl ammonium hydroxide yield is 90.7%, the results are shown in table 2.
Table 2.
Triethylamine/acetone triethylamine/etamon chloride triethylamine/monochloroethane reaction times yield
Numbering
/ mol ratio/mol ratio/mol ratio/hour/% (weight)
Embodiment 31: 1.82 1: 0.18 1: 1 48 74.2
Embodiment 11: 1.82 1: 0.18 1: 2 48 89.6
Embodiment 41: 1.82 1: 0.18 1: 3 48 90.7
By table 2 data as can be known, the concentration that suitably improves reactant monochloroethane helps improving the yield of reaction.
Embodiment 5
121 gram (1.2 moles) triethylamines, 36 gram etamon chlorides, 150 milliliters of acetone, 153 gram (2.4 moles) monochloroethane, all the other are with embodiment 1, and the tetraethyl ammonium hydroxide yield is 86.9%, the results are shown in table 3.
Embodiment 6
121 gram (1.2 moles) triethylamines, 36 gram etamon chlorides, 75 milliliters of acetone, 153 gram (2.4 moles) monochloroethane, all the other are with embodiment 1, and the tetraethyl ammonium hydroxide yield is 87.5%, the results are shown in table 3.
Embodiment 7
121 gram (1.2 moles) triethylamines, 36 gram etamon chlorides, 50 milliliters of acetone, 153 gram (2.4 moles) monochloroethane, all the other are with embodiment 1, and the tetraethyl ammonium hydroxide yield is 76.4%, the results are shown in table 3.
Table 3.
Triethylamine/acetone triethylamine/etamon chloride triethylamine/monochloroethane reaction times yield
Numbering
/ mol ratio/mol ratio/mol ratio/hour/% (weight)
Embodiment 51: 2.73 1: 0.18 1: 2 48 86.9
Embodiment 11: 1.82 1: 0.18 1: 2 48 89.6
Embodiment 61: 1.36 1: 0.18 1: 2 48 88.4
Embodiment 71: 0.91 1: 0.18 1: 2 48 76.4
Table 3 is the result show, suitable acetone solvent consumption can obtain higher yield.
Embodiment 8
121 gram (1.2 moles) triethylamines, 45.7 gram tetraethylammonium bromides, 100 milliliters of acetone, 153 gram (2.4 moles) monochloroethane, all the other are with embodiment 1, and the tetraethyl ammonium hydroxide yield is 85.5%, the results are shown in table 4.
Table 4.
Triethylamine/acetone triethylamine/tensio-active agent triethylamine/monochloroethane yield
Number table surface-active agent title
/ mol ratio/mol ratio/mol ratio/% (weight)
Embodiment 1 etamon chloride 1: 1.82 1: 0.18 1: 2 89.6
Embodiment 8 tetraethylammonium bromides 1: 1.82 1: 0.18 1: 2 85.5
Table 4 is the result show, all can obtain higher yield with quaternary ammonium salt as tensio-active agent.
Embodiment 9
121 gram (1.2 moles) triethylamines, 18 gram etamon chlorides, 100 milliliters of acetone, 153 gram (2.4 moles) monochloroethane, all the other are with embodiment 1, and the tetraethyl ammonium hydroxide yield is 65.7%, the results are shown in table 5.
Embodiment 10
121 gram (1.2 moles) triethylamines, with 54 etamon chlorides, 100 milliliters of acetone, 153 gram (2.4 moles) monochloroethane, all the other are with embodiment 1, and the tetraethyl ammonium hydroxide yield is 91.2%, the results are shown in table 5.
Table 5.
Triethylamine/acetone triethylamine/etamon chloride three/mol ratio ethamine yield
Numbering
/ mol ratio/mol ratio/monochloroethane/% (weight)
Embodiment 91: 1.82 1: 0.09 1: 2 65.7
Example example 11: 1.82 1: 0.18 1: 2 89.6
Embodiment 10 1: 1.82 1: 0.27 1: 2 91.2
Table 5 is the result show, the amount that suitably increases the tensio-active agent etamon chloride helps improving yield.
Embodiment 11
121 gram (1.2 moles) triethylamines, 36 gram etamon chlorides, 100 milliliters of acetonitriles, 153 gram (2.4 moles) monochloroethane, all the other are with embodiment 1, and the tetraethyl ammonium hydroxide yield is 90.0%, the results are shown in table 6.
Embodiment 12
121 gram (1.2 moles) triethylamines, 36 gram etamon chlorides, 100 milliliters of dimethyl sulfoxide solvents, 153 gram (2.4 moles) monochloroethane, all the other are with embodiment 1, and the tetraethyl ammonium hydroxide yield is 90.4%, the results are shown in table 6.
Table 6.
Solvent load triethylamine/etamon chloride triethylamine/monochloroethane yield
Numbering solvent title
/ milliliter/mol ratio/mol ratio/% (weight)
Embodiment 1 acetone 100 1: 0.18 1: 2 89.6
Embodiment 11 acetonitriles 100 1: 0.18 1: 2 90.0
Embodiment 12 dimethyl sulfoxide (DMSO) 100 1: 0.18 1: 2 90.4
Table 6 data show that the above-mentioned three kinds of nonionic solvents of employing all can obtain higher yield.
Embodiment 13
Except that temperature of reaction is 70 ℃, all the other conditions are with embodiment 1, and the tetraethyl ammonium hydroxide yield is 68.7%, the results are shown in table 7.
Embodiment 14
Except that temperature of reaction is 120 ℃, all the other conditions are with embodiment 1, and the tetraethyl ammonium hydroxide yield is 73.2%, the results are shown in table 7.
Table 7.
Temperature of reaction triethylamine/acetone triethylamine/etamon chloride triethylamine/monochloroethane yield
Numbering
/ ℃/mol ratio/mol ratio/mol ratio/% (weight)
Embodiment 13 70 1: 1.82 1: 0.18 1: 2 68.7
Embodiment 1 100 1: 1.82 1: 0.18 1: 2 89.6
Embodiment 14 120 1: 1.82 1: 0.18 1: 2 73.2
Table 7 has been investigated the influence of differing temps to reaction, and the result shows that suitable reaction temperature is 80～110 ℃.
Embodiment 15
Except that not opening the stirring, all the other conditions are with embodiment 1, and the tetraethyl ammonium hydroxide yield is 85.7%, the results are shown in table 8.
Table 8.
Triethylamine/acetone triethylamine/etamon chloride triethylamine/monochloroethane yield
The numbering stirring state
/ mol ratio/mol ratio/mol ratio/% (weight)
Embodiment 1 stirred 1: 1.82 1: 0.18 1: 2 89.6
Embodiment 15 did not stir 1: 1.82 1: 0.18 1: 2 85.7
Table 8 data show, add tensio-active agent and can save stirring, can obtain higher yield equally.
Claims (9)
1, a kind of method for preparing tetraethyl ammonium hydroxide, its preparation process is:
(1) with quaternary ammonium salt cationic surfactant, be selected from acetone, acetonitrile, dimethyl sulfoxide (DMSO), Nitromethane 99Min., dimethyl formamide, N,N-DIMETHYLACETAMIDE, tetramethyl-urea, 1, the organic solvent of the bis ether of 1-titanium dioxide tetramethylene sulfide or ethylene glycol and triethylamine place an encloses container, sealing back with the interior air of inert gas replacement container to oxygen level in volume percent less than after 1.0%, introduce monochloroethane again, the mol ratio of triethylamine and monochloroethane is 1: 0.5～1: 4.0, triethylamine be selected from acetone, acetonitrile, dimethyl sulfoxide (DMSO), Nitromethane 99Min., dimethyl formamide, N,N-DIMETHYLACETAMIDE, tetramethyl-urea, 1, the mol ratio of the organic solvent of the bis ether of 1-titanium dioxide tetramethylene sulfide or ethylene glycol is 1: 1.0～1: 2.8, the mol ratio of triethylamine and quaternary ammonium salt cationic surfactant is 1: 0.10～1: 0.30
(2) temperature of reaction was reacted 12～96 hours down for 50～120 ℃, then, cooled off, isolates crystalloid product etamon chloride,
(3) with dissolved in distilled water, this crystalloid etamon chloride of dilution,, make the tetraethyl ammonium hydroxide dilute solution through the strongly basic anionic resin exchange,
(4) concentrating under reduced pressure obtains the tetraethyl ammonium hydroxide product.
2, according to the described preparation method of claim 1, it is characterized in that said quaternary ammonium salt cationic surfactant, be selected from acetone, acetonitrile, dimethyl sulfoxide (DMSO), Nitromethane 99Min., dimethyl formamide, N,N-DIMETHYLACETAMIDE, tetramethyl-urea, 1, the water content of the organic solvent of the bis ether of 1-titanium dioxide tetramethylene sulfide or ethylene glycol, monochloroethane, triethylamine is by weight percentage all less than 3.0%.
3, according to the described preparation method of claim 1, it is characterized in that said triethylamine and be selected from acetone, acetonitrile, dimethyl sulfoxide (DMSO), Nitromethane 99Min., dimethyl formamide, N,N-DIMETHYLACETAMIDE, tetramethyl-urea, 1, the mol ratio of the organic solvent of the bis ether of 1-titanium dioxide tetramethylene sulfide or ethylene glycol is 1: 1.3～1: 2.0.
4, according to claim 1,2,3 described preparation methods, it is characterized in that said acetone, acetonitrile, dimethyl sulfoxide (DMSO), Nitromethane 99Min., dimethyl formamide, N,N-DIMETHYLACETAMIDE, the tetramethyl-urea, 1 of being selected from, the organic solvent of the bis ether of 1-titanium dioxide tetramethylene sulfide or ethylene glycol is preferably acetone, acetonitrile or dimethyl sulfoxide (DMSO).。
5, according to the described preparation method of claim 1, the mol ratio that it is characterized in that said triethylamine and monochloroethane is 1: 1.5～1: 3.0.
6, according to the described preparation method of claim 1, the mol ratio that it is characterized in that said triethylamine and quaternary ammonium salt cationic surfactant is 1: 0.15～1: 0.30.
7,, it is characterized in that said quaternary ammonium salt cationic surfactant is meant etamon chloride or tetraethylammonium bromide according to claim 1 or 6 described preparation methods.
8,, it is characterized in that said temperature of reaction is 80～110 ℃ according to the described preparation method of claim 1.
9,, it is characterized in that the said reaction times is 36～60 hours according to the described preparation method of claim 1.
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| CN105294455B (en) * | 2015-10-09 | 2017-10-27 | 南京工业大学 | Method for preparing tetrabutyl ammonium hydroxide aqueous solution by anion exchange |
| CN106518687A (en) * | 2016-09-09 | 2017-03-22 | 华东理工大学 | Efficient preparation method of high-purity tetraethyl ammonium chloride |
| CN108586261A (en) * | 2018-01-20 | 2018-09-28 | 盐城泛安化学有限公司 | A kind of preparation method of high-purity etamon chloride |
| CN113235117B (en) * | 2021-05-12 | 2022-02-22 | 肯特催化材料股份有限公司 | Production process of high-concentration tetrapropylammonium hydroxide and high-concentration tetrapropylammonium hydroxide prepared by same |
| CN113846337A (en) * | 2021-09-17 | 2021-12-28 | 镇江润晶高纯化工科技股份有限公司 | Method for preparing high-purity tetraethylammonium hydroxide through continuous electrolysis |
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