CN104876886B - Preparation method of tridemorph quaternary ammonium hydroxide - Google Patents
Preparation method of tridemorph quaternary ammonium hydroxide Download PDFInfo
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- CN104876886B CN104876886B CN201510179832.9A CN201510179832A CN104876886B CN 104876886 B CN104876886 B CN 104876886B CN 201510179832 A CN201510179832 A CN 201510179832A CN 104876886 B CN104876886 B CN 104876886B
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- quaternary ammonium
- tridemorph
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- tridemorph quaternary
- ammonium salt
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- 238000002360 preparation method Methods 0.000 title claims abstract description 17
- 239000000908 ammonium hydroxide Substances 0.000 title abstract 3
- 238000006243 chemical reaction Methods 0.000 claims abstract description 15
- YTOPFCCWCSOHFV-UHFFFAOYSA-N 2,6-dimethyl-4-tridecylmorpholine Chemical compound CCCCCCCCCCCCCN1CC(C)OC(C)C1 YTOPFCCWCSOHFV-UHFFFAOYSA-N 0.000 claims abstract description 6
- -1 tridemorph quaternary ammonium salt Chemical class 0.000 claims description 15
- 239000007787 solid Substances 0.000 claims description 10
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 claims description 6
- 238000001914 filtration Methods 0.000 claims description 6
- 230000026030 halogenation Effects 0.000 claims description 6
- 238000005658 halogenation reaction Methods 0.000 claims description 6
- 150000008282 halocarbons Chemical class 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- MPPPKRYCTPRNTB-UHFFFAOYSA-N 1-bromobutane Chemical compound CCCCBr MPPPKRYCTPRNTB-UHFFFAOYSA-N 0.000 claims description 3
- RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical compound [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 claims description 3
- 229910001863 barium hydroxide Inorganic materials 0.000 claims description 3
- 239000000706 filtrate Substances 0.000 claims description 3
- WBHQBSYUUJJSRZ-UHFFFAOYSA-M sodium bisulfate Chemical compound [Na+].OS([O-])(=O)=O WBHQBSYUUJJSRZ-UHFFFAOYSA-M 0.000 claims description 3
- 229910000342 sodium bisulfate Inorganic materials 0.000 claims description 3
- 239000012467 final product Substances 0.000 claims description 2
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 claims description 2
- 238000001953 recrystallisation Methods 0.000 claims description 2
- 229910052708 sodium Inorganic materials 0.000 claims description 2
- 239000011734 sodium Substances 0.000 claims description 2
- UREZNYTWGJKWBI-UHFFFAOYSA-M benzethonium chloride Chemical compound [Cl-].C1=CC(C(C)(C)CC(C)(C)C)=CC=C1OCCOCC[N+](C)(C)CC1=CC=CC=C1 UREZNYTWGJKWBI-UHFFFAOYSA-M 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Substances OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract description 18
- 239000003054 catalyst Substances 0.000 abstract description 13
- 239000003225 biodiesel Substances 0.000 abstract description 10
- 230000000694 effects Effects 0.000 abstract description 4
- 230000003197 catalytic effect Effects 0.000 abstract description 2
- 150000001875 compounds Chemical class 0.000 abstract description 2
- 238000011084 recovery Methods 0.000 abstract description 2
- 230000002152 alkylating effect Effects 0.000 abstract 1
- 238000005349 anion exchange Methods 0.000 abstract 1
- 239000002585 base Substances 0.000 description 18
- 238000004519 manufacturing process Methods 0.000 description 8
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- 239000003921 oil Substances 0.000 description 5
- 235000019198 oils Nutrition 0.000 description 5
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 230000031709 bromination Effects 0.000 description 3
- 238000005893 bromination reaction Methods 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 235000014593 oils and fats Nutrition 0.000 description 3
- 125000001453 quaternary ammonium group Chemical group 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Natural products C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000006555 catalytic reaction Methods 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 2
- 238000007711 solidification Methods 0.000 description 2
- 230000008023 solidification Effects 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 2
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- VMKOFRJSULQZRM-UHFFFAOYSA-N 1-bromooctane Chemical compound CCCCCCCCBr VMKOFRJSULQZRM-UHFFFAOYSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- NJWIMFZLESWFIM-UHFFFAOYSA-N 2-(chloromethyl)pyridine Chemical compound ClCC1=CC=CC=N1 NJWIMFZLESWFIM-UHFFFAOYSA-N 0.000 description 1
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 1
- 229910021536 Zeolite Inorganic materials 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000005815 base catalysis Methods 0.000 description 1
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
- 229940073608 benzyl chloride Drugs 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 235000009508 confectionery Nutrition 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000013461 design Methods 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
- 230000007613 environmental effect Effects 0.000 description 1
- 150000002148 esters Chemical group 0.000 description 1
- 235000021050 feed intake Nutrition 0.000 description 1
- 238000011031 large-scale manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000003444 phase transfer catalyst Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 210000000582 semen Anatomy 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 238000013517 stratification Methods 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
- C11C3/00—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom
- C11C3/04—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by esterification of fats or fatty oils
- C11C3/10—Ester interchange
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D265/28—1,4-Oxazines; Hydrogenated 1,4-oxazines
- C07D265/30—1,4-Oxazines; Hydrogenated 1,4-oxazines not condensed with other rings
-
- 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
- B01J31/0234—Nitrogen-, phosphorus-, arsenic- or antimony-containing compounds
- B01J31/0235—Nitrogen containing compounds
- B01J31/0244—Nitrogen containing compounds with nitrogen contained as ring member in aromatic compounds or moieties, e.g. pyridine
-
- 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
- B01J31/0234—Nitrogen-, phosphorus-, arsenic- or antimony-containing compounds
- B01J31/0271—Nitrogen-, phosphorus-, arsenic- or antimony-containing compounds also containing elements or functional groups covered by B01J31/0201 - B01J31/0231
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
- C10L1/00—Liquid carbonaceous fuels
- C10L1/02—Liquid carbonaceous fuels essentially based on components consisting of carbon, hydrogen, and oxygen only
-
- 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
- B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
- B01J2231/40—Substitution reactions at carbon centres, e.g. C-C or C-X, i.e. carbon-hetero atom, cross-coupling, C-H activation or ring-opening reactions
- B01J2231/49—Esterification or transesterification
-
- 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
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E50/00—Technologies for the production of fuel of non-fossil origin
- Y02E50/10—Biofuels, e.g. bio-diesel
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Materials Engineering (AREA)
- General Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a preparation method of tridemorph quaternary ammonium hydroxide, which comprises the following steps: alkylating tridemorph, carrying out anion exchange and alkalifying. The compound is used as a catalyst in grease-methanol ester exchange reaction for preparing biodiesel. The tridemorph quaternary ammonium hydroxide used as the catalyst for preparing biodiesel has excellent catalytic activity, can be easily separated after the reaction finishes, and can still keep higher activity after repeated recovery.
Description
The application is application number：201410069592.2, the applying date：2014.2.27, title " tridemorph quaternary ammonium base and
The divisional application of Preparation Method And The Use ".
Technical field
The present invention relates to a kind of tridemorph quaternary ammonium base and its production and use.
Background technology
Being widely used for quaternary ammonium base, can be used as the template of Zeolite synthesis, phase transfer catalyst, base catalyst etc..Often
The quaternary ammonium base seen has tetramethyl ammonium hydroxide, tetrabutylammonium etc., and they can be used for the life of biodiesel as catalyst
Produce, but they are after the completion of reaction, it is impossible to directly reclaim and recycle, it is therefore desirable to which a kind of catalysis activity of design synthesis is excellent
Quaternary ammonium base that is good, can recycling, while the production technology of biodiesel can be simplified, reduces production cost.
The content of the invention
It is an object of the invention to provide a kind of catalytic performance it is excellent, it is easy recovery and reusable tridemorph quaternary ammonium
Alkali and its production and use.
The present invention technical solution be：
A kind of tridemorph quaternary ammonium base, is characterized in that：Structural formula is：
R be normal-butyl, n-octyl, benzyl or 2- picolyls, C13H27For tridecyl.
A kind of preparation method of tridemorph quaternary ammonium base, is characterized in that：Comprise the following steps：
1) preparation of halogenation tridemorph quaternary ammonium salt：Tridemorph reacts 24 with equimolar halogenated hydrocarbons at 100～120 DEG C
～72h, Jing recrystallization, obtains faint yellow solid or dope, as halogenation tridemorph quaternary ammonium salt；
2) preparation of hydrogen sulfate tridemorph quaternary ammonium salt：The 1) halogenation tridemorph quaternary ammonium salt that step reaction is obtained with etc. rub
Your sodium bisulfate reacts 3～6h in 90 DEG C, and the sodium halide solid that sucking filtration is generated except dereaction obtains the hydrogen sulfate ten of yellow oily
Morpholine quaternary ammonium salt；
3) preparation of tridemorph quaternary ammonium base：The 2) hydrogen sulfate tridemorph quaternary ammonium salt that step reaction is obtained be dissolved in after water with
Equimolar barium hydroxide solution reacts 2～4h, and the barium sulfate solid that sucking filtration is generated except dereaction, filtrate branch vibration layer is obtained final product
The tridemorph quaternary ammonium base (in half solidification shape during low temperature) of yellow, viscous.
The synthetic route of tridemorph quaternary ammonium base is as follows：
The preparation method of described tridemorph quaternary ammonium base, is characterized in that：The halogenated hydrocarbons are n-butyl bromide, n-octyl
Bromine, benzyl chloride or 2- chloromethylpyridine.
A kind of tridemorph quaternary ammonium base is characterized in that as the application of catalyst for ester exchange reaction：Comprise the following steps：
Oils and fatss, methanol 1: 6～10 feed intake in molar ratio, then put into the catalyst tridemorph quaternary ammonium of oil quality 1～5%
Alkali, flow back 2～4h, reactant liquor is cooled down, is stood, and (simple filtration, you can reclaim, can be direct in half solidification shape precipitation for catalyst
For next round reaction), remaining is divided into two-layer, and upper strata is biodiesel, and Jing distillations obtain finished product, and lower floor is that methanol and glycerol are mixed
Compound, by separated.
The oils and fatss are vegetable oil or treated waste oil.
The present invention has advantages below：
Because of the tridecyl structure of unique oxaza and long-chain so as to unique physicochemical property, especially it
Viscosity by temperature change significantly, when higher than 60 DEG C, viscosity is little, agitated, good with oils and fatss, methanol mixed performance, it is ensured that
High catalysis activity, when less than 20 DEG C, semi-solid separates out into high-viscosity, it is easy to other materials (such as biodiesel, sweet
Oil, methanol) separate.Can recycle repeatedly as catalyst, still keep higher activity.Preparation method is simple, production cost
Relative moderate, is adapted to large-scale production.As the catalyst of production biodiesel, the production procedure of biodiesel is simplified, and
Production process is substantially without waste water, environmental protection.
With reference to embodiment, the invention will be further described.
Specific embodiment
Embodiment 1：The preparation of bromination tridemorph normal-butyl ammonium
44.6g (0.150mol) tridemorphs and stirring reaction 48h at 120 DEG C of 20.6g (0.150mol) n-butyl bromide, obtain
Yellow semisolid crude product, Jing re-crystallizing in ethyl acetate obtains the bromination tridemorph normal-butyl ammonium 63.2g of faint yellow solid, yield
96.9%.
Embodiment 2：The preparation of N- normal-butyl tridemorph disulfates
43.4g (0.100mol) bromination tridemorph normal-butyl ammonium and 12.0g (0.100mol) sodium bisulfate, 90 DEG C of stirrings
Reaction 4h, is filtered to remove the sodium bromide solid that reaction is generated, and obtains the N- normal-butyl tridemorph disulfates of yellow oily
43.5g, yield 96.2%.
Embodiment 3：The preparation of N- normal-butyl tridemorph quaternary ammonium bases
22.6g (0.0500mol) N- normal-butyl tridemorph disulfates are dissolved in 100mL water and contain 8.6g
(0.050mol) aqueous solution stirring reaction 3h of barium hydroxide, is filtered to remove the barium sulfate solid that reaction is generated, and filtrate point removes water
Layer, obtains the N- normal-butyl tridemorph quaternary ammonium base 18.1g of yellow, viscous, yield 97.3%.
The measurement result of gained N- normal-butyl tridemorph quaternary ammonium bases：
Proton nmr spectra (1H NMR,300MHz,D2O) δ 3.66-3.62 (m, 2H), 3.51-3.48 (m, 4H), 3.24-
3.22 (m, 4H), 1.34-1.32 (m, 22H), 1.73 (m, 4H), 1.21 (d, J=7.2Hz, 6H), 0.97 (t, J=7.2Hz,
3H), 0.96 (t, J=7.2Hz, 3H).
Fourier transform infrared spectroscopy (pressing potassium bromide troche)：3415cm-1(roomy peak) is H-O-The stretching vibration peak of key；
2962cm-1、2873cm-1For the stretching vibration peak of methyl c h bond；2929cm-1For the stretching vibration peak of the c h bond of methylene；
1458cm-1、1378cm-1For the flexural vibrations peak of the c h bond of methyl；1333cm-1For the flexural vibrations peak of c h bond on morpholine ring；
1179cm-1、1146cm-1For C-N+The stretching vibration peak of key；1082cm-1、1046cm-1For the stretching vibration peak of C-O keys.
Embodiment 4：N- normal-butyl tridemorph quaternary ammonium base catalysis for preparing biodiesel oil
Electric blender, reflux condensing tube are installed on 250mL three-necked bottles, 100g soybean oils, 35mL methanol, 5g N- is added
Normal-butyl tridemorph quaternary ammonium base, back flow reaction 3h, by reactant liquor cooling, stratification, is recovered by filtration catalyst, and remaining is divided into
Two-layer, lower floor is glycerol and carbinol mixture (can be separately recovered by distillation), and upper strata is biodiesel crude product, and Jing distillations are obtained
Sterling 96.4g, yield 96.4% (in terms of Semen sojae atricolor oil quality).
Embodiment 5：Catalyst repeat performance
By the separating obtained catalyst of previous round for next round test, step is with example 4, the biological bavin obtained by five wheel tests
Oily yield is respectively 96.4%, 96.0%, 95.4%, 94.6%, 93.6% and (supplements catalyst as appropriate, carry can yield
It is high).
Claims (1)
1. a kind of preparation method of tridemorph quaternary ammonium base, is characterized in that：Comprise the following steps：
1) preparation of halogenation tridemorph quaternary ammonium salt：Tridemorph and equimolar halogenated hydrocarbons react 24 at 100～120 DEG C～
72h, Jing recrystallization, obtains faint yellow solid or dope, as halogenation tridemorph quaternary ammonium salt；
2) preparation of hydrogen sulfate tridemorph quaternary ammonium salt：The 1) halogenation tridemorph quaternary ammonium salt that step reaction is obtained with it is equimolar
Sodium bisulfate reacts 3～6h in 90 DEG C, and the sodium halide solid that sucking filtration is generated except dereaction obtains the hydrogen sulfate 13 of yellow oily
Hyamine；
3) preparation of tridemorph quaternary ammonium base：The 2) hydrogen sulfate tridemorph quaternary ammonium salt that step reaction is obtained be dissolved in after water with etc. rub
Your barium hydroxide solution reacts 2～4h, and the barium sulfate solid that sucking filtration is generated except dereaction, filtrate branch vibration layer obtains final product yellow
Thick tridemorph quaternary ammonium base；
The halogenated hydrocarbons are n-butyl bromide；
The tridemorph quaternary ammonium base, structural formula is：
R is normal-butyl.
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| CN201510179832.9A CN104876886B (en) | 2014-02-27 | 2014-02-27 | Preparation method of tridemorph quaternary ammonium hydroxide |
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| CN201410069592.2A CN103833663B (en) | 2014-02-27 | 2014-02-27 | Tridemorph quaternary ammonium base as well as preparation method and application thereof |
| CN201510179832.9A CN104876886B (en) | 2014-02-27 | 2014-02-27 | Preparation method of tridemorph quaternary ammonium hydroxide |
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|---|---|---|---|---|
| CN101525318A (en) * | 2009-04-21 | 2009-09-09 | 南通维立科化工有限公司 | Method for preparing 2, 6-dimethyl-N-tridecyl drewamine |
| WO2010127231A2 (en) * | 2009-05-01 | 2010-11-04 | Signal Investment And Management Co. | Moisturizing antimicrobial composition |
| CN103013680A (en) * | 2012-12-17 | 2013-04-03 | 常州大学 | Method of utilizing dual-function ionic liquid to catalyze waste fat and oil in one step to prepare biodiesel |
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| CN101157667A (en) * | 2007-11-12 | 2008-04-09 | 天津工业大学 | Morpholine quaternary ammonium salt ion liquid and preparation method thereof |
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2014
- 2014-02-27 CN CN201510179832.9A patent/CN104876886B/en not_active Expired - Fee Related
- 2014-02-27 CN CN201510182174.9A patent/CN104818126B/en not_active Expired - Fee Related
- 2014-02-27 CN CN201410069592.2A patent/CN103833663B/en not_active Expired - Fee Related
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101525318A (en) * | 2009-04-21 | 2009-09-09 | 南通维立科化工有限公司 | Method for preparing 2, 6-dimethyl-N-tridecyl drewamine |
| WO2010127231A2 (en) * | 2009-05-01 | 2010-11-04 | Signal Investment And Management Co. | Moisturizing antimicrobial composition |
| CN103013680A (en) * | 2012-12-17 | 2013-04-03 | 常州大学 | Method of utilizing dual-function ionic liquid to catalyze waste fat and oil in one step to prepare biodiesel |
Non-Patent Citations (3)
| Title |
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| 吗啡啉碱性离子液体催化合成油酸甲酯;王吉林 等;《燃料化学学报》;20130131;第41卷(第1期);第86页左栏1.2.1，第87页 图1 * |
| 离子液体1-乙基-3-甲基咪唑醋酸盐的制备及用于纤维素溶解纺丝的研究进展;程春祖 等;《高分子通报》;20110831(第8期);第25页 1.3 * |
| 离子液体的性质及其在催化反应中的应用;王均凤 等;《过程工程学报》;20030431;第3卷(第2期);第179页 2.2.2 * |
Also Published As
| Publication number | Publication date |
|---|---|
| CN104818126A (en) | 2015-08-05 |
| CN103833663B (en) | 2015-07-08 |
| CN104818126B (en) | 2017-12-08 |
| CN103833663A (en) | 2014-06-04 |
| CN104876886A (en) | 2015-09-02 |
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