CN108727180A - A kind of method of surface amination Sn-Beta molecular sieve catalytics carbohydrate lactic acid producing - Google Patents
A kind of method of surface amination Sn-Beta molecular sieve catalytics carbohydrate lactic acid producing Download PDFInfo
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- CN108727180A CN108727180A CN201810424336.9A CN201810424336A CN108727180A CN 108727180 A CN108727180 A CN 108727180A CN 201810424336 A CN201810424336 A CN 201810424336A CN 108727180 A CN108727180 A CN 108727180A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
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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
- B01J29/00—Catalysts comprising molecular sieves
- B01J29/04—Catalysts comprising molecular sieves having base-exchange properties, e.g. crystalline zeolites
- B01J29/06—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof
- B01J29/70—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of types characterised by their specific structure not provided for in groups B01J29/08 - B01J29/65
- B01J29/7049—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of types characterised by their specific structure not provided for in groups B01J29/08 - B01J29/65 containing rare earth elements, titanium, zirconium, hafnium, zinc, cadmium, mercury, gallium, indium, thallium, tin or lead
- B01J29/7057—Zeolite Beta
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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
- B01J2229/00—Aspects of molecular sieve catalysts not covered by B01J29/00
- B01J2229/10—After treatment, characterised by the effect to be obtained
- B01J2229/18—After treatment, characterised by the effect to be obtained to introduce other elements into or onto the molecular sieve itself
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Abstract
The present invention relates to a kind of preparation methods of surface amination Sn-Beta molecular sieve catalytics carbohydrate lactic acid producing.Include the following steps：Commerical grade Beta molecular sieves are placed in 20 h of dealuminzation in the three-necked flask containing appropriate nitric acid, are made without aluminium Beta molecular sieves（deAl-Beta）；Tin acetate is added, Sn-Beta molecular sieves are made through solid liposome nanoparticle method with deAl-Beta molecular sieves；Sn-Beta molecular sieves are scattered in absolute ethyl alcohol, the difunction catalyst Sn-Beta-NH that amination reagent condensing reflux is made after amination is added2Molecular sieve；Carbohydrate and catalyst are added in reactor by a certain percentage, are 150-230 DEG C in reaction temperature, progress hydro-thermal reaction obtains target product lactic acid under conditions of the reaction time is 0.5 h-8 h.It is easy to get the present invention relates to catalyst and of low cost, technique is concise, easy to operate, realizes that saccharide compound is efficient, highly selective, high yield prepares lactic acid.
Description
Technical field
The present invention relates to the technique that a kind of carbohydrate produces lactic acid, especially a kind of surface amination Sn-Beta molecular sieve catalytics
The method of carbohydrate lactic acid producing, belongs to environment chemical engineering field.
Background technology
As the increasingly depleted and the mankind of fossil resource are to the growing interest of environmental problem, seek a kind of renewable and environment
Friendly alternative energy source is extremely urgent.In numerous regenerative resources, biomass with its derive from a wealth of sources with it is environmental-friendly and by
The favor of numerous researchers.Biomass is generated in nature by photosynthesis as a kind of renewable resource.The whole world is annual
About produce 17,000,000,000 tons of biomass.Conversion of biomass raw material, which is chemicals, can mitigate the dependence to petroleum resources, moreover it is possible to subtract
Few pollution of the fossil resource to environment, is one of the desirable route for solving global energy and environmental problem, there is huge exploitation
Foreground.
Lactic acid（LA）It is a kind of important products of biomass transformation process, since it is in medicine, food, chemical industry, material system
It makes and all there is wide application, social required quantity increasingly to increase in the fields such as daily necessities.Currently, the mode of production of LA is more
It is made in a manner of anaerobic fermentation and chemical catalysis etc..The technique that anaerobic fermentation produces lactic acid is considerably complicated, and the production cycle is long, subsequently
Separation is complicated, and will generate a large amount of calcium sulfate waste residues in process of production, thus inefficiency and not environmentally（Journal of
Chemical Technology & Biotechnology, 2006, 7, 1119-1129）.Compared with Unareobic fermentation, change
Catalysis method rapid reaction, bazardous waste is few and yield is higher, is the scientific research hot spot of current researcher.Wherein, Denmark is special
Profit（PA 200801556, PA 200900757）In reported glucose, fructose, sugarcane for the first time with solid Lewis acid catalyst
The method of the one step production lactic acid such as sugar obtains highest lactic acid yield and reaches 30%.
In recent years in order to improve lactic acid yield, researcher is once by building alkaline system, such as at Ba (OH)2
（ChemSusChem, 2013, 6, 989-992）And NaOH（Green Chemistry, 2014, 9, 4234-4240）It is molten
In liquid, the yield of catalysis glucose lactic acid producing 60% or so is obtained.But alkali is to the seriously corroded of common response device, thus it is right
Reactor material requirement is very high, and the product finally obtained after reacting is lactate, it is still necessary to be neutralized with a large amount of acid
To obtain lactic acid, operation sequence and cost are considerably increased.Therefore, big rule of the alkaline reaction system of exploiting economy environmental protection to LA
Mould production is of great significance.
Invention content
The purpose of the present invention is to provide a kind of methods of surface amination Sn-Beta molecular sieve catalytics carbohydrate lactic acid producing.
To achieve the goals above, the present invention uses following technical scheme：
A kind of Sn-Beta-NH proposed by the present invention2The method that molecular sieve catalytic converts carbohydrate lactic acid producing, is as follows：
By 45 mg-225 mg carbohydrates, 120-220 mg Sn-Beta-NH2Molecular sieve catalyst and 10 mL solvents sequentially add
Into polytetrafluoroethylcontainer container tank, then after polytetrafluoroethylcontainer container tank is put into stainless steel cauldron, it is placed in baking oven, waits for baking oven
Start timing when rising to 150 DEG C -230 DEG C, after reacting the h of 0.5 h ~ 8, reaction mixture is centrifuged, with micro-sampling tolerance
It takes supernatant liquor by 0.22 μm of water phase membrane filtration, high performance liquid chromatography is used after being used in combination deionized water to dilute 10 times（HPLC）
Analysis test.
In the present invention, the carbohydrate is any in glucose, fructose, sucrose, starch or lactose.
In the present invention, Sn-Beta-NH2The preparation method of molecular sieve catalyst is as follows：
（1）Commerical grade Beta molecular sieves are weighed, are placed in the three-necked flask containing nitric acid（It is thrown in per 1g commerical grade Beta molecular sieves
Add 20 mL nitric acid）, under the conditions of 80 DEG C, with 200 rpm stir speed (S.S.) dealuminzations 20h；Mixture after dealuminzation through supercentrifuge from
The heart detaches, and control rotating speed is 4000 rpm, then washs the solid component after centrifugation several times with distilled water, until cleaning solution pH value is aobvious
When neutral, solid component is dried 8-10 hours to get no aluminium Beta molecular sieves under the conditions of 150 DEG C（deAl-Beta）；
（2）By tin acetate and step（1）Obtained deAl-Beta molecular sieves mixing（0.2 g tin acetates are added per 1g molecular sieves）
Afterwards, 30min is ground, the mixture after grinding obtains Sn-Beta molecular sieve catalysts in 550 DEG C of 6 h of tubular type kiln roasting；
（3）Before carrying out surface amination, by step（2）Obtained Sn-Beta molecular sieve catalysts are first done under the conditions of 120 DEG C
Dry 2h, to remove the impurity molecules such as moisture of Sn-Beta molecular sieve catalyst surface physics absorption；Weigh Sn-Beta points of 0.5g
Sub- sieve catalyst is scattered in 250 mL absolute ethyl alcohols, and 0.1 μ L-200 μ L amination reagents are then added, are condensed under the conditions of 80 DEG C
Flow back 6 h；It is filtered after being cooled to room temperature, a large amount of absolute ethyl alcohols is used in combination to wash, 80 DEG C of drying obtain the Sn-Beta- after amination
NH2Molecular sieve catalyst.
In the present invention, the amination reagent is 3- aminopropyl trimethoxysilanes（APTMS）Or 3- aminopropyl-triethoxies
Silane（APTES）In it is any.
In the present invention, the solvent is water.
Compared with the existing technology, the present invention has the following advantages and beneficial effect：
1. catalyst used herein is cheap, synthesis is simple, and reaction raw materials are cheap and easy to get, and reaction condition is mildly controllable,
LA yields are up to 50% or more；
2. not needing high-pressure inert gas protection in reaction process of the present invention, there is good application prospect.
Description of the drawings
Fig. 1 is CO of the Beta molecular sieves before and after APTMS aminations2- TPD collection of illustrative plates.
Fig. 2 is Py-IR collection of illustrative plates of the Beta molecular sieves before and after APTMS aminations.
Fig. 3 is Sn-Beta molecular sieves when the amination amount of APTMS is 30 μ L, Sn-Beta-NH2(30)The XPS spectrum of catalyst
Figure.
Specific implementation mode
Below by embodiment combination attached drawing, the present invention is described in further detail.
Embodiment 1
By 225 mg glucose, the Sn-Beta-NH that 160 mg APTMS dosages are 30 uL2(30)Molecular sieve catalyst and 10 mL
Distilled water sequentially adds in polytetrafluoroethylcontainer container tank, then polytetrafluoroethylcontainer container tank is put into stainless steel cauldron and is placed on baking
In case.2 h of timing when baking oven rises to 190 DEG C of reaction temperature.After reaction, reaction mixture is centrifuged, and uses micro-sampling
Tolerance takes supernatant liquor by 0.22 μm of organic membrane filtration, and high performance liquid chromatography is used after being used in combination deionized water to dilute 10 times
（HPLC）Analysis test.The result shows that inversion rate of glucose 100%, lactic acid yield 56%.
Embodiment 2
The present embodiment is as different from Example 1：Sn-Beta-NH used2(0)Molecular sieve catalyst APTMS dosages are 0 uL（I.e.
Sn-Beta molecular sieves）, other steps, parameter and operation are same as Example 1.Inversion rate of glucose is under the embodiment
97%, lactic acid yield 23%.
Embodiment 3
The present embodiment is as different from Example 1：Sn-Beta-NH used2(10)Molecular sieve catalyst APTMS dosages are 10 uL,
Other steps, parameter and operation are same as Example 1.Inversion rate of glucose is 100% under the embodiment, and lactic acid yield is
35%。
Embodiment 4
The present embodiment is as different from Example 1：Sn-Beta-NH used2(50)Molecular sieve catalyst APTMS dosages are 50 uL,
Other steps, parameter and operation are same as Example 1.Inversion rate of glucose is 100% under the embodiment, and lactic acid yield is
52%。
Embodiment 5
The present embodiment is as different from Example 1：Sn-Beta-NH used2(70)Molecular sieve catalyst APTMS dosages are 70 uL,
Other steps, parameter and operation are same as Example 1.Inversion rate of glucose is 100% under the embodiment, and lactic acid yield is
49%。
Embodiment 6
The present embodiment is as different from Example 1：Sn-Beta-NH used2(90)Molecular sieve catalyst APTMS dosages are 90 uL,
Other steps, parameter and operation are same as Example 1.Inversion rate of glucose is 100% under the embodiment, and lactic acid yield is
47%。
Embodiment 7
The present embodiment is as different from Example 1：Sn-Beta-NH used2(120)Molecular sieve catalyst APTMS dosages are 120
UL, other steps, parameter and operation are same as Example 1.Inversion rate of glucose is 100% under the embodiment, and lactic acid yield is
44%。
Embodiment 8
The present embodiment is as different from Example 1：Sn-Beta-NH used2(150)Molecular sieve catalyst APTMS dosages are 150
UL, other steps, parameter and operation are same as Example 1.Inversion rate of glucose is 100% under the embodiment, and lactic acid yield is
31%。
Embodiment 9
The present embodiment is as different from Example 1：Sn-Beta-NH used2(200)Molecular sieve catalyst APTMS dosages are 200
UL, other steps, parameter and operation are same as Example 1.Inversion rate of glucose is 100% under the embodiment, and lactic acid yield is
30%。
Embodiment 10
The present embodiment is as different from Example 1：Time used is 0.5 h, other steps, parameter and liquid-phase chromatographic analysis operation
It is same as Example 1.Inversion rate of glucose is 97% under the embodiment, lactic acid yield 34%.
Embodiment 11
The present embodiment is as different from Example 1：Time used is 1 h, other steps, parameter and liquid-phase chromatographic analysis operation are equal
It is same as Example 1.Inversion rate of glucose is 98% under the embodiment, lactic acid yield 50%.
Embodiment 12
The present embodiment is as different from Example 1：Time used is 3 h, other steps, parameter and liquid-phase chromatographic analysis operation are equal
It is same as Example 1.Inversion rate of glucose is 100% under the embodiment, lactic acid yield 56%.
Embodiment 13
The present embodiment is as different from Example 1：Time used is 4 h, other steps, parameter and liquid-phase chromatographic analysis operation are equal
It is same as Example 1.Inversion rate of glucose is 98% under the embodiment, lactic acid yield 57%.
Embodiment 14
The present embodiment is as different from Example 1：Time used is 5 h, other steps, parameter and liquid-phase chromatographic analysis operation are equal
It is same as Example 1.Inversion rate of glucose is 100% under the embodiment, lactic acid yield 57%.
Embodiment 15
The present embodiment is as different from Example 1：Time used is 6 h, other steps, parameter and liquid-phase chromatographic analysis operation are equal
It is same as Example 1.Inversion rate of glucose is 100% under the embodiment, lactic acid yield 58%.
Embodiment 16
The present embodiment is as different from Example 1：Time used is 7 h, other steps, parameter and liquid-phase chromatographic analysis operation are equal
It is same as Example 1.Inversion rate of glucose is 100% under the embodiment, lactic acid yield 57%.
Embodiment 17
The present embodiment is as different from Example 1：Time used is 8 h, other steps, parameter and liquid-phase chromatographic analysis operation are equal
It is same as Example 1.Inversion rate of glucose is 100% under the embodiment, lactic acid yield 57%.
Embodiment 18
The present embodiment is as different from Example 1：The quality of glucose used is 45 mg, other steps, parameter and liquid chromatogram
Analysis operation is same as Example 1.Inversion rate of glucose is 100% under the embodiment, lactic acid yield 67%.
Embodiment 19
The present embodiment is as different from Example 1：The quality of glucose used is 135 mg, other steps, parameter and liquid phase color
Spectrum analysis operation is same as Example 1.Inversion rate of glucose is 100% under the embodiment, lactic acid yield 63%.
Embodiment 20
The present embodiment is as different from Example 1：The quality of glucose used is 315 mg, other steps, parameter and liquid phase color
Spectrum analysis operation is same as Example 1.Inversion rate of glucose is 100% under the embodiment, lactic acid yield 46%.
Embodiment 21
The present embodiment is as different from Example 1：The quality of glucose used is 405 mg, other steps, parameter and liquid phase color
Spectrum analysis operation is same as Example 1.Inversion rate of glucose is 100% under the embodiment, lactic acid yield 39%.
Embodiment 22
The present embodiment is as different from Example 1：The quality of glucose used is 495 mg, other steps, parameter and liquid phase color
Spectrum analysis operation is same as Example 1.Inversion rate of glucose is 97% under the embodiment, lactic acid yield 29%.
Embodiment 23
The present embodiment is as different from Example 1：The quality of glucose used is 585 mg, other steps, parameter and liquid phase color
Spectrum analysis operation is same as Example 1.Inversion rate of glucose is 96% under the embodiment, lactic acid yield 28%.
Embodiment 24
The present embodiment is as different from Example 1：The quality of glucose used is 675 mg, other steps, parameter and liquid phase color
Spectrum analysis operation is same as Example 1.Inversion rate of glucose is 96% under the embodiment, lactic acid yield 23%.
Embodiment 25
The present embodiment is as different from Example 1：Carbohydrate used is sucrose, Sn-Beta-NH used2(10)Molecular sieve catalyst
APTMS dosages are 10 uL, other steps, parameter and operation are same as Example 1.Sucrose conversion is under the embodiment
100%, lactic acid yield 58%.
Embodiment 26
The present embodiment is as different from Example 1：Carbohydrate used is sucrose, Sn-Beta-NH used2(30)Molecular sieve catalyst
APTMS dosages are 30 uL, other steps, parameter and operation are same as Example 1.Sucrose conversion is under the embodiment
100%, lactic acid yield 50%.
Embodiment 27
The present embodiment is as different from Example 1：Carbohydrate used be starch, other steps, parameter and operation with 1 phase of embodiment
Together.Lactic acid yield is 20% under the embodiment.
Embodiment 28
The present embodiment is as different from Example 1：Carbohydrate used be lactose, other steps, parameter and operation with 1 phase of embodiment
Together.Lactic acid yield is 30% under the embodiment.
Embodiment 29
The present embodiment is as different from Example 1：Amination reagent used be APTES, other steps, parameter and operation with implementation
Example 1 is identical.Inversion rate of glucose is 100% under the embodiment, lactic acid yield 54%.
This hair can be understood and applied the above description of the embodiments is intended to facilitate those skilled in the art
It is bright.Person skilled in the art obviously easily can make various modifications to these embodiments, and described herein
General Principle is applied in other embodiment without having to go through creative labor.Therefore, the present invention is not limited to implementations here
Example, those skilled in the art's announcement according to the present invention, improvement and modification made without departing from the scope of the present invention all should be
Within protection scope of the present invention.
Claims (5)
1. a kind of Sn-Beta-NH2The method that molecular sieve catalytic converts carbohydrate lactic acid producing, it is characterised in that be as follows：
By 45 mg-225 mg carbohydrates, 120-220 mg Sn-Beta-NH2Molecular sieve catalyst and 10 mL solvents are added sequentially to
In polytetrafluoroethylcontainer container tank, then after polytetrafluoroethylcontainer container tank is put into stainless steel cauldron, it is placed in baking oven, waits for baking oven liter
Start timing when to 150 DEG C -230 DEG C, after reacting the h of 0.5 h ~ 8, reaction mixture is centrifuged, and is measured with microsyringe
Supernatant liquor uses high performance liquid chromatography by 0.22 μm of water phase membrane filtration after being used in combination deionized water to dilute 10 times（HPLC）Point
Analysis test.
2. Sn-Beta-NH according to claim 12The method that molecular sieve catalytic converts carbohydrate lactic acid producing, it is characterised in that
The carbohydrate is any in glucose, fructose, sucrose, starch or lactose.
3. Sn-Beta-NH according to claim 12The method that molecular sieve catalytic converts carbohydrate lactic acid producing, it is characterised in that
Sn-Beta-NH2The preparation method of molecular sieve catalyst is as follows：
（1）Commerical grade Beta molecular sieves are weighed, are placed in the three-necked flask containing nitric acid（It is thrown in per 1g commerical grade Beta molecular sieves
Add 20 mL nitric acid）, under the conditions of 80 DEG C, with 200 rpm stir speed (S.S.) dealuminzations 20h；Mixture after dealuminzation through supercentrifuge from
The heart detaches, and control rotating speed is 4000 rpm, then washs the solid component after centrifugation several times with distilled water, until cleaning solution pH value is aobvious
When neutral, solid component is dried 8-10 hours to get no aluminium Beta molecular sieves under the conditions of 150 DEG C（deAl-Beta）；
（2）By tin acetate and step（1）Obtained deAl-Beta molecular sieves mixing（0.2 g tin acetates are added per 1g molecular sieves）
Afterwards, 30min is ground, the mixture after grinding obtains Sn-Beta molecular sieve catalysts in 550 DEG C of 6 h of tubular type kiln roasting；
（3）Before carrying out surface amination, by step（2）Obtained Sn-Beta molecular sieve catalysts are first done under the conditions of 120 DEG C
Dry 2h, to remove the impurity molecules such as moisture of Sn-Beta molecular sieve catalyst surface physics absorption；Weigh Sn-Beta points of 0.5g
Sub- sieve catalyst is scattered in 250 mL absolute ethyl alcohols, and 0.1 μ L-200 μ L amination reagents are then added, are condensed under the conditions of 80 DEG C
Flow back 6 h；It is filtered after being cooled to room temperature, a large amount of absolute ethyl alcohols is used in combination to wash, 80 DEG C of drying obtain the Sn-Beta- after amination
NH2Molecular sieve catalyst.
4. Sn-Beta-NH according to claim 32The method that molecular sieve catalytic converts carbohydrate lactic acid producing, it is characterised in that
The amination reagent is 3- aminopropyl trimethoxysilanes（APTMS）Or 3- aminopropyl triethoxysilanes（APTES）In it is any
Kind.
5. Sn-Beta-NH according to claim 12The method that molecular sieve catalytic converts carbohydrate lactic acid producing, it is characterised in that
The solvent is water.
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| CN111807955A (en) * | 2020-08-10 | 2020-10-23 | 中国科学院上海高等研究院 | Method for continuously and efficiently preparing lactate |
| CN114272954A (en) * | 2021-04-06 | 2022-04-05 | 天津师范大学 | Catalyst for preparing methyl lactate by biomass glycerol one-step method and preparation method and application thereof |
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| CN114272954B (en) * | 2021-04-06 | 2023-05-12 | 天津师范大学 | Catalyst for preparing methyl lactate from biomass glycerin by one-step method, preparation method and application |
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Application publication date: 20181102 |