CN106187682A - A kind of preparation method of decanol - Google Patents
A kind of preparation method of decanol Download PDFInfo
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- CN106187682A CN106187682A CN201610471474.3A CN201610471474A CN106187682A CN 106187682 A CN106187682 A CN 106187682A CN 201610471474 A CN201610471474 A CN 201610471474A CN 106187682 A CN106187682 A CN 106187682A
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- oxide
- decanol
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
- C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
- C07C29/143—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of ketones
- C07C29/145—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of ketones with hydrogen or hydrogen-containing gases
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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
- B01J29/08—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of the faujasite type, e.g. type X or Y
- B01J29/16—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of the faujasite type, e.g. type X or Y containing arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
- B01J29/166—Y-type faujasite
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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
- B01J2229/186—After treatment, characterised by the effect to be obtained to introduce other elements into or onto the molecular sieve itself not in framework positions
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- Organic Chemistry (AREA)
- Crystallography & Structural Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
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Abstract
The invention discloses the preparation method of a kind of decanol, comprise the steps: under nitrogen protection, to be mixed with Polyethylene Glycol by catalyst；It is subsequently adding reactant 2 decanone, in hydrogen atmosphere, pressure 6 8MPa, temperature 18 28 DEG C, stirring reaction 18 64 hours, product is concentrated under reduced pressure to give product decanol by after rapid column chromatography.The present invention is by the following technical solutions: catalyst amount is little, environmentally safe, and 2 decanone conversion ratios can be made to reach 99.9%, prepares the purity of decanol up to 99.9%.
Description
Technical field
The present invention relates to technical field of chemical synthesis, it is prepared by original raw material for particularly relating to a kind of employing 2-decanone
The preparation method of decanol.
Background technology
Decanol has another name called Decanol/decanol/1-decanol/ten carbon alcohol/nonyl carbinol, has and has that wax is fragrant, fragrant and sweet, the fragrance of a flower, fruital
Colourless transparent liquid as fragrance, with the blended liquid phase of citronellol orrisroot oil.Close for making artificial Oleum Rosae Rugosae, orange blossom type and gold
Joyous type essence etc..It is also used for lube oil additive processed, plasticizer, adhesive etc..
It is one of fundamental reaction in organic chemistry that C=O base in aldehyde ketone functional group is reduced into corresponding alcohol, typically has
The reaction of two types can realize this transformation: direct hydrogenation thing reduces, catalytic hydrogenation.
Traditional catalytic hydrogenation uses the metal catalytics such as Ni, Pt, as Chinese patent (CN102557867) is invented
A kind of method of preparing alcohol by hydrogenating relative ketone, uses SiO2The Ni catalyst of load, reaction is entered in fixed bed reactors
OK, 2-decanone conversion ratio 93.3%, the method relates to the step such as activation of catalyst, gas shield, and process is loaded down with trivial details, and cost is high,
And by-product is many.
At present, high fatty alcohol many employings organo-metallic catalyst catalytic hydrogenation, the letter of this kind of method step are prepared in ketone hydrogenation
Single, conversion ratio is high.As patent WO2011033022 has invented a kind of novel metal Os catalyst, catalytic hydrogenation 2-decanone
Conversion ratio is 95%, and its course of reaction need to use substantial amounts of alkali with solvent, and the garbage that industrialized production produces is many, to environment
Unfriendly.
Summary of the invention
The technical problem to be solved in the present invention is to provide a kind of energy consumption low for the deficiencies in the prior art, catalyst amount
Little, environmentally safe, 2-decanone conversion ratio can be made to reach 99.9%, prepare the purity of decanol up to
The preparation method of the decanol of 99.9%.
The present invention by the following technical solutions, the preparation method of a kind of decanol, comprise the steps: under nitrogen protection,
Catalyst is mixed with Polyethylene Glycol；
It is subsequently adding reactant decanone, in hydrogen atmosphere, pressure 6-8MPa, temperature 18-28 DEG C, stirring reaction 18-64
Hour, product is concentrated under reduced pressure to give product decanol by after rapid column chromatography.
The following is further improvement of the present invention:
Described catalyst is made up of the material of following weight portion: molybdenum oxide 5 parts, cobalt oxide 6 parts, tungsten oxide 3 parts, nickel oxide 3
Part, potassium oxide 4 parts, six ammonium chloropalladates 8 parts, white carbon black 3 parts, Pulvis Talci 6 parts, 8 parts of molecular sieve, amorphous silica-alumina 10 parts；
The preparation method of above-mentioned catalyst, comprises the steps:
1), by above-mentioned molybdenum oxide 5 parts, cobalt oxide 6 parts, tungsten oxide 3 parts, nickel oxide 3 parts, potassium oxide 4 parts, six ammonium chloropalladates 8
Part, white carbon black 3 parts, Pulvis Talci 6 parts, 8 parts of molecular sieve, 10 parts of mix homogeneously of amorphous silica-alumina, compressing, obtain complex catalyst precursor
Body；
2), adding in plasma daughter generator by catalyst precursor in step 1, the power adjusting plasma generator is
Carry out plasma-activated during 50-1000W, and plasma activation time is 3～40min；
Step 2) cavity of plasma generator is metallic cavity or glass chamber；Exciting electrode is low frequency electrode, penetrates
Frequently electrode or microwave electrodes；
Step 2) in, when described catalyst precursor is inserted described plasma generator, first that hydrogenation catalyst is uniform
Be placed in the container that electric conductivity is good, container is placed in plasma generator, opens vacuum pump, at plasma
The vacuum of 10-50Pa is formed in the vacuum cavity of generator；
Step 2) described in the exciting electrode of plasma generator be radio-frequency electrode, radio-frequency electrode power is 60-100W.
The present invention is by the following technical solutions: catalyst amount is little, environmentally safe, can make 2-decanone
Conversion ratio reaches 99.9%, prepares the purity of decanol up to 99.9%
The present invention uses above-mentioned catalyst, and selectivity is high, runs 5000 hours continuously, still keeps higher activity and stablizes
Property, the catalyst pore volume of the present invention is 1mL/g, and specific surface area is 500m2/ g, the pore volume shared by hole of bore dia ＜ 3nm
Accounting for less than the 25% of total pore volume, pore volume shared by the hole of bore dia ＞ 15nm accounts for more than the 25% of total pore volume, meleic acid amount
0.220-0.520mmol/g。
Detailed description of the invention
Embodiment, the preparation method of a kind of decanol, comprise the steps: under nitrogen protection, by catalyst and ethylene glycol
Mixing, is subsequently adding reactant 2-decanone, in hydrogen atmosphere, pressure 6-8MPa, temperature 18-28 DEG C, stirring reaction 18-
64 hours, product is concentrated under reduced pressure to give product decanol by after rapid column chromatography.
Described catalyst is made up of the material of following weight portion: molybdenum oxide 5 parts, cobalt oxide 6 parts, tungsten oxide 3 parts, oxidation
3 parts of nickel, potassium oxide 4 parts, six ammonium chloropalladates 8 parts, white carbon black 3 parts, Pulvis Talci 6 parts, 8 parts of molecular sieve, amorphous silica-alumina 10 parts.
The weight of catalyst accounts for the 0.5% of ethylene glycol gross weight, and catalyst accounts for addition 2-with the weight of the mixture of ethylene glycol
The 0.1% of decanone gross weight.
Described molecular sieve is Y type molecular sieve, β zeolite, ZSM-2 molecular sieve and the mixture of SAPO-11 molecular sieve, Y
The mass ratio of type molecular sieve, β zeolite, ZSM-5 molecular sieve and SAPO-11 molecular sieve is 5:3:2:1.
The relative crystallinity of described SAPO-11 molecular sieve is 98%, and crystal particle diameter is 2.5 μm.
The relative crystallinity 95%～110% of described Y type molecular sieve, crystal particle diameter is 1.8 μm.
Described amorphous silica-alumina comprises silicon oxide 8wt%-50wt%, and specific surface area is 700-800m2/ g, pore volume is
1.6-1.8ml/g, bore dia 8-15nm, shared pore volume accounts for the 95%-98% of total pore volume, and infrared total acid content is 0.30-
0.45mmol/g, middle strong acid amount/infrared total acid content is 0.56-0.81, and L acid amount/B acid amount is 1.40-2.30.
The preparation method of described amorphous silica-alumina is as follows:
A, respectively preparation sodium aluminate solution and sodium silicate solution；
B, by sodium aluminate solution adds part or all of sodium silicate solution, then pass to CO2Gas, controlling reaction temperature is
10-40 DEG C, the pH value controlling cemented into bundles is 8-11；Wherein as the CO being passed through2 Gas flow accounts for the 40% of total intake
～100%, add excess silicon acid sodium solution；
C, at the control temperature and pH value of step b, the mixture of step b gained ventilates and stablizes 40-60 minute；
D, by step c gained solidliquid mixture filter, Cake Wash；
E, the filter cake of step d gained is pulled an oar, then carry out hydrothermal treatment consists, through filtering, being dried, obtain amorphous silica-alumina；Institute
The hydrothermal conditions stated is as follows: at 120-150 DEG C, processes 2-5 hour under 0.5-4.0MPa water vapor pressure.
In step b, as the CO being passed through2When gas flow accounts for the 50%-80% of total intake, add surplus
Remaining sodium silicate solution.
In described step a, the concentration of sodium aluminate solution is 15-55g Al2O3/ l, sodium silicate solution dense
Degree is 50-200g SiO2/l。
Step b adds all or part of sodium silicate solution, is whole sodium silicate solutions of being added
5wt%-100wt%.
Described CO2The concentration of gas is 30v%-60v%.
The detailed process employing following methods of step b:
(1), in sodium aluminate, add whole sodium silicate after, be passed through CO2Gas；
(2), in sodium aluminate, after addition part sodium silicate, it is passed through whole CO2Gas, then adds excess silicon in mixture
Acid sodium solution；
(3), in sodium aluminate, after addition part sodium silicate, it is passed through part CO2Gas, more logical CO2Gas is while adding
Enter excess silicon acid sodium solution.
Washing described in step d is that 50-90 DEG C of deionized water of filter cake is washed till neutrality.
Making beating described in step e is to be 8:1-10:1 by solid-liquid volume ratio, and add water in filter cake making beating.
Drying condition described in step e is as follows: dry 6-8 hour at 110-130 DEG C.
The preparation method of above-mentioned Y type molecular sieve includes following process: fresh NaY Crystallization of Zeolite serosity is filtering
Rinsing molecular sieve filter cake with the alkali liquor of molecular sieve butt quality 4-6 times during separation, concentration of lye is 0.001-0.5mol/L, alkali
Liquid temp is 30-90 DEG C；Then above-mentioned NaY molecular sieve filter cake is pulled an oar, adds the compound solution containing H+ ion,
The pH value making NaY molecular sieve pulp is maintained at 2.5-7.0, and reaction temperature is 5-100 DEG C, exchange reaction 0.2-6
Hour, swap with the sodium in zeolite with H+, after H+ exchange, have filtration, washing, roasting process.
The preparation method of above-mentioned catalyst, comprises the steps:
1), by above-mentioned molybdenum oxide 5 parts, cobalt oxide 6 parts, tungsten oxide 3 parts, nickel oxide 3 parts, potassium oxide 4 parts, six ammonium chloropalladates 8
Part, white carbon black 3 parts, Pulvis Talci 6 parts, 8 parts of molecular sieve, 10 parts of mix homogeneously of amorphous silica-alumina, compressing, obtain complex catalyst precursor
Body；
2), adding in plasma daughter generator by catalyst precursor in step 1, the power adjusting plasma generator is
Carry out plasma-activated during 50-1000W, and plasma activation time is 3～40min；
Step 2) cavity of plasma generator is metallic cavity or glass chamber；Exciting electrode is low frequency electrode, penetrates
Frequently electrode or microwave electrodes；
Step 2) in, when described catalyst precursor is inserted described plasma generator, first that hydrogenation catalyst is uniform
Be placed in the container that electric conductivity is good, container is placed in plasma generator, opens vacuum pump, at plasma
The vacuum of 10-50Pa is formed in the vacuum cavity of generator；
Step 2) described in the exciting electrode of plasma generator be radio-frequency electrode, radio-frequency electrode power is 60-100W.
Claims (2)
1. the preparation method of a decanol, it is characterised in that: comprise the steps: under nitrogen protection, by catalyst and poly-second
Glycol mixes；
It is subsequently adding reactant 2-decanone, in hydrogen atmosphere, pressure 6-8MPa, temperature 30-40 DEG C, stirring reaction 18-64
Hour, product is concentrated under reduced pressure to give product decanol by after rapid column chromatography.
The preparation method of decanol the most according to claim 1, it is characterised in that: described catalyst is by the thing of following weight portion
Matter forms: molybdenum oxide 5 parts, cobalt oxide 6 parts, tungsten oxide 3 parts, nickel oxide 3 parts, potassium oxide 4 parts, six ammonium chloropalladates 8 parts, white carbon black
3 parts, Pulvis Talci 6 parts, 8 parts of molecular sieve, amorphous silica-alumina 10 parts；
The preparation method of above-mentioned catalyst, comprises the steps:
1), by above-mentioned molybdenum oxide 5 parts, cobalt oxide 6 parts, tungsten oxide 3 parts, nickel oxide 3 parts, potassium oxide 4 parts, six ammonium chloropalladates 8
Part, white carbon black 3 parts, Pulvis Talci 6 parts, 8 parts of molecular sieve, 10 parts of mix homogeneously of amorphous silica-alumina, compressing, obtain complex catalyst precursor
Body；
2), adding in plasma generator by catalyst precursor in step 1, the power adjusting plasma generator is
Carry out plasma-activated during 50-1000W, and plasma activation time is 3-40min；
Step 2) cavity of plasma generator is metallic cavity or glass chamber；
Step 2) in, when described catalyst precursor is inserted described plasma generator, first by hydrogenation catalyst equably
It is placed in the container that electric conductivity is good, container is placed in plasma generator, opens vacuum pump, send out at plasma
The vacuum of 10-50Pa is formed in the vacuum cavity of raw device；
Step 2) described in the exciting electrode of plasma generator be radio-frequency electrode, radio-frequency electrode power is 60-100W.
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| Application Number | Priority Date | Filing Date | Title |
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| CN201610471474.3A CN106187682A (en) | 2016-06-27 | 2016-06-27 | A kind of preparation method of decanol |
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| CN201610471474.3A CN106187682A (en) | 2016-06-27 | 2016-06-27 | A kind of preparation method of decanol |
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Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3980718A (en) * | 1971-01-13 | 1976-09-14 | Yeda Research & Development Co. Ltd. | Production of alcohols by reduction of carbonyl compounds with a crystalline aluminosilicate-isopropanol system |
| CN101185893A (en) * | 2006-11-17 | 2008-05-28 | 南化集团研究院 | Catalyst for preparation of decyl alcohols by gas-phase hydrogenation of decylenaldehydes and preparation method thereof |
| CN101376104A (en) * | 2007-08-31 | 2009-03-04 | 赢创奥克森诺有限责任公司 | Hydrogenation catalyst and method for the production of alcohols by hydrogenating carbonyl compounds |
| KR101219258B1 (en) * | 2009-10-08 | 2013-01-10 | 주식회사 엘지화학 | Method For The Hydrogenation Of Aldehydes And Apparatus Using The Same |
-
2016
- 2016-06-27 CN CN201610471474.3A patent/CN106187682A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3980718A (en) * | 1971-01-13 | 1976-09-14 | Yeda Research & Development Co. Ltd. | Production of alcohols by reduction of carbonyl compounds with a crystalline aluminosilicate-isopropanol system |
| CN101185893A (en) * | 2006-11-17 | 2008-05-28 | 南化集团研究院 | Catalyst for preparation of decyl alcohols by gas-phase hydrogenation of decylenaldehydes and preparation method thereof |
| CN101376104A (en) * | 2007-08-31 | 2009-03-04 | 赢创奥克森诺有限责任公司 | Hydrogenation catalyst and method for the production of alcohols by hydrogenating carbonyl compounds |
| KR101219258B1 (en) * | 2009-10-08 | 2013-01-10 | 주식회사 엘지화학 | Method For The Hydrogenation Of Aldehydes And Apparatus Using The Same |
Non-Patent Citations (1)
| Title |
|---|
| CHANGJUN LIU等: "Plasma methods for preparing green catalysts: Current status and perspective", 《CHINESE JOURNAL OF CATALYSIS》 * |
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