CN102513107A - Copper-based catalyst for neopentylene glycol preparation from hydrogenation method and preparation method thereof - Google Patents
Copper-based catalyst for neopentylene glycol preparation from hydrogenation method and preparation method thereof Download PDFInfo
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Abstract
A copper-based catalyst for neopentylene glycol preparation from a hydrogenation method and a preparation method thereof. The method comprises steps of: first preparing a copper sulphate aqueous solution; adding refined diatomite into the mixed liquor and stirring; adjusting a pH value by sodium hydroxide; filtering by a plate frame filter press; airing a filter cake and conveying the filter cake into an air-flow drier by a feeding machine; drying by air-flow hot air; and drying and packaging to obtain a finished product. The copper-based catalyst comprises copper oxide accounting for 65-80% of a gross weight of the catalyst and silica accounting for 20-35% of the gross weight of the catalyst. Usage of the catalyst generates no waste water, so as to mitigate environmental pollution; the catalyst has stable property, low price and no safety hidden trouble of a nickel system catalyst; the catalyst has small granularity but lager disperse area to facilitate a hydrogenation reaction; and the catalyst can be applied to neopentylene glycol preparation from hydrogenation in a temperature scope of 150-170 DEG C, and a conversion efficiency of the neopentylene glycol reaches higher than 99%.
Description
Technical field
The present invention relates to catalyst technical field, particularly a kind of hydrogenation method prepares neopentyl glycol with copper-based catalysts and preparation method thereof.
Background technology
Neopentyl glycol (NPG) is widely used in producing all kinds of high performance resins, plasticizer, synthetic lubricant fluid, surfactant and ibuprofen pharmaceutical etc.Early stage formates method production technology is replaced by advanced condensation hydrogenation method abroad; Hydrogenation method is produced neopentyl glycol technology and is comprised that formalin and isobutylaldehyde aldol condensation under base catalyst (organic amine, phase transfer catalyst and anion exchange resin) effect generates hydrogenation of hydroxypentylaldehyd, HPA, makes neopentyl glycol with its hydrogenation then.The hydrogenation catalyst that adopts mainly contains 3 types: nickel system, copper system and noble metal series catalysts.But the nickel catalyst catalytic activity is low, inactivation is fast, is difficult to continuously and large-scale production, and required hot conditions has increased the probability of hydrogenation of hydroxypentylaldehyd, self condensation, has reduced selectivity of neopentyl glycol and product quality.The noble metal series catalysts shows activity and selectivity preferably under lower temperature and pressure condition, but catalyst costs an arm and a leg the production cost height.And Cu-series catalyst has shown activity and selectivity preferably in the technology of hydrogenation preparing neopentyl glycol, and low price, has the good industrial prospect.At number of patent application is to have put down in writing a kind of method for preparing neopentyl glycol in 200910200143.4 the Chinese patent invention application; It has adopted copper-based catalysts; Wherein copper content is 20-50 weight %, contains in chromium, cobalt, the aluminum and zinc one or more mixture in the catalyst, and their content is 1-25 weight %; The carrier of catalyst is an inorganic oxide, can be one or more mixtures in gama-alumina, silica and the molecular sieve.In the patent No. is 201010229538.1 Chinese patent invention application; Put down in writing a kind of preparation method of neopentyl glycol; It has adopted copper-based catalysts; Copper-based catalysts comprises the CuO of 80-90 part, the MnO of 4-7 part and the ZnO of 2-5 part, in the concentrate of hydrogenation of hydroxypentylaldehyd,, adds the absolute methanol of concentrate weight 1%～10% and the copper-based catalysts of concentrate weight 0.2%～3%, under 1.5～8.5MPa condition, hydrogenation of hydroxypentylaldehyd, is carried out hydrogenation at 90 ℃～150 ℃ of temperature, pressure; Hydrogenation time 0.3～2.5h obtains comprising the mixture of neopentyl glycol.Because generate in the reaction of neopentyl glycol at hydrogenation, reaction temperature is high more, reaction rate is fast more, and catalyst grain size is more little, and it disperses area big more, helps hydrogenation reaction.
Summary of the invention
In order to overcome the defective of above-mentioned prior art, the object of the present invention is to provide a kind of hydrogenation method to prepare neopentyl glycol with copper-based catalysts and preparation method thereof, have in the applied environment of 150-170 ℃ high temperature the performance of catalytic hydrogenation efficiently; And reach the purpose that reduces cost and improve safety in utilization.
This catalyst comprises that granularity is Powdered cupric oxide and the silica complex of 1-10 μ m, and wherein cupric oxide is the 65-80% that active component accounts for total catalyst weight, and silica accounts for the 20-35% of total catalyst weight as carrier.
As the best, wherein cupric oxide accounts for the 72-80% of total catalyst weight, the 20-28% of silica comprises total catalyst weight.
Can adopt following method to prepare this catalyst: step 1, preparation Kocide SD deposition: the copper-bath of preparation 0.05-0.1mol/L; In reactor, adding copper-bath and average grain diameter earlier is the terra silicea purificata of 1-2 μ m; The mass ratio of copper sulphate is 20-35:130-160 in terra silicea purificata and the copper-bath; Under 35-42 ℃ of temperature conditions, stir, add the sodium hydroxide solution that concentration is 0.1mol/L immediately, keep 35-42 ℃ of temperature conditions the pH value to be transferred to 8-11 through the addition of control sodium hydroxide solution; Stirred 3-5 hour, mixing speed is 200-400r/min; Step 2, gained solution in the step 1 filtered through plate and frame filter press obtain filter cake; Filter cake is conveyed into pneumatic conveyer dryer with feeding machine; Oven dry is after classifying device for powder is isolated the powder that granularity is 1～10 μ m, and this powder is hydrogenation method and prepares neopentyl glycol and use copper-based catalysts.
In the step 2 in the pneumatic conveyer dryer gas flow temperature be controlled at 100-130 ℃.
Earlier to filter good in illumination again after 2-4 time, temperature-5～37 ℃, relative humidity through water washing be that airing 1 day is sent into feeding machine after the airing completion again under 10～60% the environmental condition to filter cake in the step 2.In the washing process impurity such as sodium sulphate are washed.
Preparation method of the present invention is active component with the cupric oxide, and terra silicea purificata is a carrier, prepares hydrogenation method with coprecipitation and prepares neopentyl glycol and use copper-based catalysts, produces neopentyl glycol thereby reach in the applied environment of high temperature efficiently catalytic hydrogenation.
The present invention compared with prior art has the following advantages and the high-lighting effect; Adopt this catalyst hydrogenation method to produce neopentyl glycol, emit no waste water, thereby alleviated pollution environment; This catalyst property is stable, low price, the potential safety hazard of no nickel catalyst; Catalyst grain size is more little, and it disperses area big more, helps hydrogenation reaction, so this catalyst grain size is controlled at 1～10 μ m, this catalyst can be in 150-170 ℃ of temperature range the hydrogenation preparing neopentyl glycol, and the transformation efficiency of neopentyl glycol reaches more than 99%.
The specific embodiment
Embodiment one
Present embodiment may further comprise the steps:
Step 1, employing coprecipitation prepare the Kocide SD deposition, and the copper-bath of preparation 0.05mol/L is prepared the 0.1mol/L sodium hydroxide solution simultaneously; In reactor, add copper-bath and terra silicea purificata (average grain diameter is 2 μ m) earlier, the mass ratio of terra silicea purificata and copper sulphate is 35:130, under 35 ℃ of temperature conditions, stirs; Add prepared sodium hydroxide solution immediately; The pH value is transferred to 8, stirred 3 hours, mixing speed is 200r/min; Reaction equation is:
Step 2, gained solution in the step 1 filtered through plate and frame filter press process filter cake; It is under 10% the environmental condition that filter cake earlier filters good in illumination again after 2 times, temperature-5 ℃, relative humidity through water washing, airing 1 day, and airing is sent into feeding machine after accomplishing again; Be conveyed into pneumatic conveyer dryer with feeding machine; Gas flow temperature is controlled at 100 ℃, and oven dry is after classifying device for powder is isolated the powder that granularity is 1～10 μ m, and this powder is used copper-based catalysts for the products obtained therefrom hydrogenation method prepares neopentyl glycol.Reaction equation is:
The hydrogenation method of present embodiment gained prepares neopentyl glycol and uses copper-based catalysts, and its molecular formula is expressed as CuO-SiO
2, its component is: cupric oxide accounts for 65% of total catalyst weight, 35% of silica comprises total catalyst weight.
With the absolute methanol that adds its weight 8% in the concentrate of hydrogenation of hydroxypentylaldehyd; Be delivered in 10 liters the tubular type high-pressure reactor with 0.2 liter/minute speed then; Prepare at hydrogenation method that neopentyl glycol exists with copper-based catalysts, carry out hydrogenation under 160 ℃ of temperature and the pressure 4.2MPa condition; Obtain comprising the mixture of neopentyl glycol, wherein hydrogenation method prepares neopentyl glycol with copper-based catalysts (CuO-SiO
2) consumption is 1.0% of concentrate weight.
Contrast groups I: adopted composite catalyst (as using CuO, MnO and ZnO) in the past; Be delivered to 0.1 liter/minute speed in 10 liters the tubular type high-pressure reactor; Prepare at hydrogenation method that neopentyl glycol exists with copper-based catalysts, carry out hydrogenation under 120 ℃ of temperature and the pressure 8.5MPa condition, obtain comprising the mixture of neopentyl glycol, if improve its transfer rate; The conversion ratio of neopentyl glycol obviously descends; Wherein the copper-based catalysts consumption is 1.0% of a concentrate weight, and copper-based catalysts comprises 86 parts of CuO by weight, 7 parts of 7 parts of MnO and ZnO.The form of its contrast is following:
Through gas-chromatography embodiment 1 is analyzed with the neopentyl glycol mixture that contrast groups makes, its result sees table 1:
Can find out through last table; Use this catalyst can under the condition that improves catalyst transport speed, improve the conversion ratio of neopentyl glycol; Reduced the content of impurity; For the Purification of back has alleviated burden, and can under the lower situation of higher temperature and pressure, carry out the preparation of neopentyl glycol, the danger of equipment and energy loss be decline greatly all.
Embodiment two
Step 1, employing coprecipitation prepare the Kocide SD deposition, and the copper-bath of preparation 0.1mol/L is prepared the 0.1mol/L sodium hydroxide solution simultaneously; In reactor, adding copper-bath and average grain diameter earlier is the terra silicea purificata of 2 μ m, and the mass ratio of terra silicea purificata and copper sulphate is 28:144, under 37 ℃ of temperature conditions, stirs; Add prepared sodium hydroxide solution immediately; The pH value is transferred to 9, stirred 4 hours, mixing speed is 300r/min; Its reaction equation is:
Step 2, gained solution in the step 1 filtered through plate and frame filter press process filter cake; Filter cake earlier under good in illumination again behind the water washing filter 23 time, 37 ℃ of temperature, relative humidity are 60% environmental condition, airing 1 day, airing is sent into feeding machine after accomplishing again; Be conveyed into pneumatic conveyer dryer with feeding machine; Gas flow temperature is controlled at 130 ℃, and oven dry is after classifying device for powder is isolated the powder that granularity is 1～10 μ m, and this powder is used copper-based catalysts for the products obtained therefrom hydrogenation method prepares neopentyl glycol.Its reaction equation is:
The hydrogenation method of present embodiment gained prepares neopentyl glycol and uses copper-based catalysts, and its molecular formula is expressed as CuO-SiO
2, its component is: cupric oxide accounts for 72% of total catalyst weight, 28% of silica comprises total catalyst weight.
With the absolute methanol that adds its weight 8% in the concentrate of hydrogenation of hydroxypentylaldehyd; Be delivered in 10 liters the tubular type high-pressure reactor with 0.25 liter/minute speed then; Prepare at hydrogenation method that neopentyl glycol exists with copper-based catalysts, carry out hydrogenation under 170 ℃ of temperature and the pressure 4.2MPa condition; Obtain comprising the mixture of neopentyl glycol, wherein hydrogenation method prepares neopentyl glycol with copper-based catalysts (CuO-SiO
2) consumption is 1.5% of concentrate weight.
Control Group II: adopt composite catalyst (as using CuO, MnO and ZnO); With the absolute methanol that adds its weight 8% in the concentrate of hydrogenation of hydroxypentylaldehyd; Composite catalyst is delivered in 10 liters the tubular type high-pressure reactor with 0.15 liter/minute speed then; Prepare at hydrogenation method that neopentyl glycol exists with copper-based catalysts, carry out hydrogenation under 140 ℃ of temperature and the pressure 8.5MPa condition, obtain comprising the mixture of neopentyl glycol, wherein the copper-based catalysts consumption is 1.5% of a concentrate weight; Copper-based catalysts comprises 86 parts of CuO by weight, 7 parts of 7 parts of MnO and ZnO.
Through gas-chromatography embodiment 2 is analyzed with the neopentyl glycol mixture that contrast groups makes, its result sees table 2:
Can find out through last table; Use this catalyst can under the condition that improves catalyst transport speed, improve the conversion ratio of neopentyl glycol; Reduced the content of impurity; For the Purification of back has alleviated burden, and can under the lower situation of higher temperature and pressure, carry out the preparation of neopentyl glycol, the danger of equipment and energy loss be decline greatly all.
Embodiment three
Step 1, employing coprecipitation prepare the Kocide SD deposition, and the copper-bath of preparation 0.1mol/L is prepared the 0.1mol/L sodium hydroxide solution simultaneously; In reactor, add copper-bath and terra silicea purificata (average grain diameter is 2 μ m) earlier, the mass ratio of terra silicea purificata and copper sulphate is 20:160, under 40 ℃ of temperature conditions, stirs; Add prepared sodium hydroxide solution immediately; The pH value is transferred to 10, stirred 4 hours, mixing speed is 350r/min; Its reaction equation is:
Step 2, gained solution in the step 1 filtered through plate and frame filter press process filter cake; Filter cake earlier under good in illumination again behind the water washing filter 23 time, 20 ℃ of temperature, relative humidity are 30% environmental condition, airing 1 day, airing is sent into feeding machine after accomplishing again; Be conveyed into pneumatic conveyer dryer with feeding machine; Gas flow temperature is controlled at 120 ℃, and oven dry is after classifying device for powder is isolated the powder that granularity is 1～10 μ m, and this powder is used copper-based catalysts for the products obtained therefrom hydrogenation method prepares neopentyl glycol.Its reaction equation is:
The hydrogenation method of present embodiment gained prepares neopentyl glycol and uses copper-based catalysts, and its molecular formula is expressed as CuO-SiO
2, wherein cupric oxide accounts for 80% of total catalyst weight, 20% of silica comprises total catalyst weight.
With the absolute methanol that adds its weight 8% in the concentrate of hydrogenation of hydroxypentylaldehyd; Be delivered in 10 liters the tubular type high-pressure reactor with 0.3 liter/minute speed then; Prepare at hydrogenation method that neopentyl glycol exists with copper-based catalysts, carry out hydrogenation under 150 ℃ of temperature and the pressure 4.2MPa condition; Obtain comprising the mixture of neopentyl glycol, wherein hydrogenation method prepares neopentyl glycol with copper-based catalysts (CuO-SiO
2) consumption is 2.0% of concentrate weight.
Control group III: adopt composite catalyst (as using CuO, MnO and ZnO); With the absolute methanol that adds its weight 8% in the concentrate of hydrogenation of hydroxypentylaldehyd; Composite catalyst is delivered in 10 liters the tubular type high-pressure reactor with 0.15 liter/minute speed then; Prepare at hydrogenation method that neopentyl glycol exists with copper-based catalysts, carry out hydrogenation under 90 ℃ of temperature and the pressure 8.5MPa condition, obtain comprising the mixture of neopentyl glycol, wherein the copper-based catalysts consumption is 2.0% of a concentrate weight; Copper-based catalysts comprises 86 parts of CuO by weight, 7 parts of 7 parts of MnO and ZnO.
Through gas-chromatography embodiment 3 is analyzed with the neopentyl glycol mixture that control group makes, its result sees table 3:
Can find out through last table; Use this catalyst can under the condition that improves catalyst transport speed, improve the conversion ratio of neopentyl glycol; Reduced the content of impurity; For the Purification of back has alleviated burden, and can under the lower situation of higher temperature and pressure, carry out the preparation of neopentyl glycol, the danger of equipment and energy loss be decline greatly all.
Embodiment four
Step 1, employing coprecipitation prepare the Kocide SD deposition, and the copper-bath of preparation 0.05mol/L is prepared the 0.1mol/L sodium hydroxide solution simultaneously; In reactor, add copper-bath and terra silicea purificata (average grain diameter is 2 μ m) earlier, the mass ratio of terra silicea purificata and copper sulphate is 30:140, under 42 ℃ of temperature conditions, stirs; Add prepared sodium hydroxide solution immediately; The pH value is transferred to 11, stirred 5 hours, mixing speed is 400r/min; Its reaction equation is:
Step 2, gained solution in the step 1 filtered through plate and frame filter press process filter cake; It is under 30% the environmental condition that filter cake earlier filters good in illumination again after 4 times, 25 ℃ of temperature, relative humidity through water washing, airing 1 day, and airing is sent into feeding machine after accomplishing again; Be conveyed into pneumatic conveyer dryer with feeding machine; Gas flow temperature is controlled at 110 ℃, and oven dry is after classifying device for powder is isolated the powder that granularity is 1～10 μ m, and this powder is used copper-based catalysts for the products obtained therefrom hydrogenation method prepares neopentyl glycol.Its reaction equation is:
The hydrogenation method of present embodiment gained prepares neopentyl glycol and uses copper-based catalysts, and its molecular formula is expressed as CuO-SiO
2, wherein cupric oxide accounts for 70% of total catalyst weight, 30% of silica comprises total catalyst weight.
With the absolute methanol that adds its weight 8% in the concentrate of hydrogenation of hydroxypentylaldehyd; Be delivered in 10 liters the tubular type high-pressure reactor with 0.3 liter/minute speed then; Prepare at hydrogenation method that neopentyl glycol exists with copper-based catalysts, carry out hydrogenation under 165 ℃ of temperature and the pressure 4.2MPa condition; Obtain comprising the mixture of neopentyl glycol, wherein hydrogenation method prepares neopentyl glycol with copper-based catalysts (CuO-SiO
2) consumption is 2.0% of concentrate weight.
Control group IV: adopt composite catalyst (as using CuO, MnO and ZnO); With the absolute methanol that adds its weight 8% in the concentrate of hydrogenation of hydroxypentylaldehyd; Composite catalyst is delivered in 10 liters the tubular type high-pressure reactor with 0.15 liter/minute speed then; Prepare at hydrogenation method that neopentyl glycol exists with copper-based catalysts, carry out hydrogenation under 120 ℃ of temperature and the pressure 8.5MPa condition, obtain comprising the mixture of neopentyl glycol, wherein the copper-based catalysts consumption is 2.0% of a concentrate weight; Copper-based catalysts comprises 86 parts of CuO by weight, 7 parts of 7 parts of MnO and ZnO.
Through gas-chromatography embodiment 4 is analyzed with the neopentyl glycol mixture that contrast groups makes, its result sees table 4:
Can find out through last table; Use this catalyst can under the condition that improves catalyst transport speed, improve the conversion ratio of neopentyl glycol; Reduced the content of impurity; For the Purification of back has alleviated burden, and can under the lower situation of higher temperature and pressure, carry out the preparation of neopentyl glycol, the danger of equipment and energy loss be decline greatly all.
Claims (5)
1. hydrogenation method prepares neopentyl glycol and uses copper-based catalysts; It is characterized in that; This catalyst comprises that granularity is Powdered cupric oxide and the silica complex of 1-10 μ m; Wherein cupric oxide is the 65-80% that active component accounts for total catalyst weight, and silica accounts for the 20-35% of total catalyst weight as carrier.
2. hydrogenation method as claimed in claim 1 prepares neopentyl glycol and uses copper-based catalysts, it is characterized in that cupric oxide accounts for the 72-80% of total catalyst weight, the 20-28% of silica comprises total catalyst weight.
3. hydrogenation method prepares the preparation method of neopentyl glycol with copper-based catalysts; It is characterized in that may further comprise the steps: step 1, preparation Kocide SD deposition: the copper-bath of preparation 0.05-0.1mol/L; In reactor, adding copper-bath and average grain diameter earlier is the terra silicea purificata of 1-2 μ m, and the mass ratio of copper sulphate is 20-35:130-160 in terra silicea purificata and the copper-bath, under 35-42 ℃ of temperature conditions, stirs; Add the sodium hydroxide solution that concentration is 0.1mol/L immediately; Keep 35-42 ℃ of temperature conditions through the addition of control sodium hydroxide solution the pH value to be transferred to 8-11, stirred 3-5 hour, mixing speed is 200-400r/min; Step 2, gained solution in the step 1 filtered through plate and frame filter press obtain filter cake; Filter cake is conveyed into pneumatic conveyer dryer with feeding machine; Oven dry is after classifying device for powder is isolated the powder that granularity is 1～10 μ m, and this powder is hydrogenation method and prepares neopentyl glycol and use copper-based catalysts.
4. the preparation method described in claim 3 is characterized in that in the step 2 that gas flow temperature is controlled at 100-130 ℃ in the pneumatic conveyer dryer.
5. the preparation method described in claim 3; It is characterized in that filter cake in the step 2 earlier through water washing filter after 2-4 time again illumination well, temperature-5～37 ℃, relative humidity be under 10～60% the environmental condition; Airing 1 day, airing is sent into feeding machine after accomplishing again.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106824239A (en) * | 2017-01-13 | 2017-06-13 | 中国石油化工股份有限公司 | Furfural hydrogenation prepares catalyst of furfuryl alcohol and preparation method thereof |
| CN115069268A (en) * | 2022-08-02 | 2022-09-20 | 山东鲁新设计工程有限公司 | Catalyst for preparing neopentyl glycol by high pressure method |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0474143A (en) * | 1990-07-13 | 1992-03-09 | Mitsubishi Gas Chem Co Inc | Production of neopentyl glycol |
| CN1328986A (en) * | 1994-05-19 | 2002-01-02 | 巴斯福股份公司 | Method for preparation of alcohol |
| CN101735015A (en) * | 2009-12-18 | 2010-06-16 | 上海华谊丙烯酸有限公司 | Method for preparing neopentylene glycol |
| CN101863738A (en) * | 2010-07-19 | 2010-10-20 | 淄博明新化工有限公司 | Method for preparing neopentyl glycol |
-
2011
- 2011-12-20 CN CN 201110428668 patent/CN102513107B/en not_active Expired - Fee Related
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0474143A (en) * | 1990-07-13 | 1992-03-09 | Mitsubishi Gas Chem Co Inc | Production of neopentyl glycol |
| CN1328986A (en) * | 1994-05-19 | 2002-01-02 | 巴斯福股份公司 | Method for preparation of alcohol |
| CN101735015A (en) * | 2009-12-18 | 2010-06-16 | 上海华谊丙烯酸有限公司 | Method for preparing neopentylene glycol |
| CN101863738A (en) * | 2010-07-19 | 2010-10-20 | 淄博明新化工有限公司 | Method for preparing neopentyl glycol |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106824239A (en) * | 2017-01-13 | 2017-06-13 | 中国石油化工股份有限公司 | Furfural hydrogenation prepares catalyst of furfuryl alcohol and preparation method thereof |
| CN106824239B (en) * | 2017-01-13 | 2019-10-01 | 中国石油化工股份有限公司 | Furfural hydrogenation prepares catalyst of furfuryl alcohol and preparation method thereof |
| CN115069268A (en) * | 2022-08-02 | 2022-09-20 | 山东鲁新设计工程有限公司 | Catalyst for preparing neopentyl glycol by high pressure method |
| CN115069268B (en) * | 2022-08-02 | 2024-05-14 | 山东鲁新设计工程股份有限公司 | Catalyst for preparing neopentyl glycol by high-pressure method |
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