CN104128185A - Tetralin synthesis catalyst, and preparation method and application thereof - Google Patents
Tetralin synthesis catalyst, and preparation method and application thereof Download PDFInfo
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- CN104128185A CN104128185A CN201410317690.3A CN201410317690A CN104128185A CN 104128185 A CN104128185 A CN 104128185A CN 201410317690 A CN201410317690 A CN 201410317690A CN 104128185 A CN104128185 A CN 104128185A
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Abstract
The invention relates to a tetralin synthesis catalyst comprising nickel and an auxiliary agent. The catalyst is characterized in that the catalyst comprises, by mass, 3-30% of nickel element, 0-5% of the auxiliary agent element, and balance of a carrier. The catalyst provided by the invention has the advantages of simple preparation process and low cost.
Description
Technical field
The present invention relates to a kind of Catalysts and its preparation method and using method of tetrahydrobiopterin synthesis naphthalene.
Background technology
Naphthane (being again tetrahydronaphthalene, tetralin) is a kind of alicyclic aromatic hydrocarbon.Naphthane is water insoluble, miscible with many common solvent (ethanol, ether, acetone, acetic acid, benzene and benzinum etc.), is desirable high boiling solvent, can be widely used in the industrial circles such as paint, coating, ink, carbide alloy, medicine, papermaking.Naphthane mainly, as producing tetralone, is also used as the solvent of grease, wax, resin and paint, and can be made into mixture as the fuel of internal combustion engine with benzene and ethanol, also as terebinthine substitute in glazing agent and coating.Nearest research shows, in fuel cell, naphthane is a kind of good hydrogen atom donor, and its ability of supplying with fast hydrogen atom is that decahydronaphthalene is incomparable, therefore very likely becomes cheapness of new generation, high efficient energy sources.
The seventies, due to the development of pesticide producing, the naphthane high in the urgent need to purity, sulfur content is low.Fushun oil research institute has carried out the research that naphthalene hydrogenation is produced naphthane, and the end of the year 1974, has completed small-scale test.Subsequently, by Dalian Grease Chemical Plant, in 1976, complete scale-up, built up 100 tons/year and 30 tons/year of experimental rigs.Naphthane is in a large number for the manufacture of the intermediate alpha naphthol (alpha naphthol claims again 1-naphthols, alpha-Naphthol) of pesticide sevin.The aspects such as alpha naphthol is a kind of important fine-chemical intermediate, is widely used in medicine, agricultural chemicals, dyestuff, spices manufacture, and chiral catalyst is synthetic.Owing in recent years developing the new purposes of many alpha naphthols, cause market demand constantly to increase.
The production of naphthane is in the market mainly the hydrogenation that comes from naphthalene, but because naphthalene hydrogenation is a consecutive reaction: naphthalene one step hydrogenation obtains naphthane, the further hydrogenation of naphthane generates decahydronaphthalene, the product of hydrogenation reaction is the mixture of naphthane and decahydronaphthalene normally, need to add after a step distillation operation separates two kinds of materials and come into operation, complex operation complexity and operating cost are high.More for the research of naphthalene hydrogenation production decahydronaphthalene at present, but less for the research of naphthalene hydrogenation production naphthane, and also naphthane is selectively desirable not enough.The patent of the naphthalene hydrogenation tetrahydrobiopterin synthesis naphthalene of at present domestic applications only has (201210007610.5) two of Fushun Petrochemical Research Institute (201110170289.8) and Dalian University of Technology, and employing is the catalyst of sulphided state (nickel molybdenum si molecular sieves) and carbonization state (nickel molybdenum tungsten) respectively.In addition, noble metal and transition metal etc. also can be used as the catalyst of naphthalene hydrogenation tetrahydrobiopterin synthesis naphthalene.As above in patent, the catalyst preparation process of sulphided state and carbonization state is complicated, and the noble metal catalyst price now studies have reported that is high, so the application of transition-metal catalyst has broad prospects.
Summary of the invention
The object of the present invention is to provide a kind of preparation technology simple, Catalysts and its preparation method and the application of the tetrahydrobiopterin synthesis naphthalene that cost is low.
Catalyst of the present invention comprises nickel and auxiliary agent, it is characterized in that catalyst quality percentage is that nickel element content is 3%～30%, and auxiliary element content is 0%～5%, and all the other are carrier.
Auxiliary element as above comprises one or more of cobalt, molybdenum, tungsten, zirconium, yttrium, cerium, lanthanum and manganese etc.
Carrier is γ-Al
2o
3.
Preparation method of the present invention comprises the steps:
1) preparation of catalyst precursor: adopt incipient impregnation, after the solable matter of nickel and auxiliary agent and additive are dissolved in water, join γ-Al
2o
3on carrier, after dipping 5～10 h, pour out clear liquid, at 50～150 ℃, dry 2～10 h, obtain catalyst precursor;
2) pretreatment of catalyst precursor: catalyst precursor is carried out to roasting or do not carry out roasting, then reduce under hydrogen atmosphere.The temperature of roasting is 350～550 ℃, and the time of roasting is 2～8h; The hydrogen flow rate of reduction is 10～130mL/min, and the temperature of reduction is 300～800 ℃, and the time of reduction is 10 min～5h.
In catalyst preparation process, the solable matter of nickel comprises nickel nitrate and nickel acetate.The solable matter of auxiliary agent is respectively cobalt nitrate, ammonium molybdate, ammonium metatungstate, zirconium nitrate, zirconyl nitrate, yttrium nitrate, cerous nitrate, lanthanum nitrate or manganese nitrate.
Additive comprises citric acid, tartaric acid, oxalic acid, acetic acid, one or more of ethanol and ethylenediamine etc.The addition of additive is 0～3 times of metallic element mole total amount in nickel and auxiliary agent solable matter.
Catalyst application of the present invention:
First naphthalene for mixing, naphthalene: cyclohexane=0.08～0.15:1 is placed in autoclave in mass ratio with solvent cyclohexane, then according to naphthalene: the ratio of catalyst (mass ratio)=2～4:1 joins in autoclave by catalyst fast, after in autoclave, air drains, pass into hydrogen and boost to 2～5 MPa, reaction temperature is 80～350 ℃, mixing speed is 600～800 rpm, and the reaction time is 0.5～4 h.
The present invention compared with prior art tool has the following advantages:
1, the conversion ratio of naphthalene of the present invention can reach 95%～100%, naphthane be selectively 97%～99%.
2, method for preparing catalyst is simple, and cost is low.
3, reaction temperature and pressure are lower, and the reaction time is short.
The specific embodiment
Embodiment 1
Adopt incipient impregnation, after fully dissolving in water by the nickel acetate of metallic nickel content 10wt% in catalyst, join γ-Al
2o
3, after 5 h, pour out clear liquid, at 120 ℃, dry 5 h, do not carry out roasting, after 430 ℃ of reduction 4 h, lower standby with reducing gas protection under the hydrogen flow rate of 30 mL/min.Solution 40 mL that the mass concentration ratio that adds naphthalene and solvent cyclohexane in 0.1 L high-pressure stirring reactor is 0.09 and catalyst 1.5 g, at pressure 2 MPa, 80 ℃ of reaction temperatures, under the condition of mixing speed 750 rpm, reaction 2h.The hydrogenation reaction conversion ratio of naphthalene reaches 99%, and naphthane selectively reaches 97%.
Embodiment 2
Adopt incipient impregnation, after fully dissolving in water by the nickel acetate of metallic nickel content 10wt% in catalyst, join γ-Al
2o
3, after 5 h, pour out clear liquid, at 150 ℃, dry 2h, does not carry out roasting, after 430 ℃ of reduction 4 h, lower standby with reducing gas protection under the hydrogen flow rate of 30 mL/min.Solution 40 mL that the mass concentration ratio that adds naphthalene and solvent cyclohexane in 0.1 L high-pressure stirring reactor is 0.15 and catalyst 1.5 g, at pressure 3 MPa, 130 ℃ of reaction temperatures, under the condition of mixing speed 800 rpm, reaction 2h.The hydrogenation reaction conversion ratio of naphthalene reaches 95%, and naphthane selectively reaches 99%.
Embodiment 3
Adopt incipient impregnation, by the nickel acetate of metallic nickel content 20wt% in catalyst, the ammonium metatungstate of auxiliary agent W content 5wt% after abundant dissolving, joins γ-Al by nickel acetate and ammonium metatungstate in water
2o
3, after 10 h, pour out clear liquid, dry 8 h at 150 ℃, after 450 ℃ of roasting 4 h, 430 ℃ of reduction 4 h under the hydrogen flow rate of 30 mL/min, lower standby with reducing gas protection.Solution 40 mL that the mass concentration ratio that adds naphthalene and solvent cyclohexane in 0.1 L high-pressure stirring reactor is 0.09 and catalyst 1.5 g, at pressure 4 MPa, 130 ℃ of reaction temperatures, under the condition of mixing speed 750 rpm, reaction 2 h.The hydrogenation reaction conversion ratio of naphthalene reaches 100%, and naphthane selectively reaches 99%.
Embodiment 4
Adopt incipient impregnation, by the ammonium metatungstate of the nickel acetate of metallic nickel content 20wt% in catalyst, auxiliary agent W content 4.5wt% and auxiliary agent zirconium content 0.5wt% zirconium nitrate, after nickel acetate, ammonium metatungstate and zirconium nitrate are fully dissolved in water, join γ-Al
2o
3, after 8 h, pour out clear liquid, dry 8 h at 150 ℃, after 450 ℃ of roasting 4 h, 430 ℃ of reduction 4 h under the hydrogen flow rate of 30 mL/min, lower standby with reducing gas protection.Solution 40 mL that the mass concentration ratio that adds naphthalene and solvent cyclohexane in 0.1 L high-pressure stirring reactor is 0.08 and catalyst 1.5 g, at pressure 4 MPa, 130 ℃ of reaction temperatures, under the condition of mixing speed 750 rpm, reaction 2 h.The hydrogenation reaction conversion ratio of naphthalene reaches 100%, and naphthane selectively reaches 99%.
Embodiment 5
Adopt incipient impregnation, by the nickel nitrate of metallic nickel content 6.5wt% in catalyst, additive ethanol is 0.5 times of nickel mole, and additive tartaric acid is 0.5 times of nickel mole, and nickel nitrate, ethanol and tartaric acid fully after dissolving, are joined to γ-Al in water
2o
3, after 5 h, pouring out clear liquid, dry 5 h at 120 ℃ after 300 ℃ of roasting 8 h, obtain catalyst after 300 ℃ of reduction 5 h under the hydrogen flow rate of 30 mL/min, and catalyst is lower standby with reducing gas protection.Solution 40 mL that the mass concentration ratio that adds naphthalene and solvent cyclohexane in 0.1 L high-pressure stirring reactor is 0.09 and catalyst 1.5 g, at pressure 3 MPa, 110 ℃ of reaction temperatures, under the condition of mixing speed 650 rpm, reaction 2h.The hydrogenation reaction conversion ratio of naphthalene reaches 100%, and naphthane selectively reaches 98%.
Embodiment 6
Adopt incipient impregnation, by the nickel nitrate of metallic nickel content 10wt% in catalyst, additive ethylenediamine is 2 times of nickel mole, and nickel nitrate and ethylenediamine fully after dissolving, are joined to γ-Al in water
2o
3, after 5 h, pour out clear liquid, dry 10 h at 50 ℃, after 450 ℃ of roasting 4 h, 430 ℃ of reduction 5 h under the hydrogen flow rate of 10 mL/min, lower standby with reducing gas protection.Solution 40 mL that the mass concentration ratio that adds naphthalene and solvent cyclohexane in 0.1 L high-pressure stirring reactor is 0.09 and catalyst 1.5 g, at pressure 3 MPa, 130 ℃ of reaction temperatures, under the condition of mixing speed 650 rpm, reaction 2h.The hydrogenation reaction conversion ratio of naphthalene reaches 100%, and naphthane selectively reaches 98%.
Embodiment 7
Adopt incipient impregnation, by the nickel acetate of metallic nickel content 3wt% in catalyst, the ammonium metatungstate of auxiliary agent W content 1wt% and auxiliary agent lanthanum content 0.5wt% lanthanum nitrate, after nickel acetate, ammonium metatungstate and lanthanum nitrate are fully dissolved in water, join γ-Al
2o
3, after 5 h, pour out clear liquid, dry 8 h at 120 ℃, after 550 ℃ of roasting 2 h, after 800 ℃ of reduction 10 min, lower standby with reducing gas protection under the hydrogen flow rate of 30 mL/min.Solution 40 mL that the mass concentration ratio that adds naphthalene and solvent cyclohexane in 0.1 L high-pressure stirring reactor is 0.09 and catalyst 1.5 g, at pressure 5MPa, 80 ℃ of reaction temperatures, under the condition of mixing speed 750 rpm, reaction 4 h.The hydrogenation reaction conversion ratio of naphthalene reaches 97%, and naphthane selectively reaches 99%.
Embodiment 8
Adopt incipient impregnation, by the nickel nitrate of metallic nickel content 20wt% in catalyst, additive oxalic acid is 2 times of nickel mole, and nickel nitrate and oxalic acid fully after dissolving, are joined to γ-Al in water
2o
3, after 8 h, pour out clear liquid, dry 8 h at 120 ℃, after 450 ℃ of roasting 4 h, 430 ℃ of reduction 5 h under the hydrogen flow rate of 30 mL/min, lower standby with reducing gas protection.Solution 40 mL that the mass concentration ratio that adds naphthalene and solvent cyclohexane in 0.1 L high-pressure stirring reactor is 0.09 and catalyst 1.0 g, at pressure 4 MPa, 350 ℃ of reaction temperatures, under the condition of mixing speed 750 rpm, reaction 0.5 h.The hydrogenation reaction conversion ratio of naphthalene reaches 100%, and naphthane selectively reaches 97%.
Embodiment 9
Adopt incipient impregnation, press the nickel acetate of metallic nickel content 20wt% in catalyst, the ammonium metatungstate of auxiliary agent W content 5wt% and additive citric acid are nickel and tungsten mole total amount 3 times, after nickel acetate, ammonium metatungstate and citric acid are fully dissolved in water, join γ-Al
2o
3, after 10 h, pour out clear liquid, dry 8 h at 120 ℃, after 450 ℃ of roasting 4 h, 430 ℃ of reduction 4 h under the hydrogen flow rate of 30 mL/min, lower standby with reducing gas protection.Solution 40 mL that the mass concentration ratio that adds naphthalene and solvent cyclohexane in 0.1 L high-pressure stirring reactor is 0.09 and catalyst 0.7 g, at pressure 4 MPa, 130 ℃ of reaction temperatures, under the condition of mixing speed 750 rpm, reaction 1 h.The hydrogenation reaction conversion ratio of naphthalene reaches 100%, and naphthane selectively reaches 99%.
Claims (8)
1. a catalyst for tetrahydrobiopterin synthesis naphthalene, is characterized in that catalyst comprises nickel and auxiliary agent, it is characterized in that catalyst quality percentage is that nickel element content is 3%～30%, and auxiliary element content is 0%～5%, and all the other are carrier.
2. the catalyst of a kind of tetrahydrobiopterin synthesis naphthalene as claimed in claim 1, is characterized in that described auxiliary element comprises one or more in cobalt, molybdenum, tungsten, zirconium, yttrium, cerium, lanthanum, manganese.
3. the catalyst of a kind of tetrahydrobiopterin synthesis naphthalene as claimed in claim 1, is characterized in that described carrier is γ-Al
2o
3.
4. the preparation method of the catalyst of a kind of tetrahydrobiopterin synthesis naphthalene as described in claim 1-3 any one, is characterized in that comprising the steps:
The preparation of catalyst precursor: adopt incipient impregnation, after the solable matter of nickel and auxiliary agent and additive are dissolved in water, join γ-Al
2o
3on carrier, after dipping 5～10 h, pour out clear liquid, at 50～150 ℃, dry 2～10 h, obtain catalyst precursor;
The pretreatment of catalyst precursor: catalyst precursor is carried out to roasting or do not carry out roasting, then reduce under hydrogen atmosphere;
The temperature of roasting is 350～550 ℃, and the time of roasting is 2～8h; The hydrogen flow rate of reduction is 10～130mL/min, and the temperature of reduction is 300～800 ℃, and the time of reduction is 10 min～5h.
5. the preparation method of the catalyst of a kind of tetrahydrobiopterin synthesis naphthalene as claimed in claim 4, the solable matter that it is characterized in that described nickel comprises nickel nitrate and nickel acetate, and the solable matter of auxiliary agent is cobalt nitrate, ammonium molybdate, ammonium metatungstate, zirconium nitrate, zirconyl nitrate, yttrium nitrate, cerous nitrate, lanthanum nitrate or manganese nitrate.
6. the preparation method of the catalyst of a kind of tetrahydrobiopterin synthesis naphthalene as claimed in claim 4, is characterized in that described additive comprises citric acid, tartaric acid, oxalic acid, acetic acid, one or more in ethanol, ethylenediamine.
7. the preparation method of the catalyst of a kind of tetrahydrobiopterin synthesis naphthalene as claimed in claim 4, the addition that it is characterized in that described additive is 0～3 times of metallic element mole total amount in nickel and auxiliary agent solable matter.
8. the application of the catalyst of a kind of tetrahydrobiopterin synthesis naphthalene as described in claim 1-3 any one, is characterized in that comprising the steps:
First naphthalene for mixing, naphthalene: cyclohexane=0.08～0.15:1 is placed in autoclave in mass ratio with solvent cyclohexane, then according to naphthalene: catalyst quality joins in autoclave than the ratio that is 2～4:1 by catalyst fast, after in autoclave, air drains, pass into hydrogen and boost to 2～5 MPa, reaction temperature is 80～350 ℃, mixing speed is 600～800 rpm, and the reaction time is 0.5～4 h.
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| CN106076402A (en) * | 2016-06-13 | 2016-11-09 | 北京化工大学 | The preparation method and applications of the grade hole MFI nanometer sheet that a kind of high dispersive nickel surface is modified |
| CN108325517A (en) * | 2018-01-18 | 2018-07-27 | 中国石油大学(华东) | A kind of catalyst and preparation method thereof for naphthalene selective hydrogenation production naphthane |
| CN109289860A (en) * | 2018-09-29 | 2019-02-01 | 中国科学院山西煤炭化学研究所 | The catalyst and preparation method of Hydrorefining of Industrial Naphthalene production refined naphthalene by-product naphthane and application |
| CN110903154A (en) * | 2019-11-29 | 2020-03-24 | 大连理工大学 | Novel process for preparing tetrahydronaphthalene from double-circulation naphthalene oil |
| CN114471570A (en) * | 2020-10-23 | 2022-05-13 | 中国石油化工股份有限公司 | Naphthalene selective hydrogenation catalyst, and preparation method and application thereof |
| CN116037124A (en) * | 2021-10-28 | 2023-05-02 | 中国石油化工股份有限公司 | Preparation method of pre-reduction hydrogenation catalyst containing nickel and zirconium |
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Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106076402A (en) * | 2016-06-13 | 2016-11-09 | 北京化工大学 | The preparation method and applications of the grade hole MFI nanometer sheet that a kind of high dispersive nickel surface is modified |
| CN106076402B (en) * | 2016-06-13 | 2018-11-16 | 北京化工大学 | A kind of preparation method and applications of the grade hole MFI nanometer sheet of high dispersive nickel surface modification |
| CN108325517A (en) * | 2018-01-18 | 2018-07-27 | 中国石油大学(华东) | A kind of catalyst and preparation method thereof for naphthalene selective hydrogenation production naphthane |
| CN108325517B (en) * | 2018-01-18 | 2020-10-09 | 中国石油大学(华东) | Catalyst for producing tetrahydronaphthalene by naphthalene selective hydrogenation and preparation method thereof |
| CN109289860A (en) * | 2018-09-29 | 2019-02-01 | 中国科学院山西煤炭化学研究所 | The catalyst and preparation method of Hydrorefining of Industrial Naphthalene production refined naphthalene by-product naphthane and application |
| CN109289860B (en) * | 2018-09-29 | 2021-08-20 | 中国科学院山西煤炭化学研究所 | Catalyst for producing refined naphthalene and byproduct tetrahydronaphthalene by hydrofining industrial naphthalene and preparation method and application thereof |
| CN110903154A (en) * | 2019-11-29 | 2020-03-24 | 大连理工大学 | Novel process for preparing tetrahydronaphthalene from double-circulation naphthalene oil |
| CN114471570A (en) * | 2020-10-23 | 2022-05-13 | 中国石油化工股份有限公司 | Naphthalene selective hydrogenation catalyst, and preparation method and application thereof |
| CN114471570B (en) * | 2020-10-23 | 2024-01-30 | 中国石油化工股份有限公司 | Naphthalene selective hydrogenation catalyst and preparation method and application thereof |
| CN116037124A (en) * | 2021-10-28 | 2023-05-02 | 中国石油化工股份有限公司 | Preparation method of pre-reduction hydrogenation catalyst containing nickel and zirconium |
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