CN102513146A - Catalyst for compounding 2, 6-dimethylnaphthalene and preparing method thereof - Google Patents

Catalyst for compounding 2, 6-dimethylnaphthalene and preparing method thereof Download PDF

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CN102513146A
CN102513146A CN2011103760455A CN201110376045A CN102513146A CN 102513146 A CN102513146 A CN 102513146A CN 2011103760455 A CN2011103760455 A CN 2011103760455A CN 201110376045 A CN201110376045 A CN 201110376045A CN 102513146 A CN102513146 A CN 102513146A
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dimethylnaphthalene
catalyst
charcoal
synthetic
gel
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CN102513146B (en
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王亚涛
房承宣
胡浩权
郭学华
靳立军
于泳
彭胜
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Kailuan Energy Chemical Co Ltd
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Abstract

The invention discloses a catalyst for compounding 2, 6-dimethylnaphthalene and a preparing method thereof. The weight ratio of main components of the catalyst is: Na 2O 0.25-0.5 parts, SiO 2 1.0 parts, tetrapropyl ammonium bromide (TPABr) 0.05-0.2 parts, Al2O3 0.01-0.03 parts, Fe2O3 0.01-0.03 parts, H2PO4- 0.03-0.06 parts and carbon aerogel 22-45 parts. The catalyst for compounding the 2, 6-dimethylnaphthalene and the preparing method of the catalyst are used in an alkylation reaction of 2-methylnaphthalene and methanol, the selectivity and yield of the 2, 6-dimethylnaphthalene respectively reach 50% and 17% and are obviously better than those of a common molecular sieve catalyst.

Description

Be used for Synthetic 2, the Catalysts and its preparation method of 6-dimethylnaphthalene
Technical field
The present invention relates to a kind of catalyst, especially a kind of Synthetic 2 that is used for, the Catalysts and its preparation method of 6-dimethylnaphthalene.
Background technology
2,6-dialkyl group naphthalene is as the important intermediate of synthesized high-performance polyester material, generate after its oxidation 2, the PEN (PEN) that 6-naphthalenedicarboxylic acid and ethylene glycol polymerization make is a kind of novel polyester-type material.Compare with PETG (PET) at present commonly used, PEN performance aspect numerous all is superior to PET, is the substitute of following PET.The key that PEN commercially produces is a starting monomer 2, the source of 6-naphthalenedicarboxylic acid and cost.The principal element that restricting current PEN comes into the market on a large scale is the raw material of synthetic PEN---2, and 6-dialkyl group naphthalene costs an arm and a leg.
Contain naphthalene compound with other and compare, 2, the 6-dimethylnaphthalene is simple and do not have the carbon atom loss and the most economical with its easy oxidation, oxidizing process, and therefore cheap, the process of exploitation is simple 2, and 6-dimethylnaphthalene technology is the basis of realizing PEN large-scale production.Some major companies of the world have begun to be correlated with 2, the R&D work of 6-dimethylnaphthalene.
2,6-dimethylnaphthalene synthesis technique comprises two types of direct extraction method and chemical synthesis.Direct extraction method is to be raw material with coal tar wash oil, pyrolysis gas oil and petroleum cracking heavy aromatics etc., through series of process direct separation such as rectifying, crystallizations, but because in coal tar wash oil and the petroleum cracking heavy aromatics 2; 6-dimethylnaphthalene content is merely 1-2 wt%, also be difficult to satisfy reality to the PEN development need even all utilize, and dimethylnaphthalene isomer is many; Separation difficulty, efficient are low; Can not be as 2,6-dimethylnaphthalene main source must be through the chemical synthesis preparation.
Chemical synthesis comprises that with toluene, xylenes, naphthalene, methyl naphthalene and multi-methylnaphthalene etc. be raw material, through series of chemical preparation 2,6-dimethylnaphthalene process.Contain methyl naphthalene component abundant, relative low price (comprising 1-methyl naphthalene and 2-methyl naphthalene) in the coal tar, so the rational and efficient use of methyl naphthalene has significant effects for the value that promotes coal tar and the development of Coal Chemical Industry industry.At present; Amoco and Mitsubishi are only to have two families to realize 2 in the world, 6-dimethylnaphthalene suitability for industrialized production enterprise, and the technology of employing all is raw material with the ortho-xylene; Through preparing 2 with processes such as butadiene side chain alkylation, dehydrocyclization, dehydroaromatizationof, isomerization; The 6-dimethylnaphthalene needs each step intermediate product separated and can carry out just that next step is synthetic, therefore has the process complicacy, process route is long and problems such as cost height.
2 of the synthetic high added value of zeolite catalysis 2-methyl naphthalene and methanol alkylation selectivity, 6-dimethylnaphthalene have advantages such as process route is short, raw material sources are extensive, low price, are a kind of synthetic routes with potentiality to be exploited, thereby are to study focus at present.
Summary of the invention
The technical problem that the present invention will solve provides a kind of Synthetic 2 that is used for, and the Catalysts and its preparation method of 6-dimethylnaphthalene is used for 2-methyl naphthalene and methanol alkylation Synthetic 2, the reaction of 6-dimethylnaphthalene, obtain desirable 2,6-dimethylnaphthalene yield.
For solving the problems of the technologies described above, among the present invention respectively the weight proportion of this catalyst component be: Na 20.25～0.5 part of O, SiO 21.0 part, 0.05～0.2 part of TPABr, Al 2O 30.01～0.03 part, Fe 2O 30.01～0.03 part, H 2PO 4 -0.03～0.06 part with 22～45 parts of charcoal-aero gels.
The weight proportion of the preferred catalyst component of the present invention is: Na 20.32 part of O, SiO 21.0 part, 0.1 part of TPABr, Al 2O 30.01 part, Fe 2O 30.0163 part, H 2PO 4 -0.0489 30 parts of part and charcoal-aero gels.
The inventive method adopts following processing step preparation:
(1) calculates also raw materials weighing NaOH, waterglass, TPAOH (aq, 20%), Al (NO according to the proportioning of each composition 3) 39H 2O, Fe 2(SO 4) 3, NaH 2PO 4And charcoal-aero gel;
(2) waterglass and NaOH solution are mixed, add TPAOH solution, stir;
(3) with Al (NO 3) 39H 2O solution and above-mentioned mixed liquor mix, and add Fe again 2(SO 4) 3, stir;
(4) in above-mentioned mixed liquor, add NaH 2PO 4Solution, dry charcoal-aero gel is added in the back that stirs, and stirs;
(5) with the aging gel that obtains of said mixture, gel carries out crystallization and obtains sample then;
(6) described sample is through suction filtration, washing, drying, and template is removed in last, roasting, makes described catalyst.
Add NaH in the said step of the inventive method (4) 2PO 4Stir 1～3h behind the solution, add the charcoal-aero gel of 120 ℃ of down dry 3～6h then.
In the said step of the inventive method (5), the aging at normal temperatures 20～25h of mixture, the gained gel is in 175 ℃ of following crystallization 70～75h.
In the said step of the inventive method (6), template is removed in 550 ℃ of following roastings at last in 120 ℃ of drying 3～5h in sample washing back, makes catalyst.
Adopt the beneficial effect that technique scheme produced to be: the present invention is a kind of methyl naphthalene alkylation catalyst; The alkylated reaction that is used for 2-methyl naphthalene and methyl alcohol; Target product 2; The selectivity of 6-dimethylnaphthalene and yield reach 50% and 17% respectively, obviously are superior to existing common molecular sieve catalyst.
The specific embodiment
Below in conjunction with specific embodiment the present invention is done further detailed explanation.
The ZSM-5 zeolite molecular sieve is a kind of desirable 2-methyl naphthalene alkylation catalyst material, but in use has 2-methyl naphthalene conversion ratio and 2, problem such as lower and easy inactivation of 6-dimethylnaphthalene selectivity.After the process modification makes it possess special composition and pore passage structure, can obtain desirable catalytic effect.
2,6-dimethylnaphthalene molecule has and ZSM-5 zeolite cavity similar sizes, runs into very big diffusional resistance during molecule turnover ZSM-5, and this situation hinders finishes carbon precursor disengaging catalyst activity position, makes catalyst carbon deposit make its inactivation.Fe is a transition metal, and atomic size is bigger than Al, introduces zeolitic frameworks, can increase pore volume, reduces the current resistance of molecule, reduces carbon deposit, improves catalyst life.Simultaneously, behind the Al element with the Fe instead of part, the ZSM-5 acid strength is improved, and can increase catalytic activity, improves 2-methyl naphthalene conversion ratio.
Through discovering, in the building-up process of zeolite, adding charcoal-aero gel can increase the zeolite pore volume, thereby obviously improves the conversion ratio of 2-methyl naphthalene.But excessive charcoal-aero gel can reduce the mesoporous content of zeolite on the contrary, causes the total pore volume of zeolite to reduce, thereby reduces the conversion ratio of 2-methyl naphthalene.After the charcoal-aero gel addition acquires a certain degree; Mesoporous amount minimizing causes reactant and the product diffusion in catalyst to reduce; The selectivity that less molecule is generated improves, and 2, the molecular dimension of 6-dimethylnaphthalene is compared less with most of homologue; Help zeolite to 2, the 6-dimethylnaphthalene select the shape effect.Therefore the addition of charcoal-aero gel has a suitable scope.
Comprehensive 2-methyl naphthalene conversion ratio and 2,, the 6-dimethylnaphthalene is double factor optionally, and the weight proportion of each composition of catalyst provided by the invention is: sodium oxide molybdena (Na 2O) 0.25～0.5 part, silica (SiO 2) 1.0 parts, 0.05～0.2 part of 4-propyl bromide (TPABr), aluminium oxide (Al 2O 3) 0.01～0.03 part, di-iron trioxide (Fe 2O 3) 0.01～0.03 part, dihydrogen phosphate (H 2PO 4 -) 0.03～0.06 part with 22～45 parts of charcoal-aero gels.
Embodiment 1: originally be used for Synthetic 2, the catalyst of 6-dimethylnaphthalene adopts following preparation method.
By weight Na 2O:SiO 2: TPAOH:Al 2O 3: Fe 2O 3: H 2PO 4 -: charcoal-aero gel=0.32:1.0:0.1:0.01:0.0163:0.0489:30, calculate and take by weighing raw material NaOH, waterglass, TPAOH (aq, 20%), Al (NO 3) 39H 2O, Fe 2(SO 4) 3, NaH 2PO 4And charcoal-aero gel.
Waterglass NaOH solution is mixed, add TPAOH (aq), stir; With Al (NO 3) 39H 2O solution and above-mentioned mixed liquor mix, and add Fe again 2(SO 4) 3, stir; In above-mentioned mixed liquor, add NaH 2PO 4Solution behind the powerful stirring 2h, adds 120 ℃ of charcoal-aero gels of dry 5h down, stirs; With the aging at normal temperatures 22h of said mixture, the gained gel is in 175 ℃ of following crystallization 72h.Through suction filtration, deionized water fully washs with above-mentioned gained sample, in 120 ℃ of dry 4h, and removes template in 550 ℃ of following roastings, makes this catalyst.Through detecting, the weight proportion of each composition in this catalyst is: Na 20.32 part of O, SiO 21.0 part, 0.1 part of TPABr, Al 2O 30.01 part, Fe 2O 30.0163 part, H 2PO 4 -0.0489 30 parts of part, charcoal-aero gels.
At 400 ℃, 2-methyl naphthalene mass space velocity is 0.5 h -1, under the condition of 2-methyl naphthalene: methyl alcohol: mesitylene=1:1:3 (mol ratio), above-mentioned catalyst is used for 2-methyl naphthalene and methanol alkylation Synthetic 2, in the reaction of 6-dimethylnaphthalene.Through reaction in 8 hours, the selectivity of 2-methyl naphthalene, dimethylnaphthalene selectivity, 2,6/2,7-DMN ratio, 2, the selectivity of 6-DMN and yield can reach 44%, 78%, 2.7,49% and 17% respectively.
Embodiment 2: originally be used for Synthetic 2, the catalyst of 6-dimethylnaphthalene adopts following preparation method.
By weight Na 2O:SiO 2: TPAOH:Al 2O 3: Fe 2O 3: H 2PO 4 -: charcoal-aero gel=0.25:1.0:0.2:0.02:0.01:0.06:22, calculate and take by weighing raw material NaOH, waterglass, TPAOH (aq, 20%), Al (NO 3) 39H 2O, Fe 2(SO 4) 3, NaH 2PO 4And charcoal-aero gel.
Waterglass NaOH solution is mixed, add TPAOH (aq), stir; With Al (NO 3) 39H 2O solution and above-mentioned mixed liquor mix, and add Fe again 2(SO 4) 3, stir; In above-mentioned mixed liquor, add NaH 2PO 4Solution behind the powerful stirring 1h, adds 120 ℃ of charcoal-aero gels of dry 6h down, stirs; With the aging at normal temperatures 20h of said mixture, the gained gel is in 175 ℃ of following crystallization 70h.Through suction filtration, deionized water fully washs with above-mentioned gained sample, in 120 ℃ of dry 5h, and removes template in 550 ℃ of following roastings, makes this catalyst.Through detecting, the weight proportion of each composition in this catalyst is: Na 20.25 part of O, SiO 21.0 part, 0.2 part of TPABr, Al 2O 30.02 part, Fe 2O 30.01 part, H 2PO 4 -0.06 22 parts of part, charcoal-aero gels.
Adopt embodiment 1 described process conditions, above-mentioned catalyst is used for 2-methyl naphthalene and methanol alkylation Synthetic 2, in the reaction of 6-dimethylnaphthalene.Through reaction in 8 hours, the selectivity of 2-methyl naphthalene, dimethylnaphthalene selectivity, 2,6/2,7-DMN ratio, 2, the selectivity of 6-DMN and yield can reach 45%, 79%, 2.8,47% and 18% respectively.
Embodiment 3: originally be used for Synthetic 2, the catalyst of 6-dimethylnaphthalene adopts following preparation method.
By weight Na 2O:SiO 2: TPAOH:Al 2O 3: Fe 2O 3: H 2PO 4 -: charcoal-aero gel=0.5:1.0:0.05:0.03:0.03:0.03:45, calculate and take by weighing raw material NaOH, waterglass, TPAOH (aq, 20%), Al (NO 3) 39H 2O, Fe 2(SO 4) 3, NaH 2PO 4And charcoal-aero gel.
Waterglass NaOH solution is mixed, add TPAOH (aq), stir; With Al (NO 3) 39H 2O solution and above-mentioned mixed liquor mix, and add Fe again 2(SO 4) 3, stir; In above-mentioned mixed liquor, add NaH 2PO 4Solution behind the powerful stirring 3h, adds 120 ℃ of charcoal-aero gels of dry 3h down, stirs; With the aging at normal temperatures 25h of said mixture, the gained gel is in 175 ℃ of following crystallization 75h.Through suction filtration, deionized water fully washs with above-mentioned gained sample, in 120 ℃ of dry 3h, and removes template in 550 ℃ of following roastings, makes this catalyst.Through detecting, the weight proportion of each composition in this catalyst is: Na 20.5 part of O, SiO 21.0 part, 0.05 part of TPABr, Al 2O 30.03 part, Fe 2O 30.03 part, H 2PO 4 -0.03 45 parts of part, charcoal-aero gels.
Adopt embodiment 1 described process conditions, above-mentioned catalyst is used for 2-methyl naphthalene and methanol alkylation Synthetic 2, in the reaction of 6-dimethylnaphthalene.Through reaction in 8 hours, the selectivity of 2-methyl naphthalene, dimethylnaphthalene selectivity, 2,6/2,7-DMN ratio, 2, the selectivity of 6-DMN and yield can reach 44%, 77%, 2.6,48% and 17% respectively.

Claims (6)

1. one kind is used for Synthetic 2, and the catalyst of 6-dimethylnaphthalene is characterized in that, this catalyst predominant quantity proportioning is: Na 20.25～0.5 part of O, SiO 21.0 part, 0.05～0.2 part of TPABr, Al 2O 30.01～0.03 part, Fe 2O 30.01～0.03 part, H 2PO 4 -0.03～0.06 part with 22～45 parts of charcoal-aero gels.
2. the Synthetic 2 that is used for according to claim 1, the catalyst of 6-dimethylnaphthalene is characterized in that, this catalyst predominant quantity proportioning is: Na 20.32 part of O, SiO 21.0 part, 0.1 part of TPABr, Al 2O 30.01 part, Fe 2O 30.0163 part, H 2PO 4 -0.0489 30 parts of part and charcoal-aero gels.
3. claim 1, the 2 described Synthetic 2s that are used for; The Preparation of catalysts method of 6-dimethylnaphthalene; It is characterized in that the processing step of this method is: also raw materials weighing NaOH, waterglass, TPAOH (aq, 20%), Al (NO are calculated according to the proportioning of each composition in (1) 3) 39H 2O, Fe 2(SO 4) 3, NaH 2PO 4And charcoal-aero gel;
(2) waterglass and NaOH solution are mixed, add TPAOH solution, stir;
(3) with Al (NO 3) 39H 2O solution and above-mentioned mixed liquor mix, and add Fe again 2(SO 4) 3, stir;
(4) in above-mentioned mixed liquor, add NaH 2PO 4Solution, dry charcoal-aero gel is added in the back that stirs, and stirs;
(5) with the aging gel that obtains of said mixture, gel carries out crystallization and obtains sample then;
(6) described sample is through suction filtration, washing, drying, and template is removed in last, roasting, makes described catalyst.
4. the Synthetic 2 that is used for according to claim 3, the Preparation of catalysts method of 6-dimethylnaphthalene is characterized in that: add NaH in the said step (4) 2PO 4Stir 1～3h behind the solution, add the charcoal-aero gel of 120 ℃ of down dry 3～6h then.
5. the Synthetic 2 that is used for according to claim 3, the Preparation of catalysts method of 6-dimethylnaphthalene is characterized in that: in the said step (5), the aging at normal temperatures 20～25h of mixture, the gained gel is in 175 ℃ of following crystallization 70～75h.
6. according to claim 3, the 4 or 5 described Synthetic 2s that are used for; The Preparation of catalysts method of 6-dimethylnaphthalene is characterized in that: in the said step (6), sample washing back is in 120 ℃ of drying 3～5h; Remove template in 550 ℃ of following roastings at last, make catalyst.
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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN107970992A (en) * 2017-10-27 2018-05-01 苏州盖德精细材料有限公司 A kind of preparation method and applications of the load swage molecular sieve catalyst based on polyvinyl butyral resin template
CN109746035A (en) * 2017-11-01 2019-05-14 中国石油化工股份有限公司 Method for dimethylbenzene and methanol side chain alkylation system the first and second benzene and methyl styrene

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS6097923A (en) * 1983-11-02 1985-05-31 Mitsubishi Chem Ind Ltd Contact isomerization of dimethylnaphthalene containing methylnaphthalene
JPH09241185A (en) * 1996-03-08 1997-09-16 Cosmo Sogo Kenkyusho:Kk Production of dialkylnaphthalene
CN101417234A (en) * 2007-10-24 2009-04-29 中国科学院大连化学物理研究所 Preparation method of catalyst for shape-selective alkylation of naphthalene to produce 2,6-di(tert butyl)naphthalene
CN101618335A (en) * 2009-08-06 2010-01-06 上海卓悦化工科技有限公司 Method for preparing catalyst for compounding p-diethylbenzene by alkylation reaction of ethylbenzene and ethane or alcohol
CN102125868A (en) * 2011-01-26 2011-07-20 浙江师范大学 Method for preparing microporous-mesoporous composite Fe-ZSM-5 zeolite molecular sieve catalyst

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS6097923A (en) * 1983-11-02 1985-05-31 Mitsubishi Chem Ind Ltd Contact isomerization of dimethylnaphthalene containing methylnaphthalene
JPH09241185A (en) * 1996-03-08 1997-09-16 Cosmo Sogo Kenkyusho:Kk Production of dialkylnaphthalene
CN101417234A (en) * 2007-10-24 2009-04-29 中国科学院大连化学物理研究所 Preparation method of catalyst for shape-selective alkylation of naphthalene to produce 2,6-di(tert butyl)naphthalene
CN101618335A (en) * 2009-08-06 2010-01-06 上海卓悦化工科技有限公司 Method for preparing catalyst for compounding p-diethylbenzene by alkylation reaction of ethylbenzene and ethane or alcohol
CN102125868A (en) * 2011-01-26 2011-07-20 浙江师范大学 Method for preparing microporous-mesoporous composite Fe-ZSM-5 zeolite molecular sieve catalyst

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN107970992A (en) * 2017-10-27 2018-05-01 苏州盖德精细材料有限公司 A kind of preparation method and applications of the load swage molecular sieve catalyst based on polyvinyl butyral resin template
CN109746035A (en) * 2017-11-01 2019-05-14 中国石油化工股份有限公司 Method for dimethylbenzene and methanol side chain alkylation system the first and second benzene and methyl styrene
CN109746035B (en) * 2017-11-01 2021-11-30 中国石油化工股份有限公司 Method for preparing methyl ethyl benzene and methyl styrene by side chain alkylation of xylene and methanol

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