CN115490615B - Preparation method of isophthalonitrile - Google Patents
Preparation method of isophthalonitrile Download PDFInfo
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- CN115490615B CN115490615B CN202211251379.4A CN202211251379A CN115490615B CN 115490615 B CN115490615 B CN 115490615B CN 202211251379 A CN202211251379 A CN 202211251379A CN 115490615 B CN115490615 B CN 115490615B
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- Prior art keywords
- isophthalonitrile
- isophthalic acid
- preparation
- caconi
- molecular sieve
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- LAQPNDIUHRHNCV-UHFFFAOYSA-N isophthalonitrile Chemical compound N#CC1=CC=CC(C#N)=C1 LAQPNDIUHRHNCV-UHFFFAOYSA-N 0.000 title claims abstract description 48
- 238000002360 preparation method Methods 0.000 title claims abstract description 44
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 claims abstract description 96
- 239000003054 catalyst Substances 0.000 claims abstract description 58
- 238000006243 chemical reaction Methods 0.000 claims abstract description 39
- GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 claims abstract description 31
- 229910052901 montmorillonite Inorganic materials 0.000 claims abstract description 31
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims abstract description 24
- 239000002808 molecular sieve Substances 0.000 claims abstract description 23
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 claims abstract description 23
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims abstract description 21
- 239000010936 titanium Substances 0.000 claims abstract description 21
- 229910052719 titanium Inorganic materials 0.000 claims abstract description 21
- 239000000047 product Substances 0.000 claims abstract description 16
- 239000000203 mixture Substances 0.000 claims abstract description 14
- 239000012043 crude product Substances 0.000 claims abstract description 13
- 238000011049 filling Methods 0.000 claims abstract description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 18
- 239000011259 mixed solution Substances 0.000 claims description 17
- ZCCIPPOKBCJFDN-UHFFFAOYSA-N calcium nitrate Chemical compound [Ca+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O ZCCIPPOKBCJFDN-UHFFFAOYSA-N 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 13
- 238000001035 drying Methods 0.000 claims description 12
- 238000001704 evaporation Methods 0.000 claims description 11
- 239000008367 deionised water Substances 0.000 claims description 9
- 229910021641 deionized water Inorganic materials 0.000 claims description 9
- 229910021586 Nickel(II) chloride Inorganic materials 0.000 claims description 7
- QMMRZOWCJAIUJA-UHFFFAOYSA-L nickel dichloride Chemical compound Cl[Ni]Cl QMMRZOWCJAIUJA-UHFFFAOYSA-L 0.000 claims description 7
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 6
- 159000000007 calcium salts Chemical class 0.000 claims description 6
- 150000001868 cobalt Chemical class 0.000 claims description 6
- 229940011182 cobalt acetate Drugs 0.000 claims description 6
- QAHREYKOYSIQPH-UHFFFAOYSA-L cobalt(II) acetate Chemical compound [Co+2].CC([O-])=O.CC([O-])=O QAHREYKOYSIQPH-UHFFFAOYSA-L 0.000 claims description 6
- 150000002815 nickel Chemical class 0.000 claims description 6
- UFMZWBIQTDUYBN-UHFFFAOYSA-N cobalt dinitrate Chemical compound [Co+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O UFMZWBIQTDUYBN-UHFFFAOYSA-N 0.000 claims description 4
- 229910001981 cobalt nitrate Inorganic materials 0.000 claims description 4
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 3
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 claims description 3
- MQRWBMAEBQOWAF-UHFFFAOYSA-N acetic acid;nickel Chemical compound [Ni].CC(O)=O.CC(O)=O MQRWBMAEBQOWAF-UHFFFAOYSA-N 0.000 claims description 3
- 239000011575 calcium Substances 0.000 claims description 3
- 229910052791 calcium Inorganic materials 0.000 claims description 3
- VSGNNIFQASZAOI-UHFFFAOYSA-L calcium acetate Chemical compound [Ca+2].CC([O-])=O.CC([O-])=O VSGNNIFQASZAOI-UHFFFAOYSA-L 0.000 claims description 3
- 229960005147 calcium acetate Drugs 0.000 claims description 3
- 235000011092 calcium acetate Nutrition 0.000 claims description 3
- 239000001639 calcium acetate Substances 0.000 claims description 3
- 239000001110 calcium chloride Substances 0.000 claims description 3
- 229910001628 calcium chloride Inorganic materials 0.000 claims description 3
- 229910017052 cobalt Inorganic materials 0.000 claims description 3
- 239000010941 cobalt Substances 0.000 claims description 3
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 3
- 229910052759 nickel Inorganic materials 0.000 claims description 3
- 229940078494 nickel acetate Drugs 0.000 claims description 3
- UGACIEPFGXRWCH-UHFFFAOYSA-N [Si].[Ti] Chemical compound [Si].[Ti] UGACIEPFGXRWCH-UHFFFAOYSA-N 0.000 claims description 2
- GVPFVAHMJGGAJG-UHFFFAOYSA-L cobalt dichloride Chemical compound [Cl-].[Cl-].[Co+2] GVPFVAHMJGGAJG-UHFFFAOYSA-L 0.000 claims description 2
- 230000008020 evaporation Effects 0.000 claims description 2
- KBJMLQFLOWQJNF-UHFFFAOYSA-N nickel(ii) nitrate Chemical compound [Ni+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O KBJMLQFLOWQJNF-UHFFFAOYSA-N 0.000 claims description 2
- 238000003889 chemical engineering Methods 0.000 abstract description 2
- 239000012847 fine chemical Substances 0.000 abstract description 2
- 230000000052 comparative effect Effects 0.000 description 13
- 239000000463 material Substances 0.000 description 8
- 238000002156 mixing Methods 0.000 description 7
- 239000002994 raw material Substances 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical group CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 238000009776 industrial production Methods 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 238000000465 moulding Methods 0.000 description 3
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- CRQQGFGUEAVUIL-UHFFFAOYSA-N chlorothalonil Chemical compound ClC1=C(Cl)C(C#N)=C(Cl)C(C#N)=C1Cl CRQQGFGUEAVUIL-UHFFFAOYSA-N 0.000 description 2
- 229910052809 inorganic oxide Inorganic materials 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229910052710 silicon Inorganic materials 0.000 description 2
- 239000010703 silicon Substances 0.000 description 2
- 238000001308 synthesis method Methods 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- 239000005747 Chlorothalonil Substances 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical group C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical group [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical group [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 239000004677 Nylon Substances 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical group [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical group O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- FDLQZKYLHJJBHD-UHFFFAOYSA-N [3-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=CC(CN)=C1 FDLQZKYLHJJBHD-UHFFFAOYSA-N 0.000 description 1
- 238000010669 acid-base reaction Methods 0.000 description 1
- 238000005576 amination reaction Methods 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 229910052787 antimony Inorganic materials 0.000 description 1
- 239000003899 bactericide agent Substances 0.000 description 1
- 229910052797 bismuth Inorganic materials 0.000 description 1
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- 229910052792 caesium Inorganic materials 0.000 description 1
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical group [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000004880 explosion Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 239000011777 magnesium Chemical group 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 229920006391 phthalonitrile polymer Polymers 0.000 description 1
- 229920005749 polyurethane resin Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000012041 precatalyst Substances 0.000 description 1
- 230000003449 preventive effect Effects 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000011734 sodium Chemical group 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000005728 strengthening Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C253/00—Preparation of carboxylic acid nitriles
- C07C253/22—Preparation of carboxylic acid nitriles by reaction of ammonia with carboxylic acids with replacement of carboxyl groups by cyano groups
-
- 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
- B01J29/89—Silicates, aluminosilicates or borosilicates of titanium, zirconium or hafnium
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C253/00—Preparation of carboxylic acid nitriles
- C07C253/32—Separation; Purification; Stabilisation; Use of additives
- C07C253/34—Separation; Purification
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C255/50—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton to carbon atoms of non-condensed six-membered aromatic rings
- C07C255/51—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton to carbon atoms of non-condensed six-membered aromatic rings containing at least two cyano groups bound to the carbon skeleton
-
- 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
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/584—Recycling of catalysts
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention belongs to the technical field of fine chemical engineering, and particularly relates to a preparation method of isophthalonitrile. The preparation method comprises the following steps: s1, selecting a mixture of CaCoNi/titanium silicalite molecular sieve and montmorillonite as a catalyst bed; s2, filling the catalyst bed prepared in the step S1 into a fixed bed reactor; s3, feeding the isophthalic acid feeder after metering into a preheating section, and feeding the isophthalic acid feeder and ammonia gas into a catalyst bed for reaction after preheating; s4, rectifying and purifying the crude product to obtain the product isophthalonitrile. The preparation method of the isophthalonitrile has higher yield.
Description
Technical Field
The invention belongs to the technical field of fine chemical engineering. More specifically, it relates to a process for producing isophthalonitrile.
Background
Isophthalonitrile (IPN) is an important intermediate for the preparation of organic compounds. The IPN is subjected to chlorination reaction to prepare tetrachloro isophthalonitrile (chlorothalonil), which is an efficient, broad-spectrum, low-toxicity and low-residue pesticide bactericide and mildew preventive; the IPN is subjected to hydrogenation reaction to obtain m-xylylenediamine. Is a resin curing agent with excellent performance, and is also a raw material of polyurethane resin and nylon resin. The simplest and economical industrial production method of m-phthalonitrile is that m-xylene is prepared by gas phase ammoxidation under the action of a catalyst.
CN101906045B discloses a method for preparing aniline by benzene through one-step direct amination, which uses benzene as raw material, ammonia water as ammoniating agent, hydrogen peroxide as oxidant, acetonitrile as solvent, metal-loaded TS-1 as catalyst, and the one-step aniline synthesis method is characterized by high aniline yield, mild reaction condition, simple preparation process of the catalyst, low cost and easy availability of raw materials, low cost, high yield, and simple and feasible green synthesis method.
CN109876794B discloses a special catalyst for preparing isophthalonitrile by m-xylene ammoxidation, wherein the carrier is silica gel, the main catalyst is three components of V, mo and Sb, and the cocatalyst is at least one of components D and E; the active components are expressed as follows: VMo b Sb c D d E e O x The method comprises the steps of carrying out a first treatment on the surface of the The D is boron, chromium, titanium, phosphorus, nickel, bismuth, manganese, iron, cobalt, copper, zinc or tin; e is potassium, lithium, sodium, cesium, magnesium or calcium. The invention also discloses a preparation method and application of the catalyst. The invention uses the group containing lone electron pair on silicon to carry out Lewis acid-base reaction with inorganic element, thereby strengthening the effect of inorganic oxide and carrier; at the same time, inorganic oxide is dispersed more uniformlyEven, the catalyst component loss is less, the catalytic activity is high, the selectivity is good, and the service life of the industrial catalyst is prolonged from one year to more than two years. The catalyst has simple preparation method and good thermal stability and mechanical strength, and can be used in fixed bed reactors and fluidized bed reactors.
CN112961074a discloses a method for synthesizing isophthalonitrile, which uses m-xylene as raw material, and sequentially oxidizes the raw material in the presence of a pre-catalyst and a post-catalyst to obtain high-quality isophthalonitrile. Compared with the existing industrial process, the method can greatly improve the yield of the isophthalonitrile, improve the utilization rate of raw materials, has little three wastes, avoids using a complex purification process, greatly simplifies the process and realizes the green industrialization of the isophthalonitrile.
As described above, although the production of isophthalonitrile can be achieved in the prior art, the yield is low, the reaction is required to be carried out in a closed vessel, and the reaction is carried out in air, which is liable to cause explosion and is disadvantageous for industrial production.
Disclosure of Invention
The invention aims to overcome the defects and shortcomings in the prior art and provide a preparation method of isophthalonitrile. The preparation method comprises the following steps: s1, selecting a mixture of CaCoNi/titanium silicalite molecular sieve and montmorillonite as a catalyst bed; s2, filling the catalyst bed prepared in the step S1 into a fixed bed reactor; s3, feeding the isophthalic acid feeder after metering into a preheating section, and feeding the isophthalic acid feeder and ammonia gas into a catalyst bed for reaction after preheating; s4, rectifying and purifying the crude product to obtain the product isophthalonitrile. The preparation method of the isophthalonitrile has higher yield.
The invention aims to provide a preparation method of isophthalonitrile.
The above object of the present invention is achieved by the following technical scheme:
a method for producing isophthalonitrile, comprising the steps of:
s1, selecting a mixture of CaCoNi/titanium silicalite molecular sieve and montmorillonite as a catalyst bed;
s2, filling the catalyst bed prepared in the step S1 into a fixed bed reactor;
s3, feeding the isophthalic acid feeder after metering into a preheating section, and feeding the isophthalic acid feeder and ammonia gas into a catalyst bed for reaction after preheating;
s4, rectifying and purifying the crude product to obtain the product isophthalonitrile.
Preferably, in the step S1, the mass ratio of the CaCoNi/titanium silicalite molecular sieve to the montmorillonite is 1:0.3-0.5; the ratio of the calcium, cobalt, nickel and titanium silicalite molecular sieves is 10mmol: 1-3 mmol: 2-4 mmol: 3-5 g.
Preferably, in the step S3, the preheating temperature is 420-450 ℃, and the reaction conditions are as follows: the molar ratio of isophthalic acid to ammonia gas is: 1:2 to 20; the reaction pressure is normal pressure to 5Mpa, and the space velocity of isophthalic acid is 0.1 to 1h -1 。
Preferably, the titanium silicalite molecular sieve is at least one of TS-1, TS-2 or Ti-HMS.
Preferably, in the step S1, the preparation method of the cacon/titanium silicalite molecular sieve includes the following steps:
dissolving calcium salt, cobalt salt and nickel salt in deionized water to prepare a mixed solution, adding a titanium silicalite molecular sieve into the mixed solution, uniformly dispersing by ultrasonic, evaporating water under reduced pressure at a certain temperature, forming, drying and roasting to obtain the CaCoNi/titanium silicalite molecular sieve.
Preferably, the calcium salt is at least one of calcium nitrate, calcium acetate and calcium chloride; the cobalt salt is at least one of cobalt nitrate, cobalt acetate and cobalt chloride; the nickel salt is at least one of nickel nitrate, nickel acetate and nickel chloride.
Preferably, the ratio of the calcium salt, cobalt salt, nickel salt and titanium silicalite molecular sieve is 10mmol: 1-3 mmol: 2-4 mmol: 3-5 g.
Preferably, the temperature of the reduced pressure evaporation to dryness is 60-80 ℃.
Preferably, the drying is performed at 100-140 ℃ for 12-16 h.
Preferably, the roasting is carried out at 500-600 ℃ for 4-8 hours.
Preferably, the CaCoNi/titanium silicalite molecular sieve and montmorillonite are uniformly mixed to obtain the mixture.
The invention has the following beneficial effects:
(1) According to the invention, caCoNi is loaded by the titanium-silicon molecular sieve, and the conversion rate of raw materials and the selectivity of products are improved by the mutual coordination of the molecular sieve and the active components, so that the yield is influenced;
(2) The product yield is further improved through CaCoNi/titanium silicon molecular sieve and montmorillonite;
(3) The catalyst of the invention has simple preparation process, low cost and easy obtainment, and is beneficial to industrial production.
Detailed Description
The present invention is further illustrated below with reference to specific examples, which are not intended to limit the invention in any way. Unless specifically stated otherwise, the reagents, methods and apparatus employed in the present invention are those conventional in the art.
Reagents and materials used in the following examples are commercially available unless otherwise specified.
Example 1
A preparation method of isophthalonitrile is characterized by comprising the following steps: the preparation method comprises the following steps:
s1, selecting a mixture of 1Kg CaCoNi/TS-2 and montmorillonite as a catalyst bed layer;
s2, filling the catalyst bed prepared in the step S1 into a fixed bed reactor;
s3, feeding the isophthalic acid feeder after metering into a preheating section, wherein the preheating temperature is 435 ℃, and feeding the isophthalic acid feeder and ammonia gas into a catalyst bed for reaction after preheating; the reaction conditions are as follows: the molar ratio of isophthalic acid to ammonia gas is: 1:7, preparing a base material; the reaction pressure is 1.4Mpa, and the space velocity of isophthalic acid is 0.5h -1 ；
S4, rectifying and purifying the crude product to obtain the product isophthalonitrile. Wherein the mass ratio of CaCoNi/TS-2 to montmorillonite is 1:0.4.
The preparation method of CaCoNi/TS-2 comprises the following steps:
dissolving 10mmol of calcium nitrate, 2mmol of cobalt acetate and 3mmol of nickel chloride in 50mL of deionized water to prepare a mixed solution, adding 4g of TS-2 into the mixed solution, uniformly dispersing by ultrasonic, evaporating water at 70 ℃ under reduced pressure, forming, drying at 120 ℃ for 14h, and roasting at 550 ℃ for 6h to obtain CaCoNi/TS-2;
and uniformly stirring and mixing the CaCoNi/TS-2 and montmorillonite according to the mass ratio of 1:0.4 to obtain the catalyst.
Example 2
A preparation method of isophthalonitrile is characterized by comprising the following steps: the preparation method comprises the following steps:
s1, selecting a mixture of 1Kg CaCoNi/TS-1 and montmorillonite as a catalyst bed;
s2, filling the catalyst bed prepared in the step S1 into a fixed bed reactor;
s3, feeding the isophthalic acid feeder after metering into a preheating section, wherein the preheating temperature is 450 ℃, and feeding the isophthalic acid feeder and ammonia gas into a catalyst bed for reaction after preheating; the reaction conditions are as follows: the molar ratio of isophthalic acid to ammonia gas is: 1:20, a step of; the reaction pressure is 0.1Mpa, and the space velocity of isophthalic acid is 1h -1 ；
S4, rectifying and purifying the crude product to obtain the product isophthalonitrile. The mass ratio of CaCoNi/TS-1 to montmorillonite is 1:0.5.
The preparation method of CaCoNi/TS-1 comprises the following steps:
dissolving 10mmol of calcium acetate, 3mmol of cobalt nitrate and 2mmol of nickel chloride in 50mL of deionized water to prepare a mixed solution, adding 5g of TS-1 into the mixed solution, uniformly dispersing by ultrasonic, evaporating water at 80 ℃ under reduced pressure, molding, drying at 140 ℃ for 12h, and roasting at 600 ℃ for 4h to obtain CaCoNi/TS-1;
and uniformly stirring and mixing the CaCoNi/TS-1 and montmorillonite according to the mass ratio of 1:0.5 to obtain the catalyst.
Example 3
A preparation method of isophthalonitrile is characterized by comprising the following steps: the preparation method comprises the following steps:
s1, selecting a mixture of 1Kg CaCoNi/Ti-HMS and montmorillonite as a catalyst bed layer;
s2, filling the catalyst bed prepared in the step S1 into a fixed bed reactor;
s3, feeding the isophthalic acid feeder after metering into a preheating section, wherein the preheating temperature is 420 ℃, and feeding the isophthalic acid feeder and ammonia gas into a catalyst bed for reaction after preheating; the reaction conditions are as follows: the molar ratio of isophthalic acid to ammonia gas is: 1:2; the reaction pressure is 5Mpa, and the space velocity of isophthalic acid is 0.1h -1 ；
S4, rectifying and purifying the crude product to obtain the product isophthalonitrile. The mass ratio of CaCoNi/Ti-HMS to montmorillonite is 1:0.3.
The preparation method of the CaCoNi/Ti-HMS comprises the following steps:
dissolving 10mmol of calcium chloride, 1mmol of cobalt nitrate and 4mmol of nickel acetate in 50mL of deionized water to prepare a mixed solution, adding 3g of Ti-HMS into the mixed solution, uniformly dispersing by ultrasonic, evaporating water at 60 ℃ under reduced pressure, forming, drying at 100 ℃ for 16h, and roasting at 500 ℃ for 8h to obtain CaCoNi/Ti-HMS;
and uniformly stirring and mixing the CaCoNi/Ti-HMS and montmorillonite according to the mass ratio of 1:0.3 to obtain the catalyst.
Comparative example 1
A preparation method of isophthalonitrile is characterized by comprising the following steps: the preparation method comprises the following steps:
s1, selecting a mixture of 1Kg CaCo/TS-2 and montmorillonite as a catalyst bed;
s2, filling the catalyst bed prepared in the step S1 into a fixed bed reactor;
s3, feeding the isophthalic acid feeder after metering into a preheating section, wherein the preheating temperature is 435 ℃, and feeding the isophthalic acid feeder and ammonia gas into a catalyst bed for reaction after preheating; the reaction conditions are as follows: the molar ratio of isophthalic acid to ammonia gas is: 1:7, preparing a base material; the reaction pressure is 1.4Mpa, and the space velocity of isophthalic acid is 0.5h -1 ；
S4, rectifying and purifying the crude product to obtain the product isophthalonitrile. Wherein the mass ratio of CaCo/TS-2 to montmorillonite is 1:0.4.
The preparation method of the CaCo/TS-2 comprises the following steps:
dissolving 10mmol of calcium nitrate and 5mmol of cobalt acetate in 50mL of deionized water to prepare a mixed solution, adding 4g of TS-2 into the mixed solution, uniformly dispersing by ultrasonic, evaporating water at 70 ℃ under reduced pressure, molding, drying at 120 ℃ for 14h, and roasting at 550 ℃ for 6h to obtain CaCo/TS-2;
and uniformly stirring and mixing the CaCo/TS-2 and montmorillonite according to the mass ratio of 1:0.4 to obtain the catalyst.
Comparative example 2
A preparation method of isophthalonitrile is characterized by comprising the following steps: the preparation method comprises the following steps:
s1, selecting a mixture of 1Kg of CaNi/TS-2 and montmorillonite as a catalyst bed layer;
s2, filling the catalyst bed prepared in the step S1 into a fixed bed reactor;
s3, feeding the isophthalic acid feeder after metering into a preheating section, wherein the preheating temperature is 435 ℃, and feeding the isophthalic acid feeder and ammonia gas into a catalyst bed for reaction after preheating; the reaction conditions are as follows: the molar ratio of isophthalic acid to ammonia gas is: 1:7, preparing a base material; the reaction pressure is 1.4Mpa, and the space velocity of isophthalic acid is 0.5h -1 ；
S4, rectifying and purifying the crude product to obtain the product isophthalonitrile. Wherein, the mass ratio of the CaNi/TS-2 to the montmorillonite is 1:0.4.
The preparation method of the CaNi/TS-2 comprises the following steps:
dissolving 10mmol of calcium nitrate and 5mmol of nickel chloride in 50mL of deionized water to prepare a mixed solution, adding 4g of TS-2 into the mixed solution, uniformly dispersing by ultrasonic, evaporating water at 70 ℃ under reduced pressure, molding, drying at 120 ℃ for 14h, and roasting at 550 ℃ for 6h to obtain CaNi/TS-2;
and uniformly stirring and mixing the obtained CaNi/TS-2 and montmorillonite according to the mass ratio of 1:0.4 to obtain the catalyst.
Comparative example 3
A preparation method of isophthalonitrile is characterized by comprising the following steps: the preparation method comprises the following steps:
s1, selecting a mixture of 1Kg CaCoNi and montmorillonite as a catalyst bed layer;
s2, filling the catalyst bed prepared in the step S1 into a fixed bed reactor;
s3, feeding the isophthalic acid feeder after metering into a preheating section, wherein the preheating temperature is 435 ℃, and feeding the isophthalic acid feeder and ammonia gas into a catalyst bed for reaction after preheating; the reaction conditions are as follows: the molar ratio of isophthalic acid to ammonia gas is: 1:7, preparing a base material; the reaction pressure is 1.4Mpa, and the space velocity of isophthalic acid is 0.5h -1 ；
S4, rectifying and purifying the crude product to obtain the product isophthalonitrile. Wherein the mass ratio of CaCoNi to montmorillonite is 1:0.4.
The preparation method of CaCoNi comprises the following steps:
dissolving 10mmol of calcium nitrate, 2mmol of cobalt acetate and 3mmol of nickel chloride in 50mL of deionized water to prepare a mixed solution, evaporating water at 70 ℃ under reduced pressure, forming, drying at 120 ℃ for 14h, and roasting at 550 ℃ for 6h to obtain CaCoNi;
and uniformly stirring and mixing the CaCoNi and montmorillonite according to the mass ratio of 1:0.4 to obtain the catalyst.
Comparative example 4
A preparation method of isophthalonitrile is characterized by comprising the following steps: the preparation method comprises the following steps:
s1, selecting a mixture of 1Kg TS-2 and montmorillonite as a catalyst bed layer;
s2, filling the catalyst bed prepared in the step S1 into a fixed bed reactor;
s3, feeding the isophthalic acid feeder after metering into a preheating section, wherein the preheating temperature is 435 ℃, and feeding the isophthalic acid feeder and ammonia gas into a catalyst bed for reaction after preheating; the reaction conditions are as follows: the molar ratio of isophthalic acid to ammonia gas is: 1:7, preparing a base material; the reaction pressure is 1.4Mpa, and the space velocity of isophthalic acid is 0.5h -1 ；
S4, rectifying and purifying the crude product to obtain the product isophthalonitrile. Wherein the mass ratio of TS-2 to montmorillonite is 1:0.4.
And uniformly stirring and mixing TS-2 and montmorillonite according to the mass ratio of 1:0.4 to obtain the catalyst.
Comparative example 5
A preparation method of isophthalonitrile is characterized by comprising the following steps: the preparation method comprises the following steps:
s1, selecting 1Kg CaCoNi/TS-2 as a catalyst bed layer;
s2, filling the catalyst bed prepared in the step S1 into a fixed bed reactor;
s3, feeding the isophthalic acid feeder after metering into a preheating section, wherein the preheating temperature is 435 ℃, and feeding the isophthalic acid feeder and ammonia gas into a catalyst bed for reaction after preheating; the reaction conditions are as follows: the molar ratio of isophthalic acid to ammonia gas is: 1:7, preparing a base material; the reaction pressure is 1.4Mpa, and the space velocity of isophthalic acid is 0.5h -1 。
S4, rectifying and purifying the crude product to obtain the product isophthalonitrile.
The preparation method of CaCoNi/TS-2 comprises the following steps:
dissolving 10mmol of calcium nitrate, 2mmol of cobalt acetate and 3mmol of nickel chloride in 50mL of deionized water to prepare a mixed solution, adding 4g of TS-2 into the mixed solution, uniformly dispersing by ultrasonic, evaporating water at 70 ℃ under reduced pressure, forming, drying at 120 ℃ for 14h, and roasting at 550 ℃ for 6h to obtain CaCoNi/TS-2.
Comparative example 6
A preparation method of isophthalonitrile is characterized by comprising the following steps: the preparation method comprises the following steps:
s1, selecting 1Kg of montmorillonite mixture as a catalyst bed;
s2, filling the catalyst bed prepared in the step S1 into a fixed bed reactor;
s3, feeding the isophthalic acid feeder after metering into a preheating section, wherein the preheating temperature is 435 ℃, and feeding the isophthalic acid feeder and ammonia gas into a catalyst bed for reaction after preheating; the reaction conditions are as follows: the molar ratio of isophthalic acid to ammonia gas is: 1:7, preparing a base material; the reaction pressure is 1.4Mpa, and the space velocity of isophthalic acid is 0.5h -1 ；
S4, rectifying and purifying the crude product to obtain the product isophthalonitrile.
The specific test results of examples 1-3 and comparative examples 1-6 are shown in Table 1:
TABLE 1
| Description of the embodiments | Yield% | Description of the embodiments | Yield% |
| Example 1 | 99.2 | Comparative example 3 | 92.8 |
| Example 2 | 98.3 | Comparative example 4 | 78.5 |
| Example 3 | 98.6 | Comparative example 5 | 83.5 |
| Comparative example 1 | 97.2 | Comparative example 6 | 66.9 |
| Comparative example 2 | 96.9 |
As can be seen from table 1, the isophthalonitrile prepared by the preparation method of the present invention has excellent yield, and the product yield is significantly improved by using the catalyst of the present invention, utilizing the interaction between components.
The above examples are preferred embodiments of the present invention, but the embodiments of the present invention are not limited to the above examples, and any other changes, modifications, substitutions, combinations, and simplifications that do not depart from the spirit and principle of the present invention should be made in the equivalent manner, and the embodiments are included in the protection scope of the present invention.
Claims (6)
1. A preparation method of isophthalonitrile is characterized by comprising the following steps:
the preparation method comprises the following steps:
s1, selecting a mixture of CaCoNi/titanium silicalite molecular sieve and montmorillonite as a catalyst bed;
s2, filling the catalyst bed prepared in the step S1 into a fixed bed reactor;
s3, feeding the isophthalic acid feeder after metering into a preheating section, and feeding the isophthalic acid feeder and ammonia gas into a catalyst bed for reaction after preheating;
s4, rectifying and purifying the crude product to obtain the product isophthalonitrile;
in the step S1, the mass ratio of the CaCoNi/titanium silicalite molecular sieve to the montmorillonite is 1:0.3-0.5; the ratio of the calcium, cobalt, nickel and titanium silicalite molecular sieves is 10mmol: 1-3 mmol: 2-4 mmol: 3-5 g;
in the step S3, the preheating temperature is 420-450 ℃, and the reaction conditions are as follows: the molar ratio of isophthalic acid to ammonia gas is: 1:2 to 20; the reaction pressure is normal pressure to 5MPa, and the space velocity of isophthalic acid is 0.1 to 1h -1 ；
The titanium-silicon molecular sieve is at least one of TS-1, TS-2 or Ti-HMS;
in the step S1, the preparation method of the CaCoNi/titanium silicalite molecular sieve comprises the following steps:
dissolving calcium salt, cobalt salt and nickel salt in deionized water to prepare a mixed solution, adding a titanium silicalite molecular sieve into the mixed solution, uniformly dispersing by ultrasonic, evaporating water under reduced pressure at a certain temperature, forming, drying and roasting to obtain the CaCoNi/titanium silicalite molecular sieve.
2. The process for producing isophthalonitrile according to claim 1, wherein:
the calcium salt is at least one of calcium nitrate, calcium acetate and calcium chloride; the cobalt salt is at least one of cobalt nitrate, cobalt acetate and cobalt chloride; the nickel salt is at least one of nickel nitrate, nickel acetate and nickel chloride.
3. The process for producing isophthalonitrile according to claim 1, wherein:
the ratio of the calcium salt, the cobalt salt, the nickel salt and the titanium silicalite molecular sieve is 10mmol: 1-3 mmol: 2-4 mmol: 3-5 g.
4. The process for producing isophthalonitrile according to claim 1, wherein:
the temperature of the reduced pressure evaporation to dryness is 60-80 ℃.
5. The process for producing isophthalonitrile according to claim 1, wherein:
the drying is that the drying is carried out for 12 to 16 hours at the temperature of 100 to 140 ℃; the roasting is carried out for 4-8 hours at 500-600 ℃.
6. The process for producing isophthalonitrile according to claim 1, wherein:
the CaCoNi/titanium silicalite molecular sieve and montmorillonite are uniformly mixed to obtain a mixture.
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Citations (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4189580A (en) * | 1977-08-18 | 1980-02-19 | Bayer Aktiengesellschaft | Process for the preparation of nitriles |
| JPS63243064A (en) * | 1987-03-31 | 1988-10-07 | Mitsui Toatsu Chem Inc | Production of benzonitriles |
| IN187529B (en) * | 1994-02-24 | 2002-05-11 | Council Scient Ind Res | |
| CN102219711A (en) * | 2010-04-15 | 2011-10-19 | 中国石油化工股份有限公司 | Method for preparing isophthalodinitrile |
| CN104148077A (en) * | 2014-09-01 | 2014-11-19 | 常熟昊虞电子信息科技有限公司 | Preparation method for nickel cobalt/montmorillonite catalyst |
| CN109761851A (en) * | 2017-11-09 | 2019-05-17 | 中国石化扬子石油化工有限公司 | A kind of preparation method of isophthalodinitrile |
| CN109876794A (en) * | 2018-12-17 | 2019-06-14 | 中南民族大学 | Ammoxidation reaction prepares the special-purpose catalyst and preparation method and purposes of m-dicyanobenzene |
| CN111848447A (en) * | 2019-04-24 | 2020-10-30 | 山东华鲁恒升化工股份有限公司 | Method for preparing adiponitrile by gas-phase ammoniation and dehydration of adipic acid |
| CN112934225A (en) * | 2019-12-11 | 2021-06-11 | 中国科学院大连化学物理研究所 | Bimetallic component isophthalonitrile hydrogenation catalyst, preparation and application thereof |
| CN112961074A (en) * | 2021-02-04 | 2021-06-15 | 鞍山七彩化学股份有限公司 | Method for synthesizing isophthalonitrile |
| CN115135634A (en) * | 2020-10-30 | 2022-09-30 | 锦湖石油化学株式会社 | System for producing phthalonitrile compound and method for producing phthalonitrile compound using same |
-
2022
- 2022-10-13 CN CN202211251379.4A patent/CN115490615B/en active Active
Patent Citations (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4189580A (en) * | 1977-08-18 | 1980-02-19 | Bayer Aktiengesellschaft | Process for the preparation of nitriles |
| JPS63243064A (en) * | 1987-03-31 | 1988-10-07 | Mitsui Toatsu Chem Inc | Production of benzonitriles |
| IN187529B (en) * | 1994-02-24 | 2002-05-11 | Council Scient Ind Res | |
| CN102219711A (en) * | 2010-04-15 | 2011-10-19 | 中国石油化工股份有限公司 | Method for preparing isophthalodinitrile |
| CN104148077A (en) * | 2014-09-01 | 2014-11-19 | 常熟昊虞电子信息科技有限公司 | Preparation method for nickel cobalt/montmorillonite catalyst |
| CN109761851A (en) * | 2017-11-09 | 2019-05-17 | 中国石化扬子石油化工有限公司 | A kind of preparation method of isophthalodinitrile |
| CN109876794A (en) * | 2018-12-17 | 2019-06-14 | 中南民族大学 | Ammoxidation reaction prepares the special-purpose catalyst and preparation method and purposes of m-dicyanobenzene |
| CN111848447A (en) * | 2019-04-24 | 2020-10-30 | 山东华鲁恒升化工股份有限公司 | Method for preparing adiponitrile by gas-phase ammoniation and dehydration of adipic acid |
| CN112934225A (en) * | 2019-12-11 | 2021-06-11 | 中国科学院大连化学物理研究所 | Bimetallic component isophthalonitrile hydrogenation catalyst, preparation and application thereof |
| CN115135634A (en) * | 2020-10-30 | 2022-09-30 | 锦湖石油化学株式会社 | System for producing phthalonitrile compound and method for producing phthalonitrile compound using same |
| CN112961074A (en) * | 2021-02-04 | 2021-06-15 | 鞍山七彩化学股份有限公司 | Method for synthesizing isophthalonitrile |
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