CN115945216A - Copper-tetramethylguanidine hydrochloride catalyst for hydrochlorination of acetylene, preparation method and application - Google Patents
Copper-tetramethylguanidine hydrochloride catalyst for hydrochlorination of acetylene, preparation method and application Download PDFInfo
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- CN115945216A CN115945216A CN202211067760.5A CN202211067760A CN115945216A CN 115945216 A CN115945216 A CN 115945216A CN 202211067760 A CN202211067760 A CN 202211067760A CN 115945216 A CN115945216 A CN 115945216A
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- copper
- acetylene
- catalyst
- hydrochlorination
- tetramethylguanidine hydrochloride
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- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 title claims abstract description 70
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 title claims abstract description 70
- 239000003054 catalyst Substances 0.000 title claims abstract description 65
- 238000007038 hydrochlorination reaction Methods 0.000 title claims abstract description 37
- -1 Copper-tetramethylguanidine hydrochloride Chemical compound 0.000 title claims abstract description 35
- 238000002360 preparation method Methods 0.000 title abstract description 17
- GMGZEOLIKDSQTL-UHFFFAOYSA-N 1,1,3,3-tetramethylguanidine;hydrochloride Chemical compound [Cl-].CN(C)C(N)=[N+](C)C GMGZEOLIKDSQTL-UHFFFAOYSA-N 0.000 claims abstract description 19
- 238000001035 drying Methods 0.000 claims abstract description 16
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 claims abstract description 11
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 30
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 21
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 21
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims description 21
- 238000007259 addition reaction Methods 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 15
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 12
- 229910052802 copper Inorganic materials 0.000 claims description 12
- 239000010949 copper Substances 0.000 claims description 12
- 238000005470 impregnation Methods 0.000 claims description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- 230000009471 action Effects 0.000 claims description 3
- 238000009776 industrial production Methods 0.000 claims description 3
- 239000007788 liquid Substances 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 description 8
- 230000003197 catalytic effect Effects 0.000 description 7
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 6
- 150000004699 copper complex Chemical class 0.000 description 6
- 229910052799 carbon Inorganic materials 0.000 description 5
- 230000008569 process Effects 0.000 description 5
- 239000003446 ligand Substances 0.000 description 4
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 4
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 3
- JPVYNHNXODAKFH-UHFFFAOYSA-N Cu2+ Chemical compound [Cu+2] JPVYNHNXODAKFH-UHFFFAOYSA-N 0.000 description 3
- 239000002262 Schiff base Substances 0.000 description 3
- 150000004753 Schiff bases Chemical class 0.000 description 3
- 229910001431 copper ion Inorganic materials 0.000 description 3
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 3
- 229910052753 mercury Inorganic materials 0.000 description 3
- 229920000915 polyvinyl chloride Polymers 0.000 description 3
- 239000004800 polyvinyl chloride Substances 0.000 description 3
- 239000005997 Calcium carbide Substances 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 239000002131 composite material Substances 0.000 description 2
- 229910052737 gold Inorganic materials 0.000 description 2
- 229960002523 mercuric chloride Drugs 0.000 description 2
- LWJROJCJINYWOX-UHFFFAOYSA-L mercury dichloride Chemical compound Cl[Hg]Cl LWJROJCJINYWOX-UHFFFAOYSA-L 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 229910000510 noble metal Inorganic materials 0.000 description 2
- 229910052707 ruthenium Inorganic materials 0.000 description 2
- 230000002194 synthesizing effect Effects 0.000 description 2
- CLZWAWBPWVRRGI-UHFFFAOYSA-N tert-butyl 2-[2-[2-[2-[bis[2-[(2-methylpropan-2-yl)oxy]-2-oxoethyl]amino]-5-bromophenoxy]ethoxy]-4-methyl-n-[2-[(2-methylpropan-2-yl)oxy]-2-oxoethyl]anilino]acetate Chemical compound CC1=CC=C(N(CC(=O)OC(C)(C)C)CC(=O)OC(C)(C)C)C(OCCOC=2C(=CC=C(Br)C=2)N(CC(=O)OC(C)(C)C)CC(=O)OC(C)(C)C)=C1 CLZWAWBPWVRRGI-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- CQGDLUZXSAXPRC-UHFFFAOYSA-N Cl.[Cu].C#C Chemical compound Cl.[Cu].C#C CQGDLUZXSAXPRC-UHFFFAOYSA-N 0.000 description 1
- 239000012691 Cu precursor Substances 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- WDIHJSXYQDMJHN-UHFFFAOYSA-L barium chloride Chemical compound [Cl-].[Cl-].[Ba+2] WDIHJSXYQDMJHN-UHFFFAOYSA-L 0.000 description 1
- 229910001626 barium chloride Inorganic materials 0.000 description 1
- AIYUHDOJVYHVIT-UHFFFAOYSA-M caesium chloride Chemical compound [Cl-].[Cs+] AIYUHDOJVYHVIT-UHFFFAOYSA-M 0.000 description 1
- VYLVYHXQOHJDJL-UHFFFAOYSA-K cerium trichloride Chemical compound Cl[Ce](Cl)Cl VYLVYHXQOHJDJL-UHFFFAOYSA-K 0.000 description 1
- RCTYPNKXASFOBE-UHFFFAOYSA-M chloromercury Chemical compound [Hg]Cl RCTYPNKXASFOBE-UHFFFAOYSA-M 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- GVPFVAHMJGGAJG-UHFFFAOYSA-L cobalt dichloride Chemical compound [Cl-].[Cl-].[Co+2] GVPFVAHMJGGAJG-UHFFFAOYSA-L 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 230000000536 complexating effect Effects 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000002105 nanoparticle Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000001132 ultrasonic dispersion Methods 0.000 description 1
Classifications
-
- 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
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
Abstract
The invention discloses a copper-tetramethylguanidine hydrochloride catalyst for acetylene hydrochlorination and a preparation method and application thereof, wherein the catalyst consists of copper chloride and tetramethylguanidine hydrochloride and is prepared by adopting an ultrasonic dipping-microwave drying mode.
Description
Technical Field
The invention belongs to the field of catalysts, and particularly relates to a copper catalyst for addition reaction of acetylene and hydrogen chloride.
Background
Polyvinyl chloride is one of five general resins and has wide application in many fields, vinyl Chloride Monomer (VCM) for synthesizing polyvinyl chloride mainly has an acetylene method and an ethylene method, in China, due to the restriction of a resource structure of rich coal and less oil, the acetylene hydrochlorination method taking calcium carbide as a raw material is the main process for synthesizing the vinyl chloride monomer in China at present, and HgCl is used in the method 2 the/C is a catalyst, the reaction is exothermic, and the mercuric chloride is molecular crystal, so that the mercuric chloride is easy to sublimate and causes serious pollution to the environment. In 2013, 19/1, the united states environmental planning agency made a detailed regulation on the specific emission limits through the international public convention water insurance policy aimed at controlling and reducing mercury emissions globally to reduce the damage of mercury to the environment and human health. In recent years, the mercury-free catalyst for acetylene hydrochlorination mainly comprises noble metals Au and Ru, but the noble metals Au and Ru are too high in cost and cannot be applied industrially.
Patent No. CN202110882564.2 discloses a copper-based composite catalyst for hydrochlorination of acetylene and a method thereof, wherein the catalyst takes active carbon pretreated by Schiff base as a carrier, and loads a copper-amino acid complex and cocatalysts of cesium chloride, barium chloride, cobalt chloride, cerium chloride and the like. Firstly, performing Schiff base pretreatment on activated carbon, dropwise adding amino acid into copper chloride to prepare a copper-amino acid complex, then jointly impregnating the copper-amino acid complex and a cocatalyst component on the Schiff base pretreated activated carbon, drying to obtain a copper-based composite catalyst, and impregnating for multiple times to obtain a catalyst with high metal content; the patent number CN202110205264.0 discloses an insoluble copper complex catalyst for catalyzing acetylene hydrochlorination and a preparation method thereof, which relate to the technical field of catalyst preparation. The preparation method comprises the following steps: firstly, uniformly mixing two components of a carrier, a copper precursor and a surfactant, adding a third component, and then impregnating and thermally activating to obtain the copper-based catalyst. Because the complex formed by Cu- (n +) and some ligands is lack of solubility and even insoluble, the preparation method changes the adding sequence of the Cu- (n +) and some ligands, and can effectively improve the dispersibility of the active component on the carrier;
patent number CN201810775463.3 discloses a copper complex catalyst for hydrochlorination of acetylene and a preparation method thereof. A copper complex catalyst for acetylene hydrochlorination is composed of a carrier and a copper complex, wherein the copper complex is loaded on the surface of the carrier; the copper complex is formed by complexing copper chloride and an organic phosphoric acid ligand.
Disclosure of Invention
The invention aims to provide a copper-tetramethylguanidine hydrochloride catalyst for acetylene hydrochlorination and a preparation method thereof.
The technical scheme of the invention is as follows: a copper-tetramethylguanidine hydrochloride catalyst for acetylene hydrochlorination is composed of copper chloride, tetramethylguanidine hydrochloride and carrier activated carbon.
The copper-tetramethylguanidine hydrochloride catalyst for acetylene hydrochlorination comprises, by weight, 10 to 25% of copper element, 5 to 15% of tetramethylguanidine hydrochloride and the balance of carrier activated carbon.
The copper-tetramethylguanidine hydrochloride catalyst for acetylene hydrochlorination is characterized in that the copper element in the catalyst is copper chloride.
The preparation method of the copper-tetramethylguanidine hydrochloride catalyst for acetylene hydrochlorination is characterized by comprising the steps of ultrasonic impregnation and microwave drying.
The preparation method of the copper-tetramethylguanidine hydrochloride catalyst for acetylene hydrochlorination comprises the following specific steps: (1) preparing copper chloride-tetramethylguanidine hydrochloride impregnation liquid; (2) under the action of ultrasonic waves, impregnating copper chloride-tetramethylguanidine hydrochloride with activated carbon; (3) and drying the water content to be less than 0.3% by adopting a microwave drying mode.
The application of the copper-tetramethylguanidine hydrochloride catalyst for acetylene hydrochlorination is used for the addition reaction of acetylene and hydrogen chloride.
The application of the copper-tetramethylguanidine hydrochloride catalyst for acetylene hydrochlorination has the following conditions of addition reaction of acetylene and hydrogen chloride: the temperature is 90-180 ℃, the molar ratio of acetylene to hydrogen chloride is 1.05-1.1, and the space velocity and flow rate of acetylene in industrial production are 15-50h -1 。
An application of tetramethylguanidine hydrochloride in preparing a catalyst for acetylene hydrochlorination.
Compared with the prior art, (1) the catalyst does not contain mercury element, thus effectively solving the problem of mercury pollution in the calcium carbide process polyvinyl chloride industry, and the catalyst has no pollution to the environment;
(2) in the process of catalyzing the reaction of acetylene and hydrogen chloride by the acetylene hydrochlorination catalyst, the reaction mechanism is that the hydrogen chloride is firstly combined with metal ions and then undergoes an addition reaction with the acetylene, the tetramethylguanidine hydrochloride is selected as a ligand, and the tetramethylguanidine hydrochloride contains chloride ions, so that in the actual application process, the activation period is short, the addition reaction of acetylene molecules and hydrogen chloride molecules is accelerated, and the carbon deposition reaction is avoided;
(3) the nitrogen atom in the tetramethylguanidine hydrochloride is coordinated with the divalent copper ion, so that the divalent copper ion can be stabilized, the divalent copper ion is inhibited from being converted to a low valence state, and the catalyst has good stability.
(4) When the loading capacity of copper chloride and tetramethylguanidine hydrochloride in the catalyst is large, copper on the surface of the catalyst can be loaded in the form of large particles, the catalytic activity center can not fully play a catalytic role, and the copper and the tetramethylguanidine hydrochloride on the surface of the catalyst can be loaded in the form of nano particles by adopting an ultrasonic dispersion method in the impregnation process, so that the catalyst has more active point positions, large dispersion degree and high catalytic conversion rate.
(5) In the traditional preparation process of the acetylene copper hydrochloride catalyst, a drying method is adopted for drying, a large amount of water vapor can carry catalytic active components of copper chloride and tetramethylguanidine hydrochloride to be condensed on the surface of carrier active carbon, the catalytic components are loaded in a cluster form, and a catalytic active center can not fully play a catalytic role.
Detailed Description
The present invention will be further described with reference to the following examples and comparative examples, which are not intended to limit the scope of the present invention.
Examples are given. A copper-tetramethylguanidine hydrochloride catalyst for acetylene hydrochlorination is composed of copper chloride, tetramethylguanidine hydrochloride and carrier activated carbon.
The copper-tetramethylguanidine hydrochloride catalyst for acetylene hydrochlorination comprises, by weight, 10 to 25% of copper element, 5 to 15% of tetramethylguanidine hydrochloride and the balance of carrier activated carbon.
The copper-tetramethylguanidine hydrochloride catalyst for acetylene hydrochlorination is characterized in that the copper element in the catalyst is copper chloride.
The preparation method of the copper-tetramethylguanidine hydrochloride catalyst for acetylene hydrochlorination is characterized by preparing the catalyst by an ultrasonic dipping-microwave drying method.
The preparation method of the copper-tetramethylguanidine hydrochloride catalyst for acetylene hydrochlorination comprises the following specific steps: (1) preparing copper chloride-tetramethylguanidine hydrochloride impregnation liquid; (2) under the action of ultrasonic waves, impregnating copper chloride-tetramethylguanidine hydrochloride with activated carbon; (3) drying the water content to be less than 0.3% by adopting a microwave drying mode.
The application of the copper-tetramethylguanidine hydrochloride catalyst for acetylene hydrochlorination is used for the addition reaction of acetylene and hydrogen chloride.
The application of the copper-tetramethylguanidine hydrochloride catalyst for acetylene hydrochlorination is characterized in that the conditions of the addition reaction of acetylene and hydrogen chloride are as follows: the temperature is 90-180 ℃, the molar ratio of acetylene to hydrogen chloride is 1.05-1.1, and the space velocity and flow rate of acetylene in industrial production are 15-50h < -1 >.
An application of tetramethylguanidine hydrochloride in preparing a catalyst for acetylene hydrochlorination.
Example 1
A copper-tetramethyl guanidine hydrochloride catalyst for hydrochlorinating acetylene, its preparation method and application are disclosed, the catalyst contains CuCl 2 ·2H 2 The catalyst is prepared from O40%, tetramethylguanidine hydrochloride 12% and carrier active carbon 48% by an ultrasonic impregnation-microwave drying method, and is used for the addition reaction of acetylene and hydrogen chloride, and the addition reaction conditions of the acetylene and the hydrogen chloride are as follows: the temperature is 90-180 ℃, the molar ratio of acetylene to hydrogen chloride is 1.05, the conversion rate of acetylene is 99.8% when the space velocity of acetylene is 25h-1, and the selectivity of chloroethylene is 99.7%.
Example 2
Copper-tetramethylguanidine hydrochloride catalyst for acetylene hydrochlorination and preparation thereof
The method and the application are that the component content of the catalyst is CuCl calculated by weight 2 ·2H 2 The catalyst is prepared from O35%, tetramethylguanidine hydrochloride 15% and carrier active carbon 50% by an ultrasonic impregnation-microwave drying method, and is used for the addition reaction of acetylene and hydrogen chloride, wherein the addition reaction conditions of acetylene and hydrogen chloride are as follows: the temperature is 90-180 ℃, the molar ratio of acetylene to hydrogen chloride is 1.05, and the space velocity and flow rate of acetylene are 20h -1 The conversion of acetylene was 99.7% and the selectivity of vinyl chloride was 99.7%.
Example 3
Copper-tetramethylguanidine hydrochloride catalyst for acetylene hydrochlorination and preparation thereof
The method and the application are that the component content of the catalyst is CuCl calculated by weight 2 ·2H 2 The catalyst is prepared from 45% of O, 10% of tetramethylguanidine hydrochloride and 45% of carrier activated carbon by an ultrasonic impregnation-microwave drying method, and is used for the addition reaction of acetylene and hydrogen chloride, wherein the addition reaction conditions of the acetylene and the hydrogen chloride are as follows: the temperature is 90-180 ℃, the molar ratio of acetylene to hydrogen chloride is 1.05, and acetylene is emptyThe flow rate is 22h -1 The acetylene conversion was 99.7% and the vinyl chloride selectivity was 99.7%.
Claims (8)
1. The copper-tetramethylguanidine hydrochloride catalyst for acetylene hydrochlorination is characterized by consisting of copper chloride, tetramethylguanidine hydrochloride and carrier activated carbon.
2. The copper-tetramethylguanidine hydrochloride catalyst for acetylene hydrochlorination according to claim 1, wherein the catalyst comprises 10 to 25% by weight of copper element, 5 to 15% by weight of tetramethylguanidine hydrochloride, and the balance of carrier activated carbon.
3. The copper-tetramethylguanidine hydrochloride catalyst for hydrochlorination of acetylene according to claim 1, wherein the copper element in the catalyst is copper chloride.
4. The method for preparing a copper-tetramethylguanidine hydrochloride catalyst for hydrochlorination of acetylene according to any one of claims 1 to 3, characterized in that it is prepared by ultrasonic impregnation-microwave drying.
5. The method for preparing the copper-tetramethylguanidine hydrochloride catalyst for acetylene hydrochlorination according to claim 4, which is characterized by comprising the following steps: (1) preparing copper chloride-tetramethylguanidine hydrochloride impregnation liquid; (2) under the action of ultrasonic waves, impregnating copper chloride-tetramethylguanidine hydrochloride with activated carbon; (3) and drying the water content to be less than 0.3% by adopting a microwave drying mode.
6. Use of a copper-tetramethylguanidine hydrochloride catalyst for the hydrochlorination of acetylene according to any of claims 1 to 3, characterized by the addition reaction of acetylene with hydrogen chloride.
7. The use of the copper-tetramethylguanidine hydrochloride catalyst for hydrochlorination of acetylene according to claim 6, characterized in that: acetylene and hydrogen chlorideThe conditions of the addition reaction are: the temperature is 90-180 ℃, the molar ratio of acetylene to hydrogen chloride is 1.05-1.1, and the space velocity and flow rate of acetylene in industrial production are 15-50h -1 。
8. The application of the tetramethylguanidine hydrochloride is characterized in that: application of guanidine tetramethylguanidine hydrochloride in preparing a catalyst for acetylene hydrochlorination.
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