CN112723995B - Tert-butyl alcohol refining catalyst and preparation method and application thereof - Google Patents

Tert-butyl alcohol refining catalyst and preparation method and application thereof Download PDF

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CN112723995B
CN112723995B CN201911030787.5A CN201911030787A CN112723995B CN 112723995 B CN112723995 B CN 112723995B CN 201911030787 A CN201911030787 A CN 201911030787A CN 112723995 B CN112723995 B CN 112723995B
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lanthanum
platinum
tert
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CN112723995A (en
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徐会青
张信伟
李�杰
刘全杰
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Sinopec Dalian Petrochemical Research Institute Co ltd
China Petroleum and Chemical Corp
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Sinopec Dalian Research Institute of Petroleum and Petrochemicals
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C31/00—Saturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
    • C07C31/02—Monohydroxylic acyclic alcohols
    • C07C31/12—Monohydroxylic acyclic alcohols containing four carbon atoms
    • 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
    • B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
    • B01J23/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
    • B01J23/54—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
    • B01J23/56—Platinum group metals
    • B01J23/63—Platinum group metals with rare earths or actinides
    • 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
    • B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
    • B01J37/0009—Use of binding agents; Moulding; Pressing; Powdering; Granulating; Addition of materials ameliorating the mechanical properties of the product catalyst
    • B01J37/0018—Addition of a binding agent or of material, later completely removed among others as result of heat treatment, leaching or washing,(e.g. forming of pores; protective layer, desintegrating by heat)
    • 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
    • B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
    • B01J37/08—Heat treatment
    • B01J37/082—Decomposition and pyrolysis
    • B01J37/086—Decomposition of an organometallic compound, a metal complex or a metal salt of a carboxylic acid
    • 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
    • B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
    • B01J37/16—Reducing
    • B01J37/18—Reducing with gases containing free hydrogen
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/74—Separation; Purification; Use of additives, e.g. for stabilisation
    • C07C29/88—Separation; Purification; Use of additives, e.g. for stabilisation by treatment giving rise to a chemical modification of at least one compound
    • C07C29/90—Separation; Purification; Use of additives, e.g. for stabilisation by treatment giving rise to a chemical modification of at least one compound using hydrogen only

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Abstract

The invention discloses a preparation method of a tertiary butanol refining catalyst, which comprises the following steps: (1) Preparing a mixed solution containing a platinum complex and a mesoporous organic template; (2) preparing La modified silicon dioxide; (3) And (3) kneading the mixed solution prepared in the step (1) and the La modified silicon dioxide prepared in the step (2) to form the tert-butyl alcohol refining catalyst. The catalyst prepared by the method has excellent removal capacity for impurities such as organic peroxide, organic acid ester and the like in the tert-butyl alcohol raw material, and the removal rate of the impurities reaches more than 99%.

Description

Tert-butyl alcohol refining catalyst and preparation method and application thereof
Technical Field
The invention relates to a tert-butyl alcohol (TBA) refined catalyst, a preparation method and application thereof, in particular to a high-activity tert-butyl alcohol (TBA) refined catalyst, and a preparation method and application thereof.
Background
Propylene oxide is the third largest propylene derivative besides polypropylene and acrylonitrile, and is an important basic organic chemical raw material. The method is mainly used for producing polyether polyol, nonionic surfactant, propylene carbonate and propylene glycol, is an important raw material of fine chemical products, and is widely applied to industries such as automobiles, buildings, food, tobacco, medicine, cosmetics and the like.
The existing propylene oxide production technology mainly comprises the following steps: chlorohydrin process, co-oxidation process, direct oxidation process. The environmental disadvantages of the chlorohydrin process have led to the gradual market withdrawal of this route. The new project mainly considers a co-oxidation method and a direct oxidation method. The co-oxidation process comprises: ethylbenzene co-oxidation (PO/SM), isobutane co-oxidation (PO/TBA, PO/MTBE), cumene oxidation (CHP). The PO/MTBE combination unit comprises: the method comprises the unit processes of iso-butane oxidation, propylene epoxidation, product separation and purification, TBA refining, MTBE synthesis and the like. Among them, the TBA material after epoxidation contains impurities such as organic acid esters, peroxides, etc., which may adversely affect the subsequent synthesis of MTBE. Therefore, before entering the MTBE synthesis unit, the TBA is purified to remove impurities.
The TBA feedstock from the PO/MTBE complex contains a variety of impurities, including organic acid ester impurities: tert-butyl formate (TBF), isobutyl formate (IBF), organic peroxide impurities including: t-butyl hydroperoxide (TBHP), di-t-butyl peroxide (DTBP). These four impurities have negative effects on downstream processes and therefore must be treated to remove the impurities before entering the downstream processes.
Disclosure of Invention
Aiming at the defects of the prior art, the invention provides a tertiary butanol refining catalyst, a preparation method and application thereof. The catalyst has excellent removal capability on impurities such as organic peroxides (TBHP, DTBP), organic acid esters (TBF, IBF) and the like in TBA raw materials, and the removal rate of the impurities reaches more than 99%.
A preparation method of a tertiary butanol refining catalyst comprises the following steps:
(1) Preparing a mixed solution containing a platinum complex and a mesoporous organic template;
(2) Preparing La modified silicon dioxide;
(3) And (3) kneading the mixed solution prepared in the step (1) and the La modified silicon dioxide prepared in the step (2) to form the tert-butyl alcohol refining catalyst.
In the above method, the platinum complex is an organic platinum complex, wherein the organic platinum complex is preferably one or more of dichloro-1, 2-cyclohexanediamine platinum, 1-cyclobutane dicarboxylic acid diammine platinum and 1, 2-diaminocyclohexane oxalic acid diammine platinum, and more preferably 1, 1-cyclobutane dicarboxylic acid diammine platinum.
In the method, the mesoporous organic template is preferably one or more of ethylene oxide-polypropylene oxide-polyethylene oxide triblock copolymer (P123), polyoxyethylene polyoxypropylene ether block copolymer (F127) and fatty alcohol polyoxyethylene ether (AEO), and more preferably ethylene oxide-polypropylene oxide-polyethylene oxide triblock copolymer (P123).
In the above method, the mass content (in terms of Pt) of the platinum complex in the mixed solution is 0.5% to 10%, preferably 1.0% to 5%; the mass content of the mesoporous organic template agent is 0.5-10%, preferably 1.0-5.0%, and the balance is water.
In the above method, the pH of the mixed solution is adjusted to 2 to 5, preferably 2 to 3, and the acidic solution used is acetic acid or hydrochloric acid, preferably acetic acid. The pH value of the mixed solution is adjusted to ensure that the platinum complex is further and intensively adsorbed on the mesoporous organic template.
In the method, the mixed solution further contains macromolecular organic matters, and the macromolecular organic matters are selected from one or more of synthetic cellulose, polymeric alcohol, acrylic acid polymer with the molecular weight of 200-10000 and maleic acid copolymer. The synthetic cellulose is selected from one or more of carboxymethyl cellulose, methyl cellulose, ethyl cellulose and hydroxy cellulose. The polymeric alcohol is selected from one or more of polyethylene glycol, polypropylene alcohol and polyvinyl alcohol. The mass content of the macromolecular organic matters in the mixed solution is 0.5-10 percent, preferably 1.0-5.0 percent.
In the above method, the La-modified silica is obtained by supporting La on a silica powder, for example, by introducing La to a silica powder by an impregnation method and drying. The drying temperature is 80-220 ℃, and preferably 120-180 ℃; the drying time is 6-48 hours, and the drying time is 10-20 hours. The La-modified silicon dioxide contains 0.5-10% of lanthanum calculated by oxide, and preferably 1.0-5.0%. The lanthanum precursor is one or more of nitrate, sulfate and chloride of the lanthanum precursor, and preferably is nitrate.
In the method, one or more of a peptizing agent and an extrusion assistant can be added in the step (3) during the forming process. The drying and roasting conditions after molding are as follows: the drying temperature is 80-200 ℃, and the drying time is 6-48 hours; the roasting is carried out in an oxygen-containing atmosphere, and the roasting condition is that the roasting temperature is 300-800 ℃, and the roasting time is 4-10 hours.
The tertiary butanol refining catalyst prepared by the method comprises the following components, by weight, 0.1% -1.0% of Pt in terms of simple substance, preferably 0.2% -0.5%; the lanthanum content, calculated as oxide, is between 0.5% and 10.0%, preferably between 1.0% and 5.0%.
The catalyst is used for refining tertiary butanol, and the catalyst needs to be pretreated before use, namely, the hydrogenation active metal component is converted into an elemental substance, and wet reduction or dry reduction can be adopted, and dry reduction is preferred. The dry reduction can adopt pure hydrogen or hydrogen containing inert gas, wherein the volume content of the hydrogen is 5-100%, and preferably 50-100%; the reduction conditions were as follows: the pressure is normal pressure to 10MPa, preferably 2 MPa to 8MPa; the temperature is 200-600 ℃, preferably 300-400 ℃; the reduction time is 2 to 12 hours, preferably 2 to 6 hours, and the volume ratio of the gas agent (i.e. the volume ratio of the hydrogen to the catalyst) is 500 to 1500, preferably 800 to 1200.
The catalyst is used for refining tertiary butanol, and the reaction conditions are as follows: adopting a fixed bed reactor, wherein the tert-butyl alcohol raw material: the mass ratio of water is (20-120): 1, preferably (80 to 100): 1; the volume ratio of the tert-butyl alcohol raw material to the hydrogen is (10-100): 1, preferably (20 to 40): 1; the space velocity of the feeding volume is 0.5 h -1 ～3.0 h -1 Preferably for 1.5 h -1 ～2.5 h -1 (ii) a The reaction temperature is 150-300 ℃, and preferably 170-210 ℃; the reaction pressure is 0.5MPa to 5MPa, preferably 1.5MPa to 3 MPa.
Compared with the prior art, the method can effectively remove impurities in the tert-butyl alcohol raw material to obtain the refined tert-butyl alcohol.
Detailed Description
The action and effect of the present invention will be further described below with reference to examples and comparative examples, but the following examples and comparative examples are not intended to limit the present invention, and the% in the present invention is not particularly limited as long as it is a mass percentage.
The chromatographic analysis conditions of the tert-butyl alcohol raw material and the product are as follows: an Agilent 7890A gas chromatograph, a FID detector and a DB-1301 chromatographic column, and an internal standard method is adopted for quantitative analysis, wherein the internal standard substance is benzyl alcohol. The method for calculating the impurity removal rate comprises the following steps:
Figure 694876DEST_PATH_IMAGE001
example 1
Adding 10 g of 1, 1-cyclobutane dicarboxylic acid diammine platinum and 5.0 g of P123 into 100g of deionized water, adding acetic acid to adjust the pH value to be about 2, stirring at normal temperature for 20min to form a platinum-containing organic template agent, adding 5.0 g of carboxymethyl cellulose (with the molecular weight of 3000) into the solution, and continuously stirring at normal temperature for 40min to obtain a platinum-containing precursor required by the experiment, wherein the sample number is Sov-1.
Weighing 50g of silicon dioxide (with the particle size of 80 nm), adding 150ml of distilled water, stirring to mix uniformly, and weighing lanthanum nitrate (La) 2 O 3 Calculated) is added into the solution according to the mass percentage (based on the weight of the catalyst) of 2.5 percent, and the reaction is stopped after the solution is stirred for 42 hours at normal temperature; drying at 150 ℃ for 5 hours, and roasting at 650 ℃ for 5 hours to obtain the catalytic material precursor, numbered AS-1, required by the experiment.
Sov-1 and AS-1 were mixed and 25% (based on the weight of the catalyst, the same applies hereinafter) of ammonia-type silica Sol (SiO) 2 30 percent of starch and 10 percent of water, fully mixing the materials under the condition of continuous stirring, kneading the mixture into a plastic paste, forming a cylindrical orifice plate with the diameter of 2.0mm, drying the orifice plate at 120 ℃ for 12 hours, and roasting the orifice plate at 550 ℃ for 4 hours to obtain the catalyst, which is A1.
The catalyst evaluation is carried out in a fixed bed continuous micro flow reactor, the catalyst is reduced for 4 hours at 350 ℃ in the hydrogen atmosphere in advance, after the reduction is finished, the temperature of the reactor is reduced to a set value, and the raw material is introduced for carrying out the tertiary butanol refining reaction. The reaction conditions are as follows: the volume ratio of the tert-butyl alcohol raw material to the hydrogen is 30: 1; the space velocity of the feeding volume is 2.5 h -1 (ii) a The reaction temperature is 190 ℃; the reaction pressure was 2.0 MPa.
The catalyst composition is shown in Table 1, and the reaction results are shown in Table 2.
Example 2
Catalyst preparation and evaluation the same as example 1 except that: in the step 1, the carboxymethyl cellulose is changed into polyvinyl alcohol (molecular weight is 2000) powder, the content is 1.8 percent, and the numbering is as follows: sov-2.
The catalyst composition is shown in Table 1, and the reaction results are shown in Table 2.
Example 3
Catalyst preparation and evaluation the same as example 1 except that: 1, 2-diaminocyclohexane platinum oxalate is used for replacing 1, 1-diaminobutane dicarboxylic acid diammine platinum, carboxymethyl cellulose is changed into polypropylene alcohol (molecular weight is 2000) powder, and the mixture is stirred at normal temperature for 50min, and the number is Sov-3.
The catalyst composition is shown in Table 1, and the reaction results are shown in Table 2.
Example 4
Catalyst preparation and evaluation the same as example 1 except that: 1, 2-diaminocyclohexanepolyoxalate is used for replacing 1, 1-diaminocyclobutane dicarboxylic acid diammine platinum, and carboxymethyl cellulose is changed into acrylic acid polymer (molecular weight is 1500), and the number is Sov-4.
The catalyst composition is shown in Table 1, and the reaction results are shown in Table 2.
Example 5
Catalyst preparation and evaluation the same as example 1 except that: dichloro-1, 2-cyclohexanediamine platinum is used to replace 1, 1-cyclobutane dicarboxylic acid diammine platinum, and carboxymethyl cellulose (molecular weight is 3000) is changed into carboxymethyl cellulose (molecular weight is 4000), and the number is Sov-5.
The catalyst composition is shown in Table 1, and the reaction results are shown in Table 2.
Example 6
Catalyst preparation and evaluation the same as example 1 except that: platinum diammine 1, 1-cyclobutanedicarboxylate was added to F127, numbered: sov-6. The drying temperature was 120 ℃ and the drying time was 16 hours.
The catalyst composition is shown in Table 1, and the reaction results are shown in Table 2.
Example 7
Catalyst preparation and evaluation the same as example 1 except that: 1, 1-cyclobutane dicarboxylic acid diammine platinum is added into AEO, and carboxymethyl cellulose is changed into polyethylene glycol (molecular weight is 3000), and the number: sov-7. The drying temperature is 170 ℃, and the drying time is 24 hours; the calcination temperature of the carrier is 550 ℃ and the calcination time is 7.5 hours.
The catalyst composition is shown in Table 1, and the reaction results are shown in Table 2.
Figure 625923DEST_PATH_IMAGE002

Claims (10)

1. A preparation method of a tertiary butanol refining catalyst comprises the following steps:
(1) Preparing a mixed solution containing a platinum complex and a mesoporous organic template;
(2) Preparing lanthanum-modified silicon dioxide;
(3) Kneading and molding the mixed solution prepared in the step (1) and the lanthanum-modified silicon dioxide prepared in the step (2) to prepare a refined tert-butyl alcohol catalyst;
the platinum complex in the step (1) is one or more of dichloro-1, 2-cyclohexanediamine platinum, 1-cyclobutane dicarboxylic acid diammine platinum and 1, 2-diaminocyclohexane oxalic acid platinum, the mesoporous organic template is one or more of polyethylene oxide-polypropylene oxide-polyethylene oxide triblock copolymer, polyoxyethylene polyoxypropylene ether segmented copolymer and fatty alcohol polyoxyethylene ether, and the mass content of the platinum complex in the mixed solution is 0.5-10% by weight of a platinum simple substance; the mass content of the mesoporous organic template agent is 0.5-10%;
the lanthanum-modified silicon dioxide in the step (2) is prepared by loading lanthanum on silicon dioxide powder, wherein the mass content of lanthanum in the lanthanum-modified silicon dioxide is 0.5-10% in terms of oxide, and the lanthanum precursor is one or more of corresponding nitrate, sulfate and chloride.
2. The method of claim 1, wherein: and (2) adjusting the pH value of the mixed solution to 2-5 in the step (1).
3. The method of claim 1, wherein: the mixed solution in the step (1) contains macromolecular organic matters, and the macromolecular organic matters are selected from one or more of synthetic cellulose, polymeric alcohol, acrylic acid polymer with the molecular weight of 200-10000 and maleic acid copolymer.
4. The method of claim 3, wherein: the synthetic cellulose is selected from one or more of carboxymethyl cellulose, methyl cellulose, ethyl cellulose and hydroxy cellulose; the polymeric alcohol is selected from one or more of polyethylene glycol, polypropylene alcohol and polyvinyl alcohol.
5. The method of claim 3, wherein: the mass content of the macromolecular organic matters in the mixed solution is 0.5-10%.
6. The method of claim 1, wherein: loading lanthanum on silicon dioxide powder by an impregnation method, drying and roasting to obtain the catalyst.
7. The method of claim 6, wherein: the drying temperature is 80-220 ℃; the drying time is 6 to 48 hours.
8. The method of claim 1, wherein: and (3) adding one or more of peptizing agent and extrusion aid in the forming process, wherein the drying and roasting conditions after forming are as follows: the drying temperature is 80-200 ℃, and the drying time is 6-48 hours; the roasting is carried out in oxygen-containing atmosphere, the roasting condition is that the roasting temperature is 300-800 ℃, and the roasting time is 4-10 hours.
9. A catalyst prepared by the process of any one of claims 1 to 8, wherein: based on the weight of the final catalyst, the content of platinum in terms of simple substance is 0.1% -1.0%; the content of lanthanum is 0.5-10.0% calculated by oxide.
10. The use of the catalyst according to claim 9 for purification of t-butanol, characterized in that: the reaction conditions were as follows: adopting a fixed bed reactor, wherein the tert-butyl alcohol raw material: the mass ratio of water is (20-120): 1; the volume ratio of the tert-butyl alcohol raw material to the hydrogen is (10-100): 1; the volume space velocity of the tert-butyl alcohol raw material is 0.5 h -1 ～3.0 h -1 (ii) a The reaction temperature is 150-300 ℃; the reaction pressure is 0.5 MPa-5 MPa.
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Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS60212235A (en) * 1984-04-06 1985-10-24 Matsushita Electric Ind Co Ltd Preparation of catalyst
CN106140225A (en) * 2015-03-27 2016-11-23 中国石油化工股份有限公司 A kind of catalyst with silicon dioxide as carrier and its preparation method and application
CN109772439A (en) * 2017-11-14 2019-05-21 中国石油化工股份有限公司 A kind of tert-butyl alcohol catalyst for refining and its preparation method and application

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS60212235A (en) * 1984-04-06 1985-10-24 Matsushita Electric Ind Co Ltd Preparation of catalyst
CN106140225A (en) * 2015-03-27 2016-11-23 中国石油化工股份有限公司 A kind of catalyst with silicon dioxide as carrier and its preparation method and application
CN109772439A (en) * 2017-11-14 2019-05-21 中国石油化工股份有限公司 A kind of tert-butyl alcohol catalyst for refining and its preparation method and application

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