CN104028311A - Chemical regeneration method of catalyst for oxo-synthesis of butanol and octanol - Google Patents
Chemical regeneration method of catalyst for oxo-synthesis of butanol and octanol Download PDFInfo
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- CN104028311A CN104028311A CN201410313294.3A CN201410313294A CN104028311A CN 104028311 A CN104028311 A CN 104028311A CN 201410313294 A CN201410313294 A CN 201410313294A CN 104028311 A CN104028311 A CN 104028311A
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Abstract
The invention discloses a chemical regeneration method of a catalyst for oxo-synthesis of butanol and octanol. The chemical regeneration method includes the following steps that (1) free S<2-> and Cl<-> in a mother solution of the catalyst for oxo-synthesis of butanol and octanol are removed; (2) impurities in noble metal complexes formed by complexation of impurities and noble metals in the mother solution of the catalyst for oxo-synthesis of butanol and octanol are removed; (3) a regenerant C and an excessive amount of regenerant B are added into the mother solution of the catalyst, wherein the regenerant C is organic acid; (4) the mother solution of the catalyst for oxo-synthesis of butanol and octanol is washed several times through a regenerant A till the remaining regenerant B and the remaining regenerant C in the mother solution are washed away. Through the method, metal ions such as Fe<3+> and Ne<2+> and S<2-> in the catalyst for oxo-synthesis of butanol and octanol are reduced, permanently poisoned ions in the catalyst for oxo-synthesis of butanol and octanol are reduced, and the catalytic activity is stimulated.
Description
Technical field
The present invention relates to a kind of chemical regeneration method of permanent fouled catalyst, the invention particularly relates to a kind of method of fourth octanol oxo catalyst chemical regeneration.
Background technology
Catalyst mother liquor in fourth octanol carbonyl synthesizer feeds intake operation from original, along with the long-play of catalyst mother liquor, catalytic activity can slowly reduce, some toxic agent, the inhibitor (as S, Cl etc.) brought into due to reaction raw materials (synthesis gas, propylene), solvent (butyraldehyde) can cause catalytic activity to reduce rapidly simultaneously.For toxic agent, in production technology, the toxic component in raw material (synthesis gas, propylene) is had to strict control index, and fourth octanol carbongl group synthesis reaction technique has designed purifier to raw material, carries out strict detoxification process, and the activity of catalyst is only understood slow decreasing.Inhibitor can cause that catalyst activity reduces, but this reduction is not permanent.Main inhibitor in reaction system comprises: carboxylic acid (butyric acid), ethyl propyl methacrylaldehyde (EPA), propyl group diphenylphosphine (PDPP), butadiene/allene etc.
In existing patent, CN1403604 provides a kind of method that reclaims metal rhodium from the light base catalyst waste solution of alkene.This patent adopts the method for decompression distillation, evaporation and ashing to reclaim germanium metal, comparatively desirable for the recovering effect of rhodium in low concentration rhodium waste liquid especially.Reclaim after rhodium powder, more synthetic rhodium complex catalyst.The method is that technological process is long based on the reclaiming again of rhodium powder in rhodium complex catalyst waste liquid, and rhodium powder loses greatly in whole removal process.
CN101690898 discloses a kind of method of preparing Complex of Ge catalyst from carbonylation of olefin rhodium catalyst waste reaction solution.Be characterized in adopting the mixed solution of nitric acid and hydrogen peroxide to process the rhodium-containing waste reaction solution of preparing the light base catalyst of alkene, by bony with triphenyl the aqueous solution obtaining, hydrochloric acid and reaction of carbon monoxide, obtain two (triphenylphosphine) carbonyl radium chloride precipitation, the treated bony acetylacetone,2,4-pentanedione rhodium carbonyl of triphenyl or three (triphenylphosphine) carbonyl radium chloride catalyst of being converted into of isolated precipitation.The method processing be to prepare the waste reaction solution producing in rhodium complex catalyst process, compare obviously different from the decaying catalyst reactant liquor producing in process units: component is simple, and level of deactivation is little.Although therefore the method can obtain active higher catalyst, reaction process is many, long flow path, and in precipitation process, germanium loss is large, and catalyst inactivation is larger, and rhodium loss is more.
US4861918 discloses the method for the tertiary organophosphite ligand compound of a kind of rhodium one carbonylating catalyst regeneration, comprising:, under the carbonylation condition of non-water, mix the composition catalyst that contains above-mentioned part inactivation (1) with organic reagent; (2) remove the catalyst-initiator forming in (1).Regenerative response reagent used in patent is expensive, is difficult to obtain, and is unfavorable for commercial Application.
US5237106 introduced a kind of with propargyl alcohol and carboxylic acid processing section inactivation carbonylation rhodium complex catalyst to improve the process of its catalytic activity.This patent is taking propargyl alcohol and acetic acid as reaction reagent, and reaction pressure is normal pressure, has reacted rear and has neutralized with triethanolamine solution.The difficult point of this reaction is how to suppress the polymerization of propargyl alcohol in regenerative response process, improves the activity of regenerated catalyst.Patent does not openly suppress the method for propargyl alcohol polymerization, and propargyl alcohol consumption is large, has on the implementation certain difficulty.
CN102950027A and CN102950028A have introduced respectively propargyl alcohol, acetic acid, triethanolamine.At a certain temperature rhodium phosphine catalyst is regenerated as regenerative agent, bring up to 75% through regeneration rear catalyst activity from 28%, wherein chlorinity is reduced to 7mg/kg from 29mg/kg.This regeneration technology shows that this chemical regeneration is only for suppressing toxic agent Cl-successful.
Summary of the invention
The object of the invention is to overcome the deficiency of existing technique, provide one to reduce Fe in fourth octanol oxo catalyst
3+, Ne
2+and S
2-deng metal ion, reduce permanent poisoning ion in fourth octanol oxo catalyst, excite the fourth octanol oxo catalyst chemical regeneration method of catalytic activity.
A kind of fourth octanol oxo catalyst chemical regeneration method of the present invention, it comprises the following steps:
(1) remove the S of free state in fourth octanol oxo catalyst mother liquor
2-and Cl
-, concrete steps are: under the fourth octanol carbongl group synthesis reaction process conditions under nonproductive state, regenerative agent A is evenly mixed with fourth octanol oxo catalyst mother liquor, to being present in the S of the free state in fourth octanol oxo catalyst mother liquor
2-and Cl
-wash, make to produce in catalyst mother liquor fourth octanol oxo catalyst phase and the layering of regenerative agent A phase, S
2-and Cl
-transfer to regenerative agent A mutually in, retain fourth octanol oxo catalyst phase, the regenerative agent A phase of draining, described regenerative agent A is desalted water mutually;
(2) remove the impurity in the noble metal complexes that in fourth octanol oxo catalyst mother liquor, impurity and noble metal complexing form, concrete steps are: the fourth octanol oxo catalyst mother liquor of reservation is warming up to 60 DEG C-65 DEG C mutually, then the regenerative agent B that by temperature is 20-55 DEG C adds in the fourth octanol oxo catalyst mother liquor after intensification, regenerative agent B reacts with the impurity in noble metal complexes and within 8-12 hour, forms new Complexes, thereby realize separating of impurity and noble metal, described regenerative agent B is that mass percent concentration is 1-38% alkanolamine solution, in mother liquor, the mass ratio of the content of noble metal and regenerative agent B addition is 1:20～20:1,
(3) then regenerative agent C is added in catalyst mother liquor and excessive regenerative agent B, described regenerative agent C is organic acid;
(4) with regenerative agent A cyclic washing fourth octanol oxo catalyst mother liquor several, until wash regenerative agent B and regenerative agent C remaining in mother liquor off.
While adopting the inventive method, there is following effect:
Reduce Fe in fourth octanol oxo catalyst
3+, Ne
2+and S
2-deng metal ion, reduce permanent poisoning ion in fourth octanol oxo catalyst, excite catalytic activity.
Detailed description of the invention
Below in conjunction with specific embodiment, the present invention is described in detail.
A kind of fourth octanol oxo catalyst chemical regeneration method of the present invention, it comprises the following steps: (1) removes the S of free state in fourth octanol oxo catalyst mother liquor
2-and Cl
-concrete steps are: (low pressure carbongl group synthesis reaction technological parameter is OXO response parameter to the fourth octanol carbongl group synthesis reaction process conditions under nonproductive state, can be referring to " several process route comparisons of the synthetic butyraldehyde of propylene oxo synthesis " Agricultural University Of Hunan's journal, in August, 2014, the 30th the 4th phase of volume) under, regenerative agent A is evenly mixed with fourth octanol oxo catalyst mother liquor, to being present in the S of the free state in fourth octanol oxo catalyst mother liquor
2-and Cl
-wash, make to produce in catalyst mother liquor fourth octanol oxo catalyst phase and the layering of regenerative agent A phase, S
2-and Cl
-transfer to regenerative agent A mutually in, retain fourth octanol oxo catalyst phase, the regenerative agent A phase of draining, described regenerative agent A is desalted water mutually; (2) remove in fourth octanol oxo catalyst mother liquor impurity as S
2-, Cl
-, Fe
3+, and Ni
2+impurity in the noble metal complexes forming with noble metal complexing is as S
2-, Cl
-, Fe
3+, and Ni
2+concrete steps are: the fourth octanol oxo catalyst mother liquor of reservation is warming up to 60 DEG C-65 DEG C mutually, then the regenerative agent B that by temperature is 20-55 DEG C adds in the fourth octanol oxo catalyst mother liquor after intensification, (the preferred mode that adopts spray adds, prevent from adding rear skewness, the time of contact that can increase alkanolamine solution and catalyst mother liquor simultaneously, prevent the polymerization of the butyraldehyde in mother liquor.) impurity in regenerative agent B and noble metal complexes is as S
2-, Cl
-, Fe
3+, and Ni
2+react and within 8-12 hour, form new Complexes, thereby realize separating of impurity and noble metal, described regenerative agent B is that mass percent concentration is 1-38% alkanolamine solution, and in mother liquor, the mass ratio of the content of noble metal and regenerative agent B addition is 1:20～20:1; Described alkanolamine solution can adopt the one in monoethanolamine, diethanol amine, triethanolamine or diisopropanolamine (DIPA); (3) then regenerative agent C is added in catalyst mother liquor and excessive regenerative agent B, prevent the remnants of regenerative agent B, cause fourth octanol oxo catalyst to suppress the generation of toxic agent octenal (EPA), EHA (EHA), described regenerative agent C can be organic acid, as the one in acetic acid, propionic acid or butyric acid; (4) with regenerative agent A cyclic washing fourth octanol oxo catalyst mother liquor several, until wash regenerative agent B and regenerative agent C remaining in mother liquor off.
Embodiment 1
The activity of the fourth octanol oxo catalyst mother liquor catalyst of butyl octanol unit declines suddenly, shows as operating load and reduces, and propylene, hydrogen, carbon monoxide pressure of tension obviously go up simultaneously.Catalyst poisoning, through determining that to the active testing of catalyst in reactor activity has been reduced to 26%.
For above-mentioned situation, adopt following methods to fourth octanol oxo catalyst chemical regeneration:
(1) remove the S of free state in fourth octanol oxo catalyst mother liquor
2-and Cl
-, concrete steps are: under the fourth octanol carbongl group synthesis reaction process conditions under nonproductive state, regenerative agent A is evenly mixed with fourth octanol oxo catalyst mother liquor, to being present in the S of the free state in fourth octanol oxo catalyst mother liquor
2-and Cl
-wash, make to produce in catalyst mother liquor fourth octanol oxo catalyst phase and the layering of regenerative agent A phase, S
2-and Cl
-transfer to regenerative agent A mutually in, retain fourth octanol oxo catalyst phase, the regenerative agent A phase of draining, described regenerative agent A is desalted water mutually;
(2) the impurity concrete steps of removing in the noble metal complexes that in fourth octanol oxo catalyst mother liquor, impurity and noble metal complexing form are: the fourth octanol oxo catalyst mother liquor of reservation is warming up to 62 DEG C mutually, then the regenerative agent B that by temperature is 45 DEG C adds in the fourth octanol oxo catalyst mother liquor after intensification, and the impurity in regenerative agent B and noble metal complexes is as S
2-, Cl
-, Fe
3+, and Ni
2+react and form new Complexes in 10 hours, thereby realize separating of impurity and noble metal, described regenerative agent B is that mass percent concentration is 25% monoethanolamine solution, and in mother liquor, the mass ratio of the content of noble metal and regenerative agent B addition is 1:20;
(3) then regenerative agent C is added in catalyst mother liquor and excessive regenerative agent B, described regenerative agent C is acetic acid;
(4) with regenerative agent A cyclic washing fourth octanol oxo catalyst mother liquor several, until wash regenerative agent B and regenerative agent C remaining in mother liquor off.
By adopting the inventive method to regenerate to catalyst chemical, the activity of rhodium catalyst has been brought up to 64% left and right from original 26%, and from poisoning 96 DEG C of reaction temperature are reduced to 87.5 DEG C, produce Load lifting to 100%.
Embodiment 2
The activity of the catalyst of the fourth octanol oxo catalyst mother liquor in butyl octanol unit declines suddenly, shows as operating load and reduces, and propylene, hydrogen, carbon monoxide pressure of tension obviously go up simultaneously.Catalyst poisoning, through determining that to the active testing of catalyst in reactor activity has been reduced to 28%.
For above-mentioned situation, adopt following methods to fourth octanol oxo catalyst chemical regeneration:
(1) remove the S of free state in fourth octanol oxo catalyst mother liquor
2-and Cl
-, concrete steps are: under the fourth octanol carbongl group synthesis reaction process conditions under nonproductive state, regenerative agent A is evenly mixed with fourth octanol oxo catalyst mother liquor, to being present in the S of the free state in fourth octanol oxo catalyst mother liquor
2-and Cl
-wash, make to produce in catalyst mother liquor fourth octanol oxo catalyst phase and the layering of regenerative agent A phase, S
2-and Cl
-transfer in regenerative agent A phase mother liquor, retain fourth octanol oxo catalyst phase, the regenerative agent A phase of draining, described regenerative agent A is desalted water mutually;
(2) the impurity concrete steps of removing in the noble metal complexes that in fourth octanol oxo catalyst mother liquor, impurity and noble metal complexing form are: the fourth octanol oxo catalyst mother liquor of reservation is warming up to 60 DEG C mutually, then the regenerative agent B that by temperature is 20 DEG C adopts the mode of spray to add in the fourth octanol oxo catalyst mother liquor after intensification, and the impurity in regenerative agent B and noble metal complexes is as S
2-, Cl
-, Fe
3+, and Ni
2+react and form new Complexes in 12 hours, thereby realize separating of impurity and noble metal, described regenerative agent B is that mass percent concentration is 1% diethanolamine solution, and in mother liquor, the mass ratio of the content of noble metal and regenerative agent B addition is 20:1;
(3) then regenerative agent C is added in catalyst mother liquor and excessive regenerative agent B, described regenerative agent C is propionic acid;
(4) with regenerative agent A cyclic washing fourth octanol oxo catalyst mother liquor several, until wash regenerative agent B and regenerative agent C remaining in mother liquor off.
By adopting the inventive method to regenerate to catalyst chemical, the activity of rhodium catalyst has been brought up to 66% left and right from original 28%, and from poisoning 96 DEG C of reaction temperature are reduced to 87.5 DEG C, produce Load lifting to 100%.
Embodiment 3
Fourth octanol oxo catalyst mother liquor Partial Elements after poisoning exceeds standard, wherein S:0.137%, and Na:62.79ppm, Ni51.2ppm, Fe:24.77ppm, S exceeds standard 1370 times, and Cl exceeds standard 4.5 times.
For above-mentioned situation, adopt following methods to fourth octanol oxo catalyst chemical regeneration:
(1) remove the S of free state in fourth octanol oxo catalyst mother liquor
2-and Cl
-, concrete steps are: under the fourth octanol carbongl group synthesis reaction process conditions under nonproductive state, regenerative agent A is evenly mixed with fourth octanol oxo catalyst mother liquor, to being present in the S of the free state in fourth octanol oxo catalyst mother liquor
2-and Cl
-wash, make to produce in catalyst mother liquor fourth octanol oxo catalyst phase and the layering of regenerative agent A phase, S
2-and Cl
-transfer to regenerative agent A mutually in, retain fourth octanol oxo catalyst phase, the regenerative agent A phase of draining, described regenerative agent A is desalted water mutually;
(2) the impurity concrete steps of removing in the noble metal complexes that in fourth octanol oxo catalyst mother liquor, impurity and noble metal complexing form are: the fourth octanol oxo catalyst mother liquor of reservation is warming up to 65 DEG C mutually, then the regenerative agent B that by temperature is 55 DEG C adopts the mode of spray to add in the fourth octanol oxo catalyst mother liquor after intensification, and the impurity in regenerative agent B and noble metal complexes is as S
2-, Cl
-, Fe
3+, and Ni
2+react and form new Complexes in 8 hours, thereby realize separating of impurity and noble metal, described regenerative agent B is that mass percent concentration is 38% diisopropanol amine aqueous solution, and in mother liquor, the mass ratio of the content of noble metal and regenerative agent B addition is 1:1;
(3) then regenerative agent C is added in catalyst mother liquor and excessive regenerative agent B, described regenerative agent C is butyric acid;
(4) with regenerative agent A cyclic washing fourth octanol oxo catalyst mother liquor several, until wash regenerative agent B and regenerative agent C remaining in mother liquor off.
Fourth octanol oxo catalyst mother liquor Partial Elements content after chemical regeneration is S:9.8ppm, Na:5.79ppm, and Ni2.1ppm, Fe:1.2ppm, Cl does not detect.
Claims (4)
1. a fourth octanol oxo catalyst chemical regeneration method, is characterized in that it comprises the following steps:
(1) remove the S of free state in fourth octanol oxo catalyst mother liquor
2-and Cl
-, concrete steps are: under the fourth octanol carbongl group synthesis reaction process conditions under nonproductive state, regenerative agent A is evenly mixed with fourth octanol oxo catalyst mother liquor, to being present in the S of the free state in fourth octanol oxo catalyst mother liquor
2-and Cl
-wash, make to produce in catalyst mother liquor fourth octanol oxo catalyst phase and the layering of regenerative agent A phase, S
2-and Cl
-transfer to regenerative agent A mutually in, retain fourth octanol oxo catalyst phase, the regenerative agent A phase of draining, described regenerative agent A is desalted water mutually;
(2) remove the impurity in the noble metal complexes that in fourth octanol oxo catalyst mother liquor, impurity and noble metal complexing form, concrete steps are: the fourth octanol oxo catalyst mother liquor of reservation is warming up to 60 DEG C-65 DEG C mutually, then the regenerative agent B that by temperature is 20-55 DEG C adds in the fourth octanol oxo catalyst mother liquor after intensification, regenerative agent B reacts with the impurity in noble metal complexes and within 8-12 hour, forms new Complexes, thereby realize separating of impurity and noble metal, described regenerative agent B is that mass percent concentration is 1-38% alkanolamine solution, in mother liquor, the mass ratio of the content of noble metal and regenerative agent B addition is 1:20～20:1,
(3) then regenerative agent C is added in catalyst mother liquor and excessive regenerative agent B, described regenerative agent C is organic acid;
(4) with regenerative agent A cyclic washing fourth octanol oxo catalyst mother liquor several, until wash regenerative agent B and regenerative agent C remaining in mother liquor off.
2. fourth octanol oxo catalyst chemical regeneration method according to claim 1, is characterized in that: in described step (2), regenerative agent B adopts the mode of spray to add in the fourth octanol oxo catalyst mother liquor after intensification.
3. fourth octanol oxo catalyst chemical regeneration method according to claim 1 and 2, is characterized in that: described alkanolamine solution adopts the one in monoethanolamine, diethanol amine, triethanolamine or diisopropanolamine (DIPA).
4. fourth octanol oxo catalyst chemical regeneration method according to claim 3, is characterized in that: described regenerative agent C is organic acid, as the one in acetic acid, propionic acid or butyric acid.
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Citations (6)
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|---|---|---|---|---|
| US3555098A (en) * | 1967-12-13 | 1971-01-12 | Union Oil Co | Hydroformylation |
| CN1040746A (en) * | 1988-08-12 | 1990-03-28 | 联合碳化化学品及塑料有限公司 | The reactivation of carbonylating catalyst |
| CN1040825A (en) * | 1988-08-12 | 1990-03-28 | 联合碳化化学品及塑料有限公司 | From non-polar organic solutions, reclaim catalytic metal |
| CN1066009A (en) * | 1991-03-18 | 1992-11-11 | 联合碳化化学品及塑料技术公司 | The reactivation of carbonylation reaction catalyst |
| US5466644A (en) * | 1991-10-24 | 1995-11-14 | Hoechst Aktiengesellschaft | Reactivation of water-soluble hydroformylation catalysts |
| CN102950028A (en) * | 2011-08-31 | 2013-03-06 | 中国石油化工股份有限公司 | Regeneration method for inactivated rh-p (rhodium-phosphine) complex catalyst for carbonylation reaction |
-
2014
- 2014-07-02 CN CN201410313294.3A patent/CN104028311B/en active Active
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3555098A (en) * | 1967-12-13 | 1971-01-12 | Union Oil Co | Hydroformylation |
| CN1040746A (en) * | 1988-08-12 | 1990-03-28 | 联合碳化化学品及塑料有限公司 | The reactivation of carbonylating catalyst |
| CN1040825A (en) * | 1988-08-12 | 1990-03-28 | 联合碳化化学品及塑料有限公司 | From non-polar organic solutions, reclaim catalytic metal |
| CN1066009A (en) * | 1991-03-18 | 1992-11-11 | 联合碳化化学品及塑料技术公司 | The reactivation of carbonylation reaction catalyst |
| US5466644A (en) * | 1991-10-24 | 1995-11-14 | Hoechst Aktiengesellschaft | Reactivation of water-soluble hydroformylation catalysts |
| CN102950028A (en) * | 2011-08-31 | 2013-03-06 | 中国石油化工股份有限公司 | Regeneration method for inactivated rh-p (rhodium-phosphine) complex catalyst for carbonylation reaction |
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Application publication date: 20140910 Assignee: Tianjin Jiuda Technology Co.,Ltd. Assignor: TIANJIN BOHUA YONGLI CHEMICAL INDUSTRY Co.,Ltd. Contract record no.: X2021120000034 Denomination of invention: A chemical regeneration method of butanol octanol carbonyl synthesis catalyst Granted publication date: 20160615 License type: Common License Record date: 20211229 |