CN104371784A - Liquefied petroleum gas alcohol-amine desulfurization method - Google Patents
Liquefied petroleum gas alcohol-amine desulfurization method Download PDFInfo
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Abstract
The invention provides a liquefied petroleum gas alcohol-amine desulfurization method. The method comprises the following steps: removing oxygen gas from an alcohol-amine water solution, then contacting the alcohol-amine water solution with liquefied petroleum gas to carry out alcohol-amine desulfurization reactions, and collecting the liquefied petroleum gas product. The provided alcohol-amine desulfurization method can avoid or reduce the generation of disulfides and polysulfide, liquefied petroleum gas without disulfides or polysulfide is provided for the alkali solution desulfurization technology, thus the desulfurization efficiency of the alkali solution desulfurization technology is prominently improved, and the sulfides in the liquefied petroleum gas are radically removed.
Description
Technical field
The present invention relates to the sulfur method of liquefied petroleum gas (LPG), particularly a kind of hydramine sulfur method of liquefied petroleum gas (LPG).
Background technology
As everyone knows, MTBE(methyl tertiary butyl ether) be non-hydrocarbons high-octane rating blending component maximum in China's gasoline, can quality of gasoline be significantly improved.But under existing working condition, obviously containing sulfide in the MTBE of output, generally sulphur content reaches 60 ~ 300mg/kg, and the sulphur content in the MTBE of part manufacturer production is sometimes especially up to 2000mg/kg.
MTBE can be synthesized in acid condition by iso-butylene and methyl alcohol, industrial direct use containing iso-butylene liquefied petroleum gas (LPG) in as raw material, the production cost of MTBE is significantly reduced.But international standard does not become the requirement of sulphur content in civil LPG for many years, and its standard is for being not more than 343mg/m always
3(about corresponding to 150mg/kg), and be significantly improve for the requirement of sulfur content in gasoline, the sulphur content starting the state II gasoline performed for such as 2005 requires to be not more than 500mg/kg, requires that sulphur content is not more than 150mg/kg during 2008 years state of enforcement III.State Environmental Protection Administration explicitly calls for, and require during nationwide state of enforcement IV in 2014 that sulphur content is not more than 50mg/kg, subsequently during state of enforcement V, sulphur content is not more than the standard of 10mg/kg, and urban is as Beijing state of enforcement V gasoline standard.
Find in research, in the building-up process of MTBE, partial vulcanization thing in liquefied petroleum gas (LPG) is converted into the sulfide in MTBE, but because the requirement of liquefied petroleum gas (LPG) sulphur content is substantially constant, the sulfur removal technology of liquefied petroleum gas (LPG) in factory, operational condition is caused to change little, make the sulphur content of the liquefied petroleum gas (LPG) of producing qualified, but be generally 2 ~ 3 times of sulphur content in liquefied petroleum gas (LPG) by the sulphur content of this liquefied petroleum gas (LPG) production MTBE, as sulphur content 200mg/m
3the liquefied petroleum gas (LPG) of (about corresponding to 80mg/kg) is after gas divides, and the sulphur content in C4 is about 400mg/m
3(about corresponding to 180mg/kg), the sulphur content in the MTBE of production is about 400mg/kg.
Due to the quick upgrading of quality of gasoline, requirement for sulphur content is more and more stricter, the sulphur content problem of MTBE is become increasingly conspicuous, if significantly do not reduce the sulphur content in MTBE, following MTBE can cannot call in gasoline because sulphur content is too high, and this will cause existing MTBE production equipment to use, or future significantly raises the production cost of domestic gasoline, the direct production and supply affecting gasoline, also has influence on the Appropriate application of refinery's liquefied petroleum gas (LPG) resource.
On the other hand, although do not significantly improve for the requirement of civil LPG sulphur content, in some fields, also more and more higher for the requirement of sulphur content in liquefied petroleum gas (LPG).Such as both at home and abroad the be not more than 200mg/kg of the requirement of sulphur content from the nineties in last century is dropped to and present be not more than 10mg/kg in Vehicular liquefied petroleum gas standard, during as industrial chemicals or synthetic oil raw material, sulphur content for liquefied petroleum gas (LPG) also has very strict requirement, sometimes even requires to reach without sulphur (below 0.5mg/kg).
Having a kind of method of conventional desulfurization, is the hybrid C 4 re-distillation again after being divided by gas, and be cut into light C4 and heavy C4, wherein the iso-butylene content of light C4 is higher, and sulphur content is lower, and as etherificate or raw material for alkylation, the sulphur content of the MTBE obtained after etherificate is also lower; Heavy C4 is then mainly as the blending stock of liquefied petroleum gas (LPG), and the most of sulfide in C4 concentrates on this cut.The shortcoming one of this technique is that redistilled energy consumption is higher, and two is that cause being difficult to be separated thoroughly, the sulphur content of the MTBE that result obtains also is difficult to take off below 10mg/kg because the light C4 such as C4 medium sulphide content boiling point and iso-butylene is more or less the same.
CN 101077984 describes a kind of method of liquefied petroleum gas (LPG) deep desulfuration, liquefied petroleum gas (LPG) after alcohol amine removal hydrogen sulfide, make carbonyl sulfide hydrolysis by hydrolyst and be desulfurized agent to absorb, realize removing of inorganic sulfur in liquefied gas, mercaptan in liquefied gas is converted into disulphide by the oxygen being decomposed generation by hydrogen peroxide under catalytic condition under mercaptan-eliminating catalyst effect, by rectifying, obtain the liquefied petroleum gas (LPG) of low-sulfur.
CN 1687327 provides a kind of method alkyl sulfhydrate contained in liquefied petroleum gas being converted into disulphide, the method pumps into air or oxygen to removing being in the liquefied petroleum gas (LPG) of flow state after hydrogen sulfide treatment through hydramine method, in flowing, air or oxygen dissolution are in liquefied petroleum gas (LPG), when the liquefied petroleum gas (LPG) that this is dissolved with air or oxygen by be arranged in fixed-bed reactor there is the beds of mercaptan conversion catalyst performance time, under the effect of catalyzer, alkyl sulfhydrate contained in liquefied petroleum gas is oxidized to disulphide by the oxygen in liquefied petroleum gas (LPG).
CN 1702157 discloses the method for desulfuration purification catalytic liquefied petroleum gas, catalytic liquefied petroleum gas after alcohol amine removal of H2S process is hydrolyzed by hydrolytic catalyst of carbonyl sulfur bed and is removed the hydrogen sulfide of generation after carbonylsulfide process by sorbent material by the method, tertbutyl peroxide is added again in catalytic liquefied petroleum gas, the mercaptan oxidation in liquefied petroleum gas (LPG) is made to become disulphide, if rectifying further, can obtain the liquefied petroleum gas (LPG) of low sulfur content.
These methods, to a certain extent can inorganic sulfur in effective elimination liquefied petroleum gas (LPG) and organosulfur, or by organic sulfur conversion.Common feature is all adopt conventional desulfuration processing method for liquefied petroleum gas (LPG) itself, has all carried out simple oxidation process to mercaptan.But in fact use superoxide to have very large potential safety hazard as the source of oxygenant or oxygen in liquefied petroleum gas (LPG) factory, and be distillate liquefied oil gas again after disulphide by the mercaptan oxidation in liquefied petroleum gas (LPG), liquefied petroleum gas (LPG) is needed all again to gasify, ensure the thorough separation of the disulphide at the bottom of tower, the energy consumption of operation is very high, but also again enters the problem in the liquefied petroleum gas (LPG) steamed after there is disulphide or polysulfide decomposed.
Existing LPG Desulfurization technique encounters bottleneck: be reduced to a certain degree in sulphur content, no matter adopt great cost, sulphur content no longer reduce or improvement amplitude very little, but resource is at double consumed in vain: add device, multiplex auxiliary agent, consume a large amount of alkali lye and amine liquid, significantly increase the environmental protection treatment pressure of alkaline sewage simultaneously.
Find under study for action, liquefied petroleum gas (LPG) is from contact hydramine, and just have part mercaptan oxidation to be disulphide and polysulfide, oxygenant is wherein come from the dissolved oxygen in hydramine and the micro amount of oxygen voltinism material in hydramine.Generate disulphide or polysulfide can not by follow-up (alkali lye) remove, these disulphide in liquefied petroleum gas (LPG) or polysulfide are by " permanent resident " wherein; When the sulfide that these are dissolved in liquefied petroleum gas (LPG) runs into strongly acidic cation-exchange, part can produce high boiling thioether with isobutene reaction, the thioether generated residues in MTBE as high boiling polysulfide, almost becomes whole contributors of MTBE sulphur content.
Summary of the invention
The invention provides a kind of hydramine sulfur method of liquefied petroleum gas (LPG).
Hydramine sulfur method of the present invention comprises: to contact with liquefied petroleum gas (LPG) carry out hydramine desulphurization reaction by removing the aqueous alkanolamine after oxygen, collect liquefied petroleum gas product.
The described oxygen that removes removes dissolved oxygen in aqueous alkanolamine and gas phase oxygen, can remove the oxygen in hydramine or water respectively, also directly can remove the oxygen in aqueous alkanolamine.
The structure of described hydramine is: R
1r
2n-R
3, R
1, R
2, R
3hydrogen, C
1-C
4the alkyl of alkyl or hydroxyl, wherein at least one group is the alkyl containing a hydroxyl, and hydroxyl and atom N non-conterminous, Monoethanolamine MEA BASF (MEA), diethanolamine (DEA), diisopropanolamine (DIPA) (DIPA), N methyldiethanol amine (MDEA), N can be selected, one or more in N-diethylethanolamine (DEEA), N-ethyldiethanolamine (EDEA), monoisopropanolamine (MIPA) and tri-isopropanolamine (TIDP), one or more in preferred Monoethanolamine MEA BASF, diethanolamine, diisopropanolamine (DIPA) and N methyldiethanol amine.
Described hydramine accounts for 10 ~ 70% of aqueous alkanolamine total mass, and preferably 15 ~ 50%, most preferably 20 ~ 40%.
Main containing C in described liquefied petroleum gas (LPG)
3~ C
20alkane, aromatic hydrocarbons, alkene or their mixture.Sulfide in liquefied petroleum gas (LPG) is mainly H
2s, mercaptan, carbonylsulfide.
After the oxygen contained in described aqueous alkanolamine contacts with liquefied petroleum gas (LPG), can be disulphide or polysulfide by the mercaptan oxidation in liquefied petroleum gas (LPG), these disulphide generated or polysulfide to be difficult to remove by follow-up alkali lye sulfur removal technology and reside in liquefied petroleum gas (LPG), therefore the oxygen in aqueous alkanolamine is only removed, liquefied petroleum gas (LPG) without disulphide and polysulfide could be provided for next step alkali lye sulfur removal technology, thus improve the desulfuration efficiency of alkali lye sulfur removal technology, finally thoroughly remove the sulfide in liquefied petroleum gas (LPG).
One or more in physics method of deoxidation, chemical method of deoxidation and biological method of deoxidation can be adopted to remove the oxygen in aqueous alkanolamine.
Described physics method of deoxidation comprise in thermal de-aeration, deaeration in condenser and parsing deoxidation method one or more.
Described thermal de-aeration is in a heated condition, reduces the solubleness of oxygen in aqueous alkanolamine, and the oxygen in aqueous alkanolamine is constantly overflowed, thus removes oxygen, the preferably Heating temperature of more than 100 DEG C.
Described deaeration in condenser removes oxygen under vacuum, carries out preferably be less than the condition of 0.001MPa at pressure under.
Described parsing deoxygenation is the gas that utilizes concentration of oxygen gas large and/or hydrocarbon ils and want the aqueous alkanolamine of deoxygenation to contact or mix, and the oxygen in aqueous alkanolamine is resolved in the large gas of described concentration of oxygen gas and/or hydrocarbon ils.The gas preferred nitrogen that described concentration of oxygen gas is large and/or rare gas element.Without the liquid hydrocarbon of sulphur under the preferred normal temperature and pressure of the hydrocarbon ils that described concentration of oxygen gas is large, one or more of such as gasoline, kerosene, diesel oil, hexane and heptane, the preferred sulphur content of the described liquid hydrocarbon without sulphur is lower than the liquid hydrocarbon of 10ppm.
Described chemical method of deoxidation is contacted with reductor by aqueous alkanolamine or mixes the oxygen removed in aqueous alkanolamine, and described reductor is the reducing substances that can not react with oxygen generation redox reaction and with described aqueous alkanolamine.
Described reductor can select in gaseous state reductor, liquid deoxidizer and solid-state reductor one or more, the preferred H of described gaseous state reductor
2, CO or hydrazine, described liquid state or solid-state reductor can select ketoxime class, aldoxime class, hydrazine class, sulphite, one or more in reducing metal and reductibility resin, such as can select DMKO (acetoxime, DMKO), Diacetylmonoxime, ethylidenehydroxylamine, hydrazine hydrate, one or more in S-WAT and vitamin-E, the preferred reducing metal bits of described reducing metal and/or sponge state reducing metal, such as steel cuttings can be selected, sponge iron, the preferred hydroquinone type of described reductibility resin, sulfydryl class, one or more in pyridines and ferrocene resinoid, such as can select Resorcinol resinoid, sulfydryl resinoid.
The preferred add-on of described reductor is 0.1 ~ 200mg/L of described aqueous alkanolamine.
Described biological method of deoxidation in aqueous alkanolamine, adds deoxidation microorganism and/or deoxidation plant remove oxygen wherein.
The content of described oxygen in aqueous alkanolamine is generally more than 10mg/L; Remove after oxygen through the inventive method, the oxygen content in aqueous alkanolamine is below 0.1mg/L.
Described aqueous alkanolamine is as follows with the preferred processing condition of liquefied petroleum gas (LPG) generation hydramine desulphurization reaction after removing oxygen:
The volume ratio of described aqueous alkanolamine and liquefied petroleum gas (LPG) is 1:1 ~ 1:100, preferred 1:1 ~ 1:50; Contact Temperature is 10 ~ 80 DEG C, preferably 20 ~ 60 DEG C, most preferably 30 ~ 50 DEG C.
The generation of disulphide, polysulfide can be avoided or reduce to hydramine sulfur method of the present invention, for next step alkali lye sulfur removal technology provides the liquefied petroleum gas (LPG) without disulphide or polysulfide, significantly improve the desulfuration efficiency of next step alkali lye sulfur removal technology, thus thoroughly remove the sulfide in liquefied petroleum gas (LPG).
Embodiment
Unless stated otherwise, the per-cent below mentioned is mass percent.
In the present invention, raw materials used source is as follows:
Catalytic liquefied petroleum gas, takes from the stable liquefied gas of China Petrochemical Corp. subordinate refinery MIP technique;
Coking liquefied petroleum gas (LPG), takes from the stable liquefied gas of China Petrochemical Corp. subordinate refinery delay coking process;
Before desulfurization, after desulfurization, the sulphur content of liquefied petroleum gas (LPG) adopts SH/T0222 method to measure, and sulfur speciation distribution adopts GC-SCD method to measure.
Embodiment 1
The hydramine sweetening agent SSH-3 of Taihu Lake, Changzhou Chemical Co., Ltd. and distilled water are hybridly prepared into the aqueous alkanolamine that content is 30%.Catalytic liquefied petroleum gas to be desulfurization is the stable liquefied gas taking from China Petrochemical Corp. subordinate refinery MIP technique.
Before desulfurization, nitrogen is carried out to aqueous alkanolamine and remove oxygen treatments applied, use sintered metal net as divider, when the nitrogen volume passed into is equivalent to 1 times of aqueous alkanolamine volume, terminate the process removing oxygen.
Laboratory desulfurizer carries out desulfurization test, the processing condition adopted are: the aqueous alkanolamine after removing oxygen and catalytic liquefied petroleum gas are in packing tower counter current contact, Contact Temperature is 40 DEG C, the volume ratio of aqueous alkanolamine and liquefied petroleum gas (LPG) is 1:2.5, and during the liquid of catalytic liquefied petroleum gas, volume space velocity is 10h
-1.
Comparative example 1
Desulfurization test, with embodiment 1, does not just remove the process of oxygen to aqueous alkanolamine, but directly uses aqueous alkanolamine to carry out desulfurization test to catalytic liquefied petroleum gas.
Raw materials used catalytic liquefied petroleum gas and after embodiment 1, comparative example 1 desulfurization process the composition of liquefied petroleum gas (LPG) medium sulphide content in table 1.
Table 1
| Various sulfide content | Catalytic liquefied petroleum gas | Embodiment 1 | Comparative example 1 |
| Sulphur content/% | 0.1213 | 0.0648 | 0.0660 |
| Hydrogen sulfide sulphur/% | 0.0554 | 0.0003 | 0.0005 |
| Carbonylsulfide/% | 0.0018 | 0.0002 | 0.0001 |
| Mercaptan sulfur/% | 0.0635 | 0.0649 | 0.0478 |
| Disulphide sulphur/% | 0.0001 | 0.0002 | 0.0131 |
| Polysulfide sulphur/% | 0.0000 | 0.0001 | 0.0012 |
Embodiment 2
The hydramine composite desulfurizing agent (main component is N methyldiethanol amine) Jiangsu being innovated Chemical Co., Ltd. is hybridly prepared into distilled water the aqueous alkanolamine that content is 28%.Coking liquefied petroleum gas (LPG) to be desulfurization takes from the stable liquefied gas of the delay coking process of China Petrochemical Corp. subordinate refinery.
Before desulfurization, thermal de-aeration is carried out to aqueous alkanolamine, aqueous alkanolamine is heated to 100 DEG C, heat half an hour, then leave standstill and terminate the process removing oxygen half an hour.
Laboratory desulfurizer carries out desulfurization test, the processing condition adopted are: the aqueous alkanolamine after removing oxygen and coking liquefied petroleum gas (LPG) are in packing tower counter current contact, Contact Temperature is 42 DEG C, the volume ratio of aqueous alkanolamine and liquefied petroleum gas (LPG) is 1:1.5, and during the liquid of catalytic liquefied petroleum gas, volume space velocity is 8h
-1.
Comparative example 2
Desulfurization test condition, with embodiment 2, does not just remove the process of oxygen to aqueous alkanolamine, but directly uses aqueous alkanolamine to carry out desulfurization test to coking liquefied petroleum gas (LPG).
Coking liquefied petroleum gas (LPG) used and after embodiment 2, comparative example 2 desulfurization process the composition of liquefied petroleum gas (LPG) medium sulphide content in table 2.
Table 2
| Various sulfide content | Coking liquefied petroleum gas (LPG) | Embodiment 2 | Comparative example 2 |
| Sulphur content/% | 3.4252 | 0.4310 | 0.4398 |
| Hydrogen sulfide sulphur/% | 2.9500 | 0.0013 | 0.0025 |
| Carbonylsulfide/% | 0.0221 | 0.0022 | 0.0018 |
| Mercaptan sulfur/% | 0.4356 | 0.4289 | 0.4122 |
| Disulphide sulphur/% | 0.0011 | 0.0001 | 0.0222 |
| Polysulfide sulphur/% | 0.0002 | 0.0000 | 0.0052 |
| Other Sulfur/% | 0.0010 | 0.0011 | 0.0013 |
Embodiment 3
The hydramine sweetening agent SSH-3 of Taihu Lake, Changzhou Chemical Co., Ltd. and distilled water are hybridly prepared into the aqueous alkanolamine that content is 30%.Pending catalytic liquefied petroleum gas takes from the stable liquefied gas of the MIP technique of China Petrochemical Corp. subordinate refinery.
In aqueous alkanolamine, add the hydrazine hydrate that concentration is 45%, its addition is the 10mg/kg of aqueous alkanolamine.
The LPG Desulfurization device in laboratory carries out desulfurization test, the processing condition adopted are: aqueous alkanolamine and catalytic liquefied petroleum gas are in packing tower counter current contact, Contact Temperature is 40 DEG C, the volume ratio of aqueous alkanolamine and liquefied petroleum gas (LPG) is 1:2.5, and during the liquid of catalytic liquefied petroleum gas, volume space velocity is 10h
-1.
Comparative example 3
Desulfurization test, with embodiment 3, does not just add hydrazine hydrate in aqueous alkanolamine, but directly uses aqueous alkanolamine to carry out desulfurization test to catalytic liquefied petroleum gas.
Raw materials used catalytic liquefied petroleum gas and after embodiment 3, comparative example 3 desulfurization process the composition of liquefied petroleum gas (LPG) medium sulphide content in table 3.
Table 3
| Various sulfide content | Catalytic liquefied petroleum gas | Embodiment 3 | Comparative example 3 |
| Sulphur content/% | 0.1213 | 0.0647 | 0.0660 |
| Hydrogen sulfide sulphur/% | 0.0554 | 0.0002 | 0.0005 |
| Carbonylsulfide/% | 0.0018 | 0.0001 | 0.0001 |
| Mercaptan sulfur/% | 0.0635 | 0.0635 | 0.0478 |
| Disulphide sulphur/% | 0.0001 | 0.0000 | 0.0131 |
| Polysulfide sulphur/% | 0.0000 | 0.0000 | 0.0012 |
Claims (12)
1. a hydramine sulfur method for liquefied petroleum gas (LPG), comprising: to contact with liquefied petroleum gas (LPG) carry out hydramine desulphurization reaction by removing the aqueous alkanolamine after oxygen, collect liquefied petroleum gas product.
2. in accordance with the method for claim 1, it is characterized in that, adopt in physics method of deoxidation, chemical method of deoxidation and biological method of deoxidation one or more remove oxygen in aqueous alkanolamine.
3. in accordance with the method for claim 2, it is characterized in that, described physics method of deoxidation comprise in thermal de-aeration, deaeration in condenser and parsing deoxidation method one or more.
4. in accordance with the method for claim 3, it is characterized in that, described parsing deoxygenation is the gas that utilizes concentration of oxygen gas large and/or hydrocarbon ils and want the aqueous alkanolamine of deoxygenation to contact or mix, and the oxygen in aqueous alkanolamine is resolved in the large gas of described concentration of oxygen gas and/or hydrocarbon ils.
5. in accordance with the method for claim 2, it is characterized in that, described chemical method of deoxidation is contacted with reductor by aqueous alkanolamine or mixes the oxygen removed in aqueous alkanolamine, described reductor is the reducing substances that can not react with oxygen generation redox reaction and with described aqueous alkanolamine, and described reductor is one or more in gaseous state reductor, liquid deoxidizer and solid-state reductor.
6. in accordance with the method for claim 5, it is characterized in that, described gaseous state reductor is H
2, CO or hydrazine.
7. in accordance with the method for claim 5, it is characterized in that, described liquid state or solid-state reductor are one or more in ketoxime class, aldoxime class, hydrazine class, sulphite, reducing metal and reductibility resin.
8. in accordance with the method for claim 5, it is characterized in that, described liquid state or solid-state reductor are one or more in DMKO, Diacetylmonoxime, ethylidenehydroxylamine, hydrazine hydrate, S-WAT and vitamin-E.
9. in accordance with the method for claim 7, it is characterized in that, described reductibility resin be selected from hydroquinone type, sulfydryl class, pyridines and ferrocene resinoid one or more.
10. in accordance with the method for claim 5, it is characterized in that, the add-on of described reductor is 0.1 ~ 200mg/L of described aqueous alkanolamine.
11. in accordance with the method for claim 2, it is characterized in that, described biological method of deoxidation in aqueous alkanolamine, adds deoxidation microorganism and/or deoxidation plant remove oxygen wherein.
12. according to the method one of claim 1-11 Suo Shu, it is characterized in that, described aqueous alkanolamine is as follows with the processing condition of liquefied petroleum gas (LPG) generation hydramine desulphurization reaction after removing oxygen: the volume ratio of described aqueous alkanolamine and liquefied petroleum gas (LPG) is 1:1 ~ 1:100, and Contact Temperature is 10 ~ 80 DEG C.
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Application publication date: 20150225 |