CN109053647A - A kind of production technology of preparing cis-anhydride by n-butane oxidation - Google Patents
A kind of production technology of preparing cis-anhydride by n-butane oxidation Download PDFInfo
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- CN109053647A CN109053647A CN201810968284.1A CN201810968284A CN109053647A CN 109053647 A CN109053647 A CN 109053647A CN 201810968284 A CN201810968284 A CN 201810968284A CN 109053647 A CN109053647 A CN 109053647A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/60—Two oxygen atoms, e.g. succinic anhydride
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Abstract
The invention discloses a kind of techniques of preparing cis-anhydride by n-butane oxidation, belong to maleic anhydride production field.The present invention is to obtain a kind of production technology of the production of the n butane oxidation under lower operating pressure maleic anhydride by improving the production technology of former benzene oxidatoin legal system cis-butenedioic anhydride.Specifically this technique uses homemade catalyst, so that reaction is had preferable selectivity and yield under lower pressure, while not only having vitalized prior art but also save the cost.
Description
Technical field
The present invention relates to maleic anhydride production fields, and positive fourth is used under lower operating pressure more specifically to one kind
The production technology of alkoxide production maleic anhydride.
Background technique
Maleic anhydride abbreviation cis-butenedioic anhydride also known as maleic anhydride are a kind of important Organic Chemicals, are to be only second to benzene
The big organic acid anhydride in the third place in the world of acid anhydride and aceticanhydride, is widely used in the industries such as petrochemical industry, food processing, medicine, building materials.Due to tool
The advantages that standby raw material is inexpensive, and pollution is relatively light, carbon atom utilization rate height and maleic anhydride production at low cost, preparing cis-anhydride by n-butane oxidation
Technology is increasingly becoming the main route of maleic anhydride production, and has the tendency that gradually substituted benzene oxidizing process.Domestic benzene method maleic anhydride production dress
The test for being faced with process route upgrading is set, two kinds of route main differences are raw materials for production, operating condition and oxidation catalyst, benzene
Oxidizing process uses benzene for raw material, and gas phase oxidation occurs on vanadium molybdenum series catalyst surface with air at 0.05-0.06MPa,
It obtains the reaction containing cis-butenedioic anhydride and generates gas；N butane oxidation method uses normal butane for raw material, at 0.19-0.22MPa with air
Gas phase oxidation occurs in vanadium phosphorus oxygen series Catalysts, obtains the reaction containing cis-butenedioic anhydride and generates gas.
Two kinds of raw material routes must use the catalyst of different systems, and n butane oxidation legal system maleic anhydride unit can only use vanadium
Phosphorus oxygen series catalysts.Since by catalyst operant conditioning, existing vanadium-phosphor oxide catalyst also can not be suitable in benzene oxidatoin legal system
Stable operation on the process units of acid anhydride.Therefore, original benzene oxidatoin legal system maleic anhydride unit usually scraps processing.If passing through technology
It improves upgrading to recycle former benzene subtraction unit, utilization rate of equipment and installations can be improved and reduce investment amount.In order to meet this requirement,
The present invention provides specific process modification methods.
Summary of the invention
The purpose of the present invention is overcome the deficiencies of the prior art and provide one kind to be changed by former benzene oxidatoin legal system cis-butenedioic anhydride raw material route
Cause the process program suitable for n butane oxidation method.
The production technology of benzene oxidatoin legal system cis-butenedioic anhydride, usually by benzene storage tank, blower, air heater, empty benzene mixer, fixation
Bed reactor, level-one gas cooler, portion's cooler, absorption tower, rectified purified and tail gas incinerator each unit form.Due to liquid
State benzene is different from the condition of storage of liquid normal butane, which requires newly-built liquid normal butane storage tank and matched depot.Change
Technique after making is newly-increased with lower unit: normal butane storage tank, normal butane evaporator and superheater, trimethyl phosphate (TMP) addition system
System, empty hydrocarbon mixer, secondary gas cooler and boiler water heater；Transformation is with lower unit: blower (improves fan outlet pressure
Head), reactor outlet pipeline (original carbon steel pipe line is changed to stainless steel), (more heat-exchange carrier simultaneously increases tail gas incinerator
Heat exchanger area), in addition to it need to increase newly and said units are transformed, need replacing the vanadium phosphorus oxygen for having and having operability under lower pressure
Catalyst.
After transformation for produce preparing cis-anhydride by n-butane oxidation the specific process steps are as follows:
(1) liquid normal butane enters normal butane evaporator in normal butane storage tank, is sent into normal butane superheater after heating vaporization,
Obtain normal butane steam；
(2) TMP is squeezed into TMP evaporator through pump, enters normal butane pipeline and step after being mixed TMP steam with nitrogen
(1) the butane steam mixing in, obtains organic steam；
(3) enter sky hydrocarbon mixer and having in step (2) through air of the blower pressurization again after air heater heats
The mixing of machine steam, obtained mixed gas enter the tubular fixed-bed reactor that catalyst is housed, the gas after reaction together
Enter second level air cooler after level-one air cooler and enter back into the cooling of portion's cooler, reactant after cooling enters crude anhydride separator, gas
Body enters absorption tower, and liquid crude anhydride enters crude anhydride tank.It is collected in sour water tank after into the part acid anhydrides washing on absorption tower, finally
Cis-butenedioic anhydride product is refining to obtain together with the acid anhydrides in crude anhydride tank.
Normal butane flow is 0.09-0.10kg/Tube/h in the step (1), and normal butane vapourizing temperature is 40~60
DEG C, overtemperature is 100~150 DEG C.
TMP concentration is the 0.5-3.0ppm of tubular fixed-bed reactor inlet gas total volume in the step (3).
Air mass flow is 2.0-2.1NCM/Tube/h in the step (3), makes fan outlet air by technological transformation
Moulding pressure is 60~99kPa, and heating temperature is 150~180 DEG C.
Preparing cis-anhydride by n-butane oxidation is strong exothermal reaction, and the heat supply for the industrial reactor that the present invention uses and shifting heat are to pass through
What the fused salt that the sodium nitrite and mixture of potassium nitrate that certain proportion is prepared are formed after melting was adjusted, pass through the temperature for adjusting fused salt
(abbreviation salt temperature) adjusts reaction temperature,
Fixed bed reaction pressure is 60~99kPa in the step (3), and temperature of molten salt is 405~415 DEG C, hot spot temperature
Degree is 430~450 DEG C.Reactor outlet generates gas bag and contains cis-butenedioic anhydride, normal butane, oxygen, nitrogen and byproducts of carbon monoxide, dioxy
Change the gaseous mixture of carbon, acetic acid and acrylic acid.
Level-one air cooler is cooled to 180~220 DEG C in the step (3), and second level air cooler is cooled to 145~165 DEG C.
Wherein oxidized byproduct acrylic acid can polymerize in second level air cooler, it is therefore desirable to and two second level air cooler switchings use,
Guarantee system continuous operation.Simultaneously in order to guarantee the cooling temperature of second level air cooler, into second level air cooler boiler water need through
Enter second level air cooler after crossing boiler heating, boiler water heater outlet boiler water temperature is 140~160 DEG C.
Cooler mixed gas temperature after cooling is 58~60 DEG C in the middle part of the step (3), liquid cis-butenedioic anhydride after cooling
Weight accounting is 30~50%.If portion's cooler needs to clean, switchable bypass enters absorption tower and carries out water absorption, is done using water molten
Agent collects maleic anhydride in sour water tank in the form of maleic acid aqueous solution.
The maleic anhydride entered in the mixed gas on water absorption tower in the step (3) is water-soluble with maleic acid
The form of liquid is collected, and normal butane, oxygen, nitrogen and oxidized byproduct carbon monoxide, the carbon dioxide for having neither part nor lot in reaction enter tail
Gas incinerator, is vented after burning.
The catalyst that the present invention selects can be known catalysts existing, applied to preparing cis-anhydride by n-butane oxidation, can also
To use a kind of catalyst disclosed by the invention (abbreviation NSMA-C4SL-2 type catalyst).Use catalyst in the prior art
Preparing cis-anhydride by n-butane oxidation may be implemented, but the yield of product and selectivity are lower, and cannot achieve long-period stable operation.This
Invention uses NSMA-C4SL-2 type catalyst, and not only the selectivity of product is good, high income, but also can realize that long period stablizes fortune
Row.
NSMA-C4SL-2 type catalyst is using diatomite as carrier, and the weight content of carrier is 20%~40%, active group
Divide general formula are as follows: V1.0PaMobOm, wherein it be 0.05~0.5, m is oxygen needed for meeting each element chemical valence that a, which is 0.8~1.5, b,
Atomicity.
NSMA-C4SL-2 type catalyst the preparation method comprises the following steps:
The diatomite of (1) 100~400 mesh is distributed in isobutanol, benzyl alcohol and isooctyl acid molybdenum mixed solution 90~130
DEG C and -5~-30Kpa pressure under reaction form suspension；
(2) vanadic anhydride is added in suspension and concentrated phosphoric acid, the precipitating of generation deposits on diatomite, passed through
Filter, 100~150 DEG C of dryings 4~for 24 hours, 200~400 DEG C of 1~8h of roasting form presoma；
(3) after presoma is granulated into 10~60 mesh, use graphite as lubricant tabletting at hollow cylinder, 400~
10~20h is activated at 500 DEG C into catalyst.
Using technical solution provided by the invention, there is following remarkable result:
(1) present invention is to be transformed out to be suitable for butane oxidation system on the basis of benzene oxidatoin legal system maleic anhydride production process flow
The technique of cis-butenedioic anhydride, this technique increase newly normal butane storage tank, normal butane evaporator and superheater, TMP add-on system, empty hydrocarbon mixer,
The equipment of secondary gas cooler and boiler water heater unit, these newly-increased units can make the main of benzene oxidatoin method production procedure
Equipment is rationally recycled, and existing fixed assets are vitalized.
(2) the use NSMA-C4SL-2 type catalyst of this technique, has preparing cis-anhydride by n-butane oxidation under lower pressure
Preferable selectivity and yield, improve productive profit.
(3) according to the improved process program of the present invention, from long-term running industrial production angle, normal butane
About 4000 yuan/ton of price, about 6350 yuan/ton of the price of petrobenzene, about 2000 yuan/ton cheaper than petrobenzene of normal butane, Ke Yijie
About cost brings preferable economic benefit.
Detailed description of the invention
Fig. 1 is benzene oxidatoin method production procedure block diagram；
Fig. 2 is the improved protocol procedures block diagram suitable for preparing cis-anhydride by n-butane oxidation.
Specific embodiment
The present invention is furtherd elucidate below by embodiment.
Embodiment 1:
With stirring, heating and condensation reflux unit reaction kettle in, be added isobutanol 5500g, benzyl alcohol 1100g,
Isooctyl acid molybdenum 63.2g, being stirring evenly and then adding into average particle size is 180 mesh diatomite 720g, continues stirring 0.5h and obtains uniformly
Suspension controls 95 ± 5 DEG C of the temperature, ± 5kPa of pressure -25,100% phosphatase 79 50g and vanadic anhydride is at the uniform velocity added in 1h
860g then proceedes to back flow reaction 6h at this temperature and pressure, and cooling after reaction, filtering, filter cake is at 130 ± 10 DEG C
Dry 18h, roasts 8h at 310 ± 10 DEG C, obtains active presoma.Active presoma is granulated into the particle of 10~20 mesh,
Be then mixed into the graphite of 4% (wt), tabletting at outer diameter 5mm, internal diameter 2.2mm, height 5mm hollow cylinder, then 470 ±
10 DEG C of activation 6h obtain catalyst group as V1.0P1.0Mo0.1Om/ diatomite 40% (wt), m are to meet needed for each element chemical valence
Oxygen atomicity.
Embodiment 2:
With stirring, heating and condensation reflux unit reaction kettle in, be added isobutanol 5000g, benzyl alcohol 1000g,
Isooctyl acid molybdenum 48.5g, being stirring evenly and then adding into average particle size is 360 mesh diatomite 486g, continues stirring 0.5h and obtains uniformly
Suspension controls 115 ± 5 DEG C of the temperature, ± 5kPa of pressure -15, and the oxidation of 100% phosphatase 11 000g and five two is at the uniform velocity added in 3h
Vanadium 660g then proceedes to back flow reaction 5h at this temperature and pressure, and cooling after reaction, filtering, filter cake is in 120 ± 10 DEG C
Lower dry 20h, roasts 6h at 310 ± 10 DEG C, obtains active presoma.Active presoma is granulated into the grain of 10~20 mesh
Son, is then mixed into the graphite of 2% (wt), then tabletting exists at the hollow cylinder of outer diameter 5mm, internal diameter 2.2mm, height 5mm
470 ± 10 DEG C of activation 6h obtain catalyst group as V1.0P1.4Mo0.1Om/ diatomite 33% (wt), m are to meet each element chemical valence
Required oxygen atomicity.
Process example:
The reactor that following embodiments use is fixed bed reactors, and isometric reaction tube, the length is 4000mm, instead
Answering device caliber is 21mm, and catalyst uses NSMA-C4SL-2 type catalyst, and filling height is 3500mm.
Following embodiments use ten thousand tons of benzene method maleic anhydride process units after Replacement procedure, such as Fig. 2.Liquid in butane storage tank
Normal butane enters normal butane evaporator, is heated to the normal butane superheater of 100~150 DEG C of feeding after 40~60 DEG C of vaporizations, obtains
TMP is squeezed into TMP evaporator through pump, enters normal butane pipeline and normal butane after being mixed TMP steam with nitrogen by normal butane steam
Steam mixing, obtains organic steam, is forced into sky of the 60~99kPa again after air heater heats 150~180 DEG C through blower
Gas enters sky hydrocarbon mixer and mixes with organic steam, and obtained mixed gas enters the fixed bed shell and tube that catalyst is housed together
Reactor, the gas after reaction enter 145~165 DEG C of second level air cooler again after level-one air cooler is cooled to 180~220 DEG C
Entrance cooler is cooling, and wherein the temperature of second level air cooler is provided by 140~160 DEG C of boiler water, reactant after cooling into
Enter crude anhydride separator, gas enters absorption tower, and liquid crude anhydride enters crude anhydride tank.It is collected after into the part acid anhydrides washing on absorption tower
In sour water tank, cis-butenedioic anhydride product is finally refining to obtain together with the acid anhydrides in crude anhydride tank.
Embodiment 3:
Air mass flow is 2.05NCM/Tube/h, normal butane flow is that 0.096kg/Tube/h, TMP volume content are
1.5ppm, reactor inlet pressure 60kPaG, 410 DEG C of temperature of molten salt, 440 DEG C of hot(test)-spot temperature, n-butane conversion 82.0%, dress
It makes an inventory after setting stable operation 720h, oxidization-hydrogenation ratio 90%, purification yield is 92%, and products material consumption per ton is
1.207t, normal butane average price take 4000 yuan it is per ton, products material cost per ton be 4828 yuan；The device is using benzene as raw material route
When, ton products material consumption be 1.150t, petrobenzene average price take 6350 yuan it is per ton, products material cost per ton be 7303 yuan；Skill
The cost of material for changing rear ton product reduces by 2475 yuan.
Embodiment 4:
Air mass flow 2.05NCM/Tube/h, normal butane flow 0.096kg/Tube/h, TMP volume content are 1.5ppm,
Reactor inlet pressure 90kPaG, 405 DEG C of temperature of molten salt, 435 DEG C of hot(test)-spot temperature.N-butane conversion 82.0%, device are stablized
It makes an inventory after operation 720h, oxidization-hydrogenation ratio 92%, purification yield is 92%, and products material consumption per ton is 1.181t, just
Butane average price take 4000 yuan it is per ton, products material cost per ton be 4724 yuan；When the device is using benzene as raw material route, product per ton
Consumption of raw materials is 1.150t, petrobenzene average price take 6350 yuan it is per ton, products material cost per ton is 7303 yuan；Ton product after technological transformation
Cost of material reduce by 2579 yuan.
The present invention is not limited to the above embodiment the specific technical solution, all technical sides formed using equivalent replacement
Case is the range that the present invention is protected.
Claims (6)
1. a kind of technique of preparing cis-anhydride by n-butane oxidation, which is characterized in that the technique the following steps are included:
TMP steam enters empty hydrocarbon mixer after mixing with normal butane steam together with air and mixes, and mixed gas, which enters to be equipped with, urges
The fixed bed reactors of agent, the gas after reaction obtain cis-butenedioic anhydride product through cooling after purification；The catalyst is with diatomite
For carrier, the weight content of carrier is 20%~40%, active component general formula are as follows: V1.0PaMobOm, wherein a be 0.8~
1.5, b for 0.05~0.5, m be oxygen atomicity needed for meeting each element chemical valence.
2. technique according to claim 1, it is characterised in that: the preparation of the catalyst includes the following steps:
The diatomite of (1) 100~400 mesh is distributed in isobutanol, benzyl alcohol and isooctyl acid molybdenum mixed solution at 90~130 DEG C ,-
Reaction forms suspension under 5~-30Kpa pressure；
(2) vanadic anhydride is added in suspension and concentrated phosphoric acid, the precipitating of generation deposits on diatomite, by filtering, 100
~150 DEG C of dryings 4~for 24 hours, 200~400 DEG C of 1~8h of roasting form presoma；
(3) after presoma is granulated into 10~60 mesh, use graphite as lubricant tabletting at hollow cylinder, at 400~500 DEG C
10~20h is at catalyst for lower activation.
3. technique according to claim 1, it is characterised in that: normal butane steam flow is 0.09~0.10kg/Tube/h.
4. technique according to claim 1, it is characterised in that: air mass flow is 2.0~2.1NCM/Tube/h；Gaseous mixture
TMP volume content is 0.5~3.0ppm in body.
5. technique according to claim 1, it is characterised in that: fixed bed reaction pressure is 60~99kPa, and temperature of molten salt is
405~415 DEG C, hot(test)-spot temperature is 430~450 DEG C.
6. technique according to claim 1, it is characterised in that: the gas after the reaction is laggard by level-one air cooler
Enter second level air cooler and enter back into the cooling of portion's cooler, level-one air cooler temperature is 180~220 DEG C, the cooling temperature of second level air cooler
It is provided by boiler water vapour, temperature is 145~165 DEG C.
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112705233A (en) * | 2019-10-24 | 2021-04-27 | 中国石油化工股份有限公司 | Vanadium phosphorus oxygen catalyst and preparation method and application thereof |
| CN115487753A (en) * | 2021-06-18 | 2022-12-20 | 济南隆凯能源科技有限公司 | Method and device for preparing acid anhydride by partial oxidation of hydrocarbon with variable-concentration feed |
| CN116082281A (en) * | 2023-02-22 | 2023-05-09 | 彭西周 | Process for recovering maleic anhydride from maleic anhydride-containing gas |
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| CN112705233A (en) * | 2019-10-24 | 2021-04-27 | 中国石油化工股份有限公司 | Vanadium phosphorus oxygen catalyst and preparation method and application thereof |
| CN115487753A (en) * | 2021-06-18 | 2022-12-20 | 济南隆凯能源科技有限公司 | Method and device for preparing acid anhydride by partial oxidation of hydrocarbon with variable-concentration feed |
| CN116082281A (en) * | 2023-02-22 | 2023-05-09 | 彭西周 | Process for recovering maleic anhydride from maleic anhydride-containing gas |
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