CN109913255A - A method of utilizing TDI tar residue liquid fuel was prepared - Google Patents
A method of utilizing TDI tar residue liquid fuel was prepared Download PDFInfo
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- CN109913255A CN109913255A CN201910304883.8A CN201910304883A CN109913255A CN 109913255 A CN109913255 A CN 109913255A CN 201910304883 A CN201910304883 A CN 201910304883A CN 109913255 A CN109913255 A CN 109913255A
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Abstract
The present invention is a kind of to utilize toluene diisocyanate (TDI) tar residue liquid fuel was prepared method.The tar residue particle generated in TDI production process is polished, it is placed in high-temperature high-pressure reaction kettle, low boiling-point and polarity solvent is added according to a certain percentage, stirs evenly.Control temperature, pressure and time carry out resolution reaction, obtain resolution solidliquid mixture.Filtering, is separated by solid-liquid separation, and resolution filtrate and resolution solid residue are respectively obtained.It is spare to clear up solid residue.It clears up filtrate and adds mixed fuel accelerating agent according to certain mass percent, obtain liquid fuel.The tar residue method of disposal is at low cost, simple process, easy to operate, condition is easily-controllable and equipment investment is few.Liquid fuel calorific value is high, Fuel emission secondary pollution risk is small.Ecological environment is protected while generating biggish economic benefit again, realizes recycling, the target of minimizing, the energy-saving and emission-reduction of innoxious recycling and environmental protection of tar residue solid waste.
Description
Technical field
The invention belongs to chemical industry recovery technology fields, are related to a kind of method using TDI tar residue liquid fuel was prepared.
Background technique
Liquid fuel is a major class of fuel.The liquid combustible of thermal energy or kinetic energy can be generated.Mainly contain hydrocarbonization
Close or mixtures thereof object.There are gasoline, kerosene as obtained by PETROLEUM PROCESSING, diesel oil, fuel oil etc. by what is be process, by oily page
Shale oil obtained by rock destructive distillation, and the artificial petroleum etc. synthesized by carbon monoxide and hydrogen.In face of the exhaustion of fossil energy, including
Substitution liquid fuel including biomass fuel is most potential novel alternative energy source.
By agricultural crop straw and agricultural machining residue, the life for industrializing the preparations such as waste water and waste residue, domestic waste
Thing liquid fluid fuel is the environmentally protective energy, and thoroughly, thermal conversion efficiency is high for burning, and discharge main component is water and carbon dioxide
Based on, environmental pollution is small, is the following most cleaning, environmentally friendly, most potential fuel.
Biological liquid fuel has apparent economic benefit, and high thermal efficiency is its best feature.Due to its preparation or close
It is big at technical difficulty, need deep technical research and practice.
Toluene di-isocyanate(TDI) (Toluene Dissocyanate, TDI), there is 2,4- toluene di-isocyanate(TDI) and 2,6-
Two kinds of isomers of toluene di-isocyanate(TDI), commodity are mostly the mixture of two kinds of isomers.
In recent years, as the development of polyurethane industries among others is to the demand substantial increase of TDI, domestic growth rate in recent years
7%.It is predicted according to units concerned, the consumption demand of whole world TDI will be increased in coming 10 years with the speed in year 4%.It is international
Very big development space is all had with the domestic market TDI.
Whole world TDI production method is still using light phosgenation as main method.The gas making of light phosgenation production process, water-gas
The processes such as purification, carbon monoxide purification, optical self-encoding, catalyst preparation, TDA production, TDI production and the storage of intermediate products and finished product
During depositing etc., the pollutants such as large quantity of exhaust gas, waste water, waste residue can be generated.Wherein, TDI tar residue is to produce in TDI production process
Raw one kind solid waste particle.
The main source that the solid waste generated in TDI production process generates: (1) Zhi Qi workshop section, main generation residue are active
Charcoal, molecular sieve, silica gel and a small amount of catalyst platinum, palladium, iron and manganese etc..(2) chlorination workshop section generates carbon black.(3) TDI workshop section generates
Ortho-toluene diamine (OTD).(4) optical self-encoding generates active carbon.(5) TDI recycling generates tar residue particle.
Studies have shown that it is that isocyanates is that TDI recycling, which generates the main component of tar residue particle, by high-temperature process
It is main, with polymer such as urea, biuret and polymerization biurets.These polymer contain prepare biological liquid fuel needed for master
Want constituent.
How to take effective technical method, be translated into calorific value is high, pollution less, environmental-friendly substance there is weight
Want meaning.
Existing more mature TDI tar residue method of disposal, relates generally to following three methods: distillation-evaporation, steaming
Evaporate-reduction method and distillation-combustion method etc..Its object is to intermediate products or spin-offs needed for recycling production TDI.
Above-mentioned main three kinds of methods of disposal for tar residue are introduced separately below.
No matter-evaporation or distillation-reduction method are distilled.Tar residue, through strong base solution+high boiling organic solvent+also
Former agent, high temperature, high pressure/vacuum are segmented rectifying, low boiling point small-molecule substance and high boiling substance are separately recovered.
Such method advantage: rate of recovery height (more than 90%), low in the pollution of the environment.Major defect is that equipment investment is more, technique control
System is complicated and stringent, operation difficulty is big, easy secondary generation poisonous and harmful substance, such as the waste liquid containing a large amount of strong base substances, useless
Slag is also easy to produce secondary environmental pollution.
Bi Rongshan etc. is respectively in a kind of " continous way removal methods for heavy oil agent method TDI residue " (number
CN105384633B) and " a kind of continous way removing means for heavy oil agent method TDI residue " (CN105523925B) two is special
It is successively disclosed in sharp letter of authorization, tar residue is generated when producing TDI using higher boiling heavy oil agent method as raw material, uses heavy oil agent isophthalic
Dicarboxylate (DEIP) realizes recycling DEIP using distillation and evaporation.
Li Guixian etc. " a method of draped over one's shoulders in DEIP " (CN101717335B) patent right book in recycling TDI residue
Dew, it is characterized in that by TDI produce in after the free TDI of the higher boiling residue removal that generates, remaining solid residue is extracting
Below the critical-temperature of agent, critical pressure is by extractant (including methanol, ethyl alcohol, benzene and toluene) of ethyl alcohol hereinafter, extracted
It takes, 15 ~ 25min of extraction time, solid-to-liquid ratio 1:4 ~ 1:16, residue particles partial size is 100 mesh screenings.In stirred autoclave
DEIP and the recycling in TDI residue are extracted by extractant.
Specific reaction condition: TDI solid residue a) is ground into particle, is sieved later, its purpose is to be had
Effect extraction particle sieves with 100 mesh sieve lower object after crushing.B) screenings and extractant are added in stirred autoclave, in reaction pressure
2 ~ 6MPa of power, 150 ~ 250 DEG C of temperature extracted.C) recycling obtains DEIP from extraction later liquid.It extracts in engineering
Extractant can be utilized with iterative cycles.
Distillation-reduction method.Tar residue is segmented rectifying in strong base solution, through high temperature, high pressure/vacuum, has in higher boiling
Under the coexisting of solvent and reducing agent, reduction organic product is obtained.
Chen Shuxia etc. is disclosed in CN100400520C " extracts methyl-o-phenylenediamine and its synthesis from TDI organic detritus
Distillation-restoring method of TTA ".
Under the coexisting of high boiling organic solvent, reducing agent sodium nitrite is added in distillation process, obtains methyl neighbour benzene two
Amine (TDA) finally obtains tolytriazole sodium salt salt (TTA).Its particular content includes, with TDI organic detritus raw material, one
Under fixed temperature, pressure, methyl-o-phenylenediamine is extracted from TDI organic detritus using the method for dissolution, vacuum extraction rectifying, it will
Methyl-o-phenylenediamine and excessive sodium nitrite solution press one-step synthesis methylbenzotriazole (TTA) product in using.Its TDI
Temperature of charge in organic detritus purification process is 160 ~ 190 DEG C, and 50 ~ 380Pa of vacuum degree in reaction kettle, TTA synthesize work
Sequence is 250 ± 20 DEG C, pressure 4.6 ~ 5.2MPa constant temperature and pressure synthetic reaction 3.5 ~ 4 hours in temperature.
Liu Jun use " TDI residue ordinary-pressure hydrolysis prepare 2,4- diaminotoluene " (Foreign Capital in China, in September, 2012, total the
273 phases, 284 ~ 285).Specific steps: residue is added in high boiling solvent, and dry three neck round bottoms are added together with NaOH solution and burn
Bottle, electronics universal furnace are heated to established temperature, constant temperature reflux, mechanical stirring.Reaction is completed, and reaction solution is filtered, filtrate
It is extracted with extract liquor, then extraction liquid is evaporated under reduced pressure, obtain flaxen oily liquids, cooling is the hydrolysate 2,4- of solid
Diaminotoluene.
Zhang Lianming etc. propose " analysis and utilization of heavy oil agent TDI tar residue " (chemical industry progress, 2015 volume 34 the 3rd
Phase, 863 ~ 866).TDI is made by being dissolved in heavy oil agent dimethyl isophthalate (DEIP) and excessive phosgene reaction.It should
Tar residue contains the DEIP of polymerization biuret and nearly 50%, which can hydrolyze.Specific practice is, lower
At a temperature of, short time residue is hydrolyzed in alkaline system (NaOH solution), generates M-phthalic acid sodium salt, hydrochloric acid tune pH
=2, it generates M-phthalic acid and is slightly soluble in water, so that be precipitated becomes precipitating in the solution, obtain M-phthalic acid finished product.
Tar residue and heavy oil are mixed and burned method.The method is exactly to utilize the small-molecule substances such as carbon, hydrogen and oxygen in residue
Flammable characteristic not only reaches burning and obtains a large amount of heat but also the final purpose of minimizing disposition residue.This method advantage is obvious, if
Standby less investment, technological operation is simple, recycles a large amount of heat.Disadvantage are as follows: it is big, remaining that utility, disposal of pollutants can not be recycled
Secondary residual amount is big.
Seen using alcoholysis reaction by report that lipid material is converted to oil fuel is quite a few.For example, Wang Lian mandarin duck etc. is " super
Application of the critical methanol in chemical reaction " (chemical progress, in May, 2010,796 ~ 802.) refer to " system of 3.2 biodiesel
Standby ... Deimrbas points out biodiesel tool obtained under overcritical low-carbon alcohols to based on different material grease ... ... respectively
There is excellent comprehensive performance."
Huang Jie etc. is in the research of mechanism of degradation " polybutylene terephthalate (PBT) in supercritical methanol " (colleges and universities' chemical engineering science
Report, 2 months 2007,48 ~ 53) in report: " in supercritical region polybutylene terephthalate (PBT) (PBT) can be achieved completely drop
Solution, primary product are dimethyl terephthalate (DMT) (DMT) and butanediol (BG) ".
It covers and is disclosed in " energy-saving alcohol-based fuel " (CN106281485A) in star: " 62 ~ 86 parts of methanol, diesel oil 12 ~ 24
Part, 0.6 ~ 1.8 part of nitric acid hexamethylene rouge, 0.5 ~ 1.7 part of nitric acid isooctyl, 4- tert-butyl -2,6-Bis(1-methylethyl)phenol 0.4 ~ 1.6
Part, 2,4- 0.3 ~ 0.9 part of dimethylanilines, 0.1 ~ 0.7 part of tri-tert phosphate ester, 0.01 ~ 0.07 part of glycerine, burning promotes
0.03 ~ 0.15 part of agent, 0.1 ~ 1.3 part of detergent.Energy-saving alcohol-based fuel of the invention has anti-oxidant, combustion-supporting, anticorrosive, anti-
The effects of jelly, peace and quiet and raising Cetane number."
Xiao Changgen discloses " methanol 80 ~ 85%, first in " a kind of environmental protection alcohol-based fuel and preparation method thereof " (CN108707485A)
Base tertbutyl ether 4 ~ 7%, water 4-7%, sec-Butyl Acetate 2 ~ 5%, triethylamine 1 ~ 4%, hydrogen peroxide 0.5 ~ 2%, complexing of glycin iron 0.5 ~
2%, sodium hydroxide 0.5 ~ 2%.... compared with existing alcohol-based fuel, the calorific value of alcohol-based fuel of the present invention is higher and sulphur contains
It measures low."
This method advantage is: solid wastes recycling, minimizing utilization efficiency are high.TDI tar residue particle is cleared up, low boiling point is recycled
Small organic molecule and related inorganic object.This method simple process, easy to operate, condition is easily-controllable, equipment investment is less and
Cost recovery is low.Liquid fuel calorific value is high, Fuel emission secondary pollution risk is small.Conducive to energy-saving and emission-reduction, environmental protection.
Summary of the invention
In order to overcome the shortcomings of the prior art, more effectively realize that recycling, minimizing, harmlessness disposing TDI are burnt
The target of oil residue utilizes TDI tar residue liquid fuel was prepared method the present invention provides a kind of,
The technical scheme is that a kind of utilize TDI tar residue liquid fuel was prepared method, include the following steps:
Step 1) by TDI tar residue solid particulate materials, mechanical lapping is powder；Weigh ground TDI tar residue powder
It is placed in the high-temperature high-pressure reaction kettle with agitating device, low boiling-point and polarity solvent, mixing is added by solid-to-liquid ratio 1:1 ~ 20kg/L
And stir evenly, obtain the solidliquid mixture containing TDI tar residue；
Step 2) reaction kettle of solidliquid mixture will be included from room temperature to 100 ~ 350 DEG C, keep 2 ~ 12MPa of pressure, heat preservation
15 ~ 120min of time carries out resolution reaction, obtains resolution solidliquid mixture, depressurizes and be cooled to room temperature normal pressure；
Step 3) resolution solidliquid mixture is separated by solid-liquid separation, respectively obtain resolution filtrate and resolution solid residue；Use low boiling
Point-polarity solvent washing resolution residual residue, merges with resolution filtrate, obtains clearing up total filtrate；
Step 4) toward addition fuel combination promotor in total filtrate is cleared up, it stirs evenly, obtains liquid feul.
Further to improve, the low boiling-point and polarity solvent is a kind of or several solvents mixtures, the polarity of solvent
Parameter is 2 ~ 8, and boiling point is 60 ~ 160 DEG C；
It is further to improve, the low boiling-point and polarity solvent include: in structure hydrocarbon oxygen atomicity ratio be 1 ~ 8:4 ~ 10:1 ~ 2
Alcohols material, letones, Ester and arene substance or derivative.
Further to improve, the method also includes step 4) fuel accelerating agent is added into the total filtrate of resolution, stirring is equal
It is even；The fuel accelerating agent is ferrocene, ferrocenyl methyl ketone, tert-butyl ferrocene, vinyl ferrocene and its ferrocene
One or more mixtures of spin-off.
This method advantage is: solid wastes recycling, minimizing utilization efficiency are high.TDI tar residue particle is cleared up, is recycled low
Boiling point small organic molecule and related inorganic object.This method simple process, easy to operate, condition is easily-controllable, equipment investment is less
And cost recovery is low.Liquid fuel calorific value is high, Fuel emission secondary pollution risk is small.Conducive to energy-saving and emission-reduction, environmental protection.
Detailed description of the invention
The invention will be further described in conjunction with the embodiments with reference to the accompanying drawings.
Fig. 1 is process flow chart of the invention.
Specific embodiment
Implementation method one.
By TDI tar residue solid material, through mechanical lapping at the TDI tar residue powder of 80 ~ 200 mesh partial sizes；It weighs
Appropriate ground TDI tar residue powder is placed in the high-temperature high-pressure reaction kettle with agitating device, by solid-to-liquid ratio 1:10(matter
Amount: volume ratio, kilogram: rise) methanol solvate is added, it is mixed and stirred for uniformly, obtaining the solidliquid mixture 1 containing TDI tar residue.
By the high-temperature high-pressure reaction kettle for including solidliquid mixture 1 from room temperature to 230 DEG C ~ 250 DEG C, 4 ~ 6MPa of pressure, heat preservation are kept
15 ~ 120min of time carries out resolution reaction, obtains resolution solidliquid mixture 2.High-temperature high-pressure reaction kettle switch is closed, is depressurized and cold
But to normal temperature and pressure.
Resolution solidliquid mixture 2 is separated by solid-liquid separation, resolution filtrate and resolution solid residue are respectively obtained.On a small amount of
It states methanol solvate washing resolution solid residue 3 ~ 5 times.It is spare to clear up solid residue.Gained washing filtrate and above-mentioned resolution are filtered every time
Liquid merges, and obtains total filtrate.Into total filtrate, ferrocene is added in 1:5 by mass percentage, is stirred evenly, and liquid fuel is made.
Implementation method two.
By TDI tar residue solid material, through mechanical lapping at the TDI tar residue powder of 80 ~ 200 mesh partial sizes；It weighs
Appropriate ground TDI tar residue powder is placed in the high-temperature high-pressure reaction kettle with agitating device, by solid-to-liquid ratio 1:10(matter
Amount: volume ratio, kilogram: rise) isopropanol solvent is added, it is mixed and stirred for uniformly, obtaining the solidliquid mixture containing TDI tar residue
1.By the high-temperature high-pressure reaction kettle for including solidliquid mixture 1 from room temperature to 240 DEG C ~ 260 DEG C, 4 ~ 6MPa of pressure is kept, is protected
Warm 15 ~ 120min of time carries out resolution reaction, obtains resolution solidliquid mixture 2.High-temperature high-pressure reaction kettle switch is closed, decompression is simultaneously
It is cooled to room temperature normal pressure.
Resolution solidliquid mixture 2 is separated by solid-liquid separation, resolution filtrate and resolution solid residue are respectively obtained.Using a small amount of different
Propanol solvent washing resolution solid residue 3 ~ 5 times.It is spare to clear up solid residue.Gained washing filtrate and above-mentioned resolution filtrate every time
Merge, obtains total filtrate.Into total filtrate, ferrocenyl methyl ketone additive is added in 1:5 by mass percentage, is stirred evenly, and liquid is made
Fluid fuel.
Implementation method three.
By TDI tar residue solid material, through mechanical lapping at the TDI tar residue powder of 200 mesh partial sizes；It weighs appropriate
Ground TDI tar residue powder is placed in the high-temperature high-pressure reaction kettle with agitating device, by solid-to-liquid ratio 1:10(mass: body
Product ratio, kilogram: rise) acetic acid solvent is added, it is mixed and stirred for uniformly, obtaining the solidliquid mixture 1 containing TDI tar residue.It will be interior
High-temperature high-pressure reaction kettle containing solidliquid mixture 1 keeps 3 ~ 5MPa of pressure, soaking time from room temperature to 240 DEG C ~ 260 DEG C
15 ~ 120min carries out resolution reaction, obtains resolution solidliquid mixture 2.High-temperature high-pressure reaction kettle switch is closed, depressurizes and is cooled to
Normal temperature and pressure.
Resolution solidliquid mixture 2 is separated by solid-liquid separation, resolution filtrate and resolution solid residue are respectively obtained.On a small amount of
It states acetic acid solvent washing resolution solid residue 3 ~ 5 times.It is spare to clear up solid residue.Gained washing filtrate and above-mentioned resolution are filtered every time
Liquid merges, and obtains total filtrate.Into total filtrate, ferrocene is added in 1:5 by mass percentage, is stirred evenly, and liquid fuel is made.
The foregoing is merely preferable implementation use-cases of the invention, are not intended to limit the scope of the present invention.It is all
Within the spirit and principles in the present invention, made any modification, equivalent replacement and improvement etc., should be included in of the invention
Within protection scope.
Claims (3)
1. a kind of method using TDI tar residue liquid fuel was prepared, which comprises the steps of:
Step 1) by TDI tar residue solid particulate materials, mechanical lapping is powder；Weigh ground TDI tar residue powder
It is placed in the high-temperature high-pressure reaction kettle with agitating device, low boiling-point and polarity solvent, mixing is added by solid-to-liquid ratio 1:1 ~ 20kg/L
And stir evenly, it obtains containing TDI tar residue solidliquid mixture；
Step 2) reaction kettle of TDI tar residue solidliquid mixture will be included from room temperature to 100 ~ 350 DEG C, keep pressure 2
~ 12MPa, 15 ~ 120min of soaking time carry out resolution reaction, obtain resolution solidliquid mixture, depressurize and be cooled to room temperature normal pressure；
Step 3) resolution solidliquid mixture is separated by solid-liquid separation, respectively obtain resolution filtrate and resolution solid residue；Use low boiling
For several times, washing filtrate merges point-polarity solvent washing resolution solid residue with resolution filtrate, obtains clearing up total filtrate；
Step 4) toward addition fuel combination promotor in total filtrate is cleared up, it stirs evenly, obtains liquid feul.
2. a kind of method using TDI tar residue liquid fuel was prepared as described in claim 1, it is characterised in that: described
It is 2 ~ 8 that low boiling-point and polarity solvent, which is by polarity parameters, and boiling point is 60 ~ 160 DEG C one kind or the mixture of several solvents；
The low boiling-point and polarity solvent include: in structure hydrocarbon oxygen atomicity ratio be 1 ~ 8:4 ~ 10:1 ~ 2 alcohols material, ketone
Substance, Ester and arene substance or derivative.
3. a kind of method using TDI tar residue liquid fuel was prepared as described in claim 1, it is characterised in that: described
Fuel accelerating agent be ferrocene, ferrocenyl methyl ketone, tert-butyl ferrocene, vinyl ferrocene and its Ferrocene-Derived product
One or more mixtures.
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| CN201910304883.8A CN109913255B (en) | 2019-04-16 | 2019-04-16 | Method for preparing liquid fuel by using TDI tar residues |
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Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101709234A (en) * | 2009-11-11 | 2010-05-19 | 济南开发区星火科学技术研究院 | Methanol diesel fuel complex additive and preparation method thereof |
| CN101717335A (en) * | 2009-12-10 | 2010-06-02 | 甘肃银达化工有限公司 | Method for recovering DEIP in TDI residues |
| CN104232180A (en) * | 2014-10-17 | 2014-12-24 | 广西丰泰能源防爆科技有限公司 | Methanol diesel fuel |
| CN105384644A (en) * | 2015-11-20 | 2016-03-09 | 联化科技（德州）有限公司 | Method for treating isocyanate residues |
-
2019
- 2019-04-16 CN CN201910304883.8A patent/CN109913255B/en active Active
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101709234A (en) * | 2009-11-11 | 2010-05-19 | 济南开发区星火科学技术研究院 | Methanol diesel fuel complex additive and preparation method thereof |
| CN101717335A (en) * | 2009-12-10 | 2010-06-02 | 甘肃银达化工有限公司 | Method for recovering DEIP in TDI residues |
| CN104232180A (en) * | 2014-10-17 | 2014-12-24 | 广西丰泰能源防爆科技有限公司 | Methanol diesel fuel |
| CN105384644A (en) * | 2015-11-20 | 2016-03-09 | 联化科技（德州）有限公司 | Method for treating isocyanate residues |
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