CN1045967A - Utilize adiponitrile tar to prepare the method for hexanodioic acid - Google Patents
Utilize adiponitrile tar to prepare the method for hexanodioic acid Download PDFInfo
- Publication number
- CN1045967A CN1045967A CN 89105038 CN89105038A CN1045967A CN 1045967 A CN1045967 A CN 1045967A CN 89105038 CN89105038 CN 89105038 CN 89105038 A CN89105038 A CN 89105038A CN 1045967 A CN1045967 A CN 1045967A
- Authority
- CN
- China
- Prior art keywords
- adiponitrile
- tar
- acid
- reaction
- crystallization
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 239000002253 acid Substances 0.000 title claims abstract description 30
- BTGRAWJCKBQKAO-UHFFFAOYSA-N adiponitrile Chemical compound N#CCCCCC#N BTGRAWJCKBQKAO-UHFFFAOYSA-N 0.000 title claims abstract description 26
- 238000000034 method Methods 0.000 title claims abstract description 25
- 238000006243 chemical reaction Methods 0.000 claims abstract description 25
- 239000000203 mixture Substances 0.000 claims abstract description 5
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 claims description 30
- 238000002425 crystallisation Methods 0.000 claims description 16
- 230000008025 crystallization Effects 0.000 claims description 16
- 235000011037 adipic acid Nutrition 0.000 claims description 15
- 239000001361 adipic acid Substances 0.000 claims description 15
- 239000003513 alkali Substances 0.000 claims description 12
- 239000012530 fluid Substances 0.000 claims description 12
- 150000007522 mineralic acids Chemical class 0.000 claims description 12
- 238000003756 stirring Methods 0.000 claims description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 10
- 239000000706 filtrate Substances 0.000 claims description 8
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 6
- 238000006460 hydrolysis reaction Methods 0.000 claims description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 5
- 239000012065 filter cake Substances 0.000 claims description 5
- 238000011010 flushing procedure Methods 0.000 claims description 5
- 238000001914 filtration Methods 0.000 claims description 4
- 238000010438 heat treatment Methods 0.000 claims description 4
- 229910021529 ammonia Inorganic materials 0.000 claims description 3
- 238000001035 drying Methods 0.000 claims description 3
- 239000006210 lotion Substances 0.000 claims description 3
- 238000007670 refining Methods 0.000 claims description 3
- 238000005406 washing Methods 0.000 claims description 3
- 238000004090 dissolution Methods 0.000 claims description 2
- 230000007062 hydrolysis Effects 0.000 claims description 2
- 230000003301 hydrolyzing effect Effects 0.000 claims description 2
- 239000000376 reactant Substances 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 238000010992 reflux Methods 0.000 claims 2
- 239000012141 concentrate Substances 0.000 claims 1
- 230000008901 benefit Effects 0.000 abstract description 3
- 239000002699 waste material Substances 0.000 abstract description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 17
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- 238000005903 acid hydrolysis reaction Methods 0.000 description 2
- 238000005904 alkaline hydrolysis reaction Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- NICLKHGIKDZZGV-UHFFFAOYSA-N 2-cyanopentanoic acid Chemical compound CCCC(C#N)C(O)=O NICLKHGIKDZZGV-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- OSNDUYDDOHEKEE-UHFFFAOYSA-N azepane-2,7-dione Chemical compound O=C1CCCCC(=O)N1 OSNDUYDDOHEKEE-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- -1 hexanoyl acid amide Chemical class 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000000452 restraining effect Effects 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The present invention utilizes adiponitrile tar to prepare the method for hexanodioic acid, and it is to take the reaction that is hydrolyzed under acidity or alkaline condition of adiponitrile tar is generated hexanodioic acid, hexanodioic acid is separated from mixture again, thereby has been made pure hexanodioic acid.
Use the method for preparing hexanodioic acid, not only economical, effectively utilized adiponitrile tar, improve economic benefit, and prevented the pollution that these wastes bring to environment again.
Description
The present invention relates to a kind of method of producing hexanodioic acid.
It is reported that generally adopt alcohol, oxidation of ketones method and butadiene process to prepare hexanodioic acid at present, though these two kinds of methods are the main method of producing hexanodioic acid at present, it has weak points such as complex process, condition harshness, cost height both at home and abroad.
The objective of the invention is in order to make full use of adiponitrile tar, the hexanodioic acids of producing some high economic worths more, adiponitrile tar is turned waste into wealth, and reduce the environmental pollution that adiponitrile tar is brought, a kind of method of utilizing adiponitrile tar to prepare hexanodioic acid is provided.
The present invention realizes that the technical solution of above-mentioned purpose is: being used in the adiponitrile tar by product that produces in the adiponitrile treating process is the feedstock production hexanodioic acid.Mainly utilize carbon six components such as hexanoyl acid amide, cyanopentanoic acid, adipimide and adiponitrile that contain in the adiponitrile tar, make these compounds issue unboiled water and separate reaction, generate hexanodioic acid at acidity or alkaline condition.Then again hexanodioic acid is separated from mixture, thereby made pure hexanodioic acid.Its concrete grammar is as follows:
Method 1: adiponitrile tar is placed reaction vessel, add inorganic acid fluid then, and heating, stir and to make it under refluxad carry out acid hydrolytic reaction, cool off after the reaction, filter, with the gained filter cake with heat again, stir after inorganic alkali lye mixes, make it be carried out to reactant salt.Cool off after the reaction, filter, gained filtrate is mixed with inorganic acid fluid carry out acidifying, separate out crystallization of adipic acid, filter then and obtain crystallization of adipic acid.Also can be, and use activated carbon decolorizing with the crystallization of adipic acid water dissolution of gained, carry out condensing crystal after the decolouring, filter and make refining hexanodioic acid.The concentration of its inorganic acid fluid is 20-70%, and its hydrolysis reaction is under 60-120 ℃ temperature, stirs 4-16 hour.The concentration of its inorganic alkali lye is 5-65%.The weight ratio of its adiponitrile tar and inorganic acid fluid consumption is 1: 3～17.
Several principal reactions of acidic hydrolysis:
Method 2: adiponitrile tar is placed reaction vessel, add inorganic alkali lye then, and heating, stir and to make it under refluxad carry out basic hydrolysis, simultaneously the ammonia that discharges in the reaction process is absorbed with acid solution.Cool off after the reaction, filter,, then washing lotion and filtrate are mixed the flushing of gained filter cake water.Mix back adding inorganic acid fluid and carry out acidifying, separate out crystallization of adipic acid.Filter then,, carry out drying after the flushing the crystallization of adipic acid water flushing of gained.The concentration of its inorganic alkali lye is 10-50%.Its hydrolysis reaction is under 60～120 ℃ of temperature, stirs 4～16 hours.The concentration of its inorganic acid fluid is 10～90%.Its adiponitrile tar and inorganic alkali lye weight ratio are 1: 2.5～14.
Several principal reactions of alkaline hydrolysis:
Advantage of the present invention is: not only economical, effectively utilized adiponitrile tar because to have adopted with adiponitrile tar is the method for feedstock production hexanodioic acid, and improve economic benefit, and prevented the pollution that these wastes bring to environment again.
Embodiment 1: acidic hydrolysis system hexanodioic acid
In 500 milliliters there-necked flask, add 110 ml concns and be 30% stream acid solution, add adiponitrile tar 100 grams again, and stir, simultaneously heat temperature raising with 180 rev/mins speed, making it is reaction 6 hours under 100 ℃ the condition in temperature of reaction, make its cooling after the reaction, and filter, removing after the filtrate with 100 ml concns is that 25% alkali lye mixes with filter cake, heat temperature raising then, the speed with 180 rev/mins under 50 ℃ condition stirred 1 hour.Cool off behind the question response, filter, and be that 20% sulfuric acid is 1.6 with making it be acidified to pH value filtrate mixing with concentration, separate out crystallization of adipic acid, take out crystallization of adipic acid by filtering.In order to obtain refining hexanodioic acid, used water is dissolved crystallization of adipic acid, and decolours with gac, carries out condensing crystal after the decolouring again, has just obtained pure hexanodioic acid after the filtration.
Embodiment 2: alkaline hydrolysis system hexanodioic acid
In 500 milliliters there-necked flask, add the 100 dintrile tar of restraining oneself, add 100 ml concns again and be 25% alkali lye (NaOH), and stir with 200 rev/mins speed, heat temperature raising simultaneously, making it is reaction 4 hours under 100 ℃ the condition in temperature of reaction.And the ammonia that discharges in the reaction process is absorbed with sulfuric acid liquid.Make its cooling after the reaction, and filter, remove after the filtrate with twice of 20 milliliters of cold water flush, then washing lotion and filtrate are mixed, mix the back add concentration be 20% dilute sulfuric acid solution to be acidified to pH value be 1.6, separate out crystallization of adipic acid, by filtering crystallization of adipic acid is taken out, and, wash the back and under 70 ℃ condition, carry out drying with the less water flushing.
Claims (10)
1, a kind of method of utilizing adiponitrile tar to prepare hexanodioic acid, it is characterized in that adiponitrile tar is placed reaction vessel, add inorganic acid fluid then, and heating, stirring makes it carry out acid hydrolytic reaction under the condition that refluxes, cool off after the reaction, filter, with the gained filter cake with heat again after inorganic alkali lye mixes, stirring makes it be carried out to reactant salt, cool off after the reaction, filter, gained filtrate mixed with inorganic acid fluid carry out acidifying, separate out crystallization of adipic acid, filter then and obtain crystallization of adipic acid, also can be with the crystallization of adipic acid water dissolution of gained, and use activated carbon decolorizing, concentrate after the decolouring, crystallization, filtration makes refining hexanodioic acid.
2, method according to claim 1 is characterized in that said inorganic acid fluid, and concentration is 20～70%.
3, method according to claim 1 is characterized in that said hydrolysis reaction, is to stir under 60～120 ℃ temperature 4～16 hours.
4, method according to claim 1 is characterized in that said inorganic alkali lye, and concentration is 5～65%.
5, method according to claim 1 is characterized in that said adiponitrile tar and inorganic acid fluid weight ratio are 1: 3～17.
6, a kind of method of utilizing adiponitrile tar to prepare hexanodioic acid, it is characterized in that adiponitrile tar is placed reaction vessel, add inorganic alkali lye then, and heating, stirring makes it carry out basic hydrolysis under the condition that refluxes, simultaneously the ammonia that discharges in the reaction process is absorbed with acid solution, cool off after the reaction, filter, gained filter cake water is washed, then washing lotion and filtrate are mixed, mix back adding inorganic acid fluid and carry out acidifying, separate out crystallization of adipic acid, filter then, the crystallization of adipic acid water of gained is washed, carry out drying after the flushing.
7, method according to claim 6 is characterized in that said inorganic alkali lye, and concentration is 10～50%.
8, method according to claim 6 is characterized in that said hydrolysis reaction, is to stir 4～16 hours under 60～120 ℃ of temperature.
9, method according to claim 6 is characterized in that said inorganic acid fluid, and concentration is 10～90%.
10, method according to claim 6 is characterized in that said adiponitrile tar and inorganic alkali lye weight ratio are 1: 2.5～14.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 89105038 CN1045967A (en) | 1989-03-25 | 1989-03-25 | Utilize adiponitrile tar to prepare the method for hexanodioic acid |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 89105038 CN1045967A (en) | 1989-03-25 | 1989-03-25 | Utilize adiponitrile tar to prepare the method for hexanodioic acid |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN1045967A true CN1045967A (en) | 1990-10-10 |
Family
ID=4855810
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN 89105038 Pending CN1045967A (en) | 1989-03-25 | 1989-03-25 | Utilize adiponitrile tar to prepare the method for hexanodioic acid |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN1045967A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN100368047C (en) * | 2002-12-27 | 2008-02-13 | 住友化学株式会社 | Crystallization method and crystallization apparatus |
-
1989
- 1989-03-25 CN CN 89105038 patent/CN1045967A/en active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN100368047C (en) * | 2002-12-27 | 2008-02-13 | 住友化学株式会社 | Crystallization method and crystallization apparatus |
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| PB01 | Publication | ||
| C01 | Deemed withdrawal of patent application (patent law 1993) | ||
| WD01 | Invention patent application deemed withdrawn after publication |