CN1923799A - Method of recovering o-aminobenzoic acid from mother liquid or waste water - Google Patents
Method of recovering o-aminobenzoic acid from mother liquid or waste water Download PDFInfo
- Publication number
- CN1923799A CN1923799A CNA2006100415293A CN200610041529A CN1923799A CN 1923799 A CN1923799 A CN 1923799A CN A2006100415293 A CNA2006100415293 A CN A2006100415293A CN 200610041529 A CN200610041529 A CN 200610041529A CN 1923799 A CN1923799 A CN 1923799A
- Authority
- CN
- China
- Prior art keywords
- anthranilic acid
- acid
- waste water
- resin
- flow velocity
- 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.)
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- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 title claims abstract description 64
- 238000000034 method Methods 0.000 title claims abstract description 13
- 239000002351 wastewater Substances 0.000 title claims abstract description 12
- 239000007788 liquid Substances 0.000 title abstract description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims abstract description 33
- 239000002253 acid Substances 0.000 claims abstract description 16
- 239000011347 resin Substances 0.000 claims abstract description 13
- 229920005989 resin Polymers 0.000 claims abstract description 13
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims abstract description 6
- 229910052708 sodium Inorganic materials 0.000 claims abstract description 6
- 239000011734 sodium Substances 0.000 claims abstract description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 21
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 18
- 238000001179 sorption measurement Methods 0.000 claims description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 15
- 239000012452 mother liquor Substances 0.000 claims description 13
- -1 o-amino benzoyl Chemical group 0.000 claims description 13
- 239000000243 solution Substances 0.000 claims description 12
- 238000010521 absorption reaction Methods 0.000 claims description 11
- 238000011084 recovery Methods 0.000 claims description 11
- 239000002585 base Substances 0.000 claims description 8
- 239000003456 ion exchange resin Substances 0.000 claims description 8
- 229920003303 ion-exchange polymer Polymers 0.000 claims description 8
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 claims description 6
- 229920006395 saturated elastomer Polymers 0.000 claims description 6
- KVNYFPKFSJIPBJ-UHFFFAOYSA-N 1,2-diethylbenzene Chemical compound CCC1=CC=CC=C1CC KVNYFPKFSJIPBJ-UHFFFAOYSA-N 0.000 claims description 4
- 238000004821 distillation Methods 0.000 claims description 4
- 238000002203 pretreatment Methods 0.000 claims description 3
- KIRUFUYXANNTBH-UHFFFAOYSA-N 2-aminobenzoic acid ethanol Chemical compound C(C)O.NC1=C(C(=O)O)C=CC=C1 KIRUFUYXANNTBH-UHFFFAOYSA-N 0.000 claims description 2
- 239000003513 alkali Substances 0.000 claims description 2
- 239000007864 aqueous solution Substances 0.000 claims description 2
- 230000001105 regulatory effect Effects 0.000 claims description 2
- NKBWAYZCDQRZEJ-UHFFFAOYSA-N C=CC1=CC=CC=C1.CCC1=CC=CC=C1CC Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1CC NKBWAYZCDQRZEJ-UHFFFAOYSA-N 0.000 abstract description 2
- 238000004064 recycling Methods 0.000 abstract 2
- 238000005342 ion exchange Methods 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 9
- 238000003795 desorption Methods 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- SXNZFKZMKXCAFD-UHFFFAOYSA-N 2-aminobenzoic acid;sodium Chemical compound [Na].NC1=CC=CC=C1C(O)=O SXNZFKZMKXCAFD-UHFFFAOYSA-N 0.000 description 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- 239000003463 adsorbent Substances 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000003810 ethyl acetate extraction Methods 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C227/38—Separation; Purification; Stabilisation; Use of additives
- C07C227/40—Separation; Purification
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a recycling method of o-aminobenzoic acid from mother liquid or waste water, which comprises the following steps: loading weak alkaline ion exchanging resin or phenylethene-diethyl benzene strong-polar large-hole adsorbing resin in the adsorbing column; adding acid or alkaline to adjust pH value for mother liquid or waste water; assembling adsorbing column under 5-40 deg.c with flow speed at 2-4BV/h; eluting through 2-6% sodium hydroxide solution under 25-45 deg.c with flow speed at 2-3BV/h; recycling sodium o-aminobenzoic solution.
Description
Technical field
The present invention relates to the recovery of anthranilic acid, specifically, is with the method recovery mother liquor of resin absorption and desorb or the anthranilic acid in the waste water.
Background technology
Anthranilic acid is produced in the mother liquor, contain 0.4% the anthranilic acid of having an appointment, existing production technique often adopts the ethyl acetate extraction method to reclaim, the rate of recovery only about 63%, simultaneously because ethyl acetate solubleness in water is bigger, need adopt distillation method that ethyl acetate in the waste water is reclaimed again, so energy consumption height, ethyl acetate waste are big.
Summary of the invention
To be a kind of employing weakly alkaline or macroporous adsorbent resin adsorb anthranilic acid under pH2-8,5-40 ℃, flow velocity 2-4BV/h condition in the present invention, use sig water (is representative with the sodium hydroxide solution) or organic solvent (is representative with ethanol) to carry out desorption again, reclaim anthranilic acid sodium or anthranilic acid and organic solvent.
The objective of the invention is to be achieved through the following technical solutions:
A kind of method that from mother liquor or waste water, reclaims anthranilic acid, it is made up of following steps basically:
Step 1, pack in adsorption column weak-base ion-exchange resin or vinylbenzene-strong polar macroporous adsorption resin of diethylbenzene type carry out pre-treatment routinely,
Step 2, the mother liquor that will contain anthranilic acid or waste water add acid or alkali and regulate pH, adopt weak-base ion-exchange resin, and pH regulator adopts strong polar macroporous adsorption resin to 7-8, and then pH regulator is to 2-3,
Step 3, step 2 is regulated the mother liquor that contains anthranilic acid behind the pH or waste water under 5-40 ℃, the condition of flow velocity 2-4BV/h, by the adsorption column that step 1 is installed, anthranilic acid is by resin absorption,
Step 4, when the adsorption column of step 3 absorption anthranilic acid is saturated, adsorption column obtains the o-amino benzoyl acid sodium aqueous solution and reclaims with the aqueous sodium hydroxide solution of 2-6% wash-out under 25-45 ℃, flow velocity 2-3BV/h condition.
The method of above-mentioned recovery anthranilic acid, step 4 can be used ethanol, methyl alcohol or acetone wash-out under 40-60 ℃, flow velocity 2-3BV/h condition instead, obtain anthranilic acid ethanol, methyl alcohol or acetone soln, reclaim anthranilic acid and ethanol, methyl alcohol or acetone through distillation.
The method of recovery anthranilic acid of the present invention, simple, the former water treatment that contains anthranilic acid 4500mg/L can be become contain below the anthranilic acid 1000mg/L, the rate of recovery reaches about 80%.
Embodiment
The invention will be further described by the following examples.
Embodiment 1
Get anthranilic acid synthesis mother liquid 500ml, the o-amino benzoyl acid concentration is 4500mg/L, and adding sulfuric acid or sodium hydroxide adjusting mother liquor PH is 7-8; Get weak-base ion-exchange resin (the 335 type weak-base ion-exchange resins that the Shanghai China scientific and technological trading company of shake produces) 10ml and adorn post; adsorb after being processed into the OH type with dilute sulphuric acid, diluted sodium hydroxide solution; 5 ℃ of adsorption temps; flow velocity 2BV/h; absorption effluent o-amino benzoyl acid concentration is 765mg/L, the rate of recovery 83%.Adsorb saturated back with 2% sodium hydroxide solution 35 ℃ of temperature, desorption obtains the o-amino benzoyl acid sodium solution during flow velocity 2BV/h, desorption rate 98.6%.
Embodiment 2
Get anthranilic acid synthesis mother liquid 500ml, the o-amino benzoyl acid concentration is 4500mg/L, adds sulfuric acid or sodium hydroxide and regulates mother liquor PH=7; Get weak-base ion-exchange resin (the 335 type weak-base ion-exchange resins that the Shanghai China scientific and technological trading company of shake produces) 10ml and adorn post; after being processed into the Cl type, rare potassium hydroxide solution, dilute hydrochloric acid adsorbs; 40 ℃ of adsorption temps; flow velocity 4BV/h; absorption effluent o-amino benzoyl acid concentration is 990mg/L, the rate of recovery 78%.Adsorb saturated back with 4% sodium hydroxide solution 45 ℃ of temperature, desorption obtains the o-amino benzoyl acid sodium solution during flow velocity 3BV/h, desorption rate 98.6%.
Embodiment 3
Get anthranilic acid synthesis mother liquid 500ml, the o-amino benzoyl acid concentration is 4500mg/l, adds sulfuric acid and regulates mother liquor PH=3;
Get strong polar macroporous adsorption resin (the strong polar macroporous adsorption resin of NKA-2 type of vinylbenzene-diethylbenzene structure that Tianjin Nankai chemical plant produces) 10ml and adorn post, pre-treatment is as follows: handle and be washed to neutrality with 4% hydrochloric acid, acetone, 4% sodium hydroxide solution successively.
Absorption: 25 ℃ of adsorption temps, flow velocity 3BV/h, absorption effluent o-amino benzoyl acid concentration is 1080mg/l, the rate of recovery 76%.Adsorb saturated back with 4% sodium hydroxide solution 90 ℃ of temperature, desorption during flow velocity 1BV/h obtains the o-amino benzoyl acid sodium solution, desorption rate 98.6%.
Embodiment 4
Get anthranilic acid synthesis mother liquid 500ml, the o-amino benzoyl acid concentration is 4500mg/l, adds sulfuric acid and regulates mother liquor PH=3; Get strong polar macroporous adsorption resin (the NKA-2 type that Tianjin Nankai chemical plant produces) 10ml and adorn post, pretreatment process is the same; During absorption, 35 ℃ of temperature, flow velocity 6BV/h, absorption effluent o-amino benzoyl acid concentration is 1260mg/l, the rate of recovery 72%.Adsorb saturated back and use industrial alcohol 60 ℃ of temperature, desorption obtains the anthranilic acid ethanolic soln during flow velocity 3BV/h, and fractionation by distillation obtains anthranilic acid and ethanol, desorption rate 99.5%.
Embodiment 5
With embodiment 4, but elutriant makes acetone into, and eluting temperature makes 40 ℃ into, and its result is with embodiment 4.
Embodiment 6
With embodiment 4, but elutriant makes methyl alcohol into, and its result is with embodiment 4.
Claims (2)
1. method that reclaims anthranilic acid from mother liquor or waste water is characterized in that it is made up of following steps basically:
Step 1, pack in adsorption column weak-base ion-exchange resin or vinylbenzene-strong polar macroporous adsorption resin of diethylbenzene type carry out pre-treatment routinely,
Step 2, the mother liquor that will contain anthranilic acid or waste water add acid or alkali and regulate pH, adopt weak-base ion-exchange resin, and pH regulator adopts strong polar macroporous adsorption resin to 7-8, and then pH regulator is to 2-3,
Step 3, step 2 is regulated the mother liquor that contains anthranilic acid behind the pH or waste water under 5-40 ℃, the condition of flow velocity 2-4BV/h, by the adsorption column that step 1 is installed, anthranilic acid is by resin absorption,
Step 4, when the adsorption column of step 3 absorption anthranilic acid is saturated, adsorption column obtains the o-amino benzoyl acid sodium aqueous solution and reclaims with the aqueous sodium hydroxide solution of 2-6% wash-out under 25-45 ℃, flow velocity 2-3BV/h condition.
2. the method for recovery anthranilic acid according to claim 1, it is characterized in that: step 4 is used ethanol, methyl alcohol or acetone wash-out under 40-60 ℃, flow velocity 2-3BV/h condition instead, obtain anthranilic acid ethanol, methyl alcohol or acetone soln, reclaim anthranilic acid and ethanol, methyl alcohol or acetone through distillation.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB2006100415293A CN100364962C (en) | 2006-09-12 | 2006-09-12 | Method of recovering o-aminobenzoic acid from mother liquid or waste water |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB2006100415293A CN100364962C (en) | 2006-09-12 | 2006-09-12 | Method of recovering o-aminobenzoic acid from mother liquid or waste water |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1923799A true CN1923799A (en) | 2007-03-07 |
| CN100364962C CN100364962C (en) | 2008-01-30 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNB2006100415293A Expired - Fee Related CN100364962C (en) | 2006-09-12 | 2006-09-12 | Method of recovering o-aminobenzoic acid from mother liquid or waste water |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN100364962C (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102190590A (en) * | 2011-03-25 | 2011-09-21 | 天津市鑫卫化工有限责任公司 | Method for recovering anthranilic acid from mother liquor waste water |
| CN103408177A (en) * | 2013-08-02 | 2013-11-27 | 盐城师范学院 | Method for treating and recycling waste water in anthranilic acid production technology |
| CN104016871A (en) * | 2014-06-11 | 2014-09-03 | 广东顺德天新环保科技有限公司 | Method for recycling anthranilic acid from methyl anthranilate wastewater |
| WO2018114841A1 (en) | 2016-12-20 | 2018-06-28 | Covestro Deutschland Ag | Process for preparing aminobenzoic acid or an aminobenzoic acid conversion product |
| CN111003846A (en) * | 2019-12-27 | 2020-04-14 | 苏州博睿特环保科技有限公司 | Recycling treatment method for anthranilic acid production wastewater |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2243553C1 (en) * | 2003-10-08 | 2004-12-27 | Государственное образовательное учреждение Воронежская государственная технологическая академия | Method of determining 4-aminobenzoic acid in aqueous solutions |
-
2006
- 2006-09-12 CN CNB2006100415293A patent/CN100364962C/en not_active Expired - Fee Related
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102190590A (en) * | 2011-03-25 | 2011-09-21 | 天津市鑫卫化工有限责任公司 | Method for recovering anthranilic acid from mother liquor waste water |
| CN103408177A (en) * | 2013-08-02 | 2013-11-27 | 盐城师范学院 | Method for treating and recycling waste water in anthranilic acid production technology |
| CN104016871A (en) * | 2014-06-11 | 2014-09-03 | 广东顺德天新环保科技有限公司 | Method for recycling anthranilic acid from methyl anthranilate wastewater |
| CN104016871B (en) * | 2014-06-11 | 2016-04-13 | 北京惠宇乐邦环保科技有限公司 | A kind of method reclaiming anthranilic acid from methyl o-aminobenzoate waste water |
| WO2018114841A1 (en) | 2016-12-20 | 2018-06-28 | Covestro Deutschland Ag | Process for preparing aminobenzoic acid or an aminobenzoic acid conversion product |
| CN110088080A (en) * | 2016-12-20 | 2019-08-02 | 科思创德国股份有限公司 | The method for preparing aminobenzoic acid or aminobenzoic acid subsequent products |
| US10968466B2 (en) | 2016-12-20 | 2021-04-06 | Covestro Deutschland Ag | Process for preparing aminobenzoic acid or an aminobenzoic acid conversion product |
| CN111003846A (en) * | 2019-12-27 | 2020-04-14 | 苏州博睿特环保科技有限公司 | Recycling treatment method for anthranilic acid production wastewater |
Also Published As
| Publication number | Publication date |
|---|---|
| CN100364962C (en) | 2008-01-30 |
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| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C14 | Grant of patent or utility model | ||
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Granted publication date: 20080130 Termination date: 20091012 |