CN107973713A - A kind of method that acetic acid is recycled from nitric-acetic-nitrate mixed liquor - Google Patents
A kind of method that acetic acid is recycled from nitric-acetic-nitrate mixed liquor Download PDFInfo
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- CN107973713A CN107973713A CN201711415201.8A CN201711415201A CN107973713A CN 107973713 A CN107973713 A CN 107973713A CN 201711415201 A CN201711415201 A CN 201711415201A CN 107973713 A CN107973713 A CN 107973713A
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- China
- Prior art keywords
- acetic acid
- mixed liquor
- acid
- nitric
- nitrate
- 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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- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 title claims abstract description 274
- 229910002651 NO3 Inorganic materials 0.000 title claims abstract description 20
- 238000000034 method Methods 0.000 title claims abstract description 17
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims abstract description 28
- 229910017604 nitric acid Inorganic materials 0.000 claims abstract description 28
- 239000002253 acid Substances 0.000 claims abstract description 16
- 238000006386 neutralization reaction Methods 0.000 claims abstract description 14
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 claims abstract description 12
- 238000004064 recycling Methods 0.000 claims abstract description 12
- 238000001704 evaporation Methods 0.000 claims abstract description 10
- 238000000746 purification Methods 0.000 claims abstract description 9
- 239000000203 mixture Substances 0.000 claims abstract description 5
- 230000003472 neutralizing effect Effects 0.000 claims abstract description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 23
- 230000008020 evaporation Effects 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 2
- 238000013019 agitation Methods 0.000 claims description 2
- 239000003513 alkali Substances 0.000 claims description 2
- 239000002585 base Substances 0.000 claims description 2
- 238000009833 condensation Methods 0.000 claims description 2
- 230000005494 condensation Effects 0.000 claims description 2
- 239000000463 material Substances 0.000 claims description 2
- 238000002156 mixing Methods 0.000 claims description 2
- 150000002500 ions Chemical class 0.000 claims 1
- 238000004821 distillation Methods 0.000 abstract description 3
- -1 nitroacetyl Chemical group 0.000 abstract 1
- PAWQVTBBRAZDMG-UHFFFAOYSA-N 2-(3-bromo-2-fluorophenyl)acetic acid Chemical compound OC(=O)CC1=CC=CC(Br)=C1F PAWQVTBBRAZDMG-UHFFFAOYSA-N 0.000 description 7
- 239000012071 phase Substances 0.000 description 5
- 238000000926 separation method Methods 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 239000000470 constituent Substances 0.000 description 2
- 238000005265 energy consumption Methods 0.000 description 2
- POCJOGNVFHPZNS-ZJUUUORDSA-N (6S,7R)-2-azaspiro[5.5]undecan-7-ol Chemical compound O[C@@H]1CCCC[C@]11CNCCC1 POCJOGNVFHPZNS-ZJUUUORDSA-N 0.000 description 1
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 1
- 239000005695 Ammonium acetate Substances 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 239000000028 HMX Substances 0.000 description 1
- BSPUVYFGURDFHE-UHFFFAOYSA-N Nitramine Natural products CC1C(O)CCC2CCCNC12 BSPUVYFGURDFHE-UHFFFAOYSA-N 0.000 description 1
- 239000000020 Nitrocellulose Substances 0.000 description 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229940043376 ammonium acetate Drugs 0.000 description 1
- 235000019257 ammonium acetate Nutrition 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical group 0.000 description 1
- WURBFLDFSFBTLW-UHFFFAOYSA-N benzil Chemical compound C=1C=CC=CC=1C(=O)C(=O)C1=CC=CC=C1 WURBFLDFSFBTLW-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- POCJOGNVFHPZNS-UHFFFAOYSA-N isonitramine Natural products OC1CCCCC11CNCCC1 POCJOGNVFHPZNS-UHFFFAOYSA-N 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 230000000802 nitrating effect Effects 0.000 description 1
- 238000006396 nitration reaction Methods 0.000 description 1
- 230000001546 nitrifying effect Effects 0.000 description 1
- 229920001220 nitrocellulos Polymers 0.000 description 1
- VLZLOWPYUQHHCG-UHFFFAOYSA-N nitromethylbenzene Chemical compound [O-][N+](=O)CC1=CC=CC=C1 VLZLOWPYUQHHCG-UHFFFAOYSA-N 0.000 description 1
- UZGLIIJVICEWHF-UHFFFAOYSA-N octogen Chemical compound [O-][N+](=O)N1CN([N+]([O-])=O)CN([N+]([O-])=O)CN([N+]([O-])=O)C1 UZGLIIJVICEWHF-UHFFFAOYSA-N 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- FGIUAXJPYTZDNR-UHFFFAOYSA-N potassium nitrate Chemical compound [K+].[O-][N+]([O-])=O FGIUAXJPYTZDNR-UHFFFAOYSA-N 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000010025 steaming Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
- C07C51/43—Separation; Purification; Stabilisation; Use of additives by change of the physical state, e.g. crystallisation
- C07C51/44—Separation; Purification; Stabilisation; Use of additives by change of the physical state, e.g. crystallisation by distillation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
- C07C51/487—Separation; Purification; Stabilisation; Use of additives by treatment giving rise to chemical modification
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Crystallography & Structural Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a kind of method that acetic acid is recycled in nitrate mixed liquor from nitroacetyl, kettle is neutralized by being added after pending spent acid analysis metering wherein nitric acid, nitric acid is neutralized to the neutralizer for neutralizing kettle addition equimolar amounts again, spent acid overflow after neutralization enters evaporator, evaporator controls temperature, steam thick acetic acid, the main composition for evaporating raffinate is more than 60% nitrate, the thick acetic acid gas phase evaporated is directly entered purification of acetic acid tower, atmospheric distillation obtains the recycling acetic acid of purity more than 99%, the present invention can improve acetic acid yield, reduce equipment investment and energy expenditure, also operation is made to obtain necessarily simplifying operation.
Description
Technical field
The present invention relates to processing separation process technical field, in particular to one kind from nitric-acetic-nitrate mixed liquor
The method of middle recycling acetic acid.
Background technology
Industrially, nitric acid can be used to prepare acetic acid nitrocellulose with acetic acid, in medicine preparation mesosome benzil
During also have the application of nitric acid and acetic acid, nitric acid and acetic acid or mixture or a kind of practical nitrating agent of acetic anhydride, can
Phenyl nitromethane is prepared for nitrofying aromatic hydrocarbon side chain, such as with the mixture nitration of toluene of nitric acid and acetic acid, is also used for nitrifying
The ratio of ortho-product is improved during aromatic compound, especially suitable for nitrification amine to prepare nitramine, such as nitre solution Wu Luotuo
Product prepare octogen.Above-mentioned during these, acetic acid is to participate in esterification a bit, some are not involved in chemical anti-in itself
Should, only aid in the nitrification and oxidizing process for nitric acid to provide environment, therefore lead in the mixed liquor after separating product except acetic acid
Often also contain a small amount of nitric acid and nitrate, acetic acid therein need to be recycled by these spent acid.It is typically industrially at present
Heavy constituents such as first rectifying removing nitric acid, nitrate, then rectifying is carried out to the thick acetic acid of overhead extraction, then obtain purity 99% with
The mode of upper acetic acid is recycled.
The recycling of acetic acid mainly includes two parts：1st, the removing of nitric acid and salt；2nd, acetic acid is refined.
Technical process is two tower distillation processes used by industrial at present, is specially：Pending spent acid is first
Steam tower into acetic acid, produce aqueous thick acetic acid by rectifying tower top, tower reactor isolate containing nitric acid, acetic acid and ammonium nitrate and
The residual night of other heavy constituents, tower reactor generally regard temperature interval and produce.(since nitric acid and acetic acid can form binary azeotrope, azeotropic
Nitric acid 34%, acetic acid 66% are formed, therefore tower bottoms acetic acid content is higher).The thick acetic acid of overhead extraction enters back into purification of acetic acid
Tower, the main separating acetic acid of the tower and water, overhead extraction contain the acid water of micro-acetic acid, and tower reactor obtains returning for purity more than 99%
Receive acetic acid.
The shortcomings that flow, is：A, during rectifying separation nitric acid, since nitric acid and acetic acid have maximum boiling point, tower
Kettle nitric acid can suppress the evaporation of acetic acid, reduce the yield for steaming acetic acid；B, rectifying column contains stripping section, can promote acetic acid and water
Separation, acetic acid is tended to tower reactor, this also causes acetic acid yield to reduce；C, since the latent heat difference of acetic acid, nitric acid and water is larger,
Rectifying separation it is larger to liquid phase load fluctuation in tower, it is desirable to tower size it is larger；D, the thick acetic acid that tower top steams needs cold
Purification of acetic acid tower is entered back into after solidifying, adds energy consumption.
The content of the invention
For above-mentioned problems of the prior art, the present invention provides one kind from nitric-acetic-nitrate mixed liquor
The method for recycling acetic acid.
To achieve the above object, the present invention provides following technical solution：
A kind of method that acetic acid is recycled from nitric-acetic-nitrate mixed liquor, mainly includes the following steps that：
A) nitric-acetic-nitrate mixed liquor is placed in neutralization kettle, is added to neutralizing in kettle and nitric acid equimolar amounts in mixed liquor
Neutralizer, fully agitation mixing neutralizes kettle top portion and is equipped with and neutralize kettle condenser, and condensation neutralizes the material of heat release evaporation；
B) the direct overflow of mixed liquor after neutralizing is evaporated into evaporator, and raffinate is steamed from base of evaporator emission treatment
Thick acetic acid gas phase be directly entered purification of acetic acid tower；
C) thick acetic acid bottom of towe after rectifying obtains the acetic acid of refined recycling, and tower top obtains acid water.
Preferably, nitric acid content is no more than 20% in mixed liquor in step a), and acetic acid content is more than 50%, and nitrate content is not
More than 20%, water content is equilibrium composition；Nitrate is nitrate soluble easily in water, soluble easily in water to refer to that solubility is more than 10 grams.
Preferably, neutralizer is the alkali or its acetate for the cation that salt is corresponded in mixed liquor.
Preferably, the neutralization mode in step a) is by analyzing metering in advance, is then directly mixed to be neutralized again.
Preferably, in step c), thick acetic acid is that acetic acid and water are steamed by way of directly evaporating.
The present invention to above-mentioned technique there are the shortcomings that improved, mainly include：A, add neutralizer make nitric acid not with
Free state exists, neutralizer and the corresponding nitrate of nitric acid reaction generation.So destroy nitric acid, acetic acid forms the ring of azeotropic
Border, is not required to separate nitric acid with rectifying, and nitrate can be removed using evaporation, while steams acetic acid, and such evaporator replaces essence
Tower is evaporated, that is, saves equipment investment, and reduces complicated degree, while the yield of acetic acid can also be improved；B, evaporate
Thick acetic acid it is not condensed directly gas phase enter treating column recovery of acetic acid, the energy consumption for the treatment of column can be reduced；
The present invention can improve acetic acid yield, reduce equipment investment and energy expenditure, also make operation obtain necessarily simplifying operation, with mesh
Preceding known procedures are compared, and flow of the present invention has the following advantages：
A, nitric acid is not contained in the spent acid after neutralizing, can directly steam thick acetic acid, tower reactor loss acetic acid is reduced, improves acetic acid
Yield；
B, the thick acetic acid steamed can not be condensed direct gas phase and enter purification of acetic acid tower, reduce the energy of device operation
Consumption；
C, evaporation operation difficulty is operated less than rectifying column；
D, the equipment investment of flow is less than existing distillation process after improving, and modified flow can reduce equipment investment.
Brief description of the drawings
Fig. 1 is the process flow chart of the present invention.
In figure：1：Neutralization kettle, 2：Neutralization kettle condenser, 3：Evaporator, 4：Purification of acetic acid tower, 5：Treating column condenser, 6：
Refined tower reboiler.
Embodiment
It is right with reference to the attached drawing of the present invention in order to make those skilled in the art more fully understand technical scheme
Technical scheme carries out clear, complete description, and based on the embodiment in the application, those of ordinary skill in the art exist
The other similar embodiments obtained on the premise of not making creative work, should all belong to the scope of the application protection.
Specific embodiment 1：
Pending 1460 kg/h of spent acid S1 flows (nitric acid 6%, acetic acid 63%, water 25.5%, ammonium nitrate 5.5%), which enters, neutralizes kettle 1,
Add the 25% ammonium hydroxide S2 of 94.7kg/h after analysis metering, neutralization obtain spent acid S3 after the neutralization of 1554.7kg/h (acetic acid 59.2%,
Water 28.5%, ammonium nitrate 12.3%), the spent acid after neutralization is evaporated to 130.7 DEG C into evaporator 3, steams the thick acetic acid of 1285kg/h
S5 (acetic acid 68%, water 32%), evaporation raffinate 269.7kg/h S4 (acetic acid 17%, ammonium nitrate 71%, water 12%), this process acetic acid
Yield up to 95%.
The thick acetic acid of gas phase of 1285kg/h enters purification of acetic acid tower 4, and rectifying obtains the acid water S6 (acetic acid of 414.4kg/h
2%), bottom of towe obtains the recycling acetic acid S7 of 870.6kg/h purity 99.4%.
Specific embodiment 2：
Pending 2500 kg/h of spent acid S1 flows (nitric acid 2.5%, acetic acid 67%, water 27.5%, ammonium nitrate 3%), which enters, neutralizes kettle 1,
Add the ammonium acetate S2 of 76.5kg/h after analysis metering, neutralization obtain spent acid S3 after the neutralization of 2576.5kg/h (acetic acid 67.3%,
Water 26.7%, ammonium nitrate 6%), the spent acid after neutralization is evaporated to 132.6 DEG C into evaporator 3, steams the thick acetic acid S5 of 2359.1kg/h
(acetic acid 71.8%, water 28.2%), evaporation raffinate 217.4kg/h S4 (acetic acid 18.8%, ammonium nitrate 71%, water 10.2%).Thick acetic acid
Gas phase enters purification of acetic acid tower 4, and rectifying obtains the acid water S6 (acetic acid 2%) of 670.3kg/h, and it is pure that bottom of towe obtains 1688.8kg/h
The recycling acetic acid S7 of degree 99.5%.
Moreover, it will be appreciated that although the present specification is described in terms of embodiments, not each embodiment is only wrapped
Containing an independent technical solution, this narrating mode of specification is only that those skilled in the art should for clarity
Using specification as an entirety, the technical solutions in the various embodiments may also be suitably combined, forms those skilled in the art
It is appreciated that other embodiment.
Claims (5)
- A kind of 1. method that acetic acid is recycled from nitric-acetic-nitrate mixed liquor, it is characterised in that mainly including following step Suddenly：Nitric-acetic-nitrate mixed liquor is placed in neutralization kettle, is added to neutralizing in kettle and nitric acid equimolar amounts in mixed liquor Neutralizer, fully agitation mixing, neutralizes kettle top portion equipped with kettle condenser, condensation is neutralized and neutralizes the material of heat release evaporation；The direct overflow of mixed liquor after neutralization is evaporated into evaporator, and raffinate is steamed from base of evaporator emission treatment Thick acetic acid gas phase is directly entered purification of acetic acid tower；Thick acetic acid bottom of towe after rectifying obtains the acetic acid of refined recycling, and tower top obtains acid water.
- 2. the method for recycling acetic acid according to claim 1, it is characterised in that nitric acid content is not in mixed liquor in step a) More than 20%, acetic acid content is more than 50%, and nitrate content is no more than 20%, and water content is equilibrium composition；Nitrate is soluble easily in water Nitrate.
- 3. the method for recycling acetic acid according to claim 1, it is characterised in that neutralizer is the sun that salt is corresponded in mixed liquor The alkali of ion or its acetate.
- 4. the method for recycling acetic acid according to claim 1, it is characterised in that the neutralization mode in step a) is by pre- First analysis metering, then directly mixes to be neutralized again.
- 5. the method for recycling acetic acid according to claim 1, it is characterised in that in step c), thick acetic acid is by direct The mode of evaporation steams acetic acid and water.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201711415201.8A CN107973713A (en) | 2017-12-25 | 2017-12-25 | A kind of method that acetic acid is recycled from nitric-acetic-nitrate mixed liquor |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201711415201.8A CN107973713A (en) | 2017-12-25 | 2017-12-25 | A kind of method that acetic acid is recycled from nitric-acetic-nitrate mixed liquor |
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|---|---|
| CN107973713A true CN107973713A (en) | 2018-05-01 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201711415201.8A Pending CN107973713A (en) | 2017-12-25 | 2017-12-25 | A kind of method that acetic acid is recycled from nitric-acetic-nitrate mixed liquor |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109052355A (en) * | 2018-08-07 | 2018-12-21 | 安庆市鑫祥瑞环保科技有限公司 | The method of phosphoric acid and acetic acid is recycled from waste aluminum etching solution |
| CN111072785A (en) * | 2019-12-03 | 2020-04-28 | 北京理工大学 | Preparation method of high-nitrogen-content nitrified bamboo cellulose |
| CN114292181A (en) * | 2022-01-27 | 2022-04-08 | 西安海泽微流工程技术有限公司 | Process for recovering acetic acid from 2-methyl-5-nitroimidazole nitration completion liquid |
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| CN1086205A (en) * | 1992-10-26 | 1994-05-04 | 大连市轻化工研究所 | The method of preparing n-hexyl acid by secondary-octanol nitric acid oxydation |
| TW200635848A (en) * | 2005-04-06 | 2006-10-16 | Hiforce Chemicals Corp | Method of recycling nitric acid, acetic acid or their salts from a waste solution including nitric acid, acetic acid and a third acid |
-
2017
- 2017-12-25 CN CN201711415201.8A patent/CN107973713A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1086205A (en) * | 1992-10-26 | 1994-05-04 | 大连市轻化工研究所 | The method of preparing n-hexyl acid by secondary-octanol nitric acid oxydation |
| TW200635848A (en) * | 2005-04-06 | 2006-10-16 | Hiforce Chemicals Corp | Method of recycling nitric acid, acetic acid or their salts from a waste solution including nitric acid, acetic acid and a third acid |
Non-Patent Citations (1)
| Title |
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| 倪冲: "从电子加工行业产生的混合废酸中回收乙酸的方法和机理研究", 《中国优秀硕士学位论文全文数据库 工程科技I辑》 * |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109052355A (en) * | 2018-08-07 | 2018-12-21 | 安庆市鑫祥瑞环保科技有限公司 | The method of phosphoric acid and acetic acid is recycled from waste aluminum etching solution |
| CN111072785A (en) * | 2019-12-03 | 2020-04-28 | 北京理工大学 | Preparation method of high-nitrogen-content nitrified bamboo cellulose |
| CN111072785B (en) * | 2019-12-03 | 2020-12-01 | 北京理工大学 | Preparation method of high-nitrogen-content nitrified bamboo cellulose |
| CN114292181A (en) * | 2022-01-27 | 2022-04-08 | 西安海泽微流工程技术有限公司 | Process for recovering acetic acid from 2-methyl-5-nitroimidazole nitration completion liquid |
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Application publication date: 20180501 |