CN101130496A - Method for removing heavy hydrocarbon from reaction product of preparation of sec-butyl acetate - Google Patents
Method for removing heavy hydrocarbon from reaction product of preparation of sec-butyl acetate Download PDFInfo
- Publication number
- CN101130496A CN101130496A CNA2007100357413A CN200710035741A CN101130496A CN 101130496 A CN101130496 A CN 101130496A CN A2007100357413 A CNA2007100357413 A CN A2007100357413A CN 200710035741 A CN200710035741 A CN 200710035741A CN 101130496 A CN101130496 A CN 101130496A
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- China
- Prior art keywords
- heavy hydrocarbon
- water
- sec
- butyl acetate
- acetate
- 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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- 229930195733 hydrocarbon Natural products 0.000 title claims abstract description 74
- 150000002430 hydrocarbons Chemical class 0.000 title claims abstract description 74
- 239000004215 Carbon black (E152) Substances 0.000 title claims abstract description 72
- 238000000034 method Methods 0.000 title claims abstract description 23
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 title claims description 30
- 239000007795 chemical reaction product Substances 0.000 title claims description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 65
- 239000000463 material Substances 0.000 claims abstract description 43
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 abstract description 20
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract description 9
- 239000012535 impurity Substances 0.000 abstract description 3
- 150000001336 alkenes Chemical class 0.000 abstract description 2
- 238000005265 energy consumption Methods 0.000 abstract description 2
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 abstract description 2
- 238000010030 laminating Methods 0.000 abstract 1
- 238000010533 azeotropic distillation Methods 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 9
- 238000005516 engineering process Methods 0.000 description 7
- 238000000926 separation method Methods 0.000 description 7
- 239000000047 product Substances 0.000 description 6
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 6
- 239000000470 constituent Substances 0.000 description 5
- 239000002994 raw material Substances 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 241000282326 Felis catus Species 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 230000003116 impacting effect Effects 0.000 description 3
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000007701 flash-distillation Methods 0.000 description 2
- 239000008369 fruit flavor Substances 0.000 description 2
- 239000012451 post-reaction mixture Substances 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 230000003245 working effect Effects 0.000 description 2
- 239000002253 acid Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229940043232 butyl acetate Drugs 0.000 description 1
- 238000007036 catalytic synthesis reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- -1 isobutyl ester Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a separating method of impurity such as heavy hydrocarbon from reacting product in the acetate para-butyl making technique reacted by acetic acid and C4 olefin, which is characterized by the following: extracting materials from heavy hydrocarbon enriching area; contacting the material and water sufficiently; laminating the heavy hydrocarbon and water naturally; draining the heavy hydrocarbon; injecting water into the system again. The method can strip heavy hydrocarbon in the reacting product to prepare acetate para-butyl, which improves the quality of the product and modifies the operating condition to reduce the energy consumption.
Description
Technical field
The present invention relates to a kind ofly prepare in the technology of sec-butyl acetate the method that heavy hydrocarbon is separated from reaction product at acetate and C4 olefine reaction.
Background technology
Sec-butyl acetate also claims acetate butyl ester, acetate second butyl ester in addition, be one of four kinds of isomer of butylacetate, for liquid colourless, inflammable, that have the fruit flavor, in most of the cases all similar to the performance of other isomer, solubilized various kinds of resin and organism.Positive butyl ester and isobutyl ester that its boiling point is commonly used are low, and velocity of evaporation is very fast.Main as solvent, medicine industry, reaction medium, extraction agent component, metal cleaner, fruit flavors etc.
For traditional technology, utilize 1-butylene, 2-butylene to have for raw material and acetic acidreaction prepare sec-butyl acetate that raw material sources are wide and inexpensive, good in economic efficiency, advantages of environment protection, therefore, its synthesising process research has obtained extensive concern.
But utilize the research of the separation and purification technology of acetate and 1-butylene, 2-butylene prepared in reaction sec-butyl acetate to report less.
The US5457228 United States Patent (USP) has been reported a kind of method of utilizing acetate and 1-butylene and 2-butylene reaction catalytic Synthesis of sec-Butyl Acetate, and olefin conversion that obtains and selectivity of product are all higher.For its separation method, mention in the patent and utilize distillation just sec-butyl acetate can be separated from reaction mixture.But patent is not announced concrete separation method, does not announce after separating the purity that product reached yet.
The inventor in application number is the Chinese patent application of 200710200148X, disclose a kind of from acetate and butylene or hybrid C 4 post reaction mixture the method for the secondary butyl ester of separating acetic acid: (1) acetate and hybrid C 4 post reaction mixture enter flashing tower, by flash distillation from unreacted hybrid C 4 of flash distillation removed overhead and light constituent; (2) the flashing tower bottom product enters azeotropy rectification column, adds entrainer A, by azeotropic distillation with sec-butyl acetate and separated from acetic acid; (3) azeotropic distillation cat head material enters treating tower, obtains sec-butyl acetate by rectifying; (4) amount that contains entrainer A when acetate from the extraction of azeotropy rectification column bottom to reaction impact or to catalyst activity with when impacting work-ing life, azeotropy rectification column bottom material enters sour upgrading tower, add entrainer B, through azeotropic distillation again, acetate is concentrated acetate recycle after concentrating; Or: the amount that contains entrainer A when the acetate from the extraction of azeotropy rectification column bottom can be to not impacting of reacting, and in the time of also can and not impacting work-ing life catalyst activity, azeotropy rectification column bottom material directly loops back reactive system and utilizes.
Above-mentioned all utilize acetate and butylene or hybrid C 4 for the technology of feedstock production sec-butyl acetate in all not mentioned raw material butylene or hybrid C 4 polymerization can take place forms heavy hydrocarbon, more propose to remove the method for heavy hydrocarbon in the reaction product.
Summary of the invention
The technical problem to be solved in the present invention provides and a kind ofly prepares in the technology of sec-butyl acetate at acetate and C4 olefine reaction, the method that impurity such as heavy hydrocarbon are separated from reaction product, this method energy consumption material consumption is low, take off heavy hydrocarbon efficient height, and can improve process conditions, improves the quality of products.
The present invention solves the problems of the technologies described above by the following technical programs:
A kind of method for preparing impurity such as heavy hydrocarbon in the sec-butyl acetate reaction product that removes is extracted material out from the heavy hydrocarbon enrichment region, this material fully contacted with water, and heavy hydrocarbon and water natural layering in the material, the heavy hydrocarbon layer discharge with top refills system with following water layer.
The heavy hydrocarbon of indication of the present invention is a raw material C4 polymerized product.Adopt method of the present invention can remove carbonatoms in the molecule, especially easily remove carbonatoms in the molecule more than or equal to 10 heavy hydrocarbon more than or equal to 8 heavy hydrocarbon.
The heavy hydrocarbon enrichment region of indication of the present invention is meant the higher zone of heavy hydrocarbon relative concentration in the material, and its heavy hydrocarbon mass content is greater than 1%, refers in particular to heavy hydrocarbon mass content in the system greater than 5% part.After separating unreacted C4 and light constituent, profit uses water as entrainer, and azeotropic separation acetate and sec-butyl acetate are the heavy hydrocarbon enrichment region in the bottom of azeotropy rectification column.
Extract material out from the heavy hydrocarbon enrichment region, fully contact with water.The mass rate of water is 0～20 with the mass flow of materials ratio, and the mass rate that is preferably water is 0～10 with the mass flow of materials ratio.Mass rate as water compares greater than 20 with mass flow of materials, then consumes too big.The mass rate of water and mass flow of materials are than being 0 to be meant the water layer of material by leaving standstill.
From the material that the heavy hydrocarbon enrichment region is extracted out, contain acetate, sec-butyl acetate and heavy hydrocarbon.Wherein, acetate can be miscible with water, sec-butyl acetate is slightly soluble in water, and heavy hydrocarbon is insoluble in water, and heavy hydrocarbon and sec-butyl acetate density are littler than water, so when the material of extracting out from the heavy hydrocarbon enrichment region with after water fully contacts, will natural layering, heavy hydrocarbon is in the upper strata, and water is in lower floor, top heavy hydrocarbon layer is discharged, following water layer is refilled system.Because sec-butyl acetate can discharge system with heavy hydrocarbon, increased material loss, so should reduce the sec-butyl acetate content in the material extracted out as far as possible.Because sec-butyl acetate and water form azeotrope, distillate from the azeotropic distillation cat head, the sec-butyl acetate at the bottom of azeotropy rectification column is then less relatively.
The invention has the advantages that but effective elimination prepares the heavy hydrocarbon in the sec-butyl acetate reaction product, improve operational condition, the material consumption that cuts down the consumption of energy, and can improve the quality of products.
Description of drawings
Fig. 1 is adopted heavy hydrocarbon water wash column process schematic representation by embodiment 1,2;
Fig. 2 is adopted heavy hydrocarbon water wash column process schematic representation by embodiment 3.
The heavy hydrocarbon water wash column is a packing tower.
Embodiment
The present invention is further illustrated by following examples, but content not thereby limiting the invention.
Embodiment 1:
In former process, reaction mixture is removed unreacted C4 and light constituent, to mix with water again, profit uses water as entrainer, and azeotropic separation acetate and sec-butyl acetate are the heavy hydrocarbon enrichment region in the bottom of azeotropy rectification column.Referring to Fig. 1, to extract material at the bottom of the azeotropy rectification column out and enter heavy hydrocarbon water wash column bottom, mass flow of materials is 100Kg/hr.Water is injected heavy hydrocarbon water wash column top, and the quality flow is 800Kg/hr (mass rate of water is 8 with the mass flow of materials ratio).After water contacted with material is reverse, heavy hydrocarbon was discharged from the top of heavy hydrocarbon water wash column, and water is extracted out from heavy hydrocarbon water wash column bottom, and injected system again.
By above operation, can in time the heavy hydrocarbon of reaction gained and the heavy hydrocarbon of system's accumulative total be discharged, heavy hydrocarbon mass content at the bottom of the azeotropy rectification column is controlled at about 1～5%, and reduced the fouling of azeotropic distillation bottom reboiler, device continuous operation 1 month, the azeotropic distillation bottom reboiler does not have obvious scale formation.
Embodiment 2:
In former process, reaction mixture is removed unreacted C4 and light constituent, to mix with water again, profit uses water as entrainer, and azeotropic separation acetate and sec-butyl acetate are the heavy hydrocarbon enrichment region in the bottom of azeotropy rectification column.Referring to Fig. 1, to extract material at the bottom of the azeotropy rectification column out and enter heavy hydrocarbon water wash column bottom, mass flow of materials is 100Kg/hr.Water is injected heavy hydrocarbon water wash column top, and the quality flow is 150Kg/hr (mass rate of water is 1.5 with the mass flow of materials ratio).After water contacted with material is reverse, heavy hydrocarbon was discharged from the top of heavy hydrocarbon water wash column, and water is extracted out from heavy hydrocarbon water wash column bottom, and injected system again.
By above operation, can in time the heavy hydrocarbon of reaction gained and the heavy hydrocarbon of system's accumulative total be discharged, heavy hydrocarbon mass content at the bottom of the azeotropy rectification column is controlled at about 1～5%, and reduced the fouling of azeotropic distillation bottom reboiler, device continuous operation 6 months, the azeotropic distillation bottom reboiler does not have obvious scale formation.
The contrast experiment:
Will not extract material at the bottom of the azeotropy rectification column out and wash, then the heavy hydrocarbons content at the bottom of the azeotropy rectification column increases gradually, and after 1 month, the heavy hydrocarbon mass content reaches about 30% in the azeotropic distillation bottoms material, and the fouling of azeotropic distillation bottom reboiler is serious.The direct influence of reboiler fouling is: the reboiler poor heat transfer, the azeotrope of sec-butyl acetate and water can not steam cat head, causes inferior separating effect.
Embodiment 3:
In former process, reaction mixture is removed unreacted C4 and light constituent, to mix with water again, profit uses water as entrainer, and azeotropic separation acetate and sec-butyl acetate are the heavy hydrocarbon enrichment region in the bottom of azeotropy rectification column.Referring to Fig. 2, to extract material at the bottom of the azeotropy rectification column out and enter the heavy hydrocarbon water wash column bottom that water is housed in the tower, mass flow of materials is 100Kg/hr; Water leaves standstill motionlessly in the heavy hydrocarbon water wash column, and promptly the mass rate of water is 0 with the mass flow of materials ratio.When material was poured in the tower, water was with after material fully contacts, and heavy hydrocarbon is discharged from the top of heavy hydrocarbon water wash column.When the acid content in the heavy hydrocarbon greater than 0.5% the time, with the water injected system in the heavy hydrocarbon water wash column, and to heavy hydrocarbon water wash column make up water.
By above operation, can in time the heavy hydrocarbon of reaction gained and the heavy hydrocarbon of system's accumulative total be discharged, heavy hydrocarbons content at the bottom of the azeotropy rectification column is controlled at about 1～5%, and reduced the fouling of azeotropic distillation bottom reboiler, device continuous operation 80 days, the azeotropic distillation bottom reboiler does not have obvious scale formation.
Claims (3)
1. one kind removes the method for preparing heavy hydrocarbon in the sec-butyl acetate reaction product, it is characterized in that: extract material out from the heavy hydrocarbon enrichment region, this material is fully contacted heavy hydrocarbon and water natural layering in the material with water, top heavy hydrocarbon layer is discharged, following water layer is refilled system.
2. method according to claim 1 is characterized in that: describedly extract material out from the heavy hydrocarbon enrichment region, fully contact with water, the mass rate of its water is 0～20 with the mass flow of materials ratio.
3. method according to claim 2 is characterized in that: describedly extract material out from the heavy hydrocarbon enrichment region, fully contact with water, the mass rate of its water is 0～10 with the mass flow of materials ratio.
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB2007100357413A CN100445259C (en) | 2007-09-14 | 2007-09-14 | Method for removing heavy hydrocarbon from reaction product of preparation of sec-butyl acetate |
| BRPI0815874-6A BRPI0815874B1 (en) | 2007-09-14 | 2008-06-25 | METHOD FOR REMOVING HEAVY HYDROCARBONS FROM REACTION PRODUCTS IN THE PRODUCTION OF SEC-BUTYL ACETATE |
| JP2010524336A JP5194124B2 (en) | 2007-09-14 | 2008-06-25 | Method for removing heavy hydrocarbons from reaction products producing sec-butyl acetate |
| EP08757843A EP2192104B1 (en) | 2007-09-14 | 2008-06-25 | A process of removing hydrocarbons from the reaction products of producing sec-butyl acetate |
| US12/675,576 US8373003B2 (en) | 2007-09-14 | 2008-06-25 | Method of removing heavy hydrocarbons from reaction products in the production of sec-butyl acetate |
| AT08757843T ATE537137T1 (en) | 2007-09-14 | 2008-06-25 | METHOD FOR REMOVAL HYDROCARBONS FROM THE REACTION PRODUCTS OF THE PRODUCTION OF ACETIC ACID-SEC-BUTYL ESTER |
| PCT/CN2008/071434 WO2009033381A1 (en) | 2007-09-14 | 2008-06-25 | A process of removing heavier hydrocarbons from the reaction products of producing sec-butyl acetate |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB2007100357413A CN100445259C (en) | 2007-09-14 | 2007-09-14 | Method for removing heavy hydrocarbon from reaction product of preparation of sec-butyl acetate |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN101130496A true CN101130496A (en) | 2008-02-27 |
| CN100445259C CN100445259C (en) | 2008-12-24 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNB2007100357413A Active CN100445259C (en) | 2007-09-14 | 2007-09-14 | Method for removing heavy hydrocarbon from reaction product of preparation of sec-butyl acetate |
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| Country | Link |
|---|---|
| CN (1) | CN100445259C (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102282237A (en) * | 2008-12-09 | 2011-12-14 | 美国Gtc技术有限责任公司 | Heavy hydrocarbon removal systems and methods |
| CN104529764A (en) * | 2014-11-29 | 2015-04-22 | 惠州中创化工有限责任公司 | Method for extracting sec-butyl acetate by-product heavy hydrocarbon |
| CN106457065A (en) * | 2014-01-24 | 2017-02-22 | Gtc科技美国有限责任公司 | Heavy hydrocarbon removal |
| CN107324973A (en) * | 2017-07-05 | 2017-11-07 | 巨化集团技术中心 | A kind of preparation method of perfluoroalkyl ethanol |
| CN112920049A (en) * | 2019-12-05 | 2021-06-08 | 湖南中创化工股份有限公司 | Method and device for preparing tert-butyl acetate |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE69117871T2 (en) * | 1990-10-31 | 1996-11-07 | Daicel Chem | Process for the preparation of a lower alkyl acetate |
| US5384426A (en) * | 1992-12-08 | 1995-01-24 | Daicel Chemical Industries, Ltd. | Process for the preparation of isopropyl acetate |
-
2007
- 2007-09-14 CN CNB2007100357413A patent/CN100445259C/en active Active
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102282237A (en) * | 2008-12-09 | 2011-12-14 | 美国Gtc技术有限责任公司 | Heavy hydrocarbon removal systems and methods |
| CN102282237B (en) * | 2008-12-09 | 2015-07-22 | 美国Gtc技术有限责任公司 | Heavy hydrocarbon removal systems and methods |
| CN106457065A (en) * | 2014-01-24 | 2017-02-22 | Gtc科技美国有限责任公司 | Heavy hydrocarbon removal |
| CN106457065B (en) * | 2014-01-24 | 2019-12-10 | Gtc科技美国有限责任公司 | Heavy hydrocarbon removal |
| CN104529764A (en) * | 2014-11-29 | 2015-04-22 | 惠州中创化工有限责任公司 | Method for extracting sec-butyl acetate by-product heavy hydrocarbon |
| CN104529764B (en) * | 2014-11-29 | 2016-08-24 | 惠州宇新化工有限责任公司 | A kind of method extracting sec-butyl acetate by-product heavy hydrocarbon |
| CN107324973A (en) * | 2017-07-05 | 2017-11-07 | 巨化集团技术中心 | A kind of preparation method of perfluoroalkyl ethanol |
| CN112920049A (en) * | 2019-12-05 | 2021-06-08 | 湖南中创化工股份有限公司 | Method and device for preparing tert-butyl acetate |
| CN112920049B (en) * | 2019-12-05 | 2022-07-15 | 湖南中创化工股份有限公司 | Method and device for preparing tert-butyl acetate |
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| Publication number | Publication date |
|---|---|
| CN100445259C (en) | 2008-12-24 |
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Owner name: HUNAN ZHONGCHUANG CHEMICAL CO., LTD. Free format text: FORMER OWNER: HU XIANNIAN Effective date: 20090619 |
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Effective date of registration: 20090619 Address after: Yunxi District, Yueyang, Changling, Hunan Patentee after: HUNAN ZHONGCHUANG CHEMICAL CO., LTD. Address before: Yueyang City, Hunan province Yunxi Changling Hunan in the creation of Chemical Co., Ltd. Patentee before: Hu Xiannian |