CN100506780C - Process for preparing and extracting tert-butyl acetate - Google Patents
Process for preparing and extracting tert-butyl acetate Download PDFInfo
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- CN100506780C CN100506780C CNB2006100319385A CN200610031938A CN100506780C CN 100506780 C CN100506780 C CN 100506780C CN B2006100319385 A CNB2006100319385 A CN B2006100319385A CN 200610031938 A CN200610031938 A CN 200610031938A CN 100506780 C CN100506780 C CN 100506780C
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- butyl acetate
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- WMOVHXAZOJBABW-UHFFFAOYSA-N tert-butyl acetate Chemical compound CC(=O)OC(C)(C)C WMOVHXAZOJBABW-UHFFFAOYSA-N 0.000 title claims abstract description 33
- 238000004519 manufacturing process Methods 0.000 title description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims abstract description 26
- 238000000034 method Methods 0.000 claims abstract description 26
- 238000005886 esterification reaction Methods 0.000 claims abstract description 25
- 230000032050 esterification Effects 0.000 claims abstract description 24
- 150000002148 esters Chemical class 0.000 claims abstract description 18
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 claims abstract description 14
- 239000002253 acid Substances 0.000 claims abstract description 9
- 239000003054 catalyst Substances 0.000 claims abstract description 8
- 238000010992 reflux Methods 0.000 claims abstract description 3
- 238000006243 chemical reaction Methods 0.000 claims description 15
- 239000004215 Carbon black (E152) Substances 0.000 claims description 6
- 229930195733 hydrocarbon Natural products 0.000 claims description 6
- 150000002430 hydrocarbons Chemical class 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- 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 5
- 239000003456 ion exchange resin Substances 0.000 claims description 5
- 229920003303 ion-exchange polymer Polymers 0.000 claims description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 4
- 241000282326 Felis catus Species 0.000 claims description 2
- 239000011347 resin Substances 0.000 abstract 1
- 229920005989 resin Polymers 0.000 abstract 1
- 239000002994 raw material Substances 0.000 description 12
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 10
- 239000000047 product Substances 0.000 description 8
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 6
- 150000001336 alkenes Chemical class 0.000 description 6
- WHNQTHDJEZTVHS-UHFFFAOYSA-N 3-(1,3-benzothiazol-2-yl)propanoic acid Chemical compound C1=CC=C2SC(CCC(=O)O)=NC2=C1 WHNQTHDJEZTVHS-UHFFFAOYSA-N 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 238000005516 engineering process Methods 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 4
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 3
- 239000012346 acetyl chloride Substances 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- XMPZTFVPEKAKFH-UHFFFAOYSA-P ceric ammonium nitrate Chemical compound [NH4+].[NH4+].[Ce+4].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O XMPZTFVPEKAKFH-UHFFFAOYSA-P 0.000 description 2
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 238000005070 sampling Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 239000011592 zinc chloride Substances 0.000 description 2
- 235000005074 zinc chloride Nutrition 0.000 description 2
- XTFIVUDBNACUBN-UHFFFAOYSA-N 1,3,5-trinitro-1,3,5-triazinane Chemical compound [O-][N+](=O)N1CN([N+]([O-])=O)CN([N+]([O-])=O)C1 XTFIVUDBNACUBN-UHFFFAOYSA-N 0.000 description 1
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
- 239000000020 Nitrocellulose Substances 0.000 description 1
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 238000006137 acetoxylation reaction Methods 0.000 description 1
- 238000007171 acid catalysis Methods 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- CCGKOQOJPYTBIH-UHFFFAOYSA-N ethenone Chemical compound C=C=O CCGKOQOJPYTBIH-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- MHCFAGZWMAWTNR-UHFFFAOYSA-M lithium perchlorate Chemical compound [Li+].[O-]Cl(=O)(=O)=O MHCFAGZWMAWTNR-UHFFFAOYSA-M 0.000 description 1
- 229910001486 lithium perchlorate Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 229920001220 nitrocellulos Polymers 0.000 description 1
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000003672 processing method Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- -1 tin halides Chemical class 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
The invention discloses a preparing and extracting method of tert-butyl acetate, which is characterized by the following: adding acetate and C4 with isobutene continuously at 1:0.30-1:5.00 molar rate in the esterification tower with strong acid ionic exchange resin catalyst; setting inlet air-speed of acetate at 0.5-5.0 h-1 and catalyst quantity at 30-90 ml and pressure at 0.5-2.0 Mpa at 30-110 deg.c; obtaining coarse ester; sending ester in the separating tower; controlling top-gas reflux temperature at 85-100 deg.c to deacidify; dehydrocarbylating at 70-85 deg.c; dealcoholizing at 78-90 deg.c; rectifying between 90 and 100 to obtain the product.
Description
One, technical field:
The present invention relates to a kind of method of producing tert.-butyl acetate, particularly relate to a kind of with acetate and C
4Method for feedstock production and extracting tert-butyl acetate.
Two, background technology:
Tert.-butyl acetate is a kind of colourless liquid, can be dissolved in acetate with alcohol, ether mix, and is water-soluble hardly, is shockproof dose of good gasoline, can be used as the solvent of nitrocellulose etc.
The method of present industrial production tert.-butyl acetate has: 1. acetic anhydride method: with the trimethyl carbinol and acetic anhydride is the raw material synthesis of acetic acid tert-butyl ester, use therein catalyzer has zinc chloride, lithium chloride, lithium perchlorate, ceric ammonium nitrate, pyridine, triethylamine, 4-Dimethylamino pyridine (DMAP), tin tetrachloride etc., but the very easy moisture absorption of zinc chloride, organic amine all has pungent odor and certain toxicity, and cost is higher; 2. acetyl chloride method: with the trimethyl carbinol and Acetyl Chloride 98Min. is the raw material synthesis of acetic acid tert-butyl ester, and use therein catalyzer has N, N-xylidine and magnesium; 3. be the raw material synthesis of acetic acid tert-butyl ester with the trimethyl carbinol and ketene, use therein catalyzer has acid catalyst and tin halides.More than three kinds of methods all used the trimethyl carbinol to do raw material, but the trimethyl carbinol is sterically hindered very big, and intramolecular dehydration very easily takes place again, so the reaction with the aforesaid method synthesis of acetic acid tert-butyl ester is had relatively high expectations, productive rate is lower, and side reaction is many, especially can not use the catalyzer of water separation capability; 4. react by the acid catalysis acetoxylation of iso-butylene and acetate and produce tert.-butyl acetate.Three kinds of acid alcohol esterification techniques of this method and front are compared, and superiority is embodied in following two aspects: (1) adopts alkene to do raw material, can reduce production costs relatively; (2) acid/alkene technology belongs to typical green chemical industry technology.Therefore acid/alkene method must be the main method of producing tert.-butyl acetate.But the weak point of this method is Ta Nei regular meeting in the reaction process situation of accumulation of (iso-butylene) dimer and catalyst failure takes place; cause forming the parking of mud shape settling and ultimate demand and clean out tower, and the dipolymer of alkene has increased the separation and purification difficulty of tert.-butyl acetate.
In order to reduce or to eliminate the associated problem of prior art and, wish to use the material that more is easy to get than pure iso-butylene to produce tert.-butyl acetate with the expensive problem of refining iso-butylene.In recent years, have bibliographical information under the effect of a kind of big net type strongly acidic ion-exchange resin catalyst, to produce tert.-butyl acetate, but the employed catalyzer of this technology is not high to the selectivity of tert.-butyl acetate by the mixture of acetate, diacetyl oxide and methyl tertiary butyl ether (MTBE) or Ethyl Tertisry Butyl Ether (ETBE).
By acetic anhydride method, the thick ester of acetyl chloride method synthetic, the method of purifying generally is that to be washed till the ester layer with 10% salt of wormwood or sodium carbonate solution again after washing with water be neutrality, the ester layer of telling distills after with anhydrous magnesium sulfate drying, and the cut of collecting 95～96 ℃ is product.The thick ester of other method synthetic generally is to carry out rectifying.The purity of the tert.-butyl acetate that is obtained by these methods is generally 99.0%.Up to now, adopt acetate and the C that contains certain iso-butylene
4Reaction obtains thick ester, and the method that pass through depickling again, take off hydrocarbon, dealcoholysis obtains purity 99.5% above tert.-butyl acetate is not appeared in the newspapers.
Three, summary of the invention:
The invention reside in provides a kind of plentiful C of refinery that adopts
4Be raw material, production cost is low, the processing method of the preparation tert.-butyl acetate that product purity is high.
The present invention is achieved through the following technical solutions: a kind of method for preparing tert.-butyl acetate, acetate and the C that contains iso-butylene
4Add continuously and be equipped with in the esterification column of strong acid ion exchange resin catalyzer, the mol ratio of acetate and iso-butylene is 1: 0.30～1: 5.00, is 0.5～5.0h in the charging air speed of acetate
-1, catalyst levels is 30～90ml, pressure 0.5～2.0MPa carries out esterification under 30～110 ℃ of conditions of temperature of reaction, obtains thick ester; Thick ester is sent into knockout tower, by control cat head gas phase reflux temperature in depickling between 85～100 ℃, taking off hydrocarbon, dealcoholysis between 78～90 ℃ between 70～85 ℃, rectifying obtains the tert.-butyl acetate product between 90～100 ℃ at last.
Can add 1～15% water in the described acetate, to generate the polymerization that the by product trimethyl carbinol suppresses alkene.
Also can directly add 5～20% alcohol in the described acetate, to suppress the polymerization of alkene.
Described esterification column can have two esterification columns simultaneously, the thick ester that comes out from first esterification column again with the C that replenishes
4Enter second esterification column and react, the charging air speed of thick ester is 1.0～2.0h
-1, other esterification conditions are identical with first esterification column.
Raw material of the present invention can be pure iso-butylene, also can be the C that contains iso-butylene of refinery's by-product
4Or contain other materials of iso-butylene.
The present invention adopts the plentiful C of refinery
4Be raw material, can reduce production cost of products significantly, also overcome the branch water difficulty that classical acid/pure technology exists simultaneously, the problem that causes energy expenditure to increase; Realized continuous esterification and separated purification, the product content of tert.-butyl acetate can reach more than 99.5%.
Four, description of drawings:
Fig. 1 is a process flow sheet of the present invention;
Among the figure: R-1 is an esterification column, and R-2 is an esterification column, and T-3 is a knockout tower, and T-4 is a knockout tower, and V-5 is that storage sample jar, V-6 are storage sample jars.
Five, embodiment:
The present invention is further described with specific embodiment with reference to the accompanying drawings below:
Acetate and C
4Reaction be acid catalyzed reaction, can be intermittently or continuous operation mode.Tube inner diameter 16mm, catalyzer adopts strong acid ion exchange resin, and loaded catalyst is 30ml～90ml, and acetate is squeezed into the constant-flux pump metering, adopts temperature controlling instruments to carry out temperature control.Experiment T-1, T-2, T-3, T-4 are raw materials used is acetate and C
4, acetate is sent into certain speed in the esterification column that ion-exchange resin catalyst is housed, and keeps stable C
4Exhaust flow (60ml/min), pressure 0.8MPa changes temperature of reaction, reacts sampling in 6～7 hours and analyzes.Thick ester in depickling between 85～100 ℃, taking off hydrocarbon, dealcoholysis between 78～90 ℃ between 70～85 ℃, rectifying obtains the tert.-butyl acetate product between 90～100 ℃ at last.The results are shown in Table 1.
The result of table 1, the synthetic thick tert.-butyl acetate of change temperature of reaction
Experiment T-5, T-6, T-8, T-10, T-11 is raw materials used is acetate, water and C
4, experiment T-7 is raw materials used to be acetate, pure and mild C
4, T-9 is with acetate and C in experiment
4Be raw material, keeping temperature of reaction is 65 ℃, changes acetate air speed and reaction pressure, and other conditions are with embodiment 1.Thick ester in depickling between 85～100 ℃, taking off hydrocarbon, dealcoholysis between 78～90 ℃ between 70～85 ℃, rectifying obtains the tert.-butyl acetate product between 90～100 ℃ at last.The results are shown in Table 2.
The result of table 2, change acetate air speed and the synthetic thick tert.-butyl acetate of reaction pressure
The C that tert.-butyl acetate crude product (the containing tert.-butyl acetate 18.97%) circulation that is obtained by first esterification column enters second esterification column and replenishes
4Esterification takes place, control C
4Exhaust flow 60ml/min.Keep 65 ℃ of temperature of reaction, change reaction pressure and the tert.-butyl acetate crude product sample introduction air speed T-12,13,14,15,16 that experimentizes, other conditions are reacted 3 hours sampling analysis with embodiment 1.Thick ester in depickling between 85～100 ℃, taking off hydrocarbon, dealcoholysis between 78～90 ℃ between 70～85 ℃, rectifying obtains the tert.-butyl acetate product between 90～100 ℃ at last.The results are shown in Table 3.
The result of table 3, change reaction pressure and tert.-butyl acetate crude product sample introduction air speed synthesis of acetic acid tert-butyl ester circulating reaction
Claims (4)
1, a kind of method for preparing tert.-butyl acetate is characterized in that: acetate and the C that contains iso-butylene
4Add continuously and be equipped with in the esterification column of strong acid ion exchange resin catalyzer, the mol ratio of acetate and iso-butylene is 1:0.30～1:5.00, at the charging air speed 0.5～5.0h of acetate
-1, catalyst levels is 30～90ml, pressure 0.5～2.0MPa carries out esterification under 30～110 ℃ of conditions of temperature of reaction, obtains thick ester; Thick ester is sent into knockout tower, by control cat head gas phase reflux temperature in depickling between 85～100 ℃, taking off hydrocarbon, dealcoholysis between 78～90 ℃ between 70～85 ℃, rectifying obtains the tert.-butyl acetate product between 90～100 ℃ at last.
2, the method for preparing tert.-butyl acetate according to claim 1 is characterized in that: add 1～15% water in the described acetate.
3, the method for preparing tert.-butyl acetate according to claim 1 is characterized in that: add 5～20% alcohol in the described acetate.
4, the method for preparing tert.-butyl acetate according to claim 1 is characterized in that: described esterification column has two esterification columns simultaneously, the thick ester that comes out from first esterification column again with the C that replenishes
4Enter second esterification column and react, the charging air speed of thick ester is 1.0～2.0h
-1, other esterification conditions are identical with first esterification column.
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| CNB2006100319385A CN100506780C (en) | 2006-07-04 | 2006-07-04 | Process for preparing and extracting tert-butyl acetate |
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| CNB2006100319385A CN100506780C (en) | 2006-07-04 | 2006-07-04 | Process for preparing and extracting tert-butyl acetate |
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| CN100506780C true CN100506780C (en) | 2009-07-01 |
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Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101402566B (en) * | 2008-07-16 | 2013-01-09 | 岳阳桦科化工有限责任公司 | Method for producing high-purity low-class fatty acid ester |
| CN101691496B (en) * | 2009-09-17 | 2012-01-25 | 湖南长岭石化科技开发有限公司 | Method for modifying catalytic gasoline and reducing alkene |
| KR20110077120A (en) * | 2009-12-30 | 2011-07-07 | 에스케이이노베이션 주식회사 | Method for preparing tert-butyl acetate |
| CN102146019B (en) * | 2011-02-22 | 2013-05-15 | 湖南长岭石化科技开发有限公司 | Method for preparing alcohols from olefin |
| CN104418688A (en) * | 2013-08-19 | 2015-03-18 | 湖南长岭石化科技开发有限公司 | Method for separating and purifying isobutylene from mixed C4 |
| CN106316840A (en) * | 2016-08-23 | 2017-01-11 | 深圳市普利凯新材料股份有限公司 | Method for preparing and purifying tertbutyl propionate |
| CN108658763A (en) * | 2018-06-21 | 2018-10-16 | 岳阳富和科技有限公司 | A kind of to generate isooctene using acetic acid mixing C4, repeated hydrogenation produces the manufacturing method of high pure isooctane |
| 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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