CN102234230A - Process method for synthesizing sec-butyl acetate from C4 fractions - Google Patents
Process method for synthesizing sec-butyl acetate from C4 fractions Download PDFInfo
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- CN102234230A CN102234230A CN2010101665979A CN201010166597A CN102234230A CN 102234230 A CN102234230 A CN 102234230A CN 2010101665979 A CN2010101665979 A CN 2010101665979A CN 201010166597 A CN201010166597 A CN 201010166597A CN 102234230 A CN102234230 A CN 102234230A
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Abstract
The invention relates to a process method for synthesizing sec-butyl acetate from C4 fractions. The process method is characterized in that acetic acid and C4 fractions are used as raw materials, macroporous strongly-acidic cation exchange resin is used as a catalyst, a 3-5-segment tubular fixed-bed reactor is employed, the acetic acid is fed in only one step, the C4 fractions are fed segment by segment, and the molar ratio of acetic acid to olefin in each segment of the reactor is greater than 9 when the total molar ratio of acetic acid to olefin in the reaction is 2-3; and an olefin polymerization inhibitor is simultaneously added to the reaction system at the adding amount of 20-200 mu g/g, and reaction is carried out at the reaction temperature of 50-120 DEG C and the reaction pressure of 1.0-2.0 MPa to generate sec-butyl acetate. The method has the advantages and effects that the selectivity of sec-butyl acetate is improved, the catalyst can be recycled and has long life, and the product has good quality.
Description
Technical field
The present invention relates to a kind of processing method of dividing synthetic 2-butyl acetate, belong to the organic chemical industry field with the C4 gold-plating.
Background technology
2-butyl acetate is a kind of good organic solvent, and it is widely used in cellulose nitrate, coating, leatheroid, medicine, printing ink and the plastics industry.The method of traditional mode of production 2-butyl acetate is to adopt the intermittent type still reaction both at home and abroad, is the reaction of catalyst acetic acid and butanols with sulfuric acid.Owing to produce water simultaneously in acetic acid and the esterified by butyl alcohol process, and water not only can cause the ester hydrolysis reaction of the reversed reaction of esterification, simultaneously because water and acetic acid azeotropic, cause the difficulty in the separation, therefore research now mainly concentrates in the direct esterification of acetic acid and butylene, has all reported acetic acid and the iso-butylene method that N-BUTYL ACETATE is produced in esterification under acidic ion exchange resin catalysis as US601807A and US5994578.Production for 2-butyl acetate, Chinese patent CN10112656A proposed modified resin catalyst at sour alkene than 1: the method for acetic acid synthesized secondary butyl ester under the condition of 1.15-1.80, because alkene takes place in the esterification under an acidic catalyst catalysis, also polymerization reaction take place is produced by products such as C8, C12 and C16, the selectivity of 2-butyl acetate is up to 98%, not only reduce the yield of 2-butyl acetate, and influence quality product.And Chinese patent CN101143819A has reported the method that adopts the acetic acid synthesized secondary butyl ester of catalytic distillation technology with the C4 raw material, though the 2-butyl acetate selectivity can reach 99%, but do not contain 1 in the C4 raw material that it adopts, the 3-divinyl, and the 1,3-butadiene content in the oil refining enterprise C 4 fraction is higher, if satisfy this processing requirement, must take the noble metal catalyst process for selective hydrogenation to handle not only technical process complexity, and process cost height.
The main source of C 4 fraction is the catalytic cracking unit of refinery factory at present, development trend along with crude oil heaviness and poor qualityization, catalytic cracking unit is for improving the light-end products yield, must improve the operating severity of catalytic cracking unit, contain in the refining plant C 4 cut 1, the 3-butadiene content is more and more higher, with high by 1, the refining plant C 4 cut of 3-butadiene content is the acetic acid synthesized secondary butyl ester of raw material, no matter adopt which kind of solid acid catalyst, 1,3-butadiene self all can polymerization reaction take place formation colloid cover in the catalyst active center, reduces catalyst life; Because 1,3-butadiene has high reaction activity, self-polymerization simultaneously also with the C4 raw material in other C 4 fraction reaction produce C8, C12 and C16 even high molecular weight polymers more, thereby reduce the selectivity that C 4 fraction generates 2-butyl acetate, influence quality product.Have not yet to see about reducing the report of 1,3-butadiene Dichlorodiphenyl Acetate Zhong Ding ester synthesis reaction solution.
Summary of the invention
Purpose of the present invention just for the shortcoming that overcomes above-mentioned prior art with not enough and a kind of processing method with the acetic acid synthesized secondary butyl ester of C 4 fraction is provided, thereby can obtain the product of high yield, high-quality, highly selective.
The objective of the invention is to realize by following technical proposal:
A kind of processing method with the acetic acid synthesized secondary butyl ester of C 4 fraction, with acetic acid and C 4 fraction is raw material, the macropore strong acid cation exchange resin is a catalyzer, adopt 3～5 sections calandria type fixed bed reactor to carry out, the disposable charging of acetic acid, the C 4 fraction sectional feeding reacts under the condition that total acetic acid and olefin molar ratio are 2-3, and ester acid and olefin molar ratio are greater than 9 in every section reactor; Add the alkene stopper simultaneously in reaction system, its add-on is 20-200 μ g/g, is 50-120 ℃ in temperature of reaction, and reaction pressure is that the 1.0-2.0MP reaction generates 2-butyl acetate;
Described C 4 fraction is a kind of raw material that contains high 1,3-butadiene that refinery factory catalytic cracking unit obtains, and described alkene stopper is RP-1412, described macropore strong acid cation exchange resin, model: A-35, K-300, D-06.
Described processing method, concrete steps are:
Macropore strong acid cation exchange resin butt amount is packed in the jacketed type hydro-thermal calandria type fixed bed reactor tubulation of stainless steel tube by the equal equal portions of section, be that the acetic acid of 2-3 and C 4 fraction are packed in the basin again with olefin molar ratio in acetic acid and the C 4 fraction, and adding alkene level of inhibitor is 20-200 μ g/g in acetic acid, acetic acid passes through each section feeding continuously from first section top, again ester acid and C 4 fraction olefin molar ratio are communicated with the acetic acid pipe of each section respectively greater than 9 amount and mix each section of feeding afterwards, in temperature of reaction is 50-120 ℃, and reaction pressure is that the 1.0-2.0MP reaction generates 2-butyl acetate; 2-butyl acetate is purified through separating with the component distillation of entrainer except that acetic acid with water with unreacted acetic acid, obtains the 2-butyl acetate product.
Acetic acid air speed and total acid alkene pump into reactor than by volume pump, C 4 fraction is by setting air speed and sour alkene than required total amount segmentation, pump into each section reactor respectively, guarantee sour alkene mol ratio in every section reaction mass greater than 9, alkene stopper add-on is the 20-200 μ g/g of combined feed total feed.Temperature of reaction is 60-120 ℃, and reaction pressure is 1.0-2.0MPa, reaction pressure by reactor after the back pressure valve regulation, it is 0.5-1.5h-1 that the C4 gold-plating divides the charging mass space velocity.Reaction product by reactor after back pressure valve decompression back flow into the C 4 fraction flashing tower, 2-butyl acetate separates through component distillation with unreacted acetic acid and removes the acetic acid purification, entrainer is a water.
Method of the present invention is a raw material with acetic acid and C 4 fraction, and acetic acid is dewatering agent, to the resin catalyst activation of dewatering; The macropore strong acid cation exchange resin is a catalyzer, the alkene stopper, wherein the main source of C 4 fraction is the catalytic cracking unit of refinery factory, development trend along with crude oil heaviness and poor qualityization, catalytic cracking unit must improve the operating severity of catalytic cracking unit for improving the light-end products yields, contain in the refining plant C 4 cut 1, the 3-butadiene content is more and more higher, it consists of, mass percent: Trimethylmethane 40.83%, normal butane 12.54%, anti-butylene 15.10%, n-butene 17.25%, iso-butylene 0.20%, maleic 13.54%, 1,3-butadiene 0.56%; Contain the butylene more than 45% in the C 4 fraction, can be used as the raw material of acetic acid synthesized secondary butyl ester.
The macropore strong acid cation exchange resin is a catalyzer, and highly acid B acid position is provided, and activation C4 alkene generates 2-butyl acetate, model A-35, K-300, D-06 with acetic acid generation addition reaction.
The alkene stopper is selected RP-1412 for use, mainly stops alkene in the C 4 fraction, and the polyreaction of 1,3-butadiene on an acidic catalyst especially prolongs catalyzer work-ing life, stops C4mono-olefin generation polymerization side reactions simultaneously.
Owing to take technique scheme to make the present invention compared with the prior art have following advantage and effect:
(1) selects that sour alkene mol ratio improves C 4 fraction transformation efficiency height greater than 9.0 in C 4 fraction sectional feeding and acetic acid reaction and the every section reactor for use, can reach 90%; Product 2-butyl acetate selectivity height can reach more than 99%; Total acid alkene mol ratio is low, and the later separation load is little;
(2) owing in reaction mass, add efficient alkene stopper, reduce that unsaturated component forms the colloid amount in the C 4 fraction on catalyzer, prolonged catalyzer work-ing life, high-efficiency polymerization inhibitor and acetic acid mix, but are insoluble to 2-butyl acetate, can recycle repeatedly,
(3) improve the selectivity that C 4 fraction is produced 2-butyl acetate, can reach more than 99%, improve the quality of products.
Description of drawings
Fig. 1 is a process method flow chart of the present invention,
Among the figure: 1-acetic acid tank, 2-C4 cut storage tank, 3-acetic acid fresh feed pump, 4,5, each section of 6-acetic acid pipeline, 7,8, each section of 9-reactor, 10-unreacted C 4 fraction flashing tower, 11,12, each section feeding pump of 13-C4 cut.
Embodiment
Embodiment raw material C 4 fraction is taken from the Sinopec Shijiazhuang MTBE of refinery company device, it consists of (mass percent): Trimethylmethane 40.83%, normal butane 12.54%, anti-butylene 15.10%, n-butene 17.25%, iso-butylene 0.20%, maleic 13.54%, 1,3-butadiene 0.56%, total butylene 45.09%.
Embodiment 1
By process method equipment schema shown in Figure 1, with the macropore strong acid cation exchange resin, model A-35, the butt 90g part that evenly classifies in three categories, every part 30 gram, being respectively charged into 3 internal diameters is 10 millimeters, the shell and tube reactor 7 of long 80 millimeters stainless steel tubes, 8,9, shell side leads to hot water, the storage tank 1 of again acetic acid being packed into, C 4 fraction is packed in the storage tank 2, both olefin molar ratio are 3, and in acetic acid, add alkene stopper RP-1412, and content is 100 μ g/g, acetic acid passes through each section feeding continuously from first section top with pump 3, per hour the acetic acid inlet amount is 120 grams, again ester acid and C 4 fraction olefin molar ratio are passed through the volume pump 11 of each section respectively greater than 9 amount, 12,13 with acetic acid pipe 4,5,6 are communicated with the mixing back feeds each section, total air speed is pressed 1.0h-1, and total feed is 90 Grams Per Hours, and every inlet amount of 3 fresh feed pumps is 30 Grams Per Hours, in temperature of reaction is 50 ℃, and reaction pressure is that the 2.0MP reaction generates 2-butyl acetate; 2-butyl acetate is purified through separating with the component distillation flashing tower 10 of entrainer except that acetic acid with water with unreacted acetic acid, obtains the 2-butyl acetate product.
Embodiment 2:
With embodiment 1 equipment, increase a reactor (accompanying drawing does not show), with the macropore strong acid cation exchange resin, model K-300, butt 120g evenly is divided into 4 equal portions, every part 30 gram, being respectively charged into 4 internal diameters is 10 millimeters, the logical hot water of the shell and tube 1,000 reactor shell sides of long 80 millimeters stainless steel tubes, the storage tank 1 of again acetic acid being packed into, C 4 fraction is packed in the storage tank 2, both olefin molar ratio are 2, and in acetic acid, add alkene stopper RP-1412, and content is 200 μ g/g, acetic acid passes through each section feeding continuously from first section top with pump, per hour the acetic acid inlet amount is 192 grams, again ester acid and C 4 fraction olefin molar ratio are communicated with mixing each section of feeding afterwards by the volume pump of each section respectively greater than 9 amount with the acetic acid pipe, total air speed is pressed 0.8h-1, and total feed is 96 Grams Per Hours, and every inlet amount of 4 fresh feed pumps is 30 Grams Per Hours, in temperature of reaction is 100 ℃, and reaction pressure is that the 1.5MP reaction generates 2-butyl acetate; 2-butyl acetate is purified through separating with the component distillation flashing tower 10 of entrainer except that acetic acid with water with unreacted acetic acid, obtains the 2-butyl acetate product.
With embodiment 1 equipment, increase by two reactors (accompanying drawing does not show), with the macropore strong acid cation exchange resin, model D-06, butt 150g evenly is divided into 5 equal portions, every part 30 gram, being respectively charged into 5 internal diameters is 10 millimeters, the logical hot water of the shell and tube 1,000 reactor shell sides of long 80 millimeters stainless steel tubes, the storage tank 1 of again acetic acid being packed into, C 4 fraction is packed in the storage tank 2, both olefin molar ratio are 2, and in acetic acid, add alkene stopper RP-1412, and content is 20 μ g/g, acetic acid passes through each section feeding continuously from first section top with pump, per hour the acetic acid inlet amount is 150 grams, again ester acid and C 4 fraction olefin molar ratio are communicated with mixing each section of feeding afterwards by the volume pump of each section respectively greater than 9 amount with the acetic acid pipe, total air speed is pressed 0.5h-1, and total feed is 75 Grams Per Hours, and every inlet amount of 5 fresh feed pumps is 30 Grams Per Hours, in temperature of reaction is 150 ℃, and reaction pressure is that the 1.0MP reaction generates 2-butyl acetate; 2-butyl acetate is purified through separating with the component distillation flashing tower 10 of entrainer except that acetic acid with water with unreacted acetic acid, obtains the 2-butyl acetate product.
Comparative Examples 1:
Take by weighing commercially available macropore strong acid cation exchange resin, model A-35, butt 90 gram, the part that evenly classifies in three categories, every part 30 gram is equipped with 3 internal diameters and is 10 millimeters, the shell and tube reactor of long 80 millimeters stainless steel tubes in being respectively charged into, and shell side leads to hot water.80 ℃ of temperature of reaction, the total air speed of refining plant C 4 is pressed 1.0h-1, and total feed is 90 Grams Per Hours, and every inlet amount of 3 fresh feed pumps is 30 Grams Per Hours; Acid alkene mol ratio is calculated by 3.0, per hour the acetic acid inlet amount is 120 grams, level of inhibitor is 0 μ g/g in the acetic acid, react after 3 hours, per hour get gaseous sample and liquid sample respectively from C 4 fraction flashing tower T1 top of tower and bottom respectively, carry out stratographic analysis, calculate C4 transformation efficiency and reaction preference, data are listed in table 1.
Comparative Examples 2:
Take by weighing commercially available macropore strong acid cation exchange resin, model D-06, butt 90 gram, the part that evenly classifies in three categories, every part 30 gram is equipped with 3 internal diameters and is 10 millimeters, the shell and tube reactor of long 80 millimeters stainless steel tubes in being respectively charged into, and shell side leads to hot water.80 ℃ of temperature of reaction, the total air speed of refining plant C 4 is pressed 1.0h-1, and reaction refining plant C 4 feedstock is directly pumped into by pump 2, and inlet amount is 90 Grams Per Hours, not separated charging; Acid alkene mol ratio is calculated by 3.0, per hour the acetic acid inlet amount is 120 grams, level of inhibitor is 0 μ g/g in the acetic acid, react after 3 hours, per hour get gaseous sample and liquid sample respectively from C 4 fraction flashing tower T1 top of tower and bottom respectively, carry out stratographic analysis, calculate C4 transformation efficiency and reaction preference, data are listed in table 1.
Table 1 embodiment and Comparative Examples comparing result
| Embodiment 1 | |
|
Comparative Examples 1 | Comparative Examples 2 | |
| Separate unit reactor acid alkene ratio | 9.0 | 9.0 | 9.0 | 9.0 | 3.0 |
| The C4 transformation efficiency, % | 79.5 | 86.27 | 91.48 | 75.43 | 71.51 |
| The 2-butyl acetate selectivity, % | 99.34 | 99.54 | 98.55 | 97.24 | 95.22 |
| C8 content, % | 0.66 | 0.46 | 1.23 | 2.43 | 4.23 |
| C12 content, % | Do not detect | Do not detect | 0.22 | 0.33 | 0.55 |
| React gum level on 100 hours rear catalysts, % | 0.02 | 0.02 | 0.09 | 0.42 | 0.95 |
Claims (2)
1. processing method with the acetic acid synthesized secondary butyl ester of C 4 fraction, it is characterized in that: with acetic acid and C 4 fraction is raw material, the macropore strong acid cation exchange resin is a catalyzer, adopt 3～5 sections calandria type fixed bed reactor to carry out, the disposable charging of acetic acid, the C 4 fraction sectional feeding reacts total acetic acid and olefin molar ratio and is under 2～3 the condition, and ester acid and olefin molar ratio are greater than 9 in every section reactor; Add the alkene stopper simultaneously in reaction system, its add-on is 20～200 μ g/g, is 50～120 ℃ in temperature of reaction, and reaction pressure is 1.0～2.0MP, and reaction generates 2-butyl acetate,
Described C 4 fraction is a kind of raw material that contains high 1,3-butadiene that refinery factory catalytic cracking unit obtains, and described alkene stopper is RP-1412,
Described macropore strong acid cation exchange resin, model: A-35, K-300, D-06.
2. the processing method with the acetic acid synthesized secondary butyl ester of C 4 fraction according to claim 1, it is characterized in that these technology concrete steps are: macropore strong acid cation exchange resin butt amount is packed in the jacketed type hydro-thermal calandria type fixed bed reactor tubulation of stainless steel tube by the equal equal portions of section, be that the acetic acid of 2-3 and C 4 fraction are packed in the basin again with olefin molar ratio in acetic acid and the C 4 fraction, and the adding level of inhibitor is 20～200 μ g/g in acetic acid, acetic acid passes through each section feeding continuously from first section top, again ester acid and C 4 fraction olefin molar ratio are communicated with the acetic acid pipe of each section respectively greater than 9 amount and mix each section of feeding afterwards, in temperature of reaction is 50-120 ℃, and reaction pressure is that the 1.0-2.0MP reaction generates 2-butyl acetate; 2-butyl acetate is purified through separating with the component distillation of entrainer except that acetic acid with water with unreacted acetic acid, obtains the 2-butyl acetate product.
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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102344364A (en) * | 2011-11-24 | 2012-02-08 | 长春工业大学 | Method for producing sec-butyl acetate by synthesizing acetic acid and mixed C4 |
| CN102964243A (en) * | 2012-11-16 | 2013-03-13 | 北京石油化工学院 | Preparation method of sec-butyl acetate |
| CN103172492A (en) * | 2011-12-23 | 2013-06-26 | 北京石油化工学院 | Preparation method of sec-butyl alcohol |
| CN103508884A (en) * | 2012-06-15 | 2014-01-15 | 中国石油化工股份有限公司 | Method for preparing sec-butyl acetate through utilizing etherification C4 fraction |
| CN104557523A (en) * | 2014-08-28 | 2015-04-29 | 丹东明珠特种树脂有限公司 | Catalyst loading method for synthesizing sec-butyl acetate |
| CN106397189A (en) * | 2016-08-30 | 2017-02-15 | 江西盛伟科技股份有限公司 | Synthesis method of tert-butyl chloroacetate |
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| CN101486640A (en) * | 2009-01-13 | 2009-07-22 | 湖南瑞源石化股份有限公司 | Preparation of sec-butyl acetate |
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Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102344364A (en) * | 2011-11-24 | 2012-02-08 | 长春工业大学 | Method for producing sec-butyl acetate by synthesizing acetic acid and mixed C4 |
| CN103172492A (en) * | 2011-12-23 | 2013-06-26 | 北京石油化工学院 | Preparation method of sec-butyl alcohol |
| CN103172492B (en) * | 2011-12-23 | 2017-02-08 | 北京石油化工学院 | Preparation method of sec-butyl alcohol |
| CN103508884A (en) * | 2012-06-15 | 2014-01-15 | 中国石油化工股份有限公司 | Method for preparing sec-butyl acetate through utilizing etherification C4 fraction |
| CN103508884B (en) * | 2012-06-15 | 2015-09-16 | 中国石油化工股份有限公司 | One utilizes C after ether 4cut prepares the method for 2-butyl acetate |
| CN102964243A (en) * | 2012-11-16 | 2013-03-13 | 北京石油化工学院 | Preparation method of sec-butyl acetate |
| CN102964243B (en) * | 2012-11-16 | 2017-07-11 | 北京石油化工学院 | The preparation method of sec-Butyl Acetate |
| CN104557523A (en) * | 2014-08-28 | 2015-04-29 | 丹东明珠特种树脂有限公司 | Catalyst loading method for synthesizing sec-butyl acetate |
| CN104557523B (en) * | 2014-08-28 | 2016-11-23 | 丹东明珠特种树脂有限公司 | A kind of Catalyst packing method synthesizing sec-Butyl Acetate |
| CN106397189A (en) * | 2016-08-30 | 2017-02-15 | 江西盛伟科技股份有限公司 | Synthesis method of tert-butyl chloroacetate |
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Application publication date: 20111109 |