CN101570500B - Method and equipment for preparing aromatic sulfonic acid by gas-phase sulphonation of aromatic organic compound - Google Patents
Method and equipment for preparing aromatic sulfonic acid by gas-phase sulphonation of aromatic organic compound Download PDFInfo
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- CN101570500B CN101570500B CN2009100743465A CN200910074346A CN101570500B CN 101570500 B CN101570500 B CN 101570500B CN 2009100743465 A CN2009100743465 A CN 2009100743465A CN 200910074346 A CN200910074346 A CN 200910074346A CN 101570500 B CN101570500 B CN 101570500B
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Abstract
The invention relates to a method and equipment for preparing aromatic sulfonic acid by the gas-phase sulfuric anhydride sulphonation of aromatic organic compounds with a rotating packed bed. The method solves the problems of the existing method in which the aromatic sulfonic acid is prepared by the sulphonation of aromatic organic compounds using sulfuric anhydride gas as sulphonating agent. The method is as follows: the aromatic organic compounds and the mixed sulfuric anhydride gas enter the started rotating packed bed and come into contact to produce partial sulphonation reaction; the liquid product after reaction enters a tubular heat exchanger and the reaction proceeds; and the aromatic sulfonic acid is obtained. The equipment comprises the rotating packed bed; the liquid inlet of the rotating packed bed is connected with a raw material storage tank; the gas inlet of the rotating packed bed is connected with the mixed sulfuric anhydride gas source; and the liquid outlet of the rotating packed bed is connected with a product storage tank through the tubular heat exchanger. The invention has the advantages of easy control of reaction temperature, reduction of the possibility ofsubsidiary reaction, enhancement of reactive selectivity, avoidance of environmental pollution, energy saving, small equipment volume, light weight, convenient installation and maintenance, and conve nient starting and shutdown.
Description
Technical field
The present invention relates to a kind of rotary packed bed method and apparatus for preparing aromatics sulfonic acid by gas phase sulfur trioxide sulfonated aromatic type organic that utilizes.
Background technology
Aromatics sulfonic acid is with sulphonating agent generation sulfonation reactions such as fragrant type organic matter and the vitriol oil, oleum or sulphur trioxides and the sulfonic acid type organic that obtains.With the vitriol oil or oleum is sulphonating agent when carrying out sulfonation reaction, has water to generate in the reaction process, can form spent acid, contaminate environment, and etching apparatus is unfavorable for the carrying out of sulfonation reaction; And be that sulphonating agent is when carrying out sulfonation reaction with the gas sulphur trioxide; Have that the sulfonation ability is strong, transformation efficiency is high, product purity is high and does not produce characteristics such as spent acid; But its technology and method are confined to the organic sulfonation of macromolecule more at present; For small molecular weight organism such as benzene, the organic sulfonation of toluene, especially thermo-sensitivity, then study less.Sulfonation reactor commonly used at present has still formula, pot group type, membrane type, jet-type etc.Wherein still formula and the alternate contact area of pot group type sulfonation reactor are little, the mass-and heat-transfer weak effect, and production efficiency is low; The film sulfonation reactor complex structure, the processing of equipment, manufacturing and setting accuracy require all higher, and investment cost is big; Turndown ratio is little, and the start-stop car is inconvenient, and heat interchanging area is limited; Some quick strong exothermal reaction is easy to generate local superheating; The carrying out that is unfavorable for sulfonation reaction especially for the organic sulfonation of some thermo-sensitivity, can reduce the selectivity of product.
The patent of invention of carrying out sulfonation reaction with jet sulfonation reactor mainly contains: (US 4113438 in U.S. Chemithon company; 1978) ram-jet formula sulfonation reactor (ImpactJet Reactor); This reactor drum atomizes high speed charging organism through Venturi; Form huge surface-area, and with the SO that introduces simultaneously
3-air mixture carries out violent sulfonation reaction of moment in nozzle trunnion portion, and and then reaction mixture by the cooling of cold cycle material chilling, avoids system temperature too high, influences product color.According to patent report, this device can be used for the sulfonation of plurality of raw materials such as dodecylbenzene, alcohol ether and terminal olefin; The injection circulation reactor of University Of Tianjin (CN96107060) sprays sulfonation reaction with high speed liquid phase workmanship as medium; Adopt and force the outer circulation interchanger; And the sulfonation of toluene studied; It is reported that this technology has solved the problem of heat extraction cooling, the products obtained therefrom quality is better, and this device can be used for the sulfonation of plurality of raw materials such as benzene, korenyl, fatty alcohol-ether and terminal olefin.More than the common ground of several kinds of reactor drums are the purposes that must repeatedly circulate and just can reach the cooling heat extraction and improve transformation efficiency sulfonated products; And sulfonation reaction is a fast strong exothermic process; Comprise a series of complex reaction (parallel reactor and consecutive reaction), repeatedly circulation causes the generation of side reaction easily, influences quality product; And the viscosity of sulfonated products also is unfavorable for circulation and injection far above raw material under high conversion.So according to reaction characteristics, the sulfonation reactor that exploitation is suitable is optimized technology, has very important significance to obtain the highly purified sulfonic acid product of high quality.
Summary of the invention
The present invention is that sulphonating agent sulfonated aromatic type organic prepares the problems referred to above that exist in the method for aromatics sulfonic acid in order to solve in the prior art with the gas sulphur trioxide; A kind of method and apparatus of preparing aromatic sulfonic acid by gas-phase sulphonation of aromatic organic compound is provided; It utilizes rotary packed bed efficient mass transfer characteristic that sulfonation reaction is once accomplished; Liquid product does not circulate to suppress the generation of side reaction; Thereby improve the purity and the yield of aromatics sulfonic acid, reach the purpose of enhancing productivity, cutting down the consumption of energy and reducing environmental pollution.
The present invention adopts following technical scheme to realize:
The method of preparing aromatic sulfonic acid by gas-phase sulphonation of aromatic organic compound; It is characterized in that step is following: open rotary packed bed; Fragrant type organic matter gets into rotary packed bed by rotary packed bed liquid-inlet; The sulphur trioxide mixed gas feeds rotary packed bed from rotary packed bed gas feed, liquid phase contacts in rotary packed bed filler with gas phase partly sulfonated reaction takes place, and reacted liquid product is discharged from rotary packed bed liquid exit; Get into tubular heat exchange and continue reaction, obtain product.
Temperature of reaction is 0 ℃～60 ℃ in rotary packed bed and the tubular heat exchange; The sulphur trioxide gas mixture is to be got by nitrogen, rare gas element or dry air dilution sulphur trioxide; Sulphur trioxide concentration in the sulphur trioxide gas mixture is 4%～12%v/v; The mol ratio of sulphur trioxide and fragrant type organic matter is 0.3～1.05: 1, and rotary packed bed rotating speed is 500～3000r/min.
The reacted gaseous product of being discharged by rotary packed bed pneumatic outlet gets into the distribution mixing tank after separating drying treatment, satisfy to get into after the distribution condition rotary packed bedly, recycles.
Fragrant type organic matter is benzene or toluene or dodecylbenzene.
Said fragrant type organic matter is a benzene, and rotary packed bed interior reaction temperature is 20 ℃～60 ℃, and the concentration of sulphur trioxide is 4%～9%v/v in the said sulphur trioxide gas mixture, and it is 0.5～1: 1 that sulphur trioxide and benzene add rotary packed bed interior mol ratio.
Said fragrant type organic matter is a toluene, and rotary packed bed interior reaction temperature is 0 ℃～10 ℃, and the concentration of sulphur trioxide is 6%～9%v/v in the said sulphur trioxide gas mixture, and it is 0.3～0.4: 1 that sulphur trioxide and toluene add rotary packed bed interior mol ratio.
Said fragrant type organic matter is a dodecylbenzene; Rotary packed bed interior reaction temperature is 50 ℃～60 ℃; The concentration of sulphur trioxide is 4%～12%v/v in the sulphur trioxide gas mixture, and it is 1.00～1.05: 1 that sulphur trioxide and dodecylbenzene add rotary packed bed interior mol ratio.
Realize the equipment of described preparing aromatic sulfonic acid by gas-phase sulphonation of aromatic organic compound method; Comprise rotary packed bed; Rotary packed bed liquid-inlet links to each other with the raw material storage tank; Rotary packed bed gas feed links to each other with sulphur trioxide mixing source of the gas, and rotary packed bed liquid exit links to each other with the product storage tank through tubular heat exchange.
Rotary packed bed shell is generally round shape, and shell is provided with the heat-eliminating medium chuck outward.
The raw material storage tank links to each other with rotary packed bed liquid-inlet through interchanger, pump and the liquid meter that is connected successively.
Rotary packed bed pneumatic outlet links to each other with the gas inlet of gas drier with the distribution mixing tank through gas-liquid separation device, and the pneumatic outlet of distribution mixing tank links to each other with rotary packed bed gas feed through gas meter.
The relative prior art of method and apparatus of the present invention has following beneficial effect:
What (1) the present invention adopted rotary packed bedly has a mass-transfer efficiency efficiently, can make gas-liquid contact mixing fast, has increased the gas-to-liquid contact area; Strengthened the contact effect, gas-liquid contact time is short, makes gas liquid reaction in this procedure division reaction; Thermal discharge is little; Temperature of reaction is controlled easily,, can be controlled at temperature well 0～10 ℃ optimum range especially for the sulfonation reaction of some heat-sensitive substances such as toluene.
(2) subsequent reactions is accomplished in tubular heat exchange, because interchanger is not easy to produce back-mixing, has reduced the generation of side reaction.In the sulfonation reaction of toluene, can effectively cut off the consecutive reaction approach, under the situation that does not add the agent of any resistance sulfone sulfonated products in the growing amount of ditolyl sulfone be controlled at below 1.3%; On the other hand, liberated heat shifts out rapidly easily, easy control of temperature; The carrying out that helps sulfonation reaction, the content that can make tosic acid in the sulfonated products is near 90%, and the content of m-toluene sulfonic acid can be controlled in below 1.0%; Thereby improved the selectivity of reaction.
(3) the gas phase recycle system has realized that tail gas does not discharge in this reactor drum, and sulphur trioxide recycles, and the distribution amount greatly reduces.Avoided contaminate environment, resource is recycled, and has practiced thrift the energy.
(4) the present invention adopted rotary packed bedly has advantages such as equipment volume is little, light weight, installation and maintenance are convenient, the start-stop car is convenient.
Description of drawings
Fig. 1 is the structural representation of the equipment of preparing aromatic sulfonic acid by gas-phase sulphonation of aromatic organic compound of the present invention
Among the figure: 1-raw material storage tank; The 2-interchanger; The 3-pump; 4,11,17,20-valve; The 5-liquid meter; The rotary packed bed liquid exit of 6-; 7-heat-eliminating medium chuck; The rotary packed bed liquid-inlet of 8-; 9-is rotary packed bed; The rotary packed bed pneumatic outlet of 10-; The 12-gas-liquid separation device; The outlet of 13-heat-eliminating medium; The 14-motor; The rotary packed bed gas feed of 15-; The 16-gas meter; 18-distribution mixing tank; The 19-gas meter, the 21-gas drier; 22-product storage tank; The 23-tubular heat exchange, the 24-cooling medium inlet.
Embodiment
Be described further in conjunction with the accompanying drawing specific embodiments of the invention.
A kind of method of preparing aromatic sulfonic acid by gas-phase sulphonation of aromatic organic compound, concrete technological process is following:
Open rotary packed bed 9; Regulate rotating speed at 500r/min～3000r/min; Fragrant type organic matter is got into rotary packed bed 9 with certain flow velocity by rotary packed bed liquid-inlet 8 through liquid meter by pump 3; The sulphur trioxide mixed gas of certain volume concentration is fed rotary packed bed 9 from rotary packed bed gas inlet 15 through gas meter 19, it is 0.3～1.05 that the volumetric concentration of regulating flow velocity and the sulphur trioxide mixed gas of fragrant type organic matter makes the mol ratio of sulphur trioxide and fragrant type organic matter: 1 gets final product.Gas phase and liquid phase rapid mixing the in rotary packed bed 9 carried out partial reaction; Reacted liquid product gets into tubular heat exchange 23 by rotary packed bed liquid exit 6 and lowers the temperature rapidly; In suitable temperature (according to the processing requirement of the fragrant type organic matter that is sulfonated; TR in the shell-and-tube reactor is controlled at 0 ℃～60 ℃) continue to accomplish reaction down, obtain product, get into product storage tank 22; The gaseous product that rotary packed bed internal reaction produces gets into gas-liquid separation devices 12 through rotary packed bed pneumatic outlet 9, after gas drier 21 (in adorn 98.3% vitriol oil) drying treatment, gets into distribution mixing tank 18 again and recycles.
Fragrant type organic matter of the present invention is benzene or toluene or dodecylbenzene.The concentration of sulphur trioxide is 4%～12% (v/v) in the sulphur trioxide gas mixture, and this sulphur trioxide gas mixture is to be got by nitrogen, rare gas element or dry air dilution sulphur trioxide, and rotary packed bed and temperature of reaction tubular heat exchange is 0 ℃～60 ℃
Realize the equipment of described preparing aromatic sulfonic acid by gas-phase sulphonation of aromatic organic compound method; Comprise rotary packed bed 9; Rotary packed bed liquid-inlet 8 links to each other with raw material storage tank 1; Rotary packed bed gas feed 15 links to each other with sulphur trioxide mixing source of the gas, and rotary packed bed liquid exit 6 links to each other with product storage tank 22 through tubular heat exchange 23.
Rotary packed bed 9 shell is a round shape, and shell is provided with heat-eliminating medium chuck 7 outward, has cooling medium inlet 24 and heat-eliminating medium outlet 13 on the heat-eliminating medium chuck 7.
Raw material storage tank 1 links to each other with rotary packed bed liquid-inlet 8 through interchanger 2, pump 3 and the liquid meter 5 that is connected successively.The sulfonation of thermo-sensitivity fragrant type organic matter, raw material will be through interchanger 2 processing of lowering the temperature before getting into rotary packed bed 9.
Rotary packed bed pneumatic outlet 10 links to each other with the gas inlet of gas drier 21 with distribution mixing tank 18 through gas-liquid separation device 12, and the pneumatic outlet of distribution mixing tank 18 links to each other with rotary packed bed gas feed 10 through gas meter 19.
Embodiment 1: the sulfonation of toluene
Adopt device flow process shown in Figure 1 to carry out the sulfonation of toluene.Adjusting rotary packed bed 9 rotating speed is 3000r/min; Raw material toluene cools to-5 ℃～0 ℃ through interchanger 2 before getting into rotary packed bed 9; The flow of the toluene of entering system is 6kg/h, and the flow of the gas mixture of trioxygen-containing sulphur 6% (v/v) (all the other are dry air) is 7Nm
3/ h, reaction is after liquid exit 6 gets into tubular heat exchange 23 to two kinds of raw materials rapidly in rotary packed bed 9, and the cooling holding temperature is at 0 ℃～10 ℃, and reacted product gets into product storage tank 22.The mol ratio that said sulphur trioxide and toluene add in this reactive system is 0.3: 1.The content of para-isomeride accounts for 87%-90% in the toluenesulphonic acids that reaction produces, and meta-isomer content is not more than 1.0%.
Embodiment 2: the sulfonation of benzene
Adopt device flow process shown in Figure 1 to carry out the sulfonation of benzene.Adjusting rotary packed bed 9 rotating speed is 500r/min, and the flow that gets into the benzene of system is 5kg/h, and the flow of the gas mixture of trioxygen-containing sulphur 8% (v/v) (all the other are dry air) is 9N m
3/ h, reaction is after liquid exit 6 gets into external heat exchanger 23 to two kinds of raw materials rapidly in rotary packed bed 9, and the cooling holding temperature is at 20 ℃～60 ℃, and reacted product gets into product storage tank 22.The mol ratio that said sulphur trioxide and said benzene add in this reactive system is 0.5: 1.
Embodiment 3: the sulfonation of benzene
Adopt device flow process shown in Figure 1 to carry out the sulfonation of benzene.Adjusting rotary packed bed 9 rotating speed is 1500r/min, and the flow that gets into the benzene of system is 5kg/h, and the flow of the gas mixture of trioxygen-containing sulphur 4% (v/v) (all the other are dry air) is 36Nm
3/ h, reaction is after liquid exit 6 gets into external heat exchanger 23 to two kinds of raw materials rapidly in rotary packed bed 9, and the cooling holding temperature is at 20 ℃～30 ℃, and reacted product gets into product storage tank 22.The mol ratio that said sulphur trioxide and said benzene add in this reactive system is 1: 1.
Embodiment 4: the sulfonation of dodecylbenzene
Adopt device flow process shown in Figure 1 to carry out the sulfonation of dodecylbenzene.Used korenyl is that the rotating speed of industrial korenyl (average molar mass is 240) adjustment rotary packed bed 9 is 1000r/min, and the flow that gets into the korenyl of system is 6kg/h, and the flow of the gas mixture of trioxygen-containing sulphur 12% (v/v) (all the other are dry air) is 5Nm
3/ h, reaction is after liquid exit 6 gets into external heat exchanger 23 to two kinds of raw materials rapidly in rotary packed bed 9, and the cooling holding temperature is at 50 ℃～60 ℃, and reacted product gets into product storage tank 22.The mol ratio that said sulphur trioxide and said korenyl add in this reactive system is 1.05: 1.
Embodiment 5: the sulfonation of dodecylbenzene
Adopt device flow process shown in Figure 1 to carry out the sulfonation of dodecylbenzene.Used korenyl is that the rotating speed of industrial korenyl (average molar mass is 240) adjustment rotary packed bed 9 is 2000r/min, and the flow that gets into the korenyl of system is 6kg/h, and the flow of the gas mixture of trioxygen-containing sulphur 6% (v/v) (all the other are dry air) is 10Nm
3/ h, reaction is after liquid exit 6 gets into external heat exchanger 23 to two kinds of raw materials rapidly in rotary packed bed 9, and the cooling holding temperature is at 50 ℃～55 ℃, and reacted product gets into product storage tank 22.The mol ratio that said sulphur trioxide and said korenyl add in this reactive system is 1.03: 1.
Claims (2)
1. the method for a preparing aromatic sulfonic acid by gas-phase sulphonation of aromatic organic compound; It is characterized in that step is following: open rotary packed bed; It is 0 ℃～60 ℃ that fragrant type organic matter gets into temperature by rotary packed bed liquid-inlet; Rotating speed is the rotary packed bed of 500～3000r/min, and the sulphur trioxide mixed gas feeds rotary packed bed from rotary packed bed gas feed, and wherein said sulphur trioxide gas mixture is to be got by nitrogen, rare gas element or dry air dilution sulphur trioxide; Sulphur trioxide concentration in the sulphur trioxide gas mixture is 4%～12%v/v; The mol ratio of sulphur trioxide and fragrant type organic matter is 0.3～1.05: 1, and liquid phase contacts in rotary packed bed filler with gas phase partly sulfonated reaction takes place, and reacted liquid product is discharged from rotary packed bed liquid exit; The entering temperature is that 0 ℃～60 ℃ tubular heat exchange continues reaction, obtains product;
Wherein said fragrant type organic matter is benzene, toluene or dodecylbenzene;
When stating fragrant type organic matter and be benzene, rotary packed bed interior reaction temperature is 20 ℃～60 ℃, and the concentration of sulphur trioxide is 4%～9%v/v in the said sulphur trioxide gas mixture, and the mol ratio that sulphur trioxide and benzene add in rotary packed bed is 0.5～1: 1;
When said fragrant type organic matter was toluene, rotary packed bed interior reaction temperature was 0 ℃～10 ℃, and the concentration of sulphur trioxide is 6%～9%v/v in the said sulphur trioxide gas mixture, and it is 0.3～0.4: 1 that sulphur trioxide and toluene add rotary packed bed interior mol ratio;
When said fragrant type organic matter is dodecylbenzene; Rotary packed bed interior reaction temperature is 50 ℃～60 ℃; The concentration of sulphur trioxide is 4%～12%v/v in the sulphur trioxide gas mixture, and it is 1.00～1.05: 1 that sulphur trioxide and dodecylbenzene add rotary packed bed interior mol ratio.
2. equipment of realizing the described preparing aromatic sulfonic acid by gas-phase sulphonation of aromatic organic compound method of claim 1; It is characterized in that comprising rotary packed bed (9); The shell of rotary packed bed (9) is a round shape; Shell is provided with heat-eliminating medium chuck (7) outward; Rotary packed bed liquid-inlet (8) links to each other with raw material storage tank (1); Raw material storage tank (1) links to each other with rotary packed bed liquid-inlet (8) through interchanger (2), pump (3) and the liquid meter (5) that is connected successively, and rotary packed bed pneumatic outlet (10) links to each other with the gas inlet of gas drier (21) with distribution mixing tank (18) through gas-liquid separation device (12), and the pneumatic outlet of distribution mixing tank (18) links to each other with rotary packed bed gas feed (15) through gas meter (19); Rotary packed bed gas feed (15) links to each other with sulphur trioxide mixing source of the gas, and rotary packed bed liquid exit (6) links to each other with product storage tank (22) through tubular heat exchange (23).
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| CN103936636B (en) * | 2013-01-23 | 2016-05-25 | 中国科学院大连化学物理研究所 | A kind of toluene sulfonation is prepared the method for p-methyl benzenesulfonic acid |
| CN104744314A (en) * | 2015-03-07 | 2015-07-01 | 甘肃兴荣精细化工有限公司 | Preparation method for heavy alkylbenzene sulfonic acid |
| CN106179133B (en) * | 2016-08-09 | 2018-12-07 | 北京化工大学 | A kind of rotary packed bed reactor of improved enzymatic and its application in fatty acid is prepared in enzymatic grease hydrolysis |
| CN106946745A (en) * | 2017-04-27 | 2017-07-14 | 山东星之联生物科技股份有限公司 | The preparation method of sodium p styrene sulfonate |
| CN113477188B (en) * | 2021-07-02 | 2023-08-29 | 北京化工大学 | Immersed rotary packed bed reactor and application thereof |
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| CN2892854Y (en) * | 2006-01-26 | 2007-04-25 | 中北大学 | Equipment for removing free formaldehyde in urea-formaldehyde resin |
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| CN2892854Y (en) * | 2006-01-26 | 2007-04-25 | 中北大学 | Equipment for removing free formaldehyde in urea-formaldehyde resin |
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| 喻华兵等.旋转填料床最新研究进展.《化学工程师》.2005,第113卷(第2期),35-37. * |
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