CN100410224C - New method of preparing tert-butyl phenol by alkylation of phenol and isobutene - Google Patents
New method of preparing tert-butyl phenol by alkylation of phenol and isobutene Download PDFInfo
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- CN100410224C CN100410224C CNB2006101341827A CN200610134182A CN100410224C CN 100410224 C CN100410224 C CN 100410224C CN B2006101341827 A CNB2006101341827 A CN B2006101341827A CN 200610134182 A CN200610134182 A CN 200610134182A CN 100410224 C CN100410224 C CN 100410224C
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- Prior art keywords
- gas
- liquid
- reaction
- iso
- butylene
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- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 title claims abstract description 44
- 238000000034 method Methods 0.000 title claims abstract description 21
- WJQOZHYUIDYNHM-UHFFFAOYSA-N 2-tert-Butylphenol Chemical compound CC(C)(C)C1=CC=CC=C1O WJQOZHYUIDYNHM-UHFFFAOYSA-N 0.000 title claims abstract description 7
- 238000005804 alkylation reaction Methods 0.000 title abstract 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 title description 2
- 230000029936 alkylation Effects 0.000 title 1
- 239000007788 liquid Substances 0.000 claims abstract description 43
- 238000006243 chemical reaction Methods 0.000 claims abstract description 39
- 150000002989 phenols Chemical class 0.000 claims abstract description 9
- 239000011344 liquid material Substances 0.000 claims abstract description 4
- 230000000694 effects Effects 0.000 claims description 3
- GJYCVCVHRSWLNY-UHFFFAOYSA-N 2-butylphenol Chemical group CCCCC1=CC=CC=C1O GJYCVCVHRSWLNY-UHFFFAOYSA-N 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 239000002994 raw material Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 239000006193 liquid solution Substances 0.000 description 2
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 230000003712 anti-aging effect Effects 0.000 description 1
- 239000012752 auxiliary agent Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000012847 fine chemical Substances 0.000 description 1
- 230000008676 import Effects 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 238000005504 petroleum refining Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/582—Recycling of unreacted starting or intermediate materials
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The present invention relates to a new method for preparing tert-butyl phenol by utilizing phenols and isobutylene and making them produce alkylation reaction. Said method is characterized by that on the basis of gas-liquid reaction equipment a Venturi ejector or gas-liquid mixing pump and a feed liquor circulating pump are added, so that the unreacted isobutylene can be further absorbed and fed into reaction still, under the action of ejector and feed liquor circulating pump the isobutylene gas and liquid material can be continuously circulated in the system so as to make the gas-liquid reaction be more uniform.
Description
Technical field
The invention belongs to the chemical industry technical field, the method for a kind of phenols and isobutene reaction is provided.
Background technology
Tertiary butyl phenols is important organic synthesis raw material and the intermediate of a big class in the field of fine chemical, is widely used in to make medicine, auxiliary agent etc.Some self is exactly Chemicals such as anti-aging agent, oxidation inhibitor, stopper and stablizer, is indispensable additive in petroleum refining industry, petroleum chemical enterprise and the macromolecular material industry.China's tertiary butyl phenols causes satisfying domestic growing market demands because outmoded, the production cost of production technique is too high.
At present, the following two kinds of methods of the many employings of the reaction of phenols and iso-butylene, the one, simple gas liquid reaction.Because this reaction belongs to gas liquid reaction, certainly exist the uneven problem of gas-liquid mixed, the reaction of phenol and iso-butylene is abundant inadequately, a large amount of iso-butylenes diffuse as tail gas, not only wasted a large amount of raw materials, and environment is had certain pollution, though equipment is simple, invest lessly, but the utilization ratio of iso-butylene is very low, certainly will increase the cost of product like this.The 2nd, reactive liquid solution.This method adopts high pressure to make iso-butylene liquefaction, reactive liquid solution is more even, there be not the problem and a large amount of wasting phenomenon of raw material thing of vent gas treatment in the iso-butylene of liquefaction and phenols reaction, improve iso-butylene body and function rate, but owing to need the condition of pressurization, there is requirement special to equipment, must increases the fund input of equipment like this.All there is certain shortcoming in present two kinds of methods, can't reach the purpose that reduces cost.
Summary of the invention
The invention provides a kind of phenols and iso-butylene and carry out the method that alkylated reaction prepares tert-butyl phenol, this method makes gas liquid reaction more even, and almost emission-free generation, has improved the utilization ratio of iso-butylene, device is simple, reduces the production cost of tertiary butyl phenols greatly.
The present invention is achieved through the following technical solutions:
A kind of phenols and iso-butylene carry out the method that alkylated reaction prepares tert-butyl phenol, it is characterized in that: this method is to add venturi-type eductors or gas-liquid mixing pump and feed liquid recycle pump on the basis of gas-liquid reaction apparatus, unreacted iso-butylene is absorbed once more, enter reactor, isobutene gas and liquid material are under the effect of venturi-type eductors or gas-liquid mixing pump and feed liquid recycle pump, constantly circulation makes gas liquid reaction more even in system.
The device that described method adopted is: gas-liquid reaction apparatus top is provided with venturi-type eductors or gas-liquid mixing pump and feed liquid recycle pump, and the gas-liquid reaction apparatus sidepiece is provided with prolong and is connected with surge flask, and surge flask connects U-tube manometer.
The invention has the beneficial effects as follows: this method makes gas liquid reaction more even, and almost emission-free generation, has improved the utilization ratio of iso-butylene, and device is simple, reduces the production cost of tertiary butyl phenols greatly.
Description of drawings
Fig. 1 is the structure iron of reaction unit.
The mark sequence number is expressed as follows respectively in the accompanying drawing: 1---reaction flask, and 2 one prolongs, 3---venturi-type eductors, 4---the feed liquid recycle pump, 5---surge flask, 6---U-tube manometer
Embodiment
A kind of phenols and iso-butylene carry out the method that alkylated reaction prepares tert-butyl phenol, this method is to add venturi-type eductors (or gas-liquid mixing pump) and feed liquid recycle pump on the basis of gas-liquid reaction apparatus, unreacted iso-butylene is absorbed once more, enter reactor, isobutene gas and liquid material are under the effect of venturi-type eductors or gas-liquid mixing pump and feed liquid recycle pump, constantly circulation makes gas liquid reaction more even in system.
The device that described method adopted is: see Fig. 1, gas-liquid reaction apparatus 1 top is provided with venturi-type eductors 3 (or gas-liquid mixing pump) and feed liquid recycle pump 4, gas-liquid reaction apparatus 1 sidepiece is provided with prolong 2 and is connected with surge flask 5, and surge flask 5 connects U-tube manometer 6.
Be the device reaction data contrast that adds venturi-type eductors and feed liquid recycle pump and do not add venturi-type eductors below:
Embodiment 1:(does not add the device reaction data of venturi-type eductors)
Having stirring, adding p-cresol 54g in the four-hole reaction flask of the 250mL of condensing works, the vitriol oil is made catalyzer, consumption 1.35g.Be warming up to 60-65 ℃, feed isobutene gas.The tail gas iso-butylene diffuses, monitor through gas-chromatography in the reaction process, BHT content reaches 90% when above, stop to feed iso-butylene, gas flow: 150ml/min, time 3.5h, experiment is 78g with the iso-butylene amount, the theoretical consumption of iso-butylene is 56g, has 30% iso-butylene to diffuse as tail gas approximately, and utilization ratio is 70%.
Embodiment 2:(adds venturi-type eductors and feed liquid recycle pump and does not add the device reaction data of venturi-type eductors)
Operate according to embodiment 1, reaction unit adds feed liquid recycle pump and venturi-type eductors, replaces whole system with iso-butylene earlier, open injector and feed liquid recycle pump simultaneously, and the transport portion iso-butylene, treat by U-tube manometer, measure and be negative pressure in the still, illustrate that entering the interior isobutene gas of still reacts, import iso-butylene again, so circulation is monitored BHT content to reach 90% until gas-chromatography, stop to feed iso-butylene, till reaction finishes.The accumulative total reaction is time 2.5h, and the accumulative total experiment is 58.95g with iso-butylene amount amount, and theoretical value is 56g, and iso-butylene does not almost have waste, and utilization ratio can be up to 95%.And shortened the reaction times, reduced energy consumption.
Claims (2)
1. phenols and iso-butylene carry out the method that alkylated reaction prepares tert-butyl phenol, it is characterized in that: this method is to add venturi-type eductors or gas-liquid mixing pump and feed liquid recycle pump on the basis of gas-liquid reaction apparatus, unreacted iso-butylene is absorbed once more, enter reactor, isobutene gas and liquid material are under the effect of venturi-type eductors or gas-liquid mixing pump and feed liquid recycle pump, constantly circulation makes gas liquid reaction more even in system.
2. the device that adopted of the described method of claim 1, it is characterized in that: be provided with venturi-type eductors or gas-liquid mixing pump and feed liquid recycle pump on gas-liquid reaction apparatus top, the gas-liquid reaction apparatus sidepiece is provided with prolong and is connected with surge flask, and surge flask connects U-tube manometer.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB2006101341827A CN100410224C (en) | 2006-11-07 | 2006-11-07 | New method of preparing tert-butyl phenol by alkylation of phenol and isobutene |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB2006101341827A CN100410224C (en) | 2006-11-07 | 2006-11-07 | New method of preparing tert-butyl phenol by alkylation of phenol and isobutene |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1948247A CN1948247A (en) | 2007-04-18 |
| CN100410224C true CN100410224C (en) | 2008-08-13 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNB2006101341827A Expired - Fee Related CN100410224C (en) | 2006-11-07 | 2006-11-07 | New method of preparing tert-butyl phenol by alkylation of phenol and isobutene |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN100410224C (en) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102464999B (en) * | 2010-11-05 | 2015-04-15 | 中国石油化工股份有限公司 | Oil gas absorption recovering method |
| CN102465000B (en) * | 2010-11-05 | 2015-02-18 | 中国石油化工股份有限公司 | Condensation recycling method of oil gas |
| CN102167709B (en) * | 2011-03-10 | 2013-11-06 | 常熟新特化工有限公司 | Method for preparing Tetrakis (hydroxymethyl) phosphonium chloride |
| CN102180905B (en) * | 2011-03-10 | 2013-11-06 | 常熟新特化工有限公司 | Preparation method of tetrakis(hydroxymethyl)phosphonium chloride-urea precondensate |
| CN102180904B (en) * | 2011-03-10 | 2013-09-18 | 常熟新特化工有限公司 | Preparation method for tetrakis hydroxymetyl phosphonium sulfuric |
| CN111393266A (en) * | 2020-02-21 | 2020-07-10 | 江苏迈达新材料股份有限公司 | BHT alkylation tail gas isobutene recovery process |
| CN111408319B (en) * | 2020-03-26 | 2022-01-28 | 北京理工大学 | Method for preparing p-tert-butyl toluene |
| CN113636916B (en) * | 2021-09-17 | 2023-08-29 | 陕西万汇能聚科技有限公司 | Method for synthesizing 2,4, 6-tri-tert-butylphenol |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH06298688A (en) * | 1993-04-19 | 1994-10-25 | Fuji Photo Film Co Ltd | Production of alkyl-substituted hydroquinone |
| CN1193007A (en) * | 1998-01-22 | 1998-09-16 | 义县精细化工总厂 | Process for synthesizing mixed tertbutyl-phenol |
| CN1313270A (en) * | 2000-03-13 | 2001-09-19 | 锦州石化天元集团公司 | Process for preparing 2,6-di-tear-butyl p-cresol |
-
2006
- 2006-11-07 CN CNB2006101341827A patent/CN100410224C/en not_active Expired - Fee Related
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH06298688A (en) * | 1993-04-19 | 1994-10-25 | Fuji Photo Film Co Ltd | Production of alkyl-substituted hydroquinone |
| CN1193007A (en) * | 1998-01-22 | 1998-09-16 | 义县精细化工总厂 | Process for synthesizing mixed tertbutyl-phenol |
| CN1313270A (en) * | 2000-03-13 | 2001-09-19 | 锦州石化天元集团公司 | Process for preparing 2,6-di-tear-butyl p-cresol |
Non-Patent Citations (2)
| Title |
|---|
| 2-叔丁基对甲苯酚的合成研究. 索陇宁.精细石油化工进展，第2卷第7期. 2001 |
| 2-叔丁基对甲苯酚的合成研究. 索陇宁.精细石油化工进展，第2卷第7期. 2001 * |
Also Published As
| Publication number | Publication date |
|---|---|
| CN1948247A (en) | 2007-04-18 |
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Effective date of registration: 20151125 Address after: 114044 Liaoning city of Anshan province high tech Zone Anqian Road No. 301 Patentee after: Sinosteel Anshan Research Institute of Thermo-energy Co., Ltd. Address before: 114044 Liaoning city of Anshan province Anqian high tech Development Zone, Road No. 301 Patentee before: National Zhongwei Coking Techn Engineering Research Center Co., Ltd. |
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| CF01 | Termination of patent right due to non-payment of annual fee | ||
| CF01 | Termination of patent right due to non-payment of annual fee |
Granted publication date: 20080813 Termination date: 20161107 |