CN1019011B - Method for recovering acrylic acid from acrylic acid waste oil - Google Patents
Method for recovering acrylic acid from acrylic acid waste oilInfo
- Publication number
- CN1019011B CN1019011B CN 89102172 CN89102172A CN1019011B CN 1019011 B CN1019011 B CN 1019011B CN 89102172 CN89102172 CN 89102172 CN 89102172 A CN89102172 A CN 89102172A CN 1019011 B CN1019011 B CN 1019011B
- Authority
- CN
- China
- Prior art keywords
- acrylic acid
- waste oil
- dimer
- vinylformic acid
- acid
- 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.)
- Expired
Links
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 title claims abstract description 60
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 title claims abstract description 27
- 239000002699 waste material Substances 0.000 title claims abstract description 25
- 238000000034 method Methods 0.000 title claims abstract description 20
- CYUZOYPRAQASLN-UHFFFAOYSA-N 3-prop-2-enoyloxypropanoic acid Chemical compound OC(=O)CCOC(=O)C=C CYUZOYPRAQASLN-UHFFFAOYSA-N 0.000 claims abstract description 33
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 12
- 238000004821 distillation Methods 0.000 claims abstract description 6
- 238000007670 refining Methods 0.000 claims abstract description 6
- 239000002904 solvent Substances 0.000 claims abstract description 6
- 238000010792 warming Methods 0.000 claims description 6
- 239000007864 aqueous solution Substances 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 2
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims 1
- 238000000926 separation method Methods 0.000 claims 1
- 238000000354 decomposition reaction Methods 0.000 abstract description 7
- 238000011084 recovery Methods 0.000 abstract description 7
- 230000008901 benefit Effects 0.000 abstract description 3
- 238000010438 heat treatment Methods 0.000 abstract description 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 6
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 239000010409 thin film Substances 0.000 description 3
- 238000010586 diagram Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 238000000197 pyrolysis Methods 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 238000007599 discharging Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 238000011221 initial treatment Methods 0.000 description 1
- -1 it consists of Chemical compound 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 238000000053 physical method Methods 0.000 description 1
- 238000005086 pumping Methods 0.000 description 1
- 239000010819 recyclable waste Substances 0.000 description 1
Images
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The present invention is a process for recovering acrylic acid from waste oil containing acrylic acid and acrylic acid dimer. The specific embodiment adopts a heating decomposition distillation device, waste oil containing acrylic acid and acrylic acid dimer is heated to 110-150 ℃ under normal pressure for decomposition distillation, and simultaneously solvent process water is added, so that the decomposition of acrylic acid dimer and the distillation of acrylic acid are facilitated. The method can recover more than 80 percent of acrylic acid in the waste oil, so that the total recovery rate of the acrylic acid in the acrylic acid refining system is improved to 99-99.5 percent from the original 98.5 percent, which is equivalent to increase the yield by 1 percent, and the economic benefit is obvious.
Description
The present invention for a kind of from the waste oil that contains vinylformic acid and acrylic acid dimer the method for acrylic acid.
In acrylic acid production process,, be to adopt thin-film evaporator that the vinylformic acid in the waste oil, acrylic acid dimer and hydroquinone of polymerization retarder are once reclaimed at present always have a certain amount of vinylformic acid and acrylic acid dimer and other high boiling material to discharge with waste oil.This method is better to the recovering effect of hydroquinone of polymerization retarder, but because heat transfer is not good, it is bad that acrylic acid dimer decomposes effect, and the material thickness, easily stops up and falls the liquid mouth, still has a certain amount of two olefin(e) acids and acrylic acid dimer to can not get reclaiming.Produce 30000 tons of acrylic acid production equipments per year as a cover and discharge 650 tons of waste oil approximately every year, wherein have to be vinylformic acid and acrylic acid dimer more than 50%.The waste oil of the discharging use that only acts as a fuel at present causes great waste.The objective of the invention is further to adopt physical method, the acrylic acid dimer in the vinylformic acid waste oil is decomposed, and vinylformic acid is fully reclaimed.
Technical solution of the present invention is to adopt thermal degradation distillatory device, the waste oil that will contain vinylformic acid and acrylic acid dimer is warming up to 110～150 ℃ under normal pressure, carry out destructive distillation, for reducing waste oil viscosity, be easy to decomposition and acrylic acid distillation of acrylic acid dimer, also add solvent process water simultaneously, the add-on of process water is vinylformic acid and acrylic acid dimer gross weight 1.5～5 times in the waste oil.Turn back in the vinylformic acid refining system decomposing the acrylic acid solution that reclaims, again process water is separated.
Reclaim process flow diagram with reference to vinylformic acid, the invention will be further described.
Waste oil after thin-film evaporator 1 primary treatment enters storage tank 2, join continuously in the storage tank 3 with pump 6, be warming up to 110～150 ℃ by chuck, process water also adds in the storage tank 3 after metering, the acrylic acid solution that obtains behind the destructive distillation returns the vinylformic acid refining system, raffinate enters in the storage tank 4 continuously, is sent to waste oil storage tank 5 through pump 7 again.
Accompanying drawing: vinylformic acid reclaims process flow diagram
The 1-thin-film evaporator
2,3,4,5-storage tank
6,7-pump
The 8-steam jacket
The 9-heating coil
W-solvent process water
The AA-acrylic acid aqueous solution
Ls-steam
The Lc-steam condensate
Several embodiments of the present invention are provided below.
Embodiment 1: get waste oil 1000 grams that contain vinylformic acid and acrylic acid dimer, it consists of, vinylformic acid 12.79%, acrylic acid dimer 54.25%, phenylformic acid 3.25%, Resorcinol 8.81%, other 20.9%, drop in 1000 milliliters of matrasss, be warming up to 145 ℃, add process water 1500 grams, when distillation yield is 2500 milliliters, record in the distillate, vinylformic acid 24.51%, acrylic acid dimer 0.3%, raffinate 337.1 grams, wherein vinylformic acid 9.06%, acrylic acid dimer 11.18%.This shows that the rate of decomposition of acrylic acid dimer is 91.35%, acrylic acid rate of recovery is 89.8%.
Embodiment 2: get waste oil 1000 grams that contain vinylformic acid and acrylic acid dimer, wherein vinylformic acid 12.13%, acrylic acid dimer 43.81%, phenylformic acid 3.52%, Resorcinol 11.55%, drop in 1000 milliliters of matrasss, be warming up to 140 ℃ under the normal pressure, add process water 1400 grams, when distillate is 2750 milliliters, wherein vinylformic acid is 17.84%, acrylic acid dimer 0.19%, and this moment, raffinate was 423 grams, wherein vinylformic acid 10.58%, acrylic acid dimer 8.15%, the rate of decomposition of acrylic acid dimer are 91.2%, and acrylic acid rate of recovery is 86.8%.
Embodiment 3: will contain vinylformic acid waste oil and put into continuously in the storage tank by 80kg/hr, and feed 6kg/cm by steam jacket
2Steam, keep the interior temperature of storage tank at 143 ℃, continuously join storage tank in by 140kg/hr process water, continuous distilled acrylic acid aqueous solution is turned back in the vinylformic acid refining system by 180kg/hr with pump, record the distillate composition and contain vinylformic acid 22.2%, acrylic acid dimer 0.3%, raffinate also are continuously discharged in another storage tank, with the past waste oil basin of pumping.Contain vinylformic acid 9.98% in this raffinate, acrylic acid dimer 10.25%.Acrylic acid rate of recovery is 90.1%.
Embodiment 4: get waste oil 1000 grams that contain vinylformic acid and acrylic acid dimer, wherein vinylformic acid 12.29%.Acrylic acid dimer 54.15%.Phenylformic acid 3.28%.Resorcinol 8.59% drops in 1000 milliliters of matrasss.Be warming up to 113 ℃ under the normal pressure.Add process water 3300 grams.When distillate is 5500 milliliters, record vinylformic acid 14.56% in the distillate.Acrylic acid dimer 0.08%.This moment, raffinate was 418 grams.Wherein vinylformic acid 10.8%.Acrylic acid dimer 6.53%.The rate of decomposition of acrylic acid dimer is that 94.1% acrylic acid rate of recovery is 87.7%.
Advantage of the present invention is: equipment, technology are simple, easy to operate, solvent is inexpensive, wide material sources, adopt acrylic acid and acrylic acid dimer more than 80% in the recyclable waste oil of the present invention, the rate of recovery that makes the acrylic acid refining system can be equivalent to increase output 1%, remarkable in economical benefits after bringing up to 99～99.5% 1 cover acrylic acid production devices and adopt the present invention by original 98.5%.
Claims (1)
1, a kind of from vinylformic acid waste oil the method for acrylic acid.It is characterized in that: the waste oil that will contain vinylformic acid and acrylic acid dimer is warming up to 110～150 ℃ under normal pressure.Be incorporated as 1.5～5 times solvent process water of vinylformic acid and acrylic acid dimer gross weight in the vinylformic acid waste oil simultaneously.Send out and separate distillation, the acrylic acid aqueous solution that reclaims is turned back in the vinylformic acid refining system, separation of propylene acid and solvent process water.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 89102172 CN1019011B (en) | 1989-04-15 | 1989-04-15 | Method for recovering acrylic acid from acrylic acid waste oil |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 89102172 CN1019011B (en) | 1989-04-15 | 1989-04-15 | Method for recovering acrylic acid from acrylic acid waste oil |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1046324A CN1046324A (en) | 1990-10-24 |
| CN1019011B true CN1019011B (en) | 1992-11-11 |
Family
ID=4854562
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN 89102172 Expired CN1019011B (en) | 1989-04-15 | 1989-04-15 | Method for recovering acrylic acid from acrylic acid waste oil |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN1019011B (en) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP4302934B2 (en) | 2002-04-25 | 2009-07-29 | 株式会社日本触媒 | Decomposition method of Michael adduct |
| KR100714631B1 (en) * | 2004-04-29 | 2007-05-07 | 주식회사 엘지화학 | Recovery method of acrylic acid |
| CN100398505C (en) * | 2006-07-28 | 2008-07-02 | 沈福昌 | Treatment method of acrylic acid and esters waste oil resource |
| CN105753688B (en) * | 2016-03-29 | 2018-01-05 | 黄河三角洲京博化工研究院有限公司 | A kind of method of acrylic acid dimer in reduction acrylic acid |
| CN108774124A (en) * | 2018-08-07 | 2018-11-09 | 陈惠双 | A method of the acrylic acid from the waste oil containing acrylic acid dimer |
-
1989
- 1989-04-15 CN CN 89102172 patent/CN1019011B/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| CN1046324A (en) | 1990-10-24 |
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Legal Events
| Date | Code | Title | Description |
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| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C06 | Publication | ||
| PB01 | Publication | ||
| C13 | Decision | ||
| GR02 | Examined patent application | ||
| C14 | Grant of patent or utility model | ||
| GR01 | Patent grant | ||
| C53 | Correction of patent of invention or patent application | ||
| COR | Change of bibliographic data |
Free format text: CORRECT: PATENTEE; FROM: DONGFANG CHEMICAL PLANT, BEIJING, THE EAST CHEMICAL PLANT,BEIJING TO: DONGFANG CHEMICAL FACTORY, BEIJING CHEMICAL INDUSTRY GROUP CO., LTD. |
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| CP01 | Change in the name or title of a patent holder |
Patentee after: Dongfang Chemical Plant, Beijing Chemical Industry Group Co., Ltd. Patentee before: Dongfang Chemical Plant, Beijing |
|
| C15 | Extension of patent right duration from 15 to 20 years for appl. with date before 31.12.1992 and still valid on 11.12.2001 (patent law change 1993) | ||
| OR01 | Other related matters | ||
| C19 | Lapse of patent right due to non-payment of the annual fee | ||
| CF01 | Termination of patent right due to non-payment of annual fee |