CN1050311C - Method for producing high-purity butene-1 - Google Patents
Method for producing high-purity butene-1 Download PDFInfo
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- CN1050311C CN1050311C CN94110735A CN94110735A CN1050311C CN 1050311 C CN1050311 C CN 1050311C CN 94110735 A CN94110735 A CN 94110735A CN 94110735 A CN94110735 A CN 94110735A CN 1050311 C CN1050311 C CN 1050311C
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- butene
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- butadiene
- hydrogenation
- carbon
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- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 title claims abstract description 94
- 238000004519 manufacturing process Methods 0.000 title description 2
- 238000005984 hydrogenation reaction Methods 0.000 claims abstract description 33
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims abstract description 30
- 239000000463 material Substances 0.000 claims abstract description 17
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 claims abstract description 16
- 238000000034 method Methods 0.000 claims abstract description 14
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 12
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 12
- 150000001993 dienes Chemical class 0.000 claims abstract description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 8
- 150000001345 alkine derivatives Chemical class 0.000 claims abstract description 8
- 239000001257 hydrogen Substances 0.000 claims abstract description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 8
- 239000001282 iso-butane Substances 0.000 claims abstract description 8
- 150000001875 compounds Chemical class 0.000 claims abstract description 4
- 239000003054 catalyst Substances 0.000 claims description 9
- 238000010992 reflux Methods 0.000 claims description 8
- 238000005516 engineering process Methods 0.000 claims description 7
- 235000013847 iso-butane Nutrition 0.000 claims description 7
- 238000006266 etherification reaction Methods 0.000 claims description 5
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 claims description 5
- 229920000642 polymer Polymers 0.000 claims description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
- 238000009835 boiling Methods 0.000 claims description 3
- 238000000926 separation method Methods 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 239000011593 sulfur Substances 0.000 claims 1
- 239000012535 impurity Substances 0.000 abstract description 6
- 238000005265 energy consumption Methods 0.000 abstract description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 1
- 239000001301 oxygen Substances 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 238000000746 purification Methods 0.000 abstract 1
- 238000007086 side reaction Methods 0.000 abstract 1
- 150000003568 thioethers Chemical class 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 10
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 8
- 239000002994 raw material Substances 0.000 description 7
- 230000000694 effects Effects 0.000 description 5
- 238000006317 isomerization reaction Methods 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- IJDNQMDRQITEOD-UHFFFAOYSA-N sec-butylidene Natural products CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 5
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 4
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 238000009833 condensation Methods 0.000 description 4
- 230000005494 condensation Effects 0.000 description 4
- IAQRGUVFOMOMEM-ONEGZZNKSA-N trans-but-2-ene Chemical compound C\C=C\C IAQRGUVFOMOMEM-ONEGZZNKSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 229930195735 unsaturated hydrocarbon Natural products 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
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 2
- 239000005864 Sulphur Substances 0.000 description 2
- 238000006477 desulfuration reaction Methods 0.000 description 2
- 230000023556 desulfurization Effects 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000005194 fractionation Methods 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- 239000001294 propane Substances 0.000 description 2
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 2
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 239000012808 vapor phase Substances 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- 235000013844 butane Nutrition 0.000 description 1
- 238000004523 catalytic cracking Methods 0.000 description 1
- 238000005336 cracking Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000004230 steam cracking Methods 0.000 description 1
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Abstract
The invention relates to a novel process for producing high-purity butene-1 from C4, which is characterized in that the volatility difference and azeotropic property between impurity compounds and C four components are utilized, isobutane is removed through a fractionating tower, trace sulfides, oxygen-containing compounds, carbon three diene and alkyne are removed, the materials can directly enter a selective hydrogenation reactor to enable butadiene to be mono-olefine so as to be further removed and separated, purification is not needed, the process flow is simplified, the energy consumption is reduced, the hydrogen partial pressure in the selective hydrogenation process is reduced, side reactions are reduced, the yield of butene-1 is improved, and the total yield reaches 85-92%.
Description
Annotate the preparation side that the present invention relates to butene-1.
Mixed c 4 is produced in paying of refinery catalytic cracking unit and ethene steam cracking device, it is the cheap raw material of producing butene-1, particularly (lead into methyl tertiary butyl ether(MTBE) with the methyl alcohol reaction by isobutene through etherification reaction for this mixed c 4, as Chinese patent 88109705.5,89105325.5 etc.), removed with the very approaching isobutene of butene-1 boiling point after, producing high-purity butylene-1 by its residue carbon four is the process route of economical rationality the most, remove in the residue carbon four after the etherificate and contain butene-1, iso-butane, normal butane, beyond anti-butene-2 and small amount of carbon three hydrocarbon, also contain the 1,3-butadiene equal altitudes unsaturated hydrocarbons about 1% (M/M), need remove the 1,3-butadiene very approaching owing to produce high-purity butylene-1 with the butene-1 boiling point.The method of prior art has two kinds, a kind of is degree of depth extract and separate butadiene, as Japan Patent 58-126820, but this method can only make the butadiene content in carbon four logistics reduce to 60-80PPM, when the content of the butene-1 in the carbon four is lower than 50% such as catalytically cracked C four, the concentration of butadiene will can not satisfy polymer grade butene-1 quality requirement greater than 120PPM in the product butene-1, and the investment cost of this method is also higher.Another kind method is to utilize to select the method for hydrogenation to remove butadiene, and on general palladium catalyst, but the butene-1 isomery turns to butene-2, the butene-1 yield is descended, but German patent DE 3.426.349 thinks behind butene-1 isomerization rate and the hydrogenation that the butadiene residual volume is relevant in the logistics, the butadiene residual volume is more little, and the butene-1 isomerization rate is high more.Therefore before hydrogenation earlier through twice separated, make butene-1 be concentrated to 85%～90% after, select the hydrogenation and removing butadiene again, can improve butadiene residual volume in the logistics behind hydrogenation like this, take this to improve the butene-1 yield.But in fact, butene-1 concentration improves the isomerization speed of daring to increase butene-1, the trace sulfide that is contained in the methyl alcohol that the isobutene etherification technology is produced, dimethyl ether, water and the catalytically cracked C four is all to the hydrogenation reaction of butadiene inhibitory action to some extent, do not turn to butene-2 but do not influence the butene-1 isomery, therefore can not significantly improve the butene-1 yield; Material repeatedly passes through separated, and energy consumption is big.Domestic imported technology will be adsorbed earlier, purified treatment such as drying, Merox desulfurization before hydrogenation, long flow path, energy consumption height.
The objective of the invention is to utilize the characteristic of system itself, when separating the iso-butane bigger first than butene-1 volatility, remove above-mentioned objectionable impurities, make and select hydrogenation process than under to carry out at lower temperature and hydrogen/diolefin, reduce the butene-1 isomerization rate as far as possible, improve the butene-1 yield, technical process is simplified, energy consumption and cost descend.
The objective of the invention is to realize by following design:
In technology of the present invention, at first in a precision fractionation tower, separate the bigger iso-butane of volatility, main is simultaneously by the control operation condition, reach following purpose: select the harmful impurity of hydrogenation catalyst when 1. utilizing azeotropic properties or volatility difference to remove minor amount of water in the carbon four, methyl alcohol, sulfide, dimethyl ether etc., make the content of these impurity both satisfy the purity requirement of polymer grade butene-1, do not influence the activity and stability of selecting hydrogenation catalyst again.2.. remove carbon three diolefins and alkynes, thereby reduce the density of hydrogen in the hydrogenation process, reduce the butene-1 isomery and turn to, improve the yield of butene-1 along pair reactions such as anti-butene-2 and butene-1 deep hydrogenation generation normal butanes.
The material that separates after the said components directly enters the selective hydrogenation reaction device, make 1.3-butadiene equal altitudes hydrogenation of unsaturated hydrocarbons generate corresponding monoolefine, separate normal butane and suitable anti-butene-2 through a precision fractionation tower at last, thereby obtain polymer grade height butene-1.
Accompanying drawing is a process flow diagram.The mixed c 4 raw material that comes from ether-based device enters fractionating column [2] after preheater [1] is preheated to 40 ℃～80 ℃, the cat head vapor phase product partly or entirely enters return tank [4] after the condensation through condenser [3], partial condensation liquid is back to tower [2] top through reflux pump [5], rest materials goes out device through pipeline [6], and the water-phase product of separating out in the return tank [4] is discharged by pipeline [7].Tower still material part is returned tower [2] bottom after reboiler [8] is heated, it is to reduce to through cooler [9] that uniform temperature is laggard goes into to select hydrogenation reactor [10], enters fractionating column [11] after making diolefin and alkynes be converted into monoolefine with hydrogen reaction under the effect of catalyst.Vapor-phase material enters return tank [13] after condenser 12 whole condensations, partial condensation liquid is back to tower [11] top through reflux pump [14], and all the other go out device as product through pipeline [15].Tower still material part is returned tower [11] bottom through reboiler [16], and all the other go out device through pipeline [17].
The operating pressure of fractionating column [2] is 0.6--2.0MPa, and operating temperature 40--90 ℃, reflux ratio is 10--200, and number of theoretical plate is the 60--200 piece.
0.6--2.0MPa is pressed in the operation of selective hydrogenation reaction device [10], and operating temperature 40--80 ℃, hydrogen feeding amount is 1.0--2.0 a times of stoichiometry desirable value, and liquid hourly space velocity (LHSV) is 2.--50h
-1The activity of such catalysts component is a palladium, and carrier is Al
2O
3General selection hydrogenation catalyst.
The operating pressure 0.4--1.0MPa of fractionating column [11], operating temperature 40--100 ℃, reflux ratio 2--60, number of theoretical plate 60--200 piece.
Effect of the present invention has reached the purpose of foregoing invention, utilize the character of impurity compound and carbon four systems, when separating the light component iso-butane, remove selecting harmful impurity of hydrogenation catalyst and carbon three height unsaturated hydrocarbons, make hydrogenation catalyst keep high selection hydrogenation activity; Course of reaction is carried out under the condition that more relaxes, thereby suppressed the isomerization reaction of butene-1, improved the butene-1 yield, owing to need before hydrogenation, butene-1 be concentrated through twice separated, need before hydrogenation, not adsorb drying, purified treatment such as desulfurization earlier yet, therefore simplified technology, reduce investment, reduced cost and energy consumption, and improved the yield of butene-1, reach 85--92%, and prior art butene-1 yield is 80--84%.(Deutsche Bundespatent 3426349)
Further specify the present invention with embodiment below:
Embodiment 1. is raw materials used to be that cracking c_4 is through the residue C-4-fraction behind the etherification technology, operating condition sees attached list 1, the composition of raw material composition, fractionating column [2] tower still material, selective hydrogenation reaction device [10] outlet material and product is listed in subordinate list 2 tables, the butene-1 yield is 96.1% in the tower [2], select hydrogenation process butene-1 yield 98.7%, butene-1 yield 96.7% in the tower [11], the butene-1 total recovery is 91.7%
The operating parameter of subordinate list 1. embodiment 1
| | | Tower 11 | |
| Operating pressure MPa | 0.56 | 1.0 | 0.52 |
| Cat head or reactor inlet temperature ℃ | 47 | 45 | 48 |
| Tower still or reactor outlet temperature ℃ | 60 | 63 | 60 |
| Reflux ratio | 130 | / | 35 |
| Liquid hourly space velocity (LHSV) h -1 | / | 20 | / |
| Hydrogen and diolefin mol ratio | / | 1.3 | / |
The composition (M/M%) of each material among subordinate list 2. embodiment 1
| | Tower | 2 tower still things | Material behind the hydrogenation | Product | |
| Propane+propylene M/M% | 0.11 | / | / | / | |
| Iso-butane M/M% | 2.32 | 0.09 | 0.09 | 0.10 | |
| Normal butane M/M% | 6.55 | 7.46 | 7.87 | 0.23 | |
| Isobutene M/M% | 0.10 | 0.14 | 0.14 | 0.29 | |
| Butene-1 M/M% | 66.22 | 64.62 | 63.72 | 99.17 | |
| Butene-2 M/M% | 23.21 | 26.58 | 28.18 | 0.21 | |
| 1,3-butadiene PPM | 12000 | 11.300 | ＜20 | ＜20 | |
| C4 alkynes PPM | 300 | 80 | ＜5 | ＜5 | |
| C3 diolefin+alkynes PPM | 150 | ＜150 | ＜2 | ＜2 | |
| Dimethyl ether PPM | 2100 | ＜5 | ＜5 | ＜5 | |
| Methyl alcohol PPM | 185 | ＜5 | ＜5 | ＜5 | |
| Water PPM | 345 | ＜20 | ＜20 | ＜20 | |
| Sulphur PPM | ＜2 | ＜1 | ＜1 | ＜1 |
The operating condition of subordinate list 3. embodiment 2
| | Reactor [10] | | |
| Operating pressure, MPa | 0.65 | 1.0 | 0.60 |
| Cat head or reactor inlet temperature, ℃ | 49 | 45 | 56 |
| Tower still or reactor outlet temperature, ℃ | 62 | 59 | 67 |
| Reflux ratio | 45 | / | 28 |
| Liquid hourly space velocity (LHSV), h -1 | / | 25 | / |
| Hydrogen and diolefin mol ratio | / | 1.2 | / |
The composition of each material among subordinate list 4. embodiment 2
| | Tower | 2 tower still things | Material behind the hydrogenation | Product | |
| Propane+propylene M/M% | 4.62 | / | / | / | |
| Iso-butane M/M% | 36.73 | 0.01 | 0.01 | 0.02 | |
| Normal butane M/M% | 10.17 | 17.53 | 18.20 | 0.27 | |
| Isobutene M/M% | 0.08 | 0.14 | 0.14 | 0.32 | |
| Butene-1 M/M% | 30.82 | 51.09 | 50.17 | 99.14 | |
| Butene-2 M/M% | 17.15 | 29.57 | 31.48 | 0.25 | |
| 1.3-butadiene PPm | 9360 | 161.00 | 25 | 52 | |
| C4 alkynes PPm | 273 | 471 | ＜5 | ＜5 | |
| C3 diene+alkynes PPM | 714 | ＜2 | ＜2 | ＜2 | |
| Dimethyl ether PPm | 1920 | ＜5 | ＜5 | ＜5 | |
| Methyl alcohol PPM | 69 | ＜5 | ＜5 | ＜5 | |
| Water PPm | 301 | ＜20 | ＜20 | ＜20 | |
| Sulphur PPm | 29 | 2.5 | 2.5 | ＜1 |
Claims (4)
1. method of producing high-purity butylene-1 by etherification technology residue c4 fraction comprises the selection hydrogenation of butadiene and removes, and the separation of other carbon four components beyond the butene-1, it is characterized in that:
A. at first in the fractionating column [2] that separates light component, separate in the iso-butane, remove oxygenatedchemicals, sulfur-containing compound and carbon three diolefins, alkynes etc. selecting the harmful material of hydrogenation catalyst;
B. directly enter the selective hydrogenation reaction device from separating the next material of light component fractionating column [2], remove butadiene and the C very approaching with the butene-1 boiling point
4Alkynes; Reacting rear material can obtain the polymer grade high-purity butylene-1 through separated tower [11] again;
C. the operating pressure 0.6-2.0Mpa of light component knockout tower [2], operating temperature 40-90 ℃, reflux ratio 10-200.
2. by the described method of claim 1, it is characterized in that the number of theoretical plate 60-200 piece of tower [2].
3. by the described method of claim 1, it is characterized in that the operating pressure 0.6-2.0Mpa of selective hydrogenation reaction device [10], operating temperature 40-80 ℃, hydrogen feeding amount is 1.0-2.0 a times of stoichiometry desirable value.
4. by the described method of claim 1, it is characterized in that the operating pressure 0.6-1.0Mpa of product knockout tower [11], operating temperature 40-90 ℃, reflux ratio 10-60, number of theoretical plate 60-200 piece.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN94110735A CN1050311C (en) | 1994-08-01 | 1994-08-01 | Method for producing high-purity butene-1 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN94110735A CN1050311C (en) | 1994-08-01 | 1994-08-01 | Method for producing high-purity butene-1 |
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| Publication Number | Publication Date |
|---|---|
| CN1116126A CN1116126A (en) | 1996-02-07 |
| CN1050311C true CN1050311C (en) | 2000-03-15 |
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| Application Number | Title | Priority Date | Filing Date |
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| CN94110735A Expired - Fee Related CN1050311C (en) | 1994-08-01 | 1994-08-01 | Method for producing high-purity butene-1 |
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Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7528290B2 (en) * | 2006-12-28 | 2009-05-05 | Uop Llc | Apparatuses and methods for separating butene-1 from a mixed C4 feed |
| CN101362671B (en) * | 2008-09-12 | 2011-09-07 | 中国石油化工股份有限公司 | Method for preparing polymer grade 1-butene by high sulfur content four carbon compounds catalysis from refinery |
| CN101519337B (en) * | 2009-03-25 | 2012-12-05 | 中国石油化工股份有限公司 | Method for fine desulfurization of high-sulfur C4 of refineries |
| CN101973835A (en) * | 2010-10-18 | 2011-02-16 | 天津市泰旭物流有限公司 | Technology for purifying butylene by adopting chemical separation method |
| CN114456029A (en) * | 2020-10-21 | 2022-05-10 | 中国石油化工股份有限公司 | Method and apparatus for producing 1-butene from tetracarbon |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SU1747435A1 (en) * | 1990-06-07 | 1992-07-15 | Научно-производственное объединение по разработке и внедрению нефтехимических процессов "Леннефтехим" | Method of 1,4-diacetoxybutane synthesis |
| RU2032649C1 (en) * | 1992-01-16 | 1995-04-10 | Акционерное общество закрытого типа Промышленно-финансовая группа Ассоциации "Внедрение" | Process for preparing both isoprene and 3-methylbutene-1 |
-
1994
- 1994-08-01 CN CN94110735A patent/CN1050311C/en not_active Expired - Fee Related
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SU1747435A1 (en) * | 1990-06-07 | 1992-07-15 | Научно-производственное объединение по разработке и внедрению нефтехимических процессов "Леннефтехим" | Method of 1,4-diacetoxybutane synthesis |
| RU2032649C1 (en) * | 1992-01-16 | 1995-04-10 | Акционерное общество закрытого типа Промышленно-финансовая группа Ассоциации "Внедрение" | Process for preparing both isoprene and 3-methylbutene-1 |
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| CN1116126A (en) | 1996-02-07 |
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