CN113387906B - Method for continuously producing epoxypropane derivative by using propane - Google Patents
Method for continuously producing epoxypropane derivative by using propane Download PDFInfo
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- CN113387906B CN113387906B CN202110737508.XA CN202110737508A CN113387906B CN 113387906 B CN113387906 B CN 113387906B CN 202110737508 A CN202110737508 A CN 202110737508A CN 113387906 B CN113387906 B CN 113387906B
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- propylene
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- propane
- propylene oxide
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- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 title claims abstract description 100
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical class CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 title claims abstract description 70
- 239000001294 propane Substances 0.000 title claims abstract description 49
- 238000000034 method Methods 0.000 title claims abstract description 36
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 93
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims abstract description 78
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims abstract description 40
- 239000000047 product Substances 0.000 claims abstract description 31
- 239000001257 hydrogen Substances 0.000 claims abstract description 21
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 21
- 239000004721 Polyphenylene oxide Substances 0.000 claims abstract description 20
- 229920000570 polyether Polymers 0.000 claims abstract description 20
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 15
- 238000006356 dehydrogenation reaction Methods 0.000 claims abstract description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 13
- 238000000746 purification Methods 0.000 claims abstract description 8
- 238000006703 hydration reaction Methods 0.000 claims abstract description 7
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 37
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 35
- 238000006243 chemical reaction Methods 0.000 claims description 32
- 239000003054 catalyst Substances 0.000 claims description 19
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 claims description 15
- 150000002431 hydrogen Chemical class 0.000 claims description 15
- 238000006735 epoxidation reaction Methods 0.000 claims description 13
- 238000005984 hydrogenation reaction Methods 0.000 claims description 13
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 claims description 12
- 150000004056 anthraquinones Chemical class 0.000 claims description 12
- 238000007254 oxidation reaction Methods 0.000 claims description 12
- 238000005336 cracking Methods 0.000 claims description 9
- 238000006116 polymerization reaction Methods 0.000 claims description 8
- 230000003647 oxidation Effects 0.000 claims description 7
- 239000007789 gas Substances 0.000 claims description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N glycerol group Chemical group OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 6
- 238000007670 refining Methods 0.000 claims description 6
- 230000036571 hydration Effects 0.000 claims description 5
- 239000000463 material Substances 0.000 claims description 5
- 239000002351 wastewater Substances 0.000 claims description 5
- 239000012224 working solution Substances 0.000 claims description 5
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 claims description 4
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 4
- 239000007795 chemical reaction product Substances 0.000 claims description 4
- 239000010936 titanium Substances 0.000 claims description 4
- 229910052719 titanium Inorganic materials 0.000 claims description 4
- 229910018601 Ni—Ti—Si Inorganic materials 0.000 claims description 3
- 229910018725 Sn—Al Inorganic materials 0.000 claims description 3
- 230000006835 compression Effects 0.000 claims description 3
- 238000007906 compression Methods 0.000 claims description 3
- 238000001704 evaporation Methods 0.000 claims description 3
- 230000008020 evaporation Effects 0.000 claims description 3
- 238000000605 extraction Methods 0.000 claims description 3
- 239000007788 liquid Substances 0.000 claims description 3
- 238000010791 quenching Methods 0.000 claims description 3
- 230000000171 quenching effect Effects 0.000 claims description 3
- 238000011084 recovery Methods 0.000 claims description 3
- 238000000926 separation method Methods 0.000 claims description 3
- 229910004298 SiO 2 Inorganic materials 0.000 claims description 2
- 239000002808 molecular sieve Substances 0.000 claims description 2
- 229910052710 silicon Inorganic materials 0.000 claims description 2
- 239000010703 silicon Substances 0.000 claims description 2
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 claims description 2
- 238000010924 continuous production Methods 0.000 claims 7
- 239000002994 raw material Substances 0.000 abstract description 19
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 abstract description 10
- 238000002360 preparation method Methods 0.000 abstract description 6
- 239000003570 air Substances 0.000 abstract description 5
- 239000006227 byproduct Substances 0.000 abstract description 4
- 230000000052 comparative effect Effects 0.000 description 27
- 230000000694 effects Effects 0.000 description 11
- 238000004519 manufacturing process Methods 0.000 description 5
- YEVQZPWSVWZAOB-UHFFFAOYSA-N 2-(bromomethyl)-1-iodo-4-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=C(I)C(CBr)=C1 YEVQZPWSVWZAOB-UHFFFAOYSA-N 0.000 description 4
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 4
- DKGAVHZHDRPRBM-UHFFFAOYSA-N tertiry butyl alcohol Natural products CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 4
- 238000005516 engineering process Methods 0.000 description 3
- HWOWEGAQDKKHDR-UHFFFAOYSA-N 4-hydroxy-6-(pyridin-3-yl)-2H-pyran-2-one Chemical compound O1C(=O)C=C(O)C=C1C1=CC=CN=C1 HWOWEGAQDKKHDR-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 238000004939 coking Methods 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 2
- 238000003795 desorption Methods 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 229910052747 lanthanoid Inorganic materials 0.000 description 2
- 150000002602 lanthanoids Chemical class 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- SJEBAWHUJDUKQK-UHFFFAOYSA-N 2-ethylanthraquinone Chemical group C1=CC=C2C(=O)C3=CC(CC)=CC=C3C(=O)C2=C1 SJEBAWHUJDUKQK-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 229910052684 Cerium Inorganic materials 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical group [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 229910010413 TiO 2 Inorganic materials 0.000 description 1
- 229910003082 TiO2-SiO2 Inorganic materials 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- 229910052790 beryllium Inorganic materials 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- XENVCRGQTABGKY-ZHACJKMWSA-N chlorohydrin Chemical compound CC#CC#CC#CC#C\C=C\C(Cl)CO XENVCRGQTABGKY-ZHACJKMWSA-N 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 229910052681 coesite Inorganic materials 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 229910052906 cristobalite Inorganic materials 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 229910052746 lanthanum Inorganic materials 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 238000011112 process operation Methods 0.000 description 1
- 229910052706 scandium Inorganic materials 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229910052682 stishovite Inorganic materials 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229910052905 tridymite Inorganic materials 0.000 description 1
- 238000011144 upstream manufacturing Methods 0.000 description 1
- 238000003809 water extraction Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
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-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D301/00—Preparation of oxiranes
- C07D301/02—Synthesis of the oxirane ring
- C07D301/03—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds
- C07D301/12—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds with hydrogen peroxide or inorganic peroxides or peracids
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
- C01B15/00—Peroxides; Peroxyhydrates; Peroxyacids or salts thereof; Superoxides; Ozonides
- C01B15/01—Hydrogen peroxide
- C01B15/013—Separation; Purification; Concentration
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
- C01B15/00—Peroxides; Peroxyhydrates; Peroxyacids or salts thereof; Superoxides; Ozonides
- C01B15/01—Hydrogen peroxide
- C01B15/027—Preparation from water
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
- C01B3/00—Hydrogen; Gaseous mixtures containing hydrogen; Separation of hydrogen from mixtures containing it; Purification of hydrogen
- C01B3/02—Production of hydrogen or of gaseous mixtures containing a substantial proportion of hydrogen
- C01B3/22—Production of hydrogen or of gaseous mixtures containing a substantial proportion of hydrogen by decomposition of gaseous or liquid organic compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/09—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis
- C07C29/10—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis of ethers, including cyclic ethers, e.g. oxiranes
- C07C29/103—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis of ethers, including cyclic ethers, e.g. oxiranes of cyclic ethers
- C07C29/106—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis of ethers, including cyclic ethers, e.g. oxiranes of cyclic ethers of oxiranes
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C5/00—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms
- C07C5/32—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by dehydrogenation with formation of free hydrogen
- C07C5/327—Formation of non-aromatic carbon-to-carbon double bonds only
- C07C5/333—Catalytic processes
- C07C5/3335—Catalytic processes with metals
- C07C5/3337—Catalytic processes with metals of the platinum group
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D301/00—Preparation of oxiranes
- C07D301/32—Separation; Purification
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/04—Compounds containing oxirane rings containing only hydrogen and carbon atoms in addition to the ring oxygen atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2523/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00
- C07C2523/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of noble metals
- C07C2523/54—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of noble metals combined with metals, oxides or hydroxides provided for in groups C07C2523/02 - C07C2523/36
- C07C2523/56—Platinum group metals
- C07C2523/62—Platinum group metals with gallium, indium, thallium, germanium, tin or lead
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- 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
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- Y02P30/40—Ethylene production
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Abstract
The invention discloses a method for continuously producing a propylene oxide derivative by using propane, wherein a dehydrogenation-cracking-hydrogenation-oxidation-epoxidation-polymerization-hydration reaction route is arranged in a propylene oxide device, a polyether device and a propylene glycol device of 5-90 ten thousand tons per year, propane, water and air are used as raw materials, hydrogen by-product of propane dehydrogenation is used as a raw material for preparing hydrogen peroxide, and insufficient hydrogen is supplemented by using methanol or methane through a cracking-purification process technical route. The method realizes the industrial continuous preparation of the downstream derivative polyether of the propylene oxide and the propylene glycol product by using the cheap propane raw material at 6.31-116.18 ten thousand tons per year, wherein the polyether comprises 8 series of soft, semi-hard and hard products with different brands, the utilization rate of the propane raw material is improved to 98.28-99.67%, the consumption of the propane is reduced to 0.0991-3.0189 ten thousand tons per year, and the problem of large raw material consumption in the prior art is better solved.
Description
Technical Field
The invention relates to a production method of chemical products, in particular to a method for continuously producing epoxypropane derivatives by using propane.
Background
The technological production technology of propylene oxide PO at home and abroad mainly comprises a chlorohydrin CHPO method, a propylene oxide/styrene PO/SM co-oxidation method, a propylene oxide/tert-butyl alcohol PO/TBA co-oxidation method, a cumene oxidation CHPPO method and a hydrogen peroxide oxidation HPPO method, wherein propylene is used as a raw material for preparing propylene oxide, an upstream propylene preparation device, a propylene oxide device, a downstream polyether device and a propylene glycol device are independently arranged, and the propylene is stored and transported and related materials are repeatedly fed and discharged, so that the loss and consumption of the propylene are large.
Patent application No. cn200710010674.x discloses that in an annular gap formed by a double-layer glass medium, propane molecules generate isopropyl radicals and n-propyl radicals under the action of energetic electrons formed by plasma, wherein the isopropyl radicals interact with active oxygen substances formed by oxygen molecules in the plasma to perform selective oxidation reaction to generate propylene oxide. In examples 1 to 3, the propane conversion rate was 8.4 to 39.2% and the propylene oxide selectivity was 5.1 to 9.4%.
Patent application No. CN201810699480.3 discloses a process for preparing hydrocarbons by using methanol as a solvent in the production process of propylene oxide, and hydrogen and propylene which are byproducts in the process of preparing hydrocarbons by using methanol are used for preparing hydrogen peroxide, so that the problem of the source of the hydrogen peroxide is solved, and the concept of atomic economy is met. The produced propylene byproduct is used as a raw material of the propylene oxide, and the steam consumption is reduced by more than 50 percent. In the embodiments 1 to 3, a methanol-to-aromatics process technology is adopted, 180 ten thousand tons of methanol raw materials are consumed, and 45.5 to 61.0 ten thousand tons of aromatics are co-produced while 25 ten thousand tons of propylene oxide products are produced; by adopting the process technology of preparing olefin from methanol, 180 ten thousand tons of methanol raw materials are consumed, and 32.0 ten thousand tons of ethylene and propylene are co-produced while 25 ten thousand tons of propylene oxide products are produced.
In summary, in the prior art, the problems of large consumption and large loss of the propane raw material exist in the process of preparing the propylene oxide and the derivatives thereof by using cheap propane or methanol as the raw material.
Disclosure of Invention
The invention aims to: the invention aims to provide a method for continuously and industrially producing products such as propylene oxide downstream derivative polyether, propylene glycol and the like with high added value in a large-scale commercial way by adopting cheap propane raw materials.
The technical scheme is as follows: the method for continuously producing the epoxypropane derivative by using the propane comprises the following steps:
(1) the propane enters a dehydrogenation unit, a quenching unit, a compression unit and a separation unit to obtain propylene and hydrogen, the propylene is divided into epoxydized propylene and propylene products, and the propylene products are sent out;
(2) the methanol is divided into cracked methanol and epoxidized methanol, the cracked methanol enters a cracking unit and a purification unit to obtain cracked hydrogen and desorbed gas, and the desorbed gas is sent out of the room;
(3) the hydrogen gas and the hydrogen gas are combined into hydrogenated hydrogen gas, the hydrogenated hydrogen gas, water and air enter a hydrogenation unit, an oxidation unit, an extraction unit and a concentration unit to obtain hydrogen peroxide and waste water, and the waste water is sent out;
(4) the epoxidation propylene, the epoxidation methanol and the hydrogen peroxide enter an epoxidation unit for epoxidation reaction, and then enter a refining unit and a recovery unit to obtain a propylene oxide product and recover propylene glycol, propylene glycol monomethyl ether and propylene glycol monomethyl ether, wherein the propylene glycol monomethyl ether and the propylene glycol monomethyl ether are respectively sent out;
(5) dividing propylene oxide into nine, enabling the first eight strands of propylene oxide to respectively enter 8 polymerization units, carrying out polymerization reaction under different process conditions to generate different polyether reaction products, and enabling the polyether reaction products to pass through 8 refining units to obtain 8 polyether products with different brands and respectively sending out the polyether products;
(6) and finally, the propylene oxide enters a hydration unit, an evaporation unit and a purification unit to obtain propylene glycol, the propylene glycol and the recovered propylene glycol are combined into a propylene glycol product, and the propylene glycol product is sent out.
Wherein, in the step (2), the cracked methanol can be replaced by methane.
In the step (1), the reaction pressure of the dehydrogenation unit is 0.05-0.85 MPaA, the reaction temperature is 410-610 ℃, the catalyst is Pt-Sn-Al oxide, the water is vaporized into water vapor, and the molar ratio of the water vapor to the propane is 1.0-10.0: 1, the mass airspeed of propane is 3.0-8.0 h -1 。
The steam is combined with propane 1 into dehydrogenation unit a1 as a diluent to prevent coking of propane 1 on the catalyst surface.
The catalyst is Pt-Sn-Al oxide and comprises the following components: 0.1 to 5 parts of Pt or an oxide thereof; 0.1 to 5 parts of Sn or an oxide thereof; 90-99 parts of a composite oxide M1-M2-A1-O carrier, wherein M1 is selected from at least one element in IIA group elements and a mixture of at least one element in IIIB group elements, and M2 is selected from at least one lanthanide; wherein the group IIIB element is selected from Sc or Y; the IIA group element is selected from Be, Mg, Ca, Sr or Ba; the lanthanide is selected from La or Ce; the preparation method of the M1-M2-A1-O carrier comprises the following steps: weighing soluble salts of M1, M2 and A1 with required contents, dissolving the soluble salts in a proper amount of deionized water, uniformly mixing, slowly dripping ammonia water under continuous stirring, and adjusting the pH value to 7-10; and aging, filtering, drying and roasting the product to obtain the M1-M2-A1-O carrier.
In the step (2), the reaction pressure of the cracking unit is 0.90-1.60 MPaA, the reaction temperature is 215-260 ℃, the catalyst is Cu-Ni-Ti-Si oxide, the water is vaporized into steam, the molar ratio of the steam to the cracked methanol is 1.1-2.6: 1.
the steam is combined with the cracked methanol 7 and enters the cracking unit B1 as a diluent to prevent the cracked methanol 7 from coking on the surface of the catalyst.
The catalyst is a copper catalyst which is a Cu-Ni-Ti-Si oxide and comprises CuO-NiO/TiO2-SiO2, and the molar ratio of the elements of each component is Cu: ni: ti: si ═ 6: 1.2: 0.5: 0.7.
in the step (3), the reaction pressure of the hydrogenation unit is 0.20-4.60 MPaA, the reaction temperature is 38-75 ℃, the catalyst is a Pd-Pt active component anthraquinone hydrogenation catalyst, and the volume flow ratio of hydrogenation hydrogen to working liquid is 0.5-10.0: 1, the material volume airspeed is 4.0-20.0 h -1 。
The anthraquinone is 2-ethyl anthraquinone, the working solution consists of anthraquinone, heavy aromatic hydrocarbon and trioctyl phosphate, and the volume ratio of the heavy aromatic hydrocarbon to the trioctyl phosphate is 6.0-1.0: 1, the concentration of the anthraquinone in the working solution is 30-150 g/L, and the anthraquinone is subjected to hydrogenation reaction to generate hydrogenated anthraquinone.
In the step (3), the reaction pressure of the oxidation unit is 0.25-0.60 MPaA, the reaction temperature is 45-55 ℃, and the volumetric flow ratio of air to working liquid is 5.0-40.0: 1, the material volume airspeed is 4.0-120.0 h -1 。
The working solution consists of hydrogenated anthraquinone, heavy aromatic hydrocarbon and trioctyl phosphate, and the volume ratio of the heavy aromatic hydrocarbon to the trioctyl phosphate is (6.0-1.0): 1, the concentration of hydrogenated anthraquinone in the working solution is 30-150 g/L, the hydrogenated anthraquinone is subjected to oxidation reaction to generate oxidized anthraquinone, and the oxidized anthraquinone is subjected to water extraction to obtain hydrogen peroxide.
In the step (4), the reaction pressure of the epoxidation unit is 0.40-5.60 MPaA, the reaction temperature is 20-95 ℃, the catalyst is a TS-1 type titanium silicalite molecular sieve, and the mass ratio of titanium to silicon is SiO 2 ：TiO 2 10-200: 1, the molar ratio of the epoxidized methanol to the hydrogen peroxide is 4.0-18.0: 1, the mol ratio of the epoxidized propylene to the hydrogen peroxide is 1.2-10.0: 1, the weight space velocity of the epoxidized propylene is 0.5-8.0 h -1 。
In the step (5), the reaction pressure of the 8 polymerization units is 0.10-0.60 MPaA, the reaction temperature is 100-150 ℃, and the catalyst is glycerol.
In the step (6), the reaction pressure of the hydration unit (G1) is 1.10-3.60 MPaA, the reaction temperature is 150-200 ℃, the molar ratio of water to the last strand of propylene oxide is 5.0-30.0: 1.
wherein the reaction pressure of the cracking unit (B1) is 0.10-1.00 MPaA, the reaction temperature is 450-950 ℃, the catalyst is Fe-Co-Ni-Mn-Cr oxide, and the volume space velocity of methane is 1.0-60.0 h -1 。
The catalyst is any one or more of metals Fe, Co, Ni, Mn and Cr in Fe-Co-Ni-Mn-Cr oxide.
Has the advantages that: compared with the prior art, the invention has the following remarkable advantages: in a device for large-scale commercial continuous industrial production of propylene oxide by a hydrogen peroxide method with nominal capacity of 5-90 ten thousand tons per year, a downstream derivative polyether device and a propylene glycol device, a process technical route of 'dehydrogenation-quenching-compression-separation-hydrogenation-oxidation-extraction-concentration-epoxidation-refining-recovery-polymerization-refinement-hydration-evaporation-purification' is arranged, and cheap propane, water and air are used as raw materials to continuously prepare products such as the derivative polyether with high added value at the downstream of the propylene oxide and the propylene glycol. Meanwhile, hydrogen gas which is a byproduct of propane dehydrogenation is reasonably used as a raw material for preparing hydrogen peroxide, and insufficient hydrogen gas is supplemented by methanol or methane through a 'cracking-purifying' process technical route. Therefore, products such as downstream derivative polyether of propylene oxide, propylene glycol and the like are continuously prepared in a propane industrialized mode for 6.31-116.18 ten thousand tons per year, wherein the polyether comprises 8 series of soft, semi-hard and hard products with different brands, the utilization rate of propane raw materials is improved to 98.28-99.67%, the consumption of propane is reduced to 0.0991-3.0189 ten thousand tons per year, and a good technical effect is achieved.
Drawings
FIG. 1 is a process flow diagram of the present invention.
Detailed Description
The technical scheme of the invention is further explained by combining the attached drawings.
Examples 1 to 8
With reference to fig. 1, the process flow of the method for continuously producing the propylene oxide derivative from propane according to the present invention is as follows: the propane 1 from the outside enters a dehydrogenation unit A1 for dehydrogenation reaction to generate propylene, and then is cooled by a quenching unit A2, a compression unit A3 is pressurized, a separation unit A4 separates propylene 8 and hydrogen 9, wherein the propylene 8 is divided into two parts, the propylene epoxide 13 and a propylene product 17 are obtained, and the propylene product 17 is sent out of the outside. Methanol 2 from the outside is divided into two parts, namely cracked methanol 7 and epoxidized methanol 10, the cracked methanol 7 enters a cracking unit B1 to undergo cracking reaction to generate hydrogen, and the hydrogen 11 is purified by a purification unit B2 to obtain cracked hydrogen and residual desorption gas 18, and the desorption gas 18 is sent out of the outside. The cracked hydrogen 11 and the hydrogen 9 produced by the device are combined into one and combined into hydrogenated hydrogen 4. The hydrogenated hydrogen 4, water 5 and air 6 from the outside enter a hydrogenation unit C1 for hydrogenation reaction, then enter an oxidation unit C2 for oxidation reaction to generate hydrogen peroxide, then an extraction unit C3 extracts and a concentration unit C4 concentrates the hydrogen peroxide 12, and the rest waste water 19 is sent out of the outside. The epoxidation propylene 13 produced by the device and epoxidation methanol 10 from outside and hydrogen peroxide 12 produced by the device enter an epoxidation unit D1 to carry out epoxidation reaction to generate a propylene oxide product, the propylene oxide product is divided into propylene oxide 14 and other propylene oxides, the other propylene oxides are refined into the propylene oxide 14 through a refining unit D2, and the propylene oxide 14, the propylene glycol monomethyl ether 32 and the propylene glycol monomethyl ether 33 are recovered through a recovery unit D3. Wherein the propylene glycol monomethyl ether 32 and the propylene glycol monomethyl ether 33 are discharged to the outside. The 14-part of propylene oxide produced by the device is nine, the front eight strands of propylene oxide respectively enter 8 polymerization units E1-E8, polymerization is carried out under different process conditions to generate different polyether reaction products, and the polyether products 21-28 with different brands are refined and respectively sent out of the house through 8 refining units F1-F8. The last segment of propylene oxide in the propylene oxide 14 enters a hydration unit G1 for hydration reaction, propylene glycol 16 is purified through an evaporation unit G2 and a purification unit G3, the propylene glycol 16 and the recovered propylene glycol 15 produced by the device are combined into one, and the combined propylene glycol product 31 is sent out.
The cracked methanol 7 from outside the present example can be replaced by methane 3.
The specific process parameters and technical effects of this example are shown in the attached table 1.
Table 1 attached hereto, examples 1 to 8, specific process parameters and technical effects
Comparative examples 1 to 8
The method comprises the steps of arranging comparative examples 1 to 8, independently arranging a propylene oxide preparation device and a propylene oxide device through propane dehydrogenation and a downstream polyether device and a propylene glycol device in a propylene oxide device with nominal capacity of 5-90 ten thousand tons per year, and obtaining the technical effects shown in the attached table 2 under the conditions that the process operation parameters are the same and the same propylene oxide derivative product is obtained through production and preparation.
Table 2 accompanying technical effects of comparative examples 1 to 8
Comparative examples 9 to 14
The comparative examples 9 to 14 are arranged, the nominal capacity of the propylene oxide device is kept unchanged at 5-90 ten thousand tons/year, the propylene preparation device by propane dehydrogenation is independently arranged, and the technical effects are shown in the attached table 3.
TABLE 3 technical effects of comparative examples 9 to 14
| Attached table 3 | Comparative example 9 | Comparative example 10 | Comparative example 11 | Comparative example 12 | Comparative example 13 | Comparative example 14 |
| Nominal capacity of PO (ten thousand tons/year) | 5 | 10 | 30 | 35 | 60 | 90 |
| Propane dehydrogenation PDH device | ||||||
| Dehydrogenation pressure (MPaA) | 0.23 | 0.78 | 0.32 | 0.66 | 0.41 | 0.54 |
| Dehydrogenation reaction temperature (. degree.C.) | 434 | 579 | 456 | 550 | 481 | 523 |
| Water/propane (mol/mol) | 2.2 | 8.8 | 3.6 | 7.4 | 4.8 | 5.8 |
| Propane Mass space velocity (h) -1 ) | 3.6 | 7.3 | 4.2 | 6.1 | 4.4 | 5.0 |
| Propane consumption (ten thousand tons/year) | 4.86 | 9.76 | 29.41 | 34.38 | 59.05 | 88.75 |
| Propylene yield (ten thousand tons/year) | 4.24 | 8.52 | 25.64 | 29.97 | 51.49 | 77.39 |
The consumption of the propane in the prior art comparative examples 9 to 14 is 4.86 to 88.75 ten thousand tons/year, and the consumption of the propane in the invention examples 1 to 6 is reduced to 4.76 to 85.73 ten thousand tons/year.
Comparative examples 15 to 20
The comparative examples 15 to 20 are arranged, the nominal capacity of the propylene oxide device is kept unchanged at 5-90 ten thousand tons/year, the propylene oxide device is independently arranged, and the technical effects are shown in the attached table 4.
TABLE 4 technical effects of comparative examples 15 to 20
| Attached table 4 | Comparative example 15 | Comparative example 16 | Comparative example 17 | Comparative example 18 | Comparative example 19 | Comparative example 20 |
| Nominal capacity of PO (ten thousand tons/year) | 5 | 10 | 30 | 35 | 60 | 90 |
| Propylene oxide HPPO device | ||||||
| Epoxidation pressure (MPaA) | 0.66 | 5.01 | 1.39 | 4.04 | 2.34 | 3.17 |
| Epoxidation reaction temperature (. degree. C.) | 28 | 81 | 39 | 73 | 51 | 64 |
| SiO2/TiO2(wt/wt) | 32 | 177 | 53 | 130 | 76 | 99 |
| methanol/Hydrogen peroxide (mol/mol) | 5.7 | 16.1 | 7.3 | 14.0 | 9.4 | 11.8 |
| Propene/hydrogen peroxide (mol/mol) | 1.8 | 8.8 | 3.2 | 7.4 | 4.8 | 6.0 |
| Propylene weight space velocity (h) -1 ) | 1.3 | 7.2 | 2.7 | 6.4 | 4.4 | 5.5 |
| Propylene consumption (ten thousand tons/year) | 4.24 | 8.52 | 25.64 | 29.97 | 51.49 | 77.39 |
| Propylene oxide yield (ten thousand tons/year) | 5.10 | 10.25 | 30.87 | 36.09 | 61.99 | 93.17 |
The propylene consumption of the prior art comparative examples 15 to 20 is 4.24 to 77.39 ten thousand tons/year, and the propylene consumption of the invention in the examples 1 to 6 is reduced to 4.15 to 74.76 ten thousand tons/year.
Comparative examples 21 to 26
The technical effects are shown in the attached table 5 by arranging the comparative examples 21 to 26 and independently arranging the polyether device and the propylene glycol device while keeping the nominal capacity of the propylene oxide device unchanged at 5-90 ten thousand tons/year.
TABLE 5 technical effects of comparative examples 21 to 26
The consumption of the propylene oxide in the prior art comparative examples 21 to 26 is 5.10 to 93.17 ten thousand tons/year, and the consumption of the propylene oxide in the invention examples 1 to 6 is reduced to 5.00 to 90.00 ten thousand tons/year.
As can be seen from the attached tables 1 to 5:
in a propylene oxide device with nominal capacity of 5-90 ten thousand tons per year, under the condition that the same technological operation parameters are the same, and the same propylene oxide derivative polyether and propylene glycol products are produced and obtained at 6.31-116.18 ten thousand tons per year, the consumption of the propane raw material in the prior art is 4.86-88.75 ten thousand tons per year, the consumption of the propane raw material in the invention is 4.76-85.73 ten thousand tons per year, the absolute consumption of the propane raw material is reduced at 0.0991-3.0189 ten thousand tons per year, and the relative consumption of the propane raw material is reduced at 2.08-3.52%.
Claims (8)
1. A method for continuously producing a propylene oxide derivative from propane, characterized by comprising the steps of:
(1) the propane (1) enters a dehydrogenation unit (A1), a quenching unit (A2), a compression unit (A3) and a separation unit (A4) to obtain propylene (8) and hydrogen (9), the propylene (8) is divided into an epoxidized propylene (13) and a propylene product (17), and the propylene product (17) is sent out;
(2) the methanol (2) is divided into cracked methanol (7) and epoxidized methanol (10), the cracked methanol (7) enters a cracking unit (B1) and a purification unit (B2) to obtain cracked hydrogen (11) and desorbed gas (18), and the desorbed gas (18) is sent out;
(3) the cracking hydrogen (11) and the hydrogen (9) are combined into hydrogenation hydrogen (4), the hydrogenation hydrogen (4), water (5) and air (6) enter a hydrogenation unit (C1), an oxidation unit (C2), an extraction unit (C3) and a concentration unit (C4) to obtain hydrogen peroxide (12) and waste water (19), and the waste water (19) is sent out;
(4) epoxidizing propylene (13), epoxidized methanol (10) and hydrogen peroxide (12) in an epoxidation unit (D1), and then in a refining unit (D2) and a recovery unit (D3) to obtain a propylene oxide product (14) and recover propylene glycol (15), propylene glycol monomethyl ether (32) and propylene glycol monomethyl ether (33), wherein the propylene glycol monomethyl ether (32) and the propylene glycol monomethyl ether (33) are respectively sent out;
(5) dividing propylene oxide (14) into nine, respectively feeding the first eight strands of propylene oxide into 8 polymerization units (E1) - (E8), carrying out polymerization reaction under different process conditions to generate different polyether reaction products, and respectively sending out 8 polyether products (21) - (28) with different brands through 8 refining units (F1) - (F8);
(6) and finally, feeding a stream of propylene oxide into a hydration unit (G1), an evaporation unit (G2) and a purification unit (G3) to obtain propylene glycol (16), combining the propylene glycol (16) and the recovered propylene glycol (15) into a propylene glycol product (31), and sending the propylene glycol product (31) out.
2. The process for the continuous production of a propylene oxide derivative from propane according to claim 1, characterized in that: in the step (1), the reaction pressure of the dehydrogenation unit (A1) is 0.05-0.85 MPaA, the reaction temperature is 410-610 ℃, the catalyst is Pt-Sn-Al oxide, and the mass space velocity of the propane (1) is 3.0-8.0 h < -1 >.
3. The process for the continuous production of a propylene oxide derivative from propane according to claim 1, characterized in that: in the step (2), the reaction pressure of the cracking unit (B1) is 0.90-1.60 MPaA, the reaction temperature is 215-260 ℃, and the catalyst is Cu-Ni-Ti-Si oxide.
4. The process for the continuous production of a propylene oxide derivative from propane according to claim 1, characterized in that: in the step (3), the reaction pressure of the hydrogenation unit (C1) is 0.20-4.60 MPaA, the reaction temperature is 38-75 ℃, the catalyst is a Pd-Pt active component anthraquinone hydrogenation catalyst, and the volume flow ratio of the hydrogenation hydrogen (4) to the working liquid is 0.5-10.0: 1, the material volume airspeed is 4.0-20.0 h < -1 >.
5. The process for the continuous production of a propylene oxide derivative from propane according to claim 1, characterized in that: in the step (3), the reaction pressure of the oxidation unit (C2) is 0.25-0.60 MPaA, the reaction temperature is 45-55 ℃, and the volume flow ratio of air (6) to working solution is 5.0-40.0: 1, and the material volume space velocity is 4.0-120.0 h < -1 >.
6. The process for the continuous production of a propylene oxide derivative from propane according to claim 1, characterized in that: in the step (4), the reaction pressure of the epoxidation unit (D1) is 0.40-5.60 MPaA, the reaction temperature is 20-95 ℃, the catalyst is a TS-1 type titanium silicalite molecular sieve, and the mass ratio of titanium to silicon is SiO 2: TiO2= 10-200: 1, the mol ratio of the epoxidized methanol (10) to the hydrogen peroxide (12) is 4.0-18.0: 1, the mol ratio of the epoxidized propylene (13) to the hydrogen peroxide (12) is 1.2-10.0: 1, the weight space velocity of the epoxidized propylene (13) is 0.5-8.0 h < -1 >.
7. The process for the continuous production of a propylene oxide derivative from propane according to claim 1, characterized in that: in the step (5), the reaction pressure of the 8 polymerization units (E1) - (E8) is 0.10-0.60 MPaA, the reaction temperature is 100-150 ℃, and the catalyst is glycerol.
8. The process for the continuous production of a propylene oxide derivative from propane, as claimed in claim 1, wherein: in the step (6), the reaction pressure of the hydration unit (G1) is 1.10-3.60 MPaA, the reaction temperature is 150-200 ℃, and the molar ratio of water to the last strand of propylene oxide is 5.0-30.0: 1.
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Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5599956A (en) * | 1996-02-22 | 1997-02-04 | Uop | Integrated process for the production of propylene oxide |
| CN1688560A (en) * | 2002-08-30 | 2005-10-26 | 巴斯福股份公司 | Integrated method for synthesising propylene oxide |
| CN108997263A (en) * | 2018-06-29 | 2018-12-14 | 华电煤业集团有限公司 | A kind of system and method for propylene oxide co-production aromatic hydrocarbons |
| CN109219598A (en) * | 2016-05-17 | 2019-01-15 | 赢创德固赛有限公司 | The integrated approach of propylene and propylene oxide is prepared by propane |
-
2021
- 2021-06-30 CN CN202110737508.XA patent/CN113387906B/en active Active
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5599956A (en) * | 1996-02-22 | 1997-02-04 | Uop | Integrated process for the production of propylene oxide |
| CN1688560A (en) * | 2002-08-30 | 2005-10-26 | 巴斯福股份公司 | Integrated method for synthesising propylene oxide |
| CN109219598A (en) * | 2016-05-17 | 2019-01-15 | 赢创德固赛有限公司 | The integrated approach of propylene and propylene oxide is prepared by propane |
| CN108997263A (en) * | 2018-06-29 | 2018-12-14 | 华电煤业集团有限公司 | A kind of system and method for propylene oxide co-production aromatic hydrocarbons |
Non-Patent Citations (1)
| Title |
|---|
| HPPO工艺技术概况和生产工艺中涉及的关键问题;姜祥兵;《吉林化工学院学报》;20190331;第36卷(第3期);9-16 * |
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