CN105237456B - 一种吡咯烷酮类产品的生产方法 - Google Patents
一种吡咯烷酮类产品的生产方法 Download PDFInfo
- Publication number
- CN105237456B CN105237456B CN201510679900.8A CN201510679900A CN105237456B CN 105237456 B CN105237456 B CN 105237456B CN 201510679900 A CN201510679900 A CN 201510679900A CN 105237456 B CN105237456 B CN 105237456B
- Authority
- CN
- China
- Prior art keywords
- reactor
- dehydrogenation
- amination
- pyrrolidones
- catalyst
- 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.)
- Active
Links
- 150000004040 pyrrolidinones Chemical class 0.000 title claims abstract description 50
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 30
- 238000005576 amination reaction Methods 0.000 claims abstract description 56
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical class OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 claims abstract description 44
- 239000003054 catalyst Substances 0.000 claims abstract description 44
- 238000006243 chemical reaction Methods 0.000 claims abstract description 41
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 claims abstract description 28
- 238000000034 method Methods 0.000 claims abstract description 19
- 239000002994 raw material Substances 0.000 claims abstract description 13
- 238000000926 separation method Methods 0.000 claims abstract description 9
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 52
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 32
- 229910021529 ammonia Inorganic materials 0.000 claims description 26
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 22
- 230000010354 integration Effects 0.000 claims description 21
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical group O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 18
- 150000001412 amines Chemical class 0.000 claims description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 17
- 239000007791 liquid phase Substances 0.000 claims description 12
- 239000007788 liquid Substances 0.000 claims description 11
- 239000000203 mixture Substances 0.000 claims description 11
- 239000000377 silicon dioxide Substances 0.000 claims description 10
- 229910052802 copper Inorganic materials 0.000 claims description 9
- 239000010949 copper Substances 0.000 claims description 8
- 239000000463 material Substances 0.000 claims description 8
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 7
- 239000002808 molecular sieve Substances 0.000 claims description 7
- 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 7
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000000376 reactant Substances 0.000 claims description 6
- RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Natural products C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 6
- 229910052751 metal Inorganic materials 0.000 claims description 5
- 239000002184 metal Substances 0.000 claims description 5
- 238000002156 mixing Methods 0.000 claims description 5
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 claims description 5
- CPLXHLVBOLITMK-UHFFFAOYSA-N Magnesium oxide Chemical compound [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 claims description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 4
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 claims description 4
- 229910052810 boron oxide Inorganic materials 0.000 claims description 4
- 238000006555 catalytic reaction Methods 0.000 claims description 4
- JKWMSGQKBLHBQQ-UHFFFAOYSA-N diboron trioxide Chemical compound O=BOB=O JKWMSGQKBLHBQQ-UHFFFAOYSA-N 0.000 claims description 4
- 238000007670 refining Methods 0.000 claims description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 4
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 claims description 4
- 239000007789 gas Substances 0.000 claims description 3
- 229910052759 nickel Inorganic materials 0.000 claims description 3
- RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical compound [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 claims description 3
- 239000011787 zinc oxide Substances 0.000 claims description 3
- 229910001928 zirconium oxide Inorganic materials 0.000 claims description 3
- 239000004411 aluminium Substances 0.000 claims description 2
- 229910052782 aluminium Inorganic materials 0.000 claims description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 2
- BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 claims description 2
- 239000000292 calcium oxide Substances 0.000 claims description 2
- ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 claims description 2
- 229910017052 cobalt Inorganic materials 0.000 claims description 2
- 239000010941 cobalt Substances 0.000 claims description 2
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 2
- 239000000395 magnesium oxide Substances 0.000 claims description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims 2
- 230000003647 oxidation Effects 0.000 claims 2
- 238000007254 oxidation reaction Methods 0.000 claims 2
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 claims 1
- 229910052788 barium Inorganic materials 0.000 claims 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 claims 1
- 230000003139 buffering effect Effects 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 claims 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims 1
- 229910052726 zirconium Inorganic materials 0.000 claims 1
- 238000006356 dehydrogenation reaction Methods 0.000 abstract description 20
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical class CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 abstract description 17
- 238000005265 energy consumption Methods 0.000 abstract description 12
- 230000008901 benefit Effects 0.000 abstract description 4
- 238000000746 purification Methods 0.000 abstract description 3
- ZFPGARUNNKGOBB-UHFFFAOYSA-N 1-Ethyl-2-pyrrolidinone Chemical class CCN1CCCC1=O ZFPGARUNNKGOBB-UHFFFAOYSA-N 0.000 abstract description 2
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical class CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 abstract description 2
- 239000000047 product Substances 0.000 description 40
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 18
- 239000000126 substance Substances 0.000 description 11
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 8
- 238000011068 loading method Methods 0.000 description 6
- 238000002425 crystallisation Methods 0.000 description 5
- 230000008025 crystallization Effects 0.000 description 5
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 229910052681 coesite Inorganic materials 0.000 description 4
- 229910052906 cristobalite Inorganic materials 0.000 description 4
- 150000003053 piperidines Chemical class 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 229910052682 stishovite Inorganic materials 0.000 description 4
- 229910052905 tridymite Inorganic materials 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- 235000011114 ammonium hydroxide Nutrition 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 150000002431 hydrogen Chemical class 0.000 description 3
- -1 pipecoline Chemical class 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 239000004149 tartrazine Substances 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- QOZOFODNIBQPGN-UHFFFAOYSA-N 2,4-dimethylpiperidine Chemical class CC1CCNC(C)C1 QOZOFODNIBQPGN-UHFFFAOYSA-N 0.000 description 2
- SDGKUVSVPIIUCF-UHFFFAOYSA-N 2,6-dimethylpiperidine Chemical compound CC1CCCC(C)N1 SDGKUVSVPIIUCF-UHFFFAOYSA-N 0.000 description 2
- IDWRJRPUIXRFRX-UHFFFAOYSA-N 3,5-dimethylpiperidine Chemical class CC1CNCC(C)C1 IDWRJRPUIXRFRX-UHFFFAOYSA-N 0.000 description 2
- JEGMWWXJUXDNJN-UHFFFAOYSA-N 3-methylpiperidine Chemical class CC1CCCNC1 JEGMWWXJUXDNJN-UHFFFAOYSA-N 0.000 description 2
- UZOFELREXGAFOI-UHFFFAOYSA-N 4-methylpiperidine Chemical class CC1CCNCC1 UZOFELREXGAFOI-UHFFFAOYSA-N 0.000 description 2
- 239000004229 Alkannin Substances 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 229910019580 Cr Zr Inorganic materials 0.000 description 2
- 229910019817 Cr—Zr Inorganic materials 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- JEYWNNAZDLFBFF-UHFFFAOYSA-N Nafoxidine Chemical compound C1CC2=CC(OC)=CC=C2C(C=2C=CC(OCCN3CCCC3)=CC=2)=C1C1=CC=CC=C1 JEYWNNAZDLFBFF-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 239000003905 agrochemical Substances 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 239000012847 fine chemical Substances 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- 238000010574 gas phase reaction Methods 0.000 description 2
- SWTFBLUIBHXOAH-UHFFFAOYSA-N n-butylhydroxylamine Chemical compound CCCCNO SWTFBLUIBHXOAH-UHFFFAOYSA-N 0.000 description 2
- 229950002366 nafoxidine Drugs 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 150000003233 pyrroles Chemical class 0.000 description 2
- 239000002151 riboflavin Substances 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- 230000001629 suppression Effects 0.000 description 2
- ADVWVIQNAOXLCV-UHFFFAOYSA-N 2,2,6,6-tetramethylpiperazine Chemical class CC1(C)CNCC(C)(C)N1 ADVWVIQNAOXLCV-UHFFFAOYSA-N 0.000 description 1
- RKMGAJGJIURJSJ-UHFFFAOYSA-N 2,2,6,6-tetramethylpiperidine Chemical class CC1(C)CCCC(C)(C)N1 RKMGAJGJIURJSJ-UHFFFAOYSA-N 0.000 description 1
- MZNSQRLUUXWLSB-UHFFFAOYSA-N 2-ethenyl-1h-pyrrole Chemical compound C=CC1=CC=CN1 MZNSQRLUUXWLSB-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 229920001007 Nylon 4 Polymers 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- QVQLCTNNEUAWMS-UHFFFAOYSA-N barium oxide Inorganic materials [Ba]=O QVQLCTNNEUAWMS-UHFFFAOYSA-N 0.000 description 1
- CSSYLTMKCUORDA-UHFFFAOYSA-N barium(2+);oxygen(2-) Chemical compound [O-2].[Ba+2] CSSYLTMKCUORDA-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000004359 castor oil Substances 0.000 description 1
- 235000019438 castor oil Nutrition 0.000 description 1
- 239000012459 cleaning agent Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 150000003997 cyclic ketones Chemical class 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000007872 degassing Methods 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 238000003795 desorption Methods 0.000 description 1
- 230000005611 electricity Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
- 229910002804 graphite Inorganic materials 0.000 description 1
- 239000010439 graphite Substances 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 231100000086 high toxicity Toxicity 0.000 description 1
- 230000002779 inactivation Effects 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- 239000012774 insulation material Substances 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 230000002045 lasting effect Effects 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 239000005416 organic matter Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000004597 plastic additive Substances 0.000 description 1
- 239000003880 polar aprotic solvent Substances 0.000 description 1
- 239000003495 polar organic solvent Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000003239 pyrrolones Chemical class 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 230000011218 segmentation Effects 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 238000009834 vaporization Methods 0.000 description 1
- 230000008016 vaporization Effects 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/24—Oxygen or sulfur atoms
- C07D207/26—2-Pyrrolidones
- C07D207/263—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms
- C07D207/267—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to the ring nitrogen atom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Pyrrole Compounds (AREA)
Abstract
Description
运行时间(h) | GBL(wt%) | THF(wt%) | 正丁醇(wt%) | α-吡咯烷酮(wt%) |
30 | 0.021 | 0.011 | 0.002 | 99.15 |
720 | 0.019 | 0.013 | 0.002 | 99.12 |
运行时间(h) | BDO(wt%) | THF(wt%) | 正丁醇(wt%) | NMP(wt%) | GBL(wt%) |
150 | 0.012 | 0.014 | 0.002 | 68.710 | 29.231 |
750 | 0.014 | 0.018 | 0.002 | 68.641 | 29.204 |
运行时间(h) | GBL(wt%) | THF(wt%) | 正丁醇(wt%) | NMP(wt%) |
30 | 0.008 | 0.020 | 0.002 | 99.35 |
720 | 0.009 | 0.021 | 0.002 | 99.32 |
运行时间(h) | GBL(wt%) | THF(wt%) | 正丁醇(wt%) | BDO(wt%) |
30 | 97.75 | 0.70 | 0.21 | 0.15 |
750 | 97.70 | 0.73 | 0.22 | 0.20 |
Claims (10)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201510679900.8A CN105237456B (zh) | 2015-10-19 | 2015-10-19 | 一种吡咯烷酮类产品的生产方法 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201510679900.8A CN105237456B (zh) | 2015-10-19 | 2015-10-19 | 一种吡咯烷酮类产品的生产方法 |
Publications (2)
Publication Number | Publication Date |
---|---|
CN105237456A CN105237456A (zh) | 2016-01-13 |
CN105237456B true CN105237456B (zh) | 2017-12-22 |
Family
ID=55035329
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN201510679900.8A Active CN105237456B (zh) | 2015-10-19 | 2015-10-19 | 一种吡咯烷酮类产品的生产方法 |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN105237456B (zh) |
Families Citing this family (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN108774163B (zh) * | 2018-07-17 | 2021-07-06 | 天津中福环保科技股份有限公司 | 一种锂电池生产中nmp回收提纯精密处理的方法 |
CN110183370B (zh) * | 2019-06-28 | 2022-04-29 | 迈奇化学股份有限公司 | 一种n-乙基吡咯烷酮的工业生产方法 |
CN110526849B (zh) * | 2019-09-29 | 2021-05-11 | 迈奇化学股份有限公司 | 一种1,4-丁二醇胺化制备烷基吡咯烷酮的方法 |
CN111892525A (zh) * | 2020-05-08 | 2020-11-06 | 迈奇化学股份有限公司 | 一种液晶面板用n-甲基吡咯烷酮及其生产工艺 |
CN112500269B (zh) * | 2020-11-09 | 2023-01-13 | 万华化学集团股份有限公司 | 一种cdol脱氢制备cdon混合物冷却的装置***和方法 |
CN112341339A (zh) * | 2020-11-30 | 2021-02-09 | 江苏凯美普瑞工程技术有限公司 | 一种合成1,4-丁二胺的方法和装置 |
CN113563247B (zh) * | 2021-08-11 | 2022-03-25 | 安徽晟捷新能源科技股份有限公司 | 一种利用1,4-丁二醇制备n-甲基吡咯烷酮的方法 |
CN117185979A (zh) * | 2023-09-11 | 2023-12-08 | 北京恒瑞新霖科技有限公司 | 一种节能型吡咯烷酮的制备方法 |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101903344A (zh) * | 2007-12-21 | 2010-12-01 | 梨树化学株式会社 | N-甲基吡咯烷酮的制备方法 |
CN101987831A (zh) * | 2009-07-29 | 2011-03-23 | Sk能源株式会社 | 制备n-甲基吡咯烷酮的方法 |
CN102029156A (zh) * | 2009-10-07 | 2011-04-27 | Sk能源株式会社 | 由1,4-丁二醇制备γ-丁内酯和N-甲基吡咯烷酮的方法 |
CN102070501A (zh) * | 2009-11-25 | 2011-05-25 | Sk能源株式会社 | 由1,4-丁二醇制备n-甲基吡咯烷酮的方法 |
-
2015
- 2015-10-19 CN CN201510679900.8A patent/CN105237456B/zh active Active
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101903344A (zh) * | 2007-12-21 | 2010-12-01 | 梨树化学株式会社 | N-甲基吡咯烷酮的制备方法 |
CN101987831A (zh) * | 2009-07-29 | 2011-03-23 | Sk能源株式会社 | 制备n-甲基吡咯烷酮的方法 |
CN102029156A (zh) * | 2009-10-07 | 2011-04-27 | Sk能源株式会社 | 由1,4-丁二醇制备γ-丁内酯和N-甲基吡咯烷酮的方法 |
CN102070501A (zh) * | 2009-11-25 | 2011-05-25 | Sk能源株式会社 | 由1,4-丁二醇制备n-甲基吡咯烷酮的方法 |
Non-Patent Citations (2)
Title |
---|
Modified ZSM-5 Catalysts for the Synthesis of Five- and Six-Membered Heterocyclics;Yarlagadda V.et al.;《J. Org. Chem.》;19941231;第59卷(第14期);第3998-4000页 * |
Synthetic Zeolites as Catalysts for the Ring Conversion of γ-Butyrolactone into 1-Substituted 2-Pyrrolidinones;Kou T.et al.;《Bulletin of the Chemical Society of Japan》;19771031;第50卷(第10期);第2518-2519页 * |
Also Published As
Publication number | Publication date |
---|---|
CN105237456A (zh) | 2016-01-13 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN105237456B (zh) | 一种吡咯烷酮类产品的生产方法 | |
CN102617518B (zh) | 顺酐气相加氢一步法制备四氢呋喃 | |
EP2730566B1 (en) | Method for producing tetrahydrofuran | |
CN114100640B (zh) | 无机固体超强酸负载钯催化剂及其制备方法和生产1,4-丁二醇的方法 | |
CN109748804A (zh) | 异丙醇胺的生产方法 | |
CN103467263A (zh) | 一种异佛尔酮的制备方法 | |
CN107903146B (zh) | 一种催化氧化1-己烯制备1,2-己二醇的方法 | |
CN104557454B (zh) | 一种醋酸加氢制备高品质乙醇的方法 | |
CN109704907A (zh) | 抽余油制备己烷的方法 | |
CN102794185B (zh) | 制备1,3-二氧戊环的方法及所用催化剂和装置 | |
CN109704908B (zh) | 芳烃抽余油制备己烷的方法 | |
CN109796304A (zh) | 一种bed的合成方法 | |
CN109438216A (zh) | 一种高纯度异辛酸的制备方法 | |
CN100413856C (zh) | 一种威士忌内酯的制备方法 | |
CN105566064B (zh) | 一种醋酸加氢制备乙醇的方法 | |
WO2013030287A1 (de) | Verfahren zur herstellung von eddn und/oder edmn durch umsetzung von fach und eda | |
CN105481649B (zh) | 一种乙酸加氢制备乙醇的方法 | |
CN113277996A (zh) | 一种灵活生产四氢呋喃和γ-丁内酯的方法 | |
US3067255A (en) | Production of ethylene diamine | |
JP6015169B2 (ja) | テトラヒドロフランの製造方法 | |
CN105566060B (zh) | 醋酸加氢制备乙醇的方法 | |
CN104557453B (zh) | 一种醋酸加氢制备乙醇的方法 | |
CN115850073B (zh) | 一种制备甲基丙烯酸甲酯的方法及装置 | |
CN115806495B (zh) | 联产丙二醇甲醚和异丙醇胺的方法 | |
CN112279783B (zh) | 一种超临界条件下制备3-羟基丙腈的方法 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
C06 | Publication | ||
PB01 | Publication | ||
C10 | Entry into substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
GR01 | Patent grant | ||
GR01 | Patent grant | ||
TR01 | Transfer of patent right | ||
TR01 | Transfer of patent right |
Effective date of registration: 20180725 Address after: 457000 the west section of Shengli Road, Puyang, Henan Province Patentee after: MYJ CHEMICAL CO.,LTD. Address before: No. 19 Qingyuan North Road, Huangcun, Daxing District, Beijing Patentee before: BEIJING INSTITUTE OF PETROCHEMICAL TECHNOLOGY |
|
PE01 | Entry into force of the registration of the contract for pledge of patent right | ||
PE01 | Entry into force of the registration of the contract for pledge of patent right |
Denomination of invention: A production method of pyrrolidone products Effective date of registration: 20230724 Granted publication date: 20171222 Pledgee: Bank of China Limited by Share Ltd. Puyang branch Pledgor: MYJ CHEMICAL CO.,LTD. Registration number: Y2023980049672 |
|
CP03 | Change of name, title or address |
Address after: 457000 the west section of Shengli Road, Puyang, Henan Province Patentee after: New Maiqi Materials Co.,Ltd. Country or region after: China Address before: 457000 the west section of Shengli Road, Puyang, Henan Province Patentee before: MYJ CHEMICAL CO.,LTD. Country or region before: China |