RU2005714C1 - Способ непрерывного получения альдегидов c7-c17 - Google Patents
Способ непрерывного получения альдегидов c7-c17 Download PDFInfo
- Publication number
- RU2005714C1 RU2005714C1 SU884613118A SU4613118A RU2005714C1 RU 2005714 C1 RU2005714 C1 RU 2005714C1 SU 884613118 A SU884613118 A SU 884613118A SU 4613118 A SU4613118 A SU 4613118A RU 2005714 C1 RU2005714 C1 RU 2005714C1
- Authority
- RU
- Russia
- Prior art keywords
- hydroformylation
- aldehyde
- zone
- products
- product
- Prior art date
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- 150000001299 aldehydes Chemical class 0.000 title claims abstract description 99
- 238000000034 method Methods 0.000 title claims description 53
- 230000008569 process Effects 0.000 title claims description 17
- 238000003786 synthesis reaction Methods 0.000 title abstract 2
- 230000015572 biosynthetic process Effects 0.000 title description 33
- 239000003446 ligand Substances 0.000 claims abstract description 43
- 150000001336 alkenes Chemical class 0.000 claims abstract description 35
- 238000007037 hydroformylation reaction Methods 0.000 claims description 87
- 239000007788 liquid Substances 0.000 claims description 51
- 239000003054 catalyst Substances 0.000 claims description 42
- 239000006227 byproduct Substances 0.000 claims description 40
- 238000009833 condensation Methods 0.000 claims description 29
- 230000005494 condensation Effects 0.000 claims description 29
- 239000012442 inert solvent Substances 0.000 claims description 20
- 238000011027 product recovery Methods 0.000 claims description 12
- 239000007859 condensation product Substances 0.000 claims description 9
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims description 7
- 239000007795 chemical reaction product Substances 0.000 claims description 5
- 230000008929 regeneration Effects 0.000 claims description 4
- 238000011069 regeneration method Methods 0.000 claims description 4
- 238000005516 engineering process Methods 0.000 claims description 2
- 238000010924 continuous production Methods 0.000 claims 1
- BDDWSAASCFBVBK-UHFFFAOYSA-N rhodium;triphenylphosphane Chemical compound [Rh].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 BDDWSAASCFBVBK-UHFFFAOYSA-N 0.000 claims 1
- 229910052703 rhodium Inorganic materials 0.000 abstract description 33
- 239000010948 rhodium Substances 0.000 abstract description 33
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 abstract description 33
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 abstract description 30
- 239000000203 mixture Substances 0.000 abstract description 21
- 238000006243 chemical reaction Methods 0.000 abstract description 14
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 abstract description 6
- 229910000073 phosphorus hydride Inorganic materials 0.000 abstract description 3
- 239000000126 substance Substances 0.000 abstract description 3
- 230000003197 catalytic effect Effects 0.000 abstract description 2
- 239000003153 chemical reaction reagent Substances 0.000 abstract 2
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 230000000694 effects Effects 0.000 abstract 1
- 239000000047 product Substances 0.000 description 76
- 238000009835 boiling Methods 0.000 description 50
- 239000002904 solvent Substances 0.000 description 43
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- 230000000052 comparative effect Effects 0.000 description 14
- 239000007789 gas Substances 0.000 description 14
- GYHFUZHODSMOHU-UHFFFAOYSA-N nonanal Chemical compound CCCCCCCCC=O GYHFUZHODSMOHU-UHFFFAOYSA-N 0.000 description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
- 238000000926 separation method Methods 0.000 description 12
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 11
- -1 alkyl radical Chemical class 0.000 description 10
- 238000004821 distillation Methods 0.000 description 10
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- 239000001257 hydrogen Substances 0.000 description 9
- 229910052739 hydrogen Inorganic materials 0.000 description 9
- 239000013638 trimer Substances 0.000 description 9
- 229910002091 carbon monoxide Inorganic materials 0.000 description 8
- 229910017052 cobalt Inorganic materials 0.000 description 8
- 239000010941 cobalt Substances 0.000 description 8
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 8
- 238000005984 hydrogenation reaction Methods 0.000 description 8
- 125000004432 carbon atom Chemical group C* 0.000 description 7
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 7
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- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 6
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- 238000002474 experimental method Methods 0.000 description 6
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- 239000000498 cooling water Substances 0.000 description 4
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- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 4
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- AFFLGGQVNFXPEV-UHFFFAOYSA-N 1-decene Chemical compound CCCCCCCCC=C AFFLGGQVNFXPEV-UHFFFAOYSA-N 0.000 description 3
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- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 2
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- 150000002334 glycols Chemical class 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
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- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 239000011574 phosphorus Substances 0.000 description 2
- 229920001451 polypropylene glycol Polymers 0.000 description 2
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- 238000010992 reflux Methods 0.000 description 2
- BGHCVCJVXZWKCC-UHFFFAOYSA-N tetradecane Chemical compound CCCCCCCCCCCCCC BGHCVCJVXZWKCC-UHFFFAOYSA-N 0.000 description 2
- HVLLSGMXQDNUAL-UHFFFAOYSA-N triphenyl phosphite Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)OC1=CC=CC=C1 HVLLSGMXQDNUAL-UHFFFAOYSA-N 0.000 description 2
- KMPQYAYAQWNLME-UHFFFAOYSA-N undecanal Chemical compound CCCCCCCCCCC=O KMPQYAYAQWNLME-UHFFFAOYSA-N 0.000 description 2
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- CKGKXGQVRVAKEA-UHFFFAOYSA-N (2-methylphenyl)-phenylmethanone Chemical compound CC1=CC=CC=C1C(=O)C1=CC=CC=C1 CKGKXGQVRVAKEA-UHFFFAOYSA-N 0.000 description 1
- 239000001893 (2R)-2-methylbutanal Substances 0.000 description 1
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- QZYDOKBVZJLQCK-UHFFFAOYSA-N 1,2-diethoxybenzene Chemical compound CCOC1=CC=CC=C1OCC QZYDOKBVZJLQCK-UHFFFAOYSA-N 0.000 description 1
- OIAQMFOKAXHPNH-UHFFFAOYSA-N 1,2-diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC=C1C1=CC=CC=C1 OIAQMFOKAXHPNH-UHFFFAOYSA-N 0.000 description 1
- VQOXUMQBYILCKR-UHFFFAOYSA-N 1-Tridecene Chemical compound CCCCCCCCCCCC=C VQOXUMQBYILCKR-UHFFFAOYSA-N 0.000 description 1
- CRSBERNSMYQZNG-UHFFFAOYSA-N 1-dodecene Chemical compound CCCCCCCCCCC=C CRSBERNSMYQZNG-UHFFFAOYSA-N 0.000 description 1
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 1
- BPIUIOXAFBGMNB-UHFFFAOYSA-N 1-hexoxyhexane Chemical compound CCCCCCOCCCCCC BPIUIOXAFBGMNB-UHFFFAOYSA-N 0.000 description 1
- DKZRLCHWDNEKRH-UHFFFAOYSA-N 1-nonoxynonane Chemical compound CCCCCCCCCOCCCCCCCCC DKZRLCHWDNEKRH-UHFFFAOYSA-N 0.000 description 1
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- LCZVSXRMYJUNFX-UHFFFAOYSA-N 2-[2-(2-hydroxypropoxy)propoxy]propan-1-ol Chemical compound CC(O)COC(C)COC(C)CO LCZVSXRMYJUNFX-UHFFFAOYSA-N 0.000 description 1
- FHVRTMVXBVDWCK-UHFFFAOYSA-N 2-methyl-2-prop-2-enoxypropane Chemical compound CC(C)(C)OCC=C FHVRTMVXBVDWCK-UHFFFAOYSA-N 0.000 description 1
- JSDZSLGMRRSAHD-UHFFFAOYSA-N 3-methylbutan-2-ylcyclopropane Chemical compound CC(C)C(C)C1CC1 JSDZSLGMRRSAHD-UHFFFAOYSA-N 0.000 description 1
- RITONZMLZWYPHW-UHFFFAOYSA-N 3-methylhex-1-ene Chemical compound CCCC(C)C=C RITONZMLZWYPHW-UHFFFAOYSA-N 0.000 description 1
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- UXMQORVHJMUQFD-UHFFFAOYSA-N Heptanophenone Chemical compound CCCCCCC(=O)C1=CC=CC=C1 UXMQORVHJMUQFD-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical class C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 150000001241 acetals Chemical class 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 125000003158 alcohol group Chemical group 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000005036 alkoxyphenyl group Chemical group 0.000 description 1
- 150000005215 alkyl ethers Chemical class 0.000 description 1
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical class COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- GPMUMMNTAZMBEC-UHFFFAOYSA-N bis(oxomethylidene)rhodium Chemical compound [Rh].[O+]#[C-].[O+]#[C-] GPMUMMNTAZMBEC-UHFFFAOYSA-N 0.000 description 1
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 1
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- 238000010586 diagram Methods 0.000 description 1
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- 150000005575 dimethoxybenzenes Chemical class 0.000 description 1
- CZZYITDELCSZES-UHFFFAOYSA-N diphenylmethane Chemical compound C=1C=CC=CC=1CC1=CC=CC=C1 CZZYITDELCSZES-UHFFFAOYSA-N 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
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- 150000004820 halides Chemical class 0.000 description 1
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- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
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- 239000007791 liquid phase Substances 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene-acid Natural products C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 1
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- RPGWZZNNEUHDAQ-UHFFFAOYSA-N phenylphosphine Chemical compound PC1=CC=CC=C1 RPGWZZNNEUHDAQ-UHFFFAOYSA-N 0.000 description 1
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- 238000004064 recycling Methods 0.000 description 1
- 150000003283 rhodium Chemical class 0.000 description 1
- 150000003333 secondary alcohols Chemical class 0.000 description 1
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- 238000012360 testing method Methods 0.000 description 1
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- IAQRGUVFOMOMEM-ONEGZZNKSA-N trans-but-2-ene Chemical compound C\C=C\C IAQRGUVFOMOMEM-ONEGZZNKSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- YFNKIDBQEZZDLK-UHFFFAOYSA-N triglyme Chemical compound COCCOCCOCCOC YFNKIDBQEZZDLK-UHFFFAOYSA-N 0.000 description 1
- 239000007861 trimeric product Substances 0.000 description 1
- FIQMHBFVRAXMOP-UHFFFAOYSA-N triphenylphosphane oxide Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=O)C1=CC=CC=C1 FIQMHBFVRAXMOP-UHFFFAOYSA-N 0.000 description 1
- IQKSLJOIKWOGIZ-UHFFFAOYSA-N tris(4-chlorophenyl)phosphane Chemical compound C1=CC(Cl)=CC=C1P(C=1C=CC(Cl)=CC=1)C1=CC=C(Cl)C=C1 IQKSLJOIKWOGIZ-UHFFFAOYSA-N 0.000 description 1
- WXAZIUYTQHYBFW-UHFFFAOYSA-N tris(4-methylphenyl)phosphane Chemical compound C1=CC(C)=CC=C1P(C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 WXAZIUYTQHYBFW-UHFFFAOYSA-N 0.000 description 1
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB8616038 | 1986-07-01 | ||
| GB868616038A GB8616038D0 (en) | 1986-07-01 | 1986-07-01 | Process |
| PCT/GB1987/000408 WO1988000179A2 (en) | 1986-07-01 | 1987-06-12 | Process for the production of aldehydes by hydroformylation |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| RU2005714C1 true RU2005714C1 (ru) | 1994-01-15 |
Family
ID=10600364
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU884613118A RU2005714C1 (ru) | 1986-07-01 | 1988-12-30 | Способ непрерывного получения альдегидов c7-c17 |
Country Status (4)
| Country | Link |
|---|---|
| GB (1) | GB8616038D0 (enrdf_load_stackoverflow) |
| IN (1) | IN170023B (enrdf_load_stackoverflow) |
| RU (1) | RU2005714C1 (enrdf_load_stackoverflow) |
| ZA (1) | ZA874528B (enrdf_load_stackoverflow) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2719438C2 (ru) * | 2015-11-10 | 2020-04-17 | Дау Текнолоджи Инвестментс Ллк | Способ получения альдегидов |
| RU2788171C2 (ru) * | 2018-05-30 | 2023-01-17 | Дау Текнолоджи Инвестментс Ллк | Способы регулирования процессов гидроформилирования |
-
1986
- 1986-07-01 GB GB868616038A patent/GB8616038D0/en active Pending
-
1987
- 1987-06-09 IN IN429/MAS/87A patent/IN170023B/en unknown
- 1987-06-23 ZA ZA874528A patent/ZA874528B/xx unknown
-
1988
- 1988-12-30 RU SU884613118A patent/RU2005714C1/ru active
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2719438C2 (ru) * | 2015-11-10 | 2020-04-17 | Дау Текнолоджи Инвестментс Ллк | Способ получения альдегидов |
| RU2788171C2 (ru) * | 2018-05-30 | 2023-01-17 | Дау Текнолоджи Инвестментс Ллк | Способы регулирования процессов гидроформилирования |
Also Published As
| Publication number | Publication date |
|---|---|
| GB8616038D0 (en) | 1986-08-06 |
| IN170023B (enrdf_load_stackoverflow) | 1992-01-25 |
| ZA874528B (en) | 1988-04-27 |
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