ZA200402797B - Process for the preparation of isopropanol. - Google Patents
Process for the preparation of isopropanol. Download PDFInfo
- Publication number
- ZA200402797B ZA200402797B ZA200402797A ZA200402797A ZA200402797B ZA 200402797 B ZA200402797 B ZA 200402797B ZA 200402797 A ZA200402797 A ZA 200402797A ZA 200402797 A ZA200402797 A ZA 200402797A ZA 200402797 B ZA200402797 B ZA 200402797B
- Authority
- ZA
- South Africa
- Prior art keywords
- benzene
- acetone
- isopropanol
- hydrogenation
- products
- Prior art date
Links
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 title claims abstract description 118
- 238000000034 method Methods 0.000 title claims abstract description 41
- 238000002360 preparation method Methods 0.000 title claims abstract description 9
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims abstract description 152
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims abstract description 114
- 238000005984 hydrogenation reaction Methods 0.000 claims abstract description 33
- 238000000926 separation method Methods 0.000 claims abstract description 17
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims abstract description 9
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 44
- 239000000047 product Substances 0.000 claims description 29
- 239000003054 catalyst Substances 0.000 claims description 26
- 229910052759 nickel Inorganic materials 0.000 claims description 21
- 239000006227 byproduct Substances 0.000 claims description 19
- 239000007788 liquid Substances 0.000 claims description 17
- 239000001257 hydrogen Substances 0.000 claims description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims description 16
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 claims description 14
- 238000006243 chemical reaction Methods 0.000 claims description 12
- 239000007795 chemical reaction product Substances 0.000 claims description 10
- 238000004064 recycling Methods 0.000 claims description 7
- FRIBMENBGGCKPD-UHFFFAOYSA-N 3-(2,3-dimethoxyphenyl)prop-2-enal Chemical compound COC1=CC=CC(C=CC=O)=C1OC FRIBMENBGGCKPD-UHFFFAOYSA-N 0.000 claims description 6
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 3
- 230000002152 alkylating effect Effects 0.000 claims description 2
- 230000001590 oxidative effect Effects 0.000 claims description 2
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 1
- 238000004821 distillation Methods 0.000 description 18
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 14
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 14
- 238000010543 cumene process Methods 0.000 description 12
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 8
- 239000007789 gas Substances 0.000 description 7
- 229910052751 metal Inorganic materials 0.000 description 7
- 239000002184 metal Substances 0.000 description 7
- SVTBMSDMJJWYQN-UHFFFAOYSA-N 2-methylpentane-2,4-diol Chemical compound CC(O)CC(C)(C)O SVTBMSDMJJWYQN-UHFFFAOYSA-N 0.000 description 6
- 239000000377 silicon dioxide Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 3
- 229940051250 hexylene glycol Drugs 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- MGNZXYYWBUKAII-UHFFFAOYSA-N cyclohexa-1,3-diene Chemical compound C1CC=CC=C1 MGNZXYYWBUKAII-UHFFFAOYSA-N 0.000 description 2
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 239000002356 single layer Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- NUMXHEUHHRTBQT-AATRIKPKSA-N 2,4-dimethoxy-1-[(e)-2-nitroethenyl]benzene Chemical compound COC1=CC=C(\C=C\[N+]([O-])=O)C(OC)=C1 NUMXHEUHHRTBQT-AATRIKPKSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 241000518994 Conta Species 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- 208000009989 Posterior Leukoencephalopathy Syndrome Diseases 0.000 description 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
- 239000003463 adsorbent Substances 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
- 150000001555 benzenes Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 210000005056 cell body Anatomy 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 239000012084 conversion product Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 1
- JYVHOGDBFNJNMR-UHFFFAOYSA-N hexane;hydrate Chemical compound O.CCCCCC JYVHOGDBFNJNMR-UHFFFAOYSA-N 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
Classifications
-
- 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
- C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
-
- 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
- C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
- C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
- C07C29/143—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of ketones
- C07C29/145—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of ketones with hydrogen or hydrogen-containing gases
-
- 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
- C07C29/74—Separation; Purification; Use of additives, e.g. for stabilisation
- C07C29/88—Separation; Purification; Use of additives, e.g. for stabilisation by treatment giving rise to a chemical modification of at least one compound
- C07C29/90—Separation; Purification; Use of additives, e.g. for stabilisation by treatment giving rise to a chemical modification of at least one compound using hydrogen only
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C39/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
- C07C39/02—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring monocyclic with no unsaturation outside the aromatic ring
- C07C39/04—Phenol
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Steroid Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP01309673 | 2001-11-16 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200402797B true ZA200402797B (en) | 2004-12-23 |
Family
ID=8182464
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200402797A ZA200402797B (en) | 2001-11-16 | 2004-04-13 | Process for the preparation of isopropanol. |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US6939995B2 (cg-RX-API-DMAC7.html) |
| EP (1) | EP1463700B1 (cg-RX-API-DMAC7.html) |
| JP (1) | JP2004536147A (cg-RX-API-DMAC7.html) |
| KR (1) | KR20040055805A (cg-RX-API-DMAC7.html) |
| CN (1) | CN1266100C (cg-RX-API-DMAC7.html) |
| AT (1) | ATE361270T1 (cg-RX-API-DMAC7.html) |
| AU (1) | AU2002342904A1 (cg-RX-API-DMAC7.html) |
| BR (1) | BR0214170A (cg-RX-API-DMAC7.html) |
| DE (1) | DE60219960T2 (cg-RX-API-DMAC7.html) |
| ES (1) | ES2286298T3 (cg-RX-API-DMAC7.html) |
| MX (1) | MXPA04004553A (cg-RX-API-DMAC7.html) |
| RU (1) | RU2296740C2 (cg-RX-API-DMAC7.html) |
| TW (1) | TWI266762B (cg-RX-API-DMAC7.html) |
| WO (1) | WO2003011801A2 (cg-RX-API-DMAC7.html) |
| ZA (1) | ZA200402797B (cg-RX-API-DMAC7.html) |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10008924A1 (de) * | 2000-02-25 | 2001-09-06 | Phenolchemie Gmbh & Co Kg | Verfahren zur Herstellung von Phenol |
| TWI301480B (en) * | 2001-11-16 | 2008-10-01 | Shell Int Research | Process for the hydrogenation of acetone |
| DE102005035816A1 (de) * | 2005-07-30 | 2007-02-01 | Oxeno Olefinchemie Gmbh | Verfahren zur Hydrierung von Oxo-Aldehyden mit hohen Estergehalten |
| KR100874774B1 (ko) * | 2006-08-21 | 2008-12-19 | 이수화학 주식회사 | 이소프로판올 및 고순도 노말파라핀의 동시 제조방법 |
| KR101066703B1 (ko) * | 2006-11-21 | 2011-09-21 | 미쓰이 가가쿠 가부시키가이샤 | 알킬화 방향족 화합물의 제조방법 및 페놀의 제조방법 |
| JP5255318B2 (ja) * | 2007-04-18 | 2013-08-07 | 三井化学株式会社 | アルキル化芳香族化合物の製造方法およびフェノールの製造方法 |
| US7799958B2 (en) | 2007-10-04 | 2010-09-21 | Barclays Bank Plc | Process for the production of iso-propanol by liquid phase hydrogenation |
| KR20110082156A (ko) * | 2008-10-06 | 2011-07-18 | 바져 라이센싱 엘엘씨 | 큐멘의 제조방법 |
| CN102690172A (zh) * | 2011-03-25 | 2012-09-26 | 中国石油化工股份有限公司 | 丙酮加氢生产异丙醇的方法 |
| JP2015166315A (ja) * | 2012-06-27 | 2015-09-24 | 三井化学株式会社 | イソプロパノールの製造方法 |
| CN103539635B (zh) * | 2012-07-12 | 2016-07-13 | 中国石油化工股份有限公司 | 用于丙酮加氢制备异丙醇的方法 |
| CN109851467A (zh) * | 2012-07-26 | 2019-06-07 | 巴杰许可有限责任公司 | 制备枯烯的方法 |
| CN103772145B (zh) * | 2012-10-23 | 2016-09-21 | 中国石油化工股份有限公司 | 一种丙酮加氢制异丙醇的分离方法 |
| RU2519950C1 (ru) * | 2013-03-05 | 2014-06-20 | Федеральное государственное бюджетное образовательное учреждение высшего профессионального образования "Волгоградский государственный технический университет" (ВолгГТУ) | Способ получения первичных или вторичный спиртов |
| CN106008186B (zh) * | 2016-06-02 | 2018-05-15 | 南京师范大学 | 一种异丙醇、丙酮及水混合溶液的分离方法 |
| EP4488252A1 (en) * | 2022-08-22 | 2025-01-08 | LG Chem, Ltd. | Method for preparing isopropyl alcohol |
| EP4549622A1 (en) | 2023-10-31 | 2025-05-07 | Basf Se | Hydrogenation of carbonyl compounds using hydrogen with low deuterium content |
| WO2025105774A1 (ko) * | 2023-11-15 | 2025-05-22 | 주식회사 엘지화학 | 이소프로필 알코올의 제조방법 |
| CN120641387A (zh) * | 2023-11-15 | 2025-09-12 | 株式会社Lg化学 | 纯化异丙醇的方法 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL59261C (cg-RX-API-DMAC7.html) | 1941-09-05 | |||
| JPS5550704B2 (cg-RX-API-DMAC7.html) * | 1972-06-08 | 1980-12-19 | ||
| US4480134A (en) * | 1983-04-05 | 1984-10-30 | General Electric Company | Process for preparing phenol and acetone from cumene |
| JP2774607B2 (ja) * | 1988-09-30 | 1998-07-09 | 三井化学株式会社 | フェノールの製造方法およびその製造時の副生アセトンからプロピレンを得る方法 |
| US5017729A (en) * | 1988-09-30 | 1991-05-21 | Mitsui Petrochemical Industries, Ltd. | Phenol preparation process and propylene recovery therefrom |
| CA2003925C (en) | 1988-11-28 | 1999-11-23 | Shintaro Araki | Preparation of cumene through alkylation of an aromatic compound and preparation of phenol through cumene |
| FR2656300B1 (fr) | 1989-12-21 | 1993-06-11 | Inst Francais Du Petrole | Procede de production de phenol. |
| DE10008924A1 (de) * | 2000-02-25 | 2001-09-06 | Phenolchemie Gmbh & Co Kg | Verfahren zur Herstellung von Phenol |
| KR100852565B1 (ko) * | 2000-09-25 | 2008-08-18 | 엑손모빌 케미칼 패턴츠 인코포레이티드 | 페놀 생산에서 분해 유출물의 수소화 방법 |
| JP4754058B2 (ja) * | 2000-10-16 | 2011-08-24 | 三井化学株式会社 | イソプロピルアルコールの製造方法 |
-
2002
- 2002-11-11 TW TW091133010A patent/TWI266762B/zh active
- 2002-11-12 CN CNB02822695XA patent/CN1266100C/zh not_active Ceased
- 2002-11-12 WO PCT/EP2002/012650 patent/WO2003011801A2/en not_active Ceased
- 2002-11-12 EP EP02779551A patent/EP1463700B1/en not_active Revoked
- 2002-11-12 AU AU2002342904A patent/AU2002342904A1/en not_active Abandoned
- 2002-11-12 AT AT02779551T patent/ATE361270T1/de not_active IP Right Cessation
- 2002-11-12 ES ES02779551T patent/ES2286298T3/es not_active Expired - Lifetime
- 2002-11-12 JP JP2003516996A patent/JP2004536147A/ja active Pending
- 2002-11-12 DE DE60219960T patent/DE60219960T2/de not_active Revoked
- 2002-11-12 KR KR10-2004-7007252A patent/KR20040055805A/ko not_active Ceased
- 2002-11-12 RU RU2004118066/04A patent/RU2296740C2/ru not_active IP Right Cessation
- 2002-11-12 BR BR0214170-1A patent/BR0214170A/pt not_active IP Right Cessation
- 2002-11-14 US US10/294,192 patent/US6939995B2/en not_active Expired - Fee Related
-
2004
- 2004-04-13 ZA ZA200402797A patent/ZA200402797B/en unknown
- 2004-05-13 MX MXPA04004553A patent/MXPA04004553A/es active IP Right Grant
Also Published As
| Publication number | Publication date |
|---|---|
| TW200407288A (en) | 2004-05-16 |
| RU2004118066A (ru) | 2006-01-10 |
| JP2004536147A (ja) | 2004-12-02 |
| MXPA04004553A (es) | 2004-08-13 |
| BR0214170A (pt) | 2004-09-28 |
| DE60219960T2 (de) | 2008-01-17 |
| WO2003011801A3 (en) | 2004-02-19 |
| CN1585734A (zh) | 2005-02-23 |
| WO2003011801A2 (en) | 2003-02-13 |
| DE60219960D1 (de) | 2007-06-14 |
| EP1463700A2 (en) | 2004-10-06 |
| ES2286298T3 (es) | 2007-12-01 |
| KR20040055805A (ko) | 2004-06-26 |
| CN1266100C (zh) | 2006-07-26 |
| AU2002342904A1 (en) | 2003-02-17 |
| EP1463700B1 (en) | 2007-05-02 |
| US6939995B2 (en) | 2005-09-06 |
| TWI266762B (en) | 2006-11-21 |
| RU2296740C2 (ru) | 2007-04-10 |
| US20030149314A1 (en) | 2003-08-07 |
| ATE361270T1 (de) | 2007-05-15 |
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