CA1057313A - Process for the continuous production of 2-ethyl hexanol - Google Patents
Process for the continuous production of 2-ethyl hexanolInfo
- Publication number
- CA1057313A CA1057313A CA232,598A CA232598A CA1057313A CA 1057313 A CA1057313 A CA 1057313A CA 232598 A CA232598 A CA 232598A CA 1057313 A CA1057313 A CA 1057313A
- Authority
- CA
- Canada
- Prior art keywords
- ethyl
- zone
- hexenal
- condensation
- ethyl hexenal
- 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.)
- Expired
Links
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 title claims abstract description 30
- 238000000034 method Methods 0.000 title claims abstract description 19
- 230000008569 process Effects 0.000 title claims abstract description 13
- 238000010924 continuous production Methods 0.000 title claims abstract description 7
- PYLMCYQHBRSDND-UHFFFAOYSA-N 2-ethyl-2-hexenal Chemical compound CCCC=C(CC)C=O PYLMCYQHBRSDND-UHFFFAOYSA-N 0.000 claims abstract description 55
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical compound CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 claims abstract description 47
- 238000005984 hydrogenation reaction Methods 0.000 claims abstract description 41
- 239000000047 product Substances 0.000 claims abstract description 32
- 239000007859 condensation product Substances 0.000 claims abstract description 30
- 238000009833 condensation Methods 0.000 claims abstract description 24
- 230000005494 condensation Effects 0.000 claims abstract description 24
- 239000003054 catalyst Substances 0.000 claims abstract description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 17
- -1 alkali metal salts Chemical class 0.000 claims abstract description 12
- 239000012074 organic phase Substances 0.000 claims abstract description 11
- 229910052783 alkali metal Inorganic materials 0.000 claims abstract description 10
- 238000000926 separation method Methods 0.000 claims abstract description 10
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims abstract description 9
- 230000006872 improvement Effects 0.000 claims abstract description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 6
- 239000001257 hydrogen Substances 0.000 claims abstract description 6
- 238000004064 recycling Methods 0.000 claims abstract description 4
- 238000001704 evaporation Methods 0.000 claims description 2
- 230000008020 evaporation Effects 0.000 claims description 2
- 229920000053 polysorbate 80 Polymers 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 abstract description 5
- 238000009835 boiling Methods 0.000 description 14
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 230000000694 effects Effects 0.000 description 8
- 239000000203 mixture Substances 0.000 description 7
- 238000004821 distillation Methods 0.000 description 5
- 239000007792 gaseous phase Substances 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 239000003518 caustics Substances 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 150000001299 aldehydes Chemical class 0.000 description 3
- 150000001340 alkali metals Chemical class 0.000 description 3
- 230000007423 decrease Effects 0.000 description 3
- 230000006866 deterioration Effects 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- MBDOYVRWFFCFHM-SNAWJCMRSA-N (2E)-hexenal Chemical compound CCC\C=C\C=O MBDOYVRWFFCFHM-SNAWJCMRSA-N 0.000 description 2
- HSJKGGMUJITCBW-UHFFFAOYSA-N 3-hydroxybutanal Chemical compound CC(O)CC=O HSJKGGMUJITCBW-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- 230000009471 action Effects 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 229910001220 stainless steel Inorganic materials 0.000 description 2
- 239000010935 stainless steel Substances 0.000 description 2
- FMBAIQMSJGQWLF-UHFFFAOYSA-N 2-ethyl-3-hydroxyhexanal Chemical class CCCC(O)C(CC)C=O FMBAIQMSJGQWLF-UHFFFAOYSA-N 0.000 description 1
- MBDOYVRWFFCFHM-UHFFFAOYSA-N 2-hexenal Chemical compound CCCC=CC=O MBDOYVRWFFCFHM-UHFFFAOYSA-N 0.000 description 1
- 241000518994 Conta Species 0.000 description 1
- 102000018361 Contactin Human genes 0.000 description 1
- 108060003955 Contactin Proteins 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- YZCKVEUIGOORGS-NJFSPNSNSA-N Tritium Chemical compound [3H] YZCKVEUIGOORGS-NJFSPNSNSA-N 0.000 description 1
- 238000005882 aldol condensation reaction Methods 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000002939 deleterious effect Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 230000002542 deteriorative effect Effects 0.000 description 1
- 230000009977 dual effect Effects 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 229910000000 metal hydroxide Inorganic materials 0.000 description 1
- 150000004692 metal hydroxides Chemical class 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000036647 reaction Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 238000005201 scrubbing Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000011144 upstream manufacturing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
- C07C45/72—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups
- C07C45/74—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups combined with dehydration
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19742437957 DE2437957B2 (de) | 1974-08-07 | 1974-08-07 | Verfahren zur kontinuierlichen herstellung von 2-aethylhexanol |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1057313A true CA1057313A (en) | 1979-06-26 |
Family
ID=5922623
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA232,598A Expired CA1057313A (en) | 1974-08-07 | 1975-07-31 | Process for the continuous production of 2-ethyl hexanol |
Country Status (10)
| Country | Link |
|---|---|
| JP (1) | JPS5141309A (de) |
| AT (1) | AT335989B (de) |
| BR (1) | BR7505008A (de) |
| CA (1) | CA1057313A (de) |
| DE (1) | DE2437957B2 (de) |
| FR (1) | FR2282417A1 (de) |
| GB (1) | GB1462328A (de) |
| PL (1) | PL99233B1 (de) |
| RO (1) | RO72483A (de) |
| SE (1) | SE421304B (de) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2404955C1 (ru) * | 2009-05-27 | 2010-11-27 | Общество с ограниченной ответственностью "Оксохимнефть" | Способ получения 2-этилгексанола |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS50111966A (de) * | 1974-02-11 | 1975-09-03 | ||
| DE2713434C3 (de) * | 1977-03-26 | 1980-10-23 | Ruhrchemie Ag, 4200 Oberhausen | Verfahren zur Herstellung von 2-Äthylhexanol |
| US4528405A (en) * | 1983-12-30 | 1985-07-09 | Union Carbide Corporation | Aldol condensation of enolizable aldehydes using a metal carboxylate catalyst |
| DE3530839A1 (de) * | 1985-08-29 | 1987-03-05 | Ruhrchemie Ag | Verfahren zur herstellung von 2-ethylhexanol |
| JPS62278816A (ja) * | 1986-05-28 | 1987-12-03 | Yagi Antenna Co Ltd | タイマ回路 |
| GB9615050D0 (en) * | 1996-07-17 | 1996-09-04 | Exxon Chemical Patents Inc | Recycle and recovery of useful products from heavy aldol by-products |
| JP4003361B2 (ja) * | 1998-11-27 | 2007-11-07 | 三菱化学株式会社 | アルコールの製造方法 |
| DE10252173B3 (de) * | 2002-11-09 | 2004-06-03 | Celanese Chemicals Europe Gmbh | Verfahren zur Gewinnung von aliphatischen C3-C10-Alkoholen aus Hochsiedern |
| DE102009050345A1 (de) | 2009-10-22 | 2011-06-01 | Süd-Chemie AG | Aldolkondensation in Gegenwart von Hydrotalciten |
| CN103864587B (zh) * | 2012-12-10 | 2016-05-11 | 中国石油天然气股份有限公司 | 一种合成2-乙基-2-己烯醛的方法 |
-
1974
- 1974-08-07 DE DE19742437957 patent/DE2437957B2/de not_active Ceased
- 1974-09-09 AT AT722674A patent/AT335989B/de not_active IP Right Cessation
-
1975
- 1975-07-29 FR FR7523675A patent/FR2282417A1/fr active Granted
- 1975-07-30 SE SE7508638A patent/SE421304B/xx not_active IP Right Cessation
- 1975-07-31 GB GB3207475A patent/GB1462328A/en not_active Expired
- 1975-07-31 PL PL18243375A patent/PL99233B1/pl unknown
- 1975-07-31 RO RO7583031A patent/RO72483A/ro unknown
- 1975-07-31 CA CA232,598A patent/CA1057313A/en not_active Expired
- 1975-08-06 BR BR7505008A patent/BR7505008A/pt unknown
- 1975-08-07 JP JP9625275A patent/JPS5141309A/ja active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2404955C1 (ru) * | 2009-05-27 | 2010-11-27 | Общество с ограниченной ответственностью "Оксохимнефть" | Способ получения 2-этилгексанола |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5141309A (en) | 1976-04-07 |
| PL99233B1 (pl) | 1978-06-30 |
| GB1462328A (en) | 1977-01-26 |
| FR2282417A1 (fr) | 1976-03-19 |
| SE421304B (sv) | 1981-12-14 |
| RO72483A (ro) | 1981-06-30 |
| SE7508638L (sv) | 1976-02-09 |
| AU8359875A (en) | 1977-02-03 |
| BR7505008A (pt) | 1976-08-03 |
| DE2437957A1 (de) | 1976-02-26 |
| FR2282417B1 (de) | 1977-12-09 |
| ATA722674A (de) | 1976-08-15 |
| DE2437957B2 (de) | 1976-06-16 |
| AT335989B (de) | 1977-04-12 |
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