DE2252685B2 - Verfahren zur Herstellung von tert-Butanol - Google Patents
Verfahren zur Herstellung von tert-ButanolInfo
- Publication number
- DE2252685B2 DE2252685B2 DE2252685A DE2252685A DE2252685B2 DE 2252685 B2 DE2252685 B2 DE 2252685B2 DE 2252685 A DE2252685 A DE 2252685A DE 2252685 A DE2252685 A DE 2252685A DE 2252685 B2 DE2252685 B2 DE 2252685B2
- Authority
- DE
- Germany
- Prior art keywords
- tert
- butanol
- sulfuric acid
- percent
- weight
- 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.)
- Withdrawn
Links
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 title claims description 210
- 238000000034 method Methods 0.000 title claims description 25
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 111
- 239000000203 mixture Substances 0.000 claims description 81
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 claims description 51
- 239000004215 Carbon black (E152) Substances 0.000 claims description 37
- 229930195733 hydrocarbon Natural products 0.000 claims description 32
- 238000000605 extraction Methods 0.000 claims description 31
- 150000002430 hydrocarbons Chemical class 0.000 claims description 28
- OXRWGVGJVIXCBV-UHFFFAOYSA-N 2-methylpropan-2-ol;sulfuric acid Chemical compound CC(C)(C)O.OS(O)(=O)=O OXRWGVGJVIXCBV-UHFFFAOYSA-N 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 claims description 4
- 230000000887 hydrating effect Effects 0.000 claims description 3
- 230000036571 hydration Effects 0.000 description 30
- 238000006703 hydration reaction Methods 0.000 description 30
- 238000004821 distillation Methods 0.000 description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 14
- 239000012074 organic phase Substances 0.000 description 11
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 10
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 6
- 238000000926 separation method Methods 0.000 description 6
- FXNDIJDIPNCZQJ-UHFFFAOYSA-N 2,4,4-trimethylpent-1-ene Chemical compound CC(=C)CC(C)(C)C FXNDIJDIPNCZQJ-UHFFFAOYSA-N 0.000 description 5
- -1 B. propane Chemical class 0.000 description 5
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical class CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 5
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- 235000013844 butane Nutrition 0.000 description 2
- 238000003776 cleavage reaction Methods 0.000 description 2
- 230000018044 dehydration Effects 0.000 description 2
- 238000006297 dehydration reaction Methods 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 230000007017 scission Effects 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 2
- UZFMOKQJFYMBGY-UHFFFAOYSA-N 4-hydroxy-TEMPO Chemical compound CC1(C)CC(O)CC(C)(C)N1[O] UZFMOKQJFYMBGY-UHFFFAOYSA-N 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- IYABWNGZIDDRAK-UHFFFAOYSA-N allene Chemical compound C=C=C IYABWNGZIDDRAK-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- QNRMTGGDHLBXQZ-UHFFFAOYSA-N buta-1,2-diene Chemical compound CC=C=C QNRMTGGDHLBXQZ-UHFFFAOYSA-N 0.000 description 1
- VRCOHSLPAXOLLJ-UHFFFAOYSA-N buta-1,3-diene 2-methylpropane Chemical compound C=CC=C.CC(C)C VRCOHSLPAXOLLJ-UHFFFAOYSA-N 0.000 description 1
- IUFXKTIZXZVLJC-UHFFFAOYSA-N buta-1,3-diene;2-methylprop-1-ene Chemical compound CC(C)=C.C=CC=C IUFXKTIZXZVLJC-UHFFFAOYSA-N 0.000 description 1
- ZOJPPDGPQOHPKT-UHFFFAOYSA-N butane 2-methylprop-1-ene Chemical compound CCCC.CC(C)=C ZOJPPDGPQOHPKT-UHFFFAOYSA-N 0.000 description 1
- SUAICDWVYXQSNC-UHFFFAOYSA-N butane;2-methylpropane Chemical compound CCCC.CC(C)C SUAICDWVYXQSNC-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000005336 cracking Methods 0.000 description 1
- 238000006356 dehydrogenation reaction Methods 0.000 description 1
- 238000007700 distillative separation Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229920006158 high molecular weight polymer Polymers 0.000 description 1
- 239000001282 iso-butane Substances 0.000 description 1
- 235000013847 iso-butane Nutrition 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- MWWATHDPGQKSAR-UHFFFAOYSA-N propyne Chemical compound CC#C MWWATHDPGQKSAR-UHFFFAOYSA-N 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 238000005292 vacuum distillation 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
- C07C29/74—Separation; Purification; Use of additives, e.g. for stabilisation
- C07C29/76—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment
- C07C29/86—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment by liquid-liquid treatment
-
- 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
- C07C29/03—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by addition of hydroxy groups to unsaturated carbon-to-carbon bonds, e.g. with the aid of H2O2
- C07C29/04—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by addition of hydroxy groups to unsaturated carbon-to-carbon bonds, e.g. with the aid of H2O2 by hydration of carbon-to-carbon double bonds
- C07C29/05—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by addition of hydroxy groups to unsaturated carbon-to-carbon bonds, e.g. with the aid of H2O2 by hydration of carbon-to-carbon double bonds with formation of absorption products in mineral acids and their hydrolysis
- C07C29/06—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by addition of hydroxy groups to unsaturated carbon-to-carbon bonds, e.g. with the aid of H2O2 by hydration of carbon-to-carbon double bonds with formation of absorption products in mineral acids and their hydrolysis the acid being sulfuric acid
-
- 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
- C07C29/76—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment
- C07C29/80—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment by distillation
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Environmental & Geological Engineering (AREA)
- General Life Sciences & Earth Sciences (AREA)
- Geochemistry & Mineralogy (AREA)
- Geology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (11)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2252685A DE2252685B2 (de) | 1972-10-27 | 1972-10-27 | Verfahren zur Herstellung von tert-Butanol |
| CA183,981A CA1010065A (en) | 1972-10-27 | 1973-10-23 | Manufacture of t-butanol |
| NL7314625A NL7314625A (en, 2012) | 1972-10-27 | 1973-10-24 | |
| AT906573A AT326621B (de) | 1972-10-27 | 1973-10-25 | Verfahren zur herstellung von tert. butanol |
| JP48119477A JPS49132004A (en, 2012) | 1972-10-27 | 1973-10-25 | |
| FR7338134A FR2204600B1 (en, 2012) | 1972-10-27 | 1973-10-25 | |
| ZA738284A ZA738284B (en) | 1972-10-27 | 1973-10-26 | Manufacture of t-butanol |
| GB4991373A GB1444968A (en) | 1972-10-27 | 1973-10-26 | Manufacture of t-butanol |
| IT53380/73A IT997708B (it) | 1972-10-27 | 1973-10-26 | Procedimento per la produzione di terz butanolo |
| BE137159A BE806634A (fr) | 1972-10-27 | 1973-10-29 | Procede de preparation du t-butanol |
| US05/586,540 US3950442A (en) | 1972-10-27 | 1975-06-13 | Manufacture of t-butanol |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2252685A DE2252685B2 (de) | 1972-10-27 | 1972-10-27 | Verfahren zur Herstellung von tert-Butanol |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2252685A1 DE2252685A1 (de) | 1974-05-02 |
| DE2252685B2 true DE2252685B2 (de) | 1979-12-06 |
Family
ID=5860193
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2252685A Withdrawn DE2252685B2 (de) | 1972-10-27 | 1972-10-27 | Verfahren zur Herstellung von tert-Butanol |
Country Status (10)
| Country | Link |
|---|---|
| JP (1) | JPS49132004A (en, 2012) |
| AT (1) | AT326621B (en, 2012) |
| BE (1) | BE806634A (en, 2012) |
| CA (1) | CA1010065A (en, 2012) |
| DE (1) | DE2252685B2 (en, 2012) |
| FR (1) | FR2204600B1 (en, 2012) |
| GB (1) | GB1444968A (en, 2012) |
| IT (1) | IT997708B (en, 2012) |
| NL (1) | NL7314625A (en, 2012) |
| ZA (1) | ZA738284B (en, 2012) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0175443A3 (en) * | 1984-09-17 | 1986-07-02 | Exxon Research And Engineering Company | Improved alcohol recovery process |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6596913B1 (en) * | 2001-02-23 | 2003-07-22 | Catalytic Distillation Technologies | Recovery of tertiary butyl alcohol |
| DE10241762A1 (de) * | 2002-09-10 | 2004-03-18 | Oxeno Olefinchemie Gmbh | Verfahren zur Herstellung von wasserfreiem tert.-Butanol |
| JP5680268B2 (ja) * | 2008-09-03 | 2015-03-04 | 東ソー株式会社 | ｔ−ブチルアルコール溶液及びその製造法 |
| FR2936526A1 (fr) * | 2008-09-29 | 2010-04-02 | Arkema France | Fabrication d'hydroperoxyde de tertiobutyle a partir de matieres renouvelables, hydroperoxyde de tertiobutyle obtenu et utilisations |
| JPWO2016080531A1 (ja) * | 2014-11-20 | 2017-09-07 | 国立大学法人名古屋大学 | ブタノールの濃縮脱水方法 |
-
1972
- 1972-10-27 DE DE2252685A patent/DE2252685B2/de not_active Withdrawn
-
1973
- 1973-10-23 CA CA183,981A patent/CA1010065A/en not_active Expired
- 1973-10-24 NL NL7314625A patent/NL7314625A/xx not_active Application Discontinuation
- 1973-10-25 JP JP48119477A patent/JPS49132004A/ja active Pending
- 1973-10-25 FR FR7338134A patent/FR2204600B1/fr not_active Expired
- 1973-10-25 AT AT906573A patent/AT326621B/de not_active IP Right Cessation
- 1973-10-26 IT IT53380/73A patent/IT997708B/it active
- 1973-10-26 ZA ZA738284A patent/ZA738284B/xx unknown
- 1973-10-26 GB GB4991373A patent/GB1444968A/en not_active Expired
- 1973-10-29 BE BE137159A patent/BE806634A/xx unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0175443A3 (en) * | 1984-09-17 | 1986-07-02 | Exxon Research And Engineering Company | Improved alcohol recovery process |
Also Published As
| Publication number | Publication date |
|---|---|
| CA1010065A (en) | 1977-05-10 |
| IT997708B (it) | 1975-12-30 |
| GB1444968A (en) | 1976-08-04 |
| ATA906573A (de) | 1975-03-15 |
| FR2204600B1 (en, 2012) | 1978-09-15 |
| DE2252685A1 (de) | 1974-05-02 |
| BE806634A (fr) | 1974-04-29 |
| ZA738284B (en) | 1974-10-30 |
| FR2204600A1 (en, 2012) | 1974-05-24 |
| JPS49132004A (en, 2012) | 1974-12-18 |
| AT326621B (de) | 1975-12-29 |
| NL7314625A (en, 2012) | 1974-05-01 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DD147664A5 (de) | Verfahren zur gleichzeitigen herstellung von reinem methyl-tert.-butylether | |
| EP0141316B1 (de) | Verfahren zur Gewinnung von Isopren aus einem C5-Kohlenwasserstoffgemisch | |
| DE2724365A1 (de) | Verfahren zum trennen eines c tief 4 -kohlenwasserstoffgemisches durch extraktive destillation | |
| EP2545019B1 (de) | Verfahren zur destillativen gewinnung von rein-1,3-butadien aus roh-1,3-butadien | |
| DE2705538A1 (de) | Verfahren zur reindarstellung von methyl-tert.-butylaether | |
| DE2400260C3 (de) | Verfahren zur Abtrennung von Methacrolein aus einer Gasreaktionsmischung | |
| DE3628008C1 (en, 2012) | ||
| DE3442937C2 (de) | Verfahren zur kontinuierlichen Herstellung von 1,2-Pentandiol | |
| DE2945075C2 (en, 2012) | ||
| DE2252685B2 (de) | Verfahren zur Herstellung von tert-Butanol | |
| DE69605460T2 (de) | Verfahren zur Herstellung von Isopropylalkohol | |
| EP0216991B1 (de) | Verfahren zur Trennung von paraffinischen und olefinischen C4-Kohlenwasserstoffen | |
| DE69516098T2 (de) | Verfahren zur Herstellung von Isopropylalkohol durch Hydratisierung von Propylen | |
| DE2521965C3 (de) | Verfahren zur Abtrennung von Butadien aus einem Strom von C4 -Kohlenwasserstoffen | |
| DE2100424C3 (de) | Verfahren zur Abtrennung von 2 Chlor 1,3 butadien | |
| EP0005788B1 (de) | Verfahren zur Gewinnung von Butadien-1,3 aus einem C4-Kohlenwasserstoffgemisch | |
| EP0016474A1 (de) | Verfahren zur Gewinnung eines konjugierten Diolefins aus einem C 4- oder C 5-Kohlenwasserstoffgemisch | |
| DE2110031A1 (de) | Verfahren zur Abtrennung von Methacrolein | |
| DE10249379A1 (de) | Verfahren zur kontinuierlichen Rückführung des bei der Oxidation von Olefinen mit Hydroperoxiden nicht umgesetzten Olefins mittels Lösungsmittelwäsche | |
| DE2747762A1 (de) | Verfahren zur kontinuierlichen epoxidation von alkenen und deren derivaten | |
| DE1543173B2 (de) | Verfahren zur Herstellung und Gewinnung von Propenoxid, Essigsäure und anderen wertvollen Oxidationsprodukten | |
| DE2542203C2 (de) | Verfahren zur Herstellung von Äthanol oder 2-Propanol durch direkte Hydratation von Äthylen oder Propylen | |
| EP0149145A2 (de) | Verfahren zur Trennung eines C4-Kohlenwasserstoffgemisches durch Extraktivdestillation | |
| DE1202778B (de) | Verfahren zur kontinuierlichen Aufarbeitung von Essigsaeure enthaltenden Gemischen | |
| DE968890C (de) | Verfahren zur Trennung von Gemischen, die Kohlenwasserstoffe und einwertige Alkohole enthalten |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| BHN | Withdrawal |