DE2110584A1 - Verfahren zur Herstellung von Isopentanhydroperoxyd bzw. Isopren - Google Patents
Verfahren zur Herstellung von Isopentanhydroperoxyd bzw. IsoprenInfo
- Publication number
- DE2110584A1 DE2110584A1 DE19712110584 DE2110584A DE2110584A1 DE 2110584 A1 DE2110584 A1 DE 2110584A1 DE 19712110584 DE19712110584 DE 19712110584 DE 2110584 A DE2110584 A DE 2110584A DE 2110584 A1 DE2110584 A1 DE 2110584A1
- Authority
- DE
- Germany
- Prior art keywords
- isopentane
- methyl
- oxidation
- hydroperoxide
- butanol
- 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.)
- Pending
Links
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 title claims description 36
- ZXBPNIWBHIXVDM-UHFFFAOYSA-N hydrogen peroxide;2-methylbutane Chemical compound OO.CCC(C)C ZXBPNIWBHIXVDM-UHFFFAOYSA-N 0.000 title claims description 25
- 238000000034 method Methods 0.000 title claims description 18
- 238000004519 manufacturing process Methods 0.000 title claims description 13
- 230000008569 process Effects 0.000 title claims description 12
- QWTDNUCVQCZILF-UHFFFAOYSA-N isopentane Chemical compound CCC(C)C QWTDNUCVQCZILF-UHFFFAOYSA-N 0.000 claims description 107
- AFABGHUZZDYHJO-UHFFFAOYSA-N dimethyl butane Natural products CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 claims description 53
- MSXVEPNJUHWQHW-UHFFFAOYSA-N 2-methylbutan-2-ol Chemical compound CCC(C)(C)O MSXVEPNJUHWQHW-UHFFFAOYSA-N 0.000 claims description 21
- 230000003647 oxidation Effects 0.000 claims description 19
- 238000007254 oxidation reaction Methods 0.000 claims description 19
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 18
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 17
- BKOOMYPCSUNDGP-UHFFFAOYSA-N 2-methylbut-2-ene Chemical compound CC=C(C)C BKOOMYPCSUNDGP-UHFFFAOYSA-N 0.000 claims description 11
- 239000012429 reaction media Substances 0.000 claims description 11
- 238000006735 epoxidation reaction Methods 0.000 claims description 10
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 9
- 239000006227 byproduct Substances 0.000 claims description 9
- 239000007788 liquid Substances 0.000 claims description 9
- 230000003197 catalytic effect Effects 0.000 claims description 8
- 150000003509 tertiary alcohols Chemical class 0.000 claims description 8
- 230000015572 biosynthetic process Effects 0.000 claims description 7
- 229910001882 dioxygen Inorganic materials 0.000 claims description 7
- 239000007791 liquid phase Substances 0.000 claims description 6
- BCJPEZMFAKOJPM-UHFFFAOYSA-N 2-ethyl-3-methyloxirane Chemical compound CCC1OC1C BCJPEZMFAKOJPM-UHFFFAOYSA-N 0.000 claims description 5
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims description 5
- 239000011261 inert gas Substances 0.000 claims description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- FRDAATYAJDYRNW-UHFFFAOYSA-N 3-methyl-3-pentanol Chemical compound CCC(C)(O)CC FRDAATYAJDYRNW-UHFFFAOYSA-N 0.000 claims description 4
- 238000000746 purification Methods 0.000 claims description 3
- 238000006317 isomerization reaction Methods 0.000 claims description 2
- GNLZSEMKVZGLGY-UHFFFAOYSA-N pentane-2,2-diol Chemical compound CCCC(C)(O)O GNLZSEMKVZGLGY-UHFFFAOYSA-N 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 description 28
- QPRQEDXDYOZYLA-UHFFFAOYSA-N 2-methylbutan-1-ol Chemical compound CCC(C)CO QPRQEDXDYOZYLA-UHFFFAOYSA-N 0.000 description 12
- MHNNAWXXUZQSNM-UHFFFAOYSA-N 2-methylbut-1-ene Chemical compound CCC(C)=C MHNNAWXXUZQSNM-UHFFFAOYSA-N 0.000 description 10
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 8
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 7
- 238000004821 distillation Methods 0.000 description 7
- 238000012360 testing method Methods 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- 239000001282 iso-butane Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- -1 Isopropyl-isobutyl Chemical group 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- HYTRYEXINDDXJK-UHFFFAOYSA-N Ethyl isopropyl ketone Chemical compound CCC(=O)C(C)C HYTRYEXINDDXJK-UHFFFAOYSA-N 0.000 description 2
- 235000010650 Hyssopus officinalis Nutrition 0.000 description 2
- 240000001812 Hyssopus officinalis Species 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- 229910000831 Steel Inorganic materials 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 150000001336 alkenes Chemical class 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 2
- 239000004327 boric acid Substances 0.000 description 2
- 229910052810 boron oxide Inorganic materials 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 230000018044 dehydration Effects 0.000 description 2
- 238000006297 dehydration reaction Methods 0.000 description 2
- JKWMSGQKBLHBQQ-UHFFFAOYSA-N diboron trioxide Chemical compound O=BOB=O JKWMSGQKBLHBQQ-UHFFFAOYSA-N 0.000 description 2
- 150000002009 diols Chemical class 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 2
- 230000001590 oxidative effect Effects 0.000 description 2
- 150000002924 oxiranes Chemical class 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 239000010959 steel Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- XRXANEMIFVRKLN-UHFFFAOYSA-N 2-hydroperoxy-2-methylbutane Chemical compound CCC(C)(C)OO XRXANEMIFVRKLN-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 235000013601 eggs Nutrition 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 239000000806 elastomer Substances 0.000 description 1
- 238000007701 flash-distillation Methods 0.000 description 1
- OYMKLTPMFOCLTL-UHFFFAOYSA-N hydrogen peroxide;2-methylpropane Chemical compound OO.CC(C)C OYMKLTPMFOCLTL-UHFFFAOYSA-N 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 239000011733 molybdenum Substances 0.000 description 1
- 238000005502 peroxidation Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N sec-butylidene Natural products CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- 150000003333 secondary alcohols Chemical class 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C409/00—Peroxy compounds
- C07C409/02—Peroxy compounds the —O—O— group being bound between a carbon atom, not further substituted by oxygen atoms, and hydrogen, i.e. hydroperoxides
- C07C409/04—Peroxy compounds the —O—O— group being bound between a carbon atom, not further substituted by oxygen atoms, and hydrogen, i.e. hydroperoxides the carbon atom being acyclic
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C407/00—Preparation of peroxy compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7011121A FR2082823A5 (enExample) | 1970-03-27 | 1970-03-27 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2110584A1 true DE2110584A1 (de) | 1971-10-21 |
Family
ID=9053035
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19712110584 Pending DE2110584A1 (de) | 1970-03-27 | 1971-03-05 | Verfahren zur Herstellung von Isopentanhydroperoxyd bzw. Isopren |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US3855314A (enExample) |
| AT (2) | AT313862B (enExample) |
| BE (1) | BE764646A (enExample) |
| CA (1) | CA948651A (enExample) |
| DE (1) | DE2110584A1 (enExample) |
| FR (1) | FR2082823A5 (enExample) |
| GB (1) | GB1337765A (enExample) |
| LU (1) | LU62859A1 (enExample) |
| NL (1) | NL7103729A (enExample) |
| RO (1) | RO57817A (enExample) |
| SE (1) | SE372255B (enExample) |
| ZA (1) | ZA711690B (enExample) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4408081A (en) * | 1981-10-05 | 1983-10-04 | Shell Oil Company | Process for oxidation of isobutane |
| US4408082A (en) * | 1981-10-05 | 1983-10-04 | Shell Oil Company | Oxidation of isobutane in the dense phase and at low oxygen concentration |
| US4404406A (en) * | 1981-10-05 | 1983-09-13 | Shell Oil Company | Oxidation of isobutane under super-critical conditions |
| RU2220136C2 (ru) * | 2001-11-02 | 2003-12-27 | Открытое акционерное общество Научно-исследовательский институт "Ярсинтез" | Способ получения гидроперекисей трет-алканов |
| CN105439822B (zh) * | 2014-08-27 | 2017-06-23 | 湖南中创化工股份有限公司 | 一种异丁烷氧化制备叔丁醇的方法 |
| CN112608210B (zh) * | 2020-11-27 | 2022-05-10 | 信汇科技有限公司 | 一种烷烃氧化制备其过氧化物的选择性提高方法 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2733270A (en) * | 1956-01-31 | Preparation of aldehydes | ||
| NL81914C (enExample) * | 1953-01-16 | |||
| US2845461A (en) * | 1956-04-12 | 1958-07-29 | Shell Dev | Non-catalytic liquid phase isobutane oxidation |
| US2862973A (en) * | 1956-04-27 | 1958-12-02 | Shell Dev | Di-tertiary-alkyl peroxide production |
| BE680852A (enExample) * | 1965-05-25 | 1966-11-14 | ||
| NL136293C (enExample) * | 1966-10-26 |
-
1970
- 1970-03-27 FR FR7011121A patent/FR2082823A5/fr not_active Expired
-
1971
- 1971-03-05 DE DE19712110584 patent/DE2110584A1/de active Pending
- 1971-03-15 ZA ZA711690A patent/ZA711690B/xx unknown
- 1971-03-18 AT AT235171A patent/AT313862B/de not_active IP Right Cessation
- 1971-03-19 NL NL7103729A patent/NL7103729A/xx unknown
- 1971-03-22 BE BE764646A patent/BE764646A/xx unknown
- 1971-03-24 SE SE7103830A patent/SE372255B/xx unknown
- 1971-03-25 CA CA108,721A patent/CA948651A/en not_active Expired
- 1971-03-25 US US00127958A patent/US3855314A/en not_active Expired - Lifetime
- 1971-03-25 LU LU62859D patent/LU62859A1/xx unknown
- 1971-03-26 RO RO66395A patent/RO57817A/ro unknown
- 1971-04-19 GB GB2545371*A patent/GB1337765A/en not_active Expired
-
1973
- 1973-01-04 AT AT00089/73A patent/AT311930B/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| GB1337765A (en) | 1973-11-21 |
| BE764646A (fr) | 1971-09-22 |
| AT311930B (de) | 1973-11-15 |
| CA948651A (en) | 1974-06-04 |
| NL7103729A (enExample) | 1971-09-29 |
| FR2082823A5 (enExample) | 1971-12-10 |
| US3855314A (en) | 1974-12-17 |
| SE372255B (enExample) | 1974-12-16 |
| AT313862B (de) | 1974-03-11 |
| LU62859A1 (enExample) | 1971-08-13 |
| RO57817A (enExample) | 1975-06-15 |
| ZA711690B (en) | 1972-03-29 |
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