PL110592B1 - Method of producing methyl-tert.butyl ether - Google Patents
Method of producing methyl-tert.butyl ether Download PDFInfo
- Publication number
- PL110592B1 PL110592B1 PL19333076A PL19333076A PL110592B1 PL 110592 B1 PL110592 B1 PL 110592B1 PL 19333076 A PL19333076 A PL 19333076A PL 19333076 A PL19333076 A PL 19333076A PL 110592 B1 PL110592 B1 PL 110592B1
- Authority
- PL
- Poland
- Prior art keywords
- isobutene
- methanol
- reaction
- mixture
- reaction mixture
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 35
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 title claims abstract description 17
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 169
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 claims abstract description 122
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims abstract description 71
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims abstract description 38
- 238000006243 chemical reaction Methods 0.000 claims abstract description 38
- 239000003054 catalyst Substances 0.000 claims abstract description 35
- 239000000203 mixture Substances 0.000 claims abstract description 34
- 229930195733 hydrocarbon Natural products 0.000 claims abstract description 33
- 239000012071 phase Substances 0.000 claims abstract description 32
- 150000002430 hydrocarbons Chemical class 0.000 claims abstract description 30
- 239000004215 Carbon black (E152) Substances 0.000 claims abstract description 11
- 239000007791 liquid phase Substances 0.000 claims abstract description 6
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical class CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 claims abstract description 6
- 238000005406 washing Methods 0.000 claims abstract description 6
- AQEFLFZSWDEAIP-UHFFFAOYSA-N di-tert-butyl ether Chemical compound CC(C)(C)OC(C)(C)C AQEFLFZSWDEAIP-UHFFFAOYSA-N 0.000 claims abstract 2
- 239000011541 reaction mixture Substances 0.000 claims description 34
- 125000004432 carbon atom Chemical group C* 0.000 claims description 14
- 238000004821 distillation Methods 0.000 claims description 8
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 claims description 7
- 239000007858 starting material Substances 0.000 claims description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 239000008246 gaseous mixture Substances 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 238000000197 pyrolysis Methods 0.000 abstract description 5
- 238000004523 catalytic cracking Methods 0.000 abstract description 2
- 235000011149 sulphuric acid Nutrition 0.000 abstract 3
- 239000001117 sulphuric acid Substances 0.000 abstract 3
- 235000013844 butane Nutrition 0.000 abstract 1
- 239000007795 chemical reaction product Substances 0.000 abstract 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 abstract 1
- 239000007789 gas Substances 0.000 description 8
- 238000001816 cooling Methods 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- 239000002253 acid Substances 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 2
- 239000003377 acid catalyst Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000001273 butane Substances 0.000 description 2
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 238000006356 dehydrogenation reaction Methods 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
- 239000000446 fuel Substances 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 238000004064 recycling Methods 0.000 description 2
- CHRJZRDFSQHIFI-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;styrene Chemical compound C=CC1=CC=CC=C1.C=CC1=CC=CC=C1C=C CHRJZRDFSQHIFI-UHFFFAOYSA-N 0.000 description 1
- JILHZKWLEAKYRC-UHFFFAOYSA-N 1-methoxy-2,2-dimethylpropane Chemical compound COCC(C)(C)C JILHZKWLEAKYRC-UHFFFAOYSA-N 0.000 description 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical group COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
- 241000047703 Nonion Species 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001336 alkenes Chemical class 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
- 230000033228 biological regulation Effects 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000001944 continuous distillation Methods 0.000 description 1
- 229910052593 corundum Inorganic materials 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000011010 flushing procedure Methods 0.000 description 1
- 239000002638 heterogeneous catalyst Substances 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- -1 methyl-tert-butyl Chemical group 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000008237 rinsing water Substances 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 238000005201 scrubbing Methods 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 229910001845 yogo sapphire Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/05—Preparation of ethers by addition of compounds to unsaturated compounds
- C07C41/06—Preparation of ethers by addition of compounds to unsaturated compounds by addition of organic compounds only
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C7/00—Purification; Separation; Use of additives
- C07C7/148—Purification; Separation; Use of additives by treatment giving rise to a chemical modification of at least one compound
- C07C7/14875—Purification; Separation; Use of additives by treatment giving rise to a chemical modification of at least one compound with organic compounds
- C07C7/14891—Purification; Separation; Use of additives by treatment giving rise to a chemical modification of at least one compound with organic compounds alcohols
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Analytical Chemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Water Supply & Treatment (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HUMA002724 HU175954B (en) | 1975-10-29 | 1975-10-29 | Process for direct separation of isobutylene form mixtures of hydrocarbones |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PL110592B1 true PL110592B1 (en) | 1980-07-31 |
Family
ID=10998814
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL19333076A PL110592B1 (en) | 1975-10-29 | 1976-10-28 | Method of producing methyl-tert.butyl ether |
Country Status (16)
| Country | Link |
|---|---|
| JP (1) | JPS5257103A (enExample) |
| AT (1) | AT346297B (enExample) |
| BE (1) | BE847862A (enExample) |
| CA (1) | CA1077066A (enExample) |
| CS (1) | CS205045B2 (enExample) |
| DD (1) | DD126591A1 (enExample) |
| DE (1) | DE2649623A1 (enExample) |
| FR (1) | FR2329622A1 (enExample) |
| GB (1) | GB1532477A (enExample) |
| HU (1) | HU175954B (enExample) |
| IT (1) | IT1079198B (enExample) |
| NL (1) | NL7611965A (enExample) |
| PL (1) | PL110592B1 (enExample) |
| RO (1) | RO71263A (enExample) |
| SU (1) | SU915797A3 (enExample) |
| YU (1) | YU39977B (enExample) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2928509A1 (de) * | 1979-07-14 | 1981-01-29 | Basf Ag | Verfahren zur gemeinsamen herstellung von methyl-tert.-butylaether und gewinnung von isobuten |
| DE2928510A1 (de) * | 1979-07-14 | 1981-01-29 | Basf Ag | Verfahren zur gewinnung von isobuten aus isobuten enthaltenden c tief 4 -kohlenwasserstoffgemischen |
| NZ197347A (en) * | 1980-06-12 | 1983-06-14 | British Petroleum Co | Dehydroisomerisation of n-butane to isobutene |
| CN113582801B (zh) * | 2020-04-30 | 2023-09-05 | 中国石油化工股份有限公司 | 混合碳四选择性叠合制备异辛烯的工艺 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3121124A (en) * | 1959-05-04 | 1964-02-11 | Sinclair Research Inc | Tertiary olefin separation via etherification |
| US3170000A (en) * | 1962-10-24 | 1965-02-16 | Sinclair Research Inc | Tertiary olefin separation via etherification with small surface area catalysts |
| JPS5126401B1 (enExample) * | 1969-03-12 | 1976-08-06 |
-
1975
- 1975-10-29 HU HUMA002724 patent/HU175954B/hu unknown
-
1976
- 1976-09-27 AT AT712976A patent/AT346297B/de not_active IP Right Cessation
- 1976-09-30 FR FR7629363A patent/FR2329622A1/fr active Granted
- 1976-10-07 GB GB4168876A patent/GB1532477A/en not_active Expired
- 1976-10-14 YU YU253076A patent/YU39977B/xx unknown
- 1976-10-21 SU SU762414047A patent/SU915797A3/ru active
- 1976-10-25 CA CA264,132A patent/CA1077066A/en not_active Expired
- 1976-10-26 DD DD19545576A patent/DD126591A1/xx unknown
- 1976-10-26 CS CS688076A patent/CS205045B2/cs unknown
- 1976-10-27 JP JP12929876A patent/JPS5257103A/ja active Granted
- 1976-10-27 RO RO7688240A patent/RO71263A/ro unknown
- 1976-10-28 PL PL19333076A patent/PL110592B1/pl unknown
- 1976-10-28 IT IT2882476A patent/IT1079198B/it active
- 1976-10-28 NL NL7611965A patent/NL7611965A/xx not_active Application Discontinuation
- 1976-10-29 BE BE171988A patent/BE847862A/xx not_active IP Right Cessation
- 1976-10-29 DE DE19762649623 patent/DE2649623A1/de not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| AT346297B (de) | 1978-11-10 |
| DD126591A1 (enExample) | 1977-07-27 |
| HU175954B (en) | 1980-11-28 |
| YU253076A (en) | 1982-05-31 |
| JPS5614089B2 (enExample) | 1981-04-02 |
| FR2329622B1 (enExample) | 1980-07-25 |
| BE847862A (fr) | 1977-02-14 |
| YU39977B (en) | 1985-06-30 |
| SU915797A3 (en) | 1982-03-23 |
| JPS5257103A (en) | 1977-05-11 |
| FR2329622A1 (fr) | 1977-05-27 |
| CS205045B2 (en) | 1981-04-30 |
| CA1077066A (en) | 1980-05-06 |
| GB1532477A (en) | 1978-11-15 |
| IT1079198B (it) | 1985-05-08 |
| RO71263A (ro) | 1981-06-26 |
| DE2649623A1 (de) | 1977-05-12 |
| ATA712976A (de) | 1978-03-15 |
| NL7611965A (nl) | 1977-05-03 |
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