DE2031900C3 - Verfahren zur Herstellung von Isopren - Google Patents
Verfahren zur Herstellung von IsoprenInfo
- Publication number
- DE2031900C3 DE2031900C3 DE2031900A DE2031900A DE2031900C3 DE 2031900 C3 DE2031900 C3 DE 2031900C3 DE 2031900 A DE2031900 A DE 2031900A DE 2031900 A DE2031900 A DE 2031900A DE 2031900 C3 DE2031900 C3 DE 2031900C3
- Authority
- DE
- Germany
- Prior art keywords
- isoprene
- dehydration
- buten
- methyl
- phosphoric acid
- 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
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 title claims description 42
- 238000000034 method Methods 0.000 title claims description 17
- 238000004519 manufacturing process Methods 0.000 title claims description 8
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 36
- 239000003054 catalyst Substances 0.000 claims description 21
- 230000018044 dehydration Effects 0.000 claims description 21
- 238000006297 dehydration reaction Methods 0.000 claims description 21
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 18
- CPJRRXSHAYUTGL-UHFFFAOYSA-N isopentenyl alcohol Chemical compound CC(=C)CCO CPJRRXSHAYUTGL-UHFFFAOYSA-N 0.000 claims description 9
- 239000011261 inert gas Substances 0.000 claims description 8
- 239000008262 pumice Substances 0.000 claims description 8
- 239000004575 stone Substances 0.000 claims description 6
- 230000003197 catalytic effect Effects 0.000 claims description 5
- 239000012876 carrier material Substances 0.000 claims description 3
- 150000007522 mineralic acids Chemical class 0.000 claims description 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 12
- 239000007858 starting material Substances 0.000 description 11
- HNVRRHSXBLFLIG-UHFFFAOYSA-N 3-hydroxy-3-methylbut-1-ene Chemical compound CC(C)(O)C=C HNVRRHSXBLFLIG-UHFFFAOYSA-N 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 9
- 239000000203 mixture Substances 0.000 description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 5
- 239000002245 particle Substances 0.000 description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- BZAZNULYLRVMSW-UHFFFAOYSA-N 2-Methyl-2-buten-3-ol Natural products CC(C)=C(C)O BZAZNULYLRVMSW-UHFFFAOYSA-N 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- VBPSVYDSYVJIPX-UHFFFAOYSA-N methylbutenol Natural products CCC=C(C)O VBPSVYDSYVJIPX-UHFFFAOYSA-N 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 238000003379 elimination reaction Methods 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 230000036571 hydration Effects 0.000 description 2
- 238000006703 hydration reaction Methods 0.000 description 2
- 239000013067 intermediate product Substances 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 150000003138 primary alcohols Chemical class 0.000 description 2
- 150000003509 tertiary alcohols Chemical class 0.000 description 2
- JEYLKNVLTAPJAF-UHFFFAOYSA-N xi-3-Methyl-3-buten-2-ol Chemical compound CC(O)C(C)=C JEYLKNVLTAPJAF-UHFFFAOYSA-N 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- GDKSTFXHMBGCPG-UHFFFAOYSA-N 4,4-dimethyl-1,3-dioxane Chemical compound CC1(C)CCOCO1 GDKSTFXHMBGCPG-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 241000282376 Panthera tigris Species 0.000 description 1
- 241000589614 Pseudomonas stutzeri Species 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000003158 alcohol group Chemical group 0.000 description 1
- 125000000746 allylic group Chemical group 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000000447 dimerizing effect Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 239000008246 gaseous mixture Substances 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 238000006317 isomerization reaction Methods 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000012495 reaction gas Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 229920003051 synthetic elastomer Polymers 0.000 description 1
- 239000005061 synthetic rubber Substances 0.000 description 1
- 150000003505 terpenes Chemical class 0.000 description 1
- 235000007586 terpenes Nutrition 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- B01J27/14—Phosphorus; Compounds thereof
- B01J27/16—Phosphorus; Compounds thereof containing oxygen, i.e. acids, anhydrides and their derivates with N, S, B or halogens without carriers or on carriers based on C, Si, Al or Zr; also salts of Si, Al and Zr
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C1/00—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon
- C07C1/20—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from organic compounds containing only oxygen atoms as heteroatoms
- C07C1/24—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from organic compounds containing only oxygen atoms as heteroatoms by elimination of water
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2527/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- C07C2527/14—Phosphorus; Compounds thereof
- C07C2527/16—Phosphorus; Compounds thereof containing oxygen
- C07C2527/167—Phosphates or other compounds comprising the anion (PnO3n+1)(n+2)-
- C07C2527/173—Phosphoric acid or other acids with the formula Hn+2PnO3n+1
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2031900A DE2031900C3 (de) | 1970-06-27 | 1970-06-27 | Verfahren zur Herstellung von Isopren |
| US00155242A US3714285A (en) | 1970-06-27 | 1971-06-21 | Manufacture of isoprene |
| FR7122812A FR2099832A5 (https=) | 1970-06-27 | 1971-06-23 | |
| NL7108739A NL7108739A (https=) | 1970-06-27 | 1971-06-24 | |
| BE768976A BE768976A (fr) | 1970-06-27 | 1971-06-24 | Procede de preparation d'isoprene |
| CA116,730A CA960230A (en) | 1970-06-27 | 1971-06-25 | Manufacture of isoprene |
| GB2983071A GB1346825A (en) | 1970-06-27 | 1971-06-25 | Manufacture of isoprene |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2031900A DE2031900C3 (de) | 1970-06-27 | 1970-06-27 | Verfahren zur Herstellung von Isopren |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2031900A1 DE2031900A1 (de) | 1972-01-05 |
| DE2031900B2 DE2031900B2 (de) | 1978-04-27 |
| DE2031900C3 true DE2031900C3 (de) | 1979-02-01 |
Family
ID=5775152
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2031900A Expired DE2031900C3 (de) | 1970-06-27 | 1970-06-27 | Verfahren zur Herstellung von Isopren |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US3714285A (https=) |
| BE (1) | BE768976A (https=) |
| CA (1) | CA960230A (https=) |
| DE (1) | DE2031900C3 (https=) |
| FR (1) | FR2099832A5 (https=) |
| GB (1) | GB1346825A (https=) |
| NL (1) | NL7108739A (https=) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5177290A (en) * | 1991-01-10 | 1993-01-05 | Exxon Chemical Patents Inc. | Isoprene process |
| WO2014015210A2 (en) * | 2012-07-20 | 2014-01-23 | Glycos Biotechnologies, Inc. | Microorganisms and processes for the conversion of glycerol to isoprene |
| SG11201709802XA (en) | 2015-06-03 | 2017-12-28 | Kuraray Co | Method for producing conjugated diene |
| KR102338451B1 (ko) * | 2016-05-06 | 2021-12-10 | 주식회사 쿠라레 | 공액 디엔의 제조 방법 |
| IT201900025000A1 (it) | 2019-12-20 | 2021-06-20 | Versalis Spa | Procedimento per la produzione di dieni. |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB345270A (en) * | 1928-12-18 | 1931-03-18 | Ig Farbenindustrie Ag | Manufacture of butadiene or its homologues |
| US1923569A (en) * | 1929-07-22 | 1933-08-22 | Ig Farbenindustrie Ag | Production of diolefines |
| CH509241A (de) * | 1967-02-25 | 1971-06-30 | Basf Ag | Verfahren zur Herstellung von Verbindungen mit Alk-3-en-1-ol-Struktur |
| DE1928632A1 (de) * | 1969-06-06 | 1970-12-10 | Basf Ag | Verfahren zur Herstellung von Isopren |
-
1970
- 1970-06-27 DE DE2031900A patent/DE2031900C3/de not_active Expired
-
1971
- 1971-06-21 US US00155242A patent/US3714285A/en not_active Expired - Lifetime
- 1971-06-23 FR FR7122812A patent/FR2099832A5/fr not_active Expired
- 1971-06-24 BE BE768976A patent/BE768976A/xx unknown
- 1971-06-24 NL NL7108739A patent/NL7108739A/xx unknown
- 1971-06-25 CA CA116,730A patent/CA960230A/en not_active Expired
- 1971-06-25 GB GB2983071A patent/GB1346825A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DE2031900B2 (de) | 1978-04-27 |
| BE768976A (fr) | 1971-12-24 |
| NL7108739A (https=) | 1971-12-29 |
| CA960230A (en) | 1974-12-31 |
| DE2031900A1 (de) | 1972-01-05 |
| GB1346825A (en) | 1974-02-13 |
| US3714285A (en) | 1973-01-30 |
| FR2099832A5 (https=) | 1972-03-17 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| EHJ | Ceased/non-payment of the annual fee |