DE2247308A1 - Verfahren zur herstellung von mcymol - Google Patents
Verfahren zur herstellung von mcymolInfo
- Publication number
- DE2247308A1 DE2247308A1 DE19722247308 DE2247308A DE2247308A1 DE 2247308 A1 DE2247308 A1 DE 2247308A1 DE 19722247308 DE19722247308 DE 19722247308 DE 2247308 A DE2247308 A DE 2247308A DE 2247308 A1 DE2247308 A1 DE 2247308A1
- Authority
- DE
- Germany
- Prior art keywords
- toluene
- catalyst
- cymene
- propylene
- amount
- 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
- 238000004519 manufacturing process Methods 0.000 title description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 198
- XCYJPXQACVEIOS-UHFFFAOYSA-N 1-isopropyl-3-methylbenzene Chemical compound CC(C)C1=CC=CC(C)=C1 XCYJPXQACVEIOS-UHFFFAOYSA-N 0.000 claims description 48
- 239000003054 catalyst Substances 0.000 claims description 42
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 36
- 239000000203 mixture Substances 0.000 claims description 35
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 34
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 31
- 239000011541 reaction mixture Substances 0.000 claims description 31
- 239000000463 material Substances 0.000 claims description 29
- HFPZCAJZSCWRBC-UHFFFAOYSA-N p-cymene Chemical compound CC(C)C1=CC=C(C)C=C1 HFPZCAJZSCWRBC-UHFFFAOYSA-N 0.000 claims description 25
- 238000000034 method Methods 0.000 claims description 18
- 239000002689 soil Substances 0.000 claims description 16
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 15
- 230000029936 alkylation Effects 0.000 claims description 12
- 238000005804 alkylation reaction Methods 0.000 claims description 12
- 238000006243 chemical reaction Methods 0.000 claims description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 11
- 229930007927 cymene Natural products 0.000 claims description 10
- 238000006317 isomerization reaction Methods 0.000 claims description 9
- 238000010555 transalkylation reaction Methods 0.000 claims description 9
- 230000015572 biosynthetic process Effects 0.000 claims description 6
- 238000004821 distillation Methods 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims 1
- 239000000047 product Substances 0.000 description 12
- 238000000926 separation method Methods 0.000 description 12
- WWRCMNKATXZARA-UHFFFAOYSA-N 1-Isopropyl-2-methylbenzene Chemical compound CC(C)C1=CC=CC=C1C WWRCMNKATXZARA-UHFFFAOYSA-N 0.000 description 10
- 238000003756 stirring Methods 0.000 description 8
- 125000000352 p-cymenyl group Chemical class C1(=C(C=C(C=C1)C)*)C(C)C 0.000 description 6
- 238000002156 mixing Methods 0.000 description 5
- 238000004064 recycling Methods 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- 238000002474 experimental method Methods 0.000 description 4
- 239000002808 molecular sieve Substances 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 3
- 239000011269 tar Substances 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 238000009825 accumulation Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002152 alkylating effect Effects 0.000 description 1
- 230000001174 ascending effect Effects 0.000 description 1
- 238000003287 bathing Methods 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000007809 chemical reaction catalyst Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- -1 des m-cymene isomers Chemical class 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229940082150 encore Drugs 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 238000001030 gas--liquid chromatography Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000012432 intermediate storage Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000002407 reforming Methods 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 238000004062 sedimentation Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C15/00—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts
- C07C15/02—Monocyclic hydrocarbons
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2/00—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms
- C07C2/54—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition of unsaturated hydrocarbons to saturated hydrocarbons or to hydrocarbons containing a six-membered aromatic ring with no unsaturation outside the aromatic ring
- C07C2/64—Addition to a carbon atom of a six-membered aromatic ring
- C07C2/66—Catalytic processes
- C07C2/68—Catalytic processes with halides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2/00—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms
- C07C2/54—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition of unsaturated hydrocarbons to saturated hydrocarbons or to hydrocarbons containing a six-membered aromatic ring with no unsaturation outside the aromatic ring
- C07C2/64—Addition to a carbon atom of a six-membered aromatic ring
- C07C2/66—Catalytic processes
- C07C2/70—Catalytic processes with acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C7/00—Purification; Separation; Use of additives
- C07C7/04—Purification; Separation; Use of additives by distillation
-
- 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
- C07C2527/06—Halogens; Compounds thereof
- C07C2527/08—Halides
- C07C2527/10—Chlorides
- C07C2527/11—Hydrogen chloride
-
- 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
- C07C2527/06—Halogens; Compounds thereof
- C07C2527/125—Compounds comprising a halogen and scandium, yttrium, aluminium, gallium, indium or thallium
- C07C2527/126—Aluminium chloride
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (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)
- Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US18674071A | 1971-10-05 | 1971-10-05 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2247308A1 true DE2247308A1 (de) | 1973-04-12 |
Family
ID=22686108
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19722247308 Pending DE2247308A1 (de) | 1971-10-05 | 1972-09-27 | Verfahren zur herstellung von mcymol |
Country Status (8)
| Country | Link |
|---|---|
| JP (1) | JPS4844222A (OSRAM) |
| BE (1) | BE789654A (OSRAM) |
| CA (1) | CA956329A (OSRAM) |
| DE (1) | DE2247308A1 (OSRAM) |
| FR (1) | FR2156061B1 (OSRAM) |
| GB (1) | GB1408058A (OSRAM) |
| IT (1) | IT968608B (OSRAM) |
| NL (1) | NL7213525A (OSRAM) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2415836C2 (ru) * | 2009-03-19 | 2011-04-10 | Общество с ограниченной ответственностью "НИПИМ-Новые химические технологии" (ООО "НИПИМ-НХИМТЕК") | Способ получения чистой изофталевой кислоты и сопутствующих продуктов из изомеров цимола и диизопропилбензола |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB600505A (en) * | 1944-09-26 | 1948-04-12 | Standard Oil Dev Co | An improved alkylation of aromatic hydrocarbons |
| GB754872A (en) * | 1953-06-29 | 1956-08-15 | Hercules Powder Co Ltd | Improvements in or relating to the preparation of a mixture of cymene isomers rich in m- and p-cymene |
-
0
- BE BE789654D patent/BE789654A/xx unknown
-
1972
- 1972-08-28 CA CA150,346A patent/CA956329A/en not_active Expired
- 1972-09-27 DE DE19722247308 patent/DE2247308A1/de active Pending
- 1972-10-03 GB GB4561172A patent/GB1408058A/en not_active Expired
- 1972-10-03 JP JP47098695A patent/JPS4844222A/ja active Pending
- 1972-10-04 IT IT30074/72A patent/IT968608B/it active
- 1972-10-05 NL NL7213525A patent/NL7213525A/xx unknown
- 1972-10-05 FR FR7235292A patent/FR2156061B1/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| NL7213525A (OSRAM) | 1973-04-09 |
| FR2156061B1 (OSRAM) | 1976-03-26 |
| BE789654A (fr) | 1973-02-01 |
| JPS4844222A (OSRAM) | 1973-06-26 |
| IT968608B (it) | 1974-03-20 |
| CA956329A (en) | 1974-10-15 |
| GB1408058A (en) | 1975-10-01 |
| FR2156061A1 (OSRAM) | 1973-05-25 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OHJ | Non-payment of the annual fee |