DE2236988C3 - Verfahren zur Gewinnung von Styrol - Google Patents
Verfahren zur Gewinnung von StyrolInfo
- Publication number
- DE2236988C3 DE2236988C3 DE19722236988 DE2236988A DE2236988C3 DE 2236988 C3 DE2236988 C3 DE 2236988C3 DE 19722236988 DE19722236988 DE 19722236988 DE 2236988 A DE2236988 A DE 2236988A DE 2236988 C3 DE2236988 C3 DE 2236988C3
- Authority
- DE
- Germany
- Prior art keywords
- styrene
- alpha
- phenylethanol
- distillation
- acetophenone
- 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
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 title claims description 90
- 238000000034 method Methods 0.000 title claims description 24
- 238000004519 manufacturing process Methods 0.000 title claims description 9
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 claims description 76
- 238000004821 distillation Methods 0.000 claims description 32
- WAPNOHKVXSQRPX-UHFFFAOYSA-N 1-phenylethanol Chemical compound CC(O)C1=CC=CC=C1 WAPNOHKVXSQRPX-UHFFFAOYSA-N 0.000 claims description 30
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 27
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 claims description 20
- 230000018044 dehydration Effects 0.000 claims description 13
- 238000006297 dehydration reaction Methods 0.000 claims description 13
- 229920000642 polymer Polymers 0.000 claims description 11
- 238000006116 polymerization reaction Methods 0.000 claims description 10
- 239000007791 liquid phase Substances 0.000 claims description 9
- 239000000203 mixture Substances 0.000 claims description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
- 239000003112 inhibitor Substances 0.000 claims description 6
- 238000006356 dehydrogenation reaction Methods 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 239000002243 precursor Substances 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 description 24
- 239000011593 sulfur Substances 0.000 description 24
- 150000003464 sulfur compounds Chemical class 0.000 description 11
- 230000015572 biosynthetic process Effects 0.000 description 10
- 239000000047 product Substances 0.000 description 9
- 238000000926 separation method Methods 0.000 description 7
- WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 description 6
- 239000003921 oil Substances 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 5
- 238000002156 mixing Methods 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 238000005194 fractionation Methods 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- 238000011084 recovery Methods 0.000 description 3
- 238000010626 work up procedure Methods 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- 229940046892 lead acetate Drugs 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- WYRSGXAIHNMKOL-UHFFFAOYSA-N $l^{1}-sulfanylethane Chemical class CC[S] WYRSGXAIHNMKOL-UHFFFAOYSA-N 0.000 description 1
- NVKHKMBMLSFNNU-UHFFFAOYSA-N C=CC1=CC=CC=C1.[S] Chemical compound C=CC1=CC=CC=C1.[S] NVKHKMBMLSFNNU-UHFFFAOYSA-N 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 1
- MRRWPCWICIRLDJ-UHFFFAOYSA-N [S].CCO Chemical compound [S].CCO MRRWPCWICIRLDJ-UHFFFAOYSA-N 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 230000036571 hydration Effects 0.000 description 1
- 238000006703 hydration reaction Methods 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 238000011165 process development Methods 0.000 description 1
- 239000010802 sludge Substances 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Classifications
-
- 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
- C07C7/00—Purification; Separation; Use of additives
- C07C7/20—Use of additives, e.g. for stabilisation
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (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)
- Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US16658871A | 1971-07-27 | 1971-07-27 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2236988A1 DE2236988A1 (de) | 1973-02-08 |
| DE2236988B2 DE2236988B2 (de) | 1975-01-09 |
| DE2236988C3 true DE2236988C3 (de) | 1975-08-21 |
Family
ID=22603942
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19722236988 Expired DE2236988C3 (de) | 1971-07-27 | 1972-07-27 | Verfahren zur Gewinnung von Styrol |
Country Status (8)
| Country | Link |
|---|---|
| JP (1) | JPS5038086B1 (enExample) |
| BE (1) | BE786687A (enExample) |
| DE (1) | DE2236988C3 (enExample) |
| ES (1) | ES405201A1 (enExample) |
| FR (1) | FR2147193B1 (enExample) |
| GB (1) | GB1398855A (enExample) |
| IT (1) | IT961726B (enExample) |
| NL (1) | NL7210025A (enExample) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS59123019U (ja) * | 1983-02-07 | 1984-08-18 | 株式会社川田製作所 | 粉粒体の供給装置 |
-
0
- BE BE786687D patent/BE786687A/xx unknown
-
1972
- 1972-07-20 NL NL7210025A patent/NL7210025A/xx unknown
- 1972-07-26 GB GB3497672A patent/GB1398855A/en not_active Expired
- 1972-07-26 FR FR7226828A patent/FR2147193B1/fr not_active Expired
- 1972-07-27 JP JP7275518A patent/JPS5038086B1/ja active Pending
- 1972-07-27 IT IT5180672A patent/IT961726B/it active
- 1972-07-27 DE DE19722236988 patent/DE2236988C3/de not_active Expired
- 1972-07-27 ES ES405201A patent/ES405201A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| GB1398855A (en) | 1975-06-25 |
| BE786687A (fr) | 1973-01-25 |
| IT961726B (it) | 1973-12-10 |
| DE2236988A1 (de) | 1973-02-08 |
| FR2147193A1 (enExample) | 1973-03-09 |
| DE2236988B2 (de) | 1975-01-09 |
| NL7210025A (enExample) | 1973-01-30 |
| FR2147193B1 (enExample) | 1977-12-30 |
| ES405201A1 (es) | 1975-07-16 |
| JPS5038086B1 (enExample) | 1975-12-06 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| E77 | Valid patent as to the heymanns-index 1977 | ||
| 8339 | Ceased/non-payment of the annual fee |