JPS6247853B2 - - Google Patents
Info
- Publication number
- JPS6247853B2 JPS6247853B2 JP54003832A JP383279A JPS6247853B2 JP S6247853 B2 JPS6247853 B2 JP S6247853B2 JP 54003832 A JP54003832 A JP 54003832A JP 383279 A JP383279 A JP 383279A JP S6247853 B2 JPS6247853 B2 JP S6247853B2
- Authority
- JP
- Japan
- Prior art keywords
- stage
- distillation
- temperature
- styrene
- residue
- 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 claims description 65
- 238000000034 method Methods 0.000 claims description 40
- 238000004821 distillation Methods 0.000 claims description 37
- WAPNOHKVXSQRPX-UHFFFAOYSA-N 1-phenylethanol Chemical compound CC(O)C1=CC=CC=C1 WAPNOHKVXSQRPX-UHFFFAOYSA-N 0.000 claims description 26
- 238000006297 dehydration reaction Methods 0.000 claims description 19
- 229920000642 polymer Polymers 0.000 claims description 17
- XPNGNIFUDRPBFJ-UHFFFAOYSA-N alpha-methylbenzylalcohol Natural products CC1=CC=CC=C1CO XPNGNIFUDRPBFJ-UHFFFAOYSA-N 0.000 claims description 14
- 230000018044 dehydration Effects 0.000 claims description 13
- 238000004519 manufacturing process Methods 0.000 claims description 4
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 18
- 239000000178 monomer Substances 0.000 description 18
- 238000010992 reflux Methods 0.000 description 18
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 16
- 239000002243 precursor Substances 0.000 description 15
- 239000007791 liquid phase Substances 0.000 description 14
- 239000003054 catalyst Substances 0.000 description 13
- 238000009835 boiling Methods 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 11
- 238000010926 purge Methods 0.000 description 11
- 230000000052 comparative effect Effects 0.000 description 9
- 238000000998 batch distillation Methods 0.000 description 6
- 239000012429 reaction media Substances 0.000 description 6
- 239000000463 material Substances 0.000 description 5
- 238000011084 recovery Methods 0.000 description 5
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 4
- 238000002485 combustion reaction Methods 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 238000005194 fractionation Methods 0.000 description 4
- 239000012071 phase Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 238000005292 vacuum distillation Methods 0.000 description 4
- 238000005516 engineering process Methods 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 238000011437 continuous method Methods 0.000 description 2
- 238000010924 continuous production Methods 0.000 description 2
- 238000006356 dehydrogenation reaction Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000004508 fractional distillation Methods 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- -1 Alpha-methylbenzyl Chemical group 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 229910000975 Carbon steel Inorganic materials 0.000 description 1
- 241001292396 Cirrhitidae Species 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- 239000010962 carbon steel Substances 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 238000001944 continuous distillation Methods 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 239000000806 elastomer Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000010574 gas phase reaction Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 239000003317 industrial substance Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 231100000989 no adverse effect Toxicity 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 238000000197 pyrolysis Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 238000011282 treatment Methods 0.000 description 1
- 238000009489 vacuum treatment Methods 0.000 description 1
- 239000012808 vapor phase Substances 0.000 description 1
- 239000002912 waste gas 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
- 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
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US87054378A | 1978-01-16 | 1978-01-16 | |
| US91812478A | 1978-06-22 | 1978-06-22 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS54130523A JPS54130523A (en) | 1979-10-09 |
| JPS6247853B2 true JPS6247853B2 (de) | 1987-10-09 |
Family
ID=27128165
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP383279A Granted JPS54130523A (en) | 1978-01-16 | 1979-01-16 | Method of recovering monomers from polymer contained residue which is formed in dehydrating alphaamethylbenzylalcohol |
Country Status (8)
| Country | Link |
|---|---|
| JP (1) | JPS54130523A (de) |
| BR (1) | BR7900172A (de) |
| DE (1) | DE2901548C3 (de) |
| ES (1) | ES476891A1 (de) |
| FR (1) | FR2414486A1 (de) |
| GB (1) | GB2012810B (de) |
| IT (1) | IT1117202B (de) |
| NL (1) | NL7900081A (de) |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3526674A (en) * | 1968-08-05 | 1970-09-01 | Halcon International Inc | Process for the dehydration of aralkanols |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2929855A (en) * | 1958-03-28 | 1960-03-22 | Union Carbide Corp | Hydrogenolysis of styrene residues |
-
1979
- 1979-01-05 NL NL7900081A patent/NL7900081A/xx not_active Application Discontinuation
- 1979-01-11 BR BR7900172A patent/BR7900172A/pt unknown
- 1979-01-15 FR FR7900875A patent/FR2414486A1/fr active Granted
- 1979-01-16 DE DE2901548A patent/DE2901548C3/de not_active Expired
- 1979-01-16 GB GB791570A patent/GB2012810B/en not_active Expired
- 1979-01-16 ES ES476891A patent/ES476891A1/es not_active Expired
- 1979-01-16 IT IT47664/79A patent/IT1117202B/it active
- 1979-01-16 JP JP383279A patent/JPS54130523A/ja active Granted
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3526674A (en) * | 1968-08-05 | 1970-09-01 | Halcon International Inc | Process for the dehydration of aralkanols |
Also Published As
| Publication number | Publication date |
|---|---|
| ES476891A1 (es) | 1979-10-16 |
| NL7900081A (nl) | 1979-07-18 |
| GB2012810B (en) | 1982-05-26 |
| BR7900172A (pt) | 1979-08-14 |
| DE2901548A1 (de) | 1979-07-19 |
| FR2414486B1 (de) | 1983-07-29 |
| DE2901548C3 (de) | 1981-08-27 |
| DE2901548B2 (de) | 1980-11-27 |
| FR2414486A1 (fr) | 1979-08-10 |
| IT7947664A0 (it) | 1979-01-16 |
| IT1117202B (it) | 1986-02-17 |
| GB2012810A (en) | 1979-08-01 |
| JPS54130523A (en) | 1979-10-09 |
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