CA1056852A - Thermolysis of styrene oxide - Google Patents
Thermolysis of styrene oxideInfo
- Publication number
- CA1056852A CA1056852A CA217,706A CA217706A CA1056852A CA 1056852 A CA1056852 A CA 1056852A CA 217706 A CA217706 A CA 217706A CA 1056852 A CA1056852 A CA 1056852A
- Authority
- CA
- Canada
- Prior art keywords
- sulfonate
- styrene oxide
- base number
- thermolysis
- reaction
- 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
- AWMVMTVKBNGEAK-UHFFFAOYSA-N Styrene oxide Chemical compound C1OC1C1=CC=CC=C1 AWMVMTVKBNGEAK-UHFFFAOYSA-N 0.000 title claims abstract description 60
- 238000001149 thermolysis Methods 0.000 title claims abstract description 25
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims abstract description 65
- DTUQWGWMVIHBKE-UHFFFAOYSA-N phenylacetaldehyde Chemical compound O=CCC1=CC=CC=C1 DTUQWGWMVIHBKE-UHFFFAOYSA-N 0.000 claims abstract description 54
- 238000006243 chemical reaction Methods 0.000 claims abstract description 41
- -1 alkaline earth metal sulfonate Chemical class 0.000 claims abstract description 28
- 229910052791 calcium Inorganic materials 0.000 claims abstract description 27
- 239000011575 calcium Substances 0.000 claims abstract description 27
- 229940100595 phenylacetaldehyde Drugs 0.000 claims abstract description 27
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims abstract description 23
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims abstract description 22
- 229910052749 magnesium Inorganic materials 0.000 claims abstract description 21
- 239000011777 magnesium Substances 0.000 claims abstract description 21
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims abstract description 20
- 239000007795 chemical reaction product Substances 0.000 claims abstract description 12
- 238000010438 heat treatment Methods 0.000 claims abstract description 8
- 238000000034 method Methods 0.000 claims description 32
- 230000008569 process Effects 0.000 claims description 28
- 125000004432 carbon atom Chemical group C* 0.000 claims description 13
- 150000008055 alkyl aryl sulfonates Chemical class 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 239000012442 inert solvent Substances 0.000 claims description 8
- 229910001220 stainless steel Inorganic materials 0.000 claims description 4
- 239000010935 stainless steel Substances 0.000 claims description 4
- 239000003054 catalyst Substances 0.000 claims description 2
- 239000000243 solution Substances 0.000 claims 6
- 230000002401 inhibitory effect Effects 0.000 abstract description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 75
- 239000000203 mixture Substances 0.000 description 17
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 10
- 239000007788 liquid Substances 0.000 description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 10
- 230000035484 reaction time Effects 0.000 description 9
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 8
- 230000005764 inhibitory process Effects 0.000 description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 238000004587 chromatography analysis Methods 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 230000008707 rearrangement Effects 0.000 description 5
- 229910000831 Steel Inorganic materials 0.000 description 4
- 150000001342 alkaline earth metals Chemical class 0.000 description 4
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 239000010959 steel Substances 0.000 description 4
- GVKPUBOGCQBJGW-UHFFFAOYSA-N C1(=CC=CC=C1)CC=O.C1C(C2=CC=CC=C2)O1 Chemical compound C1(=CC=CC=C1)CC=O.C1C(C2=CC=CC=C2)O1 GVKPUBOGCQBJGW-UHFFFAOYSA-N 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 125000005228 aryl sulfonate group Chemical group 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000002161 passivation Methods 0.000 description 3
- 230000000737 periodic effect Effects 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-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
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 150000001241 acetals Chemical class 0.000 description 2
- 239000003377 acid catalyst Substances 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- 229910052788 barium Inorganic materials 0.000 description 2
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- 230000005484 gravity Effects 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 125000001273 sulfonato group Chemical class [O-]S(*)(=O)=O 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- SSZACLYPEFCREM-UHFFFAOYSA-N 2-benzyl-1,3-dioxolane Chemical compound C=1C=CC=CC=1CC1OCCO1 SSZACLYPEFCREM-UHFFFAOYSA-N 0.000 description 1
- 229910000619 316 stainless steel Inorganic materials 0.000 description 1
- NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 239000005864 Sulphur Substances 0.000 description 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 150000001553 barium compounds Chemical class 0.000 description 1
- ZWHHNIIGJYNOCC-UHFFFAOYSA-N benzene;calcium Chemical compound [Ca].C1=CC=CC=C1 ZWHHNIIGJYNOCC-UHFFFAOYSA-N 0.000 description 1
- 229940092714 benzenesulfonic acid Drugs 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229940043430 calcium compound Drugs 0.000 description 1
- 150000001674 calcium compounds Chemical class 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000005112 continuous flow technique Methods 0.000 description 1
- 230000009089 cytolysis Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000011010 flushing procedure Methods 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000013383 initial experiment Methods 0.000 description 1
- 238000007689 inspection Methods 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000002304 perfume Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 238000000197 pyrolysis Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 239000012808 vapor phase Substances 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/56—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds
- C07C45/57—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with oxygen as the only heteroatom
- C07C45/58—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with oxygen as the only heteroatom in three-membered rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (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 |
|---|---|---|---|
| US434675A US3927110A (en) | 1974-01-18 | 1974-01-18 | Thermolysis of styrene oxide |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1056852A true CA1056852A (en) | 1979-06-19 |
Family
ID=23725205
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA217,706A Expired CA1056852A (en) | 1974-01-18 | 1975-01-10 | Thermolysis of styrene oxide |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US3927110A (forum.php) |
| JP (1) | JPS50106933A (forum.php) |
| BE (1) | BE824482A (forum.php) |
| CA (1) | CA1056852A (forum.php) |
| CH (1) | CH590806A5 (forum.php) |
| DE (1) | DE2501341C2 (forum.php) |
| FR (1) | FR2258358B1 (forum.php) |
| GB (1) | GB1435292A (forum.php) |
| IT (1) | IT1028426B (forum.php) |
| NL (1) | NL7500407A (forum.php) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1152297B (it) * | 1982-07-28 | 1986-12-31 | Anic Spa | Procedimento per l'isomerizzazione di ossido di stirene od omologhi a beta-fenilaldeidi |
| DE3542994A1 (de) * | 1985-12-05 | 1987-06-11 | Basf Ag | Basisch substituierte phenylacetaldehyde, ihre herstellung und diese enthaltende arzneimittel |
| US4650908A (en) * | 1985-12-23 | 1987-03-17 | The Dow Chemical Company | Production of arylacetaldehydes |
| KR100431516B1 (ko) * | 1996-12-23 | 2004-07-16 | 에스케이 주식회사 | 균주를 이용한 페닐아세트알데하이드의 제조방법 |
| CN104926760B (zh) * | 2015-06-10 | 2016-11-09 | 大连理工大学 | 一种低温分离环氧苯乙烷与苯乙醛的装置及方法 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1069609B (de) * | 1959-11-26 | Deutsche Gold- und Silber Schei deanstalt vormals Roessler Frankfurt/M | Verfahren zur Herstellung von Phenylacetaldehyd | |
| US2628255A (en) * | 1951-01-02 | 1953-02-10 | Dow Chemical Co | Production of arylacetaldehydes |
| US3067256A (en) * | 1959-06-22 | 1962-12-04 | Hoechst Ag | Process for preparing aldehydes by isomerization of alpha-olefin oxides |
| US3122588A (en) * | 1960-05-31 | 1964-02-25 | Union Carbide Corp | Process for the production of aldehydes |
-
1974
- 1974-01-18 US US434675A patent/US3927110A/en not_active Expired - Lifetime
-
1975
- 1975-01-10 CA CA217,706A patent/CA1056852A/en not_active Expired
- 1975-01-14 NL NL7500407A patent/NL7500407A/xx not_active Application Discontinuation
- 1975-01-15 DE DE2501341A patent/DE2501341C2/de not_active Expired
- 1975-01-17 JP JP50007173A patent/JPS50106933A/ja active Pending
- 1975-01-17 IT IT19350/75A patent/IT1028426B/it active
- 1975-01-17 CH CH58075A patent/CH590806A5/xx not_active IP Right Cessation
- 1975-01-17 FR FR7501401A patent/FR2258358B1/fr not_active Expired
- 1975-01-17 GB GB214575A patent/GB1435292A/en not_active Expired
- 1975-01-17 BE BE152454A patent/BE824482A/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| JPS50106933A (forum.php) | 1975-08-22 |
| FR2258358A1 (forum.php) | 1975-08-18 |
| BE824482A (fr) | 1975-05-15 |
| IT1028426B (it) | 1979-01-30 |
| DE2501341A1 (de) | 1975-07-24 |
| AU7738475A (en) | 1976-07-22 |
| FR2258358B1 (forum.php) | 1979-08-17 |
| US3927110A (en) | 1975-12-16 |
| DE2501341C2 (de) | 1983-10-06 |
| GB1435292A (en) | 1976-05-12 |
| NL7500407A (nl) | 1975-07-22 |
| CH590806A5 (forum.php) | 1977-08-31 |
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