CA1077505A - Process for simultaneously producing p-toluic acid and alkylene oxide - Google Patents
Process for simultaneously producing p-toluic acid and alkylene oxideInfo
- Publication number
- CA1077505A CA1077505A CA255,195A CA255195A CA1077505A CA 1077505 A CA1077505 A CA 1077505A CA 255195 A CA255195 A CA 255195A CA 1077505 A CA1077505 A CA 1077505A
- Authority
- CA
- Canada
- Prior art keywords
- toluic acid
- per
- acid
- toluic
- solution
- 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
- LPNBBFKOUUSUDB-UHFFFAOYSA-N p-toluic acid Chemical compound CC1=CC=C(C(O)=O)C=C1 LPNBBFKOUUSUDB-UHFFFAOYSA-N 0.000 title claims abstract description 126
- 125000002947 alkylene group Chemical group 0.000 title claims abstract description 17
- 238000000034 method Methods 0.000 title claims description 16
- 238000006243 chemical reaction Methods 0.000 claims abstract description 53
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims abstract description 32
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims abstract description 32
- WJJMNDUMQPNECX-UHFFFAOYSA-N dipicolinic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=N1 WJJMNDUMQPNECX-UHFFFAOYSA-N 0.000 claims abstract description 25
- 150000001336 alkenes Chemical class 0.000 claims abstract description 23
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims abstract description 20
- 239000003381 stabilizer Substances 0.000 claims abstract description 15
- 150000004965 peroxy acids Chemical class 0.000 claims abstract description 13
- 239000005725 8-Hydroxyquinoline Substances 0.000 claims abstract description 8
- 229960003540 oxyquinoline Drugs 0.000 claims abstract description 8
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 claims abstract description 8
- WWFMINHWJYHXHF-UHFFFAOYSA-N [6-(hydroxymethyl)pyridin-2-yl]methanol Chemical compound OCC1=CC=CC(CO)=N1 WWFMINHWJYHXHF-UHFFFAOYSA-N 0.000 claims abstract description 5
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims abstract description 4
- 239000005977 Ethylene Substances 0.000 claims abstract description 4
- 239000002904 solvent Substances 0.000 claims description 36
- 238000006735 epoxidation reaction Methods 0.000 claims description 18
- FXLOVSHXALFLKQ-UHFFFAOYSA-N p-tolualdehyde Chemical compound CC1=CC=C(C=O)C=C1 FXLOVSHXALFLKQ-UHFFFAOYSA-N 0.000 claims description 18
- 238000003756 stirring Methods 0.000 claims description 12
- -1 fatty acid ester Chemical class 0.000 claims description 7
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 5
- RXKJFZQQPQGTFL-UHFFFAOYSA-N dihydroxyacetone Chemical group OCC(=O)CO RXKJFZQQPQGTFL-UHFFFAOYSA-N 0.000 claims description 5
- 239000000194 fatty acid Substances 0.000 claims description 5
- 229930195729 fatty acid Natural products 0.000 claims description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- 239000007789 gas Substances 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- 238000006701 autoxidation reaction Methods 0.000 claims 1
- 239000000243 solution Substances 0.000 description 67
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 60
- 239000000047 product Substances 0.000 description 29
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 22
- 239000003054 catalyst Substances 0.000 description 21
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- 238000004821 distillation Methods 0.000 description 14
- 230000001590 oxidative effect Effects 0.000 description 12
- 230000003647 oxidation Effects 0.000 description 10
- 238000007254 oxidation reaction Methods 0.000 description 10
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 9
- 238000011084 recovery Methods 0.000 description 9
- 239000002253 acid Substances 0.000 description 8
- GVPFVAHMJGGAJG-UHFFFAOYSA-L cobalt dichloride Chemical compound [Cl-].[Cl-].[Co+2] GVPFVAHMJGGAJG-UHFFFAOYSA-L 0.000 description 7
- 229940097267 cobaltous chloride Drugs 0.000 description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- SIOXPEMLGUPBBT-UHFFFAOYSA-N picolinic acid Chemical compound OC(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-N 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 5
- ZWLPBLYKEWSWPD-UHFFFAOYSA-N o-toluic acid Chemical compound CC1=CC=CC=C1C(O)=O ZWLPBLYKEWSWPD-UHFFFAOYSA-N 0.000 description 4
- 239000006227 byproduct Substances 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- 229940032007 methylethyl ketone Drugs 0.000 description 3
- 229940081066 picolinic acid Drugs 0.000 description 3
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical class [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical class [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- QAHREYKOYSIQPH-UHFFFAOYSA-L cobalt(II) acetate Chemical compound [Co+2].CC([O-])=O.CC([O-])=O QAHREYKOYSIQPH-UHFFFAOYSA-L 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- FQENQNTWSFEDLI-UHFFFAOYSA-J sodium diphosphate Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]P([O-])(=O)OP([O-])([O-])=O FQENQNTWSFEDLI-UHFFFAOYSA-J 0.000 description 2
- 229940048086 sodium pyrophosphate Drugs 0.000 description 2
- 235000019818 tetrasodium diphosphate Nutrition 0.000 description 2
- 239000001577 tetrasodium phosphonato phosphate Substances 0.000 description 2
- BXGYYDRIMBPOMN-UHFFFAOYSA-N 2-(hydroxymethoxy)ethoxymethanol Chemical compound OCOCCOCO BXGYYDRIMBPOMN-UHFFFAOYSA-N 0.000 description 1
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical class [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical class [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 1
- OVBJJZOQPCKUOR-UHFFFAOYSA-L EDTA disodium salt dihydrate Chemical compound O.O.[Na+].[Na+].[O-]C(=O)C[NH+](CC([O-])=O)CC[NH+](CC([O-])=O)CC([O-])=O OVBJJZOQPCKUOR-UHFFFAOYSA-L 0.000 description 1
- QPCDCPDFJACHGM-UHFFFAOYSA-N N,N-bis{2-[bis(carboxymethyl)amino]ethyl}glycine Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(=O)O)CCN(CC(O)=O)CC(O)=O QPCDCPDFJACHGM-UHFFFAOYSA-N 0.000 description 1
- CVZWMOALRGVDCH-UHFFFAOYSA-N O.O.CC(O)=O.CC(O)=O.CC(O)=O.CC(O)=O Chemical compound O.O.CC(O)=O.CC(O)=O.CC(O)=O.CC(O)=O CVZWMOALRGVDCH-UHFFFAOYSA-N 0.000 description 1
- 229920000388 Polyphosphate Polymers 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 238000010923 batch production Methods 0.000 description 1
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Chemical class 0.000 description 1
- 150000001868 cobalt Chemical class 0.000 description 1
- 239000010941 cobalt Chemical class 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical class [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Chemical class 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- PMNYTGAGAKEGJE-UHFFFAOYSA-N ethane-1,2-diamine;sodium Chemical compound [Na].[Na].NCCN PMNYTGAGAKEGJE-UHFFFAOYSA-N 0.000 description 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 239000001205 polyphosphate Substances 0.000 description 1
- 235000011176 polyphosphates Nutrition 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- ZNNZYHKDIALBAK-UHFFFAOYSA-M potassium thiocyanate Chemical compound [K+].[S-]C#N ZNNZYHKDIALBAK-UHFFFAOYSA-M 0.000 description 1
- 229940116357 potassium thiocyanate Drugs 0.000 description 1
- BALXUFOVQVENIU-KXNXZCPBSA-N pseudoephedrine hydrochloride Chemical compound [H+].[Cl-].CN[C@@H](C)[C@@H](O)C1=CC=CC=C1 BALXUFOVQVENIU-KXNXZCPBSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000007142 ring opening reaction Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000001577 simple distillation Methods 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical class [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D301/00—Preparation of oxiranes
- C07D301/02—Synthesis of the oxirane ring
- C07D301/03—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds
- C07D301/14—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds with organic peracids, or salts, anhydrides or esters thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Epoxy Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP50080734A JPS525704A (en) | 1975-06-30 | 1975-06-30 | Process for simultaneous preparation of p-toluic acid analkylene oxide |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1077505A true CA1077505A (en) | 1980-05-13 |
Family
ID=13726600
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA255,195A Expired CA1077505A (en) | 1975-06-30 | 1976-06-18 | Process for simultaneously producing p-toluic acid and alkylene oxide |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US4243599A (OSRAM) |
| JP (1) | JPS525704A (OSRAM) |
| CA (1) | CA1077505A (OSRAM) |
| DE (1) | DE2629188C3 (OSRAM) |
| FR (1) | FR2316238A1 (OSRAM) |
| GB (1) | GB1512147A (OSRAM) |
| IT (1) | IT1062387B (OSRAM) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE500388C2 (sv) * | 1990-06-13 | 1994-06-13 | Eka Nobel Ab | Förfarande för framställning av epoxider |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE513531A (OSRAM) * | 1952-07-14 | |||
| US3341556A (en) * | 1959-01-22 | 1967-09-12 | Celanese Corp | Process for the production of propylene oxide |
| US3192254A (en) | 1959-10-19 | 1965-06-29 | Shawinigan Chem Ltd | Stabilization of peracids with picolinic acid |
| US3192255A (en) * | 1960-01-18 | 1965-06-29 | Shawinigan Chem Ltd | Stabilization of peracetic acid with quinaldic acid |
| FR1284101A (fr) * | 1960-01-18 | 1962-02-09 | Shawinigan Chem Ltd | Stabilisation de peracides, en particulier de solutions brutes d'acide peracétique |
| US3168554A (en) | 1960-05-26 | 1965-02-02 | Union Carbide Corp | Stabilizers for peracids |
| FR1300781A (fr) * | 1960-05-26 | 1962-08-10 | Union Carbide Corp | Procédé de stabilisation de peracides |
| DE1165009B (de) * | 1960-08-22 | 1964-03-12 | Wacker Chemie Gmbh | Verfahren zur Herstellung von wasserfreien Peressigsaeureloesungen |
| DE1240515B (de) * | 1964-10-22 | 1967-05-18 | Knapsack Ag | Verfahren zur kontinuierlichen Herstellung von Epoxyverbindungen |
| GB1282775A (en) | 1968-08-28 | 1972-07-26 | Japan Gas Chemical Co | Improvements in or relating to the preparation of terephthalic acid |
-
1975
- 1975-06-30 JP JP50080734A patent/JPS525704A/ja active Granted
-
1976
- 1976-06-16 US US05/696,761 patent/US4243599A/en not_active Expired - Lifetime
- 1976-06-17 GB GB25183/76A patent/GB1512147A/en not_active Expired
- 1976-06-18 CA CA255,195A patent/CA1077505A/en not_active Expired
- 1976-06-28 IT IT68597/76A patent/IT1062387B/it active
- 1976-06-29 FR FR7619748A patent/FR2316238A1/fr active Granted
- 1976-06-29 DE DE2629188A patent/DE2629188C3/de not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| GB1512147A (en) | 1978-05-24 |
| IT1062387B (it) | 1984-10-10 |
| FR2316238A1 (fr) | 1977-01-28 |
| DE2629188B2 (de) | 1978-05-03 |
| FR2316238B1 (OSRAM) | 1978-11-17 |
| DE2629188C3 (de) | 1979-01-04 |
| JPS5640142B2 (OSRAM) | 1981-09-18 |
| DE2629188A1 (de) | 1977-01-20 |
| JPS525704A (en) | 1977-01-17 |
| US4243599A (en) | 1981-01-06 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |