CA1093098A - Traduction non-disponible - Google Patents

Traduction non-disponible

Info

Publication number: CA1093098A
Authority: CA; Canada
Prior art keywords: toluene derivative; per mole; reaction; amount; toluene
Prior art date: 1977-08-15
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

Application number

CA294,239A

Other languages

English (en)

Inventor

Juichi Imamura

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Nippon Soda Co Ltd

National Institute of Advanced Industrial Science and Technology AIST

Sanko Co Ltd

Original Assignee

Agency of Industrial Science and Technology

Nippon Soda Co Ltd

Sanko Chemical Co Ltd

Priority date (The priority date 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 date listed.)

1977-08-15

Filing date

1978-01-03

Publication date

1981-01-06

1978-01-03 Application filed by Agency of Industrial Science and Technology, Nippon Soda Co Ltd, Sanko Chemical Co Ltd filed Critical Agency of Industrial Science and Technology

1981-01-06 Application granted granted Critical

1981-01-06 Publication of CA1093098A publication Critical patent/CA1093098A/fr

Status Expired legal-status Critical Current

Links

238000007254 oxidation reaction Methods 0.000 title claims abstract description 92
150000003613 toluenes Chemical class 0.000 title claims abstract description 61
238000000034 method Methods 0.000 title claims abstract description 49
230000008569 process Effects 0.000 title claims abstract description 32
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 title claims abstract description 22
238000004519 manufacturing process Methods 0.000 title claims abstract description 9
230000003647 oxidation Effects 0.000 title claims description 63
238000006243 chemical reaction Methods 0.000 claims abstract description 182
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims abstract description 81
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract description 68
229910052794 bromium Inorganic materials 0.000 claims abstract description 65
239000002904 solvent Substances 0.000 claims abstract description 34
150000001868 cobalt Chemical class 0.000 claims abstract description 28
150000004671 saturated fatty acids Chemical class 0.000 claims abstract description 28
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 27
239000000126 substance Substances 0.000 claims abstract description 24
150000008064 anhydrides Chemical class 0.000 claims abstract description 15
239000007791 liquid phase Substances 0.000 claims abstract description 13
125000001424 substituent group Chemical group 0.000 claims abstract description 12
125000001183 hydrocarbyl group Chemical group 0.000 claims abstract description 10
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 9
229910001882 dioxygen Inorganic materials 0.000 claims abstract description 9
150000001298 alcohols Chemical class 0.000 claims abstract description 7
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 7
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 171
239000007858 starting material Substances 0.000 claims description 104
229910052760 oxygen Inorganic materials 0.000 claims description 73
239000001301 oxygen Substances 0.000 claims description 71
239000000203 mixture Substances 0.000 claims description 57
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 55
239000007800 oxidant agent Substances 0.000 claims description 52
SQYNKIJPMDEDEG-UHFFFAOYSA-N paraldehyde Chemical compound CC1OC(C)OC(C)O1 SQYNKIJPMDEDEG-UHFFFAOYSA-N 0.000 claims description 30
229960003868 paraldehyde Drugs 0.000 claims description 30
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 29
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 27
UDONPJKEOAWFGI-UHFFFAOYSA-N 1-methyl-3-phenoxybenzene Chemical group CC1=CC=CC(OC=2C=CC=CC=2)=C1 UDONPJKEOAWFGI-UHFFFAOYSA-N 0.000 claims description 23
239000012295 chemical reaction liquid Substances 0.000 claims description 21
125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims description 10
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 9
GYPMBQZAVBFUIZ-UHFFFAOYSA-N 1,2-dimethoxy-4-methylbenzene Chemical compound COC1=CC=C(C)C=C1OC GYPMBQZAVBFUIZ-UHFFFAOYSA-N 0.000 claims description 8
OSIGJGFTADMDOB-UHFFFAOYSA-N 1-Methoxy-3-methylbenzene Chemical compound COC1=CC=CC(C)=C1 OSIGJGFTADMDOB-UHFFFAOYSA-N 0.000 claims description 8
150000003839 salts Chemical class 0.000 claims description 8
ABJOFFUIJZDZBE-UHFFFAOYSA-N 1,2-diethoxy-4-methylbenzene Chemical compound CCOC1=CC=C(C)C=C1OCC ABJOFFUIJZDZBE-UHFFFAOYSA-N 0.000 claims description 6
230000036961 partial effect Effects 0.000 claims description 4
IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical group [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 claims description 3
125000005843 halogen group Chemical group 0.000 claims description 3
WMXFNCKPYCAIQW-UHFFFAOYSA-N 1,2-dimethoxy-3-methylbenzene Chemical group COC1=CC=CC(C)=C1OC WMXFNCKPYCAIQW-UHFFFAOYSA-N 0.000 claims description 2
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
150000001879 copper Chemical class 0.000 claims description 2
WSQCPEYUHYGRJY-UHFFFAOYSA-N 1,2-diethoxy-3-methylbenzene Chemical compound CCOC1=CC=CC(C)=C1OCC WSQCPEYUHYGRJY-UHFFFAOYSA-N 0.000 claims 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
229910052799 carbon Inorganic materials 0.000 claims 1
150000001299 aldehydes Chemical class 0.000 abstract description 26
JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 95
-1 cerium ion Chemical class 0.000 description 72
238000002474 experimental method Methods 0.000 description 56
ZBYYWKJVSFHYJL-UHFFFAOYSA-L cobalt(2+);diacetate;tetrahydrate Chemical compound O.O.O.O.[Co+2].CC([O-])=O.CC([O-])=O ZBYYWKJVSFHYJL-UHFFFAOYSA-L 0.000 description 54
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 48
239000003054 catalyst Substances 0.000 description 39
150000001875 compounds Chemical class 0.000 description 28
239000000047 product Substances 0.000 description 28
239000010941 cobalt Substances 0.000 description 24
229910017052 cobalt Inorganic materials 0.000 description 23
230000001590 oxidative effect Effects 0.000 description 23
239000007795 chemical reaction product Substances 0.000 description 22
GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 21
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 16
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 16
125000001033 ether group Chemical group 0.000 description 16
CHLICZRVGGXEOD-UHFFFAOYSA-N 1-Methoxy-4-methylbenzene Chemical compound COC1=CC=C(C)C=C1 CHLICZRVGGXEOD-UHFFFAOYSA-N 0.000 description 14
239000007789 gas Substances 0.000 description 14
239000007788 liquid Substances 0.000 description 14
RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 14
IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 12
150000002500 ions Chemical class 0.000 description 12
IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 12
230000000694 effects Effects 0.000 description 11
229910001868 water Inorganic materials 0.000 description 11
AMXOYNBUYSYVKV-UHFFFAOYSA-M lithium bromide Chemical compound [Li+].[Br-] AMXOYNBUYSYVKV-UHFFFAOYSA-M 0.000 description 10
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
238000003756 stirring Methods 0.000 description 9
POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 description 8
HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 8
239000000460 chlorine Substances 0.000 description 8
229940011182 cobalt acetate Drugs 0.000 description 8
QAHREYKOYSIQPH-UHFFFAOYSA-L cobalt(II) acetate Chemical compound [Co+2].CC([O-])=O.CC([O-])=O QAHREYKOYSIQPH-UHFFFAOYSA-L 0.000 description 8
235000019260 propionic acid Nutrition 0.000 description 8
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 8
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
230000000875 corresponding effect Effects 0.000 description 7
230000002829 reductive effect Effects 0.000 description 7
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 6
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
239000007864 aqueous solution Substances 0.000 description 6
230000009286 beneficial effect Effects 0.000 description 6
230000015572 biosynthetic process Effects 0.000 description 6
ZTQSAGDEMFDKMZ-UHFFFAOYSA-N butyric aldehyde Natural products CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 6
239000007810 chemical reaction solvent Substances 0.000 description 6
QGUAJWGNOXCYJF-UHFFFAOYSA-N cobalt dinitrate hexahydrate Chemical compound O.O.O.O.O.O.[Co+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O QGUAJWGNOXCYJF-UHFFFAOYSA-N 0.000 description 6
AMFIJXSMYBKJQV-UHFFFAOYSA-L cobalt(2+);octadecanoate Chemical compound [Co+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O AMFIJXSMYBKJQV-UHFFFAOYSA-L 0.000 description 6
QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 6
IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 6
239000001632 sodium acetate Substances 0.000 description 6
235000017281 sodium acetate Nutrition 0.000 description 6
238000011282 treatment Methods 0.000 description 6
BZRRQSJJPUGBAA-UHFFFAOYSA-L cobalt(ii) bromide Chemical compound Br[Co]Br BZRRQSJJPUGBAA-UHFFFAOYSA-L 0.000 description 5
238000000354 decomposition reaction Methods 0.000 description 5
VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 5
238000004821 distillation Methods 0.000 description 5
230000001965 increasing effect Effects 0.000 description 5
GEMHFKXPOCTAIP-UHFFFAOYSA-N n,n-dimethyl-n'-phenylcarbamimidoyl chloride Chemical compound CN(C)C(Cl)=NC1=CC=CC=C1 GEMHFKXPOCTAIP-UHFFFAOYSA-N 0.000 description 5
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
230000009257 reactivity Effects 0.000 description 5
238000005406 washing Methods 0.000 description 5
FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 description 4
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 4
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 4
NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 4
239000002253 acid Substances 0.000 description 4
125000000217 alkyl group Chemical group 0.000 description 4
150000001491 aromatic compounds Chemical class 0.000 description 4
QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 4
239000003153 chemical reaction reagent Substances 0.000 description 4
239000003795 chemical substances by application Substances 0.000 description 4
GAYAMOAYBXKUII-UHFFFAOYSA-L cobalt(2+);dibenzoate Chemical compound [Co+2].[O-]C(=O)C1=CC=CC=C1.[O-]C(=O)C1=CC=CC=C1 GAYAMOAYBXKUII-UHFFFAOYSA-L 0.000 description 4
230000000052 comparative effect Effects 0.000 description 4
239000011521 glass Substances 0.000 description 4
PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
238000010992 reflux Methods 0.000 description 4
239000011734 sodium Substances 0.000 description 4
229910052708 sodium Inorganic materials 0.000 description 4
DTFKRVXLBCAIOZ-UHFFFAOYSA-N 2-methylanisole Chemical compound COC1=CC=CC=C1C DTFKRVXLBCAIOZ-UHFFFAOYSA-N 0.000 description 3
MRLGCTNJRREZHZ-UHFFFAOYSA-N 3-phenoxybenzaldehyde Chemical compound O=CC1=CC=CC(OC=2C=CC=CC=2)=C1 MRLGCTNJRREZHZ-UHFFFAOYSA-N 0.000 description 3
229910000619 316 stainless steel Inorganic materials 0.000 description 3
RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 3
WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
229910021503 Cobalt(II) hydroxide Inorganic materials 0.000 description 3
DJTZIDSZSYWGKR-UHFFFAOYSA-N acetic acid tetrahydrate Chemical compound O.O.O.O.CC(O)=O DJTZIDSZSYWGKR-UHFFFAOYSA-N 0.000 description 3
239000003513 alkali Substances 0.000 description 3
125000003118 aryl group Chemical group 0.000 description 3
150000003935 benzaldehydes Chemical class 0.000 description 3
235000019445 benzyl alcohol Nutrition 0.000 description 3
239000006227 byproduct Substances 0.000 description 3
229910001429 cobalt ion Inorganic materials 0.000 description 3
ASKVAEGIVYSGNY-UHFFFAOYSA-L cobalt(ii) hydroxide Chemical compound [OH-].[OH-].[Co+2] ASKVAEGIVYSGNY-UHFFFAOYSA-L 0.000 description 3
230000003247 decreasing effect Effects 0.000 description 3
238000002290 gas chromatography-mass spectrometry Methods 0.000 description 3
229910000042 hydrogen bromide Inorganic materials 0.000 description 3
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 3
239000012046 mixed solvent Substances 0.000 description 3
229940078487 nickel acetate tetrahydrate Drugs 0.000 description 3
OINIXPNQKAZCRL-UHFFFAOYSA-L nickel(2+);diacetate;tetrahydrate Chemical compound O.O.O.O.[Ni+2].CC([O-])=O.CC([O-])=O OINIXPNQKAZCRL-UHFFFAOYSA-L 0.000 description 3
239000005297 pyrex Substances 0.000 description 3
230000035484 reaction time Effects 0.000 description 3
238000011160 research Methods 0.000 description 3
229920006395 saturated elastomer Polymers 0.000 description 3
235000003441 saturated fatty acids Nutrition 0.000 description 3
WCOYPFBMFKXWBM-UHFFFAOYSA-N 1-methyl-2-phenoxybenzene Chemical compound CC1=CC=CC=C1OC1=CC=CC=C1 WCOYPFBMFKXWBM-UHFFFAOYSA-N 0.000 description 2
PETRWTHZSKVLRE-UHFFFAOYSA-N 2-Methoxy-4-methylphenol Chemical compound COC1=CC(C)=CC=C1O PETRWTHZSKVLRE-UHFFFAOYSA-N 0.000 description 2
ZBCATMYQYDCTIZ-UHFFFAOYSA-N 4-methylcatechol Chemical compound CC1=CC=C(O)C(O)=C1 ZBCATMYQYDCTIZ-UHFFFAOYSA-N 0.000 description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
229910021576 Iron(III) bromide Inorganic materials 0.000 description 2
UIQWBVPFHHQZHH-UHFFFAOYSA-N OOOOOOOOOOOOOO Chemical compound OOOOOOOOOOOOOO UIQWBVPFHHQZHH-UHFFFAOYSA-N 0.000 description 2
CQGRLHBOVUGVEA-UHFFFAOYSA-N OOOOOOOOOOOOOOO Chemical compound OOOOOOOOOOOOOOO CQGRLHBOVUGVEA-UHFFFAOYSA-N 0.000 description 2
HFEFMUSTGZNOPY-UHFFFAOYSA-N OOOOOOOOOOOOOOOO Chemical compound OOOOOOOOOOOOOOOO HFEFMUSTGZNOPY-UHFFFAOYSA-N 0.000 description 2
BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-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
FXXACINHVKSMDR-UHFFFAOYSA-N acetyl bromide Chemical compound CC(Br)=O FXXACINHVKSMDR-UHFFFAOYSA-N 0.000 description 2
SWLVFNYSXGMGBS-UHFFFAOYSA-N ammonium bromide Chemical compound [NH4+].[Br-] SWLVFNYSXGMGBS-UHFFFAOYSA-N 0.000 description 2
238000004458 analytical method Methods 0.000 description 2
125000003710 aryl alkyl group Chemical group 0.000 description 2
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
150000003938 benzyl alcohols Chemical class 0.000 description 2
238000009835 boiling Methods 0.000 description 2
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
AERUOEZHIAYQQL-UHFFFAOYSA-K cerium(3+);triacetate;hydrate Chemical compound O.[Ce+3].CC([O-])=O.CC([O-])=O.CC([O-])=O AERUOEZHIAYQQL-UHFFFAOYSA-K 0.000 description 2
229910052801 chlorine Inorganic materials 0.000 description 2
XLJKHNWPARRRJB-UHFFFAOYSA-N cobalt(2+) Chemical compound [Co+2] XLJKHNWPARRRJB-UHFFFAOYSA-N 0.000 description 2
238000001816 cooling Methods 0.000 description 2
QTMDXZNDVAMKGV-UHFFFAOYSA-L copper(ii) bromide Chemical compound [Cu+2].[Br-].[Br-] QTMDXZNDVAMKGV-UHFFFAOYSA-L 0.000 description 2
125000000753 cycloalkyl group Chemical group 0.000 description 2
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
PLXSXOUOWRGVOZ-UHFFFAOYSA-L dibromocobalt;hexahydrate Chemical compound O.O.O.O.O.O.Br[Co]Br PLXSXOUOWRGVOZ-UHFFFAOYSA-L 0.000 description 2
235000014113 dietary fatty acids Nutrition 0.000 description 2
DENRZWYUOJLTMF-UHFFFAOYSA-N diethyl sulfate Chemical compound CCOS(=O)(=O)OCC DENRZWYUOJLTMF-UHFFFAOYSA-N 0.000 description 2
229940008406 diethyl sulfate Drugs 0.000 description 2
235000019439 ethyl acetate Nutrition 0.000 description 2
229930195729 fatty acid Natural products 0.000 description 2
239000000194 fatty acid Substances 0.000 description 2
150000004665 fatty acids Chemical class 0.000 description 2
239000000945 filler Substances 0.000 description 2
238000004817 gas chromatography Methods 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
238000011065 in-situ storage Methods 0.000 description 2
230000006698 induction Effects 0.000 description 2
230000002401 inhibitory effect Effects 0.000 description 2
239000013067 intermediate product Substances 0.000 description 2
KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 2
150000002576 ketones Chemical class 0.000 description 2
230000000670 limiting effect Effects 0.000 description 2
230000001035 methylating effect Effects 0.000 description 2
238000002156 mixing Methods 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 2
239000012071 phase Substances 0.000 description 2
238000000926 separation method Methods 0.000 description 2
238000007086 side reaction Methods 0.000 description 2
229910000077 silane Inorganic materials 0.000 description 2
229920002545 silicone oil Polymers 0.000 description 2
235000011121 sodium hydroxide Nutrition 0.000 description 2
FEONEKOZSGPOFN-UHFFFAOYSA-K tribromoiron Chemical compound Br[Fe](Br)Br FEONEKOZSGPOFN-UHFFFAOYSA-K 0.000 description 2
238000010792 warming Methods 0.000 description 2
KGANAERDZBAECK-UHFFFAOYSA-N (3-phenoxyphenyl)methanol Chemical compound OCC1=CC=CC(OC=2C=CC=CC=2)=C1 KGANAERDZBAECK-UHFFFAOYSA-N 0.000 description 1
XPHQNMNGUGOWGU-UHFFFAOYSA-N (3-phenoxyphenyl)methyl acetate Chemical compound CC(=O)OCC1=CC=CC(OC=2C=CC=CC=2)=C1 XPHQNMNGUGOWGU-UHFFFAOYSA-N 0.000 description 1
VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 1
MPPPKRYCTPRNTB-UHFFFAOYSA-N 1-bromobutane Chemical compound CCCCBr MPPPKRYCTPRNTB-UHFFFAOYSA-N 0.000 description 1
CYNYIHKIEHGYOZ-UHFFFAOYSA-N 1-bromopropane Chemical compound CCCBr CYNYIHKIEHGYOZ-UHFFFAOYSA-N 0.000 description 1
RMSGQZDGSZOJMU-UHFFFAOYSA-N 1-butyl-2-phenylbenzene Chemical group CCCCC1=CC=CC=C1C1=CC=CC=C1 RMSGQZDGSZOJMU-UHFFFAOYSA-N 0.000 description 1
UALKQROXOHJHFG-UHFFFAOYSA-N 1-ethoxy-3-methylbenzene Chemical compound CCOC1=CC=CC(C)=C1 UALKQROXOHJHFG-UHFFFAOYSA-N 0.000 description 1
BYCXSXPCTRWKRR-UHFFFAOYSA-N 1-methyl-4-octoxybenzene Chemical compound CCCCCCCCOC1=CC=C(C)C=C1 BYCXSXPCTRWKRR-UHFFFAOYSA-N 0.000 description 1
SSTNIXFHCIOCJI-UHFFFAOYSA-N 1-methyl-4-phenoxybenzene Chemical class C1=CC(C)=CC=C1OC1=CC=CC=C1 SSTNIXFHCIOCJI-UHFFFAOYSA-N 0.000 description 1
IMPIIVKYTNMBCD-UHFFFAOYSA-N 2-phenoxybenzaldehyde Chemical compound O=CC1=CC=CC=C1OC1=CC=CC=C1 IMPIIVKYTNMBCD-UHFFFAOYSA-N 0.000 description 1
125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
XMTQQYYKAHVGBJ-UHFFFAOYSA-N 3-(3,4-DICHLOROPHENYL)-1,1-DIMETHYLUREA Chemical compound CN(C)C(=O)NC1=CC=C(Cl)C(Cl)=C1 XMTQQYYKAHVGBJ-UHFFFAOYSA-N 0.000 description 1
PGSWEKYNAOWQDF-UHFFFAOYSA-N 3-methylcatechol Chemical compound CC1=CC=CC(O)=C1O PGSWEKYNAOWQDF-UHFFFAOYSA-N 0.000 description 1
UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
229910052684 Cerium Inorganic materials 0.000 description 1
229910021589 Copper(I) bromide Inorganic materials 0.000 description 1
229910021590 Copper(II) bromide Inorganic materials 0.000 description 1
229910002651 NO3 Inorganic materials 0.000 description 1
VEQPNABPJHWNSG-UHFFFAOYSA-N Nickel(2+) Chemical compound [Ni+2] VEQPNABPJHWNSG-UHFFFAOYSA-N 0.000 description 1
NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
KUGRPPRAQNPSQD-UHFFFAOYSA-N OOOOO Chemical compound OOOOO KUGRPPRAQNPSQD-UHFFFAOYSA-N 0.000 description 1
DTAFLBZLAZYRDX-UHFFFAOYSA-N OOOOOO Chemical compound OOOOOO DTAFLBZLAZYRDX-UHFFFAOYSA-N 0.000 description 1
OZBZONOEYUBXTD-UHFFFAOYSA-N OOOOOOOOO Chemical compound OOOOOOOOO OZBZONOEYUBXTD-UHFFFAOYSA-N 0.000 description 1
YAVWDJDEOLOYQO-UHFFFAOYSA-N OOOOOOOOOO Chemical compound OOOOOOOOOO YAVWDJDEOLOYQO-UHFFFAOYSA-N 0.000 description 1
JWOLLWQJKQOEOL-UHFFFAOYSA-N OOOOOOOOOOOOO Chemical compound OOOOOOOOOOOOO JWOLLWQJKQOEOL-UHFFFAOYSA-N 0.000 description 1
208000036366 Sensation of pressure Diseases 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
229960000583 acetic acid Drugs 0.000 description 1
JUXKWQJJNGJGQO-UHFFFAOYSA-L acetic acid cobalt(2+) diacetate tetrahydrate Chemical compound O.O.O.O.[Co++].CC(O)=O.CC([O-])=O.CC([O-])=O JUXKWQJJNGJGQO-UHFFFAOYSA-L 0.000 description 1
238000013019 agitation Methods 0.000 description 1
150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
229910001513 alkali metal bromide Inorganic materials 0.000 description 1
229910052784 alkaline earth metal Inorganic materials 0.000 description 1
150000001347 alkyl bromides Chemical class 0.000 description 1
PQLAYKMGZDUDLQ-UHFFFAOYSA-K aluminium bromide Chemical compound Br[Al](Br)Br PQLAYKMGZDUDLQ-UHFFFAOYSA-K 0.000 description 1
125000003277 amino group Chemical group 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
150000008378 aryl ethers Chemical class 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
JCRJODALBCWSFP-UHFFFAOYSA-N benzene;cobalt Chemical compound [Co].C1=CC=CC=C1.C1=CC=CC=C1 JCRJODALBCWSFP-UHFFFAOYSA-N 0.000 description 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
150000001649 bromium compounds Chemical class 0.000 description 1
125000001246 bromo group Chemical group Br* 0.000 description 1
RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 1
230000006208 butylation Effects 0.000 description 1
239000001110 calcium chloride Substances 0.000 description 1
229910001628 calcium chloride Inorganic materials 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
150000001735 carboxylic acids Chemical class 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
239000003518 caustics Substances 0.000 description 1
230000008859 change Effects 0.000 description 1
TZWGXFOSKIHUPW-UHFFFAOYSA-L cobalt(2+);propanoate Chemical compound [Co+2].CCC([O-])=O.CCC([O-])=O TZWGXFOSKIHUPW-UHFFFAOYSA-L 0.000 description 1
FJDJVBXSSLDNJB-LNTINUHCSA-N cobalt;(z)-4-hydroxypent-3-en-2-one Chemical compound [Co].C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O FJDJVBXSSLDNJB-LNTINUHCSA-N 0.000 description 1
239000013256 coordination polymer Substances 0.000 description 1
239000012043 crude product Substances 0.000 description 1
125000000000 cycloalkoxy group Chemical group 0.000 description 1
125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
230000007547 defect Effects 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
239000003814 drug Substances 0.000 description 1
238000001035 drying Methods 0.000 description 1
230000003028 elevating effect Effects 0.000 description 1
238000005516 engineering process Methods 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 1
239000012847 fine chemical Substances 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
229910001385 heavy metal Inorganic materials 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
150000002440 hydroxy compounds Chemical class 0.000 description 1
230000006872 improvement Effects 0.000 description 1
239000012535 impurity Substances 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
239000003999 initiator Substances 0.000 description 1
229910001503 inorganic bromide Inorganic materials 0.000 description 1
150000002484 inorganic compounds Chemical class 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
125000005928 isopropyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 description 1
239000003446 ligand Substances 0.000 description 1
125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 1
239000011572 manganese Substances 0.000 description 1
229940071125 manganese acetate Drugs 0.000 description 1
UOGMEBQRZBEZQT-UHFFFAOYSA-L manganese(2+);diacetate Chemical compound [Mn+2].CC([O-])=O.CC([O-])=O UOGMEBQRZBEZQT-UHFFFAOYSA-L 0.000 description 1
239000000463 material Substances 0.000 description 1
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
GQKZBCPTCWJTAS-UHFFFAOYSA-N methoxymethylbenzene Chemical class COCC1=CC=CC=C1 GQKZBCPTCWJTAS-UHFFFAOYSA-N 0.000 description 1
150000005172 methylbenzenes Chemical class 0.000 description 1
125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000001624 naphthyl group Chemical group 0.000 description 1
229910001453 nickel ion Inorganic materials 0.000 description 1
150000005526 organic bromine compounds Chemical class 0.000 description 1
239000002304 perfume Substances 0.000 description 1
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
230000001737 promoting effect Effects 0.000 description 1
230000006207 propylation Effects 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
238000011084 recovery Methods 0.000 description 1
230000009467 reduction Effects 0.000 description 1
238000009738 saturating Methods 0.000 description 1
238000004904 shortening Methods 0.000 description 1
PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
230000003407 synthetizing effect Effects 0.000 description 1
PUGUQINMNYINPK-UHFFFAOYSA-N tert-butyl 4-(2-chloroacetyl)piperazine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCN(C(=O)CCl)CC1 PUGUQINMNYINPK-UHFFFAOYSA-N 0.000 description 1
125000003396 thiol group Chemical group [H]S* 0.000 description 1
125000003944 tolyl group Chemical group 0.000 description 1
FMGDJQPRGBQGAI-UHFFFAOYSA-K tribromoalumane hexahydrate Chemical compound O.O.O.O.O.O.[Al+3].[Br-].[Br-].[Br-] FMGDJQPRGBQGAI-UHFFFAOYSA-K 0.000 description 1
HGBOYTHUEUWSSQ-UHFFFAOYSA-N valeric aldehyde Natural products CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 description 1
125000005023 xylyl group Chemical group 0.000 description 1
NWONKYPBYAMBJT-UHFFFAOYSA-L zinc sulfate Chemical compound [Zn+2].[O-]S([O-])(=O)=O NWONKYPBYAMBJT-UHFFFAOYSA-L 0.000 description 1

Classifications

- 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

Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CA294,239A 1977-08-15 1978-01-03 Traduction non-disponible Expired CA1093098A (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
JP52097646A JPS5850205B2 (ja)	1977-08-15	1977-08-15	２個の脂肪族エ−テル基を持つベンズアルデヒド及びベンジルアルコ−ルの製造方法
JP97646/77		1977-08-15

Publications (1)

Publication Number	Publication Date
CA1093098A true CA1093098A (fr)	1981-01-06

Family

ID=14197867

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA294,239A Expired CA1093098A (fr)	1977-08-15	1978-01-03	Traduction non-disponible

Country Status (2)

Country	Link
JP (1)	JPS5850205B2 (fr)
CA (1)	CA1093098A (fr)

1977
- 1977-08-15 JP JP52097646A patent/JPS5850205B2/ja not_active Expired
1978
- 1978-01-03 CA CA294,239A patent/CA1093098A/fr not_active Expired

Also Published As

Publication number	Publication date
JPS5850205B2 (ja)	1983-11-09
JPS5432428A (en)	1979-03-09

Legal Events

Date	Code	Title	Description
1998-01-06	MKEX	Expiry

Publication	Publication Date	Title
Kharasch et al.	1958	Communications-A New Method of Introducing Peroxy Groups into Organic Molecules
JPS61293932A (ja)	1986-12-24	多芳香族化合物およびその製法
JP2916277B2 (ja)	1999-07-05	ｔｅｒｔ−ブチルヒドロペルオキシドからｔｅｒｔ−ブチルアルコールの触媒的製造法
GB1563078A (en)	1980-03-19	Process for the preparation of 2,5-dichlorophenol
JP2592922B2 (ja)	1997-03-19	ｔｅｒｔ−ブチルアルコ−ルの製造方法
CA1041543A (fr)	1978-10-31	Synthese de composes phenoxyles formyles
US4970338A (en)	1990-11-13	Preparation process of biphenyl-4,4'-dicarboxylic acid
JP2001502692A (ja)	2001-02-27	ナブメトン又はその前駆物質の製造
EP0374850B1 (fr)	1994-03-09	Procédé pour la fabrication de l'acide alpha-(4-isobutylphényl)propionique ou son précurseur
EP0220835A1 (fr)	1987-05-06	Procédé pour la dimérisation d'halogénures aromatiques
US5091594A (en)	1992-02-25	Process for the production of 2,6-di-tert-butylphenol
US5166419A (en)	1992-11-24	Method for preparing α-(4-isobutylphenyl) propionic acid or its precursor
EP0282063B1 (fr)	1991-10-16	Hydrocarbures contenant le fragment 1-(3-vinylphényl)-1-phényl et procédés pour les préparer
EP0160721A1 (fr)	1985-11-13	Procédé d'oxydation pour la préparation d'esters aryliques
US4272634A (en)	1981-06-09	Process for the production of intermediate oxidation products of toluenes having ether linkages
KR810001885B1 (ko)	1981-11-20	에테르 결합을 갖는 톨루엔의 산화중간체의 제조 방법
US4560809A (en)	1985-12-24	Alkylation process
US20240208892A1 (en)	2024-06-27	Extraction method
US4456555A (en)	1984-06-26	Manufacture of aryl esters
CA1265158A (fr)	1990-01-30	Methode de preparation de 3-ethylbenzophenone
US4447656A (en)	1984-05-08	Solvent system for oxidative coupling process
GB2155921A (en)	1985-10-02	Process for producing 4-alkyl-4'-formylbiphenyl
JPH0742247B2 (ja)	1995-05-10	〔（１−フェニルエテニル）フェニル〕プロピオン酸および／またはそのエステルの製造方法
JPH0210813B2 (fr)	1990-03-09
JPS6155898B2 (fr)	1986-11-29