JPS61500547A - ｐ−アルケニルフエノ−ルおよびそられの引続く酸化による置換ベンズアルデヒドの形成方法 - Google Patents

ｐ−アルケニルフエノ−ルおよびそられの引続く酸化による置換ベンズアルデヒドの形成方法

Info

Publication number: JPS61500547A
Authority: JP; Japan
Prior art keywords: hydrocarbyl; reaction; substituted; solvent; dihydrocarbyl
Prior art date: 1983-11-15
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.): Pending

Application number

JP50014483A

Other languages

English (en)

Japanese (ja)

Inventor

エベリイ，チヤールズ　レイ

ローパー，ジエリイ　モンロウ

Original Assignee

エシル　コ−ポレ−シヨン

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.)

1983-11-15

Filing date

1983-11-15

Publication date

1986-03-27

1983-11-15 Application filed by エシル　コ−ポレ−シヨン filed Critical エシル　コ−ポレ−シヨン

1986-03-27 Publication of JPS61500547A publication Critical patent/JPS61500547A/ja

Status Pending legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims description 45
238000007254 oxidation reaction Methods 0.000 title description 3
150000003935 benzaldehydes Chemical class 0.000 title description 2
230000003647 oxidation Effects 0.000 title description 2
238000006243 chemical reaction Methods 0.000 claims description 47
239000000376 reactant Substances 0.000 claims description 33
239000002904 solvent Substances 0.000 claims description 28
150000001412 amines Chemical class 0.000 claims description 20
150000001299 aldehydes Chemical class 0.000 claims description 19
125000004432 carbon atom Chemical group C* 0.000 claims description 18
-1 Aliphatic aldehydes Chemical class 0.000 claims description 16
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 13
239000001301 oxygen Substances 0.000 claims description 13
229910052760 oxygen Inorganic materials 0.000 claims description 13
239000011541 reaction mixture Substances 0.000 claims description 13
239000003054 catalyst Substances 0.000 claims description 11
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 10
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 9
239000002253 acid Substances 0.000 claims description 9
125000000217 alkyl group Chemical group 0.000 claims description 9
150000007513 acids Chemical class 0.000 claims description 8
229930195733 hydrocarbon Natural products 0.000 claims description 7
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 6
239000007789 gas Substances 0.000 claims description 6
150000002430 hydrocarbons Chemical class 0.000 claims description 6
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
239000000203 mixture Substances 0.000 claims description 6
HHVIBTZHLRERCL-UHFFFAOYSA-N sulfonyldimethane Chemical compound CS(C)(=O)=O HHVIBTZHLRERCL-UHFFFAOYSA-N 0.000 claims description 6
229910052784 alkaline earth metal Inorganic materials 0.000 claims description 5
239000000010 aprotic solvent Substances 0.000 claims description 5
238000009835 boiling Methods 0.000 claims description 5
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
ROSDSFDQCJNGOL-UHFFFAOYSA-N protonated dimethyl amine Natural products CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims description 5
239000004215 Carbon black (E152) Substances 0.000 claims description 4
AMIMRNSIRUDHCM-UHFFFAOYSA-N Isopropylaldehyde Chemical compound CC(C)C=O AMIMRNSIRUDHCM-UHFFFAOYSA-N 0.000 claims description 4
150000008044 alkali metal hydroxides Chemical class 0.000 claims description 4
239000002585 base Substances 0.000 claims description 4
230000015572 biosynthetic process Effects 0.000 claims description 4
KSMVZQYAVGTKIV-UHFFFAOYSA-N decanal Chemical compound CCCCCCCCCC=O KSMVZQYAVGTKIV-UHFFFAOYSA-N 0.000 claims description 4
JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 claims description 4
IAZDPXIOMUYVGZ-UHFFFAOYSA-N dimethyl sulfoxide Natural products CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 4
GVWISOJSERXQBM-UHFFFAOYSA-N n-methylpropan-1-amine Chemical compound CCCNC GVWISOJSERXQBM-UHFFFAOYSA-N 0.000 claims description 4
229910052783 alkali metal Inorganic materials 0.000 claims description 3
125000004429 atom Chemical group 0.000 claims description 3
230000003197 catalytic effect Effects 0.000 claims description 3
239000007795 chemical reaction product Substances 0.000 claims description 3
150000003335 secondary amines Chemical class 0.000 claims description 3
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 2
XGQJZNCFDLXSIJ-UHFFFAOYSA-N Pentadecanal Natural products CCCCCCCCCCCCCCC=O XGQJZNCFDLXSIJ-UHFFFAOYSA-N 0.000 claims description 2
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 claims description 2
WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical compound CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 claims description 2
LIWAQLJGPBVORC-UHFFFAOYSA-N ethylmethylamine Chemical compound CCNC LIWAQLJGPBVORC-UHFFFAOYSA-N 0.000 claims description 2
150000002989 phenols Chemical class 0.000 claims description 2
UHUFTBALEZWWIH-UHFFFAOYSA-N tetradecanal Chemical compound CCCCCCCCCCCCCC=O UHUFTBALEZWWIH-UHFFFAOYSA-N 0.000 claims description 2
125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 claims description 2
NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 claims 2
150000008282 halocarbons Chemical class 0.000 claims 2
HTZXFIALJSIFMB-UHFFFAOYSA-N 2,6-ditert-butyl-4-(2-methylprop-1-enyl)phenol Chemical compound CC(C)=CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 HTZXFIALJSIFMB-UHFFFAOYSA-N 0.000 claims 1
QCOGKXLOEWLIDC-UHFFFAOYSA-N N-methylbutylamine Chemical compound CCCCNC QCOGKXLOEWLIDC-UHFFFAOYSA-N 0.000 claims 1
IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 claims 1
ZTQSAGDEMFDKMZ-UHFFFAOYSA-N butyric aldehyde Natural products CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 claims 1
UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 claims 1
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 1
WDZVNNYQBQRJRX-UHFFFAOYSA-K gold(iii) hydroxide Chemical class O[Au](O)O WDZVNNYQBQRJRX-UHFFFAOYSA-K 0.000 claims 1
RIVIDPPYRINTTH-UHFFFAOYSA-N n-ethylpropan-2-amine Chemical compound CCNC(C)C RIVIDPPYRINTTH-UHFFFAOYSA-N 0.000 claims 1
LZOZLBFZGFLFBV-UHFFFAOYSA-N sulfene Chemical compound C=S(=O)=O LZOZLBFZGFLFBV-UHFFFAOYSA-N 0.000 claims 1
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 34
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
239000000047 product Substances 0.000 description 13
229910052799 carbon Inorganic materials 0.000 description 8
BKIMMITUMNQMOS-UHFFFAOYSA-N nonane Chemical compound CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 description 8
238000002360 preparation method Methods 0.000 description 7
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
150000001875 compounds Chemical class 0.000 description 6
ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 6
239000001257 hydrogen Substances 0.000 description 6
229910052739 hydrogen Inorganic materials 0.000 description 6
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
125000001183 hydrocarbyl group Chemical group 0.000 description 4
239000000543 intermediate Substances 0.000 description 4
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 4
238000003756 stirring Methods 0.000 description 4
125000001424 substituent group Chemical group 0.000 description 4
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
125000003710 aryl alkyl group Chemical group 0.000 description 3
LRHPLDYGYMQRHN-UHFFFAOYSA-N butyl alcohol Substances CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 3
125000000753 cycloalkyl group Chemical group 0.000 description 3
238000004519 manufacturing process Methods 0.000 description 3
150000003839 salts Chemical class 0.000 description 3
239000000126 substance Substances 0.000 description 3
QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 2
CRBJBYGJVIBWIY-UHFFFAOYSA-N 2-isopropylphenol Chemical compound CC(C)C1=CC=CC=C1O CRBJBYGJVIBWIY-UHFFFAOYSA-N 0.000 description 2
IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
239000002841 Lewis acid Substances 0.000 description 2
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
239000003513 alkali Substances 0.000 description 2
150000001342 alkaline earth metals Chemical class 0.000 description 2
125000003118 aryl group Chemical group 0.000 description 2
HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
150000001555 benzenes Chemical class 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
238000003776 cleavage reaction Methods 0.000 description 2
VILAVOFMIJHSJA-UHFFFAOYSA-N dicarbon monoxide Chemical group [C]=C=O VILAVOFMIJHSJA-UHFFFAOYSA-N 0.000 description 2
238000004821 distillation Methods 0.000 description 2
238000002474 experimental method Methods 0.000 description 2
239000011521 glass Substances 0.000 description 2
VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 description 2
239000012442 inert solvent Substances 0.000 description 2
150000007517 lewis acids Chemical class 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
230000035484 reaction time Effects 0.000 description 2
CPRMKOQKXYSDML-UHFFFAOYSA-M rubidium hydroxide Chemical compound [OH-].[Rb+] CPRMKOQKXYSDML-UHFFFAOYSA-M 0.000 description 2
230000007017 scission Effects 0.000 description 2
150000003457 sulfones Chemical class 0.000 description 2
150000003512 tertiary amines Chemical class 0.000 description 2
150000003613 toluenes Chemical class 0.000 description 2
YBNZVBUWVIIJND-UHFFFAOYSA-N (2z)-1-cyclononyl-2-diazocyclononane Chemical compound [N-]=[N+]=C1CCCCCCCC1C1CCCCCCCC1 YBNZVBUWVIIJND-UHFFFAOYSA-N 0.000 description 1
KYVBNYUBXIEUFW-UHFFFAOYSA-N 1,1,3,3-tetramethylguanidine Chemical compound CN(C)C(=N)N(C)C KYVBNYUBXIEUFW-UHFFFAOYSA-N 0.000 description 1
ZXHQLEQLZPJIFG-UHFFFAOYSA-N 1-ethoxyhexane Chemical compound CCCCCCOCC ZXHQLEQLZPJIFG-UHFFFAOYSA-N 0.000 description 1
PKFWNYFJULYNFI-UHFFFAOYSA-N 2,3-diphenylbenzene-1,4-diol Chemical class C=1C=CC=CC=1C=1C(O)=CC=C(O)C=1C1=CC=CC=C1 PKFWNYFJULYNFI-UHFFFAOYSA-N 0.000 description 1
DKCPKDPYUFEZCP-UHFFFAOYSA-N 2,6-di-tert-butylphenol Chemical compound CC(C)(C)C1=CC=CC(C(C)(C)C)=C1O DKCPKDPYUFEZCP-UHFFFAOYSA-N 0.000 description 1
DUCSXVAAPCQAEP-UHFFFAOYSA-N 2,6-dibenzylphenol Chemical compound C1=CC=C(CC=2C=CC=CC=2)C(O)=C1CC1=CC=CC=C1 DUCSXVAAPCQAEP-UHFFFAOYSA-N 0.000 description 1
BGRKGHSKCFAPCL-UHFFFAOYSA-N 2-(2-methylbutan-2-yl)phenol Chemical compound CCC(C)(C)C1=CC=CC=C1O BGRKGHSKCFAPCL-UHFFFAOYSA-N 0.000 description 1
WJQOZHYUIDYNHM-UHFFFAOYSA-N 2-tert-Butylphenol Chemical group CC(C)(C)C1=CC=CC=C1O WJQOZHYUIDYNHM-UHFFFAOYSA-N 0.000 description 1
FUGYGGDSWSUORM-UHFFFAOYSA-N 4-hydroxystyrene Chemical compound OC1=CC=C(C=C)C=C1 FUGYGGDSWSUORM-UHFFFAOYSA-N 0.000 description 1
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical group N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
229910021577 Iron(II) chloride Inorganic materials 0.000 description 1
229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
QCYOIFVBYZNUNW-BYPYZUCNSA-N N,N-dimethyl-L-alanine Chemical compound CN(C)[C@@H](C)C(O)=O QCYOIFVBYZNUNW-BYPYZUCNSA-N 0.000 description 1
CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
229910000831 Steel Inorganic materials 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
230000002411 adverse Effects 0.000 description 1
238000005575 aldol reaction Methods 0.000 description 1
229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
150000001336 alkenes Chemical class 0.000 description 1
230000029936 alkylation Effects 0.000 description 1
238000005804 alkylation reaction Methods 0.000 description 1
239000003963 antioxidant agent Substances 0.000 description 1
RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical compound [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 description 1
229910001863 barium hydroxide Inorganic materials 0.000 description 1
229910021538 borax Inorganic materials 0.000 description 1
WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
150000001721 carbon Chemical group 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
239000012141 concentrate Substances 0.000 description 1
238000010276 construction Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
239000013078 crystal Substances 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
150000004662 dithiols Chemical class 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000000605 extraction Methods 0.000 description 1
238000000855 fermentation Methods 0.000 description 1
230000004151 fermentation Effects 0.000 description 1
239000012467 final product Substances 0.000 description 1
238000004817 gas chromatography Methods 0.000 description 1
239000003502 gasoline Substances 0.000 description 1
239000010931 gold Substances 0.000 description 1
229910052737 gold Inorganic materials 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
235000010299 hexamethylene tetramine Nutrition 0.000 description 1
239000004312 hexamethylene tetramine Substances 0.000 description 1
125000001145 hydrido group Chemical group *[H] 0.000 description 1
150000002431 hydrogen Chemical class 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
125000004356 hydroxy functional group Chemical group O* 0.000 description 1
239000003112 inhibitor Substances 0.000 description 1
NMCUIPGRVMDVDB-UHFFFAOYSA-L iron dichloride Chemical compound Cl[Fe]Cl NMCUIPGRVMDVDB-UHFFFAOYSA-L 0.000 description 1
RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000011968 lewis acid catalyst Substances 0.000 description 1
239000007788 liquid Substances 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
239000010687 lubricating oil Substances 0.000 description 1
238000004949 mass spectrometry Methods 0.000 description 1
239000000463 material Substances 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
150000004692 metal hydroxides Chemical class 0.000 description 1
238000002156 mixing Methods 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
239000003921 oil Substances 0.000 description 1
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
125000000962 organic group Chemical group 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
239000000575 pesticide Substances 0.000 description 1
239000002530 phenolic antioxidant Substances 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
239000004033 plastic Substances 0.000 description 1
229920000642 polymer Polymers 0.000 description 1
235000011056 potassium acetate Nutrition 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
BHZRJJOHZFYXTO-UHFFFAOYSA-L potassium sulfite Chemical compound [K+].[K+].[O-]S([O-])=O BHZRJJOHZFYXTO-UHFFFAOYSA-L 0.000 description 1
235000019252 potassium sulphite Nutrition 0.000 description 1
238000003825 pressing Methods 0.000 description 1
125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
150000003254 radicals Chemical class 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
238000010992 reflux Methods 0.000 description 1
WPFGFHJALYCVMO-UHFFFAOYSA-L rubidium carbonate Chemical compound [Rb+].[Rb+].[O-]C([O-])=O WPFGFHJALYCVMO-UHFFFAOYSA-L 0.000 description 1
229910000026 rubidium carbonate Inorganic materials 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
235000010339 sodium tetraborate Nutrition 0.000 description 1
239000012265 solid product Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000010959 steel Substances 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
235000011149 sulphuric acid Nutrition 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
229950011008 tetrachloroethylene Drugs 0.000 description 1
238000004809 thin layer chromatography Methods 0.000 description 1
230000001256 tonic effect Effects 0.000 description 1
BSVBQGMMJUBVOD-UHFFFAOYSA-N trisodium borate Chemical compound [Na+].[Na+].[Na+].[O-]B([O-])[O-] BSVBQGMMJUBVOD-UHFFFAOYSA-N 0.000 description 1
239000002023 wood Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C47/00—Compounds having —CHO groups
- C07C47/52—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings
- C07C47/56—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings containing hydroxy groups
- C07C47/565—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings containing hydroxy groups all hydroxy groups bound to the ring
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/11—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions increasing the number of carbon atoms
- C07C37/20—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions increasing the number of carbon atoms using aldehydes or ketones
- 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
- C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
- C07C45/32—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen
- C07C45/37—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen of >C—O—functional groups to >C=O groups
- C07C45/38—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen of >C—O—functional groups to >C=O groups being a primary hydroxyl group

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

JP50014483A 1983-11-15 1983-11-15 ｐ−アルケニルフエノ−ルおよびそられの引続く酸化による置換ベンズアルデヒドの形成方法 Pending JPS61500547A (ja)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
PCT/US1983/001815 WO1985002178A1 (en)	1983-11-15	1983-11-15	PROCESS FOR p-ALKENYL PHENOLS AND THEIR SUBSEQUENT OXIDATION FORMING SUBSTITUTED BENZALDEHYDES

Publications (1)

Publication Number	Publication Date
JPS61500547A true JPS61500547A (ja)	1986-03-27

Family

ID=22175588

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP50014483A Pending JPS61500547A (ja)	1983-11-15	1983-11-15	ｐ−アルケニルフエノ−ルおよびそられの引続く酸化による置換ベンズアルデヒドの形成方法

Country Status (3)

Country	Link
EP (1)	EP0163633A4 (de)
JP (1)	JPS61500547A (de)
WO (1)	WO1985002178A1 (de)

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US2841623A (en) *	1957-05-08	1958-07-01	Shell Dev	Process for the alkylation of phenols
US3435061A (en) *	1965-01-06	1969-03-25	Standard Oil Co	Manufacture of aromatic aldehydes and nitriles
US3413347A (en) *	1966-01-26	1968-11-26	Ethyl Corp	Mannich reaction products of high molecular weight alkyl phenols, aldehydes and polyaminopolyalkyleneamines
US3592951A (en) *	1967-12-28	1971-07-13	Ethyl Corp	Process for alkylating a phenol
DE2363464C3 (de) *	1973-12-20	1981-10-22	Bayer Ag, 5090 Leverkusen	Verfahren zur Herstellung von p-Alkenylphenolen
US4009210A (en) *	1975-05-07	1977-02-22	Gulf Oil Corporation	Process for manufacturing 3,5-ditert.butyl-4-hydroxybenzaldehyde by formylation of 2,6-ditert.butylphenol
US4215229A (en) *	1978-06-15	1980-07-29	Koppers Company, Inc.	Process for alkylating phenolic compounds to produce ortho- and para-monoalkylated phenols and 2,4- and 2,6-dialkylated phenols

1983
- 1983-11-15 EP EP19840900176 patent/EP0163633A4/de not_active Withdrawn
- 1983-11-15 JP JP50014483A patent/JPS61500547A/ja active Pending
- 1983-11-15 WO PCT/US1983/001815 patent/WO1985002178A1/en not_active Ceased

Also Published As

Publication number	Publication date
EP0163633A4 (de)	1986-04-15
EP0163633A1 (de)	1985-12-11
WO1985002178A1 (en)	1985-05-23

Publication	Publication Date	Title
US4085146A (en)	1978-04-18	Process for preparing o-hydroxyarylaldehydes
HU198437B (en)	1989-10-30	Process for producing mono- or bis-carbonyl-compounds
US4283564A (en)	1981-08-11	Process for preparing methacrolein
JP3562586B2 (ja)	2004-09-08	化学的方法
US5783737A (en)	1998-07-21	Process for the preparation of 3-carboxy-4-hydroxybenzaldehides and derivatives thereof
JPS6317816B2 (de)	1988-04-15
US4361709A (en)	1982-11-30	Process for the production of o-alkylated phenols
US4016212A (en)	1977-04-05	Process for the preparation of aldehydes
US4048239A (en)	1977-09-13	Process for the ortho alkylation of phenols using aldehydes and hydrogen in the presence of a copper-chromium catalyst
US6184421B1 (en)	2001-02-06	Method for preparing a 4-hydroxybenzaldehyde and derivatives
US2885385A (en)	1959-05-05	Polyphenylol derivatives of olefinic aldehydes
US4816596A (en)	1989-03-28	Process for preparing trifluoroethoxybenzene or trifluoroethylthiobenzene
US20030144541A1 (en)	2003-07-31	Process for preparing alpha-halogenated retones
JPH0517381A (ja)	1993-01-26	アルコキシド触媒作用による縮合アルコールの製造方法
US4435605A (en)	1984-03-06	Process for preparation of 2-phenylethyl alcohols from aromatic aldehydes
KR20000049122A (ko)	2000-07-25	2-히드록시벤조산 및 4-히드록시벤즈알데히드 및 유도체의 선택적 제조 방법
CA1184569A (en)	1985-03-26	Chemical process for the preparation of para-alkenyl phenol
WO1985002178A1 (en)	1985-05-23	PROCESS FOR p-ALKENYL PHENOLS AND THEIR SUBSEQUENT OXIDATION FORMING SUBSTITUTED BENZALDEHYDES
Popp et al.	1964	Reisert compound studies. VI. The condensation of aldehydes with 2‐benzoyl‐1, 2‐dihydroisoquinaldonitrile
CA1216308A (en)	1987-01-06	Process for oxidizing p-alkenylphenols
US4562297A (en)	1985-12-31	Aldehyde synthesis
EP0027426B1 (de)	1983-04-06	Verfahren zur Herstellung von 3-(3,5-di-tert.-Alkyl-4-hydroxyphenyl)-2,2-disubstituierten Propionaldehyden
SU560873A1 (ru)	1977-06-05	Способ получени метакролеина и окиси изобутилена
US3257465A (en)	1966-06-21	Secondary acetylenic carbinols
US2483566A (en)	1949-10-04	Catalytic acylation of aromatic compounds