JPS5912647B2 - 不飽和ケトンの製法 - Google Patents

不飽和ケトンの製法

Info

Publication number: JPS5912647B2
Authority: JP; Japan
Prior art keywords: group; alkyl group; acid; carbon atoms; reaction
Prior art date: 1972-11-17
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

JP48127799A

Other languages

English (en)

Japanese (ja)

Other versions

JPS4981309A (2

Inventor

ゲ−ツノルベルト

フイツシヤ− ロマ−ン

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.)

BASF SE

Original Assignee

BASF SE

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.)

1972-11-17

Filing date

1973-11-15

Publication date

1984-03-24

1973-11-15 Application filed by BASF SE filed Critical BASF SE

1974-08-06 Publication of JPS4981309A publication Critical patent/JPS4981309A/ja

1984-03-24 Publication of JPS5912647B2 publication Critical patent/JPS5912647B2/ja

Status Expired legal-status Critical Current

Links

150000002576 ketones Chemical class 0.000 title claims description 10
238000004519 manufacturing process Methods 0.000 title claims description 6
238000006243 chemical reaction Methods 0.000 claims description 31
125000000217 alkyl group Chemical group 0.000 claims description 16
125000004432 carbon atom Chemical group C* 0.000 claims description 12
XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 claims description 8
125000002723 alicyclic group Chemical group 0.000 claims description 7
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
125000002947 alkylene group Chemical group 0.000 claims description 4
239000000126 substance Substances 0.000 claims description 4
125000002252 acyl group Chemical group 0.000 claims description 2
125000001931 aliphatic group Chemical group 0.000 claims description 2
125000004430 oxygen atom Chemical group O* 0.000 claims description 2
229920006395 saturated elastomer Polymers 0.000 claims description 2
125000001183 hydrocarbyl group Chemical group 0.000 claims 1
239000002253 acid Substances 0.000 description 20
150000001875 compounds Chemical class 0.000 description 14
ASUAYTHWZCLXAN-UHFFFAOYSA-N prenol Chemical compound CC(C)=CCO ASUAYTHWZCLXAN-UHFFFAOYSA-N 0.000 description 11
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
GLZPCOQZEFWAFX-UHFFFAOYSA-N Geraniol Chemical compound CC(C)=CCCC(C)=CCO GLZPCOQZEFWAFX-UHFFFAOYSA-N 0.000 description 8
239000003054 catalyst Substances 0.000 description 8
238000000034 method Methods 0.000 description 8
UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 7
239000011541 reaction mixture Substances 0.000 description 7
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 6
230000002378 acidificating effect Effects 0.000 description 6
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 6
150000007513 acids Chemical class 0.000 description 5
150000004808 allyl alcohols Chemical class 0.000 description 5
238000009835 boiling Methods 0.000 description 5
239000007795 chemical reaction product Substances 0.000 description 5
238000004821 distillation Methods 0.000 description 5
239000000203 mixture Substances 0.000 description 5
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 4
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
150000001735 carboxylic acids Chemical class 0.000 description 4
235000019441 ethanol Nutrition 0.000 description 4
239000002904 solvent Substances 0.000 description 4
KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 4
YYPNJNDODFVZLE-UHFFFAOYSA-N 3-methylbut-2-enoic acid Chemical compound CC(C)=CC(O)=O YYPNJNDODFVZLE-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
239000005792 Geraniol Substances 0.000 description 3
GLZPCOQZEFWAFX-YFHOEESVSA-N Geraniol Natural products CC(C)=CCC\C(C)=C/CO GLZPCOQZEFWAFX-YFHOEESVSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
235000011054 acetic acid Nutrition 0.000 description 3
150000002148 esters Chemical class 0.000 description 3
229940113087 geraniol Drugs 0.000 description 3
239000007791 liquid phase Substances 0.000 description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
235000019260 propionic acid Nutrition 0.000 description 3
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 3
239000007858 starting material Substances 0.000 description 3
SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
NSPPRYXGGYQMPY-UHFFFAOYSA-N 3-Methylbuten-2-ol-1 Natural products CC(C)C(O)=C NSPPRYXGGYQMPY-UHFFFAOYSA-N 0.000 description 2
JMEYZBYPGKGSKR-UHFFFAOYSA-N 5,5-diethoxy-1,3,3-trimethylcyclohexene Chemical compound CCOC1(OCC)CC(C)=CC(C)(C)C1 JMEYZBYPGKGSKR-UHFFFAOYSA-N 0.000 description 2
239000005711 Benzoic acid Substances 0.000 description 2
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 2
WRYNUJYAXVDTCB-UHFFFAOYSA-M acetyloxymercury Chemical compound CC(=O)O[Hg] WRYNUJYAXVDTCB-UHFFFAOYSA-M 0.000 description 2
239000001361 adipic acid Substances 0.000 description 2
235000011037 adipic acid Nutrition 0.000 description 2
150000001299 aldehydes Chemical class 0.000 description 2
235000010233 benzoic acid Nutrition 0.000 description 2
150000001244 carboxylic acid anhydrides Chemical class 0.000 description 2
HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 2
KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 2
LGYTZKPVOAIUKX-UHFFFAOYSA-N kebuzone Chemical compound O=C1C(CCC(=O)C)C(=O)N(C=2C=CC=CC=2)N1C1=CC=CC=C1 LGYTZKPVOAIUKX-UHFFFAOYSA-N 0.000 description 2
229960000194 kebuzone Drugs 0.000 description 2
238000006386 neutralization reaction Methods 0.000 description 2
235000006408 oxalic acid Nutrition 0.000 description 2
WLJVNTCWHIRURA-UHFFFAOYSA-N pimelic acid Chemical compound OC(=O)CCCCCC(O)=O WLJVNTCWHIRURA-UHFFFAOYSA-N 0.000 description 2
238000002360 preparation method Methods 0.000 description 2
239000000047 product Substances 0.000 description 2
239000001384 succinic acid Substances 0.000 description 2
238000010626 work up procedure Methods 0.000 description 2
CZDWPBFILCBJJM-UHFFFAOYSA-N (1-acetyloxy-3,5,5-trimethylcyclohex-2-en-1-yl) acetate Chemical compound CC(=O)OC1(OC(C)=O)CC(C)(C)CC(C)=C1 CZDWPBFILCBJJM-UHFFFAOYSA-N 0.000 description 1
CRDAMVZIKSXKFV-FBXUGWQNSA-N (2-cis,6-cis)-farnesol Chemical compound CC(C)=CCC\C(C)=C/CC\C(C)=C/CO CRDAMVZIKSXKFV-FBXUGWQNSA-N 0.000 description 1
239000000260 (2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-ol Substances 0.000 description 1
JKQXZKUSFCKOGQ-JLGXGRJMSA-N (3R,3'R)-beta,beta-carotene-3,3'-diol Chemical compound C([C@H](O)CC=1C)C(C)(C)C=1/C=C/C(/C)=C/C=C/C(/C)=C/C=C/C=C(C)C=CC=C(C)C=CC1=C(C)C[C@@H](O)CC1(C)C JKQXZKUSFCKOGQ-JLGXGRJMSA-N 0.000 description 1
QAFYGHBGWCPRCI-CSKARUKUSA-N (3e)-4,8-dimethylnona-3,7-dien-2-one Chemical compound CC(C)=CCC\C(C)=C\C(C)=O QAFYGHBGWCPRCI-CSKARUKUSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 1
OXAKRYLGXMEFHA-UHFFFAOYSA-N 10,10-dimethoxy-2,6-dimethylundeca-2,6,8-triene Chemical compound COC(C)(OC)C=CC=C(C)CCC=C(C)C OXAKRYLGXMEFHA-UHFFFAOYSA-N 0.000 description 1
HEWZVZIVELJPQZ-UHFFFAOYSA-N 2,2-dimethoxypropane Chemical compound COC(C)(C)OC HEWZVZIVELJPQZ-UHFFFAOYSA-N 0.000 description 1
LDRWAWZXDDBHTG-UHFFFAOYSA-N 3,5,5-trimethylcyclohex-2-en-1-ol Chemical compound CC1=CC(O)CC(C)(C)C1 LDRWAWZXDDBHTG-UHFFFAOYSA-N 0.000 description 1
XKTYXVDYIKIYJP-UHFFFAOYSA-N 3h-dioxole Chemical compound C1OOC=C1 XKTYXVDYIKIYJP-UHFFFAOYSA-N 0.000 description 1
LDBGZRVFPBCKTB-UHFFFAOYSA-N 4,8,12-trimethyltrideca-3,7,11-trien-2-one Chemical compound CC(C)=CCCC(C)=CCCC(C)=CC(C)=O LDBGZRVFPBCKTB-UHFFFAOYSA-N 0.000 description 1
GCHJBJOOADXJFT-UHFFFAOYSA-N 4-hydroxy-2-methylbut-2-enal Chemical compound O=CC(C)=CCO GCHJBJOOADXJFT-UHFFFAOYSA-N 0.000 description 1
RBVBAHQZJGVUIF-UHFFFAOYSA-N 4-methoxy-3-methylbut-2-en-1-ol Chemical compound COCC(C)=CCO RBVBAHQZJGVUIF-UHFFFAOYSA-N 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
GLZPCOQZEFWAFX-JXMROGBWSA-N Nerol Natural products CC(C)=CCC\C(C)=C\CO GLZPCOQZEFWAFX-JXMROGBWSA-N 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
235000021355 Stearic acid Nutrition 0.000 description 1
JKQXZKUSFCKOGQ-LQFQNGICSA-N Z-zeaxanthin Natural products C([C@H](O)CC=1C)C(C)(C)C=1C=CC(C)=CC=CC(C)=CC=CC=C(C)C=CC=C(C)C=CC1=C(C)C[C@@H](O)CC1(C)C JKQXZKUSFCKOGQ-LQFQNGICSA-N 0.000 description 1
QOPRSMDTRDMBNK-RNUUUQFGSA-N Zeaxanthin Natural products CC(=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C1=C(C)CCC(O)C1(C)C)C=CC=C(/C)C=CC2=C(C)CC(O)CC2(C)C QOPRSMDTRDMBNK-RNUUUQFGSA-N 0.000 description 1
150000001241 acetals Chemical class 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
125000003545 alkoxy group Chemical group 0.000 description 1
150000005215 alkyl ethers Chemical class 0.000 description 1
JKQXZKUSFCKOGQ-LOFNIBRQSA-N all-trans-Zeaxanthin Natural products CC(=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C1=C(C)CC(O)CC1(C)C)C=CC=C(/C)C=CC2=C(C)CC(O)CC2(C)C JKQXZKUSFCKOGQ-LOFNIBRQSA-N 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
235000021466 carotenoid Nutrition 0.000 description 1
150000001747 carotenoids Chemical class 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
238000004140 cleaning Methods 0.000 description 1
229940125904 compound 1 Drugs 0.000 description 1
238000001816 cooling Methods 0.000 description 1
-1 cyclic acetal Chemical class 0.000 description 1
150000002085 enols Chemical class 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
229940043259 farnesol Drugs 0.000 description 1
229930002886 farnesol Natural products 0.000 description 1
230000002349 favourable effect Effects 0.000 description 1
238000004508 fractional distillation Methods 0.000 description 1
150000002430 hydrocarbons Chemical group 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
238000009776 industrial production Methods 0.000 description 1
239000013067 intermediate product Substances 0.000 description 1
238000006317 isomerization reaction Methods 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
150000002905 orthoesters Chemical class 0.000 description 1
125000004043 oxo group Chemical group O=* 0.000 description 1
150000002989 phenols Chemical class 0.000 description 1
239000000049 pigment Substances 0.000 description 1
239000002798 polar solvent Substances 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
230000035945 sensitivity Effects 0.000 description 1
238000000926 separation method Methods 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
CRDAMVZIKSXKFV-UHFFFAOYSA-N trans-Farnesol Natural products CC(C)=CCCC(C)=CCCC(C)=CCO CRDAMVZIKSXKFV-UHFFFAOYSA-N 0.000 description 1
KBPHJBAIARWVSC-XQIHNALSSA-N trans-lutein Natural products CC(=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C1=C(C)CC(O)CC1(C)C)C=CC=C(/C)C=CC2C(=CC(O)CC2(C)C)C KBPHJBAIARWVSC-XQIHNALSSA-N 0.000 description 1
CMSYDJVRTHCWFP-UHFFFAOYSA-N triphenylphosphane;hydrobromide Chemical compound Br.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 CMSYDJVRTHCWFP-UHFFFAOYSA-N 0.000 description 1
239000002351 wastewater Substances 0.000 description 1
239000001775 zeaxanthin Substances 0.000 description 1
229940043269 zeaxanthin Drugs 0.000 description 1
235000010930 zeaxanthin Nutrition 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C403/00—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone
- C07C403/02—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone having side-chains containing only carbon and hydrogen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C403/00—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone
- C07C403/14—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone having side-chains substituted by doubly-bound oxygen atoms
- 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
- C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
- C07C45/511—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups
- C07C45/513—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups the singly bound functional group being an etherified hydroxyl group
- 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
- C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
- C07C45/511—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups
- C07C45/515—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups the singly bound functional group being an acetalised, ketalised hemi-acetalised, or hemi-ketalised hydroxyl group
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated

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)

JP48127799A 1972-11-17 1973-11-15 不飽和ケトンの製法 Expired JPS5912647B2 (ja)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DE2256347A DE2256347C3 (de)	1972-11-17	1972-11-17	Verfahren zur Herstellung von α,β -ungestättigten Ketonen
DE2256347		1972-11-17

Publications (2)

Publication Number	Publication Date
JPS4981309A JPS4981309A (2)	1974-08-06
JPS5912647B2 true JPS5912647B2 (ja)	1984-03-24

Family

ID=5861964

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP48127799A Expired JPS5912647B2 (ja)	1972-11-17	1973-11-15	不飽和ケトンの製法

Country Status (9)

Country	Link
US (1)	US3932462A (2)
JP (1)	JPS5912647B2 (2)
BE (1)	BE807427A (2)
CA (1)	CA1007646A (2)
CH (1)	CH602538A5 (2)
DE (1)	DE2256347C3 (2)
FR (1)	FR2207111B1 (2)
GB (1)	GB1443218A (2)
NL (1)	NL182724C (2)

Families Citing this family (16)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4058536A (en) *	1971-11-17	1977-11-15	Basf Aktiengesellschaft	Production of high molecular weight α,β-unsaturated aldehydes
JPS5175014A (en) *	1974-12-21	1976-06-29	Teijin Ltd	Fuhowaarudehidono seizoho
DE3013565A1 (de) *	1980-04-09	1981-10-15	Consortium für elektrochemische Industrie GmbH, 8000 München	Neue (beta) - a -ungesaettigte ketone und isoprenoide 2,6-dienone, verfahren zu deren herstellung und ihre verwendung als geruchs- und geschmacksstoffe
US4497827A (en) *	1982-08-30	1985-02-05	Syntex (U.S.A.) Inc.	Arachidonic acid analogues as anti-inflammatory and anti-allergic agents
US4613706A (en) *	1984-04-20	1986-09-23	International Flavors & Fragrances Inc.	Isomer-directed process for producing asymmetric ketones using catalytic Claisen rearrangement of allylic ethers, intermediates, and uses of products and intermediates of process in perfumery
US4616095A (en) *	1984-04-20	1986-10-07	International Flavors & Fragrances Inc.	Isomer-directed process for producing asymmetric ketones using catalytic claisen rearrangement of allylic ethers, intermediates, and uses of products and intermediates of process in perfumery
JPS62178539A (ja) *	1986-01-31	1987-08-05	Kuraray Co Ltd	α，β−不飽和ケトン誘導体及びそれを含有する香料組成物
US5827652A (en)	1995-10-31	1998-10-27	Applied Food Biotechnology, Inc.	Zeaxanthin formulations for human ingestion
DE19961030A1 (de) *	1999-12-16	2001-06-21	Haarmann & Reimer Gmbh	Aromen und Aromakompositionen enthaltend 4,8-Dimethyl-3,7-nonadien-2-on und ein Verfahren zu dessen Herstellung
DE19961598A1 (de) *	1999-12-21	2001-07-05	Haarmann & Reimer Gmbh	Parfümkomposition enthaltend 4,8-Dimethyl-3,7-nonadien-2-on
US7691406B2 (en) *	2000-10-27	2010-04-06	ZeaVision LLC.	Zeaxanthin formulations for human ingestion
US8088363B2 (en)	2002-10-28	2012-01-03	Zeavision Llc	Protection against sunburn and skin problems with orally-ingested high-dosage zeaxanthin
US9192586B2 (en)	2003-03-10	2015-11-24	Zeavision Llc	Zeaxanthin formulations with additional ocular-active nutrients, for protecting eye health and treating eye disorders
US20070082066A1 (en) *	2003-05-07	2007-04-12	Gierhart Dennis L	Use of zeaxanthin to reduce light hyper-sensitivity, photophobia, and medical conditions relating to light hyper-sensitivity
US7941211B2 (en) *	2003-11-17	2011-05-10	Zeavision, Llc.	Preloading with macular pigment to improve photodynamic treatment of retinal vascular disorders
US20060089411A1 (en) *	2004-08-07	2006-04-27	Gierhart Dennis L	Treatment of Stargardt's disease and other lipofuscin disorders with combined retinaldehyde inhibitor and zeaxanthin

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3655768A (en) *	1968-11-13	1972-04-11	Basf Ag	Production of alk-1-en-6-ones

1972
- 1972-11-17 DE DE2256347A patent/DE2256347C3/de not_active Expired
1973
- 1973-11-06 NL NLAANVRAGE7315205,A patent/NL182724C/xx not_active IP Right Cessation
- 1973-11-13 US US05/415,414 patent/US3932462A/en not_active Expired - Lifetime
- 1973-11-13 FR FR7340296A patent/FR2207111B1/fr not_active Expired
- 1973-11-14 CH CH1597073A patent/CH602538A5/xx not_active IP Right Cessation
- 1973-11-15 JP JP48127799A patent/JPS5912647B2/ja not_active Expired
- 1973-11-15 CA CA185,878A patent/CA1007646A/en not_active Expired
- 1973-11-16 GB GB5321973A patent/GB1443218A/en not_active Expired
- 1973-11-16 BE BE137843A patent/BE807427A/xx not_active IP Right Cessation

Also Published As

Publication number	Publication date
FR2207111A1 (2)	1974-06-14
US3932462A (en)	1976-01-13
NL7315205A (2)	1974-05-21
CH602538A5 (2)	1978-07-31
CA1007646A (en)	1977-03-29
BE807427A (fr)	1974-05-16
NL182724B (nl)	1987-12-01
GB1443218A (en)	1976-07-21
NL182724C (nl)	1988-05-02
DE2256347A1 (de)	1974-05-22
DE2256347B2 (de)	1981-02-05
JPS4981309A (2)	1974-08-06
DE2256347C3 (de)	1982-01-07
FR2207111B1 (2)	1978-12-29

Publication	Publication Date	Title
JPS5912647B2 (ja)	1984-03-24	不飽和ケトンの製法
US2434110A (en)	1948-01-06	Process for hydrating olefinic aldehydes
JP2001504834A (ja)	2001-04-10	第三アリルアルコールとアルケニルアルキルエーテルとの反応によるγ，δ−不飽和ケトンの製法
US2501144A (en)	1950-03-21	Unsaturated aldehydes and preparation thereof
JPS5826331B2 (ja)	1983-06-02	立体規制されたファルネシル酢酸エステルの製造方法
US3408388A (en)	1968-10-29	Process for preparing esters of unsaturated alcohols from monoesters of saturated 2, 2, 4-trisubstituted-1, 3-diols
US3954804A (en)	1976-05-04	Production of high molecular weight unsaturated ketones
US3057888A (en)	1962-10-09	Processes for and intermediates in the manufacture of unsaturated aldehydes and ketones
KR20010074970A (ko)	2001-08-09	캐롤 반응에 의한 γ,δ-불포화 케톤의 제조 방법
US3184432A (en)	1965-05-18	Process for the production of cyclododecane derivatives
US2920081A (en)	1960-01-05	Production of 2, 5-dialkoxy-tetrahydrofuran
US3236869A (en)	1966-02-22	Allenic acids
US2429411A (en)	1947-10-21	I-alkoxy-z
JPH10147548A (ja)	1998-06-02	γ，δ−不飽和ケトンの製法
US20020169342A1 (en)	2002-11-14	Process for the preparation of unsaturated ketones
US2987524A (en)	1961-06-06	Process for preparing cyclic
JP7619946B2 (ja)	2025-01-22	二環式エノールエーテルの製造方法
US3250815A (en)	1966-05-10	Bicyclo (2.2.1) heptyl carbinols
US3287372A (en)	1966-11-22	Process and intermediates for manufacture of 2-(dialkylmethyl)-5-alkyl-2-cyclohexen-1-ones
CA1111055A (en)	1981-10-20	Cyclohexene derivatives and their preparation
US2583112A (en)	1952-01-22	Process for the oxidation of acetals to acids
US2702823A (en)	1955-02-22	Substituted dialdehydes and preparation of the same
US3057914A (en)	1962-10-09	Process for the preparation of isobutyrate esters
US3549693A (en)	1970-12-22	Process for producing acetoacetic acid esters
US3468927A (en)	1969-09-23	Process for preparing pimelic acid and a 2,2-dialkyl-1,3-propanediol