DE2525625A1 - 1,4-cyclohexadien-1-carboxaldehyd- syn-oxime, verfahren zu ihrer herstellung und ihre verwendung - Google Patents
1,4-cyclohexadien-1-carboxaldehyd- syn-oxime, verfahren zu ihrer herstellung und ihre verwendungInfo
- Publication number
- DE2525625A1 DE2525625A1 DE19752525625 DE2525625A DE2525625A1 DE 2525625 A1 DE2525625 A1 DE 2525625A1 DE 19752525625 DE19752525625 DE 19752525625 DE 2525625 A DE2525625 A DE 2525625A DE 2525625 A1 DE2525625 A1 DE 2525625A1
- Authority
- DE
- Germany
- Prior art keywords
- oxime
- carboxaldehyde
- syn
- cyclohexadiene
- water
- 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.)
- Withdrawn
Links
- 238000000034 method Methods 0.000 title claims description 18
- 238000004519 manufacturing process Methods 0.000 title description 4
- TVNCGUMKOPEJPX-UHFFFAOYSA-N cyclohexa-1,4-diene-1-carbaldehyde Chemical compound O=CC1=CCC=CC1 TVNCGUMKOPEJPX-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 28
- 150000002923 oximes Chemical class 0.000 claims description 25
- -1 1-methoxyethyl group Chemical group 0.000 claims description 8
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- OTRRWCPCFKIMRE-UHFFFAOYSA-N 4-(methoxymethyl)cyclohexa-1,4-diene-1-carbaldehyde Chemical compound COCC1=CCC(C=O)=CC1 OTRRWCPCFKIMRE-UHFFFAOYSA-N 0.000 claims description 3
- 235000013305 food Nutrition 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- IJNJLGFTSIAHEA-UHFFFAOYSA-N prop-2-ynal Chemical compound O=CC#C IJNJLGFTSIAHEA-UHFFFAOYSA-N 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- 239000011541 reaction mixture Substances 0.000 claims 2
- CHVMYQYERXJJMF-UHFFFAOYSA-N 2-(methoxymethyl)buta-1,3-diene Chemical compound COCC(=C)C=C CHVMYQYERXJJMF-UHFFFAOYSA-N 0.000 claims 1
- 235000013361 beverage Nutrition 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 60
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 35
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 35
- 239000000243 solution Substances 0.000 description 34
- 239000000047 product Substances 0.000 description 20
- 150000001299 aldehydes Chemical class 0.000 description 18
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- 239000000203 mixture Substances 0.000 description 15
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 15
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 14
- 238000003756 stirring Methods 0.000 description 12
- 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 9
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- 239000000284 extract Substances 0.000 description 9
- 235000003599 food sweetener Nutrition 0.000 description 9
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 9
- 239000003765 sweetening agent Substances 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 238000005481 NMR spectroscopy Methods 0.000 description 8
- 238000010438 heat treatment Methods 0.000 description 8
- 239000012535 impurity Substances 0.000 description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- 239000007788 liquid Substances 0.000 description 7
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 7
- 235000017557 sodium bicarbonate Nutrition 0.000 description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 235000009508 confectionery Nutrition 0.000 description 6
- 239000000796 flavoring agent Substances 0.000 description 6
- 238000002329 infrared spectrum Methods 0.000 description 6
- 238000004458 analytical method Methods 0.000 description 5
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- 239000013078 crystal Substances 0.000 description 5
- 150000001993 dienes Chemical class 0.000 description 5
- 235000019634 flavors Nutrition 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 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
- 229930006000 Sucrose Natural products 0.000 description 4
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 4
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 4
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 239000005720 sucrose Substances 0.000 description 4
- LPINISQDAWNRAE-UHFFFAOYSA-N 4-(1-methoxyethyl)cyclohexa-1,4-diene-1-carbaldehyde Chemical compound COC(C)C1=CCC(C=O)=CC1 LPINISQDAWNRAE-UHFFFAOYSA-N 0.000 description 3
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 150000004703 alkoxides Chemical class 0.000 description 3
- 229910021529 ammonia Inorganic materials 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- MGNZXYYWBUKAII-UHFFFAOYSA-N cyclohexa-1,3-diene Chemical class C1CC=CC=C1 MGNZXYYWBUKAII-UHFFFAOYSA-N 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- 239000010410 layer Substances 0.000 description 3
- 229910052744 lithium Inorganic materials 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 239000012047 saturated solution Substances 0.000 description 3
- LLVWLCAZSOLOTF-UHFFFAOYSA-N 1-methyl-4-[1,4,4-tris(4-methylphenyl)buta-1,3-dienyl]benzene Chemical class C1=CC(C)=CC=C1C(C=1C=CC(C)=CC=1)=CC=C(C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 LLVWLCAZSOLOTF-UHFFFAOYSA-N 0.000 description 2
- MSHFRERJPWKJFX-UHFFFAOYSA-N 4-Methoxybenzyl alcohol Chemical compound COC1=CC=C(CO)C=C1 MSHFRERJPWKJFX-UHFFFAOYSA-N 0.000 description 2
- ZNBNBTIDJSKEAM-UHFFFAOYSA-N 4-[7-hydroxy-2-[5-[5-[6-hydroxy-6-(hydroxymethyl)-3,5-dimethyloxan-2-yl]-3-methyloxolan-2-yl]-5-methyloxolan-2-yl]-2,8-dimethyl-1,10-dioxaspiro[4.5]decan-9-yl]-2-methyl-3-propanoyloxypentanoic acid Chemical compound C1C(O)C(C)C(C(C)C(OC(=O)CC)C(C)C(O)=O)OC11OC(C)(C2OC(C)(CC2)C2C(CC(O2)C2C(CC(C)C(O)(CO)O2)C)C)CC1 ZNBNBTIDJSKEAM-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 235000018185 Betula X alpestris Nutrition 0.000 description 2
- 235000018212 Betula X uliginosa Nutrition 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- 206010013911 Dysgeusia Diseases 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- 235000019270 ammonium chloride Nutrition 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 description 2
- 235000011089 carbon dioxide Nutrition 0.000 description 2
- 235000014171 carbonated beverage Nutrition 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000010828 elution Methods 0.000 description 2
- 238000001640 fractional crystallisation Methods 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 229910000378 hydroxylammonium sulfate Inorganic materials 0.000 description 2
- 238000011835 investigation Methods 0.000 description 2
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000012452 mother liquor Substances 0.000 description 2
- KVKFRMCSXWQSNT-UHFFFAOYSA-N n,n'-dimethylethane-1,2-diamine Chemical compound CNCCNC KVKFRMCSXWQSNT-UHFFFAOYSA-N 0.000 description 2
- 150000002825 nitriles Chemical class 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- GEVPUGOOGXGPIO-UHFFFAOYSA-N oxalic acid;dihydrate Chemical compound O.O.OC(=O)C(O)=O GEVPUGOOGXGPIO-UHFFFAOYSA-N 0.000 description 2
- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000012312 sodium hydride Substances 0.000 description 2
- 229910000104 sodium hydride Inorganic materials 0.000 description 2
- 238000000859 sublimation Methods 0.000 description 2
- 230000008022 sublimation Effects 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 235000019605 sweet taste sensations Nutrition 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- SQCWXTCIGOVJIK-UHFFFAOYSA-N 1,3-dimethyl-2-(4-methylphenyl)imidazolidine Chemical compound CN1CCN(C)C1C1=CC=C(C)C=C1 SQCWXTCIGOVJIK-UHFFFAOYSA-N 0.000 description 1
- NTVROKXHNKOSKT-UHFFFAOYSA-N 1-(4-methoxycyclohexa-1,4-dien-1-yl)ethanol Chemical compound COC1=CCC(C(C)O)=CC1 NTVROKXHNKOSKT-UHFFFAOYSA-N 0.000 description 1
- CEQACJSYZXQWRM-UHFFFAOYSA-N 1-methoxy-3-methylbuta-1,3-diene Chemical compound COC=CC(C)=C CEQACJSYZXQWRM-UHFFFAOYSA-N 0.000 description 1
- XBPSYUUYMMVQOE-UHFFFAOYSA-N 1-methoxy-4-(1-methoxyethyl)cyclohexa-1,4-diene Chemical compound COC(C)C1=CCC(OC)=CC1 XBPSYUUYMMVQOE-UHFFFAOYSA-N 0.000 description 1
- DXWSFXNBGFSTQM-UHFFFAOYSA-N 1-methoxy-4-(methoxymethyl)cyclohexa-1,4-diene Chemical compound COCC1=CCC(OC)=CC1 DXWSFXNBGFSTQM-UHFFFAOYSA-N 0.000 description 1
- GSRDUGHNGOULRG-UHFFFAOYSA-N 2-(cyclohexen-1-yl)-1,3-dimethylimidazolidine Chemical compound CN1CCN(C)C1C1=CCCCC1 GSRDUGHNGOULRG-UHFFFAOYSA-N 0.000 description 1
- LVRSTLPAXUEFPA-UHFFFAOYSA-N 2-cyclohexa-1,4-dien-1-yl-1,3-dimethylimidazolidine Chemical compound CN1CCN(C)C1C1=CCC=CC1 LVRSTLPAXUEFPA-UHFFFAOYSA-N 0.000 description 1
- VYGCGKNTNUJJLC-UHFFFAOYSA-N 4-(1-methoxyethyl)cyclohexa-1,4-diene-1-carbonitrile Chemical compound COC(C)C1=CCC(C#N)=CC1 VYGCGKNTNUJJLC-UHFFFAOYSA-N 0.000 description 1
- PPJVAHFUPRHWDY-UHFFFAOYSA-N 4-(methoxymethyl)cyclohex-3-en-1-one Chemical compound COCC1=CCC(=O)CC1 PPJVAHFUPRHWDY-UHFFFAOYSA-N 0.000 description 1
- SXULUUGVQKDQFL-UHFFFAOYSA-N 4-(methoxymethyl)cyclohexa-1,4-diene-1-carbonitrile Chemical compound COCC1=CCC(C#N)=CC1 SXULUUGVQKDQFL-UHFFFAOYSA-N 0.000 description 1
- UMQPLDZASWPEFG-UHFFFAOYSA-N 4-ethylcyclohexa-1,4-diene-1-carbaldehyde Chemical compound CCC1=CCC(C=O)=CC1 UMQPLDZASWPEFG-UHFFFAOYSA-N 0.000 description 1
- IUUULXXWNYKJSL-UHFFFAOYSA-N 4-methoxy-alpha-methylbenzyl alcohol Chemical compound COC1=CC=C(C(C)O)C=C1 IUUULXXWNYKJSL-UHFFFAOYSA-N 0.000 description 1
- 235000013162 Cocos nucifera Nutrition 0.000 description 1
- 244000060011 Cocos nucifera Species 0.000 description 1
- 238000005698 Diels-Alder reaction Methods 0.000 description 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
- WRYCSMQKUKOKBP-UHFFFAOYSA-N Imidazolidine Chemical compound C1CNCN1 WRYCSMQKUKOKBP-UHFFFAOYSA-N 0.000 description 1
- XCOJIVIDDFTHGB-UEUZTHOGSA-N Perillartine Chemical compound CC(=C)[C@H]1CCC(\C=N\O)=CC1 XCOJIVIDDFTHGB-UEUZTHOGSA-N 0.000 description 1
- 206010035148 Plague Diseases 0.000 description 1
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
- 241000607479 Yersinia pestis Species 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 150000003934 aromatic aldehydes Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 235000021028 berry Nutrition 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cis-cyclohexene Natural products C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 208000017541 congenital adrenal hyperplasia due to cytochrome P450 oxidoreductase deficiency Diseases 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- UVJHQYIOXKWHFD-UHFFFAOYSA-N cyclohexa-1,4-diene Chemical compound C1C=CCC=C1 UVJHQYIOXKWHFD-UHFFFAOYSA-N 0.000 description 1
- OANSOJSBHVENEI-UHFFFAOYSA-N cyclohexene-1-carbaldehyde Chemical compound O=CC1=CCCCC1 OANSOJSBHVENEI-UHFFFAOYSA-N 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 238000010575 fractional recrystallization Methods 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- FXLOVSHXALFLKQ-UHFFFAOYSA-N p-tolualdehyde Chemical compound CC1=CC=C(C=O)C=C1 FXLOVSHXALFLKQ-UHFFFAOYSA-N 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
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000006748 scratching Methods 0.000 description 1
- 230000002393 scratching effect Effects 0.000 description 1
- 238000000526 short-path distillation Methods 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 230000009278 visceral effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C249/00—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C249/04—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton of oximes
- C07C249/08—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton of oximes by reaction of hydroxylamines with carbonyl compounds
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
- A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
- A23L27/30—Artificial sweetening agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/32—Oximes
- C07C251/34—Oximes with oxygen atoms of oxyimino groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
- C07C251/36—Oximes with oxygen atoms of oxyimino groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with the carbon atoms of the oxyimino groups bound to hydrogen atoms or to acyclic carbon 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
- C07C45/44—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reduction and hydrolysis of nitriles
-
- 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
- C07C45/56—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds
- C07C45/562—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with nitrogen as the only hetero atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C47/00—Compounds having —CHO groups
- C07C47/38—Unsaturated compounds having —CHO groups bound to carbon atoms of rings other than six—membered aromatic rings
- C07C47/42—Unsaturated compounds having —CHO groups bound to carbon atoms of rings other than six—membered aromatic rings with a six-membered ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Health & Medical Sciences (AREA)
- Nutrition Science (AREA)
- Engineering & Computer Science (AREA)
- Food Science & Technology (AREA)
- Polymers & Plastics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Seasonings (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US477995A US3919318A (en) | 1974-06-10 | 1974-06-10 | 1,4-Cyclohexadiene-1-carboxaldehyde syn-oxime synthetic sweetening agents |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2525625A1 true DE2525625A1 (de) | 1975-12-18 |
Family
ID=23898134
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19752525625 Withdrawn DE2525625A1 (de) | 1974-06-10 | 1975-06-09 | 1,4-cyclohexadien-1-carboxaldehyd- syn-oxime, verfahren zu ihrer herstellung und ihre verwendung |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US3919318A (enExample) |
| JP (1) | JPS517155A (enExample) |
| AR (1) | AR205382A1 (enExample) |
| BE (1) | BE830890A (enExample) |
| CA (1) | CA1048060A (enExample) |
| DE (1) | DE2525625A1 (enExample) |
| DK (1) | DK261875A (enExample) |
| FR (1) | FR2273801A1 (enExample) |
| GB (1) | GB1476556A (enExample) |
| NL (1) | NL7506766A (enExample) |
| NO (1) | NO140379C (enExample) |
| SE (1) | SE422055B (enExample) |
| SU (1) | SU632689A1 (enExample) |
| ZA (1) | ZA753217B (enExample) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PH12012501992A1 (en) | 2010-04-15 | 2013-01-14 | Chromocell Corp | Compounds, compositions, and methods for reducing or eliminating bitter taste |
| MX355775B (es) | 2011-10-20 | 2018-04-30 | Chromocell Corp | Compuestos, composiciones y metodos para reducir o eliminar el sabor amargo. |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3833654A (en) * | 1973-05-16 | 1974-09-03 | Stanford Research Inst | Sweeteners based on syn oximes of 4-(methoxysubstituted)-1-cyclohexene-1-carboxaldehydes |
-
1974
- 1974-06-10 US US477995A patent/US3919318A/en not_active Expired - Lifetime
-
1975
- 1975-01-01 AR AR259082A patent/AR205382A1/es active
- 1975-05-19 ZA ZA00753217A patent/ZA753217B/xx unknown
- 1975-05-20 GB GB2156775A patent/GB1476556A/en not_active Expired
- 1975-05-23 NO NO751839A patent/NO140379C/no unknown
- 1975-06-04 CA CA228,476A patent/CA1048060A/en not_active Expired
- 1975-06-05 SE SE7506441A patent/SE422055B/xx unknown
- 1975-06-06 NL NL7506766A patent/NL7506766A/xx not_active Application Discontinuation
- 1975-06-09 SU SU752144123A patent/SU632689A1/ru active
- 1975-06-09 FR FR7517914A patent/FR2273801A1/fr active Granted
- 1975-06-09 JP JP50068678A patent/JPS517155A/ja active Pending
- 1975-06-09 DE DE19752525625 patent/DE2525625A1/de not_active Withdrawn
- 1975-06-10 DK DK261875A patent/DK261875A/da unknown
- 1975-07-01 BE BE157893A patent/BE830890A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| BE830890A (fr) | 1975-11-03 |
| GB1476556A (en) | 1977-06-16 |
| DK261875A (da) | 1975-12-11 |
| NL7506766A (nl) | 1975-12-12 |
| AU8141275A (en) | 1976-11-25 |
| ZA753217B (en) | 1976-04-28 |
| JPS517155A (enExample) | 1976-01-21 |
| SE422055B (sv) | 1982-02-15 |
| SU632689A1 (ru) | 1978-11-15 |
| NO140379B (no) | 1979-05-14 |
| FR2273801A1 (fr) | 1976-01-02 |
| FR2273801B1 (enExample) | 1979-06-22 |
| CA1048060A (en) | 1979-02-06 |
| NO751839L (enExample) | 1975-12-11 |
| SE7506441L (sv) | 1975-12-11 |
| US3919318A (en) | 1975-11-11 |
| AR205382A1 (es) | 1976-04-30 |
| NO140379C (no) | 1979-08-22 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8128 | New person/name/address of the agent |
Representative=s name: MUELLER, H., DIPL.-ING., PAT.-ANW., 8000 MUENCHEN |
|
| 8110 | Request for examination paragraph 44 | ||
| 8139 | Disposal/non-payment of the annual fee |