DE1094749B - Verfahren zur Herstellung von 4, 4-dialkyl-2-vinyl- und 4, 4-dialkyl-2-isopropenylsubstituierten Oxazolinen und 5, 6-Dihydro-4H-1, 3-oxazinen sowie deren Spiranen - Google Patents
Verfahren zur Herstellung von 4, 4-dialkyl-2-vinyl- und 4, 4-dialkyl-2-isopropenylsubstituierten Oxazolinen und 5, 6-Dihydro-4H-1, 3-oxazinen sowie deren SpiranenInfo
- Publication number
- DE1094749B DE1094749B DER21143A DER0021143A DE1094749B DE 1094749 B DE1094749 B DE 1094749B DE R21143 A DER21143 A DE R21143A DE R0021143 A DER0021143 A DE R0021143A DE 1094749 B DE1094749 B DE 1094749B
- Authority
- DE
- Germany
- Prior art keywords
- amino
- dialkyl
- methyl
- ester
- isopropenyl
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 16
- 150000002918 oxazolines Chemical class 0.000 title claims description 11
- YWOIQIYQBRDOQA-UHFFFAOYSA-N 5,6-dihydro-4h-1,3-oxazine Chemical class C1COC=NC1 YWOIQIYQBRDOQA-UHFFFAOYSA-N 0.000 title claims description 7
- 238000002360 preparation method Methods 0.000 title claims description 4
- 150000002148 esters Chemical class 0.000 claims description 28
- 238000006243 chemical reaction Methods 0.000 claims description 22
- 238000009835 boiling Methods 0.000 claims description 19
- 239000000203 mixture Substances 0.000 claims description 13
- 239000003054 catalyst Substances 0.000 claims description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 9
- 238000006116 polymerization reaction Methods 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 239000003112 inhibitor Substances 0.000 claims description 8
- 238000004821 distillation Methods 0.000 claims description 7
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 229910052751 metal Inorganic materials 0.000 claims description 5
- 239000002184 metal Substances 0.000 claims description 5
- 125000002524 organometallic group Chemical group 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 230000000737 periodic effect Effects 0.000 claims description 2
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 150000001721 carbon Chemical group 0.000 claims 1
- 239000003245 coal Substances 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- -1 alkyl radicals Chemical class 0.000 description 16
- VXUYXOFXAQZZMF-UHFFFAOYSA-N titanium(IV) isopropoxide Chemical compound CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C VXUYXOFXAQZZMF-UHFFFAOYSA-N 0.000 description 14
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 12
- 125000005397 methacrylic acid ester group Chemical group 0.000 description 11
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 229910052782 aluminium Inorganic materials 0.000 description 6
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 5
- SMZOGRDCAXLAAR-UHFFFAOYSA-N aluminium isopropoxide Chemical compound [Al+3].CC(C)[O-].CC(C)[O-].CC(C)[O-] SMZOGRDCAXLAAR-UHFFFAOYSA-N 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 238000006386 neutralization reaction Methods 0.000 description 5
- JTTMYKSFKOOQLP-UHFFFAOYSA-N 4-hydroxydiphenylamine Chemical compound C1=CC(O)=CC=C1NC1=CC=CC=C1 JTTMYKSFKOOQLP-UHFFFAOYSA-N 0.000 description 4
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-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
- 150000001412 amines Chemical class 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- IMSODMZESSGVBE-UHFFFAOYSA-N 2-Oxazoline Chemical compound C1CN=CO1 IMSODMZESSGVBE-UHFFFAOYSA-N 0.000 description 3
- UZAAWTQDNCMMEX-UHFFFAOYSA-N 4,4-dimethyl-2-prop-1-en-2-yl-5h-1,3-oxazole Chemical compound CC(=C)C1=NC(C)(C)CO1 UZAAWTQDNCMMEX-UHFFFAOYSA-N 0.000 description 3
- 241000227653 Lycopersicon Species 0.000 description 3
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 3
- 150000001414 amino alcohols Chemical class 0.000 description 3
- 238000013459 approach Methods 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 230000000855 fungicidal effect Effects 0.000 description 3
- 239000000417 fungicide Substances 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 239000007921 spray Substances 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- SPSSULHKWOKEEL-UHFFFAOYSA-N 2,4,6-trinitrotoluene Chemical compound CC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O SPSSULHKWOKEEL-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- WYHLKHURMRDRTG-UHFFFAOYSA-N 2-amino-2-methyloctan-1-ol Chemical compound CCCCCCC(C)(N)CO WYHLKHURMRDRTG-UHFFFAOYSA-N 0.000 description 2
- GVHJMGYIHVKAKN-UHFFFAOYSA-N 3-amino-3,4-dimethylpentan-1-ol Chemical compound CC(C)C(C)(N)CCO GVHJMGYIHVKAKN-UHFFFAOYSA-N 0.000 description 2
- PHRHXTTZZWUGNN-UHFFFAOYSA-N 3-amino-3-methylbutan-1-ol Chemical compound CC(C)(N)CCO PHRHXTTZZWUGNN-UHFFFAOYSA-N 0.000 description 2
- YGLJTUYWVXVLEU-UHFFFAOYSA-N 3-amino-3-methylundecan-1-ol Chemical compound NC(CCO)(CCCCCCCC)C YGLJTUYWVXVLEU-UHFFFAOYSA-N 0.000 description 2
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 2
- 241000196324 Embryophyta Species 0.000 description 2
- 241000233866 Fungi Species 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 2
- WUGQZFFCHPXWKQ-UHFFFAOYSA-N Propanolamine Chemical compound NCCCO WUGQZFFCHPXWKQ-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 244000061456 Solanum tuberosum Species 0.000 description 2
- 235000002595 Solanum tuberosum Nutrition 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000004703 alkoxides Chemical class 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- CBTVGIZVANVGBH-UHFFFAOYSA-N aminomethyl propanol Chemical compound CC(C)(N)CO CBTVGIZVANVGBH-UHFFFAOYSA-N 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 235000013399 edible fruits Nutrition 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 238000005194 fractionation Methods 0.000 description 2
- 239000010985 leather Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 125000005395 methacrylic acid group Chemical group 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 235000012015 potatoes Nutrition 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 239000000015 trinitrotoluene Substances 0.000 description 2
- 229910052726 zirconium Inorganic materials 0.000 description 2
- ZNZCBZJTANSNGL-UHFFFAOYSA-N 1-n,2-n-diphenylbenzene-1,2-diamine Chemical compound C=1C=CC=C(NC=2C=CC=CC=2)C=1NC1=CC=CC=C1 ZNZCBZJTANSNGL-UHFFFAOYSA-N 0.000 description 1
- SQAINHDHICKHLX-UHFFFAOYSA-N 1-naphthaldehyde Chemical compound C1=CC=C2C(C=O)=CC=CC2=C1 SQAINHDHICKHLX-UHFFFAOYSA-N 0.000 description 1
- JZODKRWQWUWGCD-UHFFFAOYSA-N 2,5-di-tert-butylbenzene-1,4-diol Chemical compound CC(C)(C)C1=CC(O)=C(C(C)(C)C)C=C1O JZODKRWQWUWGCD-UHFFFAOYSA-N 0.000 description 1
- NDBACGDBUINENU-UHFFFAOYSA-N 2-amino-2,3-dimethylbutan-1-ol Chemical compound CC(C)C(C)(N)CO NDBACGDBUINENU-UHFFFAOYSA-N 0.000 description 1
- YEMAIZYKPDFKNU-UHFFFAOYSA-N 2-amino-2,4-dimethylpentan-1-ol Chemical compound CC(C)CC(C)(N)CO YEMAIZYKPDFKNU-UHFFFAOYSA-N 0.000 description 1
- 229940058020 2-amino-2-methyl-1-propanol Drugs 0.000 description 1
- QHKGDMNPQAZMKD-UHFFFAOYSA-N 2-amino-2-methylbutan-1-ol Chemical compound CCC(C)(N)CO QHKGDMNPQAZMKD-UHFFFAOYSA-N 0.000 description 1
- XVLZSRHRQSCUDP-UHFFFAOYSA-N 2-amino-2-methyldecan-1-ol Chemical compound CCCCCCCCC(C)(N)CO XVLZSRHRQSCUDP-UHFFFAOYSA-N 0.000 description 1
- KIOCABJEBRVQNM-UHFFFAOYSA-N 2-amino-2-methylhexan-1-ol Chemical compound CCCCC(C)(N)CO KIOCABJEBRVQNM-UHFFFAOYSA-N 0.000 description 1
- LAXOIQQEPAILKS-UHFFFAOYSA-N 2-amino-2-methylnonan-1-ol Chemical compound CCCCCCCC(C)(N)CO LAXOIQQEPAILKS-UHFFFAOYSA-N 0.000 description 1
- ATRNFARHWKXXLH-UHFFFAOYSA-N 2-amino-2-methylpentan-1-ol Chemical compound CCCC(C)(N)CO ATRNFARHWKXXLH-UHFFFAOYSA-N 0.000 description 1
- RBTBFTRPCNLSDE-UHFFFAOYSA-N 3,7-bis(dimethylamino)phenothiazin-5-ium Chemical compound C1=CC(N(C)C)=CC2=[S+]C3=CC(N(C)C)=CC=C3N=C21 RBTBFTRPCNLSDE-UHFFFAOYSA-N 0.000 description 1
- HRVFEIFVSYJKQM-UHFFFAOYSA-N 3-amino-3,4,5-trimethylnonan-1-ol Chemical compound NC(CCO)(C(C(CCCC)C)C)C HRVFEIFVSYJKQM-UHFFFAOYSA-N 0.000 description 1
- IWQUGWVRKXZDFL-UHFFFAOYSA-N 3-amino-3,4-dimethylheptan-1-ol Chemical compound NC(CCO)(C(CCC)C)C IWQUGWVRKXZDFL-UHFFFAOYSA-N 0.000 description 1
- DBWRZMQABAHQCO-UHFFFAOYSA-N 3-amino-3-methylheptan-1-ol Chemical compound CCCCC(C)(N)CCO DBWRZMQABAHQCO-UHFFFAOYSA-N 0.000 description 1
- KFGAOLOVOZOVLO-UHFFFAOYSA-N 3-amino-3-methylhexan-1-ol Chemical compound CCCC(C)(N)CCO KFGAOLOVOZOVLO-UHFFFAOYSA-N 0.000 description 1
- VUGFXAKHVHYYJG-UHFFFAOYSA-N 3-amino-3-methylnonan-1-ol Chemical compound CCCCCCC(C)(N)CCO VUGFXAKHVHYYJG-UHFFFAOYSA-N 0.000 description 1
- WIKUCGJLELHSGA-UHFFFAOYSA-N 3-amino-3-methylpentan-1-ol Chemical compound CCC(C)(N)CCO WIKUCGJLELHSGA-UHFFFAOYSA-N 0.000 description 1
- BAGLAURKIQVJJQ-UHFFFAOYSA-N 3-amino-4-ethyl-3-methylnonan-1-ol Chemical compound NC(CCO)(C(CCCCC)CC)C BAGLAURKIQVJJQ-UHFFFAOYSA-N 0.000 description 1
- ZIIGIOHQSPOFKT-UHFFFAOYSA-N 4,4-dimethyl-2-prop-1-en-2-yl-5,6-dihydro-1,3-oxazine Chemical group C(=C)(C)C=1OCCC(N1)(C)C ZIIGIOHQSPOFKT-UHFFFAOYSA-N 0.000 description 1
- BZBJRZFMZVXWDX-UHFFFAOYSA-N 4,4-dimethyl-2-prop-1-enyl-5h-1,3-oxazole Chemical compound CC=CC1=NC(C)(C)CO1 BZBJRZFMZVXWDX-UHFFFAOYSA-N 0.000 description 1
- SKSNKHKNPOOVDA-UHFFFAOYSA-N 4,4-dimethyl-5,6-dihydro-1,3-oxazine Chemical compound CC1(N=COCC1)C SKSNKHKNPOOVDA-UHFFFAOYSA-N 0.000 description 1
- IQOZTIKBIHWYQQ-UHFFFAOYSA-N 4h-1,3-oxazine Chemical class C1C=COC=N1 IQOZTIKBIHWYQQ-UHFFFAOYSA-N 0.000 description 1
- UFTHEDBYLPFRDP-UHFFFAOYSA-N 5,6-dihydro-2h-oxazine Chemical class C1CC=CNO1 UFTHEDBYLPFRDP-UHFFFAOYSA-N 0.000 description 1
- HDLIVQSXVDEDLW-UHFFFAOYSA-N CO.C(C=C)(=O)OCC Chemical compound CO.C(C=C)(=O)OCC HDLIVQSXVDEDLW-UHFFFAOYSA-N 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical class [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 description 1
- 241001667714 Macrosporium Species 0.000 description 1
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical group COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 1
- 241001518731 Monilinia fructicola Species 0.000 description 1
- PDSRSCNGYWQMMT-UHFFFAOYSA-N NC(CO)(C(C(CC)CC)CC)C Chemical compound NC(CO)(C(C(CC)CC)CC)C PDSRSCNGYWQMMT-UHFFFAOYSA-N 0.000 description 1
- SWLFVNVRQRAEIS-UHFFFAOYSA-N NC(CO)(C(C(CCCC)C)C)C Chemical compound NC(CO)(C(C(CCCC)C)C)C SWLFVNVRQRAEIS-UHFFFAOYSA-N 0.000 description 1
- 231100000674 Phytotoxicity Toxicity 0.000 description 1
- 244000061458 Solanum melongena Species 0.000 description 1
- 235000002597 Solanum melongena Nutrition 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- JPUHCPXFQIXLMW-UHFFFAOYSA-N aluminium triethoxide Chemical compound CCO[Al](OCC)OCC JPUHCPXFQIXLMW-UHFFFAOYSA-N 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 229940116318 copper carbonate Drugs 0.000 description 1
- GEZOTWYUIKXWOA-UHFFFAOYSA-L copper;carbonate Chemical compound [Cu+2].[O-]C([O-])=O GEZOTWYUIKXWOA-UHFFFAOYSA-L 0.000 description 1
- VAROLYSFQDGFMV-UHFFFAOYSA-K di(octanoyloxy)alumanyl octanoate Chemical compound [Al+3].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O.CCCCCCCC([O-])=O VAROLYSFQDGFMV-UHFFFAOYSA-K 0.000 description 1
- IZDIMNIIEWWUKS-UHFFFAOYSA-N ethanol;methyl prop-2-enoate Chemical compound CCO.COC(=O)C=C IZDIMNIIEWWUKS-UHFFFAOYSA-N 0.000 description 1
- 125000002573 ethenylidene group Chemical group [*]=C=C([H])[H] 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- UMIGRJFRSQMGCJ-UHFFFAOYSA-N ethyl prop-2-enoate;methyl 2-methylprop-2-enoate;methyl prop-2-enoate Chemical compound COC(=O)C=C.CCOC(=O)C=C.COC(=O)C(C)=C UMIGRJFRSQMGCJ-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000008396 flotation agent Substances 0.000 description 1
- 230000002538 fungal effect Effects 0.000 description 1
- 229910052733 gallium Inorganic materials 0.000 description 1
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000035800 maturation Effects 0.000 description 1
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 description 1
- 229960000907 methylthioninium chloride Drugs 0.000 description 1
- 238000013021 overheating Methods 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000009877 rendering Methods 0.000 description 1
- 239000005871 repellent Substances 0.000 description 1
- 230000002940 repellent Effects 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 125000003003 spiro group Chemical group 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- MYWQGROTKMBNKN-UHFFFAOYSA-N tributoxyalumane Chemical compound [Al+3].CCCC[O-].CCCC[O-].CCCC[O-] MYWQGROTKMBNKN-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/08—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D263/10—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D263/12—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with radicals containing only hydrogen and carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D265/04—1,3-Oxazines; Hydrogenated 1,3-oxazines
- C07D265/06—1,3-Oxazines; Hydrogenated 1,3-oxazines not condensed with other rings
- C07D265/08—1,3-Oxazines; Hydrogenated 1,3-oxazines not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US58417156A | 1956-05-11 | 1956-05-11 | |
| US58417256A | 1956-05-11 | 1956-05-11 | |
| US584173A US2831858A (en) | 1956-05-11 | 1956-05-11 | Oxazine and oxazoline derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1094749B true DE1094749B (de) | 1960-12-15 |
Family
ID=27416427
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT1067437D Pending DE1067437B (de) | 1956-05-11 | Verfahren zur Herstellung von 4,4-dialkyl-2vinyl- und 4,4-dialkyl-2-isopropenylsu'bstituierten Oxazolinen und 5,6-Dihydro-4H!-1,3-oχ3zinen sowie deren Spiranen | |
| DER21143A Pending DE1094749B (de) | 1956-05-11 | 1957-05-11 | Verfahren zur Herstellung von 4, 4-dialkyl-2-vinyl- und 4, 4-dialkyl-2-isopropenylsubstituierten Oxazolinen und 5, 6-Dihydro-4H-1, 3-oxazinen sowie deren Spiranen |
| DER21141A Pending DE1088494B (de) | 1956-05-11 | 1957-05-11 | Verfahren zur Herstellung von 4,4-dialkyl-2-vinyl- und 4,4-dialkyl-2-isopropenyl-substituierten Oxazolinen und 5,6-Dihydro-4H-1,3-oxazinen sowie deren Spiranen |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT1067437D Pending DE1067437B (de) | 1956-05-11 | Verfahren zur Herstellung von 4,4-dialkyl-2vinyl- und 4,4-dialkyl-2-isopropenylsu'bstituierten Oxazolinen und 5,6-Dihydro-4H!-1,3-oχ3zinen sowie deren Spiranen |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DER21141A Pending DE1088494B (de) | 1956-05-11 | 1957-05-11 | Verfahren zur Herstellung von 4,4-dialkyl-2-vinyl- und 4,4-dialkyl-2-isopropenyl-substituierten Oxazolinen und 5,6-Dihydro-4H-1,3-oxazinen sowie deren Spiranen |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US2831858A (Direct) |
| BE (1) | BE557414A (Direct) |
| CH (1) | CH383971A (Direct) |
| DE (3) | DE1094749B (Direct) |
| FR (1) | FR1180666A (Direct) |
| GB (1) | GB834308A (Direct) |
| NL (2) | NL105271C (Direct) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2207576A1 (de) * | 1972-02-18 | 1973-08-23 | Basf Ag | Oxazolidinderivate |
| EP0315856A1 (de) * | 1987-11-10 | 1989-05-17 | Henkel Kommanditgesellschaft auf Aktien | Verfahren zur Herstellung von 2-Alkyl- bzw. 2-Alkenyl- oxazolinen |
| EP0394854A1 (de) * | 1989-04-28 | 1990-10-31 | Henkel Kommanditgesellschaft auf Aktien | Verfahren zur Herstellung von 2-Alkyl- bzw. Alkenyl-2-oxazolinen aus Fettsäureglyceriden |
| EP0394849A1 (de) * | 1989-04-28 | 1990-10-31 | Henkel Kommanditgesellschaft auf Aktien | Verfahren zur Herstellung von 2-Oxazolinen |
Families Citing this family (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2897182A (en) * | 1957-09-06 | 1959-07-28 | Rohm & Haas | Oxazine and oxazoline polymers |
| US2993031A (en) * | 1958-05-22 | 1961-07-18 | Dow Chemical Co | Nu-isopropenyl-cyclic carbamate compounds and polymers thereof |
| US2992219A (en) * | 1958-09-19 | 1961-07-11 | Eastman Kodak Co | Phosphorothiolothionates derived from 5, 6-dihydro-4h-1, 3-oxazines and 5, 6-dihydro-4h-1, 3-thiazines |
| US2974140A (en) * | 1959-03-04 | 1961-03-07 | Miles Lab | Substituted 2-alkenyltetrahydro-1, 3-oxazines |
| BE614214A (Direct) * | 1961-02-22 | |||
| DE1261261B (de) | 1966-09-23 | 1968-02-15 | Huels Chemische Werke Ag | Waermehaertbare UEberzugsmittel |
| DE1644760A1 (de) * | 1966-12-24 | 1971-03-04 | Huels Chemische Werke Ag | Verfahren zum Herstellen von UEberzuegen |
| US3687888A (en) * | 1969-10-30 | 1972-08-29 | Commercial Solvents Corp | Terpolymer latex emulsions |
| US3678065A (en) * | 1970-12-09 | 1972-07-18 | Commercial Solvents Corp | Production of hydroxymethyl vinyl oxazoline |
| US3708334A (en) * | 1971-03-22 | 1973-01-02 | Commercial Solvents Corp | Method of marking the skin or fur of animals |
| DE2329545C2 (de) * | 1973-06-09 | 1986-06-12 | Bayer Ag, 5090 Leverkusen | 1,2-Bis-oxazolinyl-(2)-cyclobutane und Verfahren zu ihrer Herstellung |
| US3886128A (en) * | 1973-10-15 | 1975-05-27 | Commercial Solvents Corp | Oxazoline emulsifier in polymerization of styrene and butadiene |
| US4153566A (en) * | 1974-03-27 | 1979-05-08 | Exxon Research & Engineering Co. | Oxazoline additives useful in oleaginous compositions |
| CA1048507A (en) * | 1974-03-27 | 1979-02-13 | Jack Ryer | Additive useful in oleaginous compositions |
| US4157243A (en) * | 1974-12-06 | 1979-06-05 | Exxon Research & Engineering Co. | Additive useful in oleaginous compositions |
| US4178375A (en) * | 1976-08-06 | 1979-12-11 | Sterling Drug Inc. | Preserving and disinfecting method employing certain oxazines |
| DE2704904A1 (de) * | 1977-02-05 | 1978-08-10 | Henkel Kgaa | Kosmetische mittel mit einem gehalt an haut-feuchthaltemitteln |
| US4256592A (en) * | 1979-10-11 | 1981-03-17 | Mobil Oil Corporation | Phosphorus-containing compounds and lubricants containing same |
| US4255271A (en) * | 1979-11-20 | 1981-03-10 | Mobil Oil Corporation | Phosphorus-containing compounds and lubricants containing same |
| US4253973A (en) * | 1979-11-20 | 1981-03-03 | Mobil Oil Corporation | Phosphorus-containing compounds and lubricants containing same |
| US4357464A (en) * | 1981-04-15 | 1982-11-02 | The Dow Chemical Company | Removal of 2-isopropenyl-2-oxazoline monomer |
| US4508869A (en) * | 1983-06-14 | 1985-04-02 | The Dow Chemical Company | Latexes of polymers having pendant coreactive and oxazoline groups |
| WO1989008099A1 (en) * | 1988-02-25 | 1989-09-08 | The Dow Chemical Company | Process for preparing n-(hydroxyalkyl)-2-unsaturated amides and 2-alkenyl oxazolines |
| US6063885A (en) * | 1998-03-10 | 2000-05-16 | S. C. Johnson Commercial Markets, Inc. | Oxazoline or oxazine methacrylate aqueous coating compositions |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US913514A (en) * | 1908-11-30 | 1909-02-23 | Farbenfab Vorm Bayer F & Co | Red dye. |
| US2243295A (en) * | 1939-11-15 | 1941-05-27 | Purdue Research Foundation | Process for the production of n-substituted (arylalkyl) amines |
| US2623013A (en) * | 1949-09-24 | 1952-12-23 | Koppers Co Inc | Ion-exchange resins from a vinyl pyridine or a vinyl quinoline and a vinyl ethinyl hydrocarbon |
| US2634259A (en) * | 1951-07-31 | 1953-04-07 | Arnold Hoffman & Co Inc | Polymerization process for n-vinyl pyrrolidone |
| US2665271A (en) * | 1951-10-25 | 1954-01-05 | Gen Aniline & Film Corp | Polymerization of n-vinyl lactams |
| US2739948A (en) * | 1951-11-21 | 1956-03-27 | Koppers Co Inc | Ion-exchange resins from divinyl pyridine |
-
0
- DE DENDAT1067437D patent/DE1067437B/de active Pending
-
1956
- 1956-05-11 US US584173A patent/US2831858A/en not_active Expired - Lifetime
-
1957
- 1957-05-07 GB GB14475/57A patent/GB834308A/en not_active Expired
- 1957-05-10 NL NL217156A patent/NL105271C/xx active
- 1957-05-10 FR FR1180666D patent/FR1180666A/fr not_active Expired
- 1957-05-11 DE DER21143A patent/DE1094749B/de active Pending
- 1957-05-11 DE DER21141A patent/DE1088494B/de active Pending
- 1957-05-11 BE BE557414D patent/BE557414A/xx unknown
- 1957-05-11 CH CH4596657A patent/CH383971A/fr unknown
-
1959
- 1959-11-06 NL NL245078A patent/NL105450C/xx active
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2207576A1 (de) * | 1972-02-18 | 1973-08-23 | Basf Ag | Oxazolidinderivate |
| EP0315856A1 (de) * | 1987-11-10 | 1989-05-17 | Henkel Kommanditgesellschaft auf Aktien | Verfahren zur Herstellung von 2-Alkyl- bzw. 2-Alkenyl- oxazolinen |
| EP0394854A1 (de) * | 1989-04-28 | 1990-10-31 | Henkel Kommanditgesellschaft auf Aktien | Verfahren zur Herstellung von 2-Alkyl- bzw. Alkenyl-2-oxazolinen aus Fettsäureglyceriden |
| EP0394849A1 (de) * | 1989-04-28 | 1990-10-31 | Henkel Kommanditgesellschaft auf Aktien | Verfahren zur Herstellung von 2-Oxazolinen |
| WO1990013546A1 (de) * | 1989-04-28 | 1990-11-15 | Henkel Kommanditgesellschaft Auf Aktien | Verfahren zur herstellung von 2-oxazolinen |
| WO1990013545A1 (de) * | 1989-04-28 | 1990-11-15 | Henkel Kommanditgesellschaft Auf Aktien | Verfahren zur herstellung von 2-alkyl- bzw. alkenyl-2-oxazolinen aus fettsäureglyceriden |
Also Published As
| Publication number | Publication date |
|---|---|
| GB834308A (en) | 1960-05-04 |
| DE1088494B (de) | 1960-09-08 |
| DE1067437B (de) | 1959-10-22 |
| NL105450C (Direct) | 1963-07-15 |
| US2831858A (en) | 1958-04-22 |
| FR1180666A (fr) | 1959-06-08 |
| CH383971A (fr) | 1964-11-15 |
| BE557414A (Direct) | 1957-11-12 |
| NL105271C (Direct) | 1963-07-15 |
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