CH399430A - Verfahren zur Herstellung von Polychlorpropionsäurechloriden - Google Patents

Verfahren zur Herstellung von Polychlorpropionsäurechloriden

Info

Publication number: CH399430A
Authority: CH; Switzerland
Prior art keywords: acid; parts; carbon atoms; chlorination; mixture
Prior art date: 1959-10-20

Application number

CH1169260A

Other languages

German (de)

English (en)

Inventor

Adolf Dr Hrubesch

Herbert Dr Friederich

Original Assignee

Basf Ag

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.)

1959-10-20

Filing date

1960-10-19

Publication date

1965-09-30

1960-10-19 Application filed by Basf Ag filed Critical Basf Ag

1965-09-30 Publication of CH399430A publication Critical patent/CH399430A/de

Links

239000002253 acid Substances 0.000 title claims description 29
150000001805 chlorine compounds Chemical class 0.000 title claims description 20
238000000034 method Methods 0.000 title claims description 12
238000002360 preparation method Methods 0.000 title description 4
238000005660 chlorination reaction Methods 0.000 claims description 56
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 53
239000000460 chlorine Substances 0.000 claims description 53
229910052801 chlorine Inorganic materials 0.000 claims description 53
239000003054 catalyst Substances 0.000 claims description 25
FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 claims description 25
229910052757 nitrogen Inorganic materials 0.000 claims description 22
125000004432 carbon atom Chemical group C* 0.000 claims description 20
238000006243 chemical reaction Methods 0.000 claims description 20
125000000217 alkyl group Chemical group 0.000 claims description 10
150000008064 anhydrides Chemical class 0.000 claims description 10
KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 9
150000004985 diamines Chemical class 0.000 claims description 9
235000014113 dietary fatty acids Nutrition 0.000 claims description 6
229930195729 fatty acid Natural products 0.000 claims description 6
239000000194 fatty acid Substances 0.000 claims description 6
150000003856 quaternary ammonium compounds Chemical class 0.000 claims description 6
125000001931 aliphatic group Chemical group 0.000 claims description 5
HNYOPLTXPVRDBG-UHFFFAOYSA-N barbituric acid Chemical compound O=C1CC(=O)NC(=O)N1 HNYOPLTXPVRDBG-UHFFFAOYSA-N 0.000 claims description 5
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 5
150000007513 acids Chemical class 0.000 claims description 4
150000007933 aliphatic carboxylic acids Chemical class 0.000 claims description 4
150000003857 carboxamides Chemical class 0.000 claims description 4
150000004665 fatty acids Chemical class 0.000 claims description 4
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 3
150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 3
238000004519 manufacturing process Methods 0.000 claims description 3
150000003512 tertiary amines Chemical class 0.000 claims description 3
125000005270 trialkylamine group Chemical group 0.000 claims description 3
AVWRKZWQTYIKIY-UHFFFAOYSA-N ureidocarboxylic acid Natural products NC(=O)NC(O)=O AVWRKZWQTYIKIY-UHFFFAOYSA-N 0.000 claims description 3
239000000203 mixture Substances 0.000 description 59
BCCCFAMZWBDOKK-UHFFFAOYSA-N 2,2,3,3,3-pentachloropropanoyl chloride Chemical class ClC(=O)C(Cl)(Cl)C(Cl)(Cl)Cl BCCCFAMZWBDOKK-UHFFFAOYSA-N 0.000 description 19
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 19
238000004821 distillation Methods 0.000 description 17
RWFNATDTLRLEAG-UHFFFAOYSA-N 2,2,3,3-tetrachloropropanoyl chloride Chemical group ClC(Cl)C(Cl)(Cl)C(Cl)=O RWFNATDTLRLEAG-UHFFFAOYSA-N 0.000 description 16
239000007789 gas Substances 0.000 description 15
239000000047 product Substances 0.000 description 15
238000009835 boiling Methods 0.000 description 14
QFMWUUALQWGFAG-UHFFFAOYSA-N 3,3,3-trichloropropanoyl chloride Chemical compound ClC(=O)CC(Cl)(Cl)Cl QFMWUUALQWGFAG-UHFFFAOYSA-N 0.000 description 11
238000001816 cooling Methods 0.000 description 11
239000000706 filtrate Substances 0.000 description 10
239000007788 liquid Substances 0.000 description 10
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 7
150000001408 amides Chemical class 0.000 description 7
-1 fatty acid chlorides Chemical class 0.000 description 7
239000000155 melt Substances 0.000 description 7
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
150000001412 amines Chemical class 0.000 description 6
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 6
229910000041 hydrogen chloride Inorganic materials 0.000 description 6
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
238000010992 reflux Methods 0.000 description 6
239000007787 solid Substances 0.000 description 6
125000003118 aryl group Chemical group 0.000 description 5
150000001875 compounds Chemical class 0.000 description 5
238000003756 stirring Methods 0.000 description 5
AGULWIQIYWWFBJ-UHFFFAOYSA-N 3,4-dichlorofuran-2,5-dione Chemical compound ClC1=C(Cl)C(=O)OC1=O AGULWIQIYWWFBJ-UHFFFAOYSA-N 0.000 description 4
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 4
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
150000007656 barbituric acids Chemical class 0.000 description 4
201000006747 infectious mononucleosis Diseases 0.000 description 4
238000002844 melting Methods 0.000 description 4
230000008018 melting Effects 0.000 description 4
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
150000002763 monocarboxylic acids Chemical class 0.000 description 4
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
239000002904 solvent Substances 0.000 description 4
239000000126 substance Substances 0.000 description 4
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
SDYWXFYBZPNOFX-UHFFFAOYSA-N 3,4-dichloroaniline Chemical compound NC1=CC=C(Cl)C(Cl)=C1 SDYWXFYBZPNOFX-UHFFFAOYSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
238000010521 absorption reaction Methods 0.000 description 3
DYRDKSSFIWVSNM-UHFFFAOYSA-N acetoacetanilide Chemical compound CC(=O)CC(=O)NC1=CC=CC=C1 DYRDKSSFIWVSNM-UHFFFAOYSA-N 0.000 description 3
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
239000012267 brine Substances 0.000 description 3
239000012043 crude product Substances 0.000 description 3
239000013078 crystal Substances 0.000 description 3
238000002425 crystallisation Methods 0.000 description 3
230000008025 crystallization Effects 0.000 description 3
230000002363 herbicidal effect Effects 0.000 description 3
RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical class CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 3
239000008262 pumice Substances 0.000 description 3
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 3
239000004575 stone 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
LUBJCRLGQSPQNN-UHFFFAOYSA-N 1-Phenylurea Chemical compound NC(=O)NC1=CC=CC=C1 LUBJCRLGQSPQNN-UHFFFAOYSA-N 0.000 description 2
BCOSEZGCLGPUSL-UHFFFAOYSA-N 2,3,3-trichloroprop-2-enoyl chloride Chemical compound ClC(Cl)=C(Cl)C(Cl)=O BCOSEZGCLGPUSL-UHFFFAOYSA-N 0.000 description 2
CXJAFLQWMOMYOW-UHFFFAOYSA-N 3-chlorofuran-2,5-dione Chemical compound ClC1=CC(=O)OC1=O CXJAFLQWMOMYOW-UHFFFAOYSA-N 0.000 description 2
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
JOOXCMJARBKPKM-UHFFFAOYSA-N 4-oxopentanoic acid Chemical compound CC(=O)CCC(O)=O JOOXCMJARBKPKM-UHFFFAOYSA-N 0.000 description 2
DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
WDJHALXBUFZDSR-UHFFFAOYSA-N Acetoacetic acid Natural products CC(=O)CC(O)=O WDJHALXBUFZDSR-UHFFFAOYSA-N 0.000 description 2
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
241000255925 Diptera Species 0.000 description 2
ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
ATHHXGZTWNVVOU-UHFFFAOYSA-N N-methylformamide Chemical compound CNC=O ATHHXGZTWNVVOU-UHFFFAOYSA-N 0.000 description 2
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
235000021355 Stearic acid Nutrition 0.000 description 2
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
241000607479 Yersinia pestis Species 0.000 description 2
WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 2
239000012346 acetyl chloride Substances 0.000 description 2
150000008065 acid anhydrides Chemical class 0.000 description 2
DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 description 2
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
125000003277 amino group Chemical group 0.000 description 2
229910021529 ammonia Inorganic materials 0.000 description 2
WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
239000006227 byproduct Substances 0.000 description 2
PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
WOWBFOBYOAGEEA-UHFFFAOYSA-N diafenthiuron Chemical compound CC(C)C1=C(NC(=S)NC(C)(C)C)C(C(C)C)=CC(OC=2C=CC=CC=2)=C1 WOWBFOBYOAGEEA-UHFFFAOYSA-N 0.000 description 2
150000001470 diamides Chemical class 0.000 description 2
JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
238000009826 distribution Methods 0.000 description 2
POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
235000019253 formic acid Nutrition 0.000 description 2
238000007710 freezing Methods 0.000 description 2
230000008014 freezing Effects 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 2
FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
239000012442 inert solvent Substances 0.000 description 2
230000000749 insecticidal effect Effects 0.000 description 2
239000007791 liquid phase Substances 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
KAONDSIEAGDWKS-UHFFFAOYSA-N n,n-dipropylbutanamide Chemical compound CCCN(CCC)C(=O)CCC KAONDSIEAGDWKS-UHFFFAOYSA-N 0.000 description 2
AAJQYMJRUXQQCP-UHFFFAOYSA-N n-benzyldodecanamide Chemical compound CCCCCCCCCCCC(=O)NCC1=CC=CC=C1 AAJQYMJRUXQQCP-UHFFFAOYSA-N 0.000 description 2
IXODJGLAVBPVSW-UHFFFAOYSA-N n-benzyloctadecanamide Chemical compound CCCCCCCCCCCCCCCCCC(=O)NCC1=CC=CC=C1 IXODJGLAVBPVSW-UHFFFAOYSA-N 0.000 description 2
125000004433 nitrogen atom Chemical group N* 0.000 description 2
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 2
WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 2
WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 2
229910052698 phosphorus Inorganic materials 0.000 description 2
239000011574 phosphorus Substances 0.000 description 2
KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
239000007858 starting material Substances 0.000 description 2
239000008117 stearic acid Substances 0.000 description 2
238000005292 vacuum distillation Methods 0.000 description 2
238000010626 work up procedure Methods 0.000 description 2
OBETXYAYXDNJHR-SSDOTTSWSA-M (2r)-2-ethylhexanoate Chemical compound CCCC[C@@H](CC)C([O-])=O OBETXYAYXDNJHR-SSDOTTSWSA-M 0.000 description 1
GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 1
HMUNWXXNJPVALC-UHFFFAOYSA-N 1-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical group C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)C(CN1CC2=C(CC1)NN=N2)=O HMUNWXXNJPVALC-UHFFFAOYSA-N 0.000 description 1
KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical class C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 1
WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 1
IPKCHUGFUGHNRZ-UHFFFAOYSA-N 2,2-dichloropropanoyl chloride Chemical compound CC(Cl)(Cl)C(Cl)=O IPKCHUGFUGHNRZ-UHFFFAOYSA-N 0.000 description 1
MZFVOEKQRZQKFO-UHFFFAOYSA-N 2,3,3,3-tetrachloropropanoyl chloride Chemical compound ClC(=O)C(Cl)C(Cl)(Cl)Cl MZFVOEKQRZQKFO-UHFFFAOYSA-N 0.000 description 1
ISPYQTSUDJAMAB-UHFFFAOYSA-N 2-chlorophenol Chemical class OC1=CC=CC=C1Cl ISPYQTSUDJAMAB-UHFFFAOYSA-N 0.000 description 1
YTPZZUAPUOFFID-UHFFFAOYSA-N 2-ethyl-n,n-dipropylhexanamide Chemical compound CCCCC(CC)C(=O)N(CCC)CCC YTPZZUAPUOFFID-UHFFFAOYSA-N 0.000 description 1
WLJVXDMOQOGPHL-PPJXEINESA-N 2-phenylacetic acid Chemical compound O[14C](=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-PPJXEINESA-N 0.000 description 1
OBKXEAXTFZPCHS-UHFFFAOYSA-N 4-phenylbutyric acid Chemical compound OC(=O)CCCC1=CC=CC=C1 OBKXEAXTFZPCHS-UHFFFAOYSA-N 0.000 description 1
KXOZJFGEGGNJDX-UHFFFAOYSA-N 5,5-dibutyl-1,3-diazinane-2,4,6-trione Chemical compound CCCCC1(CCCC)C(=O)NC(=O)NC1=O KXOZJFGEGGNJDX-UHFFFAOYSA-N 0.000 description 1
FTOAOBMCPZCFFF-UHFFFAOYSA-N 5,5-diethylbarbituric acid Chemical compound CCC1(CC)C(=O)NC(=O)NC1=O FTOAOBMCPZCFFF-UHFFFAOYSA-N 0.000 description 1
LAOZSCRCYVBSJA-UHFFFAOYSA-N 5,5-dimethyl-1,3-diazinane-2,4,6-trione Chemical compound CC1(C)C(=O)NC(=O)NC1=O LAOZSCRCYVBSJA-UHFFFAOYSA-N 0.000 description 1
XICPRTQGMNZJLE-UHFFFAOYSA-N 5-(2-phenylethyl)-1,3-diazinane-2,4,6-trione Chemical compound O=C1NC(=O)NC(=O)C1CCC1=CC=CC=C1 XICPRTQGMNZJLE-UHFFFAOYSA-N 0.000 description 1
241000254032 Acrididae Species 0.000 description 1
FDQGNLOWMMVRQL-UHFFFAOYSA-N Allobarbital Chemical compound C=CCC1(CC=C)C(=O)NC(=O)NC1=O FDQGNLOWMMVRQL-UHFFFAOYSA-N 0.000 description 1
239000005711 Benzoic acid Substances 0.000 description 1
VSSANXMMYIXUFN-UHFFFAOYSA-N CCCCCCCCCCC(C(O)=O)N(C)C(NC)=O Chemical compound CCCCCCCCCCC(C(O)=O)N(C)C(NC)=O VSSANXMMYIXUFN-UHFFFAOYSA-N 0.000 description 1
239000005635 Caprylic acid (CAS 124-07-2) Substances 0.000 description 1
239000004215 Carbon black (E152) Substances 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
XGIAHMUOCFHQTI-UHFFFAOYSA-N Cl.Cl.Cl.Cl.CC Chemical compound Cl.Cl.Cl.Cl.CC XGIAHMUOCFHQTI-UHFFFAOYSA-N 0.000 description 1
NDUPDOJHUQKPAG-UHFFFAOYSA-N Dalapon Chemical compound CC(Cl)(Cl)C(O)=O NDUPDOJHUQKPAG-UHFFFAOYSA-N 0.000 description 1
BWLUMTFWVZZZND-UHFFFAOYSA-N Dibenzylamine Chemical compound C=1C=CC=CC=1CNCC1=CC=CC=C1 BWLUMTFWVZZZND-UHFFFAOYSA-N 0.000 description 1
XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical compound C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-N 0.000 description 1
241000255581 Drosophila <fruit fly, genus> Species 0.000 description 1
PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
239000005639 Lauric acid Substances 0.000 description 1
MGJKQDOBUOMPEZ-UHFFFAOYSA-N N,N'-dimethylurea Chemical compound CNC(=O)NC MGJKQDOBUOMPEZ-UHFFFAOYSA-N 0.000 description 1
SUAKHGWARZSWIH-UHFFFAOYSA-N N,N‐diethylformamide Chemical compound CCN(CC)C=O SUAKHGWARZSWIH-UHFFFAOYSA-N 0.000 description 1
AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methylaniline Chemical compound CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 1
235000021314 Palmitic acid Nutrition 0.000 description 1
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
241000344246 Tetranychus cinnabarinus Species 0.000 description 1
235000011054 acetic acid Nutrition 0.000 description 1
229960000880 allobarbital Drugs 0.000 description 1
OBETXYAYXDNJHR-UHFFFAOYSA-N alpha-ethylcaproic acid Natural products CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 1
229940051881 anilide analgesics and antipyretics Drugs 0.000 description 1
150000003931 anilides Chemical class 0.000 description 1
229960002319 barbital Drugs 0.000 description 1
239000002585 base Substances 0.000 description 1
AITBHTAFQQYBHP-UHFFFAOYSA-N benzene;pyridine Chemical compound C1=CC=CC=C1.C1=CC=NC=C1 AITBHTAFQQYBHP-UHFFFAOYSA-N 0.000 description 1
235000010233 benzoic acid Nutrition 0.000 description 1
PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000004202 carbamide Substances 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
239000001569 carbon dioxide Substances 0.000 description 1
229910002092 carbon dioxide Inorganic materials 0.000 description 1
KXDHJXZQYSOELW-UHFFFAOYSA-N carbonic acid monoamide Natural products NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 1
150000001735 carboxylic acids Chemical class 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
239000012230 colorless oil Substances 0.000 description 1
125000000753 cycloalkyl group Chemical group 0.000 description 1
125000003963 dichloro group Chemical group Cl* 0.000 description 1
WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical compound CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 description 1
230000008030 elimination Effects 0.000 description 1
238000003379 elimination reaction Methods 0.000 description 1
241001233957 eudicotyledons Species 0.000 description 1
238000004508 fractional distillation Methods 0.000 description 1
239000004009 herbicide Substances 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
239000011261 inert gas Substances 0.000 description 1
239000013067 intermediate product Substances 0.000 description 1
FBAFATDZDUQKNH-UHFFFAOYSA-M iron chloride Chemical compound [Cl-].[Fe] FBAFATDZDUQKNH-UHFFFAOYSA-M 0.000 description 1
125000000468 ketone group Chemical group 0.000 description 1
229940040102 levulinic acid Drugs 0.000 description 1
229910001507 metal halide Inorganic materials 0.000 description 1
150000005309 metal halides Chemical class 0.000 description 1
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
238000000465 moulding Methods 0.000 description 1
QYIYWUBFHJEWPO-UHFFFAOYSA-N n,n-dibutyl-3-oxobutanamide Chemical compound CCCCN(CCCC)C(=O)CC(C)=O QYIYWUBFHJEWPO-UHFFFAOYSA-N 0.000 description 1
YIGDAUZSYXKBHT-UHFFFAOYSA-N n,n-dibutylbutanamide Chemical compound CCCCN(CCCC)C(=O)CCC YIGDAUZSYXKBHT-UHFFFAOYSA-N 0.000 description 1
IMNDHOCGZLYMRO-UHFFFAOYSA-N n,n-dimethylbenzamide Chemical compound CN(C)C(=O)C1=CC=CC=C1 IMNDHOCGZLYMRO-UHFFFAOYSA-N 0.000 description 1
LVDFMQLCDCNNKK-UHFFFAOYSA-N n-(6-formamidohexyl)formamide Chemical compound O=CNCCCCCCNC=O LVDFMQLCDCNNKK-UHFFFAOYSA-N 0.000 description 1
WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
CPKRCGUDZGKAPJ-UHFFFAOYSA-N n-benzyl-2-phenylacetamide Chemical compound C=1C=CC=CC=1CNC(=O)CC1=CC=CC=C1 CPKRCGUDZGKAPJ-UHFFFAOYSA-N 0.000 description 1
LKQUCICFTHBFAL-UHFFFAOYSA-N n-benzylbenzamide Chemical compound C=1C=CC=CC=1C(=O)NCC1=CC=CC=C1 LKQUCICFTHBFAL-UHFFFAOYSA-N 0.000 description 1
OHWQEBAVEDXXDM-UHFFFAOYSA-N n-benzylbutanamide Chemical compound CCCC(=O)NCC1=CC=CC=C1 OHWQEBAVEDXXDM-UHFFFAOYSA-N 0.000 description 1
WJWAWHQJIVUVGL-UHFFFAOYSA-N n-cyclohexyloctadecanamide Chemical compound CCCCCCCCCCCCCCCCCC(=O)NC1CCCCC1 WJWAWHQJIVUVGL-UHFFFAOYSA-N 0.000 description 1
MJCJUDJQDGGKOX-UHFFFAOYSA-N n-dodecyldodecan-1-amine Chemical compound CCCCCCCCCCCCNCCCCCCCCCCCC MJCJUDJQDGGKOX-UHFFFAOYSA-N 0.000 description 1
OLAPPGSPBNVTRF-UHFFFAOYSA-N naphthalene-1,4,5,8-tetracarboxylic acid Chemical compound C1=CC(C(O)=O)=C2C(C(=O)O)=CC=C(C(O)=O)C2=C1C(O)=O OLAPPGSPBNVTRF-UHFFFAOYSA-N 0.000 description 1
JCXJVPUVTGWSNB-UHFFFAOYSA-N nitrogen dioxide Inorganic materials O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 1
229960002446 octanoic acid Drugs 0.000 description 1
239000003921 oil Substances 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
DDBREPKUVSBGFI-UHFFFAOYSA-N phenobarbital Chemical compound C=1C=CC=CC=1C1(CC)C(=O)NC(=O)NC1=O DDBREPKUVSBGFI-UHFFFAOYSA-N 0.000 description 1
229960003424 phenylacetic acid Drugs 0.000 description 1
239000003279 phenylacetic acid Substances 0.000 description 1
229920000642 polymer Polymers 0.000 description 1
230000001737 promoting effect Effects 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
RCOUWKSZRXJXLA-UHFFFAOYSA-N propylbarbital Chemical compound CCCC1(CCC)C(=O)NC(=O)NC1=O RCOUWKSZRXJXLA-UHFFFAOYSA-N 0.000 description 1
150000003242 quaternary ammonium salts Chemical class 0.000 description 1
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 1
230000009183 running Effects 0.000 description 1
239000000243 solution Substances 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
239000011593 sulfur Substances 0.000 description 1
150000003510 tertiary aliphatic amines Chemical class 0.000 description 1
KJAMZCVTJDTESW-UHFFFAOYSA-N tiracizine Chemical compound C1CC2=CC=CC=C2N(C(=O)CN(C)C)C2=CC(NC(=O)OCC)=CC=C21 KJAMZCVTJDTESW-UHFFFAOYSA-N 0.000 description 1
IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
239000012808 vapor phase Substances 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/58—Preparation of carboxylic acid halides

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Engineering & Computer Science (AREA)
Oil, Petroleum & Natural Gas (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

CH1169260A 1959-10-20 1960-10-19 Verfahren zur Herstellung von Polychlorpropionsäurechloriden CH399430A (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DEB55236A DE1135443B (de)	1959-10-20	1959-10-20	Verfahren zur Herstellung von Gemischen aus Polychlorpropionsaeure-chloriden

Publications (1)

Publication Number	Publication Date
CH399430A true CH399430A (de)	1965-09-30

Family

ID=6970929

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH1169260A CH399430A (de)	1959-10-20	1960-10-19	Verfahren zur Herstellung von Polychlorpropionsäurechloriden

Country Status (3)

Country	Link
BE (1)	BE596182A (fr)
CH (1)	CH399430A (fr)
DE (1)	DE1135443B (fr)

1959
- 1959-10-20 DE DEB55236A patent/DE1135443B/de active Pending
1960
- 1960-10-19 CH CH1169260A patent/CH399430A/de unknown
- 1960-10-19 BE BE596182A patent/BE596182A/fr unknown

Also Published As

Publication number	Publication date
BE596182A (fr)	1961-04-19
DE1135443B (de)	1962-08-30

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DE3200069A1 (de)	1983-07-14	Verfahren zur herstellung von 2,4,6-trichloranilin
EP0027941B1 (fr)	1982-12-08	Procédé de préparation d'halogénures d'acide carboxylique
EP0676389B1 (fr)	1999-09-01	Procédé pour la préparation du chlorure de l'acide O-chlorométhyl benzoique
CH628877A5 (de)	1982-03-31	Verfahren zur herstellung von acylcyaniden.
EP0031504A1 (fr)	1981-07-08	Procédé de préparation de chlorures d'acides carboxyliques
AT218494B (de)	1961-12-11	Verfahren zur Herstellung von Polychlorpropionsäurechloriden
DE69210309T2 (de)	1996-09-12	Verfahren zur Herstellung von Alkyl-3-Chloroanthranilaten
CH399430A (de)	1965-09-30	Verfahren zur Herstellung von Polychlorpropionsäurechloriden
EP1598331B1 (fr)	2009-07-15	Procédé pour la préparation de l' anhydride phtalique
DE69010571T2 (de)	1995-03-02	Verfahren zur Herstellung von Acylcyaniden.
DE3029368C2 (fr)	1990-12-13
DE1245967B (de)	1967-08-03	Verfahren zur Herstellung von S.S-Diamino-o-chlor-pyrazincarbonsäurealkylestern
DE2057956A1 (de)	1972-06-08	Verfahren zur Herstellung von aliphatischen Carbonsaeurechloriden
WO2004022520A1 (fr)	2004-03-18	Procede de fabrication de dichlorure d'acide phtalique
DE3016119C2 (fr)	1988-07-21
EP0394644A2 (fr)	1990-10-31	Dérivés de halogenobenzènes
DE69004974T2 (de)	1994-06-09	Herstellung von 2-Chlorterephthalsäurechlorid.
EP0251041A1 (fr)	1988-01-07	Procédé de préparation d'acide 2,3,5,6-tétrafluoro-benzoique et les composés de benzochlorure 2,3,5,6-tétrachloro-4-trifluoro-méthylique et le benzofluorure 2,3,5,6-tétrafluoro-4-trifluoro-méthylique
EP0052817A1 (fr)	1982-06-02	Procédé pour la préparation de 4-chloro-2,6-dialcoyl anilines
DE2240663B2 (de)	1979-11-08	Verfahren zur Herstellung von a -Chloracrylsäure
DE102004058519A1 (de)	2006-06-14	Verfahren zum Herstellen von 3-Halophthalsäuredichloriden
DE1921662C3 (de)	1976-09-30	Verfahren zur Reinigung von Malonsäuredinitril
DE2937836A1 (de)	1981-04-09	Verfahren zur herstellung von 5-(2,2,2-trihalogenethyl)-dialkyl-tetrahydrofuran-2-onen
DE2201899A1 (de)	1972-08-31	Verfahren zur Herstellung von 2,2,6-Trichlorcyclohexanon und -Masse