DE2451634A1 - Trichloraethyliden-bis(isocyaniddichlorid) - Google Patents
Trichloraethyliden-bis(isocyaniddichlorid)Info
- Publication number
- DE2451634A1 DE2451634A1 DE19742451634 DE2451634A DE2451634A1 DE 2451634 A1 DE2451634 A1 DE 2451634A1 DE 19742451634 DE19742451634 DE 19742451634 DE 2451634 A DE2451634 A DE 2451634A DE 2451634 A1 DE2451634 A1 DE 2451634A1
- Authority
- DE
- Germany
- Prior art keywords
- bis
- trichloroethylidene
- chlorine
- formamide
- excess
- 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
- RLAROPIDCNCRNR-UHFFFAOYSA-N Cl.Cl.[C-]#N Chemical compound Cl.Cl.[C-]#N RLAROPIDCNCRNR-UHFFFAOYSA-N 0.000 title claims description 15
- 239000000460 chlorine Substances 0.000 claims description 17
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 16
- 229910052801 chlorine Inorganic materials 0.000 claims description 16
- GHFMCHQWRFPHLL-UHFFFAOYSA-N n-(2,2,2-trichloro-1-formamidoethyl)formamide Chemical compound O=CNC(C(Cl)(Cl)Cl)NC=O GHFMCHQWRFPHLL-UHFFFAOYSA-N 0.000 claims description 16
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 14
- 239000011541 reaction mixture Substances 0.000 claims description 14
- -1 Trichloroethylidene Chemical group 0.000 claims description 13
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical group ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 claims description 12
- 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 claims description 11
- 239000003701 inert diluent Substances 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 5
- 150000001805 chlorine compounds Chemical class 0.000 claims description 5
- 239000000203 mixture Substances 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 claims description 4
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 claims description 4
- 229950011008 tetrachloroethylene Drugs 0.000 claims description 4
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims description 3
- 238000010992 reflux Methods 0.000 description 14
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 12
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 10
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 9
- 239000003085 diluting agent Substances 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 8
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 241000196324 Embryophyta Species 0.000 description 5
- 239000004480 active ingredient Substances 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- 238000004821 distillation Methods 0.000 description 5
- 229920006395 saturated elastomer Polymers 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 206010061217 Infestation Diseases 0.000 description 4
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 4
- 238000004587 chromatography analysis Methods 0.000 description 4
- 230000007717 exclusion Effects 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- PBKONEOXTCPAFI-UHFFFAOYSA-N 1,2,4-trichlorobenzene Chemical compound ClC1=CC=C(Cl)C(Cl)=C1 PBKONEOXTCPAFI-UHFFFAOYSA-N 0.000 description 3
- 241000227653 Lycopersicon Species 0.000 description 3
- 238000009835 boiling Methods 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
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 2
- 241000255925 Diptera Species 0.000 description 2
- 241000255581 Drosophila <fruit fly, genus> Species 0.000 description 2
- 125000002877 alkyl aryl group Chemical group 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 239000007859 condensation product Substances 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
- RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 description 2
- 229920000151 polyglycol Polymers 0.000 description 2
- 239000010695 polyglycol Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 2
- 238000005292 vacuum distillation Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 238000010626 work up procedure Methods 0.000 description 2
- PANVCEBTPSTUEL-UHFFFAOYSA-N 1,1,2,3,3-pentachloropropane Chemical compound ClC(Cl)C(Cl)C(Cl)Cl PANVCEBTPSTUEL-UHFFFAOYSA-N 0.000 description 1
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 description 1
- 241000233614 Phytophthora Species 0.000 description 1
- 241000233622 Phytophthora infestans Species 0.000 description 1
- 241000255588 Tephritidae Species 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 230000000855 fungicidal effect Effects 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 230000000749 insecticidal effect Effects 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- HFFLGKNGCAIQMO-UHFFFAOYSA-N trichloroacetaldehyde Chemical compound ClC(Cl)(Cl)C=O HFFLGKNGCAIQMO-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
- C07C51/60—Preparation of carboxylic acid halides by conversion of carboxylic acids or their anhydrides or esters, lactones, salts into halides with the same carboxylic acid part
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)
- Agricultural Chemicals And Associated Chemicals (AREA)
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19742451634 DE2451634A1 (de) | 1974-10-30 | 1974-10-30 | Trichloraethyliden-bis(isocyaniddichlorid) |
| GB4144075A GB1475048A (en) | 1974-10-30 | 1975-10-09 | N,n-2,2,2-trichloroethylidene-bis-carbonimidoyl-dichloride |
| US05/626,409 US3966812A (en) | 1974-10-30 | 1975-10-28 | Trichloroethylidene-bis-(isocyanide-dichloride) and process for making same |
| JP50128980A JPS5168525A (en) | 1974-10-30 | 1975-10-28 | Torikuroruechiriden bisu * isoshianido jikurorido * noseizoho |
| NL7512670A NL7512670A (nl) | 1974-10-30 | 1975-10-29 | Werkwijze voor het bereiden van trichloorethyli- deenbis-(isocyanidedichloride). |
| BE161346A BE834981A (fr) | 1974-10-30 | 1975-10-29 | Trichlorethylidene-bis(dichlorure de carbylamine) |
| FR7533254A FR2289491A1 (fr) | 1974-10-30 | 1975-10-30 | Trichlorethylidene-bis-(dichlorure de carbylamine) |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19742451634 DE2451634A1 (de) | 1974-10-30 | 1974-10-30 | Trichloraethyliden-bis(isocyaniddichlorid) |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2451634A1 true DE2451634A1 (de) | 1976-05-06 |
Family
ID=5929627
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19742451634 Pending DE2451634A1 (de) | 1974-10-30 | 1974-10-30 | Trichloraethyliden-bis(isocyaniddichlorid) |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US3966812A (enExample) |
| JP (1) | JPS5168525A (enExample) |
| BE (1) | BE834981A (enExample) |
| DE (1) | DE2451634A1 (enExample) |
| FR (1) | FR2289491A1 (enExample) |
| GB (1) | GB1475048A (enExample) |
| NL (1) | NL7512670A (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4240977A (en) * | 1977-11-29 | 1980-12-23 | Bayer Aktiengesellschaft | 2-Cyanoethyl isocyanide dichloride |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3267144A (en) * | 1963-10-28 | 1966-08-16 | Olin Mathieson | Process for preparing selected bis |
| DE1618401C3 (de) * | 1967-04-07 | 1974-08-08 | Bayer Ag, 5090 Leverkusen | Verfahren zur Herstellung von 2-Chlor-alkyl-isocyaniddichloriden neben Dichloralkanen |
| US3795706A (en) * | 1971-07-09 | 1974-03-05 | Allied Chem | Fluoroperhalodiazaolefins and their method of preparation |
-
1974
- 1974-10-30 DE DE19742451634 patent/DE2451634A1/de active Pending
-
1975
- 1975-10-09 GB GB4144075A patent/GB1475048A/en not_active Expired
- 1975-10-28 US US05/626,409 patent/US3966812A/en not_active Expired - Lifetime
- 1975-10-28 JP JP50128980A patent/JPS5168525A/ja active Pending
- 1975-10-29 BE BE161346A patent/BE834981A/xx unknown
- 1975-10-29 NL NL7512670A patent/NL7512670A/xx not_active Application Discontinuation
- 1975-10-30 FR FR7533254A patent/FR2289491A1/fr active Granted
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4240977A (en) * | 1977-11-29 | 1980-12-23 | Bayer Aktiengesellschaft | 2-Cyanoethyl isocyanide dichloride |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2289491B1 (enExample) | 1979-01-05 |
| BE834981A (fr) | 1976-04-29 |
| US3966812A (en) | 1976-06-29 |
| FR2289491A1 (fr) | 1976-05-28 |
| GB1475048A (en) | 1977-06-01 |
| JPS5168525A (en) | 1976-06-14 |
| NL7512670A (nl) | 1976-05-04 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OHN | Withdrawal |