CA1081248A - Trifluoromethanesulfonates - Google Patents

Trifluoromethanesulfonates

Info

Publication number: CA1081248A
Authority: CA; Canada
Prior art keywords: bis; char; bromine; ester; radical
Prior art date: 1977-06-27
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired

Application number

CA281,483A

Other languages

English (en)

Inventor

Charles E. Reineke

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Dow Chemical Co

Original Assignee

Dow Chemical Co

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.)

1977-06-27

Filing date

1977-06-27

Publication date

1980-07-08

1977-06-27 Application filed by Dow Chemical Co filed Critical Dow Chemical Co

1977-06-27 Priority to CA281,483A priority Critical patent/CA1081248A/fr

1980-07-08 Application granted granted Critical

1980-07-08 Publication of CA1081248A publication Critical patent/CA1081248A/fr

Status Expired legal-status Critical Current

Links

125000002827 triflate group Chemical class FC(S(=O)(=O)O*)(F)F 0.000 title description 2
239000000203 mixture Substances 0.000 claims abstract description 55
125000003118 aryl group Chemical group 0.000 claims abstract description 23
239000000178 monomer Substances 0.000 claims abstract description 23
150000001244 carboxylic acid anhydrides Chemical class 0.000 claims abstract description 13
-1 tribromophenoxy Chemical group 0.000 claims description 66
229920001577 copolymer Polymers 0.000 claims description 20
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 19
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 19
229910052794 bromium Inorganic materials 0.000 claims description 19
125000004432 carbon atom Chemical group C* 0.000 claims description 17
150000002148 esters Chemical class 0.000 claims description 17
150000008064 anhydrides Chemical group 0.000 claims description 13
125000004429 atom Chemical group 0.000 claims description 11
150000001875 compounds Chemical class 0.000 claims description 9
239000000460 chlorine Substances 0.000 claims description 8
229910052801 chlorine Inorganic materials 0.000 claims description 8
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 7
239000001257 hydrogen Substances 0.000 claims description 7
229910052739 hydrogen Inorganic materials 0.000 claims description 7
125000001246 bromo group Chemical group Br* 0.000 claims description 4
PBBIOTYXFUGTIA-UHFFFAOYSA-N [3-bromo-2,2-bis(bromomethyl)propyl] trifluoromethanesulfonate Chemical compound FC(F)(F)S(=O)(=O)OCC(CBr)(CBr)CBr PBBIOTYXFUGTIA-UHFFFAOYSA-N 0.000 claims description 3
125000000217 alkyl group Chemical group 0.000 claims description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
TZOPQGMMSVSNBM-UHFFFAOYSA-N [2-(bromomethyl)-3-(2,4,6-tribromophenoxy)-2-[(2,4,6-tribromophenoxy)methyl]propyl] trifluoromethanesulfonate Chemical compound BrC=1C=C(Br)C=C(Br)C=1OCC(CBr)(COS(=O)(=O)C(F)(F)F)COC1=C(Br)C=C(Br)C=C1Br TZOPQGMMSVSNBM-UHFFFAOYSA-N 0.000 claims description 2
125000004435 hydrogen atom Chemical class [H]* 0.000 claims 1
229920000642 polymer Polymers 0.000 abstract description 22
230000015572 biosynthetic process Effects 0.000 abstract description 9
ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical class OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 abstract description 5
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 33
239000000654 additive Substances 0.000 description 18
229910052799 carbon Inorganic materials 0.000 description 18
150000008648 triflates Chemical class 0.000 description 17
230000000996 additive effect Effects 0.000 description 15
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 13
238000002485 combustion reaction Methods 0.000 description 11
150000001721 carbon Chemical group 0.000 description 10
150000003254 radicals Chemical class 0.000 description 10
ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 10
WJKHJLXJJJATHN-UHFFFAOYSA-N triflic anhydride Chemical compound FC(F)(F)S(=O)(=O)OS(=O)(=O)C(F)(F)F WJKHJLXJJJATHN-UHFFFAOYSA-N 0.000 description 10
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
125000001183 hydrocarbyl group Chemical group 0.000 description 9
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 8
150000003077 polyols Chemical class 0.000 description 8
239000000243 solution Substances 0.000 description 8
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 8
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 7
239000000463 material Substances 0.000 description 7
238000000034 method Methods 0.000 description 7
229920005862 polyol Polymers 0.000 description 7
239000000047 product Substances 0.000 description 7
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
238000002360 preparation method Methods 0.000 description 6
239000000539 dimer Substances 0.000 description 5
150000002894 organic compounds Chemical class 0.000 description 5
WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 5
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
239000007787 solid Substances 0.000 description 5
239000013638 trimer Substances 0.000 description 5
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 4
239000004793 Polystyrene Substances 0.000 description 4
ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 4
230000000694 effects Effects 0.000 description 4
229910052736 halogen Inorganic materials 0.000 description 4
125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 4
238000002844 melting Methods 0.000 description 4
230000008018 melting Effects 0.000 description 4
SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 4
AHHWIHXENZJRFG-UHFFFAOYSA-N oxetane Chemical compound C1COC1 AHHWIHXENZJRFG-UHFFFAOYSA-N 0.000 description 4
238000001953 recrystallisation Methods 0.000 description 4
239000012265 solid product Substances 0.000 description 4
238000003756 stirring Methods 0.000 description 4
QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 4
QEJPOEGPNIVDMK-UHFFFAOYSA-N 3-bromo-2,2-bis(bromomethyl)propan-1-ol Chemical compound OCC(CBr)(CBr)CBr QEJPOEGPNIVDMK-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
238000005481 NMR spectroscopy Methods 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
125000005997 bromomethyl group Chemical group 0.000 description 3
239000007795 chemical reaction product Substances 0.000 description 3
239000003795 chemical substances by application Substances 0.000 description 3
229930195733 hydrocarbon Natural products 0.000 description 3
238000002156 mixing Methods 0.000 description 3
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 3
229910052760 oxygen Inorganic materials 0.000 description 3
229920002223 polystyrene Polymers 0.000 description 3
229960005335 propanol Drugs 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
241000894007 species Species 0.000 description 3
238000005292 vacuum distillation Methods 0.000 description 3
CHUGKEQJSLOLHL-UHFFFAOYSA-N 2,2-Bis(bromomethyl)propane-1,3-diol Chemical compound OCC(CO)(CBr)CBr CHUGKEQJSLOLHL-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
XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 2
235000007320 Avena fatua Nutrition 0.000 description 2
244000075850 Avena orientalis Species 0.000 description 2
KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
239000004215 Carbon black (E152) Substances 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
241000196324 Embryophyta Species 0.000 description 2
OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 2
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
240000006394 Sorghum bicolor Species 0.000 description 2
235000011684 Sorghum saccharatum Nutrition 0.000 description 2
241000256247 Spodoptera exigua Species 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
235000005373 Uvularia sessilifolia Nutrition 0.000 description 2
HNKJDSDREJCMHR-UHFFFAOYSA-N [3-bromo-2,2-bis(bromomethyl)propyl] acetate Chemical compound CC(=O)OCC(CBr)(CBr)CBr HNKJDSDREJCMHR-UHFFFAOYSA-N 0.000 description 2
238000012644 addition polymerization Methods 0.000 description 2
125000002723 alicyclic group Chemical group 0.000 description 2
125000001931 aliphatic group Chemical group 0.000 description 2
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
230000004888 barrier function Effects 0.000 description 2
238000009835 boiling Methods 0.000 description 2
238000001816 cooling Methods 0.000 description 2
125000000753 cycloalkyl group Chemical group 0.000 description 2
238000005695 dehalogenation reaction Methods 0.000 description 2
230000001419 dependent effect Effects 0.000 description 2
239000012153 distilled water Substances 0.000 description 2
238000001035 drying Methods 0.000 description 2
150000002170 ethers Chemical class 0.000 description 2
230000001747 exhibiting effect Effects 0.000 description 2
238000000605 extraction Methods 0.000 description 2
238000001125 extrusion Methods 0.000 description 2
238000001914 filtration Methods 0.000 description 2
150000002367 halogens Chemical class 0.000 description 2
229920001519 homopolymer Polymers 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
KPSSIOMAKSHJJG-UHFFFAOYSA-N neopentyl alcohol Chemical compound CC(C)(C)CO KPSSIOMAKSHJJG-UHFFFAOYSA-N 0.000 description 2
239000001301 oxygen Substances 0.000 description 2
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
229910052938 sodium sulfate Inorganic materials 0.000 description 2
235000011152 sodium sulphate Nutrition 0.000 description 2
238000001228 spectrum Methods 0.000 description 2
238000002411 thermogravimetry Methods 0.000 description 2
229920001169 thermoplastic Polymers 0.000 description 2
LRBTYZFAUUQWGA-UHFFFAOYSA-N (3-bromo-2,2-dimethylpropyl) trifluoromethanesulfonate Chemical compound BrCC(C)(C)COS(=O)(=O)C(F)(F)F LRBTYZFAUUQWGA-UHFFFAOYSA-N 0.000 description 1
RAROPDMZUWJCEE-UHFFFAOYSA-N 1,1,1,12,12,12-hexachlorododecane Chemical compound ClC(CCCCCCCCCCC(Cl)(Cl)Cl)(Cl)Cl RAROPDMZUWJCEE-UHFFFAOYSA-N 0.000 description 1
BBEAZDGZMVABIC-UHFFFAOYSA-N 1,1,1,3,3,3-hexachloropropane Chemical compound ClC(Cl)(Cl)CC(Cl)(Cl)Cl BBEAZDGZMVABIC-UHFFFAOYSA-N 0.000 description 1
QXSZNDIIPUOQMB-UHFFFAOYSA-N 1,1,2,2-tetrabromoethane Chemical compound BrC(Br)C(Br)Br QXSZNDIIPUOQMB-UHFFFAOYSA-N 0.000 description 1
QFQZKISCBJKVHI-UHFFFAOYSA-N 1,2,3,4,5,6-hexabromocyclohexane Chemical compound BrC1C(Br)C(Br)C(Br)C(Br)C1Br QFQZKISCBJKVHI-UHFFFAOYSA-N 0.000 description 1
AQPHBYQUCKHJLT-UHFFFAOYSA-N 1,2,3,4,5-pentabromo-6-(2,3,4,5,6-pentabromophenyl)benzene Chemical group BrC1=C(Br)C(Br)=C(Br)C(Br)=C1C1=C(Br)C(Br)=C(Br)C(Br)=C1Br AQPHBYQUCKHJLT-UHFFFAOYSA-N 0.000 description 1
ACRQLFSHISNWRY-UHFFFAOYSA-N 1,2,3,4,5-pentabromo-6-phenoxybenzene Chemical compound BrC1=C(Br)C(Br)=C(Br)C(Br)=C1OC1=CC=CC=C1 ACRQLFSHISNWRY-UHFFFAOYSA-N 0.000 description 1
LLVVSBBXENOOQY-UHFFFAOYSA-N 1,2,3,4,5-pentabromobenzene Chemical compound BrC1=CC(Br)=C(Br)C(Br)=C1Br LLVVSBBXENOOQY-UHFFFAOYSA-N 0.000 description 1
HGRZLIGHKHRTRE-UHFFFAOYSA-N 1,2,3,4-tetrabromobutane Chemical compound BrCC(Br)C(Br)CBr HGRZLIGHKHRTRE-UHFFFAOYSA-N 0.000 description 1
DEIGXXQKDWULML-UHFFFAOYSA-N 1,2,5,6,9,10-hexabromocyclododecane Chemical compound BrC1CCC(Br)C(Br)CCC(Br)C(Br)CCC1Br DEIGXXQKDWULML-UHFFFAOYSA-N 0.000 description 1
SHKKTLSDGJRCTR-UHFFFAOYSA-N 1,2-dibromoethylbenzene Chemical compound BrCC(Br)C1=CC=CC=C1 SHKKTLSDGJRCTR-UHFFFAOYSA-N 0.000 description 1
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BHDSTKOBYRZUJW-UHFFFAOYSA-N 2,2-bis[(2,4,6-tribromophenoxy)methyl]propane-1,3-diol Chemical compound BrC=1C=C(Br)C=C(Br)C=1OCC(CO)(CO)COC1=C(Br)C=C(Br)C=C1Br BHDSTKOBYRZUJW-UHFFFAOYSA-N 0.000 description 1
DAYGMTZDTVBMPO-UHFFFAOYSA-N 2,2-dimethylpropyl trifluoromethanesulfonate Chemical compound CC(C)(C)COS(=O)(=O)C(F)(F)F DAYGMTZDTVBMPO-UHFFFAOYSA-N 0.000 description 1
GDMBPPMGWKQBAE-UHFFFAOYSA-N 2-(bromomethyl)-2-ethylpropane-1,3-diol Chemical compound CCC(CO)(CO)CBr GDMBPPMGWKQBAE-UHFFFAOYSA-N 0.000 description 1
NZCWASFCVGLUQM-UHFFFAOYSA-N 2-(chloromethyl)-2-ethylpropane-1,3-diol Chemical compound CCC(CO)(CO)CCl NZCWASFCVGLUQM-UHFFFAOYSA-N 0.000 description 1
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125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
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125000005024 alkenyl aryl group Chemical group 0.000 description 1
125000003342 alkenyl group Chemical group 0.000 description 1
125000002877 alkyl aryl group Chemical group 0.000 description 1
125000005907 alkyl ester group Chemical group 0.000 description 1
239000002168 alkylating agent Substances 0.000 description 1
229940100198 alkylating agent Drugs 0.000 description 1
XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 1
230000000845 anti-microbial effect Effects 0.000 description 1
239000004599 antimicrobial Substances 0.000 description 1
239000002216 antistatic agent Substances 0.000 description 1
125000003710 aryl alkyl group Chemical group 0.000 description 1
150000007860 aryl ester derivatives Chemical class 0.000 description 1
239000012298 atmosphere Substances 0.000 description 1
238000000498 ball milling Methods 0.000 description 1
AOJDZKCUAATBGE-UHFFFAOYSA-N bromomethane Chemical compound Br[CH2] AOJDZKCUAATBGE-UHFFFAOYSA-N 0.000 description 1
CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-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
150000001735 carboxylic acids Chemical class 0.000 description 1
239000004359 castor oil Substances 0.000 description 1
235000019438 castor oil Nutrition 0.000 description 1
238000006243 chemical reaction Methods 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
230000000052 comparative effect Effects 0.000 description 1
238000013329 compounding Methods 0.000 description 1
238000006482 condensation reaction Methods 0.000 description 1
238000010276 construction Methods 0.000 description 1
235000005822 corn Nutrition 0.000 description 1
239000012043 crude product Substances 0.000 description 1
125000000392 cycloalkenyl group Chemical group 0.000 description 1
125000004367 cycloalkylaryl group Chemical group 0.000 description 1
150000001934 cyclohexanes Chemical class 0.000 description 1
238000006298 dechlorination reaction Methods 0.000 description 1
238000007033 dehydrochlorination reaction Methods 0.000 description 1
150000001993 dienes Chemical class 0.000 description 1
239000003814 drug Substances 0.000 description 1
238000007345 electrophilic aromatic substitution reaction Methods 0.000 description 1
238000000921 elemental analysis Methods 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
239000003063 flame retardant Substances 0.000 description 1
239000000446 fuel Substances 0.000 description 1
JLYXXMFPNIAWKQ-GNIYUCBRSA-N gamma-hexachlorocyclohexane Chemical compound Cl[C@H]1[C@H](Cl)[C@@H](Cl)[C@@H](Cl)[C@H](Cl)[C@H]1Cl JLYXXMFPNIAWKQ-GNIYUCBRSA-N 0.000 description 1
239000007792 gaseous phase Substances 0.000 description 1
ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
125000001188 haloalkyl group Chemical group 0.000 description 1
125000003106 haloaryl group Chemical group 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
239000004009 herbicide Substances 0.000 description 1
CAYGQBVSOZLICD-UHFFFAOYSA-N hexabromobenzene Chemical compound BrC1=C(Br)C(Br)=C(Br)C(Br)=C1Br CAYGQBVSOZLICD-UHFFFAOYSA-N 0.000 description 1
GTVRLHPVICIJFQ-UHFFFAOYSA-N hexane;tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl.CCCCCC GTVRLHPVICIJFQ-UHFFFAOYSA-N 0.000 description 1
150000002431 hydrogen Chemical class 0.000 description 1
229910000042 hydrogen bromide Inorganic materials 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
239000003112 inhibitor Substances 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
230000005764 inhibitory process Effects 0.000 description 1
238000001746 injection moulding Methods 0.000 description 1
230000000749 insecticidal effect Effects 0.000 description 1
239000002917 insecticide Substances 0.000 description 1
238000009413 insulation Methods 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
229960002809 lindane Drugs 0.000 description 1
239000007788 liquid Substances 0.000 description 1
238000011068 loading method Methods 0.000 description 1
YFESJHPTNWYOCO-UHFFFAOYSA-N loprodiol Chemical compound OCC(CO)(CCl)CCl YFESJHPTNWYOCO-UHFFFAOYSA-N 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
238000000691 measurement method Methods 0.000 description 1
QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
229910052753 mercury Inorganic materials 0.000 description 1
SNVLJLYUUXKWOJ-UHFFFAOYSA-N methylidenecarbene Chemical compound C=[C] SNVLJLYUUXKWOJ-UHFFFAOYSA-N 0.000 description 1
230000005012 migration Effects 0.000 description 1
238000013508 migration Methods 0.000 description 1
229940055036 mycobacterium phlei Drugs 0.000 description 1
125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
150000002825 nitriles Chemical class 0.000 description 1
150000002896 organic halogen compounds Chemical class 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
BNIXVQGCZULYKV-UHFFFAOYSA-N pentachloroethane Chemical compound ClC(Cl)C(Cl)(Cl)Cl BNIXVQGCZULYKV-UHFFFAOYSA-N 0.000 description 1
PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
230000000704 physical effect Effects 0.000 description 1
239000000049 pigment Substances 0.000 description 1
239000003505 polymerization initiator Substances 0.000 description 1
229920000098 polyolefin Polymers 0.000 description 1
229920000166 polytrimethylene carbonate Polymers 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
235000019423 pullulan Nutrition 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
230000009257 reactivity Effects 0.000 description 1
238000007151 ring opening polymerisation reaction Methods 0.000 description 1
239000002002 slurry Substances 0.000 description 1
239000000779 smoke Substances 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
125000003011 styrenyl group Chemical group [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
239000000126 substance Substances 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
229920001059 synthetic polymer Polymers 0.000 description 1
239000003784 tall oil Substances 0.000 description 1
HWCKGOZZJDHMNC-UHFFFAOYSA-M tetraethylammonium bromide Chemical group [Br-].CC[N+](CC)(CC)CC HWCKGOZZJDHMNC-UHFFFAOYSA-M 0.000 description 1
239000003017 thermal stabilizer Substances 0.000 description 1
239000012815 thermoplastic material Substances 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
229920001567 vinyl ester resin Polymers 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
238000005406 washing Methods 0.000 description 1
230000004580 weight loss Effects 0.000 description 1

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CA281,483A 1977-06-27 1977-06-27 Trifluoromethanesulfonates Expired CA1081248A (fr)

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Application Number	Priority Date	Filing Date	Title
CA281,483A CA1081248A (fr)	1977-06-27	1977-06-27	Trifluoromethanesulfonates

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Application Number	Priority Date	Filing Date	Title
CA281,483A CA1081248A (fr)	1977-06-27	1977-06-27	Trifluoromethanesulfonates

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CA1081248A true CA1081248A (fr)	1980-07-08

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CA281,483A Expired CA1081248A (fr)	1977-06-27	1977-06-27	Trifluoromethanesulfonates

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CA (1)	CA1081248A (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4801721A (en) *	1984-08-16	1989-01-31	Ryan James W	Stereospecific synthesis of carboxyalkyl peptides

1977
- 1977-06-27 CA CA281,483A patent/CA1081248A/fr not_active Expired

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4801721A (en) *	1984-08-16	1989-01-31	Ryan James W	Stereospecific synthesis of carboxyalkyl peptides

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Date	Code	Title	Description
1997-07-08	MKEX	Expiry

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US4252967A (en)	1981-02-24	Dihaloneopentyl silicate flame retardants
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US5824241A (en)	1998-10-20	Brominated tetrabromophthalate ester flame retardants flame retardant polymer compositions

CA1081248A - Trifluoromethanesulfonates - Google Patents

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Applications Claiming Priority (1)

Publications (1)

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ID=4108989

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Cited By (1)

Cited By (1)

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