CH435229A - Verfahren zur Herstellung eines neuen Halogenpropans - Google Patents
Verfahren zur Herstellung eines neuen HalogenpropansInfo
- Publication number
- CH435229A CH435229A CH1494363A CH1494363A CH435229A CH 435229 A CH435229 A CH 435229A CH 1494363 A CH1494363 A CH 1494363A CH 1494363 A CH1494363 A CH 1494363A CH 435229 A CH435229 A CH 435229A
- Authority
- CH
- Switzerland
- Prior art keywords
- difluoropropane
- chloro
- bromo
- bromine
- anesthetic
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 11
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 title description 4
- 238000004519 manufacturing process Methods 0.000 title description 4
- 229910052736 halogen Inorganic materials 0.000 title description 3
- 150000002367 halogens Chemical class 0.000 title description 3
- 239000001294 propane Substances 0.000 title description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 12
- ZASIITYHGCXAIU-UHFFFAOYSA-N 1-bromo-1-chloro-2,2-difluoropropane Chemical compound CC(F)(F)C(Cl)Br ZASIITYHGCXAIU-UHFFFAOYSA-N 0.000 claims description 11
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 11
- 229910052794 bromium Inorganic materials 0.000 claims description 11
- OOXYGJSMTMPTFW-UHFFFAOYSA-N 1-chloro-2,2-difluoropropane Chemical compound CC(F)(F)CCl OOXYGJSMTMPTFW-UHFFFAOYSA-N 0.000 claims description 7
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 6
- 239000000460 chlorine Substances 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- 230000031709 bromination Effects 0.000 claims description 5
- 238000005893 bromination reaction Methods 0.000 claims description 5
- 238000005660 chlorination reaction Methods 0.000 claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 4
- WSECXBNDYYTSGU-UHFFFAOYSA-N 1-bromo-2,2-difluoropropane Chemical compound CC(F)(F)CBr WSECXBNDYYTSGU-UHFFFAOYSA-N 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 2
- 230000001419 dependent effect Effects 0.000 claims 1
- 230000003444 anaesthetic effect Effects 0.000 description 10
- 206010002091 Anaesthesia Diseases 0.000 description 9
- 230000037005 anaesthesia Effects 0.000 description 9
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- 239000001301 oxygen Substances 0.000 description 9
- 229910052760 oxygen Inorganic materials 0.000 description 9
- 239000011521 glass Substances 0.000 description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 241000283973 Oryctolagus cuniculus Species 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000003983 inhalation anesthetic agent Substances 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 241000699670 Mus sp. Species 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- ATJSHGXKPLTCEG-UHFFFAOYSA-N 1-chloro-1,1-difluoropropane Chemical compound CCC(F)(F)Cl ATJSHGXKPLTCEG-UHFFFAOYSA-N 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 238000005194 fractionation Methods 0.000 description 3
- BCQZXOMGPXTTIC-UHFFFAOYSA-N halothane Chemical compound FC(F)(F)C(Cl)Br BCQZXOMGPXTTIC-UHFFFAOYSA-N 0.000 description 3
- 230000029058 respiratory gaseous exchange Effects 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- 229940035674 anesthetics Drugs 0.000 description 2
- 230000036772 blood pressure Effects 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 239000003193 general anesthetic agent Substances 0.000 description 2
- 229960003132 halothane Drugs 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- MGSRCZKZVOBKFT-UHFFFAOYSA-N thymol Chemical compound CC(C)C1=CC=C(C)C=C1O MGSRCZKZVOBKFT-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- ZNRFPPAXFPJZRQ-UHFFFAOYSA-N 1-bromo-1,1-difluoropropane Chemical compound CCC(F)(F)Br ZNRFPPAXFPJZRQ-UHFFFAOYSA-N 0.000 description 1
- OPLWDQVQIWKMSG-UHFFFAOYSA-N 1-chloro-1-fluoropropane Chemical compound CCC(F)Cl OPLWDQVQIWKMSG-UHFFFAOYSA-N 0.000 description 1
- LVZWSLJZHVFIQJ-UHFFFAOYSA-N Cyclopropane Chemical compound C1CC1 LVZWSLJZHVFIQJ-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
- GQPLMRYTRLFLPF-UHFFFAOYSA-N Nitrous Oxide Chemical compound [O-][N+]#N GQPLMRYTRLFLPF-UHFFFAOYSA-N 0.000 description 1
- 239000005844 Thymol Substances 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical compound C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 230000034994 death Effects 0.000 description 1
- 231100000517 death Toxicity 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 238000002224 dissection Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 210000001105 femoral artery Anatomy 0.000 description 1
- DLEGDLSLRSOURQ-UHFFFAOYSA-N fluroxene Chemical compound FC(F)(F)COC=C DLEGDLSLRSOURQ-UHFFFAOYSA-N 0.000 description 1
- 229950010045 fluroxene Drugs 0.000 description 1
- 210000004013 groin Anatomy 0.000 description 1
- 230000026030 halogenation Effects 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 210000004072 lung Anatomy 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- RFKMCNOHBTXSMU-UHFFFAOYSA-N methoxyflurane Chemical compound COC(F)(F)C(Cl)Cl RFKMCNOHBTXSMU-UHFFFAOYSA-N 0.000 description 1
- 229960002455 methoxyflurane Drugs 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229910052573 porcelain Inorganic materials 0.000 description 1
- MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 1
- 229960004919 procaine Drugs 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 230000011514 reflex Effects 0.000 description 1
- 230000000241 respiratory effect Effects 0.000 description 1
- 229960000790 thymol Drugs 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 238000009834 vaporization Methods 0.000 description 1
- 230000008016 vaporization Effects 0.000 description 1
- 229960000834 vinyl ether Drugs 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C19/00—Acyclic saturated compounds containing halogen atoms
- C07C19/08—Acyclic saturated compounds containing halogen atoms containing fluorine
- C07C19/14—Acyclic saturated compounds containing halogen atoms containing fluorine and bromine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/02—Halogenated hydrocarbons
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
- C07C17/10—Preparation of halogenated hydrocarbons by replacement by halogens of hydrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB4624862A GB1004637A (en) | 1962-12-07 | 1962-12-07 | A halogenated propane |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH435229A true CH435229A (de) | 1967-05-15 |
Family
ID=10440455
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1494363A CH435229A (de) | 1962-12-07 | 1963-12-06 | Verfahren zur Herstellung eines neuen Halogenpropans |
Country Status (8)
| Country | Link |
|---|---|
| BE (1) | BE640851A (enrdf_load_stackoverflow) |
| CH (1) | CH435229A (enrdf_load_stackoverflow) |
| DE (1) | DE1224290B (enrdf_load_stackoverflow) |
| DK (1) | DK109324C (enrdf_load_stackoverflow) |
| FR (2) | FR1561903A (enrdf_load_stackoverflow) |
| GB (1) | GB1004637A (enrdf_load_stackoverflow) |
| NL (2) | NL126372C (enrdf_load_stackoverflow) |
| SE (1) | SE304000B (enrdf_load_stackoverflow) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2629775C3 (de) * | 1976-07-02 | 1979-03-01 | Kali-Chemie Ag, 3000 Hannover | Verfahren zur Herstellung von Brom-(chlor)-fluorkohlenwasserstoffen |
-
0
- NL NL301147D patent/NL301147A/xx unknown
- NL NL126372D patent/NL126372C/xx active
-
1962
- 1962-12-07 GB GB4624862A patent/GB1004637A/en not_active Expired
-
1963
- 1963-11-29 DE DEJ24826A patent/DE1224290B/de active Pending
- 1963-12-02 DK DK562363A patent/DK109324C/da active
- 1963-12-05 BE BE640851A patent/BE640851A/xx unknown
- 1963-12-05 SE SE1349863A patent/SE304000B/xx unknown
- 1963-12-06 CH CH1494363A patent/CH435229A/de unknown
- 1963-12-06 FR FR956407A patent/FR1561903A/fr not_active Expired
-
1964
- 1964-03-05 FR FR966252A patent/FR3729M/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| GB1004637A (en) | 1965-09-15 |
| DE1224290B (de) | 1966-09-08 |
| NL301147A (enrdf_load_stackoverflow) | |
| NL126372C (enrdf_load_stackoverflow) | |
| BE640851A (enrdf_load_stackoverflow) | 1964-06-05 |
| FR3729M (fr) | 1965-12-06 |
| SE304000B (enrdf_load_stackoverflow) | 1968-09-16 |
| FR1561903A (enrdf_load_stackoverflow) | 1969-04-04 |
| DK109324C (da) | 1968-04-16 |
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