BE567029A - - Google Patents
Info
- Publication number
- BE567029A BE567029A BE567029DA BE567029A BE 567029 A BE567029 A BE 567029A BE 567029D A BE567029D A BE 567029DA BE 567029 A BE567029 A BE 567029A
- Authority
- BE
- Belgium
- Prior art keywords
- dichloro
- propanediol
- phenyl
- formula
- radical
- Prior art date
Links
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 claims description 21
- 229920000166 polytrimethylene carbonate Polymers 0.000 claims description 17
- 238000000034 method Methods 0.000 claims description 13
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 12
- 239000007788 liquid Substances 0.000 claims description 9
- 238000006243 chemical reaction Methods 0.000 claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 7
- 150000002148 esters Chemical class 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- YGYAWVDWMABLBF-UHFFFAOYSA-N phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 7
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- YBBRCQOCSYXUOC-UHFFFAOYSA-N Sulfuryl chloride Chemical group ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 claims description 5
- -1 cyclic carbonic acid ester Chemical class 0.000 claims description 5
- 150000002009 diols Chemical class 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- HPQVWDOOUQVBTO-UHFFFAOYSA-N lithium aluminium hydride Substances [Li+].[Al-] HPQVWDOOUQVBTO-UHFFFAOYSA-N 0.000 claims description 4
- OCZDCIYGECBNKL-UHFFFAOYSA-N lithium;alumanuide Chemical group [Li+].[AlH4-] OCZDCIYGECBNKL-UHFFFAOYSA-N 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 239000012320 chlorinating reagent Substances 0.000 claims description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 239000003153 chemical reaction reagent Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- RRVFYOSEKOTFOG-UHFFFAOYSA-N 1-phenylpropane-1,3-diol Chemical compound OCCC(O)C1=CC=CC=C1 RRVFYOSEKOTFOG-UHFFFAOYSA-N 0.000 claims 1
- 125000005083 alkoxyalkoxy group Chemical group 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 24
- 239000000203 mixture Substances 0.000 description 12
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 239000002253 acid Substances 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- 125000004494 ethyl ester group Chemical group 0.000 description 8
- YXFVVABEGXRONW-UHFFFAOYSA-N toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- UIIMBOGNXHQVGW-UHFFFAOYSA-M NaHCO3 Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- 229940091110 Antipyrine Drugs 0.000 description 5
- VEQOALNAAJBPNY-UHFFFAOYSA-N Phenazone Chemical compound CN1C(C)=CC(=O)N1C1=CC=CC=C1 VEQOALNAAJBPNY-UHFFFAOYSA-N 0.000 description 5
- 229960005222 phenazone Drugs 0.000 description 5
- SCYJEJYTVSCOCR-UHFFFAOYSA-N 2,2-dichloro-1-phenylpropane-1,3-diol Chemical compound OCC(Cl)(Cl)C(O)C1=CC=CC=C1 SCYJEJYTVSCOCR-UHFFFAOYSA-N 0.000 description 4
- 238000007792 addition Methods 0.000 description 4
- 150000005676 cyclic carbonates Chemical class 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- VMOJSOGJATVMTQ-UHFFFAOYSA-N 2,2-dichloro-3-oxo-3-phenylpropanoic acid Chemical compound OC(=O)C(Cl)(Cl)C(=O)C1=CC=CC=C1 VMOJSOGJATVMTQ-UHFFFAOYSA-N 0.000 description 3
- HXUIDZOMTRMIOE-UHFFFAOYSA-N 3-oxo-3-phenylpropionic acid Chemical compound OC(=O)CC(=O)C1=CC=CC=C1 HXUIDZOMTRMIOE-UHFFFAOYSA-N 0.000 description 3
- 230000000875 corresponding Effects 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
- KIUGWPDQHKXJHE-UHFFFAOYSA-N (2,2-dichloro-3-hydroxy-3-phenylpropyl) carbamate Chemical compound NC(=O)OCC(Cl)(Cl)C(O)C1=CC=CC=C1 KIUGWPDQHKXJHE-UHFFFAOYSA-N 0.000 description 2
- 150000000185 1,3-diols Chemical class 0.000 description 2
- WNLMYNASWOULQY-UHFFFAOYSA-N 4-tert-butylbenzoyl chloride Chemical compound CC(C)(C)C1=CC=C(C(Cl)=O)C=C1 WNLMYNASWOULQY-UHFFFAOYSA-N 0.000 description 2
- MYPNDOCQMCPPQZ-UHFFFAOYSA-N C(C)OC1=CC=C(C(=O)C(C(=O)O)(Cl)Cl)C=C1 Chemical compound C(C)OC1=CC=C(C(=O)C(C(=O)O)(Cl)Cl)C=C1 MYPNDOCQMCPPQZ-UHFFFAOYSA-N 0.000 description 2
- XYIBRDXRRQCHLP-UHFFFAOYSA-N Ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000002178 crystalline material Substances 0.000 description 2
- GKKZMYDNDDMXSE-UHFFFAOYSA-N ethyl 3-oxo-3-phenylpropanoate Chemical compound CCOC(=O)CC(=O)C1=CC=CC=C1 GKKZMYDNDDMXSE-UHFFFAOYSA-N 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L mgso4 Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 239000011343 solid material Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 2
- CHPAYVRWDWTJAT-UHFFFAOYSA-N 2-benzoyl-3,3,3-trifluoropropanoic acid Chemical class OC(=O)C(C(F)(F)F)C(=O)C1=CC=CC=C1 CHPAYVRWDWTJAT-UHFFFAOYSA-N 0.000 description 1
- WQIJVLLYFOYDCL-UHFFFAOYSA-N 3-(2-chlorophenyl)-3-oxopropanoic acid Chemical compound OC(=O)CC(=O)C1=CC=CC=C1Cl WQIJVLLYFOYDCL-UHFFFAOYSA-N 0.000 description 1
- HNQFHCIUQADONE-UHFFFAOYSA-N 3-(3-methylphenyl)-3-oxopropanoic acid Chemical compound CC1=CC=CC(C(=O)CC(O)=O)=C1 HNQFHCIUQADONE-UHFFFAOYSA-N 0.000 description 1
- SXWYNNNJFJPDNK-UHFFFAOYSA-N 3-(4-ethoxyphenyl)-3-oxopropanoic acid Chemical compound CCOC1=CC=C(C(=O)CC(O)=O)C=C1 SXWYNNNJFJPDNK-UHFFFAOYSA-N 0.000 description 1
- FBLNSQMYGLIFII-UHFFFAOYSA-N 3-(4-methoxyphenyl)-3-oxopropanoic acid Chemical compound COC1=CC=C(C(=O)CC(O)=O)C=C1 FBLNSQMYGLIFII-UHFFFAOYSA-N 0.000 description 1
- WDJHALXBUFZDSR-UHFFFAOYSA-N Acetoacetic acid Natural products CC(=O)CC(O)=O WDJHALXBUFZDSR-UHFFFAOYSA-N 0.000 description 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N Aluminium hydride Chemical compound [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- PASDCCFISLVPSO-UHFFFAOYSA-N Benzoyl chloride Chemical class ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
- WQCGHRRRJDAFJM-UHFFFAOYSA-N COC(C(=O)O)(C(C1=CC=CC=C1)=O)OC Chemical compound COC(C(=O)O)(C(C1=CC=CC=C1)=O)OC WQCGHRRRJDAFJM-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate dianion Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- MDAMADAVNNPVRD-UHFFFAOYSA-N ClC(C(O)(C1=C(C=CC=C1)CCCC)Cl)CO Chemical compound ClC(C(O)(C1=C(C=CC=C1)CCCC)Cl)CO MDAMADAVNNPVRD-UHFFFAOYSA-N 0.000 description 1
- BPTAIKQMPRPGKW-UHFFFAOYSA-N ClC(C(O)C1=CC=C(C=C1)OCC)(CO)Cl Chemical compound ClC(C(O)C1=CC=C(C=C1)OCC)(CO)Cl BPTAIKQMPRPGKW-UHFFFAOYSA-N 0.000 description 1
- JXTHNDFMNIQAHM-UHFFFAOYSA-N Dichloroacetic acid Chemical compound OC(=O)C(Cl)Cl JXTHNDFMNIQAHM-UHFFFAOYSA-N 0.000 description 1
- SRTHRWZAMDZJOS-UHFFFAOYSA-N Lithium hydride Chemical compound [H-].[Li+] SRTHRWZAMDZJOS-UHFFFAOYSA-N 0.000 description 1
- 229940035363 MUSCLE RELAXANTS Drugs 0.000 description 1
- 229940083876 Muscle relaxants FOR TREATMENT OF HEMORRHOIDS AND ANAL FISSURES FOR TOPICAL USE Drugs 0.000 description 1
- 241000287531 Psittacidae Species 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N Sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 210000000278 Spinal Cord Anatomy 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N acetic acid ethyl ester Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 1
- 238000005904 alkaline hydrolysis reaction Methods 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-N carbamate Chemical compound NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 1
- 229940112021 centrally acting muscle relaxants Carbamic acid esters Drugs 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 230000003001 depressive Effects 0.000 description 1
- 229960005215 dichloroacetic acid Drugs 0.000 description 1
- 150000002168 ethanoic acid esters Chemical class 0.000 description 1
- TUIRQRHLTQSYCN-UHFFFAOYSA-N ethyl 3-(4-ethoxyphenyl)-3-oxopropanoate Chemical compound CCOC(=O)CC(=O)C1=CC=C(OCC)C=C1 TUIRQRHLTQSYCN-UHFFFAOYSA-N 0.000 description 1
- AEGOOHDAUMBYHG-UHFFFAOYSA-N ethyl 3-(4-tert-butylphenyl)-3-oxopropanoate Chemical compound CCOC(=O)CC(=O)C1=CC=C(C(C)(C)C)C=C1 AEGOOHDAUMBYHG-UHFFFAOYSA-N 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- QDHHCQZDFGDHMP-UHFFFAOYSA-N monochloramine Chemical compound ClN QDHHCQZDFGDHMP-UHFFFAOYSA-N 0.000 description 1
- 239000003158 myorelaxant agent Substances 0.000 description 1
- 230000001264 neutralization Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- DNIAPMSPPWPWGF-UHFFFAOYSA-N propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BE567029A true BE567029A (es) |
Family
ID=186927
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BE567029D BE567029A (es) |
Country Status (1)
| Country | Link |
|---|---|
| BE (1) | BE567029A (es) |
-
0
- BE BE567029D patent/BE567029A/fr unknown
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