CA1053699A - Series paires d'acides w-amines - Google Patents

Series paires d'acides w-amines

Info

Publication number: CA1053699A
Authority: CA; Canada
Prior art keywords: temperature; telomers; acid; process according; iii
Prior art date: 1975-12-24
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

CA242,591A

Other languages

English (en)

Other versions

CA242591S (en

Inventor

Rakhil K. Freidlina

Tamara T. Vasilieva

Felix K. Velichko

Alexandr B. Terentiev

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.)

INSTITUT ELEMENTOORGANICHESKIKH SOEDINENY AKADEMII NAUK SSSR

Original Assignee

INSTITUT ELEMENTOORGANICHESKIKH SOEDINENY AKADEMII NAUK SSSR

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.)

1975-12-24

Filing date

1975-12-24

Publication date

1979-05-01

1975-12-24 Application filed by INSTITUT ELEMENTOORGANICHESKIKH SOEDINENY AKADEMII NAUK SSSR filed Critical INSTITUT ELEMENTOORGANICHESKIKH SOEDINENY AKADEMII NAUK SSSR

1975-12-24 Priority to CA242,591A priority Critical patent/CA1053699A/fr

1979-05-01 Application granted granted Critical

1979-05-01 Publication of CA1053699A publication Critical patent/CA1053699A/fr

Status Expired legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims abstract description 46
230000008569 process Effects 0.000 title claims abstract description 26
238000004519 manufacturing process Methods 0.000 title claims abstract description 15
150000004702 methyl esters Chemical class 0.000 claims abstract description 36
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims abstract description 30
238000005915 ammonolysis reaction Methods 0.000 claims abstract description 25
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims abstract description 19
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims abstract description 14
239000005977 Ethylene Substances 0.000 claims abstract description 14
229910021529 ammonia Inorganic materials 0.000 claims abstract description 14
239000011347 resin Substances 0.000 claims abstract description 8
229920005989 resin Polymers 0.000 claims abstract description 8
235000011054 acetic acid Nutrition 0.000 claims abstract description 6
CHRJZRDFSQHIFI-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;styrene Chemical compound C=CC1=CC=CC=C1.C=CC1=CC=CC=C1C=C CHRJZRDFSQHIFI-UHFFFAOYSA-N 0.000 claims abstract description 5
229910052736 halogen Inorganic materials 0.000 claims abstract description 5
239000003999 initiator Substances 0.000 claims abstract description 5
-1 halogen acetic acids Chemical class 0.000 claims abstract description 4
238000007348 radical reaction Methods 0.000 claims abstract description 3
235000013350 formula milk Nutrition 0.000 claims description 24
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 18
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 16
238000009835 boiling Methods 0.000 claims description 14
239000003054 catalyst Substances 0.000 claims description 9
239000001257 hydrogen Substances 0.000 claims description 9
229910052739 hydrogen Inorganic materials 0.000 claims description 9
229910052763 palladium Inorganic materials 0.000 claims description 9
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 6
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 5
229910000041 hydrogen chloride Inorganic materials 0.000 claims description 5
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 4
DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims description 2
150000003510 tertiary aliphatic amines Chemical class 0.000 claims description 2
229910052725 zinc Inorganic materials 0.000 claims description 2
239000011701 zinc Substances 0.000 claims description 2
125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims 1
238000006116 polymerization reaction Methods 0.000 abstract description 2
239000002253 acid Substances 0.000 description 34
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
239000000047 product Substances 0.000 description 19
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
239000000460 chlorine Substances 0.000 description 11
229940093470 ethylene Drugs 0.000 description 10
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
150000002148 esters Chemical class 0.000 description 9
230000007062 hydrolysis Effects 0.000 description 9
238000006460 hydrolysis reaction Methods 0.000 description 9
238000006722 reduction reaction Methods 0.000 description 9
125000004494 ethyl ester group Chemical group 0.000 description 8
238000001704 evaporation Methods 0.000 description 8
230000008020 evaporation Effects 0.000 description 8
VHFUHRXYRYWELT-UHFFFAOYSA-N methyl 2,2,2-trichloroacetate Chemical compound COC(=O)C(Cl)(Cl)Cl VHFUHRXYRYWELT-UHFFFAOYSA-N 0.000 description 7
239000000203 mixture Substances 0.000 description 7
239000000243 solution Substances 0.000 description 7
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
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
229960002684 aminocaproic acid Drugs 0.000 description 6
TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 6
229940124277 aminobutyric acid Drugs 0.000 description 5
BTCSSZJGUNDROE-UHFFFAOYSA-N gamma-aminobutyric acid Chemical compound NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 0.000 description 5
239000011541 reaction mixture Substances 0.000 description 5
150000007513 acids Chemical class 0.000 description 4
235000001014 amino acid Nutrition 0.000 description 4
238000004508 fractional distillation Methods 0.000 description 4
YDCHPLOFQATIDS-UHFFFAOYSA-N methyl 2-bromoacetate Chemical compound COC(=O)CBr YDCHPLOFQATIDS-UHFFFAOYSA-N 0.000 description 4
229910001220 stainless steel Inorganic materials 0.000 description 4
239000010935 stainless steel Substances 0.000 description 4
238000003756 stirring Methods 0.000 description 4
229940086542 triethylamine Drugs 0.000 description 4
PAOHAQSLJSMLAT-UHFFFAOYSA-N 1-butylperoxybutane Chemical group CCCCOOCCCC PAOHAQSLJSMLAT-UHFFFAOYSA-N 0.000 description 3
UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
150000001413 amino acids Chemical class 0.000 description 3
239000007864 aqueous solution Substances 0.000 description 3
239000001110 calcium chloride Substances 0.000 description 3
229910001628 calcium chloride Inorganic materials 0.000 description 3
238000006243 chemical reaction Methods 0.000 description 3
239000007795 chemical reaction product Substances 0.000 description 3
HKMLRUAPIDAGIE-UHFFFAOYSA-N methyl 2,2-dichloroacetate Chemical compound COC(=O)C(Cl)Cl HKMLRUAPIDAGIE-UHFFFAOYSA-N 0.000 description 3
239000002904 solvent Substances 0.000 description 3
OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 2
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
125000005907 alkyl ester group Chemical group 0.000 description 2
235000011114 ammonium hydroxide Nutrition 0.000 description 2
239000003814 drug Substances 0.000 description 2
JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 2
238000001030 gas--liquid chromatography Methods 0.000 description 2
150000002367 halogens Chemical class 0.000 description 2
230000008018 melting Effects 0.000 description 2
238000002844 melting Methods 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
238000011027 product recovery Methods 0.000 description 2
HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 2
239000002994 raw material Substances 0.000 description 2
238000011084 recovery Methods 0.000 description 2
229920006395 saturated elastomer Polymers 0.000 description 2
238000005406 washing Methods 0.000 description 2
OBLYWUBMZGHQDN-UHFFFAOYSA-N 2,2-dichlorobutanoic acid Chemical compound CCC(Cl)(Cl)C(O)=O OBLYWUBMZGHQDN-UHFFFAOYSA-N 0.000 description 1
SZIFAVKTNFCBPC-UHFFFAOYSA-N 2-chloroethanol Chemical compound OCCCl SZIFAVKTNFCBPC-UHFFFAOYSA-N 0.000 description 1
KXPULUVMTDIQOQ-UHFFFAOYSA-N 4,4,4-trichlorobutanoic acid Chemical compound OC(=O)CCC(Cl)(Cl)Cl KXPULUVMTDIQOQ-UHFFFAOYSA-N 0.000 description 1
241001474374 Blennius Species 0.000 description 1
WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 description 1
229910000831 Steel Inorganic materials 0.000 description 1
150000001243 acetic acids Chemical class 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
210000003169 central nervous system Anatomy 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
229910017052 cobalt Inorganic materials 0.000 description 1
239000010941 cobalt Substances 0.000 description 1
238000005520 cutting process Methods 0.000 description 1
238000006114 decarboxylation reaction Methods 0.000 description 1
210000003298 dental enamel Anatomy 0.000 description 1
238000004821 distillation Methods 0.000 description 1
229940079593 drug Drugs 0.000 description 1
238000001035 drying Methods 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
238000005194 fractionation Methods 0.000 description 1
230000008570 general process Effects 0.000 description 1
235000013922 glutamic acid Nutrition 0.000 description 1
239000004220 glutamic acid Substances 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
150000002431 hydrogen Chemical class 0.000 description 1
238000005984 hydrogenation reaction Methods 0.000 description 1
239000013067 intermediate product Substances 0.000 description 1
229910052742 iron Inorganic materials 0.000 description 1
229910052753 mercury Inorganic materials 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
229910000069 nitrogen hydride Inorganic materials 0.000 description 1
238000005086 pumping Methods 0.000 description 1
230000036647 reaction Effects 0.000 description 1
239000012495 reaction gas Substances 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
239000011369 resultant mixture Substances 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
239000010959 steel Substances 0.000 description 1
125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
238000001356 surgical procedure Methods 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical class OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1

Landscapes

Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CA242,591A 1975-12-24 1975-12-24 Series paires d'acides w-amines Expired CA1053699A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA242,591A CA1053699A (fr)	1975-12-24	1975-12-24	Series paires d'acides w-amines

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CA242,591A CA1053699A (fr)	1975-12-24	1975-12-24	Series paires d'acides w-amines

Publications (1)

Publication Number	Publication Date
CA1053699A true CA1053699A (fr)	1979-05-01

Family

ID=4104848

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA242,591A Expired CA1053699A (fr)	1975-12-24	1975-12-24	Series paires d'acides w-amines

Country Status (1)

Country	Link
CA (1)	CA1053699A (fr)

1975
- 1975-12-24 CA CA242,591A patent/CA1053699A/fr not_active Expired

Publication	Publication Date	Title
NO132616B (fr)	1975-09-01
US4079068A (en)	1978-03-14	Manufacture of tetrahydrofuran from the diacetate of 1,4-butanediol
CA1053699A (fr)	1979-05-01	Series paires d'acides w-amines
RU1836333C (ru)	1993-08-23	Способ получени @ -Бутиробетаина
US3896149A (en)	1975-07-22	Novel pyrrolidone derivatives and manufacturing the same
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