ES370147A1 - A procedure to manufacture ciclopropilamin. (Machine-translation by Google Translate, not legally binding) - Google Patents
A procedure to manufacture ciclopropilamin. (Machine-translation by Google Translate, not legally binding)Info
- Publication number
- ES370147A1 ES370147A1 ES370147A ES370147A ES370147A1 ES 370147 A1 ES370147 A1 ES 370147A1 ES 370147 A ES370147 A ES 370147A ES 370147 A ES370147 A ES 370147A ES 370147 A1 ES370147 A1 ES 370147A1
- Authority
- ES
- Spain
- Prior art keywords
- reaction mixture
- yield
- alkali metal
- cyclopropane
- aqueous solution
- 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.)
- Expired
Links
- 238000004519 manufacturing process Methods 0.000 title 1
- 238000000034 method Methods 0.000 title 1
- 239000011541 reaction mixture Substances 0.000 abstract 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 4
- 229910052783 alkali metal Inorganic materials 0.000 abstract 4
- -1 alkali metal hypochlorite Chemical class 0.000 abstract 4
- AIMMVWOEOZMVMS-UHFFFAOYSA-N cyclopropanecarboxamide Chemical compound NC(=O)C1CC1 AIMMVWOEOZMVMS-UHFFFAOYSA-N 0.000 abstract 4
- 239000007864 aqueous solution Substances 0.000 abstract 3
- HTJDQJBWANPRPF-UHFFFAOYSA-N Cyclopropylamine Chemical compound NC1CC1 HTJDQJBWANPRPF-UHFFFAOYSA-N 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 229910021529 ammonia Inorganic materials 0.000 abstract 2
- 239000012074 organic phase Substances 0.000 abstract 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 abstract 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- YMGUBTXCNDTFJI-UHFFFAOYSA-M cyclopropanecarboxylate Chemical compound [O-]C(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-M 0.000 abstract 1
- 238000004821 distillation Methods 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- WQYVRQLZKVEZGA-UHFFFAOYSA-N hypochlorite Inorganic materials Cl[O-] WQYVRQLZKVEZGA-UHFFFAOYSA-N 0.000 abstract 1
- 239000007788 liquid Substances 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 238000004064 recycling Methods 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 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
- C07C51/09—Preparation of carboxylic acids or their salts, halides or anhydrides from carboxylic acid esters or lactones
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)
Abstract
Cyclopropylamine is prepared by first adding an alkali metal hypochlorite to an aqueous solution of cyclopropane-carboxamide to yield an intermediate reaction mixture wherein substantial conversion to the alkali metal cyclopropane carboxylate has been prevented and then reacting the intermediate reaction mixture with an alkali metal hydroxide to yield a reaction mixture containing cyclopropylamine in aqueous solution. The cyclopropane carboxamide may be prepared by (a) reacting a lower alkyl C 1-4 4-chloro butyrate with an alkali metal alkoxide in an inert organic liquid to yield a reaction mixture containing lower alkyl C 1-4 cyclopropane carboxylate, (b) reacting ammonia with the reaction mixture from step (a) in the presence of alkali metal alkoxide and a lower alkanol C 1-4 to yield a reaction mixture containing cyclopropane carboxamide, (c) removing the lower alkanol C 1-4 and unreacted ammonia and ester by distillation to yield an overhead distillate, (d) adding water to the residual mixture and separating the organic phase and an aqueous solution of cyclopropane carboxamide, (e) recycling the organic phase to step (a).
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US75628868A | 1968-08-29 | 1968-08-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES370147A1 true ES370147A1 (en) | 1971-04-01 |
Family
ID=25042820
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES370147A Expired ES370147A1 (en) | 1968-08-29 | 1969-08-01 | A procedure to manufacture ciclopropilamin. (Machine-translation by Google Translate, not legally binding) |
Country Status (6)
| Country | Link |
|---|---|
| JP (1) | JPS51104B1 (en) |
| CH (1) | CH503691A (en) |
| DE (1) | DE1939759B2 (en) |
| ES (1) | ES370147A1 (en) |
| FR (1) | FR2016569A1 (en) |
| GB (1) | GB1257097A (en) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5391001A (en) * | 1977-01-22 | 1978-08-10 | Sumitomo Metal Ind Ltd | Control method for raw material particle size distribution in sintering pallet |
| DE3026094C2 (en) * | 1980-07-10 | 1983-01-05 | Degussa Ag, 6000 Frankfurt | Process for the preparation of cyclopropanecarboxamides |
| FI86889C (en) * | 1984-03-29 | 1992-10-26 | Lonza Ag | Process for the preparation of L-carnitine in a microbiological manner |
| US4590292A (en) * | 1985-06-10 | 1986-05-20 | Ciba-Geigy Corporation | Process for the manufacture of cyclopropylamine |
| JPH0291049A (en) * | 1988-09-21 | 1990-03-30 | Lonza Ag | Method for producing r-butyrobetaine |
| DE3836782A1 (en) * | 1988-10-28 | 1990-05-31 | Bayer Ag | METHOD FOR PRODUCING CYCLOPROPANCARBONIC ACID AMIDE |
| DE3836917A1 (en) * | 1988-10-29 | 1990-05-17 | Bayer Ag | PROCESS FOR THE PREPARATION OF CYCLOPROPYLAMINE |
| DE4222497A1 (en) * | 1992-07-09 | 1994-01-13 | Huels Chemische Werke Ag | Process for the production of chlorine-free methyl cyclopropanecarboxylate |
| DE4400328A1 (en) * | 1994-01-07 | 1995-07-13 | Huels Chemische Werke Ag | Process for the preparation of cyclopropanecarboxamide |
| CN1050597C (en) * | 1995-11-15 | 2000-03-22 | 中国石油化工总公司上海石油化工研究院 | Process for synthesizing cyclopropyl carboxylic ester |
| DE19617991A1 (en) * | 1996-05-04 | 1997-11-13 | Huels Chemische Werke Ag | Process for the continuous production of esters of thermally labile acids |
| DE19830633A1 (en) * | 1998-07-09 | 2000-01-13 | Degussa | Process for the preparation of cyclopropylamine |
| DE10162684A1 (en) | 2001-12-19 | 2003-07-10 | Bayer Ag | Process for the production of amines |
| US6683216B1 (en) | 2002-11-06 | 2004-01-27 | Eastman Chemical Company | Continuous process for the preparation of amines |
-
1969
- 1969-08-01 ES ES370147A patent/ES370147A1/en not_active Expired
- 1969-08-05 DE DE19691939759 patent/DE1939759B2/en not_active Withdrawn
- 1969-08-06 GB GB1257097D patent/GB1257097A/en not_active Expired
- 1969-08-26 FR FR6929134A patent/FR2016569A1/fr not_active Withdrawn
- 1969-08-28 CH CH1306069A patent/CH503691A/en not_active IP Right Cessation
- 1969-08-29 JP JP6810169A patent/JPS51104B1/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| GB1257097A (en) | 1971-12-15 |
| FR2016569A1 (en) | 1970-05-08 |
| JPS51104B1 (en) | 1976-01-05 |
| DE1939759B2 (en) | 1979-07-19 |
| CH503691A (en) | 1971-02-28 |
| DE1939759A1 (en) | 1970-03-05 |
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