DE3024694A1 - Multicyclisches verfahren zur herstellung von n,n,n',n' -tetraacetylaethylendiamin - Google Patents
Multicyclisches verfahren zur herstellung von n,n,n',n' -tetraacetylaethylendiaminInfo
- Publication number
- DE3024694A1 DE3024694A1 DE19803024694 DE3024694A DE3024694A1 DE 3024694 A1 DE3024694 A1 DE 3024694A1 DE 19803024694 DE19803024694 DE 19803024694 DE 3024694 A DE3024694 A DE 3024694A DE 3024694 A1 DE3024694 A1 DE 3024694A1
- Authority
- DE
- Germany
- Prior art keywords
- cycle
- acetic anhydride
- acetic acid
- tetraacetylethylenediamine
- distilled
- 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.)
- Granted
Links
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 title claims abstract description 206
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 title claims abstract description 146
- 238000006243 chemical reaction Methods 0.000 title claims abstract description 24
- 239000012190 activator Substances 0.000 title abstract description 3
- 239000003599 detergent Substances 0.000 title abstract description 3
- 150000001412 amines Chemical class 0.000 title 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 title 1
- 239000005977 Ethylene Substances 0.000 title 1
- FUSUHKVFWTUUBE-UHFFFAOYSA-N buten-2-one Chemical group CC(=O)C=C FUSUHKVFWTUUBE-UHFFFAOYSA-N 0.000 title 1
- BGRWYDHXPHLNKA-UHFFFAOYSA-N Tetraacetylethylenediamine Chemical compound CC(=O)N(C(C)=O)CCN(C(C)=O)C(C)=O BGRWYDHXPHLNKA-UHFFFAOYSA-N 0.000 claims abstract description 41
- 238000000034 method Methods 0.000 claims abstract description 41
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims abstract description 23
- 239000007788 liquid Substances 0.000 claims abstract description 17
- 238000001953 recrystallisation Methods 0.000 claims abstract description 14
- WNYIBZHOMJZDKN-UHFFFAOYSA-N n-(2-acetamidoethyl)acetamide Chemical compound CC(=O)NCCNC(C)=O WNYIBZHOMJZDKN-UHFFFAOYSA-N 0.000 claims abstract description 11
- 239000011541 reaction mixture Substances 0.000 claims description 26
- 238000004821 distillation Methods 0.000 claims description 24
- 239000000203 mixture Substances 0.000 claims description 13
- 238000010626 work up procedure Methods 0.000 claims description 9
- 238000001816 cooling Methods 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 238000005191 phase separation Methods 0.000 claims description 5
- 230000015572 biosynthetic process Effects 0.000 claims description 3
- 238000004064 recycling Methods 0.000 claims description 2
- 239000002002 slurry Substances 0.000 claims 1
- 229940012017 ethylenediamine Drugs 0.000 abstract 1
- 150000008064 anhydrides Chemical class 0.000 description 5
- 125000004122 cyclic group Chemical group 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 239000012535 impurity Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000002253 acid Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000006735 deficit Effects 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- DAKZISABEDGGSV-UHFFFAOYSA-N n-(2-aminoethyl)acetamide Chemical compound CC(=O)NCCN DAKZISABEDGGSV-UHFFFAOYSA-N 0.000 description 1
- 238000004537 pulping Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/90—Carboxylic acid amides having nitrogen atoms of carboxamide groups further acylated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/02—Preparation of carboxylic acid amides from carboxylic acids or from esters, anhydrides, or halides thereof by reaction with ammonia or amines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/90—Carboxylic acid amides having nitrogen atoms of carboxamide groups further acylated
- C07C233/91—Carboxylic acid amides having nitrogen atoms of carboxamide groups further acylated with carbon atoms of the carboxamide groups bound to acyclic carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19803024694 DE3024694A1 (de) | 1980-06-30 | 1980-06-30 | Multicyclisches verfahren zur herstellung von n,n,n',n' -tetraacetylaethylendiamin |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19803024694 DE3024694A1 (de) | 1980-06-30 | 1980-06-30 | Multicyclisches verfahren zur herstellung von n,n,n',n' -tetraacetylaethylendiamin |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE3024694A1 true DE3024694A1 (de) | 1982-01-28 |
| DE3024694C2 DE3024694C2 (enrdf_load_stackoverflow) | 1991-03-07 |
Family
ID=6106011
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19803024694 Granted DE3024694A1 (de) | 1980-06-30 | 1980-06-30 | Multicyclisches verfahren zur herstellung von n,n,n',n' -tetraacetylaethylendiamin |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE3024694A1 (enrdf_load_stackoverflow) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0070432A1 (de) * | 1981-07-11 | 1983-01-26 | Bayer Ag | Verfahren zur Herstellung von gereinigtem Tetraacetylethylendiamin (TAED) |
| EP0238958A2 (de) | 1986-03-22 | 1987-09-30 | Henkel Kommanditgesellschaft auf Aktien | Verfahren zur Reinigung von Tetraacetylethylendiamin |
| EP0484634A1 (en) * | 1990-11-09 | 1992-05-13 | CAFFARO S.p.A. | Process for the purification of tetraacetylethylene diamine (TAED) |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1335204A (en) * | 1970-07-07 | 1973-10-24 | Unilever Ltd | Preparation of polyacetylalkylene diamines |
| DE2816174A1 (de) * | 1978-04-14 | 1979-10-25 | Hoechst Ag | Verfahren zur herstellung von n,n,n',n'-tetraacetylaethylendiamin |
| DE2832021A1 (de) | 1978-07-21 | 1980-01-31 | Basf Ag | Verfahren zur herstellung von tetraacetylaethylendiamin |
-
1980
- 1980-06-30 DE DE19803024694 patent/DE3024694A1/de active Granted
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1335204A (en) * | 1970-07-07 | 1973-10-24 | Unilever Ltd | Preparation of polyacetylalkylene diamines |
| DE2816174A1 (de) * | 1978-04-14 | 1979-10-25 | Hoechst Ag | Verfahren zur herstellung von n,n,n',n'-tetraacetylaethylendiamin |
| DE2832021A1 (de) | 1978-07-21 | 1980-01-31 | Basf Ag | Verfahren zur herstellung von tetraacetylaethylendiamin |
Non-Patent Citations (1)
| Title |
|---|
| J.Chem.Educ., Bd. 14, 1939, S. 141-2 * |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0070432A1 (de) * | 1981-07-11 | 1983-01-26 | Bayer Ag | Verfahren zur Herstellung von gereinigtem Tetraacetylethylendiamin (TAED) |
| EP0238958A2 (de) | 1986-03-22 | 1987-09-30 | Henkel Kommanditgesellschaft auf Aktien | Verfahren zur Reinigung von Tetraacetylethylendiamin |
| EP0484634A1 (en) * | 1990-11-09 | 1992-05-13 | CAFFARO S.p.A. | Process for the purification of tetraacetylethylene diamine (TAED) |
Also Published As
| Publication number | Publication date |
|---|---|
| DE3024694C2 (enrdf_load_stackoverflow) | 1991-03-07 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| 8172 | Supplementary division/partition in: |
Ref country code: DE Ref document number: 3051126 Format of ref document f/p: P |
|
| Q171 | Divided out to: |
Ref country code: DE Ref document number: 3051126 |
|
| 8127 | New person/name/address of the applicant |
Owner name: WARWICK INTERNATIONAL LTD., LEEDS, GB |
|
| 8128 | New person/name/address of the agent |
Representative=s name: DANNENBERG, G., DIPL.-ING., 6000 FRANKFURT WEINHOL |
|
| 8127 | New person/name/address of the applicant |
Owner name: WARWICK INTERNATIONAL LTD., LEEDS, GB |
|
| 8128 | New person/name/address of the agent |
Representative=s name: DANNENBERG, G., DIPL.-ING., 6000 FRANKFURT WEINHOL |
|
| AH | Division in |
Ref country code: DE Ref document number: 3051126 Format of ref document f/p: P |
|
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8327 | Change in the person/name/address of the patent owner |
Owner name: WARWICK INTERNATIONAL GROUP PLC, LEEDS, GB |
|
| 8327 | Change in the person/name/address of the patent owner |
Owner name: WARWICK INTERNATIONAL GROUP LTD., LEEDS, GB |
|
| 8327 | Change in the person/name/address of the patent owner |
Owner name: WARWICK INTERNATIONAL GROUP LTD., LEEDS, GB |
|
| 8327 | Change in the person/name/address of the patent owner |
Owner name: WARWICK INTERNATIONAL GROUP LTD., LEEDS, GB |
|
| 8339 | Ceased/non-payment of the annual fee |