JPH0531539B2 - - Google Patents
Info
- Publication number
- JPH0531539B2 JPH0531539B2 JP7532485A JP7532485A JPH0531539B2 JP H0531539 B2 JPH0531539 B2 JP H0531539B2 JP 7532485 A JP7532485 A JP 7532485A JP 7532485 A JP7532485 A JP 7532485A JP H0531539 B2 JPH0531539 B2 JP H0531539B2
- Authority
- JP
- Japan
- Prior art keywords
- butyl
- liquid phase
- hydroquinone
- phenyl
- acid
- 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 - Lifetime
Links
- 239000007791 liquid phase Substances 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 14
- SJSZBOAQWPKFMU-UHFFFAOYSA-N n-(1-acetamidoethyl)acetamide Chemical compound CC(=O)NC(C)NC(C)=O SJSZBOAQWPKFMU-UHFFFAOYSA-N 0.000 claims description 9
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 claims description 8
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 claims description 8
- 238000010438 heat treatment Methods 0.000 claims description 8
- 238000001704 evaporation Methods 0.000 claims description 7
- 230000008020 evaporation Effects 0.000 claims description 7
- 239000003112 inhibitor Substances 0.000 claims description 7
- 238000006116 polymerization reaction Methods 0.000 claims description 7
- 238000001816 cooling Methods 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims description 6
- 238000005979 thermal decomposition reaction Methods 0.000 claims description 6
- PWWSSIYVTQUJQQ-UHFFFAOYSA-N distearyl thiodipropionate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)CCSCCC(=O)OCCCCCCCCCCCCCCCCCC PWWSSIYVTQUJQQ-UHFFFAOYSA-N 0.000 claims description 4
- RQAKESSLMFZVMC-UHFFFAOYSA-N n-ethenylacetamide Chemical compound CC(=O)NC=C RQAKESSLMFZVMC-UHFFFAOYSA-N 0.000 claims description 4
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 claims description 4
- 238000010992 reflux Methods 0.000 claims description 4
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 claims description 3
- 235000010354 butylated hydroxytoluene Nutrition 0.000 claims description 3
- XACQZFVINUCPQX-UHFFFAOYSA-N 1-n-phenyl-2-n-propan-2-ylbenzene-1,2-diamine Chemical compound CC(C)NC1=CC=CC=C1NC1=CC=CC=C1 XACQZFVINUCPQX-UHFFFAOYSA-N 0.000 claims description 2
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 claims description 2
- GHKOFFNLGXMVNJ-UHFFFAOYSA-N Didodecyl thiobispropanoate Chemical compound CCCCCCCCCCCCOC(=O)CCSCCC(=O)OCCCCCCCCCCCC GHKOFFNLGXMVNJ-UHFFFAOYSA-N 0.000 claims description 2
- XQVWYOYUZDUNRW-UHFFFAOYSA-N N-Phenyl-1-naphthylamine Chemical compound C=1C=CC2=CC=CC=C2C=1NC1=CC=CC=C1 XQVWYOYUZDUNRW-UHFFFAOYSA-N 0.000 claims description 2
- KEQFTVQCIQJIQW-UHFFFAOYSA-N N-Phenyl-2-naphthylamine Chemical compound C=1C=C2C=CC=CC2=CC=1NC1=CC=CC=C1 KEQFTVQCIQJIQW-UHFFFAOYSA-N 0.000 claims description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims description 2
- CZBZUDVBLSSABA-UHFFFAOYSA-N butylated hydroxyanisole Chemical compound COC1=CC=C(O)C(C(C)(C)C)=C1.COC1=CC=C(O)C=C1C(C)(C)C CZBZUDVBLSSABA-UHFFFAOYSA-N 0.000 claims description 2
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 claims description 2
- 229950000688 phenothiazine Drugs 0.000 claims description 2
- NGFBEQCLQRWZGA-UHFFFAOYSA-N C.C=CC(C(=O)O)C1=CC(=C(C(=C1)C(C)(C)C)O)C(C)(C)C.C=CC(C(=O)O)C1=CC(=C(C(=C1)C(C)(C)C)O)C(C)(C)C.C=CC(C(=O)O)C1=CC(=C(C(=C1)C(C)(C)C)O)C(C)(C)C.C=CC(C(=O)O)C1=CC(=C(C(=C1)C(C)(C)C)O)C(C)(C)C Chemical compound C.C=CC(C(=O)O)C1=CC(=C(C(=C1)C(C)(C)C)O)C(C)(C)C.C=CC(C(=O)O)C1=CC(=C(C(=C1)C(C)(C)C)O)C(C)(C)C.C=CC(C(=O)O)C1=CC(=C(C(=C1)C(C)(C)C)O)C(C)(C)C.C=CC(C(=O)O)C1=CC(=C(C(=C1)C(C)(C)C)O)C(C)(C)C NGFBEQCLQRWZGA-UHFFFAOYSA-N 0.000 claims 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000000654 additive Substances 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
- -1 butylhydroxyanisole Chemical compound 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 238000000197 pyrolysis Methods 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 238000007086 side reaction Methods 0.000 description 2
- 150000005208 1,4-dihydroxybenzenes Chemical class 0.000 description 1
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 150000003151 propanoic acid esters Chemical class 0.000 description 1
- 239000005297 pyrex Substances 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 238000010517 secondary reaction Methods 0.000 description 1
- 239000011949 solid catalyst Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP7532485A JPS61236757A (ja) | 1985-04-11 | 1985-04-11 | エチリデンビスアセトアミドの熱分解方法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP7532485A JPS61236757A (ja) | 1985-04-11 | 1985-04-11 | エチリデンビスアセトアミドの熱分解方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS61236757A JPS61236757A (ja) | 1986-10-22 |
| JPH0531539B2 true JPH0531539B2 (enrdf_load_stackoverflow) | 1993-05-12 |
Family
ID=13572969
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP7532485A Granted JPS61236757A (ja) | 1985-04-11 | 1985-04-11 | エチリデンビスアセトアミドの熱分解方法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS61236757A (enrdf_load_stackoverflow) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2002167369A (ja) * | 2000-09-19 | 2002-06-11 | Showa Denko Kk | 高重合性ｎ−ビニルカルボン酸アミドの製造方法 |
-
1985
- 1985-04-11 JP JP7532485A patent/JPS61236757A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS61236757A (ja) | 1986-10-22 |
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