DE3043374A1 - Verfahren zur herstellung von methylenbis-(methylanthranilat) - Google Patents
Verfahren zur herstellung von methylenbis-(methylanthranilat)Info
- Publication number
- DE3043374A1 DE3043374A1 DE19803043374 DE3043374A DE3043374A1 DE 3043374 A1 DE3043374 A1 DE 3043374A1 DE 19803043374 DE19803043374 DE 19803043374 DE 3043374 A DE3043374 A DE 3043374A DE 3043374 A1 DE3043374 A1 DE 3043374A1
- Authority
- DE
- Germany
- Prior art keywords
- methylene bis
- methyl anthranilate
- reaction
- catalyst
- methylanthranilate
- 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.)
- Withdrawn
Links
- XEZPSTVEIZNGRR-UHFFFAOYSA-N 2-amino-5-[(4-amino-3-methoxycarbonylphenyl)methyl]benzoic acid methyl ester Chemical compound C1=C(N)C(C(=O)OC)=CC(CC=2C=C(C(N)=CC=2)C(=O)OC)=C1 XEZPSTVEIZNGRR-UHFFFAOYSA-N 0.000 title claims description 7
- 238000004519 manufacturing process Methods 0.000 title description 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 27
- VAMXMNNIEUEQDV-UHFFFAOYSA-N methyl anthranilate Chemical compound COC(=O)C1=CC=CC=C1N VAMXMNNIEUEQDV-UHFFFAOYSA-N 0.000 claims description 24
- 239000003054 catalyst Substances 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 14
- 229940102398 methyl anthranilate Drugs 0.000 claims description 12
- 238000006243 chemical reaction Methods 0.000 claims description 10
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 5
- 229910052710 silicon Inorganic materials 0.000 claims description 5
- 239000010703 silicon Substances 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 3
- 229910004298 SiO 2 Inorganic materials 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 150000007513 acids Chemical class 0.000 description 3
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 3
- 238000005260 corrosion Methods 0.000 description 3
- 230000007797 corrosion Effects 0.000 description 3
- 238000006386 neutralization reaction Methods 0.000 description 3
- KGRVJHAUYBGFFP-UHFFFAOYSA-N 2,2'-Methylenebis(4-methyl-6-tert-butylphenol) Chemical compound CC(C)(C)C1=CC(C)=CC(CC=2C(=C(C=C(C)C=2)C(C)(C)C)O)=C1O KGRVJHAUYBGFFP-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 239000013067 intermediate product Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000004848 polyfunctional curative Substances 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000004970 Chain extender Substances 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 239000007862 dimeric product Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000005227 gel permeation chromatography Methods 0.000 description 1
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/92—Ketonic chelates
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/099,779 US4252981A (en) | 1979-12-03 | 1979-12-03 | Synthesis of methylene bis(methylanthranilate) |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE3043374A1 true DE3043374A1 (de) | 1981-06-19 |
Family
ID=22276580
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19803043374 Withdrawn DE3043374A1 (de) | 1979-12-03 | 1980-11-17 | Verfahren zur herstellung von methylenbis-(methylanthranilat) |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US4252981A (OSRAM) |
| JP (1) | JPS5822141B2 (OSRAM) |
| CA (1) | CA1146959A (OSRAM) |
| DE (1) | DE3043374A1 (OSRAM) |
| FR (1) | FR2471367A1 (OSRAM) |
| GB (1) | GB2064516B (OSRAM) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS60119431U (ja) * | 1983-12-12 | 1985-08-12 | マルホ発條工業株式会社 | 欠陥錠剤選別装置 |
| US4775720A (en) * | 1987-10-29 | 1988-10-04 | International Flavors & Fragrances Inc. | Schiff base reaction products of aldehydes and alkyl anthranilates and organoleptic uses thereof |
| US4824828A (en) * | 1987-10-29 | 1989-04-25 | International Flavors & Fragrances Inc. | Schiff base reaction products of aldehydes and alkyl anthranilates and organoleptic uses thereof |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH586189A5 (OSRAM) * | 1970-01-28 | 1977-03-31 | Bayer Ag |
-
1979
- 1979-12-03 US US06/099,779 patent/US4252981A/en not_active Expired - Lifetime
-
1980
- 1980-07-03 JP JP55090026A patent/JPS5822141B2/ja not_active Expired
- 1980-10-24 GB GB8034383A patent/GB2064516B/en not_active Expired
- 1980-11-04 CA CA000363965A patent/CA1146959A/en not_active Expired
- 1980-11-17 DE DE19803043374 patent/DE3043374A1/de not_active Withdrawn
- 1980-12-02 FR FR8025546A patent/FR2471367A1/fr active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| US4252981A (en) | 1981-02-24 |
| FR2471367B1 (OSRAM) | 1983-01-21 |
| FR2471367A1 (fr) | 1981-06-19 |
| JPS5679655A (en) | 1981-06-30 |
| CA1146959A (en) | 1983-05-24 |
| JPS5822141B2 (ja) | 1983-05-06 |
| GB2064516B (en) | 1983-07-20 |
| GB2064516A (en) | 1981-06-17 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8139 | Disposal/non-payment of the annual fee |