DE2027502C3 - Verfahren zur Herstellung von Cyanacrylsäureestern - Google Patents
Verfahren zur Herstellung von CyanacrylsäureesternInfo
- Publication number
- DE2027502C3 DE2027502C3 DE2027502A DE2027502A DE2027502C3 DE 2027502 C3 DE2027502 C3 DE 2027502C3 DE 2027502 A DE2027502 A DE 2027502A DE 2027502 A DE2027502 A DE 2027502A DE 2027502 C3 DE2027502 C3 DE 2027502C3
- Authority
- DE
- Germany
- Prior art keywords
- depolymerization
- acid esters
- reaction
- residues
- cyanoacrylic 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
Links
- 238000000034 method Methods 0.000 title claims description 21
- 238000004519 manufacturing process Methods 0.000 title description 8
- IJVRPNIWWODHHA-UHFFFAOYSA-N 2-cyanoprop-2-enoic acid Chemical class OC(=O)C(=C)C#N IJVRPNIWWODHHA-UHFFFAOYSA-N 0.000 title description 4
- 238000006243 chemical reaction Methods 0.000 claims description 16
- 239000011541 reaction mixture Substances 0.000 claims description 8
- 239000007788 liquid Substances 0.000 claims description 7
- MWCLLHOVUTZFKS-UHFFFAOYSA-N Methyl cyanoacrylate Chemical compound COC(=O)C(=C)C#N MWCLLHOVUTZFKS-UHFFFAOYSA-N 0.000 claims description 5
- 238000009835 boiling Methods 0.000 claims description 5
- 238000010438 heat treatment Methods 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 4
- 238000006116 polymerization reaction Methods 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 3
- 239000010409 thin film Substances 0.000 claims description 3
- 229920001651 Cyanoacrylate Polymers 0.000 claims 2
- NLCKLZIHJQEMCU-UHFFFAOYSA-N cyano prop-2-enoate Chemical class C=CC(=O)OC#N NLCKLZIHJQEMCU-UHFFFAOYSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 description 12
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 10
- DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 150000002148 esters Chemical class 0.000 description 9
- 239000003112 inhibitor Substances 0.000 description 8
- -1 cyanoacetic acid ester Chemical class 0.000 description 6
- 239000006185 dispersion Substances 0.000 description 6
- YSMRWXYRXBRSND-UHFFFAOYSA-N TOTP Chemical compound CC1=CC=CC=C1OP(=O)(OC=1C(=CC=CC=1)C)OC1=CC=CC=C1C YSMRWXYRXBRSND-UHFFFAOYSA-N 0.000 description 4
- 238000013459 approach Methods 0.000 description 4
- 229920002721 polycyanoacrylate Polymers 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- 238000007792 addition Methods 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 150000004702 methyl esters Chemical class 0.000 description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 2
- LJCFOYOSGPHIOO-UHFFFAOYSA-N antimony pentoxide Chemical compound O=[Sb](=O)O[Sb](=O)=O LJCFOYOSGPHIOO-UHFFFAOYSA-N 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 229910000634 wood's metal Inorganic materials 0.000 description 2
- JIGUICYYOYEXFS-UHFFFAOYSA-N 3-tert-butylbenzene-1,2-diol Chemical compound CC(C)(C)C1=CC=CC(O)=C1O JIGUICYYOYEXFS-UHFFFAOYSA-N 0.000 description 1
- MGWGWNFMUOTEHG-UHFFFAOYSA-N 4-(3,5-dimethylphenyl)-1,3-thiazol-2-amine Chemical compound CC1=CC(C)=CC(C=2N=C(N)SC=2)=C1 MGWGWNFMUOTEHG-UHFFFAOYSA-N 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 1
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
- UEZVMMHDMIWARA-UHFFFAOYSA-N Metaphosphoric acid Chemical compound OP(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-N 0.000 description 1
- 229930040373 Paraformaldehyde Natural products 0.000 description 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical group [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- MLIREBYILWEBDM-UHFFFAOYSA-N anhydrous cyanoacetic acid Natural products OC(=O)CC#N MLIREBYILWEBDM-UHFFFAOYSA-N 0.000 description 1
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 1
- 150000004056 anthraquinones Chemical class 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- ZIUSEGSNTOUIPT-UHFFFAOYSA-N ethyl 2-cyanoacetate Chemical compound CCOC(=O)CC#N ZIUSEGSNTOUIPT-UHFFFAOYSA-N 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000010408 film Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 125000001188 haloalkyl group Chemical group 0.000 description 1
- 229910000040 hydrogen fluoride Inorganic materials 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 1
- ANGDWNBGPBMQHW-UHFFFAOYSA-N methyl cyanoacetate Chemical compound COC(=O)CC#N ANGDWNBGPBMQHW-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- JCXJVPUVTGWSNB-UHFFFAOYSA-N nitrogen dioxide Inorganic materials O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 1
- 229920002866 paraformaldehyde Polymers 0.000 description 1
- OXNIZHLAWKMVMX-UHFFFAOYSA-N picric acid Chemical compound OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-N 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920000137 polyphosphoric acid Polymers 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 238000007493 shaping process Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000008053 sultones Chemical class 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 150000008027 tertiary esters Chemical class 0.000 description 1
- 238000010792 warming Methods 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
- C07C255/00—Carboxylic acid nitriles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2027502A DE2027502C3 (de) | 1970-05-29 | 1970-05-29 | Verfahren zur Herstellung von Cyanacrylsäureestern |
| US00145242A US3728373A (en) | 1970-05-29 | 1971-05-20 | Method for making cyanacrylic acid esters |
| CH755971A CH556329A (de) | 1970-05-29 | 1971-05-24 | Verfahren zur herstellung von cyanacrylsaeureestern. |
| NLAANVRAGE7107351,A NL170849C (nl) | 1970-05-29 | 1971-05-27 | Werkwijze ter bereiding van cyaanacrylzuuresters. |
| AT458971A AT315813B (de) | 1970-05-29 | 1971-05-27 | Verfahren zur Herstellung von Cyanacrylsäureestern |
| BE767840A BE767840A (fr) | 1970-05-29 | 1971-05-28 | Procede de preparation d'esters cyanacryliques |
| FR7119528A FR2093870A5 (enExample) | 1970-05-29 | 1971-05-28 | |
| GB1786071A GB1333493A (en) | 1970-05-29 | 1971-05-28 | Process for the manufacture of cyanacrylic acid esters |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2027502A DE2027502C3 (de) | 1970-05-29 | 1970-05-29 | Verfahren zur Herstellung von Cyanacrylsäureestern |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2027502A1 DE2027502A1 (de) | 1971-12-09 |
| DE2027502B2 DE2027502B2 (de) | 1979-10-04 |
| DE2027502C3 true DE2027502C3 (de) | 1980-06-19 |
Family
ID=5773048
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2027502A Expired DE2027502C3 (de) | 1970-05-29 | 1970-05-29 | Verfahren zur Herstellung von Cyanacrylsäureestern |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US3728373A (enExample) |
| AT (1) | AT315813B (enExample) |
| BE (1) | BE767840A (enExample) |
| CH (1) | CH556329A (enExample) |
| DE (1) | DE2027502C3 (enExample) |
| FR (1) | FR2093870A5 (enExample) |
| GB (1) | GB1333493A (enExample) |
| NL (1) | NL170849C (enExample) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3409716A1 (de) * | 1984-03-16 | 1985-09-19 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von (alpha)-cyanacrylsaeureestern |
| US5436363A (en) * | 1994-10-03 | 1995-07-25 | Industrial Technology Research Institute | Method for making alkyl-α-cyanoacrylate from depolymerization of poly(alkyl-α-cyanoacrylate) |
| US6420590B1 (en) * | 2000-10-31 | 2002-07-16 | Closure Medical Corporation | Continuous processes and apparatus for forming cyanoacetate and cyanoacrylate |
| WO2004106284A1 (ja) * | 2003-05-30 | 2004-12-09 | Toagosei Co., Ltd. | 精製２−シアノアクリレートの製造方法 |
| US8975435B2 (en) * | 2009-05-07 | 2015-03-10 | Optmed, Inc. | Methylidene malonate process |
| JP2014532625A (ja) | 2011-10-19 | 2014-12-08 | シラス・インコーポレイテッド | メチレンβ−ジケトンモノマー、メチレンβ−ジケトンモノマーを製造するための方法、これらから作られる重合可能な組成物および製品 |
| US8829225B2 (en) | 2012-01-28 | 2014-09-09 | Optmed, Inc. | Purification of 1,1-disubstituted ethylene |
| WO2013149168A1 (en) | 2012-03-30 | 2013-10-03 | Bioformix, Inc. | Composite and laminate articles and polymerizable systems for producing the same |
| EP3626784A1 (en) | 2012-03-30 | 2020-03-25 | Sirrus, Inc. | Ink and coating formulations and polymerizable systems for producing the same |
| US10047192B2 (en) | 2012-06-01 | 2018-08-14 | Sirrus, Inc. | Optical material and articles formed therefrom |
| EP2920231B1 (en) | 2012-11-16 | 2020-05-06 | Sirrus, Inc. | Plastics bonding systems and methods |
| EP3712928A1 (en) | 2012-11-30 | 2020-09-23 | Sirrus, Inc. | Composite compositions for electronics applications |
| US9334430B1 (en) | 2015-05-29 | 2016-05-10 | Sirrus, Inc. | Encapsulated polymerization initiators, polymerization systems and methods using the same |
| US9217098B1 (en) | 2015-06-01 | 2015-12-22 | Sirrus, Inc. | Electroinitiated polymerization of compositions having a 1,1-disubstituted alkene compound |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2721858A (en) * | 1954-03-10 | 1955-10-25 | Eastman Kodak Co | Method of making alpha-cyanoacrylates |
| US2784215A (en) * | 1954-04-07 | 1957-03-05 | Eastman Kodak Co | Monomeric esters of alpha-cyanoacrylic acid and their preparation |
| US3254111A (en) * | 1960-12-09 | 1966-05-31 | Eastman Kodak Co | Esters of alpha-cyanoacrylic acid and process for the manufacture thereof |
| US3465027A (en) * | 1965-12-09 | 1969-09-02 | Eastman Kodak Co | Process for manufacture of high purity alpha-cyanoacrylates |
-
1970
- 1970-05-29 DE DE2027502A patent/DE2027502C3/de not_active Expired
-
1971
- 1971-05-20 US US00145242A patent/US3728373A/en not_active Expired - Lifetime
- 1971-05-24 CH CH755971A patent/CH556329A/xx not_active IP Right Cessation
- 1971-05-27 NL NLAANVRAGE7107351,A patent/NL170849C/xx not_active IP Right Cessation
- 1971-05-27 AT AT458971A patent/AT315813B/de not_active IP Right Cessation
- 1971-05-28 FR FR7119528A patent/FR2093870A5/fr not_active Expired
- 1971-05-28 BE BE767840A patent/BE767840A/xx not_active IP Right Cessation
- 1971-05-28 GB GB1786071A patent/GB1333493A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DE2027502A1 (de) | 1971-12-09 |
| BE767840A (fr) | 1971-11-29 |
| NL170849B (nl) | 1982-08-02 |
| AT315813B (de) | 1974-06-10 |
| GB1333493A (en) | 1973-10-10 |
| NL7107351A (enExample) | 1971-12-01 |
| NL170849C (nl) | 1983-01-03 |
| FR2093870A5 (enExample) | 1972-01-28 |
| CH556329A (de) | 1974-11-29 |
| DE2027502B2 (de) | 1979-10-04 |
| US3728373A (en) | 1973-04-17 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) |