DE1668767C3 - Verfahren zur Hydrodimerisation von Acrylsäurederlvaten - Google Patents
Verfahren zur Hydrodimerisation von AcrylsäurederlvatenInfo
- Publication number
- DE1668767C3 DE1668767C3 DE1668767A DE1668767A DE1668767C3 DE 1668767 C3 DE1668767 C3 DE 1668767C3 DE 1668767 A DE1668767 A DE 1668767A DE 1668767 A DE1668767 A DE 1668767A DE 1668767 C3 DE1668767 C3 DE 1668767C3
- Authority
- DE
- Germany
- Prior art keywords
- ammonia
- reaction
- derivatives
- acrylic acid
- hydrodimerization
- 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 13
- 150000001252 acrylic acid derivatives Chemical class 0.000 title claims 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical group N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 45
- 229910021529 ammonia Inorganic materials 0.000 claims description 20
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 15
- 229910000497 Amalgam Inorganic materials 0.000 claims description 15
- 238000006243 chemical reaction Methods 0.000 claims description 14
- 239000000047 product Substances 0.000 claims description 11
- 239000012429 reaction media Substances 0.000 claims description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 10
- 239000003513 alkali Substances 0.000 claims description 7
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 claims description 6
- -1 Amine salt Chemical class 0.000 claims description 4
- 239000007788 liquid Substances 0.000 claims description 4
- 235000019270 ammonium chloride Nutrition 0.000 claims description 3
- 238000009835 boiling Methods 0.000 claims description 3
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 150000001340 alkali metals Chemical class 0.000 claims description 2
- 239000007795 chemical reaction product Substances 0.000 claims description 2
- 238000004821 distillation Methods 0.000 claims description 2
- 239000011541 reaction mixture Substances 0.000 claims description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 3
- 239000003638 chemical reducing agent Substances 0.000 claims 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 claims 2
- ATHHXGZTWNVVOU-UHFFFAOYSA-N N-methylformamide Chemical compound CNC=O ATHHXGZTWNVVOU-UHFFFAOYSA-N 0.000 claims 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 claims 2
- 125000005250 alkyl acrylate group Chemical group 0.000 claims 2
- 150000003863 ammonium salts Chemical class 0.000 claims 2
- 239000012736 aqueous medium Substances 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 239000000178 monomer Substances 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- 239000007787 solid Substances 0.000 claims 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical group [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims 1
- 239000004952 Polyamide Substances 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 235000011037 adipic acid Nutrition 0.000 claims 1
- 239000001361 adipic acid Substances 0.000 claims 1
- 150000001279 adipic acids Chemical class 0.000 claims 1
- 150000001408 amides Chemical class 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 claims 1
- 229910052921 ammonium sulfate Inorganic materials 0.000 claims 1
- 235000011130 ammonium sulphate Nutrition 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 claims 1
- 239000006227 byproduct Substances 0.000 claims 1
- LYKJEJVAXSGWAJ-UHFFFAOYSA-N compactone Natural products CC1(C)CCCC2(C)C1CC(=O)C3(O)CC(C)(CCC23)C=C LYKJEJVAXSGWAJ-UHFFFAOYSA-N 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 claims 1
- 238000001704 evaporation Methods 0.000 claims 1
- 230000008020 evaporation Effects 0.000 claims 1
- 239000000835 fiber Substances 0.000 claims 1
- 238000005984 hydrogenation reaction Methods 0.000 claims 1
- 239000012535 impurity Substances 0.000 claims 1
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 claims 1
- 239000004033 plastic Substances 0.000 claims 1
- 229920003023 plastic Polymers 0.000 claims 1
- 229920002647 polyamide Polymers 0.000 claims 1
- 150000005599 propionic acid derivatives Chemical class 0.000 claims 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims 1
- 239000000376 reactant Substances 0.000 claims 1
- 238000011084 recovery Methods 0.000 claims 1
- 230000003252 repetitive effect Effects 0.000 claims 1
- CESKLHVYGRFMFP-UHFFFAOYSA-N sulfonmethane Chemical compound CCS(=O)(=O)C(C)(C)S(=O)(=O)CC CESKLHVYGRFMFP-UHFFFAOYSA-N 0.000 claims 1
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 claims 1
- 238000009834 vaporization Methods 0.000 claims 1
- 230000008016 vaporization Effects 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 11
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 10
- BTGRAWJCKBQKAO-UHFFFAOYSA-N adiponitrile Chemical compound N#CCCCCC#N BTGRAWJCKBQKAO-UHFFFAOYSA-N 0.000 description 10
- 229910052708 sodium Inorganic materials 0.000 description 10
- 239000011734 sodium Substances 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- MJGFBOZCAJSGQW-UHFFFAOYSA-N mercury sodium Chemical compound [Na].[Hg] MJGFBOZCAJSGQW-UHFFFAOYSA-N 0.000 description 7
- 229910001023 sodium amalgam Inorganic materials 0.000 description 7
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
- 238000004508 fractional distillation Methods 0.000 description 3
- 229910052700 potassium Inorganic materials 0.000 description 3
- 239000011591 potassium Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 2
- 229910000567 Amalgam (chemistry) Inorganic materials 0.000 description 1
- 101000927799 Homo sapiens Rho guanine nucleotide exchange factor 6 Proteins 0.000 description 1
- 102100033202 Rho guanine nucleotide exchange factor 6 Human genes 0.000 description 1
- 239000004809 Teflon Substances 0.000 description 1
- 229920006362 Teflon® Polymers 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- GGNALUCSASGNCK-UHFFFAOYSA-N carbon dioxide;propan-2-ol Chemical compound O=C=O.CC(C)O GGNALUCSASGNCK-UHFFFAOYSA-N 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000002826 coolant Substances 0.000 description 1
- QHDRKFYEGYYIIK-UHFFFAOYSA-N isovaleronitrile Chemical compound CC(C)CC#N QHDRKFYEGYYIIK-UHFFFAOYSA-N 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- FOBREYJMSUUGLF-UHFFFAOYSA-N n,n-dimethylmethanamine;hypochlorous acid Chemical compound ClO.CN(C)C FOBREYJMSUUGLF-UHFFFAOYSA-N 0.000 description 1
- 210000003739 neck Anatomy 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical compound FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C253/00—Preparation of carboxylic acid nitriles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C253/00—Preparation of carboxylic acid nitriles
- C07C253/30—Preparation of carboxylic acid nitriles by reactions not involving the formation of cyano groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IL2634366A IL26343A (en) | 1966-08-16 | 1966-08-16 | Process for the hydrodimerization of acrylic acid derivatives |
| IL2708966 | 1966-12-19 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE1668767A1 DE1668767A1 (de) | 1971-01-28 |
| DE1668767B2 DE1668767B2 (de) | 1974-05-30 |
| DE1668767C3 true DE1668767C3 (de) | 1975-01-30 |
Family
ID=26320427
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1668767A Expired DE1668767C3 (de) | 1966-08-16 | 1967-08-16 | Verfahren zur Hydrodimerisation von Acrylsäurederlvaten |
Country Status (12)
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE602004019759D1 (de) * | 2003-01-23 | 2009-04-16 | Teijin Ltd | Festphasenpolymerimerisation |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3193574A (en) * | 1960-05-08 | 1965-07-06 | Katchalsky Aharon | Process for the preparation of adiponitrile by dimerization of acrylonitrile |
| GB1157441A (en) * | 1964-06-02 | 1969-07-09 | Ici Ltd | Reductive Dimerisation of Unsaturated Nitriles |
-
1967
- 1967-06-28 SE SE09501/67*A patent/SE326699B/xx unknown
- 1967-06-29 NO NO168835A patent/NO120521B/no unknown
- 1967-07-05 AT AT624067A patent/AT272300B/de active
- 1967-07-21 US US655008A patent/US3519674A/en not_active Expired - Lifetime
- 1967-08-09 NL NL6710958A patent/NL6710958A/xx unknown
- 1967-08-11 LU LU54297D patent/LU54297A1/xx unknown
- 1967-08-12 ES ES344061A patent/ES344061A1/es not_active Expired
- 1967-08-14 CH CH1140867A patent/CH468960A/fr unknown
- 1967-08-14 GB GB37173/67A patent/GB1152104A/en not_active Expired
- 1967-08-14 BE BE702635D patent/BE702635A/xx unknown
- 1967-08-16 DE DE1668767A patent/DE1668767C3/de not_active Expired
- 1967-08-16 CS CS5879A patent/CS149414B2/cs unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DE1668767B2 (de) | 1974-05-30 |
| NL6710958A (enrdf_load_stackoverflow) | 1968-02-19 |
| SE326699B (enrdf_load_stackoverflow) | 1970-08-03 |
| AT272300B (de) | 1969-07-10 |
| DE1668767A1 (de) | 1971-01-28 |
| BE702635A (enrdf_load_stackoverflow) | 1968-02-14 |
| CH468960A (fr) | 1969-02-28 |
| ES344061A1 (es) | 1968-11-01 |
| US3519674A (en) | 1970-07-07 |
| NO120521B (enrdf_load_stackoverflow) | 1970-11-02 |
| LU54297A1 (enrdf_load_stackoverflow) | 1968-03-25 |
| CS149414B2 (enrdf_load_stackoverflow) | 1973-07-05 |
| GB1152104A (en) | 1969-05-14 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) |