DE2421408A1 - Verfahren zur herstellung von butendioldiacetaten - Google Patents
Verfahren zur herstellung von butendioldiacetatenInfo
- Publication number
- DE2421408A1 DE2421408A1 DE2421408A DE2421408A DE2421408A1 DE 2421408 A1 DE2421408 A1 DE 2421408A1 DE 2421408 A DE2421408 A DE 2421408A DE 2421408 A DE2421408 A DE 2421408A DE 2421408 A1 DE2421408 A1 DE 2421408A1
- Authority
- DE
- Germany
- Prior art keywords
- palladium
- butadiene
- reaction
- arsenic
- antimony
- 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- Withdrawn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
- 238000000034 method Methods 0.000 title claims description 10
- 238000004519 manufacturing process Methods 0.000 title description 5
- LMNKSQUFMGNXAW-UHFFFAOYSA-N 1-acetyloxybut-1-enyl acetate Chemical compound CCC=C(OC(C)=O)OC(C)=O LMNKSQUFMGNXAW-UHFFFAOYSA-N 0.000 title description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 27
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 20
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 18
- 238000006243 chemical reaction Methods 0.000 claims description 14
- 229910052787 antimony Inorganic materials 0.000 claims description 9
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 claims description 9
- 229910052785 arsenic Inorganic materials 0.000 claims description 9
- RQNWIZPPADIBDY-UHFFFAOYSA-N arsenic atom Chemical compound [As] RQNWIZPPADIBDY-UHFFFAOYSA-N 0.000 claims description 9
- 229910052763 palladium Inorganic materials 0.000 claims description 9
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims description 8
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 8
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 8
- 239000001301 oxygen Substances 0.000 claims description 8
- 229910052760 oxygen Inorganic materials 0.000 claims description 8
- 229910052714 tellurium Inorganic materials 0.000 claims description 8
- PORWMNRCUJJQNO-UHFFFAOYSA-N tellurium atom Chemical compound [Te] PORWMNRCUJJQNO-UHFFFAOYSA-N 0.000 claims description 8
- 239000007789 gas Substances 0.000 claims description 7
- ORTVZLZNOYNASJ-UPHRSURJSA-N (z)-but-2-ene-1,4-diol Chemical compound OC\C=C/CO ORTVZLZNOYNASJ-UPHRSURJSA-N 0.000 claims description 6
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 6
- 229910052698 phosphorus Inorganic materials 0.000 claims description 6
- 239000011574 phosphorus Substances 0.000 claims description 6
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 claims description 4
- 229910052711 selenium Inorganic materials 0.000 claims description 4
- 239000011669 selenium Substances 0.000 claims description 4
- 239000007787 solid Substances 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 2
- 101001003187 Hordeum vulgare Alpha-amylase/subtilisin inhibitor Proteins 0.000 claims 1
- 239000003054 catalyst Substances 0.000 description 10
- 229910052797 bismuth Inorganic materials 0.000 description 7
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- -1 palladium chloride Chemical class 0.000 description 4
- 239000012071 phase Substances 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 3
- 150000002941 palladium compounds Chemical class 0.000 description 3
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 3
- 229940065287 selenium compound Drugs 0.000 description 3
- 150000003343 selenium compounds Chemical class 0.000 description 3
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 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 2
- CPLXHLVBOLITMK-UHFFFAOYSA-N Magnesium oxide Chemical compound [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- IJJWOSAXNHWBPR-HUBLWGQQSA-N 5-[(3as,4s,6ar)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]-n-(6-hydrazinyl-6-oxohexyl)pentanamide Chemical compound N1C(=O)N[C@@H]2[C@H](CCCCC(=O)NCCCCCC(=O)NN)SC[C@@H]21 IJJWOSAXNHWBPR-HUBLWGQQSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- NMQQBXHZBNUXGJ-SNAWJCMRSA-N [(1e)-buta-1,3-dienyl] acetate Chemical compound CC(=O)O\C=C\C=C NMQQBXHZBNUXGJ-SNAWJCMRSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 229910001570 bauxite Inorganic materials 0.000 description 1
- NMQQBXHZBNUXGJ-UHFFFAOYSA-N buta-1,3-dienyl acetate Chemical compound CC(=O)OC=CC=C NMQQBXHZBNUXGJ-UHFFFAOYSA-N 0.000 description 1
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 229910052570 clay Inorganic materials 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000008246 gaseous mixture Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- HBEQXAKJSGXAIQ-UHFFFAOYSA-N oxopalladium Chemical compound [Pd]=O HBEQXAKJSGXAIQ-UHFFFAOYSA-N 0.000 description 1
- 150000002940 palladium Chemical class 0.000 description 1
- 229910003445 palladium oxide Inorganic materials 0.000 description 1
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 1
- GPNDARIEYHPYAY-UHFFFAOYSA-N palladium(ii) nitrate Chemical compound [Pd+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O GPNDARIEYHPYAY-UHFFFAOYSA-N 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-N phosphoric acid Substances OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 239000008262 pumice Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 150000003342 selenium Chemical class 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- LAJZODKXOMJMPK-UHFFFAOYSA-N tellurium dioxide Chemical compound O=[Te]=O LAJZODKXOMJMPK-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/04—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides onto unsaturated carbon-to-carbon bonds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/04—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides onto unsaturated carbon-to-carbon bonds
- C07C67/05—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides onto unsaturated carbon-to-carbon bonds with oxidation
- C07C67/055—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides onto unsaturated carbon-to-carbon bonds with oxidation in the presence of platinum group metals or their compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Priority Applications (11)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2421408A DE2421408A1 (de) | 1974-05-03 | 1974-05-03 | Verfahren zur herstellung von butendioldiacetaten |
| NL7505032A NL7505032A (nl) | 1974-05-03 | 1975-04-28 | Werkwijze voor het bereiden van buteendioldia- cetaten. |
| FR7513199A FR2269518B3 (enExample) | 1974-05-03 | 1975-04-28 | |
| US05/572,133 US4038307A (en) | 1974-05-03 | 1975-04-28 | Manufacture of butenediol diacetates |
| BE155950A BE828588A (fr) | 1974-05-03 | 1975-04-30 | Procede de preparation de diacetates de butene-diol |
| SU752128753A SU618033A3 (ru) | 1974-05-03 | 1975-04-30 | Способ получени диацетанов бутен2-диолов |
| CA225,888A CA1061361A (en) | 1974-05-03 | 1975-04-30 | Manufacture of butenediol diacetates |
| AT338975A AT339872B (de) | 1974-05-03 | 1975-05-02 | Verfahren zur herstellung von butendioldiacetaten |
| GB18368/75A GB1501004A (en) | 1974-05-03 | 1975-05-02 | Manufacture of butenediol diacetates |
| IT22974/75A IT1037825B (it) | 1974-05-03 | 1975-05-02 | Processo per la preparazione di butendioldiacetati |
| JP50053284A JPS50154204A (enExample) | 1974-05-03 | 1975-05-06 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2421408A DE2421408A1 (de) | 1974-05-03 | 1974-05-03 | Verfahren zur herstellung von butendioldiacetaten |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2421408A1 true DE2421408A1 (de) | 1975-11-13 |
Family
ID=5914573
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2421408A Withdrawn DE2421408A1 (de) | 1974-05-03 | 1974-05-03 | Verfahren zur herstellung von butendioldiacetaten |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US4038307A (enExample) |
| JP (1) | JPS50154204A (enExample) |
| AT (1) | AT339872B (enExample) |
| BE (1) | BE828588A (enExample) |
| CA (1) | CA1061361A (enExample) |
| DE (1) | DE2421408A1 (enExample) |
| FR (1) | FR2269518B3 (enExample) |
| GB (1) | GB1501004A (enExample) |
| IT (1) | IT1037825B (enExample) |
| NL (1) | NL7505032A (enExample) |
| SU (1) | SU618033A3 (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4160115A (en) | 1977-09-22 | 1979-07-03 | Imperial Chemical Industries Limited | Process for the manufacture of butenediol |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4121039A (en) * | 1977-09-26 | 1978-10-17 | Gaf Corporation | Process for producing an unsaturated glycol diester using a catalyst comprising palladium containing thorium as a promotor |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4827290B1 (enExample) * | 1969-03-18 | 1973-08-21 | ||
| DE2217452C3 (de) * | 1971-04-17 | 1978-03-16 | Mitsubishi Chemical Industries, Ltd., Tokio | Verfahren zur Herstellung von 1,4-Diacyloxybuten-(2) |
| JPS5212686B2 (enExample) * | 1973-05-22 | 1977-04-08 |
-
1974
- 1974-05-03 DE DE2421408A patent/DE2421408A1/de not_active Withdrawn
-
1975
- 1975-04-28 FR FR7513199A patent/FR2269518B3/fr not_active Expired
- 1975-04-28 NL NL7505032A patent/NL7505032A/xx not_active Application Discontinuation
- 1975-04-28 US US05/572,133 patent/US4038307A/en not_active Expired - Lifetime
- 1975-04-30 BE BE155950A patent/BE828588A/xx unknown
- 1975-04-30 CA CA225,888A patent/CA1061361A/en not_active Expired
- 1975-04-30 SU SU752128753A patent/SU618033A3/ru active
- 1975-05-02 GB GB18368/75A patent/GB1501004A/en not_active Expired
- 1975-05-02 AT AT338975A patent/AT339872B/de not_active IP Right Cessation
- 1975-05-02 IT IT22974/75A patent/IT1037825B/it active
- 1975-05-06 JP JP50053284A patent/JPS50154204A/ja active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4160115A (en) | 1977-09-22 | 1979-07-03 | Imperial Chemical Industries Limited | Process for the manufacture of butenediol |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS50154204A (enExample) | 1975-12-12 |
| FR2269518B3 (enExample) | 1978-11-10 |
| US4038307A (en) | 1977-07-26 |
| BE828588A (fr) | 1975-10-30 |
| GB1501004A (en) | 1978-02-15 |
| ATA338975A (de) | 1977-03-15 |
| AT339872B (de) | 1977-11-10 |
| NL7505032A (nl) | 1975-11-05 |
| IT1037825B (it) | 1979-11-20 |
| FR2269518A1 (enExample) | 1975-11-28 |
| SU618033A3 (ru) | 1978-07-30 |
| CA1061361A (en) | 1979-08-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| 8130 | Withdrawal |