NO126363B - - Google Patents
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- Publication number
- NO126363B NO126363B NO01625/69A NO162569A NO126363B NO 126363 B NO126363 B NO 126363B NO 01625/69 A NO01625/69 A NO 01625/69A NO 162569 A NO162569 A NO 162569A NO 126363 B NO126363 B NO 126363B
- Authority
- NO
- Norway
- Prior art keywords
- ester
- section
- zone
- pipe
- alcohol
- Prior art date
Links
- 150000002148 esters Chemical class 0.000 claims description 50
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 30
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 25
- 230000018044 dehydration Effects 0.000 claims description 21
- 238000006297 dehydration reaction Methods 0.000 claims description 21
- 239000002253 acid Substances 0.000 claims description 19
- 238000000034 method Methods 0.000 claims description 15
- 238000000926 separation method Methods 0.000 claims description 15
- 238000006243 chemical reaction Methods 0.000 claims description 11
- 238000004821 distillation Methods 0.000 claims description 8
- 238000009835 boiling Methods 0.000 claims description 6
- 238000010924 continuous production Methods 0.000 claims description 5
- 238000005886 esterification reaction Methods 0.000 claims description 5
- 239000000203 mixture Substances 0.000 description 22
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 21
- 239000007788 liquid Substances 0.000 description 12
- 239000000047 product Substances 0.000 description 9
- 239000011541 reaction mixture Substances 0.000 description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 239000010410 layer Substances 0.000 description 6
- 239000000376 reactant Substances 0.000 description 6
- XLLIQLLCWZCATF-UHFFFAOYSA-N 2-methoxyethyl acetate Chemical compound COCCOC(C)=O XLLIQLLCWZCATF-UHFFFAOYSA-N 0.000 description 5
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
- SVONRAPFKPVNKG-UHFFFAOYSA-N 2-ethoxyethyl acetate Chemical compound CCOCCOC(C)=O SVONRAPFKPVNKG-UHFFFAOYSA-N 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 230000003248 secreting effect Effects 0.000 description 4
- 230000001105 regulatory effect Effects 0.000 description 3
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 2
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 2
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 2
- -1 CH^-COO-(CH2 ^-O-CH^ Chemical compound 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 2
- 238000010908 decantation Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 239000003456 ion exchange resin Substances 0.000 description 2
- 229920003303 ion-exchange polymer Polymers 0.000 description 2
- PGMYKACGEOXYJE-UHFFFAOYSA-N pentyl acetate Chemical compound CCCCCOC(C)=O PGMYKACGEOXYJE-UHFFFAOYSA-N 0.000 description 2
- JTXMVXSTHSMVQF-UHFFFAOYSA-N 2-acetyloxyethyl acetate Chemical compound CC(=O)OCCOC(C)=O JTXMVXSTHSMVQF-UHFFFAOYSA-N 0.000 description 1
- 229940093475 2-ethoxyethanol Drugs 0.000 description 1
- HXDLWJWIAHWIKI-UHFFFAOYSA-N 2-hydroxyethyl acetate Chemical compound CC(=O)OCCO HXDLWJWIAHWIKI-UHFFFAOYSA-N 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000012141 concentrate Substances 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
- 230000000694 effects Effects 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- DKJCSMHIPYRALV-UHFFFAOYSA-N methoxymethyl propanoate Chemical compound CCC(=O)OCOC DKJCSMHIPYRALV-UHFFFAOYSA-N 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 150000002976 peresters Chemical class 0.000 description 1
- 229920000172 poly(styrenesulfonic acid) Polymers 0.000 description 1
- 229940005642 polystyrene sulfonic acid Drugs 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 239000011949 solid catalyst Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B25—HAND TOOLS; PORTABLE POWER-DRIVEN TOOLS; MANIPULATORS
- B25G—HANDLES FOR HAND IMPLEMENTS
- B25G3/00—Attaching handles to the implements
- B25G3/02—Socket, tang, or like fixings
- B25G3/12—Locking and securing devices
- B25G3/30—Locking and securing devices comprising screwed sockets or tangs
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B25—HAND TOOLS; PORTABLE POWER-DRIVEN TOOLS; MANIPULATORS
- B25G—HANDLES FOR HAND IMPLEMENTS
- B25G3/00—Attaching handles to the implements
- B25G3/02—Socket, tang, or like fixings
- B25G3/12—Locking and securing devices
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/08—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/48—Separation; Purification; Stabilisation; Use of additives
- C07C67/52—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation
- C07C67/54—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation by distillation
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Mechanical Engineering (AREA)
- Crystallography & Structural Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR79000487 | 1968-06-12 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO126363B true NO126363B (ja) | 1973-01-29 |
Family
ID=9696343
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO01625/69A NO126363B (ja) | 1968-06-12 | 1969-04-19 |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US3681204A (ja) |
| JP (1) | JPS5343484B1 (ja) |
| BR (1) | BR6909326D0 (ja) |
| CS (1) | CS176116B2 (ja) |
| DE (1) | DE1919527C3 (ja) |
| ES (1) | ES368127A1 (ja) |
| FR (1) | FR1575909A (ja) |
| GB (1) | GB1204987A (ja) |
| NO (1) | NO126363B (ja) |
| PL (1) | PL80065B1 (ja) |
| RO (1) | RO57696A (ja) |
| SE (1) | SE362412B (ja) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2240317C3 (de) * | 1971-08-21 | 1975-07-10 | Asahi Kasei Kogyo K.K., Osaka (Japan) | Verfahren zur Wiedergewinnung erneut einsetzbarer palladiumhaltiger Katalysatoren aus flüssigen Reaktionsgemischen, die bei der Herstellung von Essigsäurearylestern anfallen |
| NL7501253A (nl) * | 1974-02-15 | 1975-08-19 | Basf Ag | Werkwijze voor het winnen van mierezuur. |
| US4138473A (en) * | 1977-10-31 | 1979-02-06 | Gieck Joseph F | Process for recovering sulfur from sour gas |
| DE3235531A1 (de) * | 1982-09-25 | 1984-03-29 | Chemische Werke Hüls AG, 4370 Marl | Verfahren zur veresterung von essigsaeure mit alkoholen, die 4 und mehr c-atome enthalten, sowie mit glykolethern |
| DE3475188D1 (ja) * | 1983-03-17 | 1988-12-22 | Atlantic Richfield Company | |
| US4502923A (en) * | 1983-10-06 | 1985-03-05 | Monsanto Company | Production of high purity alkyl glyoxylate by plural stage distillation |
| DE3337101A1 (de) * | 1983-10-12 | 1985-05-02 | Chemische Werke Hüls AG, 4370 Marl | Verfahren zur veresterung von essigsaeure mit alkoholen, deren essigsaeureester hoeher sieden als essigsaeure |
| GB8605753D0 (en) * | 1986-03-08 | 1986-04-16 | Bp Chem Int Ltd | Chemical process |
| GB8618892D0 (en) * | 1986-08-01 | 1986-09-10 | Davy Mckee Ltd | Process |
| US4740272A (en) * | 1987-03-31 | 1988-04-26 | Davy Mckee (London) Limited | Separation of monoalkyl maleate from dialkyl maleate |
| US5618973A (en) * | 1994-11-10 | 1997-04-08 | Union Carbide Chemicals & Plastics Technology Corporation | Esterification process |
| WO2013143825A1 (en) | 2012-03-30 | 2013-10-03 | Exxonmobil Chemical Patents Inc. | Esterification process |
| US9481628B2 (en) | 2012-03-30 | 2016-11-01 | Exxonmobil Chemical Patents Inc. | Esterification process |
-
1968
- 1968-06-12 FR FR79000487A patent/FR1575909A/fr not_active Expired
-
1969
- 1969-03-18 JP JP2014569A patent/JPS5343484B1/ja active Pending
- 1969-04-17 DE DE1919527A patent/DE1919527C3/de not_active Expired
- 1969-04-19 NO NO01625/69A patent/NO126363B/no unknown
- 1969-05-09 GB GB23877/69A patent/GB1204987A/en not_active Expired
- 1969-05-28 BR BR209326/69A patent/BR6909326D0/pt unknown
- 1969-06-04 SE SE07919/69A patent/SE362412B/xx unknown
- 1969-06-11 RO RO60224A patent/RO57696A/ro unknown
- 1969-06-11 CS CS4129A patent/CS176116B2/cs unknown
- 1969-06-11 US US832074A patent/US3681204A/en not_active Expired - Lifetime
- 1969-06-11 PL PL1969134121A patent/PL80065B1/pl unknown
- 1969-07-06 ES ES368127A patent/ES368127A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| GB1204987A (en) | 1970-09-09 |
| BR6909326D0 (pt) | 1973-04-05 |
| SE362412B (ja) | 1973-12-10 |
| ES368127A1 (es) | 1971-05-01 |
| RO57696A (ja) | 1975-02-15 |
| CS176116B2 (ja) | 1977-06-30 |
| DE1919527B2 (de) | 1975-01-23 |
| JPS5343484B1 (ja) | 1978-11-20 |
| FR1575909A (ja) | 1969-07-25 |
| DE1919527C3 (de) | 1975-09-11 |
| DE1919527A1 (de) | 1969-12-18 |
| US3681204A (en) | 1972-08-01 |
| PL80065B1 (en) | 1975-08-30 |
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