GB1217000A - Improvements in or relating to the production of propylene oxide and propylene glycol and its esters - Google Patents
Improvements in or relating to the production of propylene oxide and propylene glycol and its estersInfo
- Publication number
- GB1217000A GB1217000A GB1658068A GB1658068A GB1217000A GB 1217000 A GB1217000 A GB 1217000A GB 1658068 A GB1658068 A GB 1658068A GB 1658068 A GB1658068 A GB 1658068A GB 1217000 A GB1217000 A GB 1217000A
- Authority
- GB
- United Kingdom
- Prior art keywords
- propylene
- propylene glycol
- propylene oxide
- acid
- esters
- 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
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 title abstract 18
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 title abstract 5
- 150000002148 esters Chemical class 0.000 title abstract 4
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 abstract 6
- 239000000203 mixture Substances 0.000 abstract 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 abstract 3
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- -1 alkyl ketone Chemical class 0.000 abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
- 230000003647 oxidation Effects 0.000 abstract 2
- 238000007254 oxidation reaction Methods 0.000 abstract 2
- 150000004965 peroxy acids Chemical class 0.000 abstract 2
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 abstract 2
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 abstract 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 abstract 1
- 150000001242 acetic acid derivatives Chemical class 0.000 abstract 1
- 125000005907 alkyl ester group Chemical group 0.000 abstract 1
- 239000004202 carbamide Substances 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 229910001385 heavy metal Inorganic materials 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 229910052500 inorganic mineral Inorganic materials 0.000 abstract 1
- 150000002500 ions Chemical class 0.000 abstract 1
- 150000002576 ketones Chemical class 0.000 abstract 1
- 239000011707 mineral Substances 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D301/00—Preparation of oxiranes
- C07D301/02—Synthesis of the oxirane ring
- C07D301/03—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds
- C07D301/14—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds with organic peracids, or salts, anhydrides or esters thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/48—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by oxidation reactions with formation of hydroxy groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Epoxy Compounds (AREA)
Abstract
1,217,000. Propylene glycol and its esters and propylene oxide. PETROCARBON DEVELOPMENTS Ltd. 8 April, 1969 [5 April, 1968], No. 16580/68. Heading C2C. Propylene oxide, propylene glycol or an ester thereof are prepared by reacting propylene with an equilibrium mixture comprising at least one carboxylic acid of formula RCOOH, in which R is hydrogen, phenyl or a C 1 -C 5 alkyl radical optionally substituted by one or more electrophilic substituents, a peracid or mixture of peracids corresponding to the carboxylic acid(s), hydrogen peroxide and water, the amount of water present being controlled during the oxidation to produce at least one compound selected from propylene oxide, propylene glycol and its esters with the acid RCOOH, the reaction being effected in the absence of mineral acid and heavy metal ions. The equilibrium mixture may be obtained by mixing an adduct of urea/hydrogen peroxide with an extracting solvent consisting of an alkyl ketone containing up to 7 carbon atoms, an alkyl ester containing up to 7 carbon atoms or a C 1 -C 4 alkyl ortho-phosphate and mixing or replacing the ketone in the resulting solution with the carboxylic acid(s) of formula RCOOH. Examples are given of the oxidation of propylene with an equilibrium mixture containing acetic acid, hydrogen peroxide, peracetic acid and water to give propylene oxide and propylene glycol. When additional water is added to the mixture acetates of propylene glycol are also formed.
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1658068A GB1217000A (en) | 1968-04-05 | 1968-04-05 | Improvements in or relating to the production of propylene oxide and propylene glycol and its esters |
| DE19691917031 DE1917031A1 (en) | 1968-04-05 | 1969-04-02 | Process for the oxidation of propylene |
| NL6905300A NL6905300A (en) | 1968-04-05 | 1969-04-03 | |
| FR6910508A FR2007403B1 (en) | 1968-04-05 | 1969-04-04 | |
| BE731090D BE731090A (en) | 1968-04-05 | 1969-04-04 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1658068A GB1217000A (en) | 1968-04-05 | 1968-04-05 | Improvements in or relating to the production of propylene oxide and propylene glycol and its esters |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1217000A true GB1217000A (en) | 1970-12-23 |
Family
ID=10079879
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1658068A Expired GB1217000A (en) | 1968-04-05 | 1968-04-05 | Improvements in or relating to the production of propylene oxide and propylene glycol and its esters |
Country Status (5)
| Country | Link |
|---|---|
| BE (1) | BE731090A (en) |
| DE (1) | DE1917031A1 (en) |
| FR (1) | FR2007403B1 (en) |
| GB (1) | GB1217000A (en) |
| NL (1) | NL6905300A (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2519298B2 (en) * | 1975-04-30 | 1981-06-04 | Bayer Ag, 5090 Leverkusen | Process for the continuous production of propylene oxide |
| DE2519297B2 (en) * | 1975-04-30 | 1981-05-14 | Bayer Ag, 5090 Leverkusen | Process for the continuous production of propylene oxide |
-
1968
- 1968-04-05 GB GB1658068A patent/GB1217000A/en not_active Expired
-
1969
- 1969-04-02 DE DE19691917031 patent/DE1917031A1/en active Pending
- 1969-04-03 NL NL6905300A patent/NL6905300A/xx unknown
- 1969-04-04 BE BE731090D patent/BE731090A/xx unknown
- 1969-04-04 FR FR6910508A patent/FR2007403B1/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FR2007403B1 (en) | 1974-06-14 |
| DE1917031A1 (en) | 1969-10-23 |
| FR2007403A1 (en) | 1970-01-09 |
| NL6905300A (en) | 1969-10-07 |
| BE731090A (en) | 1969-10-06 |
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