CN1059664C - Preparation of alkyl phenol polyoxyvinyl ether benzoate - Google Patents
Preparation of alkyl phenol polyoxyvinyl ether benzoate Download PDFInfo
- Publication number
- CN1059664C CN1059664C CN96115847A CN96115847A CN1059664C CN 1059664 C CN1059664 C CN 1059664C CN 96115847 A CN96115847 A CN 96115847A CN 96115847 A CN96115847 A CN 96115847A CN 1059664 C CN1059664 C CN 1059664C
- Authority
- CN
- China
- Prior art keywords
- preparation
- alkylphenol polyoxyethylene
- polyoxyethylene ether
- reaction
- benzoyl chloride
- 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 - Fee Related
Links
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 title claims abstract description 12
- 238000002360 preparation method Methods 0.000 title claims abstract description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 title description 17
- -1 alkyl phenol Chemical compound 0.000 title description 16
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 claims abstract description 10
- 239000012043 crude product Substances 0.000 claims abstract description 10
- 239000007864 aqueous solution Substances 0.000 claims abstract description 9
- 238000006243 chemical reaction Methods 0.000 claims abstract description 9
- 238000005886 esterification reaction Methods 0.000 claims abstract description 7
- 230000035484 reaction time Effects 0.000 claims abstract description 5
- 238000005406 washing Methods 0.000 claims abstract description 4
- 239000000047 product Substances 0.000 claims abstract description 3
- 229940051841 polyoxyethylene ether Drugs 0.000 claims abstract 7
- 229920000056 polyoxyethylene ether Polymers 0.000 claims abstract 7
- 239000000203 mixture Substances 0.000 claims abstract 2
- 230000032050 esterification Effects 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 abstract description 4
- 239000002360 explosive Substances 0.000 abstract description 3
- 238000000034 method Methods 0.000 abstract 1
- 230000003068 static effect Effects 0.000 description 7
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 5
- 125000001033 ether group Chemical group 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- HMWIHOZPGQRZLR-UHFFFAOYSA-N 2-hexadecylphenol Chemical compound CCCCCCCCCCCCCCCCC1=CC=CC=C1O HMWIHOZPGQRZLR-UHFFFAOYSA-N 0.000 description 2
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- MTZQAGJQAFMTAQ-UHFFFAOYSA-N ethyl benzoate Chemical compound CCOC(=O)C1=CC=CC=C1 MTZQAGJQAFMTAQ-UHFFFAOYSA-N 0.000 description 2
- 238000009776 industrial production Methods 0.000 description 2
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000013543 active substance Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 239000002283 diesel fuel Substances 0.000 description 1
- 239000003502 gasoline Substances 0.000 description 1
- 239000003350 kerosene Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 239000003348 petrochemical agent Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
本发明提供一种烷基酚聚氧乙烯醚苯甲酸酯的制备方法，包括烷基酚聚氧乙烯醚与苯甲酰氯的酯化反应及水洗，烷基酚聚氧乙烯醚与苯甲酰氯以1∶1.05-1.2的摩尔比加入反应釜混合反应，反应温度控制在230-80℃，压力为1个大气压，反应时间为2-4小时，静止分离掉水溶液得粗品。该制备方法和现有技术相比，具有设计合理、工艺简单、产品应用范围广、可完全替代现有的易燃、易爆、易污染环境的有机溶剂，且成本低廉等特点，因而，具有很好的推广使用价值。The present invention provides a kind of preparation method of alkylphenol polyoxyethylene ether benzoate, comprise the esterification reaction of alkylphenol polyoxyethylene ether and benzoyl chloride and washing, alkylphenol polyoxyethylene ether and benzoyl chloride Put it into the reactor at a molar ratio of 1:1.05-1.2 and mix it for reaction. The reaction temperature is controlled at 230-80°C, the pressure is 1 atmosphere, and the reaction time is 2-4 hours. The aqueous solution is separated at rest to obtain the crude product. Compared with the prior art, the preparation method has the characteristics of reasonable design, simple process, wide range of product applications, can completely replace the existing organic solvents that are flammable, explosive, and easy to pollute the environment, and has low cost. Very good value for promotion.
Description
The present invention relates to a kind of synthetic method of nontoxic, pollution-free, non-stimulated tensio-active agent, specifically a kind of preparation method of alkyl phenol polyoxyvinyl ether benzoate.
In industrial production, the workman often will be cleaned and overhaul by machinery equipment and component thereof that greasy filth pollutes those, in the prior art those machinery equipment of being polluted by greasy filth and component thereof being cleaned employed clean-out system is gasoline, kerosene, diesel oil, zellon and other organic solvents, or use mixed solvent behind these solvent complexes, the deficiency of its existence is that above-mentioned clean-out system all is petrochemicals, except the cost height, also have explosive, inflammable, not easy to store and the transportation, be difficult to after the use recycle, directly environment is caused severe contamination etc., also do not have good clean-out system to substitute above-mentioned organic solvent at present and be used for industrial production.
The purpose of this invention is to provide that a kind of production cost that can substitute organic cleaning solvent fully is low, environmentally safe, can be used for the preparation method of industrial alkyl phenol polyoxyvinyl ether benzoate on a large scale.
The objective of the invention is to realize in the following manner, adopt alkylphenol polyoxyethylene and Benzoyl chloride to carry out esterification and generate the alkyl phenol polyoxyvinyl ether benzoate crude product, through washing, water was made elaboration in static minute again.
The preparation method of alkyl phenol polyoxyvinyl ether benzoate of the present invention, comprise the esterification and the washing of alkylphenol polyoxyethylene and Benzoyl chloride, esterification be with alkylphenol polyoxyethylene and Benzoyl chloride with 1: the mol ratio of 1.05-1.2 adds the reactor hybrid reaction, temperature of reaction is controlled at 80-230 ℃, pressure is 1 normal atmosphere, reaction times is 2-4 hour, and static separation is removed the aqueous solution and got crude product.
The raw material alkylphenol polyoxyethylene can be that the polymerization degree is n=3-13,
The ether chain is
Alkylphenol polyoxyethylene and the alkyl phenol polyoxyvinyl ether benzoate compound that generated of Benzoyl chloride.With 70-90 ℃ of gained crude product heating, remove the aqueous solution after static and get elaboration.
The concrete preparation method of alkyl phenol polyoxyvinyl ether benzoate of the present invention is as follows:
Embodiment one
1: 1.05 in molar ratio proportioning is calculated and got the polymerization degree is that n=3-13 ether chain molecular formula is:
200 kilograms of nonyl phenol polyethenoxy ethers with molecular formula be
52.6 kilograms of input reactors of Benzoyl chloride in carry out the heated and stirred esterification, temperature of reaction is controlled at 90 ℃, pressure is 1 normal atmosphere, the reaction times is 3 hours, static 1 hour, separates and to remove the aqueous solution and get crude product.
70 ℃ of static aqueous solution of removing of nonyl phenol polyethenoxy ester benzoic ether crude product heating that reaction is generated get elaboration.
Embodiment two
1: 1.05 in molar ratio proportioning is calculated and got the polymerization degree is that n=3-13 ether chain molecular formula is:
200 kilograms of hexadecyl phenol polyethenoxy ethers with molecular formula be
49.88 kilograms of Benzoyl chlorides, drop in the reactor and heat esterification, temperature of reaction is controlled at 200 ℃, pressure is 1 normal atmosphere, the reaction times is 2 hours, static 1 hour, separates and removes the aqueous solution and get crude product.To react and generate 90 ℃ of hexadecyl phenol polyethenoxy ester benzoic ether crude product heating, and remove the aqueous solution after static to get elaboration.
The preparation method of alkyl phenol polyoxyvinyl ether benzoate of the present invention is compared with existing technology, Have that reasonable in design, technology is simple, the product applied range, can substitute fully existing inflammable, The organic solvent of explosive, easy contaminated environment, and the characteristics such as with low cost, thereby, have well Popularizing value.
Claims (2)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN96115847A CN1059664C (en) | 1996-06-21 | 1996-06-21 | Preparation of alkyl phenol polyoxyvinyl ether benzoate |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN96115847A CN1059664C (en) | 1996-06-21 | 1996-06-21 | Preparation of alkyl phenol polyoxyvinyl ether benzoate |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1169980A CN1169980A (en) | 1998-01-14 |
| CN1059664C true CN1059664C (en) | 2000-12-20 |
Family
ID=5123057
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN96115847A Expired - Fee Related CN1059664C (en) | 1996-06-21 | 1996-06-21 | Preparation of alkyl phenol polyoxyvinyl ether benzoate |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN1059664C (en) |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0241985A2 (en) * | 1986-04-15 | 1987-10-21 | The Procter & Gamble Company | Capped 1,2-propylene terephthalate-polyoxyethylene terephthalate polyesters useful as soil release agents |
| CN1109048A (en) * | 1994-12-28 | 1995-09-27 | 段奎敏 | Benzoic acid C12-15Synthesis of alcohol ester and application in cosmetics |
-
1996
- 1996-06-21 CN CN96115847A patent/CN1059664C/en not_active Expired - Fee Related
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0241985A2 (en) * | 1986-04-15 | 1987-10-21 | The Procter & Gamble Company | Capped 1,2-propylene terephthalate-polyoxyethylene terephthalate polyesters useful as soil release agents |
| CN1109048A (en) * | 1994-12-28 | 1995-09-27 | 段奎敏 | Benzoic acid C12-15Synthesis of alcohol ester and application in cosmetics |
Also Published As
| Publication number | Publication date |
|---|---|
| CN1169980A (en) | 1998-01-14 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US5110972A (en) | Process for recycling silicone scrap and products relating thereto | |
| JPS58125798A (en) | Organic gel | |
| DE59503856D1 (en) | AMPHIPHILE POLYESTER, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE IN DETERGENTS | |
| JPH07197047A (en) | Diesel fuel and its production | |
| WO2012039912A1 (en) | An environmentally friendly base fluid to replace toxic mineral oil-based base fluids | |
| CN102206156A (en) | Method of Comprehensive Utilization of CTA Residue Resource | |
| CN1059664C (en) | Preparation of alkyl phenol polyoxyvinyl ether benzoate | |
| US3053783A (en) | Water soluble polyesters of benzene polycarboxylic acids | |
| CN1059663C (en) | Method for preparation of alkyl polyoxyethylene ether benzoate | |
| CN103554462B (en) | A kind of preparation method containing hyper-branched polyester dispersion agent | |
| CN106966559B (en) | Oil sludge treatment dispersant, preparation method and application thereof | |
| CN100564600C (en) | Corrosion inhibitor formulations with improved performance, lower toxicity and reduced production hazards | |
| JPH04216868A (en) | Bituminous substance containing hydrolyzed or alcoholyzed polymer residue | |
| US7045492B2 (en) | Cleaning composition comprising cationic surfactants, chelant, and an alcohol solvent mixture | |
| CN110483299B (en) | Polymerizable surfactant containing aromatic hydrocarbon structure and preparation method thereof | |
| US2679522A (en) | Esters of oxypropylated glycols and polycarboxylic acids | |
| Bratton et al. | The role of oligomers in the synthesis of polysilanes by the Wurtz reductive coupling reaction | |
| US2790777A (en) | Process of breaking petroleum emulsions and compositions therefor | |
| CN1492007A (en) | Paint remover and preparing method | |
| CN116239484B (en) | Monoamino polycarboxylic amphoteric and viscoelastic surfactant, and preparation method and application thereof | |
| US3117107A (en) | Copolyesters | |
| KR100998243B1 (en) | Cleaning composition for high viscosity metalworking oil | |
| CN103911231A (en) | Automobile windshield cleaning agent | |
| US2490748A (en) | Preparation of esters of acids of phosphorus | |
| CN104072741B (en) | A kind of polyester polyol and polyurethane foaming agent and preparation method |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C14 | Grant of patent or utility model | ||
| GR01 | Patent grant | ||
| C19 | Lapse of patent right due to non-payment of the annual fee | ||
| CF01 | Termination of patent right due to non-payment of annual fee |