Hxadecyltrimethylammonium bromide ("Cetrimide") is still quite lipophilic so maybe it can substitute for Aliquat 336. It is cheap and easy to get, as it is used in the preparation of shampoo's :
http://www.hkmj.org.hk/skin/govformu.htm (http://www.hkmj.org.hk/skin/govformu.htm)
Don't know if a polysorbate will work, do you have any refs on the subject ?
What about PEG400?
Polyethyleneglycols with molecular weights of 200-600 (particularly PEG 400) works very good as a PTC, and can usually be crashed out from the organic phase by dilution with ether...
In some reactions the free OH groups can also be modified to bear other substituents to modify its properties, for example by attaching phenylphosphines and adding Pd salts you can make a recoverable homogenous catalyst support for all kinds of Pd-catalyzed reactions, as a substitute for Pd(PPh3)3. Example: Post 446706 (https://www.thevespiary.org/talk/index.php?topic=6370.msg44670600#msg44670600)
(Rhodium: "PEG as support/PTC in Pd-catalyzed cross-couplings", Chemistry Discourse)
Most of the article discusses educational aspects of the reaction so I'll type the parts that most benefit bees along with the test reaction so that it is clear how they tested it. It is basically the addition of dichlorocarbene, generated from NaOH and CHCl3 under PTC conditions, to cyclohexene. This is the article that makes me grin whenever walking past the fabric softeners in the supermarket. :)
Fabric Softeners as Phase Transfer Catalysts in Organic Synthesis, J. Chem. Educ. 68, 69-70 (1991):
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Experimental
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To 10 mL of 50% (w/w) aqueous sodium hydroxide solution in a 100-mL round-bottom flask was added 5 mL of cyclohexene and 20 mL of chloroform. Then 2 mL of the fabric softener to be tested was added to the mixture. The stoppered two-phase mixture was stirred magnetically at ~1000 rpm using a 1-in. Teflon-coated stirring bar. The reaction mixture turned turbid as some white emulsion started to form after 15 to 20 min.
The reaction was monitored by GC at 15- to 20-min time intervals. The stirrer was turned off, and 1-mL GC samples were taken from the top organic layer of reaction mixture. The samples were passed through some anhydrous sodium sulfate packed in a Pasteur pipet to remove any of the white emulsion and moisture. The GC experiments were carried out using a 3 mm X 1 m SE-30 column installed in a Hitachi 163 gas chromatograph with flame ionization detector and a Hitachi 561 recorder. In a larger scale experiment, 15 mL of the sodium hydroxide solution, 20 mL of chloroform, 20 mL of cyclohexene, and 8 mL of the fabric softener were stirred for 5 h as above. after simple work up and distillation (collected between 192-198 °C), NMR pure 7,7-dichlorobicyclo[4.1.0]heptane was obtained in 51% Yield1.
Results and Discussion
The reaction times of each fabric softener used were summarized in the table. For 2 mL of the fabric softeners used, the reactions were completed within 2 h with the exception of one brand (run 4, table). Two control experiments were also carried out. Without the fabric softener, the reaction did not proceed as indicated by GC. When a typical phase transfer catalyst, Aliquat 336 (methyltrioctylammonium chloride, 2 mol % to cyclohexene) was used in the reaction, the reaction was also completed in 2 h. This indicated that the effect of 2 mL of fabric softener was roughly equivalent to that of 2 mol % of a typical phase transfer catalyst.
One sample tried did not work well as a phase transfer catalyst (run 4, table). It may be due to the fact that another active ingredient such as noncationic softening agent was used in the formula. It is also worth noting that the concentrated formula (run 3) did not work better as a phase transfer agent than the regular formula (run 2).
Place of Reaction
Fabric softener Manufacture cents/mL time (h)
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1. Soft Great Japan 0.14 1.50
2. Comfort UK 0.16 1.33
3. Concentrated Comfort UK 0.23 1.33
4. Bonnie Hubbard Canada 0.12 >4a
5. Softlan US 0.13 2.00
6. Park'n Hong Kong 0.11 1.00
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aReaction was not completed after 4 h.
[...]
References
1. J. Chem. Educ. 55, 350 and 429 (1978)