Talk:Nonylphenol

This article was the subject of an educational assignment in 2013 Q3. Further details were available on the "Education Program:Boston College/Environmental Disruptors of Development (Spring 2014)" page, which is now unavailable on the wiki.

Chembox is not Nonylphenol

Chembox is not that of 4-Nonylphenol, but that of 4-(2,6-Dimethylheptan-4-yl)phenol. All interwikis are wrong too. Albmont (talk) 13:51, 14 March 2010 (UTC)[reply]

I still think the article (and the interwikis) are confusing. If "Nonylphenol" is a mixture of all isomers except 4-(n-nonyl)-phenol, then I think the article should be renamed to something else (like "Nonylphenol (mixture)"). OTOH, maybe there should be two articles with details about the two compounds for which we have chemboxes: the ramified version, and the para-linear-version. Albmont (talk) 17:07, 14 March 2010 (UTC)[reply]

I sympathize with your views completely, but ... mixtures are the rule in the world of surfactants, coatings, plasticizers, etc. By getting too picky about exact meanings, we could in fact diminish the usefulness of the article. IMHO, an article on, say, 1-nonyl-4-phenol would possibly be a disservice because 1-nonyl-4-phenol is not used for anything, ever. In terms of readership, I am thinking of people who are interested in both the applications and environmental/safety aspects. They want to understand the mixture. We should still be able to construct a ChemBox. ChemAbs assigns CAS#'s to mixtures, we have m.p. and b.p. ranges, ranges for formulae, etc. Thanks for noticing this issue, which deserves further thought and possibly some policy decisions. --Smokefoot (talk) 17:37, 14 March 2010 (UTC)[reply]

Oh, I just noticed the problem, the ChemBox apparently is written for a single isomer. I guess we could delete it, or move it to this talk page. I would be surprised if much 1-nonyl-4-phenol is available, esp since alkylation of phenol with 1-nonene would give the 2-nonyl-4-phenol.--Smokefoot (talk) 17:55, 14 March 2010 (UTC)[reply]

So I think the best solution would be to create two more articles, one for each isomer, and keep this article. Albmont (talk) 01:51, 15 March 2010 (UTC)[reply]

Yep, I agree. Would you create the article? Thanks again, --Smokefoot (talk) 02:43, 15 March 2010 (UTC)[reply]

I am very bad at creating articles. And most of them are marked for deletion. But I may help mounting the Chemboxes. Albmont (talk) 17:03, 15 March 2010 (UTC)[reply]

Okay, we have 1-nonyl-4-phenol with new fig. You might check the data to be sure that they are for the straightchain isomer. And when you get a chance, please recheck nonylphenol. See you around, --Smokefoot (talk) 00:08, 16 March 2010 (UTC)[reply]

Checking 1-Nonyl-4-phenol: I think the CAS Number is wrong, because it points to a site where the synonyms are (2,6-Dimethylheptan-4-yl)phenol, n-Nonylphenol, a mixture of aklyl-phenol isomers, and/or a mixture of isomers and ethers.

BTW, how reliable are those internet sites that give information about compounds? For example, http://msds.chem.ox.ac.uk/NO/nonylphenol.html and http://www.lookchem.com/4-NONYLPHENOL/ give the CAS Number as 104-40-5; whilehttp://www.chemindustry.com/chemicals/043619.html gives 68152-92-1 (with the confusion of the linear para isomer and the mixture).

I am afraid eventually it will be impossible to find reliable internet sources outside of wikipedia, as most sites copy from wikipedia and don't bother to check the primary or secondary sources. Albmont (talk) 12:32, 16 March 2010 (UTC)[reply]

Checking Nonylphenol: I just noticed that the compound name does not match the image! The image is 4-(2,4-dimethyl-heptan-3-yl)-phenol, and not 4-(2,6-dimethyl-heptan-4-yl)-phenol. The site where the CAS number points is wrong too. Albmont (talk) 12:37, 16 March 2010 (UTC)[reply]
Checking pt:Nonilfenol: the Chembox is that of a branched isomer, the text is that of the mixture, and the (supposedly) reliable source is that of the linear para isomer. But I am suspicious of everything that comes from the g*vernment (if you can't read Portuguese, the site describes commercial Nonylphenol, with 90% para-nonylphenol, 4% orto-nonylphenol and 5% 2,4-dinonylphenol; this may explain why the data differs slightly from de:Nonylphenol:

Freezing point (Ponto de fusão -10 x Schmelzpunkt 2)
Boiling point (Ponto de ebulição 304 x Siedepunkt 295-304) Albmont (talk) 12:55, 16 March 2010 (UTC)[reply]

For those that are still following this: I created the article pt:4-n-Nonilfenol, corresponding to 1-Nonyl-4-phenol, using the German chembox in de:Nonylphenol as basis. For this compound (and not for the class of nonylphenols) it seems that the chemboxes are different - I checked the pt: chembox, and it seems consistent with the sources. I suggest that this discussion continues (if anyone wants to continue!) in Talk:1-Nonyl-4-phenol. Albmont (talk) 13:28, 19 May 2010 (UTC)[reply]

February 2014

Here is a list of review articles that will be consulted when expanding the article:

Sonnenschein, Carlos, and Ana M. Soto. "An Updated Review of Environmental Estrogen and Androgen Mimics and Antagonists." The Journal of Steroid Biochemistry and Molecular Biology 65.1-6 (1998): 143-50. Juli12Anne (talk) 20:49, 17 February 2014 (UTC)[reply]

Asimakopoulos, Alexandros G., Nikolaos S. Thomaidis, and Michael A. Koupparis. "Recent Trends in Biomonitoring of Bisphenol A, 4-t-octylphenol, and 4-nonylphenol." Toxicology Letters 210.2 (2012): 141-54. Web.

Jie, Xu, Li Jianmei, Feng Zheng, Gong Lei, Zhang Biao, and Yu Jie. "Neurotoxic Effects of Nonylphenol: A Review." Wiener Klinische Wochenschrift 125.3-4 (2013): 61-70. Web.

Ponzo, Osvaldo J., and Carbone Silvia. "Evidence of Reproductive Disruption Associated with Neuroendocrine Changes Induced by UV–B Filters, Phtalates and Nonylphenol during Sexual Maturation in Rats of Both Gender." Toxicology 311.1-2 (2013): 41-51. Web.

OliviaHall10 (talk) 20:32, 17 February 2014 (UTC)[reply]

This article published by the EPA in 2010 goes into the human health and environmental affects of NPs and NPEs and what the next steps for regulating these chemicals are:

EPA. 2010. Nonylphenol (NP) and Nonylphenal Ethoxylates (NPEs) Action Plan. February, 2014. Juli12Anne (talk) 20:58, 19 February 2014 (UTC)[reply]

Here is a tentative summary for the layout of the revised page:

Chemical structure and properties

Structure—talk about nonylphenols and nonylphenol ethoxylates

Production

Uses

Detergents—laundry detergents,

Occurrence in the environment

Water supplies—we will discuss how manufacturers release NPs and NPEs into the environment and how they subsequently enter water systems.

Environmental Hazards

Aquatic toxicity

Health Hazards

Toxicity—provide levels of exposure that have been to cause adverse effects.

Endocrine Disruption—discuss what physiological effects are seen in model organisms (mice). For example: decreases in epididymal sperm density or testicular sperm head counts, increased in estrous cycle length, etc.

Protection policies

OliviaHall10 (talk) 21:07, 19 February 2014 (UTC)[reply]

Review of Article

Thanks for the reviews, guys! We added a ton more wikilinks and found a few more sources, as well. We agreed on the need for information about bioaccumulation, so we added a few sentences about this in both the environmental and human health sections. Additionally, we added a bit about the breakdown/metabolism of NP, as suggested. We also added more in the policy section. We also added more about associations with NP exposure and breast cancer. Finally, we changed the layout of the article for clarity. Thanks for the suggestions!

OliviaHall10 (talk) 01:52, 5 May 2014 (UTC)[reply]

Peer Review #1: Overall great job, this was a strong and informative article. The article flows very nicely throughout, the headings and subheadings were very helpful to understand all the information presented. The information regarding the health and environmental effect were presented in a matter-of-fact way in which I could not easily detect any biases. In general I would like to see more citations and wiki links to help lay readers understand the more scientific aspects of the article better. Also a quick read through of the article for grammatical errors would be helpful to improve the flow of the article.

Introduction: This should be expanded to provide a more comprehensive summary of what is to be presented in the article. I suggest a clearer explanation of the applications/ uses/ where NP might be found in daily life, and an expansion on the health and environmental hazards that the chemical poses, so that readers know why they need to read on.

Structure and basic properties: Strong section, my only comment would be working at making this section a little easier to read for someone who does not have a very strong chemistry background. This might be done through more expansive explanations or simply by adding wikilinks.

Production: I found the natural occurrence in the velvet worm very interesting. As I understand it, the primary use of NP is as an intermediate to NPEs, which isn’t explicitly stated in this section. I was a bit confused about the motivation/ discovery of NP in the first place, which could be expanded upon in this section. Also is the annual 100-500million lbs production worldwide?

Applications: Informative and concise section, which is good. I would like to have had wikilinks to each of the applications. Then in the last sentence of the first paragraph, specifically what “household detergents outside of Europe” are APEs used in?

Prevalence in the Environment: This section nicely explains how NP gets into the environment and might stay in the environment. Expansion of the persistence/ bioaccumulation of NP in the environment might be better stressed. I would edit the wording of the first sentence of the second paragraph for clarity, I was confused about how it said that occurrence of NP in aquatic environments was not well studied, but then it seemed as though the first paragraph discussed NP in rivers.

Health and environmental Hazards: Overall a highly informative, interesting, and thought provocative section. All of the information was presented in a very neutral and unbiased way, clearly aimed at simply informing/ warning readers about what is known about effects of NP. Again, thoroughly wikifying this section would make it much easier for lay readers to get through and understand all the information presented.
- Environmental: I suggest expanding upon the endocrine disrupting actions of NP in aquatic organisms. Are there specific studies that have looked at the different effects of NP on the environment? If so, citing these might makes the information more powerful. I was also just wondering if there were any other non-aquatic/ non-human organisms which are adversely affected by NP?
- Human Health: The readability of this section would benefit from splitting up the xenoestrogenic information from the health effects into two different sections. The last sentence should either be expanded upon or included in the previous paragraph explaining the detrimental health effects of NP.
- Human Exposure: I suggest switching/ including this subsection with the Human health subsection to improve the flow of the article, because as I was going through the Human health subsection I kept wondering how NP got into the body in the first place. I would have appreciated a better explanation of the metabolism of NP within the body.

Regulation: Again I complement the neutral nature of this section, concentrating on worldwide regulation of NP rather then just from the US perspective. I really liked how you mentioned less damaging/ hazardous NP replacements as a solution, it might be interesting to expand upon topic if there is any more information available about this.

In general I enjoyed reading this article, found it highly informative, and learned a lot about a subject that I had very little background. Good job!

chingla 22:51, 10 April 2014 (UTC)[reply]

Peer Review #2. This is the peer review of this article by Brichr1520. Great, interesting article!

The overall article is incredibly interesting and provides a great summary of academic findings and knowledge about nonylphenol. While the sections could benefit from some structural reorganization, the approach is balanced and overall neutral, which is usually difficult when attempting to describe what harmful effects nonylphenol poses. The article relies on fourteen sources, so more research (if available) on some aspects listed below may help the reader. The language of the article is well-written and understandable for a broad audience. It would also be interesting to include any tables or figures from the scientific resources as a visual, if possible.

Introduction:

This section needs to be expanded beyond just a few sentences. I would suggest providing a summary of the main points in the article, with a greater emphasis on the chemistry and uses of nonylphenols. When explaining the uses thereof, I would at least list a few descriptions of where nonylphenol is found, and maintain a sense of neutrality. Consequently, I would focus less on describing the “attracted attention” based on environmental impacts, as this has a negative (though true) connotation and seldom invites a reader to continue. Some suggestions on achieving this are to attribute the rise in attention to nonylphenol through another use (perhaps mentioned in your “Did you Know?,” or that nonylphenol occurs naturally), or to write about the potential environmental impacts significantly more neutral; it would be helpful to evade words such as “pervasive,” for instance.

Furthermore, to an average person who knows little about “organic compounds,” the introduction may confuse readers. Currently, the introduction is written as though for a more advanced audience, such as chemists or biologists more knowledgeable about “organic compounds.” I would write at least another sentence or two describing this and how nonylphenol correlates to “organic compounds,” making it more readable for a broader audience.

Structure and basic properties:

This section demonstrates great, logical flow of ideas and a good description of NPs’ chemical structure and tendencies. There were a couple minor grammatical issues, which are now resolved.

In the first paragraph of the section, the description states, “A branched nonylphenol, 4-nonylphenol, is the most widely produced and marketed nonylphenol.” What does “widely produced” and “marketed” reference? Is this a hint at its uses? If so, it would be helpful to very briefly introduce the uses, such as “marketed nonylphenol for the production of ____.” This would improve the readability and allow the reader to make or recognize connections for later sections of the article.

It may also be beneficial to provide a very brief description of alkylphenols and APEs and a bit more detail on its correlation to nonylphenol for the reader, if this information is available, so as to provide a more balanced background to nonylphenols themselves for the reader.

Production:

The information provided is incredibly interesting, especially about the velvet worms. Do any other organisms exhibit this defense mechanism? Has production of synthetic nonylphenol as a “High Production Volume Chemical” been modeled on the discovery of the velvet worm? These two questions may help to expand the section.

It may also benefit the overall flow of the article to combine the “Production” and “Applications” sections into one section. Placing the information about the velvet worm could commence the section. If there are any connections to the synthetic production of nonylphenol based on the velvet worm discovery, this information may provide a useful link to the applications and uses.

Prevalence in the environment:

This section is a great, albeit brief, introduction to broader environmental issues. Thus, it may be beneficial to combine this section with the “Health and environmental hazards” section, using the “Prevalence” section as the introduction; this would improve the readability of the article. There were also a few grammatical issues, which have been addressed.

The most interesting part in this section was the connection between sewage sludge and agriculture. To emphasize the effects of nonylphenols in sewage and potentially in agriculture, a discussion about its potential effects on food security, and what this means for the environment and public health, would immensely benefit this point and the broader article.

Health and environmental hazards:

In the “environmental” sub-section, a wikilink of steriodgenesis would be helpful to the reader, if available. To further expand this sub-section, broader implications of the studies on fish to impact on other organisms should be stated. It would also be beneficial to talk about other short-term and long-term effects on the environment, such as bioaccumulation in soil or water. The connection between nonylphenol and breast tumor cell proliferation is interesting, but needs elaboration, such as describing the mechanisms thereof and its further repercussions on human health. This section provides a good variety of multidimensional information from the perspective that it does not analyze nonylphenol strictly in the U.S., but rather looks at Europe and Taiwan as well.

Regulation:

This is a great section with a multi-perspective on regulations of nonylphenol. However, the information jumps from the EU to the U.S. to Asia and back to Europe, so structural reorganization of the second paragraph would enhance the readability. In the second paragraph the description states, “In other Asian and South American countries there is still a large about of APE's and little regulation” – large what? This section would also benefit from elaboration of what specific countries in the mentioned regions are doing both from a policy and from a direction action perspectives.

Brichr1520 (talk) 18:51, 11 April 2014 (UTC)Brichr1520[reply]

missing sections and comment on references

This article misses "see also" WP:ALSO and "external links" Wikipedia:External links.--Wuerzele (talk) 02:38, 12 April 2014 (UTC)[reply]

Also, I suggest to use references that do not require a subscription whenever possible. Without exception none of the 12 references from scientific journals were accessible (only the 2 policy related refs) . I recommend to use Environmenatl Health Perspectives; it is open access and has tons of relevant articles.--Wuerzele (talk) 02:52, 12 April 2014 (UTC)[reply]

Additional Suggestions

This was a very informative article! However, I have a few suggestions:

- I would, if possible, expand upon the cancer section. Do nonylphenols only cause breast cancer or are people at risk for other reproductive tract cancers as well?

- I would possibly move the Human Exposure Section further towards the top. I think it should also be its own major section as it is very important. People want to know how this chemical affects them, how they will come into contact with nonylphenols, and how to avoid them.

- How do nonylphenols affect fish? Does it kill them or affect their reproduction in any way?

I really liked your Regulations section as it gave examples of how the government is working towards decreasing the amount of nonylphenols in the atmosphere and leaves the reader with a sense of hope.

Sej942 (talk) 02:14, 2 February 2015 (UTC)[reply]

Concerning your second point: Do you know Wikipedia:Manual of Style/Chemistry/Chemicals? --Leyo 10:06, 2 February 2015 (UTC)[reply]

Furthermore, please aim for WP:SECONDARY, i.e. cite books and reviews, steering away from websites and primary journals. --Smokefoot (talk) 14:15, 2 February 2015 (UTC)[reply]

2D structure

Is this representation correct? It does not match that on PubChem (https://pubchem.ncbi.nlm.nih.gov/compound/4-nonylphenol). I took the SMILES string from the wiki article and used it with ToxTree and OECD QSAR. Both returned the PubChem version.

213.253.35.226 (talk) 15:19, 23 April 2020 (UTC)[reply]